Thirty Days to Jenny Ch. 2

"Cute," Alison said.

Jeff whirled around, nearly falling off the shoes, and began stammering apologies and explanations. He'd been ironing some things for her like he usually did, and well, he wanted to see what they looked like or—or. He stood there, looking stumped. He seemed to understand that his reasoning made little sense but he couldn't come up with anything better.

"Honey, we have to talk."

Alison had decided that morning to stop calling him by his boy-name. He wasn't ready yet for his new girl name, but it was time to stop allowing him to associate with a name that was no longer suited to his developing gender. From now on, if she or anyone had to call him by name, they would simply use the initial J. Jeff hadn't commented one way or another since she started using his initial. Perhaps he thought it was just a new nickname, a short-hand way of saying his name, and it was, in a way, but not for the name he thought.

She could see how upset her boyfriend was as he sat on the end of the bed. Alison took a moment to take in the image. With his highlighted, spiky hair and pale polished nails, his short skirt, halter, and sexy shoes, he looked like a perky young housewife or a new secretary at her office. He was looking down at the floor, as if ashamed of himself, his hands folded tightly in his lap, bare legs crossed at the knee, a shoe dangling nervously from his painted toes. He was trying not to meet her eyes and suddenly Alison realized why. She reached down, touched his chin, and gently lifted his face.

"Oh my god," she said.

His lips were lightly glossed and his eyes were somewhat awkwardly made up, but as Julia had predicted, quite stunning.

"You're wearing makeup sweetie."

"I didn't mean to," he sputtered, and gestured uncertainly towards her dresser where the makeup lay. He started to cry. "I mean I don't know why…"

"It's okay, baby."

"I'm not sure how…"

"It's alright." Alison knelt down, and put her arms around her boyfriend's shoulders. "It's okay honey. Sssh…sssh… Everything's alright."

When she sat back on her heels, Jeff was still sniffling, looking down, wiping his eyes. Alison had never seen him cry before.

"Please don't hate me," his voice quavered.

"Oh darling, I don't hate you. There's nothing wrong with who you are."

"I just don't understand why I'm like this."

"It's just who you are darling. Don't fight it. You do it because it feels right."

Her boyfriend nodded. "It does feel right," he said.

"And you like the way you look. Don't you?"

He nodded again.

"I do too."

"Really?" he said in a tiny voice, looking up from under teary lashes. "You're not just saying that? You really mean it?"

"Yes I do, darling." Alison said. "But," and the next part she knew had to be handled tactfully, "I think it's time you started getting your own things. You know, just to start. Some panties and nighties. Maybe some jeans and blouses. You can't wear my clothes all the time." She decided to try a little humor. "After all, I need them."

She saw the look of uncertainty on her boyfriend's face. "My own…clothes?"

"Sure," Alison said, trying to sound as matter-of-fact as possible. She'd read on the 30 Days to Jenny website that a large part of a new sissy's reprogramming depended on him believing that his changes were completely normal. "Don't you think it would be nice to have your own clothes to wear around the house?"

"Yes," her boyfriend sniffed and then a shy smile played on his painted lips. "I think that would be nice."

Alison returned his smile and patted his smooth, soft, bare arm. She looked at the triple rows of gold studs in the lobes of each of his ears and remembered how she'd taken him to have them pierced earlier as a kind of halfway to Jenny celebration. It had been an impulsive thing to do but Alison wanted to commemorate the day some way.

"I don't want you to feel at all uncomfortable dressing in front of me, sweetheart. Okay? Honey why are you crying again?"

"I'm just happy I guess," he said, smiling, tears running down his cheeks. "I was hoping you'd say it was okay. I mean, its just us, right? No one else has to know?"

"Of course not darling."

At that moment, the phone rang.

"Would you get that."

"'kay," Jeff said, dabbing at his smudged eyes with a tissue Alison had given him. He walked a little unsteadily across the bedroom in his heels, hips rolling, ass shifting inside the tight miniskirt. He picked up the phone, his voice still a little shaky. "Hello?"

Alison sat on the bed and watched her boyfriend in fascination. He apologized to the caller, explained that he'd been a little upset, and then seemed to brighten, answering questions and making small-talk in a chirpy little voice, giggling every so often in a cute flirtatious. Alison shook her head. This is amazing, she thought. She smiled at the nerve. Jeff held out the phone.

"It's for you."

"Who is it?" Alison asked, trying not to give herself away.

"It's Kurt," Jeff said happily.

