What’s your gender? Man
How old are you? 44
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? Engaged/Married (monogamous)
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 30+
How many hookup stories have you here posted before? 3
Hot Young Adventure
How long ago did this hookup happen? 10 years ago
What was your relationship status at the time? In a relationship (monogamous)
How would you best classify this hookup? Fuck-buddies / Booty call
How long did you know the person before this hookup? For 1 to 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? Tanya was the sister of a girl I knew. We really didn’t know each other or have a relationship, but we would run into each other from time to time and she seemed nice. She was 12 years younger than me and was a single mom. She had a tight body and long blonde hair. I didn’t really think much about her before she initiated some interaction.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Tanya worked at a coffee shop I frequented and I was meeting a coworker there for work when she asked if I would help her with something in the kitchen. She asked me to help her get something off the top shelf, so I lent a hand and she offered a big smile and a thank you. She also rubbed up against me when she grabbed the box from me. I didn’t think much more of it until she sent me a message on FB later that night. She said thank you and I said no problem. We chatted a bit before she said, “I really didn’t need help, I just wanted you to notice me and start a conversation”. After that, the conversation turned sexual and she suggested she could stop by my house sometime. My girlfriend at the time lived in another town, so I said sure, and that we could figure something out. Then we exchanged numbers.
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? The next day, she sent me a text asking if she could swing by after work and before she picked up her son. I said sure, and in about an hour I had a knock at my door. Tanya was there and she came in, putting her arms around me and giving me a long kiss. I commented that was a good way to get me to notice her. I sat down with her and we chatted for a bit. She asked me if I would show her the house and I guessed where this was going. We made our way through the tour, and when we got to the master bedroom she said, “this is what I was looking for,” and grabbed my hand, leading me to the bed, and pulling me on top of her with another kiss. As we made out, she unbuttoned my pants and started rubbing my cock. I felt her up through her bra and it was clearly time to undress. I took her shirt off and undid her belt so I could pull her pants off. I left her socks on and started to undo her bra as I kissed her. Her tits were perky and she had nice small nipples that were hard. I sucked on them as my hand made its way down into her panties and explored from her landing strip down to her swollen lips that I parted to slip a couple fingers inside.
She twisted her body toward me and rolled me over, kissing her way down to my cock that she took in her mouth. After a great blowjob, she sat up on her knees and removed her panties. Then she straddled me, sliding my hard cock inside of her without a condom. I took a deep breath as she lowered herself all the way onto me then slowly began to grind on top of me. I played with her nipples while kissing her, and let her lead the pass as she bounced on my cock. She was clearly in the lead at this point and continued to dictate what she wanted, rolling us over and taking me missionary with her legs wrapped around me. I was wanting a couple positions myself, so I rolled her part way onto her stomach and kept pumping as I straddled her legs like scissors. I really wanted her doggy and eventually pulled her up to her knees so I could enter her deep and hard. She arched her back and I reached around to grab her breasts and pinch her nipples. My cock was hard and as I started to pound more vigorously, the sound of my balls slapping against her was drown out by her pants and moans with each thrust. I could feel her anticipation building and was trying to hold out, but when she put her head into a pillow and arched her back I could feel her squeezing tight around me and I lost it, cumming inside of her. I kept pumping until my balls were empty. She turned around and pulled me tight, wanting to cuddle. We laid there and talked, her telling me she didn’t want a relationship because she didn’t think people would approve, but that she hoped we could do this on a regular basis. That got me hard again and I fucked her one more time, just pounding away at her in missionary while I wicked on her tits until I came again. She said she needed to go pick up her son and got dressed at that point and left.
How sexually satisfying was this hookup? Very
Did you have an orgasm? Yes, more than 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? Tanya and I met up a couple more times. Once was a random stop at her house years later where we snuck away to fuck quickly in their bedroom as her son was older and less innocent. She lives in another town now, but I chatted her while writing this story to tell her I miss our visits.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Birth control pill / patch / ring / injection / implant, Sterilization
What were your motives for this hookup? 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? My ex wife. She liked to tell me about her slutiness, so I shared my story about my much younger fuck buddy who she knew.
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
Why do you regret this hookup? Nothing
What was the BEST thing about this hookup? Fucking a much younger woman.
All things considered, how POSITIVE was this experience? Very positive
Anything else you want to add about this hookup? We continued to hook up as I was in a committed relationship and she was engaged. She made it clear that I could fuck her up until the night she got married. She wouldn’t fuck me after that, but her marriage didn’t last long, lucky me.
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