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 women's 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 nice 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
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 bucked helpless 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
"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
for me. 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 left my sore as planted firmly in place on the "sissy spikes" (as she called
"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 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. "Thank you my dearest Mistress for allowing me to
bring you pleasure", I sobbed through the tears.
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, learning her tastes so
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
"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
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
"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 would
be 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 both live in my 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.