tagTranssexuals & CrossdressersNew Years in New York

New Years in New York


Disclaimer: The following story contain explicit descriptions of consensual sexual activity and are not suitable for reading by anyone under the age of 18, or anyone offended by reading such material. These acts include bisexuality, cross-dressing and other fetishes and perversions.

This story is pure fiction and fantasy. I encourage everyone to practice safe sex. The story is the property of the Author. Any feedback would be greatly appreciated. Thanks.


My name is Kevin, I am 28 years old and single. I am 5'10" tall, weigh 150 pounds, I have short blonde hair and blue eyes.

It was my first trip to New York. I had recently started a job as a reporter for a small TV station in Raleigh, NC. I convinced management to send me to New York to cover the ball drop on News Year Eve.

It was my first big assignment and I was excited and eager to show what I could do. It was just me and my camera man Robert. The drive up was uneventful and Robert and I seemed to feel at ease with each other.

We arrived a couple of days early, on December 29, so we could do a couple of stories leading up to New Years eve. A couple of human interest stories and maybe a story or two on the history of the New Years eve celebration at Times Square.

Let me tell you about Robert, he is tall with curly brown hair and brown eyes, He is in great shape and he is with a different girlfriend each time I see him away from the station. Robert said he had an Aunt and uncle who lived on Long Island and that was the reason he wanted this assignment so bad.

Since Robert was going to stay with his Aunt and cousins, he said that we only needed to get one hotel room. We arrived at the hotel around 5:30 and Robert put his suitcase in the room and grabbed his overnight bag. He said he was taking the subway to his aunts house and would be back around 9 in the morning so we could scout locations to broadcast from during New Years Eve.

After Robert left I opened the mini bar and fixed myself a mixed drink of vodka and orange juice. I sipped my drink and flipped through the channels on TV. After about an hour I decided to take a long shower. I keep my body shaved except for the hair on my head.

When I finished my shower I dried off and decided it was time to become Joanna. That is right, I have been a cross dresser since I was 15. I love women but there have been a few times I had sex with a man so I guess I was bi, but deep down I saw myself as a woman when I dressed.

I am sure Robert wondered why I had so many suitcases. Little did he know that tow suitcases had all of my feminine clothes in it. I started not to bring Joanna's suitcases with me, but since I would have the hotel room all to myself I could not resist turning Joanna lose on the Big Apple.

It was almost 6:30 when I started my transformation. The first thing I did was to slide my pink garter belt up my waist. I always get a tingle when I feel the garters hit my thighs.

I took out a pair of white silk stockings and sat on the bed. I slowly rolled the stockings up my smooth legs and attached the stocking tops to the garter belt. Next came the lacy pink panties with the little bow in front.

I had to stop and fix myself another drink to settle my nerves. I gulp this one down and returned to dressing. I hooked the pink lacy bra together, then turned it around and slipped the straps up my arms. It was a padded bra and gave me a nice set of 34 C Breasts.

I decided on a short black pleated skirt. I had a very small cock but the pleats helped me conceal what I did have even when I was hard. I put on a thin silk blouse that allowed just a glimpse of my pink bra. I thought about wearing a camisole over the bra but I liked how the bra peaked out when I left the first two buttons undone on my blouse.

So far so good. I took out my makeup case and put on blush and eye liner, not to much though. I painted my lips a deep red color. Next I took out my long red wig and fixed it into place. Then I brushed it out. I looked into the mirror and saw a fairly attractive red head looking back at me. I know I would never be considered beautiful but I thought I looked good.

It was time for another drink. I was starting to feel really good. I slipped on my two inch black heels and when I tried to stand I was a little light headed. My intention was to just dress up and stay in my room.

At around 8 the phone rang and it was the station Manger calling to make sure we had arrived ok. She said she could not wait to see the stories we would do. After I hung up the phone I checked myself in the full length mirror again. I decided that I looked to damn good to stay in my room. I mean what would be the harm of getting a drink in the hotel bar?

I put on a silver necklace and the matching bracelet and ear rings. I grabbed my little black purse, put some tissues, my lipstick, some money and my hotel key into it and I was ready to go. I checked myself in the mirror one last time then headed out.

