Date: Sun, 1 Aug 2021 13:58:15 -0400 (EDT) From: E MOSER Subject: Boy-Girl Sleepl Overs - a Samantha story - Trans - High School. Boy-Girl Sleep Overs by Larry Marian Here I am again! This new English teacher really likes to have us write. Unlike other English teachers who assign five paragraphs or two pages or 10,000 words, this guy says - " Do the assignment. " Well, I sort of figured that an essay on our James gang boy-girl sleep overs might not be what he wanted. But we evaded our teachers - and our parents - or at least where I was concerned, or the other members of the James gang. But since the James gang had been in existence for some five or six years, we'd learned some stuff. One was our neighborhoods had alleys between yards so it was easy to get from house to house for various reasons, One of those reasons, of course, was me, as I was a certified girl, even if I went by "Sam" and not "Samantha" until I met "Toni" who turned out to be "Tony". But even before that we had to do some spying stuff after I turned ten. Even my older brother Jack helped me crash James gang sleep overs during which I learned about oral sex from the older boys. Anyway, one Saturday night the stars and gods shown upon us. At the time I was eleven and had a great girl friend named Marilyn who was thirteen. Marilyn and Jack seemed to hit it off as they were the same age. There affection turned out to be a great shock in my life. But what happened was two things. The first was a sleep over with just Marilyn, or so I thought. The second was another sleep over where my brother went on a scout thing and it was just me and three of the James gang. I got challenged to describe my most embarrassing moment. Oh, shit. I had to tell the first story first to the three present members of the James Gang. "Thanks a lot, guys, but here goes. I guess you know that Jack and Marilyn have sort of gotten to be real good friends. So two weeks ago, she came to spend the night with me - not Jack. "Despite her spending the night with me, the three of us lay on my bed, with Marilyn and Jack cuddled up, arms around each other. Did Jack get his hand on Marilyn's boob? Hard to say." "Get to the gory details," Pete demanded. I was eleven, remember? I stuck my tongue out at him. Now Jack and I both knew our mom could have a demanding voice, and all three of us heard, "Jack, you and Samantha (this was back when I still could not get my parents to call me `Sam') make sure Marilyn has everything she needs. All three of you get ready for bed. " So I watched my brother kiss my best friend, then leave with a wink and a grin before Marilyn and I got ready for bed, me in a two piece innocent nightie and Marilyn in pjs that sort of looked girlish. "Dad made me bring these. Fathers can be such jerks," she said, buttoning the top. I smiled at her, letting her know I totally agreed. Anyway, fifteen minutes later, my bugler mother called, "In bed ten minutes. Jack, you go last. Girls, give Jack room." So, in fifteen minutes, Marilyn and I lay in my bed, which had been my grandparents when they were married - not sure I always remembered what it was called, but not a queen, but a nice size for the two of us. A bit of playing around and Marilyn and I acted like we were going to sleep. Wonder of wonders, I did! So something later, I woke up, looked at my phone and saw that it was almost four and Marilyn was not in bed with me. All kinds of stuff flashed through my mind, but they got cut off when Marilyn came in quietly and closed the door. I didn't wait, but turned on the bedside light. No crap. Marilyn was a mess! She's put on lipstick which had gotten smeared all over her face. Her hair looked a mess of jumbles at the least. More telling, even for an eleven year old me, was the fact that I plainly saw her pajama top's top button was in the second hole and then two buttons missed, so there was a gap revealing a teen age boob, while her pants also had a button problem revealing what my Grannie called "your unseen...". "You and Jack have fun, Marilyn?" I asked as calmly as I could. After all, all I'd done so far was allow Pete to kiss me and try to get his tongue in my mouth. That hadn't happened. "Yeah. Me and Jack... your brother ... well, he asked me to come see him after we went to bed. I did." I had to say she looked a bit embarrassed. I knew I shouldn't, but I had to find out at three AM what happened. "So what happened, Marilyn? I mean, smeared lipstick, hair all over, your clothes all jumbled. I almost think you and Jack did it." There was a pregnant pause. The three members of the James Gang hearing my confession all looked at me with varying degrees of shock. "Of course Jack and Marilyn didn't screw," Alvin said, while Chuck and Eddie nodded their heads. "They did," I said to the James Gang guys. "You want the story or not?" "Yeah. Go ahead," Chuck said. "Let's hear it." "Sure," I said to my three "brothers." They smiled at me as though they were ready for my joke. Marilyn looked at me and said "I went to Jack's room like we agreed after you went to