Personal Ad Mayhem

Hello everyone, this is my first attempt at writing a story for literotica so please be kind! Any and all feedback is encouraged!

The story is purely fictional and a work of my own.

Tw: This will be a transman/cis-man pairing story so there will be piv sex, and the trans man’s genitals are discussed using female gendered words. If this isn’t your thing feel free to click away!

“Fuck!” I thought to myself as the sudden realization hit that my computer crashed, deleting everything I spent all semester working on.

Maybe I should start by saying “Hello! My name is Blake. I’m a 19 year old college student and I’m a transman.” This isn’t how I introduce myself in person, but I’m going to use this space as a journal so why not be 100% transparent.

I’ve known I was different since I was a kid and I realized I was trans by middle school. My parents were shocked at first but things kinda settled down as time passed. At 5’4” and 120lbs soaking wet I did my best to blend into the crowd but I stuck out like a sore thumb.

Now in my second year of college I was more stressed than ever with classes, group projects, exams, term papers oh my! It felt like I was on a ferris wheel that won’t stop.

I checked the time and it was 9:38pm on a Friday night and there I was writing a term paper instead of partying. All the work I had put into this for nothing now that my computer was fried.

“Fuck! What am I going to do now?” I thought to myself. I made my way back to my dorm and spent some time scrolling my phone trying to think of a way to clear my mind.

“I know what I’ll do. I’ll check the local personal ads and see if I can get up to some fun”

I had found the site by accident after overhearing two guys talking about it in the library. They probably assumed that no one could hear them.

After doing some digging online I spent weeks reading through each ad. Reading about the nasty and freaky things men wanted to do to each or have done to themselves. A familiar blush washed over my cheeks just thinking about some of these things imagining it was being done to me.

I spent a lot of time lurking and never really had the nerve to post until now. I knew I needed to relieve some stress so I got to work drafting up and drafted an ad to get some attention.

“19yo college ftm looking to relieve some pent up stress. Be local and able to pick me up. Please no flakes” There. Short and sweet. Something vague to keep guys guessing. At the last minute I decided to include the sluttiest picture I could find. In my opinion I looked hot, I was wearing a ratty old shirt I cut just short enough to show skin and barely cover my full chest, the tiniest pair of briefs I had that were visible underneath a pair of shorts two sizes too small.

“Post. Now it's time to wait.” I told myself. A familiar heat began stirring in my groin as I waited and imagined all sorts of fun to be had.

I pictured meeting a stranger and our attraction to one another instantaneous. Two bodies connecting and our mouths telling us all we needed to know about each other. Starting with gentle kisses while our hands explored each other's bodies slowly the kiss grew deeper.

Our mouths grew open and our tongues tangled, seemingly fighting for dominance. His hands would move slowly from top of my shoulders and arms to my back pressing me closer to him as I felt his hardness press up against my crotch. Feeling the heat growing between us. I move my hands up and down his back feeling his hard back begging him to get closer to me.

We would take our shirts off first and slowly he would move his hands down my back and his fingertips made my skin feel like it was on fire. Electricity ran down my spine as I felt him move further and further down. His hands cupped my ass while I pressed my nails in his skin hoping to mark him.

In reality I had moved my hand down to my crotch pressing firmly over my crotch feeling the heat growing all the while. I moved my hand in circles over my crotch while a familiar wetness started to seep through my shorts. Before I had the chance to take things further I heard a ping from my phone alerting me to responses to my ad.

Looking at my inbox there were about a dozen or so replies so far but they weren’t very promising. Most were one word responses or faceless pictures taken at bad angles.

I nearly decided to throw in the towel before I got one last response from someone who said they were 40 years old, a firefighter, 5’9” with a muscular build, a beard, recently tested, and mobile. Cha ching! He sounded hot and his email also said he wanted to fool around and cum inside me. This last bit intrigued me as I felt a heat start stirring in my pussy. I was always safe and tested once a year since I rarely hookup so the thought of a stranger cumming inside excited me. I’ve been on T for about a year and had an IUD implant because of my last bf so I let the horny feelings take over.

