30 Days To Jenny (Days 21-25) free porn video

30 Days to Jenny By Monika Ikon Day 21 After their date the night before, Alison asked Kurt back to her place and they fucked each other to a sound sleep. Kurt had woken up just before dawn and slipped out of bed, figuring he needed to clear out before Alison's boyfriend Jeff, still plugged and sleeping in the other room, woke up and found him in the apartment. Alison pulled Kurt back to bed and told him there was no need to leave. According to what she'd read on the 30-Day to Jenny website, her darling little sissy should be two-thirds of the way to total feminization by now?and well beyond any macho jealousy. Kurt seemed unsure?but when she reached over and coaxed him to a rock- hard morning erection, he seemed more than willing to put Alison's theory to the test. Besides, her little pansy-boyfriend was by now so soft and unathletic, Alison could have physically dominated him herself! So following a leisurely morning fuck and shower, they sat at the kitchen table in their bathrobes (Alison had given Kurt one of Jeff's old ones). They sipped coffee, played footsie, and recounted the highlights of their torrid sexcapades over the last 18 hours. Any moment, Jeff would walk in on them, and there'd be no mistaking what they'd been up to all night and all morning. It would be the first time Alison's sissified boyfriend would see her with another guy. She couldn't wait. As it turned out, they didn't have to wait long. Kurt's eyes widened in disbelief when Jeff came bouncing into the kitchen with a cheery "Hi guys!" He was wearing a short pink silk robe over his matching pink silk nightie that barely covered his plump tush. On his bare feet, toenails polished a matching pink, he wore a pair of open-toed mules with a little bit of pink fluff on each instep. Alison's little darling was already listening to the 30-Days to Jenny tape through his special pink-plastic walkman. Standing on tiptoes in his sandals, he got a glass down from the cabinet and poured himself some orange juice. He took three of his special girl-vitamins from each of the bottles on top of the fridge and swallowed them down. "This is Kurt," Alison said to her pretty, perky sissyboy when he turned back to the table all smiles. "Kurt this is?umm?Jenny." "Why, it's so nice to meet you Jenny," Kurt said without missing a beat. He stood and accepted Jeff's limp-wristed hand. "Your girlfriend's told me so much about you." Kurt took in the spectacle of Alison's old boyfriend from pretty head to painted toes. He looked like he was going to bust out in laughing at any moment and Alison had to restrain herself from giving him a warning kick. Still, she had to admit, the absurdity of having Jeff meet her new lover while in full sissy mode was almost too much to be believed. Alison watched Jeff carefully for any sign of discomfort?any sign that he recognized at all what was really happening, or that he remembered his old self. But in his vacant, pretty eyes she detected no awareness whatsoever, nothing but a wide-eyed, girlish innocence as he prattled away to her handsome new lover. Good god, she thought?and nearly laughed out loud herself. Jeff?or should she say, Jenny?was actually flirting with Kurt! "Okay Jen," Alison said, playfully, "you're going to talk poor Kurt's head off and he's too much of a gentleman to sit down while you're still babbling. How about you go get the coffee pot and give his cup a refill?" "Ooops! Sorry!" her budding little sissy-maid said. The sweet thing even put his pretty hand to his lips. "I can be such a chatter-box." And with that, he minced on his pink high-heeled mules to the counter, returned with the coffee pot, and bent over the table to fill Kurt's cup. The little cutie seemed totally unaware that he'd let his nightie and silk robe ride up in back. Or was he? Either way, Alison figured she'd have to teach the poor thing to be more careful. After all, there was no telling what effect his sweet girlish charms might have on the wrong man. Day 22 What can you do when your boyfriend's a sissy? Needless to say, Alison had the full sympathy?and universal envy?of all her girlfriends. They all agreed that she was perfectly justified in taking a lover. After all, a woman needed a real man and taking one look at Jeff in the salon chair with cotton balls between his freshly painted toes and foil wraps in his soon-to-be-highlighted hair, there was no question that by no definition of the term could he be considered a "real man." Add to that, the fact that Alison's old boyfriend was making some changes in his new look to attract the dumb but gorgeous hunk at the video store where he worked?and one could easily make the argument that Jeff was no longer a man at