This is my first attempt at a story so any feedback would be greatly
appreciated. Feel free to email me about anything: feedback requests or
just to chat.
When I was 16, in spite of my shyness and not being in anyway incredibly
attractive, I somehow landed myself a girlfriend 2 years older than me. I
was quite short for a boy then, around 5’7 and very slim having not yet
developed much muscle. I had shoulder length brown hair and bright green
eyes and I simply couldn’t believe my luck in getting this girl. She was
called Jess, a beautiful redhead with a body to die for and an appetite for
sex even my youthful virility could hardly satisfy – not that we didn’t
try, constantly.
Jess was insatiable, and very domineering she took the lead in everything
and I happily followed. Naturally this spilt over into sex and we quickly
found we both loved it when she took control in the bedroom. It started off
pretty simply, just her on top during sex and often teasing me before
allowing me to cum, but as we shared our fantasies, things got crazier and
crazier. She often teased me that I looked quite pretty and even a little
girly, she told me guys would love me and after some time I told her that I
did have fantasies about being with men from time to time. I was happy she
didn’t really mind and even seemed excited by it so I grew more and more
confident sharing with her. Eventually I told her something I never dreamed
I’d tell anyone. I loved panties, I’d been dressing up since I was 11 and
always wanted to do it for someone else. Incredibly, so beyond my wildest
dreams, she thought this was amazing; she instantly made me strip off and
put on her panties that she had been wearing whilst we talked. What
followed was some amazing sex, her naked and me in a blue thong happy to
totally accepted. I showed her websites that I liked and she researched the
whole thing seemingly overnight. Before I knew it I wore her panties most
times we had sex and sometimes she gave me a pair to take home, telling me
I must wear them to school the next day. She’d make me put them on before
we went out with our friends telling me she wanted me to remember I was her
little sissy (her new name for me). I’d love it but constantly worry I’d be
caught and I guess she just loved having that control over me.
And now you have the background, let the story begin.
I never really fitted in with Jess’ friends so I was always nervous when we
hung out with them and this night was no exception. We’d gone to a party
full of people she knew and I was just her little tag along boyfriend, I
had no idea this night would be a very fond memory for me and later fuel my
fantasies for years to come.
I tried to mingle at the party, drinking and chatting to random groups but
I always returned to Jess getting bored of the people I was with or not
finding anyone to talk to at all. The party was just getting kind of dull
when Jess decided to change things dramatically. She came and told me to
come inside with her as we were all hanging out in the garden, and without
another word I followed her inside and upstairs to a bathroom. She locked
the door and started to kiss me, I got hard immediately as we made out
squashed in the bathroom. She undid my jeans and started stroking my cock
and said “I’m so fucking horny; I have a special plan for tonight baby”
“What is it?” I asked
“Shh now, you’ll see”, she said as she pulled her panties off and lifted
her skirt “now eat my cunt bitch”
I immediately fell to my knees and started licking her soaking wet pussy,
whatever her plan was it had got her damn hot and. hard as I was, I knew
I’d be going along with it.
“Take off your jeans and boxers baby, I wanna see you wank that cock when
you eat me”
I struggled to get them off as I remained on the floor and stuck between
her legs, but eventually I was naked from the waist down. I started jacking
off as I ate her sweet pussy and I thought I could see what was coming, I’d
be wearing her thong she’d thrown on the floor when I left the room, I was
sure of it. I wasn’t wrong but that wasn’t even half of what she had in
mind.
She started to moan and writhe against the wall as I continued to lick her
clit, sucking it into my mouth and flicking my tongue across it.
‘Oooooh’ she moaned, rubbing her pussy on my face as she came. She
momentarily sank against the wall before seemingly coming back to life.
“Mmm that was good baby, but now it’s your”
I stood up, anticipating what was to come, her blowjobs were
incredible. She sank to her knees and took my balls in her mouth. I moan
allowed and she smiled, “you enjoy that don’t you baby?”
“uhuh” I managed to sigh and she engulfed my entire cock in her mouth.
“You’ve always wanted to be in my place though haven’t you sissy?” she
asked as she pulled off my cock
“Mmm yeah, I’ve always wanted to try sucking a big hard cock” I could
hardly believe the things I said when she wanted me to.
