The call from Mistress Andrea made my day. I hadn't seen her for over a week and was
looking forward to playing with her & having my chastity finally removed. You should
know that Mistress and I have known each other for many years and have I always
enjoyed being her sissy sub.
Lately she has been training me to be more feminine in appearance. I have been
required to buy woman’s stretch pants and blouses for daily wear to work, and always
have fresh manis and pedis and mascara on at all times. She will often message me
during the day and have me send her a photo of what I am wearing. I am given points
for being properly dressed and negative points if i don’t meet her approval. I am in
chastity now for not meeting her requirements.
It has been hard to get used to going to work everyday in feminine clothing and I do
get some looks at the office. Most of the female staff think I look pretty. I think
they think I am in transition but haven't said anything openly about it. But lets face
it readers, women can tell if you are wearing womens pants. Some of the guys don’t talk
to me anymore and others don’t seem to notice. My hair is below my shoulders now and in
a more fem style than just an old hippie pony tail. Luckily my company has a very open
mind to trans folk so they do not hassle me about it.
I recently had to start wearing a light pink lipstick to my work wear. I find I have to keep it refreshed all the time in case she calls and wants a pic because I never know when or if she will call. My panty
girdles keep my chastity tucked away and I present a mostly smooth figure in my stretch
pants and I don’t dress much different from the rest of the women in my office it
seems. Mistress keeps teasing me that she should get me implants so I can wear pretty
bras instead of just a lacy cami under my blouses. That would be such a permanent step
I am not sure if i could do that. She says she may keep me in chastity until I beg for
them. I kind of laugh that off hoping she isn't really serious. That would make it so
hard to ever going back to being a guy.
So anyway, I was looking forward to spending some time with Mistress this weekend and
was so glad when we got off work Friday. I hopped into my Miata and headed to
mistresses lovely home. By the end of the weekend I would be out of chastity, and get
back to male mode after a nice orgasm.
Mistress greeted me at the door and she was looking beautiful as always in a leather
mini, spiked heels and a leather vest with nothing under it. Dinner was on the table
and we enjoyed some wine and small talk as we ate. She seemed to be in a good mood and
promised something different this weekend that would change our dynamic. A sly grin on
her face as she said that. I cleaned the dishes and the kitchen after we ate as she
enjoyed some wine in the living room. When I joined her she told me to drop my pants
and girdle. She unlocked my chastity and told me to shower and dress in the clothes
she left out for me.
After showering with the fragrant shower gel I found a pretty pink baby doll and
matching ruffled panties on the bed. A pair of pink peep toe pumps completed the
outfit. I made my way back to Mistress Andrea and thanked her for the pretty new
outfit. She stood and hugged me tight, kissing me deeply causing me to become erect in
my panties. Mistress then led me to the playroom and secured me to her torture rack.
Wrists in leather cuffs secured over head. Feet pulled apart and fastened to the
bottom of the frame.
"Well my dear sissy Brenda, I have decided on a new training course for you" she
whispered in my ear while teasing my nipples. "In the past you have been such a good
girl for me but we need to step your training up a notch or 2, or 3." she smiled. We
always seem to play for a day or two and you serve me so well I just love it. Then you
get your orgasm and seem to loose all interest in being my sissy for a while. Isn’t
that true? I looked at her wondering where this was leading.
"Answer me slut" she demanded. I meekly replied "yes Mistress Andrea".
"And that's why you have been in chastity these last 10 days. To prepare you for
tonight." "What we have done in the past, that's all about to change my little toy.
This is no longer going to be about your orgasm. Going forward this is going to be
about my needs and your doing it all for me not that silly little clit of yours."
"I am going to drain your sissy eggs of all there juice before I start tormenting you.
Then when you normally are finished and losing that lovely sissy desire we are going
to continue our play. You are going to experience all that delicious torment you love
when you are all excited. You are not going to have a safe word. You are just going to
learn how to accept your place beneath me however I want. You will feel every stroke
of my crop and cane and they will feel more intense than ever before. It will feel
like total punishment without all that sissy juice in your eggs. You will be begging
for mercy like never before. You will cry. you will suffer. And in the end you will
beg me to never let you be a man again. You will beg me to be my sissy for ever. You
will learn to submit on demand no matter what your sissy clit tells you."
