Date: Tue, 1 Feb 2022 13:12:27 -0500 From: Joey Martin Subject: Role of a lifetime - part 1 The following is a fictional fantasy of mine; the most endearing of my inner desires. It's a love story to the boy I wish I'd been and also to my childhood friends I wish I'd shared deeper intimacy with. I hope you enjoy it. This is part of my series. More to come! Role of a Lifetime Part 1 By J Martin -------- Foreword --------- Sam (Samantha) is the protagonist of this short story. He is a boy of 12 who was born with undescended testicles that his parents chose not to correct. His folks believed Sam was born as God intended and thought it foolish to assume they had authority to change His will. Perhaps related to Sam's cryptorchidism, he grew more feminine with every passing year. Sam was a beautiful and loving child who never shied from affection - displaying empathy and wisdom far beyond his peers and even his elders. He loved being with people, actively listening and studying those around him. His desire to connect with and become enlightened by his community, helped to ignite his passion for acting. Sam is the only child born to his parents William and Margret. William was a wealthy old man of 75 when Sam was born. As successful and admired as William was, he felt Sam was his greatest achievement in life and cherished his boy from the moment of Sam's first breath until William's final breath 5 years later. William's love for Sam was matched only by his mother Margret whose unconditional love for Sam blossomed the boy into a stunningly beautiful and wise young boy. Margret was a young woman of 26 and doctoral candidate of 17th century literature when Sam was born. William met Margret during a fundraiser for university and fell deeply in love, despite their dramatic age difference. Widowed at the age of 31, Margret was the sole heir to Williams fortune and left her literary career behind to care for Sam. They lived in a very wealthy community of successful and enlightened intellectuals. Their community was strong and supportive; thriving youths were of abundance and Sam was no exception. Sam began acting at a very young age. He studied movements and mannerisms of those around him and mirrored their behavior when he engaged with them. Margret would read to Sam for hours a day while Sam acted out different roles as he interpreted them. He and his mother reveled in their play time so much that Margret founded a young actors foundation in their town where Sam could take part in numerous productions put on for the community. By the age of 12, Sam had established himself as the standout performer, taking leading roles in every production; a credential he earned from hard work and innate talent, not nepotism. Sam's physical and biological nature allowed him to play female roles convincingly. The balance of his effeminate and masculine natures gifted him great versatility and insight. He was androgynous, with shoulder length brown hair, a glowingly fair complexion, thin frame with feminine hips, a buttocks that shames all known renaissance sculptures; soft a-cup sized breasts adorned with puffy bright pink nipples; his face was so beautiful that every man or woman was taken breathless by his presence - deep blue eyes, large like a doe; dense and lengthy eyelashes, perfect and symmetrical bone structure, and the most invitingly red full lips - perhaps Sam is, the most objectively beautiful human on earth. A gorgeous boy with features any young girl would die to see in their mirrors. Characters Matt - Sam's best friend, 12 yo and theater enthusiast Cam - Other best friend, 12 yo, star athlete and actor Pete, Dell and Ben - close friends of Sam and active in the young actors foundation, ages 12-13. ----------- Chapter 1: The Role ---------- (Sam is the protagonist and is the "I" from here on) "I wrote it last night... the climactic scene. It's got passion, turmoil and beautiful imagery. We must rehearse exhaustively to capture the powerful performances it deserves." I exclaimed to Matt, clenching his shoulders and making strong eye contact so as to stamp the importance of my words into the fiber of his being. "Ok. Ok. I got it. You know I trust you and your writing. I love your plays and I don't need to be under your spell to appreciate their importance and beauty... sooooo?! I'm dying here! I must read it now!" Matt replied I gave Matt the scene I'd written late into the previous night. The text, filled with my own lust and fantasies disguised into the characters John and Mary, paints a forbidden love that envelopes the step siblings. I identify and play the role of Mary whose reciprocated love/lust for her stepbrother John (I identify him as Matt) boils over into this pivotal scene in which the embrace, kiss, and make love for the first time as teen virgins. John is closely based on Matt, who I am in love with and have desires to make my boyfriend. Mary is me, or at least my perception of my desired image of me. I know I'm gay and I've never actually told anyone or even "messed around" but I fantasize about making love to boys and more pointedly, Matt. Even though our town is quite sheltered and progressive, the culture is not devoid of the global patriarchal influence of Hetero norms, thus my apprehension towards jumping Matt's bones (one bone in particular, hehe). I adored watching Matt read over my scripts, his intensity and expressions adorned his