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.
NEW YEARS IN NEW YORK
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.
First I started planting sloppy wet kisses up and down the shaft of his cock. Then I licked the underside of the shaft. By now his cock was completely hard and was probably close to nine inches. No wonder Robert did so well with women.
I took his cock into my mouth and started to suck it. I kept my hand at the base of his cock as I started working my mouth up and down the shaft. Each time I went down I would take more and more of his cock and when I pulled back you could a dark red ring from my lisp tick where I had stopped.
I was not able to take all nine inches into my mouth but I did manage at least seven. Robert must have been enjoying himself because he had his head back and his eyes closed. He was emitting soft moans of pleasure.
Robert had stamina and it took over twenty-five minutes of me sucking his cock before I felt a hand at the back of my head forcing me to suck harder and bob my head up and down faster.
I was rewarded for all my hard work when Robert gave a loud grunt and shot a huge load of cum into my mouth. I felt strand after strand hit the back of my throat forcing me to swallow as fast as I could. Still there was so much that some dribble out of the corners of my mouth and down my chin.
Robert finally let go of my head but I continued to milk his cock with my mouth. He eventually pushed me away and told me to go touch up my makeup, we were going out to diner.
After I made myself presentable again, we went down and caught a taxi. Robert told him the address of the restaurant and we pulled away. Robert pulled me close and I rested my head on his shoulder and I felt Robert's hand on my thigh slowly caressing the bare skin just above the stocking tops.
He said that he had not thought to ask if I had a feminine name I went by because he did not think calling me Kevin, bitch, slut or whore in public was a good idea. I told him it was Joanna.
We arrived at a fancy French restaurant and I asked Robert how would we ever get in since a place like this would be booked up weeks in advance, especially over the holiday season.
Robert just smiled at me and said he had a plan. His cousin was the head waiter for the place but it may take more than that. I was enjoying being out on the town as Joanna and I was busy taking in al the sights and sounds of New York so I did not think anything about it and just figured he would have to bribe him a little.
When we entered Robert introduced me to his cousin Richard and asked if he could squeeze us in. Richard said he would try but it might be a while. Robert leaned in and whispered something in his cousins ear and when he did, I caught Richard's eyes going up and down my body.
Richard grinned and said he thought he could work something out. It turned out that Richard had more pull that I thought he did because soon Robert and I was seated a romantic table tucked into the back corner of the restaurant. It was very secluded, no one passed by.
It was a lovely meal and Robert was an exceptional conversationalist. I was almost convinced I was on a real date. It was almost time to order desert when Richard came by our table.
He stood right next to me and got very close. I heard him ask Richard if I was ready to do it. I looked at them both and asked, "do what?"
Robert gave me one of those looks and said that part of the deal was that if Richard got us in I would give him a hand job. I think Richard expected me to say no or at least resist a little. I thought a hand job for a great evening was a spectacular deal so I smiled up at Richard and asked him where he wanted to do it.
He glanced around and quickly unzipped his fly. I reached out to fondle his cock and squeeze the head. He was already hard as I started working my hand up and down the shaft. He was nowhere near as big as Robert or Steve for that matter but it felt good in my hand.
Richard was enjoying the hand job but it was taking him way to long and I was afraid someone would see what I was doing so I decided to hurry things along, I leaned down and gave the head of his cock a few good licks, then took the head into my mouth as I quickly worked my hand up and down the shaft. I thought Richard was going to collapse when he started cumming.
He managed to stay on his feet. I liked his cock clean then tucked it back into his pants and zipped him up just as the waitress brought our dessert.
She caught me pushing a errant drop of his cum into my mouth and the look on Richard's face. As she set my chocolate moose in front of me she winked at me and said that she hoped I enjoyed my desert as much as I had enjoyed Richard.
Richard over heard her and slapped her playfully on the butt and told her to mind her own business. They both were laughing as they left the table.
Later during the cab ride back to the hotel, Robert said "You really enjoy being a woman don't you?"
I told him I enjoyed it a lot, and this had already been the most exciting couple of days of my life and we still had at least one more day and night left in New York, even if we were working tomorrow night.
Robert hugged me and told me that tonight was not over yet. When we got back to the hotel we stopped at the bar for a couple of drinks, I was not going to over do it like the night before so I ordered a black cherry Mojito and nursed my drink as I watched the people.