I was hard as a rock as she reached her now gloved hand down to my sissy clit. Surely
she was just saying all that to tease me and get me excited to serve and suffer for
her. Pulling my clit out of my panty she kissed me deeply then pulled a small stool in
front of me and sat down, still holding my hot clitty. She stroked it slowly at first
and soon picked up the pace. "I want you to squirt for me Brenda" she told me. "I want
all that juice out so we can start you new training". She picked up the pace and and
had me close to cumming. I tried hard to hold back. Maybe she was serious about all
that she said. Oh shit, i thought to myself. I really am in trouble now.
Mistress stood up and held a bottle of poppers under my nose. I felt myself getting
weaker. Helpless in her hands. "That’s a good girl Brenda, so helpless to resist
mistress. Now be a good girl and give me all that sissy juice from your eggs so we can
really get started."
Between her soft leather gloves on my clitty and the poppers making me weak, I could
hold back no longer. I had been locked up over a week and needed to release. In just
a few quick minutes Mistress Andrea had me pumping my juices out into her hands. My
knees were buckling under me and I screamed with sissy delight as stream after stream
filled her hands with milky white sissy cum. I felt totally exhausted and empty as
mistress slowed her strokes down finally stopping.
I watched as she grabbed a penis gag and coated it with cum. "Open" she commanded. I
didn’t want to but had no choice as her hand cupped my empty eggs. I opened wide and
took the penis plug in my mouth as she buckled it behind my head. "That’s a good girl
Brenda, clean all that yummy cummy off the cock. I saw her grab a medium butt plug and
coat it with the remaining cum, and disappear behind me. she held it to my bottom and
told me to push back onto it. As she again held my eggs I pushed back and allowed her
to fill me.
"How does it feel to be filled with a cummy cock at both ends sissy?" I bet you will
love getting used to that wont you? She sat back down on the stool and took my spent
clitty in her hands. She started stroking in gently looking up at my fearful
eyes."Ready for round 2 sissy?"
I shook my head no, but mistress just started stroking harder. "This is when the fun
really begins sissy. At least fun for me. I bet this sissy clit is just so overly
sensitive now that you squirted it isn't it?"
I nodded vigorously as I could while still tasting my cum in my mouth. Mistress
stroked with one hand and palmed the clit head with her other hand. The torment was
intense. She just laughed at me. " This is how I am going to break your man habits
forever Brenda. Look how you are reacting. Its like someone was tearing your clit off.
I bet this is just driving you crazy inside isn't it? Yes, I know it is. And I am not
going to stop anytime soon. At least not before you empty those sissy eggs again" she
laughed.
I was helpless to stop her and could only suffer this extreme torment. "When I am
finished you will be begging to be a girl Brenda. You will wish you had no sissy
clitty. You will beg for my cane on your ass and clit. You will beg to have your
clitty locked away to protect it from abuse. You will beg to lick my dirty ass. You
will beg for my affections. You will beg for the privilege of serving me, without ever
a promise of releasing your sissy clit. You will beg for me to spread Oestrogel cream
on you daily to feminize you more and make your sissy breasts grow for me. You will
beg me not to let you be a man ever again. You will only ever be allowed to release
your sissy cream before we play because you want to devote your thoughts to me fully,
always, never to be bothered with thoughts of your own pleasure again."
"Now sissy, nod your head if you understand what is happening!" Nod your head to
confirm that you are my property to train and torment. Nod your head to be mine
forever. And give me the last of that cum."
I nodded my head yes in hopes that she would release me. She increased her stroking
and somehow my sissy clit produced more cream for her as I bucked helplessly in my bonds.
She reached up and removed my gag. She filled my mouth with the fresh cream and went
back to stroking me.