gorgeous face. I loved that he always read my work with such earnestness and excitement and today was no different. His eyes bulged and mouth dropped open, he licked his lips and slowly stroked his cheek as he absorbed line after line of my symbolic love letter to him about our first sexual experience by way of John and Mary. He flipped the page and was now 2 paragraphs away from the scene's conclusion - "John and Mary broke their kiss momentarily to shed their clothes one last time as individuals. Now completely nude, they become one forever, linked at the holiest of places of flesh. End scene" The scene is the raciest thing I'd every written and I scaled it down tremendously. I wanted to write the passionate intercourse they had; to describe Mary worshipping Johns penis and everything up to and including their simultaneous orgasm that saturated their bodies. I'm not sure my mother or the community would've signed off on that production, hahahaha. Not to mention, my complete lack of sexual experience leaves me, even a highly empathetic boy, unqualified to scribe such literature. Not to say I haven't consumed many hours of porn and i know how things work but i know it's far different in practice. In short, I had to leave out the good parts. Matt just finished reading when he looked up at me with a look of awe and joy. "This is incredible Sam! Truly your best work. God! I'm so lucky I get to play John. I'm really going to nail this Sam. I won't let you down... shall we rehearse now? Can we please?" "Yes yes. Let's get into some wardrobe and makeup for some enhancement. I'll need 15 minutes. Go and grab something from wardrobe. Remember, it's modern day so something current you think embodies John." I said as I made my way to my wardrobe closet. I have acquired a massive collection of costumes and wardrobe from my years of acting. My room with the additional closets, is the size of a modest home at 1500 sq ft. Essentially, I have an entire wing of my home all to myself. In my wardrobe, I chose a crop top and stretchy, black booty shorts - Mary is beautiful and creative with a body that is heart stopping. I don't want to go overboard with the makeup - I know I look quite feminine already, so some nude lipstick, eye liner, mascara and subtle blush should do it. For hair, I'm choosing to wear it in a high pony tail because in the scene, Mary has just returned from ballet practice. After finishing up, I come back into my room ready to rehearse. Matt is dressed as John in mesh basketball shorts and a tank top... swoon! He looks so sexy dressed like a jock and even at 12, Matt had a cut little body. As I walked over to Matt, he drank me in; his mouth open at the sight of my crotch. I'd tucked my quite small penis back with a tight thong under my booty shorts. I could've had a pussy and no one would ever suspect me as a boy. "Hey John. Wanna play?" I teased matt, stroking his arm and chest with my hands. He swallowed hard and gave me the cutest dorky 12 yo boy smile - as if he were approached by a busty high school bombshell. I felt very flattered and he stuttered out "uhhhh. Uh huh. I mean... yeah! Yes. Ugh. Very much!" We rehearsed the first page a few times, giving each other notes and really dialing in the performances. After every pass, we fell further and further into character - even my bedroom changed into johns bedroom in my mind. We'd gone over the first page for close to an hour and we felt good enough to move on to the conclusion page. This was the page I'd been waiting to rehearse since writing it last night - the first kiss, the nudity and the implication of virgin sex. I honestly didn't know what would happen when we rehearsed it. What I did know was, bad or good, I was about to take a giant leap into my fantasies. As we acted out that fateful page, our intensity grew, our bodies inched closer together, long pauses of sensual eye contact accompanied each passing line. Then the narration read of their first passionate kiss... intense eye contact, bodies slowly drifting into each other... I held my breath and did everything to communicate my desire for Matt. Then, it happened. Our lips met and a shockwave jolted through me. I couldn't see or hear anything, I could only feel his lips on mine. We embraced, kissing more deeply now after the initial shock. In unison, we opened our mouths and danced our tongues around. We were full on making out. After a very long minute, Matt showed no signs of slowing up and I certainly wasn't going to stop wherever this was going. The intensity built as Matt's hand found my butt and groped, squeezed and caressed it. I followed suit, and moved my hand over his cock and pet it through his shorts. The seal of our lips broke only to gasp and moan for the pleasure we felt. I couldn't quite fully ponder this thought at the time, but was matt making out with me? Or was he, John, kissing Mary. If the former, then he's an amazing actor! Matt's other hand went up my shirt to fondle my breasts - I knew my breasts weren't normal for a boy and were bigger than most girls in my grade. I felt like a real girl in that moment. My ballless cock was throbbing and struggling to bust free from the confines of my panties. Matt's cock felt so much bigger than mine and was rigid like a steel pipe. I had to at least see it, to touch its skin, I needed it. Fuck it. I reached into his shorts and grasped it firmly then began