My First MILF

by Joe

What’s your gender? Man
How old are you? 30
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Dating casually
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? >50
How many hookup stories have you here posted before? 0

My First MILF

How long ago did this hookup happen? 12 years ago

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

How would you best classify this hookup? Friends-with-benefits

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? Kristi was short. She had long brown hair and hazel eyes. She was 22 yrs old and a mother of one. She got pregnant at a young age and the father hit the road. She hasn’t heard from him in years. Her family was supportive until she dropped out of high school and got a job at the mall working most evenings. Now that her daughter is old enough to start school, Kristi decided to take classes at the satellite campus of a local junior college. I was 18 at the time and fresh off a wild summer break. My parents insisted I try college so I enrolled at the same junior college for a few classes.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She was in my first class and instantly began making eyes at me. Our schedules were similar: class, one hour break, then another class. At first I thought she was my age or a year older. We began talking and she told me her story. We instantly got flirty and when we sat outside at a picnic table she would place her hand on my leg. I’d return the favor. She had smooth legs. We shared stories of each other’s wild pasts. Some of the stories she shared were crazy! She was a wild child! She told me it was hard being a single mom because guys usually ran off and weren’t interested in ‘dating’. The only thing I could say is, “It’s been a while since I’d been on a date too.” She grabbed my hand and said, “I’m not talking about dating. There’s no way I could juggle a boyfriend right now. I’m talking about getting laid. It’s been a long time and I’m overdue.” I winked and said, “I get it.” I told her if we can work things out we should do it sometime. She gave me a peck on the cheek and rubbed her hand across my crotch. Later that day we walked to our cars together and she surprised me with a kiss.

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 arrived at our first class the next week, there was a note on the door: “Class canceled due to instructor illness.” Now we had two and a half house between classes. She asked what I was going to do. I lived 30 minutes away and planned to hang out. She lived 10 minutes away and asked if I would like to come by her place for ‘fun’. I gave her a naughty grin and wink and we took her car. On the way, I asked if we needed to stop to get condoms. She said it was my call, she’s wasn’t worried about anything and she had IUDs. We both agreed condoms were not necessary.

We got inside her place, she jumped up on me, and we kissed. All our clothes were off. I was already hard and she got on top. She was wet and I went inside her easily. I played with her tits and held her ass while she rode on my cock. She had an orgasm and I released inside her at the same time. We took a break and did it again. This time we did doggy. When we finished she gave me a deep kiss and thanked me. We still had time so we hung out. She fixed sandwiches and we watched TV until it was time to go back.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? We hooked up many more times that semester. We tried to get a similar schedule for the next semester but it didn’t work out. We stayed in touch but gradually slowed down seeing each other because her work schedule changed, her daughter was getting older and doing sports, and I switched to a four-year university. We hooked up once a month for a little while then we stopped. Currently, we follow each other and chat on social media but that’s the extent of it.

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, Attraction to partner(s)

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 few friends. They told me I was the first in our group to nail a hot MILF.

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

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? She was the best partner I’d ever been with up to that point.

What was the WORST thing about this hookup? We slowly grew apart.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not at all. I’m still single and casually hooking up.

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? More people should be open to casual sex.

What do you think about the Casual Sex Project? Nice place to share stories and read people’s experiences.

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