Tricia's Summer Project

Before he could react further, the warmth of her body was upon him, her fingers intertwined with his, her breath against his neck as she told him to relax, that it would feel good and he'd promised, after all, to do as asked and he'd said he wanted to learn.

He was about to ask if he could cum when she pulled his head to the side and her lips found his. The kiss silenced him and she whispered for him to relax then pushed his head down into the pillow so his ass rose in invitation, telling him to hold them there. With these words she slid a lubricated finger inside him which loosened and relaxed quicker than expected, quickly adding a second, pumping it in and out as he felt a pressure building as if he was going to somehow cum inside his body, warm ripples passing through his abdomen and down to his toes which, she noticed, were tightly curled up around the straps of the heels. Right at the point he didn't think he could take it anymore, she removed her fingers and replaced them with the slick head of the dildo, which she rubbed against his opening.

"Exhale," she said and as he did he relaxed and the head popped inside. For a couple seconds it stung, and then it didn't and then it felt amazing. Was that wrong?

Tricia read his thoughts. "It's okay. You're doing great. And now you've got your first cock in your pussy. Congratulations."

Tricia could feel him giving himself to her, with each thrust a little resistance melted away as he learned to accept it inside her. Eventually she withdrew, letting him collapse into the sheets while she removed the dildo from the harness, and gathered the other two from the bed stand. As he lay motionless, she worked the eight inch one inside him, again he resisted, then pushed back hard against her. This one was longer and thicker and she watched him stretch and buck against it until, as with the first, he'd taken its entire length.

In a matter-of-fact assessment, she told him she'd never seen someone take so much cock the first time. Alex whimpered in response. Writhed a little. Reached back with both hands to pull at his soft cheeks. The site of his hands rubbing his round, and rather cute, butt was almost too much for Tricia.

"More?"

He whimpered a "Yes."

Onto the harness went the largest one. Heavy and much too thick for her to get her fingers all the way around, she told him she called this one the "Slut-maker."

"You'll be tender after, but wake up aching for it. They all do."

Like the slut he was becoming, Alex pushed his ass up in the air even higher and she slid the head inside—he cried out. The thing was truly huge. She'd intended to relax him with a little teasing and not put too much in him, and was about to pull the head out to let him catch his breath but he arched his back, burying the full length of the shaft inside him and grinding the base of the dildo in the harness against her clit and she lost control, pushing into him as deep as she could, the weight of her body on top of him and she came quick and hard, her already wet thighs getting so slick she wondered if it might be coating the shaft of the cock as she drove it into him, not stopping, and he moaned in response and began a deep gutteral moan that turned into something primal and his legs began to shake as they bucked against one another, an intense spasm of pleasure passed through the core of his body. Still she didn't stop and Alex was surprised and almost a little frightened to feel it happening again, then again, each time causing him to moan in a way he had no control over, he'd never felt more vulnerable and was powerless to do anything but let her take him.

Finally sated, Tricia slowed down, wrapping him in her arms and kissing him while he lay still underneath her. She kissed his closed eyes noticing a little wetness around one of the lids and again she told him he'd done great and she knew the first time was intense. He opened his eyes.

"Does this mean I'm...?"

"It means you're learning what feels good and you're open."

Alex had no response to this other than that he didn't care what he was, he just knew he wanted more.

"I guess the real question is what do you think you are?"

Alex surprised her by kissing her hard, then moving to her ear where he whispered that he was her slut. After another long kiss, Tricia slowly extricated herself and lay beside him. Instinctively, he rolled against her and wrapped an arm across her waist. Between them, on the sheets, she could see a clear wetness the size of a small dinner plate—she'd unintentionally milked him, rubbing his prostate so his seminal fluid leaked out of his diminished penis without the full sensation and release of orgasm. The effect sometimes was to make him more desperate to cum, but also more difficult as most of what constituted cum was seminal fluid so his tank was effectively close to empty. She'd read about milking men when keeping them in chastity, it provided them with some release while also keeping them in need and focused on behaving as desired. If done long enough, a week or two, or three, a man who was then allowed to cum would cum hard, shooting a substance thicker and whiter than normal. But that was with a man, to let a sissy cum like that seemed like a silly idea.

