Crossdressing faggot meets a brutish construction worker

I’m David and from a pretty young age it was clear that I was definitely less than straight. Growing up I was the stereotypical gay kid, never letting what other at school would say about me. Because of my supportive parents and a little clique I had found, high school really wasn’t as bad as it could have been for a gay teen growing up in the early 2000s. In college I got sucked into the local drag scene immediately and was spat out even more of a fag. 

After graduating I moved to NYC and started to crossdress in public more and more. Because of my years of experience with the art form, if you passed me by on the street you would be none the wiser that I was a guy. Part of the enjoyment of it was that I had this little secret held above everyone’s heads and the whole lie was right in front of their eyes.

Most weekend days I was either with my friends or I was crossdressing, going to eat somewhere far away just so I could walk around for a while. On my way down to Chinatown I passed by a patch of construction. As I passed by I heard a whistle and “Hey beautiful, lookin sexy tonight.” I whipped my head around to see a burly man leaning on a shovel. I didn’t know if I should have been disgusted or flattered and in that moment of confusion just kept on walking.

Letting my eyes stick on him, I checked out the man who had catcalled me earlier. The next day, coming back from a night on the town with friends, I properly stared at him, watching his strong back and arms while he worked. For the next week I had a new routine and would crossdress everyday, completely infatuated with this total stranger.

At the end of the week I got dinner to go and sat myself on a stoop, eating my food and watching the construction workers. I looked up at him and his partially exposed and extremely hairy chest and belly, fantasizing about him. I fantasized about him dominating me, fucking me. I thought about how big his dick must be and how much I wanted to suck it. I thought about a lot of things and before I knew it I wasn’t even paying the real man any attention. 

As I smiled down at my sandwich I heard a “Hey beautiful, If you’re going to pay me so much attention, why don’t you just go ahead and ask me out?” I looked up in shock to see the man who catcalled me, letting silence fall after his question. His eyes drifted down and seemed to be taken aback. I followed his eyes and looked down to realize I had developed a hard on, which created an obvious bulge in my skirt. I looked up to see a smirk on the man’s face. “A fag, eh? Heh… I like that too.” “Uh, u-“ “Name’s Joel, if you want somethin good, meet me here tomorrow at eight.” “O-okay… David, by the way.” He said “ Well, David, I’ve got to get back to work, see ya later” with a wink.

When I got home I could barely contain myself. I practically tore my clothes off, fingering myself while thinking about that experience and what could lie ahead. I took my other hand and began to jack off. Fantasizing about Joel pushed me over the edge, cumming all over myself.

The next day I walked over to the construction sight to meet up with Joel. I looked ahead of me but didn’t see him anywhere. Suddenly I felt him grab my ass, saying “Im really glad you came” with a growl in his voice. I turned around to see him still in his dirty construction outfit. It was almost comical the contest between him and me, dressed fairly fancily. We walked over to the curb and called a taxi.

There was already another woman inside so me and Joel were forced to sit squished together. He put his arm around me, pulling me in closer to his side. Now so close to him, I could smell the intoxicating musky scent coming from him. I could smell the sweat from a day out in the sun and it made my cock stiffen inside of the cab. 

When we got to our destination, Joel opened up the door and let me out of the car. We walked into and up the stairs of his apartment building, up to his door. He unlocked the door and led me to the bedroom. He dimmed the lights and started to play music from a cd stereo machine. He quickly stripped off his clothing, leaving them in pile on the floor. He then helped me out of my dress, making sure to feel at my asshole. 

Now able to see him in full, Joel was a very burly man, covered in dark thick hair from head to toe. He sported an impressive gut which gave him a very solid look. I looked down to see a very impressive package. It didn’t seem he cared much for “manscaping”, with a big thick bush of pubes at the base of his cock and a set of hairy balls. His balls were seriously massive, bigger than anyone’s I had ever saw and hanged low. Above his low hangers was his flaccid, uncut cock, which was very thick. 

I knelt down, sucking on his big balls, and made my way to his dick. I slipped my tongue under his foreskin, sucking his tip. “Fuck, pick up the pace” he said, forcing my head to the base of his cock. Grabbing my head, he started fucking my mouth, without much attention to me. He didn’t face-fuck me for long, pushing my head of his dick, leaving saliva dripping from my mouth.

“Lets get to the good stuff” he said while pushing me onto the bed. He laid on top of me, kissing my face roughly and messily while he grinded his cock up against mine.

“Turn around, let me say that ass.” I obeyed, flipping over, exposing my ass to him. “Aw, how thoughtful” he said as he inspected the but plug stretching my hole. He took hold of it, sliding it out of me, leaving me gaping open. Grabbing a bottle of lube he got me ready.

He mounted my ass, pushing my head down and my ass up. “Show me that hole, bitch.”  He led his cock into my ass, pushing all the way in. The sudden shock of his cock fully in my ass made me gasp. He got right to it, fucking me mercilessly right away. His shaft pumped in and out of my, making me erupt with pleasure. His big, heavy balls slapped up against mine every time he would thrust, creating an audible noise. Up top I could feel his big, hairy belly on top of my ass as he went in and out of me. 

He tore my ass apart, rapidly fucking me as I moaned with every thrust. He continued to fuck me, even after I had covered the sheets beneath me with cum, but it didn’t seem like he was close. After at least 10 minutes  of pounding my ass he slowed down, placing a foot on my back, plunging his cock even deeper. After several minutes of him abusing my hole I felt his cock seize up, pumping cum into my ass, while he moaned loudly. He pulled his cock out of my ass, letting some of his seed leak out with it. 

He flipped me over, smothering my face with his armpit. A day’s worth of sweat gave him a very strong, musky odor. At first objecting, I quickly gave into it, taking in long breaths and licking at his thick, dark hair. After a while, he let me out of his grasp saying “Don’t think I didn’t see you in the cab, you little slut, I know you love this.” I had no other option but to agree with him. 

Afterword, in the shower, I helped rub out the sweat and grime of his day from his thick body hair, which covered him from head to toe. During the shower Joel nibbled and kissed at my neck and face while he massages my asshole, letting the rest of his seed slip out.

After drying off, he gave me a bag for my clothes and a pair of his own for the ride home. His pants and short barely fit me, hanging loosely over my body. I got home and immediately fell asleep, exhausted. In the morning I looked over to his belonging, he would surely need those back right? I guess I'll just have to return them soon.