DEFINITION: "Click-bait" is a web page link designed to entice users to go to a certain web-page or video. Click-bait headlines typically aim to exploit the "curiosity gap", providing just enough information to make readers curious, but not enough to satisfy their curiosity without clicking through to the linked content. – per Wikipedia. Be careful what you click on!
Click-bait is a web page link designed to entice users to go to a certain web-page or video. Click-bait headlines typically aim to exploit the "curiosity gap", providing just enough information to make readers curious, but not enough to satisfy their curiosity without clicking through to the linked content. – per Wikipedia.
The Setup
Jack was an unmarried recent college graduate with a degree in corporate finance and a minor in Social Media. He was in his first year with a Big Ten accounting firm and was working towards an MBA. His future looked bright. He was active with social media postings, tweets and blogging. He had accounts with Facebook, Pinterest, Twitter, LinkedIn, Instagram, Google +, and several other web based outlets; he was a frequent participant. He also was an extremely proficient, but discreet, cross-dresser.
Jack first became aware of his feminine side at age ten. More than twelve years later he had a complete ‘Jackie’ wardrobe and indulged himself as often as possible. He was adept at makeup with emphasis on the eyes. He had his ears pierced at age 13. His makeup collection was complete. Being single he never slept in pajamas; always a baby doll or chemise. His robe was a silk kimono; his slippers were fur trimmed mules with a two inch heel. His natural hair color was brunette. ‘Jackie’ was his chosen femme name.
In the privacy of his condo he routinely web-surfed cross-dressing web sites and had his favorite sites book marked. Some sites were stories, one was for social conversations, advice, and idea exchange relating to the CD/TG community, and another was videos and photos of cross-dressers. Some of his bookmarked sites were porn.
Jack had recently become enthralled with male-to-female photo morphing sites. He liked the fact that he could try a variety of makeup, hair styles and looks and not having to go to the trouble of makeup application, removal, reapplying, etc.; it was all virtual. Just upload a good selfie head shot and play around with no hassle; find a look, hair color or style he liked and then click and save. He had a special computer file labeled ‘Jackie’ where he saved and stored his better looks. His digital photo ‘saves’ didn’t totally disguise Jack. You would think it was Jack’s beautiful twin sister but there was no mistaking or hiding the innate ‘Jack qualities’. He made a very pretty woman.
Trans Form You
Trying to find a better male to female morphing site he stumbled into TransFormU.com that would, in addition to hair and makeup head shots, give you the option of selecting body shapes, breast size, and cleavage options. It also had a clothing, jewelry, shoes and lingerie feature where you could try these items on your virtual body. A finished effort through, TransFormU, would have your perfectly made up, feminine face, on a beautiful woman’s body, dressed or undressed to your specifications. TransFormU.com was perfect in many ways.
Jack was enthralled with making Jackie look and dress beautiful and therefore he was enthralled with the TransformU website. The site offered many options not found on any website that Jack had ever found. Once you had your basic image selected and ‘saved’ you could simply click on what look, image or profession you wanted to look like. With a single mouse click you could be dressed to look like a cheerleader, bride, rock star, a domination mistress, school girl, a nursing mother, etc. There were anime, adult baby, sissy, and biker bitch options. There even was a ‘slut-me-up’ button.
Another unique feature was that once you had the look you wanted you could have your femme photo placed with a background that matched your outfit. The selections were amazingly real world in appearance; if you were in a swim suit you could be shown on a beach, in a wedding dress you could be in a church, as a cheerleader you could be on a football field, as a biker bitch in a bar… just click and choose. The effects were endless and all were fantastically real looking.
Jack had visited the TransFormU site twice, trying to become familiar with how to use the many features. It was on his third visit when he found the site had added a new, adult, feature. It was a beta feature. Once you had selected your complete ‘look’ you would click on the ‘slut-me-up’ options and, for a small $50 fee, the site would put you, in your chosen image, into a two minute computer-generated imagery porn movie! $200 got you five vignettes. A finished movie looked exactly like the real thing. A person could experience, virtually, the desires, impulses and sex acts that they may have thought about, or even dreamed about, but which they would never actually do or act upon.
‘Be the slut you yearn to be’ without the fear of STDs, societal scorn or family drama.
A practical aspect of TransFormU.com was the ability for you to work on several projects concurrently, save them all on the site, and add new features to them until they were complete before saving and downloading them all at once. Among the still photos Jack had already saved was Jackie as a long haired blond with a 40D breast, impressive cleavage, nude, wearing high heels and made up like a runway model. He added scarlet lipstick and finger nails for the effect he liked.
Saving and building on this basic virtual image Jack clicked on ‘lingerie mode’ placing Jackie in matching red garter belt and panty set, black stockings, a black and red pushup bustier (with lace trim) that emphasized cleavage. Jack added black four inch pump heels, sexy gold chandelier earrings, show girl makeup and long brunette hair. For a background he had Jackie standing, with her hands on her hips, at the foot of a magnificent bed in a beautiful boudoir setting.
Jack also refined the classic cross-dressers fantasy of wearing a wedding dress. For a background he opted for a soothing mountain meadow setting. Jackie made a beautiful bride. Finding a ‘waif’ option Jack added this look giving Jackie a more provocative, pouty, look. Just one click of his mouse made it happen.
Another effort for Jackie was the bikini swim suit option. He swapped her into a red hair pixie cut hair style, increased the feminine arch of her eyebrows and opted for a skimpy pushup top that gave Jackie an outstanding cleavage. The string bikini bottom was barely there and was erotic for him to look at. He selected a Laguna Beach setting to complete this fantasy. Jackie looked hot!
The final scenario Jack created was that of the perfect Sissy. Black patent leather Mary Jane shoes and white leggings were easily added. His Sissy dress had a large bow in the back. And of course his face was perfectly made-up. Let your imagination complete your mental image of what this entailed.
Developing each image took a pleasant toll on Jack and his arousal increased the more he explored what he could do with Jackie and TransFormU. He had all his virtual creations ‘saved’ and ready for download to his laptop. Yet there was one additional feature of TranForm he wanted to use; the ‘Slut-Me-Up’ option. Before attempting this he wanted to switch to Jackie mode; it would fit with what he was about to do.
A repressed and tightly controlled fantasy for Jack was having a sexual relationship with a man. It was a fantasy that he doubted he would ever act on. He was, he thought, very much in control of his desires, impulses and fantasies. What would it be like to be on the receiving end of a steamy, same sex, relationship while in full Jackie mode? There were tastes, sensations, and lusty feelings he secretly yearned for. He was curious.
Before trying the beta ‘Slut-Me-Up’ feature Jack went to his kitchen and mixed himself a Tito’s vodka and Sprite. Taking his drink to his bedroom he swapped from his male clothes to Jackie clothes. This didn’t take long as he had been wearing lingerie under his pants and shirt all day at work as he usually did. He slipped breast forms into his bra, pulled on a pair of lacy peach shorty pettipants (for tactile reasons), donned a cute, flowered, romper and inserted 2 inch gold hoop earrings into his waiting ears. He already had his garter belt and cinnamon stockings on which made slipping into his black ballet style shoes easy; they were well broke in.
Jack went to his vanity, sat down and applied some facial make-up, eyeliner, a bit of eye shadow and mascara. His hair was long enough that he could easily backcomb it a bit and shape a believable pixie hairstyle. A blast of hairspray maintained his femininity. Finding his favorite shade of lipstick he expertly enhanced his lips. He gave himself a spritz of perfume and was ready to try the ‘Slut-Me-Up’ option on TransFormU. He wanted to be a bit naughty when he made virtual Jackie naughty.
The growing bulge in her French cut panties urged Jackie to lie down on the bed to relive her building lust. Jackie had a pressing date with TransFormU and didn’t want to take the time so she folded some tissues and placed them in her panties to soak up the pre-seminal oozing. Grabbing her purse, that held her credit card, Jackie went back to her lounging chair and her laptop.
Sitting back in her chair Jackie took another swig of her drink, retrieved her credit card, logged into TransFormU and prepared to get slutty. She was weighing which version of virtual Jackie to make “slutty”. ‘Lingerie Jackie’ or ‘Bride Jackie’? They both seemed like exciting and very worthwhile options.
Jackie carefully entered her credit card number, and when prompted, selected Lingerie Jackie. She had a couple more criteria to click on. For ‘select a place’ (for her movie to take place in) she chose the ‘bedroom’ option, and for the ‘with who’ drop down menu she clicked on ‘two men’, making a promise to herself to next time try the ‘man + woman’ scenario. Her final choice was ‘voluntary or rape’? Jackie wanted to be a willing participant in whatever would be depicted. She smiled as she thought about how the final product would play out.
Before clicking on the ‘Slut-Me-Up’ icon Jackie modified her ‘self’ by switching to long platinum blond hair, added bangs and ultra sexy, vixen looking, eyebrows; it completed the look she was trying for. Taking another sip of her drink Jackie took a deep breath, exhaled, and clicked on the ‘Slut-Me-Up’ icon. A notice appeared on the screen indicating that the process could take 10 to 15 minutes to complete. She leaned back in her chair, closed her eyes, tried to relax and waited.
Her mind was racing even though her eyes were closed. There were so many ways that she could be slutty! As she considered the possibilities her penis began growing and throbbing in anticipation. With eyes still closed she rolled up the leg of her jumper and was able to feel and stroke the bulge in her panties. She hooked her right thumb onto the elastic band at the top of her panties and pulled them slightly down. Using her right index finger she pushed aside the tissues she had placed there earlier.
Jackie began a slow circling of her cockhead, making an effort to spread her natural lubricant around and around the tip. Using the same finger she spread her slippery pre-seminal fluid down and around the corona of her penis. The mental images she was envisioning, as she waited, combined with the copious amount of pre-cum she was producing, were overwhelming and would soon need to be dealt with. Before she could take matters into her own hand her laptop beeped her back to the present. “Done” was the one word message overlaid onto the TransFormU opening screen.
Jackie licked her wet fingers out of reflex and pulled her panties and romper back into place and leaned forward to pick up her mouse. She clicked the ‘preview’ icon and leaned back again.
The Preview
The two minute, $50 mini-porn movie was just that; very graphic, very erotic and very XXX rated. It was well worth what Jackie had paid. Watching the preview, prior to downloading, was like living the experience without actually having to get down on your knees in front of your lover. Jackie watched herself pull a man’s penis from his boxer shorts, kiss the head and suck and swirl him with the timing of a pro. The moment of her ‘boy friends’ ejaculation was graphically captured; dribbles of cum were seen running down her chin as she tried to swallow. Her rigid penis was clearly visible.
The second man she had requested showed up half way through her two minute performance. Jackie could be seen eagerly bringing ‘man 2’ to a firm erection with her mouth, returning to her in-progress blowjob on ‘man 1’ while guiding ‘man2’s’ penis to her rectum and pulling the first two inches of ‘man 2’into her rectum. Very slutty! The close-ups were amazing in their detail.
Jackie had clearly been ‘slutted-up’! ‘Man 2’ could be seen giving Jackie a reach around as he plowed her ass. One of the more graphic scenes has Jackie with her legs over the shoulders of ‘man 2’ while being slow fucked, bare back, by him… she was clearly enjoying it. Another scene had her up ‘man 1’s’ ass all the way up to the base of her shaft. And then the mini-movie was over. Computer-generated imagery (CGI) has cum a long way.
Jackie found herself extremely aroused by watching her ‘movie’ and was panting like a dog in heat. The movie was all she had hoped for. It definitely was for personal viewing only. It was NOT ‘work place safe’.