all! Alison had already explained to Rafe, as best you could explain anything to that luscious lunkhead, about Jeff's gender dysphoria. After patiently assuring Rafe that gender dysphoria had nothing to do with the disease Lou Gherig had, or that "awesome-smart physicist dude in the wheelchair," she managed to garner his assurance that he'd do his best to look after Alison's little sissy in her absence. Secretly, of course, she hoped that her encouragement would soon lead to Rafe balling Jeff senseless. She knew she'd have to bide my time, but she was fairly certain that when she was through with Jeff, her lovesick pansy would be transformed into the hot little fuckmachine of Rafe's most x-rated wet-dreams. Meanwhile, Alison talked to the other girls in the beauty shop about her new lover Kurt. She described in salacious detail every aspect of her lover's attributes and performance. While they were all 100% agreed that Alison had every right to cheat on Jeff, they were nonetheless shocked that she could felt free to talk so openly about having sex with another man right in front of her feminized boyfriend even if he was listening to the 30-Days tape while having his eyebrows waxed. "Oh Jenny loves Kurt, don't you darling?" Alison said. Jeff looked up from admiring his new nail wraps. He turned off the pink walkman when he realized Alison was talking to him. "Kurt?" he said. "Yes, my boyfriend Kurt. I was just telling the girls how much you like him. Just this morning you were ironing his shirt for him, remember?" Alison felt a little tingle when she remembered the thrill of watching her boyfriend in a short silk kimono and puffy pink slippers ironing one of Kurt's monogrammed "power" shirts while they lie in bed, cuddling, Kurt's morning load of semen leaking out of Alison's still trembling cunt. Jeff giggled. "Kurt's soooo cute. And he's such a good dresser. I wonder what Rafe would look like in a suit?hmmm?." Jeff seemed lost once again in a contemplation of his nails and Alison continued recounting Kurt's sexual prowess to her girlfriends. How much harder, bigger, and more skillful Kurt was with his cock than any man she'd ever slept with, how she felt herself falling in love with him, how she thought that he might really be "the one." If any of what she was saying registered on Jeff, her old boyfriend didn't show it by so much as a flutter of his long, mascaraed eyelashes. When it was time to leave, the girls all gave Jeff a round of applause as he twirled around to show off his new perm of loose, bouncy blonde curls. Dressed in a halter-top and hip-hugging jeans, slipping his bare feet into a pair of rubber flip-flops to protect his new pedicure, Jeff was ready for an afternoon of shopping at the mall. The mission: to buy a new outfit for his upcoming movie date with Rafe. Of course, it wasn't so much a "date" as far as Rafe was concerned?more like an evening out with a friend from work who was going through some "changes." But Alison had her hopes that Rafe would quickly take advantage of the "situation"?and the new Strawberry's in the mall had just the clothes to send the signal. The 30-Days tape had already gotten Jeff used to the idea of wearing girl-clothes full-time; all Alison had to do was reinforce the idea in a positive way?as if wearing women's clothes were simply the most natural thing in the world for Jeff to do. And looking at her freshly- minted sissy prancing past the storefronts and attracting the sex- hungry gazes of passing men and teenage boys, it actually did seem the most natural thing in the world that Jeff should be wearing girl's clothes. What else would such a feminine creature wear?! To Alison's delight, Jeff went straight to a rack of the sexiest dresses in the store without any prodding from her at all. He showed not the slightest trace of self-consciousness when he picked out an adorable off-the-shoulder, red-and-white polka-dot dress with slightly puffy half-sleeves. The waist was cinched delectably tight accentuating his curves and the hemline hung just above his knees. With an unerring instinct for cuteness, Jeff picked out the perfect sissy shoes to compliment the look: a pair of red sandals with a 4-inch heel and a little red bow on each instep. "They'll match my new toenail polish perfectly!" he squealed excitedly. "Oh Allie, do you really think Rafe will like me in this outfit?" "Honey, if he doesn't, then he's got to be a sissy." Of course the sarcasm went straight over Jeff's pretty, bouncy blonde head. Instead, Alison watched in wry amusement as her old boyfriend basically pleaded with her to be completely feminized. God the people who made that tape are good, she thought. "Oh can I please please please have this outfit?" Jeff said, holding