How i became a sissy slut
- 1 year ago
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From Virgin Loser To Sissy Slut 1 free porn video
I was a 23 year old virgin. I had always known that I was a submissive
sissy, but I was getting tired of being a loser who couldn't get laid. I
had been on Grindr for over a year, and never found anyone to fuck me. I
knew most guys didn't want a sissy, so I spent all that time masquerading
as just a regular bottom boy, but I still wasn't having any luck.
One day I found a profile that caught my attention "2 Tops 4 Bottom," so
I decided to message them. They were just two guys that were looking for
some three-way fun. One guy was a year younger than me and the other was
34. After exchanging some pictures they were actually interested in
fucking me, so we decided I would go to their house that Friday.
We chatted more throughout the week, however I still didn't know exactly
what kind of relationship John, the younger guy, and Matt, the older guy
had.
I guess at this point I should tell you more about my virginal sissy
life. I started buying women's clothes and dressing up right after I
learned to drive. Soon I started buying dildos and butt plugs. When I
learned about chastity, I immediately bought a cb600s. I soon found that
even that was too big for my tiny clitty, so I saved up and got a custom
cage with a PA piercing. I started wearing my cage all the time, but
without a keyholder I never lasted more than a few days before taking it
off and cumming. I was also wearing panties everyday, and wore a butt
plug most of the time.
On Thursday I realized that i needed some boy underwear, and I really
wanted to impress these guys, so I went to a nearby Calvin Klein store
for some new undies. I found some sexy pink briefs that I knew I'd look
good in.
When Friday evening came around, I was so excited. I took off the lacy
blue panties that I'd been wearing all day, Then I took out my butt plug
and reapplied lube before putting it back in. John and Matt already knew
about my piercing but i had no intentions of scaring them off with my
kinks. I removed my chastity cage and replaced it with a normal ring in
my clitty piercing. I then put on my new boy undies, they felt so
foreign. It was so weird having so much room down there, it was even
weirder to be able to actually touch my clitty and balls through the
fabric without my cage in the way. I wanted to put my panties and cage
back on, but I knew that would scare Matt and John off. I decided to
leave on my boy undies, but I put some clean red and black striped
panties and my chastity cage in my bag along with clean clothes for
tomorrow. Just before I walked out the door, I grabbed the matching bra
to my panties and tossed it in the my bag as well
After a drive that seemed like forever, I arrived at Matt's house. They
were very welcoming and I could definitely tell that they wanted to make
me comfortable for my first time. So when I got there, we just cuddled up
on the couch and hung out. After about an hour, I could tell that Matt
was a dom and John was a sub, even though they were trying to act like a
normal couple.
Eventually John went to the kitchen to get some snacks, and that's when I
made my move. I nervously got on my knees in front of Matt and started
unzipping his pants. "I see you're warming up to this," said Matt.
"Yes, I'm ready to suck your cock," I said.
I took Matt's giant hard cock in my hands, "It's so big!," I thought. I
anxiously kissed the tip and then took it in my mouth. I circled his big
juicy head for a few seconds with my tongue, then I took his entire
length in my mouth. I slowly licked and sucked for a few minutes, until
Matt grabbed my head and started fucking my face. I licked and squeezed
it as hard as I could, and soon I could feel his cock begin to swell with
an impending orgasm. He shoved his cock down my throat when I felt the
first string of cum shoot from his cock. Then he pulled out and squirted
four more shots of cum on my face, and said, "That was pretty good for
your first time."
Matt pulled me up and took me to his bedroom,and we started undressing. I
decided to leave my undies on for now though. Then he called out for John
to meet us there. He asked if it would be ok for John to lick the cum off
my face and I said that it would be fine. When John arrived Matt told him
to clean off my face. John and I laid back onto the bed and he started to
lick my face clean. When he finished, he kissed me and we swirled the cum
around in our mouths. After we swallowed the cum, John started
undressing, and Matt laid down on the right side of the bed.
When Matt rolled over onto his side facing me, I decided to cuddle up to
him and be little spoon. He then wrapped his arm around me while I
pressed my ass into his crotch. He immediately felt my butt plug pressing
against him, so he reached down and felt up my ass. "I like when naughty
bottoms run around with plugs in their asses," he said, "I bet it has
kept you horny all day."
"It keeps me super horny. I love spending all day plugged; the thought of
having a little sexy secret in public is the best," I say.
As I watched John unbutton his shirt and pull down his pants, I couldn't
help but think about what just happened. Matt told him to clean off my
face and he simply did it, no questions asked. It's becoming clear to me
that there is some kind of bdsm element to Matt and John's relationship,
and they're trying to play it down in order to have this threesome with
me me. I'm definitely going to find out more about this after sex.
When John finished undressing, he climbed into bed and leaned against the
headboard with his semi-hard cock positioned beside my chest. I rolled
over about halfway, leaving my ass pressed into Matt, but with my mouth
ready to go down on John. I took John's cock in my mouth and slowly began
sucking. When it reached its full size, I saw that it was way bigger than
my tiny clitty, but it was nothing compared to Matt's giant cock.
All this time Mark was rubbing, squeezing and twisting my nipples with
one hand, and he was rubbing my clitty and ass with the other (of course
I'm referring to it as my dick since they don't know I'm really a sissy).
Eventually, I couldn't take it anymore, and pulled off of John's cock. "I
need a cock in my ass NOW!," I exclaimed, while jumping up and pulling
off my undies. We decided John would fuck me first since he was smaller.
