Old Crush Guilt With A Twist

by Buggyflauto

What’s your gender? Man
How old are you? Mid 20s
What’s your race/ethnicity? Southeast Asian
What continent do you live on? Asia
What’s your current relationship status? In a serious relationship (monogamous)
How religious are you? A little
What’s your sexual orientation? Heterosexual

Old Crush Guilt With A Twist

What was your relationship status at the time? In a relationship (open)

How would you best classify this hookup? One-night stand

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? She was a very old friend from childhood. We basically grew up together. I loved her and confessed before but she did not accept me probably because I was younger than her. But we still were extremely close friends and stayed close till today. She has a boyfriend of a few years.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She is working in another city, she came back to attend a mutual friend’s baby party. She asked to stay in my home as her boyfriend could not get time off to accompany her and she didn’t want to waste money on a room herself. but I had just recently begun seeing another girl so I politely declined. She got a room at a fancy hotel in the city centre. We sat beside each other at the dinner, and decided to go for drinks afterwards to catch up.

After consuming a bottle of wine together she was slightly tipsy but still seemed to want to to talk. I won’t pretend that I still found her attractive, and said so. I suggested taking a bottle back to her room but she said she was sharing it with another woman who was also attending the party. We ended up going to my place in the end.

I opened another bottle of wine and we got through about half of it while continuing to talk. 1 thing led to another, when she said she felt tired and had some back pains, I offered to give her a massage and she accepted.

She laid down on the sofa face down, I got on top of her and began rubbing and massaging. She obviously liked it. Being slightly drunk myself, I gently lifted up her shirt, unclasped her bra and continued massaging her with lotion. When she did not object, I began pressing my cock against her and she began moaning softly and meeting my movements.

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 softly kissed her ears and said I wish I could treat you like this every day, since the day we met. She just moaned and turned around, and I started kissing her. She froze up slightly but I continued while caressing her. As she relaxed, we started exploring each other more, I continued teasing her with my lower body while touching her lightly at her breasts and cheeks. In the end, we both came to our senses before things went further, staring into each other’s eyes, with regret in my heart, and I think, in hers too.

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? She dressed, we were awkwardly quiet for a while, then we continued talking as if nothing happened, finished off the rest of the wine and with happy smiles and good friendship feelings, I sent her back to her hotel.

Early in the morning, I was awakened by a message from her. Oh god, her boyfriend had a plan with her friend, and was waiting in the room to surprise her, with a ring and he proposed!

And now I have to live with some guilt of our reckleness that night.

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

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

What substances did your partner(s) consume? Alcohol

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