Mark's Odd Night

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A very strange woman takes Mark on a sissy adventure.
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Menthol cigarettes were not my thing, but when that cute girl from work asks if you wanna go have a smoke, you're not gonna complain about her offering you a Newport. The smoke danced through the air, framing the beauty of the woman who stood across from me. She had gorgeous red hair, which flowed down to her shoulders framing her face as well as her sheer green dress framed her picturesque figure. Her green eyes sparkled behind the cloud of cigarette smoke and it was all I could do to not be completely hypnotized.

"Thanks for the cigarette Amy," I said as I tried and failed to avoid staring at the beautiful woman. I had met her in the employee café less than a week prior. When I saw her I dismissed any silly ideas of asking her out, seeing as how out of my Amygue she was, but she had approached me. We worked in different departments but she had invited me out for a smoke a few times. I always brought my trademark Lucky Strikes, but today they had somehow gone missing, so she had graciously offered to share one of hers.

"Oh it's no trouble," she said, her voice had an almost musical quality to it. "Besides," she said, hypnotically, "you'll pay me back."

Her words were pronounced with utter finality. As if they were a statement of fact roughly equivalent to 'an object in motion stays in motion unless acted on by an external force'. I would definitely pay her back. "Of course," I said, "it's only polite."

"Yes," she said, "but does custom only dictate that a cigarette must be exchanged for a cigarette? Surely there are other things which may be exchanged." I was confused, and possibly hopeful that I was bound to get laid. My latter suspicion was confirmed as she Amyned in to kiss me. "A bargain sealed with a kiss."

She put out her own cigarette and walked inside. I tried to follow her, and possibly to ask what the hell that had meant, but once I had finished putting out my cigarette the elevator doors were already closing behind her.

I walked back inside to my cubicle, and plopped into my chair with a dissatisfied grunt. My password had become muscle memory by this point and the clickity-clackity of the keyboard teased my ears as I tried to get back into the motion of work. I stared at the spreadsheet in front of me and tried to find any and all motivation I could to get through the day. The kiss I had shared with Amy came back to me. I remembered it better than anything I could recall. It was as if I was kissing her all over again. That gave me my little push over the wall of awful and I began moving my mouse, still cursing the me I was in highschool who thought becoming a CPA was the way to go.

About a week of me never managing to find Amy passed before I found myself at a bar, alone. My eyes wandered around, looking at all the pretty women I would one hundred percent strike out with. However, I was in a celebratory mood and would likely go for it anyway, just because my spirits were high. Finally being rid of a bitchy IRS auditor who literally drew frowny faces on tax forms I had personally filled out myself was cause to get drunk on the good shit.

Then I spotted Amy, her trademark red hair now falling upon a thin green halter top, which paired well with her blue jeans and cowboy boots. She was sitting at the other side of the bar, and I was surprised that I hadn't noticed her there before. Once she discovered that I had noticed her she got up and walked over towards me, her hips swaying from side to side and finally finding a place against the bar. She Amyned on the bar and ran her fingers through my hair as she made a show of sitting down on the seat next to me. Then again, she was sexy enough that she made a show of everything she did.

"You know Mark," she said, "It's weird seeing you without a tie, but I sure don't mind."

"You look pretty nice dressed casually yourself," I replied.

She giggled, and it carried all the magic you could imagine with it. "Why thank you," she said, "I say you have got to be the cutest CPA I have ever met."

"Well you have got to be the prettiest," i said Amyving the silence in the air so that she could state her occupation.

"Lawyer," she said simply.

"Lawyer I have ever met." I finished.

We talked about work for a few minutes before I saw her shift gears a little bit. She eyed me, almost cat-like and said "well i do say we have a contract that you haven't fulfilled yet."

"Oh yeah, and what do I owe you?" I asked in the best flirtatious voice I could muster.

"Come with me and I'll show you." She got up and walked towards the women's bathroom. Her ass held by the jeans catching the eye of every red blooded male, and most red blooded females at that, in the entire room. Her hips swayed and I followed her. I felt the guys behind me both cheering me on and damning me to the depths of hell within their minds.

Upon entering the empty bathroom she locked the door and said "and here we are, to fulfill our bargain." My penis began flooding with blood as i began trying to move. "Take off your clothes" she ordered and I followed mindlessly.

