Second Extra Conquest



What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Iowa
Highest education received: High school diploma
What’s your occupation? Maintenance management
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Sex addict
How many sexual partners have you had in your life (including oral sex)? +/-15 and growing
How many hookup stories have you here posted before? One

Second Extra Conquest

How long ago did this hookup happen? 10 years ago

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? Just met that day

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? After meeting my first extra-marital friend on Craigslist, I turned to it again for a second (concurrent) playmate. This time I posted an ad and received a reply quickly from a younger lady that was going through a divorce (ironically because her husband cheated on her). So, I had only physically met her about 30 minutes before I was inside her. We met at a restaurant after she got off work, went straight to her house a couple minutes away, and two minutes after walking in the door we were passionately making out.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My ad was pretty clear on what I was and was not wanting. So, like I said before, there was no time wasted with idle chitchat pre-sex. I suppose in this instance I clearly instigated it. I wrote the ad and once we were in her house, I grabbed her and started kissing her. Pretty remarkable for a shy boy from Iowa.

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? Within a few minutes of standing in the doorway kissing and touching, she asked me if I would like to go to her bedroom. I told her I really didn’t care if we went to the bedroom, the couch, or the floor – I just wanted her. She took my hand and led me to her room where we both instinctively started stripping. She laid back on the bed and pulled me down with her, until I hovered over her. She reached down to guide me inside her, but I couldn’t even start to get in her because she was dry. I was very surprised by this and she was very embarrassed. She told me she didn’t get wet when she was nervous (which over the course of our relationship, it was never a problem again). So, I assured her it was okay as I went down on her. It didn’t take long to get her wet and I typically would love to spend a long time between a woman’s legs, but I didn’t stay very long there. Her response was good enough, but one of the finest joys of eating pussy (and I consider myself a pussy eating connoisseur) is the taste. I’ve found every woman has a unique flavor and they’re all different – some better than others, and some an acquired taste, but all, at least eventually, scrumptious. She had no foul odor. She had no strange taste. She had no dirt, no lint, nothing like that. She had, instead, absolutely no scent or flavor whatsoever. Her pussy was…….bland. It looked nice. She was perfectly smooth because instead of shaving, she plucked herself.

Anyway, once the juices were flowing, I came back above and kissed her deeply while I slid my cock inside her. She felt bland too. It was still good, just not intense. She sighed that sweet sigh that only a woman in intense lustful pleasure can make.

She liked what I did (except trying to finger her anus-she exposed that as a no-no right away). Any position. Any depth. Anything.

Second, when she rode me (one of my preferred positions), she had a strange angle that she ground at. I don’t know how to explain it. Apparently her soon to be ex-husband’s dick was shaped like a question mark. It hurt. It felt like she was going to snap my cock off at the root. I absolutely loved it. It was the most intensely pleasurable pain I had ever felt.

Third, she was multi-orgasmic. This was a first for me. I had by this time trained myself to last a very long time. I don’t remember how many times she came that first time but, I would say it was on the order of six. And that was with absolutely no break in the fucking. She only took a break once to go pee.

Fourth, she was a screamer. Like bust my eardrums, wake the neighbors, screamer. I wasn’t sure what to make of that.

Fifth, when we finally did finish, she was looking at me all sweetly. That “I think I’m in love” look. I told her not to fall in love, I wasn’t getting divorced. She told me she thought it might be to late.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, multiple

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? By this point, I had already become a little numb about what I was doing to my wife, so I was just generally satisfied. We agreed to meet again, soon. I really liked that I had pleasured her so. I was more turned on by what I could do to her than what I was getting. In retrospect, I wish I had left after one night. She ended up letting me use her as my own personal, secret, anytime booty call for a couple years. I didn’t ask or expect her to be exclusive to me. I certainly wasn’t to her. Every now and then she’d get with another guy to try to make me jealous but it really didn’t even come close to working. That actually surprised me. I look back now and see just how much I took advantage of her.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

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

To whom did you talk about the hookup? How did they react? A couple of buddies. They weren’t surprised.

How would you best summarize people’s reactions about this hookup? Neutral

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? Very

Do you regret this hookup? Somewhat

Why do you regret this hookup? It was nice to have a pretty girl who never turned me down. She gave me a key to the house so that I could come have her anytime I wanted. If she was asleep, I would come in and wake her to fuck and then leave when I wanted. But, that was really selfish. I didn’t like who I became.

What was the BEST thing about this hookup? Sex on demand.

What was the WORST thing about this hookup? Girl in love with a dirtbag (me).

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. I don’t like the emotional toll this stuff takes on people. This one didn’t hurt me but it hurt her. I finally ended the affair because one of my other flings demanded it.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup? No.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? Casual sex is always bad. It feels really good at the moment but, in the end, someone is damaged, even if not “hurt”.

What do you think about the Casual Sex Project? Interesting

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