by L

Gender: Male
Age: 30
Race/ethnicity: White
Current location: California
Highest education received: College degree (eg., BA, BS)
Occupation: Security
Relationship status: Living with Someone
Religious affiliation: Christian
How religious are you? A little
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 15
How many hookup stories have you here posted before? This is my first

First Casual Experience if There Is Such a Thing

How long ago did this hookup happen? Six Years

How would you best classify this hookup? Friends With Benifits

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? I will call her Bree, she actually has a rather unusual name but she is a reporter with a TV News station and if I used her actual name many people would recognize including those she knows.  She was 22 then two years younger than me, five seven with long black hair and thin with a small chest and pale skin.  She was also quite inked up on her arms and chest and back.  We had worked a retail job together for about six months before we hooked up.  We shared a lot in common, the same tastes in music and movies and TV shows.  We worked together closely and had also been out for drinks a few times before this.  I would like to add that with how she acted I didn’t think Bree liked men before we hooked up.  I liked her and considered us friends, and looking back I think I was a little attracted to her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Now I had been dealing with a lot, my girlfriend of more than two years had dumped me and a week later I had lost my job.  I had been deeply in love with her and had been considering asking her to marry me and our breakup had been quite brutal and sudden.  I had also lost my job a week later and couldn’t find work in the same field.  I spent several months out of work and couldn’t find another in my field and finally took a retail job at an electronics store to bring some money in.
Bree had started work there just a month before me and we ended up both working the in store pickup counter, back then a new thing. We talked a lot and got quite friendly and even went out for drinks a few times and had hung out.

One day after work she asked me out for drinks and we went to a bar a few blocks from work.  Bree would be the first one to admit she came onto me. A few drinks in, Bree put her hand on my thigh and kissed me and then moved her hand to my cock and stroked me through my pants a little. I asked where this was going and Bree responded where did I think?

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? We headed for my car where we made out on the back seat for a while. Our pants came off and I penetrated her, it had been nearly a year since I had sex so it felt great to be inside a woman again. This only lasted a few minutes as someone came out of the bar and interrupted us. Bree asked if we could go to my place since it was closest.
I drove home quickly and we made our way to the bedroom clothes basically falling off.  I helped her with her shirt and bra and grabbed at her breasts a bit. I learned she had quite a few more tattoos than I thought. I sat on the end of the bed Bree in my arms and sucked on her breasts for a while and she kept telling me that felt great and she moaned a bit. Finally Bree asked me to lean back and she sucked on my cock until it was quite hard and she mounted me and brought my hands to her hips and bounced up and down.  She got quite loud and moaned and I grabbed her breasts a few times and her thighs as well, basically grabbing her all over. I came inside her and Bree also orgasamed and then she climbed off me and laid her head on my chest. We talked about all kinds of things and I told her I thought she didn’t like men and she laughed a little when I said this.

We fell asleep and in the morning I got up before her and made Bree breakfast. She joined me at the table naked. When I asked if she was going to put clothes on Bree responded that she slept in the nude and liked to walk around naked in the morning. She then pointed at her breasts and said these are just tits.  We talked for a while, she told me she had really enjoyed last night and I had too.  We discussed where we went from here.

We watched TV for a while, a bit hard for me since Bree wouldn’t put clothes on and she stuck her hand down my pants and played with my cock a bit. Bree always was very comfortable naked. I was well aware she was not getting along with her roommate too well and Bree told me she was not in a hurry to get home. Finally around noon she asked me to run her home, she finally put her clothes on and I dropped her by her place. She kissed me goodbye and said we should do it again.

Did you have an orgasm? Did your partner(s)?: No in the car and we both did in my bed

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We didn’t and I did finish inside her.  Bree told me she was on birth control

What were your REASONS for having this hookup? I would say it was a combination of horny, loneliness, alcohol and mostly because Bree wanted to

Were alcohol or drugs involved? If so, how much? A few drinks each, enough that inhibitions were removed and I maybe should not have been driving

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? Bree and I were friends with benefits for more than two years. For me it was quite different, I had had sex before but only with someone I was in a relationship with. We would hang out, go to the movies as friends and get drinks. Often one of us would ask the other if we wanted to screw and we usually did. Bree was a lot of fun in and out of the bedroom and very different than anyone else I had ever been with. I did on one occasion put my hands on her at work when we were in the back, she gave me a kiss and told me never here. I got another job a month in which I think was good. Honestly we had sex a lot and the word changed for me because of Bree to fucking. Bree usually slept over and a ski trip turned into a weekend in bed with her. She also lived with me for a  few weeks mostly in my bed when she was between apartments.

It went on for about two years and I did date someone else briefly during that time but quickly resumed fucking Bree once we split up. Finally one night she came over, we fucked and then I fell asleep and found her sitting on the end of my bed.  She was upset and told me she had been talking about going exclusive with a guy she had been seeing. She told me she had wanted to throw me one last fuck and then she dressed and left. I would later learn she had been struggling with feelings for me. I had thought things were pretty casual between us and it was always how Bree acted but apparently that had been a front.
Now believe it or not Bree and I are actually pretty good friends, and she is my only female friend.  Sex has not been a factor for us for years.  She is now married and expecting her first kid with that guy who I actually like. I look back on our time together fondly and it was my first experience with sex outside of a relationship.

To whom did you talk about the hookup? How did they react?: Told a few friends over the years who were always impressed.  My current girlfriend did not react well when I told her and was initially quite threatened by Bree but now looks back at me and Bree as getting it out of our systems.

Was this a consensual and/or wanted experience for you? For your partner? Yes for us both

Do you regret this hookup? If so, why? Honestly not one bit, the whole thing was great

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I would say the best part was some great sex with someone I liked without a lot of emotional involvement. As for the worst part, I would say there wasn’t really a bad part, even the end wasn’t that bad. This did change how I viewed sex, before this I had only had sex with women I was in a relationship with. I now view there are two kinds of sex, one is that it can be a fun exercise between two people as it was between me and Bree and the other is that it can be a deeply intimate experience as it is between me and my current girlfriend. I would also argue having read a lot of other posts on here there is no such thing as casual sex. I feel there is nothing casual about what Bree and I did. I always felt great after sex with Bree and was a lot more self confident and sure of my self once we started hooking up.  Hell, Bree even introduced me to my current girlfriend.

All things considered, how POSITIVE was this experience? Very positive

You have a hookup story to share? Submit it here!

What’s Your Fantasy? Click here to be part of the largest survey on sexual fantasies ever!

Comments