Call it the last minute jitters if you will; but I was getting married in one week, and I was feeling unbelievably on edge. At twenty’ eight years old I figured it was time to settle down, most of my other friends already had done so, so why not.

I figured it best to do it now before we hit our thirties and all of our friends and family start bitching about it to us. The thing was…I was not really’ sure if I wanted to get married or not.

I loved Jenny, yeah; but we had drifted apart over the six years we had been dating, and part of me just didn’t’ feel the way I used to feel for her. For the first few years, we were hot. Man were so fucking hot, we were on fire. Sex at least six times a week and we weren’t’ shy about where we did it either. We would fuck in the park, in mall bathrooms, at home, in my backyard, you name it we probably did it there. But’ things just…were not like that anymore.

I won’t’ lie…acknowledging that is painful, but what can I do? I had tried to fix our problems, but whenever we would fight one of us or’ the other would always shut down. So why get married, you ask if we have so many issues? I don’t’ know;

I guess somewhere in the back of my mind I was hoping it would help us. I proposed to her during a six’ month period where things seemed to be improving, and I figured it would work. But’ shortly after I proposed, that’s’ when things went back to shit again.

Now here I was my final week as a bachelor and I had no idea what was going on inside my head. I had turned down my friends and their offers for a good bachelor party and instead opted for some time to myself, so I could try and’ clear my head. I was in Center City, alone, it was a nice summer night and I was in the mood for some drinks.

I stumbled upon a bar down around South Street and decided to go in and have some whiskey. I sat down at the bar and the bar tender approached; I gave him my order, a Jack and Coke, and he set off to prepare my drink for me while I sat and watched the TV. During a commercial break from the show that was on air, I took a brief look around the bar to see my surroundings. There weren’t’ very many people here, it was a slow Tuesday night apparently.

I sighed, thanked the bar tender, and handed him the money for my drink once he handed it to me. I took my first sip and leaned back in the bar stool, tossing around in my head the situation with me and’ Jenny. As I sat there, I noticed a beautiful young woman about my age sitting across from me with dark brown eyes and long black hair. She had two piercings on her lips, snakebites they called them usually. She also had a stud nose piercing and a sleeve of tattoos on her left arm.

She could not have been a day older than twenty’ one I thought, and she was hot as hell.

Just looking at her, I felt my cock begin to stir in my pants as I took another sip of my Jack and Coke. That’s’ when she looked over and noticed me looking at her, and I panicked looking away quickly.

I looked back a few moments later and saw her smiling back at me now. I relaxed slightly, realizing she did not seem to be angry by me looking her way. Eventually, I tried to move my attention away and focus on my drink and in doing so it wasn’t’ long before I had drank the entire beverage.

I was about to signal the bar tender, when he approached me with a fresh glass of Jack and Coke already prepared for me.

“From the lady,” he said pointing over at her. I smiled nervously and took the glass. “Thank you,” I mouthed to her and she winked at me. A few seconds later she stood up and moved around the bar, taking a seat alongside me.

“Hey…like what you see?”

I laughed feeling my stomach in knots and nodded my head. “Yeah, definitely,”

“I’m glad; my name is Leslie,” she reached her hand out to shake mine and I accepted the gesture smiling back at her as my nerves began to ease up just a little. “I’m Tom,” I said introducing myself. “Nice to meet you,”

“Likewise Tom,” she said taking a swig of her beer.

“So, what brings you here all alone on a Tuesday night? Just for fun or’ some personal reason?”

I sighed and shrugged my shoulders. I really didn’t’ want to unload my problems on some woman I just met in a bar; I did not want to come off as some emotional douche bag or something like that. “It’s nothing,” I replied softly. “Just uh…a lot on my mind, that’s all.”

“Oh,” she answered. “Well, I’m a great listener if you want to talk.”

“No, that’s…that’s okay, really. I don’t want to be that way.”

“What way? I don’t mind, really, it’s perfectly fine.”

She smiled at me and at that moment I realized, there was no way I could ignore that beautiful smile or her beautiful eyes. Her eyes seemed to stare deep into my soul, like’ she knew there was something really bugging me.

Before I knew it, we were both drinking quite heavily and soon enough I was feeling the effects of the alcohol, which helped me to open up some and talk to her about my issues a little more. I didn’t’ tell her I was engaged; I did not want to make her pissed that I was flirting with her while I was supposed to be getting married next week or something. Eventually though, I noticed she was starting to flirt with me, and I knew I would have to tell her.