stroking and petting, fondling his smooth balls. When I did that, he broke our kiss and began kissing my neck and nibbling my ear - panting his breath into me causing a shivering ecstasy to envelope my body. As he was panting, I thought I heard him whisper "Samantha". Was he calling me Samantha? In the moment, I told myself yes. Matt calling me Samantha was the most erotic thing I could imagine. It kicked me into an even higher gear and the air was thick with lust. As he groped, licked and nibbled on me, I pulled his shorts and boxers Down, liberation for his cock. He backed up slightly and removed his tank top, And I removed my crop top and admired his body. His shorts were down around his mid thigh and his 7" perfect penis rocketed up in my direction. I looked up at him, we spoke with our eyes and I knew we weren't turning back now. Matt pulled my shorts and thong off and stood back up as my dicklet sprang free, protruding out 3 inches from between my curvy hips. I was fully nude and could've cum just by having Matt's eyes on me. I looked back down at his beautiful cock, dropped to my knees and removed his shorts completely - now we were both nude. His penis was less than an inch from my face. I had only one instinct and took him in my mouth. I rolled my tongue around, tasting and smelling his intoxicating scent. He stroked my cheeks and hair softly, panting and moaning as I pleasured his cock with my mouth. His balls fascinated me since I had none, well none I'd ever seen at least, and I fondled them with one hand and palmed his abdomen with the other. I suckled at his balls and loved the taste and smell as I licked around, over and behind them. It was the best day of my life and I channeled that joy into my mouth and onto Matt's cock. I slurped and sucked and licked and moaned as best I knew how, recalling numerous pornos I'd studied intently. Matt whispered through his panting again, "aagghh Samantha mmmm baby yes". His obvious pleasure made me wild for his cock and I intensified my sucking; taking more and more, applying more pressure with my tongue and increasing my speed holistically. Gently squeezing his balls, slurping, bobbing, lapping away and securing his cock in my grasp as if I were afraid it would runaway. Then. It. Came. Matt's moans grew louder and his whole body tensed... I knew what was cumming. He clenched my head to pause my bobbing motion and with a final lick up his shaft from stem to tip, he erupted. Matt's cum poured into my mouth. Spurt after spurt pooled on my tongue and in my cheeks - it just kept cumming. I stopped bobbing but resumed a sensual tongue lapping on the underside and around the tip of Matt's cock. His sperm delivery had slowed down but with each pulse, more and more poured into me. He came for a solid minute as I savored his flavor of cum as it whooshed around. His cum seemed to have stopped so I swallowed twice to get it all down. My lips were still sealed around him and I resumed my technique but much slower - groping his cock with my tongue with purposeful laps, moving my lips up and down his shaft. His body felt limp but his cock was still hard as steel. Then he pulled out from my mouth and leaned against my bed. I looked up at him and was met with a sorrowful face. Oh no. Did he regret it? I hope I didn't scare him. Did I ruin everything? Shit. "I'm so sorry Sam. I blew it. I couldn't even make it to the sex part... I barely did any foreplay at all. You felt so good I just couldn't last. I'm so so sorry. I'll rehearse with you exhaustively until I nail this. Please know that I can do this. " matt apologized. I couldn't believe what I was hearing. He didn't think he performed well enough for me?! I had to set it straight for my sweet love Matt. "Matt, you did amazing! Honestly, I didn't even think you'd go as far as kissing me. Don't get me wrong, I definitely want to rehearse this with you exhaustively, but not bc you did poorly. Quite the opposite! That was the coolest thing that's ever happened to me, I'm still spinning. And... you didn't blow it.... I blew you, hahahaha" I said and we laughed and hugged it out. Once he settled back down, I had the urge to ask him something "Matt?" "Yeah Sam" "So. Ya know when we were just hooking up? I could've sworn I heard you whisper Samantha a few times... I wouldn't mind, I just, maybe I was hearing things with all the panting and moaning" "Um well yeah... I did. So you're not mad? Im sorry if it offends you." "Offends me? Not in the least. It made me so hot that you thought of me as a girl, as Samantha and not Sam. I really really like it. What made you think to do it?" "Thank God. I never want to hurt or offend you. And, well, Samantha was kind of something Cam and I call you in private sometimes. Like, some days you look so fucking hot that all we can talk about is how unreal you are. Like how can a boy also be the hottest girl in town? You're special. Cam and I have pondered at length about what you look like naked, what it would feel like to make out and have sex with you. I hope that doesn't weird you out. You're just irresistible." Wait... my crush, my best friend and my other best friend have a crush... on me?!?! I could've flown around my room with how many butterflies I had in my stomach. I could feel myself blushing and see Matt blushing as well. What a picture. Two puppies in love. "I'm really happy to hear you say that Matt. I'm shocked