how was your first time getting fucked by a guy?

[Secretcumlover]

I played around with a friend when I was around 12. I remember spreading my ass cheeks while he pressed the head against my asshole..but we never got it inside. We knew nothing about lube at that age..decades before the internet was born.
In my 40s I met u with a guy on CL and we hooked up a couple times . It was mainly oral but on the second trip he straddled my cock and rode it. You could see the pain and pleasure in his face and moans. Without much lube I was getting sore so had him stop. I asked if he had any lube and had him lube up my ass while I laid on my back, legs in the air and stroking my cock. He got me lubed up and soon felt the head of his small cock pushing inside me. He was only around 3" and pretty thin so it wasn't too bad and felt fucking amazing. I lifted my hips towards him to help him fuck me.. I remember moaning in pleasure amd telling him to fuck me harder. I think he got about 3 pumps in before he shot his load and stopped. I was so bummed it ended so quickly. I still hope to find a guy with a decent sized cock to fuck me someday.

[Neonaught]

My first attempt at bottoming didn't go well. He didn't know what he was doing and just shoved his cock in me and it hurt like hell. To add insult to the injury, he came in about 6 strokes and it was over before the pain passed. After that, I'm all top.

[smallandbi]

I was 21 and a guy in his late 50s was hitting onto me in a bar. He knew I was a virgin and boasted that he had a big fat cock, and he could break in me. I was excited and went back to his flat. I was drunkenly trying to fondle him through his pants. I could not really feel anything though. He pulled his pants down and freed his cock. It was no more than 2 inches at best and totally soft and very slender. I thought my cock was small, but this thing was miniature. He made me get undressed and down on all fours and smeared loads of KY jelly into and around my hole. He was franticly rubbing his cock trying to get it hard. He was struggling to get even semi hard, and could not penetrate me at all. His cock just kept bending with every attempt to fuck me. Then without any warning he came all over my bottom. Not shooting but it just oozed out and kept oozing. He apologized and said he suffered from ED and not had sex for nearly 25 years and simply got over excited. We had some more beer. We watched some gay porn, and we tried again after an hour. I sucked his old and now very shrivelled cock like a limpet. It stayed completely soft, but oddly he groaned a lot. When I flicked my tongue under the tip of his helmet, he kept saying he was about to cum again. He never did and his cock seemed to get smaller. I finally deemed it a lost cause and gave up. I made my excuses, cleaned myself up, dressed and left. I was thoroughly disappointed.

[Spininmywheels]

Spinin, the fun is in the details! You really should share.

OK by~his~side if you must.
I met a couple a while back on line and after several weeks of messaging each other we all decided to meet.
They invited me over to their home and they were the sweetest down to earth people you?d ever want to meet. When I got there we sat around taking and the wife (Jane) offered me some snacks and a beverage. During our conversations we discussed what we liked and disliked, Jane said that she doesn?t usually join in but love to watch and assist if necessary. Not long afterwards the husband (Joe) were in the living room playing with each others cocks and then proceeded to suck each other. At one point I was sitting on the edge of the couch while Joe was sucking me very nicely, I was enjoying it immensely and I leaned back on the couch with my eyes closed and enjoying the bj. As I was blissfully relaxing Jane leaned over me and placed her nipple against my lips, I opened my mouth and proceeded to suck on her tits.
Not long after that Jane suggested we move into the bedroom where we would be more comfortable. One there Joe and I continued enjoying each other as Jane watched. After a little more time Jane asked if I?ve ever been fucked by a guy? I replied no. She the asked would you like to? I without hesitation replied Yes I would.
They were both happy to here that.
I proceed to get on all fours and Joe started lubing my as up and playing with it for a while loosening it up for his entry. In the meantime Jane is talking to me and encouraging me and coaching me as things developed.
Then the time came. Joe asked if I was ready and I replied yes. He then slowly, carefully and patiently worked his hard cock into my awaiting ass. After a few minutes he was deep inside of me and now fucking in a nice rhythm. I was enjoying the hell out of it. And then when I didn?t think things could get any better the unthinkable happened. Jane knelt alongside me and started to stroke my cock.
Now I?m being fucked by a guy for the first time and being milked by his wonderful wife.
Joe continued fucking me an then blew his hot load into my Virgin ass. After Joe shot his load Jane continued milking me until I blew my load and then collapsed on the bed.
Afterwards we all laid there with great big smiles on our faces.
It was a great time. We did get together several times after that. We are still in touch but has been years since we got together. I miss them and the times we had together.

