A Weekend in Jail

This started out as a really good idea of mine, but I re-wrote it a few times and it sort of lost its spark to me. I like the end result but I am aware, things start to seem a little rushed towards the end. Regardless, I hope you all enjoy it.

*****

The gate to my cell slammed shut behind me, as the guard started walking back down the corridor and leaving me to myself; or so I thought.

It had been a long night and a crazy one at that, and now here I was sitting in a fucking jail cell. I was going to be here all weekend too, as they had informed me they could not put me in front of a judge until Monday morning; just my luck. I looked down at my hand, still black and blue from the fist fight that I had been in earlier that night.

At least the bleeding had stopped, but it was still pretty sore.

I had been out at a bar that night, drinking and ended up pretty drunk; nothing out of the ordinary for me to be honest. Some asshole decided to try and flirt with my girlfriend though, and I wasn't having that. So naturally, a fight broke out and when the police showed up, I wound up putting up a pretty big struggle with them, as well. That definitely did not help my situation any.

"What are you in for, kid?"

I jumped, startled by the voice from behind me. I had yet to turn away from the gate and hadn't noticed anyone else was in there, with me. I turned around and found myself looking at a woman in her late thirties, sitting on the bench against the back wall of the cell.

She had dirty blonde hair, pulled into a pony tail and dressed in a low-cut tank top and pink skirt with high heels.

"What's it to you?" I asked, a bit hostile at first.

"Oh, no need to be rude; just curious, that's all."

I hesitated for a moment, leaning my back against the gate and shoving my hands into my empty pockets.

"I got in a fight at some bar," I said, slurring my words a little; I was still feeling rather drunk, to be honest.

"Drinking and fighting, huh? My, what a naughty boy."

I chuckled, turning away from her again for a few moments then glancing back over my shoulder at her. "What about you?" I asked, curiously.

"What are you here for?"

"I'm a hooker," she admitted, pretty straight forward.

I had sort of figured that, judging by the way she was dressed and I assumed she must have gotten caught with a client.

"Cops walked up on me and some guy in his car. They caught us right in the middle of the dude, sucking my cock."

I blinked, surprised at that last part and wondered for a moment if maybe I had heard her wrong. I looked back at her and she smiled at me and continued explaining what had happened.

"You should have seen the look on the guys face," she laughed.

"I thought for sure he was going to have a heart attack, when the cop knocked on the window. I'm surprised he didn't, to be honest. He looks like a walking heart attack, waiting to happen."

"I'm sorry," I said, turning my full attention to her now. "Did you say...he was sucking YOUR cock? Or did I hear you wrong?"

"Oh no, you heard right; I'm a crossdresser honey."

Looking closely, I realized that there were some features that stood out and made it sound right. For the most part, she seemed pretty passable but her shoulders were a little more broad then they should probably have been. Her arms were a bit muscular, her tummy well toned like she probably worked out a little.

That voice too; it was a bit too low for my taste. Maybe it was the alcohol, that had caused me to not pick up on it right away but I definitely could see it now; this girl wasn't really a girl.

"I'm Trixie by the way," she said, softly.

"Right...I'm Bill."

"So Bill...I'm guessing you're stuck here until Monday morning, like me huh? It's a real bitch getting locked up, on a weekend."

"You guessed right," I nodded. "They said they can't get me in front of the judge until Monday morning. I don't have anyone who can bail me out either. Girlfriend is pissed off at me for even getting into this situation, and I really don't talk to my family. None of my friends have the money, either."

"At least you have friends honey," she said, a little depressed. "I don't know anyone who could bail me out; even if they had the cash."

With that said, I couldn't help but feel kind of bad for her; I stayed silent though and looked back out into the corridor, through the bars.

"So, Billy...you don't mind if I call you Billy, right?"

I laughed a little, shaking my head. People had been calling me Billy since I was a kid, so it was really no big deal to me. Trixie reached under the bunk and pulled out two cigarettes and a lighter; I was a bit surprised by that. She must have been hiding them, probably snuck them in without the guards noticing.

"You smoke?"

"Sure."

I sat down beside her on the bench, and Trixie handed me one of the cigarettes. She placed hers between her lips and lit up, before handing me the lighter for my own. I took a long drag from the cigarette and exhaled, blowing the smoke out into the cell.

