First Time for Everything

My wanting cock throbbed around my hand as I glanced down at my illuminating phone in my dark car. "Just got here" I replied, before switching internet tabs to the previously-loaded video of a blonde girl in a gloryhole.

I had a long drive that day, about 3 hours to my hometown destination. Having broken up with my girlfriend a few weeks back and not having sex since, on top of the stress from rapidly-approaching final exams, I felt pumped with a tension that I desperately was seeking relief of.

Halfway on my drive home, I pulled over to a rest stop to smoke a cigarette and use the restroom. As I stood outside the car, overlooking the trucker area of the rest stop, I remember a story a friend told me involving "lot lizards", or prostitutes that service truck stops.

Having no sexual contact in weeks, I felt my dick begin to shift in my pants. I adjusted it to the side between cigarette hits, trying to hide it at first. I began to fantasize of being one of those truckers, shot from driving all day, pulling into the stop and getting approached by a hot little piece of ass wanting nothing more than to suck and fuck you (for a bit of cash of course).

I slightly hesitated. Part of me felt disgusted to even think of this. But another part of me was feeling more and more turned on by the dirtiness of it all. My thoughts continued as I envisioned how well any prostitute must work a cock, considering it is their job and all. I have been with girls in the past that despite how much I appreciated the effort, they just could not suck a cock or ride to the point that would lead me to get slightly frustrated and then fuck the shit out of them (a win win for them?).

What would it be like to be a hot slutty girl, I continued to think. To be able to get sex so much easier from all the guys that admired you. I have always been drawn to the idea of having sex with multiple women at once, but despite multiple "down for it" girlfriends it's never came to be. If I were a hot girl I would fuck and suck multiple guys at once for money, easily.

"Did I really just think that?" I thought to myself. "Thinking of being a girl and getting gangbanged? That is so wrong.". I felt a wave of guilt begin to approach. I am a straight male, and never fantasize of other men.

But there was something about my mood that day that had me thinking different thoughts. I began to fantasize of myself being a "lot lizard", just this once.

By now my cock was begging for relief, so I decided to go to the rest stop bathroom and rub one out. I went into the stall and dropped my pants down to my ankles and began slowly stroking my unshaved cock, which was now half-hard from the walk from the car. I wanted so badly to suck a cock, and I didn't know why. I wished there was a gloryhole and a trucker in that stall.

My cock grew in size as my thoughts raced. The sound of heavy footsteps approaching, the stall door slowly opening and closing, a pair of pants and a belt dinging as they thud to the ground, then a long, thick cock slide through the gloryhole for me to drain anonymously. I imagined wrapping it around my lips and working it harder and harder until I feel it twitch then stroking it with both hands until...

I aimed my cock down in between my legs into the toilet and milked out a BIG load. I felt my thighs tremble and my eyes roll back into my head as I switched to long, tight strokes until every drop was out. I used toilet paper to wipe off the excess cum that was dripping of my deflating cock and went back outside for a cigarette.

I stood in the same spot as the last cigarette I smoked, not necessarily feeling proud that I just jacked off in a rest stop bathroom, but then again public masturbation was nothing new to me. Something about possibly getting caught has always been a turn on. But I digress...

I continued to smoke my cigarette, feeling relieved as the little remaining cum that worked its way out of my shaft was now dripping out of the end of dick, making little wet and cool contact marks on my thigh. But as I continued to smoke, I felt another urge coming on.

"I need someone to make me cum" I thought. I decided to check craigslist to see if any women were interested near by. I searched the 4 area subsections of the site and found nothing, until I searched by my home destination.

"Glory hole available NOW" was the most recent posting. My hoped turned from excited, to embarrassingly more excited when I realized that it was a gay gloryhole. I felt a mix of negative emotions telling me to stop: nervous, scared, shameful, etc. But I moreso felt emotions that grasped me at my core and told me to embrace: riskiness, using somebody for sexual pleasure, and mostly the need to cum.

After a mental battle, I decided to go through and exchange a dick pic and stats in return for the address. I made sure it was discreet and confidential, then punched the address into the GPS. I was feeling that same race of emotions multiply as I pulled up to the apartment. Me, a 26 y/o guy getting sucked off by a 40-something year old man felt so wrong it turned me on.

Fantasizing was one thing, but I don't think I could ever go through with it without blocking out the idea that it was a guy sucking me off. Loaded with a video of a hot blonde in a gloryhole, I made my way out of the car and opened the side door of the apartment. No going back now.

As I opened the apartment door, I nervously popped my head in and look around before allowing myself to walk inside. It was a pretty nice apartment with a big tv and Playstation playing some club music. There were windows with blinds dividing a room from the main room, so as instructed I lifted up the blind on the right window.

I saw a towel neatly folded over the window sill below the blinds, and knew it was the right window. I ignored the fact that it was a guy as I hit play on my phone porn video and undid my belt.

I lifted up my shirt to reveal my six pack, trying to turn whoever it was on so they would want to do a better job. I unbuttoned my pants, undid my fly, and dropped my jeans to my ankles.

I felt my soft cock sway slightly as I stood there, shirt up and cock out in some strangers apartment. I have a good size cock when hard, about 9", and truly thick.

I stood there for a couple seconds which felt like minutes waiting, then felt a hand lift up my cock and the instant warm and wet comfort of a mouth. Testosterone began to rush.

I continued to watch the porn video of a babe in her 20's, blonde, fit, with a great pair of tits. She was first teasing a good size cock through a gloryhole, before beginning to deep throat it. She looked so good doing it, and she could take it deep too. My mind remained in the video, but my body was feeling amazing in reality.

This guy was no joke. He did just as I wanted, no sensual bullshit, just went straight down to business and began sucking my soft dick hard right out of the gates. I had to rebalance myself as I literally felt my cock getting harder and harder in this mans mouth, and him responding by moaning as he clearly got more excited and worked it faster. My cock was nearly fully hard, and this poor man could only fit it nearly halfway in his mouth. I don't think he knew what he was getting himself into. But my god, could he suck a cock.

The wet and sloppy sound of my now fully hard cock being straight up worked by a stranger was only occasionally interrupted by the sexually desiring moans of the one sucking it. I began to feel dominant and powerful, as I like to feel when women. I have this stranger being the definition of my bitch on the other side of this window, literally working my cock as hard as they can when they've never seen me, and will never see me again. They know I am giving nothing and return and want nothing more than to suck my load out.

I was approaching orgasm. The man pulled it out of his mouth for the first time in at least 5 minutes since he started to take a breath. He started licking it, like he wanted to slow it down but I was not having it. I reached my arm through the gloryhole window and grabbed the back of his head before pulling it in and simultaneously pushing my cock down his throat. He gagged, but he liked it.

He now was going 100%, and as I felt the orgasm approaching I fought it as hard as I could. I wanted this to keep going. I fought it back a bit, but was no match to these cocksucking skills. Without warning, I blew my load into his mouth and he moaned. It was the best blowjob I have ever received, and he swallowed.

He kept sucking until I had to pull back a bit, and then continued to suck. I could tell he was really turned on and wanted more, but I was done and felt the guiltiest pleasure in dumping my load in his mouth and then leaving. After a minute of post-orgasm sucking, I pulled out, he double-patted my thigh as a thank you, and I closed the curtain and left.

I couldn't believe I just had the most amazing orgasm through a gloryhole window from a middle aged man. But it sure felt damn good.