Why I’ll Never Go Sharking Again

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Fun times lead to trouble with a shemale.
2.5k words
4.42
69.9k
79

Part 1 of the 3 part series

Updated 10/23/2022
Created 06/09/2012
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tsfan84
tsfan84
94 Followers

Have you ever heard of "Sharking?" Until recently, I never had either, not until my roommate Jason told me about it. Jason and I go to the University of Maryland together, and share an off campus apartment about 15 minutes off campus.

A typical Saturday for us is sitting around drinking, maybe having a few friends over, but this day was unusually slow, unusually slow until Jason turned to me, drunk as hell and said, "Marcus, let's go sharking."

"What the fuck is sharking?" I said, confused.

Jason replied, "It's when you run down on girls and either pull either their pants or tops down."

I burst out laughing at the thought off running around, exposing girls, but when I saw Jason was serious, I simply told him "You've been drinking too much, or you want to get kicked out of school."

Jason finished his beer, got up to get another one, and turned to me saying "obviously we can't do it on campus, someone will recognize us and we'll get caught, but if we drive into the city, we can easily get a few girls before the cops catch us."

I figured this was just some crazy thing white guys did when they drank too much, but after a few drinks, the idea started to sound more and more fun. So since Jason obviously had given this some thought, I turned and asked him, "How do we plan on doing this?"

Jason thought for a moment, and then said, "We drive to DC. There, no one would recognize us and I can't imagine some girl chasing us down with her pants around her ankles."

Just thinking of that image made me burst into laughter out loud. So I turned to Jason and asked, "Have you ever done this before?"

Jason replied, "No, but I've seen videos of it on the internet, one of us should sit in the car, in case we need to make a quick run. The other wears a hoodie, and some shades and just pulls and runs."

I cut Jason off to ask, "How far would I run?"

He told me, "Maybe a block or two, turn a corner, and then I pick you up, after that we go a few miles further away, then we can do it again, that way if anyone calls the police, we're long gone."

It sounded like a good plan, both me and Jason were in pretty good shape so running wasn't an issue, we weren't on the track team or anything like that, but we are both around 5'10 160 and could likely outrun a girl with her pants around her ankles.....there goes that imagine again. So I asked Jason again was he serious, and when he said "Yea," we headed out.

We hoped in the car about 15 minutes later. Both of us were wearing hoodies and shades, like we were about to rob a liquor store, and we also decided to bring a camcorder so we can watch it later. So, within minutes, we're in the city. It was also a great day for a mid-May afternoon, so there were girls ever where. Some wearing skirts, some wearing shorts, some wearing summer dresses, just looking out the window was getting me hard.

I was in a daze, trying to undress every girl I saw when Jason said, "Let's start here, I'll go first. Record everything, then when I run, meet me two blocks down, then make a right, got it?"

"Got it" I replied.

When Jason got out the car, I moved into the driver's seat. Jason posted up about two blocks ahead so he could get someone as they walked towards the camera. He was scanning the streets for his first victim, when he spotted a blond girl, with a huge rack, wearing a tube top. Jason, being the typical white guy, loved blonds, so I wasn't surprised that he started following her, but even I had to admit she was hot. She was just walking down the street, completely oblivious to what was about to occur, when Jason locked his sights onto her. I began recording as she was walking towards me, and as she got closer, I could see Jason speeding up. Right when she was about 10 feet from the car, Jason made his move and pulled her top down. Boing! Everyone saw her tits bounce a few times before she very poorly attempted to cover them with one hand while pulling her top back up with the other. As I burst into laughter, Jason went running down the block to the assigned place while she just stared in anger.

"Did you get it?" Jason asked as I picked him up.

"Hell yeah I got it. But let's move before she stumbles upon us here laughing at her."

As we drove a few blocks, Jason said "the next one, I'm pulling their pants down."

I couldn't do anything but laugh and say, "Fine, but after that it's my turn."