Alison got up to take the phone from him. "Thanks darling. Why don't you go into the bathroom and clean up. Then you can finish ironing."

She waited until her boyfriend left the room.

"Okay, I can talk now."

Kurt laughed. "I think you could talk with him on the other extension and he wouldn't get it. How's it going?"

"Now, now, don't be cruel," Alison said, smiling. She could hear Jeff humming in the bathroom next door. "Everything's right on schedule."

"Dinner tomorrow, to celebrate?"
"Love to."

day sixteen

Rafe was sitting at the kitchen table, sipping a Jolt, and glancing at the movie listings in the paper Alison had left on the kitchen table. He was cute in that X-Games, hey-dude, kind of way, and a few years earlier Alison might have made a play for him herself, but she had outgrown that type and that stage of her life. She could easily see, however, why Jeff had such a crush on him.

She had told Rafe about the slight change in her boyfriend's name, but not the real reason for it, of course. Simply that it was his new nickname.

"Cool," Rafe had said, as Jeff stood there beaming sweetly. "Let's hit the pavement, J-dude."

They had come back about fifteen minutes ago and were going back out for a post-run chocolate peanut butter smoothie, which Jeff allowed himself once a week as a special treat. But first her boyfriend had wanted to come home to "fix himself up a little." Rafe hadn't seen the need for it, naturally, but Alison could tell that he was in the habit of indulging her boyfriend.

"You look fine," he shrugged.

"Oh no," Jeff had said. "My hair is a total mess and I have to get out of these yucky clothes."

Rafe just shook his head and plopped down in a kitchen chair, hooking a long muscled leg over the armrest, one hand under his shirt, idly rubbing the golden hair on his ripped stomach. The casual, self-assured pose reminded Alison of something very familiar. It came as something of a shock when she realized what it was: it was the way her boyfriend used to sit.

Alison stood at the sink and sipped her coffee. She looked at the guy her boyfriend was so crazy about. She had given a lot of thought to what she was about to say. She started according to plan.

"You and J. are pretty good friends, aren't you?"

"Yeah babe, he's a cool little dude."

Alison took a deep breath, ignored the "babe" comment, and forced herself to go on. "He likes you a lot, you know."

Rafe grinned and looked up briefly from the paper. "Hey, what's not to like?"

"I mean it. He really likes you."

"That's cool, babe."

It was going to be a bit harder, Alison realized, than she had anticipated to get through to Rafe. "Have you ever noticed that he's, well, a little different from ordinary guys?"

"Mmm, yeah. Yeah I guess so, now that you mention it. Like at the store the dude's always breaking down crying and whatnot. It's wild. He makes a mistake at the register or someone's rude to him, and he gets all emotional."

That was news to Alison. She savored the delicious image of her adorable little sissy bursting into tears at the slightest provocation. What a change, she thought, from the way he used to be.

"What do you do," Alison asked, "when he starts crying?"

"I say, dude, chill out. It's no big deal. Like it's just a job, you know? There's always collecting carts at the mini-mart. Why the boo-hoo?"

Rafe tipped his chair back and took another swallow of Jolt. Alison was beginning to think it was hopeless.

"That's not being very sensitive, Rafe."

"What?" he said, looking a little hurt. "What am I supposed to do?"

"You might try giving him a hug."

"A hug?"

"He really thinks your special. I'm sure he'd like it if you showed you care about him. You do care about him, don't you?"

"I guess, yeah. My girlfriend says I spend more time with him than I do with her. I say, whoa, babe, I work with the dude, you know? Of course I spend more time with him. It's an 8-hour shift. Do the math, okay?"

"You have a girlfriend?"

"Hey, she's not a live-in."

"Is it serious?"

"Nah."

Alison knew that she had to hurry. Even though her boyfriend took forever lately to get ready, she expected he'd be down any moment. Fortunately, Alison didn't have to be too subtle switching subjects with Rafe.

"Rafe I wanted to discuss something serious with you."

"Shoot, babe. Hey the new Terminator is coming out."

Good grief, Alison thought. How did her boyfriend talk to this gorgeous fence-post, anway?

"Rafe, as I was saying. J. is not like other guys. He is gender dysphoric."

"Huh?"

"He suffers Gender Identity Crisis."

"Further huh, babe. I'm not following."

"He's transgendering…" Alison stopped herself. She decided to make it plain as rain. "He is really a she. He's in the process of becoming a girl."

"What, he's a homo? I mean, hey, whatever whatever, right?"

