Hi all, this is another one of my (s)exciting work trip experiences. I have combined a few of my experiences into a sequence, but all these events (though not in order as they happened) are true.
So, as it happens that I had to travel for a whole week to 3 cities. I got my travel tickets from the office. I boarded the early morning flight and reached my destination. I checked into the hotel and freshened up and went for the first of many meetings. I had a good meeting and closed the contract.
It was around 3 pm. I called the office and shared the good news. I was feeling lucky with a good start to the trip. I called up the second client and they scheduled the meeting for the next morning.
With nothing else to do for the entire afternoon, I took a cab and went to the market near my hotel to do some lingerie shopping. I paid the cab guy and walked around looking for a lingerie shop with not many customers, and after walking around for 20 minutes, I found one.
The shop had many lingerie sets on display in the window and being mid-afternoon, there was only the staff – one behind the main counter, one behind the display window (the owner I guessed), and a mid-twenties guy, both watching something on their mobile screens.
I took a deep breath and entered. They both looked up and greeted me. I took a sip of water from my water bottle and asked for a bra in my size in D cups. The assistant got up and brought me a few. I liked one and I asked if he had some of the fancy, lace bra-panty sets in my size like the ones displayed in the window.
Rohit said “sure” and showed me a few. The last box he opened had a nice red bra and matching lace panty. I chose that and then asked for a pantyhose. I paid for the stuff and went on looking for shops to buy somebody lotion, condoms, and smokes.
While buying the rest of the stuff, I saw a liquor store and also bought a bottle of whiskey. While waiting for a cab near a street market, I saw a guy selling some nice floral pattern skirts. I bought one with a nice white sleeveless top. I was all excited to get dressed up en femme and I quickly took a cab and reached my hotel.
I went to my room and threw all the new stuff on my bed, went to the bathroom and cleaned and lubed my hole. I had a warm bath, and applied lotion on my body. I dried myself and came out and headed straight to the bed and got out my new lingerie and dress. I wore the lace panty and bra, padded the bra, and then came the pantyhose.
I went to check myself in the full-length mirror in the dressing room. I got a tingle between my legs looking at the sexy girl in the mirror wearing red lingerie.
Then I came back to the bed and wore the top and skirt. To finish it all off, I wore heels. I picked my pack of smokes and lit one up and walked to the mirror again to admire myself. I was already getting hard! I saw myself in the mirror and my dick wanted to just spring out of the panty. I was now so horny that I just wanted a dick in me.
I thought of seducing the hotel staff but was scared, so I dropped the idea. I went online and checked the local ad listing for guys seeking guys/CDs (Cross Dress). I called up a couple of guys and they sounded too eager and rustic. I prefer a guy who is decent and can play for mutual fun, and is not money-minded (as they mostly are).
Finally, I found an Ad. The guy was in his late twenties, a fit guy with an almost 7″ tool (as it said in his ad details). I called him and he was quite decent to talk to. We discussed our preferences and he told me he worked at a spa and could meet me at 9 after his shift. I gave him my room number and we agreed to meet.
Let’s call him Rohit (R). It was 6 pm, so I had a good three hours before he came. I started watching the TV and dozed off.
I woke up around 8 pm. I went to the bathroom and freshened up, lubed up again, adjusted my boobie pads and dress. I opened a beer from the minibar and lit a smoke. Then I walked around the room and the sound of heels on the floor made me feel like a girl.
I finished my beer and opened another one. I was dancing to the tune of some Hindi movie songs on the telly when my phone rang. It was Rohit. He said he will be there in 15 minutes. I got excited and nervous.
I went and lubed a bit again just so that I was ready for the fun. I sipped my beer and lit a smoke. After a few minutes, my phone rang, it was Rohit. He said he is outside my room door. I took a deep breath and walked to the door (with the heels tapping the floor it made me feel so sexy).
I opened the door and it was the same guy as in the pics, on the Ad. I removed the chain and said, “Come in,” and walked back to the sitting area to get my smoke. He came in and said, “Sir, called me for a massage,”
I turned around and said, “Yes dear, I did.”
“Oh, I thought you are a girl,” he said.
“I told you I like to dress up as a girl.”
“You look pretty in the dress,” he said. I took a drag from my smoke and turned to go to the bathroom to adjust my dress and boobie pads.
I told him, “Why don’t you strip and be ready to massage me? I will be back in a minute.” I went in and adjusted my dress and pads and came out. I crushed my ciggie and saw him standing near the bed in only his boxers and I could see a semi-hard-on in them.
Rohit motioned me to lie on the bed. I lay on the bed, he came close and put his hands on my side and made me turn over face down on the bed. He started pressing, massaging my calves lightly and then a bit harder. It was quite relaxing.
