First of 5,000

by Sin

Gender: M
Age: 52
Race/ethnicity: white
Current location: US
Highest education received: College degree (eg., BA, BS)
Occupation: management
Relationship status: married
Religious affiliation: Christian
How religious are you? Somewhat
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 3
How many hookup stories have you here posted before? 0

First of 5,000

How long ago did this hookup happen? 30 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…)? First of many

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? Christy was a beautiful 30-year-old divorcee.  Very playful and fun to be around.  Compact little body.  We both worked at a large steakhouse in the western US.  All the guys that worked there were young dudes trying to get into somebody’s pants.  The waitresses and bar staff were all female and a little older.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After work the crew would always hangs out to drink.  One night Christy and I were the last two to leave.  She pulled up to me in the dark parking lot and asked if I wanted to come over to her place.  At first I told her no thanks (idiot) until she made it clear she wanted to fuck.  I was still nervous.  She lived out in the middle of nowhere and I didn’t know much about her.  I didn’t want to end up beat up by some angry boyfriend or redneck brother, so I talked her into going to the boss’ camper that he kept in the parking lot behind the restaurant.

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 just started making out.  I was young and inexperienced but passionate.  I found out that night Christy never wore anything under her uniform and after unbuttoning her work shirt and unzipping her skirt she was full fucking naked.  I stripped off my work clothes, too (I’m sure they were gross) and we got down to it.  I didn’t know much about foreplay then, but I kissed and played around with her tits before I entered her.  I hadn’t had sex in five years and was scared as hell I was going to cum right away.  She kept saying how good it felt and how long it had been since she’d had sex.  I went sooooo slow to keep from cumming.  She later said the first time was awesome because I was so gentle, but I was just trying not to blow.  I had no idea what I was doing, so I just kept going as slow as I could until she said she was cumming and stuck her legs straight up and quivered underneath me.  Naturally, I came right away, too.

Did you have an orgasm? Did your partner(s)? Both.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None.  It was the 80s.

What were your REASONS for having this hookup? She was horny.  I was too (always), but wasn’t looking.

Were alcohol or drugs involved? If so, how much? Alcohol.  Not a lot.

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? Afterwards she kept saying how good it was.  Naturally I was blown away – both by the sex and the fact that she liked it.  I had never given a woman an orgasm before.  We ended up together for 10 years and had great sex like 5000 times.  We have since broken up.

To whom did you talk about the hookup? How did they react? I had to tell my boss because we broke something on his camper.

Was this a consensual and/or wanted experience for you? For your partner? Consensual for both.

Do you regret this hookup? If so, why? No regrets.

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? This hookup led to the best sex of my life for about ten years after.  The worst part was there was a lot of drama, too.  Besides the sex, we didn’t always get along so well.

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

All things considered, how NEGATIVE was this experience? A little negative

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