Jimmy sat up in bed and felt the dry cum on his belly from last night's masturbation. A quick look at the clock told him his parent's had already left for work and their weekend trip so he knew he had nothing to worry about. The plans he had for the day could begin right now.

Stepping out of bed, he padded to the bathroom and began the process. A long shower began the day. He made sure his shapely legs were shaved silky smooth before moving to his underarms and then to his pubic area. He liked that he'd kept his pubic area trimmed so neatly and now only sported the small patch above his cock.

When he stepped out of the shower he padded dry and then brushed his long brown hair free of any tangles. He'd always worn his hair long and that fact definitely came into play now. Using the hair dryer gave his hair more softness and a little more fluffiness.

He knew each step of the process by heart and continued on to painting his toenails and then fingernails a matching shade of pink. Luckily the nail polish dried quickly so he could begin applying the makeup he'd been working on for two years.

“Okay, Deann,” he smiled as he watched the pretty girl emerging in the mirror.

Deann was his alter ego, the girl he became at every opportunity and he would remain her until late Sunday afternoon. Yes, he'd been making plans since he'd found out that his parents would be away all weekend. This would be her weekend to get out of the house and explore the world.

For two years, ever since he'd turned sixteen, he'd slowly been buying all the things a teenage girl would need, panties, bras, skirts, blouses, shoes, makeup and a ton of accessories. And of course, the breast forms he'd purchased online just three short months ago. He'd been lucky that for all intents and purposes he'd already stopped growing and now stood just a shade over five feet four inches. And along with that, he had held his weight down to just one hundred and fifteen pounds.

Today would be a first for him, taking a walk in public as Deann all the way to the convenience store nearly a half mile away. If everything went well, tomorrow he would go on a shopping trip to the mall.

Now he began becoming Deann. First thing he did was lay on the bed and press hi balls up into his body, then he tucked his dick back before folding the excess skin from his sack over it, creating a crude, but effective looking, pussy. Then came a tight green thong designed to keep everything in place. Once he'd accomplished that, he put on a lacy white bra and slid in his silicone breast forms. He loved the feel and weight of them as they moved with his body. Now he could slip on a pair of nylons and he chose a pair of beige instead of going for the sexier black ones. Rolling them up his smooth legs always felt so wonderful he had to stop and mentally fight the urge to pull his cock out and have a go at it.

A very short pastel blue mini skirt that barely covered the top of his stockings went on, followed by a white satin blouse. Next he stepped into a pair of white sandals with three inch heels. He thought about a pair with five inch heels but decided they were to blatantly sexy for his first time out. A golden chain around his left ankle came next, then three bracelets, followed by two rings, a pair of dangling earrings and a silver cross necklace.

Finally he picked up his purse and made sure his phone, license, keys and money were inside, as well as a tube of lipstick, a compact, and yes, a tampon. He was very glad that he'd spent so much time working on his walk until it had become natural to him. The shortened stride, placement of feet when walking, how to carry his arms and so forth, all added to the illusion of femininity.

“Ready for your public debut, Deann?” Jimmy asked as he took one more look in the mirror.

He opened the door and stepped outside, closing and locking it behind him. Now he was Deann, a pretty girl of eighteen, and had to think of himself as a female in everything that she did the rest of the day.

Glancing about she saw that there was no one moving anywhere on her block, which was a little disappointing but also a relief. Just a few minutes later she was crossing the street and moving into the next block. Each step gave her more confidence and now she was moving along quite nicely. A car passed and honked causing her to look at the driver and wave in response, just like so many girls she'd seen doing. Another block passed by and she felt more natural, and then another and another so that by the time she was at the store she didn't have to think so much about how she was moving and acting.

Inside the store she went to the cooler and chose her favorite soda before moving into the line waiting to check out.

“Man, it's going to be a hot one today,” the man in front of her said.

“Yes, but it's a beautiful day,” Deann replied and gave the man a smile. A bonus! She'd interacted with someone and passed the voice test.

She paid for her soda and walked outside for the return trip but paused for a moment, thinking about her plans. The walk to the store had been too quick, too easy, so she set her sights on going a little farther. There was a park just a few blocks away and she thought that would be nice. Deann took a sip of the cold soda and began walking in that direction.