Jackie adjusted her panties and romper to one side, gaining access to her throbbing penis. She picked up a box of tissues from a side table and hit the replay button. Before her personal porn video had played through to the end she had found extreme, and messy, release and self gratification. She was going to have to wash her romper. It was a memorable and joyful orgasm!
Having cleaned up and composed herself Jackie leaned over to ‘save’ her movie and four still images (bride, sissy, lingerie, and biker bitch) that she had just ‘previewed’. She clicked on the download icon. While they were downloading Jackie picked up her soiled tissues and went to change into a clean outfit. She tossed the tissues in the trash and decided to get more comfortable. After all it was a Friday evening and she had no place to go until work on Monday.
She got nude and selected tap pant underwear, a sleep bra and her silk lounging kimono. It felt good to be free of her normal bra, stockings and suspender belt. She lightly scratched her belly and breasts, walked to her vanity and changed to a lighter shade of lipstick. Smacking her lips to evenly spread her lipstick she looked in the mirror and said out loud, “Jackie, you’re such a very naughty girl. A virtual slut! And I have the video to prove it!” She blew a kiss to herself, winked, laughed and went to make herself another drink. Jackie liked her Tito’s.
She squeezed a lime into her vodka and waited for her downloads to finish. Jackie turned on some soft background music and sat back into her chair. She checked and made sure her new creations were properly in the ‘Jackie’ file on her laptop. They were. She sipped at her drink and decided to go through some emails.
The first email she read was unsettling. It was from Bob in the mail room at work. It read:
“Dearest Jackie, Thank you for trusting me to the degree that you would share your ‘special’ photos and video with me. I feel honored. Your secret is safe with me. I too have a feminine side but am too insecure to let it out. Your garter belt in your video is so yummy-sexy! And what you did to that man was very hot. If you would like to try someone new please give me a call. I’ve attached, in confidence, a picture of me in my favorite dress. Best wishes and hugs! “Diane” XOXO
Jackie’s jaw dropped. Her brain struggled to comprehend how “Diane” knew about Jackie and her movie. She refocused her eyes and read the next email:
“Miss Jackie, You are so incredibly hot! Seeing you at work I never would have expected that you could fem up so well. I had noticed that you had pierced ears but never guessed your secret. I’d like to take you on a dinner date to the Sycamore Inn sometime. I’ll leave a tube of L’oreal lipstick, with my phone number, on your desk Monday. I think the shade will look perfect on you! We have the same skin tone and it looks great on me. Call me. Yours truly, Jonny”
Jackie’s heart was pounding and her hand was shaking. How could this be happening? The numbers of unread emails were stacking up. Jackie logged back into TransFormU and immediately went to the settings area. Quickly going to the download setting Jackie gasped and slumped back into her chair. The problem was glaringly obvious; a real bone-head, amateur, mistake.
Still slumped into her chair Jackie took a large gulp of her drink and sat staring at the screen of her laptop. In the ‘download’ settings she had quickly selected ‘save’ and had left the ‘setup’ area. Looking at what she had done she saw that she had clicked on ‘save & share’! She had only wanted to ‘save’ her projects. In error she had ‘shared’ her movie and images with her entire ‘friends’ portion of her email address book. “Oh, my God… what have I done?” Life was about to get very complicated.
It could have been worse. The ‘share with’ options that were not checked included Facebook, Pinterest and several other options. In that regards Jackie was fortunate. The other piece of good news was that her email ‘friends’ has only forty entries. Some of her ‘friends’ were coworkers. This explained why Bob and Jonny had commented on her ‘movie’, so far. Thankfully the email addresses for ‘family’ and ‘work’ had been spared.
It was 9 PM Friday night and her movie had already set off a flood of emails. Some were not very nice. She only had two days to fabricate a believable explanation before reporting for work on Monday. That also meant that there were two days for more emails to roll in. “Oh, my God.”
Awakening Saturday morning Jackie lay in her bed, clad in her feminine sleep attire. She slowly stretched as she began to wake up. It had been a deep, relaxing sleep and she was enjoying the solitude and comfort of a lazy morning. And then the debacle of the night before hit home.
Jackie bolted upright in her bed and her mind began racing. “What the hell am I going to do!” she blurted out. She swung her feet over the bed, slipped into her fur trimmed mules, glanced into a mirror and fluffed her hair and went to the kitchen for coffee. She flipped the switch on the coffee maker. Glancing at her laptop she was glad that it was closed. ‘I’ll deal with that later’ she thought. Picking up her cell phone she saw that she had four messages. Setting the phone down Jackie snuck a cup of fresh coffee while the coffee pot was still brewing.
Adding a splash of milk and two teaspoons of sugar she pulled out a kitchen chair and sat down to think. ‘What the hell am I going to do?!’ she thought.
Finishing her second cup of coffee Jackie decided to shower before doing anything. Her cell phone rang and she let it go to message as she adjusted the water temperature in her shower. Whoever it was would just have to wait. Hopefully it was not her job telling her to not bother coming to work Monday. There were a few more coworkers in her email ‘friends’ that she had not heard from… yet.
The warm shower felt great and help to clear her head. Grabbing her razor and shaving foam she made quick work of making her legs nice and smooth. She shampooed and conditioned her hair, turned off the water and stepped out of the stall. She toweled her hair and patted her legs almost dry. She applied some coconut oil moisturizer to her legs and set some skinny curlers in her hair while it dried. Jackie liked the body and waves the curlers gave her.
Because it was a Saturday she pulled on a pair of French cut panties and a pair of low cut white shorts with a three inch inseam. The rolled cuffs made her shorts cuter as did the embroidered humming bird on a rear pocket. Opting for a teal colored push up demi-bra she inserted her breast forms and selected a yellow blouse that had a small white flower pattern. She buttoned a couple buttons and then knotted the shirt tails into ‘island style’. Opting for minimum makeup she chose a coral lipstick, blush on her cheek bones, and her usual black mascara.
Switching from the gold hoop earrings she inserted some cute pearl studs in her ear lobes, added several bangle bracelets and two rings. A few well placed dabs of perfume on her wrists and throat and she was ready to face the day. Slipping into a pair of leopard print flat sandals Jackie went to the living room. Looking down at her feet Jackie smiled and was glad she had recently painted her toenails a dark blue. The silver toe ring completed her. She opted to not wear her anklet. The curlers would remain in place until her hair dried.
Jackie made herself a toasted English muffin, with peanut butter and honey, and went to her laptop. She flipped open the laptop and turned it on. Her new emails were waiting.
“You disgusting pervert! How dare you send me those disgusting photos? I will have the police on you if do it again. Get some professional help.”
“I found your unsolicited images were very interesting but totally inappropriate for email. If you’d like to share your photos let me know and we can share them at my house. (You make a stunning blond.)”
“Damn, you are one hot mama! Why did you send them to ME? I’m in a relationship at present but if that changes I’ll let you know.”
“Whew”, Jackie thought, “the response isn’t as brutal as I thought it would be. Maybe there’s a way to fabricate a plausible explanation, keep my friends and my job.”
Taking a final bite of her muffin Jackie drank the last of her coffee. She reached up and felt her hair. ‘Almost dry’ she thought.
Jackie walked to her vanity, carefully removing her curlers as she walked. Using her separated fingers she slowly combed her hair upwards one time. Grabbing a can of unscented hair spray she bent at the waist, and let her hair hang down. She gave her hair a liberal spray and waited 20 seconds for the spray to firm up. Standing up she shook her head left and right a few times and checked her image in the mirror. Her hair was almost perfect. Using a brush she quickly had it the way she liked it. A final spray and she was done; a cute pixie cut in less than a minute. As long as she was at the mirror she reapplied a new fresh coat of lipstick.
Returning to the task of reading the email responses to his accidental emailing his en femme images and porn video Jackie began clicking through them.
A few replies were very negative, a few were accepting of Jackie’s hobby and a few wanted Jackie to ‘make’ them paint their nails and dress as women. And then there were some that wanted to have sex. “So far, so good” Jackie thought. And then she opened the next email.
“Jack – A copy of your video and photos were forwarded to me. They, and therefore you, reflect negatively on the corporation. Before I forward your video to HR I want to speak to you. I will call you at 12 noon Saturday. If you do not answer do not bother coming to work on Monday. If you decide to answer perhaps we can arrive at a solution.” – Mike Spence, CEO
‘Oh, my God… what have I done? What the hell am I going to do?!’ Jackie thought.
Precisely at 12 noon Jackie’s cell phone rang. On the second ring Jackie answered and stood up.
“Hello, this is Jack.”
“This is Mike Spence. Put Jackie on the phone.”
Taken aback by the request and the stern voice Jackie replied (in the same voice), “This is Jackie.”
Mr. Spence began: “Have I made it clear about how you and your video are an embarrassment to the corporation? Are you aware that your career and future are hanging by a thread… a very thin thread? And that I hold that thread.”
Jackie’s heart was pounding and her palms were getting damp. “Yes, I understand” she replied.
“Good.” Mr. Spence said in a terse tone. “We both understand your situation. Before we speak further, answer my questions. It’s obvious that you enjoy your female side. Why?”
“When I’m Jackie I feel very special. I love the taste of lipstick and the feel of nylons and lace. I find lingerie so much nicer than boring men’s clothes… you know, the usual.”
“Do you like your job? Do you want to keep your job?”
“Yes sir, I like the company and I like my job. I hope to advance to a more responsible position.”
“How far have you taken your cross-dressing? Do you shave your legs? Have you had sex with men? Your video says that you have.”
“Yes, I have shaved my legs for many years but I do no harm to the company by doing so. That video was all done with computer software. It’s not me. I’ve fantasized about sex with men before and that’s why I made the video. By mistake my images and video were accidentally sent to several people. I apologize.”
In a softer tone Mr. Spence replied with “Hmmm. Maybe there’s hope for you and we can reach a mutually beneficial arrangement. Of those photos which one do you like the most?”
Surprised at the change of tone of the conversation Jackie did not hesitate and replied, “I like my ‘lingerie mode’ first and then it’s a tie between the wedding dress and Sissy mode.”
Equally quick in his response Mr. Spence said, “I really like the ‘lingerie mode’ but I find the Sissy option is… shall we say, pleasant to consider. Your nude version is also pretty nice.”
The phone went silent. Jackie dared not say anything. She thought she could hear barely audible heavy breathing.
Mr. Spence broke the silence with “I have a proposal that could be beneficial to us both. I’ve already arranged for two days of sensitivity training at the office. You are off work, with pay, until Wednesday. You won’t have any problems at work from then on. The rest of my offer, and your career, depend upon you and your complete secrecy. I’ll have a non-disclosure agreement prepared and you will sign it.”
There was a pause and Jackie could hear ice cubes tinkle as Mr. Spence took a sip. Spence continued.
“I’ve viewed your video several times and it has awakened some very real needs and desires that I must deal with. I also like wearing lingerie and feeling slutty. It makes me feel very alive and… and very horny. To put it bluntly, I find you very attractive and I want to have sex with you. Not just once. I’m looking for a longer commitment. A one year agreement to begin with, subject to extension after six months. You would be well compensated and I’d guess that a person with your, shall we say, special ‘talents’ would need a better assignment and an office… there would be special projects that might take us out of town periodically. I have a mountain home that’s very secluded.”
Jackie was sitting in her chair, saying nothing and taking this all in. It seemed so surreal. She sensed a shift from being on the defense to being the dominant negotiator. She had something that Mike wanted very badly. He had tipped his hand. Lust can do that to a person.