I knew she deserved to know; and it was wrong of me to let her flirt with me anyway, I was supposed to be getting married in a week. But’ I could not get those words out, I couldn’t’ tell her I was engaged…I was having too much fun.

“I really like you,” she said finally. I smiled at her, feeling pretty’ drunk but’ still knowing to an extent just what I was doing right now. “I like you too,” I replied softly.

“I have to go to the bathroom, but um…how about after I come back out, we get out of here and go back to my place. We can have some fun if you want,”

I smiled and nodded my head, agreeing to go back to her apartment with her and she stood up from the stool walking off to the restroom to relieve her bladder. I sat there contemplating what I was about to do; I was about to go home with some girl I met at a bar and have sex with her, ultimately cheating on my soon-to-be wife. As I sat there weighing over these thoughts in my mind, trying to decide if I should go through with this or not, the bar tender approached me and leaned over the counter.

“I see you really seem to get along with Leslie,”

“Yeah,” I laughed nodding my head. “She’s pretty attractive.”

“That’s cool; it’s been a long time since I’ve seen her happy. Ever been with a girl like her before?”

I wasn’t’ quite sure what he meant by that, and I finished off the last of my final Jack and Coke trying to figure it out.

“No,” I said finally, figuring he was referring to how attractive she happened to be. “No, I haven’t been with anyone quite like her; but I can tell she’s something special.”

“She is, definitely. I hear she’s a real fire cracker though; try not to piss her off,”

I laughed and so did he turning away to tend to another customer. The bathroom door opened and Leslie came out, smiling at me the whole time she walked over to the counter.

“Hey, listen,” she said. “I just got a call from my roommate and she’s home a lot sooner than I thought she would be. Maybe it’s’ better if we go back to your place? If you don’t mind I mean,”

That wasn’t’ what I was hoping to hear; going back to my place to have sex with another woman was risky. Jenny was away for a few days, staying with her sister in Jersey to get ready for the wedding next week; but shit happened, and like Leslie’s roommate had come home early, there was always a chance Jenny could wind up doing the same thing and walking in on us together.

“I don’t know…my place is a wreck, and my roommate has his girl over,” I lied. “Maybe we could get a motel room? I’ll pay.”

“Hmm,” she put her hands on her hips and thought about it.

“Okay,” she replied softly with a smile. “I’m up for that if you’re willing to pay.”

And’ with that we were off, paying the bar tender and leaving the bar holding each other’s hands as we set off in search of a motel. We settled on a cheap place not far from Center City. $100 a night, which wasn’t’ bad really…if I had been thinking with a sober mind though, I would have thought how bad of an idea this really was.

I only had a credit card with me and so I paid for the room with that. We made our way up to the second floor to room 218. I inserted the key, turned it and pushed the door open, stepping inside. Leslie followed me into the small room; it looked comfortable to say the least.

A single bed, big enough for two, small kitchen, small table and a TV…your typical every day motel room I suppose. I closed the door behind us, and turned around walking right into Leslie’s arms. She pulled me close to her and kissed me right on the lips, sliding her tongue into my mouth and I groaned kissing her back. I could taste alcohol and cigarettes on her breath, but it actually sort’ of turned me on even more.

“Why don’t you go take a shower,” she said smiling. “And I’ll wait here and get ready for you.” That was odd, I thought; was it not usually the girl who went to the bathroom to freshen up before a one’ night’ stand? I shrugged it off and figured it better this way anyway.

I didn’t’ want to hook up with a random girl and give her a bad impression by smelling like sweat and alcohol, so really a shower didn’t sound half bad.

I started to undress, and as I did I lay’ my clothes out over the back of a chair at the table. I smiled at Leslie as I walked towards the bathroom. I turned on the hot water in the shower and stepped in, under the stream, and relaxed as the water soothed my aching muscles.

As I leaned back against the wall losing myself in the warm water, I felt my cock begin to rise to attention. I was very horny, and really’ excited to be hooking up with Leslie. I quickly washed up, making sure to scrub every inch of my body, before stepping out of the shower and wrapping myself in a towel and drying up.

