Turned into a Sissy

I was 20 years old and had been going out with my girlfriend for about 9 months. Everyone thought I was straight, and although I had never really acted on it, I had often had gay thoughts and wanked over other men. So when my girlfriend told me that she wanted to fuck my arse with a strap on, I was interested.

I was at university at the time but was home for the holidays. I only come home during the holidays, so at first both me and my girlfriend were super horny for each other. We'd have sex all the time but after a while we both got a bit bored of normal sex. She seemed to notice that I wasn't that keen on it, partly because I had been wanking over gay porn behind her back. She therefore thought it would be a good idea that we try something new.

"What would you be into?" I asked her, not really sure where this was leading.

"Well, there is this one thing I read about online... It kinda excited me but really not sure if you'll want to do it." I told her to just say it, so blushing she asked me "have you ever heard of pegging?"

"No, what's that?" I replied. I'd honestly had no idea what it was.

"Well it's where a girl fucks a guy. With a strap on."

I was stunned. I hurriedly replied "no, that's gay!" Although secretly the thought of being fucked did excite me, I wasn't going to act upon it.

"Honestly it's not. It's just another way of having sex, straight guys have prostates too and I've heard it feels amazing for you. Just try it for me, please."

I didn't really know why I was resisting. She wanted it, and I desperately wanted it. So eventually she persuaded me to try it. She said she would buy all the equipment and we would try it the next day.

The next day she came over to mine as usual after work, and greeted me with a big smile as I opened the door. We went upstairs to my room and as she showed me all the equipment I immediately became hard, while trying to hide it and act unsure.

"Come on, lie down" she told me. We started with the normal foreplay, kissing and undressing eachother. But when we were both naked, she suddenly stood up and said "now turn over" in a commanding voice. I did as I was told, slightly turned on by being told what to do. I felt her stroke up and down my legs, before spreading my cheeks and squirting lube onto by anus. As she did so she slowly massaged my anus with a finger, before slipping it in gently. At first my anus resisted, but there was enough lube that it slipped in easily enough. She started to finger me rhythmically before slipping a second finger in and upping the pace.

The feeling was amazing. I started to arch my back a bit, pushing myself onto her fingers and silently begging for me. I was fully erect, and pre-cum was dripping onto my bed below me. After a few minutes she stopped, and without saying anything put on the strap on and started to lube it up. I tried to turn around to look, but she grabbed my head and pushed it down into the bed.

"I want to fuck you doggystyle" she told me, so I immediately got onto my knees and stuck my arse into the air. She rubbed the dildo up and down my crack, teasing me with the thought of it, before slowly pushing against my anus. It slipped in fairly easily because of the lube, but once inside it made me gasp in pain.

"Just give it a moment" she told me. She was right, because after about 10 seconds the pain went away and I relaxed. Slowly she trusted into me. She kept going until she bottomed out, touching my prostate as she did. My dick jumped a little bit and I let out a little moan by accident. Taking that as encouragement, she started to fuck me faster.

I had never felt anything like it. I remember thinking that I wanted her to fuck me for hours, and I lost myself in the pleasure. After a few minutes she slipped out and said "get onto your back bitch". Taken aback by the tone I was quick to respond, moving onto my back and lifting my legs into the air, revealing my arse to her. She quickly inserted back inside me as I let out a gasp of pleasure. Each time she trusted inside of me my fully erect dick would do a little jump.

After a couple of minutes in the missionary position I started to feel something building inside me. "Keep it there" I told her, grabbing her arse and pulling her into me with each trust. Slowly an amazing feeling built and built, and before I knew it I came all over my stomach. I looked down in amazement. I didn't even know you could cum without using your hands, or that it could feel that good.

After that one time I felt too embarrassed to try it again, despite my girlfriend persauding me. A week later I went back to university, knowing I would have many wanks remembering that night.

***

I was lying in bed one night, just chatting with my roommate josh. Josh was an average looking bloke. He was slightly bigger than me, but that wasn't hard given how skinny I am. He had never had a girlfriend and wasn't very experienced, so used to ask me advice on girls. It was about a week into term, and he asked me what the kinkiest thing I'd ever done was.

"Oh not much really" I replied. He gave me a knowing smile, before saying "come on, tell me".

I blushed; surely he couldn't know about the pegging? "No honestly nothing" I told him.

"I saw some texts you sent your girlfriend" he told me. "You know which ones."

