New World, New Woman

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

"You know sweetie, I never saw Reggie this happy." Shelby knew sometimes a parent could overreach trying to help a child come to a self realization, but this one seemed so easy. Without the slightest hesitation, Regina took the bait.

"You're right mom, getting the Yellow Envelope was the best thing to ever happen to me. I am glad to be Regina McMartin, and not Reggie." That was it, the one thing every mother in this messed up world hoped to hear, that her daughter would not only survive, but thrive. Inevitably, mother and daughter collapsed into a huge teary hug.

The next morning Regina was up bright and early, skipped to the bathroom, sat to pee, and joyfully leaped into the shower. She was aroused beyond belief, and yet her penis lay limp and tiny. Yet unlike 72 hours ago, when arousal fogged the brain and made concentration impossible, Regina was acutely aware of every sensation and feeling. As she climbed out, she wrapped a towel around her chest and considered her arsenal for the day. She was afraid that her available wardrobe was not cute enough, or more accurately, sexy enough.

"Mom?" Regina said in a loudish whisper, softly knocking on her parents door; her dad was known to be a bit of a grump if disturbed to early on the weekends. "Mom, are you awake?"

Regina was startled by the suddenly opened door. Apparently Shelby was as awake as her daughter. Slipping into Regina's room she asked "OK, where's the good stuff?"

"What 'Good Stuff?'" Shelby replied with a coy smile.

"Mom, you know what I mean. You seem to have had every little detail planned out. Where's the stuff for me to totally blow away the boys?" Regina had serious look in her eye, reminiscent of a lioness on the hunt.

"Okay, Okay, yes I did prepare for that as well, but these are dangerous weapons, so you have to be ready." Regina had a look of greed and anticipation more pronounced than any kid on any birthday.

Shelby produced a form fitting pink dress with the tiniest straps, with an embroidered floral pattern in a matching pink thread. It was a very sleek dress that reached Regina's mid thigh, and showed of her tight cute ass in glorious fashion. To top it all off, the built in bra was complete with breast forms. Shelby also produced ferociously naughty pink lace panties. The shoes were a simple pink flat.

"No high hills?" Regina pouted.

"Honey, walking in this dress is tough enough. Besides, these shoes will give you far more options today with Jack." At that thought Regina flashed a smile that dentists across North America would kill to have in their ads.

Regina did not recognize the last item Shelby had. It was a new type of gaff to keep Regina tucked away nice and smooth, yet not visible beyond the panties. Finishing her makeup and adding a pink satin ribbon tied in actual bow, Regina realized that she was more ready to meet Jack that morning than for any other thing in her life.

Regina skipped down the stairs for breakfast, and was absolutely bulletproof when James finally started letting the wisecracks and insults fly. With absolutely nothing affecting her, he quickly ran out of steam. James was absolutely defeated, and Regina had never even fired a shot.

Jack picked her up at 10, and the light that greeted him at the door made him wonder if there was some weird solar anomaly creating a second sunrise. Jack was pretty sure even Leonardo da Vinci would have a hard time capturing Regina's smile. She was already skipping away sucking Jack along in her wake before he realized what was happening. She wrapped her arm around his and they passed happily down the street. More than a few onlookers had to think very hard before they could place the blond hurricane that was happily singing on their street. Every single wondering look was replaced by a nearly catatonic stupid glaze when they realized who this force of nature in the dazzling pink dress was.

They didn't really do much that day, mostly just walked and talked. Jack's powers of speech had returned, and Regina was happy to discuss any subject. Since Jack's family was away, they eventually wandered back to his house.

"Regina, you are amazing. The change that has come over you is spectacular. Did you see how flabbergasted Mr. Williams was? I know he's nearly 95, but still, the look on his face was priceless. It was awe with a heaping helping of horniness."

"Not uhh. You are so bad." Regina swung a throw pillow close at hand. She was sitting in the middle of the couch, turned to face Jack who was trapped against the end. Jack was far too athletic to get caught with her pillow toss, but he was not particularly inclined to move.

"I can't say that I blame him. Really, what has happened to you? Reggie was a nice guy, but there is something otherworldly about you now." Jack was looking at her intently, trying to see if it was something discernible with the naked eye.

Sitting up very straight with her arms out front, affecting her best southern accent, and kind of batting him away she asked him "Why, Jack O'Connell, are you flirting with me?" Her giggle was infectious, but also distracting from the point.

"I'm serious. Friday morning you looked like a dead woman walking. Today there is an entirely different person here. Where did you come from?" Jack was sincere, and very much wanting a sincere answer.

"I don't know, exactly. I just decided my mom made the change, and she's happy. So I decided I could be happy with the change too. Then my mom pointed out that Reggie never seemed very happy, and she was right, I have never been as happy as I have been the last 24 hours. But I gotta say your serious vibe is kind of a buzz kill." Her smile was still there, but Jack did notice the tone in the room was less light.

"Okay, no more buzz kill. You are a truly amazing person all the way through. So yes, I am flirting with you." This last admission surprised Regina a bit, it also thrilled her.

"Alright then, carry on." She hoped her smile was also flirtatious, but with so little practice, it was hard to know. "I give you permission to tell me how beautiful I am again."

