Business Trip

I was out of town on a business trip and was settled into my hotel room. After a hard day of meetings I decided it was time to unwind. Never going anywhere without my sexy clothes I began to get dressed. I was going to head to a local bar and have some drinks, maybe see what fun I can get into. I brought some really sexy stuff for this trip, but first needed to get my make up ready. I applied it painstakingly with dark eye liner and charcoal eye shadow. I put a little bit of blush on my high cheekbones and then some sexy charcoal lipstick. Next I put in my large hoop earrings and slide my fingers into several rings. Then I added some bracelets and a choker before putting on my red wig. Impressed with the results I went to get my slim body dressed. I have a very slight build for a man which helps me to pass when I am dressed. At 5'7" tall I'm not too tall and I weigh in at a slim 140 lbs. Add to that my sexy firm but round ass and I have the guys drooling. My body is shaved completely smooth and I have a belly and nipple rings. God I love to have my nipples sucked and played with, it makes me hard when a sexy guy does that.

I began dressing as I always do, rolling my thigh high stockings up my legs. I went with black tonight to match my short leather dress I was planning on wearing. Next I slid into a sexy black bra, it is purely for getting me and my men aroused as I don't stuff my self. I like the look I have with little tits that the guys can rub and get me all hot with. Finally I slipped into my black boy shorts and tucked my little girl cock in hiding. Stepping to the closet I took my dress off the hanger and stepped into it, slowly I pulled it up my body and drew the zipper up. As it closed the dress took the form of my feminine body, hugging every curve and leaving little to the imagination. With my heels in front of me I stepped on in buckling the ankles one by one. I was ready as I looked at myself in the mirror. I rubbed my hands over my sexy leather dress that came just below my stockings. I grabbed my purse and room key and was out the door.

I strutted down the hall to the elevator, as I pressed the button a man came from his room and walked up. He looked me up and down as he folded his hands in front of him.

The gentleman broke the silence, "Big date?"

I glanced at him with my ultra stuck up bitch look, "No, just going for a drink."

"Well you look too good to be going alone."

This guy was not getting the hint, "I won't be alone for long."

The elevator doors opened and he placed his hand out for me to step in first. Well at least he had manners. He stepped in behind me and pressed the button for the lobby. I stared ahead as the elevator dropped to its destination. As the doors opened he spoke again grabbing my hand.

"Well if you don't find that someone stop by my room, I love girls like you."

I stepped out and looked in my hand; it was a piece of paper with his room number on it. I thought about it as a good option if things did not work out. He was not bad to look at, no movie star but I could definitely get into sucking him. I walked out of the hotel to my car and climbed in. I have been to this particular bar before and have had some good luck so I was hopeful things would work out this time as well.

I got to the bar just before 9:30 and there was a fairly light crowd as I stepped up to the bar. I could feel some eye's on me as I climbed onto the stool and crossed my stocking covered legs. The bartender, a short older man with the look of Archie Bunker walked up with the typical towel on his shoulder to get my order. I asked for my usual Appletini. He began to make my drink as I surveyed the bar. It was lit low with accent lights along the walls and slim little pendants that hung over the booths. As I scanned to the end of the bar my drink was placed in front of me. I fished out some cash and laid it on the bar, I noticed a sexy guy at the far end looking in my direction, when I caught his eyes he smiled at me. I picked up my drink and took a sip from it, mmm it was good. He was sexy and appeared in good shape. Probably about 6'2" tall with dark brown hair, his dark eyes smoldered as he looked at me. He had a sexy masculine face and was very well dressed. I picked up the apple slice from my drink and began to rub it across my lips. Slowly pushing it past them before pulling it out, all the while staring at this Adonis.

