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What’s your gender? Man
How old are you? 28
What’s your race/ethnicity? Mixed / Multiracial
What continent do you live on? South America
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Program Manager
What’s your current relationship status? Dating casually
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 20+
How many hookup stories have you here posted before? 0

The Young MILF

How long ago did this hookup happen? Yesterday

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a month

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 a beautiful brown girl, 29, black hair, deep eyes, and unique features. She also has amazing calf muscles. We met through a dating app and after a few days of texting, we met at a bar and really hit it off. We chatted about all sorts of things, when I asked her to share her happiest memory there was some hesitation and she told me that she would share it with me if we end up going on a second date. I took this as a very promising sign. I really wanted to make a move then but she had to leave early to meet some friends so nothing happened. She is a tour guide, works a lot, and is not very responsive to texts. After a couple of times where she said she was too tired to go out, we met for coffee. She seemed a bit tense and after a few minutes of small talk, she disclosed she had an 8-year old daughter. I was a bit disappointed she wasn’t forthcoming when we first met but also didn’t really care. She was sorry for not being upfront about it on our first date and couldn’t really explain why she didn’t tell me. I walked her home and before saying goodbye I tried kissing her but she didn’t want to and gave me a long hug instead.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was a Monday and we hadn’t really talked for a couple of weeks. I decided that if anything was going to happen it needed to be soon. I texted her and invited her over to my place for some drinks. She had just gotten home and said she was extremely tired. I asked her if she could make the effort just this time as I was leaving on a business trip. She agreed as long as I picked her up and dropped her off at her place later that night. It was pretty clear by that point that we were both DTF. We had a few drinks and started kissing passionately. I suggested we moved to the bed and she agreed.

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? There was a lot of foreplay. We kissed and fondled each other for a long time. I pulled up her shirt and started kissing and sucking her nipples while rubbing her pussy over her panties. She got extremely aroused by that and clothes started to come off. Once we were naked, I continued sucking on her nipples and started fingering her. First with my middle finger and when I felt she was extremely wet I added my index finger. She started to moan very loudly and I decided to go down on her. I sucked her clit while massaging her vaginal wall. After a few minutes, she had a powerful and long orgasm. I gave her a kiss and she hugged me tightly. I was pretty hard so I put on a condom and entered her missionary. She said she hadn’t gotten laid in a long time and it showed as her pussy was very tight. After a few minutes, I started to get tired and sensed I might be losing my erection. I decided to switch positions and have her ride me. She wasn’t the best at riding cock but good enough to make me cum.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, 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? We spooned in bed until I got hard again but unfortunately I couldn’t penetrate her again because she had to go back to her place and take care of her daughter. I feel pretty great, she is the second young MILF I fuck. I enjoy the fact that young MILFs are usually DTF without any strings attached given their other priorities. I’m definitely not interested in pursuing anything serious with her and will probably follow the three strike rule. She doesn’t seem very experienced and was a bit curious about anal sex, so hopefully, I’ll get to take her anal virginity soon.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), It was easy / convenient

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

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

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

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

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

To whom did you talk about the hookup? How did they react? I haven’t shared it with 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? There was good chemistry in bed and the potential to explore more with her.

What was the WORST thing about this hookup? Nothing really.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Nope. I’m enjoying dating casually and getting laid with no strings attached.

All things considered, how POSITIVE was this experience? Fairly 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? I’m now very open to the idea of casual sex. I think it has allowed me to explore my sexuality and let off some steam. I’d like it to be more accepted in society.

What do you think about the Casual Sex Project? It’s great. I have switched from porn to this website.

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

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