Thirty Days to Jenny Ch. 2

day eleven

Well, Alison, thought, Jeff had been listening to the 30 Days to Jenny tape for ten days already and the changes in his character were dramatic. He was sweeter, more helpful around the apartment, and even more satisfying in bed. He'd started a diet, been exercising, and had taken a renewed interest in his appearance. If the changes stopped there, Alison would have to consider her money well-spent. But she found that the more her boyfriend changed, the more she wanted him to change further. She hadn't even considered it as a possibility, but Alison truly found herself enjoying what was happening to Jeff. Maybe, she thought, it was the frustrated mothering instinct inside her. Whatever it was, Alison took a real pleasure--even pride--in being a part of her boyfriend's transformation into Jenny.

She watched from the kitchen as Jeff vacuumed the living room, his smooth legs and pert butt looking adorable in a pair of her red silk running shorts. The little kerchief he'd tied around his short spiky hair was totally unnecessary, but totally cute.

Alison had pushed things a little too far the day before, bringing up that bit about Rafe, asking Jeff if he didn't think his hunky friend from the video store was cute. For a while, Alison thought she'd blown the whole thing when she saw how upset Jeff had gotten. So she'd backed off today and decided to just see what developed.

She considered it a good sign that Jeff hadn't removed the purple-glitter polish she put on his toes while he slept. In fact, he had slipped on her pair of lavender platform flip-flops as if he were almost showing off his pretty toes. And that t-shirt, he was wearing….oh, it was still his alright, but it was one of those that had faded and shrunk in the wash. Alison was going to have Jeff use it as a rag to polish the furniture, but seeing it on him, she changed her mind. Had he chosen it on purpose? Was he even aware how when he moved it showed a glimpse of his belly-button?

He had the earphones on, the walkman clipped to his waistband, and he was listening to the tape. Supposedly, he was listening to drown out the drone of the vacuum. Alison wondered just what scrumptious new thoughts were being programmed into her boyfriend's rapidly sissfying brain.

Alison knew well enough not to ask. Not today anyway. Later, when Rafe called from the videostore to set up another running date for the next morning, (was it only Alison's imagination, or was Rafe calling a lot lately?), she made a big show of leaving the room to give Jeff his privacy. She listened from the next room, of course, and how cute her little sissy sounded, all flighty and giggly, like a schoolgirl, as he talked to his boyfriend.

Not long, Alison thought, just a little wistfully, perhaps. Not long before that happens, too.

day twelve

"What's in all the boxes anyway?" Jeff asked. He was following Alison down the stairs to the storage room, carrying a box of his flannel shirts.

"Just some winter stuff," Alison said. "I figured we'd make some room in the closets for new clothes."

Jeff made an innocent joke about Alison's ever-expanding wardrobe. Alison smiled wryly. What she didn't tell him was that all of the boxes were filled with his clothes and the only wardrobe that was going to be expanded was his.

"Watch your step in those shoes," she called back over her shoulder.

Alison's boyfriend seemed to have appropriated her lavender platform flip-flops. Ever since she had painted his toenails, Jeff seemed to love going barefoot. He claimed that his own shoes were just too uncomfortable and his sweatsocks too hot. But Allison concluded that he just liked showing off his pretty toes.

He was wearing another pair of Alison's shorts, this time not merely running shorts, but genuine girl shorts. They were culottes, almost, and what was perhaps even more obvious, they were an unmistakable femme shade of pastel pink. The shirt he wore once again showed off his belly, only this time it showed off more, because it wasn't merely a shirt that had shrunken, but one that Jeff had cut off himself.

If he was at all concerned about being spotted in the hall outfitted like this, he didn't show it. And, in fact, they did run across someone: the old lady who lived in the apartment upstairs. She took one look at Jeff and looked over at Alison. For a moment, Alison thought the old lady was going to say something that would spoil everything. But she just nodded at Jeff, wished him a good morning, and turned to Alison again with a wise, pleased smile as if to say she understood everything.

When they had carried all of the boxes down to storage, Alison asked Jeff if he would carry his weight set down as well.

"I'm constantly tripping over it," she said. "Besides, you haven't lifted those things in months."

"Don't I know it," Jeff rolled his eyes. "All they do is get in the way when I vacuum."

He walked over to the barbell and sort of casually tried to lift it from the floor. To his surprise, the barbell didn't budge.

"Whoa. I guess I put on more weight than I thought."

Alison watched fascinated as Jeff readjusted his grip and stance and tried to lift the barbell again, but with no more success than before.

