My first anal experience

This story may be written over time, in parts as I may not have time to finish in a single sitting. I have been talking with other sissy's on Xhamster and that has me recalling many memories as well as fantasies. While I have had many encounters with boys and men, my first anal experience is something I have been think of as late, his name was Sam.,
Sam and I were good friends first. We had sleepovers and backyard camp outs on a pretty regular basis which were little more then cover for us to play with each others cock. On sleepovers at Sam's his bro' would join in and I would get to play with two cocks at a time. We would take turns admiring and stroking but that seemed to be as far as they were interEested in going.
After many months of nothing but fondling, I finally got the nerve to as Sam if I could suck his dick. While he was good with this idea, he made it more then clear he would not return the favor. I was okay with this situation as I felt this was what a guy like me was supposed to accept. This was my place and it excited me. Back then I had no concept of sissies, submissives but I knew even then that I liked serving others. That being used for others desires was exciting to me.
So it went like this for months. We would fondle each other, cuddle and kiss from time to time but in the end was my mouth on Sam's cock until he would spasm. On nights when I would sleep at Sam's, even find his bro's cock would find its way into my mouth. For a little sissy in the 70's this was as good as it got.
As time went on I found myself growing closer to Sam and began to get desires of... a more feminine nature? I wanted to be Sam's girlfriend and even convinced him to call me his girl when we were alone. As Sam's girlfriend I wanted to please him as any girl would. I wanted him to fuck me but was afraid he would reject me if I asked.
The answer to my dilemma came one day while doing the house laundry. I found a matching set of leotards and pantyhose. I snatched them up and quickly headed to Sam's. His family was home so we went for a walk in the woods so I could show him what I found. I asked him to turn away and wait. I got undressed and put on my treasures. When I was pleased with my outfit I put my arms around him, kissed his shoulder and asked him. "Sam can I be your girlfriend and would you fuck me like a girl?" I could feel him stiffen a little as I let go of him and stepped back expecting him to be mad or reject me in some way. I was so nervous that I had forgotten about my clothing change when he turn, looked at me at me saying "what the fuck?!" He just stared... after what seemed an hour he exclaimed he had want that since I first put his dick in my mouth..
Sam unbuckled his belt and started to remove his pants so I dropped down to help him get his cock out. I was so excited that he wanted me in this way that I was trembling as I guided his now hard dick into my mouth and began to suck. We were both overly excited and in too much of a hurry. Sam directed me to lay down on the ground. With his pants at his ankles he crawled over top me and started to kiss me. I spread my legs open and could feel his hips settle in against mine, his hard cock poking my crotch.
I fumbled with the snaps on the crotch of my leotard and finally managed to pop it open and started to dig at my pantyhose. I was able to get a small hole started in the crotch when Sam knelt between my legs and ripped the hole open. He spit on his cock, crawled back over me and started poking around for my asshole. Finally I could feel the head pushing at my hole and I spread my legs wider. I told that was the spot and he stated to push. I could feel the head of his cock start to slide into me and I was so happy. I told him to make me his girl. I knew this is what I wanted so badly and I was finally going to feel Sam's dick inside me. I was going to be his girl!
It took a few seconds to kick in and by then Sam had pushed his cock in to the balls and was pulling back for another plunge into my virgin ass, the pain was sudden and intense. I think it was a few strokes of Sam's dick before I stopped gasping and was able to beg him to pull out. He looked at me surprised but his hips were still thrusting his cock into my aching hole. I begged him again to take his dick out, that it hurt too bad. When he finally did take his dick out, I was crying. Tears were running down the sides of my cheeks and Sam said he didn't understand. As I tried to calm down I explained to him how this was my first time taking a cock in me and that I didn't know it would hurt.
We talked about it and came up with the idea to try it slowly taking little bits of his dick at a time. After some time I felt good about trying this again but Sam had gone soft so I put his dick in my mouth and started to suck him. Once he was hard I laid back offering my hole to him. Sam was pretty gentle this time, even spitting on his cock for lubricant. Slowly he pushed the head of his cock in and when I felt my ass spasm he would stop. A few times Sam had to pull his cock out and stroke it to keep it hard but rather then getting bored with this he stayed with me. Slowly, bit by bit Sam would push his member into my virgin ass.
After what seemed a half hour, Sam smiled at me and was giggling. When I asked what was so funny, Sam said his cock had been all the way in me for several minutes and I didn't even know it. I was very happy and encouraged him to start fucking me. Slowly at first Sam pulled back then pushed into my ass. While it was still a little uncomfortable I told him this was good. After several strokes of Sam's cock I began to feel good with him inside me asked him not to stop. I gave him words of encouragement, I told him how good he felt. I told him how I needed this.
Encouragement was not really necessary as Sam quickened his pace. He was breathing heavily and pumping his cock hard and fast, I knew he wouldn't take much more before he would orgasm. I told him how much I liked having him fuck me, that I loved being his girl. I raised my head to his and kissed him just as he started to orgasm. I was so happy, I had my dream, I had given Sam myself for his pleasure. I was as close to being a girl as I could realize and I was Sam's girlf riend.
Sam was laying on top of me catching his breath, I was in sissy bliss so pleased with our accomplishment when we heard someone stomping down the woods trail towards us. The shear terror of being discovered like this hit both of us as we rushed to redress ourselves. Sam had his pants up in no time but I was only half dressed when we were discovered. "what are you two doing out here" he said as I froze stiff.