Robert even managed to pull me onto the small crowded dance floor and held me in his arms as we danced to a slow song. We started kissing and I felt his hands back on my ass as we danced. I started to grind my body against his already hard cock.
Soon after that Robert asked me if I was ready to go back to the room. I told him I had been ready. He responded by telling me I was a good little whore.
Roberts hands were all over me while we were in the elevator. When we reached our floor the doors opened and they were two couples waiting. After they had got on and the doors were closing I heard the cute blonde say "He is going to get very lucky tonight" and they all laughed.
By now all pretense of Robert "forcing" me to do things were out the window, it was obvious to both of us that I wanted to be Roberts slut and would do anything to please him.
Back in the hotel room we kissed frantically as our passion over took us. I broke the kiss and smiled up at him then started to slowly undress Robert. I slide his jacket over his shoulders and off. Then I pulled his shirt from the waist of his pants and as I pulled it over his head and off I kissed his flat tummy then kissed and nibbled at his right nipple.
I undid his belt, unbuttoned his pants and let then gather around his ankles. He lifted his right foot then his left foot as I removed his shoes, shocks and slipped his pants off his body.
His hard throbbing cock was at eye level and I could not resist kissing the slit then sucking the head for a few moments.
"Baby slut, that fells good but that is not what I want right now."
I let his cock slip from my mouth, pushed him back and he fell onto the bed. As he watched, I stood up and started doing a slow sexy dance for him. As I danced I reached down and took the hem of my dress and slowly raised it exposing first my panties, them my corset eventually lifting the dress over my head and throwing it onto a chair in the corner.
I turned my back to Robert and wiggled my ass as I slide the panties down and off. I reached behind me and spread my ass cheeks as I looked over my shoulder and sexily licked my lips.
Then I said in my most feminine, most sexy voice, "Please Robert, will you make love to my tight sissy ass? Will you fuck me hard and deep and make me your bitch?"
Robert seemed to think that was a great idea because he jumped off the bed and forced me down onto my hands and knees on the hotel floor.
before I could protest, I felt the head of Robert's hard cock pressed against my anal ring. Like Steve, Robert entered me with one hard thrust. Again it hurt but I bit my lower lip and managed not to cry out in pain.
Robert did try not to be to rough, well at the beginning anyway. Soon he was ramming his rock hard cock deep into me and I felt his heavy balls slapping against my ass.
Robert surprised me when I felt his hand on my small cock. As he fucked me he started to stroke my sissy clit. I felt it build inside of me and soon I came hard.
He continued to fuck me hard before he came. When he finished shooting cum deep inside me we both collapsed on the floor. We were both covered in sweat but my sweat was mixed with cum.
After we regained our strength we crawled into bed and feel asleep. I awoke early the next morning with my back to Robert, he had his arm around me and I could feel the head of his cock nestled between my ass cheeks. I don't know what he was dreaming about but he was already rock hard.
I managed to move his arm and crawl out from under him without waking him up. I went to the bathroom to clean up and when I returned Robert was on his back snoring lightly. The sun was not up yet and I did not want to wake Robert up but I could not resist. I bent down to take his cock into my mouth again. I had planned to give Robert a nice slow blow job, but after seeing that beautiful cock sticking up I got a better idea so I crawled onto the bed and straddled Roberts cock.
I reached behind me and spread my ass cheeks again. Robert was a heavy sleeper but he woke up when I lowered my ass onto his cock. I slowly sank down until I had all nine inches in me. I sat there a few seconds and enjoy the feeling of being full.
As I started to rise up and down on Robert's cock, he reached up and started playing with my nipples. The faster I rode up and down on his cock the harder he pinched and twisted my sensitive nipples. Between the cock in my ass and the feeling of my nipples being manipulated I could not help it when I shot a load of cum onto Roberts belly and chest.
When I came, the contractions in my ass milked the cum out of Robert and he shot his second load of the night into my ass. I apologized for coming on him but Robert said it was ok, as long as I licked it clean.
First I licked the shaft and the area around the base cleaning his cock. Then I licked my way up cleaning off his belly then his chest. I could not resist nibbling his left nipple before I finally rested my head on his chest.
That is how I feel asleep as Robert covered our bodies with a sheet.
The next morning as we were getting ready to head out to do some more interviews and take some footage of the preparations for the nights celebration my cell phone rang and it was our station manager.
She said she had some bad news, the station owner refuse to pay for the satellite feed so our live broadcast had been canceled. She told me to do a couple more human interest stories if we could find them, then we could head home tomorrow.
