by Astra

Gender: Male
Age: 46
Race/ethnicity: White British
Current location: UK
Highest education received: High school diploma
Occupation: IT Manager
Relationship status: Single
Religious affiliation: Agnostic
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? 0

Tour Of The House

How long ago did this hookup happen? 5 years

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Short fling

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? 42 year old woman, rounded figure, dark hair and eyes. She was a friend and former work colleague. We’d flirted and tried cybersex before, but had just become friends and spent some time together.
I was confused about my life and didn’t have any direction. Much of our time was spent talking and analyzing people and relationships.
It started as friendship but I felt a growing attraction.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were at her house high in the moors and had planned for us to have a meal and for me to stay saturday night in the spare room.
The meal was over and we were drinking wine and as always talking.
I’d been through a bad patch lately and she was playing agony aunt and trying to help me through it.
I suddenly stated that a previous brief relationship had hurt me so much that I didn’t think I’d ever be any use to another woman and would never satisfy anyone.
She looked at me and said “Do you want to find out?”. I said Yes, and she led me upstairs to her room.

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? She asked me if I had protection, which by chance I did. She led me into the room and kissed me full on the mouth. I started to remove my clothes and she told me not to go so fast.
We kissed and explored each other, kissing and licking each part of each other’s bodies as clothing was removed until we were naked.
Laying between her legs I caressed her breasts, sucking hard and nibbling on her nipples. I licked and kissed between her breasts, my mouth moved downwards.
She ran her fingers through my hair as I performed oral on her, darting my tongue around and inside of her. She breathed harder and moaned, coaching and encouraging me.
After a few minutes she told me to kneel on the bed and applied the condom to my penis. She then guided me into her as we assumed a missionary position with her legs around my waist.
I knew I wouldn’t last long but did the best I could, finally burying my face in her neck and thrusting hard before coming loudly.

Did you have an orgasm? Did your partner(s)? I orgasmed but she didn’t.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We used a condom.

What were your REASONS for having this hookup? We had a close and flirty friendship. Her husband had dies a few years before, I needed someone. We both just needed someone I suppose.

Were alcohol or drugs involved? If so, how much? A couple of glasses of wine each.

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? I had hopes of more, and in fact it did happen later. She regretted it at first but asked later if I wanted to be her fuck buddy.
It went bad quickly. She found a married man and regaled me with stories of their sex. I finally told her I wanted nothing more to do with her.
She left me damaged, but that helped me change my life.

To whom did you talk about the hookup? How did they react? No one knows all the details.

Was this a consensual and/or wanted experience for you? For your partner? We both wanted it and consented to it.

Do you regret this hookup? If so, why? I regret this was never the start of a relationship as I think we would both have had something good from it. In the long run I’m glad it ended fast. She did use me and I found true love later.

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? It was fun. We did it again, and even tried while sunbathing on her house roof.
I realised I could have casual sex, that I knew what to do and what I wanted from life, which was love, and not casual sex!

All things considered, how POSITIVE was this experience? A little positive

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

Anything else you want to add about this hookup or anything else? Never have sex with a selfish person. If they say at first that they feel nothing for you, it’s wise to examine what you really want.

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