There was not much point in putting my clothes back on if I would just be taking them back off again to have sex in a few minutes; so instead, I emerged from the bathroom wearing only the towel to find Leslie lying on the bed with the covers pulled over her. She was leaning on her side, gazing at me with that seductive grin that I was quickly falling in love with.

“So, did you make sure to clean up real good?”

“Yeah,” I said stepping in front of the mattress and standing there. I could feel my cock aching underneath the towel. She noticed the bulge and sat up on her knees, crawling across the bed to the ledge and undoing my towel. My cock sprang free, hard as a rock and standing at full attention and Leslie giggled.

“Aw,” she said. “He looks so hard it must hurt.”

“Oh, you have no idea; whiskey has a tendency to get my hormones going,”

“Hmm…I can’t wait any longer baby,” she said. With that, she wrapped her beautiful lips around my throbbing erection and I threw my head back moaning in pleasure.

I sighed, staring up at the ceiling as Leslie bobbed her head, my cock sliding in and out of her warm wet mouth and she played with my balls. She took me deeper into her mouth and gagged as I hit the back of her throat, but succeeded in taking me all the way in regardless. She could deep throat; that was certainly a rare feature in most of the women I had been with over the years. Jenny definitely couldn’t’ do that, not that she enjoyed sucking my cock in the first place; she hated giving me blowjobs.

I ran my hand over her left arm, over the sleeve of tattoos she had and she groaned as I teased her skin with my fingertips. I looked back down at Leslie as she continued sucking and my eyes traced over the smooth skin of her back all the way down to her beautiful ass.

I reached forward, leaning over her and grabbing her left ass cheek, giving it a nice squeeze and she moaned against my dick. I groaned, shivering at the feeling of her hot breath against the head of my shaft.

I gave her a light slap and she jumped and giggled, but she never stopped sucking me. “I want to fuck you,”

I said it before I even realized the words were being’ spoken; I wanted her to bend over and let me slip my cock into her soaking wet pussy. She stopped sucking my dick and smiled up at me.

“Only if you promise to cum inside of me,”

That was risky; did not want to chance an unwanted pregnancy. Then again, I had fucked plenty of girls without condoms and none of them got pregnant. I couldn’t’ count how many times I had fucked Jenny without a condom, and not once had she gotten pregnant.

“Okay,” I replied.

“Great,” she said excitedly. “And’ it would be nice if you would give me a reach around too,”


She was still on her hands and knees, but then she straightened up and I saw it for the first time. I hadn’t’ noticed until now; she had been under the covers when I came out of the bathroom, and while she was sucking my cock she had been on her hands and knees the whole time so I couldn’t’ see. But’ hanging there between her smooth legs was a semi-erect cock, probably about eight inches long and a set of balls that hung quite low.

Suddenly, I understood what the bartender meant when he asked if I had ever been with a girl like Leslie before; he wasn’t’ referring to how beautiful she was. He was asking me if I had ever been with a transsexual before.


Leslie had turned around, her ass pointing out at me now and she was smiling back at me over her shoulder wiggling her ass as she waited for me to fuck her.

“Well? What are you waiting for sexy?”

“I uh,” I could not breathe…I could not speak. I could not find the words to say yes or no at this point and honestly I didn’t’ even know if I wanted this anymore. I was drunk sure; but I still had standards.

“What’s wrong?”

“I uh…”

“Oh fuck,” she grumbled moving out of her current position and dropping back on the mattress looking disappointed. “You didn’t know, did you?”

“No…not…not really,”

She sighed, shaking her head and lit up a cigarette, leaning back and taking a long drag before exhaling the thick white smoke.

“I’m sorry; I should have told you. That was wrong of me to just…assume you already knew.”

“No,” I replied. “It’s okay. Really; the bartender dropped a hint and I guess I just didn’t catch on to what he meant.” Leslie smiled and laughed, shaking her head.

“Yeah…Jimmy,” she said referring to the bartender. “He would know,”

I thought it over a few seconds more and made up my mind; I wasn’t’ interested in doing this. Plus’ my buzz was wearing off and as it did I began to really question whether or not I could bring myself to cheat on Jenny.

“It’s okay,” I said finally.


“I uh…yeah,”

I couldn’t’ believe I was saying it myself; maybe I was still more’ drunk then I had originally realized I was. I had to be, because I knew if I were sober, there was no way in hell I would be saying yes to having sex with a man right now. Even if that man happened to have a nice rack, beautiful eyes and’ looked and acted just like a real woman.