She started feeling around on the floor for her panties, she’d worn a pink
lacy thong to the party and it was soaked, whatever she’d been planning
obviously excited her to no end. Eventually she found what she was after
and held them near my feet.
“cmon baby let’s see my little sissy in her panties”
I loved it when she spoke to me like that, and lifted my feet one by one to
help her put the thong on me. She pulled it on and up tight between my ass
checks before telling me to turn around with my hands against the wall and
my ass sticking out.
“My little sissy has such a cute ass” as she said this she slapped it and
then pulled my cheeks apart to tease my hole. Now she made me shave totally
from the waist down (I had very little hair above the waist) and due to my
body shape I did look like quite a cute girl from behind and I absolutely
loved it when she complimented me as such.
She reached up between my legs and started to fondle my balls and cock,
occasionally licking my ass as she did, teasing me relentlessly. I loved
having my ass licked and she was an expert handling a cock, so I was in
heaven as she did this.
“Now baby you love me don’t you?” I could see the plan was about to be
revealed as she said this
“Of course, Jess”
“And you love pleasing me?” she stuck her tongue in my ass
“Oh god yes”
“I want you to do something special for me, and I know you’ll like it” she
resumed stroking my cock and I was trembling all over
“Anything jess”
“Remember that small group of boys sat at the end of the garden?”
“Uhuh”
“I want you to hang out with them and pay particular attention to the boy I
point out for you, he’s gay and always tries to pick up boys he’s not met
before at parties, especially younger ones like you”
“Sure Jess but why?” I’d never refuse her now, I was feeling way too damn
good
“I want you to see how far you can get with him, I know you’ll love it and
it’d make me so wet. You’d be in for such a reward later” with that she
span me round and sucked my cock again. I could hardly process what had
been said as I watched her sexy red head bouncing on my cock. Her hand
reached up behind me and started toying with my ass as she sucked me, I
couldn’t concentrate at all I was just loving it. And then as I got close
to cumming she stopped, “Let’s go back to the party then baby” and with
that she got up and past me my jeans as she smoothed out her skirt.
“Please do this for me baby, and I’ll make it worthwhile later”
Now this shows our relationship perfectly, here I was 16 years old wearing
a bright pink thong under my jeans at a party full of strangers, being told
by my girlfriend to seduce a guy and never, not once, did a serious thought
cross my mind to refuse her.
“Umm ok, I’ll talk to them but I don’t know what’ll happen”
“That’s fine, just accept it when he goes for you, he’ll love a sissy like
you”
With that I was lead outside and introduced to Kevin and his mates, jack
was quite handsome fairly tall with short dark hair and brown eyes and he
seemed quite pleased to meet me.
Jess introduced me as a friend of hers she
thought Kevin might get on with, he seemed to catch what she meant because
he suddenly became more interested in me. I went to sit next to him and
Jess quickly wandered off to talk to some other friends.
Kevin was actually really hot and as I sat next to him drinking, I slowly
started to enjoy his attention. I was worried at first that my thong would
show above my jeans (well it happened to the girls all the time) but as the
drinking took effect I worried less and less and just enjoyed myself with
Kevin. Soon enough I was sat with his arms around me, giggling away
listening to everyone talking, really getting into him. Kevin grew bored of
everyone else it seemed and told me to follow him, so I got up and he lead
me inside upstairs to a bedroom.
As soon as we were inside, he locked the door and turned to me.
“Well now I have you all to myself”, he smiled as he moved close to me.
“And why would you want that”, as I said this I put my hands on his chest
and smiled up at him, I wasn’t even thinking about Jess’ commands, I just
wanted him.
He didn’t even answer, he wrapped his arms around me and kissed me, I was
in heaven. He grabbed my ass through my jeans and I just melted into the
kiss. Then he threw me on the bed and climbed on top of me, kissing my lips
and neck, it made me feel so girly I couldn’t help but go along with it. I
reached out and stroked the bulge growing in his crotch, his cock felt so
big I simply had to see it.
“Well someone knows what they want”, he said as he helped me undo his
jeans, his cock sprang out and I gasped. It actually wasn’t massive, but
I’d only ever seen my cock for real before and it was certainly bigger than
mine.
