Hooking Up With A Pinup Girl 25 years Later



What’s your gender? Man
How old are you? 43
What’s your race/ethnicity? Mixed / Multiracial
What continent do you live on? North America
What country and/or city do you live in? Toronto
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Business development
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 0

Hooking Up With A Pinup Girl 25 years Later

How long ago did this hookup happen? 2 years

What was your relationship status at the time? Single

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

How long did you know the person before this hookup? For less than a year

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? The local newspaper always features a model on page 3 called the Sunshine Girl. Back in the 1990s, I was about 16 years old when I saw a model called Brenda featured there wearing a black one-piece swimsuit. She had a beautiful face and an athletic body. I practically fell in love with her. I cut out that page and was masturbating to it a few times a week. Fast forward 25 years, a new hire shows up at our workplace called Brenda. She looked familiar to me, and then I realized it was her! She was still quite attractive, still had a nice body, only she was now in her late 40s. I still wasn’t definitely sure it was her, but I became quite friendly to her. She was quite accomplished with two Masters degrees, seemed to be moving around in careers, and I found that she was single.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Things were not going well in the organization where we worked. We had a terrible CEO. Brenda and I would often go for lunch to share stories. One day, our organization was shut down. We were all bummed out. Soon to be unemployed, Brenda and I went to a bar to have drinks. Having nothing to lose, I asked her about that Sunshine Girl spread. She admitted it was indeed her. I told her how attracted I was to that spread and how I still found her attractive. She enjoyed my compliments. We were both a bit drunk when I told her if she was interested in “something more.” She said yes, and we went back to her place.

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? I was so excited that my cock was hard well before we got to her condo. If I had fucked her as a 16 year old, the experience would have been a disappointment due to inexperience. At this age now, I knew what to do. I took my my time arousing her. We kissed deep into each other’s mouths, I licked her neck and breast and body and thighs, and I enjoyed the aroma of her crotch as I gave oral. I did everything I dreamed of doing when I first saw her as a Sunshine Girl. I massaged her clitoris and finger fucked her well. I told her how beautiful she was and what a hot body she had. She finally said she wanted me inside her. I fucked her missionary and orgasmed into her. We gave each other oral, and when I was hard again, I fucked her doggy style for quite a long time before coming again. We took a break, then we fucked a third time.

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? I stayed over the night and we fucked again the next morning. We were both soon to be unemployed, and we agreed that hooking up for sex would be a great way to relieve the stress. We were both looking for a long term relationship with someone, just not each other. She was looking for someone older than me but had hard time finding the right guy. I was looking for someone younger. But neither of us were in a position to look for what we wanted since we were job-seeking. We remained FWBs, and it was immensely satisfying to both of us. She liked that a younger guy was interested in her. I liked that I was able to fuck the woman I lusted over in my teens. We saw each two to three times a week, there was one week when we spent it together at my place working on our resumes and job searches, and we even spent a few weekends together going out to movies or a museum or cooking at home. I never had so much sex in a FWB relationship.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), To feel better about myself, To cheer myself up, I was feeling lonely

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

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? No one

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? A little bit

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The sex was awesome. There was no condoms used then or in any of our hookups after because she didn’t expect to be pregnant at her age. We were never sure, but that uncertainty added to the excitement of it.

What was the WORST thing about this hookup? We both finally had to move away to different cities as we found new work. If we were younger, maybe something long term could have happened. Maybe we were developing feelings for each other. When we said good-bye, there were some tears in her eyes. When I saw that, I kissed her passionately and we had one long intense and passionate fuck before we left each other. But we still email each other a few times a year.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? Writing about this now, I get horny and I miss her. I thinking I will reach out to her and try to visit her. She’s still single, but I don’t know if she will be up for a long distance FWB relationship.

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