The masseuse worked his way up to my thighs and gave them a good massage for 5 minutes. Then his hands were on my bums.
After a couple of minutes of pressing and squeezing my bums over the skirt, he pulled down my skirt and I was there with my ass in my lace panty and hose. He started massaging in a round motion over my bums, and then he got out his bottle of oil from his bag. “You will have to remove the leggings so I can massage with oil,” he said.
“Ok dear, why don’t you remove it for me?” I said.
He slowly slid down my pantyhose and kept it on the bedside table. He then spread some oil on my thighs and calves, and with strong hands, he applied pressure and was massaging my legs.
Bit by bit, his hands moved higher towards my bums and after a few minutes, he poured some oil on my bums and started massaging and squeezing them. I let out a few soft moans and he got a signal I liked it.
He rubbed from the side to the top of my bums and then from the centre to outside. I was getting horny. He put his fingers in the sides of the panty and pulled it down all the way. He got up and sat on my legs and poured some more oil.
This time, he put some oil between my bums, the oil trickled down to my love hole. He again started massaging my bums in a circular motion and his thumbs down between my cheeks every few motions.
Suddenly, his thumb pressed down on my hole, and he tickled a bit and put some pressure on the hole. I moaned softly as I was getting horny and it felt so good.
“Your bums are so soft,” he said and squeezed my ass cheeks. (I do have soft and smooth ass cheeks).
“Mmmmm yessss,” was all I could say before he pushed his thumb right down my hole! My own dick was getting harder. He took out his thumb and put a bit more oil and in went his middle finger. A minute of pumping with his middle finger and then went in 2 fingers as deep as he could. I was clutching the pillow, lifting my ass up, and was moaning.
Rohit pumped for a few minutes and I was dripping precum. Then he got up and asked me to remove my top. I got up too and opened my top. I was again face down on the bed, all naked except for my bra. I just wanted him to fuck me right then.
He just opened the hooks of the bra from behind and poured some oil on my back and massaged me. Every once in a while, his hand would go down to my bums and he would finger me before moving back to my back and shoulders.
He put his fingers under the bra straps and wanted me to remove the bra. But I told him I want to keep the bra on. “Don’t remove this, I am a girl right now.”
He then turned me on my back and started to massage my thighs and belly. After doing that for a few minutes, he poured a few drops of oil on my navel and tickled me there. I got very horny with that, and my dick was soo hard now.
The masseuse got up and cleaned his oily hands with a towel and then started squeezing my boobs (not saying again and again that I was wearing a bra with pads). I moved my hand to his tool and it was rock hard about 6″ long.
I stroked him over his boxers. After a few strokes, he quickly got rid of his boxers to reveal a nice, shaved, clean tool dripping precum.
He turned me over in a doggy pose and went his 2 fingers again. I was so horny I was barely holding my moans. I couldn’t hold on any longer and opened the bedside drawer and gave him a condom from the pack.
Rohit opened the wrapper and I took the rubber from him and rolled it on his beautiful tool. He came behind me and slapped my bums a couple of times. He put his tool on my hole and teased me, and slapped my bums again. Then he put the tip on the entrance and pushed. The masseuse was fully in, with the first push.
He held it in for a few seconds, his tool felt so hot and hard. I was bent over and with one hand I was holding my right boob. He started full long strokes, pulling out almost fully with each stroke. I was dripping precum and it was smooth and long strokes for the next 5 minutes.
Then he pulled out and made me lay on my back and spread my legs by holding my ankles. He positioned his tool on my hole and couldn’t enter. I held his tool and positioned it, he pushed and was in. My legs held wide apart and he started pumping. My boobs were bouncing. I held my dick and was almost about to explode.
I let go of my dick and held my boobs. He was pumping me as fast he could. He had some stamina, he pumped in full strokes for the next few minutes and then he closed my legs and made me fold them with my knees on my boobs and his tool deep in me.
The massage guy started pumping again and was going soo deep I couldn’t stop moaning. “Shhh…don’t make so much noise,” he said. I still couldn’t stop moaning with his balls’ deep strokes, though I did so softly now.
After a few minutes, he pulled out, and had some water, and gave me some too. Now he made me doggy again, this time on the edge of the bed. He stood behind me and in went his rock-hard dick. He was pumping me with full strokes and his hip was slapping my ass cheeks.
“Smack,”…..he slapped my right ass cheek and then the left. “Do it softly, it hurts a bit,” I said. He did it again but softer this time.
I was about to shoot my load, and then his thrusts became harder and faster. I could sense he is about to cum. He bent down and held my boobs and pumped me fast.
Then, with one final deep thrust, he moaned and came deep in me (in the rubber) and I shot my load all over the towel on the bed.