up the little fuck-me dress and shoes. "I just have to have it. I'll just die if I don't. Please? I promise I'll do anything. I'll practically be your slave. Please?" Alison laughed. She couldn't resist teasing the haplessly ensnared sissy. "Oh so you promise to be my slave, huh? What about Kurt? Will you promise to be his slave, too?" Jeff clapped his pretty hands together. "Oh yes yes yes. I promise. I'll be both your slaves. Just please let me have this outfit." The saleswoman who'd been watching the exchange and who'd helped Jeff try on the shoes and dress winked at Alison as she rung up the purchase. Nodding her head in the direction of Jeff, who'd gone off to browse a wall of cute handbags, the saleswoman said, "That one's sure coming along nicely. A real natural. How much longer till he's done?" Alison signed the Amex receipt, handed back the pen, and glanced back at her simpering sissy. He was such a pansy already it was hard to believe it could get any better than this. She counted up the days left until Jeff's complete transformation. Then she answered the saleswoman, "Only eight more days to Jenny." Day 23 "Bedtime Jenny," Alison called out to her old boyfriend. It was 9pm and she and Kurt were going out for the evening: a late dinner and then dancing at their favorite hotspot in the city. Jeff turned off the TV in the living room where he'd been watching a style makeover show. He loved learning how to accessorize or how to mimic a designer look for less. Tonight he was watching a show on swimsuits and thinking ahead to the summer. He wondered what that cute yellow bikini he'd seen would like on him. The woman on the TV said he'd need a bikini wax, though, since the bikini was so skimpy. Jeff would have to remember to ask Alison what a bikini wax was and hope she'd let him have one. In their room, Alison and Kurt had all but finished getting ready for their evening out. Alison looked past herself in the mirror where she'd been applying her lipstick to the doorway where her sissy was standing. Looking adorable in a tiny, white satin nightie, Jeff was already dressed for bed. "Have you got your diddle sweetie?" she asked. "Yes Allie." Jeff held up the vibrating butt-plug he was carrying in his pale, feminized hand. "Good girl. Kurt honey, you're dressed and I'm running behind. Would you mind putting Jenny's plug in so I can put her down for the night?" Dressed in an expensive designer suit, Kurt was sitting in an armchair by the bed, legs splayed out, slowly puffing a cigar. He savored the scene unfolding before him like a connoisseur. "I wouldn't mind at all," he said, putting the cigar down, and grinning. He looked at Jeff standing in the doorway of the bedroom where he'd just fucked his old girlfriend. "Come here darling. I'll put your diddle in for you." The sissy smiled happily, said "thank you!" and minced his way on plastic high-heeled bedroom slippers to where Kurt sat, now at the edge of the armchair and handed Alison's lover the butt-plug. "Turn around cutie-pie?" Kurt said. Jeff did as he was told, of course, and daintily holding up the hem of the satin nightie, presented his creamy bottom to Kurt's inspection. It really was incredible how thoroughly sissified this guy was, Kurt thought, but even he had to admit, the little tart did have a cute ass. He picked up the tube of KY jelly on the floor next to the bed. He'd used the jelly only an hour before to oil up his pole in order to fuck Jeff's one-time girlfriend. Now Kurt used it on the long, triangular- shaped plug he was going to use to stuff this sissy's tush. "Do you need me to go up on my toes?" Jeff asked helpfully, scrunching up his pretty toes in the plastic heels. "No baby?just bend forward, hands on your knees?that's it. Let me just spread you open?" Kurt parted Jeff's ass cheeks and peered at the sissy's soft pink rosebud. It was an inviting target, so fresh and tight. As it was, he couldn't resist slipping a greasy finger inside the pansy. Kurt heard the pretty boytart give a little gasp and then relax around his impaling finger. Damn?the hot little slut was even rocking backwards in his sexy little slippers to fuck his hand. Alison watched, winking at her lover, as Kurt grinned back and pulled his finger out of Jeff's slurpy asshole. He pressed the tip of the rubber butt-plug against Jeff's unresisting hole and slowly pushed it home, watching it stretch out and disappear inch by inch in the sissy's pink hole. Finally, the thickest part was inside Jeff's pretty bottom and Kurt activated the switch that would start it vibrating. "Ohhh?" Jeff said. And Kurt and Alison both laughed as the simpering sissy blushed. "Thank you Kurt," Alison said. "Say thank you Jenny. Thank Kurt for putting in your diddle