The Kolkata Trip Part 1

As you all know and those who dont I am from somewhere in north India.

I am tall fair smooth and I love to crossdress when alone. I am bisexual and when alone (usually on my work trips) I dress in female lingerie and make love to a male as a woman.

So as it happened last Monday I was called for some meetings over the next 3 days in Kolkata(kol) and I took a flight and reached there around noon. I took a cab and reached my hotel in park salt lake city area. It was a nice hotel with cozy rooms. I had a shower and ordered food. I had my food and dozed off. I woke up around 4 pm and was browsing some porn along with checking my official mail. After watching some porn I was feeling a bit horny and I decided to go out and buy some lingerie and try my luck at finding a guy to have some fun.

I asked the hotel guys and found out there is mall at walking distance from the hotel and so I walked there and I was browsing the shops looking for a lingerie store. I walked around almost the entire mall but I couldnt find a lingerie store so I asked the guard where were the lingerie stores. He pointed me to a different area of the mall where there were smaller shops but all dealing in females clothes, lingerie etc…

I went there and was walking around trying to locate a shop where there were not much crowded. I saw a small shop with some cool lingerie in the window and a single customer who was buying some gel bra pads. The shop was near the entrance so I went out into the yard for a smoke so the lady would finish her shopping and leave. The area of the mall was not too crowded. In the area I was there were about 10 people in all, as it was a small area with about 20 shops and mostly ladies stuff.

We I finished the smoke and went back in, the shop was empty and I asked for my size of bra. I got a nice white one (my fav color) and a nice lace panty. The shopkeeper asked if I wanted anything else and I asked for a set of gel pads to fill the bra. My shopping over, I set off walking back to my hotel. On the way back I picked up a skirt from a street vendor sellinh ladies dresses, a pack of smokes and some whiskey( saves money as hotel alcohol is quit expensive hehehe) .

I reached back to my hotel and went to my room and I had my shopping bag in my hand and the whiskey bottle in the other, I was trying to open the door and in the process of turning the key and holding my bags I dropped the lingerie bag and out fell my bra( in box packing which shows quite obviously what is inside) and the gel pads. I unlocked the door and another guest who was staying one room away was passing behind me picked up my stuff and handed it to me. I was quite nervous now and a bit panicky. I opened my door and kept the stuff on the floor and turned to thank the guy.

Me. Thanks.

Him- no probs, happy to help.

Me- am amit from (^(^($

Him- am saurabh from &^%

We made small talk about our jobs and decided to join for a cpl of drinks in the bar at around 8 pm. ( I didnt want him to come to my room as I wanted to dress up and he would know that if he came to my room)

The hotel had a spa and I asked if I could get a massage in my room.( thinking I could try and seduce the masseuse to make love to me when I dress as a female) the y told me that they do provide massage in the room but can do so tomm as they were booked for the entire evening. So I booked one for the next morning as I my meeting was at 11:30 am.

Then I lit a smoke and got naked I went to the toilet and cleaned my hole thoroughly and lubed it up. Then I wore my bra, then my string lace panty. I then stuffed the bra with some spare socks and then put in the gel pads in the bra cups. (this was the first time I used the gel pads and it gave such a sexy shape and feeling almost as if they were real)

I then put on the tv and checked the time I still had about half an hour before I had to go down the bar for drinks with saurabh. I called up home and said all was ok and etc… I was checking my self in the full length mirror on the room wall and was getting hard looking at myself as a sexy busty gurl. I lit a smoke and was at the window smoking and stroking my cock. I had lubed my hole and the wet feeling was making me horny.

I was wearing only my bra and panty. I wore the skirt and a t shirt and was facing the mirror on the wall and doing a bit of a dance as the tv had some movie song playing on it.

I was dancing and I thought I heard a knock on the door, I ignored it and then there it was again after a minute.

Since I was dressed I opened the door a wee bit and peeped out. No one was there. Just my imagination I thought and checked the time. 5 more minutes and I would have to change back to normal and go to the bar.

I thought I will finish my smoke and change back to normal. I was near the window on the 6th floor and it was getting a bit cool in the late evening. I finished the smoke and due to the cool wind I had to go to the loo. I went did my thing and came out and as soon as I stepped out of the washroom and closed the door…

I—- (we) got a shock….

There standing in my room near the bed was saurabh. ( he came in as I had forgotten to lock the door when I was checking who knocked)

We both didnt say anything for a minute. Then I said

Me- I am soo sorry about this Ill go change(fully scared as he might react negatively and get angry or report me)

He just stood there

After another min I said again “you go to the bar I will meet you there”.

Him- yessss okk

He went out and I closed the door. My heart beating so fast I could hear it beating.

I was standing there for my heartbeat to slow down. My hands were shaking with nervousness. I went to the mini bar and opened a bottle of water and drank a cpl of sips. As soon as I had removed my t shirt to remove the pads and bra..

The door swung open and in walked saurabh (again I forgot to lock the door)

“Can we have drinks in here ??\” he asked as he walked in.

Now I was standing there with my t shirt in my hands and wearing nothing but a padded bra and a skirt.

I realised he wanted to be with me as a gurl and so I just wore my t shirt back on and said \” sure we can.\”

Me- please close the door and lock it (not wanting to take any more chances)

Him- sure

After locking door I offered him a smoke and he declined saying he did not smoke. We both sat on the 2 seater sofa in the room near the window and I was smoking and we were talking about our jobs.


