I fooled around a lot with a neighbor a number of years back. 1 on 1, and quite often we had another neighbor involved. There were a few others that got involved during those years, we fooled around as 4, and one night, 5, which is where I was first officially penatrated. Here's what happened (Cliff Notes).
During the 5some, I was essentially ushered to the bed and got on all 4's. I was the youngest, and two of the guys were much more confident and experienced. They sort of directed what transpired that night. All of the guys proceeded to inspect me. My ass would get spread, I'd feel fingers touching and prodding. One of them started to play with my balls as well. That lasted a couple minutes or so and everyone started engaging with whomever they were close to.
Over the course of the next 20-30 minutes, I let things happen, and let it come to me. I got hand jobs, gave them, one of the older guys gave me oral for about a minute. I watched my neighbor on his back and get fucked for his first time too. He made a lot of noise but I knew he enjoyed it. The younger of the two older guys crawled up by his face and fucked his mouth. Nothing was happening for me at this time, so I walked out to take a break.
Not 3 minutes later the oldest guy comes looking for me. He finds me, and we go into the other bedroom just the two of us. He obviously had just cum, but he was determined to get his cock in me. I bent over the bed, and he tried to get it in. Up to that point I'd had cock in there hundreds of times, but never penetrated (weird, I know), the tickling sensation that happens while experiencing that always drove me nuts. Couldn't get enough. He failed to get it in from that angle, and he was much bigger then my neighbor I was used to. We crawled on the bed and tried spooning. Again, no luck. He was battling staying hard. But I still loved it. Then he put me on my back and mixed it up between holding my ankles and putting my ankles crossed on his shoulder. No go. Finally, I get into doggy and spread as wide as I can get. He tried and tried. Grinded, etc. No go. By this time, my ass is in sensitive overload. Loved every second. We rejoined the group.
The other 3 were taking a break and talking. I laid on the bed on my stomach. 5 minutes or so later, he crawls on top of me, and he's somewhat hard. After a few seconds, his tip slid in. I wasn't sure what to make of it. Then he got deeper. Then he pulled my hips up into doggy and slowly fucked me. It felt warm, almost hot, pressure, and slightly stung. He kept going slow for about 3 minutes and crawled off me. Almost the second he was done, my neighbor friend throws my ankles on his shoulders, takes not more then a second or two, and finds my ass. His cock was tiny. Seriously tiny. He'd put his dick in my ass more times then I could count, but never once got it "in". That was the first time it'd been in. Even though he was tiny, he was always concrete hard. So that felt different. More like prodded. He and I had messed around for 2-3 years prior to that night. Some of the hottest sex I've had in my life was with him, but when he got on me that night, I wasn't into it. That's the only time that ever happened. I think it was because I wanted to see what happened with the other two. He crawled off me, and promptly started fucking our other neighbor.
After about 30 seconds, two hands grip my ankles and pull me to the edge of the bed. The younger of the two out of town friends wanted a turn. He put my ankles on his shoulder and worked it in. He had about a 6, to 6+ inch cock. He and I were the biggest there. He was thicker than the others too. He worked a couple minutes and finally I was feeling his hips make contact with my ass. He was bottoming out. I didn't mind the angle, but it mostly felt like pressure. Fullness. He fucked me about 5 minutes like that while the others did their thing. He stopped all of a sudden and said, I gotta move you. We went to the carpeted floor.
He put a hand on my hip and one on my shoulder blade. Universal code for, bend the fuck over. He got in. He got deep. After a minute or two, he got fast and kind of rough. Up until then I never made noise. That changed then. I reached back and put a hand on his stomach, which didn't work. Next thing I know, one of the other 3 turned the bedroom light on. I put my face down. I heard, "I think he likes it", etc. I tried briefly to move away after the light went on, no go. He had a good grip on my hips. We wore no condoms back then and he was bottomed out when he came. It horrified me for a bit after (the light going on, them watching him finish in me), but after a year or so, it got me horny as hell thinking about it.
A year later, those two older guys were over again. I don't recall saying much. Just went into the shower. When I came out, they were in my room. I didn't even look at them. Just dropped my towel and felt that hand on the back. Bend over. That afternoon lasted about an hour. I probably had a cock in my ass being fucked harder then I've ever felt for about 45 minutes of that hour.
