30 Days To Jenny: Days 10-20 free porn video

30 Days to Jenny: Days 10-20 By Monika Ikon 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 sweat socks 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! It's 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 separators. 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 telltale 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 shirttails together. He was walking in front of the mirror and looking behind him to check how the skirt made his bottom look. "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 shorthand 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, it's 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, anyway? "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, holding 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. "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 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 videostore," 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 side trip 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."