Casual Sex with an Older Black Woman from Craigslist

by Andrew

This post is sponsored by Trust Massage Oil.

What’s your gender? Man
How old are you? 26
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States. Madison, Wi.
Highest education received: Some college (currently in college)
What’s your current relationship status? Single
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? 0

Casual sex with an older black woman from craigslist

How long ago did this hookup happen? 1 month

What was your relationship status at the time? Single

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? She was a mature, african american BBW (big, beautiful woman) . Huge breasts and ass, nice big juicy lips, short hair. I’m into older, larger women, so she was perfect for me. She answered a craigslist ad I had posted searching for an older BBW interested in sex with a younger guy. She was 55, I’m 26. We chatted through email and then text for a day. I felt anxious and nervous before the hookup, but also extremely horny and excited.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She had recently moved to town and was living with her son and his wife. She didnt have any means of transportation, so I drove over to their place and picked her up. When I pulled up, I texted her that i was there, and she came out after a few minutes. She was plump, with a very dark complexion. I could see how big her tits were through the dress she was wearing. She had black/gray hair, pulled up in a small bun. She got in and we greeted each other. The drive back to my place was about 20 min, the conversation was a bit awkward at first, she expressed some nervousness about being with a younger guy, and commented about how her son was the same age as me, which turned me on a lot. Eventually we clicked and the conversation was flowing, she told me that she had just moved to Wisconsin from Florida recently, and hadn’t had any sexual interactions in a while, and that she was getting tired of ‘self-satisfaction’ AKA she was tired of masturbating and was wanting the real thing. When we pulled up at my apartment, she looked at me with a nervous but excited face, and we got out of the car and went upstairs.

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? When we got into my room, she sat down on the couch, I sat next to her and asked if I could kiss her. She said yes in a shy way, and we started making out, sucking tongues. I quickly started feeling her large breasts, and reached inside her bra to feel her nipples. I took my shirt off and she took off her bra, she started breathing heavy as i rubbed and pinched her nipples, I could tell she was getting very turned on as she reached into my pants and started rubbing my cock. After a few minutes, i pulled down her panties and spread her legs, her pussy was nice a thick, with just a bit of hair. I commented about how wet she was and she smiled and said that she usually gets very wet. I buried my face in her pussy which was drenched, and began eating her out vigorously, sliding my fingers in and out of her while working her clit with my tongue. Her pussy tasted amazing and I had her juices all over my mouth and face. She was pinching her nipples and breathing heavy, and told me how much she had needed this. After a while, we moved to the bed, i took off my shorts and boxers to reveal my throbbing hard cock. I asked her if she liked sucking cock, and she said she did. I laid on the bed as she quickly took my cock in her mouth, slobbing all over it, I almost came after a few min and had to push her back for a second to recover. She then started sucking again for a while. I pulled her up and we made out for a minute. I then laid her back and spread her big legs wide, i rubbed my cock on her clit for a bit before plunging it inside of her raw (she was 55, and told me that condoms weren’t necessary as she doesn’t get pregnant anymore because of her age, and because we were both STD free). We fucked missionary for a bit, with her legs and feet up in the air. I have a bit of a foot fetish, and she had amazingly soft feet, I asked her if I could suck her toes and she smiled and said yes, she said that she takes very good care of her feet and she was glad that I noticed. After fucking her missionary for a while, and sucking her toes/licking her feet, she commanded me to turn her over and fuck her doggy, which i gladly obliged. Her ass was huge and I smacked it hard as I pounded her pussy from behind, she yelped from pleasure. We fucked for a while and when I was about to cum, I pulled my dick out and started eating her pussy from behind. Then I put my cock back in and started thrusting hard, she was really enjoying the doggy position, and having her big ass slapped. I got close to cumming again and pulled my dick out, I asked if she would suck me off, which she did, but she didnt want me to cum in her mouth, so i asked If I could cum on her huge breasts, which she said yes to. So i stood up and she sucked her pussy juices off of my cock for a few minutes. When I couldnt hold off any longer, I pulled my cock from her wet lips and busted a huge load on her tits. It was extremely satisfying seeing my white, hot, cum running down over her big nipples. We were both pretty exhausted at that point, and I walked into the bathroom and grabbed her a towel to wipe my cum from her tits. We then got dressed and talked for a bit, agreeing that we had both had a good time and that we should meet up again in the future. We then got into my car and I drove her back home and dropped her off at her sons house.

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? After I dropped her off, I drove back home and cleaned up. I felt a little strange for the rest of the day, although I love older women and often fantasize about them, she was only the second older women I had ever been with. I was a little worried about the risk of an STD, although we discussed it beforehand, and neither of us had any history of STDs, I was still a bit worried. A few weeks later I went to the doctor and got tested, and everything was all good. I’d like to meet up with her again, but I haven’t contacted her yet. I plan to get in touch with her sometime in the near future.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Thought it was an important experience to have

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? Havent told anyone.

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? Everything, we were both very giving and enjoyed each others bodies.

What was the WORST thing about this hookup? I would have liked to cum in her mouth or inside her pussy.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Made me more open to casual sex with older women.

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

All things considered, how NEGATIVE was this experience? Not at all 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? It seems that casual sex is becoming more accepted in society. I would like to experience more casual sex with different kinds of partners, older women, married women, SSBBWs, etc.

What do you think about the Casual Sex Project? Its awesome

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