I'm Sam, 21 year old history student. Since I had a very small room near the university, I used to stay a bit late on campus each day, especially on fridays since there were far less students all around (all gone partying or drinking in the bars nearby). I loved to study and chill around the cafeteria while it was almost empty. I also liked to lurk on the hot guys that were passing by, mainly the construction workers or the uniersity maintenance staff (love dad bods). Most of them were wearing sleeveless or tanktops while working in summer, which never ceased to arouse me.
In recent weeks, I also began to have a fetish for crossdressing and I started to wear thongs and panties in class, without anyone knowing. I like the way it made my soft and round ass look even girlier, but I was keeping my fantasies for myself. I thought about dressing as a woman at the campus. I spent hours chosing the right outfits and looking at my plump ass in the mirror. I shaved everything, tried to sound even more girly (alredy had a pretty high-pitched voice) and even tried to pose a bit in front of the mirror to work on my best features. I also bought numerous dildos and started an endless journey of stretching and taking bigger and bigger things up my butt. I loved the feeling of a big object invading my ass.
I trained more and more, until one day, I actually brought woman clothes and a wig in my bag. After my last course of the day, I changed myself in the toilets after 6pm, and dressed as I girl for the very first time. After almost an hour trying some makeup, I wa satisfied with my look. Seemed girly enough, and most of all, seemed sexy enough to attract some of the few men around. There were very few people still hanging around but I spotted some constrution workers and began to walk around, trying to catch their attention. It didn't really work at first, but around 7:30, I saw a security guard walking past me.
I tell you this dude was something of a Gladiator movie. Huge guy, way past 6 feet, grumpy look, 38 years old or so, broad shoulders and visible bulge in his kaki workpants, beautifull face with a red cap. My eyes soon met a beautifull set of pecs just at my height. They were glistening under sun, compressed by a sleeveless white shirt. I could smell that he had a hardworking day.
“Miss, campus is closing early today” he says, his voice low and husky. "Might want to get near the exit soon."
At first I was surprised he actually called me miss, but it pleased me so much I tried to take the most girly voice I could.
"Oh... sorry, I didn't know. Thanks for the info. I'll be going then."
I turned and felt his powerfull gaze on my butt as I walked towards the exit . I had a red skirt that emphasized my thin legs.
“Wait... I'll show you a better way. If you want it."
I faced him, still not sure about how to behave around such an intimidating man.
"Thanks." I replied shyly. "But I don't want to disturb your from..."
"What's your name cutie ?" He asked me, cutting me off.
"Sam..."
"Nice to meet you Sam, I'm Tom." he showed me his badge, very proud. I spotted a shiny wedding ring oon his hand.
"Don't think I saw you around Sam. You're new here ?"
"Eh... not exactly, well..."
"I could show you some places around before I take my shift if you like." As he was saying that, I saw a visible twitch in his kaki pants. " Should not be too long."
His dick twitched again, growing and growing. It started to move down his left leg like a huge snake. How fat was his cock ?
I must have lost track of time looking at his cock because he smirked :
"You want it ?"
I knew exactly what he was proposing me right now and began to fear that my crossdressing fantasy could turn against me.
"Um... wait, I don't want to get into trouble."
"Relax sweetie, I'll take you to some safe spot." He got dangerously close, "Only you and me. Up for it ?"
He got closer again and I felt his powerfull cologne invade my nostrills. My cheeks turned red and I began sweating. I felt so exposed.
He lost patience and grabbed my wirst.
"Come on, follow me Sam."
We took the elevator of an administrative building which required a badge to enter. I began to fear for my security (the irony) but Tom had so much strengh and charism I could not escape his strong gripp, and amazing body.
Once we reached the 5th floor, he led me to a big bathroom stall, closed behind us and sighed.
"Nice. We don't have much time Sam."
He began to unbuckle his working pants while talking, revealing a black plaid boxers, typicall straight underwear - not the most sexy around.
"This is supposed to be my coffee time before the shift. The boys are gonna ask where the fuck I am anytime soon. Get on your knees."
I still hesitated to undress, too scared he might notice I'm not a real woman. He could get violent. What if he was hostile at queer people ?
"Wait Tom... I'm... I'm not a real..."
"Sam you came here because you wanted to fool around, ritght ?" I saw in his eyes a glint.
His smile made me think he might have guessed that I was not a girl but a slutty boy crossdressing. He didn't seem to care at least.
I nodded.
"Look, I need to nut bad and my wife can’t take me anymore. Can you at least help me with this ?” He pointed at the monster that was tenting in his plaid boxers.
He seemed almost sad when he mentionned his wife.
"Just suck it for a while, ok Sam ?"
His dickhead was now pocking under the fabric, glistening with precum. I began to think about the possibility of servicing him. If I was only sucking, he might not find out about my identity, right ?
"Sucking... Yeah... I could do that."
I kneeled down and started to touch his monster of a cock. It felt thick, very thick and hard as a rock. I could not wrap my hand around it. Eager to see it, I began to lower his boxers but he stopped me.
"We should hurry sweetie." His big hand went into the fly of his boxers and he fetched his dick, making it spring through the fabric.
His massive glans went straight at my face. It was around 8" long and very very thick. I had never seen such an impressive cock in all my slut life. He soon grabbed his heavy balls and made them go through the fly too. They were big and smelled very strong, a mix between bodywhash, sweat and musk.
"Suck on it Sam." He directed his tip towards my mouth and began pressing.
I opened my mouth as wide as I possibly could, and took his helmet inside. A strong flavour invaded my pallet and he began to thrust into my mouth repeatedly. I was struggling with only his head, it was stretching my mouth so much I had to breath fully with my nose. I tried my best to take him further, but his python of a cock was just not made for a human mouth.
