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Tell me about your wildest hookup experience

Dear BearLover1694,

I have always concerned about trolling Glory Holes. As a newbie exploring my newfound sexuality, health is a huge concern. That being said one must pursue opportunities as they present themselves. However, that is a hot story and I confess I got hard reading it.

Recently I received a package at my home and the young man that came to the door was a cute 20 something that gave me a long seductive look while I was signing for the item. He was about 5' 8" with slight build(about 150 lbs.) and short blond hair and beautiful blue eyes.

It was a warm afternoon so I asked him if he would like a bottle of water. He accepted and entered my home. He followed me into the kitchen and as I turned to him to give him his water his hand brushed across my slightly aroused bulge. Immediately I could feel my temperature rising and he must have notice as he then grabbed my now half-hard cock and lightly squeezed. I reached down and felt the bulge in his pants and judged had great potential. A smile appeared on his cute smooth face and I asked if he had time. He said "I'll make time".

I took his hand and we went into my bedroom. I, like you, prefer to have my partner stand so I went to my knees. I could see he now had a full fledged hard-on. I unbuttoned his trousers and carefully lowered his zipper. To my surprise this little guy had a marvelous 7" thick cut cock. I saw a glisten of his pre-cum and lightly licked it to taste the juice. Then I opened my mouth wide and swallowed him all the way down to the pubes and slowly withdrew, my tongue sliding along the bottom of his penis. My hands were holding both of his tight cheeks and I felt them tense and a soft groan emitted from his mouth. I increase my mouth action and he began to help with a soft jerking motion. After about 10 minutes I could tell he was enjoying it but was a ways away from Cumming.

I looked up and asked if I was pleasing him. He said yes but wanted to see my cock. I realized I was still completely clothed and mentally kicked myself for being such an amateur. We both got naked and he began to stroke me with a magical hand. I felt my knees weakening so I pushed him down on the bed an myself with him. We arranged our bodies to a 69 position so we could both play.

Now I was getting extremely excited and gasped "you are soooo hot". He stopped and turned me on my back and jumped on top of me looking straight in eyes while his left hand traveled down to my hole. Thank God I have showered and cleaned myself an hour before. He stuck 2 fingers inside me slowly widening me and relaxing the entry point. He whispered "are you a bottom?" Amateur that I am, I didn't know how to respond. I just nodded, hoping it was the right answer.

He pulled his fingers out and the tip of his cock began to probe my hole. Slowly he entered until he was completely inside me. He began with slow thrusts increasing to a point where the thrust became violent. Sweat beads formed on his forehead as our breathing became frantic. I was wailing in ecstasy from his thrusts and the fact that we weren't using lube which created a erotic pain.

My cock was as hard as it had ever been and all at once I blew my load with a loud gasp. He kept thrusting harder and harder until his reddened face took on a frantic look. Our bodies glistened with sweat and the body smells added to the pleasure. Finally, with a lout groan, he shot his load all over my prostate and kept thrusting letting his cum lube my hole.

My legs that were wrapped around his back, collapsed on the bed and I felt the weight of his 150 lbs. on top of me. I am not into kissing but I was so appreciative that did it anyway.

I asked if he would like to shower to which he nodded. We showered together, he dressed and I showed him to the door. I said "I hope you won't get in trouble with you boss for not making all of your deliveries". He said, "no worries, you were my last delivery of the day".

We both laughed and he left. I realized that I never got his name. I haven never experienced the kind of orgasms with a woman that I get from a guy.
 
Not really a hook-up per se. A friend of mine had a friend who was an amateur photographer who was looking for models. The pay wasn't much ($25/hr), but I would get some decent nude shots out of it for my GRINDR. He was older, I'd guess in his late 30s, balding/buzzed, not handsome but not ugly either. However he was tall and and appeared to be in great shape. He was broad-shouldered and muscular. His guns stretched the sleeves of his polo shirt, and had huge veins on them, which is always a big turn-on here.

I'd arrived straight from work, and I was wearing my preppie blue blazer and khakis, so we started off with some suit pics. Then I changed into gym gear, next briefs, and then we moved on to the arty nudes. All the while I'm getting increasingly horned -- I was discovering I had a serious exhibitionist streak! Finally we did some boned-up porn-like shots. He suggested the poses, though nothing in his voice suggested he was aroused in the least. The last one was me with my legs spread, spreading my cheeks and exposing my hole. After he takes a few shots he put down the camera and started eating me, then fingering me with lube. Then he stood up and put it in. I didn't see it, but it felt big. After a few preliminary thrusts he said “you want it rough?” I just nodded my head. He banged me real good, and after about three minutes began to stroke me. I shot my nut clear to my face! About a minute later he blew. It was a lot – I could feel it inside me. Then he pulled out, pulled up his pants, zipped up, picked up his camera again, told me to spread my legs and pull my cheeks apart again, and took some pictures of the damage. I never got to see his cock.