bed. He asked me to get into bed with him and I did. Soon we were kissing - I mean French kissing. It wasn't too long before I felt his hand on my breast. I was getting hot and then real hot. He unbuttoned my pj shirt and I let him take it off. You know where things were going." "Of course I had an idea, but I was still only eleven. Of course I told Marilyn I knew where things were going. Soon my thirteen year old brother was kissing and caressing Marilyn's breasts. I was a bit surprised when Marilyn told me Jack began to ease down her pj bottoms after going between her legs. But they came off and she even told me about her pubic hair covering her outer lips. "She told me Jack said softly, `It's not going to hurt and I'll take it easy, Marilyn. You'll like it." FinallyMarilyn said she rolled on her back to open her legs. My brother pulled off his boxers so Marilyn could see Jack's hard cock ready to go. "So, guys. That was the beginning, Marilyn said. She told me that after Jack took her virginity and he'd gone down on her, she sucked him off before they screwed again. Marilyn put her pjs back on, but not carefully and came back to my bedroom. " "Sounds possible," Eddie said. "Anything happen after that?" I laughed. "We both went to sleep but woke up just at dawn. The next thing we both knew was we started making out. Yeah, we were bare butt soon and Marilyn went down on me for my first time. "I think Jack and Marilyn did it several more times over the next few months. I know this. That morning while Jack took his shower and I looked at his bed there was a brownish stain in the middle of the bottom sheet. "Believe me?" I said to myself as I grabbed a picture on my phone. My three James Gang " brothers" nodded their heads. "Well, we believe you, " Chuck said, but now that you've got us all excited, you need to calm us down." "What do you mean?" I asked, feigning ignorance or something. "Well," Pete said, who was my favorite brother,"I'm looking at your white shorts and if sure looks like you're a bit excited," he said. Alvin laughed. "Seems to be Samantha is a bit damp," he said with a grin. Shit. I knew I was wet between my thighs and only my bra kept the three from seeing my nipples were hard as diamonds. "So?" I asked coyly. "So, why don't we four play, "Let's strip one piece at a time. First guy to strip has sex with Samantha first. Then second and third. Samantha gets to choose what she wants to do - BJ, pussy, butt, hj. Okay?" Chuck smiled. I played coy and said, "What is a `hj' - don't think I know what that is." Chuck looked coy - "Hand job, Sam-- antha. You beat off the guy. Sure you remember doing that to me a couple years ago." "Oh, yeah. I was still a virgin." I smiled. "So let's go. I guess the guys go Alvin, Chuck, Pete and since I'm Samantha, I go last. " So I went to the center of the bedroom and sat down on the rug. Alvin sat on my right, Chuck facing me, and Pete on my left. I counted my top, my bra, my damp shorts, bikini panties, white socks and sneakers. That was eight objects if the boys allowed my socks and shoes. If they did, it would prolong me and get the boys stripped sooner as only Alvin had an undershirt, while Alvin had on sandals and Pete had on sneakers and socks, but no t-shirt with Chuck wearing sneakers and socks. "Okay, Alvin, let's go," I said. "Let's see if any of you have a bigger cock." So one by one, first Alvin took off a sandal, Pete removed a sneaker as did Chuck while I removed a sneaker. So it went, Alvin's second sandal, then Pete, Chuck and I the second sneaker. Soon, we had footwear gone, though Alvin had no socks to take off, but his undershirt covered his chest and my bra covered my boobs. it was then that I remembered that boys had one object to admire - their cock, while I had two boobs and my pussy. Oh well, I was still trying to decide who I would suck and who I would fuck. Would it be one suck ad two fucks or vice versa, or would I think of Chuck's long but thin cock and my ass, which he'd put his pencil cock in my butt more than once. All the while we talked and joked. By the time I shucked my white shorts, they were wet in the crotch as all three boys joked about how slippery my tunnel would be. Of course, all three were nude with a hard cock sticking out in front, waiting for me to take the final strip and remove my very wet panties, Looking around, I faced Alvin first, then Chuck, and finally my first real boy friend, Pete. "Okay," I said. "Looks like Alvin stripped first, so he goes last - or is it cums last, then Pete and finally Chuck is first. " I smiled. "Chuck, you know you have a long but thin cock. You want to put your peter in my butt? It does fit nicely." "Shit, yeah, Samantha. Why not on your hands and knees?"