I was disappointed but when I told Robert he just took the news in stride. He gave me one of those sexy grins of his and said it was cool, we could just go to the countdown and enjoy ourselves and not worry about having to do a broadcast.
We spent the day doing more interviews, mostly we focused on police officers and firemen, reporting on the security plans and procedures.
After we finished filing our reports it was still early so I asked Robert what he wanted to do. He said he wanted to see what Joanna was wearing to Times Square. I told him I had only brought the little black dress from the night before and a black pleated skirt.
We were running low on money so there was no high priced fancy restaurant tonight. So while he ordered a pizza I went to become Joanna once again. When I emerged from the bathroom and did a quick spin showing off my outfit, Robert said he really liked the stockings and pink bra showing through my blouse.
After the last few days I had become more efficient in my transformation so I was done before the Pizza arrived. I had put on the outfit I had worn the first night in New York except that this time I had on a pair of white panties instead of pink.
As we ate Robert asked me questions about how old I was when I started dressing up, how did I get started, who was the first guy I dressed for ad had sex with all really personal questions.
Robert surprised me by saying that he and two of his closest friends experimented when they were in their teens. He never did more than give several hand jobs to his friends but that they went as far as sucking his cock.
When their was just one piece of pizza left Robert asked me if I wanted it, I told him no he could have it and that I wanted desert. As he ate his pizza, I slide to my knees. When we returned to the hotel room Robert had changed into a pair of lose fitting shorts so it was easy to free his cock.
I took it into my mouth and proceeded to give Robert a nice long blow job and was rewarded with a mouth full of delicious cum. I savored the taste as I swallowed. I think I was becoming addicted to cum.
After we finished eating and I touched up my lipstick it was around 8:30. Robert called his cousin Richard and asked if he was going to Times Square, he said he was so Robert told him what hotel we were in and to come by here first. We could all have a few drinks in the bar before we headed out.
Robert and I was sitting in a corner booth when Robert and another guy walked in, I later found out that it was Richards little brother Brad.
We had several beers then decided to join the crown in the streets. It was unseasonably warm so I was able to wear a light leather jacket over my short skirt and thin blouse.
Times Square was packed with close to a million people. There was no way we could get close to the center of activity but we managed to squeeze into a spot where we could at least see the ball drop.
People were blowing horns and laughing, everyone was having a great time. I felt my skirt being lifted up from behind and as I looked back I heard Robert telling his cousins what a sexy tight ass I had. I tried to push my skirt back down but they would not let me, soon each man took a turn pinching and squeezing my ass through my panties.
Robert spun me around and started kissing me, his hands went back to my ass. We made out for several minutes and then he passed me to Richard. Richard kissed me deep and passionately and he too took the chance to play with my ass.
I felt Brad nudge Richard and tell him he wanted a turn. Richard passed me to Brad and he took me into his arms, Where Richard was passionate, Brad was more forceful and aggressive. As we kissed I felt Brad squeeze my ass hard, I even felt his finger nails dig into my flesh.
After several minutes we came up for air. I realized that several people were watching us and I was embarrassed. I straitened my skirt and told Robert that I was getting cold, he pulled me into his arms and we snuggled close and kissed occasionally.
Richard whispered something into Roberts ear and from the look on Roberts face I knew they were up to something. Brad watched us closely as Richard pulled my to him and told me to grind my ass into his crotch.
When I did I felt that he was rock hard. I looked back over my shoulder to see Richard undoing his zipper. When he had his cock out he flipped my skirt up again and slide my panties to the side.
I could not believe what was happening, I was going be fucked in public in the middle of Times Square. Richard pushed forward and the head of his cock push past my anal ring.
He went slowly at first but I think he was either afraid I would make him stop or that we night get caught because he started fucking me hard and rough. The crowd was loud so just those close by heard the grunts Richard was making each time he drove into me.
I felt Richard's balls press against my ass and I knew Richard was as deep in me as he was going to get. He kept his cock deep inside me and started shooting his load.
Richard quickly pulled out and zipped up. He pushed me over to Brad and he unzipped his pants and positioned himself behind me. Brad grabbed my hair and pulled me back to him, I was glad that it held in place.
Brad entered me forcefully and started fucking me. I had not seen Brad's cock but it felt bigger than Richard's but smaller than Robert's. He was pulling my hair and calling me dirty names. Our actions were attracting a lot of attention from the people around us. the women acted like they were disgusted but the guys seemed to be enjoying the show.