This time Jack laughed. "Very well. The very first moment I saw you Friday morning I was completely tongue tied. Then when I picked you up this morning, I thought your smile was a second sunrise."

Regina was blushing in earnest now. "Wow, you are a good flirt!" She reached out and touched his knee without thinking about it, Jack definitely noticed. "I would have also accepted 'stupid mode' instead of tongue tied. But where did you get that sunrise line? That was really good!"

"Just how I felt when I saw you." Jack really didn't know what to say to her.

"Well if you had just said something charming like that Friday morning, maybe you wouldn't have had to apologize in such humiliating fashion at the dance. Seriously, do you walk around like 'MMmh M MM Mhhhhhm' on purpose?" She had been sticking her tongue out at him, contorting it into odd shapes while making the noises, and leaning in quite close.

Jack had no idea what came over him, but he just couldn't resist any longer, and he kissed her. A bit of an awkward kiss really, he moved in too fast and there was a minor nasal collision. But there would never be any mistake about what it was.

Regina was stunned, things had definitely changed between them, but had they really gotten to this point. Her mind was racing so fast but didn't it just feel right? If she was happy becoming a woman, didn't it make sense that she would happy with romance with a person she cared so much about? Wait, what kind of caring feelings does she really have for Jack? Are they really that strong? Racing as fast as it was, Regina's mind quickly decided that she needed more information.

"That was awful." Jack was starting to look terrified, 'Good' she thought. "How about you slow down a little, hold me gently, and not crash into me." She just loved Jack's stupid look. Her own solar smile, full of anticipation and lust, was making it very difficult for Jack to get his brain restarted. "Here, let me help." She placed his right hand on her shoulder, and then placed her left hand on his waist. Jack's brain finally caught up, and he was more than ready this time.

In one very elegant move he slid his right hand down her back, pulling her closer, slipping his left hand through her hair to the back of her head and pulling her face in. He helped steer her to his left; he went to his right, and waited with the slightest hesitation, to make sure there would be no collision. Regina noticed the hesitation, her brain screaming to get on with it. Jack got the reaction he was looking for, and met her gently.

This was the first romantic kiss either of them had ever had, but Jack was no dummy. He had carefully sought out advice from experienced people. He had rehearsed the move in his mind many times over the last year. Looking back on it, he would swear that he now realized Regina was the person he pictured in his rehearsals.

Regina was indeed breathless, for the romance of the moment, the deftness of the move, and her own anticipation. Slowly in the back of her mind an understanding was blossoming, that she and Jack belonged together. The Yellow Envelope was no mistake, nor was it some anonymous bureaucratic result of some number crunching computer. The Yellow Envelope was the earth bound indicator of a celestial alignment that would finally bring two soul mates together.

Regina thought she had started this, but Jack had taken over in such dashing fashion that her hands simply sat as bystanders. Now she reached up around Jack's chest, trying to pull herself closer. Jack had another deft move up his sleeve, and easily pulled her onto his lap. Her gasp, then long sigh told Jack all he needed to know. Their hands were now exploring, caressing, grabbing, stroking. Their tongues now met tentatively, cautiously, again carrying out the ballet of first kiss, first love. Regina completely surrendered to Jack; she needed his tongue to go anywhere and everywhere.

Sitting on Jack's lap Regina discovered something else, straining, charging, to join the party. Regina started swaying, rocking to see how much contact she could make. When Jack whimpered, she knew what to do. She started with very small movements, gradually increasing the size of the movements, but also trying to apply more downward pressure. Jack was groaning into her mouth, wondering himself where Regina had learned so much, or was it just her natural grace.

Jack was losing his concentration on Regina's lips, so much blood flowing so fast to his manhood. This was exactly what Regina was trying to accomplish. She released his lips, and started to work her way down his torso. She was kissing him through his shirt, touching with her hands his well muscled chest. She started zigzagging when she got to his abs, causing him to make a bizarre whimpering, panting, giggling noise.

She was going to take her time circling her final destination. Drawing circles with her finger around his crotch, her delight grew as his anticipation, and hard on grew. She looked up at him, cracking and evil smile "Jack, is this the first time you have had a boner around me?"

He didn't want to sound like a perv, but there was really only one answer "I have had a hard on around you every moment since I first saw you Friday morning." He could care less about embarrassment at this point, all he cared about was amazing blond creature he had known for years, but only just really met just two days ago.

"No wonder you were so stupid Friday morning. I really had no idea, but I am flattered. I think it's time for me to get acquainted with Little Jack." She got absolutely no resistance from Big Jack. She went as slowly as she possibly could undoing his belt, pulling on his zipper. She was just as excited as Jack, but she couldn't let him know that. Jack was worried he would explode before she even managed to get him free.

Finally the moment where she let him spring free arrived. Regina gasped in appreciation. She had seen penises before, but this was the first one that one ever stood to attention for her. This is the first one that would obey her every touch. This was the first one, probably the last one, she would ever desire.

