20 Years Wait

by Littleposh

What’s your gender? Woman
How old are you? 38
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? UK
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Chef
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 150 ish
How many hookup stories have you here posted before? None

20 Years Wait

How long ago did this hookup happen? 2 days

What was your relationship status at the time? Single

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? Just met that day

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? He was 45, tall, and well built. I had a huge crush on him when I was a teenager but hadn’t seen him in 20 years. I still had a massive crush on him and desperately wanted to make those teenage fantasies come true.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had messaged him asking him out, but then things had gone quiet for a few weeks. We started chatting again, and I figured he was fairly interested, so I just went for it and invited myself to his house.

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 caught up a little bit but went to bed before long. He was absolutely incredible in bed, one of my best. I was surprised, especially as he was quite drunk. He was very generous with his mouth and his fingers, he was complimentary. He was energetic, position’s were constantly changing. He tried for anal but his dick was so big I didn’t dare. He literally had the biggest cock I’ve ever seen. It was so thick. It was a struggle to suck him off. After sleeping for a few hours, we woke up and he fucked me. He came deep inside me and it felt so good. I think he wanted to get me squirting, but I was really nervous. I am hoping for a repeat performance so I can let go a little more.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

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 day I was buzzing. 18 year old me was thrilled! He took me home then messaged a short time after. We’ve spoken since, so I’m hoping we can do it again. I’m not especially looking for a relationship, though I wouldn’t rule anything out, but I think I could have some fun with this one.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) IUD (Intrauterine device)

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

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? I told my 2 best friends, and they were excited for me. I also told my daughter (18) where I was that night but let her draw her own conclusions about it.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Amazing sex

What was the WORST thing about this hookup? That it might not happen again

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

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I don’t know why we are so hung up on sex. I don’t see a problem with doing anything you want as long as you aren’t hurting someone else. I am a huge fan of casual sex and people who know me generally know that. It doesn’t seem to bother many people although not many others act quite as wild. I’m not ashamed of what I’ve done and plan to keep doing it until I get too old or meet the one that makes me not want others.

What do you think about the Casual Sex Project? Love the idea of it

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