“Are you there Jackie? Do you understand what I’m suggesting? It’s a win-win situation. What are your thoughts on my proposal?” There seemed to be a plaintive tone to Mike’s voice that bordered on desperation.
Hesitating a moment for effect Jackie softly replied, “It does seem like a mutually beneficial arrangement, doesn’t it?” As the proposal sank in Jackie could feel the start of an arousal. Having sex with a man AND being paid. Would that make her a whore? It didn’t really matter. It seemed like a wet dream come true.
“So what do you think, Jackie? Monday is the day after tomorrow. You’re running out of time and options. Your emails stirred up a lot of problems that the company doesn’t need. Say ‘yes’ and I’ll come to your condo tomorrow at noon. We could, if you will pardon the pun, consummate our agreement. I want you to be in the outfit I see in your lingerie photo. Is it a deal?”
Jackie smiled as she realized that she was in a position of power. She pulled the zipper down on her shorts. Holding the phone in her left hand she slowly began running her finger up and down her hardening cock. “Mr. Spence, you know I’m really a brunette, right? And in my video I’m a platinum blond, right?”
“Well, I’ll bring you a long, blond wig. Please, call me Mike.”
Jackie replied “Platinum blond, human hair, Mike.”
Dropping her voice and trying to sound sultry, Jackie added “You know Mike, sometimes I like having black hair; Sapphire black, shoulder length.”
Mike responded with “Ok, I’ll bring you two wigs and a bottle of Tito’s. Is that ok? Is there anything else?”
“Yes, there are just few things more. Don’t wear underwear, bring your favorite panties, and bring your nylons and a box of sheepskin condoms. I think you’ll like they way I feel when I’m deep inside you.”
Jackie was sure she heard a gasp from Mike who was breathing heavy like a man in lust. Continuing Jackie said, “I’m sure I have a bra that will fit you. I hope you like lace, Mike. I do.”
“I’ll see you tomorrow. By the way, I’m a 38 B.” Mike hung up.
Jackie put down her phone and giggled at the turn of events. Her future was looking brighter.
Finis?
Note to readers:
It’s the age old conundrum. There’s probably enough story left for a second chapter. But should there be another installment? I’m curious as how Bob (aka ‘Diane’), in the mail room, will interact with Jackie and I’m wondering if co-worker Jonny will actually leave Jackie the tube of lipstick he promised to leave on Jackie’s desk. Will there be other gifts left? How will the accidentally sent photos and video be resolved? And, of course, how will the arrangement between Mike and Jackie go? Will there be a trip to the mountains? A business trip to Miami or…?
"Writers must recognize the stop signs in their… stories."
Previously
“Yes, there are just few things more. Don’t wear underwear, bring your favorite panties, and bring your nylons and a box of sheepskin condoms. I think you’ll like they way I feel when I’m deep inside you.”
Jackie was sure she heard a gasp from Mike who was breathing heavy like a man in lust. Continuing, Jackie said, “I’m sure I have a bra that will fit you. I hope you like lace, Mike. I do.”
“I’ll see you tomorrow. By the way, I’m a 38 B.” Mike hung up.
Jackie put down her phone and giggled at the turn of events. Her future was looking brighter.
Things are looking better
Having gotten herself into a very dire situation when extremely compromising photos and a mini porn video were accidentally sent to the contacts in her email address book Jackie had gotten extremely luck. Not only was she not going to lose her job (and possibly many friends) Jackie was being promoted and would be involved with special projects.
The scary downside was, that for this to happen, she was going to have to fuck her boss, Mike Spence! Having viewed Jackie’s porn movie, even though it was CGI rendered, Mike was infatuated with Jackie. What added to Mike’s obsession was that he was a closeted cross-dresser that literally ached to express his feminine yearnings and for man-on-man sex.
It was a little after 1 PM on a Saturday. Jackie was feeling the need to be at her very feminine best for her boss tomorrow afternoon. Her future and career depended on it. What could she do between now and 12 noon tomorrow to look as femme as possible for Mike? A quick self assessment narrowed her options to hair, eyebrows or fingernails.
As a bonus Jackie’s “date” would be fulfilling her own latent desire to experience sex with a man. Unknown to Mike it would also be Jackie’s first foray down that forbidden trail. There were lots to be done and a short time to get it done.
And there was the nagging ‘problem’ with her sex tape and photos. She needed a way to explain them away. The photos of her in various sexy roles were the least of her worries. She could pass the photos off as a lost bet, a dare, a prank… but how to explain the porn?
Taking time to collect herself, and her thoughts, Jackie made herself a drink and went to her chair. She didn’t want to do anything brash. ‘Hair, brows or nails’? she thought. ‘I need to look more femme soon.’ Her laptop alerted her to a new email. Leaning forward she clicked it open. It was from TansFormU!
“Dear valued TransFormU beta user. You recently downloaded an end product of a TFU feature that continues to be refined. Our records show that yesterday you downloaded several still images and our ground breaking ‘Slut Me Up’ video. We omitted an important program security key which you MUST enter on the computer that was used for the download if you want to keep your items from expiring and auto deleting. Enter this security key BEFORE 6 PM PST today or you will lose ALL your creations: A147JX-G98PZ2-62KK33. We apologize for any inconvenience this oversight may have caused you. We appreciate your patronage.”
Jackie let out a loud ‘whoop!’ of excitement. A good day and a bright future just got better and brighter! She took a long sip of her drink and leaned back in her chair, laughing loudly. She re-read the email and giggled over her good fortune. ‘My “Slut Me Up” porn video and photos will automatically delete from everybody’s computer but mine! Mike doesn’t know! Nobody knows but me! They have no proof!’ Glancing at a clock she had about four hours to save her creations. She hurriedly typed in the security code to preserve her items, leaned back in her chair, and smiled like the Cheshire cat after eating a canary.
It was an amazing case of dodging a bullet, getting a second chance or whatever metaphor you wanted to use. Jackie said a silent prayer of thanks.
Jackie sipped and thought. ‘Should I cancel my date with Mike? No, I need him to conduct the sensitivity training at work or else I better never show my face there again. I need Mike in order to further my career and get a pay raise. And I need Mike because… I want a man.’
Taking another sip her pondering continued. ‘I need Mike. I need to keep Mike. I need to make Mike want me. I need to make him want to keep me. But how? I need to satisfy his desires. But how? What are his desires? He desires me to look like my porn video. But how? He desires to be femmed up (I can do that) and he desires to have sex with me (I CAN do that!)’ All was not lost.
Getting ready
‘I need to look more femme as soon as possible. Hair, brows and nails should do it’ she thought. Using the search engine on her laptop Jackie called House of Beauty Salon a block away. She explained that she wanted acrylic nails and eyebrow shaping. They had an opening and said it would take a little more than an hour and would cost $50 to $75 depending on what they did. They would be open until 6 PM. Jackie made the appointment for 3 PM. Figuring that she was off work until Wednesday that would give her Sunday, Monday and Tuesday to enjoy these feminine niceties in case she had to ‘butch it up’ with a more manly look on Wednesday. And perhaps Mike would have a solution.
Changing into a pair of mid rise denim pants and a simple print blouse Jackie applied some lipstick, grabbed her purse and left. Two hours Jackie was home and definitely looking… pretty. The beautician, upon learning that it was Jackie’s first salon visit, spent more time and effort with her. Asking if Jackie was trying for a certain vibe or look Jackie had replied, ‘Sexy, verging on slutty’.
Her acrylic fingernails were perfectly shaped and almost ¾ inches longer; definitely more girly looking than before. They were a dark scarlet as were her toenails. Her eyebrows had the super feminine thin arch seen in her ‘Slut-Me-Up’ video. As a special service to Jackie the beautician tinted Jackie’s eyelashes and eyebrows that wouldn’t fade for six weeks. There could be no going back. ‘I hope this gives Mike the hard-on that he’s looking for’ she thought.
Before returning home Jackie bought matching pairs of Silky Sheer Cocoa colored pantyhose; one for Mike and one for her, a tube of KY Jelly personal lubricant, a box of Kotex Ultra Thin Pads with wings, two deli sandwiches, and two liters of Sprite for her Tito’s.
Entering her condo she put her shopping bag down and quickly walked to her vanity mirror. She placed the Kotex Ultra Thin Pads on her vanity. Jackie sat down so she could admire her new look. She held her new dark red fingernails next to her face to confirm how they, combined with her newly tinted and shaped eyebrows and long, dark lashes, gave her the look she was striving for. ‘Damn, I’m hot!’ She used a tissue to remove her daytime lipstick and replaced it with a dark red color that closely matched her nails. Picking up her eyelash curler she gave them a nice crimping.
She had to get away from the mirror as she was infatuated with her look. Her jeans were beginning to bulge. Grabbing her cell phone she clicked off five or six selfies, making a mental note to update her TransFormU images in the near future.
Going back to the kitchen, she put the deli sandwiches and Sprite in the refrigerator and brought Mike’s new pantyhose and a pair of scissors to her usual chair. Sitting down she opened the packages and carefully cut access holes for Mike’s cock and his sphincter. ‘Best to be prepared’ she figured. She wasn’t sure how tomorrow would play out.
The evening was fading and she wanted to be bright eyed and eager for Mike. Her fate, literally, was in his hands. It was going to be an interesting day. She straightened the house a bit and retired to bed. She didn’t wear her favorite chemise thinking that she would save it for tomorrow. She removed her lipstick and climbed into bed. ‘I’ll remake the bed with my satin sheets after breakfast.’ She turned off her night light and tried for sleep.
Jackie’s alarm clock woke her at 8 AM. After coffee and breakfast Jackie spent some time to make sure that the condo and her bedroom looked nice and neat. Mike was due at noon and at 9 AM she began to get ready.
She showered and shaved all the areas that needed it and some areas that didn’t need it. She was not leaving anything up to chance. It had been months since she had shaved her crotch so she had to spend a little extra time to get it just right. ‘Mike better appreciate all this shaving’ she complained. ‘I wonder if he will be smooth. I’d like that.’
Stepping from the shower she dried and moisturized her freshly shaved legs. Once dry she tucked her penis and slipped into black French cut panties before going to work on her shag pixie cut hair style. Hairspray was the final touch. She looked pretty.
Recalling her TFU ‘lingerie mode’ look Jackie dressed in her matching red garter belt and panty set, black stockings, a black and red pushup bustier (with lace trim) that emphasized her cleavage. Her breast inserts helped her look very well endowed. She stepped into black three inch pump heels unlike the four inch heels in her CGI movie. Managing to find some dangling gold chandelier earrings she tried for the show girl/slut makeup that Mike apparently liked. On purpose she didn’t apply any eye shadow.
Sitting in her thinking chair Jackie plotted on how to keep the negotiating power she had asserted during her conversation yesterday with Mike. There were several things that were in her favor. 1- Mike didn’t know that all Jackie’s TCU images had deleted themselves by now. 2 – She had something that Mike wanted… and he had made it clear that he wanted it very much; almost desperately. Jackie made a mental note to not seem weak or desperate. She had to be in control.
With that in mind Jackie removed her earrings, placed them on her vanity, and inserted her pearl studs. Next she wiped her ‘Trollop Red’ lipstick off. There would be time for that later. She wanted Mike to see her looking fairly plain when he first arrived and would then transform to a more sultry look after he arrived. It was all about the image.
