How Was Your First Time Anal

My first time was pretty bad. We did everything there was to do over the past few years but never tried anal. He asked me if he could fuck my ass. He was small and i figured how bad could it be. After lubing up, he started to push. Even though it was small it felt huge. I begged him to hurry up and finish. It seemed like hours until he came. Was sore for hours later. Took a long time for me to enjoy anal but by then he started to get homophobic so i had to seek out others online.

 

The first girl ass i got was my neighbor. I fucked her regularly growing up. Had to try and convince her she wanted it in the ass so i started to tongue fuck her ass on a regulsr basis. One day she said i could try fucking her ass. The first time wasn't great for her but she let me try regularly here and there to mix up the action.

 

I've lost count of how many times I've topped an ass.

Funny thing is, I have the desire to be topped and I have used several different sized dildos on myself, so I know and enjoy the sensation...but I can't bring myself to bend over and allow myself to be in that submissive position. I want it...I just can't bring myself to go thru with it.

 

Most times i was riding cock or getting it missionary so it wasnt submissive for me

 

The first time I topped I was 8 and I fucked my 6 year old cousin who is a fem bottom to this day. He loved it in his ass so I obliged all night when he'd cone over. Then I stopped all that gay stuff cuz I did and still do I identify as straight but know I like being a fag so much. So it took me til I was 19 (2 years ago) me and my friend were both high and he kinda hinted and I agreed so we immediately went back to my room and I was on my knees. I had waited and fantasized so long about sucking a big cock and getting fucked that I wasn't playing around. All those Yeats of ass play I couldn't wait for the real thing. I yanked his shirts off and shoved his fat cock in my mouth. I loved the feeling of his soft cock in my mouth and feeling it grow and get hard was just amazing. So I confirmed that my cock obsession was real cyz I sucked his dick better than any girl ever sucked mine. Then he gave me head, we 69d and then he told me to get on the bed. I layed on my back as he shoved his cock right into my ass.no pain just a little discomfort fir a sec then he held my legs up whole watched him fuck my ass. Harder i moaned. He then really started to pound the shit outta me. I found my self moaninglike a bitch and my hard cock leaking cum as he drilked me. I wanted to cum from just anal so I didn't touch myself. He flipped me onto my knees and face and hit it from the back. I had to moan into the bed so my dad couldn't hear us. I wasn't even worried about coming cuz I Let go of my masculinity to really experiebce what it means to be a bottom and letting a big, dominant man have me at my mosr vulnerable moment and i loved it. I submitted to him and would gave let him fuck my ass as long as necessary. He let me ride which was so much fun cuz I was a natural. I had him moaning and as he kept saying oh fuck under Hus breath. As soon as he was loving me riding I came without any contact as I quickly hopped off his dick so that he could swallow my load. Then I sat right back on his dick and after over an hour of sex he comes so hard in my ass as I sat balls deep. I had so much fun that it became a frequent thing. He tried to get me to top and I wanted to but I knew that his tight ass would make me cum so quick that I'd be embarrassed. I went quite a while without any gay experiences after that until me and my cousin, (the same cousin that molested me and taught me how to jerk off and then had me suck his dick when I was like 6) whose one of my best friends, get drunk one night. After every one went to sleep he asked if I wanted to suck his dick which is a hell yes but I thought he was kidfing. Sure enough he walked to the back room. My heart racing from excitement and nervousness I walk back to him and we just kinda smile at each other then I drop to my knees. He pulled out his cock and it was so nice I was like damn. Average girth at about 8 inches I'd guess with dip bend in it which was so hot. I went to town on his dick. I was grabbing his ass and shoving his cock as far as it would go. He was so hard you could tell he was loving it so he said let's go outside so we don't wake your dad. We sent outside and sucked each other off. He stood me up and asked me if I wanted him to fuck me. Well of course. I got on my knees on the edge of our outdoor couch and shoved my ass out for him. Unlike the last time his dick fucking hurt but I loved the pain cuz I knew I was being a trooper for him to get his fuckin on. Plus I could feel it easing up as my dick began to get hard again and it didn't hurt so much. I started moaning and I was oozing cum like crazy. I started to moan again cuz I couldn't help myself so he pulled out since he was scared of my dad hearing us. I just wish he would've came inside me, lol. Oh well.

 

Mine too and I didn't like it at all. But not long ago I decided to try again and this time I enjoyed it.

 

I think it took a year before i enjoyed anal. There was no internet to learn from so trial and error with different lubes and positions and finally it became enjoyable. Since he wasn't much of a foreplay person i would finger my ass while i sucked him. Sometimes he couldn't last and would cum in my mouth and some times he would fuck me a little and cum in my ass.