and give him a kiss on the cheek goodnight so I can tuck you in before we leave." "Thank you Kurt," Jeff lisped. "Thank you for putting in my diddle." "Anytime babycakes," Kurt said, picking up his cigar and taking a contented puff. He patted Jeff on his plugged backside. Jeff placed his pale hands lightly on Kurt's broad shoulders for balance, leaned forward on tiptoes, and kissed him sweetly on the cheek. "Good night!" Jeff said happily. "Pleasant dreams kiddo," Kurt said. Tucked into his bed in the second room, Jeff lay curled on his side and asleep within minutes of Alison's kissing him nightie-night on the forehead. He had his pink headphones on and the 30-Days to Jenny tape was playing in a continual lullaby-loop over and over and over again. Lately, Jeff had taken to sleeping with a special "sissy sleep-aid" that the 30-Day website had supplied. It was a kind of cross between dildo and pacifier, and Jeff clutched it in his soft, prettified hand and sucked on it as he slept. The dildo was coated with a strawberry- cream flavor and laced with hormones, but more importantly, it trained and satisfied Jeff's growing oral and anal needs. Plugged in mouth and bottom, Jeff slept like a baby. After softly closing the door halfway, Alison came out to the living room where Kurt was chatting to old Mrs. Hooper. The fact was that even though Jeff's intelligence, never high to begin with, had plummeted to something below bubble-gum bimbo level, he was still an adult and didn't need someone to watch over him. But Mrs. Hooper had taken a real interest in Jeff's sissification and offered to sit in just in case the little darling woke up disoriented and panicky. "I wish they had something like the 30-Day program back in the days when I was feminizing my hubby," the old lady cackled upon hearing Jeff's latest progress report. "I had to do it the old-fashioned way, slowly and carefully. But," she brightened, "by the time Morris died, bless his heart, he was a full-fledged pansy. I buried him in a yellow chiffon dress and pearl toenail polish. His grey hair was permed and his lips were rouged. Everyone said he looked beautiful?and so he did." The old lady eyed Kurt and continued rambling. "I took a lover you know, looked something like you. Fucked him on the side all throughout my marriage. All man. No way to turn a real stud like that into a fairy. And why would a woman want to try?" She pinched Kurt's arm and winked at Alison. "Ah, if I were only twenty years younger. Had all girls myself, luckily. I'm sure I'd have turned sons into sissies if I'd had'em. By the way, can you give me the web address thingie to that 30-Day sight? My daughter Janie has a hubby that she'd like to get into panties." "No problem, Mrs. Hooper," Alison said, glancing at the clock and realizing it was time for her and Kurt to be going. "You can use my computer here to contact the site. And if you like, you can read some of Jeff's bedtime stories." Alison handed her a sheaf of feminization stories supplied by the 30- Day site and culled from various tg-archives all over the internet as the most effective for sissifying a man. "Thank you kindly," the old lady said, looking over the stories, and stopping at one in particular. "You know, I'd love Janie to turn my son-in-law into a diapered sissy. I've always wanted a sissy granddaughter?" Alison and Kurt left the old lady still talking about feminizing and infantilizing her unsuspecting son-in-law as they left to go clubbing. Meanwhile, Jeff lay snug in his pink bed, plugged by surrogate cocks fore and aft, leaking cum into his silk panties as he dreamed sexy dreams of becoming Jenny. It was a dream that would come true in exactly seven days. Day 24 The 30-Day site provided users with a listing of "sissy-friendly" doctors in their area to use for consultations, check-ups, and sundry medical advice about hormones, STDs, castration, and other vital feminization matters. Alison was taking Jeff in for what would be his first "sissy check-up." There were only two other people in the waiting room when they arrived for their 10am appointment: a pretty Asian woman and, sitting beside her, completely absorbed in a Teen Vogue, a very pretty sissy that Alison presumed was her husband. The dark-haired, 40-something sissy was wearing a pair of red hot pants that showed off his slim, smooth legs, red platform espadrille sandals, and a tiny white exercise top that left his midriff, tanned and firm, nicely exposed. Alison caught the Asian woman's attention with a knowing glance. "How many more days?" "Two," the Asian woman said with obvious pride. "I can hardly wait. And you?" "Six," Alison said, "not counting today. It's exciting, isn't it?" "It's the best," Kimiko said, introducing