I replied that I was interested in his offer and free now to meet if he could pick me up. I decided to take a picture to seal the deal so I made my way to my bed, slid my shirt and shorts off, the wetness of my pussy visible from the light briefs I was wearing. Putting a hand over my chest to cover my hardening nipples while making sure you could see the round perky mounds I took a selfie. I took a few and attached my favorite.

He replied almost as fast as I had. “You look so fucking sexy. Which dorm are you in? Let me scoop you up and we can have some fun in my car. I know somewhere no one will see us.” I had never done something like this and I started to feel the blood rush to my head in excitement. He included a few pictures of himself and to my surprise he was one of the firefighters that gave safety talks to incoming freshmen at the start of each school year. He was broad shouldered and square jawed with a dark dusting of hair covering his chest, stomach, and legs. With emerald green eyes I knew I needed him inside of me, bad.

I replied back with my dorm name and he told me he’d be there in 20 after a quick shower. I bolted up out of bed and into the shower. Working quickly I dressed in close to nothing knowing I wouldn’t be wearing it long. A pair of shorts that barely fit, an old sports bra, and a baggie hoodie to hide part of me at least.

Making my way downstairs I was grateful no one was around to see me in my desperately horny state. I felt the cool night breeze on my upper thighs and felt butterflies in my stomach as I had never done this before and here I was offering myself up to a stranger twice my age.

I told him I’d be in the parking lot near the basement exit and what I would be wearing. After a few minutes a car pulled up, a man in the driver seat rolled down the window and told me to get in.

“God you’re even better in person.” He said. A blush creeped over my cheeks. I hope he couldn’t see.

“Thank you.” I replied shyly. I’ve only been with two guys before this and had been in long term relationships with each so I had no idea what to say to a hook up. He put his hand on my thigh while he drove us to a park he knew about the tension growing thicker with each passing minute.

“Don’t be so nervous. I won’t bite.. Unless you ask.” He joked in an attempt to ease my nerves. I giggled at his comment, willing myself to relax.

After what felt like a lifetime we made it to the park, which I later found out was right by the fire station, and thankfully it was empty. He parked, stopped the car and motioned for me to sit in his lap. He had moved his seat as far as it could go and I fit perfectly.

His hands moving over my sweater undoing the zipper the moment he touched my skin it felt like I was on fire.

“God you’re so fucking sexy.” He said. I was grateful it was dark out otherwise he’d see how this comment made me blush.

I put my hands on his chest and felt his hard body up and down. “Thanks. You’re pretty fucking sexy yourself” I replied. A heat began to stir in my groin as we explored each other's bodies.

He put his hands on the back of my head and pulled me in for a kiss. Our lips met gently at first like the way you shake someone’s hands when you first meet. His mustache tickled my upper lip and I giggled. His kisses were sweet at first while his hands explored my body starting at my back and making his way towards my ass. I moved my body and started grinding my shorts covered pussy over his thigh. Feeling a wetness seep through my shorts.

I felt his tongue graze over my lips and I opened my mouth for him inviting him in for a taste. Our tongues met and danced for what seemed like ages while he made an attempt at removing my sports bra.

“Is this okay?” He asked. My chest used to be a sore subject, something I hid, it was something I started to enjoy and show off as of late.

“God yes!” I pleaded with him and he made quick work of lifting the bra over my tits. I was a little bigger than average in that area so they flopped out in an almost comical fashion, his hands making their way to my tits just as fast as they flopped out.

Seeing the lust in his eyes as he fondled my tits so grew wetter with each squeeze. I continued grinding on his thigh covering it in my nectar. My whimpers and soft moans grew louder as he continued to play.

“Can I?” he asked as he rolled my nipple between his thumb and index finger. I didn’t know what he meant but I nodded. His mouth moved to the nipple he had been playing with and he began to suck on it. Moving his tongue in circles he swirled around my nipple and I was grateful no one was around to hear how loudly I moaned.

I was so caught up in what his mouth was doing I didn’t notice his hand had made its way to the front of my shorts. Once inside his finger grazed my engorged tdick and I nearly lost it.

“You’re pretty sensitive, huh?” he asked in a teasing manner. He went back to working on my pussy moving a finger over my wet slit. I groaned into his ear.