After i was fully naked, she produced a pink satin thong from what looked like thin air, and held it before me. "This shall be your repayment. Put these on"

What the fuck? I stared at her dumbfounded and she said, "you owe me, put them on."

"This is too weird," i said reaching for my pants before she barked out her command a third time.

"Thrice I ask and done, put them on." I froze. Her words had reached through my brain and right into my soul. I didn't want to, but still I found myself compelled to comply with her demand.

"What are you?" I asked as I reached for the pair of underwear that she held out before me. By now I was absolutely terrified.

She didn't answer. By this point my penis was softer than it ever had been, but as i slid the panties.on, despite my emasculation, i found the feeling of their pressing against my asshole erotic in a wholly new way.

"Good," she said, "I suppose we could call this bargain done, but judging from the look on your face i can tell you wouldn't be opposed to continuing."

I shook my head, unsure of myself, but still wanting her.

"Well then," she said, "put the rest of your things on and let's go home." I reached for my underpants and found them gone, and I resolved myself to pull my jeans over the panties, my bare, mostly hairless ass pressing against my slacks and feeling all too exposed. Then i threw my shirt on and quickly buttoned up the buttons before following her out.

When we exited the bar I felt this weird feeling wash over me. Instead of hailing a taxi, she hailed a horse and buggy. Our city had them, sure, but I had never ridden in one before. She instructed him to take her home, and he did so. The ride home felt weird. The city felt different, like I had been whisked away to some place that looked like my hometown but wasn't.

We arrived to her apartment, and she invited me inside. "Do you want me?" She asked. I nodded. "Then you will need to do something for me first."

"You're a lawyer," i said, finding my voice finally, "you should know that's quid pro quo sexual harassment." She laughed a predators laugh and I saw her eyes turn to the slitted eyes of a cat.

"No such thing darling." She said. "First, strip." I did, and she came up to me and began caressing my body. My cock began to stir but with a harsh "no" it did not become erect. She kissed me again, and I felt a deep bond form. This was a contract.

"First things first, we're going to be shaving you." I started to back away, but one look from her cat eyes and I suddenly didn't really mind. She walked into another room and came out holding a straight razor. Fear shot up my spine and I thought to cut and run.

I twitched, but my body would not let me. She lathered my crotch with shaving gel and warned "no sudden moves, you don't want to become a eunuch yet do you?"

"Yet?" I asked. Dear God what have I gotten myself into.

"Oh don't worry, I have no plans to take your balls. However, some things trade very highly, and I'm sure they would fetch you a nice price."

A voice inside me screamed, but stayed still and determined to not lose my genitals today. She worked the straight razor so expertly that I wondered if she had done this before. Likely. Then, without warning, she applied the gel toy legs and began working them too. Admittedly I didn't have the hairiest legs I'm the first place, but it still required work to shave them.

Upon finishing she allowed me to move again, and I looked over at the large full body mirror and saw my legs. I had always been insecure about my slightly feminine figure, but I looked so good.

"Wow," she said, "so girly. If I took a picture of your lower half from behind I doubt anyone would be able to tell you were a man." I had since decided to ride this wave and just enjoy myself, and the comment just made me excited.

"No," she said again harshly. My penis began retreating and she placed a hand over it. When her hand was removed i felt the tug of gravity on my now caged cock.

"What the fuck?" I exclaimed. "You said if I let you do this I'd get to fuck you."

"I said you would get me yes, but I made no promises that you would be the active partner." Which was true. I was mad, but a deal is in fact a deal.

She handed me the pink thong and without a word from either of us I slid it on, pulling it up and up until I felt the satin across my ass. Over the next hour she got me all dolled up, with thigh highs, a skirt, a bra, which she padded so I would fit her top, a blue top, makeup and a wig. She had done everything so expertly that it would have been impossible for me not to pass as a woman.

"Wow," i said hesitantly, "I'm," my voice broke, the buried masculinity inside me not letting me speak.

"You're gorgeous," she said. My heart fluttered in a way that it never had before.

"One last thing," she pronounced, "let's go back out there, as two girls." My heart jumped into my throat as fear settled over.