The freedom she felt being out in public was exhilarating and the slight breeze going up her skit and gently caressing her was wonderful. When she arrived at the intersection across from the park she had to wait for the light to change so she could cross the street protected from the traffic. The light changed and she crossed in front of several cars, all of which had male drivers.

Once in the park she strode to one of the many covered picnic tables and sat to enjoy her new found freedom. She avoided the playground where children were playing opting instead to walk through the beautiful flower garden. On the other side of the garden she saw several boys playing basketball on one of the many fenced in courts and stopped to watch. It was a classic skins against shirts game and she took in the strong, sweaty chests on display. That the skin being shown had so strongly captured her attention caused her to pause and wonder why. She'd seen plenty of guys without shirts in her gym class but had never been as fascinated by them as she was now. Was it because she was dressed as a girl and now thinking more like a girl? Must be.

A shot was blocked and flew over the fence, bounced off the base of a tree and rolled to a stop at her feet.

“Hey, will you pass us the ball back,” one of the boys called to her.

Deann picked up the ball and looked at the tall fence in front of her and then walked it to the opening for the court. One of the skins players met her and took the ball from her.

“Thanks,” he said with a smile and for the first time recognized him as one of the boys from her neighborhood. “Do I know you?”

“Um, I don't think so,” Deann replied as she pretended to think about his question.

“Too bad. I wish I did,” he smiled and returned to his game.

Deann lingered a little longer, pretending to watch the game but actually more interested in just watching the guys. For some reason, probably because of the way she was dressed, Deann felt a slight tingling between her legs and hoped her tucking job earlier was going to keep her in place. Getting an erection wasn't part of her plans and would most certainly expose her as a male in a dress. She decided that it would be best if she walked away from the game before she found herself in a very embarrassing situation.

Tossing her empty soda bottle into the trash can, Deann reluctantly walked away. She stopped on the opposite side of the garden and dug in her purse to find her phone so she could check the time. Shocked at how much time had passed since her journey began, Deann decided to start the walk back to her house.

“Damn,” she thought and smiled, “just when I was starting to enjoy myself.”

The walk back seemed to take a little longer but she didn't mind. In fact, she felt a little disappointed when she crossed onto her own block. As far as she was concerned today had been a total success. She'd gotten out in public, interacted with three people, the female cashier, the man in line, and the guy playing basketball. On top of that she'd been honked at twice.

Finally back inside her house Deann found great pleasure in not having to hurry and change back into her male self but could remain as a girl for the rest of the weekend. She'd been in the house for only a few minutes when there was a knock on the door.

“Yes?” she said as she swing the door open. Suddenly she was face to face with the young man who had been plating basketball.

“I knew I knew you from somewhere,” he said and smiled broadly.

“Uh, no, I'm just visiting my, er, aunt and uncle.”

“Oh. Well is Jimmy here?”

“No, he went somewhere while I was out,” Deann answered bravely.

“That's too bad. Hey, could I get a glass of water?”

“Sure. Come on in,” she said and turned to go to the kitchen. “Have a seat and I'll be right back.”

“Oh, by the way, my name is Jack.”

“Hi Jack, I'm Deann.”

“Deann, huh? Pretty name for a pretty girl.”

“Thanks,” she smiled, accepting the compliment and handing him the glass of ice water.

“Did you follow me all the way from the park just to get a glass of water?”

“No, not really. I just wanted to see where you lived.”

“Whatever for?”

“Something about you made me do it. I mean, I felt a really strong attraction to you back at the court and I just had to meet you.”

“Well, honesty is a virtue,” she replied, smiling cheerfully and blushing just a bit.

“Honesty, huh? Okay, let me be perfectly honest, Jimmy.”

“Oh, you recognized me?”

“I knew you as soon as I saw you. I mean, I've seen you before when you were laying out in your backyard or just out there walking around. My bedroom overlooks your yard. Not only that but I can look right into your bedroom window and I have a few times. I've seen you changing into Deann.”

Her heart was sinking fast. All this time she'd been so careful not to arouse suspicion just to find out that her secret was known to anyone who could see into her yard.

“So what are you going to do, tell everyone about me?”