“Looks like you like my cock, kid”, I blushed as he said this and then
nodded as I licked my lips. I started stroking it again and he kissed me
long and deep. He undid the top button of my jeans and I panicked crazily
for a moment until he hushed me saying “don’t worry baby, I’ve know what’s
under there and I’ve always wanted a sissy like you”, he pulled my jeans
down a little and started stroking my cock through the lace. His tone
completely changed then, it was no longer tender he was totally commanding
from that moment on
“That’s just what you are isn’t it, kid, a little sissy”
“Mmm yes”, I moaned
“You want to be my sissy bitch don’t you?”
“Oh God, please make me your bitch Kevin” I don’t even know why I said it,
I just couldn’t resist.
“Take off everything but those panties, slut”, as he said this he stopped
stroking my cock and stood back. Quickly, I stood up and pulled my jeans
the rest of the way off and discarded my shirt just as fast. I was stood
for the first time ever, in front of a man in nothing but a little pink
thong.
Kevin walked around me as I stood there, he felt my ass and cock on his
way.
“Damn you’re a hot bitch” I almost came even as he said that.
“Well now I know you’ll do as I say there’s just one thing I want from a
slut like you right now”, he pulled out his cock, “get on your knees”.
I knelt in front of him and, grabbing hold of his hard cock, I slipped the
head into my mouth. I absolutely loved it, it didn’t even occur to me that
a short while ago I’d been the one having his cock sucked, right now I was
just this man’s slut. I devoted myself to the task of making him cum,
gagging on his cock trying to deep throat it, slurping and suck trying to
please him. He called me names constantly, calling me his slut, telling me
to suck his cock like a good bitch; I didn’t need the encouragement. Before
long he was breathing hard and pumping faster, “Swallow my cum, sissy” he
said it between breaths as he started to pump cum into my mouth, one jet,
two and then he pulled his cock out of my mouth saying “I know what my
bitch needs” and sprayed the rest of his cum over my willing slutty face.
“See you around, faggot” He said and then left me there, alone in the room
covered in cum. I got dressed, cleaned up in the bathroom and went
downstairs to find Jess waiting for me
“Having no panties around here gets you in trouble” She said with a smile
but I had no time to ask what she meant.
“C’mon, we’re going back to mine for a while”, she took my hand and lead me
all the way back to her house as I told her the story of what had happened
to me.
When we got to her house, we rushed to her room she stripped down to just
her skirt and I was in nothing but her thong once again.
“Wow baby, your story got me hot, lie back on the bed for me I want you to
eat my pussy again and I have something to tell you” I did as she said and
she straddled my face, as she did she started to tell me about her night.
“Well sissy, I guess you want to know what I did all night? I was flirting
with a group of guys to pass the time when a really hot one called Jack
felt me up. He grabbed my ass through my skirt and I thought I’d let him
have a little fun you know but then he felt up under my skirt and found out
I had no panties. Well you can guess what happened then” She paused and
started to cum from my attention, it never occurred to me to stop licking
even as she told me she’d let a guy feel her up
“Well he started playing with my pussy, right there in front of everyone. I
felt like such a whore, I loved it and it was nice being felt by a real man
you know. I was squirming there with his fingers in my cunt and people were
starting to stare to I asked him to take me inside. I’d already felt his
cock and it was huge, you’d have loved it sissy, I certainly did. We went
in the same bathroom as me and you did before and as soon as we were in I
bent over the toilet and flipped my skirt up. I begged him to fuck me, have
I ever begged you sissy? He felt so good inside my cunt, I really wanted to
let him cum there so you’d have a nice treat too but I didn’t want to get
pregnant so when he was close to cumming I got him to pull out and I sucked
him off. He tasted so good, you’d have loved it my little sissy.”
I couldn’t believe what was happening, here I was eating my girlfriend’s
cunt after it had been fucked by another guy and worse still, I was as hard
as a rock. Jess noticed this.
“Aww is my little sissy hard from my story? Do you want to cum baby? Stroke
it for me my little bitch, I’d let you fuck me but I don’t think I’d feel
it after Jack.”