Kicking off her heels she pulled on Jack’s khaki business slacks over her garter belt and nylon covered legs and slipped into a pair of Jack’s loafers. Black nylons could be seen where socks should be. Selecting one of Jack’s long sleeved white shirts she put it on, tucked it loosely into the khakis, making sure to leave the shirt cuffs unbuttoned, and the top two buttons open.
Her new scarlet fingernails showed at the end of the sleeves in contrast to the man’s white shirt. Hints of her lace bustier were, on purpose, visible at her neck. In fact her cleavage was visible. She made an erotically androgynous image standing there; a woman dressed in men’s clothes, with obvious breasts and a pixie shag hair style. Her beautifully shaped eyebrows and well defined eyelashes completed the image. The pearl studs were perfect. It was part of a plan that would, hopefully, keep her in control of the situation as well as her future.
Jackie had sensed a definite shift as who was on the offense during yesterdays call with Mike. There was a defining moment that tipped the conversation in her favor. She felt it when Mike said he wanted her… there had been a plaintive tone to Mike’s voice that bordered on desperation. Jackie wanted to maintain that leverage.
Taking care of last minute details Jackie brought an extra chair into her bedroom and placed it next to her vanity. On top of the vanity she staged several tubes of lipstick, bottles of nail polish and mascara. She placed the KY lubricant on a night stand and strategically placed some extra tissue boxes throughout her condo. Mike’s modified pantyhose were conveniently waiting on the foot of her bed.
Retreating back to her thinking chair she closed her eyes and tried to psyche herself up. There would probably be many firsts for her today and she wanted to be as prepared as possible. With her eyes closed she mentally went down a check list. How far would she let him go with her? How far would she go on him? Would he fire her? Jackie did some yoga breathing to help steady herself.
At 11:30 AM she got up and lit scented candles in the kitchen and bedroom. Checking in the mirror she thought, being in Jack’s clothes, that she looked like a not so subtle lesbian. That mental image made her giggle. She resisted the urge to apply some lipstick but did make a few brush strokes of blush to her cheekbones. She placed a solitary dot of perfume behind one ear.
Returning to the kitchen she started a pot of coffee, laid out two coffee cups and two drinking glasses, a bucket of ice and a small plate of lime wedges. She went to the living room, pulled the curtains closed and sat on the sofa to wait.
The boss arrives
Precisely at 12 noon there was a firm knocking on her door. Jackie waited for the second knock before standing and going to the door. At about the time there would have been a third knock Jackie opened the door. Standing outside was a handsome looking man that held a large shopping bag in one arm. “Hello, I’m Mike Spence” he announced.
Jackie opened the door wider and said “Please come in, Mike. Welcome to my home.” Mike looked left and right, which was a ‘tell’ of his nervousness, before stepping in. Jackie closed the door smiling at what she had just seen. ‘This is starting well’ she thought.
Mike walked over to the counter and put his bag down. He did a careful check of the condo before making eye contact. “Your place looks nice” Mike offered. Jackie stepped closer and, in a manly fashion, firmly shook Mike’s hand and said “Thank you for coming, Mike.” While still shaking Mike’s hand Jackie made a quick assessment. Jackie stood about 5’ 7 inches and it appeared Mike was maybe three inches taller. He looked to be about 150 pounds, appeared fit and could best be described as boyishly handsome. According to company literature Mike was 30 years old, unmarried and liked snow skiing. Even by Jackie’s standards Mike was handsome. He had a boyish face, check bones that begged for blush and he had no facial hair. There were remnants, in both ears, of having pierced ears at sometime. ‘He could have been worse’ she thought.
“Would you care for a cup of fresh coffee?” Mike was checking Jackie very closely. “Yes, please. Black, no sugar.” Jackie poured a cup for Mike and one for herself. She stirred in two teaspoons of sugar and a teaspoon of cream into her cup. She walked the cups over to the kitchen table and asked Mike to have a seat. He did.
Sitting in silence for an awkward moment Mike took a sip of his coffee. Jackie kept stirring her cup, not taking her eyes off Mike. Mike took another sip and then said “I told you to be dressed… differently than this. I came to see Jackie.” “Yes Mike you did. But first I’m sure you have business to resolve with Jack, right?” With a free hand Jackie widened the gap of her shirt exposing more of her bustier and cleavage. “Jack will leave once we’re done with the paperwork.” Mike’s pupils became larger. ‘Ah, another tell’. Jackie inwardly smiled and took a sip of her coffee.
“Let’s get the paperwork out of the way first. Don’t you agree?” Mike retrieved a file folder from the bag he had brought in and returned to the table with a pen. “All of the items we discussed yesterday are in this document. The term of the contract is one year with extensions available after six months. I’ve decided that you will be my Special Assistant with duties and projects determined by me. I’ve set your annual salary at $75k with a chance for performance bonuses. In return you will… (he gulped and had to take another sip of coffee to loosen his voice)… you will help and assist me as we discussed yesterday.“ Trying to sound managerial and authoritative he added “Is that clear? There is also a Non Disclosure Agreement that, if you violate it, will make your life a living hell. And there is a Sexual Exclusivity Agreement. Neither of us can have sex with anyone else. It protects us both from STDs.”
Jackie looked demurely over her cup of coffee and softly replied, “Yes, Mike. It’s clear. And will the company conduct the two day LGBTQ sensitivity training?” “Yes, it’s all set to go starting Monday.” Jackie gave Mike a perplexed look and began tapping her pretty red acrylics on the table top. “Mike, don’t you think that it would be best if the company had annual sensitivity re-training?” Jackie asked. Mike looked momentarily startled by Jackie’s boldness. He paused to give her suggestion some thought. “Yes, I think that would be the right thing to do.” Jackie reached over and placed both of her warm hands on Mike’s hand, letting them linger just a bit; she gave them a gentle squeeze and took the pen from Mike’s hand. All documents were quickly signed and Jackie pushed them back to Mike.
“Now that that’s done why don’t we get more comfortable? Would you care for a drink?” she asked. Mike nodded and they both went to the counter where the glasses were. Jackie began filling their glasses with ice and Mike reached into his bag producing the promised bottle of Tito’s vodka. Mike poured the vodka and Sprite while Jackie added the limes. She thought she saw him try to get a whiff of her perfume.
Staring at each other they both raised their glasses. “To a new future” Mike pronounced. Jackie smiled and added “And here’s to new experiences.” They clinked their glasses, took a drink and they both nervously giggled.
It was as if a heavy weight had been taken off them. The hard part, no pun intended, was behind them.
Jack leaves
“I think we are done with Jack. Let’s have seat on my couch for a bit, shall we?” Jackie instructed. With drinks in hand they walked toward the couch. Jackie paused by her thinking chair and kicked out of Jack’s loafers. She put her drink down by her laptop and removed Jack’s pants, hanging them on the back of her chair. The white shirt quickly followed. She was now standing in her ‘lingerie mode’ items. Her nylon covered feet contrasted nicely with the white carpet. Mike was watching and enjoying her transformation. Mike commented, “That outfit is fantastic! I see no maleness. It gives me a goal to strive for… with your help. It also makes me… envious.” Jackie was sure that he was going to say ‘horny’.
Jackie picked up her drink, faced Mike, struck a not so subtle slutty-girl pose and then joined Mike on the couch. They sat a half cushion away from each other. She took a sip and placed her drink on the coffee table. Jackie crossed her legs and moved next to Mike; the sound of her nylon covered legs crossing did not go unnoticed by Mike. He took a gulp of his drink and stared some more. Jackie could sense that his mind was whirling. “So, what do you think Mike? See anything you like?”
Mike gulped and tentatively put his hand on Jackie’s nylon covered knee and slowly rubbed it. “You look, and feel, stunning; much prettier than your video.” “Thank you Mike, a girl likes to hear that. I think that, with a little effort that you could look pretty too. You have a face and cheek bones that would lend themselves to being pretty.” Mike blushed and took another sip of his drink. “I would like that” he confessed.
Jackie reached over and laid her hand on Mike’s knee and suggested, “Make yourself comfortable. Kick off your shoes.” Mike quickly did. With his shoes off Jackie saw that Mike was wearing black nylons with a reinforced toe. ‘He’s got a head start it seems. I bet they are thigh high style’ she thought. Rather than ignore the elephant in the room Jackie pointed at Mike’s nylon covered toes and said “It seems we both like black stockings, Mike. I wonder what other items we share a love for. Do you like panties and lipstick, Mike?” Mike didn’t answer and his eyes diverted away from Jackie. He licked his lips. ‘Another tell’ thought Jackie. They both took a sip of their drinks and leaned back into the couch. A strong level of tenseness had vanished. ‘So far so good’ Jackie thought.
Jackie thought about moving Mike’s hand to the inside of her thigh but quickly shrugged that off. ‘Can’t be to bold… just enough to keep things in my favor. “What did you bring in the bag Mike? Did you bring your favorite panties, heels, or maybe a cute and skimpy skirt?”
Mike took a deep breath and said “I brought three wigs and some stuff.” “Three wigs, Mike? I only wanted two.” Mike blushed and replied “I brought one for me. Shoulder length strawberry blond.”
Standing up Jackie made a display of smoothing her nylons from her ankles to her thighs, adjusting the tightness of one garter. Noticing that Mike was involuntarily licking his lips Jackie flashed Mike a pretty smile and suggested “Give my garter a little pull, feel the tightness. You may need to know the proper snugness someday”. Mike hooked a finger under one garter and pulled it slightly getting a sense of what Jackie had said. He held Jackie’s garter strap for a couple seconds, stroked her nylon covered leg with his other hand, and let it go. There was a soft snap sound as the elastic snuggled back into place. “It’s like having someone playfully snap your bra strap. Has anyone pulled your bra strap, Mike?”
Waiting a moment for the reply that never came, Jackie announced, “I’ll take your bag to my bedroom, you make us another drink and then join me at my vanity. I have a chair waiting. I also have something for those dry lips. Do you like red, Mike?” Jackie grabbed the bag and went to her bedroom.
The bedroom
Mike arrived in quick order with both beverages. He stopped just inside Jackie’s bedroom door and looked around; nice, neat and feminine. He saw the contents of his bag neatly piled on Jackie’s bed, several pairs of his panties, a tube of lube, and his boring white bra lay next to the wigs. He was puzzled about the folded nylons and the box of panty liners on the vanity. He knew he didn’t bring them.
Jackie was seated at her vanity. She saw Mike in the reflection in her mirror and motioned for him to take the seat next to her. He did. Both drinks were placed on coasters on the vanity. Without turning to face Mike, Jackie said, “Just watch for now.” She picked up one tube of lipstick, extended the lipstick, gave it a smell and rolled it back into the tube, pretending it was not quite right. “Fragrance is key to a lipstick. Some smell like wax. Choose carefully.” She held it in front of Mike’s nose for him to smell. “This smells like nothing, tastes like nothing so why bother?” Mike agreed.
Grabbing a second tube of color Jackie removed the cap, gave it a whiff, nodded and began to carefully apply the scarlet red she had pre-selected. Mike sat enthralled, watching every move. “Let me smell that please,” Mike requested. “That’s a much nicer aroma.”
Jackie then began applying her eye shadow, using small sponge brushes to blend colors; smoky black, a lighter gray and some gold highlight. She was getting slutty. Mike was taking it all in. Next came her jet black eye liner and, for Mike’s benefit, Jackie used her mascara and finished with an eyelash curler. Glancing over at Mike she announced, “Almost done.” Jackie picked up her diamond chandelier earrings and easily had them in place.
