First experience

I want to tell you about my first experience in cross-dressing and what happened afterwards.
First some explanations. When I was 12 or 13 years old I was a slim and tender boy with long hair (early 70’s it was normal for boys to have long hair). I lived in a neighborhood with a lot of c***dren my age (some a few years younger or older). So I had a lot of friends to play with. One of our favorite games was “cowboy and Indians”. We played this in the woods not far from our street. It had most of the time the same scenario. The older boys (2 or 3) would be the Indians and I and the younger boys (also 2 or 3) and the girls (1 sometimes 2) would be the cowboys. The cowboys would travel thru the woods and were ambushed by the Indians. They would capture us and take us to their camp. The boys were tied to trees but the girl(s) were always taken inside their tent (to be tortured they told us, but we all know better don’t we?). Of course they always made sure we had no idea what was going on inside.
One day most of us wanted to play cowboys and Indians again but there were no girls that time. That made that the older boys didn’t really want to play (understandable isn’t it?). So I suggested that I would play the settlers woman. They agreed but only If I dressed accordingly. I know my mother had some old clothes in the attic, so I agreed. I hurried home together with my best friend and we searched in the boxes of clothes. I found an old dress that fit me rather well. First I put it on above my boy clothes but my friend told me that you could see that I was wearing my clothes underneath. He had found an old bra, some panties and nylons. He said that if I wanted to play a girl that I should dress properly. Again I agreed. I stripped naked ( it wasn’t the first time he saw me naked) and put on the panties. My friend helped me with the bra (we stuffed some old socks in) and with the nylons (damned they felt good). Then I put the dress back on. We went to the bathroom were we fixed my hair in 2 tails and I put on some lipstick. When I looked in the mirror, I really looked like a girl.
So dressed like that we hurried back to the woods. The Indians were nowhere to be seen, just one of the younger boys was waiting for us. He told us that the 2 older boys had already started the game and were waiting for us somewhere in the woods. The 3 of us started our “journey” thru Indian territory. After about 5 or 10 minutes we were ambushed. As usual we were taken to their camp, the 2 “men” were tied to trees and I (the “woman”) was taken into the tent. The tent was constructed on 4 small trees (they formed almost a perfect square). They f***ed me face down on the ground and tied my hands and feet to the 4 trees. So I was lying there spread eagle, face down. Because my legs were spread, the dress rode up and revealed the panties I was wearing. The Indians were really surprised that I was also wearing girls panties and nylons. Then they started “torturing” me. They started with spanking my panties but soon their hands were also caressing my little ass and legs. I couldn’t help it and soon felt my little friend grow bigger inside the panties. Then I felt one of them pull down the panties but of course because my legs were spread they couldn’t take them down very far but it was enough to let me lying there with my little ass naked. I remember that one of the Indians said that even without the panties I still looked like a girl. The other one replied that he wondered if I would also react as the girls they had in their before. They started spanking me again but not very hard and again soon the caressing followed. They caressed my little butt and I felt them pulling my cheeks apart. Before long I felt them caressing me between my cheeks and their fingers would close in on my little hole. When one of the Indians really touched me hole, I couldn’t help myself and pushed my butt upwards. It was one of the weirdest and most pleasant things I had ever felt. They had noticed it also and said that I really reacted like the girls. I heard one of the Indians rumble thru some stuff they had lying in the tent (I couldn’t see what). Then I felt them putting something cold and greasy between my cheeks. I tensed a bit but couldn’t move away. I asked what it was they were doing because I was getting a bit afraid. They told me to keep quiet and enjoy it. At the same time I could feel them pulling my cheeks apart again and smearing the oily substance between them. Then a finger was at my hole again and I felt it pushing in. Of course I tensed, I never had anything going in there. They told me to relax because otherwise it would hurt and they were going to do it anyway. I started to protest and one of the boys said to the other to shut me up. One of the boys came in front of me and pulled my hair to lift my head. When I looked up I saw that he had pulled down his pants and his stiff cock (compared to mine it was big) was pointing toward me. Because he pulled my hair back, I opened my mouth. I one swift move his cock was inside my mouth. He told me to suck on it and that he would hurt me if I dared to bite him. I remember that it tasted a bit strange but not dirty as I had feared. So I did as I was told (had no other choice) and strangely I started to relax. The Indian