Thirty Days to Jenny Ch. 2

"Yes," Jeff gushed. "They called me a sissy and a pansy and even a cocksucker. Wasn't that sweet?"

Alison smiled. The tape helped prepare Jeff to take the names as compliments. It was merciful, really; he was going to hear a lot of comments like that from now on. Better that he should take pride in them and consider them terms of compliment and endearment.

She pulled the vibrator away from his bottom and Jeff relaxed the provocative pre-orgasmic arch out of his spine. He moaned and his prick leaked more juice. Alison was training him to keep going for forty minutes of more or less direct stimulation. Why, she asked herself, at one point. And the answer was relatively simple: to see if she could. Jeff was her sissy and she took a certain pride in making him as perfect as possible.

"I want to be the perfect sissy," Jeff blurted out one day, apropos of nothing. "I really do. I really do. Do you think I can?" he asked her.

"Oh yes honey, I do. I really do. Would you like me to help you?"

"Oh gosh. Would you?"

"Of course darling. If that's what you want."

Jeff had folded his hands together and made a cute little pleading face. "I do. Oh thank you thank you . I love you!" he squealed, and actually clapped his hands, one of the many ultra femme gestures he'd been exhibiting lately. He threw his soft white arms around her, stood on tiptoes as she was in heels, and kissed her.

"I love you too," Alison said. And she was surprised herself at just how much she meant it.

She waited until Jeff had calmed down a little, until he was merely panting and making little whimpering, begging noises, before placing the vibrator against his bottom again. He was becoming quite adept at coming without a hand on his cock. With the help of the tape, Alison was also training him to control his orgasmic release so that he could delay his orgasms indefinitely, while still being highly aroused. Alison considered this to be a highly desirable trait for a the kind of girl that her boyfriend was fated to be. Some people, perhaps, might think that what she was doing was cruel. But, if they could only see the blissed-out look on Jeff's face right now…

"Honey I want you to count backwards from twelve," Alison said. "And when you reach zero I want you to say, 'Jenny,' and then let go. Okay?"

"Uhhh…huhh…." Jeff moaned, hardly capable of speech.

"Good. Start."

"Twelve…eleven…n-n-n-ine…"

"Ten," Alison smiled, correcting him.

"Tennn…"

"You'll get there, sweetie," she encouraged. "Keep trying."

Yes you will indeed, Alison thought.

Twelve more days to Jenny.

day nineteen

Word had spread to the girls at the salon about how much further Alison's boyfriend had descended into full sissyhood and she thought it might be fun, as well as help speed that descent, if she had them over to see for themselves how far he had come. Jeff had done all the shopping, cleaning, and baking himself. The little dear was walking around the room with a tray of homemade brownies, bending delicately at the knees, serving Alison's salon friends. He was wearing a pair of white tights and a white midi-tank top, gold hoops in his triple-pierced ears, and flat sandals that showed off the pink pedicure that Janine had given him only a few days before.

"Thank you dear," the young manicurist said as she took a brownie on a little doily that Jeff handed her. "They're quite yummy."

Jeff beamed. Alison was so proud of her sissy. She could hardly believe this was the same guy that only two weeks ago would hardly have lifted his feet so she could vacuum under them when company was expected.

"Excuse me," he said brightly. "But would anyone like some fresh-squeezed lemonade or some herbal tea?"

"I would," Danielle said. "Lemonade, that is. I'm parched."

"Okay," Jeff said. "Be back in a sec."

When he left the room, Casey turned to Julia and said, "See? We told you. Isn't it remarkable?"

"I have to admit, the change, even from just the other day, is drastic."

"He's absolutely precious," Diane said. "I may not want my hubby turned into that, but I have to admit, having a sissy around can be rather pleasant."

"You said you caught him wearing makeup?" Julia asked.

"Yes, he looked so cute too," Alison said. "Even if he did use the foundation for blush."

The girls laughed.

"Well perhaps another trip to the salon is in order," Julia said. "Shall I schedule an appointment?"

