The first time I ever saw another guy jerk off was at a nudist colony called Naked City in Indiana (near the Dunes, I think). I was 18 when I went with an older friend from work on a dare. The same friend asked me to sleep with his wife on a camping trip a year later, but that's another story.
It seemed the clientèle was enjoying the view of my naked, 18 year-old body. Unfortunately, they were slightly overweight, balding, older men and not the desperate housewives I had heard about.
I had hoped to enjoy the view of naked female bodies in the same way the old farts were enjoying me, but was sadly disappointed.
I had to admit that seeing several of the men jerking off at the sight of me walking around a pool was fascinating. My friend took it all in stride and said they probably thought we were a "couple, otherwise I would have already been propositioned.
I swam a few laps in the pool to tease the geezers, but the joke was on me when I stepped out of the pool with the start of an erection.
My friend told me that he had let guys blow him several times at this place, and he still carried on a great relationship with his wife. He had kids, a home, dog, boat, cars, etc. He just dabbled in the wild side once in awhile without anyone else knowing (except me, at that point). He asked if I was interested in letting one of the old guys blow me, and I quickly passed.
A few years went by, and after breaking up with one girlfriend and not knowing if the next was really worth staying with, I got drunk and stumbled into an adult book store with video booths.
Like my friend, I decided to experiment.
My first time walking into an adult bookstore, I had no idea what to expect. I was surprised to see all the dildos on the wall, blow-up dolls, rubber genitalia, and a video booth room.
Curious, I asked the weird-looking guy behind the tall counter how it worked. He escorted me to a booth, dropped in a few tokens labeled "Heads, I Win, Tails, You Lose" and selected a movie for me. I thanked him and watched some dated poor-quality porn for a few seconds. I pressed a button to change channels and noticed something out of the corner of my eye.
A huge dick was poking through a hole in the wall. I thought my cock was big, but this guy had me beat. Not being gay or even "bi-curious", I didn't know what to do, so I tried to ignore him. Eventually, the monster cock went away and I was out of tokens.
I bought a few more dollars' worth, hoping to find a movie to jerk off to. After I went back into the booth, I put all my tokens in the machine and went on pressing the button.
I finally found a movie of a girl getting pounded in the ass by a different guy about every 30 seconds. There must have been 5 guys taking turns, and when they were done with her ass, they moved to her mouth. I never saw anything like it. I had my pants unbuttoned and my cock out as quickly as I could.
Just then, the door to the booth opened (no locks) and a young guy (a little older than me) put his finger to his lips and made the "shhhh" sign.
He reached down and gently began stroking my cock. Then he knelt down and began blowing me. I've been given dozens of blowjobs by several girlfriends, but none ever made my knees weak like this one. At some point, he licked a finger and slid it in my ass. I really began to shake and found myself cumming hard in this guy's mouth. I expected him to spit it out right away, but he kept on sucking until I was completely dry. Then he coughed up my cum in a napkin, folded it up, and put it in his pocket. It was the strangest thing I had ever seen.
Visibly shaken, I wanted out of there. He told me to relax and wait a few minutes, and then left me alone in the booth. I walked out a few minutes later, and overheard the weird-looking guy ask a customer what he thought of some new porn star. The guy said "he looks a lot better out of his clothes".
It wasn't until I walked out the door that I realized the customer was the guy that just blew me, and he was talking about me!
I thought I had an idea of what to expect in almost every glitzy, depressing, pathetic adult book store with a video "preview booth" section: A bunch of guys looking at magazines, a few renting movies, and a few doing laps around the video booth room.
I found what I thought was one of the nicer adult book stores called Swinger's World, with some kind of coin-operated "buddy windows" in the video booths that would turn an opaque glass transparent when you deposited tokens or quarters. I thought it was a good idea to share movies, but I guess it was really to watch the other guy watch movies, jerk off, or show off.
I bought a hefty amount of tokens and merged into the traffic doing laps around the video booths. I'd pause and look at the boxes/covers of the featured videos - not really interested in who starred in what - but rather who was checking me out.
When I finally did find a booth that was reasonably clean, I put in a few tokens and found some good movies to jerk off to. Within minutes, the glass on either side of my booth started to get clearer, but not completely. I decided to see who was so interested in me, and put a few tokens in the buddy window.