She was driving me mad and she knew it. "Tell me what I want to hear now sissy girl"
" Please mistress" I begged, "Its so intense and can't take anymore". Tears were
leaking from my eyes as I begged her. "Please gracious mistress Please teach me to be
a good sissy for you. Please punish this weak sissy and train me to be your pleasure
toy. Please take control of my clitty forever and let me learn to serve only your
desires. Please teach me that my desires are meaningless. Please let me wear your
stripes across my sissy ass and clitty. Please lock my clitty away and make me into a
permanent sissy girl for you. Please teach me to enjoy my punishment for your
pleasure.
"Yes baby doll I most certainly will. How could I refuse when you asked me so nicely?"
"Now lets get started then" she said as she finally released my limp clitty. Mistress
released my legs and then my arms, and dropped my panties off. She placed a blindfold
over my eyes and led me across the room. " I have a nice comfy seat for my little
girl" she said as she moved me backward until I felt a chair behind my legs. Guiding
me gently she told me, "Sit sissy". As I contacted the chair it felt like a thousand
little spikes digging into my ass. Never mind the plug getting forced deeper. "Oww",
I screamed out as I felt mistress securing my arms and legs to the chair. I couldn't
move without the spikes tearing up my ass.
"Now hold still sissy while I have some fun with this clitty again". Mistress gently
held up my sissy clitty and gave it a few strokes. Then I heard the whoosh momentarily
before the crop came down on my clit. I yelped and squirmed only to feel the spikes
bite harder. "You need to learn to sit still while I have my fun sissy. That’s what
the spikes are for. Just enjoy the precious pain I am giving my pretty sissys clitty.
You know it makes me so hot and moist when you are suffering for me".
"Whack" The crop struck again and I again was bitten by those dam spikes. "We will
keep going till you learn to sit still hun". After another half dozen strokes of the
crop I managed to stay seated. Mistress landed another dozen strokes with the crop
telling me how good I was to let her have fun with my clitty.
"She started again with the cane. It stung even more with many strokes landing
directly on the head of my clitty. I sat as still as I could concentrating on
Mistresses words and hearing her breathing quicken with every stroke, wishing I could
see her beautiful face and smile. "Oww Oww, thank you Mistress, Please enjoy yourself
mistress" escaped from my lips. She placed a metal ring around my clit and eggs so it
would stay large for her. The strokes from the cane intensified and the pain level
made me certain my clitty was going look like a tiny black and blue worm when she was
done. I felt my sore ass planted firmly in place on the "sissy spikes" (as she called
them).
"Well I think your clitty is about all worn out Brenda, did you enjoy that?
"Yes Mistress I enjoyed you pleasuring yourself through my suffering"
" Good girl Brenda, Do you want to make your clitty squirt again? she asked stroking
my clit again.
My sore punished clitty hurt so much from her hand I replied "Oh no mistress, please
don’t make my clitty squirt anymore. Please lock it in the metal clitty cage so nothing
touches it and makes it hurt anymore" I begged her.
With the metal ring already in place Mistress slid the cage with its spiky ring in
place and I heard the lock snap shut. I felt Mistress fiddling with the lock and then
she released me from the chair. I am certain my ass was totally red from the spikes and I
hoped we were done, seeing she had locked my clitty up already. As mistress led me
towards her spanking bench I realized this was not the case. Soon I was secured to the
bench with my ass high in the air.
Mistress caressed my spiked ass and with a yank, pulled that previously cum covered
plug directly out. She was standing in front of me she told me to open my mouth and
filled it quickly with the dirty plug. "Keep that in there sissy, and make sure it
gets thoroughly cleaned, I want to have some fun with your sissy ass". I soon felt the
cane crashing into my ass. I almost swallowed the plug. I silently suffered as
mistress put 40 stripes across my ass then she went the other direction with another
set making a waffle pattern across my ass. Tears were coming down my face as mistress
removed my blindfold and the gag. After removing the plug from my mouth I said, "Thank you my dearest Mistress for allowing me to bring you pleasure".