"Hmm," he said, standing upright, a fingertip in his mouth. "Who was lifting these things anyway? Arnold Schwartzenegger?"

"You used to honey," Alison couldn't resist saying.

"Moi?" Jeff laughed, remembering the one word of French that Alison had him memorize, "Don't be silly!"
"Too bad Rafe isn't here," Alison ventured. "I bet he could lift it up easily. He looks pretty well-built."

She held her breath waiting for Jeff's response. But her boyfriend seemed to accept the comment at face-value.

"Yes. He's really strong. I get him to lift heavy boxes for me at work all the time. Uhh, where's a man when you need one?"

Jeff laughed, and Alison tried to pretend she didn't feel like fainting. Her boyfriend was continuing to remove weight plates from the barbell. Alison knew that Jeff hadn't really grown that much weaker; at least, he hadn't physically lost strength. But the tape had prepared him mentally for the time when his pretty feminized body would hardly be capable of lifting anything much heavier than cloth-covered lavender handweights. His femmy toes were scrunched inside the platform flip-flops as he strained to lift the barbell, barely getting it up to his thighs. Alison managed to collect herself enough to ask, "How much weight is on there now, honey?"

"Oh…" Jeff looked from side to side, furrowing his brow to make the mental calculation. "It looks like almost thirty pounds!"

Alison got up from the couch where she'd been watching this amazing episode in the ongoing process of her boyfriend's total emasculation. "Oh that's much to heavy," she said, easily taking up most of the weight herself. "Let me help you sweetie."

Jeff gave her a grateful look. "Unnnhhh…thanks!…its sooo heavy!"

And so it was that, with Jeff taking short, little stumbling steps behind her in his platform sandals, they carried the weight set down along with his other male stuff, never to be seen again.

day thirteen

Getting Jeff to the salon did not turn out to be nearly as difficult as Alison would have thought. She simply told him that it was right next to the bank where she had to go anyway and since she knew the owner it was the only place she could get an appointment. Besides, she argued, he couldn't very well get his arms and eyebrows waxed at the corner barber could he?

"But isn't that place just for girls?" Jeff asked.

"No, honey. It's not just a woman's salon." That wasn't strictly true, Alison thought, but soon it would be irrelevant in Jeff's case. "Men go there, too."

Her boyfriend was sitting in the chair now, wearing a pair of her purple sweatpants and a salon cape, little strips of foil in his hair. Janine, the manicurist, had finished working on his cuticles and was now applying clear polish to his nails. They had decided not to bleach his hair, but to give him frosted highlights instead. His toes, which Janine had already freshly polished in electric pink, were drying , separated by little rubber toe separaters. To Alison's surprise, Jeff hadn't balked at all about taking off his sneakers and showing his already feminized feet. The little cutie really did seem quite proud of his painted toes and enjoyed all the compliments he got from the girls in the salon, who seemed to get a great kick out of Alison's sissy-in-the-making.

Jeff yelped in surprise when the first of the wax was yanked from his arm and his eyes moistened. "That hurt," he said, with a tricked, disappointed-looking pout.

"I want you to get used to it," Allison explained. "From now on this is the way you're going to keep yourself smooth. It's much more efficient than shaving…and lasts far longer, too."

"Ow!"

"Maybe, eventually, it will be unnecessary when we start giving you…"

"Giving me, what…" Jeff started hopefully, and then "Ow!"

"Never mind," Alison said quickly. "Put your headphones on sweetie. Concentrate on the music." She paused, enjoying the wickedly delicious irony. "It's like self-hypnosis."

Jeff eagerly slipped the headphones on with the help of another one of the girls, careful not to disturb his hair. He still flinched a bit when Sandy pulled the strips off, but, all in all, he seemed to tolerate the waxing pretty well. Alison noted how thin and girlish Jeff's arms looked once they'd been completely depilated and how soft and open his face looked once his eyebrows were waxed and shaped.

"Can he hear us?" Julia, the salon owner asked, turning to Alison. "I can't tell."

"No," Alison said, smiling down at Jeff, who smiled up at her, somewhat absently. "He's pretty much in a world of his own when he listens to the tape."

"Amazing," Julia said, "simply amazing. I'd love to make him up. Give him the works. With some eyeliner those eyes would be breathtaking. He has nice lips, too." She touched his face. "Good bone structure."

"I don't think he's ready for that yet. But maybe in a week or so. This is only day thirteen."

"God, he changed that much in less than two weeks?" Casey, a bright, curly-headed blonde paralegal said. "I can't believe it."

