"You’re a Girl Now?" Ch. 04-06

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

He is a family man. Sure he is saying he's worn out now. But this is what he's used to. This is what he'll expect. A family. Children. I have no doubt he likes me but there are certain things I just can't give him...

He noticed and halted his playful chase. "Is everything alright?" By this time, we had returned to his old room.

I must have spent hundreds of nights in his room throughout my life. It was always a more comfortable and welcoming place than my own room even. Even though Gracie tried to reclaim the place, his essence still lingered about and it was a very relaxing spot to be in. Many hours were spent playing with toys. Then when we got older, we were lying on the floor, tossing a baseball up to the ceiling while we talked about girls. It was in there that he first told me he was going to join the military.

"You say you're tired now," I said and sat down on his bed again. "But you're going to want that. Eventually. You're going to want that sort of life. That American dream with the house and the kids."

"You'd look cute in an apron," he laughed and sat down on the floor in front of me. "That's a long way off. I can't be there for a kid right now. I'm out in the field all the time. Then we're deploying in a few months. Maybe one day but not now."

"So I'm right then?" I asked breathlessly. The tears involuntarily came and I felt my heart sink. He let it slip. I don't even think he realizes what he's saying right now. This isn't going to last by his own admission.

"I mean eventually," he shrugged with a confused look on his face. "If you're not okay with that, I don't want to force you. I didn't expect to be having this conversation so soon, to be honest."

"You've been really nice to me. So has your family. I've come out to you and since then I've been a girl in your eyes. These last few days have been really... validating for me. But let's face it Flint, I can't give you that. Not like a real woman."

He leaned back and sighed. "It isn't just women..." He stressed the word "...like you who can't get pregnant. When the stars are aligned, if you want, we can talk about adoption or a surrogate, or... whatever. Or even if you don't want kids, it's fine. It's all a long way off from now." Then he stood on his knees and put his hands on my thighs. He took in a long breath and slowly exhaled. I did the same and we breathed together for a moment.

Then he continued "I don't want to belittle what's troubling you, but you're getting all worked up over how you think I'm going to react to something. Or how my family is going to react. And I'm sure you're probably scared how everyone else in our life is going to react.

"I get that it hasn't been easy for you. And I don't expect you to be able to just... shut it off. Not in a few days, at least. I get it. But I'm here for you, Sammy. When something's troubling you, I don't want you to hold it in. I want you to tell me so I can tell you that everything is going to be alright. No matter how often you need it. How ever long it takes for you to know."

"I'm sorry," I choked out, eliciting another one of his breathing exercises. "It just feels too good to be true. Good things don't really happen to me."

"But they happen to me. You happened to me," he reassured me. "Besides... I'm hard headed. And you know what, Sammy?"

"What's that?" I asked and he stood up and pushed me down gently onto my back. He lied down on his side on the bed next to me. Then his strong arm effortlessly pulled me to my side. His fingers gripped the underside of my thigh and brought it up over his leg.

"I'm still gonna try to make one with you," he mischievously hissed in my ear and his hand quickly found its way up my skirt.

Chapter VI:

Even before I came out, I explored my sexuality in secret. I talked to people online, which probably wasn't the best idea in retrospect. But it opened my eyes and showed me that I could experience sexuality in a way that felt right for me.

I experimented with all sorts of things. But the one that felt like the natural conclusion were all the toys I put inside me. But then I became concerned with the preparation for these undertakings. Since my first kiss with Flint, not a moment went by that I didn't think about when it might happen.

But when I saw his cock for the first time, as hot as it made me, it was kind of terrifying. I wasn't even aware that guys could be that big in real life, at least outside of porn. Nevertheless, I had done all the appropriate prep work for this exact occasion.

While the rest of his family was at church, he had my skirt was hiked up over my waist. My leggings were pulled down over my knees. I lied on my belly on his bed with my bare ass tilted upward. My little penis and tight little balls were tucked back between my thighs.

His huge uncut monster was already wet with precum and he rubbed the head against my tiny shaft, coating it with his wetness. I felt his heavy balls drag against the backs of my thighs.

Oh God it's happening. He's going to tear me in half! I want this but I'm afraid of how much it will hurt... Then I felt him brush his cock between my cheeks, gently press against my hole and recede slightly, like it was giving my bum a warm, wet kiss. I grit my teeth and curled my toes in anticipation. Fuck! I'm not ready. This is gonna hurt...

But then he pulled back. I glanced over my shoulder to see him unbutton his shirt and reveal his broad muscular chest, which was just starting to grow back the little black hairs he usually shaved from his pecks for swimming. He took the time to get completely naked. After that, he peeled my leggings and skirt all the way off. Ok... now he's gonna do it. I sank my teeth into his pillow and shut my eyes.

