What’s your gender? Man
How old are you? mid 60s
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Retired professional
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Agnostic
How religious are you? A little
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? I’ll fuck anything that moves
How many sexual partners have you had in your life (including oral sex)? Close to 100
How many hookup stories have you here posted before? 1
Slow to Cum
How long ago did this hookup happen? On-going
What was your relationship status at the time? This is an ongoing, lifetime situation
How would you best classify this hookup? Fuck-buddies / Booty call
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? Your format doesn’t really allow for the story that follows. I have had sex with young and older females, young and older men, couples, and groups.
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 first had sex with my GF in high school. She was cute, everything a horny 18 year old wants. She loved being licked and came hard every time. She would play, suck, and fuck me whenever I wanted. Strangely, I found it difficult to cum easily. It would exhaust her trying to get me off. Mind you, I didn’t have a problem getting hard, but usually had to masturbate to actually finish.
I married for the first time in my early 20s. It was a big mistake but, that’s a different story. The marriage quickly became boring to me and my difficulty cumming continued. I always got and stayed hard but just usually didn’t cum. I was back to jacking off alone. At age 30, I started spending a lot of time and money buying the trashiest men’s mags available and jacking off in my car at lunch breaks which usually made me cum easily. I was getting a bit desperate to find a way to have another human make me cum. Believe me, this was not making my marriage happy as my wife wanted children.
When whacking to the men’s mags, I found I was getting more excited seeing cocks than pussy. Especially pics of men cumming in or on a pretty lady. The cocks excited me and made it easier to finish. When we moved out of state, I discovered adult bookstores and glory holes.
At 35, I gave my first BJ at an ABS. I was instantly addicted but found when a guy sucked me, I rarely came despite being very excited and hard. Men would go down on me for a half hour or more without coaxing out a drop. So, I usually just sucked and tried to jack off myself. Soon, I tried anal. I would put my ass to the GH and let a guy do me deep. These were the days shortly before the AIDs epidemic and I got fucked many times bareback. I loved the feeling of a man in my ass but, as always, I couldn’t cum that way.
Next, I began fucking male asses bareback at the GH. The feeling of soft flesh around my cock was stimulating. I had no ED problem and found many guys loved that I could fuck them until they came. At times, I’d plow 3 or 4 guys a night, then go to my car to finish myself off.
At around age 40, I discovered ‘Swinger’ magazines and began contacting couples for threesomes, foursomes, and whatever else was available. I played with young and older couples. An 18 year old high school couple was one of the first and I was double fucking her and actually came hard in her pussy. I though I was cured! We hung out in a motel room for a few hours and my cock never went down while we were talking. We went at it again, me in her ass this time. After she orgasmed multiple times, I was still hard. I sucked her BF. He came. I didn’t. As soon as they left the room, I JO’d within 5 minutes.
This scenario continued after my divorce. From age 40 to 60, I would fuck anyone that needed attention. My cock wasn’t as stiff anymore but, I easily got and maintained erection. I found a source for Viagra, which helped keep my 7″ hard.
Young couples were difficult to find once I hit my 60s. Older women didn’t usually turn me on, so I would try 40-45 YO couples. I found my greatest joy with bisexuals, as I loved sucking cocks and craved being fucked in my ass. But, I rarely came. I am a very masculine, straight-cut guy. No problem playing with, sucking, or fucking a man. But, not into kissing or romantic stuff. Most of the solo male ‘Swingers’ were actually gay and always wanted the kissing. That just wasn’t me so, as I grew older, I found that my options become more limited. The young ones thought I was too old and the older ones didn’t appeal to my taste.
I was resigned to relying on hand service, sometimes with a vibratory in my hole. I always came that way, with or without the Cialis. By now, at age 63, I started cruising Craigslist and found some success hooking up with older men – late 40s to late 60s. We’d get together a couple times and the guy would fuck me or, I would suck him off. They would cum every time. I wouldn’t. I probably hooked up with 50 men that way and came only once or twice. However frustrated, I did enjoy the feel of a man in me.