"You got that tape off the internet?" asked Diane, who was waiting to have her hair colored.

"Yes, I couldn't believe it would work myself," Alison admitted. "But I'm a believer now!"

"Is he really wearing panties?" Janine asked.

"Yes," Alison said, a black lace thong with purple ribbon.

"Gosh," Janine said softly, "that's really sweet."

"He sure is cute," Danielle said, looking down at Jeff, who seemed to be dozing. She was a senior VP at a local software company. She laughed. "I wonder if that tape would work on my husband Paul?"

"Yeah, I agree he's cute," said Sharon, who was in her early forties and married to a successful pediatrician. "I'm just not sure I'd want my husband to be so femmy. I like men, you know?"

"No," Danielle said. "I wouldn't want Paul in girl clothes."

Janine looked up from where she was still working on Jeff's nails. "I like pretty boys, but I'm with Danny and Sharon. I like my Ben 100% guy. Hairy, muscled, yum!"

"Me too," Casey said. "I wear the panties thank you. I don't want some guy who's trying to be cuter than me. I'm not lesbo, and if I were, I'd want a real girl."

"That's true," Julia said. "I feel the same way." She turned to Alison again. "Does he even perform anymore? Like a man, I mean."

Alison laughed. "He never really performed like a man, I'm afraid, the poor thing. But he's actually become very good in bed. Much better than before. He's sweet, and docile, and very attentive to my needs. But you're right, I'm not a lesbian and I do like a man in bed. Eventually, I'm going to want a real guy."

"Does he know?" Julia asked. "I mean how's he going to take it?"

"He'll be…otherwise occupied, I suspect."

"You mean…" Casey and Danielle looked at each other. "A guy?" They said together.

Alison nodded. "He's tending that way."

The girls in the salon greeted the news with clapping and laughter.

"Is he gay?" Diane asked.

"He wouldn't say so," Alison said. "He'd deny it up and down. And he got really upset when I sort of implied it a couple of days ago. Fact is, I wasn't even so sure at first. But well," she nodded towards her boyfriend, his slender smooth body in the salon chair, finger and toenails drying, hair in foil. "Just look at him. Would any real guy let this happen? Obviously on some level, he wants this. I'm just helping bring it out of him."

"Do you have anyone in mind?"

"There's a guy at the video store he's always talking about. He has a crush on him; it's actually quite adorable."

"Rafe?" Janine said.

"Oh god, he's such a doll," Casey chimed in. "If I weren't married I'd be jealous. Damn, I am married and I'm jealous."

"I bring my videotapes back one at a time and pay the fine just to talk to him," Danielle said.

"Oh Danielle!" Janine said.

"Well I do!"

"Do you think he'll go for our little sissy doll here?" Julia asked.

"I'm hoping. Maybe with all you guy's helping."

"Count me in," Danielle said. "If I can't have him I don't want any other girl to have him."

"Except one of our own creation," Julia added. "A girl who isn't a girl at all."

"Yes!" the other girls said in unison.

On the way home, Jeff sat in the passenger seat with his new highlight hairdo, spiky and gelled, and stared at his manicured hands.

"Like them baby?"

"Yes," he said, smiling happily. "They're so…glisteny."

Alison laughed. She thought it was cute when he made up words to describe his new femme feelings. She saw his newly shaped eyebrows come together, and knew he was trying to figure something out on his own again.

"What's the matter sweetie?"

"I just noticed. I think they made a mistake. I thought it was clear polish, but it looks like it's a little bit pink."

"Oh that's just the skin under your nails shining through," Alison said.

"Really?" He looked closely at his pale, girly hands as if they posed some kind of puzzle.

"Sure," Alison said. "They're pretty, aren't they?"

"Oh yes!" Jeff said. He looked over at Alison with a serious look on his face. "I really liked the salon. Do you think I could go back?"

This time it was Alison's turn to say, "Oh yes!"

And then, quite out of the blue, Jeff got all excited and said, "I wonder what Rafe will think of my new look. I can hardly wait until he sees me!"

day fourteen

Alison lay on her side next to Jeff, touching her vibrator to his sensitive nipples. Her boyfriend gave a cute little shudder. He was holding up the blue satin camisole top he was wearing, still more or less convinced it was a kind of tank top.

"Feel good honey?"

"Mmm, yes."