I started pumping my cock and was ready to cum in seconds, so much had
happened that night and I hadn’t come once. Jess really started grinding
her pussy on my face as I came
“You pathetic bitch, you’re getting off knowing you’re girlfriend fucked
another guy and made you eat her cunt afterwards. You’re such a sissy, you
must be a fag I bet you loved Kevin’s cock so much didn’t you. Maybe I’ll
try and get Jack to fuck both of us next time”
Jess got off me and started scooping my cum off me and into my mouth. I
swallowed it all without a word and then she told me to leave.
Hope you enjoyed, it’s my first story so I’d love feedback
Lady Libertina Xx
Published
My Girlfriend Made Me A Sissy – 2
Thank you to everyone who sent me messages about the last story, I’ve tried to include things people wanted to see in the sequel. Hope you enjoy
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I woke up, stretched out and smiled as I felt the familiar sensation of my girlfriend’s panties rubbing on my cock. The feeling instantly brought back memories of the night before: I had gone to a party with my rather dominant girlfriend; been coerced into her panties; sucked my very first cock and found out my girlfriend had fucked another guy whilst I was doing it. I loved every minute of it, my sissy-cock was rising as I remembered it all but I had to resist the temptation to touch it. Jess would kill me if she found out I’d been jacking off without her permission. I got up and with some effort of will took off the panties to go shower and get ready for the day; I was ready not a moment too soon. I came out of the shower to find my phone buzzing; I grabbed it to hear Jess’ voice.
“Morning Sissy, I assume you’re free today?”
“Yes Jess”
“Oh good, I need you to come over for a while”, and with that she hung up. I dressed quickly and ran out of the house; it wouldn’t do to keep her waiting.
I let myself into her house and ran upstairs to find her lounging on her bed, just listening to music.
“Well you took your time didn’t you?” She sounded pissed.
“I ran here as fast as I could Jess”, it was true I was breathing so heavily.
“Get over here bitch”, she grabbed my arm as she sat up and launched my over her lap “I can see I’ll have to teach you a lesson”
I knew what was about to happen, but I didn’t struggle. I was too tired so it wouldn’t help at all, Jess was pretty strong. Plus, I do think some part of me was rather looking forward to it, that is until the first blow landed. SMACK!
“Oww!”
“Shut up sissy, unless you’re going to count them keep your slutty mouth shut!” She slapped each of my ass cheeks in turn, I couldn’t believe how hard she could hit.
“2…3…4…” I started to count, hoping if I did it would please her and she’d stop sooner. I guess I could have resisted but it didn’t come to mind at all once she got going.
“Oh look how pathetic you are slut! A real man would never have let this happen to him. If Jack was here I’d probably be in your place! He definitely wouldn’t have been over my knee whatever happened”
The reference to the guy who fucked her the night before stung a little, but the fact she so happily talked about it as if my feelings on the matter were nothing actually just made me excited.
“OMG! Is my little sissy getting hard? Little is the word alright, I can just about feel something pressing against my leg”, the spanking eased a little as she laughed.
“*gasp*…30!”
“30? Well I guess that’s enough sissy”, she pushed me off her lap. “I’ve got you some presents, grab the white bag” She pointed to a white bag from some high street clothes shop next to a rather ominous looking black plastic bag. I ran to get and bring it back to her.
“Look inside sissy”
I opened it to find Jess had gotten me a lovely present, a frilly pair of pale blue high cut panties and a matching bra.
“Oh thank you jess”
“Well sissy, put them on!”
I stripped off immediately and pulled my presents on, I couldn’t believe she’d done this for me. She called me onto the bed with her and we started making out.
“Come here my little girl” She said as she pulled me towards her, I loved it when she was nice to me like this between the commanding times. As we kissed she started to rub my cock and balls through the panties, she was lay on top of me; it made me feel so feminine.
“Spread those legs baby” I opened my legs a little and her hand dipped further down, teasing my ass.
“Wouldn’t you love it if Kevin could fuck you here?”
“God yes, Jess, I was thinking about it the whole time I sucked him”
“I knew it, how could a sissy like you dream of anything else?”
She grabbed some lube from the desk near her bed and squirted some on my ass and her fingers. She held my balls in her left hand whilst she teased my ass with the right. I felt some pressure on my little hole and I could feel her pushing her middle finger in.
“Oh I love fingering my little bitch, but I know you love it too don’t you baby?”
All I could do was moan, I was in heaven whenever she played with my ass.