To my left, a middle-aged guy was all buttoned and zipped up, but fondling himself through his clothes. To my right, an older gentleman, gray hair, glasses, beard, mustache, about 6' tall and 230 lbs.
He reminded me of "Al" from the Home Improvement TV show. Why couldn't there be a hot babe in an adjacent booth once in awhile!?!
I'm not sure what the fascination was, but I found myself paying less attention to the movie and more attention to the big guy to my right. I looked at him while I slowly tugged at my cock. About a minute later, the windows were opaque again.
There was a pull on my door, but I had latched it. I waited a few seconds, buttoned up my fly, and unlatched the door. A few seconds later, there was another tug at the door. It was my large admirer.
He motioned for permission to join me in my booth. I backed further into the booth to give him room to come in. He locked the door behind him, turned around, and undid his pants.
He had intended to just jerk off with me, but I thought he was there for more. Being a little scared, a little nervous, and incredibly curious, I reached down for his cock and pulled out the fattest, shortest cock anyone could have imagined. It was in that split second I decided if I were ever going to try sucking dick, this would be the one to start on.
I knelt down, not exactly knowing what I was doing, and slowly kissed and licked the head of his dick. He stood as still as he could and just ran his fingers through my hair. Then I decided to go for it and struggled to get my mouth around his short, fat cock. Once I had it there, there wasn't much of a shaft to go back and forth on, so I caressed his balls lightly. I moved my tongue around as much as I could, but his thing was so big, about all I could do was suck while my tongue licked the underside of his cock, all the way to his balls.
Without warning, he shot his load in my mouth. I wasn't about to swallow it, but his cock was so big and throbbing, I couldn't get it out of my mouth. I gagged a few times, choked, and eventually managed to get his cock out, as well as a load of cum which ended up all over my shirt.
I'm sure everyone else doing laps must have heard what was going on. I was afraid they'd want in on the action. He was very appreciative, and asked if he could return the favor. To my surprise, my cock was rock hard throughout the entire blowjob.
I undid my jeans and took off my shirt. He took his time, turning me around, fondling my ass, spreading my cheeks, fingering my ass, and finally sucking my cock. I was about half his girth but about 4 times longer. Unlike a previous video booth blowjob, I was ready to fuck his face. I put his hands on my ass and bucked my hips into his mouth. He grabbed my ass cheeks and pulled me away, and then back in again, never gagging and matching each of my thrusts with a long suck.
He knew I was going to cum hard, and unexpectedly pushed two of his fingers into my asshole.
I wasn't really ready for that.
I came so hard, my legs were shaking and I almost collapsed right there. He swallowed my load, and then coughed it back up again. I determined that's a trick you learn when you suck a lot of dick.
He asked if I'd like to go to his place - that his wife and kids were out of town that weekend.
I declined. I was both shocked and amazed at what I just did. I had a shirt covered in his cum, cum spattered jeans, and I was out of tokens. I was about to ask him to buy more, but instead I told him to stay in the booth while I left.
I walked out of the video booth room, through the well-lit magazine racks, and out the back door - never looking up.
I was embarrassed. I was confused. I was getting an idea for a return visit.
A few weeks had passed before I became curious – again.
I was 21, but looked 17. I had been to adult bookstores with video booths at least a dozen times by now. I learned about glory holes, enemas, lubrication, the mechanics of anal sex, the prostate, and anything else I could read about. I had received two blowjobs from strangers and given one. I experienced all this while maintaining a healthy relationship with my girlfriend of 4 years.
The preparation that went into my next trip out of town and to my favorite porn shop was over the top.
I tried to imagine what kind of man I was going to experiment with next, and wondered what he would like if I offered myself to him. The more I thought, the weirder I got.
I started with my body hair. Except for the hair above my neck, I shaved, waxed, or plucked every strand of hair from my body. "Smooth" doesn't do it justice. I was satisfying taboos on multiple levels.
Then I made sure every inch of my body was clean, to include my ass. I had seen movies where girls would get fucked in the ass and moments later put that same cock in their mouths.