“Let’s do it,” I said smiling at her.

Leslie looked beyond excited as she set the cigarette down in an ash trash and got back on her knees, pulling me close to her again. She leaned up towards me and kissed me on the lips; I could taste the cigarettes on her breath.

She moved even closer and as we stood there making out I felt her grab my cock and start stroking it, against her own dick. What a strange feeling, I was getting a hand job and my cock was against another cock. When we stopped’ kissing, she smiled up at me then turned around so her ass was pointing towards me once again as it had been before.

“Well, c’mon then fuck me baby,”

I couldn’t’ hold back anymore; I was so unbelievably horny it was not even funny. I got up behind her, grabbed her hips and pulled her closer to the edge of the bed, so that the tip of my cock was’ pressed against her anus.

She moaned as I rubbed it against her ass, then’ stopped me before I could push into her. “Can’t forget the lube,” she said handing me a bottle of K.Y Jelly she pulled from her bag on the floor by the bed. I laughed and flipped the cap open, pouring a glob of lube all over my cock and rubbing it in really good, before adding some additional to her asshole. Once we were both set, I pressed my shaft to her asshole once more and pushed into her.

She grunted grabbing the bed sheets and moaning as my entire length slide right into her, balls deep inside her rectum as I clung to her hips.

“That’s it baby,” she sighed. “Oh, yeah fuck my ass baby.”

I was happy to obey that request, and I found myself pounding her now. I was slamming in and out of her ass with such force the entire mattress shook every time I pushed into her.

She was moaning, grunting, panting and screaming my name as I fucked her, and I found myself instinctively reaching around and grabbing her erect penis in my hand. It felt weird, holding another dick beside’ my own in my hand, to feel the stiffness, the veins pulsating. What the’ hell was I doing? Having sex with a girl like this; no, having sex with a man.

She looked like a woman, but I knew she was not really a woman. A real woman did not have a dick; she had a pussy.

Still, my arousal had a mind of its own and I felt myself getting closer and closer to having an orgasm. I tried to bite my lip and force it back, a mixture of rising shame and the urge to keep going a little while longer.

Finally, though, I could not hold back anymore, and with a howl’ I buried myself to the hilt inside of her and exploded. Leslie slumped forward into the mattress, and moaned as her dick began to squirt cum all over the sheets while I pumped her full of my own load.

I slumped forward, collapsing on top of her and pushing her into the mattress. She laughed, and so did I as I pulled out and rolled over next to her. Leslie crawled closer to me and lay’ her head on my chest, tracing circles with her fingertips around one of my nipples.

“That felt great,” she whispered in my ear and I groaned, my head resting on my pillow. I had to agree; but I was so fucking tired now it wasn’t’ even funny.

“How about a blowjob,”

Despite being so tired, my cock was still semi-hard so the idea of her wrapping her warm, wet lips around it once again sounded great, and just thinking of it caused me to rise to full attention again.

“Sounds good,” I replied and she giggled.

When she asked me about a blowjob though, I thought she meant did I want one; I hadn’t’ realized she meant that she wanted me to give her one, until she planted herself on my chest with her cock inches from my face and one hundred percent fully erect.

“What are you doing?” I asked, slightly surprised.

“Well, you said yes; didn’t you?”

I had no time to explain that I thought she wanted to suck me, because the next thing I knew, Leslie was cramming her big fat dick down my throat. I gagged, slurped and gurgled as she started throat fucking me, grabbing a fistful of my brown hair and pulling as she rode my face.

I was shocked to find that my own dick was throbbing now as I sucked her cock. I was actually enjoying myself; the musky aroma of her sweaty balls, the salty taste of her dick…it was all so arousing, I could not believe it.

It only took her about two minutes to hit her orgasm, and when she did I took in the warm salty flavor of her sticky cum as it shot down my throat. I gagged, but all in’ all I successfully swallowed her entire load and licked the head of her shaft clean. When I was done, Leslie collapsed next to me and within minute’s she was fast asleep, snoring softly with her face buried in the pillow.

