Oscar Night by Jennifer Brock Last year, Novelist/screenwriter David fine wore a red suit to the Academy Awards and made a joke about wearing a gown the next year. Somehow his friend clothing designer Claude Marsh and his bisexual fashion model girlfriend Maritza Delgado convinced him that the best way to make a good impression in a gown would be to present himself as convincingly female. David even agreed to get a number of surgeries, including an impressive set of breast implants. Claude hired "Feminine Deportment Coach" Kay Thomas to teach David, now known purely by the intial "Dee," how to become a woman. Dee's gone through a number of lessons, but it's now time for the one she's been dreading - Kay is making her go on a date with a man.

Part 18
Somehow, bad news always seems to travel in packs. On the same morning that Kay told Dee that everything was arranged for her date with a man on the coming Thursday night, Vanessa came over and said that Claude had finalized the design of her gown for the Academy Awards, and it required her figure to have a strongly defined waist. It required her to undergo corset training, and wear one all the time until then. It wasn’t enough just to put one on the night of the event; constant corseting would let them pull it tighter, and give her dress “the best line,” whatever that means.

She wanted to start Dee’s training right away, so they went upstairs and she had to strip down to her panties. Dee felt very self-conscious, and tried to cross her arms to cover her breasts, but Vanessa wouldn’t let her. She held open a white cotton corset she’d brought with her and had Dee step into it, then Vanessa pulled it up. It went all the way from just under her breasts, where it swept below them in a curve like an underwire, to halfway down her hips. It was fortunate that Dee had worn low-rise panties, since they’d otherwise have to come off.

Vanessa began tightening the laces, and she had Dee lean forward and hang onto the footboard of her bed. She got it to a point and tied it off, giving Dee a few minutes to get used to the constricted breathing. But then she had her give a big exhale, and pulled it even tighter. She then wrapped a measuring tape around Dee’s waist and said that she was at 29 inches, and the goal was to get her to 26 in the next ten days. Dee could barely breathe as it was, and couldn’t imagine there were another three inches of space her internal organs could get squashed into, but Vanessa was the fashion expert, so she had to trust that she knew what she was talking about.

Vanessa checked to make sure she wasn’t getting dizzy, and then helped her get dressed. Dee got to wear a pretty pink bra that only partially covered her breasts and amplified her cleavage a little. Her corset had tabs to attach garters, so Vanessa hooked some on and ran them under her panties, then rolled a sheer pair of silky stockings up her legs and clipped them to the garters. She buckled Dee’s feet into brown leather gladiator sandals with 3-inch heels and had her stand up. A clingy wrap dress in a sort of sunset-orange color went on next, and it showed off Dee’s assets nicely.

She accessorized it with a belt that accentuated her shrunken waist, and a tribal-looking necklace and earrings made of carved wooden and faux ivory beads. Kay told her to do her makeup for a “daytime glamorous” look, and she settled on powder without foundation, a coral lipstick and shimmery earth toned eyes with heavy mascara but no eyeliner, and just a hint of blush. She teased her hair up a little and spritzed on her favorite scent.

Kay had her practice all her walks again, to see how the corset impacted her movements. It seemed to help her posture on the glide, but she had to shorten her stride for the strut and it took a lot of practice to get the wiggle back into her hips for the sashay. Vanessa was impressed with how natural Dee moved in heels, and asked if she’d be interested in taking up modeling after this was all over.

Dee laughed at the idea and did agree that she’d been to enough fashion shows that she could probably handle herself on the runway, but it wasn’t something she was interested in at all. Despite the fact that they’d been working for a month to turn her into a major spectacle, she really wasn’t that comfortable being the focus of attention from strangers. Besides that, she figured that all the corsets in the world wouldn’t be enough to squeeze her down into the tiny sizes that models wear.

Vanessa said that wasn’t a good excuse, since she knew specialty plus-size models with thicker figures than Dee’s, but sensed her unease at the idea. She closed the topic by planting the seed of an idea in Dee’s head, that if she found out when all the excitement from her unveiling had died down that she liked the spotlight after all, Vanessa was sure that Claude would gladly feature Dee in a show.

After a lunch that Dee had to eat even slower and in tinier bites than ever due to her corset, Kay ran her through some more voice practice, to show her that the added note of breathiness caused by her restriction actually made her voice seem more sexily feminine. Dee felt confident that no one could possibly suspect her true identity unless she told them.

Vanessa left and told Kay to call her if she needed any help getting Dee unlaced. She said that ideally they’d want her to sleep in the corset, and Kay could loosen it an inch at bedtime, but she’d have to tighten it again in the morning, preferably even smaller than the day before. Dee would be allowed to take it off for bathing, but it would need to go right back again afterwards. And she really should wait at least twenty-four hours before taking her first bath break. Dee hoped she wouldn’t be too bruised when it was all over.

In the afternoon, Kay said that her big date would consist of dinner and dancing, and so she had enrolled Dee in a crash course in ballroom dancing. For the next four days, she’d be learning the basics, not all the fancy tricks the competitors on those dancing shows do, but it would be enough to properly handle herself on the dance floor.

Dee complained that the corset would make it difficult to properly move, but Kay pointed out that all the ladies wore corsets under their ballgowns back in the age when ballroom dancing was invented, so it’s almost as if the woman’s movements in a waltz were designed to be done wearing one. She had to agree that it made sense.

