I was 21 and I lived in an apartment complex. The couple across the hall were in their 50's. His name was Chris who I had met tin the laundry room and after weeks of flirting we finally got together. To make a long story short....Chris and I had gotten together once or twice a week in the evenings. His wife was a nurse who worked 12 hour shifts.

Our first dozen times was lots of naked play but no penetration.We were both very playfuland we very much enjoyed being naked....always naked and became close mentally as much as physically. We got to know each others dicks perfectyl as well and one night as I was on my knees and he was sitting back on the couch it seemed he was really super hard. a minor difference from his usual hardness but I did notice so as I was blowing him I made sure I got his cock extra wet with my saliva.. I was a virgin but I could see Chris was incredibly horny so I climbed on top of him and guided his cock in my ass. It took a little time but soon I was lying on my back on the couch and he was thrusting himself in me. He came hard and afterward we studied my butt to watch his cream find its way out.

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Your last sentence is incredibly hot. I find nothing sexier than feeling my partner's cum oozing out of my ass. Even more exciting if he's stuck around to watch and maybe play with it.

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I took my first load up the ass from my cousin when we were both 12. We had been sucking each other off for about a year. At first we only had dry cums but the feeling was the most intense I can ever remember. It was like being hit by a bolt of pleasure lightening.

Eventually I decided we should try fucking. His dick was only about the size of my finger so it slipped right in with only spit for lube. I loved it!

I tried to fuck him but he said it hurt too much. So I didn't get any. I let him keep fucking me though. We kept at it until we were about 17 and started getting pussy. Didn't get any cock again until I was about 40

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Love those guys that like to top but say they are to tight to bottom! The first guy to fuck me said the same thing - AFTER he took my cherry!

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Well, we were both young and I do think I was too big for him. For some reason I developed early and had almost 6" when I was 12 (too bad it didn't keep growing). Also, we didn't know about lube and I did make him bleed. So, I don't resent him. Just wish I would have found some to fuck when I was a young teen.

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You were 6" at 12? Lucky you! I think I had 6 hairs at 12 - and I was proud of it! :-)

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I said "almost". I was pretty big for my age. Unfortunately, it didn't grow much after that. Just 6" today. Guess I was an early bloomer.

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Still it would have been fun to be that big walking into the 7th grade locker room for the first time. :-)

We had "humped" as kids to - not big enough to go in that much and when we did it was more like finger size but was still great fun.

As we grew I wanted to do more with anal and sometimes the couple guys I played with would want to top - but not bottom.

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I'm all about older men too as I see some others are posting as well. I'm only 22 and I haven't been with anyone remotely close to my age. 50 and up is what I like. Their experience and appreciation is my aphrodisiac.

My first time was not at all planned. I was with my silver haired partner and He was always good for just one pop and it was usually after I would give him a nice slow but firm hand job. He would usually suck me to completion and I would finish him off after that.

This one particular night we were watching a gay gang bang where this one guy who had a similar physical likeness to me was taking cock anally from 5 others. We were both impressed but what really got me was that one guy pulled out and sprayed hard all over this guys face and after he came within 30 seconds he came again. He just kept jacking off until he squirted again. It never occurred to me that that could be done.

We talked about it in wonderment and decided you had to be really REALLY horny to do that. He asked me what he could do to me to try and cum twice like that. I told him that maybe if he fucked me while I was on my back hips lifted up that maybe I would be able to but I wasn't even sure I could take his cock anally.

