What’s your gender? Man
How old are you? 25
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Calgary
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Engineer
What’s your current relationship status? Dating casually
Religious affiliation: Christian
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)? 7
How many hookup stories have you here posted before? 0
How long ago did this hookup happen? 3 years ago
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 less than a week
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? Jenny was 23, worked as a nurse. Blonde, fit, small/medium tits with nice big nipples. She lived with her mom Tammy, who was in pretty decent shape for her age. Guessing 50? I was working on a custom harvesting crew that summer. We started in Texas and worked our way north. The crew would set up camp in some of the smaller towns along the way. We lived in long campers with not much privacy. My boss was great though. Easy to work for and he liked to tease us young guys.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We got rained out around 6 pm one day and boss said we could have the next day off so we all went to one of the bars in town for some fun. Maybe 25-30 people in there, 10 were from the harvest crew. Jenny was there with a few friends. We all noticed her and her blonde friend. I went and bought her friends a round of drinks and asked if I could sit. I made it obvious I had eyes for her and not her other friends. We ended up at the bar along talking and by end of the night kissing. She offered to come to her place to watch a movie. I figured why not. We ended up watching TV and of course fooling around. Soon we were fucking! She was amazing. Tight pussy, and she let me pull off the condom and cum on her tits. Next morning she drove me back to the campers and I got her number. We texted a bit that day and it rained so we met at the bar again that night. Tonight we left early and went to actually watch a movie. I liked her a lot. We got along great. After the movie she gave me a bj and I came in her mouth. I went down on her and she came to. I went to get some water from her kitchen when the door swung open. I was dressed but without my shirt. In walks her mom. She says you must be Ryan? I’m Tammy! Jenny told me about you. It was awkward at first but her mom was a nurse too and was just getting home from work. We ended up having a beer with all 3 of us in the living room. Her mom went to bed and I said I should leave too but Tammy insisted that I stay. Jenny and I had sex again that night with her mom just down the hall. With my boss’ permission I ended up staying at Jenny’s while we were in town. It was only a few blocks from our camp so I could easily walk to work.
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? Jenny was back to working the morning shift which meant she was gone by 630. I was usually gone by then too. We were likely gonna be in this area for a month so it was nice having a hot shower at their place every morning as opposed to the camper setup. We awoke one morning to thunder and rain, no work for me that day but Jenny had to work. I stayed in bed to catch up on some sleep. I went downstairs to the kitchen and Tammy was cooking a big breakfast. She was wearing her robe and I had to admit she looked very good for her age.
Jenny’s dad wasn’t in the picture since she was a little girl, so no husband around this house. I sat at the table and when Tammy brought the pan over with the eggs I couldn’t help stare down her partially open robe when she bent over. She caught me starring and said “checking out my hammers?” I was mortified.
She laughed and said “Don’t be embarrassed, it’s nice to be looked at by a young hung stud!” I said “hung?” Jenny told me you were a sizeable man! No wonder she’s in such a good mood. I’m not small but wouldn’t say I’m huge by any stretch.
I started to eat and the sexual tension was high. Soon Tammy was cleaning up the dishes and her robe was getting looser. Her nipples poking through told me she was naked underneath and there was no visible panty line either. I was wearing sweatpants and my dick was getting hard. She was eyeing me up as she cleaned and soon I couldn’t handle it anymore. I said “anything else Jenny has told you about me?”
Tammy turned and said “I’d rather find out for myself”.
With that she undid her robe, put her hands on her hips to give me a glimpse of a trimmed black strip on her pussy and her big soft tits. I mouthed the word wow to her and she started to walk towards me. With that I stood up, pulled down my sweats, stripped off my shirt and sat on the chair with a raging hard-on. Tammy straddled me, grabbed my dick, aimed it at her entrance and in one motion buried herself on me. There we were fucking on the kitchen chair with my face buried in her big tits.
She came so quickly that she dismounted and bent over the table, and said your turn. I fucked her doggy style for a while but wanted to see those big tits. I pulled out and led her to the couch and fucked her on her back. Her tits were flailing around when I announced I was gonna cum and asked if I should pull out. I didn’t even think of a condom and then realized she isn’t that old and could get pregnant. She said, “cum wherever, I’m fixed.”
I took that as an invitation to cum in her pussy so I let the first few spurts go inside and then pulled out and came all over her pussy and her saggy tits. Easily the biggest load I’ve had as she was covered. I spurt out that I’d never cum that much. She seemed impressed and was rubbing her pussy with one hand and and her creamed tits with the other. Reality set in and I thought about Jenny, she was so sweet and hot and although we weren’t serious, I just fucked her mom. Tammy must’ve seen my face and said not to worry. Jenny will never know so long I get a repeat performance. After that morning I became an exhausted man. Usually Jenny at night and her mom in the mornings as soon as Jenny went to work. I was often late to the morning meeting but the crew and my boss always joked that they young girl must be really clingy. Little did they know.
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? Felt guilty for sneaking around on Jenny. After I left town for our next state we texted lots. I never got the impression that her mom said anything. Went back the next year but Jenny had moved to another state to a better job. Had hoped her mom was willing to play but she said no.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal, Condoms
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)
How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it
What substances did you consume? Alcohol
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? Just my buddies back at home
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? The craziness of screwing both mom and daughter. Together would’ve been awesome
What was the WORST thing about this hookup? I love anal, neither of them wanted it.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all negative
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