Dee threw some essentials in a tooled leather handbag and grabbed a red pashmina shawl to wrap around her shoulders if a chill came on in the evening air, and they drove off to the dance studio.

Back when he was in college, a girlfriend convinced David to take a class in ballroom dancing, but Dee really didn’t remember much. That was probably a good thing, since she’d be learning the other part, and disaster could ensue if she were to suddenly try to take the lead instead of following her partner.

There were about a dozen people in the class, mostly couples (and you could tell by looking that most of the men weren’t there willingly) but a few singles. The instructor told them to get into pairs. One guy started walking toward her, but she got the sense that he was kind of slimy, and the way he ran his eyes down her body was just gross.

Dee turned and approached a nervous man standing toward the back of the room. He was slightly built but tall, in her heels her eyes were just a little below his, which were an interesting shade of bluish gray. He had wavy sandy brown hair that was probably a little overdue for a trim, and a roguish stubbly beard along his jawline. He wore a blue striped button-up shirt and a well-worn pair of blue jeans, with black loafers on his feet.

She held out her hand and said, “Hi, I’m Dee. Do you have a dance partner yet?” He shook her hand, introducing himself as Jack, and said he’d be happy to dance with her. He warned her that he didn’t really know what he was doing, so if he stepped on her toes she had his permission to go find another partner. She laughed and said she didn’t know what she was doing either, and she had spikes on her feet, so maybe he was the one who should be worried. He looked down ostensibly to look at her shoes, but she caught him checking out her legs and he blushed a little. It was cute.

They started the class by just walking in rhythm, facing their partners, but around six feet apart; no one’s toes were in any jeopardy. Dee had worried that she’d be going backward the whole time, but that wasn’t the case. The men started by stepping toward the women, and the women started by stepping back, but then they stepped to the left and the women went forward, and then stepped to the right to start again back where they started.

It was really pretty easy. Once they had the pattern down they had to do it facing their partners, with their hands touching palm to palm. When lined up, the man’s feet weren’t pointed straight at the woman’s, but parallel to them, so even if he stepped forward before she went back, he wouldn’t be stepping on her feet anyway. Jack and Dee had nothing to worry about.

Once they had that pattern down, they had to get into the real dance position. He held her right hand in his left, and placed his right hand on her back. She felt a little shiver as his fingers touched her bare skin. Her left arm got to rest on top of his. They had to go through the pattern again. The tricky part was that they needed to do it without watching their feet. They were supposed to smile and look at their partner’s face.

Jack seemed to have a particularly hard time not looking down, so Dee tried helping him out. She made a half-smile and teased him. “Are you really breaking eye contact to check your feet, or are you just trying to sneak a look down my dress?” He realized that he truly was getting an eyeful of her cleavage every time he looked down, so he became very embarrassed, and tried to stammer an apology. But she couldn’t hold a serious face to feign being offended, and soon they were laughing together.

By the time class was over, they were not only doing the foxtrot like they knew what they were doing, but they felt like old friends. She thanked him for making the class bearable, and he corrected her and said that she was the one who had been so wonderful at putting him at ease. She promised to look for him in the next session, and went to find Kay for her ride home.

It felt wrong not to bathe after all that exercise dancing, but Dee was a good girl and did as she was told. Kay let her laces out a little, and gave her a hand dressing for bed in her sleeping bra and one of her nightgowns that buttoned up in the front. Sleeping in a corset gave a new definition to the word “uncomfortable.” It reminded her of when she first came out of surgery and had to sleep perfectly flat on her back or her boobs would complain. She just had to get used to not breathing so deeply when trying to relax. She finally broke down and took one of the pills they’d given her for sleeping during her recovery and that did the trick.

Kay found her as soon as she woke up the next morning, and made her grab the bed so she could tighten her corset. She had to take three strong breaths, and on the third exhale, Kay pulled. It felt even tighter than the day before, and she needed to take a moment to let things adjust. She went into her bathroom and gave her exposed parts a spongebath with a damp washcloth and a little soap, just to not feel so gross.

Her outfit for the day started with a pretty white bra and panty set, then a pair of suntan pantyhose. Dee covered up her bra with a white lacy camisole which would look nice under the sheer white blouse she’d picked out. She paired the blouse with a crisp cotton skirt that had a white and teal paisley pattern printed on a navy blue background. For shoes she chose a funky pair of teal leather pumps. She picked some silver and turquoise jewelry pieces, including a fun pin shaped like a turtle.

The second day of dance class went well. She went straight to Jack, and everything clicked and they got back into dance position just like that. He told her she looked nice, if a little “school-marmy,” and she teased by saying she hadn’t wanted to give him any extra reasons to look down. He cutely had no response to that.

They went through the box step they’d learned the day before, and then added a couple new moves they could do to mix things up and start moving around the room instead of staying in essentially the same spot. Their teacher gave them a routine to follow, and it took three or four songs for everyone to learn it. He even got fancy and showed them a move where the ladies got to do a fun little twirl.