I had a lot to take into consideration here; I had cheated on Jenny, and not only that, but I had cheated on her with a man who lived as a woman. As the alcohol began to wear off, it began to kick in what exactly I had done. I rolled over, squeezed my eyes shut and tried to fall asleep and forget. I had to forget, for the sake of my own sanity.

The following morning, I woke with a start and inhaled the sweet scent of Leslie’s perfume from the pillows mixed with the stench of cigarettes and alcohol. I groaned, lifting my face from the pillows and rolled over to stare up at the ceiling as memories of the previous night came rushing back.

I noticed then, that Leslie was not beside me; she was gone. Where, I did not know for sure. Then I noticed the sound of the shower running, and realized she had not left, she was simply washing up. This was my chance to try and’ get out of here without having to deal with any confrontations. I wanted to forget about last night, I did not want to talk to her.

I slipped out from under the blankets and grabbed my clothes, slipping into them and being extra quiet. Once I had my shoes on and the laces tied, I made my way to the door and snuck outside into the cool morning air. I breathed a breath of relief as I made my way down the stairs and rushed home.

Once I got to my house, I tore off my clothes and got right in the shower, washing away all of the evidence of last night. I washed my cock nice and good, and scrubbed away her scent, before getting out and brushing my teeth and using mouthwash to rid myself of the taste of her cum,

I sat down on the couch and tried to relax; that wasn’t’ working though. I wound up spending the rest of the day drinking to try and’ help cope with the frustration and thousands of different thoughts flooding my brain. Two days passed by and by now I was finally starting to get my mind back in the right place; I was finally starting to readjust.

I had not thought it was going to be okay after everything that happened, but so far Jenny did not seem to suspect anything and I was adjusting to the idea of keeping it secret from her. Thursday night, I was sitting at home on my couch watching TV; I had work in the morning and was just trying to kick back and relax before going to bed. Around 9:00′ the phone rang, but I did not recognize the number on the caller ID. I picked up, lifting the phone to my ear.


“Tom…its Leslie,”

Fuck…I slammed the phone back down on the receiver and stared at it for a long time, not wanting to believe that had just happened. How the’ hell did she get my number? Why the’ hell was she even trying to get in touch with me in the first place? She knew I had a girlfriend and that we were getting married in a few short days…what was’ she thinking.

The phone rang again and I growled under my breath, snatching it up off the receiver to my ear. This time, I did not say a word I just stayed quiet.

“Tom, its Leslie…don’t hang up on me,”

“Why are you calling me…furthermore how the fuck did you get my number?”

“I looked you up,” she replied nonchalantly. “You gave me your full name, so it wasn’t’ actually all that difficult to do. That’s what phone books are for,”

This was absolutely’ crazy, there was no way this was happening.

“Why are you calling me Leslie; we can’t talk anymore. I am’ getting married in a few days, I told you that. What we did the other night-”

“What we did the other night was fucking hot,” she cut me off. “You know it was too; and I also happen to know that you don’t really want to get married. You didn’t’ even have to tell me that one, its’ written all over your face when you talk about Jenny. You love her, but not like you use to love her, so listen. We had chemistry, we really got along great and I think we both really had fun. If you’re so unhappy with Jenny, leave her for me.”

It amazed me how straight forward she was; how blunt she could be. She said it as though it were as simple as just telling Jenny and leaving her. “I can’t,” I said in a serious tone. I just could not do that, it was bad enough that I had cheated in the first place. Maybe there was some truth in what Leslie said…maybe I did not really want to marry Jenny. But’ I would not hurt her by letting her find out that I had cheated on her, and then on top of that leaving her for another man.

“I’m not gay,” I blurted out.

“Gay; who said anything about gay…you’re not gay baby, unless you think you are. I’m all woman’…maybe not ALL, but more woman then a man.”

“I just can’t okay? I’m not interested,” She sighed into the phone and before she could say anything else, I hung up and disconnected the phone from the wall so she could not call me back. Stressed, I went to the kitchen and took a shot of Jack before heading to my room and crawling into bed.

I buried my face in the pillow and tried to fall asleep; unfortunately, it took me an hour and a half to drift off though.I

woke the next morning, my memory of the phone call from Leslie was hazy, but when it came back to me’ I felt the anxiety I had felt the night before return with the memory. I took another shot of Jack and proceeded to get myself ready for work, shaving, showering and dressing and out the door.