For Alex's part, he was feeling a little tender but also a little silly and he giggled for no good reason other than the endorphin rush. The laugh and watching him kiss her, his mouth only inches from the dildo she'd just used on him, reminded her of her ultimate goals for Alex, the thought of which caused her thighs to dampen again.

"I was going to wait to teach you this, but I don't want to."

"Teach me what?" Then he saw her other hand grasping the shaft of her dildo and pointing it toward his mouth. He eyed it uncertainly. She placed one hand around her cock, the other on the back of his head. Almost every woman she knew had, at some point, had her head pushed down onto a man's cock and Alex might as well understand what that was like. He opened his mouth and within seconds she'd pumped the head inside him causing his eyes to water and for him to gag, the sound of which made her push her clit against the base of the dildo. The head was impossibly thick and his eyes filled with desperation as she whispered to herself as much as Alex, telling him to suck that cock, and that he was going to make such a pretty bitch before cumming again, and so hard she laughed a little at herself.

She put him on his back, legs up around his shoulders and spread wide. It was a highly submissive position not to mention more than a little slutty and she told him so as the cock slid inside him, stretching him further, and more easily this time, and as she did so she began rubbing a thumb on his tiny boy-clit until it was plump and stiff, her hand stroking in time with her pumping of his ass until finally she allowed him to cum—a thin white line puddling in his navel. She ran a finger through the cum and placed it on his tongue, repeating this until he was clean and only then did she withdraw. His eyes had a faraway look to them and she held him to her chest as they both fell asleep.

Alex woke up with his head resting against a breast and for a moment didn't know where he was then it came back to him, aided in no small part by some parts of his anatomy feeling a little worked over. A wave of shyness washed over him, looking up to see Tricia awake and smiling at him it dissipated somewhat but not entirely. Again, she read his thoughts and without saying anything she wrapped her arms around him and rolled on top of him, her body giving him immediate amnesia as to whatever it was that had made him shy, then he felt himself stiffen, such as it was.

"So tiny down there. I can barely feel you."

"I'm sorry..."

"No, it's the way I want it. It suits you. Doesn't it?"

It did. From somewhere south of her cleavage, Alex announced that he'd like to stay right where he was and not go anywhere.

"Ever?"

"Yes. Cancel everything. Tell the post office to stop delivering mail. I'll be here until further notice."

"We can't do that."

"I know. Jobs, life, blah blah blah."

"Actually I meant because we have to get up and go shopping."

Alex was showered and dressed in ten minutes flat.

They were almost ready to go except Alex hadn't brought a change of clothes, but the ones he'd worn weren't in bad shape so he wasn't going to worry about it until Tricia mentioned it.

"Sorry, is that gross?"

"Not at all, but clean clothes feel good after a shower, underwear at least. I can loan you some?"

"Umm..."

"Don't be silly, hold on, I'm sure I have something in your size." She rummaged through a drawer, lying and telling him she had some panties from when she was a little smaller, pulling out the pair of white bikini size sevens she'd bought the day before for this very reason, quickly pulling off the tag before Alex noticed.

Alex flushed and again she kissed him, and with her free hand helped him step into the panties. They were a stretchy nylon that drew a nice outline around what remained of his genitals.

"Hold on. Let's add this." From yet another drawer she pulled a long, slim plug about an inch wide with a flared base, it only took Alex a second to realize its use. Without being told he bent over the bed. Tenderly, she pulled down his panties, generously coated the plug with lubricant and slid it in but when she let go he couldn't keep it in place.

"Looks like my cute little girl's all stretched out."

Alex gasped at the words and she saw his clit poke against his panties.

A second plug, this one two inches wide at its widest fit snugly without any problem, after she pulled his panties up it was invisible. She kissed him again and he pulled on his jeans. She was both amazed and pleased by the ease with which he'd accepted her requests.

In the driveway, she put his leg on his thigh, "Let's chat for a second."

"Yeah, that would be a good idea."

With the occasional neighbor driving by on their way to work, Tricia explained to Alex that he'd done wonderfully so far but she wanted to be absolutely clear and to make sure he was as excited about it as she was and there was something she really wanted: for him to live with her, for one month, as a woman.