Dee finally got her bath that evening. Kay helped her out of her corset, and she looked kind of silly with vertical red stripes down her torso. It was nice to be able to breathe deeply again. She luxuriated in her bubble bath, letting her sore abdomen soak until the marks went away. And she barely had enough time for a quick rinse off in the shower before Kay came knocking to tell her time was up. Dee negotiated a few more minutes so she could wash her hair, but that was it.

Once Dee had toweled off, Kay imprisoned her in a new clean corset that Vanessa had left with her. She told Dee not to worry, that she’d done waist training with other students so she knew what she was doing. It seemed like she was even a little better at it than Vanessa was. She tightened it once, and let Dee’s organs get used to their new positions for a bit, then tightened the laces again, and on a third tightening, she had Dee stand lower so Kay could put her knee against her back for leverage. When it was all done, she fetched a measuring tape and checked Dee’s waist. Kay had gotten her down to within an inch of her target size. It took more time to get used to, but Dee figured she was hardly the first girl to suffer in order to be beautiful.

***

The day of her last dance lesson, Dee was trying to pick out an outfit that would be sexy without looking like it was trying too hard, one that would show off her best features. Standing in the closet in her bra, panties and corset waffling between three dresses, the thought hit her that she was trying to figure out which one Jack would like her in the best.

When Kay came to see why she was taking a little too long to get dressed, she found Dee sitting on the floor of her closet, weeping. She lowered herself down next to her, wrapped a reassuring arm around her, and let her lean on her shoulder. “What’s the matter, Sweetie? Did something happen?”

Dee sniffled, “I’ve lost myself. I think I snapped and went gay.”

Kay stroked her hair. “What do you mean?”

“I was choosing a dress to wear, and realized that I wanted to find one that the guy I’ve been dancing with would like.”

“Don’t worry about that. There’s nothing wrong with wanting men to think you look pretty. That’s a perfectly normal part about presenting a female appearance.”

“But that’s just it! I wasn’t trying to look good for all men; I wanted to look attractive for one specific man. I wanted this guy to want me, like sexually. I think I’ve been flirting with him all these classes without even thinking about it.”

“That’s okay, too. Flirting is a lot of fun. It shows that you’re really in touch with your feminine persona if you’ve been doing it subconsciously. It’s a good thing, really. And yes, flirting is about making someone desire you, so you want to wear something that makes him fantasize about ripping it off of you, but there’s no harm in a fantasy.”

“No? It doesn’t make me gay, though?”

“Honey, all that we’ve been working on this last month is taking your old male ego and locking it away in a box deep inside you. All that this means is that you’ve had a breakthrough in seeing yourself as completely female. Just take your old male self-concept and stick a pin in it. Allow yourself to embrace your womanhood completely. After next week and your big event, when you’re figuring out who you’re going to be everyday for the rest of your life, you can take that pin out. But for now, we don’t need him getting in the way.”

“So it’s not wrong if I want to be sexy for Jack?”

“No, it’s not. Just make sure you keep your relationship in the flirting stage. If you take things too far, you might end up in trouble. Let him undress you with his eyes, but not his fingers — they might get a surprise that could end badly.”

“Don’t worry about that. No one will be undressing anyone, not that it wouldn’t be fun. Wait, I don’t know why I said that. Where are these feelings coming from?”

“You’re just learning to accept yourself as a female. Don’t question your emotions, just let yourself feel them. Just be careful about acting on those feelings.”

“Okay, if you say so.”

“If it will help you rationalize away your unease, chalk up your attraction to this guy to the hormones you’ve been taking.”

Dee’s eyes widened in panic. “What?”

“You’ve been on a light dosage of female hormones since we started. That cream the doctor gave you that you’ve been rubbing into your breasts so they stay supple contains a small amount of estrogen. It’s so they behave like they were growing naturally. It’s why that stuff’s only available with a prescription. There’s probably been a tiny amount of growth in your actual mammary tissue, but I doubt you could see it without a microscope. Also, the herbal tea I’ve been giving you contains compounds that mimic female hormones, as well as others that reduce the impact of the male hormones your body produces naturally. Also, your body already produces some female hormones naturally, but you’re not taking anything to suppress those.”

“Really? Is there any danger that they’re making permanent changes to my body?”

Kay did her best not to laugh at the person who had undergone major surgeries to feminize her body worrying about tiny doses of hormones changing her. “No, Sweetie, the levels aren’t that high. You probably have slightly more estrogen in your bloodstream than a woman who’s passed through menopause, but nowhere near the amount in an average adult woman, let alone the body-changing surges of a girl in puberty. But the hormones are there, so use them as an excuse if you need to blame an outside influence to soothe your inner manhood enough to keep it from denying your feminine self the right to feel all that you’re feeling.”

“I suppose that makes sense.”

“Okay, now let’s get you cleaned up and looking your hottest for this guy. What did you say his name was?”

“Jack.”

“Look out Jack - Dee is going to knock you out of your socks! I just hope he’ll still be able to dance with you when there’s no blood left in his brain.” Dee actually started giggling along with Kay at that, and they worked together to pick out a killer outfit.

It had the desired effect. When she walked into the dance studio in her silk little black dress, all eyes were on her. Its layered handkerchief hem fluttered around her knees and covered up her lack of hips, and its halter-style bodice left her back and shoulders bare to feel the touch of her partner’s hand, while the neckline had a moderate V that showed off enough of her cleavage to tempt without seeming overtly slutty.

