Caught and Punished

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I could feel her balls against my chin though and for some reason the feeling was a rather arousing one.

I found myself becoming quite hard at the presence of her testicles up against my chin as she continued to thrust her dick in and out of my throat for about two minutes.

Just when I was sure she was about to cum, she stopped and pulled her dick free from my mouth smiled and kissed me on the lips. I was struggling to catch my breath, exhausted from having her crammed all the way down my gullet for nearly three whole minutes leaving me breathless.

The next thing she did was have me turn over onto my stomach, leaning over the desk with my ass pointing straight out towards her.

I didn't' quite know what to do since I'd never been with another man before let alone a transsexual, so I just stayed there waiting for her to make a move first. I jumped in surprise and yelped in pain when she suddenly slapped me across the ass.

"You've been a bad boy; trying to rob a jewelry store. Breaking the law like that. I am going to have to punish you myself. This ass is just too sweet for me to let those perverts in prison have any of it."

Honestly, considering how hot she was I would rather have her bending me over and shoving her cock up my ass then some big fat person in a prison cell or a shower room. Another slap across my ass and I yelped out in pain once again, and that was followed by three more slaps. I could see she was obviously very much into the whole dominatrix role, or at least right now' she was. She hadn't' been very much like this when she made me suck her cock a few minutes ago, but hey whatever got her off, got her off.

Finally, she stopped smacking me across the cheeks and I could feel the mushroom head of her cock rubbing against my ass crack gently probing me.

"Mmmm...this ass is so hot. I'm going to fuck the shit out of it,"

I waited nervously for the searing pain I was sure would come when she shoved her dick into my ass. We weren't' in a bedroom on a soft bed where she would have probably had a bottle of lube to make things easier, so I was expecting this to be pretty painful without any form of lubricant involved. To my surprise' though she moved away from me for a moment and opened one of the drawers in the desk pulling out a bottle of Astroglide. I sighed in relief as she popped open the bottle came back around behind me and poured some of the cool jelly all over my asshole. She rubbed it in nice and good before sitting the lube down on the desk and again probing me with her huge cock.

"You ready baby,"

The way she said it made me think back to earlier when Bill had asked outside the store if I was ready for our mission; although Bill had not referred to me as "baby" and if he had I probably would have broke his nose.

I gave my reply by pushing my ass back against her cock and she got the point, before grabbing me by the hips and pushing forward. I felt pressure and moments later, there was a sharp burning sensation as she popped right into me. She slid all the way in, in one shot thanks to the excessive amount of lubrication that she had applied and before I knew it, she was balls deep inside of my hot tight asshole.

She waited a few seconds for me to adjust before she started slowly thrusting in and out at a slow pace until I had gotten use to the feeling of fullness. I could feel a strange sensation, like' my asshole was squeezing around her cock with every thrust that she delivered. She kept sliding right over my prostate gland sending waves of pleasure rolling over me, and my own cock was now throbbing and dripping pre-cum' from the stimulation.

Harder and faster, she began to fuck me, and louder and louder' we both became with our sounds of pleasure moaning and groaning throughout it all.

I could feel her dick swelling up inside of me and hear her breathing becoming a little more erratic. I took that as a sign that she was getting close now; I wanted her to cum'

I wanted her to cum deep inside my ass, and so I started squeezing my asshole tighter around her cock to make it feel better. It seemed to be working, as she dug her nails into my hips pulling me back harder against her and forcing herself' deeper into me.

Finally, I felt it; the eruption of warmth deep inside my ass. I could feel her pumping her load into my ass like a car being' pumped with gasoline. When it was over, she slumped over me pushing me down against the desk. Her nipples dug into my back and I could feel her sweat running down all over my back and sides as she tried to recover her breath.

When she had recovered, she pulled out of my ass and I rolled over onto my back before sitting up with her cum leaking out of me and all over the place. We both laughed as she leaned in and gave me a kiss on the lips; we were finished, but for some reason I wished that' it had lasted much longer than it did.

"Well that was fun," she said as she handed me a paper towel to wipe my ass. Indeed it had been fun, and I found myself wondering if I even wanted to bother going back to Leslie after all of that. Sure' I loved her, but I was a very sexual person and she was not. She had never once given me an orgasm as intense as the one that this woman had just given me and I found myself questioning my sexuality now that we had finished.

"I uh...I never got your name," I said. She smiled at me as we started to get dressed.

"I'm Laura...you can take the necklace by the way if you want; and know that if things don't work out between you and your girlfriend for whatever reason, your more than welcome to come back to me."

Two scores there; I could take the necklace and give it to Leslie and should I decide later that I didn't want to continue my relationship with Leslie I could come back here and be with Laura.

It was definitely something I planned on taking into consideration I realized as I slipped out of the office. She followed me through the store and handed me the necklace, which she had boxed and put into a bag for me. She unlocked the door and pushed it open as I moved to slip past her and out into the mall.

I turned around and smiled, leaning in close to her and we kissed one more time before I walked away making my way towards the mall exit. I was not sure if I would ever see Laura again or not...but I had damn sure had a lot of fun with her in her office. Maybe I should try to rob this jewelry store a little more often.

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  • COMMENTS
16 Comments
AnonymousAnonymousover 4 years ago
suggestion

I would like to see a sequel of him coming back to be with her

AnonymousAnonymousover 8 years ago
🙀..... The hell

WWWWWWWHHHHHAAAAATTTT TTTTHHHHEEEE FFFFAAAAQQQQ!

LibidiotLibidiotover 9 years ago
Hot as Hell

This is basically my life

WhiskeyIsGoodWhiskeyIsGoodabout 11 years agoAuthor

It's a thought. Yes, No Thank You was about a cross-dresser, but that character wasn't exactly what you'd call a sissy boy. He was a top and a bottom and wasn't much into being humiliated....I'd actually like to continue that series, but I'm really unsure of what direction I want it to take.

AnonymousAnonymousabout 11 years ago
Suggestion

This story was great. I hope it continues. How about another story sort of like "Karlie". I like how the male in that story actually intended to find a transsexual. I also like how both partners were sober. The male in this story should be shy, possibly even a virgin (like myself). As a bisexual male, who is more interested in being bottom than top but still versatile, this is essentially my ultimate fantasy.

P.S. I do recall you doing a story involving crossdressing before ("No Thank You").

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