but very pleased. Truth is, I have a massive crush on you. I wrote this play in hopes that I could kiss you, even if it was just acting, I had to at least kiss you. And woah about Cam! You both want my cute hiney eh? Hahaha." "Samantha, you have no idea. Not just Cam and me, but also Pete, Dell and Ben - the whole town probably wants your gorgeous supple hiney. So... was that like your first time? It was for me so I hope I did ok." "Wait wait wait. Pete, Dell and Ben call me Samantha and talk about fucking me too? How's it possible that I was so naive to not see it. And yes, it was my first everything. I wanted you to be my first for EVERY thing and I'm almost there, hehe. So, like, are you going to tell Cam and the guys about this? I mean, it's ok with me. Im pretty happy that I was able to seduce you sexy boy." "You make me feel amazing. I can't believe Samantha is saying those things about me! I'd be so happy to brag to the guys about us. I feel kind of bad in a way, that they can't feel what I feel with you. I don't want to rub their face in it. Ya know?" "I get it. Well.... Hmmmm... maybe like.... Well what if, I mean if it's cool with you... what if I hookup with them as well. That way everyone is happy. My heart is with you but like you could share my mouth and hiney with them like real friends would. Only if you're cool with that." "That sounds really hot actually. Im like really in love with you and I want to be your boyfriend but we are such close friends that we should share our love right? But how do we tell them all?" My flair for drama kicked in when he asked me that and a genius idea burst forth. "Im in love with you Matt and you'll always be number 1 and my priority, my boyfriend. I just had a thought. Let's invite all the guys over for rehearsal tomorrow and you and I can do this scene in front of them. They'll be shocked! Once you cum, I'll invite them to join in... ohhhh it'll be brilliant." "You really are a genius Samantha. Now kiss me" We climbed into my bed and I straddled his waist, on top of Matt as we made out furiously. Things progressed downward and I was reveling in sucking his cock again. He pulled my head up after a few minutes and asked if we could have sex. Before the last words left his mouth I was sprinting to my bathroom to grab the lube. I know not many 12 yo boys have lube, but since I was young I've had regular enemas because of my condition. Since I was 9, I've given myself them twice a week and the lube helps the tube slide into my tight little pink hole. My last enema was this morning which is amazing timing on my part. I lubed up my insides with two fingers and brought the tube back to bed. I squirted some on Matt's cock and lathered it all over. I really wanted to watch him enter me and the mirror at the foot of my bed would be perfect. I'd spent many nights watching my fingers go in my ass as I came clear loads all over my stomach and face. Each time, wishing my fingers were matt's cock. I straddled his waist again, assuming the cowgirl position and said "I'm going to watch it go in. You can too if you look in that mirror back there". I grabbed his cock and lined it up between my two glowing white globes. The picture of his cock between my perfect ass cheeks almost made me cum. Then I felt his slippery tip kiss my bright pink virginal hole. Then I went for it, remembering the articles I'd read about how to be a bottom - go slow and push out until you accept his cock inside. Here goes nothing. I slowly sat down on Matt's cock, pressure was building as my hole was pushed further up into me. Then pop! Wooooaaahahhh. His tip was in me and it hurt bad... stay calm, breathe, push out and go slow. The pain will pass. I could see the head had disappeared inside me and it gave me the courage to press on. Make it all disappear. Get him in me. Just get him in me. I sat down more and pushed out in slow motion; I could see more and more of him slide inside of me. Slowly I worked my way down nearly to his balls when my gates flooded open and just like that, he was in. The view in the mirror could've been a Rembrandt - two bubble cheeks kissing Matt's bright pink and quite large balls. The picture was burned into my brain. It was time for some hot sex. I started to rock my butt back and forth, matt's cock gliding around inside of me felt euphoric. He was groping and sucking my breasts as I amplified my hip motion to slide him in and out. The gentle smacking noises created by my slippery hole and his penis were erotic to me - I could feel, hear, smell and taste the sex. My dicklet was sandwiched between our pelvic mounds. His skin was on my penis and it drove me wild. The sensory overload drove me to the most powerful orgasm of my life. Matt sucked my breast vigorously, his cock banging inside my walls, then I exploded. My cum burst out from our pelvic sandwich, covering Matt's torso in a clear watery gel. Because of my condition, I won't produce sperm, just a very sweet tasting semen which I really enjoy consuming while I masturbate. My head is spinning and my body is shaking in ecstasy - I feel my butt squeezing Matt's cock as my penis convulses again and again. Matt howls into my breasts, still sucking away on my hard eraser nipples. I could feel the pleasure he got from my ass squeezing around his cock. I began to really focus on my movements and technique. Gliding my ass all the way down his cock and the