Crossdresser Business Trip to South India

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Crossdresser Business Trip to South India
Sheila Boy

Mon, Jun 3, 11:09 AM

to me
Hi All.

Guess you all know i am a bisexual guy and i love to crossdress whenever i get a chance and i am alone.

Well as it happened I was on a work trip to chennai and bangalore some time back. It was not a planned one and my boss told me in the night that i had to go and all arrangements have been made. I reached by the afternoon flight, took a cab and checked into the hotel booked by the office. After completing all this and settling down in my room I decided to out and buy myself some nice gurlie stuff, as i had a cpl of days in chennai and 3 days in bangalore. I went to a nearby market and bought all i needed ( Bra, panty, stocking, skirt, top, heels )

I took an auto and rushed back to my hotel, I was very excited to try on my new lingerie and then have some fun.

The climate there is very humid and warm , so before anything else I had a shower , then i dressed in my bra and stuffed the cups with some soft cloth and wore all my other lingerie and then came the bright red skin hugging top and a white floral mini skirt. Finally finishing off by wearing the black high heels.

I was admiring my self in the mirror and my dick was tingling looking at the sexy gurl in the mirror. I walked around the room and loved the sound of my heels on the floor.
I was so horny I wanted the first man I met to fuck me. As luck would have it, the door opened suddenly and the house keeping guy came in to make the bed for the night. He saw me all dressed up, both were taken by surprise, I just ran to the bathroom and closed the door, he went out.
I came out after a minute and had a sip of cold water to calm down and there was a knoc on the door, I opened the door just a bit to peep out and it was the same guy. He motioned me let him in and said” I am a top!”
That’s all i wanted to hear. I let him in and locked the door and put the do not disturb light on.
Me- So you are a top?
Him- Yes
Me- You want to do now ?
Him – Yes, you are looking nice, ( his one hand went on my boobs and one on my bums)
Me- open your pant
He got naked waist down and held my hand took me to the bed. He lay me down on my back and was pressing my boobs over my top and rubbing his other hand between my legs( like rubbing a pussy). He was getting harder every second. Then he turned me around and slid down my stockings and panty. He was squeezing my bums and rubbing his fingers over my hole.
After a cpl of minutes he stopped, went to the washroom and brought out some body lotion and poured a generous amount on my bums.I love when some one massages my bums and i was also getting hard. He massaged them and with his fingers he rubbed my hole. Suddenly I felt a bit of pressure on my hole and in went one finger. Ohhh that felt so good, I moaned a bit and he realised I am liking it. He was sliding his finger in and out for a min and then went in second finger as i could feel my hole stretching a bit. Another two mins of squishy pumping with two fingers and then came finger number three. He folded my legs to my chest and asked me to lift my bums. He put some more lotion and had his three fingers in my hole. In out , in out , in out they went making squishing sound with each motion. I was stroking his rock hard tool. which was shaved and dripping about 6inch long.
He turned me on my side and still had his fingers in me and lay down beside me with his tool on my lips. I guessed what he wanted and i took him in my mouth. He moaned….
I don’t like sucking much but i was too horny. His fingering became faster and after a few minutes, he got up made me lay on my back. He saw the pack of condoms on the side table and opened one and rolled it on his tool in no time.
He was ready and so was I. I adjusted my boobs ( I always wear C or D cup bras as I like Big boobs). He put my ankles on his shoulders and positioned his tool on my hole, we both looked at each other and he pushed. Slowly going all the way in. The lotion and fingering had my hole so ready for the real thing. His tool felt like a hot rod entering me. He closed his eyes and held on for a few seconds.
Then he started pumping in long full strokes. Making thup thup sounds with each stroke and my tits were bouncing.
I Held my boobs with my hands and he was pumping with my legs pointing up. I was hard my self. After a few minutes of pumping he turned me side ways and entered again. His hands on my left hip and he was pumping faster. ” Ohh baby..ohhh babyyy…ohhh babbyy ” was all he was saying.
After another few mins of sideways pumping, he was filling me deep. Then he turned me doggy and got up on the bed, behind me. He was standing over me and entered me in one fast full stroke. Now he was pumping me long strokes and his balls hitting my ass.

He was going so deep, after a minute of this he got down on his knees on the bed and entered again, this time he was fondling my boobs( padded bra) over the top and pumping my hole. I was soo horny , I was stroking my own dick and was about to cum any second. He increased speed and his breathing got faster , I knew he was about to cum. He pumped real hard for half a minute and rammed his cock deep in me and filled the rubber with all his love juice. I came along with him and sprayed my cum all over the bed sheet.

