The Fleshlight Trip
by Rob Thomas


Fleshlight. Fleshjack. Pocket pussy.

It has many names, and to fleshlight lovers I’m known as a “frequent flyer.” That is, I use it regularly. And often.

I discovered the fleshlight several years ago and was immediately drawn to it. A tight hole is something I’ve never been able to resist, and when that hole is also always ready and always willing, I’m helpless. I love fucking the fleshlight because I can make it just about me and my needs. With the fleshlight my pleasure and my fantasies control, and my “flights” give me the most intense orgasms I’ve ever had.

Fucking. Flying. Jacking off.

However I’m doing it, I love doing it in different places, so when I found out I had to go out of town for work a few weeks ago I was very excited. It had been a while since I had given my dick a ride in the fleshlight and decided a hotel fuck was just what we both needed. As I packed my bag that morning I made sure to pack plenty of lube, my favorite poppers, my cock ring, and of course a fleshlight.  I have several models, but I was craving a really intense flight so I decided to take my favorite, the ultra-tight butt.  Its sweet, puckered hole drives me crazy, and the way it grips my dick never fails to completely drain my nuts.

The four-hour trip flew by as I was busy with thoughts of the flight that awaited me later that afternoon. I love having a hard-on, and that sweet, fullness in my cock was pleading for release for the full four hours. I couldn’t keep my hands from caressing my crotch as I drove, and twice I came deliciously close to shooting a load while diving. A quick jack would have been lots of fun, but quite messy, and I didn’t want to show up for my meeting with cum stains on my tie. Besides, I had better plans for later that afternoon.

When I arrived I carried my bag into the office rather than leave it in the hot car all day. That was likely not the best decision since I had a difficult time paying attention during my meeting.  I couldn’t stop thinking about the tight hole that was in my bag just a few feet away, waiting for me, and I found my gaze repeatedly drifting in that direction. Thankfully my presentation was brief, and I was able to conceal my erection for the few minutes it took. I was happy when the meeting ended early, and I was finally able to head to my hotel. I had a few hours before I had to meet the guys for dinner, and I planned to use the time well.

Once I checked-in and got to my room, I immediately unpacked my toys. As I pulled out the fleshlight it struck me that if I had left my bag in the car I would have a warm hole ready for me. However, I would shortly have it wet and warm all on my own. I decided a glass of wine would be the perfect start to my flight so I decided to head down to the bar. As I was gathering my wallet and key I saw my cock ring laying on the bed. I decided to slip it on, and slip my underwear off. I love how the cock ring lifts and shoves my dick and balls forward. It also keeps me semi-hard, giving me a nice bulge, and the feeling of my dick and balls rubbing against my jeans with every step is incredible.

I was the only person in the bar, but I didn’t much notice because the bartender had my full attention. He was probably about 26 years old, 5′ 11″, and a firm 180 lbs. He also had beautiful, full lips, and a soul patch I desperately wanted to lick. He also had a nice bulge, which also had my attention. As I was finishing my wine I looked down to admire my own bulge and noticed I had leaked precum through my jeans. It was a small drop, but I knew my dick would soon begin to flow. I quickly downed the rest of the wine and headed back to my room, thankful I had other clothes to wear later.

As I laid out everything I would need for my fleshlight ride my precum really started flowing.  I was so turned on by the bartender that I feared I wouldn’t last long, but I was craving the satisfaction that comes only from a long, slow ride. I decided to take it slow and really enjoy every second. I took a hit of popper and sat back for a minute and enjoyed the warm, initial rush.  I hadn’t eaten ass lately and was suddenly craving it, so I grabbed the fleshlight and went to work on it with my mouth. As I teased around the hole with my tongue I imagined that I had my mouth on the bartender’s ass. It was so fucking delicious. I grabbed another hit, and with the popper rushing through me I started really exploring his hole. I soon had it all the way in, tongue fucking his sweet butt as hard and as deep as I could. Damn, his hole was good, and I was anxious to slide my swollen dick into him.