Burgundy lipstick made her mouth the focal point of her face, although her lush lashes and silvery eyelids demanded attention whenever she blinked. Large gold hoops were in her ears and her hair was pulled back in a fairly casual ponytail that bounced nicely as she crossed the room. She loved the click of her four-inch stilettos, and they brought her nearly eye to eye with Jack.

He was fairly dumbfounded, and fought for the right words to tell her how incredible she looked. She thanked him with a smile that turned his insides to mush. He seemed nervous again dancing with her, and Dee thought that was a good thing.

The instructor had them review everything they’d learned, and they did a few turns around the room in a foxtrot and then a few in a waltz, and Dee was really enjoying herself. She even liked it that Jack was the one steering them, and her only job was to follow his lead, and direct him only to avoid a crash if he couldn’t see another couple coming up behind him.

They went over the cha-cha they’d started to learn in the previous class, and the teacher also showed them some rhumba and a little salsa. The fast dances were a lot of fun, and Dee loved the way they made her skirt flare. But far too quickly, the class was over.

Kay hadn’t arrived yet to pick her up, so when Jack asked if she wanted to get a coffee in the café next door, she couldn’t think of an excuse to say no. She texted Kay to let her know where to find her, and followed him over to the coffee shop. Jack was very sweet and let her pick a table while he stood in line for their order.

They chatted lightly about dancing and why they’d taken the class. He was getting ready not to embarrass himself at a charity ball his boss was throwing. He was a civil engineer and worked for a firm that was involved in some major renovation projects in the old part of the city. Dee laughed that she didn’t even know there was an old part of the city.

For her part, she told him that she’d been taking the class because her friend was making her, which was mostly true. She also had to admit that she was preparing for a blind date that would be taking her dancing, and she could read Jack’s face to see his hope fading. She did let him give her his number in case it didn’t work out with the other guy, but she wouldn’t give him hers.

She felt sorry for him, because he seemed like a decent guy; he just had bad timing. So when Kay showed up to take her home, she gave him a little hug and a kiss on the cheek, and thanked him for making learning to dance so enjoyable.

In the car, Kay told her she thought Jack was cute, and told Dee she had good taste. Dee was feeling a little sad that she’d had to turn him down, but Kay reminded her that she’d get her chance to go out with a guy soon enough. Dee wasn’t sure whether to feel dread or excitement about that.

***

Kay took Dee off her herbal tea the day before her big date. She wanted to give her libido a chance to come back. Dee was confused enough as it was, but she went along with it. That night, she had a strange dream that she didn’t quite remember but it had something to do with dancing and she thought Jack might have been there. She was also surprised to discover that for the first time in a long while, she’d awoken with an erection.

She contemplated trying to just will it away, but it had been so long since she’d had any kind of sexual thought she decided to take things into her own hands. She didn’t want a mess, so she got up and fetched a towel and her softest skin lotion from the bathroom. While she was up, she locked her bedroom door, just so Kay wouldn’t interrupt anything.

She removed her nightgown and lay in bed atop her towel wearing just her corset, and wished she had a way to take that off, too. She ran her shiny nails along her sexy, smooth legs and imagined it was the caress of a lover. She danced her fingers along the inside of her thighs and drew close enough to tease, but didn’t touch just yet.

She moved her hands up along her body to find her breasts, giving each a gentle squeeze. Her fingers naturally gravitated to her firm and eager nipples. A few drops of lotion on each hand made her thumbs slippery enough that as they traced circles around her nipples, faster and faster, it brought excitement and not pain. Her breathing became more rapid, and she worried about hyperventilating. She gave each nipple a sharp pinch and that nearly sent her over the edge.

It was time. While her left hand continued to play with a nipple, her right hand reached out and placed a dollop of lotion on the site of her hunger. She worked her hand along the shaft, letting a different finger pay a visit to the warm purple tip with each stroke.

In only a few minutes, her ministrations were rewarded with a sticky burst of relief. She had a strong urge to lick her fingers but they smelled too floral from the lotion when she got them close to her mouth. She wiped herself off on the towel and breathed as deeply as the corset would allow, savoring the afterglow for a moment.

Eventually she got out of bed, put her towel in the hamper, wrapped her sweaty body in a robe, and sought out Kay’s help so she could get her straightjacket off and take a shower. She thought that maybe Kay suspected what she’d been doing, but she didn’t say anything.

Her day was a fairly easy one. A brief review of body language, emphasizing flirtatious gestures, was followed by some practice with nighttime makeup techniques. After lunch, they watched a couple romantic comedies on DVD, and Dee had to point out how the women were using their words, postures, and fashions as tools to help get their men.

Dee had to read a romance novel at bedtime, to help put her in the right mindset for her date the next day. Fortunately, it didn’t inspire any sexy dreams, at least none she could recall.

***

Thursday Kay had gone out early and brought a shopping bag of things up to Dee’s room. “Now before I show you what I got for you, I want to make it extra clear that all I’m asking you to do tonight is go out to dinner and dancing with Joe, and behave as though you’re a woman on a date with a man, enjoying herself. That’s the only service he’s been paid to perform, and all I’ll be asking him about when I call him tomorrow is how you did in public.”

