Crossdresser Business Trip – 1

HI

This is one of my real life experiences. All my cross dressing and sex experiences are on my work trips as that is the only time I am alone and I can indulge in my pleasures ( as I live in a joint family in India so cross dressing at home or in my home town is not possible).

So here I was getting ready to go on another work trip to Lucknow ( a big town in the state of UP in India). I reached there by train around noon and since the office was about 60 kilometers out of town I hired a cab as I would be staying there overnight. I contacted the travel agent at the rail station and booked a cab and got my luggage in the cab and moved off. The driver was a guy of about 24 yrs about 5ft8 and fit named Rajesh. We drove out of the station and I asked Rajesh to stop so I could buy some smokes and then go to the market, as I had to buy some clothes. He asked me what type of clothes so I told him I need some for my wife as a gift. He took me to a part of town where there were lot shops selling all kinds of dresses for women. I told him to park and I would find some dresses and meet him back in the car.

It was lunch time and most of the shops were closed for lunch break. I was looking for a lingerie shop and I found one in a side street with only one sales guy inside and was about to close for his lunch break. He was in his late 30s I guess and a bit chubby with a half bald head. I asked him if I can come in and buy before he closes as I had to go out of town and was in a hurry. He obliged but he closed his shutter half way down so that he wont have any more customers coming in to disturb his lunch break.

I asked him to show me my size of bras and I selected a cpl of white C cup bras. He asked me “ any panties with the bras or anything else?’ I asked for lace panties in my size which was smaller when compared to bra size, he asked me ‘ this will not match the bra size , could you check the size with madam’ . I don’t know what was going on in my head but I asked him if I could smoke and he was OK with it. I offered him a cigarette and we both lit up and I just blurted out. ‘ Actually these are not for my wife but for me !!!’  Now he was silent for a bit and then he showed me some panties and I selected a white lace panty. He again asked me for any thing else and I asked for some leggings and I chose one with a floral pattern. Just then my phone rang and my client told me I would have to stay over for a cpl of nights and the owner had to go out of town and would be available the day after tomm. I finished my call and he was looking at me as I should ask him for some more stuff and I decided since I was going to stay for a cpl of days at least I asked him for a nighty. He showed me some and I chose one with string straps and see thru lace. I said ‘ I think this looks a bit small in size do you have a try room?’ he replied ‘no there is no trial room ‘. Now I said ‘ can I try at the back of the shop’. He just move out of his counter and closed the shutter all the way down and said’ You can try here no one will come, besides I never seen a guy dress as girl though I heard about it’.

SO, I opened my T shirt  and slipped on the nighty. It was a nice fit  and the satin made my dick tingle in my shorts.( I was in my travel clothes T shirt n shorts with sneakers), I said it feels OK but it would be tight once I padded the bra under it . He asked me what pads I use and I told him I just stuff the bra with spare cloth as I don’t have inserts now. He said ‘ why don’t you try it with the bra and if doesn’t fit he can show me a different size”. ‘ are you sure it is OK if I dress in the bra etc… ?’ he said ‘ sure I would love to see u in that ‘. I could see a little bulge forming in his pants.

I said it will take a little time to get dressed and if he can give me some time alone and some spare cloth so could stuff the bra. He gave me some and went out of the shop and said he would be outside and I should knock the shutter once ready. I wasn’t sure what he wanted but I agreed.

I lit a cigarette and got naked, my dick was getting hard. I tucked it in and first came the lace panty, then the bra which I stuffed with the spare cloth. Then came the floral leggings and then the nighty. The nighty was actually fitting quite well over the padded boobs. I looked into the mirror behind the counter and my dick was out of control and I had to pull down the panty and keep it straight. I adjusted my  boobs, had a sip of water, wet my hair  and lit a another smoke and ……….. then I took a deep breath and knocked on the shutter . I faced away from the shutter and smoked and in a I heard the shutter open and close. I didn’t turn back and neither of said anything for a cpl of minutes. I had finished my smoke and nervous as I was I pulled out another one and realized the lighter was on the front counter behind me.

