How was your first time

sweetnympho

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My first time, i was in a restaurant ordering food and I saw a woman (trans) staring at me. So i went to use the restroom and when i came out, he was standing outsidet the door and starting smiling when I was walking out. So i went back into the bathroom immediately and told him to come in. He was a trans and he had breast but still had a dick. Anyhow, he went in and dropped to his knees and started sucking my cock. I thought it was super hot and at the time, he looked like a woman and I had a feeling it was a guy but I just went with it becus it was exciting and hot. So after he blew me, he gave me his number. I called the next day and he said, you do know im a man right, I said yes i figured that but i want more.

So the following night, he started to suck me again, this time he got me naked and then he got naked. I saw his dick and was in amazement to see it soo close. I got soooo turned on that i dropped to my knees and started sucking my first cock, it was fucking hot as hell and I knew immediately i loved cock. So about 30min later of sucking, he talked me into bending over on his bed, he then asked if I ever been fucked and I said No, she he seem to get all excited. Minutes later he put condom on and started slowly putting his cock into my ass, I was nervous but excited. Finally he got it in my tight ass and next thing you know he started pounding my ass for about 30-40minutes. I FUCKING LOVED IT, IT FELT SOOOO GREAT!! After that i kept going back to him. It was about the 3rd time that he fucked me and he asked if he could fuck me with no condom, so i let him becus i was curious what it felt like, WELL THAT WAS THE BEST SEX EVER,,, THIS GUY FUCKED ME DOGGYSTYLE AND I WAS ABLE TO CUM WITHOUT EVEN TOUCHING MY DICK.. It was the most intense incredible orgasm cum session Ive ever had, my cock was throbbing and i was shaking and moaning sooo loud. Man that was awesome. I became his fuck toy for a while and then he moved. I once in a while call him but i never have time to meet up. Now that im thinking of it, i may go see him soon. :)

Ever since then, Ive been getting fucked by differetn guys whenever I happen to meeet a guy that' wants to fuck me. Its easy for me to meet, If i see a guy staring at me, i just go up to him and ask him if hes bi, if he says yes, i ask him if he would like to fuck me and they always say yes. I always use condoms. Anyhow, that was my first time and i was in my 20s. Im in my 30s now and still getting pounded.
 

sweetnympho

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Too bad that has been the only time that Ive had a male gspot orgasm. I been trying to get that again but cant. I had one older man do me doggy for about 30min and his dick was about 8-9" long and about 5.5" girth and he almost had me to the point and then he stopped becus he was tired. :(
 

FloridaFree

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A little awkward as I expected. :p

Didn't last as long as I wanted to, either. I felt kind of weird because she was really experienced by the time I did it the first time and she was kind of a adventurous and I didn't know anything about adventurous things yet. But it quickly got better after that and kind exploded with fun and trying new things after about a month. According to the person I had my first time with, I was "naturally gifted", which I know I am.
 

peepingtom50

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Incredible, and I've relived it many time while jacking off :)

Brother in law and I were looking at pix of the wife and jacking off. I asked him if he'd be willing to cum on my face and he said SURE!

When he was close, I got down on my knees in front of him, so he would have an easy shot. When he said "I'm cumming!" I couldn't resist and just leaned in and sucked him down. He exploded in my mouth and that set me off. I stood up quickly and shot a thick load all over his cock.

Yum :)
 

GoldStandard20XX

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It was good.

I was swinging with this couple one night, taking a break and watching him fuck her. She squirted all over him and his dick popped out, and I remember thinking how much of a turn-on it was and wondering what it'd be like to suck it. I didn't say anything to them 'cuz I wasn't sure if they got down like that, but I started searching for a couple who did. Eventually I found a couple of folks, we talked about it, set it up and made it happen. Fucking her while sucking him at the same time was a whole brand-new kind of thrill... the funny thing about it all was after we had finished, we were laying in bed together and he blurts out "That was the best head I've ever had." ***IN FRONT OF HIS WIFE!!!*** I had a good healthy laugh about that one... LMAO
 

TheRooks

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First guy: I had just found a guy on craigslist and made sure everything was safe and disease free before meeting. He was much smaller than me in height and in dick size. He couldn't keep his hands off me the whole time and never let my dick go. He basically worshipped it and kept telling me how perfect it was. It made me feel uncomfortable in general for a first time experience. He never came, he just worked on me for about 30 minutes until I finally came and I left. I chose to not see him again even though he was clearly anxious to do it again. I would just classify the whole experience as "bizarre".

First girl: Found her through OkC. She messaged me first and didn't have a profile pic. She sent some through email before we met. She moved really fast. She came right out and said she just wanted me for my dick, she was aggressive in bed and demanded anal and rough oral. For my first time with a woman, it was a little jarring. She started to get frustrated that I wasn't cumming and she told me to jerk myself off onto her chest so I did, I finished and we parted ways. I was her booty call for a couple more times until I lost interest in being used as a sex doll. She didn't even try to make me cum the last time we met up, it was all about her for around 20 minutes and then she got dressed without even asking or warning me and I was just sitting there hard and confused. Luckily the other two women I was with were much better people in general.
 
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ret

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With a guy - intense!