He illegal bahis siteleri pulled out and went to clean his cock, I lay on the bed. I got up lit a smoke and again went on the bed laying with a cpl of pillows behind my back. He came out and dressed up fast.
Him- I have to go or manager might ask why taking so long.
Me – Thanks for the fun
Him – Did you like it ?
Me- Ohh yes ,, lovely
Me- Are you on the night shift?
Him – No but I will be back tomm morning at 7AM
Me – Will you be able to come in morning?
Him – Yes sure. I will come early and come to clean your room.

Ok Thanks, see you in morning?

He dressed and left and i was there only in my top and naked bottom down and still feeling horny. I opened a beer from the mini bar and had one and the second one too in a matter of 15 mins.

I just wore my string panty and skirt back on.
I ordered a cpl more beers as there were none left in the mini bar and i went to the window and lit a smoke watching the traffic below ( my room was on 6th floor). Halfway through the smoke I noticed someone watching me from behind half closed curtain on the opposite of my room window. Suddenly the door bell rang and I heard the door handle turn. Before I could do anything to hide or rush in the bathroom, in walked the waiter with my beers. I just rushed into the bathroom, not before he saw me dressed up as a busty gurl in a mini skirt and smoking.

he kept the beers on the table and called me to sign the bill. Which I would have to come out and sign and i had no normal clothes with me in the bathroom. So I just quickly removed my top and bra and wrapped a towel around my waist making sure that the panty anad skirt is not visible, and came out to sign.
I took the bill and signed and gave it to the waiter. He was just looking at me from top to bottom. I realised he had seen me dressed up and was wondering why a gurl went in the bathroom and a half naked guy came out. I gave him a tip and said Thanks. He just stood there for a bit and then said.. ‘ you want anything more?’
Me- no thanks , I will order food later.
Him – OK. I am on night shift , if you want anything else , just call room service and ask for Dinesh.
I realised this is going to be one horny night, as there was a light bulge in his pants. ” Sure, I will call you if I need anything” I said
Him – I am free after 11 30 usually
I thought , wow , another guy for fun. ” Ok..call me around 11 30 when you are free”
I gave him another tip. He left and I opened a beer, went back to the bathroom and wore my lingerie and top again.
I remembered the voyeur across the window and i lit a smoke, adjusted my boobs and went to the window. I could see a dim light on in the voyeur’s room and suddenly there he was standing in his window watching me. The lights in my room were ON. I do like a bit of exhibitionism, I started doing a bit of a dance making it as sexy as I could and I was making sure I dont look directly towards him but I was keeping a look at his window. Then after a cpl of minutes halfway through my smoke, I removed my panty as I was getting hard and danced with my cock bouncing and in full view. I crushed the cigarette and danced fingered my hole in full view for him. I turned and while dancing I saw He had his dick out and was masturbating. He had a nice average size dick which was fully hard from the look of it.
I decided to take a chance, I waved at him and blew a kiss. He stopped his hand motion for a few seconds, but then after about half a minute he waved back. He signaled me to come over. I motioned to my dress and said not in this dress. He motioned if he could come over. I gave him the thumbs up and with my fingers told him my room number, and showed him the room phone so we could talk before we did anything more.
Sure enough …just as I closed the curtains my room phone rang….

As you read the previous part, the phone room rang.

With basic introductions over ( Lets call him Raj)
Raj- So how long will you stay here
Me- I am here fro tomm night as well
Raj – Ohhh…… I am leaving tomm evening
It was about 830 PM
Raj- Have you had dinner?
Me- No!
Raj – Would you like to join me in my room?
Me- No thanks…. I cant go out dressed like this
Raj- Ohhhhh… I was thinking maybe we can have a cpl of drinks and………..
Me- I have had my drink and what you mean by drinks and….
Raj – I mean you are looking so hot
Me- Thanks….so have you been with a gurl like me before?
Raj- No…I have seen a few shemale videos but never met anyone, am curious
Me- I am no shemale. I am a CD, just a normal guy who like to dress up differently.
Raj – Ohh…OK….So how come you have boobs and a tool?
does that mean you dont meet other men?
Me- I have put pads in my bra and The rest I wear normally.
Meeting a guy depends if I am in the mood and on the other guy. I dont like pushy guys or guys like to know personal details
Raj – OK, So can i come and meet you?
Me- You want to come to my room??????
after pause
Raj – If you dont mind!
Me What you want to do in my room, you have seen enough of me in the window
Raj – Yes, but I would love to see in person and I have such a dream of meeting a shemale. I can pay you also.

I didnt know why he said that, maybe he thought I am a call gurl. Well I didnt mind, getting a bit of cash and having fun too.
That perabet giriş would a tick on my fantasies to fulfill list.

