Hookup Stories

Hooking up with a Lesbian

No matter how much time you spend hooking up, you’re still going to come across those hooks ups that you never expected to have. They could be coming from friends that you never considered or people you work with that never seemed interested. For me, the most unexpected hook up I had was with a lesbian. This wasn’t just some bisexual girl that chose to me exclusively date women, now. She was my friend for years and she was a full-blown lesbian. We had talked about it many times in the pest and she explained that the idea of having sex with a man was kind of icky to her. I’m assuming it’s the same way that I feel about having sex with men. It’s not desirable in any way, shape, or form. Anyway, one day came when she was taking a break from her long-term girlfriend. I don’t know what was going on but they were pretty much broken up at this point. We were just hanging out one night and the subject of sex came up, like it usually did with us. She decided to open up about her sex life with other women.

She had never been penetrated

The one thing she said that blew me away was that she had never been penetrated in her life. It hadn’t happened a single time, not with a dildo, or even with fingers. It turned out that she had some sort of hang up with it and always refused it when it came up. That made her a technical virgin, or even an actual virgin, if you only consider sex between a man and a woman as counting. I guess she was only ever interested in having her clit played with whenever she got it on with someone and she was the one who normally did the penetrating anyway. She had plenty of strap ons that she used to have sex with other women, but had never experienced anything inside herself in her life. I wanted to get deeper into the subject, but that was when her mood changed and she seemed to be a little bumnmed out that she had never experienced penetration. She said that it seemed like it was enjoyable enough for the women that she did it to, but that she felt like she was missing out on something by never having it done to her. That wasn’t all she was missing, though.

She wanted to try a man

As she kept talking about all of the things that she felt she was missing out on, she started talking about men. She may not have found them overly attractive, but she started to mention how she felt like she was missing out on something. If most women liked having sex with them then it something that she should have experienced at some point. It was as if always refusing to have sex with them just became a self-fulfilling prophesy. She had never actually done it, so she had no idea is she’d actually enjoy it. It was all just one more thing that she was missing in her life and she had no idea how she’d manage to try it all out. These are the thoughts that we all have after we break up with someone and I just happened to be there while she was realizing all of it. The only difference between her r4ealizing all of these things on her own and realizing them with me is that I’m not someone to let an opportunity pass me by if I can help it.

I just made my move

I barely even thought about it when it happened. I saw and opportunity and I took it. We were close enough friends that I knew she wouldn’t have a problem with it. The only thing that could have gone wrong was her refusing me, but I was more than okay with stopping in that instance. As it turned out, she didn’t want to stop me. I moved right in and planted my mouth on hers. I knew that I was in as soon as I felt her nails dig into my back and felt her pull me toward her. She also opened up her mouth so I could slide my tongue right in. It wasn’t long at all before I was on top of her and pulling off her shirt while she pulled down my pants. She was about as enthusiastic as she could possibly be and I didn’t want to waste a single second of it. I also knew that I couldn’t be gentle. She had spent her entire life having gentle sex and being in charge of other women. She wanted to experience what it was like to be taken by a man. I had to make sure I gave that to her as much as I could.

She was virginal

I won’t go into all the details about what we did because it’s just not necessary. What I’ll say is that she was virginal between her legs. She was completely waxed and soft. She inner lips were short and she had no signs of ever having sex before. That was simply because she had never had it. I knew that I had to be gentle when I first inserted myself inside her I wanted it to be a pleasant experience for her, so I went as slowly as I could. I asked her if she was okay and she nodded. I pushed a little harder and finally made my way inside her. She was the tightest thing I had ever had sex with in my life. I just can’t describe how tight she really was. An entire life of never being penetrated made it feel like opening up a virgin for the very first time. I wanted to enjoy every second of being inside her but I knew that she wanted more. Now that she was opened up, I could open up myself a little bit.

I took her

I had to go hard, so I grabbed onto her feet. Lifted them up into the air, and just started hammering away at her. Her head banged against the arm of the sofa that we were having sex on. She couldn’t stop herself from moaning at all of the different sensations coursing through her body. She would occasionally open up her eyes and look down just so she could see my dick penetrating her over and over again. In fact, it seemed like she liked to watch a lot. I’d learn later on that just seeing a vagina was enough to get her wet. Now seeing a stiff a cock was enough to make her gush with juice. I knew that because I could feel it flood every single time she got a good look at it. She dug her nails into my hips and just held on for dear life while I pounded away at her. It was only a few minutes of work before she started to cum. She did it over and over again while I worked my way toward my own orgasm. It was right before I came that I realized she had no reason to be on birth control at all.

I just pulled out

I knew I couldn’t shoot off inside her, so I just pulled out at the last second and shot my load all over her tits. It splattered against them and it was clear that it was the first time anyone had ever cum on her. She enjoyed it, too. She couldn’t stop smiling and laughing with every single spurt. I finally finished and just sat back on the sofa with my hand on her thigh. She took the time to just lie there and start playing with my cum. She smelled it and even tasted it. Then she just started to rub it all into her boobs and chest. I just watched her enjoy her experience until she was finished. She told me that I was the best guy she had ever been with and we both laughed for a little while. It was all in good fun and I was just happy to be able to give her a first. We would have a bunch more hook ups until she ended up getting back together with her girlfriend and eventually marrying her. It was just a good time for both of us.

You never know

So, like I said, you never know where your next hook up is going to come from. It can be someone you know or it can be someone you’ve never met before. You just always have to be willing to take your shot. If I didn’t make my move then I never would have been able to experience sex with an adult virgin. It was a lot of fun and I’ll always be her first. If you get a shot, just take it and see what happens.