Him- I thought you had bought the bra for your wife when I helped you before

Me- oh no actually I like to dress when alone

Him- did you buy it today, as it was a new box I guess?

Me- yes I just bought it from the mall this evening

Him- didnt the shopkeeper ask why a guy is buying bra panty?

Me- no he was just interested to sell.

Him- you dress up quite smart!!

Me- thanks

I crushed the cigarette and make 2 drinks from the bottle I bought.

Him- thanks, how long you staying in kol?

Me- 3 more nights

Him- I am here for a week

Me- ok cool cheers( we sipped our drinks)

The time was about 8:20 pm. We chatted about general stuff and then the topic moved on to me and my dress.

Him- your boobs look quite real

Me- thanks

Him- do you have a gf or wife

Me -I have a gf, why do you ask?

Him- no no I just thought since you dress up that u might be gay

Me- am not gay I like to do with boys and girls both

Him- so when you dress like this do you do with guys?

Me- yes

I poured our third round of drinks

Him- thanks— so when you dress like girls how do you do with guys

Me- am going to the loo will be back in a min

I went in and came back wearing only my t shirt and string panty.

He was just looking at me all over. I took a sip of my drink and lit a smoke and went to the window. I was smoking and watching the traffic outside. Suddenly he came behind me and hugged me.

Me- hmm so you want to make your gf tonight

Him- yeas..Sss.. I want to try once .. Oyesses s sass

I was feeling good having his hands all over my body, he was squeezing my boobs and the gel pads made them feel quite real to touch.

I could see he was hard as wood. His dick was pushing against his pants.

I rubbed him over his pants with my hands and he was rubbing his hard on , on my bums from behind.

I finished my smoke and turned around. I put my hand on his belt and he grabbed his belt and opened it and his pants were off in a few seconds. He held my t shirt and pulled it over my head and there I was naked ( except for bra n panty) in front of his with his steel rod about 6.5 “ long and ready.

Me- you got condoms??

Him- no…. Does that mean we can’t do? He asked thinking, I guess , that it might not happen.

I went and got one from my bag. He opened the wrapper and wore the rubber on his tool.

We were rubbing bodies and fondling, or rather he was fondling my (false)boobs and rubbing my ass cheeks.

He made me lie down on the bed face down. He started rubbing my back and shoulders, kissing my neck

After a few minutes of rubbing and squeezing my ass cheeks he took some lotion from the bath and put some on my bums. I knew he was getting me ready and himself too. He spread some lotion and started massaging my bums after a cpl of mins he put some more lotion but this time between my cheeks , right on the hole.

He rubbed my cheeks and then used his finger to spread the lotion on my love hole. I was getting hard so I adjusted my tool under me.

He was rubbing his finger on my hole and suddenly he pushed it in. Then he was pumping with his finger, I was moaning a bit as it felt good. I had already lubed up and he put some more lotion and in went 2 fingers

He came on my side while I was lying on bed face down. His fingers still in me he came near my lips and put his tool in my mouth. He was hard.

Well I was a bit horny too so I sucked him . Now he was moaning, his fingers in me and dick in my mouth. “ ohhh yeas sssss babbyy yaaa suckkkk iittt””

He had some stamina and after 5-7 mins of sucking he turned me around. He came on the bed and put my ankle on his shoulders and his dick on my love hole. My hole was lubed , fingered and ready to take his manhood. He pushed but his hands were holding my ankles and he could not get it inside. I held his dick and positioned it.

He pushed and it went in half. Ohhhh it was hot and hardddd..

He closed his eyes and was still. Then he pushed again and it was fully in. He again held there for a few seconds. Then he started strokes, and making thup thup sounds. He pumped in full long slow strokes and was filling me deep.

After 5 mins of pumping with legs on shoulders he got off the bed and stood on side of bed and made me lie of one side and lift one leg. This time he entered easily and his strokes became faster and deeper. His tool was just the right size. Not too long and not too thick and he was doing it without hurting me. Just the way I love it.

The long full strokes were making my boobs bounce and I had to adjust the pads twice. He had a lot of stamina as now he made men doggy position and stood behind me and humped me. He loves doing full long deep strokes I think. And my boobs were hanging and bouncing with each stroke.

He pumped so much I just fell on the bed face down. He was so horny he just came on top and spread my ass cheeks and inserted his tool.

This time I could feel his speed getting faster and he was getting a bit wild.

His hands came and squeezed by boobs under me while his pumping got faster.

Suddenly he thrust very hard and deep and groaned. Ohhh his whole body trembled and he lay still. He squeezed my boobs and pushed his dick deep in me.

We lay still for a min and he was still hard. Then he pulled out and went in to wash his tool. I went after he did and wiped my hole and adjusted my boobie pads in the bra.

We sat down and neither of us spoke anything. I lit a smoke and I noticed he had humped for a good 25 mins.

He was feeling happy I could see it on his face. He didn’t want to wear his clothes. I wore my panty (the bra I don’t remove cause thats the boobs)

We finished our drinks.

Me- lets order some food

Him- ok

We ordered food and

Thats for part 2 people (depends on how hot your comments make me!)

Love you all.

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