clenching my hole as I glided it back up towards the tip - slide down, squeeze, pull back up, down squeeze pull, over and over. His howls changed from relaxed "mmmmmm" to throws of passionate "aaahhhh fuck oh god ahhhh. Samanthaaaaahhhh ahhh ahhh". I knew the climax of our collective virginity was happening right then. Matt pulled my body down into his, hugging around my back with one hand and grasping my ass cheek with the other. Holding me still, He began thrusting his cock in and out with longer and faster strokes. His control over my body made my skin tingle, pumping into me faster and faster until he planted deep inside me; slamming all of his cock in, his body frozen with tension as he squeeze me so tightly. In The stillness I could feel his orgasm in great detail with my ass. A flash flood of cum shot through his urethra tapping against my sphincter with every wave; his cock jumped and pulsed against the walls inside me as his geyser splashed wave after wave of cum into me. I could almost sense Matt's cum filling me up like a flood filling up a cave. I clenched my hole rhythmically to coax as much cum from him as I could. Matt's body then fell limp beneath me, loosening our embrace but still wrapped in the warmest embrace. I tucked my face into his neck, stroking his hair and giving him soft pecks with my lips. I never wanted his cock to leave my hiney. His cock still pulsed inside me, now with less frequency. He said "I love you Samantha. I love you so much." "I love you Matt. Please stay inside me. I want you in me for as long as possible." Both spent from indescribable pleasure, we must've dozed off for nearly an hour. We woke up simultaneously, his now softer cock still planted in me, my hole sealed tightly around it. We both had to pee and much to my disappointment, his cock had to leave me. I slid my hips forward and his cock popped out; cum pouring out from my hole and onto Matt's cock and pelvis. I covered my hole with my hand and waddled off of him; like dismounting a horse. I wiped up the cum in my butt and licked it off my fingers and then saw the lake of cum that covered matt's body. "Don't move. I'll clean you up baby. Just lie still" I slurped up the pool of cum on his pelvis, licked his balls and cock clean, and gave him a few sucks to empty any cum still left in his cock. The air was thick with a humid sex smell - sweat, pheromones, and a heavy aroma of cum; this should be a fragrance, or a candle scent - my new favorite smell. I suggested we shower our sticky bodies and we shared a sensual 20 mins together, bathing each other in the hot water. Before we finished, I sucked his cock again to make sure he was thoroughly pleasured when he returned home shortly. I savored his last load of cum in my mouth; I didn't swallow, I just swirled it around, tucking it away when I had to speak, and let his cum absorb into me over the next half hour. The taste of his cum was invigorating - like my own personal energy drink. It was around dinner time and Matt headed out. We ran into my mother when I walked Matt out. As was the case most days, She'd been at the country club having meetings and playing tennis. We said our goodbyes to Matt after confirming with mom that the guys could come over for rehearsal tomorrow. I was always happy to see my mom and I genuinely loved spending time and talking with her. Today, I felt pangs of guilt having lost my virginity behind her back. My attempt to stroll back up to my room we stopped when she insisted I visit with her while she cooked dinner. I did my best to direct the conversation away from what Matt and I did today, "How'd your meetings go? Figure out your backhand yet?" And so on. She obliged me in casual small talk until she didn't. Her expression became her famous look of concern - a motherly expression of protection and love. I knew that look meant a deep conversation was coming, I'd seen it many times in my life dealing with my fathers death and my medical issues over the years. Here it came... "Honey? You know you can tell me absolutely anything, right? I love you unconditionally and I will support you and your decisions always. We are all we have and we must be there for each other forever." Ok? Where was she going with this... "I know Mom" "I'm just going to say it. I got home today early and, well, I went to your room to say hi. You shouldn't feel embarrassed or ashamed, please don't. But, I saw you and Matt sleeping. I saw everything." Oh shit. Fuck. My mom is the sweetest woman in the world, but seeing me impaled by my boyfriends cock must've rocketed past what's acceptable for even the most understanding person. Anxious, I sat still and just listened. She went on, "Sammy, it's wonderful you've found your first love. It's very normal to be gay and please know that you don't have to hide it from me or from anyone, ever. I'm so proud of who you are. Your sexual identity doesn't define you, you are much more than who you love and make love to." I sensed she had a lot to say and I was already feeling far less tension with her understanding and approval, so I just listened "Matt, and really all of your friends, are wonderful. I'm so happy for you two. He's so handsome, talented and smart. Most importantly, he loves you and has always been a true friend to you. I couldn't ask for someone better to love and care for you. And... whew what a little stud. I bet you had fun on that