After a good 10 minutes of positioning and some pain he got himself in and he was thrusting pretty well and my cock was super hard and bouncing around with his thrusts. I forgot all about our plan and was really enjoying his body on top of mine and soon he was releasing cum in my ass. Right after he started jacking me off and before I knew it cum was erupting out of my cock and before I relaxed he was jacking me again to try to get me off right away for the second time. Initially I didn't think it would happen but then I reached for my asshole, inserted a finger in and as I felt his um from my ass thst was all I needed and I came again. To firsts in one night.....not too shabby.
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I was young (not that young - 18 & working a summer job), and I know now that this older guy was working me, but I didn't know it then.
I worked for him on a fishing boat. We started going back to this tiny place he kept right by the pier. He worked me slowly, first weed & beer, then straight porn, then he started blowing me. After a couple times with that, he got me to blow him of course. He than started working to my ass. He was on the couch, I would lean over and take his dick in my mouth. I remember him licking his fingers and finding my hole. "Sweet ass" I remember him saying. one day he just pulled my head up and turned me around on the couch. He pulled my jean shorts and briefs right off. He used lubed me up with crisco (remember crisco anyone?) I remember he leaned over and told me to bite the pillow if it hurt.
God damn did I bite that pillow. He pushed in slow, but steady, and started to pump. "Yeh bitch, take my cock" he said, stuff like that. It hurt, but damn it felt good. I remeber feeling his sweaty, hairy body on my back. Dropped a load right in my ass. Then, as he was getting soft, he reached down and gave my balls a squeeze. "Tell me you're my bitch" he said.
"Yes" I said. He didn't let go. "Say it."
"I'm your bitch"
"Good boy"
So my first ass fuck was from a real rough daddy, who worked me good and got what he wanted........and yeah, it was good for me too.

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Crisco? Sure would have been slippery but did it last?

On thing I find interesting - back then the guys just went for it. Not really planned or preped - just fucking.

I guess that is a good thing - if my buddy had told me the first time I needed to have an enema first I would have been "No Fucking Way!" and probably never would have tried it.

I am not into scat or anything like that - that is not where this is leading - but I find it interesting that in newer stories of guys first fuck there is lots of talk of prep - but in those of us that did it in the past it was just the fuck that mattered.

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The best lube ever invented. Crisco.

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I have two partners that always use Crisco. Its old school buteffective. One leaves it n his end table cabinet. It works really well and isn't as slippery lube. It really helps the cooking!
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While my tales will have a bit of the “If you don’t get fucked for 5 years, can I claim to be an ass virgin all over again and count that load as a first?” ring to it, I am old enough to have lived through the pre-condom AND condom eras. So I’ll be sharing about taking loads in the days of innocence, and then much later when I was thinking with my cock (and trying not to be too judgmental about it).

FIRST TIME – PRE-CONDOM 1980
Although I’d been shoving fingers, candles, assorted vegetables, and my own cum up my hole all through my adolescence and into early 20s, it wasn’t until 1980 and my 26th year that any of my sex mates expressed an interest in my butt. (Ironically, at 21 with my first boyfriend, I was the top.) And so it was that my second boyfriend (pure top, tall, nice body, clone mustache) had me moved in within a matter of weeks, and I was getting nailed and bred daily by his solid 8-inch straight-as-a-ruler cock. This went on for about six months before we became Just Roommates for another four years, and my hole-feedings grew more infrequent. Sadly, I don’t recall much about the first load he gave me, other than it was on our first date, and I do remember being very happy and very impressed with the size of his cock, along with the fact that he loved to fuck and fuck and fuck...

FIRST TIME – BAREBACK 2005 Incident No. 1
From 1985 up to 2005, I dated just a few guys who had no interest in assplay, and then I had just a few casual encounters, always with condoms on those rare times when a guy wanted to fuck me. Then in January 2005, I paid a visit to the local Baths (now gone). It was a chilly night outside and inside the baths, so I kept on my white T-shirt and white sport boxer-briefs. The military-themed Barracks basement was nearly empty, so I went all the way to the back dark corner, and took the lower of the two padded bunks, on hands and knees, sprinkling condoms around me, and hoping someone would take the bait. Eventually a pair of burly, beefy guys in their 50s came on back, and the first one had a really nice and chunky 7-inch dick. He pulled my briefs down to my knees and stroked my ass for a minute, and then with no other foreplay, that man plowed me good and hard with just precum for lube. (I was sore for days, but that taught me to carry lube at all future outings.) That dude slammed and battered my hole, huffing and puffing, and then he pushed me flat on the bunk with his full weight on me (my favorite position), blowing his load with deep loud breaths. After he came, he leaned in and asked if I was OK, and I breathlessly thanked him for the great fuck. He groaned as he rose and slid out of me, and I instantly missed his weight, his heat, and mostly his cock up my ass.