Me- you are really desperate. what you want to pay me for?
Raj – I would like to have some fun ( he said very nervously)
Me- How much will you pay( never done this before, but trying to play with him )
You want me to do you or you want to do with me?
Raj- I want to do to you, I will pay you 1K for sex ( again nervously)
Me- Make it 2K and we can spend some time together. but I will take it at my room door. then i will wear my dress
Raj – sure OK( a bit excited) I will come in 10 mins
Me- Ok.

I went to the bathroom, cleaned and lubed my hole again and adjusted my boobs and other lingerie.Wore my heels and lit a smoke
All this horny talk made drip some pre cum
I just cleaned my self and finished my beer. Was sitting on the room sofa and smoking and waiting. Well I was also a bit excited as it was my fantasy come true.
I finished my smoke and no one came so I lit another one and was browsing my office mail. Half way through the second smoke there was a know on the door, I closed my laptop and checked my self in the mirror and opened the door with the chain on and peeped out.
Yes?.Who are you?
I am Raj, we talked on the phone.
Me- Do you have my package? and he replied affirmative. I opened the latch and let him in.
He came in and I locked the door and put the Do Not Disturb tag on the door.
He was staring at me and he gave me 4 note of 500 each. (Indian Rupees )

I held his hand ( it was cold) and took him to the sofa. He sat down and I walked to the table with my heels clicking on the floor and swayed my ass a bit.
I lit one and he got up and came and hugged me from behind. I could feel his hard on poking me from behind. He brought his hands in front of me from behind and cupped my boobs and squeezed them. Then he was holding my left boob and his hand went behind me and he was rubbing my bums and with his finger he rubbed the ass crack over the panty. I was smoking and pushed back my ass when his finger rubber over my love hole.
Me- You seem in a hurry
Raj- I am so excited.
He started removing my panty and slid it down my legs. Out sprang my semi hard on. I turned around and removed his t shirt. Then opened his belt and , he wasted no time in getting naked. He was already so hard. He had a shaved dick average size but soo hard. He started pressing my boobs again and his hand again went on my bums and his finger on my love hole. My hole was already lubed and I pushed back a bit and his finger went half in. I moaned a bit as I liked it. Then he noticed and his finger went in fully and he started finger fucking me. I was pushing my ass on his finger and he slapped my ass softly with his other hand and squeezed my bums. I crushed my smoke and held his hand and took him to the bed and made sure the curtains are closed properly. I sat on the bed and he came and stood in front of me and he raised my arms and took off my top. He was nude and I was wearing only my padded bra. He made me lie on the bed on my back and lifted my legs, This time he put in 2 fingers and fucked me fast with them.
I was getting soo horny, I came in doggy pose and he again put in 2 fingers. I gave him some lube to put on my hole and his fingers. He lubed me again and pushed 2 fingers as deep as he could. I was moaning. He took the lube and put some more on my hole and some on his tool. I saw that and said ‘ Only with a condom dear ‘ and his face became a bit sad. I have condom and I gave him one from the drawer. He was excited again and rolled it on his dick. I was in doggy pose still, He slapped my ass a cpl of times and said ‘ Ready babes , here i come ‘
He positioned his tool on my love hole and pushed. All the fingering and lube made his tool go all the way in. He moaned and held it in for a few seconds. His rod was hot and I was feeling so full. I wiggled my ass a bit and he started slow and long strokes( I so love slow strokes) after a cpl of mins of slow strokes he became fast and was making thup thup sounds as his balls hit my ass bums.
He was squeezing my bums and fucking me from behind. Then he held my boobs from behind while still doing long strokes and pumping me. He did for almost 5 minutes non stop and was moaning and so was I. Then he pulled out his rod and made me lay down on my belly and spread my legs. He put some lube on my hole and put in 3 fingers and pumped fast with his fingers making squishy sounds. After a minute of fingering he spread my hole and got on top of me and entered me. He was pumping in long strokes and hitting his balls on my buns. He had some stamina and after almost 5 mins he got up. He went and have some water and I also had some. Then we both got on the bed and he motioned me to ride him cowgirl style. I adjusted by boobie pads and got on top of him . He positioned his tool under my hole and i sat on it, ohhh it went so deep. I started to and fro motion with his dick deep in me. what a feeling it was. Then after a cpl of mins he held my boobs and got up just a bit and started sucking my boobs just as if they are real. I pushed him back after a bit and started up down on his hard on. He closed his eyes and was moaning and so was I. Then suddenly he pulled me close to his chest and started pumping perabet güvenilir mi from under me in fast strokes. He was hitting deep in me.
After a cpl of mins he made me lay on my back and lifted my legs and put my knees on my chest and entered me. Now he was at speed and i could sense he was about to cumm. He pumped for another cpl of mins and then moaned and made a few long deep strokes and shot his load in the rubber with his cock fully deep inside me. Then he caught hold of my hard on and started a hand job and horny as I was, I came in a few strokes all over my belly.
He pulled out and we lay on bed catching our breath. After a cpl of mins we both got up and went to the washroom and cleaned off each others’ tools. As i was walking out of the washroom door he slapped my ass.
We both had some water and he got dressed and I lit a smoke.
Him- I will leaving tomm afternoon. Can we meet again tomm
Me- I have a meeting tomorrow, won’t be free in day.
Him – Can we do it early morning?
Me- Hmmm. you are a naughty boy!
Him – Please once
Me- Ok but you know the price( as I knew now that he was ready to pay me )
Him – sure babes, I will ring you before breakfast , then after that we can break fast and go to work.
Me- Hmmm….will be too early but I guess we can do it.

