by Ron

Gender: male
Age: 30ies
Race/ethnicity: Caucasian
Location: France
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: IT
Relationship status: engaged
Religious affiliation: atheist
How religious are you? Not at all
Sexual orientation: Heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? dominating
How many sexual partners have you had in your life (including oral sex)? 50ish
How many hookup stories have you here posted before? 0

An Escalating Sex Based Friendship

How long ago did this hookup happen? 5 years ago

How would you best classify this hookup? friends with benefits

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? she was a contractor at my company, i remember thinking “oh cute, tiny ass and beautiful eyes” at first. She seems shy, very “little girl” like (although she was 24yo). While getting introduced to other colleagues, we all agree to hang out at my place on friday before hitting the pubs.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? No planning, vodka started it. She came to my place, we bought booze. We waited for the others. They all ditched us. She thought it was some sort of trap, so she called the other guys who all confirmed they were just tired. I felt she was uncomfy, although she liked me, so i offer to call it quits for that night. She said that hell no, we might as well have a few drinks and head to town. Few drink became a lot of vodka. We never left the place: when i get drunk, i get sleepy, not horny, so i just wandered off to the bedroom and crashed. The next morning, I wake up  naked, and I never sleep naked. I’m alone so i think “WTF happened?” I go to the kitchen, and here she is, ashamed and embarassed. So I ask: what happened? She said we had sex, so i start freaking out about condoms (i am a safe sex freak), and went to the room to find a filled condom handing on my shelf (pfeew). She was terribly embarassed that I would brag about it at work and make her look like a slut. I never told anyone, and we became friends with benefits. Which gradually lead to very hardcore experiences.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? first night, i have to trust her, I have no memories of it: she joined be in bed, tried to wake me up. I didn’t. she tried again later, I did wake up, got horny, she found a condom in my drawer, put it on, she started by riding me then i apparently put her on the bed, belly against the mattress, and brutally fucked her in the ass (it seemed to her like i just went blind and it was not willingly). I was super apologetic the next day, and she simply replied “well it’s ok, i like it and guys never really dare to take you hard like in your fantasies. It hurt but it was good”.  That was the first time.

Then we talked about it, got turned on at the idea of doing it again. She said “i don’t mind being a sex friend, i just want guys to tell me what is what, not lead me on that it’s a relationship”. She was very shy and previous looking, most guys including me thought she was the romantic cutie pie, so i never quite dared to go hard at the beginning. So one day, she started teasing me, calling me impotent and not daring to bang her like a man…i ask if that’s what she really wants, because it can escalate quickly into some brutal sex. She said “show me, still waiting”. We then fucked regularly for about 6 months. it usually went like this: i was just grabbing her ass, she got turned on in 5 secs. They pulling her pants down and fucking her ass immediately. I love anal so i seized the opportunity to do it a lot with a girl who likes it. we did little oral as she claimed she didn’t like it. I mostly was doing her ass and pussy alternatively, cuming in the condom. One day after christmas break, she got addicted to swallowing. Some guy did the job of convincing her into it. I still thank him for that ! At the end of the relationship, it got pretty hardcore. She said she wanted to push the limits: we bought a dildo, made video where I was doing her with the dildo (DP), coming in her mouth, very intense anal etc. one night, we got carried away, it was the third time and I was trying to come in her mouth, but I couldn’t. She put it in her ass without the condom. At this stage, she was asking for unprotected sex and we had both been tested before, it was just me being paranoid. Unprotected anal got me going in no time, and she took it out and swallowed it all. Only after she realized she sucked me after anal. She got so carried away she didn’t realize. A sign that she was really enjoying.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? condoms. We once in 6 month didn’t use one, and for like 1 min. We had been tested before anyway.

What were your REASONS for having this hookup? understanding of each other taste, my taste for dominance and her taste for submission: we could let go fully, like with few other people.

Were alcohol or drugs involved? If so, how much? alcohol the first time, a lot. Otherwise nothing

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? awkward at the beginning, great trust and understanding on the long run

To whom did you talk about the hookup? How did they react? a few friends, they thought it seems like good fun

Was this a consensual and/or wanted experience for you? For your partner? yes, very much wanted

Do you regret this hookup? If so, why? not one bit

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? best: letting go, total sharing of our kinkiest side, being able to do things i usually don’t dare. The raw “i’ll fuck your ass anywhere anytime” experience
It confirmed that good sex is a matter of mutual understanding, communication, daring and trust. it’s never about tits and ass or technical aspects

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup or anything else? i wish we did it longer

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