Guys - tell about the first time being fucked

He was one of my best friends growing up, and summer before college, we both began experimenting. He was quite large (~7" or so), fatter at the top, and curved slightly upward.

The first time he fucked me, I was on top. It took forever to take all of him as I didn't really have much experience other than a finger or two. It also didn't help that we used Vaseline. It was all we had and since we were both virgins, we didn't use condoms.

Once I got past the fat top 1/3, I slid down him to the hilt. It took my breath away. It stung like hell for a few minutes as I just sat still, trying to adapt as he stroked my cock. Once I was brave enough, I began to ride him. It was maybe 10 thrusts before he was about to blow. He thrust hard up into me as I grinded down on him. The feeling of him filling my ass as he stroked me immediately made me cum hard. I covered his chest and and face. I even managed to land the first couple above him on the head board. To this day, I don't believe I've ever had one person cum so much inside me.

That was it. I was hooked.
 
I had always messed with my ass with toys, always wanting the real deal, when it finally happened, just thinking "This is happening this is happening" and it happened, and I loved it.
 
My first time was good but not great. Shortly after, though, I wanted more.
 
On 12/6/2022 I gave up my anal virginity. It was a special day and it left me wanting more. My Top was perfect. He seduced and prepared me until I was wanton. He Fingered me. Rimmed me. Two fingers next and then two larger fingers. I begged him three times before he boned me and even then he made me wait and wait before he mounted me. He was gentle at first but took his prize forcefully once my inner slut was triggered. We determined that we could safely bareback and so we did. He initially took me Over the sofa and then later again on a massage table; first doggy and then with my legs on his shoulders. I was given two loads and I treasured each one. I was plugged afterwards to keep his seed inside me. It was everything I had hoped it would be. I never orgasmed from being fucked but he told me to jerk off for him when we cleaned up in the shower. After our session together, my legs were wobbly and I felt a bit light headed. I think I was cock drunk. We had our second session 3 weeks later and I will visit again this Saturday. I am now his pet, his bitch and fuck toy.
 
Ive only been fucked once by this guy. He had a tiny cock and didnt use lube. He licked my ass first. Honestly it wasnt an experience i recall as being all that pleasurable. Although ive topped many times, i have fantasized about being fucked in the right conditions. Being able to clean up very good and the guy taking his time. Ive sucked many guys and fantasized later about the same guy fucking me. One of these days im going to try it myself.
 
My first time was with a transgender woman that I had been talking to for months but then met for a week together.

It was so exciting riding on the metro with her as she put my hand in her lap and I could feel her hard cock. There it was - would I be able to go through with it? What had I gotten myself into?

After we checked into the hotel and got to our room, we immediately undressed and began to kiss and play with one another. Finally I pulled her panties off to reveal her throbbing little cock. It was between 4 and 5 inches but really stiff and hard definitely ready for action. Seeing it made me realize just how much I needed it.

I wasted no time putting lubricant on her cock and a little in my hole, then I assumed the doggie position on the bed. Immediately she got behind me and I could feel the tip of her cock at the entrance to my hole. Then in one big thrust she shoved her cock completely up my ass!

OMG! My head was spinning both from the stab of pain I felt as well as the realization that it was actually truly happening. After so many fantasies over so many years, here I was bent over like a bitch with a cock in my ass. It felt unreal. Was this a dream?

After only a minute or two of vigorous fucking, she stopped her thrusting and pushed her cock in as far as she could go. This was the moment I had been waiting for. Hearing her moans and groans, I knew that she was having her orgasm and breeding me with her cum. I couldn’t feel it but it was the most sexually exciting moment of my life.

After she finished cumming, her cock stayed inside me and she leaned over me to say, “Don’t move. I am going to get hard again and fuck you some more.” Really? I could not believe what I was hearing but I followed her instructions and stayed in position with her cock still in my ass.

After only a couple of minutes, I could definitely tell that her cock getting harder and harder. Soon she was ready for round two and she fucked me again this time taking more time before cumming again.

As I was taking her second load of cum, I thought to myself, this is incredible! Here I am getting two loads of cum from this girl in a single fuck! God, she is an amazing fucker!

So she was. That night she fucked me three more times cumming in my ass each time. I felt like a wanton cock hungry slut but I knew then that I was born to be a bottom. All I want is a girl with a cock dumping her cum in my ass.
 
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You will like it, guaranteed. Getting in takes a little bit, but like I suspected it’s so much better than toys. Feeling the thrusts just brings it to a whole new level. I kept begging for harder even though he was doing the best he could. He used a rubber so I didn’t getthe full experience getting a load of cum in my ass but there was a satisfying loose feeling I had that stayed for a day or two.
 
Ive only been fucked once by this guy. He had a tiny cock and didnt use lube. He licked my ass first. Honestly it wasnt an experience i recall as being all that pleasurable. Although ive topped many times, i have fantasized about being fucked in the right conditions. Being able to clean up very good and the guy taking his time. Ive sucked many guys and fantasized later about the same guy fucking me. One of these days im going to try it myself.
Being fucked by a tiny cock is a strange experience, it's like 'have I been fucked or haven't I? It doesn't feel like I've been fucked but there's a little dribble of cum up my bum, and my friend has a very smug expression on his face!'
 