“If I was going to do that I would have said something back in the park. But I was telling the truth when I said I had a strong attraction to you,” he said. Then he asked, “How girlie do you feel when you get all dressed up?”

“Very. I feel totally like a girl when I dress.”

“Cool,” he said and then sat next to her on the couch. So close that his bare leg was touching her nylon clad leg.

He reached to her face and turned it to face him. “Girlie enough for a kiss?” Jack asked, moving closer and closer.

Deann responded and met him, her lips touching his as she experienced her very first kiss. His tongue entered her mouth and she found herself in heaven.

“I've got a secret to tell you,” Jack said after the kiss.

“You know my secret, so tell me yours.”

“I've always thought you were cute, even before seeing you dressed up. I don't know for a fact, but I think I'm gay. I mean, guys have always turned me on but when I saw you up close, I nearly sprung a boner.”

“Really? That's why I left so quickly. I was afraid I was going to get an erection and then the world would know all about me.”

“I think it would be best if we kept it a secret. You know, just between you and me,” Jack replied with a grin.

“Sounds good to me,” Deann smiled. Without realizing it she had allowed her hand to fall onto the tent he was making in his shorts.

Jack definitely noticed where her hand was and placed his hand on her nylon clad thigh, right at the edge of her skirt.

“You know, Deann, you look really, really hot.”

“Thanks. Um, so you think I would look better with black stockings?”

“Black is sexier, but then I think you'd be sexy in anything you wore, or maybe didn't wear.”

“Didn't wear? You think I should run around naked?”

“Hey, I just said you'd look sexy,” Jack replied and laughed while letting his hand roam a little across her thigh.

Deann liked the way his hand felt on her leg and especially liked the way it made her feel, a sensation she was totally unaccustomed to.

“Um, you know, that really, uh, feels good,” she said, indicating his hand.

“Yes, it really does,” he whispered and moved in to kiss her again.

Deann met him with all the passion she could muster.

Still locked at the lips, Jack took her hand and placed it directly on his aching erection. Deann, feeling his hard cock through his shorts, knew exactly what it was but she was impressed by his size. While she knew she didn't have the biggest dick in the world, she also knew that Jack's was at least three inches longer and half again as thick, maybe more. Very gently, she began caressing him, slowly taking his hardness into her hand.

“Mmm, that feels so good, Deann,” Jack moaned and let his hand ease under her short skirt, slowly creeping up to find her panty covered treasure.

“Ooo, yes, it does,” Deann groaned when his hand slipped under her panties and lightly fondled her own dick. She moved her hand to the snap holding Jack's shorts closed and deftly opened them before lowering the zipper.

“Oh, baby, please kiss my dick,” he groaned as he helped her pull his shorts down, releasing his stiff cock.

Her heart quickened just thinking about doing anything so naughty. Deann may have been totally inexperienced but she wasn't naive. She knew what he wanted and knew this would only b the start of her journey as a woman.

“I, I've never ...”

“Please!”

Deann didn't need him begging her to suck his dick, she already wanted to do exactly that, she was just trying to tell him she was a total novice at such actions and didn't want him to expect her to an expert.

Already his hard cock was rapidly approaching, or was it her that was moving toward him, not that it mattered. At last the head of his cock touched her lips and the proverbial light bulb flashed on and she knew exactly what to do. She would treat his dick the same way she'd like hers treated. After all, if those sensations made her cum, they should do the same with him.

Deann flicked her tongue out and tasted the tiny drop of precum which had formed on him. The sweet and salty taste reminded her of her own, which she loved. Pursing her lips she kissed the head of is dick, and then kissed it again, and again. She traveled his entire length, kissing and licking over and over, lost in her own thoughts.

“Ooo yea, Deann, that feels so good,” Jack moaned. “Don't stop! Aw, damn, your lips are so soft.”

His words encouraged her and she soon parted her lips and took the head of his throbbing cock into her mouth. The feel of his powerful shaft slowly gliding over her lips was the best thing she had ever felt. Deann took more of his dick totally amazed that she was actually taking a cock into her mouth and wanting more. After three inches she pulled back, reveling in the feel of him. Down her head moved once again, taking more of his cock. Up and down, lick the head, playing her tongue on the sensitive area beneath the crown.