Turning to face Mike she asked, “Is this who you expected to open the door for you today?” “Wow, you look amazing!” Mike managed to say. Jackie leaned over, grabbed Mike by the chin, pulled him closer and proceeded to kiss Mike on the lips. She made an effort to transfer as much of her lipstick as possible on to Mike’s lips. She broke the kiss with a loud smack sound and told him “I just fixed your chapped lips. Lick your lips and taste the scent. Nice, eh?” Mike was obviously in a state of bliss. The lump in his pants was also obvious.
Grabbing Mike’s chin Jackie closely inspected his lips. “Nope, this won’t do. You need more lipstick if you want full coverage. You do want better looking lips, right?” She handed Mike the open tube of lipstick. “Here doll face, do it the right way.”
With barely a hesitation Mike took the tube, leaned in towards the mirror, and carefully applied the scarlet red. Without looking around Mike lamented “This color doesn’t match by skin tone, it’s to stark.” Without being asked Mike picked up the mascara and stroked his eyelashes. Following Jackie’s lead he used the eyelash curler to give them a good crimping. Looking into the mirror he could see Jackie behind him. Jackie had assumed her now classic ‘lingerie mode’ stance. Her hands were on her hips and she was standing at the foot of her bed.
Mike stood and turned around to face Jackie. “I think you look good in lipstick, Mike, and your eyelashes make your face pop. Very nice; it’s a good start,” she said. Mike was happily grinning. A few moments passed as they stood there looking at each other. In a low sultry voice Jackie announced “Mike, it’s time to remove your clothes, right? That is part of our deal, right? You already have your shoes off; that’s when I saw your nylons, remember?”
Mike removed his shirt and hung it on the back of the vanity chair. He was nude up top. Next he dropped his pants and tossed them on the bed. He was only wearing a pair of elastic top, black, thigh high nylons. No panties. His penis wasn’t flaccid and it wasn’t erect. It appeared to be an above average eight inch with normal girth; nothing too scary. Jackie was staring and wondering to what degree she would have to be involved with it. Hands, lips or both? She had no experience, other than porn, as what to do.
“Mike, select one of your panties and put them on, ok?” Mike shuffled the panties around and selected a navy blue pair of briefs and pulled them on. Jackie continued, “Your choice in stockings is good but in the long run they become too much work. The elastic top weakens, they begin to droop and you spend your day trying to pull them up with your pants on. Eventually you’ll need a garter belt to keep them up or just switch to a garter belt and stockings now. Your other option is pantyhose. There are many styles, with and without patterns and they are convenient. The silky ones feel very nice. Have you worn pantyhose before, Mike?” Mike nodded yes.
Jackie went to her dresser and poked around. While she was looking for just the right thing she said, “Yesterday you said that you like wearing lingerie and feeling slutty, that it makes you very horny, right?” Mike quietly said, “Yes, I said that because it’s true. I get feelings and desires that I can’t explain.” Taking a matching navy blue camisole from her drawer Jackie walked over and handed it to Mike. “Here, put this on. It matches your panties and will make you look more femme. It will have to do for today.” Jackie was standing directly in front of Mike as he pulled the cami on.
Tell me what you told me
“You know what else you told me yesterday, Mike? You told me that you find me attractive. There’s one more important think that you told me. Do you remember, Mike? Tell me what else you told me yesterday. I need to hear it again.” Jackie reached forward and felt Mike’s panty encased dick. Keeping eye contact Jackie rubbed Mike’s dick, as sensuously as she could. “Does this make you feel alive, Mike? Does this make you horny, Mike? I think so, based on how big you’ve gotten. Your breathing has gotten a little rough, hasn’t it?” Mike nodded but didn’t move. His cock was protruding above his panty. Still keeping eye contact Jackie used her thumb to spread his pre-cum around and around his dick head. Mike was lightly shaking.
Using her other hand Jackie started to lightly stimulate Mike’s nipple through his camisole. Jackie leaned closer and whispered “Tell me what else you told me, Mike. We both know what you said. Tell me again, I’m waiting.” Mike closed his eyes and said “I want to have sex with you! I really want to have sex with you. I’ve never done this before but I want to have sex with you!” Jackie smiled and moved her hand so she could rub up and down Mike’s dick. “There, that wasn’t so hard to say, was it?”
Standing on her toes Jackie kissed Mike on the lips. Not getting the response she wanted Jackie kissed him with more passion than before. At the same time she slipped her hand into Mike’s panties, circled Mike’s cock at the base, her skin on his skin. She gently drew her circled her fingers tighter and stroked lightly up and down his shaft. She felt a throb. Mike’s kissing improved. “Mike, what did you say you wanted?” Mike made a slight forward thrust and gasped “I want to have sex with you!”
Jackie took Mike’s right hand and held it against her dick and made a conscious throb of her penis so Mike could feel it. Jackie moved Mike’s open palm up and down her stiffening shaft. Mike moaned. “Take my panties off, Mike. I need my panties off.” Breaking from their kissing Mike knelt down and helped Jackie step free. Her cock sprang eye level with Mike and was pointing toward the ceiling. Mike stared at it. “How do you want to do this, Mike?” asked Jackie.
Mike gently grabbed Jackie’s shaft and inspected it for a moment. Taking a deep breath, Mike slowly pulled Jackie’s penis closer to his mouth. He looked up into Jackie’s eyes, extended his tongue, and licked her cock head a couple times. “What do I do now?” Mike panted. Jackie looked down and said, “Try kissing it, Mike. Leave your lip print on it.” Mike kissed Jackie’s cock head and held his lips against it for a moment. Pulling back Mike looked at his lip print on Jackie’s cock. He circled his hand around the base of Jackie’s shaft and ran his grip up and down Jackie’s dick a few times just to see what it felt like to stroke a man’s penis. Jackie made sure to properly throb for Mike’s education. Looking up at Jackie, Mike pulled her cock back to his lips and kissed it again, this time below her glans, leaving another red lip print. Mike was finding these acts very erotic. So did Jackie. They both watched Jackie’s dick grow taller. Mike could feel the difference in Jackie’s firmness with his lips. It made his heart beat increase and his penis too.
“Are you feeling slutty yet, baby doll?” Jackie asked in a low, sultry voice. “You make me feel so good… and hard… and horny. Are you horny, Mike?” Mike softly squeezed and stroked Jackie’s shaft in reply. Fondling Jackie’s penis was becoming addictive. Jackie gave him the twitch he was looking for. Mike smiled.
Going down
Knowing the answer, but actually looking for approval, Mike asked, “Now what.” There was urgency in his voice. While waiting for a response Mike continued to gently stroke his hand up and down Jackie’s shaft. He was exploring what another man’s dick felt like. Jackie sent out another sex throb. Mike smiled at this twitch.
“Do what would make you feel good, Mike. Most girls put the dick in their mouth, seal their lips around the shaft, and suck and swirl their tongue while going up and down the shaft. Think of your mouth as the hand you jerk off with. Just go with it. Lubricate it with your tongue. Make it slippery. Bob your head if it feels right. Go faster when I’m about to cum.” Placing her hand on the back of Mike’s head Jackie gently guided him back to the task at hand.
Still on his knees Mike immediately got the hang of things and was giving an above average blowjob. Jackie had her eyes closed and was moaning and smiling at the same time. With a free hand Mike was slowly giving himself a hand job in slow rhythm with his sucking. Mike had made it to the base of Jackie’s cock more than once; Jackie began making subtle thrusting moves. “Darling, I’m getting really close… get ready!”
Mike made a final dive down Jackie’s penis. He sucked and licked and swirled his tongue, Jackie’s cock head was well back in his throat. … Jackie let loose. Several waves of cum erupted from Jackie’s cock. Mike didn’t spill a drop. He made a couple gulping movements and then a final upward cleaning suck keeping his lips sealed. Jackie’s dick popped free. Mike swallowed but remained on his knees as he recovered from giving his first blowjob. He wiped his mouth with the back of his hand. Jackie grabbed one of his arms and helped him stand.
Jackie hugged Mike and kissed him passionately on the lips. She made sure to use her tongue with the kissing. “Oh, darling, I can taste myself on your lips and it makes me feel slutty. You were superb.” Jackie made a point of rubbing Mike’s cock through his panties. His bulge felt nice. “Thank you for a great time. Come sit at the vanity for a bit. Have sip off your drink.” Mike did as he was told. After a short while Mike looked into the vanity mirror and reapplied the scarlet red lipstick, pressing his lips together for even coverage. “Where did all my lipstick go?” he asked. Pointing to her almost flaccid penis Jackie said “Look”. Mike turned and saw several red rings on Jackie’s dick. “Very impressive, Mike, you left me some trophy rings! By the way, wearing lipstick when performing a blowjob not only acts as a lubricant it also protects your lips from chaffing.” Mike nodded.
Sitting next to Mike Jackie ran her fingers through his hair and tried to sooth and calm him. “So how was it, baby doll?” Mike smiled and said “It didn’t taste bad at all and I liked the way I could feel you throb in my mouth… I felt super slutty and horny.” Taking a sip off her drink Jackie went to her lingerie drawer and brought back a navy blue 38B underwire pushup bra and a pair of breast enhancers. “Lift your arms, baby” Jackie instructed. Jackie removed Mike’s cami and placed it on the bed. Jackie put the bra on Mike, hooked it in the back, adjusted the straps, inserted the tit augmenters and pulled the cami back on Mike. “Your new tits look good on you! You earned them.” Noticing her gold hoop earrings on the top of her vanity Jackie picked them up and slipped one into Mike’s left ear. Handing Mike the other one Jackie said “You insert the other one. Stay here and I’ll be right back. Give me your drink glass.”
Jackie did some thinking while she mixed them fresh drinks. Returning to the bedroom she saw Mike was sporting both hoop earrings and was adding more mascara. His new tits were a definite improvement. Jackie sat down next to Mike and told him to close his eyes. “I’m going to add some eye shadow to show you what a little accent can do for your eyes. Next I’ll use eyeliner for an even better effect. Hold still.” A few minutes later Jackie was done. “Open your eyes, baby doll.” Mike slowly opened his eyes and checked his reflection in the mirror. He broke into a wide smile and said “Wow! My entire face looks better. I love what you did with my eyes.” His hand involuntarily fingered his earrings. He leaned over and gave Jackie a gentle kiss. “Thank you” he said. Jackie returned his kiss with more ardor and said “I’m glad you came over today Mike; it makes me feel pleasantly slutty too.” Jackie tweaked Mike’s panties and kissed him again.
Jackie handed Mike his drink. “To us!” Jackie said. Mike smiled, echoed the toast and they both took a swallow. Jackie put her hand on Mike’s knee and said, “I can’t call you Mike anymore. You’re much too pretty to be called Mike and after what you just did to my penis you deserve a new name. You earned it.
(To be continued)
Previously
“Wow! My entire face looks better. I love what you did with my eyes.” His hand involuntarily fingered his earrings. He leaned over and gave Jackie a gentle kiss. “Thank you” he said. Jackie returned his kiss with more ardor and said “I’m glad you came over today Mike; it makes me feel pleasantly slutty too.” Jackie tweaked Mike’s panties and kissed him again.
Jackie handed Mike his drink. “To us!” Jackie said. Mike smiled, echoed the toast and they both took a swallow. Jackie put her hand on Mike’s knee and said, “I can’t call you Mike anymore. You’re much too pretty to be called Mike and after what you just did to my penis you deserve a new name. You earned it.”