I meant the guy in his hotel room he had me strip to nothing but my panties I had on under my clothes then he pulled me close to him he leaned in and kissed me I kissed him back we started to make out as we did he started to play with me ass and I rubbed on his cock then he pushed me on the bed and pulled my panties off and dropped his underwear and lubed his cock and my hole pushed my legs back and slowly pushed his head in he started off slow then when he started to go faster he grab my sissy clit and jacked me off as he fucked me hard we both cummed at the same time
 
My 1st time was when I was 19, I had been secretly with the son of one of my parents friends. Back in the 1970's it was so much more taboo guys being with guys and it didn't help as I was from a large Italian Catholic family and he from an Irish Catholic one. The 3rd time we hooked up was in a secluded area I had just found with a path into the woods just larger enough to drive a car into a big open area, both the path and the clearing were totally invisible if you didn't know they were there. I fucked him that time and it was wonderful. The next time we hooked up there again as we kissed he told me he wanted to fuck me this time and we climbed into the back of my big old station wagon, with the back seat folded down it was like having your very own king sized bed back there.

As I knelt on the carpet my ass in the air and legs spread wide open he rimmed my ass, not that we knew what rimming was back then we just called it eating ass. His saliva flowed into me as his tongue buried inside and when he slowly took it out I could feel him hovering above, I was to be totally honest a bit scared but also so horny thinking about it I wasn't sure what to think. You see the scared part was his size, almost 8" and fatter than most I had seen, I had sucked his cock and he was also the very 1st guy I felt inside my throat and wanted him so much to be my 1st fuck, the horny part well you all know teenager with a cock how could I not. As he finally pressed his head against my ass and pushed his head barely forced it's way in when I felt intense pain more pain than I had ever felt, my ass tightened instinctively to prevent him from entering and he stopped pushing holding himself inside me asking me if I wanted him to stop. I shook my head telling him I wanted to go on and after relaxing as the pain subsided some I told him to push again. Half of his cock pushed in and that same pain ran through me again, I could swear it felt like even my cock was hurting from the pain not just my ass. After a long pause with my ass clenched I was able to relax again and he slipped the rest inside me holding it deep until I begged him to do it, I was so horny and even though there was still so much pain I wanted to feel his release inside me as I wanted his warm cum filling me up. After he began pushing his cock in and out of me the pain slowly drifted to a dull almost numbness and I was amazed at how my ass could possibly open so wide to take his thick shaft. It too maybe all of 6 minutes before his load shot, I could feel the warmth as his cum shot inside me and with each push inside it streamed from my ass running down my thighs.

When it was over he collapsed on top of my ass with me kneeling holding us both up, I could feel his cock shrinking inside me and as he pulled it out slowly after he became flaccid I had almost a sense of disappointment that it was gone. As we dressed I began feeling the pain I felt as he entered me and when I sat behind the steering wheel I had even more pain almost a feeling as if I was ripped or something. I dropped him off and drove home the pain subsided a bit at times but returned when I moved around on the seat. The 1st thing I did was go the the bathroom and try to see my ass in the mirror which turned out to be futile so I sat on the toilet looking at my underwear to see if there was any blood, thank God I didn't see any, I then tried to pat my ass with toilet paper and found none man I was so relieved.

The next time he fucked me a few weeks later I was so happy there was so much less pain and the following times I am happy to say there was none.
 
I posted this on a very similar thread on this site:


I have very little M2M experience. The second one involved my one and only anal experience. He fucked me.
It was strange because until this occasion I never wanted anal but it 'happened'. We met on another site and after talking things over we arranged to meet at a motorway service station for coffee and see if we wanted to take things further. Throughout all the chat leading to the meet, and indeed over coffee, it had been made plain I was not interested in anal sex either way. No problem there and we decided to get a room at the on site Premier Inn. To cut a long story short we were wanking and sucking each other when I felt an obviously lubed finger stroking around my hole. Where I thought I would react and stop him I found that it felt so hot I let him continue. His finger slipped in and oh my days it felt fantastic. After a time he whispered that he now had three fingers inside me sawing in and out. No pain at all. Well it was ace and I heard a voice that I didn't even recognise as my own saying " fuck me, please fuck me". I was literally begging him to fuck me, much to my surprise. I was mad for it!
He donned a condom, had me kneel on the edge of the bed and entered me. Jeez but I was loving it. I was being properly fucked like a slut and I wanted it to never end. Cum was leaking out of me as his cock passed back and forth over my prostate. And I mean cum. Not precum but thick ropes of cum. I seemed to be in a perpetual state of orgasm and just wanted him to keep going. Up until then I'd experienced no pain at all apart from a very brief 'sting' as his mushroom head pushed past my sphincter, only deep pleasure. However he then took it up a notch and pulled all the way out only to plunge forcefully back into me. His rather large helmet hurt big time in both directions and I was no longer enjoying this. Wasn't long before he withdrew, removed the condom and finished by spraying hot cum over my arse and balls whilst remarking upon all my spunk on the sheet. So a great although unexpected experience was somewhat spoiled by his over exuberance. Shame really because overall I had thoroughly enjoyed being his 'girl'. That came as a real shock to me.
So there you have the story of my one and only experience of anal sex. Would I succumb again? I suspect with the right man I could easily let a man take me. The issue is first finding a man for any kind of sexual interaction. I've found it impossible.
 