 

I let my cousin fuck me at 14. He was thick and he stretched me good. It hurt at first, but got so good the more he pumped his cock into me. I wanted to be fucked, so I think that made it easier for me.

 

disappointing, it felt the same as vaginal sex with a condom. so really its a nice change but no reason to do it for me. i had a friend whos wife loved anal so for some i guess its good...but for me and the people i have done it with...not so much.

 

Most girls love it because its different and can be more intense. If you play with her clit or finger her pussy or use a toy then her pleasure increases yours

 

I bottomed for the first time a couple days ago.

I've always wanted to try it but I wasn't going to hook up with some one for the sole purpose of giving up my ass. I wanted it to be one of those situations where if the opportunity arose...I would make the decision to let it happen or not.
So I hooked up with a really hot (passable) TS, and we were in bed enjoying a little foreplay before the subject came up of who was going to top and who was to bottom. I told "her"...that I always top because I'd never bottomed before and she let it be known that she would love to be my first. There was no aggressive behavior on her part, just a willingness to go there if I wanted too. She was really cool and we were having a really fun time just playing and talking in a very relaxed manner. I thought about it for a few minutes while sucking her cock...and I made the decision that I liked her...so why not!

I moved over from between her legs to over to her side so she could play with my hole. She started to rub it and massage it...getting me nice and warmed up. She asked if I was ready so I said yes. I asked her how she wanted me and she indicated doggie in the middle of the bed. I got over on my knees and arched my back and waited on her to ease her cock inside me. She was already wearing a condom so she lubed herself up and then I felt her finger lube up my hole. A few seconds later I felt the head of her cock come in contact with me before I began to feel her slowly push inside me. I could feel myself expand and except the head of her cock as it pushed past my muscle. It hurt for just a second and then I felt her push her entire length inside me. I couldn't help but flatten my chest to the bed and my back arched completely...wanting more.

She started to stroke her cock in and out of my ass as I felt her hands rubbing my thighs and squeezing my ass cheeks. She is picking up the pace and I can hear her hips slapping my cheeks and she is fucking me harder now. It felt so good...

She pulled out of me said she wanted me on my back. I flipped over and spread my legs...and she crawled in and pushed inside me again. I'm holding my legs back and she tilting her head back and closing her eyes as she slowly pushing her cock in and out...in and out. After several minutes of enjoying her cock massaging my prostate, she reached for some lube and started stroking my cock. I couldn't hold back...I told her I was cumming and she started to stroke my ass faster as she pumped my dick. I held off for as long as I could and then finally erupted with such force that I shot a huge load that completely painted my chin in warm cum.

She pulled out of me, cleaned me up and asked if I enjoyed it. Well...yeah!

I look at it like this. I'm not a total bottom now as I enjoy fucking a tight ass just as much as anything else, but at least now I can be more versatile and open in sexual situations where I'm more willing to accommodate as opposed to being one sided.

 

Wow that sounded hot.

 

Oh it was...

 

The first time was somewhat awkward since he wasn't experienced either. I'm smaller and he was a bigger guy with a thick cock, After I sucked him a while and had him good and hard, I got into doggie position and he started to work his cock slowly into me. It took a little work but once he slid all the way in I was in heaven. He started fucking me slowly and got faster and harder until he was slapping his hips against me. After a while, I was able to push back against him in rhythm. I couldn't believe I was actually doing it and how good it felt. He flipped me over on my back and fucked me with my ankles dangling by his ears until he was exhausted. It was so incredible. We met nearly every weekend after that for over a year.

 

Mine was about a month ago. I met someone on CL and we had been exchanging oral up to that point. One morning he emailed asking if I wanted to fuck him. We set the time and he came over. He still wanted to use a condom even though we had been swallowing each other for a couple of weeks. We always start out sucking each other but this time he stopped after I was fully hard. He got on all fours and since he was a virgin I look a small dildo and slid it into him first. Since that went in and out easy I got a bigger one, applied the lube, and worked that one in and out as well. When he was ready I put on the condom and lubed up. He didn't make any pain noises as I entered him, with just the head at first. I then slid the rest of my cock in. I fucked him with slow but long strokes. When I finished, I put him on his back and sucked him. I wanted to make sure he was fully hard. I applied the lube and before he knew what was happening I positioned my hole over his wet dick and sat on it as it slid into my virgin ass. No pain for me neither as I rose up and down a few times. I then came up, rolled over on my back and put my legs up. He knew what to do and put on the condom and lube. He entered me, gently at first, but then began to fuck me fairly hard. I didn't mind the pounding but was afraid he would cum too soon. He kept saying what a tight ass I had. He came much sooner than I wanted. My insides were still craving for more an hour after he left.

I really think the pain that some experience is from lack of preparation. Both of us were ass virgins and both of us are 7 inches or more.