Suddenly I could not hold back any longer and coated my panties with cum. I was lost in my own orgasm and did not realize that Brad was done and pulling out of me.
When Brad was finished, he acted embarrassed and Richard told Robert that they were taking off and left. I gave Robert a hurt look and asked him how he could pass me around like a sex toy.
Robert took me into his arms and told me to quit acting like I did not enjoy what had happened. I tried to pull away but when Robert gave one of his patented grins I could not stay mad so I did what I thought was best. I kissed him and started sucking on his tongue when he pushed it past my lips.
There were 25 minutes left before midnight and Robert spun me around. my ass was well lubricated by two loads of cum so Robert's large cock entered me easily. Robert fucked me slowly as he reached around to cup my breasts through my padded bra and blouse.
He would fuck me for a few minutes then stop and leave it buried in my ass. I started wiggling my ass to encourage him to finish. I was afraid someone would eventually call the cops on us.
As Robert groped my breasts he kissed my neck them whispered into my ear. "Most couples want to share a kiss at midnight, If I time this right, we will share an incredible cum when the clock strikes 12."
As midnight approached Robert had to stop several times to keep from cumming to soon. He would nibble on my ear and squeeze my breasts. He slid his hand under my blouse and started pinching my nipples through my bra.
At 3 minutes to midnight Robert started fucking me in earnest. He started fucking me harder and harder, when the time hit 1 minute to midnight I started pushing back to meet his thrusts. I forgot about the people around us, all I could do was concentrate on the pleasure in my ass.
I was brought out of my haze when everyone around me started counting down. 10..9..8...
We fucked faster and faster....
7...6...5...
I tried, really I did. but I could not help it and my orgasm hit me with two seconds left. I was still cumming and the waves of pleasure were going through my body as at the stroke of midnight Robert emptied his balls deep in my ass.
If Robert did not have his arms around me playing with my breasts I would have collapsed. His cock was still in me as he pulled me to a nearby wall and we leaned against it until we could recover. All I could think about was that if tonight was any indication, the new year would be incredible.
When Robert's cock finally went soft and slipped from my well fucked ass, I could feel cum running down my thighs. Robert finally turned me around and looked into my eyes, wished me a Happy New Years then we shared a long deep passionate kiss.
We hung out and watched the people and kissed occasionally. Around 2 A.M. we made it back to our room. We were both exhausted so I changed into a pink nighty and we cuddled before going to sleep.
The next morning I packed Joanna away in her suitcases and became Kevin again. I still wore a pair of panties under my clothes but it was not the same.
Robert noticed how quiet I was on the long drive home and asked me what was wrong. I told him how much fun I had while in New York and that I could not go back to living the way I did before our trip.
Robert told me he would be sure to make Joanna's life fun and exciting in the future. I did not have on feminine clothes, makeup or a wig but I still felt all sissy and dainty as I rested my head on Robert's shoulder.
I thought all of our fun was over but somewhere in Maryland Robert pulled into a truck stop for gas. When he had filled up the gas tank he pulled into a deserted part of the parking lot and stopped.
He said he had to get something out of the trunk. I didn't think much about it until Robert returned and handed me a bundle of clothes. It was my pink bra, garter belt and a pair of black stockings. He told me to get into the back seat and get dressed.
I knew better than to argue with him, besides I was starting to like the idea of sex in public. He stood outside of the car while I dressed. I did not bother with the wig but I did apply a dark red shade of lipstick. When I was done I knocked on the window and he got in beside of me in the back seat.
Robert slide his pants and underwear down and without a word he put his hand behind my head and pulled my mouth toward his crotch. I knew what he wanted and eagerly started sucking his cock.
He must have been tired because he took forever before he gave me what I wanted, what I realized I needed. He shot a big load of hot cum down my throat.
I nursed his cock until it got soft then I redressed in my male clothes. I kept on the lingerie underneath.
A week after our trip I heard through the grapevine that Robert had broken up with his latest girlfriend. She had found evidence that Robert had hooked up with someone while in New York.
Robert and I continued to see each other and within a month he had moved into my apartment building. He got a place two floors above me.
I seldom stay in my own apartment, as soon as I get home from work I would become Robert's girlfriend and love slave Joanna. We are both very happy.
The End
Again, any comments would be greatly appreciated.