We both lay down on the bed catching our breath. After getting relaxed, we got up. He started getting dressed and I wore my panty and lit a smoke.
After he got dressed and was about to leave, I asked him if he can come again early in the morning before I leave for my work. “Sure”, he said, “I will reach by 8 in the morning.”
This was a bit late as I had to get ready after the love session and have my breakfast and travel almost an hour for my meeting. I asked him if he can come early, but he said he lived on the other side of town and won’t be able to come early.
I agreed and he said he would try and make it earlier and give me a call as soon as he is about to reach my hotel.
Rohit left and I called up my regular cab guy and asked him to come in at about 9 am. Feeling satisfied after the humping, I changed into a normal t-shirt and shorts, ordered food, and had my dinner. I slept in ‘girl’ mode.
I woke up around 7, and was excited to meet Rohit. I had a nice warm bath and cleaned and lubed my hole. I adjusted my boobie pads and wore my top and skirt with them. This time, I left out the pantyhose and just wore my heels.
I was ready and checked the time. It was almost 8 and there was no call from him. I got a bit impatient as I had to leave for my meeting too and reach on time. It was almost 8:15 when he called and said that he will reach in 5 minutes. I checked myself in the mirror and again applied a bit of lube as we would not get much time for foreplay.
As luck would have it he called again and informed me that he is stuck in traffic due to road repair work about a kilometer from the hotel.
Finally, there was a knock on the door at 8:35. I peeped through the chain and saw it is Rohit. I let him in and he said, “Sorry, got late due to a traffic jam.”
“That’s OK, why don’t you strip and freshen up?” I said.
The masseuse had some water, placed his oil bottle on the bedside, and then stripped. He went to the bathroom to freshen up, and I lit a smoke and lay on the bed facing my left. I had a few puffs of the ciggie and he came out fully naked holding his clothes in his left hand.
Rohit saw me on the bed and I saw his limp tool twitch and start to rise. He placed his clothes on the sofa and came near me. He held my ankles and caressed my legs all the way up to my bums.
Rohit started squeezing them and poking his finger in my hole. I guess he realized, that I had already lubed because he didn’t go for the oil bottle on the bedside.
Rohit slid down my panty and fingered me and I was getting horny. I took a last drag of the ciggie and crushed it out. As soon as I had done that, he lay me on my back and spread my legs.
He wore a condom and came forward and positioned his tool and looked into my eyes. I closed my eyes and he pushed. What a feeling it was! a hard cock going deep in my hole. I just held my boobs and squeezed them.
He did small strokes and in a minute he was fully in. Then he started his full long strokes and man he was excited. He rammed me deep with a couple of strokes and I had to tell him not to do that.
After a few minutes of pumping with legs spread wide, he turned me over to my left facing the sofa and the full-length mirror. He held my right ankle and put it on his shoulder. We both looked at ourselves in the mirror and then at each other.
He made me remove my top. He smiled and pushed his dick deep in me. I couldn’t take my eyes off the mirror. It was like watching a CD/tranny porn movie. I touched myself and I was soo hard. After another few minutes of pounding, he turned me over in a doggy position. In went his rod.
He was pumping long strokes and suddenly, my phone rang. I checked it was the cab driver. “I will reach in 5 minutes, sir,” he said.
Rohit suddenly picked up the pace while I was talking to the cab driver. “Ya. Ok….I will come down…..in some time,” I replied between gasps and moans.
“Should I come up to take the bags?” he asked.
“No..not right….now…..I …am a bit…..busy …right…..now,” I replied. I couldn’t speak normally cause Rohit was humping me with fast long strokes.
“You seem sick, sir, are you sure I should not come up?” Now I was too horny and wanted to get back to my fucking and anyway the cab guy knew I like to CD (Cross Dress). So, just to end the call I said, “No…don’t come up, my friend is here and he is fucking me……we are….having …..some fun.”
“OK,” he replied and disconnected.
I turned and looked at Rohit. He was smiling and pumping my ass, he suddenly slapped my ass (this time it was slow ) but it felt good. He held me by my waist and his strokes became faster and deeper. I almost fell, face down on the bed twice. One last push and he rammed his tool deep and filled the rubber with all his love juice.
Rohit pulled out and went to wash. I lay on the bed to relax a bit. He came out and started getting dressed. I was on the bed, my skirt up and my tool still hard. I was lying only in a bra and skirt. I motioned him to hand me a smoke from the pack on the sofa table. I lit up and he got dressed.
He got ready to leave, and just squeezed my ass and boobs before saying, “Bye, call me when you come back to town again.”
“Sure will,” I replied. He went and I finished my smoke and had another shower and got ready to go for my meetings.
The rest will be narrated in Part 2.
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