So we finally find a suitable place, one with a few people walking around, that's when Jason says "Stop, we'll find someone here."

I pulled over and Jason said to me, "Same thing, when I run, pick me up two blocks and then to the right."

I nodded my head and said "cool."

Of course, within seconds, he picks another blond girl. She was cute, but had a small ass. Don't get me wrong, I'd hit it, but I wish he would pick a black girl so I can record that. Again, Jason is posted up about 2 blocks away as she heads in my direction. And once again, about 10 feet away from the car Jason reaches for her pants, pulls them down and runs. What was so funny, was in the shock of it all, she turns around to see who did it, not realizing that here pink thong and ass are being recorded by me.

Again I pick up Jason, and he's dying of laughter. "Did you see her face!? No wait, did you see her ass!?" Jason asked.

I simply replied "My turn" and hop out the car while he gets in the driver seat and I get in the passenger's side.

We again drive a few blocks when Jason says, "After this we should call it a day."

I say "Cool, we can come out another time and add to our video montage, but I'm definitely doing at least one before we head back."

So we ride around till we find another spot with a few people. Not too many because you never know who may want to be a hero, but enough that some will walk by. Before I get out, I tell him "I'm definitely getting a black girl."

Jason shook his head and said, "You probably shouldn't."

Puzzled, I asked him "Why?"

He answered "They're more likely to chase. I know because you're black you think you can out run anyone chasing you, but it's not worth the risk."

I said "Fine" but knew I would anyway. I gave him the same directions he gave me "two blocks ahead then on the right" and hoped out and walked off.

As I waited, and scanned, I soon found my prey. Jogging in my direction was this girl, caramel colored skin, like I wanted, cute face, thick ass, nice sized breast. She was taller than me, maybe 6'1 even, and some-what more muscular. I should have let her go past, obviously her jogging was a sign that she was in good shape, but she caught my eye and I figured I could out run her. She was listening to her iPhone, which was perfect, that way she couldn't hear me approach. I wanted to make sure Jason got this on camera, so I had to speed up to keep pace, and once again about ten feet away from I went for it. I reached for her some-what baggy shorts, grabbed as much as I could hoping to completely expose her, and pulled her pants and what-ever was underneath completely down in one pull. As I looked to marvel at her bare ass, I realized that she had a big brown cock hanging down between her legs, as I stood there shocked that this girl had a cock, a cock bigger than mine no less, she pulled her pants up, shot one evil look towards Jason in the car and began chasing me.

What the fuck was I thinking standing there giving her a chance to close the distance? What the fuck was she doing with a cock? And where the fuck am I running to? In my confusion and fear, I just picked a direction and ran, completely forgetting where I was supposed to meet Jason in case of trouble. What was worse was she was gaining on me. As I ran, and ran it became more apparent that she was going to catch me. I wondered was she going to hold me down and call the police? Or was she just going to try to kick my ass? I didn't know, but what I did know, was she was really close.

To get away from her, I was just randomly turning down street and alleys, I decide to turn down this alley to the left, and as I look back to see I created a good sized distance between me and her, I run smack dab into a ten foot high chain fence. I turn around to see if she saw me, I don't see her when I begin to climb up. All off a sudden, as I climb I feel two hands on my pants before they get ripped down. The force of her pull, not to mention trying to climb up a fence with your pants around your ankles made me fall flat on my back.

As I look up, SLAP! WHACK! I get hit in the face twice, when all I hear is "You picked the wrong one to fuck with!"

While covering my face, and going into the fetal position, expecting to get hit a few more times, I managed to plead "I'm sorry, please don't call the police."

At that moment she laughed and said "I'm not!"

I look up thinking what the fuck when I see her stroking her now 10 inch cock! I scream "No way, get the fuck off me!"

Suddenly she hits me again upside my head. I get up and attempt to hit her back, after all, she is a dude, but she quickly grabs my arm, spins me towards the fence and twist my arm behind my back. The pressure on my arm causes me to again scream in pain.