Mistress turned around and presented her bottom to me, I reached my tongue out and
slowly licked up and down her ass. I pressed my tongue deep, tasting her nether regions
intimately. She turned around and released my bonds, and gave me some water. "How are
you feeling my sissy?" she asked. "Loved and owned my Mistress" I replied. Mistress
smiled and reached down to my chastity. "Yes you are my sissy. You see this red color
on your lock? I filled it with your pretty red nail polish so now the key is as
useless as your clitty and with the spikes attached it wont be coming off again
anytime soon."
"Thank you mistress, please make me the best sissy I can be for you".
"I am not done with you yet Brenda, I'm just getting started. Now follow me".
We went to Mistresses bedroom and Mistress handed me a pretty pink panty girdle and
told me to put it on. I pulled it up tucked my chastised clitty back and smoothed the
girdle into place. Mistress told me to go stand in the corner for a minute while she
took care of some things. I didn’t see her drop her skirt and remove her vest. But I
soon felt her breathing on my neck and her bare breasts rubbing against my back. I felt
her pull the back of my girdle back firmly and putting something in it. When she
released it I realized she had fit a sheet of spikes into my girdle. she patted my ass
and I yelped from the painful spikes.
"Just a reminder for you sissy. I had a special set of spikes made to fit nicely in
your panty. Isn’t it lovely? Now let me see you walk around with it in place" She
demanded.
With every step I could feel the spikes on my already tortured ass. It made my ass
swing with every step and had Mistress laughing and enjoying my predicament. Finally
she called me to her bedside. She playfully pushed me back on the bed driving the
spikes deeper into my ass. She straddled my legs and had me suckle her beautiful b cup
breasts. I moaned in pleasure and pain loving to lick her in this way. " You love my
breasts don’t you sissy?" "Oh yes very much Mistress" I said and went back to sucking
her nipples. "And soon you will have pretty breasts just like them wont you sissy? she
asked.
So lost in loving her I replied, "Yes please Mistress, please give me girly hormones
so my breasts will grow pretty like yours Mistress" I begged her.
"Are you sure that's what you want sissy?
" Oh yes please Mistress, Please treat me with girly cream everyday so I can have
pretty breasts and never be a man again."
"Ok sissy, wait right here."
Mistress went to the bathroom and returned with a tube of prescription Oestragel
cream. She measured the correct dosage and rubbed it into my upper arms telling me
that I would soon be growing my own breasts. That there was no turning back now. That
there would be no hiding the fact that I would always be a sissy. That the man I was
for a few days after our previous dates would never exist anymore. That I would
never put my sissy clit in a vagina again. That I would learn to serve her and anyone
she commanded me to serve without complaint.
I then had to lay back on the bed so Mistress could sit on my face. The spikes still
inside my girdle being pressed into my sore flesh. My clit still limp in its cage.
Would it ever get hard again? She rode my mouth and occasionally slapped at my sissy
eggs with her crop. She explained how my body would change soon from the hormones.
That my fat would shift and my hips and ass would widen and my waist would narrow. She
told me that we would soon both live in her beach house and give all my mens clothing to
charity so she could keep track of my progress and continue my training. And she
promised me a few pretty 2 piece bathing suits to enjoy the beach in.
She told me that I made a great start today and would soon be a totally unselfish
slave, used by her as she pleases. That I would be pleasing her friends male and
female with my mouth and sissy ass as needed. That I would learn to forget I had a
sissy clitty. That if I was a good girl it may leak its sissy juice out when she or
one of her friends fuck me. Or maybe it just wont make boy juice anymore. Maybe I
have traded it to Mistress for the honor of being trained as a little pain slut sissy
for her pleasure.
Mistress soon was grinding harder on my mouth and finally collapsed in a shuddering
orgasm. Finding her breath she rolled of me and turned and kissed me deep, tasting her
own delicious juices on my face and mouth. I was in heaven from her kiss. So happy to
have pleasured her so. "Turn the lights out and lets go to bed now sissy. I got up and
before turning the switch off went to take my girdle off.