thing! Hahaha. I'm sorry. Kidding.... I guess it's just been a while since I've been with a man. Seriously though, You make a gorgeous couple." Mom and I talked through dinner and on into bedtime. We talked openly about sex, love, and even read my play aloud to her. We had no secrets between us now. She knew I was gay and told me that she'd suspected so for many many years. Just before bed, I told her that Matt called me Samantha and how good it made me feel. And how being a girl all afternoon made me feel better and more alive than ever. I'd naturally been developing feminine features more recently, but I still felt like mostly a boy. More so my father, but my parents weren't big fans of medical procedures for non-fatal conditions. They believed we are born in a purposeful image and all images should be cherished and appreciated for their differences. My mother was a bit more open minded now and became fascinated by mental health studies over the years since my Dad died. She knew the importance of positive self image and she'd dove deep into papers on gender dysmorphia. I'm pretty sure she saw it coming as I was growing into a more androgynous boy. I told her how much I felt trapped inside and I was actually a girl. I didn't want to just act in plays as a female, I wanted to live as one. Mother was supportive and we agreed I would begin hormone therapy right away. I floated off to sleep, wrapped warmly in memories of sex with Matt, my mothers love and support, and the possibilities ahead for me as I transform. ---------- Chapter 2: Undress Rehearsal ------- Pete Dell Ben and Cam I woke up at 7 that morning, so excited and nervous about they boys coming over. I just knew the day would change me and things between me and the boys for the better. If all goes smoothly, 5 of my best friends are going to have sex with me today!! I began preparing myself for them. First, I did several enemas to clean my insides thoroughly. Next, I showered and scrubbed vigorously which I followed up with a hot bath with essential oils. I sparkled that day - My milky-moist skin shined and smelled of roses, my nipples and hiney hole were identical colors, a cherubian pink like bubble gum. After doing my makeup, I went to pick out my costume. I wanted to sex it up a bit for the boys and settled on a bikini top and very short pleated mini skirt with no underwear. I looked at myself in the mirror and was almost pleased... I needed pig tails. I braided two symmetrical tails and adorned them with fluffy pink scrunches. Now I looked irresistible, hopefully, for the boys. Matt, Cam, Pete, Dell and Ben were to arrive at 10 that Saturday morning for rehearsals and Mom was going to the club around lunch time and staying through dinner. The boys and I had all day to rehearse and, hopefully, be naughty! I went downstairs to greet the boys and wish mother good morning. Mother was quite taken with my get up, assuring me that I looked irresistibly sexy and beautiful. She admired my freshly shaved legs, arms and armpits - not that I had much peach fuzz to begin with but I was completely smooth and milky all over. We talked moisturizers and other skin regimens until the boys arrived. I opened the door and jumped into character, "Hi boys. Thanks for being on time. Come in come in. Let's get upstairs and into wardrobe , we have a lot to accomplish today." Matt grinned a grinch-like smile from ear to ear, while the other boys' mouths collectively dropped to the ground. Matt was the only one not in shock and made his way in, giving me a hug and quick squeeze on my butt. As we walked in, my mother momentarily broke their deep focus on my body and out fit when she greeted them "Hi boys! So good seeing you. I'll be out of your hair in just a little while so please make yourself at home. There is plenty of food and drinks and places to rest." "Thanks Mom. We will be in my room. Have fun at the club. Come on boys... let's get to it" I responded. Matt led the way up the long sweeping staircase, I followed behind being trailed by my other 4 friends. I knew that my skirt was short enough to see up but to be sure they got an eye-full, I arched my back pushing my butt up and out so they could see I wasn't wearing any panties. I could hear their whispers behind me as they Jockeyed for position to get a good luck up my skirt. I felt so sexy and was really enjoying the exhibitionism. I quickly took control of the conversation, directing our day before anyone could comment on my outfit and appearance - I wanted it to play out organically and tease them all for a while. In wardrobe, I helped pick outfits that fit their roles but were, strategically, easy to remove. We rehearsed for an hour, the scenes that led up to my sex scene with Matt. None of them had read the new scene so it was going to be an amazing surprise for all. It was time for matt and I to do our thing so I handed Cam, Pete, Dell and Ben copies of the new scene and asked them to follow along. As Matt and I prepared, the boys read through the scene, elbowing and pointing each other in disbelief. They had a feeling they were going to witness something pretty hot, but I don't think they expected quite what would transpire over the next 8 hours. Matt and I worked the scene beautifully and were flawless up to the kiss. We began making out feverishly, matt pulling up my skirt to fondle and grope my ass and rub my tits. Matt untied my bikini