I was there for two hours. He paid me $50 and tipped me $50. I thought I should have been paying him!
 
I have several that I equate to the wildest experiences I've had, and I'll share a few here if that's okay.

A buddy and I when seniors in high school wound up doing some hot things together. We knew we couldn't do anything at either of our houses, so at school we were walking down the corridor near the end of the day, and were talking about how we still really wanted to play. So he suggested the two of us stay late at school and catch the late bus home, and we could figure something else out. After the bell, the two of us sought out a private storage area of the high school where we knew no one ever was. It was this large stairwell that circled around the back part of the auditorium and went above the top floor toward the roof. It became the area where objects were placed and left for a long time. We had the place to ourselves. This was my first fully grown, mutually consented, person to person sexual encounter, and it was with another guy. I dropped my jeans, and he dropped his pair of white painter’s pants (popular back then). He was huge compared to me, but I realized that he didn’t seem to care about that. He loved my cock and aggressively sucked me. It felt good, right, and natural. It was so hot to be looking down and watching his male head bobbing in and out as he sucked, to see his male hair moving to his actions, and his male lips tightly wrapped around the shaft of my dick, soaking me up good.* It was heaven to me.

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I had to have his as well. So I switched the action and took his large dick in my mouth. The heat, the texture on my lips and tongue, the taste, the scent of his thick bush of dirty blonde pubic hair, the pressure against the inside walls of my cheeks and the soft but significant pounding on the back of my throat… It was the perfect cocktail of combined sensations. I was a fully and firmly established cock lover. I didn’t want to be anything else. We finished ourselves off by jacking our loads into a single 3 inch wide pool of warm white cum that we shot onto one of the steps, and left it there. Our melded deposit of boy batter just waiting for the next person to discover. I often think back and wonder what that pool of cum looked like over time, and if anyone ever found it. That was hot.

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I dated this girl for the first time and over the evening we found out that we were both bi. When I took her home she hook me up with her gay brother. It was weird having sex with her brother while she watched and masturbated,
 
It had been a while since I sucked a guy off, so I posted an ad on craigslist for a blow & Go at the mall. A 25 year old guy with a 10 inch cock responded. He was going to be at the mall with his girlfriend, and would love to get sucked off.

We emailed back and forth, I had him meet me in the men's room of a store that has small rooms as stalls, not the typical dividing panels.

Since we had only exchanged descriptions, not pics, I told him to go to the handicapped stall, close the door, but not lock it, and have his cock out, and msg he was there.

I walked in the stall, I could tell he was nervous. I locked the stall door, took his cock from his hand and dropped to my knees. It took him a minute to relax and get fully hard, but in almost no time he shot his load in my mouth. I swallowed and left.

I thought I would have felt awkward or guilty after, but I didn't.
 
The day i had two big cocks at the same time in one in my ass the other down my throat they kept switching then i sucked both of them off till they filled my mouth up with their delicious loads of CUM.
 
Very sexy, lean, handsome young black guy came onto me in the steam room. He actually had lube and condoms tucked into a towel and wanted to fuck me. I told him it's too busy for that, too many guys coming in and out of the steam room. However, saw him a few months later, early on a weekend morning. No one was around. He sat next to me and we started fooling around. Again, he pulled out the condoms and lube. Well, it was quiet enough that morning. :sex:
 
That is so hot. Wish I could join you for a threesome. (I would get tested too to enjoy the full bareback experience.) :) [Meant this as reply to Zabien.]
 
meeting two strange men in glory hole and ended up going to the motel room and letting them both fuck methen i swallowed them both
 
A friend of mine want to have a 3some with her and her boyfriend. Almost from the when we started taking our clothes off her bf totally ignored her and focused completely on me.
It was flattering, but so obviously hurtful to my friend even during.
To me, very wild.
 
I met a stranger in a bathroom stall on campus and I sucked him off under the stall. We moved to a lecture hall for more room and he made me take everything off. I gave him a long slow blowjob. It was really thrilling but I don't think anyone saw us :( He exploded on my face then I spent good time swirling his cum all of my face with his cock. I ended up walking home glazed still :)
Ooh and it was recorded :)
 
In the cuddly cabin of a friends boat, they brought a guy to meet me, lots of alcohol later on a dare he fucked me in the cabin as my friend as his bf listened.
 