But the body destroying penetration didn't come. Instead, I felt his lips against the head of my little wiener poking out from behind my thighs. First, he kissed it and cupped my tight little balls in his huge hand. Then he took it in his mouth. His tongue was bigger than the whole thing and it wasn't much for him to slide his slips all the way down the base. I'm sure I wasn't even touching the back of his throat and he didn't sound like he was struggling in the slightest.

It was the first time anybody had ever gone down on me. I never imagined it happening to me, to be honest. But he did it in such a way that I felt completely at his mercy, bent over for him to toy with. He put me in a very helpless and exposed position but it only turned me on even more. When he exhaled through his nostrils, his hot breath washed over my thighs and between my cheeks. His stubble scratched against my soft skin.

"Sammy," he moaned from behind me. "Can I press your button?" He placed one finger over my bum and pressed against it gently. When I replied with a pleading "mhmm," he pushed the tip of his finger inside of me. With his other hand, he began to gently milk me.

"Right there!" I gasped and he started to massage my spot. "Oh fuck, Flint..." I whined impotently. He took this as direction to keep at the same pace. Both hands worked in the same rhythm and his touch was firm but very gentle.

"You're so cute," he teased and it was clear he was enjoying himself while he brought me closer. "Do you want to cum, baby?" When I whined in response, he laughed and kept at it and I felt like I was going to burst soon. But he must have felt it also because he slowed down just before I could climax.

"Please!" I begged and wiggled my butt and tried to push back into his hands. "Please let me cum!" I could feel the pressure building inside of me. He continued to bring me back and forth from the brink and laughed when I got louder every time.

Finally, he released me and pressed my button more deliberately. Also, his other hand wrapped around and covered my little penis completely and he squeezed and stroked it more vigorously.

I moaned into his pillow. My insides switched and cum shot out of me like never before. It shot out all over my trembling legs. My butt thrust upward and my eyes rolled to the back of my head. I had never had an orgasm quite like that before. The cum was watery and shot out of me instead of its usual ooze.

"Flint, that was... amazing," I panted while my body was still trembling. I rolled over and looked up at him. I was still wearing my "Ho Ho Ho"

sweater and there was something about being naked from the waist down that made me feel very vulnerable.

"I wanted to... you know..." He started while he sat up and pulled my legs around his hips. "But I didn't know if you were ready for that." He still had a certain hunger in his voice and I could feel his giant erection resting on top of mine, which had receded to basically a little nub. Still, he lustfully rubbed his head to mine, leaking out even more wetness.

"I have to work up to it," I said and scooted my butt closer to his hips. When I placed both of my hands on his cock and held it to my belly. The tip tickled my bellybutton underneath the hem of my sweater. "This is how far inside me you would be if you went all the way," I giggled while I lifted my sweater up and started to stroke him.

"I guess you needed a different kind of training, huh?" He asked and reached his arms around my back to pull me to a sitting position. I pumped his huge dick with both hands and I felt my own being completely smothered by his hot stones bouncing between my legs.

I could feel myself getting aroused again. He pulled my sweater off my chest and tossed it across the room. We kissed open mouthed and I shuddered with excitement. Our tongues wrestled and I was more than happy to submit.

I bit his lip softly and pressed my body closer to his. "It's just so fucking huge," I whispered "but I want to get there... I fantasize about it. I want you to fill me up. I want you to cum inside me. I want you to breed me," I pleaded and this only excited him more. He pushed me down onto my back.

Oh no, did I go to far? Is it going to happen now?

But he managed to restrain himself. As a consolation prize, he stroked himself over me and let slip a passionate groan as his cock pumped out ropes and ropes of cum. While my orgasm was thin and watery, his was thick and heavy. His cock twitched as it squirted, even making a delightfully lewd sound as it shot. He painted my little penis with the lion's share but also shot all over my belly and chest.

It was hot and I felt it ooze down my skin. There was something so primal about being covered with his seed. He was like an animal marking his territory. Asserting his dominance. I liked the feeling and I wiped some of his passion from my ribs and licked my finger.

He collapsed onto the bed next to me and we continued to make out. The combination of the scent of his cologne, he subtle scent of his sweat, and the smell from the copious amount of seed he coated me with drove me wild. He could feel me stiffen against his skin and he gripped my shaft, tracing a finger around the head. When I let out little cries from this, he laughed and asked "Do you want to cum again, Sammy?"

But I don't think he cared if I responded. Before I could say another word, he pinched and massaged the tip while we kissed.

My mind wandered back to the last few days. Up to a certain point, I was "dude" and "bro" to him. One of the boys. His best boy. And he acted that way- he was rude and belligerent, but in that funny and charming way that exists between men.

