I have a very dear friend that knows all my secrets. We have been friends since childhood and shared a lot of awakenings together. We're the same age by a couple of months and it was Angel who usually initiated most of our games. We went from, show me yours and I'll show you mine to I'll touch yours, if you touch mine in the summer of our tenth year. Angel always managed to find new ways to make the game more interesting.
We use to go up into her parent's attic and play dress-up when it rained. It was then that I got my first taste for cross-dressing. I remember the first time as clearly as if it happened only yesterday. It was a game we called "The Wedding Day". Usually, Angel would be the bride and I the groom. This time she decided we should change our roles because she was bored with it that way. At first I was a little hesitant about wearing the bridal gown, but she could talk me into almost anything if she tried hard enough. So there I was standing in front of our make believe alter saying our make believe wedding vows. We were twelve at that time, just going through puberty and from the moment the gown went over my head a strange feeling began grow inside me. My chest felt tight and my breath became labored. I felt a tingling that grew out of abdomen to encase my whole body. My erection became painful after only a few moments. My hands shook and my palms got wet.
When we said our "I do's" and Angel pronounced that it was time to kiss the bride, she wrapped her arms around me and we kissed. I could feel the heat from her flushed face and realized that she was as excited as I. My whole body shook as her abdomen came into contact with my penis.
"Wow," she exclaimed," You're thing is really hard. Let me see"
Without waiting for my answer she lifted the gown up and grasped my hard-on and squeezed. In my over-excited state I had my first ejaculation in her hand with just that one fantastic squeeze. My knees went weak and I fell against her and we both ended up on the floor. I watched as Angel brought her hand to her face and sniff at my cum. She tasted it, then licked up a little more and kissed me again and giggled as we shared my first ejaculation. The game took a new lead from then on, and every time it rained or the weather was cold enough to be allowed into the attic, we reversed roles.
We lost our virginity to each the next year after Angel saw an x-rated movie at a slumber party she went to. She also introduced me to oral sex. Every chance we got, we would go out to the bushes that started at the end of our street to our little secret place. Hidden in among the trees, we would undress and bring each other to an orgasm using our mouths on each other. Sometimes together and sometimes we took turns pleasing each other.
We became roommates after high school. I got a job at the local grocery store and Angel went to the community college. That was when Angel discovered lesbism and decided that men where not for her. The only time we shared any intimacy was when she dressed me up. Which had become a daily thing now that we lived on our own and had all the privacy we needed. I had even begun taking hormones, and my breasts where just starting to develop.
It was right after New Years Day, after one of our sessions that I confided in Angel about my desire to have sex, in-fem with a man. I had never been outside dressed and wasn't sure if I was ready to take that step yet. Though Angel assured me that I was cute enough that no one would know, I just didn't feel ready.
A couple of months went by and I had almost forgotten about that conversation. It was my day off work so I was up early and spent the morning shaving, pampering and applying make-up. I dressed in some fancy lingerie that Angel had picked out for me. I finished dressing with a black see through shirt and form-fitted jeans we found in a thrift shop.
I just finished brushing out my hair when I heard the door open, startling me. I didn't expect Angel home this early and for a moment panic set in thinking my secret would be found out.
Then I heard Angel's voice as she came through the kitchen," Oh good, your dressed already and don't you look hot."
Looking me up and she continued," I have a surprise for you, something you said you wanted at New Years."
I was momentarily stunned as dragged to the door and I tried to think of she might be talking about.
She flung the door open and yelled," Happy birthday."
I went into shock. There standing on the threshold was a really cute guy. He was a little shorter then I and had long black hair. We looked each other up and down and I noticed he had a large bulge in the crotch of his pants. Angel saw where my gaze stopped and whispered in my ear that she was told he had the biggest cock on campus.
He stepped in and held out his hand," Hy, my name is Dave. Angel showed me your picture and said you weren't seeing anyone I bugged her for a week to introduce us. I hope you don't mind."