“Ooohhh, Deann! Ooo, yea, suck my cock!”

Deann loved what she was doing and gradually picked up more and more speed, her head bobbing up and down, the slurping sounds she made filling her with lust. Faster and faster she moved and then thought about what the end game would be. She had to wonder what it felt like for a dick to cum in her mouth. Would it be like a garden hose turned on? Would he simply spill his hot seed into her? She'd gone this far and she had to know. She had to validate her urge to be a woman and this was a definite step in that direction.

“Oh damn! Oh fuck! Oh, Deann, I'm gonna cum! I'm gonna cum! Ooohhh fuck! Yea! I'm cumming!”

Deann heard his words and did what she could to prepare for his creamy prize. She wanted him to cum in her mouth. She needed this. Then she felt him stiffen and jerk before driving his cock deep into her mouth with a definite frenzy. He bucked and jumped and then it happened. Her mouth quickly filled with spurt after spurt of his cum. She swallowed some of his sperm and held some in her mouth, tasting the muskiness of him. The flavor was stronger than her own, or at least she thought so.

Deann had been so preoccupied with sucking his cock that she hadn't even realized he was jacking her off until she began cumming. Her orgasm happened just a few short seconds before his and she was very well satisfied, swallowing the last of his cum.

Now, her mouth clear of his cum, Deann began licking any trace of his seed off his cock.

“Oh fuck, Deann, that was fantastic!” Jack groaned, his hand still on her dick and coated with her cum.

Deann sat up and smiled happily. Now she really felt like a woman, one that had just pleased her man.

Jack kissed her before she even realized it but she returned his kiss with as much passion as she could.

After breaking the kiss she looked into his eyes and said, “You know, I'm hooked now. I'd like to do this again.”

“You would? Wow, that's so cool! Well, I'll tell you one thing, little lady. Any time you want to suck my dick, I'll be more than happy to let you.”

“You just let me know when, baby, I'm down for it,” Deann laughed.

“Then how about later on tonight? I need to go home and do my chores but after that?”

“Sounds like a good thing to me.”

After Jack left Deann took a shower and then got ready for her lover's return. This time she wore her five inch heels and black stockings because she knew he liked them. Besides, even with the heels on, Jack was still quite a bit taller than her. Tonight she planned to wear her best nightie, stockings and heels. She intended to be ready for him and really wanted him to fuck her mouth. Who knows what else might happen. She'd had a taste of cock and most assuredly wanted more.

As she prepared a light meal Deann thought over what she'd done and still found it hard to believe. Not only had she sucked a cock but she had thoroughly loved it and was even now planning on doing it again. Only one word came to mind and that was cocksucker. She could now call herself a cocksucker and she definitely liked the ring. Sucking cock while being so feminine brought her a little closer to her goal, which was being girlie all the time.

As she ate she considered the other thing, the act of being fucked, something which had only been in her jack off fantasies until now. Could she do something like that? Until a little while ago she hadn't even considered really sucking a cock but she'd accomplished that, and quite easily. But taking a hard dick in her asshole, well, that was another matter entirely.

Jack arrived just a little before nightfall, fresh and clean from a shower after finishing his chores. She opened the door for him, kissed him, and invited him inside and lead him by the hand to her bedroom.

“Damn, you look hot, Deann,” Jack said, removing his shirt as he watched her stretch out on the freshly made bed. In doing so Deann had flashed her bare bottom at him, inviting him.

“Come here, baby, I want to suck your dick,” Deann said, grinning lustily.

“You dress like that and I may want more than a blow job.”

“Oh? Whatever do you mean?”

“I mean, I might just want to fuck you before the night is over.”

“Fuck me? Would you really do that?”

“You better believe it.”

“But I'm a virgin.” Deann replied innocently.

“First time for everything.”

Jacks moved onto the bed with her and began kissing her while his hands roamed all over her nearly nude body.

Deann slid down in the bed and found his hard dick waiting for her. Holding his cock upright she started off by kissing his heavy balls and then licking them while inhaling his manly aroma. She found herself becoming more and more of a slut than the nice wholesome young woman she originally thought she was.

