Boss’s Friend

by Sam

Gender: Male
Age: 21
Race/ethnicity: Middle Eastern
Current location: Florida
Highest education received: College degree (eg., BA, BS)
Occupation: Student
Relationship status: Single
Religious affiliation: N/A
How religious are you? Somewhat
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 10+
How many hookup stories have you here posted before? 0

Boss’s Friend

How long ago did this hookup happen? 2 days 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…)? fuck buddies

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? Boss’s best friend, she is 20 years older than me. Met her at a meet and greet at my Boss’s birthday party. She is a bit taller than me, blonde hair, blue eyes, slim body…a typical mixture of soccer mom and the girl next door.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She started to talk to me. We hit it off really well and found out we had a lot in common. We decided to go to a bar after the party, so, after several drinks at the bar we started to talk about personal stuff. She told me that she was sexually frustrated and haven’t been with any guy since she lost her husband to cancer.

She lived far away so I suggested that she crash at my place. Surprisingly, she agreed. I bought her back to my apartment and told her that she could use my bed for the night. I told her get comfortable and then I went to take a shower.

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? As I was showering, I hear the door to my shower open. I was shocked to see her BUTT naked in front of me. She joined me in the shower.

She started kissing me, running her tongue all inside my mouth. My cock got hard instantly and before I could feel my own cock up against her body, she was already stroking it. She then started kissing down my neck…slowly to my chest…down to my stomach. I could tell she was really into it. She then slowly went down on me, getting my cock head inside of her mouth. It felt like my cock was being sucked by a wet vacuum. I was feeling her tits while she was sucking my cock, her nipples were hard as rock. I turned got off the shower and bent her on the bath tub. Even though the water was running through her pussy, I could still tell that she was really wet. I finally put my dick inside her and started fucking. That pussy felt sooooo good. It was tight, wet, sloppy and hairy. After every stroke, my legs were shaking. After a good 10 min of pounding her ass, I came inside of her.

Did you have an orgasm? Did your partner(s)? Yes, I did have an orgasm. Yes, she told me she did.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I didn’t use any condom. She was not on birth control. She took the morning after pill.

What were your REASONS for having this hookup? She was single and I was lonely. The moment was perfect.

Were alcohol or drugs involved? If so, how much? Alcohol, a lot of it.

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? After the hookup, we cuddled up together on the bed and fell asleep. She kissed me the next morning and went home. I felt a little weird that I hooked up with someone who is older than me. The experience was good. We still talk on the phone, she invited me over to her house and cooks me dinner. We are not on a relationship nor we are into FWB. We just like to sleep with each other and she enjoys my company.

To whom did you talk about the hookup? How did they react? Nobody!

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

Do you regret this hookup? If so, why? No. I always fantasized about being with an older women and now that I finally am, I don’t regret it.

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? I was finally sleeping with someone without even trying hard.

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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