I worked at a supermarket in maintenance. It was an easy job in my opinion. I changed trash, cleaned things, and kept the store taken care of for six hours straight before someone else came in and took my place. I usually always worked from 9 am to 3 pm. I did my normal routine, changing trash, taking cardboard from some of the departments to the box crusher, and a few other things before heading to the bathroom to relieve my bladder.

It was pressing noon and I would be going on break real’ soon. I was walking down isle five towards the bathrooms when I heard a familiar voice calling my name. “Tom,”

I turned around, and to my horror, there she was standing a few feet away from me smiling with that broad smile I remembered…Leslie.

“What…are you doing here?” I was really pissed off now.

“Just came to talk,” she said walking up to me and leaning against a shelf. I sighed, shaking my head in disbelief.

“At my fucking job,” I said through gritted teeth. “You came to ‘talk’ at my job? How the’ hell do’ you even know where I work? Are you some kind of fucking stalker or some shit, I mean do you not understand me when I say I don’t want to be with you?”

“God; you don’t have to be so mean about it Tom. I came to talk to you about how you took the hell off like that the other day; so why don’t you take your break and meet me out front and we’ll figure all of this out.”

Figure what out I thought as she walked away in such a confident manner I could hardly believe I had let her walk off without me saying no first. I did not know what angle she was trying to work here but there was no way I would let her win.

I clocked out for my break after I came out of the bathroom and rushed out front to get this over with’. There she was, sitting on the bench smoking a cigarette, smiling at me the whole time. She had her hair pulled into pigtails and was wearing lots of makeup. I walked over and sat down across from her and nervously tapping my foot, I cleared my throat.

“What is this about,” I asked with a start.

The look in my eyes; she had to know I was furious. The funny thing was, she seemed to take pleasure in that thought, rather than fearing my anger or backing down like’ I wished she would.

“I told you; I wanted to talk about the other night.”

“I left because I didn’t want to ‘talk’ Leslie,”

“So what Tom; that’s really fucking rude you know,”

“Look…I’m sorry okay. I just…had a hard time realizing once I sobered up that I had not only cheated on my fucking soon to be wife, but I did it with a fucking man.”

Leslie laughed, taking a drag of her cigarette and turning to face me. I shook my head as she sat there, flaunting her cleavage.

“Hello,” she said in a humorous voice. “Boobs…big beautiful boobs; I’m a woman, remember?”

“Right,” I replied annoyed. “A woman who just happens to have a dick,”

“Ouch,” she laughed. “You didn’t seem so against it when it was in your mouth.”

I shook my head, looking around nervously hoping that no customers or fellow co-workers had overheard that part. Luckily, no one was anywhere near us at the’ moment and I sighed a sigh of relief.

“Leslie…get’ to the point. What the hell do you want?”

“Oh, c’mon now…I only want to-”

“Talk right? Well my break is almost over; so we’re’ running out of time. Listen, you need to leave me alone okay, I’m’ getting married. I don’t need this shit’ from you, I made a mistake.”

She stood up and stretched, taking another drag of her cigarette before leaning against the wall behind her and smirking at me seductively.”That mistake could ruin your life if you don’t cooperate with me Tommy boy. So’ here’s’ how it’s going to go; I’m going to tell you’re soon to be wife that you fucked a tranny, and I’ll be sure to mention how you sucked my cock too.

I’m going to destroy your marriage before it even begins.”

The look on her face told me she was serious, she had the balls…literally…to do exactly what she said she was going to do. I had no doubt in my mind about that, and I realized now I had to find some way to fix this situation.


“No, I’ll do it Tom; I’ll fucking ruin your life!”

“Please, don’t do that okay? I, I’m sorry…just don’t do that,”

She smiled at me throwing her cigarette to the ground and crushing it, extinguishing the light.

“Well,” she said. “Maybe we could…work something out between the two of us. If you’re willing to that is,”

I knew she wanted something; I had known this whole time, even though she kept insisting that she only wanted to talk. I just did not know what she wanted, and I couldn’t’ come up with even an idea as to what it may be.

“What do you want Leslie; I will do anything you want.”

“How about this; how about since your break is almost over, I stop by your apartment tonight and we can have a little sit down and talk about this all. I’m sure we can come up with something,”

Did I really want her at my apartment? No, absolutely’ not, but I definitely did not want her to tell Jenny what we had done together either.