"We can start now, or whenever you're comfortable."

"But how...?"

"You can still work because your job only requires you to be online and not go into an office, right?"

This was true.

"And you'd like to learn what this is all about, yes?"

"I think so. Yes."

"Well, what I want is to transform you into the hottest, most outrageous male fantasy I can come up with." She watched him flush again, both of them knowing this was what he desired.

"Male...?"

"Yes, the stereotype, you know? Big hair, big boobs impossibly tiny waist, round butt. Barbie doesn't have much of a butt so we'll do better than her. Wear heels all the time. Lots of cleavage, heavy makeup and jewelry."

"I'd look ridiculous."

"You won't, I know a thing or two about makeup, among other things."

"Yes you do."

"It would be a gift and you're the first person I've met who seems brave enough to consider it." Tricia knew she was laying it on a little thick, but she meant it.

"I can't believe I'm saying this but — okay."

Tricia told him that was excellent, but it meant she had to make a quick call and verify an appointment.

"Where are we going?"

"Let's just say I was banking on you saying yes and planned accordingly."

Salon X's sign was as plain as one could imagine—white letters on a black background and unlike every other store in the shopping center, it had windows so heavily tinted no passersby could see inside, but once inside Alex saw nothing but shades of pink like a typical lingerie store, but with relatively little stock. It looked like what it was, a front for something else. That something else lay beyond a wide, dimly lit portal through the rear wall, though which they passed.

At the front desk, Tricia spoke to a young woman with straight black hair and an apparent addiction to eye makeup and breasts large enough to rest on her desk and next to the fashion magazine she was reading. Alex couldn't hear the conversation but the woman's demeanor went from blandly professional to a level of excitement Alex found worrisome. She spoke into an intercom and from the back emerged a woman not much smaller than Tricia in a loose-fitting gray outfit and spiky blue hair and who with business-like efficiency told the disappointed receptionist that no, she could not come and watch a Full Service treatment, introduced herself as Diane and said Alex and Tricia should follow her.

Alex soon found himself seated then laying upon a massage table sipping warm tea that had a much more soothing effect than seemed normal with the result that he soon began taking instructions without any question. The two women helped him out of his clothes, Diane complimenting him on his panties but saying they needed to go to and with Tricia watching she sifted a little white powder on his legs then dipped a flat wooden spatula into a large vat of hot wax.

"Uh oh," said Alex.

"No one said being a woman's easy." Diane smiled in a way that made Alex think she might be enjoying this a bit too much.

What followed was thirty fairly uncomfortable minutes, at the end of which Alex looked pink and utterly smooth; she'd not commented on his diminished cock, and had Tricia help wax his "boi pussy" as they called it after removing, then replacing, the plug.

"So she'll still have to shave and wax?" asked Tricia.

"Yes, but this should last a couple weeks, at a minimum, maybe as long as four."

"Oh good."

Dimly, Alex was aware things were moving quite fast, but he wasn't sure how to feel about it because he was too busy being first slipped into his panties and a waist cincher which Diane advised as preferable so they could leave it fairly loose so he could get used to it while they worked, later tightening it as necessary.

Alex placed one hand over his cock—naked in front of Tricia was one thing but in nothing but this was getting to be a bit much.

Diane laughed and apologized for forgetting but instead of handing him his clothes, stood him up, and from a drawer in the massage table removed what looked like a thong matching his light skin tone and in the same businesslike manner with which she'd removed all of his body hair she told him to step into it, removed the plug and grasped his cock, tucking it neatly into a space in the thong shaped to fit the shaft and pulled the soft skin-like material of the panties snug and only then did he realize that not only did he look completely flat, he now appeared to have a completely realistic and highly detail set of rather plump lips between his legs. His panties covered the lines where the thong touched his skin and through its sheer material no one would doubt what they saw. He looked at Tricia who smiled innocently.

"I told you you'd have all the pussy you want."

"All better?" asked Diane.

Alex was rendered quite speechless so they sat him down and went to work, the tea still had him quite relaxed but a sharp pop of pain momentarily brought Alex back to reality as they pierced his ears with two four-inch gold hoops. His navel received a silver hoop from which dangled a thin one-inch chain clipped to a tiny, red heart pendant. With what Diane described as dissolvable ink, on his lower back she added a large tribal tattoo with a thin black line that disappeared between his cheeks.