He needed no further invitation as he picked up his drink and walked up to me asking if he could have a seat. I motioned for him to sit and continued to stare at him. He introduced himself as Chris and I told him I was Katie, we sat and talked for a good long while. It was not the typical dick sucking want to get into my dress after five minutes conversation. It was more like first date getting to know you. It was sweet and I liked it. As we talked he knew I was a cross dresser and while he had never been with one, he did admit he was curious. His naive nature was very attractive and very sexy. He bought me my drinks as we talked, his hand on my thigh touching my stockings and moving up and down. My stocking tops were exposed at this point but I didn't care. I was getting really excited. I laughed at his jokes and touched his chest as we continued our flirting. As time passed and I got more and drunk I excused myself to go to the "little girl's room."

I finished in the ladies room and was applying some more lipstick when the door opened up. It was Chris and he locked it behind him. Without talking Chris walked up to me a wrapped his strong arms around me. Pressing me against the counter he put his lips to mine and invaded my mouth with his tongue. The shy gentleman from the bar was transformed into a lust filled machine and I could not wait to reap the benefits. His hands roamed over my body as his tongue moved inside my mouth with his. My hands moved down to his pants and I began to unbuckle them and slide inside. I got my first feel of his hard cock and knew I had to have it inside of my mouth. Our kiss broke and we were both breathing heavy as I dropped to my knees. His cock was free and he stood before me staring down as I placed it to my lips. There was already a drop of pre-cum on the end and I rubbed it against me, tasting his manly fluid. His cock was incredible and very hard. As I held it in my hands I gently stoked him up and down as I teased it with my mouth. I still had not put it in me, I wanted to savor it. Chris continued to moan as I slowly and deliberately worked his cock. Finally giving into my own desires I pushed him into my mouth. It filled me up pushing my jaw to its limits. His cock was not too long but it was thick, I knew it would feel wonderful in my boy pussy. I allowed him to slide in and out of my lips as I held them tight to his soft skin. His thick cock worked in and out of my mouth as I moaned in a low sexy tone. As I did, I kept a hand on his rod and one massaging his tight balls.

I pulled his cut cock from my mouth and began to run my tongue up and down its full length before plunging it back between my lips. My lipstick was wearing off as Chris watched my expert sucking in the large bathroom mirror as he talked dirty to me. He began calling me his slut and sexy girl, telling me he was going to blow his cum in my mouth. This only encouraged me further as I increased my tempo and pressure on the underside of his cock. Chris liked this as he grabbed my head and began to push his cock deep into my throat, pressing it to the back and gagging me. I had never deep throated before but always tried, well Chris was determined as his cock continued to gag me. I would take a deep breath before he drove back into me. Relaxing my throat he pushed past my gag reflex into my throat. My nose was buried into his pubic hair as he held my head in place before letting go. My hands were on his hips and eyes watered as he made his second successful attempt into me. I was able to deep throat him and had no clue how I was doing it. The fourth time he drove into me he held me tight and began to shoot his cum down my gapping throat. It just slid down as my neck muscles massaged his cock. He pulled out still shooting ropes of cum into my mouth. I swallowed every drop as his cock finally subsided.

Chris looked down at me as I cleaned his cock off of the remaining cum. I gave a few last licks as I pulled myself up and planted a big kiss on his lips. We walked out of the ladies room back to the bar and our drinks. Archie Bunker behind the bar just gave a coy smile as we touched and talked like nothing had happened. Chris was still glowing from the cock sucking he just received. I decided it was time to go and looked in my purse for my keys. That was when I noticed the room number given to me in the elevator. I had a wicked idea and quickly invited Chris to my hotel room for some more fun and surprises. I asked if he wanted to have me in a threesome, his eyes go big and he quickly agreed. I gave him my hotel, room number and key as I walked out and he took care of the bill.

I arrived at the hotel ahead of Chris and hurried up to my floor. I knocked on the door to my elevator friend. The door opened and he looked surprised to see me. I asked if he was interested in fucking me in a threesome with another guy, he was not as enthusiastic but when I reached out and began stroking his cock he could not resist. I led him down the hall to my room and pulled him into it. We were making out heavy when he broke the kiss and asked my name. I told him and he smiled, and then introduced himself as James. James was an average looking guy, not ugly but not hot like Chris. He was about 5'10"; he had a short military type haircut and surprisingly strong arms.