Dee wasn’t sure where Kay was heading, but was following her so far. “Okay, I understand.”

“When he brings you home at the end of the date, it’s up to you where you want to go with the scenario. A girl’s got her options for how to deal with a guy. You could thank him for a nice evening and send him on his way with a peck on the cheek, or you could let him walk you to your door and give him a serious good night kiss, or you could invite him in and let things get a little more physical. But either way, it’s all up to you.”

“I don’t think I’ll want to do much more than the good night kiss, but okay.”

“In case you do want to invite him in, you don’t need to worry about me being here to eavesdrop. I’ll be spending the night in a hotel, and won’t be back until noon tomorrow.”

Dee shook her head. ‘That’s expecting a little too much. I really don’t think that’s necessary.”

“It’s already been arranged. Besides, even if you’re home alone you might want to be alone to do some experimenting. If going out with Joe leaves you curious, but you don’t think you’re comfortable yet with the idea of an actual man, I got you a couple toys that you can play with.” Kay opened her shopping bag and pulled out a very realistic looking silicone penis complete with testicles, and a second slender bullet-shaped dildo. “Either of these can give you some idea of what it would be like to be penetrated, and both of them vibrate, so they’re even better than the real thing.”

Dee wanted to tell Kay to keep her toys, but she had to admit to herself that a part of her truly was curious about what it would feel like to be with a man like a real woman. She tired not to let Kay see what she was thinking, but she couldn’t help blushing.

Kay continued, pulling a large squeeze bottle out of her bag. “If you do use one of these, or if you invite Joe to spend the night, (don’t worry about him rejecting you; I know for a fact you are exactly his type) make sure you use plenty of lube. Use too much and you might make a little mess, but if you don’t use enough you can get really badly hurt, so try to err on the side of excess. Liberally coat your little friend, and also give yourself a good couple of squirts directly.”

Even though she was somewhat accepting of the idea of being penetrated, having to think about the specific mechanics involved made Dee very uncomfortable. It wasn’t a part of her anatomy she regularly gave a lot of thought to.

And Kay wasn’t done discussing that area. “To really properly prepare yourself for sex with either an actual man or one of these substitute men here, it’s polite to make sure you’re nice and clean for him and have plenty of room inside.” She pulled out a box of six disposable enemas. “One of these should be enough, but if you’re really worried about being a good hostess before you invite a guest over, a second one to make sure should be enough for peace of mind. I wouldn’t do more than two in a row, though. I just get the big box to save money.”

Having to think about cleaning herself out before shoving something up there made it feel more real, and Dee had to concentrate to remain calm. When she’d settled down, she hid the new toys in the drawer of her nightstand, and put the big box in the cabinet in her bathroom.

After finishing her sex talk, Kay gave Dee a hand getting ready for her date. Dee was relieved to learn that she’d be set be free from the corset for an extended time. She had to wear an elastic waist cincher instead, but it wasn’t quite as tight as the corset, and she could take it off and put it on without needing assistance.

Dee spent extra time tucking and taping her extra bits back in place, and then pulled on a pair of black satin panties that had extra padding in the buns and hips to round out her figure. She wore a coordinating lacy black strapless bra that had just a little bit of push-up in its cups. Her legs were encased in a pair of sheer black seamed stockings with silicone tops that stayed up without the need of garters, and a pair of sexy peeptoe slingbacks that showed off her red lacquered toenails went on her feet.

Her fingers were also done in a shiny fire engine red. They contrasted nicely with the deep purple minidress she pulled over her head. It had tiny spaghetti straps and when Kay zipped it up, it clung tightly to her curves. Her boobs were very nicely framed in the low scooping neckline, and the hemline came to only five inches or so below the swell of her sexy faux derriere.

Kay worked with a curling iron to give Dee a partial updo, with her hair gathered back but then released in a cascade of ringlets. Her makeup was also flashier than usual, with shimmering powder over a flawless foundation base, and a few more shimmers on her shoulders and décolletage. Enough blush went on her cheeks to contour her cheekbones, and extended wearing bright red lipstick with a shiny topcoat made her lips seem to beg to be kissed. Smoky smudged eyeshadow covered her lids, and her eyes were outlined with crisp black eyeliner and volumizing black mascara. She even used an eyelash curler to make her eyes seem larger.

For jewelry she wore a triple-strand silver chain necklace that helped highlight her cleavage, and long dangling silver chandelier earrings. Four silver bangles went on her left wrist along with a bracelet watch, and a silver ring with what looked like a pair of amethysts went on the middle finger of her right hand.

Dee looked in the mirror and worried that maybe they’d gone a little overboard. She looked a little too sexy; would she be sending Joe the wrong message? Would people think she was some kind of hooker? Kay tried to ease her fears by saying she didn’t look like a cheap tramp; she was clearly wearing quality designer clothes. Sure she looked sexy, but that was just because Dee would have looked sexy even without special clothes and makeup. She didn’t look like a hooker, just the beautiful woman she was, dressed up for a night on the town with her date.

It was too late to change, so she just had to trust Kay’s judgement. She checked her watch and saw that she was late. She was glad that Joe seemed to be running late, too. Kay spoke up and said that Joe was already there. He’d shown up while Dee was dressing, and Kay had shown him in. He was waiting downstairs for her, but Dee didn’t need to worry — a gentleman expects to have to wait for his lady to get ready.