"Definitely," Alison said.

"Make mine at the same time," Casey said.

"Mine too," said Diane and Danielle in unison. "I wouldn't want to miss that for the world," Danielle added.

Jeff came back with the pitcher of lemonade and filed Danielle's glass. "Can I get anyone anything else?"

"Why don't you just leave the pitcher on the table honey," Alison said. "Sit down for a while. You haven't been off your pretty feet all afternoon."

"Okay," Jeff smiled. He put the lemonade on the coffee table, slipped off his sandals, and tucked his legs under him on the couch. "What were you guys talking about anyway?"

"Oh Danielle was just talking about your friend from the video store," Casey said. "Weren't you Danielle?"

"Yes sweetie," Alison said, patting Jeff's bare white shoulder. "Danielle thinks he's just the cutest, don't you?"

"He's gorgeous," Danielle gushed. "I'll bet all the pretty girls who come into the store flirt with him outrageously."

"I was returning Kate and Leopold last week," Diane said, "and these two little hotties were chatting him up." She turned to Jeff. "Oh you weren't there honey."

"Do you ever get jealous," Casey asked him. The look on his face, Alison thought, was priceless. Then Casey added, "Oh I didn't mean that way."

Everyone laughed except Jeff, who only smiled, nervously.

Casey continued. "I just mean with him getting all the attention."

"Oh that's not nice," Julia interjected in a mock sympathetic tone. "I'm certain J. gets attention."

"I was only fooling. Of course he must," Casey said. "He's quite a little hottie himself, with his new style."

The girls laughed again and Alison watched her boyfriend with keen interest. He was blushing, staring down at his ankles, self-consciously playing with his toes.

"Does he have a girlfriend?" Danielle asked.

"Yes," Jeff said, with an involuntary sigh, still looking at his feet.

"Oh poo," Janine said. "Not that I'd cheat or anything. Although with that hunk I just might think about it."

"Please Janine," Diane said, "for a roll in the hay with Rafe, you'd cheat on a threesome with Russell Crowe and Ben Affleck."

"Who wouldn't?" Casey added, laughing.

"Good point," said Danielle.

"I have a feeling," Alison offered, "that it's not totally paradise between those two."
"Really?" Casey asked. "Tell."

Alison turned to Jeff. "What did you tell me about her, sweetie?"

Jeff looked up. He didn't seem to want to talk about his subject at all. "Oh, she's just really on him all the time. You know, just nagging him about money and stuff like that. She says, he's too immature and not ambitious enough. She gives him such a hard time."

"Uggh," Danielle said. "Why does he put up with it? Is his girlfriend that hot?"

"I saw her a couple of times at the videstore," Diane said. "She's gorgeous. Great figure, fantastic boobs, lips like a love doll. Totally hot."

Casey nodded, "That explains it. Guys will put up with anything for a hot girl."

"Hot schmot," Diane said. "It's probably half silicone."

"Yes," Julia said. "Amazing things can be done with a little makeup and plastic."

"Either way," Janine said, "she's probably got her hooks in deep. Poor guy."

"Oh well," Danielle said. "That's too bad. He's probably hopelessly in love with her by now."

"He'll be married before you know it," Casey said, "to some girl who doesn't appreciate him for the gorgeous hunkness he is and who will try to change him completely. What a shame. Especially when there's probably some other girl who can appreciate him just as he is, pining away for him." Casey turned to Jeff. "It must be hard to see that, huh?," she said. "Being his friend and caring about him and all."

"Where are you going honey?" Alison asked, pretending not to know very well what was troubling him, as her boyfriend suddenly swung his legs off the sofa, and hurried from the room.

"I have to…check something…in the k-kitchen," he said. But he didn't go to the kitchen. Instead the girls heard his soft skipping steps hurrying down the hall and then the bedroom door shut. "Listen," Alison said, holding up her finger for silence. The girls were quiet for a moment and listened to the muffled sounds drifting from the room down the hall.

