by

What’s your gender? Man
How old are you? 50’s
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? East Coast
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Businessman
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity?  Prefer women while ocassionally bedding men. Just enjoy sex when it’s presented.
How many sexual partners have you had in your life (including oral sex)? Thirty-ish
How many hookup stories have you here posted before? This is my second. My first was ‘I was seduced by an older muscleman.’

Penetrated By An Older Muscleman At Sea

How long ago did this hookup happen? Decades ago, when I was lithe, handsome, muscular and was attractive to both women and men.

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a month

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? This was with the same older male bodybuilder that had seduced me before. If I was 18, he was in his mid-forties perhaps. He was a little taller than me, muscular, white, bronze skin, blue eyes, big chin, blonde Nordic hair. He looked incredible nude, with an ’80’s bush above his upward-shaped banana member. He had a huge smile and a patient, warm way about him. He was very gentle and friendly, which eased my extreme nervousness during our first sexual encounter.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? He called me the next week and asked me out, which I said yes but that I was in the process of asking out a very pretty and voluptuous Polynesian girl so I was hoping to see him discreetly. He said yes to my request and asked if I’d like to come to his boat and ‘lay out and get some sun’ with him. I said yes. I had met the Polynesian girl just that week, and all I could think of was having sex her and this guy separately yet during the same day. It aroused me to think of me fucking her and him fucking me. I was young, horny and eager to experiment sexually.

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? I met him at his boat and he drove us out on the water to a secluded spot (I’m being vague about location and geography here). He had been super-discreet when we met among the crowds. He was still a bronzed, bulging mass of muscles and his skimpy 80’s short-shorts and tank top aroused me. The sun was strong and I was still nervous. He stopped the boat, turned and while we were under the shade of the boat cover, reached out under my shorts and began to fondle my penis again. I started to get hard and he reached over and kissed me passionately while 18 year old me stood there rather awkwardly. He laid out towels on the back deck and told me to undress. It was bright sun and the water lapped at the boat while we pulled our tanks off but kept our shorts on, but we were both hard for each other as we laid down. As soon as we were horizontal he reached over and started to fondle me under my shorts as he asked me if I was still nervous. I blurted, “I want to have sex with you, but I’m not going to initiate it.” He smiled, leaned over and kissed me, and we french-kissed as he slid my shorts down my body. I was nude before him and aroused and very attracted to him. We gasped with heat and arousal as we made out almost violently. He whispered that he wanted to butt-fuck me, and I said okay but that I had never done that before. He said he had some lube and a condom ready and I said okay again, but that I wanted us to suck each other’s dicks first. He said okay as he hurridly pulled his shorts off, but that we had to look out for other boaters, that we could get in trouble as two men fucking outdoors. He was nude and his curving-upwards banana beckoned me, so I began to jerk him off while we made out. We sucked each other’s dicks, he looking up in case someone was nearby, but we never heard any boats around us during our encounter. He pulled back and semi-stood up to get what turned out to be the lube and rubber, and I lay there looking up at the sky and I choked up a little bit and thought oddly of what the Polynesian girl was doing when he came back. We made out some more very passionately, then he rolled me over onto my back on the back deck. He was on top of me, kissing my neck and sliding his erection over my ass cheeks. I spread my legs wide open, thinking it made me look sexier to him. I asked him if he preferred younger men and he said yes. I felt the wetness of the lube being spread between my buttocks and anus, and he then started to enter me. It hurt at first, but it was very wet and fluid and he started to slowly buttfuck me. I lay there with my legs wide open as he fucked me, his massive body atop mine. At last he orgasmed inside me while in mid-thrust, calling my name as he came. He stayed inside me, and I could feel his penis pulsing inside me, having shot it’s semen into the condom. I remember thinking it would have been mush sexier to have had him cum inside me, but appreciated the safety of the rubber. He pulled out and rolled over next to me and thanked me. I rolled over onto my back and we kissed butterly kisses of satisfaction. He held me for a few minutes before pulling his condom off, I still remember seeing the ball of semen at the tip of the tied-off rubber. He took some baby oil out and began to massage me, and it aroused me, and he then jerked me off while kissing me until I shot semen up into the air and over us. He gave me towel to clean myself off with and after dressing puttering around the water for a bit, we drove back.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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? He told me he wanted to see me again, no strings, and i told him that I wanted to date women freely yet see him when I became horny for him. It was kind of a silly thing to request, but I was young and enjoying my experimenting with sex. I felt fine as I drove home, and over the next few days I pleasured myself thinking of the encounter. It did arouse me to think of sleeping with this beautiful Polynesian girl while thinking of him, and vice-versa. I decided to not tell either one about the other, and enjoyed my secret.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Thought it was an important experience to have, I was feeling lonely, Submission / Relinquishing power, Making new friends, Boredom, Just happened, I don’t know why, just went along with it, It was easy / convenient

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

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? I told a few women later that I had fucked a few men, and more were put off than aroused. So I just decided to keep my bisexual experiences to myself. The few times I was seriously dating a woman while secretly having sex with men were some of the most exhilarating times of my life. I would think of her pussy while I was giving a man head, and would dream of a man’s member while eating out my date or girlfriend.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

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? Laying there and telling him that I would have sex with him but that he would have to initiate our encounter. I deep-throated him, he was larger than most of the other men I bedded, both older and younger than myself. I never dated anyone under age, yet I did have sex with significantly older men than myself.

What was the WORST thing about this hookup? In our haste, I did not get the chance to experiment with penetrating him, though that came later, and with other men my age in particularly. Most of the older men ended up buttfucking me. Most of the men I bedded my age I ended up either atop them or we mutually penetrated each other.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I was enthralled by the kinkiness, secretness if you will and the taboo of the whole thing.
Just enjoyed my youth and sexuality.

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

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

Anything else you want to add about this hookup? Yes, I made it clear to him to reach out to me by phone as a friend as we went along, so that the women in my life always just saw him that way, a distant friend, not knowing he was bedding me as I was bedding them.

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? I enjoyed casual sex, enjoyed that period in my life and regret nothing. Enjoy the format here and hope to post more of my experiences in the future.

What do you think about the Casual Sex Project? It’s a healthy tool for healthy sex.

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