"You from around here?" she asked, suddenly.

"Born and raised; Northeast Philly."

"Nice. You got it made, you know. I was raised in Kensington, not a good neighborhood at all I'm sure you're aware."

"My folks grew up down there," I replied.

"I spent the first nine years of my life there, before we moved to the Northeast."

"Lucky you got out. My parents were both drunks and they threw me out on the streets, when I was seventeen. Haven't seen or heard from either of them since."

"I'm sorry to hear that..."

I really was sorry; the alcohol was wearing off and with it, so was the adrenaline from the fight earlier. Trixie seemed like a pretty nice person, who had been through a shitty life and somehow it had led her to prostitution; it's all about survival.

I wasn't the type of person to judge anyone and figured it really wasn't any of my business anyway. We were quiet again for a few minutes, before Trixie leaned forward and looked over at me.

"Hey, can I ask you a question?"

"Sure," I nodded, without hesitation.

"You ever sucked a cock before?"

Now that question, had come completely out of left field. I blinked, surprised at how straight forward she was and I couldn't help but laugh; a bit nervously.

"Uh no, no I've never done that before; I'm straight, so..."

"Nothing gay about it," she shrugged. "Some straight guys like to experiment, that's all."

"Right...um...are you trying to hint, that you want me to..."

"Well, I wasn't trying to ask outright; thought that might be a little awkward. But yeah, I was wondering if you would."

Wow, I thought to myself; what a weekend it was so far.

"Right, well...no, I'm sorry. I'm not really interested."

"Oh, come on babe. I could really use a hand, I'm so fucking horny! See, when we got busted in that car those damn cops caught us right in the middle of the act. I never got to finish and I've just been so horny, ever since."

"That's what masturbation is for."

"Yeah, of course! But it doesn't beat the real thing...you're a guy, you should know right?"

She placed her hand on my knee and I looked down, noticing the bulge in her skirt; she had a hard on. I jumped up from the bench and moved to the other side of the cell, staring at her long and hard. "I said, no thank you..."

I leaned my back against the wall and slid down to the floor, pulling my knees to my chest and keeping my eyes on her. After a few moments, Trixie stood up and slowly started walking across the cell and stopped right in front of me. Her bulge was just inches from my face, and she lifted her skirt and pulled her panties to the side; out flopped the biggest cock I had ever seen.

Fully erect, she was probably around ten inches and easily put my seven and a half to shame.

"Go on baby," she whispered, running her hands through my hair. "Just give it a try; no one has to know."

I slid across the floor, moving away from her and stood up. I pushed past her and walked back over to the benc, sitting down again. Once again, I repeated myself...

"No thank you."

With that, I laid down and kept my back against the wall, so she couldn't try anything. Trixie stood in the spot where I had left her for a while, leaning against the wall and stroking her cock slowly. We kept eye contact for a few minutes, as she jerked her dick and I kept looking away and looking back, hoping she had stopped; only to find she was still going.

Eventually though, she gave up with a frustrated sigh and sat down on the other bench, staring at the wall and paying no more attention to me.

I closed my eyes and after a few minutes, I drifted off to sleep.

I was awoken at some point in the middle of the night, to what felt like someone holding me in their arms. I could feel warm breath against the back of my neck, and something hard poking at my ass. It took a few moments to register and when it did, my eyes snapped wide open. At some point during the night, I had rolled over so that I was now facing the bench and had left myself wide open to Trixie, who I was confident was the one holding me at that moment.

I realized that my pants had also been removed and I could feel what I assumed was her cock, probing my asshole. She kept gently thrusting her hips forward, humping my ass and threatening to shove that monster cock in my hole. I was just about to push her away, when Trixie rolled me over onto my back and sat right on my chest.

Her cock was right in my face and she smirked at me, stroking herself slowly.

"Stay quiet and don't move."

Before I could say a word, Trixie leaned forward and shoved her cock right between my lips. I gagged, as she pushed all the way into my throat and my eyes welled up with tears as my gag reflex went crazy.

"Ohhh, fuck!" she moaned, grabbing my head and thrusting in and out of my mouth.