I didn’t need much lube since he was wet with my spit. His hole was also now warm from my tongue fucking. I wanted a hands-free ride so I slipped the fleshlight between the mattress and box springs, and as I slid my cock into his warm ass I knew my planning and waiting were going to pay off with an incredible orgasm.  I had his ass at the perfect height and angle for some deep thrusting, and began slamming my dick into him. With each thrust my balls slammed his hole with a loud, painful slap. I was in heaven, but I was fast approaching my point of no return, and knew I had to stop if I was to have the long ride I needed so much. I hated to pull out of his warm ass, but I knew I’d be back inside soon, ready to give us both what we needed.

I pulled the fleshlight from its mount and pulled up a chair. As I slowly slid the fleshlight down my shaft I noticed the full-length mirror across the room. I love watching, and being watched, so I pulled the chair as close to the mirror as I could, and sat down and spread my legs so I could get a good look at my throbbing cock and balls. I took another deep hit of popper and held it as long as I could, wanting my body to absorb every molecule. Then I started working the fleshlight up and down my dick. Rather than my own reflection in the mirror I saw the bartender sitting across from me, watching me, encouraging me. Fucking incredible. Nothing gets me off better than having a man watch me, and as we locked on to each other’s eyes I began to cum.  The feeling radiated from my dick all the way up to my head and back down; I felt as though my entire body was cumming. As my prostate contracted, sending squirt after squirt of my cum into his sweet hole, I looked into his eyes, wanting him to know that he had made me come. And that my warm cum was just for him.

I was exhausted, but very satisfied. And also running late. I quickly straightened up the room, carried my toys to the bathroom and jumped in the shower. After a quick piss to move the rest of the cum out of my dick, I headed out to dinner. As I passed through the lobby I took a brief detour and saw that my sweet boy was still behind the bar.

After a quick dinner I decided to swing back by the bar and have another glass of wine before heading up to my room. I also wanted another look at the sweet ass I had fucked earlier. The bartender was still working, but was busy talking to another customer.  I sat down a few bar stools away, and the bartender immediately remembered me and brought me another glass of wine. Earlier I had been so fixated on his lips and bulge I didn’t notice his name tag: Josh.

He and the other customer continued to chat, and while I couldn’t hear everything the other guy said, his demeanor implied he was flirting with Josh, and I noticed that the bulge in Josh’s already tight jeans was even larger than before. I enjoyed watching the scene play out, as evidenced by my own growing bulge, but decided to call it a night and head back to my room.

Upon entering my room I headed to the bathroom, and upon entering I saw the fleshlight, quickly realizing I hadn’t cleaned it before I left. I was immediately hard again.

I love sloppy seconds- especially when the first load is also mine.  I immediately had my mouth on Josh’s ass again, tongue fucking his hole as deep as I could, almost cumming when his ass let go of my first load, sending it down my throat. Fucking incredible. Knowing my cum had been in his hole, waiting for me, was so goddamn hot. I pulled myself away from his butt and quickly undressed, all the while savoring the taste of cum in my mouth.  As a string of precum hung from my dick I grabbed the fleshlight, lube and popper and headed for the bed. My previous ride in Josh’s hole was so intense I wanted another just like it. I returned it to its mount, lubed up my cock, and slowly inserted my swollen head just slightly inside his spit-lubed hole. As I held myself inside I took a deep hit of popper and just held my dick there, admiring the hot scene- my cock in Josh’s hole- as the popper rush swept over me.

I began to slowly fuck his amazing ass, losing track of time. I wanted to savor the moment, but I was impatient to fill Josh’s ass with my cum, once again making his hole mine.  I could feel my prostate begin to swell, and then the contractions started, pumping my cum through my shaft and into Josh. It was so intense and I didn’t want it to end. I didn’t want Josh to ever let go of my dick, so as I gave him the last drops of my cum I just held myself inside him, savoring the last minutes we’d have together. As I finally slipped my dick out, my second cum load slowly flowed from his beautiful hole.


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