I was in my early 20's, not a lot of sexual experience but a lot of porn watching. I was moving to a metropolitan area; it was late a night. As I was approaching the town, I stopped at a rest stop to take a piss. There was only one other car in the parking area; as I walked past the other car, I noticed the driver was reading. I headed on in and went to the urinals. Standing there feeling the pleasure of emptying my bladder, I noticed saw the note written on the wall - "Show hard for BJ". I wasn't sure what it meant, but had a suspicion. Then I heard a car door shut and went back to the matter at hand - draining my bladder. Next thing I know, there's a guy standing at the urinal next to me and I could tell he was staring at me. (Keep in mind, I had no idea about cruising or anon sex at a rest stop or any of that!) So I glanced over to see why he was looking at me and that's when I saw him stroking his amazing cock and then I knew what the note meant! I wanted it, but I was so unprepared and out of my league. I tucked my cock back into my pants and high tailed it out of there! But stopped in the foyer area to catch my breath, gather my thoughts, and try to decide what to do. While I looking at the various displays the Highway Department had put up, he comes out and also stops at the drinking fountain. While he's taking a drink, I could tell he was staring at my crotch! And that turned me on. So I went back into restroom to the urinal, took out my cock and started stroking it. He came back in and stood at the urinal next to me, took his out and was stroking it! Man was I turned on, but as nervous as all get out!! The though of having sex in a public place had never entered my mind before!! It was a tremendous turn on! But I was anxious and new to all of the this! So back into my pants went my dick and back outside to the foyer I went and stopped again at the posters. He comes back out and this time he starts talking to me - asking me if I've ever had sex with a guy before - I said no, but that I want to - and he says some other things to help me calm down, which all that did help. So finally we go back into the restroom and he has me drop my pants and he got down on his knees and started sucking my cock. Oh my! What a sensation that was! He gave great head - awesome! When I came, he swallowed all of it and drained me dry! Wow!!! I was hooked on getting blow jobs and doing at the rest stops! Over the next several years, I visited that one many times and had some other wonderful times with other hot dudes!
 

stongthumbs

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Even though I consider myself "straight" my first time was with another guy years ago. I think we were about 12 or 13 and I chalked it up to just experimenting...but the experiment happened quite a few times that year.
[Backstory]
I was more in the popular group while he was in the AP crowd, but it was jr. high, so stereotypes weren't really labelled. We had a sleepover and were sneaking out to smoke a cigarette, and while peeing he said "check this out". I looked over and he had a semi while flopping it around pissing everywhere; he was average to slightly below. He said it was my turn so I gave mine a little tug and starting going, while noticing him staring at it very intensely. We were both curious but he asked if I every had a handjob. I said no! He reached down and grabbed my semi, so I grabbed his. We instantly got hard together. Occasionally over the next year we exchanged quite a few blowjobs while keeping it secret from anyone and everyone. Eventually after a summer break not hanging out at all, he got permission to drive his family boat to the island to camp by himself...

We went over with liquor and a tiny amount of weed planning to get fucked up (had never gotten drunk or high before). We set up a campfire and tent on the beach next to the dune. I had made out with and got/gave oral to a girl while away that summer so I wasn't really expecting to do much. We started drinking and talking about our summers with the sound of waves crashing and the stereo in the background. We started playing truth or dare and both ended up sitting naked next to the fire quickly into the game. And just like the first time, we both went to pee together. When he grabbed my cock he said "holy shit! when did you get so big?" "Um, I don't know. Is it bigger?" That turned me on like I had never been before. We sat on the blanket next to the fire while he sucked my cock viciously. My dick was absolutely throbbing but I couldn't get there. He asked if I had sex yet. I hadn't, so he asked if I wanted to see what it would feel like. He bent over next to the fire and spread his cheeks, while looking back at me. I had a massive erection and went for it. I pushed in just past the head a few times. He was seemingly in pain and enjoying it, while I was in amazement of the sensation. It was so tight I couldn't hold it for more than a few minutes. I exploded inside him while he jacked off. We masturbated about 6 more times that night.

That was my first and only homosexual experience.
 

jeffbh8428

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With a girl the first time was incredibly awkward... And lasted about a minute before I pulled out and came all over her stomach. She was not impressed because we had to go back into a party...

With a guy was much more thought out, it was my first summer home from college and I was horny and wanted to experiment. I had given quite a few BJs to guys at school but I really wanted to bottom. A friend of a friend contacted me online and said his parents were out of town for a week and invited me to come hang. We had a drunken conversation the last month of school where I shared my bottom fantasy and he wanted to fulfill it. He was avg size, about 6" and cut, and was on the chubby side, but I liked it. We were both inexperienced so we weren't using a rubber, he had me bend over the couch and he slid it in..I had used plenty of toys so I knew I could take it, and he came after 3 or 4 pumps.. Lol!! I was more than disappointed. We were young so he was ready to again immediately, and wow!! I came without touching my cock at all. I had my ankles over his shoulder and was pounding me hard and for about 15-20 minutes. I came all over my chest and then he finished in my ass again... I miss those carefree days lol...
 

HJ1958

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Depends on what you mean the first time. First time fucking a girl, guy? first time getting a blow job by a girl. guy? First time topping a guy? First time, bottoming for a guy? Every one of these experiences has each been different. some awesome, so not so, some kinda disappointing