Cross Dressing In Goa Part 1

I am Sumit, a regular reader and fan of ISS. This is my first time so kindly ignore spelling mistakes. I am a19 year old chubby boy. I am fair and 5 feet 4 inches tall. This incident happened when I went to Goa with my friends.

After semester exam, my classmates decided to visit Goa to relax. We reached Goa early in morning. Everybody was tired because of 8 hr train journey in general compartment. We all had breakfast and decided to take rest. After a while we went on beach. We played football, enjoyed in sea, had lunch in shack. All boys in my group started drinking and few girls also joined them. I was only boy who dont drink. We me and few girls decided to leave drinkers alone and roam on beach. We were there for 4-5 hours. After watching sunset we visited our friends in shack. They were wasted. We literally drag them to our hotel. As we were large group, we booked 4 rooms, 2 for boys and 2 for girls. We dumped boys in one room (as they were wasted) and drunk girls n another. We all sober people sat in one room.

We were angry because our evening plan was wasted because of drunken friends. As time passed we got bored so girls started doing makeup and hairs. I was playing game on phone. All of sudden my friend snatch my phone and said lets apply makeup on him. I resisted but finally allowed them to do it. They made me sat on stool and all girls just surrounded me. They were applying lots of cream, lipsticks and God knows what on my face. One girl bought hair extension. After one hour they showed me final result. I didnt trust my eyes. In mirror, I saw beautiful girl. I was smiling and shying as girls started “woo-ing” at me. After this we were hungry, so we went to have dinner.

I kept my makeup as girls requested me to keep it on. I was wearing Capri and t-shirt. All staff at hotel referred me as “Maam”. Every time I heard maam I used to blush. After dinner we returned to room. I was about to wash my face one of my best friends stopped me. She said she had plan and took me to another empty room. She said to me that I looked very much like a girl and should try female cloths. I was shocked and said no to her. She requested me a lot and after half hour drama we decided to flip coin. If she wins, I have to do whatever she says. We flipped coin n she won.

She shouted and starts looking for something in bag. After a minute, she removed couple of creams from her bag. One was hair removed and another was some moisturizer. I applied hair removal cream and had bath. All my body hair was gone. It was strangest feeling. Then she applied couple of creams on my whole body. I must admit, it felt good and smooth and I smelt very nice. She dropped bomb on me when she took skirt and top in kept it infornt of me. She said I had to wear it. I must confess now, I always fantasized about being a girl. So I was happy as well as nervous. I decided to wear them when she promised to keep it secret. She gave me breast form and bra. I wore them. I was completely transformed. I looked like a girl. With soft panty n bra hook poking in my back I was feeling feminine. After that we talked for hours like two girlfriends.

It was around 1 oclock at night, someone banged on our door. We both got scared. We asked who was it; we get reply as Rahul, who is our friend. Within a fraction of second my friend opened door. I was scared as I was wearing makeup and female cloths. As he was drunk he didnt recognized me. My friend closed door and we three sat on bed. He inquired about me to her; she said she is girl living in room next to her. To my surprise, my female friend n Rahul started drinking so I decided to sleep. After 11.5 hour I hear noise of glass. I woke up and saw both of them having sex. Yes they were having sex in front of me. I didnt know what to do so I decided to watch. After few min I got very horny and decided to join them. I went closed to them and started kissing Pooja on her beck while she was sucking her. She noticed me and said “I know you want this” in my ear. I smooched her. Rahul was happy to see to girls on their knees in front of him. Pooja grab my head n guided me near his cock. I resisted. Then Rahul also forced me to suck cock. I smelled and tasted precum. I sucked his cock for 10 min.

After sucking cock, Rahul started to fuck Pooja. I was licking and figuring her while he pounded her pussy. He used to remove his cock and I used to suck it. After few seconds, he started to fuck her again. Few minutes later, Pooja whispered me that “u r going to loose ur virginity”. I didnt get it. Suddenly Rahul grabbed me by my waist and pulled my ass towards him. I knew I was going to get ass fucked. Pooja applied some cream on my ass and Rahul started fingering me. She kept my panty on so that he cant see my cock directly. After some minutes, I felt tip of his cock on my ass. He whispered “here we go baby” n thrust his cock in my ass. I screamed. It was painful.

He started to fuck me and pain turned into pleasure. I went wild. Asking him to spank me, bite me, and fuck me. Pooja was dumbstruck looking at me. She said she didnt see such bitch in her life. I said u r jealous of me and smooched her. After few minutes, I felt warm inside my ass Rahul collapse on me. I knew he came in my ass. In couple of min he wake up n smooched me. He said, “u r the best bitch I have ever fucked” n went outside. I was their lying in sweat n cum of Rahul n recalling those magical words he said to me. Pooja came n said, “Tu to badi randi nikali. I know lots of guys whom u can satisfy”. I blushed and we slept.

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