She hardly needed to ask. A tell-tale little wet spot was forming on Jeff's matching tap pants, not to mention the way his rising erection was pushing them forward. She took the vibrator from his boy-tits and placed it over his crotch until his cock strained inside the silky shorts. Jeff gasped and bent his smooth legs at the knees. The wet spot widened, his cock ratcheted up a few degrees to maximum, and Alison pulled the vibrator away, leaving him moaning and thrusting his hips in the air.

"Not yet sweetie," she cooed. She placed the vibrator over his tummy, already noticeably flat from his strict new diet, and let the sensations indirectly bathe his groin. It was clear to Alison by how quickly Jeff had fallen under the suggestion of the tape that he was far more girl than she—or for that matter, he—would ever have suspected. It was also clear that her boyfriend must at the very least have very strong latent homosexual desires. But remembering his strong reaction of a few days before, Alison decided to approach Jeff's sexual re-orientation from a slightly more subtle direction.

That morning, for instance, while Jeff stood at the sink rinsing dishes before loading the dishwasher, Alison looked up from her paper and told him for the first time about Kurt, who worked in the promotions department of her firm. Carefully, she told her boyfriend how funny and intelligent Kurt was and how much she liked working with him on their latest project. Jeff had just continued loading the dishwasher, humming a little, the tune from the tape, of course, and Alison went a little further, telling Jeff that she'd probably have to start working a little late at the office with Kurt.

"He's so ambitious," Alison continued, warming up to the subject. "Everyone says he's going to be the next head of publicity."

Jeff carried the coffee pot to the table and refilled Alison's cup. Then he sat down opposite her, bare legs crossed under her pink terrycloth robe, his hands around a mug of Super-Slimming diet tea.

"Wow," he said. "He sounds perfectly dreamy. What's he look like?"

Alison smiled fondly at her boyfriend. He hadn't been the least jealous. But then he didn't understand her intentions. By the time he did, she thought, he'd share them. She alternated the vibrator now between Jeff's nipples and the base of his cock, keeping her boyfriend on the edge of what she could tell was going to be a monstrous orgasm. Jeff was making those adorable whimpering noises he'd taken to making when he had to cum and Alison knew that now was the time to put the first phase of her new plan into action.

"Pull your pants down honey," she said, and watched as Jeff shimmied the silky tap pants down, freeing his pale, smooth erection.

"All the way off," she added.

Jeff bent his legs, lifting them together, and slipped the shorts over his pretty feet.

"Keep your legs up. Spread them a little wider. That's it."

He looked quite sweet like that, Alison decided, and very femmy, the position exposing the little pink rose of his bottom. It was there that she placed the tip of the vibrator.

"Ooh," Jeff said, stiffening. "Ooh."

"It's okay dear. Just relax. Doesn't that feel good?"

She could see how the vibrations were trembling along her boyfriend's sensitive perineum and making his tight little balls tremble. His pretty cock twitched and its pink head was all shiny and sticky-looking. She touched the shaft lightly and felt the tremor of the vibrator there, too.

Jeff was touching his hard little nipples now, rubbing and squeezing them with one hand as the other reached naturally for his achingly erect penis. Alison stopped his hand.

"No honey," she said gently, but firmly. "I want you to come without that."

It took him awhile to figure it out, but her boyfriend eventually worked himself into an orgasmic rhythm. With both hands on his breasts, Jeff moved his body in a kind of humping motion, pressing himself down on the vibrator that Alison held to his puckered buttonhole. His cock was leaking and slick, wet with his juices, and Alison softly encouraged him. She wants to push the vibrator inside him, but decided that would probably only scare him at this point. Enough, she decided, for now, that he learn to associate anal stimulation directly with his orgasm.

He tucked his knees up tighter and moaned and panted. Alison saw that he'd hit upon the secret, opening and squeezing shut the cute little muscles around his anus as if milking the cock that wasn't there…yet.

Seconds later, Jeff went into his orgasm, his hot, humping body ejecting little jets of white sissycum onto his smooth, fluttering tummy.

"That's it honey, that's it!" Alison congratulated him, and herself. Dammit, Rafe, she thought, looking down at her sexy little sheboy-in-training, you're going to be one lucky bastard.

day fifteen

Halfway to Jenny. Alison no longer had any doubts whatsoever. In fifteen more days, she was certain that her boyfriend was going to be, for all practical purposes, a girl. She knew it the moment she walked into the bedroom and caught him wearing one of her wrap-around miniskirts and a pair of her high-heel red Bongo mules. He had managed to fit into one of her blouses, but unable to button it, he'd fashioned a kind of halter top by tying the shirt tails together. He was walking in front of the mirror and looking behind him to check how the skirt made his bottom look.