by Cassidy

Gender: Male
Age: 56
Race/ethnicity: Caucasian/american
Current location: Rural Pennsylvania
Highest education received: College degree (eg., BA, BS)
Occupation: Small business owner
Relationship status: Single
Religious affiliation: Protestant
How religious are you? Somewhat
Sexual orientation: Heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Swinger
How many sexual partners have you had in your life (including oral sex)? 60+
How many hookup stories have you here posted before? 2

A Life Ruined

How long ago did this hookup happen? 4 years ago

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…)? One long week

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? “MA” She was once an attractive woman who was now worn down by years of mental health issues, smoking, drugs, and alcohol. Hard core drug use in her late teens and early twenties as a party girl may have set the foundation. She came from good stock.   I knew of her in her and her extended family nearly all of my adult life.  We hooked up in our fifties.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was a quiet night when I ventured into my favorite brew pub for a beer.  It was a quiet night.   I struck up a conversation with a friend who was carrying on a conversation with  MA.  After our mutual friend left MA and I started talking about our mutual connections and life in general.  It was then that I learned that she had had a tiff with the daughter that she had been living with and was in need of a place to spend the night.  I offered her my spare bedroom for the night.  At this point there was no intention on my part for the evening to turn sexual.

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 returned to my place where we spun some tunes, had another beer and shared a nugget.  One thing led to another and she drew closer to me.  The light in my head went off when she asked me to massage her back.  After my hands went up the back of her sweater and I unclasped her bra I knew from her reaction that she wanted to be laid.  She claimed that she hadn’t been with a man for several years.  From her full bush I figured that that was true.  I looked upon it as a privilege to make love to a woman who wanted to be loved in the most intimate and delicate way.

Did you have an orgasm? Did your partner(s)? We both had orgasms.  She when I gave her oral and I later.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Due to her age pregnancy was not a concern.  Even though I used a condom I figured STD’s could still be an issue given her history.

What were your REASONS for having this hookup? Had she not made the move I would have been fine with playing the roll of a friend who offered her a place to spend the night.  As fate would have it she spent a week with me while she made arrangements to find her own housing.  While we shared the same bed we did not engage in sex until her last night when she asked if I would make love to her.

Were alcohol or drugs involved? If so, how much? Moderate alcohol and a few buds.

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? A few weeks after our week I checked up on her once.  It was New Years Eve.  After dinner at a local restaurant she  invited me back to her place. I declined.  It was one of those years that I wanted to end.

To whom did you talk about the hookup? How did they react? I deliberately flew under the radar. Only a few friends knew.  One who knew MA better than me.   A few of her family knew as we worked together to help MA find a place of her own.

Was this a consensual and/or wanted experience for you? For your partner? Consensual.  Certainly I could have had my way with her.  I am proud that I did not.

Do you regret this hookup? If so, why? I do not regret.  I was single at the time. Life is an adventure.

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? Best: The connection, even if it is brief, that two people can establish.  Worst: She had a nasty habit of smoking cigarettes when I was not around.  This incident did not change my view on sex.  It did reinforce my appreciation that for the most part I have lived a healthy lifestyle.

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup or anything else? Ironically, several years earlier,  MA’s daughter had been in a romantic relationship with  my adult son.  So MA was the 2nd woman that I hooked up with who had a daughter that my son had been with.  A few months ago I posted a story on the first woman.

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