Circumcisions were still widely practiced. The process had been improved so much that there was very little risk to the boy, very little discomfort. There was no real medical reason for it, just aesthetics. Far more often than not, women preferred the opposite of what they had before they were Processed. Shelby had been circumcised, and was thrilled when Jerry was not. Shelby chose not to circumcise her children. Regina was at this moment basking in the beauty of Jack's cut cock.

She devoured his cock with her eyes, trying to memorize every detail. The head seemed immense like a helmet. She started to touch it, tickle it. She marveled at the obedience it gave her. In a goofy, wholly unromantic moment she thought Jack's penis obeyed her like a soldier would an officer. "Soldier, ATTENTION!" she sort of yelled, mostly giggled. Jack obliged, contracting the pelvic muscle and thrusting his hips up.

"Ma'am, YES MA'AM!"

"Good, now that we've established who's in charge . . ." Her mischievous grin disappeared at the exact same moment as Jack's cock. Regina's only guide at this point is what would have felt good to Reggie. She went as far down as she could, then traced the underside with her tongue as she came back up. She tightened her lips as she went back down, and returned with the slightest pressure from her bottom teeth, drawing a startled, grateful gasp from this man that had become infinitely more important to her over the past two days. Reggie's cock could take some pressure, could be treated roughly, so she assumed, correctly, that Jack's could take more. She grabbed it firmly at the base and started stroking while her tongue danced on the head, especially tracing the crown.

Regina loved the reaction she was provoking, really loved the physical contact and intimacy with Jack. For his part, Jack was squirming like a cat in a tub, so many stimuli firing at once, so many different pleasures short circuiting his brain, so many electric sensations causing his body to convulse and spasm. Lacking much experience, Jack also lacked staying power. His breathing and moaning had given Regina enough notice, she clamped down on his head, ready to take the entire load.

Jack convulsed, exploding into the mouth belonging to the most beautiful girl he knew. He convulsed again, and again. Regina took it all, swallowing as fast as she could. Regina felt a burst of joy at the moment of Jack's orgasm. She loved Jack's body, but more she was amazed at the reaction she could provoke. She loved making him feel that good.

She was surprised how well she got the cum down, it tasted a bit bland, kind of salty, kind of watery, it definitely felt slimy. But the look on Jack's face made it something she planned to do again very soon. Jack was overcome with a feeling of pure physical bliss. He was too inexperienced to recognize clearly the emotional bliss he felt, the perfect emotional connection with that somebody special.

Jack pulled her up and began to kiss her again, and began to reach for the zipper on her dress.

"No, not now. I don't want to you to see my body right now. I don't ever want you to see that thing between my legs!" Regina was dying to have that contact with Jack, to have him inside her, but not at all before her outside matched her inside.

"Your wish is my command, not until you say OK. But I have to tell you that I think I love you, and I don't care what you look like, I see the real you, and that is who I love." The sincerity on his face was exactly what he felt in his heart.

"Oh Jack! I love you too! Thank you for understanding. Maybe it's silly, but thank you. I am going to talk to Dean Vernon tomorrow, find out how soon I can get processed. I know I want this, and I want you. I can't wait another day to get started."

They just sat snuggling and kissing for the longest time. Regina so enjoyed being wrapped up in those magnificent arms, held to that gorgeous, strong chest. Sitting there, Regina thought that the next day felt like a million years away.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
20 Comments
AnonymousAnonymousover 2 years ago

A very wonderful story. Very romantic and well written. It would be really great if you could add some additional chapters.

ColonelinguistColonelinguistabout 3 years ago

Just stumbled on to this impressive first time effort from lilmiss, six years after the fact. It’s To bad that there wasn’t a follow-up story. Like so many other reader, I feel like she left me anxious to learn more about Regina’s transformation. Such as how or if a function female uterus is created and transplanted into a mature young male.? Will reggie’s reproductive organs get removed like a gall bladder, or your tonsils?

AnonymousAnonymousabout 7 years ago

I hope there is another chapter soon & the surprise in this world when in this world, Regina gives birth to a daughter!

AnonymousAnonymousover 7 years ago
More Please

I'm glad to see this surface again. The first time I read it I thought then as I do now that it is the BEST story I've ever read. I placed a comment the first time about how eagerly I hoped to see a 2nd, 3rd or more chapters. I would love to read about her transition process and life as a woman. So far I'm only still hoping. Please, if you have any mercy in you, write more about her life. Anyway, thanks for writing what you have and posting it. Cudos!

harderthanitlooksharderthanitlooksover 8 years ago
Lucky Stumble!

Came across this by accident, LOVED IT! It flows so well, so well written, and loved that the completely improbable seems quite real. You can feel the excitement, and of course LUST, of new love.

Show More
Share this Story

Similar Stories

A Change with Sam Being kind leads to surprising and desired moments.in Transgender & Crossdressers
Changing Room Prank Mark and Greg help me discover myself with a harmless prank.in Transgender & Crossdressers
Best Friends Again His reunion with old friend goes awry.in Transgender & Crossdressers
Secrets and Surrender High school can be lonely, but shared secrets can help.in Transgender & Crossdressers
Big Dick Beauty in Space A 33rd century romance of sorts.in Transgender & Crossdressers
More Stories