tagTranssexuals & CrossdressersCaught and Punished

Caught and Punished


I had walked into the mall on a Friday afternoon with a group of my friends, Steve, Bill and Ryan. The plan was pretty' simple; Bill would stand guard while Steve, Ryan and me went into the jewelry store. Steve and Ryan would distract the clerk while I went around to one of the glass cases and picked the lock. Once I got what I needed, I would clear my throat as though I were simply coughing as a signal to let them know I was ready. Then we would get out of there, playing it casual and nothing would go wrong.

I couldn't' believe even now that I had sunk this low; but this was very important to me. See, I'm' not exactly the criminal type. I've' never stolen a thing in my life until this point actually; so why now right? Because tomorrow is my three-year anniversary with my girlfriend who I am very in love with; Leslie and I met in the tenth grade and now that we had both graduated high school, things were complicated. I was having trouble finding employment while she was going back to school; it was hard for us to get out and do things together like' we use to.

Especially when I had no money and pretty much all the money she had went towards getting back and forth to her classes, buying herself food and paying for supplies she needed for class.

I wanted more than' anything to do something nice for her for our anniversary though. I'd' sold a lot of my important belongings to make as much cash as I possibly could, and so far I had around fifty dollars. Just enough to treat her to a nice dinner and' maybe a movie. I didn't' have enough to buy her any kind of a gift though and it broke' my heart when I realized that.

Steve, Bill and Ryan...well they were use to this kind of stuff really. They were a couple of low life but they had been my friends since seventh grade and I always trusted them no matter what. So' when they realized how upset I was that I couldn't' afford to buy anything for Leslie...they asked me if I was willing to do anything to get her something nice. That's' when they came up with this plan.

I was going to steal a five thousand dollar necklace that I was pretty' sure Leslie was going to fall head over heels in love with when I gave it to her. I had to have this necklace; I had to give it to her no matter what it took. I thought the plan over a thousand times and at first, I was against it, but slowly each time I thought about it I found myself' starting to agree.

Finally, here we were at the shop about to follow through with the plan.

"Ready Nick,"

I glanced over at Bill who had spoken up, asking if I was ready or not. Technically, with my stomach in a complete knot, I didn't' feel ready at all really; but it was now or never. "Yes," I replied nervously.

Into the shop, we went with Bill staying outside leaning against a wall casually and standing guard as planned. In the event that someone should walk by and notice what I was doing while Steve and Ryan were talking to the clerk, someone would have to alert us as quickly as possible. I watched as Steve and Ryan walked over to the counter, where a beautiful tall blonde woman stood smiling at us. She had dark brown eyes and an incredible body.

"Hi, can I help you?" I heard her ask.

"Yeah uh...my friend Ryan here was looking for a birthday gift for his mom."

"Okay, what are you looking for?"

Their conversation carried on and casually, I walked around the shop for a moment trying to pretend that I was simply looking at the many different necklaces and rings and other jewelry. My heart was pounding in my chest and I began to panic as I realized I had actually forgotten which case the necklace I was looking for was' locked away inside of. As I scrambled around the shop trying hard not to make myself look suspicious, I noticed Bill eye balling me through the window as though he were getting annoyed. I tried to relax; I took several deep breaths and my erratic heart beat slowed down to normal.

Finally, there it was; my eyes fell upon the beauty that I was searching for in one of the cases on the far left hand corner of the store. Taking another deep breath, I glanced over at the counter to see that Steve and Ryan still had the clerk quite distracted with their false description of what they were looking for.

Looking over once again, I realized for the first time how oddly muscular the clerk looked for a woman. She wasn't' exactly built like a brick wall or anything, but I could see her arms were bigger than those of most girls'

She did not exactly look like the kind of woman you wanted to fuck with in an alleyway, like' she might kick your ass into the ground if you did.

I knelt down slowly and reached into my pocket pulling out the lock pick that Ryan had given me earlier. I went to work trying to pick the lock the best I could and as quickly as possible, until finally it clicked open.