Even though I had been out in public before I was still nervous as I rode the elevator down to the lobby. People were getting on and off at every floor but no one pointed and scream so I was starting to relax when I left the elevator and headed to the bar.

The bar was crowded since so many people were in town for the new years eve celebration. I made my way to the bar and order another screwdriver. I set on the stool and checked out the crowd. Some couples were trying to dance even though the space on the dance floor was limited.

As soon as I finished my drink the bartender brought me another one and told me that it was from the man at the end of the bar. I looked in the direction the bartender pointed. Oh my, a very well dressed black man held up his glass and I tried to give him one of my sexiest smiles. It must have worked because he came over to me and introduced himself as Steve. In my most feminine voice I told him my name was Joanna.

Steve was even more handsome close up. He had black hair and it was almost what I would describe as a buzz cut. He also had a mustache and a neatly trimmed beard. Steve was over 6 feet tall and it looked like he worked out.

We tried to talk over the blaring music but he had to stand close to me so we could hear each other. He was leaning in close telling me how pretty he thought I was. He also had his hand on my thigh and my skirt was pushed up exposing my stocking tops. If I had not been so drunk at this point I am sure I would have pushed my skirt down.

By now Steve was kissing my neck and nibbling on my ear. His hand had worked up ever farther. If I was not careful he would be rubbing my cock soon. I was afraid of how he would react if he found out I was not a real woman. Finally I reached down and stopped his hand.

Steve seemed disappointed but then he asked me to dance. I told him I was not a good dancer plus the floor was too crowded. He told me he did not like crowds that much but he wanted to get out of his hotel room tonight. He then said he was glad or he would not have meet such a beautiful woman. Then he kissed me. lightly at first but then more passionately and forceful.

I almost melted in his arms. Maybe it was the alcohol but I found myself kissing him back. I did not even try to stop him when he pushed his tongue past my lips. When he started exploring my mouth, I started sucking on his tongue. he pulled me off the bar stool and to my feet. I felt his hands caressing my back and then they went to my butt. Steve was squeezing my ass so hard he was all but lifting me off the floor as we kissed.

He finally broke the kiss and we parted. I reached for my drink and gulped it down. I guess I started to sway because Steve put his arm around me to steady me. He told me that he thought I needed some fresh air so he led me out of the bar. He had his hand around my waist and He never let go of me because he was afraid I would stumble and fall. I clung to his masculine body as we left the bar.

Out in the lobby Steve asked me if I wanted to call it a night and have him walk me to my room or did I want to go to his room and maybe we could get to know each other better. I just smiled and said I would love to see his room. We got off the elevator on the fifteenth floor. He finally let go of me so he could unlocked the door.

Once in his room He sat me on the bed and asked me if I wanted another drink. I told him that I did not think I needed another drink. I took his hand and pulled me him to me and told him, "All I need right now is another kiss."

We started kissing again and soon we were laying on the bed side by side with his arms around me. He started kissing his way down my neck and soon he was unbuttoning my blouse.

I was lost in the moment and soon he had my bra undone and was sucking on my nipples. Between the lust I was feeling for Steve and the alcohol I had let down my guard so when I felt his hand moving up my thigh I was slow in reacting.

Before I could stop him I felt Steve's hand on my cock. We both froze. I was afraid that Steve was going to freak and kick the crap out of me for leading him on.

Steve sat up and looked down at me. I was all but in tears as I pleaded with Steve not to be angry. I kept telling him I was sorry. I did not mean to mislead him. I had not intended for it to go this far.

Steve had still not said anything yet. Finally he just smiled, shrugged and leaned down to kiss me again. When he broke the kiss, he took me into his arms and pulled me tight. He told me that he had never ben with someone like me but that he was open minded.

He smiled again and said "You make a beautiful woman and you turn me on, I hope I did not ruin the moment."

I let out a sigh of relief and started to slide down the bed. First I removed his shoes and sock, then I undid his belt. As I did this he pulled his shirt up and off. I unbuttoned and unzipped his trousers and pulled them down his legs and off. He did not have on any underwear and his semi hard cock looked delicious so I kissed the head.