“Do you want to be a girl for me sissy?” She had that look on her face, she had a plan. I nodded eager to do whatever she wanted, I knew I’d enjoy it.
She smiled, got off me and went to her wardrobe. She came back with a short black skirt and a blue vest top.
“Put this on sissy, and then sit at my desk”
I pulled the skirt on and then the blue top and as I walked to her desk I caught a look of myself in the mirror. I was thin, absolutely no muscle and had oddly wide hips. I straightened my shoulder length hair and had, without planning to, ended up sporting a very girly haircut in my day to day life. My ass and legs looked really good in the skirt and apart from my flat chest and my face, I looked like quite a convincing and maybe even attractive girl.
“I’m going to do some make-up for you sissy, and then you’ll look perfect”
We spent the next 20 minutes with her doing my make up most of it was fairly discreet just to make me look more girly. However she outlined my eyes fairly obviously in dark eyeliner and did my lips a dark red colour, I couldn’t stop smiling when I saw myself in the mirror: I looked for all the world a flat-chested girl.
“Back soon dear”, she took the black plastic bag and left the room. I sat on the bed and just waited for her to come back.
She re-entered the room a while later, wearing some fairly baggy jeans and a plain black top, I had no idea why she’d changed to such a dull outfit but I was about to find out. She pushed my so I was lying on my back and climbed between my legs.
“You look so hot, sissy” She started kissing my lips and neck between words “In fact I can hardly say sissy, everyone would just think you were a girl”
I loved this, I had no idea why she was being so nice to me and I didn’t question it. She reached under me and I felt her pushing at my hole again. I started to moan as she pushed one finger into me and then two.
“Oh you look hot baby, do you like it when I finger your sissy pussy?”
“Yes…Jess…” I manage to get out between gasps and moans
“I know you’d love a cock right now…”, I moan louder “…and I’ve done as best I can”
She held my hand and brought it to her jeans, I can feel something in there.
“Get my cock out baby”
I opened her jeans and pulled out a flesh coloured dildo, it was about 7 inches long and rather thick looking: she was wearing a strapon.
“Stroke me” I grabbed hold of it and started to pull on her “cock”, I was amazed she’d gone this far for me.
“Oooh!” I moaned, taken by surprise as she forced a third finger into me.
“Mmm you’re good at that bitch, now let’s see how well you suck”, she straddled my face and started feeding me the cock.
Reality struck at that point, I was a 16 year old boy looking like and completely dressed as a girl sucking my girlfriends plastic cock and oddly enough, loving it.
We got into a 69 with me on top and she started playing with and licking my ass, completely ignoring my cock but that just seemed right. Hers was so much bigger and if anyone was the man in this relationship it was her, I was just a sissy. I lay there happily sucking her cock, having to idea of time passing until suddenly she stopped and told me to stay where I was. She slid out from under me and slapped my ass.
“I think it’s time we made you into a woman, sissy”
I started to feel nervous but I was so excited, I knew what was coming next. She got up on the bed behind me and flipped my skirt up exposing my panties. These were pulled down just enough to give her access to my sissy ass, and she started fingering me again
“So sissy, are you ready to get fucked”
“Oh yes, Jess please fuck me”
“You really want it don’t you slut? You’re just my bitch aren’t you?”
“Ooooooh yess I’m a slut, I love cock and I want you to fuck me because I’m your bitch, I just want to serve you all the time Jess” I somehow managed to say between moans.
“Wow sissy, I wasn’t expecting that, but I’m sure you’ve been expecting this”
And with that, I felt her fingers leave my ass and something much bigger being pressed against my hole.
“Get ready sissy” and slowly, slowly she started to push the cock into me
“Oooh my godddd, itsss soooo biiig!” I’d never had anything so big in there and it started to hurt a little
“Jess, it hurts! Please just take it out”
“No way sissy! You wanted this, just relax and you’ll love it soon” She managed to get the whole thing in my ass and then stopped. She reached around and started to play with my balls, occasionally brushing my cock. The pain left quickly and I started enjoying it again, when I began to moan from her attention to my balls she slowly started to move the cock in and out of me.
