Highest education received: Post-graduate degree (currently pursuing)
Occupation: University Development
Religious affiliation: N/A
How religious are you? Not at all
Sexual orientation: Bisexual
How many hookup stories have you here posted before? 0
Good Girl has a Hookup
How long ago did this hookup happen? Four Months
How would you best classify this hookup? One-night stand into ongoing FWBs
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? I was leaving an event and my friend and I decided to stop by the hotel bar for a few drinks after a pretty long day. I sat at the bar as she went to the restroom and an older man in his 50s struck up a conversation with me. He recognized me from the event but I was unable to place his name. We introduced ourselves and I couldn’t help but have this instant attraction to him. He was about 6’4, with dark hair with a little gray, blue eyes, and very expressive while talking. His face had crows feet as he smiled big, showing his white, straight teeth. I learned he was in his late 50s, over thirty years older than me. He was very nice and had the whole intellectual thing going. My friend began to talk to his friend when she returned, but they were both married and kept the conversation strictly about work.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I began to initiate touching and physical contact after they closed the bar and moved into seating in the middle of the hotel. Soon after, with my drink still in my hand, I went over and sat in his lap and his hand began rubbing my back and slowly down to my ass as I got chills. He held my hand with his other hand. My friend sat across from me also pretty drunk talking with his friend as we began whispering and I learned more about his army training in health professions (retired now), his undergraduate and doctoral training, etc. It was 3:00 in the morning, and I knew my friend and I had to be setting everything up at 6:30. We all got in the elevator together and my friend and his friend got off at the 5th floor. My sex interest was in the elevator with me and staying on the same floor! We slowly began kissing in the elevator and he invited me back to his room.
What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? When we walked into the room, I stripped down to my bra and panties and laid across his bed. He stripped down to his boxers and held me close, just rubbing up and down my body with one hand. Shortly after, he told me he had complications from type 1 diabetes and he had a hard time getting and staying hard, but that he loved oral and making a woman come. I put his hand beneath my panties and he began to rub my clit. Then he pulled down my bra a little and took my nipple in his mouth. I came a few times from that (I’ve learned how to have multiples) and then he began kissing down my breasts and stomach and to my v. He gave me oral and rimming and I kept coming. After a little while, I took his cock into my mouth and was able to get him very hard, at that time I flipped over onto my stomach and into doggie as he put his cock inside of me. He was able to come and we collapsed. I fell asleep in his arms. When I woke up, he gave me more oral and I came once again before rushing to my room.
I felt amazing during the hookup and felt like I was being cared for. He was definitely (and still continues to be) a great lover. In the end, we fell asleep. We have hooked up a few times since and it’s always very fulfilling.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I have the BC implant and we used the pull out method because I’d been on antibiotics. We did discuss briefly that neither one of us actively had an STI.
What were your REASONS for having this hookup? I was in the mood and very attracted to him. I wasn’t planning on hooking up with anyone, but he was very attractive.
Were alcohol or drugs involved? If so, how much? We both had some drinks earlier on, so I’m not sure how many. I was buzzed, but we both agreed about having sex and I did think about it.
What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? After we hooked up the first time, we hooked up more times over the weekend. We had downtime that next day and the following night. I like him a lot, but there’s some distance that prevents us from having a serious relationship at the moment. He is a great guy and we’ve kept in touch, continuing to talk every day.
To whom did you talk about the hookup? How did they react? About two weeks later, I told my friend and coworker that I hooked up with him. She wasn’t surprised and asked a lot of questions about the age difference and how it changed things.
Was this a consensual and/or wanted experience for you? For your partner? We both consented to having sex.
Do you regret this hookup? If so, why? I actually do not regret it at all. If anything, I wish we had gotten a chance to have had more time the first night.
What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing and what still continues to be is that he is great at oral and I cum easily. I’ve also became more comfortable with my body after being with him. I wouldn’t say the worst thing, but more unfortunate is that he has long term issues that make penetration difficult, but not impossible. Penetration is great, but it just requires an amount of awareness.
This was my first casual hookup and I have to say I have enjoyed it and it has changed my ideas on not only casual sex, but sex with age differences.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all negative