He facefucked me for a while with only a third of his cock and I was kept gagging and spitting his salty precum all over his dick. Soon, he stopped thrusting and sighed.
"Sorry, but I'm not going to cum like that. I could try your pussy instead, okay?" The way he said it was more like a order than a question.
I was surprised by his directness, but I couldn't deny the thrill that runned through my body. I was already addicted to his beautiful and huge straight cock. I nodded and Tom grabbed my hand, leading me to the sink. He lifted me against it I felt cold on my asschecks. He pressed his body against mine, his hard and shiny dick on my thigh.
Tom pulled my thong to the side, exposing my ass. He grabbed my cheeks, squeezing them tightly. “You have such a nice ass, Sam” he growled, his fingers tracing the curve of my cheeks.
He lifted me up and walked at the center of the room, my legs fully wrapping around his waist.
“Help me find your pussy Sam.”
I took his massive helmet and led it to the entrance of my ass. Soon, I felt it pressing hard against my hole. It was painfull, and Tom was not a very patient man, but I had made such a mess over his whole dick that soon, I felt his huge glans spread my sphincter and a burn rushed through me quickly.
"It's too much Tom !" I moaned in agony. "You're so big."
"Relax Sam, you're doing great !" Tom waited a bit for me to accomodate with his engorged dickhead.
"I can't."
"You can girl. I know you can."
He slowly pressed my ass on his cock, and got a little further this time. It felt like he was shoving an arm into me, and no matter how hard I tried, the pain was too intense. I cried out, the feeling of his dick inside me was so overwhelming I began to cum in my thong.
"Shhh, easy girl. That was the worse."
Tom started to fuck me with only his dickhead and a few inches, making me bounce on him casually. He began to get lost into his fucking and started to grunt like a bear in heat, his thrusts becoming harder and faster. I could feel his dick hitting my prostate with each thrust, and invading my insides further and further. Soon, Tom's glans began to reach the deepest parts of my body and my eyes got wide open from the strange felling. It was lodged so far I swear I could feel him pocking my painfull belly. I was discovering new parts of my insides that no one had explored yet and the whole thing was like an epiphany. I was made to take his monster cock up my stomach.
“Finally, someone that can take this cock!” Tom growled, his hands moving me faster.
I couln't contain my girly moans each time his dick would impale me. I loved the way Tom was treating me like a fleshlight, using my body for his own pleasure.
"You're taking"
Thrust.
"A big burden"
Thrust.
"off my wife"
Thrust.
"You know that Sam?"
I had a litteral monster cock cruching my organs and invading the deepest parts of my intimacy, meanwhile my small dick was throbbing pathetically in my thong, precum leaking from the tip. Tom couldn't see this as he was pressed hard against me, hands still gripping my butt like the claws of a tiger attached to it's prey.
After three minutes of powerfull thrusts in my cunt, his moves started to become erratic. I felt his dick swelling inside me, getting even bigger, making me moan in both pain and pleasure.
"Gonna knock you up Sam, ready?"
I feared for my body. If I was already struggling to understand how my ass would still be able to work after such a treatment, what would happen iff the guy wanted to unload inside ? I hugged him tightly and prayed that I wouldn't be crippled for life by his excess.
"Fuuuck."
Thrust.
"Cumming."
Thrust.
"In your."
Thrust.
"Pussy."
Thrust.
With a final powerfull thrust, he impaled my poor destroyed cunt on his massive dick, making it finally fit all the way inside my stomach and grunted loudly.
"Fuuuuuuck""
His heavy balls bounced under my ass cheeks and I felt a powerful spasm pass through his cock along its entire length, until a hot mess invaded my insides. The married dude was clearly frustrated and needed to unload deep, as nature had inteded, making me scream in pleasure.
"Toooom !" I yelped, the feeling of his heavy and abundant sperm coating my anal canal made me cum on the spot, again .
Tom didn't even notice I guess since he kept me deeply impaled on his huge cock.
The first load of cream was so powerfull I thought the worse was behind me but after like two seconds, I felt another surge in his dick and more spunk got unloaded in my stomach.
"Fuuuuh." He grunted again.
His baby batter was hot and reassuring, directly pumped in my stomach, making my belly bulge even more. His big balls kept twitching and filling me up until my cunt was overflowing with his cum and that whitish jets escaped in repeated impulses from my painful pussy and fell on the floor.
Tom stayed in me for a while, panting and grunting.
"Needed that so bad."
I could still feel some smaller pulses from his cockhead deep within me.
"Damn,... I hope you’re on the pill because I don’t want more kids.” He laughed, his chest heaving.
His strong arms lifted my buttocks slowly and his long cock slowly, oh so slowly slipped out of my insides, until it fell heavily on Tom's massive balls.
Cold air invaded my painfull pussy. I clearly felt heavier than before with all the cum he had deposited in me, but there was also a good amount of cum underneath us. Still carrying me, Tom walked a bit and dropped me off on a dry spot, as if I was a crate.
"Don't worry... I... I'm on the pill." I couln't walk normally and had to rely on the sink. I could feel his burning seed in my upper body.
Tom got some tissue to wipe the cum and all my juices from his dick and pulled up his kakis back, a satisfied smile on his face. “Good,” his voice low. “Because I’m going to need to fuck you again soon." He replaced his cap on his head with a smirk. "Currently working there this summer before taking the wife to the south for a while. You know, beach and barbecue stuff.”
He helped me walking, pressing me against his massive frame and began talking about his family again, as if he hadn't just cheated on his wife a minute ago. He led me to a side exit of the building.
"Alright miss. I'm going to take my shift now. This stays between us, ok ?" He laughed, spanking my painfull ass. "Stay safe and let's meet up again next week, okay ?"
I couldn't help but smile. I knew I was going to enjoy being Tom's little slut for the rest of the summer.
