[MM] My unexpected first fucking

About me, I’ve always been very fem looking, with long curly red hair, big green eyes, high cheekbones, and nice full lips. I’ve been mistaken for a girl many, many times, even to the point of being hit on by men before. I have to admit, it made me very curious about having sex with a man. I fooled around with a good friend of mine a few times and found it really turned me on.

One night not long ago, I was hanging out with a friend at his apartment. It was the middle of summer and we were bored, so we smoked some pot and were watching porn. His roommate was out for the night and I started to feel a little naughty. I don’t know what got into me, but I asked my friend if the porn was turning him on. He replied that it was, so I reached over to him and put my hand on his crotch, saying, “Let me see if you’re getting hard then.”

[MM] First time fucked and creampied

When I was younger, I had a good friend, Rob, who I used to hang out with all the time. We’d talk about everything and were very close. At one point, I knew he’d gone through a long dry stretch sexually and was very frustrated with it. One night, we were hanging out together and he asked me if I could give him a blowjob. I was taken aback by it, but I’ve always been a pleaser, someone who wants the people in my life to be happy. After a back and forth, he talked me into doing it as a favor to one of my closest friends and, to my surprise, I enjoyed giving him head and swallowing his cum. I gave him several more blowjobs after that.

One night when I was going down on him, Rob asked me if he could fuck me. I looked up at him, shocked by the question. “Are you kidding me?” I asked.

“You haven’t thought about it before?” he replied. “I’m curious what it would be like.”

“No, I’ve never thought about it,” I said, although I had to admit there was a little bit of curiosity now creeping into my mind.

My first time sucking cock [MM]

I wanted to share a story I’ve never told anyone about before. Like most guys, I was really interested in sex in my younger years. I was always very interested in girls, but every so often I would have very intense dreams or sometimes sudden fantasies about having sex with another guy. I never told anyone about those occasional fantasies and it was sometimes really embarrassing to me, but I wrote them off as just part of growing up and being curious about all things sexual.

I had a really close friend at the time, whom I’ll call Jeff. Jeff and I used to hang out all the time and we talked about everything going on in our lives, school, girls, parties, everything. One afternoon, I was hanging out at his place. We had just smoked a joint and we were both feeling pretty good, super relaxed and stoned. “Dude, I have this new porn movie I bought. Do you want to see it? Jeff asked me.

“Sure,” I replied and he got up to get it from his bedroom and put it into the DVD player. As it started up, I settled back on the couch as Jeff sat down into his lounge chair. A few minutes into the action, Jeff asks me, “Hey, can I ask you a favor?”

My supposedly innocent girlfriend surprises me with her fist in my ass [MF]

Back in my college years, I had this one girlfriend, Annie. Annie was a sweet, petite little thing, very unexperienced sexually, but very open minded and willing to try new things. And as she was willing to try new things, I was always looking to help her explore her limits.

One night when we were playing, I was going down on Annie and fingering her pussy. I had her turn over on her belly so I could finger her deep and as I went to put my tongue inside her again, I realized I had my nose in her cute little ass. I couldn’t resist myself and I went to lick her asshole, not knowing how she would react. She moaned deeply as I licked her ass, my fingers deep in her, so I kept going, my tongue working away at her sphincter, my fingers deep in her. She quickly came for me, loudly, then tumbling down with a smile on her face.