“Okay; then I’ll see you tonight around 9:00 pm, sound good?”

“Yeah fine; my address is-”

“I already know,” she said in a calm tone. “Internet,”

And’ with that, she walked off, leaving me behind in complete frustration. I sighed heavily wondering what kind of “deal” she was going to offer me tonight. I checked the time on my cell phone realizing my break was finished I had to get back into the store, clock back in and finish up’ my shift.

The rest of my day went relatively fast, and when it was over’ I clocked out and rushed home. It was only 3:00 and I had plenty of time before my little “meeting” with Leslie, but I was so nervous I ran home anyway. When I got to my apartment, I made a dash for the bathroom turning on the shower and stripping naked.

I had showered already that morning, but I needed another hot one to help calm my nerves. It was a nice technique an old psychiatrist’ taught me on relieving the effects of anxiety, and right now my anxiety was literally through the roof so I looked forward to a hot shower.

Time ticked by so slowly after the shower, and after an aching amount of’ time had passed by it was finally 8:45 when I heard a soft knock at the apartment door. Nervously, I stood up and walked across the room, trying to calm my nerves as I reached to unlock and open the door. When I pulled it open, there stood Leslie wearing a black skirt and a black band t-shirt for the band “In This Moment.”

“Hi,” she said simply, as she smiled at me. She brushed right past me into my’ apartment and dropped down onto my couch like it was nothing. Make yourself at home, I thought silently to myself.

I closed the door and walked across the room, sitting in the recliner across from her so we could sit face to face; I wanted to get this over with’. Whatever plan she had, I just wanted her to get it out in the air so we could get it done and over with once and’ for all.

“Alright,” I said starting. “Let’s talk; what do I have to do to stop you.”

“Well, I don’t know just yet. First, let me ask you, how far are you willing to go to stop me? What exactly are you willing to do to make sure I don’t’ tell Jenny what we did the other night? Because, I have quite a few ideas,”

I wasn’t’ liking the look in her eyes; that sexual look she had the same night we fucked.

“I don’t know,” I replied. “What do you want…?”

She chuckled, crossing her legs and leaning back against the couch. She took a deep breath, and exhaled, staring up at the ceiling above us as though she were thinking of something to say.


I thought she would her demands right then and’ there; I was wrong though. She was trying to torture me mentally, trying to drive me fucking insane.

“You’re being so rude; go get me something to drink. Not much of a gentlemen, are we,”

I sighed, irritated, standing up and walking to the kitchen. I forgot to ask what she wanted to drink, but I didn’t’ give a shit when I realized.

She would get whatever the’ hell I gave her and in this case it was going to be water. I had not had the chance to go shopping yet, so that was all I had in right now. I came back from the kitchen handing her the glass of water and dropping back down on the recliner across from her as she took a sip and set the glass down on the table.

She smiled at me, such a confident smile. It made me a little uncomfortable to see such confidence in her eyes right now.

“So,” she started. “About Jenny; I think I can work something out here if you really don’t want me to tell her. I’m’ not asking for much really, unless you make it more than it has to be. But’ if you say no, I will tell Jenny. No questions asked, no stopping me. So you either say yes, or I fuck your life up,”

That was pretty’ straight forward, and I could still see she was so serious.

“I want a piece of that sweet ass,”

I laughed; I couldn’t’ help it, I just let loose and cracked up laughing. She couldn’t’ be serious after all, now could she? I mean, she really wanted me to have sex with her to stop her from telling Jenny that I already had sex with her. How crazy did that sound, I knew it sounded damn crazy to me.

“I don’t know what you’re laughing at; I’m being serious Tom.”

I shifted uncomfortably in the recliner and sat on the edge of the cushion, shaking my head running a hand through my hair.

“Are you really,” I asked a little unsure. “I mean…really?”

“Yes, really; have one more night with me, and I’ll leave you alone. Completely alone, I swear. It will be like’ I never existed, you can go back to living your life without me and Jenny, most importantly, will never know. If you say no though, I will go right to her and I don’t’ think she will like what I have to say. So I suggest you make the right choice here,”

“What,” I started. “You want to reenact what we did the other night?”

“Not quite,” she laughed.

She motioned with her eyes towards her groin and suddenly I understood what she meant by “piece of that ass.” She did not’ want me to fuck HER again, like’ I had done the other night.