The second guy had a cropped beard and furry chest, and a nice hard dick. He jumped right on my vacated hole and jackhammer fucked me, fast and furious, and I was bloody fucking loving it. Then he flipped me onto my back, slammed back into me, and kept eye contact with me as he fucked the wind out of me. Finally he came with a roar, only pulling out after he caught his breath and then giving my rigid cock a friendly slap before he and his buddy took off. After my two fuckers left, I finger checked my hole and realized how wet and sloppy it was. I looked around and realized that none of the condom wrappers had been opened. Oddly enough, I wasn’t panicked by the situation, but kind of turned on as I staggered to the showers with my rigid dick leading the way. Luckily I tested negative at my next STD screening.

FIRST TIME – BAREBACK 2005 Incident No. 2
August 2:00 AM at a downtown ABS. I had a really hot time with a slim, fit guy in his late 30s with a beautiful cucumber shaped 8.5-inch cock, who joined me in my booth to kiss, suck and rim with our jeans pushed down below our knees. And then with a bit of lube he carried with him that smelled of coconut, and keeping eye contact the entire time, he had me lean back against the Buddy Glass and spread my legs as much as I could, while he reached around and spread my butt and pushed his cock between my legs. With his fingers, he pressed his cock into my asscrack, riding the length of his lightly lubed meat up and down across my hair-free bud, pushing his cockhead harder and harder against my ever-relaxing hole. My stiff cock was mashed and sliding against his abdomen, and with synchronized breathing, we were both moaning at the intense sensations we were experiencing – he with his highly sensitive cock, and me with my hole as the then, at that moment, Center Of My Universe. After a good 5-10 minutes of that intense bit of exercise, we were physically about to collapse from the awkward position, and he proposed that we go somewhere, as his favorite thing is to 69.

So we ended up at my non-air-conditioned apartment, stripping each other immediately and after plenty of mutual sucking and rimming and fingering on my sweat-soaked bed, he knelt between my legs, pushed my knees to my chest, and started to push his saliva and precum drenched cock into my smooth, spit-slick hole. I asked: “Can you stay hard with a condom?” He grinned and I scampered off the bed to get the condoms and lube that I didn’t get a chance to pull out when we arrived. Rubbered up and well-lubed, his meat sank right into me, and he fucked me in every position under the sun. It was a long, hard, fun, fantastic fuck, and when he came, his face scrunched up and he threw his head back in a silent yowl, with his body shuddering on top of me. However, when he pulled out, the condom had come off inside me. Curiously I was not alarmed, and we were both laughing as he and I slipped in fingers to fish the useless thing out of my very wet and sloppy hole. (I believe that the condom came off during the fuck and that he came in my ass, as the condom was empty and merely sticky and wet on the outside when we fished it out.)

He then wanted me to fuck him, and as he began to sit on me, I asked “Do you want a condom?” and he replied “No.” But we soon gave up because I am professional bottom, and even for his superb hairy ass, I couldn’t stay hard enough to do the job. So instead, he fucked me again, condom-free, and it was another hot ride all over my bed. I did, however, ask him to pull out so I could eat his load, but when he came, it was just barely in time for him to yank free of my hole and blow his hot cum all over my chest and abdomen. (I believe he blasted at least once or twice before pulling out.) After that, we showered and dozed for a couple of hours, and then he had to leave to join his mother for Sunday brunch. He said he wanted to see me again, and two weeks later he came by at mid-day for another round of sweat-drenched suck/rim/finger play and bare fucking, this time with him pulsing at least once inside me before pulling out to shoot over my head and onto the wall behind my bed. This guy was great sex, and the only guy since Boyfriend No. 2 I intentionally allowed to fuck me bare. Although, truth be told, I was thinking with my cock both times we got together, and I was very lucky to test negative at my next and subsequent STD screenings.

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I haven't yet had someone cum in my ass without a condom, and I'm not sure I will. All I know is ever since I was 9 or 10, I loved having stuff in my ass. It started with an enema bag/hose I found in out bathroom, and went on to stealing my mom's tampons (with the cardboard tubes, and stuffing them in while I jerked off. Im in my 50s, and married now, but I am quite bi, and love getting fucked in the ass. The local gay gym/sauna has a sling, and the first time I was in it I almost came from the excitement of laying naked in public with my legs spread and my ass out for anyone that wanted to put on a condom and stick it in. I'm going there tomorrow, and am hard as a rock just thinking about my ass getting pounded. Sorry if this is off topic!

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