So bi~his~side, is that detailed enough? I enjoyed telling it and sort of reliving it.

[friesbaconnekkid]

OK by~his~side if you must.
I met a couple a while back on line and after several weeks of messaging each other we all decided to meet.
They invited me over to their home and they were the sweetest down to earth people you?d ever want to meet. When I got there we sat around taking and the wife (Jane) offered me some snacks and a beverage. During our conversations we discussed what we liked and disliked, Jane said that she doesn?t usually join in but love to watch and assist if necessary. Not long afterwards the husband (Joe) were in the living room playing with each others cocks and then proceeded to suck each other. At one point I was sitting on the edge of the couch while Joe was sucking me very nicely, I was enjoying it immensely and I leaned back on the couch with my eyes closed and enjoying the bj. As I was blissfully relaxing Jane leaned over me and placed her nipple against my lips, I opened my mouth and proceeded to suck on her tits.
Not long after that Jane suggested we move into the bedroom where we would be more comfortable. One there Joe and I continued enjoying each other as Jane watched. After a little more time Jane asked if I?ve ever been fucked by a guy? I replied no. She the asked would you like to? I without hesitation replied Yes I would.
They were both happy to here that.
I proceed to get on all fours and Joe started lubing my as up and playing with it for a while loosening it up for his entry. In the meantime Jane is talking to me and encouraging me and coaching me as things developed.
Then the time came. Joe asked if I was ready and I replied yes. He then slowly, carefully and patiently worked his hard cock into my awaiting ass. After a few minutes he was deep inside of me and now fucking in a nice rhythm. I was enjoying the hell out of it. And then when I didn?t think things could get any better the unthinkable happened. Jane knelt alongside me and started to stroke my cock.
Now I?m being fucked by a guy for the first time and being milked by his wonderful wife.
Joe continued fucking me an then blew his hot load into my Virgin ass. After Joe shot his load Jane continued milking me until I blew my load and then collapsed on the bed.
Afterwards we all laid there with great big smiles on our faces.
It was a great time. We did get together several times after that. We are still in touch but has been years since we got together. I miss them and the times we had together.

So bi~his~side, is that detailed enough? I enjoyed telling it and sort of reliving it.

That sounds a lot like my first time, with my friends Tim and Arlene. Having her there made it especially memorable.

[Tinycockkev]

Ive been married for a long time. I have a really small dick and love small penis humiliation. I love being a sub and started sucking guys cocks when my wife is away. I really love being a tiny dick cock sucker for dom guys it?s such a turn on. The last time I was sucking this guys cock he flipped me over and fucked me hard. I had never been fucked before and I fucking loved it. I felt so submissive stroking my tiny dicklet while he fucked my ass, then pulled out and shot a huge load in my mouth, so fucking hot. I think about it all the time

[joseluis]

WOW!!! What a great story!!!

[Unholybi]

Happened just once, right after coming back from honeymoon lol I was 31 he was gorgeous young ladyboy with modest cock. He didn?t last long but we have both cum at the same time to our surprise. Never seen her after, wish we continued for longer. Since that only being pegged by my female lover. Love anal unfortunately couldn?t meet proper guy since my first and only cock so far.

i remember to this day looking back over my shoulder to find a beautiful creature happily smiling holding my hips pounding my ass, and that gorgeous yet fake breasts. Night of a long time dream come true ☺️ it’s been 8 years now and I miss you Caz

[licyou69]

It was good, but not great. The only negative aspect was he's an older guy like me and was having trouble keeping it hard. After several failed attempts at him getting in me and staying hard, he took off the condom. With a promise he wouldn't cum in me, I let him back in me bare. It felt amazing when he was finally able to work up a good stroke inside me. Unfortunately, he still wasn't able to keep it hard for long, so he pulled out and I got him to cum with a combination blowjob/handjob. At least I was able to swallow his cum instead of him dumping it into a condom. A couple of weeks later I let another man fuck me and it was amazing. He was strong, energetic, and pounded my submissive ass like I needed.

