I was 30 years old and discreetly bisexual with a repressed submissive streak. My girlfriend was on a work trip for the week. She was 28 and while things were great overall there was a distinct cock-shaped itch in my life that she couldn't scratch. Thus, almost the second she was out the door I was locking my chastity cage on my cock and sliding a plug into my ass.
I was planning on fully leaning into my submissive gay side for this week. I hopped on grindr and before too long found a nameless profile with a hot picture of a hard cock bulging in some grey undies. The bio said he was straight and looking for head and not much else.
I sent him a chat, not expecting much of it but that bulge was too tempting to ignore. Once he responded and we got chatting he seemed pretty legit and nervous about a guy sucking his cock but horny enough that he needed it. I got more details from him; he was 18, had a nice uncut 7" cock, and had never been with a guy before. Needless to say I was salivating at the opportunity.
We set out our plan. He would wait until his family went to sleep and then he would slip out of the house and I'd pick him up and suck him off in the backseat of my car in a nearby parking lot. He wanted to wear a mask and keep contact to a minimum so he could try to forget he had a guy sucking his dick. I loved the idea of anon hookups; to know I could be swallowing this guy's cock one day and then walking obliviously past him in the store the very next is very hot to me.
The sun went down and I just milled about waiting for the call. 10:00PM passed... 11:00PM passed... it was just after midnight when I was about to give up and start getting ready for bed that my phone lit up and I saw a message from him asking if I could come meet now. I dropped what I was doing and as I was heading out I saw my girlfriend's keys on the rack by the door as she had taken a rental car for the trip. I knew it was wrong, but I got very turned on thinking about slutting it up in the back of her car. I grabbed her keys and sped to his address.
He was clearly a bit anxious when he opened the door and got in but directed me to a nearby church parking lot with a nice hidden area behind the building and some trees. We hopped in the back and sat there awkwardly for a few seconds. He had asked me to only talk if he spoke to me but was now clearly letting his nerves get the best of him.
"How do you want me to start?" I asked, breaking the silence and keeping my eyes down and away from his masked face, trying to reassure him I wouldn't see his face.
"I've never done this with a guy before... how should we start?" He said in a low raspy voice.
"How about you pull your pants down and I'll show you."
He nodded his head quickly and lifted his butt up to slide his sweats and boxers down his thighs. He may have been nervous but he was visibly excited as his hardening cock flopped out before my eyes. It was dark but I could see well enough to tell this was a legit big cock with a nice downward curve in it. My first thought was how good it would feel getting fucked by him but decided not to overwhelm the poor guy.
I slid off the seat and settled in between his hairy legs and started kissing and licking the tip of his uncut cock. Before too long it was rock hard and twitching before my eyes. I licked my way slowly down the shaft towards his balls. I love sucking a man's balls so was hoping he would let me and lucky me I licked my way down and around his sack with no resistance. After a couple swirls of my tongue around each of his nuts, I felt his hand slide along the top of my head and grab a handful of hair.
"Suck those balls like you mean it!" He exclaimed as he roughly shoved my face into his crotch.
I happily sped up my tongue and sucked each ball into my mouth to give them a thorough washing. This was the first sign of feedback I had gotten and him showing some dominance turned me on even more. Once his balls were soaked with my spit he yanked me back up to face the dripping head of his cock.
"Suck my dick now, show me how deep you can take it." He demanded.
His sudden dominant attitude was doing wonders for him and I let him shove my head down deep onto his engorged cock. It was a little dry so I had to move his hand from my head so I could lick his shaft all over and get it wet. I placed his hand back on my head and he immediately shoved his cock balls deep down my throat. I could handle the length but was caught a little bit off guard that this shy 18 year old was now forcing his big hard dick into my face. He held my head there while I gagged and drooled over him then pulled me back up to his tip where he let me swirl my tongue around briefly before plunging me down on his hardness again. He found a good pace to facefuck me and just fed me his cock for a good few minutes.