CROSSDRESSER BUSINESS TRIP – PART II

Click here to read PART – I posted earlier

PART II

We started out looking for a place to have lunch. I finished my food and it was around 4 PM. Since we had to travel 60kms out of town and Rajesh told me it was not a full highway but a small road and it would take about 2 hours at least. We started off and just when we were exiting town I picked up a few cans of beer and a cpl of packs of smoke just in case I don’t get my brand in the small town. We got stuck in a traffic jam caused by a minor accident between a cpl of cars on the road and were delayed another 40mins. We finally left town at around 5 20 pm. I didn’t talk much to the cabbie as I had fallen asleep as I was tired after my romping session with Manoj( shopkeeper in Part I ). I woke up around 6 PM and asked him where we were and he replied we had just left the town and we should reach the destination at about 8 PM. I said OK and as we were out of town and as the weather was getting chilly ( it was late October) I wanted to take a piss, so I asked the driver to park on the side so I could take a piss. I got down from the car and started taking a piss and when I was tucking my dick back in my shorts I realized I was still wearing on the panties which I just bought.

I lit a smoke and offered one to Rajesh he took one even though I saw his own pack on the dash of the car. I opened a can of beer and started chit chat with the driver. During the chit chat and 3 beers down in 40 mins the topic came to massage and call girls. He said once back in Lucknow he could arrange a girl for me, I replied I would rather prefer a guy to massage me. He said a girl can give you more pleasure in massage than a guy. I asked if he can arrange a cross dresser for me. He replied that he doesn’t know any guys who dress as girls but why I need such a guy. I told him” I also like to dress like a girl’, he asked ‘ So you want to dress as a girl and want a guy to massage you or you want a cross dresser to massage you?’ . I asked him to park on the road side and I took another piss and he did also. I lit up another smoke and another opened beer and asked him if he had met any cross dresser and he replied no. “ want to see CD pics of my friend?” I asked, he said “yes”. I put on a slide show on my mobile of my own pics which started off with pics not sowing my face but in lingerie, skirts etc.. then he saw me in the pics and he kept watching till the slide show ended on the phone screen. He gave me back my phone and should we go. I got in the car and we moved off. The beers and cool wind was making me tingly. I asked him ‘ Did you like my fiend’s pics?’ he replied’ I think some are your pics. Do u really dress like that ?’ I replied “I do and am wearing a lace panty right now”. I lowered my shorts to show him. After a few minutes I asked him how much longer to reach there and he said another 1 hour minimum. “mind if I dress up fully and ride till we reach there?’ I asked. He said sure. I spotted a open air small food joint on the road side ( common in India) with the wash rooms on one side a bit away from the main eating area. It was empty except for a cpl of waiters standing outside. I told him to park and have some tea while I go and change in the rest room. I picked up the bag of newly bought lingerie and some some spare cloth from my bag to use as pads and went in. I washed my face, got naked. I wore my bra and padded it then I wore the floral leggings and the new top. I packed my normal clothes back in the bag. I peeped out and saw he was still having his tea. To pass the time I lit a smoke and puffed away. I heard the horn of the cab and I guessed that the driver was back in the car. I took a cpl of long drags of my smoke and stubbed it out. I took a deep breath and picked up my bag of normal clothes and walked out. The car’s headlights were towards me and I turned and saw the waiters looking at me. I walked the 30 mtrs or so to the car without looking towards the waiters. I got into the front next to the driver and told him to go before the waiters come looking. He moved out of the joint and drove a mile and parked the car on the road side. “why did you stop?” I asked. He turned on the light inside the car and was looking at me. He shifted a bit in his seat and finally he moved his hand to adjust his cock in his pants which I think was hard and making him uncomfortable. He held my boobs for a bit and felt my legs over the nylon leggings. “ How do I look?” I asked “ you look very hot and those boobs are quite big” he replied.

“OK lets go now, tell me when we are about to reach so I can change to normal before we check in to hotel” he said sure and we drove off. He drove at an average speed and looking at me whenever he had a chance. I was busy with my last beer and smoking looking out the left window. The car jumped over a bump on the road and I turned to look what it was and then turned to Rajesh and asked what it was, “ just a pot hole” he replied. He had one hand on the wheel and then I noticed he had pulled out his hard on and was rubbing it. “you drive let me do it for u” I held his dick)” and he just let me rub him. After a cpl of miles he slowed down while crossing a small town. The traffic was moving at a snails pace due to some cows sitting in the middle of the road. He quickly tucked his cock back in his pants and I rolled up the window as I was in the front seat and everybody could see me. I noticed a lot of bystanders looking at me as our car passed them.