herself and her sissy, "Jenny." She indicated the girly-man sitting next to her. "Steve used to play around, lose jobs, think he was god's gift to me and the world. But as Jenny, he's just so meek and agreeable?the perfect companion. I just love him like this. The 30-Day program saved our marriage. I just wish I'd known about it years ago." Just then the woman's cell phone went off. She looked at the caller ID and excused herself for a minute. "It's Ray," she explained to Alison. "My boyfriend." Alison glanced at the sexy sissy scanning the pages of the Teen Vogue at eye makeup tips. He didn't show the slightest flicker of awareness, much less jealousy, that his wife was talking to her lover right in front of him. And why should he? How could he possibly compete for the sexual attention of his pretty wife?or for that matter?any woman any more? Instead, Alison noticed that Kimiko's pansy had glanced up from his glossy magazine to appraisingly assess the sissy competition across the waiting room. Idly fingering a blonde curl, Jeff was peeking up from his Cosmo-girl horoscope at his would-be sissy rival. Outfitted in a pale-green cotton jumper and pink flip-flops with coral polish on fingers and toes, Jeff had nothing to be ashamed of in the sissy department, if Alison had to say so herself. She had to admit that she was more than a little proud of how well Jeff had turned out. Who knew that sissifying a boy could be so much fun! Alison laughed. "Go ahead, Jenny. Why don't you say hello?" She then went ahead and introduced Jeff to Kimiko's sissy. The older, dark-haired sissy looked up a bit haughtily from her magazine as Jeff approached, perhaps the last trace of his former male persona. But Alison could read through the "attitude" to the bashfulness and insecurity underneath. The pansy measured Jeff with her pretty, made-up eyes, and then held out a limp hand and said, "How are you, my name's Jenny." "Oh Jenny," Alison said, turning to Jeff. "Another girl just like you. And her name is Jenny, too. Isn't that just the sweetest coincidence?" "I like your pretty sandals," Alison's sissy said blushingly. "They look really yummy with your red toenail polish." Kimiko's sissy also blushed. "Oh thank you very much. They'd look really cute on you, too. You have such nice legs and pretty feet." The ice broken, the two sissies sat down beside each other and looked through their magazines together, picking out fashions and cooing innocently over the hot boy celebrities. "Well," Kimiko suggested after she'd finished a short, sexually teasing conversation with her lover on her cell phone, "maybe we'll have to get these two girls together sometime. After all, they do have so much in common. I mean, besides their names." The two women watched, amused, as the feminized men put their heads together, tittering like a couple of fifteen-year-old girls. Just then the nurse came out and called out the name of the next patient. "Jenny?" she started, and for a moment both sissies looked up expectantly. Everyone laughed. And then the nurse said Jeffrey's last name. "Okay Jenny," Alison said. "Time to say goodbye to your little sissy friend. I'll be sure to get Ms. Tanaka's number and maybe the two of you can have a shopping date at the mall." The examination room looked like what one might expect to find in any standard ob/gyn medical office. Jeff sat on the end of the examination table dressed in a pink paper gown, his slim, pale legs hanging down. He was listening to his pink walkman and staring somewhat absently at his toes, which he curled up to admire his latest pedicure. The doctor came in and introduced herself to Alison as Sheila Benway. She was a short, solidly-built, no-nonsense woman who Alison liked immediately. The doctor picked up Jeff's chart and scanned his blood-pressure reading, his height, his weight, his pulse. "Everything here looks to be in order. He's lost 15 pounds already. That's good. Keep him on the proscribed diet. We want him down to 112. Now let's have a look?" Dr. Benway had Jeff lay back on the table and helped Jeff put his pretty feet into the stirrups. She palpitated his abdomen, felt the glands in his neck, and then put on a pair of rubber gloves. She slicked three fingers with jelly, and slid it inside Jeff's asshole. "He's nice and relaxed," she said. "No obstructions. He's taking to the anal training very well. I guess he hasn't been fucked yet." "Not yet," Alison said, "but I think he's close." Dr Benway nodded and stripped off her gloves. She tossed them into the biohazard pail. She squeezed Jeff's titties and asked Alison about the hormone dosages she was administering. "I'm going to up the prescription," Dr. Benway said, considering the chart again. She palpated Jeff's