[JerzeeGawker]

Getting my ass cherry popped


I am a male at the time in my 30's. I was separated from wife living with an older female with benefits. GAWD could the woman moan and quick to orgasm as well as often !
I am no stranger to sucking a little, and I do me little under 6 inches in length and about 1 3/4 diameter. About like my own junk is.
So I get this hankering for a little on the side male to male. Now I am a good size city in Upstate NY off 90.
I locate a site I can try to find same sex partner willing. I get a reply as availability. NOW !
We agree to met at a flower shop where he works. Now this is before everyone started taking selfies and sex vids on their phones. I drive to the shop walk in, introduce myself and he goes and puts the closed sign up out to lunch. We go behind this curtain. Wasting no time we both drop our pants past our knees. He drops down and takes my cock into his mouth and lets it GROW ! After a minute or two he stands up. Asks me "You ever took it in the ass before ?" I told him . . " Nope Care to pop that cherry !?" His reply . . . " Love to !" With a shit eating grin on his face ( no pun intended ) I spin around and bend the knees to widen my little ass cheeks. He dropped to his knees and rimmed me a new. Jammed his tongue up my ass a good inch or so. Was amazing !!!! He applies some time of lotion and "slides" right in All the way to his ball sac ! Balls deep on the first cherry busting stiff cock ever ! After a minute or two of "getting use to it " he starts slowly pulling out. When just his head is in my tight freshly broke cherry asshole he stops, holds for a few seconds and Slides it nice and steady back in. After he bottoms is when our balls meet. The longer he fucked me the harder my dick got ! I was just about to the blowing my load point when his lets loose a stream of hot fluids filling my ass ! OMG AMAZING ! ! ! After 3 solid hot streams deep in my ass he slides our drops to his knees and cleans up the outside of my asshole and blows me till I pull out and shoot my load on his face. We cleaned up said our goodbyes and I have not had another experience like that since.

[Secretcumlover]

I played around with a friend when I was around 12. I remember spreading my ass cheeks while he pressed the head against my asshole..but we never got it inside. We knew nothing about lube at that age..decades before the internet was born.
In my 40s I met u with a guy on CL and we hooked up a couple times . It was mainly oral but on the second trip he straddled my cock and rode it. You could see the pain and pleasure in his face and moans. Without much lube I was getting sore so had him stop. I asked if he had any lube and had him lube up my ass while I laid on my back, legs in the air and stroking my cock. He got me lubed up and soon felt the head of his small cock pushing inside me. He was only around 3" and pretty thin so it wasn't too bad and felt fucking amazing. I lifted my hips towards him to help him fuck me.. I remember moaning in pleasure amd telling him to fuck me harder. I think he got about 3 pumps in before he shot his load and stopped. I was so bummed it ended so quickly. I still hope to find a guy with a decent sized cock to fuck me someday.

