Being In Bed With My Longtime Crush

by Earl

What’s your gender? Man
How old are you? 42
What’s your race/ethnicity? Southeast Asian
What continent do you live on? Asia
What country and/or city do you live in? Philippines
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Lawyer
What’s your current relationship status? Engaged/Married (monogamous)
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)? 8
How many hookup stories have you here posted before? None

Being In Bed With My Longtime Crush

How long ago did this hookup happen? 7 years ago

What was your relationship status at the time? Engaged/Married (monogamous)

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

How long did you know the person before this hookup? For more than 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? The first time I met her we were still in college. I was immediately smitten by her beautiful face. We became friends but as much as I was attracted to her, I could not get out of my relationship during that time. We then lost contact with each other and met again only after 10 years when we were both already married.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It started out with just a simple meet up. I learned that she was physically separated from her husband. From then on we would start texting each other until one day she told me she wants to have a baby with me. At first, I thought she was only kidding but when I found out that she was serious, I would not let this opportunity pass. ????

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 met at a location near her house. From there, we took a taxi going to the motel. Upon reaching our room, we immediately engaged in passionate kissing, tongue and all, and started undressing each other.

I kissed her whole body and sucked her tits/breasts. As I am going down on her, I realized she has a shaved pussy which only aroused me more because I have not fucked a woman with a shaved pussy before. However, as I started licking her pussy, she stopped me. Apparently, she was surprised because she has not experienced it before from her husband who would just fuck her missionary style.

I gave in and just asked her she can do whatever she wants with me. She gave me a blowjob and then proceeded to fuck me cowgirl style. When she reached her orgasm, we changed positions and I fucked her doggy style. And then we wrapped up with the missionary position.

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? We would then hook up several times until she claimed that she was pregnant, and left for the US. I never expected that there will come a time that I will be able to fuck my long-time crush, so it is a dream come true for me. I wish we could still meet but that is highly improbable right now given she is now stationed abroad.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Thought it was an important experience to have, To feel better about myself, To feel more desirable, To feel more confident, To cheer myself up, Power / Dominance, Submission / Relinquishing power, Didn’t want to disappoint my partner, Just happened, I don’t know why, just went along with it

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? I talked about this with a girlfriend whom I also hooked up.

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

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? As I said, it was a dream come true for me to be able to fuck my longtime crush.

What was the WORST thing about this hookup? The fact that I cheated on my wife.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really.

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

All things considered, how NEGATIVE was this experience? Fairly negative

Anything else you want to add about this hookup? I wish I could repeat it over and over again.

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 am open to casual sex as long as the partner is willing to keep secrets and knows that our relationship would not go beyond sex.

What do you think about the Casual Sex Project? It is a good forum for people like me to tell our sexual encounters anonymously.

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