Slowly and carefully, I pulled the door to the case open and reached inside. It was right within my grasp, the worst thing that could have happened occurred. As I grabbed the necklace and pulled it out, I moved to shut the door to the case only to shut it a little too hard and the case made a vibrating sound. It was assisted' by the sound of the jewelry inside clanking together and before I knew it, the clerk had looked away from my friends and noticed me.

"Hey, what the hell are you doing?"

Immediately, Steve and Ryan flew across the shop towards the exit and I jumped to my feet looking towards the door. I was about to run but found myself contemplating whether or' not I should leave the necklace. If I took it with me then I stood a bigger chance of being hunted' down by the authorities, or at least that was how I saw the situation.

The clerk jumped over the counter and to my surprise darted across the store straight towards me; damn was she fast. I threw the necklace down and darted faster than I had ever moved in my entire life towards the door. I was just inches away from making my escape out into the mall, when I felt a hand grab hold of my wrist and pull me back. I was' spun around only to have my face make contact with a fist. I was seeing stars as I stumbled backwards and she released my hand from her grip, stepping forward and delivering a second and stronger blow to the side of my head.

That one knocked me to the floor and as I looked up at her' I noticed the entire room was now spinning around me.

I glanced through the door looking for my friends; they were gone. They had left me here, abandoned me; I should have seen something like that coming, knowing how they were.

The dizziness did not stop, I found myself going in and out of consciousness for a few moments as I watched her move towards the door. She closed it and locked it, pulling down the blinds so no one outside could see into the store. Then she turned around and looked down at me, before leaning down to grab me by the arm and attempt to pull me to my feet.

As she did so, I felt myself slipping completely into unconsciousness; the next thing I knew, I was' surrounded by darkness and silence.

I woke some time later, to find myself tied to a chair in a small room. My head was pounding and I found that I was extremely thirsty and a little hungry as well. Groaning, I looked around at my surroundings; there was a desk in the right hand corner.

It was' covered with papers and other things and a phone hung on the wall right behind the desk. On the other two corners of the room were shelves with box's and what looked like folders and' such. I assumed I was in the manager's office where the clerk would hold me in custody until mall security arrived. They would take me to their office and then call the police from there; then I would be taken out in cuffs and probably have charges pressed against me for attempted robbery.

This was fucking great, I thought to myself. What the' hell was I going to tell my parents? Even better what was I going to tell Leslie when she found out I wouldn't' be able to take her out for our anniversary tomorrow night because I was in jail waiting for someone to bail me out. I just wanted to get this over with and found myself hoping that security would be here quickly.

The door to the office opened and in walked the clerk, with a sour look on her face. She shut the door and leaned against the desk staring at me for a few long moments. I wondered if she intended on even saying anything, or if she just felt the need to keep a close eye on me until security arrived.

"That was really fucking stupid," she said finally. She crossed her arms over her chest and shook her head as though she were ashamed of my actions. Who the' hell did she think she was anyway; I didn't' even know her.

"Why did you do that?"

"Why did you hit me so hard," I replied sounding a little annoyed.

"Why did I hit you; well let's see maybe because you tried to rob my fucking store and I knew I couldn't just tell you 'hey, sit down and wait while I call security' now could I?"

I leaned my head back and sighed in frustration staring up at the ceiling trying to figure out what to do next. "Look, I know this probably won't matter much," I said.

"But...if you let me go and forget all about this I swear you will never even see my face again. I promise."

She laughed and I found myself becoming a little angry with her. She pushed herself away from the desk and walked over to me, leaning down so that she was now eye to' eye with me and could look me dead in the face with those dark brown eyes.

"Are you seriously trying to talk your way out of this?"

"Maybe...I guess...I don't know okay, just please I said I won't-"

"I don't care what you said...what's your name anyway?"

I sighed and looked away for a moment then looked back at her.


"Because I need to know your name so I can tell security when they get here," she said walking away from me towards the phone. I realized now she had yet to even' call security. Regardless, I was getting the feeling that there was no way I was going to get out of this situation no matter what I did.

"Nick," I replied. "Nick Stevenson."

"Well Nick...why don't you explain to me why the hell you did this?"