top exposing my perky suckable tits and I pulled his tank off and continued making out. I then dropped to my knees, dropped his shorts and began sucking his cock in front of my friends. Their whispers were no longer whispers as the gasps and "oh shits. woah dudes. Unreals." began a symphony of approval. Next, I wanted them to see clearly when Matt's cock would go up my butt, so like yesterday, matt laid on his back in my bed while I straddled him after removing my skirt. I had already thoroughly lubricated my insides and was ready to ride Matt for all of my boys to see. The four of them huddled behind me to watch up close as I guided Matt's cock to my pretty pink hole and glide gently down into it until I had all of Matt inside of me. We wasted no time settling into a steady rhythm, making wonderful slurping and clapping sounds - his cock pumping in and out of my tight and slippery hole. With Matt deep in me and the boys watching me in awe as i rode his cock, I was beyond turned on and exploded my semen onto his stomach and chest. Matt quickly followed with his own eruption, pouring a bucket of cum deep inside of my hiney. Before calling end scene and addressing the boys, I licked Matt clean of cum as well as the puddle that leaked from inside of me. I turned and sat on the edge of my bed, facing Cam, Pete, Dell and Ben who all had priceless expressions plastered across their faces - a combination of shock, eagerness and lust. "So.... What do you guys think so far? Pretty spicy huh? Samantha gets pretty naughty don't you think?" I asked, still in feminine character. Before they answered, I couldn't help but feel the weight of the moment. For the first time in my life, I was Samantha, completely embracing femininity and presenting myself to my boys as a girl. Cam was the only one that could speak intelligibly and responded to me, "Wow. Sam...Samantha, you look so hot... I mean, you're a girl! That was unreal what you and Matt just did. I can't really process it and I'm so hard right now I can't think." I was really eager to hookup with all of them and I figure their shock would last for a while, so I said "thank you" and walked to Cam and began making out. He was really into it from the start; I stood there kissing Cam as he groped my all over , exploring every inch he'd eyed that morning. I felt more and more hands on my body, stroking up the insides of my legs, on my butt cheeks and up in my crack, and all over my stomach and tits. The four boys could have their way with me, just as I'd planned. I asked Cam to sit in a chair after I pulled his shorts and underwear off so I could kneel between his legs and suck his cock. I positioned my body so that my ass was in the air, allowing the other boys to explore my butt. Cam, like Matt, also had a gorgeous cock - 7" with smooth heavy balls and big mushroom head. I worshipped Cams cock, slurping and licking away at it wildly, while I believe Ben came behind me and began licking my ass. The sensation was new and orgasmic for me, Ben's tongue lapped and pressed at my hole, even biting my cheeks as his desire for my bottom grew. In my periphery, I saw Dell and Pete, now nude, standing and stroking their cocks, patiently waiting for their turn with me. I took Cams balls in my mouth and worked them over thoroughly as Ben was now lining up his cock to my hole, rubbing it up and down and eventually pressing in. With a pop, Bens long and skinnier penis was sucked inside me by my eager, hot and slippery hole. Cam wanted a turn in my ass as well, so after a few minutes we switched up positions. I straddled Bens waist and rode his cock while I rotated between sucking Cam, Pete and Dell until it was their turn to be in my ass. Pete was the thickest of them all and he had real pubic hair which was cool. Dell was the smallest but still respectable with a pretty pale pink 5" knob. Matt soon recovered and joined in the sucking rotation while I bounced around on Bens cock, having a great time. Then, from behind the boys, I saw mother in the doorway of my bathroom watching me. She had a shocked look on her face that quickly changed once I made eye contact with her. I froze for a second, stroking two cocks, riding one and about to stuff another in my mouth. Her look morphed into naughty smile, that of an accomplice who you shared a secret plan with. She made the shh gesture with her finger and blew me a kiss and a wave, letting me know she was leaving for the club. I winked back as I took Dells cock into my mouth and jerked Cam and Pete. Now there were definitely no secrets between me and mother. Ben began to thrust up into me and exploded inside my ass. I felt his gushing cock rocket load after load. It turned me on so much that I sucked Dells cock feverishly now, I was starving for cum. Dell quickly came in my mouth, he too cumming an enormous load onto my tongue. I gyrated my hips, grinding into Bens cock to milk more cum into my ass while I sucked more and more cum from Dell. Cam was eager to get in my ass and he wanted to watch his cock slide in and out of my ass. I suggested he sit in the chair and I backed up into reverse cowgirl, planting him deep inside of me. Dell and Ben recovered on my bed and Matt and Pete presented their cocks to my mouth. Cam loved the sight of my milky bubble butt swallow up his cock, my curvy hips bouncing up and down in his lap. After some time, cam stood us up and fucked me