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I think I was about 22 years old when it happened. I was in Texas doing some temp work and staying in a motel. I got to chatting with a guy and one thing lead to another and he ended up in my room. Things got really hot and heavy and then he asked if he could enter me. Scared at the thought I said yes. He took things nice and slow. On his back I straddled him. He lubed me and himself up and just said "lower yourself into me at your own place. I did.....slowly. But once he was all the way in.....oh my gawd! I was frantically pounding up and down on him! What a night!

In the bad room of a gay theater. It tock several trips sharing bj & watching guy bend over I desided to let my dildo stretched ass hole feel a warm, stiff cock. I was surprised how little discomfort I felt. He was rough & I loved the abuse. been used many times since.

Well, as long as fingers don't count, I'm still an anal virgin!

My finger had been in there many time (trying SO hard to do a self-prostate massage), but there have been probably just under a dozen doctors (including one female) who've had their fingers in there, as well.

While I believe I'd enjoy being fingered properly by someone who knows how to do a PM, to be honest I don't think i'd want a penis in there. To each his own, I guess....

I'm still virgin.

I was 53 (late bloomer)
I wanted fucked and found a guy on the net.Since then there have been several.
First cock I sucked was at 47.
I found both very "addictive"

I think i was 22 when i first got fucked. Sucked off the odd cock since i was 18/19 and finally wanted some cock in my ass.

I was at uni at the time and ended up chatting to a guy on a night out. We got along and while nothing happened that night we did swap numbers. Turned out he only lived a couple of streets away from me! Was both exciting and very nervous at the time.

He was good, knew my ass was virgin so took his time and he wasn't too big either. Fucked me nice and slow, at least to being with! Ended up cumming in my ass (he had a condom on) and it was so hot taking a cock and load. Met up with him a few more times after that, always a good fuck and during our last meet before i went home from uni i ended up sucking him off, swallowing his load, and, when he was hard again, he fucked me bareback and came in my ass

I was a late bloomer. I didn't start my MM activities until I was 55 years old. I had been very curious for many years but never acted on it. At this time, I had just gotten a new job and found myself traveling for three days every other week to educate customers on a new line of equipment. After about two months of this it was getting very boring. I was almost at the point of looking for another job when I looked around me while sitting at my hotel bar and noticed all the unattached men sitting around me looking as bored as I felt. I wondered if I could use the situation to my advantage by having a bi experience without having to worry about excuses to tell my wife. I looked around and spotted a man about my age and build and sat down at the bar near him. After a few minutes I struck up a conversation with him and found out that his job like mine put him on the road often. We talked jobs and sports and other miscellaneous things for about two hours before the conversation turned to sex. It turned out that like me, he had thought about bi sex but never did anything about it. We ended up going to his room and experimented. Tried BJ and I tried to swallow his cum with most of it falling out of my mouth. If I remember correctly he would not take my cum in his mouth. He wanted to try fucking my ass since his wife wouldn't let him fuck hers. He seemed to really enjoy it. On the whole we both had an enjoyable time. I have to say that I used that same bar room experience many times since that first time and had many successes over the years. Now that I'm retired I miss those traveling days.

Just lost my virginity 2 weeks ago. It took many years to get there but, I so glad it happened.

25, a mate and I were wanking while watching an old 80's porn flick on VHS, she took it up the arse, so we started talking about it. Curiosity got the better of us and so with a bit of Vaseline from the bathroom, I bent over and he slowly entered me. Hurt like shit and he had to pull out but after a break we tried again and eventually he managed to pound me. Only got a few pumps in before he blew but for me, it was the start of taking it up the arse, and loving it.

One night in the summer of 1977 when I came home from ROTC summer camp ( was curious and closted) my gay and out roommate walked up.behind me turned me around and kiissed me long and slow while he slid his hand down to my ass.

Since my cock was getting hard I moved his hand and placed it over my stuffing member and we went over to the couch for a heavy make-up session. When we came up for air he took me by the hand and as we went to my king-size water bed he said, "Time to get you naked."

He got me naked. I got him naked. He gave me my first orgasm by a man and I gave him my first hand job and tasted cum for the first time. WE did just about everything two men could do with their hands and mouths.

I woke up the next morning with his hand around my 6" cock and he told me that
he has been fantasizing making love to me ever since we met me but he thought I was straight. I told him that I wanted him in my bed since the first night we moved in. By then we were completely awake and my 6" and his 7" were completely stiff. He gave me another deep, long kiss and whispered " Can I fuck you? I replied using a smile. I reached over and handed him the tube of mY we almost used up the night before.

I rolled over on my back, raised my ass.and he slid right.in. I was so ready to fuck him that everything was truly natural. I felt his thrust and heard his happy moans. With one big final thrust he sank himself and I felt his warm man juicee flow from his cock. When he was done he smiled at me and said, Your turn" You see, Kent was an anal virgin too. But he still wins because he popped all my cherries. He was the first person to make me cum! From that day on we slept in my big bed and gave e each other big Os Is almost every night.

That weekend was the best sex I had ever had in my life. We still get together each year. I'm going up to Dallas for his birthday. Can't wait!

So yes, I was 21.

49 he had me on the beach at night. He certainly felt good

at 29 with a friend away from home. it was ok.

I was 27 when I had my ass fucked the first time. A friend/coworker and I shared a hotel room on a business trip. We'd already done oral but no fucking. The room had two beds in it, but we both slept in one for the two nights. We enjoyed ass fucking three times in two nights. That was my first time as a bottom, and although my opportunities haven't been frequent, I've enjoyed it ever since.

I am 72 Horny and still waiting for a big cock to enter me

Somewhere around 40. I had been playing dressing in panties and bras for sometime and using dildos or anything else that could be inserted for quite a while. I had also meet with a few men for oral play. Then it finally happened. I was playing with a guy one day at his place. We had been swapping oral when he rolled me on to my stomach. A squirt of lube and then I felt him probing with his finger. I finally asked if he would fuck me. He did! I loved it and have become quite a bottom.

I haven't lost it yet...but would like to

Having been married for 31 years, my first anal was after the marriage ended, at the age of 52 (2007).
I was visiting Melbourne, and went to RAM lounge above an adult video store. A few guys were there. I started playing with a lovely Asian man (nice dick). He suggested we go into the private room. There were undressed and started enjoying each others' naked bodies. He said he would like to fuck me. I took a deep breath and thought, "Here goes! He's not too big, this will be my chance. I let him know that this was my first time, and he was very respectful. I got on all fours and he (having lubed my tight hole) began to press his knob into my hole. I wasn't sure it was going to go in, but he gently persisted. As he broke through the first barrier I thought I wasn't going to be able to go through with it, but he eased in gently, and eventually was rhythmically pounding me. After a while he said I want you to turn over so I can cum. So I lay on my back on the bunk, while he stood between my legs. He lifted my legs over his shoulders and again began thrusting his dick into my now quite receptive hole.As he got closer, he started speeding up, then pulled out, tore off his condom, and let his load fly.

It was a magical evening. When I went back out onto the street, I felt like I was floating, and my mind was filled with dream-like sensations. Since then, my best fucks have been from Asian guys - partly because they are generally a bit smaller, and partly because they seem to be particularly sensitive and sensual lovers.