Where do I begin? I’m normally not very open about my private life, seeing as I grew up under the pretense that secrets are meant to be secrets. However it seems I have come to a point where I am comfortable with who I am and where I have been. Comfortable enough to bare to you all my deepest secrets.
Deep breath in, slowly let it out.
My name is Alicia, well that's my new name, my old name is Michael. If that confuses you then I should explain that I am a cross dresser, been so for about a few years. It used to be a behind closed doors kind of hobby, doing it when I was alone and for my own pleasure. I remember the first time I ever felt the smoothness of women’s underwear, the sexiness of its cuts and the feeling of it snug on my girlish bottom and penis.
Never caught, my obsession grew from just scouring my sisters’ closet to ordering my own wardrobe from random online stores. I soon amassed enough clothing to supply the female co-eds around the country. I would dress when I had the house to myself and the obsession grew from my lonesome to sharing it with others.
Finding sites online that catered to my particular fetish, I started to show myself off, dressing and taking pictures for men, and thus discovering my taste for the same sex. Teasing and cybering became my forte but soon I grew bored with it and I dared to step out of my Internet shell, and take my obsession to real life. It was tough finding someone with whom I could confide my lust and passion but soon I was able to acquire an admire, a man by the name of Mr. Carlson.
Mr. Carlson lived a few counties away but he was interested from the beginning. Sharing fantasies and some personal information I found out that he lived in the same state and even found out that he had a wife. Any normal person would probably have their mind flashing red lights screaming “STAY AWAY,” but this drew me in, this man found me sexy knowing I was a cross dresser and even found me sexier than his wife. After many excuses, my hormones got the best of me, and I decided to meet with him, and this seems like a fine place to begin my story.
Chapter 1
I stood outside of a gay bar in Scottsdale County, nervously checking my phone for both the time and to see my messages. My inbox read 0 and the time had hit 10:17 pm. Mr. Carlson was late, and I was beginning to have second thoughts. My legs turned me and I started to walk away when I heard someone call out my name.
“Michael?” a voice from behind me, called out.
I turned to see a handsome man in his late 50’s. Pepper colored hair and steel blue eyes. His black suit jacket open and collared shirt unbuttoned, the signs of the end of a work day.
“Yes," I sheepishly answered lowering my head a bit to hide my embarrassment.
Mr. Carlson looked at me and smiled then looked at the bar door. "Apologies for being so late, the wife was talking my ear off, shall we take this inside?" he said in his smooth voice that screamed scotch on the rocks and blue collared love. He pushed his hand out to hold the door open for me, and without a word, I walked in. As we entered the bar the whole atmosphere reminded me of a jazz bar. Lights on dim, music playing from the jukebox and a few men scattered around.
As I sat down Mr. Carlson moved towards the bar coming back in a few moments with two scotches on the rocks. Called it, I thought to myself as I let out a little smirk. Mr. Carlson placed my drink down in front of me then sat down opposite of me and took a long sip. He placed the glass back down licked his lips and stared at me with those steel eyes.
“What’s so amusing?” he said letting out a smile himself. God I could bury myself in that voice.
"Nothing just laughing at the oddity of this whole situation,” I replied. Grabbing my glass I immediately shot it down hoping the alcohol could numb my embarrassment.
“What’s so odd about it?” Mr. Carlson leaned in closer to me. “It’s nothing more than a bored old man and his new young friend.” His smile stayed on his face and he grabbed his glass and took another long sip, all the while not removing his stare.
“I think you know what I mean sir.” That was a bit too formal, I thought, but Mr. Carlson didn’t seem to mind as he chuckled back at me.
“No I don’t, do tell.” He’s playing that card now, not wanting to make the first move, well I’ll show him two can play at that game.
“It’s odd that a gentleman such as yourself fancies cross dressers like me.” Maybe that was a little too blunt. Perhaps I forgot how much of a lightweight I was, or maybe I forgot that I had taken a few hits from my flask on the train ride here.