The rest of the journey was uneventful except that around 8pm Rajesh parked in another food joint and I understood we were about to reach and I should change back to normal. I changed back to normal and we drove and reached the destination. I checked a cpl of hotels and checked into the second one. I got a room facing the road.

I took a shower and order food and a cpl of beers. The waiter got me the beers and told me that the food would take another 15 mins. I finished off my first beer and was browsing through the TV channels and there was a movie playing where a guy dresses as a girl as a guy’s girlfriend. I got the urge to change into ‘Sheila’ and I got out all my stuff and got naked. I wore the thongs and tucked in my shaved dick between my thighs and then came the floral leggings. I hooked the bra and padded it making sure the shape was right. Then came the nighty. I combed my hair back and wet them. I applied some cream on my face and a nice pink lipstick. (Dressing up and admiring my self in the mirror is the part I enjoy most ).

Any time now I was expecting the food to come. I sipped n my second beer and smoked looking at myself in the mirror. I heard a knock and I shouted “come in” and rushed to the toilet not to get caught by the waiter all dressed up. He came in and laid the dishes on the table and asked me to sign, I just took the bill folder in from the door and signed it and slid it back out, but the door opened to face the toilet basin with a full size mirror over it. He could easily see who was inside and in what condition. He did see me all dressed up and after I gave him the bill back he stood there for a bit and then moved away but did not go out. I peeped out thinking he had left and found him standing near the room door. He had seen me so I walked out and draped a towel over my chest. “ Are you alone, where is Sir?” he asked. Then he realized “Ohhh sorry…….no problem I shall clear the dishes later” he said. I gave him a generous tip and told him to keep it secret and come back to clear the dishes. He said “ Don’t worry. If you need anything just call room service and call for me only, my name in Ranjit”, “sure thanks” I said and he went away. I finished my food and smoked one. After a few minutes there was a knock and I peeped through the eyepiece and saw it is Ranjit and allowed him to enter. He cleared the dished and asked me if I needed anything else. I asked for a pack of condoms. Sure I wil get them for you he said, I gave him some money and he went out saying that he is busy with room service and will return with the condoms as soon as he is free. He came around 10 30 pm and handed pack of condoms and told he is not yet free and will be around mid night as some guests were having a party. I told him am tired and going to sleep and he should try to call me on my room phone before he comes. He agreed and squeezed my right boob before he went. I was getting a feeling it would be an exciting night and dozed off.

The phone rang around half past midnight and Ranjit asked me if he could come. I was wide awake as soon as I realized he was ready to come to me. I said OK and he was knocking just a minute later. I opened the door and he came in, stood just looking at me. “ SO what do you want so late at night ?”I asked. He was quite horny and I could see it in his pants. He just came near me and felt my boobs with his right hand and left hand squuzed my bums. I backed up a bit and lit a smoke. He was feeling me all over and gave a few kisses on m y neck and cheeks. Suddenly we heard voices in the hallway, sounded like 3-4 guys. We both stopped and after a min he said” Come to the terrace with me , no one will come there at this time of night. “. Now that sounded exciting and he went out. I finished my smoke and went out cautiously. The lift was off so I would have to go up the stairs. I tucked in the room key in my leggings and my pack of smokes and lighter in my hand I walked up the stairs. The teraace was two floors above mine, I reached and saw Ranjit there and opened the door for me, we both stepped out in the cold wind and he locked the door behind us.

He led to away from the terrace entrance door and started fondling my boobs and after a cpl of mins he dropped his pants and out came his hard on. He put his hands in my leggings and pulled it down along with my panty down to my knees. Then he made me bend over on the terrade wall. I gave him a condom and he slipped it on his hard on in a flash. “ Have to be quick, the manager might call me anytime” he said and put his tool on my hole and pushed. He entered half in the first stroke and then fully in the second one. HE pumped me without saying a word. He was done in about 5 minutes. The used condom went over the terrace wall into the bushes behind the hotel and Ranjit pulled up his pants and helped me pull up my panty. Then we went to the terrace door and he unlocked it and I went to my room and he went wherever he had to go. I went into my room and had a smoke and fell asleep.