At the moment all she could think about was making him cum in her mouth again, savoring the taste of his cum as it pumped into her. But she also wanted to feel his stiff member sliding in and out of her boy pussy, a thought that had been reserved for her fantasies until a very short time ago, just as cocksucking had been.

“Mmm, yea, Deann, suck my dick.”

Deann did, moving from his balls to his long shaft. She used her entire mouth to make love to his dick, lips to pump up and down, tongue to tease and play, and mouth for him to cum in. Deann knew what she wanted and how to get it.

This time around she purposefully kept her pace slow, working him right to the edge and then slacking off. Again and again she would bring him almost all the way, only to back down and let him cool off for a few seconds. Each time, however, she took a little more hard cock into her mouth, doing whatever she could to deep throat her lover.

“Ahh, fuck, Deann, I'm almost there! Ooo, yea, just a .. just a little bit more! Damn, I need to cum, baby. Ooohhh, damn, suck my cock.”

Jack worked his hand down and found her limp dick, slowly stroking her until he had her nice and hard. He knew the game well enough to understand that you needed to get your partner off as much as you needed to get off yourself.

Twisting and turning on the bed before finally pulling her over his face, Jack wanted to taste her girlie dick.

Deann finally realized what he was doing and moved to straddle his face. When he started sucking her girlie dick she thought she might lose her mind. No one had ever done anything to her and this was driving her wild with passion. Instinctively she knew she wouldn't be able to last as long as Jack so she redoubled her efforts.

“Fuck yea, Deann, make me cum!” Jack groaned, removing her dick from his mouth and stroking it as he spoke.

Deann concentrated on Jack's rigid pole, doing her best to make him cum before she shot her own load. Up and down, up and down, faster and faster Deann's head bobbed. Then she practically screamed even though her mouth was stuffed with his dick. She thought about pulling away from him but it was too late. Her cum was spurting into his awaiting mouth. Only a few seconds later her mouth was getting filled again, his hot seed exploding into her. Again and again his cock fired thick streams of hot cream into her mouth and she was forced to swallow quickly or lose it.

Jack moved Deann around and kissed her deeply, their cum mixing in each others mouth.

“Hold me,” Deann whispered after the kiss.

They lay together, Deann snuggling next to him, feeling like a woman, as she slowly floated back to earth.

When she awoke it was to the sound of Jack snoring lightly. She looked at the clock and saw it was after midnight.

“Jack? Jack, wake up! It's late.”

“Huh? What? Damn, it's after midnight!”

“Do you need to go home?” Deann asked as she sat on the side of her bed and turned on a lamp.

“Nah. I told my folks I was coming over here and we were going to play video games all night long,” he replied and slipped his arm around her waist as he scooted next to her.

“I wish you had told me. I would have let you sleep.”

“But now we're both awake,” he laughed and hugged her tightly and then whispered in her ear, “Besides, I want to do more. Have you ever thought about, uh, you know.”

“Not until today,” she answered and saw his dick beginning to come alive.

“What did you think about it?”

Smiling, Deann shyly replied, “I think I'd like you to, um, be my first. Will you be gentle?”

“You know I will,” he smiled and kissed her neck.

“Then what do you say? Would you like to make me pregnant? Or at least give it a try?”

“Damn straight I would, baby,” he smiled.

An hour later, with his cum oozing slowly out of her just fucked asshole, Deann drifted off to sleep in the arms of her new boyfriend. Yes, it had hurt a lot when he first entered her but the end result was well worth it. He had pumped her ass pussy forever, making her own cock spill another load of cum before finally sending his hot sperm deep into her, satisfying her more completely than she had ever imagined. She soon discovered what she'd overheard other girls saying about sleeping in the wet spot, and she liked it. Deann may not have been born a girl but she was determined to make up for that slight mistake.

Jack, holding her next to him while thinking that he had the absolute best of both worlds with Deann. He preferred to be with guys and Deann fit that bill. She loved to suck cock and it also seems that she liked taking it in the ass, again fitting nicely into his way of thinking. Now he had a girlfriend with a dick that could easily pass in public and be a total whore in bed. What else could he possibly ask for? His final thoughts before drifting to sleep were, wouldn't it be cool if she could get pregnant?