"God," Janine said awed, almost disbelieving. "Is he crying?"

"Yes," Alison nodded.

"Poor baby," Casey said.

Alison turned to Diane. "Did you bring me the you know what?"

"Yes, in the bag."

"Good," Alison said. "It's time to put the next phase into action."

day twenty

For the first time since he'd been listening to the tape, Jeff seemed unhappy. Not even a quick sidetrip to the mall to buy her boyfriend some stirrup pants and silver bangle bracelets did much to lighten his mood. Alison knew, of course, what was troubling her boyfriend, but she also knew it was better for him to admit it himself.

Jeff had just finished some typing Alison had brought home from the office and was sitting beside her on the couch watching a program Alison had taped about transgenderism while she proofread the typed pages. The program was a kind of documentary and Jeff had already watched several of these over the last couple of weeks. The date and times and channels were regularly posted for the wives, girlfriends, and mothers of potential "girls" on the 30 Days to Jenny website.

Alison looked up from the papers her boyfriend had typed for her. They still had some mistakes and it took him three times as long as it should have but that was okay. Jeff would soon be going to typing classes at the local community college. Alison was determined that he would make something of himself and a top-notch administrative assistant to someone like Kurt could mean good money, especially for someone as relatively unmotivated and otherwise unskilled, as Jeff. She glanced up over the papers to her sissified boyfriend. He was wearing a new "relaxing at home" outfit: a shortie pajama set of pink cotton with a darling little matching headband.

"Honey," Alison said. "What's wrong?"

"Nothing," Jeff said petulantly.

""Honey?"

"Nothing's wrong," Jeff pouted.

Alison reached for the remote and clicked off the documentary. Jeff could finish watching it later.

"I know when something is troubling you, baby. Why don't you tell me? You always feel better when you tell me, don't you?" She watched Jeff's puffy bottom lip tremble slightly. "Don't you baby?"
Jeff nodded, quickly, brushing away a tear.

"Tell me sweetie."

"It's about…"

"Go ahead," Alison said gently. "Come one. You know it will feel better."

"It's about…Rafe," Jeff said and her boyfriend seemed to suddenly change before Alison's eyes. Gone, for the moment, was any trace of the man he still was. What sat before her now, Alison knew, was a lovesick girl. "What about Rafe?"

"It's what the girls from the salon said. About him…wanting a pretty girl…that she doesn't appreciate him…and I care about him…"

It was coming out all jumbled, but Alison knew very well what her boyfriend was trying to say. Although he didn't articulate it very clearly--it was clear to anyone who was listening. She knew it best not to push Jeff to spell it out just yet. That could come later. He might panic and have a relapse into his old false male self if he were forced to hear himself say the words: I love Rafe. Instead, Alison decided to reinforce his feelings physically.

"Let's go into the bedroom honey."

Jeff got up and followed Alison down the hall. He had become accustomed to her dictating the time, place, and circumstances of their sexual encounters. It was almost as if he had no conception himself of when he was ready for sex--until he was told. Then he was ready at a moment's notice. Another prized, if nonexistent, quality that men looked for in genuine girls, Alison thought wryly.

Her boyfriend climbed up on the bed, adroitly shedding his sexy wedge-heeled sandals in the process, and, on his knees, his cute little tush in the air, he pulled down his shortie pj's. The g-string he wore followed, and his clittie sprung out, hard and leaking, between his smooth thighs. Alison climbed beside him, but not until she took out the special dildo vibrator that Diane had asked her husband to buy from a sex shop in the city. It was a large rubber and plastic affair, lifelike down to the pimpled flesh of its large balls, and clearly dwarfed Jeff's, and for that matter, most men's, genital equipment. She let Jeff see it briefly and he made a small whimper of protest, but little else, as Alison greased it liberally with vaseline and clicked it on.

With one hand placed reassuringly on the small of her boyfriend's back, Alison introduced the dildo to Jeff's pink rosebud. He moaned softly and repositioned his hips to feel the head of the dildo better.