A knocking on the door waked me up. I checked the time and it was around 4 AM. I peeped through the glass and saw it is Rajesh the driver. I let him in and in my slumber I had forgotten I was still in my nighty. He came in and asked if he could rest for a while in my room as it was getting cold out side. I said OK and fell on the bed and dozed off for another one hour.

I woke up and found him on the sofa sleeping. I got up and went to the toilet for answering nature’s call. I came out and he jerked up awake and saw me I was wearing my padded bra panty and nighty.

He was still lying on the sofa I walked up to him and picked up my cigarette pack and lit one. It took him a few seconds to get focused and then he saw me, got up and came and held me tight. Neither of us needed to say anything the obvious was about to happen. The fucking on the roof made me want to to it again in the open. So I just asked him’ will you take me for a ride dressed up?’, “sure” he said and I quickly changed from my nighty to my top and slacks. I wore a thin jacket over the top and my jeans over the leggings as it was cold outside and also as I had to cross the reception area and couldn’t do it as dressed up as Sheila.

We got in the car and he turned up the heat to make it more comfy. Once the car was warm I slipped out of the jacket and jeans as he moved the car out of the parking and we were just cruising around. There was a light fog and not many people around. After 10minutes of driving around he stopped in an alley behind a row of houses. We both rolled down the windows a bit and lit a smoke each. His left hand was on my boobs and squeezing softly as though real tits. “open your top baby” he said. I did and he came out of the car to my side and opened my door. “Lets take a walk “ he said” You want me to walk like this in the cold weather?” I asked. “ sure why not. You look soo sexy like this I will make you warm don’t worry” and I could see his dick straining against his jeans. I was getting very excited and I just wore the thin jacket over it. We walked for a bit and I was feeling the cold wind on my chest as I was wearing only my bra and the front was open to expose my tities. About a 100 mtrs from the car we came to a hedge covered my some vines, we went behind it and he looked around and dropped his pants to reveal a 7” shaved tool standing at attention. I stroked him and he pressed my ass cheeks. He kissed me on my neck and back. He then slid down my leggings and panty. He rubbed his cock on my hole and was holding my boobs from behind. I was not feeling cold any more and I gave him a condom and he wore it. He positioned his tool on my hole and held my hips and pushed. He entered in the first stroke and I moaned. I bent over and held the pole of the fence and he started full strokes. Pulling out almost fully in each stroke. He increased his speed and was pumping me in full strokes. I was moaning and he was grunting. Suddenly a guy came in the alley walking a dog on a leash. We saw him when he was about 20 mtrs from us and Rajesh signaled me to be silent though he didn’t stop fucking me. The guy with the dog was a servant from on of the houses I guess. He came near us and asked Rajesh for a light for his smoke( he didn’t see me till he was near the hedge). Rajesh stopped fucking for a min and gave him the lighter. Then that guy saw me “ be careful and hurry up before anyone else comes!” he said to Rajesh. HE lit his smoke and stood there watching us. We both realized he wanted to watch so Rajesh started fucking me real fast and I was moaning. My tities were bouncing to and fro and he was making thup thup sounds with each stroke. The servant started masturbating. Rajesh fucked me for a good 5 misn and the other guy shot his load on the hedge. Rajesh made me lift a leg and put on the hedge and fucked me  hard. I was moaning and he suddenly jerked hard and gave the final push deep in me. He shot his hot load in the rubber and held my boobs tight. He pulled out after a bit and then I stood up, the other guy’s eyes popped out and his jaw hung open when he saw my hard on dripping pre cumm. I shagged my self with a great orgasm shooting rope after rope into the hedge.

Rajesh helped me pull up my leggings and we lit a smoke each and waled to the car. The other guy followed us to the car and I kissed on the cheek before we drove back to the hotel as the sun was coming up.

We reached the hotel and Rajesh came up to my room we both had a shower and we talked about the other guy’s reactions when he saw I was a guy and that mad ehim hard again. He fucked me again before we went out for my meeting.

We came back in the evening and went for another drive.

That’s another story.