Periodically, they paused to massage a thick cream into his skin that helped calm his tender skin and almost instantly made it softer than it had ever been. The waxing of his eyebrows caught his attention, as did a tiny needle going into both his bottom and top lips which almost instantly felt as if they'd been stung by something, plumper.

Tricia, who now sat in a chair to let Diane work, smiled throughout the entire process—her expression and the sight of her nipples pressing through her blouse told him how she thought things were going. Depending on where she looked, she either saw a man or a woman. His face, shaved smooth, but otherwise untouched was decidedly male although his features weren't particularly heavy, makeup coming soon enough. His hands were a bit big but his fingers long and thin and the nails were almost too sexy for her to stand. Then there was his pussy, staring right at her. The rest of him looked male, if soft and smoother than most.

"So what do you do about the adam's apple? Scarf?"

"Where is my head today? You can use a scarf but we like these." She clipped a thick lace black choker around his neck, Alex feeling something metallic pressing against his larynx.

"Say something."

"What should—" he stopped, his voice had risen an octave or two with a raspy, breathy edge to it. "What...?" He touched his neck.

"Oh that's fun," said Tricia.

"There's a little knob in the back you can turn to adjust it as appropriate." To demonstrate, she turned it several clicks until Alex's voice sounded squeaky and a little ditzy. Both of the women laughed and Diane adjusted it downward a few clicks.

"Did you want us to help with makeup?"

"No, I can do the rest myself."

"Great, I'll leave the two of you alone. I think we showed you where everything was before. Take as much time as you need, we don't need the room for another couple of hours."

"For another full service?"

"Booked up solid all week. Ex-Marine coming in after you."

"Oh wow."

"Yeah, wife got tired of him cleaning his guns at the kitchen counter."

"Gross but...he's going along with it, or do you know?"

"She's been giving him our ultra-feminizing tea, Persuasion, for a week, told him it had more caffeine in it than coffee."

"It is strong. Is she going to keep him on it?"

"Eventually it doesn't effect you as much so eventually no but I've never had a client who didn't enjoy all this. Most of those guys are overcompensating for something anyway."

"I'm sure. Do you have...?"

"A 'pretty girl?' That's what we call them around here, and yes, you met her out front."

"Who, the girl at the desk?"

"That was my Randy. Had a landscaping business. Thought NFL Network was more important than our anniversary."

"I'm sorry."

"Don't be, Tiff's lovely now and we talked it all out. We got a little carried away with the boobs."

"Easy to do, I imagine."

"It is. So what about her?" Diane nodded in Alex's direction. "What did you use to help her open up to the idea? Persuasion or...?"

"Nope, nothing. The Acceptance you gave her's the first femme tea she's had." Tricia didn't want to get into her gift, some questions were best left with half-answers.

"Really?" To Alex: "Well aren't you sweet?"

"Last night was her first time."

"First time like...? Or first first?"

"First first."

"No."

"Yes."

"She's pretty brave. You just asked?"

"She is, and these helped." Tricia glanced at her boobs.

"They always do. You didn't have those done here did you?"

"No, they're all me."

"If more women looked like you we'd be out of business."

"Thank you."

"I had this work done here. Was a size 10 when we opened."

"No kidding? I would have never guessed."

"That's the idea isn't it?"

"Yes it is!"

They moved Alex into a salon chair where Tricia asked him how he felt.

"Honestly, I don't know...I..." He looked at his nails. "I think I feel sexy. Can I look in the mirror?"

"Not yet, but soon." Tricia opened a door next to her chair and flipped on the light switch to reveal two rows of clothes marked with sizes and running thirty feet deep. "I bet we can find something here." While Tricia sorted through the closet, Alex flipped through a thick binder provided by the salon and aimed specifically at men such as himself. Titled "The Pretty Girl Manual" it offered advice on clothes and hairstyles and picking colors and maintaining an overall feminine appearance, Alex seeking out an innocuous titled chapter called "Staying Ready" which explained how girls like him had different needs in terms of keeping their "pussies" clean and ready.