breasts again. "I think we can get a little more natural growth here before we send him in for the implants. We have C-cup potential, I'm fairly certain of it." The doctor flicked a finger across Jeff's right nipple and both nipples instantly hardened. "Look how sensitive he is," the doctor said. "And the loss of muscle tone already in his arms and legs is extremely encouraging. I suspect he's not fighting the programming very much at all anymore. His brain tells him he's weak and his body follows suit." It was true: just the other day Jeff had helped Alison carry in the groceries and literally had to drag one of the bags across the floor?a bag that Alison swept up off the floor with ease! The doctor helped slip Jeff's pale feet back out of the stirrups and had him sit up. She gently removed the pink earphones and cursorily examined his ears and throat and eyes. "Very good," Dr. Benway said, "Everything looks very good. You're doing very well Jenny. You're a very good girl." Jeff smiled. He loved to be told he was a very good girl. The phrase triggered the pleasure centers in his brain to release a flood of happy feelings. "Now Jenny," the doctor said, "I want you to answer some questions for me. They're very important. Okay?" Jeff nodded, biting his lip. Alison smirked. It was the silly thing's idea of a "serious face" and he wore it whenever he was required to think of anything more difficult than what color lipstick or toenail polish to wear. "What I want to know," Dr. Benway said, "is if you get erections anymore." Alison watched, fascinated, as Jeff's brow furrowed into a look of utter confusion. Aside from the nightly insertion of Jeff's vibrating butt-plug, she had no sexual contact with her ex-boyfriend at all anymore. According to the 30-Day site, Jeff should be well on his way to total impotence by now?the programming having deconstructed his ability to perform sexually as a normal man any more. Now, as Alison watched her old boyfriend struggling to answer Dr. Benway's simple question, what was really happening suddenly became clear. Alison was so astonished she literally had to throw her hand over her open mouth to keep from audibly gasping. Jeff had literally forgotten what an erection even was! As Dr. Benway gently tried other ways to ask the question, Alison watched in continuing astonishment as her old boyfriend looked aghast at the very idea that his little clittie, so cute and pink and soft, should get long and hard. To Jeff, the idea of having an erection was something completely outside his realm of experience. For him, anyway, not being a man, an erection was just wrong. Instead, Jeff said that sometimes he got a nice warm feeling "down there" and then everything sort of trembled and got moist and felt really good and that this usually happened when Alison or Kurt put his diddle in his bottom before bedtime. Jeff told the doctor these damning details with such a wide-eyed innocence that Alison couldn't suppress a great big smile at just how cute he looked and sounded. The doctor had Jeff put his pink earphones back on and dress and while the sissy slipped on his pink thong panties, matching bra, and green jumper, Alison asked how long her ex-boyfriend would need to listen to the 30-Day tape after the 30 days were officially over. Dr. Benway explained that the tape would have done its work by then and that Jeff would be ready for castration, cosmetic and other body- modification surgery. He might like to listen to the tape long after the 30 days were over, the way teenagers like to listen to favorite pop songs, or older people enjoy listening to music that reminds them of a particular event or an important time in their lives, but that it wouldn't make a difference one way or another. By then, the tape would have imprinted its message permanently into Jeff's brain, repeating itself, coloring everything that happened to him from now on. "Just as the 30-day site guarantees," Dr. Benway said, "your ex- boyfriend will be a fully functional sissygirl by the time it's all over. And from what I can see here today, it'll all be over pretty soon. Won't it Jenny?" Jeff looked up smiling, but obviously confused, from where he'd been glancing behind him and smoothing the panty lines from the green jumper. "I'm sorry?" he said, taking off the pink earphones, and smiling as always. The doctor said, "I said, you are turning out to be a very sweet and very pretty young lady. I'm sure you'll have all the boys chasing after you very soon." Jeff blushed and ducked his head in that adorable embarrassed way he'd developed. "Thank you?I?" Alison said, "Well there's one boy in particular, Rafe." "Allie!" Jeff said, his hands on his curvy hips. The doctor said, "Jenny, don't be embarrassed. It's