What the hell, I thought. I was already' screwed as it was I might as well just go along with whatever questions she felt she needed to ask me. The sooner she called security the sooner they would get here and the sooner the police could get me to jail and the faster I could get this all over with.

"I had to,"

She looked at me curiously as though she did not understand exactly what I meant. "What...you mean your friends forced you to do it?"

"No...no I mean, I had to. I was trying to do something nice for someone I love. My girlfriend,"

Suddenly, her demeanor changed; she moved away from the phone and leaned against the front of the desk again. The look on her face told me that she wanted me to continue explaining just what I had been thinking.

"Tomorrows our anniversary," I said. "I wanted to buy her that necklace. I couldn't' afford it though; there was just no way. My friends...they do shit like this all the time. So they offered to help me get it for her, and I said no at first but after a while I just...couldn't resist anymore."

"Well your friends did a great job at helping you didn't they," she replied sarcastically.

Yeah, they had done one hell of a job for sure. They left me here, didn't even try to help me get away with them just took off and now they were probably home relaxing safe and sound while I was stuck here waiting to have my ass hauled away to prison.

"Their assholes I guess,"

"You guess; yeah, I think their more than that." She replied.

"Look just...call security okay? I just want to get this over with."

She sighed, pushing herself up onto the desk itself and sitting down; she continued to stare at me long and hard and I was getting really annoyed.

"I've never known a criminal to do something like this just for their girlfriend or wife; you must really love her a lot."

I smiled weakly and nodded my head, looking away.

"I do,"

"Well then," she said sliding off the desk. "I have an offer to make you."

Was I hearing her right? Was she offering to bargain with me; this was completely unexpected as you might imagine. What the' hell would she possibly be willing to have me do to bargain with her here.

"How much do you love your girlfriend?"

"A lot," I replied. I noticed at that moment that she was leaning over me now and I could see perfectly her beautiful cleavage. What exactly was she getting at right here?

I had no idea, but I could smell her perfume and between that and the sight of her cleavage, I could feel my cock becoming hard in my pants.

"Enough to do anything for that necklace,"

I simply nodded my head "yes" and she smiled, backing away from me just slightly. She removed the button up shirt that she was wearing suddenly, and hung it over the back of the chair by the desk. Now I was even more confused as I watched her make this move, then turn around and smile at me.

She was now wearing a white t-shirt which had been underneath of the button' up shirt and I could see her huge tits poking through the fabric of the shirt. I was really getting' turned on just watching her stand there with that big smile on her face as she stared at me for what felt like forever.

"You know," she said. "I'm not your typical woman."

"How so," I asked.

"Well...you see I look like a woman act like a woman talk like one and smell like one yes. But there is one thing about me that is just a little different from your typical girl...let's just say I come with some extra equipment."

What the' hell did that mean, I wondered. I wasn't' exactly putting two and' two together here and she looked a little annoyed by that as she stepped closer. She started to untie me to my surprise, then she took me by the hand and pulled me forward some. She pressed her lips to mine and kissed me, before slipping her tongue into my mouth. As we stood there kissing she took both of my hands placing them on her belt for me to begin unbuckling it for her.

I undid the belt then undid the button of her pants and she grabbed my hand again, this time sliding it down her unfastened pants and into her underwear.

Further' down my hand slid until I found myself quite shocked by what I had found and the next thing I knew I was yanking my hand away and pulling away from her in surprise. I couldn't' believe it myself; the beautiful seductive clerk happened to have a cock where there should have been a pussy.

"What's the matter?" she asked me seductively.

"You uh...you're a man,"

"No, not at all; I'm all woman I just have some extra parts, that's all."

"I can't do this," I said backing further away.

"It's wrong of me to do it anyway; I have a girlfriend. Even if you were a real woman it would still be wrong."

She was still smiling at me as she stepped closer and grabbed me by the shirt leaning in closer.

"I told you I AM a woman; and what your girlfriend doesn't know won't hurt her anyway."

This was fucking crazy I couldn't' believe this was even happening.

"Here's my offer; if you get naked for me and do whatever I ask you to do, I'll let you go. I won't call security and I'll forget all about you; hell I may even let you take the ring and give it to your girlfriend anyway."