“Maybe I just fancy cute boys who like to be a little feminine,” he retorted, lifting his glass up to his lips to finish off his drink.
Still playing hard to get and with my hormones taking over I couldn’t handle the suspense anymore. “Well why don’t you find out how feminine I can be.” Wow okay Mr. Porn star, or would that be Ms. Porn star.
Either way the alcohol was definitely working, and as I leaned forward, I forgot about my little preparation. The fabric of my thong started to rub along my ass and stick out. My eyes widened as I forgot that I was this bold on a first encounter. I stood up in a haste shuffling out of my chair.
“Umm bathroom break.” I said as I broke eye contact and attempted to make my way to the bathroom.
Eventually finding the door, I ran in and immediately turned to the sink. Pouring out cool water I splashed some on my face as I took a few deep breaths. My god I can’t believe how far I was going with this. This was just a fantasy right? Lifting up my shirt I turned around and faced my rear to the mirror. Sticking out was the top of my black thong creating a cute V shape.
Nope this definitely isn't a dream. I was really wearing this and meeting with a man I met online. I should leave now before this goes to far. Tell him it was a mistake and think about this a bit more. But the alcohol was going to my head and the sight of my round perky ass in a thong was getting me hot.
I ran my hands over my behind pulling down my jeans with my thumbs letting my whole ass breath. My hardness starting to poke at the front I ran my hands down my smooth stomach feeling it. God it felt good to get a hand on it. Just then I heard the door handle and the creak of the door. Oh shit I forgot to lock it. I turned and saw Mr. Carlson walking in.
He stopped halfway then gave his little smirk seeing my in this position. Continuing in he shut the door and stared at me with those eyes as his pace brought him in front of me.
“It’s not very nice to leave someone so abruptly without an explanation. If you wanted to release some tension,” his hand outstretched and landed on my cock. Rubbing it through the black silk thong. God his hands felt so firm and soft at the same time. “you should have asked me.”
He placed his hand under my chin and brought my mouth up to his.
His kiss hit me like a wave of warmth and his tongue forced its way into my mouth to dance with mine. His hands worked there way inside my thong and he pulled my cock out to stroke it. He broke our kiss and placed his other hand on my head slowly pushing me down to my knees.
I was face to face with his crotch and my heart was beating like a drum. It seemed like forever as he unzipped his pants and pulled out his cock. Oh his cock was beautiful it wasn’t too long and it wasn’t too wide. It was dare I say perfect. I looked up at him with some worry on my face, but it was all dashed away as I saw him smiling with lust in his eyes.
“Well, show me how feminine you really can get.” His voice danced in my head and lingered there.
Coupled with the smell of his cologne on him, I was entranced. My gaze slowly turned back down to his awaiting cock. I slowly moved my head towards it and opened my mouth. Letting my tongue out to breath as it flicked over his tip. I tasted his salty pre-cum and god did it taste good. Licking more around his head I took the plunge and wrapped my lips around it. It was my first time having a real cock in my mouth and the feeling sent me over the edge. I could feel my own cock throbbing inside of my thong. I reached my hands down to caress my erection as I slid more of Mr. Carlson’s' cock into my mouth.
His moans became louder as I picked up the pace letting my lips suck off his entire length. Popping it out of my mouth I outstretched my tongue and licked its entire length. My tongue ran down to his balls as I intently licked them and took one into to my mouth to suck on. God what a slutty thing for me to do.
A month ago I was only dreaming of this but now here I am living out my wildest fantasy. I brought my hand back from my cock to his and placed it back into my mouth stroking it as my mouth engulfed it once more. Mr. Carlson placed his hand on my head as he let out a few more moans as I devoured his cock. Suddenly I felt his hand on my cheek and him forcing my mouth off.
“Wait, wait not so fast,” he said panting.
I looked up at him with a little spit still dribbling out the corner of my mouth.
“I want to fuck you,” he stated boldly. That was something I was not expecting. Up until this point I was barely able to get the tip of my dildo in my ass without stopping in pain.