"No no sissy, you will sleep with the girdle and spikes on tonight. Think of it as
part of your training. It will help you dream of your new sissy life." "And I promise
it will be an exciting new life for you. We will have to start buying you pretty bras
to show off under your sheer blouses. "I cant wait for your boobs to start growing so
your friends and everyone at your job will see are no longer a man. I bet your co-
workers will love to see that. You do realize that you wont be able to hide them? That
they will be poking off that once flat chest for all to see? You will almost be a woman but not quite. And you will never be a male again either. Just a Sissy Girl, Forever.
.
Sissy Girl Forever Part two.
No going back now.
Mistress was going to be certain that there would be no turning back for me. Over the next few weeks she made certain that I used my hormone cream daily. No my breasts haven't started to grow yet but I could notice some slow down in hair growth. My male wardrobe seemed to be dwindling, with more camis, blouses, soft pullovers and ladies pants taking their place. Of course I have only had pretty panties and tight girdles for underwear for many years already.
Mistress had treated me to a mani and pedi and my nails looked so lovely and long. I guess this was a bit more of her stepping up the game. My co-workers, at least the women, loved it when I came in with gel extended nails polished a pretty sparkling pink. They all wanted to know where I got them done so nice and we chatted about nails throughout our coffee break. Looks like I was just another of the office girls now.
I called Mistress that evening and told her about how my co-workers thought they were so pretty and how they made my hands look more slender and feminine. She told me I seemed to be enjoying the attention and my more fem look. That kind of caught me off guard a bit. I guess I was becoming more comfortable. “Just wait till you start wearing bright red lipstick every day. What will they think of you then?” she asked. I told her I thought maybe that would be too much for work. She kinda laughed and said “maybe, but I bet you will be begging for it soon. Come over after work Friday, we have plans.”
The rest of the work week went well. The women seemed more accepting of me at work even inviting me to have lunch with them twice. But I did notice them asking me to do things for them more. Simple things. Like asking me to bring them a cup of coffee if they saw me heading to the break room. Or doing come copies for them if I was heading to our office copy center. I didn’t think much of it at first, but maybe they are trying to subtly reinforce the idea that my position should be beneath them, although we all do the same planning work for the company.
My biggest problem all week was wondering what Mistress had planned for the weekend. My sissy cock strained in it's cage every night in anticipation. I headed for her home after work Friday, stopping to pick up some flowers and fine wine. After a nice dinner and most of the wine, Mistress told me to put on the outfit she had selected for me. It was hanging in her bathroom and she would help with my makeup.
A found a purple brocade under-bust corset, black panty girdle, thigh high stockings, a lacy black bra, and a deep red sheath dress and and red heels. I snugged the corset up to a point that would please Mistress Andrea and finished dressing. The dress hugged my frame and ended just above my knees. Mistress came in and while doing my makeup told me we were going to a club she knew of to chill out and dance a bit and see what develops.
Ok I was intrigued. I wonder what she means by develop? She handed me a purse for my id and stuff and we headed to town. We ended up at a well known gay bar with a large dance floor and great drinks. Finding a table Mistress ordered us Cosmos and we relaxed a bit and enjoyed some people watching. We danced to a few tunes and ordered more drinks. When I noticed a hot young guy approached our table I figures he wanted to ask Mistress to dance. I mean she looked stunning in her soft leather pants and top. How could anyone not want to be with her. I was shocked when he asked me to dance and as I glanced at Mistress as she told the young man “Brenda would love to dance with you!”
The first song was a quick paced disco number and I didn't have a problem with the heels or anything. But then the music changed to a slow ballad and Drew grabbed my hand and pulled me close. We danced through the number and I tried to play the feminine role properly, but I wasn't used to dancing backwards in heels. I could feel him getting hard as he held me close and i was actually trying to get hard in my cage as he did. I was glad when the song ended and he walked me back to the table. I thanked him for the dances as I am sure Mistress would have wanted me to do that like a proper girl. I also introduced Drew to Miss Andrea.