The story continues
As Mike continued to sit at the vanity Jackie looked around and located Mike’s strawberry blond wig. Bringing the wig and a wig cap over to where Mike sat, Jackie fitted the wig cap to Mike’s head, carefully brushed the wig, and positioned it into place. Facing Mike Jackie stepped back to make sure all was right. A few more brush strokes gave Mike some nice looking bangs. “Strawberry blond really looks good on you. You look pretty and more importantly it makes you look very girly. What do you think?” asked Jackie.
Mike stared, in awe, at his image in the vanity mirror. He shook his head to make his new hair toss about. His gold hoop earrings gently tapped his cheeks as he shook. Stopping to stare longer at the pretty image in the mirror he smiled and said “”That’s a pretty cute girl looking at me.” Picking up his tube of lipstick he leaned forward and applied more lipstick in an effort to create the ultimate image of a woman playing with her makeup. Looking up he giggled and lamented “I’d love to see what I’d look like if I was doing this but was only wearing a chemise!”
Jackie chuckled and quipped “That image (as she pointed to the reflection in the vanity mirror) would make a very interesting photo on your Christmas cards!”
Jackie stepped behind Mike with a brush and two scrunchie hair bands and she quickly created a sexy, double sided, ponytail. Each ponytail stuck out and gave Mike a young school girl look. “There’s so much that you can do with long hair. Look how this shows off your earrings.” Leaning over Mike’s shoulder Jackie gave Mike a quick kiss on his neck. “You’re looking very gender fluid at the moment” Jackie noted.
Looking at Mike’s reflection in the mirror Jackie gave his bra strap a playful snap. “Like I said you’re much too pretty to be called Mike.”
Goodbye Mike
Sitting down on the vanity seat Jackie placed her hand on Mike’s knee and asked “What do you think about ‘Michelle’ with ‘Mickey’ as a nick name?” Mike gave it a thought and said “Michelle sounds nice.” They toasted to Michelle. Michelle leaned over and gave Jackie a deeper, tongue involved, lover’s kiss. Michelle gave Jackie’s panties a reciprocal tweak. It was a beautiful thing.
Jackie pulled on a fresh pair of panties, redid her lipstick, and suggested that they return back to the living room couch for awhile. “Bring your drink, Michelle”. Before exiting the bedroom Jackie grabbed a bottle of nail polish and a pair of the custom pantyhose she had made. “Let me paint your toe nails while we talk and relax, ok? Remove your thigh highs.” Michelle did.
Jackie reached over and gave Michelle’s bare leg a gentle stroking. “Wow, you’ve got some smooth legs! Smoother than mine and I shaved my legs this morning just for you. I guess you are serious about exploring your female side” Jackie said. In reply Mickey said. “I’ve been shaving for years and have recently tried a crème. I’m not sure if it’s worth the hassle but I really like smooth legs and armpits.” He smiled and leaned back on the couch.
Shaking the bottle of blue polish Jackie asked what sort of experiences that Michelle would like to experience, what sort of help she wanted in looking feminine, how feminine did she want to go, how slutty, how permanent should these things be, and a variety of other questions. In short time all ten toes were painted bright blue. Jackie told Michelle that her blue toes would remind her of today. She applied a coat of polish ‘quick dry’ to speed up the drying process. It sure beat having to blow on her toes for five minutes.
Eventually the subject returned to ‘what next’. Michelle sat quite, in deep thought, for a period of time and had painted her own finger nails on her left hand before she spoke. “You know how I said that I want to have sex with you? I meant it. More precisely, because of your porn video, I more precisely mean that I want to have sex with you in me! I want you to fuck me and never tell anyone. That, and other reasons, is why I’m paying you $75k a year. I just want you to be gentle with me.” There was that sound of desperation that Jackie was glad to hear.
Jackie mulled over what she was just told. “No problem, Michelle, I’ll be gentle. I brought you some special pantyhose that will help us both. Your nails are dry so remove your panties and put these on. I’m going to need full access. ” Michelle found the front of the pantyhose, rolled them up as needed and easily pulled them up her legs nonchalantly smoothing them up her legs. The silky style looked great on Michelle. Jackie noted her familiarity and ease in her donning hose.
Noticing that there were two holes in the pantyhose Michelle asked. “What’s with the holes?” Jackie stuck her hand into the front hole, grabbed Michelle’s penis, and pulled it out. It looked funny hanging out like that. “The pantyhose will add to the experience. They are very silky and will enhance your feeling of being slutty and feminine. The feeling of two people fucking while both are wearing pantyhose and making love is not to be missed. It’s a beautiful thing.”
To the bedroom
“Let’s go to the bedroom, Michelle.” Michelle was leading the way. “Ok Jackie, why the opening in the rear?” Rather than say anything Jackie slipped her middle finger into Mickey ass crevice and poked her sphincter, maybe gaining a half inch of penetration. “Oooo! I think I understand.”
“Michelle, let me give you a quick explanation of what you’ve asked for and what we’re about to do. But first, I think I need a work-at-home provision added to Jack’s contract, don’t you?” Michelle stopped walking, turned to face Jackie, let out a laugh and said “Done! I might have to set up an office at my mountain home too.” Michelle hugged Jackie and gave her a sensuous kiss while rubbing her butt.
“Before the night is over you will have experienced your darkest secret (more than once), you’ll have been on your back and have had your legs over my shoulders. We will have gone through a half tube of lube and half a half box of those lambskin condoms. If you really want to feel slutty we could do it bareback… use no condom. You’ll imagine sperm wiggling around in your deepest orifice. It might enhance the slut feeling you’re searching for.”
Reaching her bed Jackie picked up the other pair of special pantyhose, cleaned off the bed, placing all items on a nearby chair, making sure to have a tube of lube within arm’s reach. Jackie placed a few hand towels and a box of baby wipes near the head of the bed.
Taking Michelle by her hand Jackie guided her to the foot of the bed. Jackie had Michelle stand with the back of her legs touching the bed. Jackie stood in front of Michelle and gave her a warm hug and a soft kiss. “Are you ready for this Michelle?” Michelle nodded and in a barely audible whisper said “Yes…I’m ready. I want you in me; I want you in me bareback. I want to see if I can feel the little swimmers.” They both giggled at Michelle’s joke. Jackie removed her panties, sat on the bed and slipped into the same style of silky pantyhose that Michelle was wearing. She stood up and walked over to Michelle to try to ease her mind about what was in store for her.
“Baby doll, here is what needs to happen. You need to make my cock as hard as possible. A repeat of the earlier blowjob would work quite well. We’ll use the wetness from what you leave on my penis as lubricant. You’ll lay on your back, on the bed, with your legs bent. I’ll crawl up between your legs and we’ll wing it from there. I will be using that other hole in your pantyhose. If we have problems we have KY on standby. I’ll be very slow and gentle. Eventually, out of pure horny lust, you’ll probably hook your legs over my shoulders so I can get in you as deep as possible. I want to feel your vertebrae with the head of my dick. You may be able to feel me squirt. As a favor for me, when you feel that, clench my dick with your sphincter muscle once or twice. It adds to my experience and may add to yours too. Especially as I withdraw. Clench and see if you can feel the veins in my shaft as I slowly pull out. I hate to be so clinical. When we’re done and rested I have a favor to ask of you. Ready?” Michelle grabbed my face and gave me a very passionate kiss. “Yes, I’m ready. Now shut up and let’s do it.”
Shut up and do it
Michelle reached into Jackie’s pantyhose hole and extracted Jackie’s penis which was already beginning to firm up. Jackie told Jackie to hold on a minute and she quickly went to the vanity and applied another coat of lipstick. Returning to Jackie she said “Sorry, I don’t want chapped lips”. She took hold of Jackie’s penis and slid to her knees and flipping her long blond hair out of the way. She began jerking Jackie off to get her hard enough to fellate. As soon as Jackie’s penis was pleasantly rigid, Michelle began sucking Jackie into her mouth. After few minutes of head bobbing, Michelle had accomplished in making Jackie hard enough for her penetration. Michelle was tempted to continue the blowjob to ejaculation but decided she had more urgent needs.
Michelle was scooting back on the bed, pulling Jackie by her wrists, up and between her legs. ‘Dang, this girl is anxious’ thought Jackie. Michelle had her legs bent and Jackie was kneeling in place. Jackie leaned forward and went in for one more kiss. Jackie too was excited since she had never fucked a man before. It was going to be a first for both of them. Being with a man was high on Jackie’s fantasy list.
Sensing a need, and to make Michelle’s first time easier, Jackie used a generous amount of KY jelly to grease her shaft thoroughly.
Widening the hole in Michelle’s pantyhose Jackie inched forward and had her penis at Michelle’s anus. Jackie was just about to begin penetration when Michelle reached down and pulled Jackie into her about an inch.
Unknown to Michelle was that this was Jackie’s first experience with this kind of sex. Jackie talked a good show but was totally improvising everything. Porn and locker room gossip was the basis for what appeared to be her prowess. Also unknown to Michelle was that Jackie was a virgin and yearned to be on the receiving of a man’s penis. For these reasons Jackie wanted to watch Michelle’s face as she was being fucked. She wanted to know what she could expect.
Michelle’s virginal tightness was an obstacle they both had to overcome. Being highly motivated, and with Jackie being compassionately gentle, full penetration was achieved. Jackie began slow fucking Michelle, partially withdrawing with each thrust, so that she could feel Michelle’s tightness with each stroke. “Are you doing ok, baby doll?” Jackie asked. “Relax yourself and it will get easier.” Michelle nodded and Jackie felt Michelle loosen up. Jackie picked up the tempo and she watched Michelle begin to smile. Michelle began to arch her back and was soon meetings Jackie forward thrusts.
As predicted by Jackie, Michelle soon had her legs over Jackie’s shoulders to attain maximum penetration, and was eagerly humping towards her first anal orgasm. The sexy feeling of their nylons rubbing and sliding together was indeed sensuous. The slick friction and sound of the materials rubbing together enhanced the moment for them both.
Pulling back a little Jackie made an effort to rub his cock head into and along Michelle’s prostate. She must have found her target as Michelle began rapidly thrusting her pelvis up to meet Jackie’s down stroke. Michelle’s eyes rolled back, she let out a load groan, and maintained her upward arching of her back. She quivered, she shook and she clenched Jackie’s shaft with her rectal muscles repeatedly and shot a stream of her warm sperm up her belly and onto her chin as she orgasmed. Michelle collapsed back onto the bed and lay still with Jackie still deep within her. Jackie shot a penile throb out to Michelle and Michelle reciprocated with a clenching of her own. They both giggled and clenched again.
“Did that feel good, baby doll?” Jackie asked. Michelle whispered “That was great… it was orgasmic.” Leaning down to kiss Michelle she used two fingers to collect some of Michelle’s goo that was on her chin. Making sure that Michelle was watching Jackie made a show of licking the sperm from her fingers. Michelle was wide eyed. Scooping up another glob onto her fingers Jackie extended her fingers and offered some to Michelle. Maintaining eye contact with Jackie Michelle sucked her seed from Jackie’s fingers performing a mini blowjob on Jackie’s fingers. A last swirl of her tongue and Michelle laid flat to relax.
Jackie was about to pull out of Michelle when Michelle grabbed her by the waist and said, “Be slow.” Jackie felt Michelle clench down on her penis as she began his withdrawal. ‘Damn, she is trying to feel my vein!’ Just as her dick popped free Jackie said “Baby doll that was a slutty move.” Michelle smiled widely at the compliment.