I'm trying my best to twist free, kick her or anything to get her off me, when I hear her spit, presumably on her dick and then suddenly, she rams it inside me.

"AWWWWWW!" I scream.

"Just be glad I spit on it" she said. "A tight virgin ass like this would be completely ripped apart if I didn't." It was the most painful thing I have ever had to endure, and I had no way of stopping her. She was bigger and stronger, and every time I tried to move, she twisted my arm further.

As my face was pushed further into the fence, and her balls slapped against my bare ass, I pleaded, no begged her to stop. All she said was, "Got....to.....teach.....perverts.....like.....you....to......not.....fuck....with....girls.....like....me."

With tears rolling down my face I tried telling her, "I had no idea, I was just having fun...I thought you were normal."

When I said that, I felt her withdraw from inside me. And for a moment, Ithought she would have mercy on me, but then WHAM! Balls deep inside me again.

I screamed in pain as she covered my mouth, and whispered in my ear, "You need to be nicer to someone with a dick inside your ass, especially a tight ass like yours. Now listen, this is going to happen whether you like it or not, you embarrassed me, then insulted me so I'm going to teach you a lesson. If you continue to fight it, I'll literally rip you apart, but if you relax, you may actually like it."

"Fuck no bitch" I said, I then felt her withdraw again and quickly blurted "Sorry please don-" WHAM!

She again whispered in my ear, "Last chance, I can be an evil bitch, or I can be nice"

I replied "Nice." She said "Fine, but if you want me to be gentle, then ask me to be nice and gentle with your sissy ass hole."

In no mood to argue, and having already seen what happens when I defy her, I simply said "please be gentle with my ass hole"

She slapped me on the ass one time and told me, "I said sissy ass hole."

Filled with embarrassment, I complied and said "please be gentle with my sissy ass hole."

My attacker, licked the tears off my face and said "Anything baby."

Realizing that this was going to happen no matter what, I began to relax and "allowed" her to go in and out of my now de-virginized ass hoping it would ease the pain. She sensed this and finally let go off my arm, but then placed both hands on my hips.

She pounded me hard. Having her complete way with my ass, but then she slowed up a bit, as if making love.

What began to bother me, more than getting fucked in the ass, was my dick was getting hard. She didn't notice right away, but when she heard light moans coming from me, she started to tease me a bit.

Locking my ear, she whispered to me, "I can always spot a bottom boy....and look at how hard you are. Too bad this is going to end soon, but I wonder"

As she said that, she began stroking my cock. As much as this hurt at first, I must admit having my hole filled while having my cock stroked was the best feeling in the world.

Wanting to hold onto what-ever masculinity I still had, I said "D...on't do that....I'm....not gay."

She laughed and said "Your dick says other-wise, I even bet you cum before I do." And she was right, after a few more strokes, I exploded onto the ground outside, while she laughed and said "Fucking bitch." Soon after I began to feel her cock pulsing in my ass and then she released her load inside me.

When she finished she let me go, I fell on the ground, cum leaking out of me, and she pulled her pants up over her cock. She reached in my pants, which were still around my ankles and pulled out my wallet. She took my ID and said "I'll visit you later and don't worry, your friend has it cumming too, but if you warn him, next time I won't be so nice." As she said that, she put her ear phones back on, and left me there, sore ass and all.

tsfan84
tsfan84
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AnonymousAnonymousabout 2 years ago

Wow I fucking love this love to swap places with that guy

wimpywelshwillywimpywelshwillyover 4 years ago

Mmmm, he got what he deserved.

AnonymousAnonymousover 5 years ago
Lucky guy

I date a trans girl who would here hate these stories, but I secretly love every chapter.

AnonymousAnonymousover 6 years ago
Liked it

Getting taught a good lesson in public by a tranny with a huge cock, what a turn on.

HurbsterHurbsterover 11 years ago

The dominance stuff is why the vampire story is waaaay better than this one.

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