The first story in this series: "Sam-The Seventh Boy" appears in the Trans section of Nifty. It's possible that the following story may belong in the same place, but may also be in Bi-Sexual - High School - which is how I will submit it. In any event, I can only hope you will enjoy the continuing adventures of a curious young teen. I'll say it again - a donation to Nifty is a donation to your pleasure.
Toni and Sam
by
Larry Marian
So, I'm back, Sam the disguised member of the James Gang. Remember them? Well, the gang is still together, though Chuck is still in middle school. I have my notebook, both for boys and girls. The girls' is pretty short, but the boy's has grown a bit longer and the frequency has increased. For one thing, I accepted both Ivan and Juan, though they didn't become members of the James Gang. The gang came to accept that Malcolm, Pete, and my brother Jack got a whole lot more oral sex than the other guys, As a general rule (as my new English teacher liked to say) Malcolm got blown by me about three times a week, with Pete at least twice and my brother Jack three or four. Of course I traded with them. Anyway when school started I wore boy clothes, jeans and some sort of a casual shirt - pull over, T, Harry Potter, what ever. No lipstick, no mascara, no eye shadow, but a top that did it's best to conceal the 30 Bs I had now. So a new person slid into the seat next to me. The person struck me as a guy trying to be a girl. Trans was mostly fine at my high school. "Hey," I said. I'm Sam. I've lived here for the past eight years. You come from another feeder middle school?" The other smiled at me, green eyes under red hair, below shoulder length. I saw a shirt that could be boy or girl and jeans, but the sneakers looked very girlish. There was also a chain around the neck. At once I assumed my neighbor had to be a girl, who wasn't keen on boys yet. "i'm Toni," came the soft response. "We moved from Texas to here." "Neat," I responded. "Glad to show you around. Lots of neat kids, really." "That would be great. Texas is just rodeos and football. I do gymnastics and soccer." Both girl sports, I thought. "I'm co-ed volleyball and tennis," I said, leaving out the fact I was still working on being on a JV team. Well, that became the beginning of a wonderful relationship as we had four classes together with lots of time to talk. Three weeks went by. I was sure that Toni was a girl, maybe hiding from what may have happened in Texas. I was not about to make a pass at Toni especially since she seemed sure I was a guy. Then in the middle of October as I sat next to Toni at lunch, she leaned over to me and said in a whisper, " My folks are going away Saturday night. Could you maybe do a sleep over with me?" At once I almost yelled "Hell, yeah. My folks already asked me when we were going to have a sleep over. And just us - fantastic." "That's great, Sam. I know you have a lot of friends. I'm just glad I can be one of yours." The girl came out in me as I gave Toni a hug. I swear his back seemed to have the form of a hard cock as I hugged. For my part, I felt my lips begin to moisten, and I didn't mean the ones I expected Toni might kiss later tonight. So then it happened. We both got ready for bed, me in a great approximation of a guy's pajamas while Toni had a two piece girlish night gown. The lights went off. We talked for a minute. Then my arm and hand went over her shoulder, as though I were giving her some room. Toni took it. Suddenly the two of us were in a clinch, then the first kiss ,which was not chaste. I was sure Toni was a guy, some form of trans. Sure, I'd played around with other girls for some four years now. But how was I going to explain his pussy where my cock ought to be? But I had to touch his vagina, to check if we were two girls. My hand reached out. "I understand, Toni," I whispered. Then my hand felt a hard cock. A large hard cock. "Sam, I know this is wrong. I'm a guy. You're a guy. We can't." We kissed again, tongues fighting. "Tony, I want you to do something." "What?" Tony asked. I slipped off my pajama bottoms, then quickly unbuttoned my top. "Run your hand up between my legs." Well he did. The first blow job I gave Tony lasted about thirty seconds, his second about two minutes. With my coaxing he made me cum in about five minutes. I'd promised Malcolm that he would be the guy to make me a woman. "I know you and Malcolm are a team," Tony breathed in my ear. "Malcolm's been first with at least two girls. I want you to be first for yourself, Tony." With that I pushed him onto his back, then climbed on top of him to position my sopping wet cunt over his hard, maybe six inch cock, then slid down it. God, we kissed. Some time later we climbed down from our climaxes and our stammering protests over which knew what first. But I couldn't stop playing with Tony's hard cock while his fingers kept being moist inside my pussy. We finally fell asleep together. I woke up first to draw the covers from our equally nude bodies. He lay on his back, his morning wood sticking straight up. My mind raced with the idea that my notebook would now have a "T" added to it. Should I count both sucking and fucking? Should I now screw Malcolm and Pete at least? Absently I drew my hand from my ass up my slit to my clit. Yes. Damp, at least. What a way to wake up Tony, seeing my 30B boobs for the first time. Well, I positioned myself looking down on him, then smiled before kissing him. In the middle of my kiss his arms came around me, drawing me to him. The kiss broke slightly. "Good morning, Sam," he said. "Good morning, Tony," I replied. "I'm Samantha now. I'm not a virgin any more. How would you like to make love this morning?" "Uh. What do they call it? Missionary?" So I rolled away from my first actual boy friend, I guess, to lie on my back, spread my eager legs, then held out my arms and hands. Tony slid in between them giving me a short vision of his cock reaching down for his target. A bit of fumbling, then I felt that flesh rod enter my pussy for the second time in her life. "Oh, shit. What if I've already made you pregnant?" Tony gasped, beginning to pull out. without thinking, my hands landed on his butt cheeks to push them and his cock deep into my waiting pussy. "Mom put me on birth control after my first period," I said. "She was afraid my playing around with boys all the time would kill the tom boy and wake up the slut. "So, Tony, lets..." We did. Twenty minutes later I positioned myself on my hands and knees for the doggy position. After that, wearing nothing but slippers for Tony and flops for me, we made breakfast together and ate, looking at each other while suggesting other ways to make love. All this time we avoided any description of what we were doing EXCEPT "making love." After we'd put our breakfast dishes in the dishwasher, Tony got behind me, kissed my ear, then said softly, "Spread your legs, darling Samantha." This I did while hep his hands on my breasts, the remove his right to guide his hard again cock into my waiting cunt. I came three more times before he was able to cum again. We returned to his bedroom still nude to sit on it while we talked about the major changes in our lives. It was then, with the covers thrown back, that I noticed the small patch of red brown on the sheet where I had laid - and been laid. Tony laughed at that which led to horsing around which led to Tony's cock getting hard again, which led to the Mason position again which led to some thick white stuff dripping from my pussy. "What's that?" Tony asked, surprise in his voice. "Gotta be your cum. I'm full of your cum, my love," I said. "I guess. You sure you won't get pregnant?" "Sure. Let's get dressed then talk about us and what's in our future. Things have changed, Tony. I want the best for us." "I do, too, Samantha." We hugged before getting dressed. The first things I put on were a pair of sexy (for me) panties and my frilly bra - the one Mom thought I wouldn't wear. Tony gave me a strange look. "You going to dress like a girl now?" Tony asked. "You going to dress like a guy now? I replied. Wearing only his boxers, Tony came over and hugged me. I felt his erection at once, but he laughed and said, "I think we need to dress like who we are, Tony." "I agree." So now I had a real boy friend, and my buds. What to do? I knew it would be fun.
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