Hi all. Guess you all know I am a bisexual guy. 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. 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 settling down in my room I decided to out and buy myself some nice girlie stuff. I had a couple 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. I 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.
My dick was tingling looking at the sexy girl 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 housekeeping 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. There was a knock on the door. I opened the door just a bit to peep out and it was the same guy.
He motioned me to 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 sign on the door.
Me- So you are a top?
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. He 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 couple of minutes, he stopped and went to the washroom. He brought a body lotion and poured a generous amount on my bums. I love when someone 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. Oh, that felt so good. I moaned a bit and he realized I am liking it. He was sliding his finger in and out for a minute. Then went in the second finger.
I could feel my hole stretching a bit. Another two minutes 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. It was shaved and dripping about 6-inch long. He turned me on my side and still had his fingers in me. He lay down beside me with his tool on my lips. I guess 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. After a few minutes, he got up made me lay on my back. He saw the pack of condoms on the side table. He 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 sounds with each stroke and my tits were bouncing. I held my boobs with my hands. He was pumping with my legs pointing up. I was hard my self.
After a few minutes of pumping, he turned me sideways and entered again. His hands were on my left hip and he was pumping faster. After another few minutes of sideways pumping, he was filling me deeply. 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 so 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. He filled the rubber with all his love juice.
I came along with him and sprayed my cum all over the bedsheet. He 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 couple of pillows behind my back. He came out and dressed up fast.
Him- I have to go or the manager might ask why I am taking so long.
Me – Thanks for the fun.
Him – Did you like it?
Me- Ohh yes, lovely. Are you on the night shift?
Him – No but I will be back tomorrow morning at 7 AM.
Me – Will you be able to come in the morning?
Him – Yes sure. I will come early and come to clean your room.
Me – Ok Thanks, see you in the morning?
He dressed and left. I was there only in my top and naked bottom down and still feeling horny. I opened a beer from the minibar and had one and a second one too in a matter of 15 minutes. I just wore my string panty and skirt back on.
I ordered a couple more beers as there were none left in the minibar.
I went to the window and lit a smoke watching the traffic below. My room was on the 6th floor. Halfway through the smoke, I noticed someone watching me from behind the half-closed curtain on the opposite of my room window. Suddenly the doorbell rang. 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 girl in a mini skirt and smoking. He kept the beers on the table and called me to sign the bill.
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. I wrapped a towel around my waist making sure that the panty and skirt are 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 realized he had seen me dressed up and was wondering why a girl went into 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 the night shift. If you want anything else, just call room service and ask for Dinesh.
I realized this is going to be one horny night, as there was a slight 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.
I lit a smoke, adjusted my boobs and went to the window. I could see a dim light on in the voyeur’s room. 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 dance making it as sexy as I could.
I was making sure I don’t look directly towards him. I was keeping a look at his window. Then after a couple 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. I 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. To be continued.
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