perfectly normal for a girl like you to have a boyfriend. Just be sure you practice safe-sex. I'm going to give you some condoms just in case. You promise to make your boyfriend use them if he puts his diddle inside your bottom, okay?" Jeff blushed furiously, taking the condom packs from the doctor. "Okay, I promise." On the drive home in the car, Jeff licked the lollipop the receptionist had given him. Alison could tell he was thinking?inasmuch as Jeff could think anymore at all?about something. When she asked what was on his mind, the little cutie said, "Do you think what the doctor said will happen?" "What's that?" Alison asked. "You know, about Rafe. That he'll want to put his diddle inside my bottom?" Alison wished she'd had a tape-recorder so she could play back the conversation for the girls at the salon. "Oh yes honey," she said, glancing over at Jeff in his jumper and sandals, his blonde curls bouncing on his bare white shoulders, "Oh I'm positive Rafe will want to put his diddle in your bottom." It was true: Alison didn't doubt that Rafe would want to fuck Jeff. Considering how the luscious little poptart in the seat beside her was turning out?the only way Rafe wouldn't want to fuck him was if he were a bigger sissy himself! Alison didn't doubt anymore that her dream would come true. In six days, Jeff would be Jenny. Day 25 "Is that you Jenny?" It was after 2am when Alison saw her sissy tiptoeing passed her bedroom door after his date with Rafe. Jeff was wearing the red-and-white polka-dot dress and holding his little red sandals. Alison didn't even have to see his stained dress or disheveled hair to guess what had happened. "Oh Jenny," she sat up in bed and clapped. "It happened! Get in here sweetie, tell me everything, everything!" Jeff poked his tousled blonde head into the room and cast a wary eye on Alison's sleeping lover. "But won't we wake Kurt?" "Don't be silly," Alison said, nudging her already roused lover fully awake. "He'll want to hear everything, too. Won't you, Kurt." Kurt sat up, scratching his hairy chest. "What's up?" "It's Jenny," Alison said. "I think she has big news for us." "No fooling," Kurt said, grinning broadly and patting the bed. "Come in little darling, hop up here and tell us all about it." Jeff sat on the side of the bed with one smooth leg tucked underneath him, the other hanging over the bed, toes just touching the floor. The breathless sissy hardly knew where to begin he was so excited. Alison had suggested the picnic lunch and helped Jeff prepare the food and pack the big straw basket. They'd picnicked in a pretty local park next to Kurt's golf club. With its many secluded spots among the trees and rocks, the park had a well-deserved reputation as a make-out haven for kids and lovers. The fact was that Alison didn't need Jeff to tell her what had happened. The record of this particular date with Rafe was too important an event to be left to chance: that's how much faith she had in the 30-Day tape by now. Alison had dispatched her two friends Diane and Tara to spy on her sporty little sissy and to take along a digicam with a powerful telephoto lens. Alison wanted a record of what she was certain would be her boyfriend's last official day as a pretend "man" and his first sexual experience as a "real" girl. She figured such a film would prove a nice keepsake to remember Jeff by when he was long gone?and a nice way to keep him from protesting what she'd done to him if he ever came to his senses. But just watching her blushing pansy recount his picnic-date with his hunky boyfriend, Alison knew there was no chance that Jeff could turn back now, even if he was aware of what had happened to him. She'd already seen the digital film hours before and she was having great fun listening to Jeff breathlessly tell Alison and Kurt in girlish detail how he'd gotten himself fucked. Rafe had carried the big straw picnic basket that Jeff had packed and followed the pansy from the parking lot across a field of wildflowers and down a little embankment to a cozy and semi-secluded spot near the river. On the way, Jeff had slipped off his sexy red sandals and strolled barefoot though the tall grass, picking daisies. On a sunny little knoll, Jeff set out the blanket and the checked tablecloth and spread out the food. Meanwhile, Rafe, that lovable lunk, laid on his back chewing a stem of grass and watched the clouds move across the sky bored out of his mind. He'd brought along a radio and tuned in the Dodger game?a decision that Diane and Tara delightfully noted had caused Jeff to momentarily pout. The eager-to-please little sissy had made sure to pack all of Rafe's favorites: Buffalo wings, potato chips, beer, cold cuts, along with some more romantic