at my rear end felt this and pushed his finger inside my hole. Gently he pushed his well greased finger deeper and deeper. Then he started to move around in circles. This felt really good and I could feel my little pecker stir to the movements he was making inside me. I heard the boy in front of me say that I must really like it because I was sucking harder. And yes, I did like it. Then I felt a second finger join the first one, stretching my little hole a bit more. Again he did this very gentle and with the lube it went in really easy. He started to move his fingers in and out of my little stretched hole. The boy in front of me had taken my head and was moving it back and forth so his cock was moving in and out my mouth in the same rhythm as the fingers were moving in and out my hole. Then the boy who’s fingers were in my hole said “I think she’s ready”. It felt a bit strange that they would refer to me as a “she”. The boy in front of me pulled his cock out of my mouth and let go of my head. He moved toward my feet. Then the fingers were pulled out of my hole. I had a strange empty feeling but that was soon over when I felt something else being pushed in. At first I didn’t know what it was but I know you already do. Slowly I felt the thing being pushed in. I tried to look back and I saw that the boy that had his cock in mouth was now on top of me and I realized that he was pushing his cock in my hole. I was afraid and tensed. Again they told me to relax because otherwise it would hurt. He held still for a couple of seconds to give me time to relax. Then he pushed in very gentle. I felt his cock go inside me. It went deeper then the fingers had done before. Surprisingly it didn’t hurt. I just had that very stretched and full feeling. After a while I really started to like it and even pushed my butt back to get more in. This of course encouraged the boy. He pushed more and more of his hard little (but for me big) cock inside me. Then I felt his pubic hair (not a lot) hit my cheeks and know that he was completely inside. He held still for a while before he pulled back almost completely out. I didn’t want him to pull out so I pushed my ass back as much as I could. When only his head was still in me he pushed back in. Still very gentle and slowly. I couldn’t help myself and moaned. Because they didn’t want the boys outside to hear me, the other boy quickly came in front of me, pulled my head back and shoved his cock in my mouth. The cock in my hole started to move faster and harder in and out my hole. Sometimes he pulled back out and then he shoved it in as hard as he could. Luckily (or not) he didn’t take very long to cum. With one big shove I felt him push all the way in and then I felt his cock grow still a little bigger. He grunted and fell on my back panting. I felt his cock shrink and he pulled out of my hole. The 2 Indians changed places. Without thinking I opened my mouth again and was rewarded with a limp cock being pushed in. The boy told me not the suck but to lick it. When I did so it tasted different than before. It was my first (but certainly not my last) taste of boy cum. The other boy of course was behind me and without any hesitation he pushed his cock in my hole. I was glad I had something back in there. He wasn’t as gentle as the other boy and started pumping with deep and fast strokes (I thought at that time but it was nothing compared to future experiences). It didn’t take him very long to cum inside my little hole. When he was finished he pulled out and came in front of me ordering me to lick his cock clean. Again I tasted the boys cum and I really started to like the taste.
After that the boy that had come first went out to see the other 2 boys (we had spend too much time inside and they were getting restless). The other boy untied me and rolled me on my back. He pulled the front of my panties down, revealing my hard little pecker. He took it in his mouth and started sucking on it. I think it only took me a couple of seconds to cum into his mouth. He sucked me until there was nothing left. Then he came over to my face and kissed me. His tongue pushed against my lips and I opened my mouth. I could taste my own cum. He hadn’t swallowed it and was now pushing it inside my mouth with his tongue. He pulled back and said that I should swallow. Of course I did.
After that we arranged our clothes and went outside. Soon the game was finished and I went back home together with my friend to change again.
What happened in the attic I will tell another time. I can also tell you that from that day on I regularly was the cowgirl (sometimes without cowboys but always with at least 2 nice Indians).
Hope you liked it. You will be hearing of me soon (I hope).

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Categories: First TimeShemales
Posted by Catharina
4 years ago    Views: 2,085
Comments (6)
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2 years ago
outstanding story. I remember my early teen years, exploring and learning about sex.
3 years ago
nice story,i really enjoyed it!
3 years ago
mmm great story, loved it came in my pants as i was reading loved it
4 years ago
Loved your story. Came right after reading it. Thanks.
4 years ago
Dit is zo'n lekker geil verhaal.
4 years ago
Great story thanks for posting it :)