“Need more.” I said as I moved my own hand down to his shorts. Feeling a hard lump I moved to the top of the shorts and pulled his cock out. It was about 7.5” and as thick as my wrist. The head was fat and glistening with his pre-cum.

He seemed to know what I meant. He teased me with his index finger at my opening and I groaned into his ear again at the pressure. His mouth moving between my tits he started pressing a finger into my pussy. He curved his finger looking for my g-spot while moving his hand in and out. I felt electricity run up my spine once he did.

“You’re such a good little slut.” He told me and I had to agree. There I was a whimpering mess for a man twice my age whose name I didn't even remember. He worked his finger in a steady rhythm, he grew confident and used his thumb to rub my tdick. I was jerking his cock hastily too overcome with the pleasure to be able to focus.

He worked a second finger inside of me and he started to pick up the pace. My moans grew louder and louder the more he worked me over. The squelching of my pussy should never really did anything for me but right here in this moment I wanted his cock to be making that noise. My wetness covering his hand and thigh I knew needed more.

“Can I?” I asked a callback to his own question. “Fuck yes you can!” he replied practically ripping my shorts off and pulling his sweats down before I could process his response.

He teased my tdick with the fat head of his cock and I was fighting back the urge to beg. I groaned with pleasure while we had our sword fight and he ran his cock up and down my slit. He took his hand off his cock and moved them to my hips. He moved my body so that my pussy was sliding over his cock covering it in my wetness.

“Fuck just fuck me” I yelled growing impatient with all the teasing.

“Now, now patience is a virtue, boy.” he replied, taking pleasure in how I was coming undone. He continued grinding our cocks together and I continued to cover his cock in my wetness.

I went for his cock and he grabbed my hand. “Impatient boy. What are the magic words?” he asked. I finally figured he wanted me to beg so I replied “Please fuck me!”

“Please fuck me, what?” he asked while teasing my opening his cock. “PLEASE FUCK ME DADDY” I replied.

“That’s a good boy” he said as he moved his wet cock to my opening, applying enough pressure to ease his head into me. Before he could get too far I put my hands on his chest so I could get used to his cock. It was just his head and I could my pussy start to stretch and burn with how full his cock made me.

He moved one hand back to my tits and started playing with my tits again. Squeezing them hard and rolling my nipple in his fingers while he eased more of his cock into me.

“Fuuuuuck. God you’re so fucking tight. I don’t know how long I’m going to last.” he said and I just now realized he had gone in bare. I was too horny to care and by then he was mostly all the way in.

“Uh uh uuuuuh” I groaned as he bottomed out and I could his pubes on my tdick. The sensation nearly caused me to see stars.

He held me there for a minute while I got used to the girth of his cock. The burn fading while my pussy was being stretched further than it had been in months.

“Fuck, you’re so big” I said and this made him chuckle. I slowly eased off of his cock and then back down. I started riding his cock while he held onto me at the hip and tit.

“God, you're such a good little slut. “Taking a stranger's cock.” “Dumb little slut I bet you do this all the time.” “Your pussy is pretty friendly I bet.” he said to me and I was too horny to respond.

He moved both of his large hands to my hips and they highlighted just how much bigger this man was. He held me in place hovering over him while he started to pound.

The sounds of his thrusts were all I could hear.

Thwack

Thwack

Thwack

He was relentless as he pounded me. I thought he split me in half.

“Look at your pretty little pussy all stretched out over my thick dad cock.” he said as he pounded harder into me. Like my moans were an invitation to go deeper.

“Uh uh uuuuuh oh god.” “Fuck yes please” “Harder. Harder. Harder.” I yelled at him. How I managed to get words out was beyond me. All of the blood had rushed from my head to my tdick and all I could focus on was cock that was splitting me in half.

Thwack

Thwack

Thwack

He slammed his cock into me and I ground my tdick into his pelvis. He stopped for a second and moved his thumb over my tdick. “Uuuh fuuuuck.” I managed to moan out. “Look at you, a whimpering little mess.” he said.

He slid his cock out of me with a loud plopping noise opened the door and carried me out to the back seat. The car was low enough that if he laid me on the seat my pussy was level with his cock.

Exposed to the open air I felt a cool breeze on my wet pussy and I begged to be stuffed again. “Please fill me, I need your cock inside of me” I yelled. This made him laugh.