Reaching for baby wipes and towels the couple cleaned up a bit and then lay on their backs, side by side, staring at the ceiling. Jackie imagined that she could hear Michelle purring. Michelle grabbed Jackie’s hand and pulled it to her lips and kissed it. “Thank you, Jackie. That felt better than I imagined. I’m sure glad I came over today. I was very nervous about how things would go. You’ve made me feel so relaxed and special. I don’t feel like a pervert being with you. It all seems so natural.” She kissed Jackie’s hand once more and then dropped their hands to the bed. Holding hands, with their fingers interlaced, they allowed themselves to recover.
Jackie rolled over facing away from Michelle, and encouraged Michelle to spoon her. Michelle pulled Jackie back until they were snug and tight. Michelle was enjoying feeling Jackie’s heart beat. She leaned forward and kissed Jackie’s neck. “You smell nice” Michelle whispered, “And even without your wig your hair looks nice. Your face and nails add to your beauty.” Michelle shot Jackie a penile throb as her penis was laying against Jackie’s butt. Jackie smiled. Reaching behind her Jackie touched Michelle’s penis and gave it a brief squeeze.
“Remember when we got on the bed that I said I would ask you for a favor when we were done?” Michelle had her eyes closed as they lay there almost entwined and managed an “Um-huh. Why do you ask?”
Jackie slowly sat up and turned to face Michelle. Looking into each other’s eyes Jackie picked up and held Michelle’s hands. “You said that you wanted to feel me inside of you, right?” Michelle nodded an affirmative ‘yes’. “I want you to be inside me. I’m a virgin and can’t think of a nicer person to give my cherry too.” Jackie pulled Michelle forward and they shared a passionate kiss.
Michelle paused a moment and said “When I first got the idea of us being together I was only interested in giving blowjobs and being taken from behind. I never really thought about being fellated or in giving anal sex. I guess I’m more of a ‘receiver’ than a ‘giver’ but I could do it, on occasion.” Jackie smiled, leaned closer, kissed her and whispered “How about helping a girl out? I need to feel what you felt. Now. You won’t know that you like or don’t like it unless you try it.” Jackie reached over and grabbed Michelle’s penis as it drooped from her pantyhose. Giving it a few gently strokes Jackie could feel it begin to swell.
Jackie leaned back and got her tube of lipstick from the vanity and returned to facing Michelle. Establishing eye contact, Jackie expertly painted her lips and tossed the tube up by the pillows. As a token of sincerity and proof of her urgent need, Jackie leaned forward, grabbed Michelle’s shaft, leaned over and kissed the top of her cock. Michelle throbbed against Jackie’s lips. Embolden by her first dark red lip print Jackie hefted and felt Michelle’s penis, gently squeezing and exploring. It felt soft and smooth. Unknown to Michelle, Jackie had never been with a man and had never touched another penis.
Looking into Michelle’s eyes Jackie pulled Michelle’s penis over to her mouth and gently gripped it, with her red lips, just behind the glans, pressing her lips snugly together, in an effort to leave a red ring, Jackie tickled Michelle’s penis with her tongue. She sucked in another inch of meat and re-gripped the shaft lower with her lips. Jackie ran her tongue up, down and around. ‘My god, I’m actually sucking a man’s dick”. Jackie could feel the penis stiffen as she sucked and licked it. Michelle clenched out a throb to tell Jackie ‘thanks’. Jackie went back down Michelle’s shaft as far as she could go and began a slow, sucking withdrawal using her tongue in a way that she liked done to her. Her mouth popped free with an audible sound.
Holding Michelle’s penis, like it was a garden hose, Jackie used her thumb to smear the pre-cum around and around the tip. Michelle sent Jackie an involuntary throb. Jackie leaned closer and gave Michelle a kiss, never stopping her thumb action. ”Well” she whispered, “could you help a girl out?” She bent over and gave Michelle’s erect penis another kiss. “Please” Jackie asked. ‘I can’t believe I‘m begging to be boned! Latent fantasy or not I hope it satisfies my curiosity’ thought Jackie to herself.
“If you want me to help you out you better stop with your thumb action.” Michelle said. Taking that as a ‘yes’ Jackie quickly moved to the end of the bed and sat with her feet on the floor. Motioning Michelle to come over Jackie grabbed Michelle’s hand and pinned her between her legs. She reached to the side of the bed and picked up a tube of lube. She removed the top.
Michelle, and her raging erection, were both ready. Jackie grabbed Michelle’s smooth penis and kissed and bobbed her head up and down it a few times. She used her tongue to shove it from her mouth. Holding Michelle’s erection with one hand Jackie used her other hand to squeeze out a thick line of lube along Michelle’s entire penis; from tip to shaft and back again. Putting the cap back on she tossed the tube back onto the bed. Jackie had an odd grin on her face. “I want it bareback too, baby doll.”
Jackie took hold of Michelle’s dick and began lubricating the entire length with long, slow pulls up and down her shaft. The gel was very effective and soon Michelle’s shaft glistened in readiness. Jackie wiped the leftover lube onto her own dick enjoying the slipperiness that would aid her first penetration. ‘God, I’m so damn horny’ thought Jackie. She leaned back onto the bed and used her legs to pull Michelle closer. “Let’s try it with you standing and we’ll move onto the bed if we have to.”
Jackie pointed her legs at the ceiling, reached back and spread her butt cheeks through her pantyhose. Michelle poked her penis through the rear hole in Jackie’s pantyhose and into Jackie’s sphincter with her cock head and stopped. Using her cock Michelle made a few circles around Jackie’s opening which helped spread the lube. Michelle noticed that Jackie’s hole was making little puckering moves of anticipation. ‘Her butt is trying to kiss my dick!’ thought Michelle. “Lean forward so I can rest my legs on your shoulders.” Jackie requested.
Michelle took a deep breath, thrust forward a little and slowly began the insertion, sliding in almost two inches. The pair of them both gasped in unison. “Wow” said Michelle, “Arrrgh!” said Jackie. Michelle pulled back and repeated the process gaining more than three inches entrance. Applying almost no pressure Michelle could feel Jackie relax and stretch. It sounded like Jackie was doing yoga or Lamaze breathing exercises. Still applying very little pressure Michelle watched in awe as her penis was slowly sucked in to Jackie’s warm ass. Her penis began to disappear deeper and deeper. “Hold on a minute”, Jackie gasped. “Let me catch my breath.” Michelle held still. Wiggling her butt and adjusting her legs so as to get more comfortable Jackie gasped out “Ok… I’m ready.”
Michelle quickly pulled back and just as quickly thrust forward. Jackie gasped. Michelle repeated her in and out technique three more times, savoring the warmth and uniform tightness around her shaft. It felt really good! Trying to be cute Jackie clenched down on Michelle’s dick and maintained a firm rectal grip. Michelle slowly pulled back enjoying the way Jackie’s sphincter milked her cock. “Jackie, I gotta tell you, I think you made a convert out of me. This feels fucking great! Our pantyhose’s rubbing together makes it even better.” Jackie had a double handful of bedspread in an effort to steady herself.
Michelle fell into a pleasant, steady rhythm that was working well for them both. Her strawberry blond hair swayed to the rhythm. Jackie had become passionate with experiencing her first fuck. She clenched, she grunted at each thrust, she wiggled and was making upwards thrusts of passion. ‘God, it is good!’ Jackie thought.
In an inspiration of lust Michelle partial withdrew from the sanctity of Jackie’s bowels. Michelle transferred some of the KY from her dick into the palm of her hand. As she thrust forward into Jackie Michelle wrapped her greased hand around Jackie’s easily available penis and began jacking her off. Jackie screamed loudly, “Don’t stop! Go faster! Faster, I’m so close…!” There was no mistaking the urgency in her voice.
Michelle was also close to orgasm and the tension was extreme. When the moment happened she yelled “Fuck!” thrust forward, and ground her shaft as deep as possible into Jackie. She shoved Jackie a foot further up the bed with just her dick and then spewed her warm seed deep in Jackie’s bowels. The feel of Michelle squirting was all it took to push Jackie over the edge into a sensory over load orgasm.
Jackie bucked upwards several times and wrapped her legs around Michelle, not wanting to let her pull free. Jackie blew her load and it leapt up to her neck and chin. It felt warm as it hit. Jackie relaxed and began softly crying, her legs hanging limp off the edge of the bed. Michelle pulled out. “That was a beautiful thing” Jackie sobbed. Michelle got on the bed and started trying to comfort Jackie, stroking her hair, kissing her face and whispering “It’s all good, all will be fine, take a few deep breaths, there, there…” Michelle grabbed a few baby wipes and began cleaning cum off of Jackie as well as the wet results of their act from her penis.
Jackie scooted herself further up the bed and laid back to compose herself. Michelle lay next to her and began kissing her forehead and eye lids. “Are you ok? Can I do anything for you?” Michelle asked. Jackie looked over, wiped her tears away, smiled beautifully and said “No, I’m ok… it’s just that… I mean… wow! I’m not sure what I expected but this moment was fantastic! How was it for you baby doll?”
Michelle flopped onto her back, stared at the ceiling and began talking. “I had no idea. I told you that I wasn’t keen on fucking people in the ass. What we did here, today, has changed my mind forever. I’m a new man… I mean, I’m a new woman. And I owe it all to you. Maybe it was the way you clenched and milked me, maybe it was because I felt so damn horny.” “And did you feel slutty?” Jackie probed. Michelle turned on to her side and faced Jackie. She smiled and gently stroked Jackie’s cheek. “Jackie, you have made me feel very slutty… and naughty and…and horny… and pretty. I can’t thank you enough. My wondering about how I could experience the things we’ve done just today are over. It could not have been any better. I’m glad I came over. There’s so much to look forward to.” Pulling Jackie closer Michelle gave her a lingering kiss of passion. “Anything else, baby doll?’
Rolling back Michelle sighed and said, “Not only did you make me feel slutty you gave me the chance to be slutty. Never in my wildest dreams did I think that I would ever give someone a blow job, be up their ass, have someone pleasure me anally, wear lingerie and makeup… or hire a full time sex partner/gender trainer” Jackie was thinking the exact same thing about her day! “You did fine on all accounts baby doll.”
Jackie gently tugged on Michelle’s hoop earring and said “It’s getting late baby doll and we have so much to do, you have so much to learn and we haven’t even tried on our beautiful wigs yet, you only have nail polish on one hand, and I’d like to see you in 3 inch pump heels.”
“We need to plan how you can wear some of your sexy lingerie under your male clothes at work and in off work activities. With a little planning we can have you wearing a bra, panties, garter belt and stockings, jewelry, light makeup, lip color, nail polish; so many ways to express your inner girly self. You need to let your hair grow so we have something to work with. Pixie shag would be a good start for you and it could easily be brushed into a guy look. You might like being adventuresome.”
Jackie crawled out of bed and immediately sat at her vanity. Applying a fresh coat of lipstick she began brushing her hair while explaining to Michelle what needed to be done today. “Let’s get out of bed and get on with our day. Come here doll face.“ She motioned for Michelle to come stand by her. Gently holding Michelle’s face Jackie expertly applied lipstick to her lips. Jackie then put a short smear of lipstick on Michelle’s and her cheekbones. “Blend it in with your finger tips and it makes a quick and easy blush. Add more if you want.” Leaning towards the vanity mirror Jackie showed Michelle what she meant, rubbing the colored streak into a healthy looking blush. Michelle followed the lead and smoothed in her own blush. “Wow, that sure makes a difference.” proclaimed Michelle. Michelle took the opportunity to add some mascara to her lashes.