In back room of a men's clothing store with salesman. It was almost in the dressing room but need lube.
 
wildest hookup experience that I ever did is quick fuck in living room while there is mom beside the room (kitchen). Mommy so busy with her cooking that didn't realize her son was fucking with his buddy. hahaha
 
Two nights ago after work i was feeling so damn horny for some cock ,my mind was set on taking a big cock down my throat and or deep in my ass i went home to shower and shave im comepletly hairless .once i got to the porn shop i went straight to the back ,it's a big shop and the boothes are big with long benches soi i put $ in the machine n got ass naked i took out my lube and put some condoms on the bench then i unlocked the door.after about five mins a latino man walked in the first i asked him was do you have a big cock if not don't waste my time he asked is 7' inches big enough ,i didn't say a word i reached for his zipper pulled his pants down and his cock hung between his legs limped i moaned and said oh yeah just what i wanted i told him to get naked and lay down on the bench,then i got between his legs grabbed his cock n started to stroke it .
To be cont....
 
Last year at the start of my last semester of college, a couple buddies took me to a gay bar in the city. I had just broken up with my fiance and I was in a really bad place emotionally. While we were dancing I noticed my Criminal Law professor in the crowd. I had only first met the man that week, but I knew for sure it was him. We made awkward eye contact a few times and then slowly made our way to each other on the dance floor. We danced for about a half hour while he whispered funny comments in my ear. It was the first time I'd laughed in so long.

Eventually, Ben whispered to me, "Would it be inappropriate of me to ask if you wanna get the hell out of here with me?" I laughed. "Very," I responded. "Let's go." I told my buddies I'd meet up with them later and then found myself walking around the city with Ben. The cold January night air had my teeth chattering, but I was too distracted by Ben's chiseled jawline and manly laugh to really notice. At some point during the conversation I had started rambling on and on about how I could never be a city guy, when Ben grabbed me and pushed me into the alley against a brick building, hard. He put his hands on my face and pulled me in for one of the most romantic kisses I'd ever experienced. "The Holiday Inn is just down the block. We could get a room there. Please, let me love you." At this point, he had given my crotch a squeeze and kissed me hard again, and I couldn't have said no if somebody paid me.

Once we got into our room, it didn't take long for the clothes to come off. Ben started sucking me in a way I'd never been sucked. There was something violent yet gentle about his technique, and I was moaning louder than I ever had in my life. When I warned him I was close to cumming, he stopped and rolled me over, giving my ass a gentle smack. Then he pushed me apart and started rimming me from behind. I gasped - this was something foreign to me as my ex refused to do that while we were together. It was considered taboo for us. As Ben probed me with his tongue, I felt something in me come alive - waves of pleasure rocking my nervous system, and I couldn't believe this was happening with a professor.

Ben must've been able to read my mind, because just as I felt an orgasm starting to build, he pulled his tongue out of me and rolled me over on my back again. "I want to look in your eyes." I couldn't believe how romantic this was for a one-night stand. He reached down off the bed into his jeans pocket and produced a condom while I laughed inside my head about the fact that he brought condoms with him to the club. He slid one on and was soon inside me. I could tell he was trying to be gentle, but I had just had a rough break-up, and I needed somebody to take it out on me. Soon my hands were on his ass, driving him into me while attempting to pick up the pace. He caught on to what I was doing and really let me have it. I couldn't stop myself - an intense orgasm rocked my body as I shook on the bed underneath him.

Typically, I was used to my ex pulling out after my orgasm, so I expected the same with Ben. I was surprised, however, when Ben's thrusting didn't stop. It was uncomfortable for me at first, but soon I started to feel that familiar pleasure and before I knew it I was screaming out moans of ecstasy again. I had four orgasms like that before Ben allowed himself to have even one. He is twelve years older than me, but it sure as hell didn't show. After that night, the two of us started seeing each other casually but ended up breaking things off after graduation, agreeing to be friends. I haven't seen him since, but boy do I think about the incredible sex we'd have every time I need a visual to get myself going.
 
That is one hot story! Sadly, my professor offered no such extra curricular benefits!
 
That is one hot story! Sadly, my professor offered no such extra curricular benefits!

I was crazy about him! He was easily the best sex I've ever had - so far. I don't think a day went by where I'd see him and he didn't end up on top of me somehow, lol. The hottest part about all of it was when we'd make eye contact in the classroom and he'd try not to smile. I'd get so hard watching him up in the front of the room lecturing about Law while all I could think about is the hot sex we'd had just two hours before. It's a shame things didn't work out with that stud!
 
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