It took me some time to realize and accept I was gay. For a long period of time I was masturbating fantasizing that I was a girl, but on most cases I was making love with another girl; that to my mind was a proof that I was not gay. Several times I was wearing my sister's underwear and clothes but I never pictured me with another man; not to mention that I had never fingered my ass.
It was summertime and I was 15; at that time we were living in Cyprus (my father was a diplomat and we moved in several countries around Europe). As my father was stationed in the capital city (Nicosia which is located in the center of island) my mother, my sister and me were enjoying our summer vacation in our beach house in a village close to Larnaca. My father was coming every weekend but that one something came up and he was not able to join us. My mother decided to visit him and I and my sister stayed at home (my sister was 19 by that time).
It was Saturday afternoon and she had arranged to go to the city to visit a friend of hers and she was going to spend the time at her place.
That was a perfect chance for me; I was really enjoying masturbating wearing my sister's clothes. Something I was not able to do for the last two weeks at the beach. A few minutes after she left I went to her room. I picked red underwear, a sexy mini skirt and a stretch top. I felt so amazed when I saw that she had a pair of stockings too, black ones. As there was no risk of someone coming I decided to try and apply some make up on me; I never did that in the past but I had seen my sister doing it so many times that I was pretty familiar with the process.
About 45 minutes later I was stunned while looking at the mirror; it was not me but a beautiful girl I was seeing.
The fact that I didn't have any body or facial hair (just pubic) was making the reflection identical to a girly one.
No need to mention that my cock was hard; I went back to my room, laid on the bed and starting touching my body. My tits, my stomach, my feet and then my balls and my cock. I started jerking thinking that I was a girl making love to another girl. I moved my hand on my back and started playing around my asshole, I did that for several minutes and I realized that it was loose; I licked my finger and moved it down there. It was painful at the beginning but I liked it. It was not long later when my whole finger was inside my ass. I kept masturbating and I was picturing myself being fucked by a man. That image did not scare me at all; on the contrary I came so hard that it took me several minutes to get my breath back. I repeated that two more times.
It was 7PM when the phone rang. It was our neighbor (a family friend too) who knew I was alone and asked me to join them for dinner at 8. She also told me that her son (a friend of mine) just came so we could meet. I rushed to clean up (and put the makeup off) and I was there at 8!!!
During dinner we were talking with Peter and he asked his parents if they were ok with him sleeping at my house. There was no issue as both houses were next to each other.
It was almost 9:30 when I and Peter got back to my place. Immediately he moved to the living room and asked me to join him. He had brought a porn tape (VHS back then) and was looking forward to see it. Me too to be honest ;)
A few minutes later we were watching porn and eventually our cocks were erected. It was Peter who first said that he could not stand it anymore and took his pants off starting to masturbate, I followed immediately. We both came a few minutes later.
Peter stood up to take a shower, a bit later I wanted to pee so I entered the bathroom. Somehow while watching the movie I didn't pay any attention on Peter's cock and right now I was watching it. It was Peter's voice which "woke" me up. What he said, is there something wrong? No, I said, I was thinking of something, nothing important.
Peter came out of the shower wearing just a towel, I went in and a few minutes later we were both sitting in our towels at the living room. Suddenly Peter got up and looked at me excited, he remembered that my sister was to stay at the town and he wanted to go at her room to see her "dirty underwear", I declined and when he moved towards my sister's room I went after him. I stopped him in front of the door and pushed him over my room on the other side. We started "fighting" and as he was stronger than me it was easy to put me down. I was laid down facing the floor and he was over me. I tried to turn around but it was impossible.
"I will let you go if you admit you are a sissy in a female voice" he said. "Never" I replied and he asked more pressure on me.
"Since you resist your punishment will be harder" he said. I couldn't understand what he meant when he grabbed a t-shirt of mine and used it to tie my hands behind my back. He then took another one and tied my fit. He stood up laughing and said "you will see now". He then let me alone and went to my sister's room. He came back a few seconds later holding black panties, a pair of stockings and a skirt. He turned me over and again I was facing the floor, he sat on me and untied my legs.
"You will see now, you didn't want to say you are a sissy. Well guess what, I will make you one now" He placed himself on top of me in a way that I could not move and not much later I was wearing (again) my sister's underwear and stockings. He thought that he was punishing me but I was excited. And pretty soon that was obvious....
"What the fuck" he said. "You like it, don't you?"
"No Peter, I do not like it" I said.
He laughed and said "yeah, I see that". He took his towel off and said "would like to have that cock?" "No I don't" I replied and managed to untie my hands. I stood up and moved against him. We ended up fighting on my bed and the result was the same as last time. Only this time I was laid down facing him and he was on top of me but very close to my face.
As he was naked his cock was almost touching my face, I took my hand in front in order to avoid it. I cannot recall how but seconds later I was jerking him. His cock was hard and strong now and as he moved a bit up I started to lick his balls. I felt drops of his warm cum on my face.
Nobody said anything for some minutes, not until Peter moved back and spotted that my cock was still hard.
He laughed again, I couldn't stop laughing too. He stood up and went to take a shower. I don't know how but I decided to go for it.
I went straight to my sister's room and when Peter came out of the shower he found a sexy girl waiting for him at the living room.
He was stunned, it was so obvious.
"Come here" I said in the most feminine voice I could. He did and there he was standing in front of me in his towel.
I took the towel off and start licking his wet cock while my hands were on his balls. I felt his hand going over my hair and heard him breathing heavier. His cock was still soft and I took it in my mouth very carefully. I felt it growing inside my mouth while I was giving him a blow. It was hard and strong now and he was moaning. I pulled myself back, turned over and bend.
He took of the skirt and the panties and moved his cock close to my ass.
"I have never done it before" I said.
"Me neither" he replied
"We will need some lubricant" I said
He went to the kitchen and returned with a bottle of local olive oil. It worked perfectly.
His cock slipped gently in my ass, I was the one moaning now as he started to fuck me slowly and gently. I was the one who started to move my ass faster and he followed. He was now fucking me hard and I loved it.
"Fuck me baby, fuck me hard" I said, "fuck me, I am your bitch baby, your sissy slut. Fuck my ass hard"
He did so; I could feel my ass on fire as his cock was getting deep inside me.
"Do you like it? Do you like being my whore?" he said
"Oh yes baby, I do, I love it, I am a slutty whore"
He was ready to cum now, his was fucking me so fast I was about to scream. All the sudden he pulled his cock out and I was feeling his cum all over my ass.
He was moaning hard and so was I. He sat next to me and I could see the excitement on his eyes.
"Did you like it baby?" I asked him. I didn't wait for the answer, I turned and moved down "let me clean you baby" I said and I took his cock on my mouth again. I tasted his cum now and I loved it.
We sat there for almost an hour, I bended over his chest and he had his hands between my hairs. I was feeling like a girl and I loved it.
"Shall we go at the bedroom?"I asked