I wanted to be prepared for anything, so I watched what I ate for 48 hours and completely cleaned myself literally inside and out.
I manicured my fingers and pedicured my toes. I put on a little cologne, but nothing overwhelming. I bought condoms, KY, and Kleenex.
Trying to cut down on things I'd have to carry, I squirted half the tube of KY into my ass. I fingered it in as best I could, and then showered again to clean off anything on the outside.
Even though it was winter, I decided to keep my clothing to a minimum. Jeans, tennis shoes, a heavy sweater, and no underwear or socks.
Like a girl on prom night, I decided this was the night I was going to go "all the way". I was just as nervous, too.
The drive to the porn shop was uneventful. It was a quiet winter's night. Not much movement in the area. A slow night at Swinger's World.
When I walked inside, it seemed I was the only one there except for the cute girl behind the counter. That was a twist! She gave me a wink and asked if I'd like some tokens. I bought about $20 worth and walked over to the boxes/covers in the video booth room. I quickly made notice of which numbers were for gay or she-male movies and then found an open booth.
About $10 into my tokens, someone else finally showed up, tugging at my door. I unlatched it to see who was there. It was a greasy-looking old guy that looked either homeless or on his deathbed. I re-latched the door.
A few minutes later, there was another tug. This time, someone else. Not what I had in mind.
I re-latched the door again, and again. This was getting depressing. Eventually, I ran out of tokens. I walked out to buy some more and found two attractive men out of the dozen or so that began the ritualistic lap around the booths.
The two men were talking to each other while looking at me, and I managed to make eye contact with one of them. He came over and asked if anything good was playing. I pointed to one of the gay movies showing a young guy sitting on an older guys cock and said, "I'd like to try that - one." He smiled at me and said, "that looks like a good one."
I walked around and tried to find the darkest corner of the booth room, and found a booth.
As soon as I walked in, I latched the door and proceeded to take off all of my clothes. I folded them up and placed them on an unused ashtray shelf next to the bucket seat in the booth. I put my shoes under the chair and soon realized I picked a booth that hadn't been cleaned in awhile - I was standing barefoot in several puddles of cum.
I took a few deep breaths and tried to relax. I tried to imagine how long it would take to get dressed in case the police paid the porn shop a visit. I also worried about the possibility of being gang-raped - not so much for the number of times I'd get fucked - but because condom use was probably not a priority in a rape and I had my whole life ahead of me.
I figured it was still early enough in the evening and the crowd would be tame, so I decided to go for it.
I unlatched the door.
I dropped a few tokens in the video machine, which is apparently like ringing the dinner bell in porn shops. The buddy windows on either side of my booth were being fed tokens almost immediately.
I heard a tug at the door, but it didn't open, at least not all the way.
The booth was dark, and except for the light from the videos being played, there were no other lights on. That made it easy for someone outside the booth to look at me, but I couldn't see him or her. I knew I was being watched. It was only a matter of time.
I turned and watched the movie, caressing my chest, stomach, legs, thighs, occasionally squeezing my cock and spreading my ass cheeks. I could feel the cum on the floor squishing between my toes.
Every once in awhile I'd turn and look at the slightly opened door.
I felt the door open by the cool air that filled the booth.
I didn't take my eyes off the movie I was watching. I felt a kiss on my ear, my neck, my back, my ass, and then the flick of a tongue between my cheeks. He pushed on the small of my back and bent me over, then had me spread my legs a little further.
I reached out and put my hands on the buddy window.
I felt like I was being frisked. He kissed my sides, my hips, and gave light bites on my ass cheeks. He reached up and spread my cheeks with both hands as his tongue darted in and out of my asshole. I arched my back and pointed my toes inward as I felt a finger slide into my anus. His finger finally went deep enough to find a well of KY.
As his finger slid in and out more easily, I could feel my cock twitch with each thrust.
After a few more kisses on my ass cheeks, my visitor removed his finger and took off his coat. I heard him place it on the chair behind me. He slowly turned me around to face him, my cock fully erect cock bouncing in front of me. I was embarrassed or ashamed that has ass fingering had produced such a reaction.