"He's not homosexual," Alison said. "He's a girl in a boy's body, at least for now."

"What do you mean, 'for now'"?

"I mean he's undergoing changes."

"Hey, that rocks. You mean, he's gonna grow tits?"

Alison tried to keep her composure. "Please don't tell him I told you. He'd die."

"Hey, I'm cool with that. I can keep a secret."

Alison came to the point she'd been working on all along. "You're his friend. You can help."

"Help? Sure. How do I do that?"

"Be nice to him. Treat him like a girl."

"Yeah, well, I shouldn't have to pull a hamstring doing that. He's not exactly Joe He-man, you know. I have to treat him like a chick as it is. I'm just glad he's not a homo. People are talking. A girl, I can handle."

"Thanks Rafe," Alison said, hoping he'd shut up, which he did when Jeff came back into the kitchen. But it wasn't just discretion that cased Rafe to stop talking. Alison's boyfriend was standing in the doorway in a pair of her denim overall shorts, a sleeveless t-shirt, and sneakers. He had his hands in his pockets and one hip thrust forward.

"I'm ready for our smoothie," he said happily, "Rafe?"

Alison looked at Jeff's friend. His mouth had dropped open and he seemed speechless for a moment. But only for a moment, unfortunately, as far as Alison was concerned.

"Dude," he said, clearly impressed.

Jeff positively glowed.

Jesus, Alison thought. A match made in heaven.

"Listen," she said, "why don't you too go to dinner and the movies tonight. I have to work late, anyway."

"Sounds good to me," Rafe said. "That new Bruce Willis action flick is playing."

"Oh Rafe, I don't think J…" Alison saw her boyfriend widen his eyes in a desperate plea for her to be quiet.

"I'd really like to see that Rafe," he said, smiling prettily.

"Cool. Let's get going."

Her boyfriend gave her a little excited wave as they headed for the door. Alison waited until they left, and then she called Casey.

day seventeen

At the mall, Alison took her boyfriend to the Gap and Old Navy, Banana Republic and anywhere else they might have both males and female clothes. Eventually, she thought, passing stores like Wet Seal or The Limited, Jeff will be shopping at those stores exclusively.

Without any coaching, he'd put on a pair of his own faded jeans, but he'd rolled the cuffs up over his ankles. He was also wearing one of Alison's old Lilith Fair t-shirts and, for some reason, he had a small hemp knapsack of hers slung over one shoulder. He wasn't wearing a single stitch of truly femme clothing, except for the white satin panties under rolled up jeans, but the overall effect was unmistakably femmy.

Alison watched her boyfriend drift inevitably towards the men's half of the store, as if out of habit, or uncertainty. But she had only to call him over to look at something she'd picked out and he hurried over to where she was holding up a blouse or girl jeans in his size. She picked out t-shirts, tank-tops, shorts, and capri-style pants. She was careful not to pick out anything that screamed "girl" and in a strange way the strategy had a reverse effect. If Alison suggested a pale blue three-quarter sleeve ribbed top discretely decorated with rhinestones, Jeff suggested the pink sleeveless alternative with a scoop neck. They left the store with several bags bursting with Jeff's new wardrobe. He didn't seem to notice the giggling high school girls and smirking housewives, whose husbands stood in the background, glowering.

"Hey, do me a favor," Alison said as they passed the mall fountains. She took a bag from Jeff's hand. The website said that at the 17th day, her sissy should already be quite susceptible to post-hypnotic suggestion. Alison was curious to see just how suggestible. She was about to be plenty surprised. "Turn your wrists out while you walk."

Jeff looked at her, then at his wrists, confused. "Like this?"

"No no," Alison put the bags down and grabbed his wrists, facing his palms forward, along with the insides of his wrists. Like this. Go ahead. Try it."

Jeff walked a few steps, stopped, and turned back to Alison, questioningly.

"That's much better," she said.

"I don't know. It feels a little strange."

"Trust me, it's a big improvement." Alison picked up their bags and they continued through the mall with Jeff practicing his new walk. He drew a few curious stares, but not that many, after all, it really wasn't that unusual to see an effeminate man walking through the mall.

With her boyfriend mincing along beside her, Alison led them to the lingerie section of one of the mall's largest department stores. The Victoria's Secret the passed on the way, she decided, would be a little too much, just yet. But that would come in time. For now Jeff seemed relatively comfortable picking out panties in the less crowded and less conspicuous department store. He was looking at a display of lace panties and Alison noted that her boyfriend seemed to prefer his underthings ultra-girly and ultra-sexy.