"Just call security," I said. "I'm not gay; I can't do this."

"There's nothing gay about it sweet heart," she laughed. "Besides," she said as she suddenly slipped out of her pants and undergarments. I could see her cock dangling now between her legs and damn was it big, bigger than mine even. She turned around and bent over giving me a perfect view of her beautiful ass with her cock and balls dangling. She slapped herself on the ass and pulled her cheeks apart exposing her pink little asshole.

"When's the last time your girlfriend let you fuck her in the ass,"

The offer was becoming surprisingly tempting to say the least. I couldn't' believe it but my own cock was actually throbbing right now and dripping pre-cum as well. In truth, Leslie never let me fuck her in the ass; she hated doing things like that, because she found them to be weird. Hell, I could rarely even get her to give me a blowjob unless I did something to "earn" it from her.

The clerk was no longer bending over for me; now she was laying' across her desk with her legs spread wide and her cock standing at full attention as she stroked it nice and slow her eyes never leaving mine the whole time. Even just watching her lay there stroking herself seemed to be arousing to me now.

"Of course if you really don't want to..." she trailed off reaching behind her and grabbing the phone from the wall. "I guess I'll just go ahead and call security."

"No," I said in a sharp tone. "I...I'll do it,"

Before I knew what the' hell I was doing I had slipped out of my t-shirt followed by my jeans and boxers. I climbed on top of the desk with her, and she reached back again hanging the phone up while smiling at me. I leaned over top of her and she stared up at me as she ran her hands up and down my back and my ass causing me to shiver.

She pulled me in close and we kissed again, this time even more passionately then the last. Our cocks were both hard as rock rubbing together and I still could not believe any of this was even really happening. I would be an idiot to turn down this offer though.

I would get off completely free of charges and possibly get to keep the ring for Leslie and on top of that' I was going to get' laid to. Not that I couldn't get laid by Leslie tomorrow night for our anniversary, but I was going to get laid by someone willing to do things that Leslie did not like to do. As we continued kissing, she grabbed hold of my cock and her own and started stroking them against one another. The friction felt good and I trembled at the feeling as my balls tightened with anticipation. I really just wanted to fuck her right here right now I didn't' want to wait anymore.

Unfortunately, she pushed me off and I thought for a moment that maybe she had changed her mind or something. She got off the desk and had me sit down on the chair where I had been sitting earlier and she got down on her knees right in front of me. I groaned leaning my head back as she leaned in close and wrapped her warm moist lips around my hard cock. Up and down her head began to bob as she took my dick in and out of her mouth, all the way back to the back of her throat. Leslie did not know how to deep throat without gagging way to much; it was one reason she hated sucking my dick.

This woman or...man...whatever you chose to call her, was doing an exceptional job though. I had never had a blowjob quite this good before,

I could feel myself starting to get close and I ran a hand through her hair as I braced myself for what I knew was going to happen at any given moment. Finally, before I could give her any warning, I thrust my hips upward shoving my dick to the back of her throat and let out a howl of pleasure as I started to cum shooting my load down her gullet.

She choked a little in surprise, but swallowed it all just like' a true cocksucker would do. I was absolutely amazed' at her skill and her willingness to swallow every' last drop.

"Oops," she said as she pulled my dick from her mouth. "You came a lot easier than I thought; you should have told me so I could have stopped."

"Stopped; why would I have wanted that,"

"Well so you could have had a piece of my ass of course," she said smiling as she turned around and waved her ass right in my face. I felt my dick responding to the beautiful sight, growing hard again already.

"To bad," she said. "You only get one shot; now it's my turn."

Before I could protest she pulled me off of the chair and had me lay on the desk where she climbed on top of me and planted her ass right on my chest. Her huge cock was now mere inches from my face as she leaned forward and crammed it down my throat causing me to choke and gag. She began throat fucking me with such force I thought for sure I was going to puke all over the place because she kept pressing against my gag reflex.

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byWhiskeyIsGood© 15 comments/ 84557 views/ 65 favorites

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