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derek

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how old where you the first time ??

Posted Jan 16, 2023

Replies13
DE
derek
derekOriginal Poster
Jan 16, 2023

the first time i got fucked in the ass i was 14 barley into puberty and it was my older 17 y/o best friend in the back seat of his car. and i still remember the event as he pulled my pant down and rolled me over so i was ass up and his nice raw uncut cock went in me i cried it hurt but i loved the feeling off all his young cum pumping inside me.....such a great memory, it went on for a couple of years until he married a lady.

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  • JD
    JdNtx82
    JdNtx82
    Jan 27, 2023

    That sounds amazing. I was probably 20 the first time I got barebacked and bred. It was with my first boyfriend in the bed of his pickup truck (Texas lol) in an abandoned quarry. Some other people who were off-roading in the area saw us pulled over and thought we needed help, so they caught him balls deep in my hole. After they left he finished in me. It hurt like hell at first but he was calm and patient and gentle with me. By the time he bred me I was totally into it.

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  • RI
    Rick
    Rick
    Feb 5, 2023

    I was 20 and, in the Navy, when I was topped for the first time. It wasn't a pleasant experience. After consuming far too much alcohol and blacking out, I found myself stripped down behind the barracks and forcibly topped. This was back in the 80's where the last thing that a man wanted to do was report being sexually assaulted. I never again drank enough to prevent myself from fighting back, and never put myself in a position where something like that could happen again.

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  • BN
    Birth name or one people call me
    Birth name or one people call me
    Feb 5, 2023

    I was late on getting fucked I was 47 realized late was Bi. I definitely enjoy being a bottom an getting filled with cocks an cum. I havent done it as often as would like because of timing an finding tops or versatile people.

    Definitely has to be bareback first time was with condom because he wanted it that way. Now I only want bareback so can feel the cum inside me feeling the warmth of it an it going inside me. Wish would of realized it sooner could of experienced some great times back in the 80s with a gay friend.

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  • NI
    Nitehawk
    Nitehawk
    Feb 5, 2023

    My first was at age 26, and very much wanted. I had practiced being penetrated many times with various objects and knew how powerful my orgasms were when my ass was filled. I had fantasized about getting fucked by a guy, so when a good looking coworker propositioned me at a department party ("I've seen you at the gym, you're pretty fit" goes a long way when you're inexperienced), I left with him to my apartment. We took some time getting nakedly and sexually acquainted, and I was sort of in awe of him and the situation anyway. After some kissing and sucking, he came on with just the right amount of masculine groaning of how much he wanted to slip into me. He knew it was my first, he was pretty experienced. We lubed, I lifted my legs over his shoulders and he slipped in gently. Wow, how different a moving dick is compared to an inanimate object. But, wow, how amazing it was looking square into his eyes. Feeling that pumping and eventual cumming. What I liked about him was that we were both versatile. I enjoyed fucking him too. Nothing like cumming inside a willing hole.

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  • GA
    Gayfeather1
    Gayfeather1
    Feb 15, 2023
    [quote]In Jr. High School with my gym teacher. Naked during lunch. Craig[/quote] Lucky you !
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  • RA
    Raymond
    Raymond
    Feb 16, 2023

    Hot!! Wish you would tell the whole story!!

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  • MA
    Matt
    Matt
    Mar 13, 2023

    13. I had been masturbating for about 3 months and was already addicted. I was at a friends playing a Star Trek board/strategy game. I was kinda bored so started playing with myself. Got hard so unzipped to make it easier. I guess I was visibly moving too much because he was like "What's doing that and looked under the table and I was busted. He was all freaked, but I was just like, "Hey, have you tried this yet?" He was just kind of stammering and I told him to just try it. He said he had but was afraid of getting caught. I was like, 'Your parents are gone all day and you got no brothers like I do." Naturally my next suggestion was to jack each other so he could pretend a girl was doing it. Then he told me he wasn't sure if he liked girls so I said then you don't need to pretend haha. So we took our clothes off and jacked each other. I tasted his cum to see if it tasted like mine and it seemed even better. So then I asked if I could suck him and he was kind of nervous, but then said OK. I sucked him and asked if he would finger my ass, which was something I'd been learning to do to myself. He got some vaseline and played with my ass and cock a bit while I sucked him hard again and then I asked him to stick it in me. He had some trouble getting it in. He really was nervous but finally, sweet heaven, he was in and lasted all of maybe 4 pumps before cumming again. Afterwards he jacked me off again and let me stick it in his mouth as I came. That summer, over the next month or so we kept playing around. The next time I ate his ass because I saw it in a porn and wanted to try it. After two more times he was ready for me fuck his ass and it was glorious. By the time school started back up we'd hooked up probably 15 times. His mom almost caught us during a sleepover. Then school started up and I moved soon after. Didn't mess around with guys again for almost 15 years.

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  • ME
    Member
    Jul 9, 2023

    38, yeah I know I took my time

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  • ME
    Member
    Aug 11, 2023

    sorry it wasn't a good experience for you. it sounds like it could have been a wonderful experience if he had taken a little more time with you.

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  • GH
    Ghostrider
    Aug 11, 2024

    I was 12 the first time. My two cousins who were 16,17 talked me into getting naked. I did next thing I knew I was laying on the bed on my back legs up and open. My oldest cousins was between my legs with his hard dick pushing at my ass. It hurt like crazy. I couldnt move so I just played there and took all 10 inches. It really hurt. He fucked me for abt 15 mins before shooting his cum in me. Then it was my younger cousins turn. Samething happened.. after that I got fucked every weekend for 5 years. Guess thats why I like dick

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  • CA
    Calidablue78
    Calidablue78
    Mar 15, 2025

    Came to realise in my 50s there was side to explore and eased ( easing ) myself in gently. Explored with a gf pegging which I enjoyed (more than she did) and occasionally pleasure myself anally.
    After Covid I felt the need for some male contact so booked a massage with a local man.
    During a very erotic session in which we were both naked, oiled and aroused he slipped his cock in me before I realised what was happening (seems very naive to say now) Despite the obvious pleasure I panicked as I really wasnt expecting now planned it to happen and asked him to stop.
    We continued to play until we both came but I did quickly regret not letting him continue.

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  • CA
    Calidablue78
    Calidablue78
    Oct 12, 2025

    My first and only to date was mid 50's.
    frustrated by a lack of male contact after the covid time i booked myself massage.
    I had only intended a massage, maybe with a little light play but i wasn't sure what was on offer and hadn't thought to ask.
    The massage was great, we were both naked and naturally i had an erection which was eventually, after some teasing and longing for his touch, he concentrated on. First with strokes, then oral while fingering my anus.
    I stroked and pleasured him orally too. It was working out well.
    He then had me sit up, then opened my legs which were hanging over the bench, and stepped between them and started frotting our cocks. I hadn't experienced this before and i was loving it.
    I looked up to the ceiling taking in the pleasure when he stopped. Looking back down i saw him place his cock below my balls.
    With my oily hole and his oily cock it slipped in with ease.
    While it felt pleasurable i had only been pegged by my girlfriend but never a guy so i was shocked and admit I panicked and asked him to stop. Which he did.
    He finished me off frotting then masturbated himself cumming over me.
    Driving home i did kind of regret stopping him.

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  • JA
    Jay
    Jay
    Jan 23, 2026

    I was eight my first time. I had three older brothers. We were raised nudist. We figured out pretty early how to enjoy our bodies.

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