He moaned as I sucked the head into my mouth and started sucking hard. As I sucked the head I reached down and started squeezing his heavy balls.

I let the cock slip from my mouth and started licking the shaft. I licked down and started sucking on his balls, causing Steve to start moaning. By now Steve was rock hard and his cock was over 7 inches long and thick.

I gave his balls one last kiss then took the cock back into my hungry mouth. I was taking all 7 inches and thought Steve would enjoy cumming in my mouth so I prepared to swallow a load of cum.

Steve had other ideas, He pushed me off of his cock and the he forcefully turned me onto my stomach. When he pushed up my skirt and ripped my panties from my body I knew what he wanted and I started begging Steve to slow down and to let me get some lube. He ignored my pleas as he shoved a pillow under me so that my ass was in the air.

He spread my ass cheeks with his hands and rammed his cock into me in one swift motion. I am sure that if they were anyone in the adjoining rooms that they heard my scream.

He pulled out until all that was left in me was the head of his cock. Then he rammed it deep again this time only stopping when he had all seven inches in me.

He kept muttering how tight my sissy cunt was as he started to fuck me in a slow rhythm. Maybe the liquor had dulled my senses because the pain quickly went away and I felt a fire start deep inside of me.

As Steve started fucking me hard and rough I reached under me to squeeze the head of my own cock, I knew it would not be long until I came.

I could not resist the feeling any longer and shot a load of cum onto the sheets underneath me. Steve continued to fuck my butt for several more minutes. Suddenly he shoved his big cock into me and held it there shooting his load deep inside of me.

After he came, Steve collapsed on top of me, we both lay there catching our breath for a few minutes then I felt Steve pull his cock out of me and I felt empty.

I felt Steve slap my butt hard as he told me to roll over. I rolled onto my back and Steve worked his way up to straddle my chest pinning my arms under him. He put his hand behind my head and pulled my mouth to his slimy cock.

I was forced to suck and lick his cock until it was clean. When he was satisfied that I had cleaned his cock properly He held my head in place and started to fuck my mouth. He did not care how much I gagged as he continued to force his cock in and out of my mouth.

He was breathing hard and it surprised me when he pulled his cock from my mouth and started cumming on my face. When my face and neck was covered in cum he got off of me and went to the bathroom and relieved himself, I was not sure what to do but I found my ruined pair of panties and used them to clean the cum from my face.

When Steve returned he couldn't look me in the eyes, finally he tried to apologize, he kept saying he was sorry for the way he had acted, he did not know what came over him.

I went to him and put my arms around him. I whispered in his ear that it was ok. I kissed his cheek and told him that sometimes I loved it rough and I thought it was hot what we did. He seemed relieved. I think he was afraid I was going to scream rape or something. We made out for a little bit longer then I went to the bathroom and cleaned up as best as I could. My makeup was ruined but I did manage to touch up my lipstick.

I got dressed and kissed Steve one more time as he walked me to the door and gave me a good bye kiss, he said he was glad he got to have some fun tonight because he was leaving tomorrow morning for San Francisco on business.

I was still a little tipsy but I managed to get back to my room without incident. I decided to shower again. When I was done I took out my favorite pink lace teddy (I really love pink lingerie) and fixed myself another drink. It was still early so I laid on the bed and watched some cheap porn on the TV.

I figured I would set the alarm clock to go off around 6 so I could change and hide all evidence of Joanna before Robert came back to the room. Between the drinks and the wild rough sex with Steve I was exhausted and drifted off to sleep. So imagine my surprise and shock when I was awaken from the sound of someone laughing. I glanced at the clock and seen that I had slept straight through the night and it was already 9 in the morning.

At some point I had rolled over onto my stomach. I just wanted to bury my face in the pillows and hope that it was a bad dream. I knew it was no dream when Robert quit laughing.

I heard him say, "Nice ass Kev, I did not know you were a sissy fag who wore lingerie."

I did not answer Robert but I sensed him coming closer, then I felt him swat my ass, not hard but enough to get my attention.

I finally rolled over and faced him. I knew my face was bright red from embarrassment. "Please do you have to speak so mean to me? I will go change and we can forget any of this ever happened."

