tagTranssexuals & CrossdressersMy Girlfriend Made Me a Sissy

My Girlfriend Made Me a Sissy


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 18, 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 turn."

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?"


"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, and I'll make it worthwhile later."

Now this shows our relationship perfectly, here I was 18 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.

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by Anonymous

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by Anonymous03/21/18


I can only fantasize. I am a girl at heart but a male in body and sucking sounds like an erotic pleasure I have never experienced first hand.

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by Anonymous12/23/17

love the story

I also am really turned on by the comment caught by wife

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