Where it happened: Dressmaker's Shop
Langauge: English
Sex: Female
Rating: 8
Category: Straight
So I have lived next door to my best friend since he and I were born. We’ve always listened to each other’s problems and just had this ‘huggy-feel better’ relationship. We’re both 16 and because of our openness and honest feelings our parents were always casual about our relationship like us. We still go to each others overnighters with each other’s friends and we still sleep together in just our underpants like All kids our age at sleepovers… It seemed so normal. I liked how my developing but still small breasts felt against his body..still do I guess. But he never really reacted to my ticked games and my ‘accidental’ touches from either me or my friends. I thought he was either as sexual or gay. So I quit pressing the point and waited til he figured it out.
One evening I went over and his mom pointed me upstairs and invited me to spend dinner and the night if my folks were okay with it..they were. (They got to hanky panky when I stayed over here..cute). I went up to the bedroom and walked in and found a girl our age that I didn’t really know (from school, I’d seen her and Jamie together) and she was putting makeup on another girl. I guessed that they were over for dinner to but asked “is Jamie around? I was kinda looking for her…and nice to meet you by the way..” The girl in the chair turned around and stood up in really gorgeous dress and heels and perfect make up dripping with a certain awe inspiring ‘sexy something’ that some girls have, and she said, “well, you’ve found her..what do you think?”
Stunned. Confused. Completely not understanding what she just said, I said, “No, the other Jamie, the one that lives here!” “And you’ve found her Belle!” She said in her soft sexy voice.. I admit I’m dumb..blonde to the roots..but I still didn’t get it. “But where’s my BFF, Jamie?” I blurted still not getting it. ‘She’ lowered her voice to ‘his’ normal tone and said “it’s me, Belle, it always has been.” I could see both intense kindness and understanding in his eyes and yet a little hurt as the realization came over me. “But you’re not a…I mean you’re a..” He laughed softly amend went back to ‘her’ voice. “Yeah, I’m that..one of those. I have a penis but somehow genetics got it wrong. My mom and dad know and terry here and now I’m trusting you.”
I couldn’t deny that she was gorgeous.. So I shut up and let her finish getting her lip gloss and eyeliner on and then we went down to supper. Her mom and dad commented on how pretty she looked and she just beamed with happiness. I guess that’s when I knew it was real. After dinner we went to the mall and a movie and I kept eying how sexy she looked from every angle. But he was 14 and I wondered how he would handle puberty..hair..stubble…erections…(I think he was already getting those for a while now.). When we got alone I asked why he never told me. He said that first look on my face scared him and he didn’t want to lose his best friend.
That night, makeup off, both in just panties in his bed I hugged him and asked him all about it. I really wanted to know. I asked him if he liked boys but he wasn’t sure yet. So I had the perfect idea and asked if he wanted to be sure. He agreed. Slowly but surely, trying to respect every reaction I ran my hands lightly over him. Feet, calves, thighs, over the panties…he certainly reacted..”are you thinking about me?” “Yeah, kinda”. I didn’t understand that but I kept going. Finally I was ready and slid his panties off with my finger tips. He wasn’t quite full hard so I took the end of it into my mouth like I’d heard my gf’s lie that they did (still, no use wasting information) he came to full attention. His balls sack nearly disappeared. His five thick inches were so strong looking and no hair yet..I think I knew that from when we showered together a few months ago. I only had a few hair wisps myself. He shuddered as I sucked him and started crying. Later he explained how badly I was confusing him but I thought it was just the experience of our first for both of us. I moved up and lay on him, kissing his tears, loving the salty taste and telling him that he’d always been my best friend and I was glad I was giving myself to him on my first time. He still didn’t talk. I think I stupidly thought he was in too much pleasure to speak. I sat up straddling him and rubbed back and forth on his perfect thick penis until I got slippery and he was ready. I told him I was ready, he looked at me so sincerely and said “okay..I really do love you.” I was awed that he felt so strongly. I arched my back and pushed him into me as I shoved myself back onto his hips. I felt the tearing inside me and decided I wouldn’t cry or make a sound. This was about him and his future sexuality! I was an idiot! The rhythm came naturally to both of us. After several minutes we were having a good time. I told him to come in me, I had birth control (he knew it was true). He began crying again and shuddering and I thought I was doing something wrong! He asked me to help him sit up so he could hug me when he came. We hugged each other so tight that there was no space or breath between us until finally he cried out “oh, God!, you’re so special Belle!” And I felt him burst inside me in warmth and wetness.something in that triggered me..I don’t know if it was actually an orgasm cuz I read that few girls get them first time. But it was an amazing, pulsating gripping airless moment between us. We both instantly began thanking each other and hugging and kissing over again and again. I’ve never felt so beautiful. He said it made him feel beautiful too..but in a different way. Like no ones ever loved him that intensely before.
We talked a lot that week. We had sex a lot that year. But it was never exactly the same thing for him. He needed the closeness, the passion and love. It was me that felt like I had lost my best lover but kept my best friend. He almost immediately started getting injections that year, he is going to get the surgery that will end it between us forever even though we haven’t done that for a while. I had a really great friend that is gay and introduced them while Jamie was in his most hot outfit. We explained the whole deal to him and he has been going out with female Jamie for the last nine months now. Jamie feels ‘At home’ in the arms of a man.. I think it’s cool that my friend could adjust to the whole transgender thing. I’m so happy for him and so sad she has to go through so much! Jamie is really private. We still cuddle naked at our sleepovers but we know that the time for that passion is past. It’s not what he really wants. Marcus (gay friend) spends occasional nights now. I spend those weekends with mom and dad now. I wouldn’t change a thing!
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