 

I had been chatting with a guy on a gay dating site and we decided to meet sort of spur of the moment.
We got a room. As soon as we were in the door we both stripped. His dick was longer than me and about as thick. We stood and caressed each other for a few minutes before he laid me on the bed and started to massage me and play with my ass.
Soon his cock was in front of me, by now I really wanted to suck him. The pronounced mushroom sloping head felt spongy and hard at the same time. I think I was going to make him cum sooner than he wanted, so he made his way down between my legs and he turned me over and lubed up after putting on a condom. As he pushed it in there was a little pain so I had him take it out and then put it in again. This time no pain at all.
His first couple of strokes were short and it felt amazing. He could tell I was ready for all eight inches and started to pump all of it in and out of my ass. I could tell with some practice I could reach a prostate orgasm because it felt so good.
Again he didn't want to cum too soon and pulled out, went and cleaned up and I sucked him again and jacked him to a finish.
That was the first and last time I got fucked.

 

My first time I was 13 and a 17 year old neighbor that I hero worshiped took advantage of me. It started in his basement when his parents were gone and he showed me girly magazines for the first time. In no time I had a tent in my shorts as he did , and took his off and suggythat I take my off and I did. We were both sitting on the couch or floor and we kind of wrested a little bit. He asked if he gave me a blow job would I give him one. I don't say yes but don't stop him. Wow, it was my first BJ and I loved it ! In no time at all I came I was cuming in his mouth and he kept sucking till I was done cuming..
No it was my turn and I got down and started sucking, I wanted to do a good job and repeated what he had done on me. His dick was longer and thicker than mine. I think I was doing a good job because I could really taste his pre-cum , but before he came he pulled out and flipped me over and pushed he dick into my ass. Using only my silva and his pre-cum he started fucking me , I was crying for him to stop but he kept pushing in . His dick felt huge and after pushing in and out for several minutes I loosed up and he started to fuck me faster. Within a couple more minutes it started to feel better and my dick was hard again. It was starting to really feel amazing and he really started fucking me hard and deep now. I was kind off in heaven and loving it now. He started breathing harder and in a couple of minutes I could fill him cuming in my ass and that caused me to blow a load and hit myself a couple of times in the face and several other shots.
He had me dress up a leave as soon as I cleaned up.
I went back to my house and had to go to the bathroom, he's cum was leaking out of my ass mixed with a little blood.
The first was a rough one. I have loved anal play every since

 

So hot
Would love to experience that

 

I was 19 first time I got fucked, and apart from some puberty play with a guy at school, this was my first gay experience. He was a bit older I think, maybe 22 and a West African with a huge cut cock. I stayed with him over a weekend and and the first night I waited for him in bed....he came out of the bathroom with a rock hard cock and I set to sucking him....I probably wasn't so good at it then and after a while he laid me on my side, lubed up and without much foreplay started to penetrate me. Yes it was painful at first but by halfway through I was enjoying it enough to push back on him as he thrusted.

Stayed with him another day and he fucked me face down on his floor the next day.

I never saw or heard from him again and while I fucked many other guys n gals it was many years before anyone fucked me again.

Simon

 

Mine was amazing. I had been sucking off a friend for a number of months. After a bit, I started fantasizing about him putting it in my ass. I'd finger myself while jerking off and knew he wouldn't fit, so I started using everyday household things to put in my tight teenage butt to stretch it out a bit. Each time I blew him I wanted to ask if he wanted to fuck but was afraid it was "too gay" and I'd chicken out. I was sleeping at his house after some drinking and knew I'd at least get to give him a totally naked, drunk, not rushed blow job (my favorite). I was on my knees with him on the couch, we were both naked and he kept leaning forward to grab and fondle my ass. After the third or fourth time I couldn't take it and asked if he wanted to fuck...I'll never forget him asking, "will it fit," and thinking "it better." I grabbed his bottle of jerk lotion, covered his cock and my ass, straddled him, and slowlyyyyy sat back on it. It hurt, just at first so I went up and down real slow until I loosened up. From there it only got better. I was so horny and turned on riding his cock with his hands all over my little ass I wanted to make out. I went in a few times but he kept directing me down to his nips. He had only been in me 5 or so minutes when I got the, "go slow dude, I'm close...where should I cum?" I asked if he wanted to cum inside me (we went bb), and 30 seconds later I got the, "I'm close dude, don't stop!" I got so excited I went a little harder and faster until he grunted, "here it comes!" Just as he started to cum he pulled me close and we started making out. We kept making out with his hands on my ass until he moved them to my cock. With his cock in me, I leaned back and let him jerk me off. I lasted maybe 30 seconds before I climaxed all over his stomach. It was an amazing experience!