John got up to put on a condom and lube up his cock while Matt took out
my plug and rubbed some lube in my hole with his fingers. When John was
ready, I laid facing up with a few pillows underneath my lower back so he
could fuck me from a more upright position. As I spread my legs, I felt
John's cock firmly press against my hole, and my clitty stood straight up
exposing my tiny size and my large piercing to both of them. They didn't
say anything about it, but I could tell they were thinking about
something.
I closed my eyes and moaned as John slowly entered, and then stopped
about halfway in. "Deeper!," I moaned, and John cautiously pushed until
he was balls deep. Then he started fucking me with short slow strokes.
Opening my eyes, I said "Take longer strokes." I moaned as John almost
pulled out and then went in balls deep at at slightly faster pace. "Just
like that. It feels so good," I said. Soon, I went limp in ecstasy, and I
turned into a moaning, whimpering mess.
I soon felt what I assumed was a mouth wrapped around my clitty, and I
jumped out of my trance. When my eyes opened, I saw Matt sucking on my
clitty while John was still fucking me. I was a little upset, but I tried
my best not to show it. For years I dreamed of just being a cumdumpster.
I just wanted to be two well used fuck holes with a completely virginal
clitty that had never felt the inside of anyone, but now that dream was
ruined. Even though I was only inside his mouth for a few seconds, I
still recieved a blowjob, and nothing can change that. I regained my
composure and gently pulled Matt away, and started stroking his cock. I
quietly said to Matt, "I'm not here to put my dick in you, I'm here to
have my mouth and my ass filled with your cock."
I knew then that Matt figured out something was up. He didn't say
anything, but I could tell from his body language. Whatever he was
thinking when he first saw my tiny, pierced clitty was confirmed when I
told him to stop going down on me. He didn't seem to want to stop the
nights activities, but I was sure we would have some kind of talk about
it later.
A little while later we decided to do doggy style, so John pulled out and
I rolled over on my arms and knees. When John pulled out, I felt so
empty. I desperately needed it back in me. I was so happy when we got
repositioned, and John went back to fucking me. I know it that it only
took a few seconds, but I was so horny that it felt like it took an
eternity to get that cock back in me. Then Matt shoved his cock in my
mouth, and I was getting fucked on both ends.
After another five minutes John is still going and hasn't cum yet, so
Matt says it's his turn with my ass. John pulls out and takes off his
condom while Matt puts on a condom. I stay in my position, my hole is
stretched out and my mouth is tired, but I have to make these men cum in
me before I finish. I take John in my mouth, while Matt lubes me up
again.
Matt didn't start off easy. He shoved his cock straight in to the hilt.
It took me by surprise, but it felt amazing. I was screaming with
pleasure. John was gentle, but Matt was rough, and rough was exactly what
I needed. It only took a few minutes until he came. I was so excited when
it happened. I was proud that I made a man cum, and Matt and John
noticed. Then Matt told John to pull out, and came around to my face. He
took off his condom, and told me to eat the cum he squeezed out of it. I
gladly took the cum, and then told me to clean his cock. I took his cock
in my mouth and cleaned the rest of his cum off of it. Matt said, "Do you
want to see your big gaping hole?"
"Totally," I replied.
Matt grabbed his phone and went to take a picture of my ass. He showed it
to me and I was amazed. My pussy was stretched out and hanging open. I
told him to send it to me so that I could remember this day forever. I
started back sucking John, and he soon filled my mouth with a huge load.
Before I was able to swallow, he kissed me and took a little bit of cum
for himself.
We chilled in bed for a few minutes, and Matt asked if I wanted to spend
the night. I was so excited that I couldn't say yes fast enough. Then he
asked if I had cum. I realized that I hadn't cum, and I told him that. He
asked if I was going to or if I wanted him to give me a hand job. I told
him no. Even though I didn't cum, I felt satisfied. I was happy with what
happened, and I was ready for bed. Besides there will be plenty of time
for that in the morning. Right?
I wanted to ask about Matt and John's relationship, but I was covered in
cum and Matt told me to go take a shower. I got out of bed, and went to
the bag that I brought. I opened it and took out my towel, toothbrush,
toothpaste, and bodywash. Then I grabbed my butt plug off of the floor
and a tube of lube before going to the bathroom. When I got there, I
washed my plug in the sink, and brushed my teeth while I waited for the
water to warm up. Before I got in the shower, I took a few selfies
because just loved the look of cum covering my face.
So I hopped in the shower, and thoroughly washed myself. When I got out,
I lubed up my plug and slid it back into my pussy.
When I arrived back in the bedroom, I saw that Matt and John weren't
there. Then I looked on the bed and had the surprise of my life. My bra
and panty set was laid out on the bed, along with my chastity cage. I
couldn't believe it! When I looked closer I saw a note. It said "We need
to talk. Put on your chastity cage, panties and bra. Then come to the
living room and kneel down facing the couch, without saying anything."
I was terrified. I looked down and saw my bag with my keys still in it. I
could climb out the window and leave if I wanted, but I'm not sure I want
that. If I stay I might regret it, but if I leave I'll definitely regret
not finding out what will happen. So, I look down at my hard clitty. If I
lock it up and hopefully give them the key, I may not cum for a long
time. I start stroking my clitty and think about how I haven't cum since
Wednesday, I may as well cum now while I still can. As I start to get
close to cumming I stopped. "I shouldn't be doing this," I think, "I
should be a good sissy and just lock up. It's what John and Matt would
want."
I let go of my clitty and thought about how to get it soft again. With
one hand I squeezed my balls as hard as I could. It hurt so bad, but it
didn't appear to be working, so I slapped my clitty really hard with my
other hand. It worked. My clitty softened up, and I locked it up in its
cage. Then I put my panties and bra on, and put the keys to my clitty in
my left bra cup.
"Time to see what happens," I thought.
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