I had also given her a blowjob the other night and I understood now that what she really wanted was probably another blowjob and a little more than that. What I did not understand’, was why. Was it because she really wanted it’ for sexual satisfaction, or was it to humiliate me.

So’ she could hold it over my head, dominate me and make me the “bitch” so to speak.

“No fucking way; you’re fucking joking. I’m not doing that.”

“Okay,” she said standing up and reaching into her pocket. She pulled out her cell phone, flipped it open and I panicked.

“Just have to make one phone call and-”

“Okay, hold the fuck on,” I shouted angrily. She glanced up from her screen at me, waiting for me to tell her why she should bother stopping.

I sighed in defeat, shaking my head. I swore I would not lose this battle, but I saw now that there was really no way I was going to win it either. “

I’ll do it,”

“Great,” she said sliding her phone back into her pocket.

Wasting little time at all, she sat back down and lifted her skirt revealing she had never even been wearing panties underneath the skirt. I shook my head, I could hardly believe I was about to follow through with this right now. I walked over towards her, getting down on my knees as her cock began to grow erect.

I had forgotten how big it actually was, yet at the same time, just staring at it and remembering how I had sucked her off the other night I felt my own dick responding, growing erect in my pants.

She stroked herself, right in front of my face, smiling the whole time; she had won. I closed my lips around her shaft, recalling the flavor of her cock as my tongue swirled around the head as it had the other night.

I heard her moan softly, grabbing a fistful of my hair and forcing her dick deeper down my throat. I choked, and I gagged, and I felt my throat tighten around her dick as she began shoving it in and out of my mouth. The same slurping and gagging sounds I was use to hearing were the sounds that I was making now, rather than someone else making them as they went down on me.

I would never admit it; but deep down, I had gotten over the disgust, and actually found myself enjoying myself. Her cock tasted good, the scent of her balls turned me on even more and I found my own dick throbbing by now.

“Mm, yeah, that’s it babe,” she moaned. “Suck that fucking cock baby,”

I bobbed my head up and down, as she still held on to a fistful of hair, thrusting in and out of my mouth. I felt her warm sweaty balls against my chin, and I moaned back at her as I flicked the tip of her dick with my tongue.

“What’s that,” she asked. “Did you just moan?”

I ignored her, not thinking it was an actual question, only to receive a light slap across the face. I was a’ bit taken back, but I stopped sucking her cock and looked up at her to wait for her to tell me why she had slapped me.

“I just asked you a fucking question,”


“Sorry what,” she asked slapping me again, a little harder this time.

“S-Sorry,” I replied, not quite’ sure what she wanted.

She slapped me a third time, this time the hardest, and I yelled in pain as my cheek stung.

“Mistress,” she yelled at me angrily. “Call me mistress!”

“Sorry Mistress, it won’t happen again,” I corrected myself.

“Good; now answer the question. Did you, or did you not just moan.”

“Yes, I did.” Another smack across the face, and I grunted, rubbing the red bruise forming on my cheek now.

“Yes, I did moan mistress,” I corrected myself again.

She shoved her cock back into my mouth, throat fucking me now and groaning the entire time.

“That’s what I thought. You are’ such a little whore Tom, you know that? You’re’ my little fucking cock sucking fucking bitch, aren’t you?”

“Yes Mistress,” I said pulling her cock from my mouth for just a moment.

“Mm,” she moaned. “Good boy; now stand up.” I followed her commands, pulling her dick from my mouth regretfully, and standing in front of her.

“Get undressed.”

Slowly, I removed my shirt, tossing it to the floor followed by my pants and my boxers. Now I stood in front of Leslie, completely naked, my hard cock pointing straight out towards her, sweat running down my chest.

“Good…turn around so I can see that ass,”

Turning around, I gave her a nice view of my ass and I heard her groan as she stroked her cock. She leaned forward and slapped my ass; I jumped in surprise and she giggled, giving it a light kiss on one of the two cheeks.

“That’s right baby; you want me to fuck that sweet ass of yours, don’t you?”

“Yes Mistress,”

“Say it,” she hissed. “Tell me you want me to fuck you in the ass.”

“I…I want you to fuck my ass please,”


I grunted, rubbing the red bruise on my ass then howled as she smacked me again, twice as hard this time and a third time the hardest of all three.

June 2018
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