In 2017, I saw a CL ad posted by a young twink type searching for a Daddy. He was 18, skinny, and claimed to be versatile. The ad didn’t show his dick but, I knew I liked young guys so, I sent him a message. I explained that I was primarily a bottom, told him what I liked and we exchanged messages.
After talking for a few days, I asked to share pics. I sent him pics of my old cock, ass and body, figuring that would be the end of the conversation. I was surprised when, next day, I received the same from him, telling me I looked to be the perfect Daddy type for him. He claimed to be 18, though I was concerned because he told me he was still in High School. He was about 5’8″, maybe 125 lbs, very skinny, kind of a feminish body. What blew me away was that, attached to this body was what appeared to be a huge dick. Though soft, it looked 7 inches. That got my interest and I suggested we meet.
He had to wait until the weekend, since school was in session. So, on a nice Spring Saturday, I drove 30 miles to meet him for the first time.
John was exactly as the photos seemed. A bit quiet but friendly, effeminate in shape. We parked on a country road and stripped. His cock was nearly erect as I lowered his underwear. He was at least 8 inches hard, with an oddly shaped shaft – it curved downward rather than up. I had sever seen one quite like his. It was also very thick and I wasn’t sure I wanted that in my ass. I played with his nipples, sucking them hard in my mouth. Then, I kissed down his body until taking his hard cock into my mouth. Playing with his balls, I took as much as possible into my mouth and began as sensual a BJ as possible. He made me stop several times to avoid cumming. I rimmed him and began playing with his ass hole but, that was too much for him. We rested a few minutes and both our cocks slumped a bit. He told me he had to be home in a half hour and asked me if I wanted to be fucked. My rising dick gave him an answer.
I laid on my back on my truck’s back seat, doors open, while he lubed his bare cock and widened my ass with fingers. I scooted to the door, hanging my ass at the end of the seat. He stood outside, lifted my legs a bit and fed his long, crooked dick up my ass. I usually feel pain being fucked so, I was very surprised that there was no hurt going in. He took his time inching into me. I had never had a cock in that deep and felt minor discomfort as it went deeper into me. He asked if he could fuck me now and I agreed. Holding my ass, he stepped up to the seat and lay down on me, kissing my neck, fondling my cock and began to move
Then, John lowered his face to mine and kissed me deeply. This was the first man I had allowed a kiss and I discovered it very erotic. I returned the kiss and he began to fuck me earnestly. Long, hard strokes, seemingly going deeper each time. I felt my insides being rearranged and loved it. Then, I felt him taking hard, fast strokes and knew he was close to erupting in me. I was lost in the pumping, deep kissing and body contact. I felt him becoming urgent in me, swelling even larger. He hammered a couple short strokes into me and I knew he was flooding my ass. The feeling was so unbelievable, I came, hard, between us.
John, an 18YO twink, had taught me how to cum. We’ve hooked up twice since then. He always wants to top me, though I have offered to return the favor and, will eventually have his ass, too. At least that’s what he’s promised. Every time we are together, I come hard. Maybe it is the kissing that sets me off, I’m not sure but, I know I love his kisses and that crooked dick in my ass.
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? We met twice since and are planning a weekend together. I’m looking forward to that. John now has a GF but assures me he still needs his Daddy.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Discussed STI testing history
What were your motives for this hookup? Fun, pleasure, horniness
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? No one. I’m very much “in the closet”.
How would you best summarize people’s reactions about this hookup? I didn’t tell anyone
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? Discovering what makes me cum.
What was the WORST thing about this hookup? Nothing.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Somewhat because I discovered kissing a man turned me on.
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? We’ve become friends outside the hookups. He’s a terrific young man.
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 wish I could be more ‘open’ with gay fucking, not so much closeted about it.
What do you think about the Casual Sex Project? Very enjoyable. I check in for new stories almost daily.
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