I've shared that with maybe 2 people.
During the 5some, I was essentially ushered to the bed and got on all 4's. I was the youngest, and two of the guys were much more confident and experienced. They sort of directed what transpired that night. All of the guys proceeded to inspect me. My ass would get spread, I'd feel fingers touching and prodding. One of them started to play with my balls as well. That lasted a couple minutes or so and everyone started engaging with whomever they were close to.
Over the course of the next 20-30 minutes, I let things happen, and let it come to me. I got hand jobs, gave them, one of the older guys gave me oral for about a minute. I watched my neighbor on his back and get fucked for his first time too. He made a lot of noise but I knew he enjoyed it. The younger of the two older guys crawled up by his face and fucked his mouth. Nothing was happening for me at this time, so I walked out to take a break.
Not 3 minutes later the oldest guy comes looking for me. He finds me, and we go into the other bedroom just the two of us. He obviously had just cum, but he was determined to get his cock in me. I bent over the bed, and he tried to get it in. Up to that point I'd had cock in there hundreds of times, but never penetrated (weird, I know), the tickling sensation that happens while experiencing that always drove me nuts. Couldn't get enough. He failed to get it in from that angle, and he was much bigger then my neighbor I was used to. We crawled on the bed and tried spooning. Again, no luck. He was battling staying hard. But I still loved it. Then he put me on my back and mixed it up between holding my ankles and putting my ankles crossed on his shoulder. No go. Finally, I get into doggy and spread as wide as I can get. He tried and tried. Grinded, etc. No go. By this time, my ass is in sensitive overload. Loved every second. We rejoined the group.
The other 3 were taking a break and talking. I laid on the bed on my stomach. 5 minutes or so later, he crawls on top of me, and he's somewhat hard. After a few seconds, his tip slid in. I wasn't sure what to make of it. Then he got deeper. Then he pulled my hips up into doggy and slowly fucked me. It felt warm, almost hot, pressure, and slightly stung. He kept going slow for about 3 minutes and crawled off me. Almost the second he was done, my neighbor friend throws my ankles on his shoulders, takes not more then a second or two, and finds my ass. His cock was tiny. Seriously tiny. He'd put his dick in my ass more times then I could count, but never once got it "in". That was the first time it'd been in. Even though he was tiny, he was always concrete hard. So that felt different. More like prodded. He and I had messed around for 2-3 years prior to that night. Some of the hottest sex I've had in my life was with him, but when he got on me that night, I wasn't into it. That's the only time that ever happened. I think it was because I wanted to see what happened with the other two. He crawled off me, and promptly started fucking our other neighbor.
After about 30 seconds, two hands grip my ankles and pull me to the edge of the bed. The younger of the two out of town friends wanted a turn. He put my ankles on his shoulder and worked it in. He had about a 6, to 6+ inch cock. He and I were the biggest there. He was thicker than the others too. He worked a couple minutes and finally I was feeling his hips make contact with my ass. He was bottoming out. I didn't mind the angle, but it mostly felt like pressure. Fullness. He fucked me about 5 minutes like that while the others did their thing. He stopped all of a sudden and said, I gotta move you. We went to the carpeted floor.
He put a hand on my hip and one on my shoulder blade. Universal code for, bend the fuck over. He got in. He got deep. After a minute or two, he got fast and kind of rough. Up until then I never made noise. That changed then. I reached back and put a hand on his stomach, which didn't work. Next thing I know, one of the other 3 turned the bedroom light on. I put my face down. I heard, "I think he likes it", etc. I tried briefly to move away after the light went on, no go. He had a good grip on my hips. We wore no condoms back then and he was bottomed out when he came. It horrified me for a bit after (the light going on, them watching him finish in me), but after a year or so, it got me horny as hell thinking about it.
A year later, those two older guys were over again. I don't recall saying much. Just went into the shower. When I came out, they were in my room. I didn't even look at them. Just dropped my towel and felt that hand on the back. Bend over. That afternoon lasted about an hour. I probably had a cock in my ass being fucked harder then I've ever felt for about 45 minutes of that hour.
I've shared that with maybe 2 people.