“Pull off your pantyhose and get a fresh pair of panties” Jackie directed. “You may want to use the restroom and clean up a bit. I see you are dribbling a little down the back of your leg. Clean that up and I’ll help you deal with it later. I’ll use the restroom first and then we’ll meet in the kitchen. I have some deli sandwiches and chips that we can eat.” She gave her hair a brief spray of lacquer and then removed her bustier. She had kept that on for Michelle’s benefit.
Adjusting her bra Jackie got busy getting dressed in the same casual, but feminine ‘beach’, gear that she had worn the day before. The only difference was she used a fresh blouse. Michelle was observing her every move. Jackie was pulling on some pretty lace trimmed French style panties but stopped when they were just above her knees. Opening the box of Kotex Lite Days pads, that was on her vanity; Jackie removed and opened a thin pad. Peeling the adhesive from the back of the pad she pressed it into her panties. Looking over to Michelle Jackie said, “Look and learn. This thin pad will soak up any leakage that you may have from having bareback anal sex. It’s an easy way to avoid a messy or embarrassing situation. You’ll hardly know it’s there. It has little plastic wings that spread out and provides better protection from ugly wet spots soaking through your clothes. Sperm will leak out no matter what you do.” Pulling her panties completely up Jackie grabbed a pad and tossed it to Michelle. Michelle stared at it in amazement. ‘My little Jackie is damn resourceful’ she thought.
Following Jackie’s suggestion Michelle lowered her panties and affixed the pad and re-positioned her panties.
Jackie continued dressing and opted for new set of cocoa colored Silky pantyhose quickly pulling them on. Next came her mid rise jeans and a blouse. She slipped into a feminine pair of sandals and started for the kitchen. “I’m going to fix us some nice deli sandwiches and chips. Call me when you’re dressed. I have an extra pair of pantyhose if you’re interested. Oh, and for God’s sake, please toss out our dirty ones.” And then she was gone.
Michelle took the time to use the rest room and cleanup a bit. Looking in the mirror Michelle took a quick inventory of her situation: Matching Navy blue bra and panties, breast enhancers, camisole, cocoa colored pantyhose, beautiful shoulder length strawberry blond hair (with dual pony tails), makeup, eye shadow, eyeliner, mascara, dark red lipstick, blue toe nails and one hand with blue polish. Michelle giggled at her own image. She smiled widely at how feminine she had become in such a short time. She was pleased.
She was about to join Jackie at the kitchen table when Jackie came back in. “Whoa, there Missy, let me see what you have going there.” No doubt about it Michelle was looking nice. “We can’t have you running around in only your camisole and panties. I have a white tennis skirt with an elastic waist that will show off your great legs and add another layer of femininity.” Jackie opened a drawer, found what she needed and brought it over to Michelle. Holding the skirt open Jackie said “Step in to this baby doll.” Michelle did and Jackie pulled it into place.
Jackie gave Michelle a hug and walked them in front of the vanity mirror. “What do you see, Michelle? Do you see the two pretty girls looking back at us?” Michelle stood in silence admiring her female self. She made a point of flipping her hair. Jackie produced a cute tennis bracelet and a gold necklace for feminine effect. Clasping the tennis bracelet closed she stepped back to admire her creation. “Damn, you’re cute”. Michelle gave Jackie a good hug and enhanced it with a long kiss. “Thank you, my Jackie. Thank, you.” Still embracing, Jackie gave Michelle’s panties a good rub; there was a stirring. Michelle felt the need to grab Jackie’s crotch and was in the process of pulling on Jackie’s zipper tab. Jackie playfully slapped Michelle’s hand away saying, “Stop that! There’s plenty of time for that later. It’s time we ate. Oh, and by the way if you were to wear a control top pantyhose it would help make that cute little bulge of your less noticeable.” Michelle added this bit of information to memory. ‘Nice to know’ she thought.
They went and sat at the kitchen table where the sandwiches, chips and olives were waiting. They made idle chatter as they ate. Jackie finished first and went and retrieved the bottle of blue nail polish, shaking it as she was sitting down. Without asking she picked up Michelle’s unpainted right hand and began stroking on the first of two coats. “I want to thank you again for helping a girl out earlier. It felt so ‘right’.” Michelle lightly blushed at the reference to their earlier love making.
While Michelle’s nails dried Jackie took the opportunity to make them both a drink. Jackie took a sip of her drink and then sat the drinks on the table. “There are a lot of decisions that need to be made by both of us. You have to decide on how femme you want to go. One thing is clear you need to build a wardrobe, get some jewelry and accessories, find clothes and colors that will accent your potential and grow out your hair and nails. And you need to let me know how often you want to ‘see me’ and how frequently feminine you want me. Am I to always be girly for you? “Jackie stopped talking and enjoyed a sip of her drink.
Pulling her chair close to Michelle Jackie continued. “Look at my face, my eyebrows, my dyed eye lashes and my nails. I had this done for you. I don’t think I can return to our office like this. It would be difficult for both of us.” Michelle gently held Jackie’s face in her hands. She ran her thumbs over Jackie’s girly eyebrows. Taking in Jackie’s face, her eyelashes and red lips Michelle leaned in and gave Jackie a soft kiss. “You’re right again. You definitely would create a distraction if you showed up at work looking like this. You are so… so… so very ‘Jackie’. I think you’re beautiful.”
Placing her hand on Jackie’s leg, Michelle continued with “We could say that you were transitioning to being a woman. We could find you a new office or job site… you could be away on a special project for weeks, maybe we could make it work. I need to be near you.” Softly holding Michelle’s hand that was on her knee, Jackie pulled that hand and pressed it to her crotch. Jackie squeezed Michelle’s hand between her legs. “I just don’t want to be your office whore.” That remark got Michele’s attention.
Leaving her hand where Jackie had placed it Michelle began to speak and also began to seriously stroke Jackie’s crotch. Her thumb was at the bottom of Jackie’s zipper and her middle finger was at the base of where Jackie’s balls should be. She stroked and asked “Have you given these things any thought?” Jackie moved her chair closer so the finger tickling pressure would be more intense. Jackie pulled her zipper down in invitation to Michelle. Michelle took the bait.
“I think,” Jackie began, “that you and the corporation need a Director of Corporate Diversity that reports directly to you.” Jackie rolled the waist bands of her pantyhose and panties as far down as she could, wiggling to loosen her jeans more, exposing about half of her penis. “I also think that you need to find a nice, near bye, condo that could function as an office and a hospitality suite for you, me and special guests.”
Michelle took more of the bait and had fully gripped Jackie’s shaft and was slowly stroking Jackie’s shaft as Jackie spoke. She adopted the ‘thumb-on-the-cum’ method of petting, spreading Jackie’s natural lubricant around and around. Jackie gave out a soft gasp and slid even closer. “Many executives have private retreats and places to relax or conduct business. You can make it happen.” Jackie’s voice was sounding raspy and urgent.
Jackie leaned back and let Michelle tug her pants off. Jackie freed her cock from the remaining confines. As a tease Jackie made her penis twitch in Michelle’s hand. Michelle giggled and playfully called Jackie a ‘slut’. Maintaining a friendly grip on Jackie’s shaft Michelle pulled it towards her, bent forward and sucked in three or four inches of Jackie’s penis. Her tonguing felt so fine to Jackie. Michelle began bobbing her head up and down Jackie’s now slick penis while still milking her with her hand.
Jackie leaned back into her chair. Michelle got down on her knees. Within minutes Michelle had taken Jackie to heaven and back.
To heaven and back
Grabbing Michelle by one hand Jackie pulled her to the bed room to reciprocate a loving blowjob. Thirty minutes later Jackie was snuggling next to Michelle and was resting on her back with her eyes closed. She was holding Michelle’s hand and could have easily fallen asleep in her contentment. Michelle tugged on Jackie’s hand and said, “I don’t want you to be my paid whore and I wouldn’t expect you to be continually dressed as a female. I think it would be wonderful if you did.”
“I also agree that you returning to your job or office is out of the question. And you’re correct that I could justify the need for ongoing diversity training and a special projects manager. The idea of having an executive retreat, other than my mountain home, is superb. On a personal level I know I’ve found someone that could help me explore my feminine side; someone that could share my new found experiences that were, until today, only far off fantasies. You’ve taught me a lot in a very short time and I feel relaxed being with you.”
Sliding out of bed Michelle sat at the vanity touching up her lipstick, mascara and hair. She removed her dual pony tails and switched to a single pony tail. She was removing the hoop earrings she had been wearing and was inserting a pair of long drop earrings that were lying in view. Snapping on the back of the final earring Michelle casually said: “In short I need you. We could use your first initial on your business cards rather than ‘Jack’ until we arrange a formal name change. How would you like to be my Director of Corporate Diversity and Special Projects? $75k a year, reporting directly to me and working off site. Will you take the job or must I offer it to someone else?”
Jackie leapt out of bed and rushed to hug and kiss Michelle. After a long and sensuous kiss they separated long enough for Jackie to say “Yes! Yes! I’ll do it! We may need to add to my title: ‘Clothing, Makeup and Gender Coordinator’.” They broke into laughter at the thought.
Michelle was heading to the kitchen in order to make them another drink. Over her shoulder she said, “I’m glad your porn tape auto destructed so you have nothing being held over your head. You have the only copy. Maybe someday we’ll have a movie night and watch it together.” She laughed out loud.
“You knew my blackmail videos had disappeared! And you never told me until now!” Jackie almost yelled. “Yes, I knew. That means you did what you did without any coercion. You had sex with me out of your own free will. You really helped a girl out. I truly appreciate that. It proves that we can trust each other. We’ve shared some extremely intimate things today.” Putting her arm around Jackie Michelle pulled her close. “I never thought I would ever say this but I am very attracted to you. You’re intelligent, resourceful, well poised and… delightfully slutty.” Michelle pulled Jackie even closer, kissed her on the cheek and held her hand. “We’re a good match! What’s that expression? ‘You complete me’.
Suddenly Jackie’s future was even brighter. And they hadn’t even made it to trying on skirts, dresses, lingerie or casual girly clothes. There’s so much to do for Michelle. Jackie actually wanted to see how Michele would look in heels.
Unlike yesterday Jackie was looking forward to what lies ahead. Giggling inwardly, Jackie wondered if Jonny from work would actually leave her the tube of lipstick that he had promised, on her desk on Monday. ‘Sure hope his copy of my porn video evaporated to’ she thought. She was very confident that it had.
“I was thinking about taking on a roommate in a month or two” Michelle began. “And my mountain house is in need of a live-in house keeper.”
(The story ends… or does it? the options are many)
A word to the wise: Be careful what you click on!
Epilogue
Here is what prompted this story. Several sites offer gender morphing or adding makeup, hair, a magazine cover of you, etc. That’s okay. However, if you are NOT careful what you click on, the site sends your femme photo to your Facebook page and will be seen by all your friends! Those pretty photos of you could result in many interesting conversations if your femme side is secret.
http://www.clipquiz.net/?all=1
Instructions
1- Click "Login with Facebook and choose profile photo"
2- Accept permission so we can list your Facebook photos
3- click the photo that best shows your face
4- Wait for your result to be ready
I almost did this in error and thought about what sort of turmoil posting such cute photos would have stirred up. On another site I got to the “review image” part of my makeover and was able to ‘save’ my photos BEFORE clicking on the “accept and continue” options. Whew! So I do have several photos of my pretty femme self; they are not seen by anyone (that I know of) but me. Have fun out there but read the fine print.
Maybe you could create a new Facebook page, have no friends, and then morph to your heart’s content. Share if you find a solution. In the mean time “Be careful what you click on”.
Here’s other sites: https://www.esteelauder.com/virtual-try-on & http://www.morphthing.com/