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On 12/6/2022 I gave up my anal virginity. It was a special day and it left me wanting more. My Top was perfect. He seduced and prepared me until I was wanton. He Fingered me. Rimmed me. Two fingers next and then two larger fingers. I begged him three times before he boned me and even then he made me wait and wait before he mounted me. He was gentle at first but took his prize forcefully once my inner slut was triggered. We determined that we could safely bareback and so we did. He initially took me Over the sofa and then later again on a massage table; first doggy and then with my legs on his shoulders. I was given two loads and I treasured each one. I was plugged afterwards to keep his seed inside me. It was everything I had hoped it would be. I never orgasmed from being fucked but he told me to jerk off for him when we cleaned up in the shower. After our session together, my legs were wobbly and I felt a bit light headed. I think I was cock drunk. We had our second session 3 weeks later and I will visit again this Saturday. I am now his pet, his bitch and fuck toy.
Good for you, buddy! Welcome to the family! :)
 
Finally, we late bloomers have something other than regrets for missed opportunities :)
 
My first time was painful. Even though he was being patient and going in a little at a time. I kept telling him to pull out because it hurt. Finally he suggested I get on top. I did and even though it was still painful I was determined to have him in me. I eased down on him gritting my teeth. When I finally felt it break the plain of pain it slid in nicely. It was sexy to hear him say ahhh there it is. I sat still for a moment to become comfortable with his cock in me then began to ride him. It was bliss.
 
First time was with a long term FWB. We had tried everything else over a period of many months when he asked me if I'd be willing to try fucking. I figured I had liked every other one if his suggestions so I'd give it a try. He patiently lubed and fingered me and slowly slid in saying he would stop anytime I was uncomfortable. The first few inches were ok but then it started to hurt and I asked him to stop. He held it there until I told him to try again, and he very slowly went deeper until he was all in. I have to admit I was glad he wasn't any bigger (maybe 6 inches). Told him to just stay like that , maybe rock a bit, and let me get used to it. He fucked me gently for about 5 minutes and then pulled out and we finished each other off as usual with hands and mouths. I honestly wasn't sure how I felt about it. But the next time we got together I wanted to try again and this time it felt good and right. In fact I wanted him inside me in every position we could think of including when we were finally in the shower cleaning up. Only been fucked by one other guy and it didn't measure up to the first. (in enjoyment not size). If I ever find a regular FWB I will try it again.
On the "flip" side, he never was able to relax enough to take me no matter how often we tried. Guess that made me the bottom?
 
First time was with a long term FWB. We had tried everything else over a period of many months when he asked me if I'd be willing to try fucking. I figured I had liked every other one if his suggestions so I'd give it a try. He patiently lubed and fingered me and slowly slid in saying he would stop anytime I was uncomfortable. The first few inches were ok but then it started to hurt and I asked him to stop. He held it there until I told him to try again, and he very slowly went deeper until he was all in. I have to admit I was glad he wasn't any bigger (maybe 6 inches). Told him to just stay like that , maybe rock a bit, and let me get used to it. He fucked me gently for about 5 minutes and then pulled out and we finished each other off as usual with hands and mouths. I honestly wasn't sure how I felt about it. But the next time we got together I wanted to try again and this time it felt good and right. In fact I wanted him inside me in every position we could think of including when we were finally in the shower cleaning up. Only been fucked by one other guy and it didn't measure up to the first. (in enjoyment not size). If I ever find a regular FWB I will try it again.
On the "flip" side, he never was able to relax enough to take me no matter how often we tried. Guess that made me the bottom?
Well, if you both enjoyed it, top, bottom, is there really any point to being pegged as type of something? 😝
 
My new boyfriend and I went up to play in the snow. Going home we were wet and cold so we got a hotel on the way down the hill. The clerk must have read us because she asked if we wanted a double bed. I said sure.
We showered, had food delivered and hopped in bed together naked for the first time. After a little playing around, he started probing me with his cock. I wasn’t too sure about losing my virginity, but there was no stopping him. He just took over which really turned me on. It hurt at first, but he kept going. Then after some nice fucking he pulled out. I was confused.
Then we made out for awhile and then he cleaned my dick and then sucked me off until I came.
When morning came we made out a bit and then he positioned me missionary style, and we kissed and kissed as he went in me. It still hurt at first but he was fucking me like a madman!
The pain was gone. It was fucking great. I’ll never forget his pulses inside of me, nor the special feeling of cum dripping out of me as he pulled out.
 
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