from behind, slapping his pelvis into my ass and exploring my depths with his near exploding cock. I worked Petes huge cock with my mouth as Cam rooted deep into me, holding me still by my hips, and ignited his cannon. Waves of his cum filled up my ass entirely now, Matt's Bens and now Cams cum began leaking out of me. Dripping down me, I reached back to wipe up the cum before it fell to the floor and licked it up. Cam stayed deep inside me and his cock twitched still, moments after his orgasm, still squirting drops into my flooded cave. Pete too was eager for a ride and Cam reluctantly exited my warm pussy. I cupped my hand under to catch the cum as it flooded out of me - I slurped it up and took Matt into my mouth again. Pete's huge cockmade it Inside of me thanks to all of the cum, but it was certainly the tightest fit and had me on the verge of my second orgasm very quickly. Pete and Matt had me spit roasted, matching their rhythm back and forth, like a well oiled machine I was rocking both cocks in and out. I began to cum again, catching the load in my hand then coating Matt's cock with it and sucking him clean. Several minutes later, Pete's full balls that were swinging up and slapping into my cock, emptied into me. He pumped and pumped and squeezed my body as his blissful orgasm washed over his body. I cleaned up his cock and cum from my ass and continued blowing Matt passionately. When he was cumming he pulled out and told me "look at me Samantha. Look at me baby. I love you" and then he jerked his cum onto my face. His load was huge and covered me forehead to chin and rubbed it all around with his cock. As I shoveled the cum into my mouth with his cock, I told him I loved him and never broke eye contact while I consumed the entirety of his cum. And just like that, I'd come out as trans to my friends and experienced the first of many orgies with them. ----- For the next hour, We talked candidly about my transition, the sex we had, my relationship with Matt and the boys, and, really, just laid it all out there. We were all thrilled to be sexually active now and pledged to remain open and honest so jealousy wouldn't ruin what could be a beautiful thing between us all. I happily agreed to satisfy all of the sexual desires whenever they needed me to - I loved the idea of being on call for them; it felt empowering to provide such pleasure for my friends. They all had sex with me several more times that day in addition to rehearsing my play and left my house more than satisfied. We agreed to meet the next day and rehearse some more and Matt decided to spend the night with me, swoon!! By the time mother got home it was just me and Matt hanging out. Mother had brought Mr. Davis home with her and suggested we have leftovers together. Mr. Davis was an old gentleman in his 70s and was on the club board with my mother. A widower for many years, Mr. Davis was successful, retired, and a very warm man; he went out of his way to speak with us youngsters when we socialized at a play or hanging at the country club; he was great with kids. We finished dinner and Matt and I were heading upstairs to my room when mother asked me for a word in private. I followed her to her room, "Honey? I'd like Mr. Davis to stay over with me tonight if that's ok with you. It's been a while since I've been with a man and our wonderful conversation last night made me think it's about time I have some lust in my life. You're growing up fast and your life is filling up, I think it's time for me to date again. Plus, seeing you this morning with the boys got me riled up... I trust everyone had an amazing day with you?" I hugged her and answered "Of course mom. I'm happy for you and I agree, you need some love and lust in your life! Mr Davis is a great man and handsome, but he's much older than you... can he provide the sex you're looking for? You're nearing your prime and you might kill him, hahaha. And yes, all the boys had a great day and I'm super excited about the future. Thanks for being cool with all the sex and stuff. It's nice they can come here and we don't have to sneak around to make love and get a little wild." Mother kissed my cheek. "That's great sweetheart. We can talk more tomorrow about your transition and I made you a doc appt for Monday. Oh, and, yes Mr Davis is plenty capable of fulfilling my needs. (Whispering to me) in fact, I got a little preview in the board room today when I gave him a blowjob. He's quite the man. I'll try and keep it down tonight. Which reminds me, I have something else to talk with about but we should save it for tomorrow. Go have fun with Matt. I love you sweetheart." Matt and I said good night to Mr Davis and mom and proceeded up to my bedroom. We made love before falling asleep and I asked him to stay inside of me all night. He spooned me from behind, both of us were nude, his cock securely planted deep inside of my cum-filled hiney. That's how I ended the best day of my life, embraced by my love; two bodies as one. End of part 1 ---------------------------------- Thank you for reading part 1 of my story. I hope it inspired you and turned you on. My hope is to encourage more writers to contribute stories in the transgender section, specifically in young friends, teen and high school. Nifty stories have helped me so much and provided such joy. I do hope more of you will consider writing more transgender stories for my enjoyment.