This is my first attempt at a story. All of it is true. I might write up other adventures I had in Europe if this is well-received. Please practice safe sex -- I'm fortunate that these events didn't result in catching any diseases.
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I was always curious about sex with men but too deep in the closet to actually meet someone in a bar or get to know them openly, so I turned to anonymous sex as an outlet. I'm a little over 6 feet tall and weighed about 200 lbs with a slight belly no matter how much I worked out, so I was a bit self-conscious of my appearance and a gloryhole satisfied my desire for cock and helped me not worry about my body or my reputation. Visiting a seedy adult shop usually resulted in me getting an anonymous blowjob. Later I tried sucking cock through a gloryhole but couldn't stand the taste of cum so I'd spit it out or let the guy shoot into my cubicle while I avoided it. Ultimately, a guy convinced me to let him fuck me, but it was painful and unpleasant. My ass was too tight, there wasn't any lube except for my spit, and it was all I could do to not run away screaming. Not fun for a first time.
But I was still interested and desperate to be filled. I tried candles and really loved the feeling of a hard shaft penetrating me, teasing my prostate, and filling me completely. My best orgasms all came with something in my ass and I was sure that the real thing would feel even better. But after that first time I knew I couldn't handle it without a lot of preparation.
Not long after this I got a chance to work in north Germany for two years in the late 80's. As a young 23 year old with no girlfriend, I jumped at the chance. Hamburg has a famous red light district and I didn't know anyone in the country, so I felt more confident exploring my wild side. I visited a "Sex Kino" to buy a butt plug, a metal cock ring, and some lube and began using the plug to loosen up my tight hole. I knew that it would keep my ass open for a while, but I wanted it to stay loose all the way to Hamburg, so I devised a plan. If I could keep the butt plug in me as long as possible my sphincter wouldn't be completely closed before some man filled it. The rest of this story is about what happened when I put my plan in action.
It was a pleasant spring Saturday and I was feeling horny. I put on my favorite Bike jockstrap. The feel of the white pouch cradling my cock and balls as well as the leg straps that I knew framed my beefy football player ass had me hard and ready for action. Then I grabbed some lube and my butt plug and moved to the bathroom. I put a generous amount of lube on both the plug and my twitching hole then pushed the plug into me. The first try didn't work so well -- my hole resisted and I felt a sharp pain. I pulled the plug back out and waited until the pain passed and tried again. This time I slowly thrust the plug in and out, gradually getting more and more of the shaft inside me, forcing my sphincter to relax. Eventually I managed to get the widest part of the plug into me without too much pain, and my ass sucked the rest of the plug into me until I felt the comforting base snug up against the outside of my hole.
The effort to get the plug in made my hard-on disappear. That was a perfect time for me to slide on a solid metal cock ring. I slowly eased each of my large balls through the ring, and then I manipulated my shrunken, soft cock through as well. As I finished the job, I stroked my cock with my greased hand to help plump it up. As the blood rushed into my cock, the ring tightened around me until my shaft was firm and hard and jutting out from my stomach. I re-arranged my jock again and admired in the mirror how the cock ring really enhanced my package and made it even sexier. The jock kept my 7" secure so I wouldn't be too obscene walking in public, but with enough bulge to draw attention. After cleaning up I slid on my tight faded jeans that had a few small holes in the crotch and ass areas. Adding a dark long-sleeved shirt, I then sat down to put on my socks and shoes. My eyes widened as I felt the plug pushed deeper in my ass and a slight moan escaped my lips. It took me a minute to catch my breath before I could finish getting ready. After a quick check of the train schedule and tossing my daypack over my shoulder, I was out the door.
The ten-minute walk to the train station allowed me time to truly enjoy the feel of what was going on under my clothing. Each step caused the plug to shift in my ass, occasionally brushing my prostate and sending a thrill through my body. I naturally rolled my hips a little to enhance the pleasure of the plug fucking me. The cock ring kept my cock hard and my balls pressed tightly against the confining pouch of my jock. The leg straps of the jock tugged at my ass and the rough fabric of the jeans rubbed directly on my ass cheeks. I purchased my round-trip train ticket to Hamburg and moved to the platform to wait for the next train. Right on time it arrived and I boarded for the hour-long journey. I quickly took my seat, moaning quietly as the now-familiar plug pushed deeper inside me. I settled in and pulled out some porn stories to read and keep me excited during the trip. I carefully made sure the cover of the book couldn't be seen by my fellow patrons.
The train wound its way through apple orchards and small towns but I paid scant notice, focused as I was on the sex that awaited me in the backstreets of Hamburg. Each bump and roll of the train caused the plug to fuck me slowly, stretching my hole, moving deeper inside me, exciting me further. As the train approached the main station I quickly ducked in to the nearest restroom, locked the door, pulled down my jeans, and removed the plug from my ass. Although I wanted to keep it in much longer, it had served its purpose of loosening up my ass for what I had planned later. I rinsed off the plug in the sink and stashed it in my pack, dressed, and headed out just as the train reached the station. I took two steps at a time up the escalator and saw the daylight swiftly fading to night as I stepped outside. Since I didn't want to carry my pack where I was going, I stashed it along with my wallet and keys into a train station locker. The cost was worth the peace of mind to know my stuff was safe while I focused on other things.