Sex With Girlfriend Turns Into Gangbang
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SissygirlForever free porn video
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 have a second earring added to each ear and 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
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
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, "it's 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 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 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 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 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 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.
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