First Time And With Friend’s Mother



What’s your gender? Man
How old are you? 55
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? San Francisco
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Engineer
What’s your current relationship status? Engaged/Married (monogamous)
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)? Many
How many hookup stories have you here posted before? This is the first

First Time And With Friend’s Mother

How long ago did this hookup happen? 34 years

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

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 as a much older married woman–the mother of another Boy Scout when I was in scouts. She was overweight, plump and round, with large breasts. She wore her dark hair long and unfashionable write rimmed glasses.

She flirted with me for a long time, making clear that she wanted a connection. She would walk up behind me and rub her breast at my elbow… and make ribald comments. It was flattering but kind of tawdry. She wasn’t attractive. But it was head turning.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? One night my parents were away for some reason, and she drove me home from some school event, except instead of going to the house she drove to the beach and parked. She said she wanted to talk “now that I was eighteen and legal”. We talked about girls and guys getting together. She told me that she’d never had a man not go after her tits. After a while, she moved to kiss me and we shared a kiss. A long series of kisses. Then she stopped me and said we needed to go somewhere private. We went to my house and instead of doing me off and leaching, she came inside.

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? In my house, things got hot quickly. We started kissing again and I felt more confident. My hands were holding her body and feeling her curves. She was wearing a long brown sundress, shapeless except around the bodice, where it outlined her breasts perfectly. I remember that it was embroidered in a kind of Mexican or Mayan pattern. We were kidding and sitting facing each other in the living room.

At some point, she touched my cock, letting herself feel how hard she made me. I let my hand wander up her skirt, feeling her thick fleshy thigh and then her ass. We were both excited now, breathing hard, flushed with it. She told me how deprived she was, neglected. How much she desired me. Then she reached down and undid my belt. Then my pants. Then she reached into my underwear and stroked me. It was heaven.

We kept kissing and I worked up the courage to touch her pussy. It was soft, surrounded by folds of flesh and well-furred. It was also soaking wet. She gasped and kissed me hard. Then she asked, “can you control it?” She meant my orgasm.

“No,” I admitted.

“I’m very fertile. Every man who has cum in me has made me pregnant. Can you control it?” She was adjusting her skirt and pushing me back. It was clear she was going to mount me. My excitement and passion were rising.

“No,” I said. “I can’t control it. I’ve dreamt this too many times.” (Her attention didn’t go unnoticed, after all.)

“Oh,” she said, and I felt the first touch of a woman’s wet nether lips. She sank down, hard and fully upon my straining manhood, paused, and then began to ride me in earnest.

Let’s be honest: that first time I didn’t last long. I came fast, hard, and hot deep within her. As deep as it was possible to go. She smiled as I roared my climax, grinding her pubic bone into mine.

After a minute she pulled off. “Good,” she said. I was all hard, ready for more, but mindful of being missed, she left.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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? She was right: she had a daughter secretly of mine, conceived no doubt that very night. I was confused, worried, thrilled, excited. There were so many conflicting things. I didn’t know how to react. I was hooked on sex (and of pregnancy risk), but she was obviously the wrong woman to get with of many levels. When she told me she was pregnant, that was amazing, and I experienced the pregnancy at one remove with her. We didn’t make love again until years later (another story), but she was my first.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Just happened, I don’t know why, just went along with it

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? A little bit

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? 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? No one. I’m admitting it here.

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? A little bit

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? The amazing feelings, how it freed my sexual feelings, the delight conceiving my daughter gave me.

What was the WORST thing about this hookup? The secrecy, the fact that I didn’t consent, the extreme stresses, especially once she turned up pregnant.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It’s the core of much of my subsequent sexual history.

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

All things considered, how NEGATIVE was this experience? A little negative

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? I’ve enjoyed both casual and committed sex. It’s been a big part of my life, sometimes causing problems. I’ve struggled with controlling it sometimes.

What do you think about the Casual Sex Project? Thanks for being here.

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