My First Anal Experience

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The first time he had a guy.
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This is my 2nd submission of my true experiences. My first story is how I experienced my first Contact with men, giving and receiving blowjobs through a gloryhole.

Months had passed since my first experience but that first experience had a great effect on me. I started going every Friday night for some quick action before I headed home from the clubs. I also like going to different bookstores because not knowing the layout and exploring the whole place was exciting.

On one particular night I did try a new bookstore and quickly found a booth with a GH. When I heard someone enter the other booth and saw the fingers through the whole I went into action. I put on my condom and stuck my dick through the hole but nothing happened. I heard a lot of movement and then the sound of his belt being undone and his pants going down. It was normal noise you hear all the time so I thought nothing of it. All of the sudden I feel pressure against my dick. This was not a warm mouth taking me in so I was confused as to what was going on when it hit me. He kept moving in and out and I realized he was trying to get fucked. All of the sudden my juices started to flow really hard. I finally felt my head enter him and slowly little by little my dick was inside him. I did nothing but let him do all the work and about three minutes of this I came. To this day I do not know how I entered him without lube. When I left all I could think about was how it would feel if I had someone do me. After three weeks of attempting to do this then chicken out at the last minute, I went for it.

There was this one bookstore that had some really good holes and action. It was late Saturday morning; I bought some lube and several condoms then headed to the bookstore. The place was packed with guys. My regular booth was being used so I started to walk around. I walk into the movie theater area and while watching the movie I noticed a tall guy in his late 30’s, long blond hair checking me out. After a while you know what certain looks mean and I knew he was looking for action. I decided to go back to the booth area and wait. As I settled against the wall in front of my favorite booth and wait for it to be free when the tall blond came by and settled himself in front of a booth which happened to be next to me. I could see in the corner of my eye the guy looking at me.

Finally! The door opens and I enter the booth, at the same time the guy in the other booth leaves so I know the Blond hair guy is now in the booth next to me. I begin to flip channels until I find a video I like. Looking at the hole I see the guy looking through the hole waiting for some action. Feeling brave all of the sudden I put my fingers through the hole and invite him to put his dick through. When I saw his dick I was shocked. It was big! Too big for me to have him fuck me, this was going to hurt. I start off giving him a blowjob, at the same time I finger myself to try and loosen myself up. I’m ready, so I take the lube and put some on the condom and some in and on my asshole.

The guy begins to insert his dick and I feel pain so I pull away and wait for it to go away. Again he tries but he is slow about it as if he knows he hurt me the first time. Once he is fully in he begins to thrust in and out real slow. Man, I started to enjoy it. This was one of the best feelings I have experienced. I could not believe how good this felt! I kept adding more lube and he kept pumping faster and faster. Looking down I noticed I was cumming! Not once did I touch my self and there was cum dripping from my dick. My whole body was relaxed and enjoying the experience. The guy started to thrust as fast as he could and then he came. He was in me for another 15 – 20 seconds before he pulled out. I did not hang around for the next guy or clean myself up.

I left the bookstore and went straight home to shower. As I was cleaning up I realized I was still horny. Even though I was cumming during the fuck I never really got myself off. As I masturbated I imagined the blond guy fucking me. Three fingers were in my ass as I played with myself. I came very hard and my whole body felt like it was cumming.

To this day I wish I had hung around to talk with the blond hair man. I would have loved to been his fuck buddy. I never saw him again but what he did to me that day left me wanting more. And I did get more but that is another story for another day.

I hope you enjoyed my story. Please contact me and let me know what you thought. I love to hear from everyone.

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15 Comments
AnonymousAnonymousover 3 years ago

I still looking for my first anal. I'm 38 and still can't find it. Guys in my area are game players and just talkers

KwhyKwhyover 5 years ago
Maybe me

I'm trying a fuck buddy myself! Maybe you live close?

AnonymousAnonymousover 6 years ago
My first time!

Wow the story was hot and it even made me masturbate! My first time I was on my

knees and I don't know why but it didn't hurt one bit even when he pushed his cock

all the way in me, he waited awhile and then began pumping me slowly with both

arms around my hip oh shit it felt so good and in only a few seconds I came and I

mean I came then he began pumping me harder and faster and harder and when he came I came again! He didn't stop pumping when he came just faster and harder then it began to hurt but it was a hurt of pleasure and I told him please don't stop I loved it so much! He asked me if I was constipated and I said no but now after being fucked

sever more times I know now!

AnonymousAnonymousabout 7 years ago
Big wish....

Thought I would like to try a bath house . But, kind of leary . Clean or take a chance. New a guy that would go often, Course he love cock, the bigger the better. We talked one night, I gave him a ride home from Bingo. He came on to me. We talked, I drove around in the country roads. The more I drove , the harder I got. He reached over and started to rub. He really got excited once he found out how big I was. And getting bigger the more he rubbed. He asked me to pull over. I found a nice secluded spot. We ended up in the back seat. He deep throated me and I got very "HOT" . My wife never liked sucking. He moaned and moaned and sucked hard and deep. He told me not to come. Telling me , he wanted me to stick it into him. I did, he groaned and moaned , saying he loved it, now come he said, I did . More to this story later. A preview , I was curious about trying to take anal penetration. Care to hear the story?925E

DeniseLDeniseLabout 7 years ago
Persistence Pays Off

I am not a glory hole fan, preferring social interaction with my partner, however the experience is well composed and written. Enjoyed the details and feelings the author imparted.