"What?" I exclaimed, "no!"

"Hush," she said soothingly, "no one will recognize you. What's your name for the night?"

I was so scared, i didn't want to go out there dressed like this. My mouth moved without even considering my fear and said "Jasmine."

She squealed in excitement and said "we're going to have such a good night Jasmine."

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The club lights flashed in warm blues, greens and reds, the music thumped with an 'untz untz untz' as Amy and I walked into the club side by side.

"I don't recall ever seeing this place," I said, trying to make my voice audible over the loud music.

"It's for a specific crowd, and has a way of going unnoticed if you're not in that crowd." She said, which despite not being very loud, I could hear perfectly.

The whole place had a very liminal feel, as if it was a place that my soul knew even if my mind didn't. Weed smoke could be detected from certain areas. The combined smell of the various perfumes, including my own feminine perfume Amy had provided me with, made the whole place a cocktail of smells that overwhelmed the analytical parts of my mind, allowing the parts obsessed with the baser functions to have their time in the sun.

We danced for a while just the two of us, but I found myself becoming more and more comfortable. Amy instructed me on how to dance more feminine, and how to really work my hips, ass and chest. Before long I had become comfortable enough that Amy and I drifted a little bit. We were still next to each other, but you could no longer say that we were dancing together.

After a few songs I found myself going up to women and dancing with them, but seeing no luck. I was a bit discouraged, but it made sense, as far as they knew, I was a woman. Then, a man, much larger than me, worked his way over and began dancing with me. He was behind me, grinding, and I, drunk on the atmosphere, let him. I gyrated my hips in front of him as he began moving his hands closer and closer to me.

Eventually he ran his fingers through my wig, and to my shock, it felt as if he was running his fingers through my actual hair. As I turned my attention to my head I realized that I could not feel my own hair mashed under the wig, but could only feel the wig as if it was my own hair. Even so, with how I was, I did not care. I went with it, and looked over at Amy who winked at me as he moved his hands around to grip my breasts.

I barely kept from moaning as he grabbed onto the mounds of flesh which had replaced the tissues Amy had placed into my loaned bra. Part of me wanted to scream, but I just went with it. For all I knew this was a dream, and Amy had just drugged and robbed me, and this was just some weird communication from my subconscious. However it happened, it felt good.

The mystery man's hands caressed my body as he leaned his head in to sniff me. Drinking in my scent evidently did something for him, as I felt his hard cock pressing into my back. Surprising even myself I not only didn't mind, but I even found myself enjoying it. I had made a man hard. A very large, and muscle bound, and oh my god this man is hot.

I turned around and placed my hands on his shoulders. He looked into my eyes and in them I saw the hunger of a wolf in the dead of winter. He had icy blue eyes and hair dyed the same color. He wore a short sleeve button down shirt that barely contained his toned arms and chest. What didn't try to escape was any belly fat, because he presumably had none. I wasn't gay, I had never been attracted to men before. Then again, right now, I was a girl, so I was as straight as they come. Though, when I turned around to look at Amy, I still wanted to fuck the shit out of her, so I guess for the moment I was as bi as they came.

My cock wanted to get hard, but the cage prevented it. Eventually my body realized that the lack of erection did not mean I could not feel the horniness elsewhere, and suddenly I felt this gaping emptiness in my ass.

"It wouldn't be a breach of contract," I heard Amy say, placing her hand on my shoulder. I still wanted her, and I would have her, but this man in front of me had me so horny, in a way I had never experienced horniness before, that I could not resist. He began leading me away, and Amy followed.

We came to a room in the back of the club. In this room was a bed and basically nothing else. As Amy shut the door behind us, I immediately dropped to my knees and dove straight for the man's belt. Even though I had never given a blowjob, I felt the muscle memory of a thousand-year-old eternally young and hot whore taking over. I undid his belt and top button, drew his fly down, and freed his cock. Its girth and length were damned impressive, and my mouth watered in anticipation.

I gripped it with my hand and pumped it a few times until a pearl of precum materialized on the tip. That was when My tongue escaped my mouth to lap up his precum before enveloping the head with my mouth. I ran the tip of his cock across my tongue as I moved my lips up and down the top of his shaft. I used my tongue to stimulate the underside of his head and sucked on his girthy cock.