What it did mean was that Dee didn’t have any time to get nervous. Her date was already there, so she wouldn’t have to waste any energy worrying about what he would be like. She could find that out as soon as she left her room. Kay organized a clutch bag for her, and picked out a wrap for her to carry, and said she’d go tell Joe that Dee was ready. Dee took a couple of deep breaths and then opened her door and did her best glide down the stairs to the foyer.

Joe followed Kay into the hallway and looked up to see his companion for the evening coming into view. First to appear were a pair of very sexy shoes — her feet weren’t too big; that was a point in her favor. The feet were topped by an incredible pair of legs and he began to think that this was going to be an easy job. She had beautiful hands with long shiny nails, and her slender arms had neither unsightly hair nor unwanted musculature. A magnificent rack caught his eye next and he was glad this time Kay had hired him to escort an actual tranny and not a guy in a dress with fake rubber tits. He wondered if she was pre- or post-op, and his eyes strayed to her crotch but he didn’t quite have the right angle to look up her dress. She spoke, and he looked up to her face. Damn! She was gorgeous! And amazingly, he was getting paid for this. For a moment he wondered if Kay was pulling a trick on him and setting him up with an actual woman for a change, but she’d said this one was one of her usual clients, but there was nothing usual about her. He’d have to bring his A game for this one.

Dee saw the man standing in the foyer looking up at her. He was tall, at least six-foot four or five. He’d be towering over her even in her heels. He was broad, too. His nicely tailored charcoal gray suit jacket did nothing to conceal his muscular shoulders, and the open buttons on his blue silk shirt showed some of the curly golden hairs on his tanned, powerful chest. He stood with his hands in his pockets, which somehow seemed to make his belt buckle catch the light from the ceiling fixture. Her eye was drawn to the shiny buckle naturally, and not because she was wondering about what was beneath it. She apologized for making him wait, but he didn’t seem to hear her. She tried again when she stepped off the stairs.

“Hi, I’m Dee. I hope I didn’t keep you waiting too long?” She held out her hand for a shake, but he took it and kissed it.

“Joe. And for someone as lovely as you, I’d wait an eternity. It will be my pleasure to be your escort for this evening. May I help you with your wrap?” He took the silk shawl from her hand and deftly draped it across her shoulders, in a move that somehow ended up with his arm around her waist. Dee wasn’t sure how to react.

Kay held the front door for the couple, wished them luck on their date, and reminded Dee that she’d see her at noon the next day. Joe hoped that implied what he thought it did.

He walked Dee to his car. It was some kind of black sports model, but she didn’t know enough about cars to name its make or model. He clicked his remote to unlock it, and opened the passenger door for her, holding it while she got in. Dee had to be very careful getting in with such a short hemline than she didn’t give him a free show as he stood by the door. She scooped her skirt behind her and backed into the seat, keeping her knees tightly squeezed together, and swung her legs in once she was seated. Joe pulled the seatbelt out for her when he saw her reaching up, and closed the door once she was tucked inside securely.

He went around to the driver’s side and got in. Dee noticed that he didn’t fasten his own seatbelt, and he turned to her and smiled after he started the engine, as though she was somehow supposed to be impressed by the hum of his motor. As they drove to the restaurant, he told her to try to forget who was paying and who was being paid to be there; she should just think of it as two people enjoying each other’s company for a night on the town. And even though he knew the kind of person Kay worked with, as far as he was concerned she was a beautiful woman, 100% complete. He’d be treating her as such, and he hoped that was how she saw herself. Joe had given that same speech dozens of times, but this was one of the rare cases where he actually meant all of it.

It did help put Dee at ease. It would be easier if she could just let go of all the baggage and circumstances that brought her to this point and just be in the moment, a woman out on a date with a man, and do whatever felt right from that perspective.

Joe asked if she wanted some music, and before she could answer he moved his hand from the gearshift to the stereo controls, letting his fingers “accidentally” brush her knee as he did so. Soft, romantic R&B came out of the six speakers that surrounded them, and Dee could feel her seat vibrate when the subwoofer hit the bass line. Joe’s style of driving on the freeway reminded Dee of Maritza, and she felt sad that her love wasn’t there. But it also reminded her that Maritza had not only given her permission to go on this date with a man, but in her Valentine letter had actually seemed to be encouraging Dee to do more than just date. So she just smiled at Joe and tried to remember the words to the old song that goes “if you can’t be with the one you love, love the one you’re with.”

Joe heard Dee kind of singing under her breath, but she was way off for the song that was playing. He’d never understand chicks, even those that used to be dudes. But she was hot, and hot excuses a whole lot of crazy. Of course, that theory had gotten him a lot of trouble in the past. She was smiling at him, so he smiled back, but that seemed to make her mad that he wasn’t keeping his eyes on the road.

They made it to the restaurant well in advance of their reservation. Joe wasn’t quite fast enough to keep the valet from opening Dee’s door for her, but he did get there on time to take her hand and help her out of the car. The valet did take a lingering look at her as she got out, but he’d have to suffer with knowing she’d be with Joe all night, and not some schmuck in a red blazer. He held out his arm, and she took it in hers, even cuddling up against him a little although that was probably mostly because of the wind. He held her tight while they waited for the claim tag from the valet.