Mistress excused us saying we had to freshen our makeup. As she got up from the table I noticed she whispered something to Drew, and we headed to the ladies room. Of course like most gay bars there were men in there as well but they parted for Mistress and I to pass. Once there she led me into a stall and told me to clean the seat for her and wait out side the door for her. When she finished she told me to enter and sit down.
“I have a present for you darling Brenda” she said as she pulled a pair of cuffs on a cord out of her designer handbag. She put one on one of my wrists fed the other end around the toilet and cuffed my other wrist. I tried to protest and she slapped my face saying only “shut up and serve Sissy. Drew will be here for you in a minute and I better get a good report back from him and his friends, or you may be stuck here even longer.”
She held some poppers under my nose and had me breath in deeply a few times. Setting the bottle on the little shelf she turned and left. My head was spinning from the poppers. I flashed back to the hypnotic videos that Mistress had me watch. The ones that kept saying how poppers make sissies love cock. Yeah, that one. It kept me from thinking clearly about how to get loose when the door popped open and Drew entered. He looked at me and the bottle of poppers. Opening the bottle he said “have some sissy sauce honey, you may need them” With that he made me sniff some more. I was floating when he dropped his pants and pulled his shaved dick from his boxers and put it to my mouth saying only “suck it popper sissy”. I was to helpless to resist at that point and opened my mouth. I felt like I was in a trance and I sucked as told and soon had a mouth full of warm creamy cum.
Drew thanked me and fed me more poppers. That dam sissy sauce made me so helpless. I wondered what would happen if someone else came in. Maybe they would free me. Just then the door opened and another young man entered and smiled when he saw me and immediately reached for the poppers. Took a couple hits and then forced me to sniff again. He soon had his cock in my waiting mouth and was pumping away. It didn't take long for him to empty his load in my mouth. He left as quick as he came in and soon the door opened again with a young woman entering next. She was about 35 with lovely breasts and a sexy figure covered with a full dress. She lifted her dress and stepped up placing it over my head. She had no panties on and as her crotch came closer to my face I felt a cock rubbing against my lips. I opened my mouth and sucked it gently till it got hard and soon had her moaning as she also squirted in my sissy mouth.
She uncovered me and undid my cuffs saying I should take them and return to my mistress. I thanked her and after she left I straightened myself out, went to the mirror and redid my makeup, then headed out to rejoin my mistress. “Did sissy Brenda enjoy herself in the bathroom?” I tried to say they forced me too suck them that I didn't really want to do it. But in the end I reported that I was a good popper slut and loved serving that way to please her. She said she will know more when she gets the report from Drew and his 2 friends. We left shortly after and I spent the rest of the weekend serving Mistress at her home. She said to plan on being there on my day off Wednesday at 11am.
Wednesday morning I was there promptly at 11. Mistress said we were heading to town and had me in a t-shirt with a long cami under it, black stretch pants and plain flats with just a hint of makeup. We pulled up at the salon she frequents and went in.
I asked what we were going to do and she said she wanted my brows waxed and shaped a bit nicer and some other little treatments. I was brought to the waxing room and seated in a comfy reclining chair. As the gal was preparing Mistress Andrea told her how she wanted them to look. I stayed quiet knowing I had no choice in the matter. She then told me that Drew and the shemale I sucked both complained that not only were my lips not red enough but seemed quite thin and should feel softer. They said it would feel so much better with plumper lips. She asked the waxing gal if they did lip plumping at the salon and was told they did.
They stepped away and chatted for a few minutes and then came back and looked at me and a few pictures in a booklet. I noticed Mistress point to one page and say “yes, that will do. As Mistress watched the gal, Sara, started trimming my eyebrows with a small scissor then applied warm wax below the brow in a well arched shape. She pressed a cloth strip to it and yanked it off, showing me all the hair that came off. A few minutes later and after a bit of tweezing she pronounced my eyes done and went away. She returned a few minutes later pushing in a small cart with some mechanical stuff on it.