James began to strip and before I knew it he was laying on the bed naked with his cock sticking up. It was not as thick as Chris but was just as long. It was covered in veins and had a bit of a curve to it. I stood by the bed and took off my tight dress for him. I then crawled over the bed letting my wig trace over his legs as I got ever closer to his engorged cock. James had his head propped up on a pillow and watched me intently. As my mouth reached his cock I let out a long hot breath over his dick, this caused it to jump. While holding myself up with both arms I licked up the length of his shaft and tasted the salty skin. I kissed his cock head before sliding the length into my mouth. This was the second cock I had in my mouth in the last two hours, and if all went well I would be getting my ass plowed soon enough. James' cock was alive in my mouth reacting to every slight lick, suck or slurp. My mouth slid up and down his shaft as the door opened and Chris walked in. He stripped down immediately and walked over to the bed. His hands grabbed my panties and he slid them down my legs exposing my smooth ass. Chris put his warm mouth over my ass and began to lick my tight hole.

I moaned around the cock that was in my mouth as his tongue licked and darted in and out of my boy pussy. My lust continued to grow and I ravaged James' cock like a slut in heat. Chris moved his hand under me and grabbed my cock; he slowly began rubbing my cock clit back and forth. Here I was on my hands and knees in a black bra, stockings and heels in a hotel room as I sucked on a hard cock and got my ass rimmed and clit stroked. Can you say heaven? My mouth was squeezing James and tongue circled his cock as he was deep in my mouth. I pulled my mouth off of him and sat up. I pulled Chris up and told him where my lube was. He lost no time in jumping up and retrieving it. He came back to my ass as my mouth got back to work on the cock before me. I rode my tongue up and down that shaft as Chris slide his large fingers into me. He fucked my ass with his fingers again causing me to moan around James' cock.

When I was good and lose I let Chris know and begged him to fuck me. James was very hot and talking dirty as Chris slide into me. It took me a moment to get used to the girth of his cock. But slowly I did and he began to push further into me. His cock felt fantastic inside of me and I found it hard to concentrate on the blowjob I was working on. Chris held my hips and drove deep into me, my mouth working James and his curved dick. I licked and sucked him as the spit and pre-cum built up in my mouth. I would stop sucking every once in a while and lick my lips as I jerked his cock. Chris was fucking me and I was blowing James for a good five minutes when my guys got the idea to lay me on my back with my head over the side of the bed.

I was on my back and put my legs on the shoulders of Chris as my head hung over the side of the bed. Chris pushed his cock back into me and James entered my mouth. I was pretty much at their mercy as each slid their cock in and out of my slut holes. I was being pushed in each direction with the thrust of each guy. They grunted and moaned as they fucked me hard. I was also moaning around the cock sliding in and out of me. James was the first to reach orgasm as he pulled out of my mouth and began shooting cum all over my face and chest. I was rubbing my nipples and squeezing my ass as his cum splattered on me. Suddenly as the last drops were falling on my Chris pulled out and began jacking his cock. The first shot hit my chin and neck. Cum dropped all over my stomach covering my belly ring and filling my belly button. Chris grunted as he squeezed the remaining drops out of his well used cock. I felt so dirty as I rubbed the cum from the two men into my skin.

I grabbed my girl cock and began rubbing it. I was going to add to the loads of cum already dumped on me. The men watched intently as I rubbed my clit and my breathing quickened. My legs were stiff as the feeling rose from my little balls and up my shaft. My cum started flying over my belly splattering all over my stomach and up onto my bra. Exhausted my hand dropped as I was on my back panting. James began to dress and was out the door while I was still recovering. Chris put his lips to mine and tenderly kissed me, sliding his tongue into my mouth. I put my arms around his neck and moaned into his mouth.