[m/f] After two years of desire I had sex with a girl in my group of friends (includes anal) | 2016

*** Like I've said in previous posts. I figured it would be fun to go back to my promiscuous (man-whore) days and recall some of the stories from back then. Not to be arrogant, but I am generally considered a really good-looking guy (used to model, 6’3”, dark hair, blue eyes, swimmers build, workout regularly), so that enabled me to have quite a fun sex life. These stories are 100% true and not embellished in any way. I think that a straight honest story even if not as exciting at times is a bigger turn on, so that is what I will continue to try to give. ***

I posted another story earlier today and figured I would knock another one out while I am in the swing of things.

I was friends with a guy we’ll call Jimmy who used to date a girl we’ll call Angie. Angie and Jimmy had broken up a couple of years prior, but would still hangout regularly. I got to know her pretty well over those couple of years of hanging out. Angie had a friend we will call Rachel. Rachel was half Hispanic/half white and looked a lot like Audrey Hepburn. She was always just so adorable yet beautiful. She was about 5’4”, very petite, perky B cup tits, and a perky bubble butt. She was exactly my kind of girl. Rachel would hangout with the group of us quite a bit and I always wanted to try to make something happen with her, but she always seemed very closed off and kind of cold. She seemed like a really nice girl, but would try to act somewhat hard like nothing bothered her. I can’t quite pinpoint how I would describe her overall, but I was intrigued to say the least. The entire two years I knew Rachel she never had a boyfriend and rarely talked about guys. She would joke sometimes with Angie about never getting any and making good use of her toys. That is the only sexual talk I had ever heard come out of Rachel, but when she talked about it my imagination ran wild.

One night we were all hanging out at a bar having a good time, but it was closing soon. Angie invited a group of us back over to her house, so we went. We continue drinking and listening to music for a while at her house. I was alone with Rachel out on the front porch and for some reason I decided to attempt to make something happen with her. I’m sure I was definitely aided by alcohol or I wouldn’t have had the balls to say anything. I just blurted out “Did you know I’ve always had a thing for you?” She turns towards me with a look of surprise. She said, “whoa, what? No, I didn’t know.” It hit me then that I had a thing for her all this time, but never even flirted or made it known in any way because she just seemed like someone who was off limits and didn’t want to date anyone.

After her initial look of surprise she kind of smiled. She stood there looking like she was pondering and said, “I wish I would have known that a long time ago.” I was relieved, because this response seemed to be fairly positive. She said, “If we’re being honest, I always kind of had a thing for you too.” My face went flush and I tried not to show my excitement. She gazed at me and we leaned into each other and enjoyed a long slow kiss. We continued to kiss very slowly and my excitement instantly made my cock hard. We could hear a couple of our friends inside headed toward the porch, so we stopped. We both knew that this would be a big deal within our group of friends and it was so new we didn’t quite know what to make of it. I was really hoping Rachel would invite me to her place. I didn’t want to invite her to mine, because I didn’t want to seem presumptuous. Unfortunately neither happened. The night ended and I stole another kiss from her just before she left.

We all hung out again a couple of nights later for another night on the town. This was a whole new experience given what happened last time. The tension between Rachel and me was palpable. I’m sure no one else noticed, but we both felt it. I couldn’t take my eyes off of her the entire night. I wanted to grab her and kiss her, squeeze her body up against mine. The night felt exhausting, because of the restraint I had to show. As we were about to leave the bar I felt her walk up and grab my arm and whisper in my ear “come to my place and hangout.”

We all left going our separate ways, but I headed to Rachel’s. I get to her apartment and we walk in together. At this point I don’t know what is going to happen. I’m not sure if she just wants to go at it or if we are just truly hanging out. I don’t want to over step my bounds at all, because I actually liked this girl. We sit down on her couch and she pours us each a glass of wine. We start talking about a million different things. We talk about life and relationships and many many things. She starts talking about how she was really hurt by a guy a few years back and it has fucked her up in regards to relationships. She told me she hadn’t had sex in two and a half years and pretty much stopped seeking out guys all together. That explained the cold vibe I felt from her and the comments to Angie about toys.

I was sitting there wondering why in the fuck she was letting me get close to her in any way then. So, I finally just asked her why. She said that she got to know me really well over the couple of years that she’d known me and really liked me and trusted me. She said if I were some guy she had met once or twice that there is no way anything would have ever come of us, because there were too many barriers. The barriers were broken down by just being around me in non-threatening situations so often and really getting to know me. I was flattered and a little intimidated that I was the guy she let break through.

She leaned over and we started kissing deep and slow. My mind was racing thinking about the fact that she hasn’t been fucked in two and a half years. That seemed like a lot of pressure to perform well, but I was fairly drunk so my anxiety quickly subsided. We kept kissing and she straddled me on the couch. I reached under the back of her shirt and undid her bra. I tossed it to the side and reached back under the front of her shirt and felt her perky breasts. Her nipples were rock hard and she began to let out slight moans as I touched them. I lowered my hands down to her hips and reached back with both hands and grabbed her ass and grinded her down into my crotch. She quickly raises her arms and does away with her shirt. I am now staring at beautiful adorable Rachel topless on top of me and I can’t get over it. I just never thought after all of this time that we would be in a moment like this. I kiss her stomach and lick up to her nipples. I tease her and flick my tongue over and around them. She shudders and lets out little moans. It may have been completely in my head, but I felt like I could tell she hadn’t been touched this way by a guy in two and a half years.