 "Fine," I said. "I have lube for your cock." I stood up. "Let me get it. I want some lube even with Alvin's thin cock." I got cat calls addressed to Alvin, but he was used to its and played it off. "Who gets in Samantha's pretty butt the most?" he asked as I retrieved the lube from it's very secret hiding spot, then gave it to him to apply. I lay down on my bed on my stomach, legs parted for Alvin. A few minutes later Alvin eased his cock into my rosebud, slowly and gently until he'd bottomed out and we began to pump as Calvin and Pete watched , cheering us on. "Okay?" Alvin asked quietly. "Doing great, Alvin," I replied. "Feels good." It did and I felt a climax coming. It did, first Alvin and then a small cum for me. We untangled, kissed, and I made way for Chuck. "So what's your pleasure, Chuck?" I asked as I looked at his very hard five inch cock pointed at me. "Well, Alvin got your backdoor. How about your front? It has some fur on top, but your back doesn't. I can get it wet with my tongue, then slip Peter into Pussy." "Sounds good to me," I said. "How about missionary?" So we did. Now the thing about Chuck was his dick length and girth was fine. It was his staying power that wasn't great. I think maybe he lasted a minute at the most. Sometimes it was in a matter of seconds before he came. This time it was maybe forty-five seconds when he moaned, "Oh, shit, cumming." He normally had a lot - apparently he didn't beat off very often. But then there was Pete - my original boy friend. Of course Tony knew all about Pete. The only thing is that I never had the two of them at the same time - yet. I was ready for him; I knew he was ready for me. I knew that Alvin and Chuck would be willing observers of what we would do. So Chuck rolled off of me as Pete dropped down beside me. Unlike Alvin and Chuck, we kissed first, deeply, of course. "Usual?" Pete asked, his mouth next to my ear. "Sure. First your licorice tasting black cock with the purple grape head with sweet cum. Then I ride that black cock while you play with my white girl 32 B boobs until you cum again." "Oh, my seven inches doesn't rate as a nigger cock any more?" I asked, again coyly. "Of course it does. You want and we finish with a thick nigga dick in yo' ass?" I smiled. "Alvin's opened me up," I said. "We just don't want them bored." I kissed Pete. "We want to see some nigger fucking," Alvin said with a laugh. "Alvin, there is only one of my brothers who can talk trash like that and that's me and Pete. You do know that!" I really glowered at Alvin while not looking at him. Instead, as Pete was on his back, I pounced on his hard seven inches of black cock with purple tip, taking the whole shaft in with one swoop. At once I began to bounce up and down on Pete's long, thick shaft, enjoying its feel with my tongue and lips. Pete's groans of content made me work harder. He began to take part in our sucking, with him using his thrusts to my lips and tongue. Finally I heard him groan, "Sam--antha. About to cum. In your mouth? I made a very garbled "Please, Pete," seconds before he creamed. I swallowed twice before releasing his ebony rod. "God, that was good, Samantha. Bet that's the best blow job ever!" We kissed, then rested for a minute or two before we began again. `Now he lay on his back, his cock again hard as I slowly slide my pussy down his shaft to bottom out before beginning to bounce up and down, his hands cupping my breasts to keep me stable. So we did it, slow at first, then faster as we both moaned. Now, guys normally cum first, but his cock's position caused it to rub my clit and I came first, not much, but enough to bring me closer to a real one. Then Pete moaned, "Oh, YEAH!" to announce his cumming. I came, too. Pete and I rested for a few minutes, then faked it. He got hard again - why am I not surprised? - I got on my hands and knees with Pete behind me so I could feel his purple head poke it's head into my butt. We lasted maybe less than a minute before he actually did cum. But that ended that night. If there had been another girl - well maybe - but there's more! as the TV game shows say. The next afternoon as school let out, Tony, breaking all his normal habits came running to me, instead of his normal stealth. "Samantha - wait up! Alvin and Chuck are looking for you. Pete is too, but for Al and Chuck!" With that, he took my hand to squeeze it - about the most we could do while still on campus. "So?" I asked, in my best Bonnie Parker accent. "It's cool," Tony replied, just as Alvin and Chuck appeared, Pete behind them, only needed a lasso to herd the other two. Minutes later I had my three James gang partners in front of Tony and me. "Samantha," Chuck said, " Me and Alvin have something to say to you and Pete. " Confused, I replied a bit sharply: "What?" "It's about yesterday. That 'N' stuff. Me and Al were confused, but Pete explained that it was one thing with some and not good with others. Sorry. Won't happen again. " I smiled at that. "Guys, we've been brothers for years. No problem. Let's go get comfortable." We smiled at them; they smiled at us. We took advantage of parents still at work. Twenty minutes later Tony lay on his back while Alvin sucked him while Chuck screwed me cowgirl style as I blew Pete. What a way to end a problem. If you enjoyed this and other works, please consider a donation to Nifty. Nifty needs the donations. Thanks.