AnonymousAnonymousover 8 years ago
My first ANA1 experience

My first experience was when i was a 14 yr old freshman in high school . I decided to skip scholl with my 2 16 yr friends to smoke some bud. We smoked about 3 bong packs in about a half hour. They went to the bedroom to gather. I hurd them blowing each other the door was cracked I took my pants of started fingering my a55 hole and ma5ter8ating. They saw me and I had my as5 hole licked while I was blowing the other guy. After a few the guy i was blowing had me ride his d¡ck omg it was the best hurt ever. Then the other guy had me start blowing him. After I blow him for a few he shoved his c0ck in my as5 they were both sctrewing me in my as5 at the same time. Then they pulled out and camed in my mouth best thing i have ever tasted in my life up to that point. They starting fingering my as5 then a hole fist went in my as5. After a few they shoved a nother fist in there. Double ana1 fisting omg it hurt sp good. Belive it or not they shoved another fist in there then a nother one. Quad ana1 fisting and elbow deep. After about 20 minutes not they're both gymnastics flexuable feaks they somehow get a foot knee deep amd then 3 more knee deep. After all that was in there i stated sucking my self and came all in my mouth. I never know an ass could be stretched out that much. That was my first experience with $€X.

AnonymousAnonymousover 9 years ago

My first fuck through a glory hole, I went there for that reason, first guy who put his cock through the hole was going to get my arse. there it was, I remember sucking it, then as it was hard, I held it, put lube on the big head and holding it, positioned it at my hole and waited, he stayed there so I eased back until I felt the head enter me, and with little back and forward movements until he was all the way in. I held still, I still remember his first movement back, then forward and I was getting my first arse fuck, bent over, perspiration dripping off me, I felt him swell and my hard cock let go, cumm shooting from me onto the floor as his cumm coated the insides of my arse. He kept going, heaven as he just stayed hard and kept fucking me, my cumm dribbling out of me, I couldn't help it as I stroked my cock, what a feeling until he eased out, I stood up, there was a finger through the whole opposite, i pushed my cock through and what little cum i had left was coaxed from me by a warm mouth. Never forgot it.

AnonymousAnonymousover 10 years ago

Like my first, I had received blowjobs at a glory hole. One day i put my cock through, the wonderful warm mouth ,then he held me and I felt a hot hole, I stayed still and he pushed back onto me, my cock entering his warm wonderful arse. he pushed back at first but then I pushed back and forward until my cumm shot into him. He held me there, squeezing , milking, then pulled away. all I heard was thanks man, I needed that. My cock was still sensitive, so I stroked it, a finger came through a hole on the other side, I pushed my cock through and was sucked as what was left of my cumm dribbled into his mouth. What a great feeling but my curiosity was aroused and so it was the next time at the gloryhole, I moved next to an occupied one, I peered through, it was an islander guy, stroking, I pushed my finger through, waited, sure enough a nice dark cock came through, I sucked it, then stopped, I turned and put my already lubed arse against the hole, waited,then a finger at my hole, he felt the lube, pulled it back, I bent over,i felt the head, he pushed, missed, I reached under, held him and he pushed, I wouldn't open, then I pushed back and the head popped into me,, pain,i jerked forward but he stayed in me, then I pushed back and I had my arse fucked for the first time his cumm blowing into me, his cock pulsing as it did so, my cumm dripping out of me. He pulled back, I stroked my cock, the rest of my cumm landing on the floor. When I dressed and left the booth, he was standing in the hallway, older than me by about 10 years. He spoke and said how good that was and handed me a paper with a mobile phone number on it. I did ring it and he would meet me at that gloryhole and fuck my arse. Once, he said lets get a room with a movie and it was the first time I felt him hold my hips as he thrust into me. The next time he asked could he bring his brother, I wasn't sure but he did and after he fucked me, his brother who was about my age pounded me, my cumm leaking out of me as he opened my arse with his thick cock, finally blasting his load deep into me. They have moved on now and so have I but when I get that itch, I go to the same gloryhole and offer up my arse to any takers. I always walk away full.

AnonymousAnonymousover 10 years ago
nice,

That first fuck is marvelous and if it is you are hooked, you just can not get enough of it, and it gets better, and you want to try bigger cocks, then even bigger, I had three regular buds all over 9" but my biggest was 12"+, what a feeling of achievement managing to take it all, and the happyness it brought him as most could not take it all.

Happy fucking mate.

AnonymousAnonymousalmost 14 years ago
awesome!

I`d give anything to have an experience like that! Gettin assfucked by an annomyous big cock through a gloryhole!! That has long been a fantasy of mine! I`ve rode my HUGE dildo many times dreaming of that and stroking my cum filled cock.

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