He kissed on the cheek and left. I changed to normal dress and ordered food. Dinesh came with my order and asked ‘ Should I come and clear the dishes late at night?’
Me- Ok come after an hour and make sure no one knows our secret.
Him – I will make sure, as only 2 waiters on night shift for this floor. So no problems.

I had my food and relaxed a bit. About 10 mins before the decided time, I got up and dressed up as Sheila, only this time I padded the bra a little more ( I love big boobs)and cleaned and lubed my love hole.
I switched on the TV put the Do Not Disturb tag on the door, lit a smoke and was waiting.
He called on my room phone and asked if he can clear the dishes and I said sure. He came a few minutes later knocked and I just called him to enter. He came in locked the door and put his tray on the table.
I was there near the bed watching TV and smoking, I motioned him to drop his pants and sit next to me. He undressed fast and came and sat next to me. he was already hard and had nice shaved tool. His tool was about slim but long and hard. I crushed out my ciggie and came back on the bed. As soon as i sat down his hands were all over me. I also caressed his body and rubbed his bums and tool. He got up and stood in front of me, I took his tool in my lips and he froze. He just kept on fondling my boobs while i sucked him. My hands were playing with his bums and i put my finger in his crack and rubbed it on his hole. I felt something creamy there and i pushed in one finger. He moaned. I stopped sucking and asked him, why he had cream on his hole. ‘ Can you do me after I do to you? ‘ he said. I was like , wow, he is a vers. I got up and slid down my panty and made him sit on the bed and stood in front of him. He rubbed his his face on my dick and I was getting a tingling and getting hard. Then he started sucking my dick and did for a few minutes till I was fully hard.
Then I pulled down my skirt and gave him a condom. He rolled it onto his tool and made lie on the bed in doggy pose. He came behind me and kept his tool at the entrance and pushed. The lube helped him slide the head in and I let out a moan. He pushed again and was half in, ‘ do slow long ones dear ‘ I said. He pushed again and went fully in. He held there for a few seconds and then he started pumping at a regular pace and doing deep thrusts. he pumped in doggy for almost 5 mins and then he moaned and pulled out cummed in the rubber. ‘ you have such a soft and tight ass ‘ he said. ‘ Thanks ‘ I said, and now made him lay on the bed on his back, I lifted his legs and put some more lube on his hole and positioned my tool on his hole. He pulled his knees to his chest and his bums raised a bit. I pushed and entered half in the first push. He moaned in pain ‘ yours is very thick ‘ he said.( I have a 6.5 inch tool and decently thick). I stopped for a min and then he nodded his head to do again. I pushed again and went in fully. He just closed his eyes and i pushed again. Then pulled out almost fully and pushed back in. He was ok now so i started pumping him.He was pressing my boobs while I was pumping him( That was such a great feeling). After a few mins I turned him doggy and entered fully in one push and he almost fell on the bed. I held his hips and pumped him deep. He was moaning a lot. I had to tell him be quiet of keep his voice down.
I pumped him doggy for a few minutes and the earlier two rounds had already made me horny enough and I was about to cum. I banged him deep hard strokes and finally thrust in as deep as I could and cummed deep in him in the condom.

We both got up and cleaned our tools. He got dressed and I was wearing my top with boobs inside and naked waist down. He cleared the dishes and went away.
I locked the door and went to sleep half nude.

I was woken up by the ringing of phone and still drowsy I answered it.
Raj- Hi, Its me Raj, can I come now?
Me – ( still drowsy) Hi, I slept a bit late, what’s the time?
Raj – 6AM
Me- Ohh Ok. Give half an hour to get ready. Call me again in half an hour.
I woke up, did my nature’s call, had a shower, and dressed up as Sheila.
He called at exactly 630 AM.
Raj – can I come now?
Me – Ok sure, please remember my gift( referring to the money)
Raj – Sure babes

After a cpl of minutes there was a knock on the door. It was Raj.

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