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.