It dawned on me that I hadn’t really gotten a look at his face so I took a better look at him in the cool moonlight and thought “damn, he’s so fucking hot. the definition of a dad.” He was tall, dark hair on his head and a full beard, broad shouldered with hard pecs and a soft dad pouch covered in a light dusting of fur.

He moved forward to play with my still wet pussy and I got a good better at his cock. It stood hard as a rock with a slight curve at the end and a purple head leaking precum. There was a full bush above his cock that looked primal compared to my shaved pussy.

“God I need more of this” he said as he kneeled to be eye level with my pussy. Gone was the need to ask instead he dove head first into my pussy. He kissed it at first, rough and deliberate. His tongue began licking up and down my wet slit as his beard was slowly being covered in my wetness.

He used the flat of his tongue to lick my wet pussy and moved a hand up to one of my nipples to play with. This drove me crazy and I was squirming in the back seat of his car covering the leather upholstery in my wetness.

The way his tongue lapped at my pussy it was like he hadn’t eaten in days. Slowly he worked his way up to my tdick and started with gentle licks. “Fuuuck” I said as he took my tdick into his mouth and began giving me the best blowjob of my life.

“Please more, I need to be filled” I whined. My pussy was aching to be filled again. He obliged and worked a finger into me as he sucked on my tdick.

“Fuuuck please I need your cock” I begged.

He finally came up for air and made quick work of stuffing my pussy. He slid in and was pounding relentlessly in my pussy while his fingers worked my tdick.

“Fuck yes baby boy. You want this load?” He asked.

“Yes please fill me daddy.” I replied.

“Fuuuck it’s been so fucking hot to see you beg.” He told me.

“Say it. Beg for my load. I’m so fucking close” He told me as I felt the curve of his cock hitting all of the right spots as he slid in and out of me.

“Fuuuck daddy.” I said. I was incapable of forming words. I was so overcome with pleasure. He was pounding deeper and harder. I could feel his cock in my throat.

“I. Need. You. To. Say. It.” He said while continuing to pump harder and deeper.

“Fuuuck fuck daddy please give me your load.” I cried out.

“OOH FUCK. Here it comes. I hope you're ready” He said while pounding me in an animalistic way. I started to feel his cock swell as my toes curled.

“Fuuuck I’m close fucking” I moaned as he kept pounding into me and feeling his hand work my tdick.

“Yeah, that’s it baby. Cum on my cock. Fuck I hope you’re ready” he said. He bent in half and laid on top of me taking my nipples in mouth again.

“FUUUUCK FUCK FUUUUCK” he yelled as he flooded my pussy with a hot load. He continued pumping his cock in and out as he shot off spurt after spurt. His cock was making a loud squelching noise as his cum mixed with my wetness and I was sure my pussy was wrecked.

With one final push he thrust deep into my pussy shooting off the last of his cum inside of me. “Oh fuck oh fuck oh fuck oh fuuuuck oooooh” I moaned as I felt my own orgasm take over.

I shut my eyes overwhelmed by what I was feeling and I swear I could see stars. I felt like I had blacked out in orgasm.

Suddenly I felt his mouth on mine and his tongue began exploring my mouth. We kissed for a moment before we both shut down. He laid on top of me breath ragged and his voice horse.

“Fuck that was so hot” he said breathlessly.

“Thanks” I replied. I still couldn’t form thoughts. We stayed like that for a few more moments before he pulled his cock with a large plop. He tossed me my clothes and told me he’d drive me home.

“Gimme your number. I need to fuck your pussy again” he said while handing me his phone. Happily I obliged and sent myself a quick text to save his number. I knew I needed him again soon.

He drove me back to the dorms casually, his hand never leaving my thighs. I can’t recall what he talked about, still unable to form thoughts. I hadn’t noticed we were at my dorm. He parked his car and we kissed goodnight with a promise to meet again soon.

I shot back into the dorm grateful it was late and no one saw me. Once in bed I looked at my phone and shot off a quick picture of my still wrecked and cum filled pussy to him. He responded with a picture of his hard cock poking out from his sweats and all he said was “how do you feel about group play?”