"I know you're hurting," Alison began, although to tell the truth, at the moment, Jeff didn't look like he was hurting at all. His lips were parted, his eyes squeezed shut, and his body was humping the dildo. "I know you want the best for Rafe. I know you care about him a great deal."

How much Jeff actually heard of Alison's words it was difficult to say. But the meaning, his conscious attention distracted as it was by his sexual excitement, was no doubt penetrating his subconscious.

"You are jealous honey. It's perfectly natural. You don't have to be ashamed," Alison continued. "It's perfectly natural for you to feel about Rafe as you do. It's perfectly natural to want him," Alison paused deliberately, and then added, "to like you best. You know you can give him what any girl can. Show him, sweetie, show him."

Jeff was breathing hard now, his smooth body trembling, his clittie drippy and gooey, and Alison knew the time had come to begin the final stage of her plan to completely sissify her boyfriend. She pressed the large head of the dildo against Jeff's asshole and after a moment of resistance Jeff relaxed his muscles and the first two inches slid with surprising ease into his bottom.

"That's it baby," Alison nearly yelped with excitement, her free hand sliding up between her own thighs, pushing aside her filmy panties, and finding her pussy, hot and wet. "Oh," she moaned, finding it somewhat hard to finish what she knew she had to say. "This is what Rafe wants baby. Open up. You can give it to him. You know you can. This is what he wants. You can give it to him…"

Jeff was rocking back now, his pink asshole stretched around the invading dildo. His clittie had gone semi-stiff with the shock of being entered, and was intermittently spurting, which caused him to push backwards and impale himself even further, although he could tolerate only about half of the dildo's length. He was moaning and whimpering and begging to be fucked but Alison could barely hear him over her own groans and cries of pleasure as she ground her pubis against her hand, three fingers deeply inside herself, and came to a mind-blowing orgasm.

Afterwards, Jeff lay on his side, on top of the sheets, sobbing softly into a pillow. Alison had cleaned her boyfriend up and helped him into a white cotton nightie, simple but sexy, and decorated with a little pink rose between where his new breasts would someday be. She had given her boyfriend a glass of warm nonfat milk and several sedatives that Diane, who was an insomniac, had helpfully provided. While the pills took effect, Alison had laid beside her boyfriend, spooning him, stroking his bare shoulder, and speaking to him in a comforting voice, assuring him that everything was going to be okay. And it was, Alison thought, in ten days everything was going to be just perfect.

Later, dressed for a late dinner, she stood in the doorway of the bedroom and looked fondly at her sleeping sissy. Jeff was still curled on his side, but the short nightie had risen up, baring his long smooth legs and exposing his pantied bottom. The panties, also white, were ultra sheer, and served basically no purpose except to hold in place a six-inch butt-plug Alison had slipped inside her boyfriend before he lapsed into unconsciousness, explaining to a groggy Jeff that it would help loosen him up. He hadn't protested. By the time Alison had pulled up his panties and patted his stuffed bottom, her boyfriend was fast asleep. The 30 Days tape was playing in a constant loop from a tape recorder on the night stand, like a lullaby.

He looked so adorable sleeping like that, Alison thought. She had arranged for the old woman down the hall, Mrs. Hooper, to sit for Jeff in case he woke up, but Alison figured he was asleep until morning. Kurt slipped his arms around her waist and stared over her shoulder at the sleeping plugged sissy on the bed.

"Is he doing what I think he's doing with his lips," he said, sounding amused, and a little mocking.

Alison nodded. "It's sweet, isn't it? she said, marveling at the little cock-sucking motions her boyfriend was making.

Kurt didn't comment on that. Instead he said, "And how much longer before…"

Suddenly Jeff moaned in his sleep. His body grew rigid, his toes curled, and he had a cute little orgasm.

"Unbelievable," Kurt said thickly. Alison felt his rock-hard cock against her back as he pressed against her.

"Ten more days," Alison said, her voice hushed in wonder. "Imagine that. Only ten more days to Jenny."