He was looking at a display of lacy thongs and couldn't seem to decide between a pink and black pair.

"Which do you like better?" he asked.

Alison was tempted to ask him which color he thought Rafe would like better, but instead advised it wise that they buy both pairs. "You never know," she said, thinking of Rafe sliding the black pair off her boyfriend's pert white ass, "when you're going to feel naughty or nice. But you want a size smaller honey. You want that thong fitting tight between your asscheeks."

Jeff blushed.

"What are you thinking?" Alison smirked.

"Oh…" Jeff said. "Oh…I…"

She let it drop, not wanting to upset him, but soon she planned on hearing everything he was thinking and fantasizing. And not long after that, she wanted to help her boyfriend turn it into reality.

He was holding a sweet little teddy, with delicate spaghetti straps, against his shoulders and looking at himself in a three-way mirror.

"Is that for you dear?"

Alison, who was standing over by the bras, smiled. Janine and Casey were right on time. Alison had arranged for her friends from the salon to meet her in the lingerie section. She hung back just a bit to watch the show. This, she thought, should be fun. The pretty redhead laughed at Jeff's obvious embarrassment.

"You do remember me, don't you? From the salon? I did your nails honey."

"Oh yes," Jeff said. He was still holding the teddy against his shoulders.

"And I'm Casey," the perky, cute blonde said. "That teddy is soooo you, sweetheart."

Alison pretended to be surprised and came over to where they were standing, hodling a little chartreuse satin nightie in Jeff's size. "Oh hi Janine! Casey!"

"I see you girls were doing a little shopping, too," Janine said, ignoring Alison's warning look. But her boyfriend either hadn't heard to didn't mind or took her remark as a joke. "I wouldn't do white though," she said, referring to Jeff's teddy. "I'd go with pink. To match your nails."

"I agree," Casey said, reaching out and touching the hem of the teddy. "Pink would look so much cuter on you."

"Really?"

Janine winked at Allison. "Oh yes darling. And look at that cute nightie Alison picked out for you. Scrumptious. Hey show us what else you bought."

Jeff opened bags and took out his new femmy purchases to show the girls. As Alison had hoped, the acceptance of other women seemed to be reinforcing his feminization programming, just as the 30 Days website had promised. Now it wasn't only his girlfriend and the tape telling him that his urges were okay, but completely "impartial" third parties.

As they all walked to the food court for lunch, Janine nudged Alison.

"God Alison," she said, watching Jeff's new swishy walk. "How did you get him to do that?"
"Easy," Alison smiled, eyes sparkling, as she watched her sissy. "The power of feminine suggestion. You haven't seen anything yet."

day eighteen

Jeff was on the bed, propped up on his elbows and knees, the back of his chartreuse nightie flipped up over his waist, his saucy white bottom raised in the air. Alison had her boyfriend spread his legs enough to separate his ass cheeks and expose his little pink hole. Below, his pretty ball sack hung defenselessly. She really thought he looked quite sexy like this and almost wished she had a penis of her own to penetrate her boyfriend's pretty ass.

Instead, she touched the large silver vibrator to his butthole and watched him squirm like a girl in heat. His little sack tightened and trembled.

Fifteen minutes ago, Jeff used his soft tongue to bring Alison to a knee-shattering orgasm. She suspected that the pleasure of that skilled mouth was the last thing she was going to give up in her relationship with Jeff. The deep programming of the tape was imparting her boyfriend with the knowledge to be a master of cunnilungus. But, as she knew from the 30 Days to Jenny website, the tape was already starting to incorporate instructions for fellatio into her boyfriend's subconscious sexual education.

Alison leaned down and peeked between Jeff's smooth white thighs to take a look at his rosy-headed little prick. It was spooling out a long strand of cum which was leaving a widening dark spot on the sheet. Poor baby, she thought. He was going to have to strip the bed and do the sheets all over again. Alison got a thrill watching her boyfriend carrying his little laundry basket, filled with his messy panties and other femmy delicates, to the laundry room. She always made certain he was somewhat underdressed for the occasion.

On time he came up, Jeff was all excited. There were some guys in the laundry room, he said, washing football jerseys or something, and he thought they looked nice so he'd decided to say hello.

"They thought everything I said was funny," her boyfriend sound delighted. "I really think they liked me."

"Really baby?" Alison said, stroking his face.