Craigslist Daddy

When I was 16 I posted a m4m craigslist ad, hours later was 69ing with a much older man at his lake house.
This was my first ever craigslist hookup, but not my first gay experience.
He lived about 10 minutes away from me, was hung, handsome, polite,and wealthy as fuck.
That night was the first of many with him until eventually he sold his house and moved to California.

Comments

Anonymous

by Anonymous on Jan 21, 2025 at 1:17 PM

I had three other boy's as boyfriends all through high-school but afterwards I was too shy to go to any of the gay meeting places mostly because I wasn't 21 and couldn't go to bar's. That's where craigslist came into play. I was nice looking and basically inexperienced except for the few other boy's in school. I was fresh meat and had a large amount of responses to pick from. I decided on older experienced one's after a first date fiasco took a month to recover from. I wasn't use to large penises and mentioned that to my suitors that responded. The guy that was 22 when I was 18 lied about his size and "just wanting to make out" when actually he was thirty something and hung like a horse and in no way concerned with my lacking experience. He slipped something into my wine and literally stretched me out painfully enjoying that he was hurting me. After that horrible experience my next time a couple of months later were wonderful men and I loved being with them.

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Anonymous

by Anonymous on Jan 21, 2025 at 8:28 PM

Well so what? You call this a confession? I did things 100 times worse for gun and profit

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Anonymous

by Anonymous on Jan 22, 2025 at 8:51 AM

I wish we still had Craigslist. Back in the day when I was traveling with my job and in hotels every night I used to use Craigslist to chat with other men because as long as I can remember I have not only been curious but I have had sex with other men.
I have a thing for naked men and their cocks. As a young boy I let my cousin fuck me all the time for years. As an adult I still like to be fucked. I have no attraction to making love with men I just like a cock up my ass and being fucked and I have a fascination with really big cocks.
I like to look at pics of naked men with huge cocks. I would get on Craigslist and search the ads and look at pics. When I find a guy with a large cock I would start a conversation. I like talking about getting fucked and taking a big cock up my ass and I love the way it feels to be penetrated. Over the years I have had oral sex with hung men and had them suck my cock but mostly I wanted to be fucked.
Three different times in my adult life I met with men more than once because they had a big cock and they could really fuck me good. These three different men after meeting me a few times to fuck me told me they had a friend that I might like to meet and on those three occasions I actually had three way sex with two men at the same time. Two men fucking me and taking turns on me. Several times me sucking on one big cock while getting my ass fucked with a big cock.
Two different times in my life I have experienced an anal DP. Two cocks in my ass at the same time. It was mind blowing both times. I have duplicated that many times with my dildos and rubber cocks.
I always played it safe but several times after multiple meetings with the same married man I let them cum in me. My cousin always came in my ass when we were young boys and I always liked it and it just felt good
Twice I had big black cock and many times big fat Hispanic cock. Mexican men are my favorite. Most have a very nice cock and love to fuck. I always got excited taking my clothes off with another man knowing he was in my hotel room to fuck me. Spreading my bare ass cheeks and letting him look at my asshole and waiting to feel his big cock touch my hole then pushing opening me up then going inside of me then feeling his long thick hard cock going all the way up inside of me then getting fucked really hard and deep.
Being talked dirty to having my ass slapped while he fucks me and my cock dripping pre cum as he pounds my ass and my asshole stretcher around a big fat cock just feels so good I could get fucked every day if I could.
Sucking cock is fine and I enjoy a long 69 but my favorite is giving up my ass to a man with a very large cock. I have used a lot of huge toys and enjoy them often. I have taken over 18” up my ass many times and I enjoy something very thick from time to time. Only once in my life have I ever had a huge cock and I met with him on 6 different occasions in a year and a half. His cock was very thick and 12” long. He was younger than me and could stay hard for a very long time. I let him cum in me every time we met because his cock felt so good in my ass I wanted him to finish inside of me.
I am married and my wife and I have several strap on cocks and she loves to fuck me at least once a week and she knows I play with toys at times when she is not around and she has watched me and used toys on me and I use toys on her also.
I have always enjoyed anal and any type of anal play and love anal toys. If I am home alone for a day or so I will stay nude and lubed and play for hours and wear a butt plug for hours. I have numerous suction cup toys that can fuck myself with hands free and what I really like is putting my cock up my ass and I really like to cum in myself and I will cum in my own ass numerous times a day when I am playing. I video myself and like to use a few mirrors to watch myself when I am playing with my toys
Many years ago I posted an ad online looking for a man to use toys on me. I asked for light bondage and to have toys used on me then to be fucked. I had a lot of responses and after 100’s of emails to different men I picked one that I liked the best and for over a year while I was working in that city he and I met almost every week and he was very good at anal play and had a nice thick 8” cock. I bought a lot of different toys and he really enjoyed tying me up working the line up my ass then hours of using my ass with my toys and his cock. He was the best dimmer I have ever had. And he would put my cock in my ass then rub and lick on my cock until I came in myself.
We acted on all his and my fantasies including him using toys and fucking me out in the woods a few times. He showed me how to take every inch of a 24” dildo and he got all of it up inside of me then had me suck his cock with it up inside of me. He could put things in my ass and make it feel so damn good that I wanted him to donut for hours. He would play with my cock stroke it jerk on it suck it pull on it and squeeze my nuts as he toyed my ass and with him there were times he made me cum so hard I got dizzy. He was just fun to play with and he knew how to use my ass and do things to me that I really liked a lot. It would be nice to have another friend like him
I guess some of us just enjoy anal and ass play. I know I sure do.

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