Well years later , I finally got my ass fucked good and hard. I started using grinder and AFF. The first guy lived about an hour away and I drove to his house and we played in his camp trailer. I sucked him off until I swallowed his load. He stayed hard and tried to fuck me. He started to cum as soon as the thick head popped in. Luckily he jumped off me and I was able to catch his second load in my mouth! A few months later I met up with a guy with a fat 6.5" cock nicknamed "the hole puncher" . We tried for about an
hour and he couldnt get the head to slide in so we gave up. Months later we gave it another shot. Thos time I fucked myself in the shower with a decent size dildo after going through my internal cleaning routine. When I got to his house i sucked hos cock for about 20 minutes because that gets me horny af! He then placed 3 pillows under my belly to lift my ass in the air. He lingered and tongued my assfrom behind while rubbing my cock. After lubing up my ass he easily slid a average size dildo right into my ass. With the dildo inside me he laid on my back and went through the humping motions. After a few minutes of this he brought the fat head of his dick to my ass and slid up and down my lubed cheeks with his cock gliding over my puckering asshole. He removed the dildo and placed his cock against my ass and pushed right in. I jumped and whimpered in pain for jist a moment but was soon lifting my ass towards him to get all of his cock inside me. Fucking him back and grinding my ass onto his cock felt fucking amazing! Soon I'm telling him , begging him to fuck me faster . A few minutes of hard fucking he told me he's going to cum . Instinctively im yelling " fuck my ass, shoot that hot cum deep inside me " . He stayed hard inside me and continued to fuck me while reaching down and rubbing my rock hard cock. I'm now laying more on my side with one leg up exposing my cum filled asshole to him. Over and over he'd pull his cock out, rub it against my asshole then slam his entire cock back inside me. The pleasure was insane!
Afterwards he had me lay on my back and slide towards the bottom of the bed where he had kneeled down to blow me. That man knows how to suck cock..WOW. within minutes I had the biggest orgasm I've had in years filling his mouth with cum. I could hear him slurping and swallowing ot down over his moans . He only lives a few blocks away and plan to make this a frequent thing. He has a buddy from out of town that stays occasionally. Supposedly he has a thick 9" cock and we are planning and all day or all night playdate soon.
I can knock a few things off my bucket list. Sucking one while the other fucks me.. a glory hole to feed me. Both of them taking turns fucking me.

[iamcontent]

I have always known I was bisexual I am 61 now had my first experience at 10/11 Cock getting sucked and vice versa. Tried getting fucked when younger was to tight not properly stretched or ready. I have fucked many holes sucked many cocks and pussies rimmed and been rimmed but the urge to getting fucked was getting overwhelmed
So finally at age 51 I brought 3 toys a 6 inch butt plug a 8 inch Dillon and a 12 inch Dildo. For 6 weeks every night I worked my way up from the 6 inches to the 12 inches.
One night I made my way to the Bathouse near me had a couple of shots and went in it was Tranny night. I put on my cock ring and did my walk around passed by a room saw a cute plump tranny on her back sucking a cock getting her tits sucked I asked to join in a d she said yes I tool her 6 incher in my mouth after 5 minutes she shot a load in my mouth I swallowed she asked the other two to leave they left she thanked me said it was one of the best BJ'S she has ever had I told her I am proud of my oral skills we started making out my 8 1/2 inch BBC got rock hard I told her I have never gotten fucked and I am ready to her she cock got hard immediately and she rimmed me for 10 minutes added some lube and entered me. I had been sniffing poppers the entire time it felt so good no pain since I was very stretched out and in lol. After 10 minutes she shot a load in me. I thanked her walked out showered and went to the sauna another guy was in there cock was about equal to mine we both blew each other I fucked him then he fucked me. In a 30 minutes span I got fucked twice by two different cocks and two different loads.
It was good a d fun

[RICKCASV]

When I first started having sex with men (age 22) I had no desire to have any kind of anal sex. I told who ever I was having sex with upfront that I was into giving and receiving hand jobs and that I really loved giving and receiving blowjobs, I would also tell them I loved sucking a man's cock and having him cum in my mouth and swallowing his cum.

Years later (age 26) when I became involved with a very good friend who was gay my attitude about anal sex began to change.. Having regular sex with him changed the way I felt about anal. One time he was giving me one of his always excellent blowjobs when he suddenly lifted both of my legs up in the air (I was sitting on his couch with him kneeling on the floor in front of me). He took his mouth off of my cock and started licking my asshole. I was startled but I decided to let him lick and kiss my asshole because it felt absolutely amazing. This went on for a good 30 minutes. It was pure ecstasy. and in some ways was more pleasurable than having him suck my cock. He didn't need to ask me if I liked it because my groans and squirming told him that I loved it.