He must have been in his late 40's or early 50's. Very business-like, slightly taller than me, broad chest, neatly trimmed gray hair, and very much the gentleman. He could have been Sean Connery's younger brother.
He told me how attractive he thought I was, and asked if I did this sort of thing often. I told him it was my second time in a video booth, and there was still a lot I was curious about.
He smiled and said he wasn't looking for much. He wanted to see my cock and taste my cum.
I asked him if he was clean (which I hoped meant disease-free) and he said he was. I said I was, too. He then proceeded to kiss my chest, sucking my nipples, and running his hands all over me.
He held both of my hands as he sat down in the chair. He asked me to raise my arms and hold my hands behind my head. As I did, my cock seemed to stand even taller, almost as if teasing my visitor.
He then leaned over and proceeded to give me one of the best blowjobs I've ever experienced. He cupped my ass from between my legs, caressed my balls, and eventually slid two fingers up my ass and began finger-fucking me. I wanted to grab his head and thrust as hard as I could down his throat, but I kept my arms up and my hands firmly behind my head. I'm surprised I lasted as long as I did. When I came, I was afraid my asshole was going to break his fingers.
He seemed to suck every drop out of me, but quickly spit it out on the floor between my legs.
It was freezing outside, cold in the porn shop, but I was burning up inside that booth. I asked if he had protection and he gave me the look of disappointment. I gave him a light rub on his growing groin and he reluctantly pulled out an extra-large condom. I tore the package open, put the condom in my mouth, and undid his pants while he sat in the chair.
I tried to be careful not to let his pants fall in the cum on the floor as I pulled out a soft, fat cock. The head was no bigger than mine, but the shaft was twice as thick as mine, if not thicker. I squatted down in between his legs, holding my cock up off the floor with one hand and caressing his balls with the other. I carefully put my mouth over the head of his cock, allowing the condom to unroll a little at a time as I moved my mouth further and further down the shaft. I watched my girlfriend do this a dozen times, so I thought I would try it. I must have gagged 2 or 3 times and finally had to finish rolling the condom down with my free hand.
I asked him if he was happy, so far. He said he was. I asked if he wanted to fuck me, and he said a blowjob would be fine. I told him after all the fingering he did to my virgin asshole; I wanted to try fitting his cock in my ass. I wanted to try going all the way.
I guess he thought all that KY was someone else's cum in my ass. When he realized that it wasn't, his cock became fully erect in a matter of seconds. It must have been only 6 inches long, but the shaft was as wide as my wrist. I asked him to keep his hands to his side (payback for making me hold my arms up for so long). He reluctantly held the sides of the chair.
I stepped back and pushed his legs together, making his cock stand up even higher. I turned around and straddled his legs, slowly stepping backward, trying not to slip on the cum on the floor.
When I thought I was directly over his cock, I reached down and held the tip to my asshole.
I looked over my shoulder and could see his eyes were locked in on my ass, hands at his side.
I let out a deep breath and lowered myself on him. It hurt so bad at first, I think I let out a yelp. I lifted myself back up and could see his hands come up for a second, then slowly go back down. I tried again, this time managing to get the head of his circumcised cock past my anus.
I didn't know how much more I would be able to take – especially being my first time.
I slowly moved up and down, arching my back. That only allowed another inch to go in. I reached back and spread my cheeks. His cock was so thick, I wondered if my asshole would ever be the same.
I'm not sure if it was the KY going to work, my asshole finally stretching, or me just getting used to the pain, but I managed to slide down another inch. I began a slow, rhythmic up and down motion and felt precum begin to pour out of my cock. Only an inch or two of his shaft was sliding in and out of my ass, but I guess that was enough to make him happy. I relaxed a little more, and decided to reward him for his patience.
I reached back for his hands and put them on my thighs. He grabbed my ass cheeks, spreading them further with each thrust. His grip was so tight, he was bruising me. I quickened the pace of my up and down movement and started to feel cum building up between my toes. My feet were slipping!
I tried to steady myself but it was too late. My feet slid out from under me and my full weight was on his cock, forcing it all the way in. The head of his tool hit deep inside me and I came instantly. He held my hips and pushed me down harder onto his cock. I felt his fat tool spasm inside me, making me shake and causing me to cum again. It was intense!