Joe was a gentleman and held the door into the restaurant for Dee, and he offered her his arm again to walk over to the hostess station to give his name. Their table wasn’t ready yet, but she said they could wait in the bar. Dee was impressed when he told her that since he was driving he didn’t want a drink before dinner, but if she wanted one he’d be happy to go with her to the bar and get a glass of water or something.

She still felt a little tense and thought that maybe a drink would help her loosed up a little, so took him up on the offer. They walked over to the bar and found a little table. The high stools were another challenge for Dee to sit without flashing anyone, but she managed to get perched and even got her legs crossed without offering a peek of her panties. Joe asked her what she wanted and then went over to the bartender to fetch a glass of house white for her and a bottled water for himself.

They tried making small talk while they waited in the bar, but they were pretending to be just a couple on a date so they couldn’t talk about his job as a paid escort, and they were pretending she was a normal woman so they couldn’t talk about her real life or the situation that had brought her to Kay, so that left very general topics of conversation. He tried sports, but she didn’t follow any. She tried talking politics, but he really didn’t have any strong opinions on issues. Since they were LA and the awards were only a few days away, he tried asking if she had any picks for the Oscars, but she claimed not to watch very many movies.

Finally, she hit upon asking if he’d always lived in California, and he told her how he’d started out in Indiana but had come west after college to seek fame and fortune in Hollywood. She talked about being from Ohio, and they started reminiscing about how things were different out on the coast than back home, and a lot of their experiences were similar. Dee only edited her story slightly, lying with a conspiratorial wink about having been a smalltown girl trying to make her way in the world, before deciding to come out to Hollywood to become famous. She also lied about still looking for fame, since she didn’t want him to figure out her real identity.

They were getting along so well, smiling and laughing and trading stories that when the hostess waved to them they didn’t see her and she had to walk to right next to them to say their table was ready. Dee’s glass of wine had worked well, and at some point in their conversation she’d touched his hand to punctuate a point, but she’d left hers there for some reason, and she was embarrassed to realize she was holding his hand when the hostess showed up.

She brought them back to the hostess station, where a waitress was waiting to bring them to a table and give them their menus. She gave them a list of specials and then gave them a few minutes to make up their minds. Dee ended up going with a Chilean sea bass special, and Joe ordered a steak. She stayed with the house white she’d been drinking and got a refill, and he got a draft beer.

Her stomach was still a little nervous, so she just poked at her salad and couldn’t finish it. She offered Joe her cherry tomatoes and he accepted, but when she stuck her fork in one and reached over to drop it on his salad plate, he took her hand and brought the fork to his mouth instead. His hand was larger and stronger than hers, and it was very easy to just let him guide her. And somehow the way his lips wrapped around the tomato was sexy as all hell. She silenced the inner voice that was trying to say that something very wrong was happening, and just went with the flow. She let her eyes meet his and licked her lips as though she’d been the one to eat the tomato. He leaned closer and her heart fluttered in anticipation, but he just brought her fork-hand to her plate for the other tomato.

She finished playing with her salad and placed the napkin from her lap onto the table. She excused herself to go to the Ladies’ and Joe actually got up too, so she’d have an easier time getting out. Impulsively, she gave him a quick peck on the lips and told him she wouldn’t be long. She wiggled a sexy sashay toward the sign indicating the restrooms, and was grateful that there was no line.

She took a stall, raised her dress and lowered her panties, hoping no one would come in and notice that her rear end came off with them. She did her business and wiped off, checking to make sure her tape still held. It did. She pulled her booty back up and pulled her dress into place, and exited the stall without getting found out. After washing her hands she checked her makeup. She literally powdered her nose, which made her chuckle, and she made a few kissy faces at the mirror to make sure that her lipstick was living up to its claims of maintaining color and shine even after eating.

She sashayed back to her table, and Joe stood up again when he saw her. The salad plates had been cleared, but their entrees hadn’t shown up yet. She touched his arm and said “I’m back. Miss me?”

As an answer, he put his hand out to keep her from sitting down. He turned toward her and moved his hand to her cheek. He turned his face toward hers and held her there as he gave her a long, full kiss. She only parted her lips briefly, to let the tip of her tongue quickly touch his, but she didn’t think he deserved more just yet.

Joe broke the kiss and sat down, hoping she didn’t notice why he needed to get his lap back under the table so urgently. This chick was definitely getting revved up, and the fact that she wasn’t completely a chick just made her even sexier to him. He hoped she didn’t get up again soon. He’d be forced between rudely staying seated and embarrassingly standing up.

Their meals showed up and they started eating. Joe casually commented that Dee’s fish looked pretty good, and she cut off a piece and held her fork out to him. He took her hand again and brought it to his mouth. He looked her straight in the eyes and declared it to be delicious, but she wasn’t sure if he meant her or the fish. He asked if she wanted to try a taste of his steak, and she said sure. He cut a slice and put it on his fork, but instead of holding it out to her, he brought the piece to his own mouth and held it between his teeth. He turned toward her, daring her to take the piece from his mouth.