selections, including cheese, a loaf of French bread, and a bottle of wine. While Rafe chowed down and listened to the game, Jeff fluttered busily around his man, making sure he was happy. Meanwhile, he nibbled daintily at a carrot stick and sipped delicately at a plastic cup of white wine. Alison had watched the film herself, had heard Diane and Tara's thunderstruck report, but she enjoyed listening to Jeff himself breathlessly tell her and Kurt how he seduced his handsome boyfriend. Why, of all things, the brazen little tartlet had snuggled up beside her supine Rafe and begun to playfully feed his Adonis grapes! Barefoot, flowers decorating his bouncy blonde hair, his polka-dot sundress practically falling off his creamy soft shoulders and hiked up over his smooth thighs, the sexy, kittenish trollop would have given even the straightest man a hard-on, especially the way he was playing slave-girl to Rafe's conquering warrior. Why, when they'd watched the film earlier, Alison had to laugh when she noticed that even Kurt needed to do a little shifting around to make himself comfortable in his pants. If Rafe hadn't noticed the erotic possibilities in the smitten sissy before, he suddenly realized them now with Jeff's hot, sexy little body dangling over him, ready to satisfy his every appetite. Looking up as if he were seeing Jeff for the first time, Rafe dispensed with the grapes and pulled the sissy's feminized hand down to his blue-jeaned crotch. You could see Jeff's momentary look of "O what am I doing, what have I gotten myself into" shock, but Rafe was no doubt used to this kind of feminine vacillation and he wasn't allowing the suddenly shy sissy any time for second thoughts. He started playing with Jeff's tits, taking one out of the low-cut bodice of the sissy's dress and sucking on the pink swollen nipple. You could see Jeff nearly swoon with pleasure. Jeff's hand was moving over the front of Rafe's jeans all by itself. "I was just going to give him a handjob," Jeff said, furrowing his pretty brow, "but he wanted something more. Oh, Alison, he wanted to put his diddle inside me right then, but I couldn't, not out in the open like that. I wanted it soooo badly but I wanted it to be right. I didn't want to lose him but I wanted him to respect me?" Jeff admitted, as if he had something to apologize for, "But still I'd waited so long so I?" Alison loved Jeff's sincerity and insecurity: it was so adorable. "So I?I gave him a blowjob instead?" Jeff told her and Kurt how he'd squirmed his way down Rafe's body, kissing as he went. Rafe obliged the sissy's worship by having his shirt open to the waist and all that sun warmed, muscled male flesh went straight to Jeff's dizzy blonde head. The sissy fumbled charmingly a bit with the button on Rafe's jeans, but he got it undone soon enough, and unzipped his prize: 7 inches of stiff, hard, cock. It must have been the tape Alison figured, the 30 Days to Jenny tape, that taught Jeff how to suck cock the way he did. It was his first time, and yet he took to it like a pro. "A natural cocksucker," Kurt had said earlier, admiringly, as he'd watched the video. And it was true: the sissy languorously licked the length his boyfriend's cock, sucked his balls between his plump lips, ran his fingers along its sides, squeezed him gently to prevent him cumming too soon. The sissy didn't just suck Rafe's beautiful cock: he worshipped it. He started and stopped, teased and pleased until Rafe couldn't hold back any longer. With both hands holding the sissy's blonde head steady, Rafe pumped his enormous wad into Jeff's pretty face. His lips and tongue working, the sissy gulped and swallowed the flood of semen without losing a single drop. "But that's not all is it, honey," Alison said, knowingly. "Something more happened, didn't it?" Her sissy boyfriend blushed and smiled: it was a special kind of smile? a girl's shy smile of carnal knowledge. It had happened! It was well after midnight, Alison noted. Officially it was day 26. But she couldn't wait until dawn. She had to hear how her sissy boyfriend lost his virginity right now. "He did it, didn't he?" Alison crowed. "He put his diddle into your bottom, didn't he, Jenny?" Jeff blushed some more, but the pretty pansy was beaming. He slowly shook his head, "yes," he squeaked. Alison clapped her hands and crowed with delight. "OOOOOHHHHH MY GOD! Oh my god, Jeff?I mean Jenny, tell us ALL about it!!! TELL US EVERYTHING!!!" The sissy clapped his hands, too. They were both bouncing up and down on the bed. Kurt chuckled, watching the "girls" get so excited. This should be good, he thought. He laced his fingers behind his bed, and leaned back against the headboard, prepared for what he was sure would be one red hot story.