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
Jan 27, 2023That 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.
ReactReply - NA
Feb 5, 2023I 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.
ReactReply - NU
Feb 5, 2023I 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.
ReactReply - NI
Feb 5, 2023My 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.
ReactReply - GA
Feb 15, 2023[quote]In Jr. High School with my gym teacher. Naked during lunch. Craig[/quote] Lucky you !ReactReply - MEMemberJul 9, 2023
38, yeah I know I took my time
ReactReply - MEMemberAug 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.
ReactReply - SWAug 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
ReactReply - CA
Mar 15, 2025Came 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.ReactReply - CAOct 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.ReactReply - BI
Jul 16, 2026I didnt actually get fucked till my late 30s. But I would play with my asshole constantly since I was probably 6 or so. I remember sticking qtips in my hole and loved the feeling. I eventually moved up to sharpie markers, and gradually thicker things I could find around the house as I got older.
ReactReply - SP
Jul 16, 2026I was experimenting with things a a 12 yo. I would put candles, pepperonis, and things like that up my ass as I was masturbating. It was really fun and my neighbor friends would get together camping and fool around at the creek and campsite . Fast forward 40 years and finally had the real thing. I met a guy at the beach and we hit it of great. Well he was my first and Ive had many since
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