She slowly brought her mouth to his, trying to just nab the piece of steak without letting him get what he wanted. But he was too fast for her and opened his mouth right when she got hers in place, and she soon found not only the steak but also his tongue inside her mouth. She leaned into it and had a little fun playing with his mouth before she backed away.

Joe didn’t want to cause too big a scene in the restaurant, so he held back on the physical stuff, but kept flirting with his eyes, and describing everything he was eating in terms that could be interpreted as talking about sex without much effort.

Dee behaved herself for the most part, but did try to get the upper hand by fiddling with her necklace, shrugging her shoulders, and leaning forward occasionally, all to make him look at her chest. Every time she caught him watching her breasts, she awarded herself a point. She didn’t finish all her entrée but still said yes when the waitress asked if they were interested in dessert. She ordered a chocolate cheesecake thing that sounded truly decadent, with two forks. Joe just wanted a coffee.

When the dessert came, she decided they needed to sit closer to share the plate, and scooted her chair over closer to his. Joe took advantage of the opportunity and reached out to put his arm around her shoulders. Dee broke off forkfuls of the treat at a time, feeding every other bite to Joe and the rest to herself, until she was full. There was a little square left, and she had them wrap it up to take home.

When Joe used his credit card to pay the check, Dee paused for a moment and thought about it. He was probably just going to pass his expenses along to Kay, and she’d probably just be passing her expenses along to Claude. So in a sense, Claude had just taken her out to dinner. That train of thought led to scary places, so she quickly derailed it and tried to get back in character.

Joe pulled out her chair and offered a hand to help her up. She accepted his assistance, and carefully smoothed her dress as she stood so no one got a free show. She grabbed her bag and he adjusted her wrap for her. She let him wrap his arm around her waist and guide her to the door. There was only a short wait for the valet, but there was a breeze so Dee snuggled up close to her date. At least her dress was tight enough that there was no danger of her skirt blowing up.

When the car pulled up, Joe opened the passenger door for her, and she gave him a quick kiss before getting in. He went around to the other side, tipped the valet, and got into his seat. She leaned over to him and said, “Would you please fasten your seatbelt this time?”

He smirked. “If you really want my belt fastened you’ll have to do it yourself.”

Dee had to undo her own belt first, but she accepted his challenge and twisted in her seat and leaned across him to grab the little metal tab by his shoulder. Joe caught her in his arms and pulled her close for a real kiss. After only a token resistance her lips yielded and accepted the invasion of his tongue. Joe was really getting into it when the driver behind him hit the horn to get him to move his car. He had to let her go.

Dee pulled away and returned to her seat, but not before buckling him in. She gladly smiled over winning that one. And if maybe her fingers brushed his crotch as she pulled the belt over and she noticed exactly how much he was in her thrall, that was just a bonus. She straightened her dress and fastened her own belt.

Joe said that Kay had told him to take Dee dancing, but if she didn’t want to they could go somewhere else and Kay wouldn’t have to know. Dee told him that she’d been taking classes specifically so that she could go dance with him, and she thought it would be fun. He agreed and hit the freeway again, to take her to one of his favorite clubs.

It was an intimate little venue where a small combo played danceable jazz. Dee imagined that before California laws got all healthy, the room would have been smoke-filled and sleepy. Even without the smoke it was still dimly lit, virtually the only fixtures were low-wattage glass globes pretending to be candles on the little tables. Joe seemed to be a regular here; the doorman let them in without charging a cover, and he seemed to congratulate him for landing a hottie.

Joe had planned his night expecting Kay’s student to be slightly passable or worse, and he almost regretted taking Dee to a shadowy dance club. She deserved to be shown off under a spotlight. But she wanted a place with ballroom music, and this was the only one he was familiar with.

They claimed a table, and he got them a couple drinks from the bar. They sat and listened to a couple songs before she seemed ready and he asked her to dance. She seemed to fit nicely in his arms, and for a beginner she was a pretty good dancer. They stayed on floor until the band took a break, when they returned to their table.

As they sipped their drinks, Dee flattered Joe. “You’re a good dancer, and it was very easy following your lead.”

He lightly stroked her hand. “I agree. We work well together.” With a wink he added, “You know, they say that you can tell by the way a couple is on the dance floor, what they’d be like in bed.”

Dee lost her breath for a moment. When the shock passed, she tried to cover by batting her eyelashes and leaning in conspiratorially. “No, I had not heard that. Do you think it’s true?”

Joe played it coy. “I don’t know. I haven’t done the research.”

Dee grinned. “Well then, let’s get back on the floor and see what kind of stamina you’ve got!” She grabbed his hand and pulled him to his feet.

They lasted through five more songs before they were both getting a little tired. Dee told Joe to take her home. She buckled him in again, and this time besides stealing a kiss he gave her bottom a little squeeze. Dee wondered if he knew he was groping a foam pad. He was a great kisser anyway.

Before she realized it, he pulled into her driveway. He got out of the car fast enough to open her door for her while she was still taking her seatbelt off. He took her arm and walked her to her door.

At the front stoop, he swept her into his arms and leaned in close. She returned his embrace, and they shared a deep, wet toe-curling kiss. Dee had a conundrum. Would she bid him good night and send him on his way, or open her door and invite him in?

*** To be continued…