I say there awkwardly in silence. "So what?" I reply.

He smiles at me before rolling over on his bed and saying "oh, nothing.."

I decided to go to sleep, so I switched the light off and tried to fall asleep. However I couldn't get the memory of my girlfriend pegging me out of my mind. The more I tried the more I thought about it, and before long I was hard at the thought of it. I started to stroke my penis, with my other hand casually toying with my anus. I lost myself in the memory of the orgasm, remembering the feeling of being fucked and the pleasure of the dildo hitting my prostate.

"Remembering it are you?" Josh suddenly said next to my bed.

"Fuck!" I replied, "what are you doing?" He was standing there naked, with his semi erect penis about a foot from my face. My eyes must have lingered on it a little too long as he chuckled and said "go on put it in your mouth."

"I'm not gay!" I exclaimed, but he only moved closer and lifted my face towards his penis. He took me not recoiling as encouragement and putting his hand on the back on my head pulled my lips onto his now hard dick. At first I froze. I had always wanted to suck a dick, but I couldn't let anyone know that.

"Don't worry, I won't tell anyone" he assured me, as if he read my mind. I couldn't resist it any longer. I slowly moved my lips up his penis, which was about 7 inches long, until I reached the head. It had a small drop of pre-cum on the tip which I licked off. Surprisingly I loved the taste, and then closed my lips over his head and moved them as far down his dick as I could. I could only manage a few inches before I thought I would gag, but josh moaned in pleasure anyway as I started to rythmically suck him off. I felt myself growing hard and started to play with his balls, before using my hands to wank him off at the same time as sucking him. He obviously loved it and groaned in pleasure. I couldn't wait for him to cum in my mouth, but just as I thought he would he pulled out. I looked up sheepishly, and he grinned at me before picking me up and tossing me onto my front.

"Wait there" he told me, before crossing over to his desk and getting a bottle of lube out of his desk. As he came back over he stroke his hand down my back, before spanking me hard. I gasped, not so secretly loving it. He opened my arse cheeks and squirted lube onto my anus, before loosening it just as my girlfriend had. Once I was ready he pulled my arse up towards him.

"Do you want me to fuck you, sissy?" he asked me as he stroked him penis up and down my crack.

"Yesss" I moaned, pushing my arse into his dick and opening my cheeks my with hands. Josh obliged, slowly pushing his dick against my anus. It entered with a pop and was again painful. However this time it subsided quicker, and I softly moaned "fuck me" at josh.

He pushed all the way into me, and it felt even better than the didlo, filling me up even more. When he bottomed out it felt like his whole head was resting against my prostate and I moaned in pleasure at it. He started to rhythmically fuck me, gently at first before becoming more forceful. He grabbed my hair, pushing my head into the bed and driving himself deeper inside of me.

I moaned loudly like a little bitch. Each trust brought immense pleasure, and the way he used me made it even better. Eventually josh picked me up, and while still inside on my flipped onto his back. I was know squatting on top of him and unsure what to do.

"Ride me you little slut" he commanded, and eagerly I obeyed. In this position his dick would reach deep inside of me, and my erect dick was bobbing up and down and dripping pre-cum everywhere. Soon the sensation started to build up again, and as I started to moan louder josh grabbed my hips and started trusting quickly in and out of me. I came all over my bed without touching my penis. Because I was facing away from him josh didn't even realise at first, and just kept fucking me like before. But I didn't want him to stop anyway.

"Now get off and lie on your back" I was told, and as quickly as I could I obeyed. As I got off his dick josh noticed the cum everywhere, and caught my eye with a grin. He then pinned my legs up behind my head and slipped deep inside of me. I was instantly hard again, and grabbed his toned arse cheeks pulling him inside of me.

"Cum inside of me" I moaned softly at josh, "please cum in me". I felt his penis twitch inside of me as I said it, and soon afterwards he picked up the pace. He was fucking me harder than ever now and his penis was rock hard, making it feel amazing.

"I'm gonna cum he moaned" and I felt his hot cum shoot inside of me. It was too much and I started to wank myself off. Within seconds and came all over my stomach as josh slowed his thrusting and softened inside of me. He eventually pulled out, his cum dripping out of me and down my arse crack, which I found strangely satisfying. I played with my anus a bit, before scooping up some cum with my finger and seductively sucking it off while making eye contact with josh.

"You're my little slut now" he told me. "And that's only the beginning."