What’s your gender? Man
How old are you? 21
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: Some college (currently in college)
What’s your occupation? Full Time student
What’s your current relationship status? In a serious relationship (monogamous)
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)? >20
How many hookup stories have you here posted before? 0
With Ex-Girlfriend’s Mom
How long ago did this hookup happen? 1 week ago
What was your relationship status at the time? Same as current status
How would you best classify this hookup? Short fling
How long did you know the person before this hookup? For more than 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? Cathy (not real name) & her husband lived in the same subdivision as my parents and were good friends. Jessica (not real name) was Cathy’s daughter. Jessica and I dated for 6 months in high school and had sex on a regular basis. Cathy was open-minded and had Jessica on birth control and didn’t mind when we had sex in Jessica’s room and even allowed me to stay the night on occasion. I broke up with Jessica because she turned into a bitch.
Cathy was in her late 40s or early 50s but looks around 30ish. She’s tall, lean, tan, jet black hair, defiantly a MILF. She works at a bank and always wears tight business skirt suits with heels.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My parents own a 45ft cabin cruiser docked at the lake and I live on it during summer break with my girlfriend but she went to Greece with her sorority and was due back in 3 weeks. It was Friday afternoon and I heard a voice on the boat saying my mom’s name. I was still in my boxer briefs as I unlatched the hatch to the rear deck. It was my mom’s friend Cathy. Dad and Cathy’s husband were out of town playing in a golf tournament and Mom had invited Cathy to go out on the boat for the weekend. Cathy called Mom. My mom’s a realtor and was busy preparing a 1.2 million house for an open house tomorrow. Cathy told Mom she would reschedule and got off the phone. Cathy was wearing a thin white sundress, glasses and a big hat. She began to leave the boat and I said, “Why leave? We can still take the boat out.” Cathy smiled and said, “Are you sure?”
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? We left the marina and cruised up the lake for 40 minutes till we reached a private cove. I dropped anchor and we decided to cool off by taking a swim. Cathy was wearing a conservative bikini but still looked sexy. While in the water, she swam up and gave me a kiss then a tug at my shorts. Her hand went down my shorts and wrapped around my cock. We kissed more, then swam back to the boat. She took off her swimsuit so it would dry. She was naked and for her age, she looked great and I loved her tiny & very thin landing strip. I knew what was about to happen so I took off my shorts. She wasted no time, got on her knees and sucked my dick. She straddled me and began riding me hard and fast. Her ass was moving 100mph on my dick. I squeezed her tits and she let out a loud “OH YES!” she had gotten off. She bent over and let me have her doggy style. I lined my dick up to her wet pussy, grabbed her hips and drove it deep inside her fast and hard. She was so tight and I was trying not to bust a nut so fast by controlling my rhythm. She loved her ass smacked and hair slightly pulled as I increased my pace. She told me it was fine to cum inside her so I did.
Afterward, I asked if she wanted me to take her back or we can stay here for the night. It was getting dark fast so she suggested we stay. I made sure the boat was anchored well then she opened a bottle of wine she brought. We talked and had sex 3 more times that night and I filled her up each time with everything I had.
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? The next morning, we had sex then swam until it was time to leave. She gave me a blowjob as I drove back to the marina. I docked the boat and before she left, she stuck her hands down my shorts and was softly massaging my sack. She looked me in the eyes and said, “Who’s better?” I looked confused. She said, “Me or Jessica? Who fucks better.” Without a delay, I grinned stared back, being truthful and with a confident tone I said, “You of course.” She smiled and said, “You’re much better than my husband.” She grabbed my phone and loaded her number and added, “Use it as often as you wish.”
Starting on Monday, she began stopping by on her way home from work for some intense sex & she leaves. I think she looks sexy in her work clothes.
I don’t know what’s going on in her life but I’m enjoying the sex for now. Being curious one Friday night, I sent her a booty call text. GR8 SUNSET 2NITE. IT WOULD B BETTER WITH A BOTTLE OF WINE & HOT MILF.” 30 minutes later she arrived wearing a bikini top & denim shorts with a bottle of wine in each hand. I noticed she was full of energy and acted like a young girl that snuck out of the house to enjoy life. We started out sipping on wine and talking for an hour. Then had lots of sex and she spent the night.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None
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? Nobody but my mom found out. I think someone at the marina tipped her off.
Surprisingly, she was somewhat calm. I’m 21 and she knows I’ve had a history of hooking up with girls. That’s why I stay on the boat when I’m in town but she was shocked I was hooking up with a married woman that was also her best friend. To protect me, Mom promised not to say anything because it might draw attention to the situation. However, I got the standard awkward questions, “How long do you plan on seeing her?” As long as she wants. “Are you using protection?” no. “What if you get her pregnant?” You will be a grandmother. End of talk.
How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)
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? Having sex with a MILF. The sex is better than my current girlfriend too. Any guy should give it a try sometime.
It wasn’t at the same time and it there was 4 years between events but now I can say I’ve had sex with a mother & daughter. The mother was the best.
What was the WORST thing about this hookup? Mom found out. I don’t like the awkward conversation.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Older women are better at sex, fun to hang out with and talk to. Right now, I love the sex but we are spending a lot more time enjoying the long evenings on the boat cuddling with a bottle of wine and having quality conversation.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all negative
You have a hookup story to share? Submit it here!