Mistress said I needed to remain very still for this part and placed a long scarf over my eyes and tied it around the back of the headrest effectively immobilizing my face. I felt my lips being wiped clean (I guess). Then I heard a buzzing from the machine on the cart and suddenly felt small needle pricks on my upper lip. Dam, she must be doing botox or something to prettify them. Mistress said they would look darling in bright red now. Sara started on the bottom lip and when I thought she was done went back to the upper. This time the sound was a different buzzing but I could not tell what was going on. I could certainly feel my lips swelling up to quite a bit larger than I was use to feeling.
When Sara finished Mistress said she would let me up now and just knew I would beg her for new bright red lipstick for my pretty lips. Untying the blindfold Mistress told me to keep my eyes closed until she said to open them. She helped me to stand and turned me to face a mirror. When she said I could look I almost passed out. Not only were my new lips very full but tattooed in pretty red script on my upper lip it said “sissy girl”, on the bottom “forever”. Holy shit. “th,th th, that’s a tattoo Mistress. How can I ever go out in public like this.” How could you let her tattoo me like that?”
“Well sissy first of all its a new kind of tattoo that will fade in about 9 months to a year so its not permanent. And if you beg me for new red lipstick to wear everyday like I said you would then it wont be a problem. So whats it going to be Brenda?”
“Oh please Mistress, may I please wear pretty red lipstick for you, please Mistress. I will always wear it and look pretty for you.”
“Yes you will wont you Brenda dear. And if you misbehave I may just take it away as punishment. Then you would be seen like this by everyone at work and everywhere else, understood? I did warn you I expected this didn't I sissy?”
“Yes Mistress”.
--------------------------------------------------------
Sissy Girl Forever, Part 3
Sara stood there laughing at me as Mistress explained how things would be for the near future. She told Miss Andrea that if I wished she could fill them in with the red right now if I wanted. But Mistress said no. She was looking forward to my rushing off to work at times forgetting to polish them. Or eating out with friends and have the lippy wear off.
They both had a good laugh at that, and as we were leaving Sara did mention that she could do tattooed eyebrows too if she wished. Mistress said she would think about it as I just rolled my eyes. Mistress thanked Sara after leaving a nice tip and we headed off to Sephora to buy lipstick.
As Mistress looked at the selection I tried my best to stand behind her and hide my swollen lips from view. A young, and of course heavily made up, salesperson asked mistress if she needed help finding the right product. Mistress told her that she wanted a certain shade of red lipstick that would wear off easily. She pointed to me saying “Its for my sissy girl, and the easy wearing type will make her remember to re-apply it often.
Mistress Andrea pulled me in front of her so the sales girl could see me and she let out a wild laugh drawing 3 or 4 other salesgirls over to see me. Even some customers could see me with my new tattooed fat lips. “Well I would normally recommend the “all-day-stay” line but if you want the type that wears off easily then lets try this one”, she said as she opened the tube and approached me with it. She carefully filled in my sore lips and my embarrassing tattoo disappeared from view. “That seems to match perfectly to hide your tattoo” she commented.
I was so relieved but then the sales girl told mistress that if I was going to be wearing lippy all the time I should have the rest of my face done properly as well. She led us to a mirror and had me sit in a stool and gave my face a full makeover in front of everyone. At least I was dressed in womens clothes and after dropping about 2 hundred dollars on make up Mistress led me out the door. I don't know what hurt more at that point, The puffy tattooed lips, the pain I felt in my chastity as I was led out of that sissifying heaven, or my ego knowing I would never be seen as male anymore. I would have to remember to come back at another time and get the all day lipstick I thought.
On the way down the block we passed a Claire's Boutique and mistress stopped to do some window shopping. “We must go in and get you some pretty things Brenda dear. After all, you will be needing it to complete your look at work now.” Mistress pulled me in and found some pretty bracelets that would fit my larger than the average woman’s wrists.