After that session I started thinking about having anal sex with him. The more I thought about it the more I knew I wanted him to fuck me. Because we were friends and he knew I was an anal virgin I knew he would be gentle. I had absolutely no interest in being a top so I focused on being a bottom. Could I actually let another man fuck me? It was one thing to give a BJ or HJ to a man and have him reciprocate but letting another man put his cock in my ass was a huge step in my bi-curious experiences.

As time went by I became more comfortable with wanting to find out what it felt like to be fucked by a man. One night, after many very hot BJ/HJ sessions over the previous months I came right out and told him I wanted him to fuck me. We were both naked when I said this so he got up and came back with some lube and began preparing his very large (8-9 inches) and very thick cock to penetrate my ass. Terry had a very large mushroom cock head and I knew it might be difficult for my ass to accept his cock. He told me that it might be painful but he would be as gentle as possible. I got into the doggy position and he rubbed some of the lube on and around my asshole. I felt one, then two and finally three of his fingers enter me in an effort to loosen me up. It felt really good having his fingers in me. He then told me he was going to put his cock in me. All of a sudden I felt an excruciating pain shoot through my lower body. I immediately made him stop but I still wanted his cock in my ass so we tried again a couple of more times but I was just too tense and inexperienced to relax and let him enter me.

Many years went by and whenever I was with a man it was always just blowjobs and hand jobs, always where I had the guy cum in my mouth and I would swallow him. Then I met a gay couple on the internet and we started e-mailing each other. I told them I wanted to suck them both off and have them cum in my mouth. I also told them that if the chemistry was right they could fuck me with the condition that they would not cum in me so I could suck them both off after they were done fucking me...

Well, the chemistry was right and when one of them said "Let's have some fucking". I asked the other one if he wanted to fuck me and he said yes and I said OK and he went to get some lube. I wondered if he would also bring back condoms with him.

While he was gone, I started sucking his partners cock to get him ready to fuck me. When the other man returned to the living room with the lube he did not have condoms. They were going to bareback me. After all these years I was going to finally find out what it is like to have a cock in my ass and I was going to do it bareback.

We had exchanged pictures and I knew I could handle the size of these two men's cocks (both about six inches or so and cut) if they decided they wanted to fuck me.. I got in the doggy position and spread my legs. I wanted it to be easy for him. I felt him put his hand on my hip and his lubed cock slid right into my ass with no resistance. He wasted no time in getting into thrusting his cock into me repeatedly and after getting used to the sensation of his cock in me I started to really like the feeling of being fucked, of knowing the cock I had been sucking earlier was now in my ass.

After about 20 minutes it was time for the other man, the one who had said "Let's have some fucking" to take his turn.. I was actually attracted to this man and not just his cock. This was very rare for me. Only three times in my life was I actually attracted to the man and his cock and this was the third time. He was a tall, lean athletic man and doggy would not work for him so he had me get down on all fours and bend at the waist so that my head went down to the floor and he entered me. .

By now I was really enjoying it. I started making noises, saying "fuck me, fuck me" and moving my ass back and forth on his cock He kept fucking me for another 15 minutes or so and then he pulled out. It was time for me to suck them off and have them cum in my mouth.

This was my first and only time in all male threesome so I was really excited about getting to suck two cocks off and swallow their cum in one night.. The first guy who fucked me said he wasn't ready yet so I told the second man I would do him first. I really like to suck cock, taking my time and exploring the man's cock and balls, finding the more sensitive spots on both when I give a blowjob. I give a really long and sensuous BJ and while I was sucking this guy off it struck me that we had gone straight from him fucking me to me taking his cock into my mouth and that this was my first ass to mouth blowjob. It wasn't long before he was cumming in my mouth with me savoring his cum, the texture and the taste. After I took my mouth off his cock I squeezed his cock and a large droplet of cum appeared on the slit at the end of his cock. I put my mouth around his cock and sucked all the cum that had not already cum out. I then did his friend and got my second load of sweet cum to swallow..