After a few minutes of trying to stimulate his head I began trying to work my way down until I felt his cock hitting my throat. By feel I could tell that I still had a decent amount of his shaft to go. I tried to relax but could not get past the barrier, so I went back up to suck the head and tried again. I got further, but did not break through. Again and again I went back up and then back down until eventually my throat relaxed and let him pass.

My throat had become a pussy and that very fact made my caged clitty leak. Eventually he grabbed my head and began pumping in and out, fucking my mouth like it was a tight warm pussy. I barely managed to breathe, and thought I was going to pass out, but I kept with it and before long I felt him pull my head off his cock. Taking his cue I stood up and presented my ass to him. I wanted him inside me.

"Stop," Amy said with authority. I turned around to look at her. She had materialized a strap on from seemingly nowhere but had not put it on yet. "Her virginity is mine," she said as she put the harness on, the cock snapping into place. As soon as she had it on and fitted correctly, the cock changed into a real cock. The straps disappeared and the silicone cock and balls fused to her naked skin, replacing her pussy.

Amy's newly minted girlcock was roughly that of the mystery man's. She leaned in and kissed me, then picked me up with ease and set me upon the bed. She moved my panties to the side and sucked on one finger. She then used that finger, wet with her spit to lube up my asshole, or more accurately my boy pussy, before returning her hand to her cock and placing her tip to my hole.

She began to push. I wanted it in me so bad, but physics is physics. It hurt. I did not cry out, but my breathing shallowed and I tried to power through it. She pulled her cock out, spit on it, rubbed it down to lube it up, and tried again. This time it was still uncomfortable, but it went in easier. Once the head passed my sphincter I felt myself relaxing into it. The pain gave way to this weird but oddly pleasurable stretching feeling. To distract me as she pushed more and more of herself into me, she lifted off my shirt, and sure enough I had tits. She squeezed them and it felt good.

"Yes," I moaned. After what felt like an eternity I felt her balls pressing against my ass. She was all the way in. With no ceremony she pulled her cock all the way back out, leaving in just the tip, and slammed back into me with such force I felt like she was threatening the structural integrity of the world. Her cat eyes bored into me as she pounded my pussy unrelentingly.

In and out, in and out, in and out. Thrust after thrust pounded into me. She moved my panties to fully expose my caged clitty. Her thrusts kept coming and kept coming and it was not long before I was a moaning puddle of goo, completely at her mercy.

"Fuck me, yes, fuck my boy pussy," I said over and over. Oh god it felt so good. I was close to cumming and so was she. She pulled out and told me to get on all fours. She positioned herself behind me and the mystery man positioned himself in front of me. She returned to pistoning into me as I opened my mouth and allowed the man to piston into my throat. The overwhelming sensory overload threatened to break my mind.

With a final scream of "yes take it" I felt Amy unload inside my ass. This was a pleasure that was unlike anything else I had ever experienced. It wasn't an orgasm, but it was close. It was sexual in a way completely different from an orgasm. She pulled out and realized that I still hadn't cum from her fucking me, so she moved to my front and the mystery man moved behind me.

He was not nearly as gentle as Amy was. He just entered and started fucking me at full pace. It was hard to focus on anything else, but AMy clearly wanted me to clean her cock. I felt so dirty sucking a cock that was just in my ass, but I did. The taste of my ass, mixed witht the saltiness of her cum was overwhelming, and I loved it.

The mystery man knew how to work a bussy and with a feminine cry I began leaking cum all over the bed. I continued whimpering as he clearly did not care if I had cum, he was going to unload. Amy for her part was hard again and had begun thrusting into my throat. The feeling of being spit roasted while cumming from anal only is unreal.

I had not come fully down from my last orgasm before I felt another crashing wave of pleasure and my clitty leaked even more. Eventually I ran out of juice to sputter but the orgasms just kept coming. Eventually I felt both cocks in me pick up pace and knew what was coming. A flood of cum hit my ass and mouth at the same time and I felt like I was being drowned in it. I came with them of course, and felt like my soul had left my body and went to a realm of pure pleasure. The cocks eventually pulled out of me leaving me a mess on the bed.

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