She looked at my face and saying I should have my ears pierced too and then she started digging through her black Coach bag finally finding what she needed. Calling the clerk over Mistress told the gal “My sissy needs her ears pierced.” The clerk, Deborah, calmly said ok and told me to have a seat in her piercing chair and she would grab her gear. When I sat down Mistress showed me what she took from her bag. It was a single standard dice. She handed it to me and told me to roll it on the counter. I did and rolled a 3. Mistress clapped and said “oh good, 3 piercings. Looks like 1 in each ear, and 1 in your tongue Brenda.
I gasped at that. I didn't mind the ears but refused to get my tongue pierced and I told Mistress how I felt. She said ok but since I did roll a 3 and I had to get 3. She pondered a bit and whispered to Deborah a minute. Mistress pointed to a starter set and Deborah set up her equipment. Deborah took a marker and marked my earlobe on the left and then the right, making certain they were even. She looked to Mistress for approval then made two more marks on each ear.
I looked at Mistress and she gently explained that I rolled a 3 and was getting 3. “But Mistress that would be 6 the way she marked it”' I complained. “Well Brenda, it's either that or your tongue. You rolled a 3 and 6 earrings is 3, it's just 3 pair” she laughed. She then leaned forward and gave me a very hot kiss on the lips making me squirm in my seat as she pulled away. It never occurred to me that she did this as a way to nonchalantly wipe away my lipstick.
Deborah cleaned my ear lobes and loaded her piercing gun. As she was going to place it for the first hole she did a double take at my lips and gasped. “Does that really say Sissy Girl Forever on her lips.” “OMG that is hysterical, I love it.” To Mistress she said “We really need to talk, this is fantastic what you are doing with her. I have been feminizing my male as well and this is so awesome of you to do this for her” she proclaimed pointing at my blushing self.
She returned to the task at hand and placed 3 studs in each of my ears. She gave me cleaning solutions and a form that explained caring for them. As I looked in the mirror I saw that my ears were now adorned with 3 nicely spaced little pink diamond studs on each side. With my Sephora face and all I looked kind of pretty even for my once male face. She then explained to Mistress Andrea that she was also a professional body piercer as a side job, usually doing them at adult fairs, bdsm events and private parties and has done some nice new things on her sissy that she would be happy to discuss at another time. She gave Mistress her card and Mistress promised to call her soon. Deborah gave us a nice discount on our purchase and gave me a little kiss on the cheek and said “Be a good girl now” as we were leaving.
As we headed back to her car she handed me my lipstick “Here you may want to hold on to this and check yourself often”. She said with a smile. “Thank you my beautiful Mistress, and thank you for all you do for me.” We were finally heading back to Mistress' home and I would have to get busy and prepare dinner. I am a pretty good cook and in no time I had dinner set out for her. She allowed me to eat with her and we enjoyed some nice wine. Mistress asked me how I felt work would go tomorrow. I told her I was a bit apprehensive as today was going to make me step up my fem look at work quite drastically. I told her that the women in the office were going to get a bit of a shock. Mistress laughed that devilish laugh of hers that made me love her so.
After dinner she retrieved a bag from the closet and handed it to me. Inside I found a new pair of stretch pants with a rear zipper and a pair of pumps with a sturdy looking 2.5” heel that was similar to what most of the ladies in the office wore. I thanked Mistress for her generosity and modeled them for her. She loved the fit but said it was too bad the chastity wasn't just a little flatter so the pants would fit smoother. “We will have to work on that” she teased. As it was getting on in the evening I needed to get home and do my own chores before work the next day.
Before I left Mistress said she downloaded some music she wanted me to listen to as I slept that night. She said she emailed it to me and I should load it on my mp3 player and use the earphones. I knew it was probably more sissy hypno stuff but could not refuse her and told her I would listen to it for her. She gave me a long deep kiss while fondling my chastity through my pants. “I love you Brenda girl, and I want you to think about moving in with me soon and give up that old “man cave” of yours, and don't forget your lipstick. “Oh yes Mistress” I swooned, and headed to my car. My head was spinning on the way home. Not only would I move in, but tomorrow I would buy a diamond ring and this weekend I will ask her to marry me.