“You have no idea how hot this looks sissy. Your ass is just eating my cock”
I was moaning aloud again and reached down to play with my cock
“Hands off that little clit sissy, I’ll tell you when you can come”
I moved my hand away and just lay there taking her cock, it was obviously getting her off because I could hear her moaning and occasionally the speed picked up and then dropped as she came.
“Oh god this is getting me hot sissy”
She wasn’t the only one, I was pushing my ass back to meet her every thrust now and moaning into her covers. I loved the feeling of her big cock inside me and I never wanted it to stop
“Oooh fuck, this is good” She was really building up for a big orgasm, I could see it coming and that just got me hotter. I really started pushing back on to her cock, I forgot it was jess, it was Kevin. Kevin, fucking me faster and faster getting ready to cum in my ass.
“Fuck me harder! Cum in me please, cum in your sissy”
“That’s right bitch, I’m fucking your sissy ass. I’m gonna cum in it and make you mine”
“Oh yes! Cum for me baby” I can’t believe I was saying these things, but it was certainly working on Jess. She was moaning louder and louder before suddenly ramming her cock all the way into me and rapidly moving it in me.
“Here you go sissy! I’m cumming in you, cumming in my little”
I was moaning like crazy as she collapsed on top of me, obviously she’d decided it was time for me to cum yet.
After a few minutes she recovered and was her usually crazy self. She pulled out of me and ripped off the strapon.
“On your back sissy”, I rolled over and lay on my back. My panties had come down around my thighs and my cock was making a little tent in my skirt. She kneeled with one leg on either side of my head and lowered her pussy down.
“Eat my pussy bitch, you’ve had your fuck and now you better say thank you properly”
I didn’t need telling twice, I was full of enthusiasm as I started to lick her pussy but she wasn’t in the mood for anything too special. She just wanted to ride my face and pretty soon I was mostly holding my tongue out and flicking it as she rubbed her cunt over my face. I felt like she was just using me, anyone would do and I loved it. Then her phone rang.
“Don’t you dare stop, sissy”, she said as she answered her phone. She started talking but I could only hear her side of the conversation and that was muffled by her thighs as she continued to ride my face.
“Hey baby, I didn’t think you’d call…. what am I up to? Nothing really”, that stung but I didn’t stop eating her and I was incredibly horny for some reason.
“You want to come round? Well… my boyfriend is here I don’t think he’d like it… yeah, it’s the boy I left with the other night… Does he know about us? Well yeah I told him, he doesn’t seem to mind all that much…”
Mind? I was lying underneath her, eating her as she spoke, I certainly wasn’t acting pissed off
“Well yeah he’s a bit pathetic to be honest” She really started grinding down on my face “He’s nothing like you, you’re a real man… you know I think he was off with that Kevin guy at the party when we fucked… yeah the gay one… Yeah it is a bit odd, I guess I’m just going out with a bit of a sissy!”
She laughed and then covered the mic on her phone as she came.
“You’re coming over anyway? Mmm that’s why I like you, you’re so commanding nothing like this pathetic wuss. What’s he doing? He’s actually eating me as we speak!”
I was mortified, how could she let him come over? And I was so embarrassed he knew what I was doing as they insulted me.
“Well you can teach him a lesson or two, but don’t hurt him… Why? Because even if you do come and fuck me more often I’m keeping him… Why would I want a pussy like him? He’s happy to just do as I say, it’s like having my own slave. He could even serve us both… We’ll see what you think once you’ve seen him baby, bye now”.
“Did you hear that sissy? Jack’s coming over to fuck me like only a real man could, maybe he’ll let you watch! You’d like that wouldn’t you?” She raised herself off my face
“Yes Jess, I’d love to see a real man fuck you”
“Hahaha you really are pathetic. Now when he gets here you will only call me mistress and if you’re a good sissy I’ll see if he’ll let you clean him off after he’s fucked me. I’m going to go get ready, stay here”
She left the room and left my lying there on her bed. My face was covered in her juices and I was still dressed like a girl, I couldn’t believe what was about to happen and I couldn’t imagine what I would be expected to do. Yet, despite everything I was still kind of excited, I was certainly hard and my main issue was that I hadn’t been allowed to cum not that my girlfriend was planning to let some guy fuck her and see me dressed
More to come soon I hope, let me know what you think
Lady Libertina Xx
Published
