Tight Squeeze

by Kiwibloke

Gender: Male
Age: 47
Race/ethnicity: European
Current location: Auckland, New Zealand
Highest education received: College degree (eg., BA, BS)
Occupation: Technical
Relationship status: Married
Religious affiliation: Christian
How religious are you? Somewhat
Sexual orientation: Mostly heterosexual
How many hookup stories have you here posted before? 4

Tight Squeeze

How long ago did this hookup happen? 4 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…)? Friends with benefits

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? Donna is an old family friend. She was single, 41, small boobs, cuddly body.
We had swapped pictures in the past and even once had a quick afternoon play.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had recently become separated, was at a loose end and my ex-friend with benefits was mucking me around. I asked Donna and her friend Lisa if they want to go local pub for drinks on Friday night and meet my FWB and see if I was just making things up with her strange behavior.

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? The night dragged on and drinks flowed fast. Donna and Lisa watched as my now ex-FWB got plastered and felt up all the young guys in bar. So their mind was set, she was no good for me. We left and went back to Donna’s by taxi.

Once inside, the girls said they were off to bed and I could have the couch as Lisa had a spare bed. I suggested a move of all three in bed, they agreed and got in their pajama’s. I don’t sleep in much so I slipped in between them in my undies.

Lisa was a stiff board and was not having anything so rolled over and shut up shop for the night while I slipped my hand down Donna’s pants with no restriction and proceeded to finger her off, her orgasm muffled by her mouth being shut. She tried to give me a handjob but was scared of Lisa finding out so gave up.

Did you have an orgasm? Did your partner(s)? Donna did have one.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None, not really needed.

What were your REASONS for having this hookup? This was just a spur of moment thing and involved lots of drinks.

Were alcohol or drugs involved? If so, how much? Lots of alcohol previous

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? Nothing happened next day, I had a coffee with them in the morning and went home.

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

Was this a consensual and/or wanted experience for you? For your partner? I am always keen and Donna & I have a strange and secret past of sharing issues and playing.

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

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? We have always been friends and it didn’t affect our relationship.

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

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

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