"I don't think so, I've never taken anythi..." My sentence was broken as Mr. Carlson bent down and embraced me in another kiss. The feeling of his lips and the smell of cologne hit me again, and I became entranced.
His mouth left mine, and I looked into his steel blue eyes. "I promise I won't hurt my little girl." He ran his hand down my arm and to my bottom as he hooked it around my hip to turn me around.
Without a second though I got onto my knees and presented my ass to him. My brain wasn't answering anymore, my body was. I felt like such a slut feeling the cool air brush along my hole. Mr. Carlson got down on his knees and placed a finger in his mouth getting it nice and wet. He popped it out and with the other hand pulled my thong to the side and slowly worked his finger in my ass.
I let out a little moan as it went in feeling the cool wetness. Soon a second finger was worked in, and I winced from the immediate pain, but I soon eased up as he massaged my insides. Pulling his finger out he then placed his cock at my hole rubbing it up and down.
“Ready baby?” he asked in the silky voice again.
How could I say no? “Fuck me sir,” I said under my breath.
Even though I couldn’t see his face, I knew he was smiling. Holding his cock, he started to push the head into my hole, and it went in with a slow pop. Another moan escaped my lips as he left the tip in and rubbed my ass cheeks giving them a light slap. God I loved the way this man handled me. Grabbing my hips he slowly pushed more of himself into me. I let out a little girlish moan as I felt him bottom out inside me.
“There’s the girl I was waiting for,” he said as he pulled back and slowly drove in me again.
I couldn’t believe how great it felt. The fullness and the warmth, it was complete ecstasy to me, and I was in heaven. He started to pick up speed as the sound of my ass hitting his hips got louder and started to echo in the bathroom. His hands reached up and grabbed at my ribs as he used me to push himself harder and faster. I lay there on my hands and knees moaning like a whore.
“You like my cock in you baby?” Oh god now he was talking dirty to me in that voice.
“Yes sir it feels so good,” I said back in between my moans.
“Do you want to be my sissy little slut?” My god this man had a way with words in normal conversation and in the heat of the moment.
“God yes sir I want to be your slut!” I screamed out as his cock was plunging into my tight asshole, his hands now at my hips as he smacked me on the ass.
“Are you going to dress up for me and service my cock at every beck and call?” He screamed at me.
It was getting too much for me. My cock was slapping back and forth as he fucked me, and I was nearing my climax.
“Yes sir I am yours!” I screamed out as my cock started to spurt cum all over the floor as Mr. Carlson was continuing to slam his cock into my asshole at a vigorous pace.
“I’m going to cum in that tight little asshole, oh god I’m going to cum!” With his last exclamation he slammed his cock balls deep into me and that’s when I felt his cum.
So hot and so much shooting into me, I could feel it filling me up deep inside. It seemed to go on forever as I leaned my face onto my hands. He slowly slid his cock out and I could feel the cum dripping out my freshly fucked hole. All I could do was lay there in complete euphoria.
Mr. Carlson stood up and placed his cock back in his pants and zipped up. Leaning down he helped me up as I pulled my thong back on and put my pants on. I was still wobbly from getting fuck and as we left the bathroom I could see the stares from the bar patrons.
Our sounds definitely were easy to pick out and in a gay bar I'm sure everyone knew what had happened. I felt like such a slut as there stares were on us and the slow feeling of Mr. Carlsons' cum dripping out of my asshole. As we got outside Mr. Carlson pulled out a business card and a pen and started writing down a small note.
“Next week on Monday be at the Scottsdale Train Station." He handed me the card, and I looked it over seeing just a time and place, "A limo will pick you up and take you to one of my apartments. I hope you plan on taking the week off.” With that he grabbed my hand and gave me one last kiss.
He turned and walked away, disappearing into the night. I stood there in awe as my mind came back to me and started to wrap itself around what had happened and the prospect of what’s to come. All I could think to myself as I walked back to the train station for my ride home was the cum now wet in my pants and the week that was about to come.