Then he said’ What’s your name?’ , ‘Sheila” I replied without turning and asked him for the lighter. He got it and came closer and then i turned around to light up. I took a cpl of drags and he was just staring at me all over and he had a huge bulge in his pants. Finally I asked ‘ does it look tight or is it OK? ‘. He came and held my boobs and adjusted them a bit and said ‘ It is fitting fine and you ……..” after a pause  he said ‘ why u want to dress like this ?’. I just took a drag and came close to him, real close and rubbed his hard on over his pants, he didn’t say anything else he got the answer I guess and his hands were all over me in a jiffy. He turned me around and suddenly I couldn’t feel his hands on me but I heard a zipper sound and pants dropping down. I turned around and faced him took the last cpl of drags from my smoke and crushed it out. He was there with his 8 incher black meat under his belly. He came close and raised my hands and slid the nighty over my head and dropped it on the counter. Now I held his dick and stroked it. ‘ you got a condom?’ I asked and he picked up his pants and got out a pack which it seems he had bought while I was changing. He opened one and wore it on is hard on. Then he pushed me down on my knees and I sucked him. His dick was hot and haarrdd. After a cpl of minutes he stood me up and made me face the counter in front of his mirror and slid my panties down from behind me. He then rubbed my hole with his finger and pushed one in. I moaned a bit and my own dick was dripping pre cumm. Then he inserted two fingers and pumped fast and stretched my hole a bit. I held his dick and motioned him to enter. He placed his tip on the entrance and pushed, it did not go in and he spit on my ass and fingered it and then pushed again. This time he entered and his this steel hard dick with no lube, I let out a shout and said’ Damn!!!!! That hurts. Hold on for a sec “. Once my hole got relaxed then I jerked my hips so he could start pumping. He started slow half strokes and gradually got his full dick balls deep in me. Now he started pumping me fast, his strokes were making me jump and my boobs to bounce. I was looking in the mirror and my didck was ready to explode. He pumped me for about 5 minutes bent over the counter and then he removed his dick and lay down on the floor and motioned me to ride him. I faced him and held his dick and positioned it on my hole and slid down on it but it coudnt enter coz his belly was in the way. So I turned around and tried reverse and this time it went in. He was too hard, I never felt a dick get soo hard, it was like a wooden dildo. I sat on his dick and with it in me fully I moved my hips to and fro and he was just moaning ‘ ooh baby , oooh baby’. He had some stamina, I started pumping up down and did for about 7-8 mins and then he pulled me off and made me doggy style on the floor. Now he entered in one brutal stroke and I fell on the ground but he just lay me down and pumped my ass. Then he again pulled up my ass and got up and again inserted in me while I was in doggy and he was standing. Damn!!! This time he went too deep I couldn’t control my pre cum from stopping. Suddenly he increased his speed and held my dick with one hand. That was it, the moment he held mine I came with such a force my cum rope flew a good two feet in the air and landed on the floor and I came and came. He then rammed one last time full deep in me and came in the rubber deep in my hole. We lay like that for a cpl of minutes and then I just saw the time, this guy( never even asked his name) had humped me for a good 25 minutes. My legs were wobbly, I couldn’t stand up. He got up lit two smokes and gave one to me and helped me stand up.

I finished my smoke and started to dress back to normal. He also wore his clothes. Then he spoke’ are you from lucknow or visiting?’ ‘visiting, am going for a cpl of days for a meeting and will be back here to catch my train back’

‘ Will you meet on your return?’ he asked. “ Sure I will if I reach your city on time and have spare time before I catch my train’ He wrote down his number and name( His name was Manoj ) and asked me to call him when I return.  Sure I said.

I had changed back to normal and he packed all my lingerie neatly in a plastic bag. I asked him how much and was glad to get a 50% discount. He thanked me and opened the shutter and let me out. I walked through the parking lot and located my cabbie.  I got in and he asked right away’ did you get a good gift for madam?’. I said yes lets get something to eat and start our journey.

The journey with Rajesh( the cabbie) turned out to be very eventful. I did order with the client I visited but the journey with Rajesh is for part II ( coming shortly)

Love you guys and thanks for reading. Leave your comments/suggestions as I am planning another trip to another client.