She pulls my shirt off over my head and it seemed like she kicked into some animalistic mode. Once she saw me with my shirt off she quickly started kissing down all over my neck and down my chest. She kissed down my abs and licked slowly up and down from my waistline to my chest while looking up at me. My cock felt like it was about to burst out of my pants at this point. She undid my belt buckle and pulls my pants and underwear off of me. She said “fuck, you have a big one” sounding excited and worried at the same time. Her concern lasted only a moment as she took it in her hand and stroked it slowly. She looked at it and watched it as her hand slid up and down on it. She looked mesmerized, not necessarily at the size, but at the fact that she had a cock in her hand after going so long without it. She then slides her lips over the head of my cock and stays there for a moment before plunging her mouth down as far as it can go on my cock. I feel my cock hit the back of her throat and she comes up slowly and then back down quicker and quicker. She stops for a moment after slightly choking and catches her breath. While catching her breath she strokes my cock, which is extremely wet with her saliva as she licks and sucks on my balls.

She asks me if I want to go in her bedroom and I say yes. We get to her bed and she takes off her pants and panties. She had the cutest perky bubble butt and I couldn’t keep my hands off of it. We stood beside the bed kissing for a couple of minutes while I groped her ass and fingered her pussy from behind. She starts to breath heavily and seems like she is somewhat close to orgasm. She turns and lies down on the bed and spreads her legs apart motioning for me to lick her pussy. I go right after it and attack her clit with my tongue while I fuck her with my fingers. She moans loudly as I try every way possible to please her. After about five minutes she screams “I’m going to cum. I’m going to cum” and begins shaking and tensing up. She recovers for a minute and motions for me to join her on the bed.

She is still lying on her back and she motions for me to get beside her face. I get beside her and she starts stroking my cock with her hand and then places it in her mouth. She slowly sucked my cock with her eyes closed looking as if she was savoring every inch in pure bliss. After a while she sits up and pushes me onto my back. She gets on top of me and straddles my cock. She is soaking wet and easily slides my cock in her pussy. She starts slowly sliding up and down on it and I am thoroughly enjoying watching as every inch slides in and out of her. We stay at this pace for a while and then she leans down to where her chest is touching mine and I grab her ass cheeks and just lower her slowly up and down on me.

After a couple of minutes she reaches back and starts fingering her ass while I fuck her. This seemed to really make her go wild. She instantly started moaning even louder than before and seemed overtaken with the sensation. I kind of had a feeling she might be into anal, but never knew for sure obviously. During one of the only two or three sexual conversations I ever heard her have with Angie, Angie said something about anal and Rachel just made some sort of comment like “they make toys for that too” or something and kind of giggled. Apparently she was realllly into it though (I found out at a later date that she for whatever reason liked anal as much as vaginal sex and often times preferred it). She continued to ride me while fingering her ass and after a few minutes she began shaking again and froze as she orgasmed.

After sitting still on my cock for a few moments while she recovered she slid off and got on all fours. She started fingering her ass again. I was staring at her doing this and wondering if I should try to fuck her in the ass or what. I didn’t want to fuck anything up with her and knew it had been forever since she had sex so I wanted to make sure she was comfortable. After a minute of this she looks back at me and says “can you help me?” She reaches over into the drawer beside her bed and pulls out some lube. I also caught a glimpse of a couple of toys. I guess it was her drawer of fun. She hands me the lube and I get my cock lubed up and then put some on my hand and spread it all over her asshole. This again was one of those moments where I stopped in my head and thought “holy shit I am spreading lube on Rachel’s ass” it was a complete mind fuck.

I positioned myself behind her and she said “go slow at first”. I kind of figured I had to go slow, because she was very petite and like she referred to earlier I am not a small guy. I pressed my cock against her ass and slowly plunged the head in. She let out a moan and said “yeah, yeah”. I slowly slid another inch or two in and she moaned even louder. I slid it back out and then back in even further. I did this a few times until all but about an inch of my cock was inside her ass. The feeling of her ass clenched tight around my cock was so intense. It took major mind control for me not to bust early on. She told me “faster”. I picked up the pace and began sliding my cock in and out of her ass with ease. She is screaming and moaning louder than she has all night. She tells me “harder”. I am slightly worried still that I am going to hurt her, so I hesitate but then decide to go for it. I start pounding her ass and at times she was taking all of me inside her down to the base of my cock. I never would have thought my entire dick would fit in her ass. She is moaning uncontrollably and rubbing her clit.

Her knees seem to be going weak and she tells me to stop and then turns and lies down on her back. She kicks her legs up in the air and places them on my shoulders. I slide my cock back into her ass with ease and she continues to rub her clit. I get back up to the pace we were at before we stopped and I can now see her face as I pound her. She looks like she is in pure bliss and she occasionally looks into my eyes as I fuck her ass. I can’t hold out much longer and tell her I’m about to cum. She looks at me and says, “Yeah cum for me”. I could tell by the way she said it and the way she was looking at me that she wanted me to cum in her ass. A few moments later I start to unload shot after shot of cum into her ass. She digs her fingernails into my back as I cum and collapse onto her.

I spent the night with her that night and we started officially dating not long after. We dated for about 7 months before things went south. She still had a lot of issues from her previous relationship that unfortunately caused problems in ours. It was really great dating her while it lasted though. Our sex life was amazing and she is the only girl I have ever been with that loved getting fucked in the ass on a regular basis (we probably had more or equal amounts of anal sex as vaginal) and asked for it.