But I will never forget the look in his eyes when he first realized how much I had changed. Maybe it was a good thing that he went away when he did. That I changed when I did. If he saw this happen day by day in tiny increments, perhaps I would still be "dude" or "bro".

I've seen that look before. It was the way he looked at other girls at our school. When he looked at me that way, I felt a change but I didn't realize it then. I flipped a switch in his head.

Though altered and feminized as I was, and tiny compared to him, I still had all the same parts as before. Maybe I was softer and curvier. More squishy. But he held between his two fingers the brutal reminder of the hand that God had dealt me.

And it was nothing at all for him. There was no uncertainty in the way that he kissed me. In the way that he touched me. In the way that he took me in his mouth or milked me.

In an instant, it was though he never saw me as a boy. Only he realized that I was poorly masquerading as one for most of my life. And the moment he saw me drop the charade, his hunter eyes locked on to me. How quickly he turned on me!

I squealed and oozed out onto my belly and all over his fingers. He brought his hand up so I could taste. Then he kissed me and licked it off of my lips.

"Sammy..." he whispered after a few moments. "I know you have your highs and lows. You kind of always did. You're in your own head a lot. But I'm here. And I'll be here tomorrow too." Only a second later, he was asleep.

And for the first time in a very long time, I slept through the night.

[Author's Note: Once again, I appreciate you reading this far. Thank you so much for your comments, ratings, and support. This was originally going to be a single short story that was a prompt from a friend but it took on a life of its own. Thanks to so many of you who want to see this to the end. By the time this gets approved, do know that I am already working on another installment. I cannot say it enough: thank you and Merry Christmas!]

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
24 Comments
jrrtolkien420jrrtolkien42011 days ago

Really good story. Love the character development. The slow burn is also really good.

Hope you finish.

I know I did.

AnonymousAnonymous4 months ago

PLEASE POST MORE OF THESE!

Usually these things are just sex scenes with interludes, but you've managed to elevate the entire genre to something that wouldn't be out of place in a Barnes & Noble!

Also, I'm pretty sure I'm trans now.

Andi_T800Andi_T8005 months ago

I really hope we get to hear how our dear Sammy and Flint are doing!!! This story is everything I have wanted out of a friends to lovers romance with a trans character 💛 how you are well, and how you know how much I LOVE and appreciate your stories!

Observer143Observer1436 months ago

Waiting for the next installment. Don't quit now. It's a good story about a transgender, more interesting than the sissy and forced stories. Keep up the good work.

SissyBoy1WarszawaSissyBoy1Warszawa8 months ago

I can't find words to express my great thanks to you @R_Violette for such a great story that gives hope, dreams into true friendship, love. Thanks to you, my heart beats strongly and with faith that there is someone who can give people like me (SissyBoy) his affection and understanding.

If I could, I would give you @R_Violette even 10 ⭐ stars. With great interest and impatience, with whirling thoughts and imaginations, I am already looking forward to the further fate of Sammy/Samantha and Flint. 📖👩🏻‍🦰👨‍❤️‍👨👨🏻‍🦱❤️👩🏻‍🦳.

ps. Sorry for grammatical errors and inaccuracies, but I don't speak English.

SissyBoy from Warsaw, Poland. 📖👩🏻‍🦳👩🏻❤️🧒🏻.

📖❤️

Nie umiem znaleźć słów aby wyrazić swoje wielkie podziękowanie dla Ciebie @R_Violette za tak wspaniałą historię, która daje nadzieję, marzenia w prawdziwą przyjaźń, miłość. Dzięki Tobie moje serce bije mocno i z wiarą że istnieje ktoś taki co może obdarować takie osoby jak Ja (SissyBoy) swoim uczuciem i zrozumieniem.

Jak bym mogł/a to dał/a bym Ci @R_Violette nawet 10 ⭐ gwiazdek. Z wielkim zainteresowaniem i niecierpliwością, z wirującymi myślami, wyobrażeniami już wypatruję na dalsze losy Sammego/Samanty i Flinta. 📖👩🏻‍🦰👨‍❤️‍👨👨🏻‍🦱❤️👩🏻‍🦳.

ps. Przepraszam za błędy i niedokładności językowe ale nie znam języka angielskiego.

SissyBoy z Warszawy, Polska. 📖👩🏻‍🦳👩🏻❤️🧒🏻.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Secrets and Surrender High school can be lonely, but shared secrets can help.in Transgender & Crossdressers
Lily in Bloom Ryan's college crush is not like what he had imagined.in Transgender & Crossdressers
Homecoming Queen A high schooler helps a friend who doesn't have a date.in Transgender & Crossdressers
I Know Sparks between me and the cute but shy T-girl next door.in Transgender & Crossdressers
More than Friends Pt. 01 Lifelong best friends become something more.in Transgender & Crossdressers
More Stories