Mixing Business with Pleasure



What’s your gender? Man
How old are you? 28
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: Some college (not currently in college)
What’s your occupation? Mechanic
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 6
How many hookup stories have you here posted before? 2

Mixing business with pleasure

How long ago did this hookup happen? 2 weeks

What was your relationship status at the time? Same as current status

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For 1 to 3 years

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 is late 30s to early 40s, her face shows her age more than her body does but still a decent face, nice size tits and a nice ass, average height and weight, she is a milf/cougar divorced with a couple kids, and she is fairly flirty/friendly. I know her because we work for the same company, but different departments. Ive always found her attractive for an older woman, a little past her prime but still got it.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It started with an unofficial Christmas party with the guys from work[mechanics] at the strippers, there were a few extras from other departments that showed up as well including her. We were there for a couple hours, had a few drinks watched a few dancers and I was ready to go, she lived in the same neighborhood as me and asked if I could give her a ride home because it was snowing out and I said yes without thinking much of it. As we are sitting waiting for the truck to warm up, she starts chatting me up, asking questions like if I had a girlfriend or a roommate which was no for both, I still didn’t think anything of it. We finally leave the parking lot and about a block from the bar she puts her hand on my thigh, I glance over at her with a surprised curious look and she just smiles but I quickly return my eyes back to the road with the heavy snow falling. She doesn’t stop and she runs her hand up my thigh and starts rubbing my cock, again I look over at her this time asking what she is doing and her response is, “It’s your lucky night, let’s go to your place.” I knew exactly what was going to happen and I knew it was probably wrong, but with a million thoughts running through my head I headed for my house trying my hardest to focus as she jerked me off.

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? She wasn’t waiting till my place and started giving me road head. I was able to hold off to my drive way where I barely got the truck stopped before exploded and she sucked it out of me, swallowing it without hesitation. When we got inside, she took charge getting me naked then stripping for me, I was still kind of shocked by what was happening and at first I just followed her lead. It didn’t take long for the reality to sink in at which point I really go into it. We went at it for a while trying many positions and she finally rode me to orgasm in cowgirl, which was too much for me. I couldn’t get her off of me in time and blew my load inside her, which worried me at first as she hadn’t mentioned she had an IUD. We laid there for a bit talking, she made it clear no one could know and assured me I didn’t need to worry about cumming in her because of the IUD. She wanted to have a shower before going home so I joined her and we fucked again. I suggested she stay the night and I could drive her to her car in the morning but she had a sitter and had to go home.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? I drove her home. I felt kind of weird but good the next day. I was worried about seeing her at work but it’s like it never happened, which is good. I have no expectations for the future. I would do it again, but I think it was a one-time thing.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) IUD (Intrauterine device)

What were your motives for this hookup? Fun, pleasure, horniness, Just happened, I don’t know why, just went along with it, It was easy / convenient

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? I don’t know / I’m not sure

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? No one

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Being with an older woman who knew what she wanted.

What was the WORST thing about this hookup? I was kind of caught off guard and maybe didn’t get to enjoy it as much as I wanted to.

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? It was different having a woman who knew exactly what she wanted. I feel I was used by her, but that’s fine.

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