"I do not think you are in any position to ask for any favors, I wonder what the station manager will think when I tell her?"

"Oh God Robert, please I am begging you, don't tell anyone, PLEASE!!"

He gave me a lecherous grin,"I tell you what, maybe we can work something out and no one will need to know."

"Thank you, Thank you, Thank you, I knew you were a good guy, I will go change right now."

I thought he was going to let me off the hook. How wrong I was.

"Stop right there, I did not tell you that you could go change."

I froze in place.

"Turn around for me and do it slowly. I want to see your outfit."

I took a deep breath and did a slow 360 degree turn.

"Not bad, now go set on the bed for me."

Please Robert can't we just get to work and put this behind us?"

"You will do as I say or I will expose your secret to everyone at the station, you know how word gets around in this business I doubt if you would ever get another job anywhere in the country."

I looked at the floor and mumbled a weak "Yes Sir."

I went to the bed and sat down. I was told to lean back and spread my legs. Then I had to start rubbing my cock through the lace of the teddy like I was rubbing my pussy and clit.

Robert then made me pull my cock free of the material and star stroking it. First he laughed at how small it was then He asked me what did I do last night and I told him I went to the bar.

"You went dressed as a woman right?"

"Yes Sir."

"Did you get hit on by any guys?"

"Just one."

"Did you leave the bar with him?"

I nodded yes.

"Where did you go?"

"To his room."

Robert ordered me to lay on my side and continue to stroke my cock with one hand while I reached behind me and start pushing a finger inside my ass.

As I pushed a finger into my ass Robert must have seen me flinch because he asked did it hurt. I told him it did.

"Why? Did you get fucked last night and your ass is sore this morning?"

I thought I was going to die from the humiliation but I managed to answer him.

Robert made me tell him all the details from last nights encounter as I laid there, jacked off and fingered my sore ass.

"I see your small cock is rock hard, are you ready to cum?"

"Yes Sir I am very close."

"OK you may Cum but when you do you had better catch every drop and lick your hand clean."

I think I started shooting before he finished the sentenced, I did as I was told and caught all my cum in my hand and when I stopped cumming I raised my hand to my lips and licked up every drop.

"Good little cum slut. Now go get dressed we have work to do. I am sure you have panties and pantyhose to wear under your male clothes, don't disapoint me."

When I was dressed and had returned to the room, Robert made me undo my pants and show him the tan pantyhose and red panties that I had on.

We walked around New York and shot some footage. I did a few interviews of people on the street, asking them if they were going to be in Times Square when the ball dropped and what were their resolutions for the new year.

We finished work for the day and had a quick snack at a local Deli that Robert liked then headed back to the room. When we entered Robert asked me where were the feminine clothes that I had brought to New York with me.

I pointed out the two suitcases and he started to go through them. He laid out a black corset with garters, black stockings, black lace panties and my very snug little black dress.

He said he would start editing and for me to go get fully dressed, makeup, wig, the works and he had better be impressed or I would not like what might happen. I started to argue but decided what was the point.

It took me almost 45 minutes to dress and do my makeup but when I entered the room Roberts jaw almost hit the floor. I guess I looked a lot better than he thought I would.

Robert recovered, "Not bad sissy bitch, get over here and see if you approve of what I have done. As I stood beside Robert and watched the video, he reached out and started feeling of my ass. He started to roughly squeeze my butt cheeks through the thin material of my dress.

I managed to tell him that he did a great editing job and I sent the file over the Internet to the station in Raleigh. I hoped that with our work done for the day that Robert would leave and go back to his Aunts place.

Robert had other plans. As soon as the file was uploaded, he stood up and started unzipping his pants. He pushed them and his underwear down to his thighs and exposed his semi hard cock. In the state that it was in it was still 6 inches long.

I was ordered to kneel in front of him and give him my best blow job. As I kneeled between Robert's legs and slowly started to run my hand up and down his cock, I thought to myself that this was not to bad, Robert was a good looking guy with a nice size cock. I quit worrying about what would happen later if Robert decided to tell someone about me and threw myself into the job at hand.

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bySissyAndi© 3 comments/ 34424 views/ 9 favorites

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