I grabbed her hips and tried to shove her off of me, but she grabbed my hands and pushed them up above my head. Pinning them down and preventing me from fighting back anymore. I hadn't realized until that moment, just how strong Trixie actually was; she had a perfect hold of my hands and I couldn't fight back.

I was forced to resign and lay there and take it, as she thrust her dick in and out of my throat. Her balls pressed up against my chin and I gagged again, spit running out the sides of my mouth.

Trixie pulled her cock out of my mouth and proceeded to smack me across the face with it about three times, before sliding off my chest and grabbing me by the hips. She flipped me over onto my stomach and got on top of me, humping me again. Once again I felt her cock, now wet with my spit, probing at my hole.

"Stop," I said, becoming frustrated and trying to push her off.

"Get the fuck off of me!"

"Relax babe," she whispered in my ear. "If you're too tense, it'll hurt even more. Calm down and maybe you'll enjoy yourself."

Without any further warning, Trixie pushed forward. I could feel the hot, spongy mushroom head of her cock pressing hard against my hole...and then it popped right into me.

I roared, burying my face in the pillow and trying to push through the pain as Trixie shoved her cock balls deep into my ass. She was splitting me in half but showing no mercy, as she quickly pulled back about halfway and slammed straight back into me again.

"Good god, Billy; your ass is so tight, it's amazing!"

I started grunting and panting, as Trixie began thrusting in and out of my ass and fucking me hard. She was being quite aggressive, holding me by the hips and pulling me back to meet her thrusts. Flesh smacked against flesh, the sound echoing through the prison cell and Trixie gave my ass a hard smack, which echoed even louder.

It was about that time, that I noticed my own cock was as hard as a rock; I couldn't understand how, since I wasn't gay and Trixie was basically forcing herself on me. I cursed my body for betraying me, as I realized I was also dripping pre-cum from my dick; there was a small pool of cum forming underneath of me.

"Look at that," Trixie said, panting and sweating.

"Looks like you've got yourself a nice little hard-on."

She reached around, wrapping her fingers around my dick and started jerking it furiously. She continued to drill my ass, slamming in and out of me while jerking my cock at the same time.

The combination of her giant cock inside of me and her hand wrapped around my own dick, was too much for me to handle and I couldn't hold back; I let out a low, and drawn out moan of pleasure taking even Trixie by surprise.

"Starting to enjoy it a little, huh?"

"N-No...fuck...stop..."

I didn't want to admit it, but yes it did feel good; the pain had subsided considerably and now I was experiencing feelings that I had never felt, in my entire life. I didn't know what to make of any of this and it was mind boggling and frustrating. I wanted her to stop but at the same time, I wanted her to keep going.

What the fuck is wrong with me, I asked myself silently.

Trixie pulled out suddenly, leaving me with an odd feeling of emptiness; my asshole was gaping. She had stretched me wide open and I could feel the cool air, rushing inside of me. Trixie flipped me over onto my back and lifted my legs high up into the air, pushing the head of her cock to my hole again and slamming right back into me. I gave a loud yelp, followed by a long groan of pleasure as she carried on fucking me silly.

I felt that familiar feeling of pressure in my balls, but this time it was so intense; more intense then I had ever felt it before. I knew I was getting close, any second now I was going to cum. I didn't want to cum though...I couldn't cum. I had to hold back and I had to stop myself.

If I came then that would mean I enjoyed it, and if I enjoyed it then that meant I was gay; right? No, there was another side of me that didn't want to cum because if I did then it would be over; I actually found myself not wanting this, to end.

I bit my lip, closed my eyes and tried desperately to think of something besides the feeling of Trixie's cock in my ass, rubbing up against my prostate.

I thought of a million things that I thought would distract me, to help fight off the approaching orgasm...nothing worked though. I felt it building stronger and stronger and before I could stop myself, my cock gave a twitch and began to pulsate as I shot off the biggest wad of cum in my life.

I cried out in pleasure, Trixie covering my mouth with her hand as she continued pumping my ass. Thick, long ropes of cum shot straight up into the air and came back down, landing on my chest and my stomach. My body trembled and my head started to spin, as Trixie laughed out loud at me.

"That's a lot of fucking cum!" she said, clearly just as impressed with my orgasm, as I was.

"Now it's my turn."

