My Lover’s Brother



What’s your gender? Man
How old are you? 60
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Florida
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Engineer
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Horny
How many sexual partners have you had in your life (including oral sex)? Many
How many hookup stories have you here posted before? Several

My Lover’s Brother

How long ago did this hookup happen? 40 yrs

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For more than 3 years

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? I had a fuck buddy, Frank, had sex with him for several years. He was 20-yrs older and I was not that fond of him but used him when horny. But he was a nice guy, nice body & good looking, professional, well off financially. He was not openly gay, in the closet.
When I had the urge, and no one else that I preferred was available, I would stop by his apartment for a romp, he would fuck & blow me. Subject of a future story. Originally he lived alone in an upscale apartment.
I had met his younger brother, Jim, at parties & local taverns. A roly-poly, short 64″, chubby, silly, giggly, happy type guy & fruity when drinking. Both were never married.
Jim had a problem holding a job & for financial reasons moved into his brothers Frank’s place. Frank would not have sex when Jim was home, nor any talk of such. Frank warned me to never say or try anything with Jim. Claimed that Jim was not gay (bullshit!) and did not know that Frank was gay. But, once, we were in the bed when Jim came home unexpectedly. The door was closed, but it was obvious, when we finally emerge, with my butt full of cum. Jim said nothing & Frank said we were discussing business.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Well, I eventually got the hots for Jim, being of the type I like and waited for an opportunity. Frank mentioned that he would be in Arizona to look for property. I had no idea when. So, I called every few days. When Jim answered & said Frank was not home, I then knew. So, one morning early, I paid a visit. Jim came to the door and said Frank was away. He would not let me in, was very nervous. So, as a rouse, I said I had to go to the toilet. Afterward, he was OK & we sat in the living room conversing. Me with a dripping hard-on in my pants. He still had his pajamas on, the thin silky clingy type. Could see his ass crack.
“Would I like a drink?” “Yes, please.” I followed him into the kitchen. He opened the fridge and bent down to get a bottle from the bottom shelf. I position myself behind him & pushed my hard-on into his crack. Two layers of cloth between us. He froze. I started to gyrate up & down pressing into his crack. He still did not move. I said, “does that bother you?” “No” “Do you like it?” “Yes”. I assumed that was an invitation. I reached around and fondled his package, a nice, now hard, thick cock. I then slid his PJs down, no underwear, smooth hairless soft butt. No lube pushed it in and started humping. All the while he stayed bending over with the fridge door open.
A good load of cum shot up his rectum, which continued leaking out the remainder of the day.
We then started to grope, kiss and feel each other. He then fucked me while in bed. The rest of the day as well as the days prior to Frank’s return was fucking & sucking. His butt was enjoyable, smooth, hairless, large and soft. Jim, when pushed, let out many secrets. He talked too much. He mentioned that Frank had warned him not to have anything sexual to do with me, or he would kick Jim out of his house. And that he and Frank pleasured each other often, going back to when Jim was 10. Frank returned and eventually found out, but his warnings were all bluff. He just wanted me for himself.
From then on, the three of us did have some good times.

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? Oral, Anal, Frenching, Feeling.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? Wish they were still around. Frank died in the 1990s, Jim in the 00s.
Frank & Jim were featured in the story of my orgy party.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? My fuck group, they liked it

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? New stuff

What was the WORST thing about this hookup? It ended

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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

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

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? If nobody is hurt (Emotionally, Physically, Mentally, Socially, Financially) then do it.

What do you think about the Casual Sex Project? Interesting, learn new ways.

You have a hookup story to share? Submit it here!