She started fucking me harder and faster, grunting, moaning and panting as she slammed in and out as hard as she could. The more she fucked me, the more the orgasm seemed to linger...like it was never going to end. My mind was still swimming and I was trying to come back down, but it just wasn't working.

Finally, Trixie leaned in close and whispered softly into my ear, "I'm going to cum in your fucking ass, Bill. I'm going to pump you full of so much cum, it will be leaking for days."

True to her word, Trixie gave one final sharp thrust and bottomed out in my ass. With a grunt, my shemale cell mate started to cum and I could feel her cock twitching inside of me. There was a feeling of warmth flowing into my hole, and it was a very strange and foreign sensation; not exactly a bad one though. Trixie kept humping me, moaning softly as she rode out her own orgasm and emptied her balls.

When she was finally done, she slowly withdrew her cock from my ass and rolled off of the bench and onto her knees on the floor. Pushing herself onto her feet, her cock dangled right beside me.

Still semi-erect, her dick dripped with cum and she stroked it for a few moments.

"That was a good fuck," she said, still a bit breathless.

She wiped the sweat from her forehead, knelt down and gave me a kiss on the lips and then returned to her own bench; leaving me to myself and my rapid thoughts of confusion.

What the fuck, did I just do?

The next morning, I woke to the sound of the guard banging his knightstick on the cell door.

It startled the hell out of me and I sat straight up on the bench and looked to the door, to find him standing on the other side and laughing at me. With an irritated sigh, I lay back down and the guard carried on his business.

"Sleep well?"

I looked over at Trixie, who was sitting up on the other bench and smiling over at me. She had a blanket covering her bottom half, as she had not put her clothes on just yet.

"How's that ass feeling?"

I was aware of the dull ache in my butt, as well as the remains of her jizz slowly oozing out of my still gaping hole.

"Sore...and wet..."

"That's normal," she said, reaching under the covers.

"Still wet, huh? Mm...turn over and let me see that hole."

What did I have to lose at this point, I thought to myself. I threw the covers off and slowly rolled over onto my stomach. Trixie watched as I reached back and spread my cheeks, revealing my loose hole, cum dripping out.

"God, that is hot."

I looked over at her and saw her reaching her hand under the blankets, clearly stroking her cock as she admired my gaping hole.

"You should come over here and help me with this morning wood."

"If I say no...are you going to force me again?"

Trixie sighed, letting go of her dick and leaning her head back against the wall. Then, she slid forward to the edge of the bench and threw the covers back, revealing her cock which was now going soft again.

"Look...I'm sorry about last night," she said.

I was surprised to hear her say that, as I really hadn't thought she regretted it.

"I mean...it was great. But I shouldn't have forced you and I probably shouldn't have been as rough as I was."

"Right," I said. "Well...thank you."

"But man you were really into it, weren't you?"

"I...n-no, I wasn't!"

"Oh come on now," Trixie laughed. "You can't lie to me. You were moaning like a little bitch, I was afraid the guards were going to hear you and come break it up. And I bet you've NEVER came as hard as you did last night. So much fucking cum!"

She had a point there; I had never experienced an orgasm, quite as intense as the one that Trixie had given me last night. I cursed myself, as I felt my dick starting to grow erect from thinking about last night. This was crazy; I really was into it, wasn't I?

"You say you're not into it," Trixie continued.

"But it looks like your friend, disagrees."

She pointed at my erection and I sighed, covering it up quickly with the blankets.

"Nothing to be ashamed of," she said. "Come over here...let's have a little more fun."

I ignored her for a few moments, before I noticed that her cock was standing at full attention once again. She wrapped her fingers around it and started stroking, smiling at me the whole time.

"I know you want this, Billy...stop trying to hide it."

Trixie stood up and started walking towards me, her cock pointing straight out as she moved across the floor. She climbed onto the bench next to me and laid down, stretching her legs out so they were resting on mine.

"Go ahead," she said. "I know you want it."

I sighed, unable to ignore the urge and leaned down, wrapping my lips around her thick pole. It felt different this time, probably because I was doing it willingly as opposed to her shoving it down my throat like she had done, the night before. I moved my head down further and further, swallowing as much of her cock as I could manage before I gagged just a little.