Thirty Days to Jenny Ch. 1

May 5, 2024 // By:analsex // No Comment

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day one

Nothing happened. In fact, it was downright disappointing. The first time Jeff had listened to the tape he pulled off the earphones of his walkman after 30 seconds and said: “What the hell is that? It’s awful. Sounds like some kind of new age crap. “

Alison was disappointed. She had expected something to happen; ok, she didn’t expect it to be “poof” instant girl, but she had hoped for some kind of sign. At the very least, she thought Jeff would feel compelled to listen to the tape. How could it possibly work if he didn’t even listen to it? Walking off to the bedroom, she chalked it up to just another internet hoax. How could she have been so stupid? There was no tape that could turn a man into a girl in 30 days. What a fucking rip-off.

She had found the sissification site by following the links backward from a site address left on a message board devoted to women dealing with “problem men.” Unlike many of the men under discussion, Jeff hadn’t cheated, hadn’t abused her, hadn’t really done much of anything. Actually, that was kind of the problem. He was one of those guys who just didn’t seem to be going anywhere. He was lazy, out-of-shape, inconsiderate, clueless, insensitive, and, worst of all, bad in bed.

She had tried to dump him, without much success; he never quite got the hint and Alison didn’t have the heart to just throw him out. What she really wanted was for Jeff to be motivated to become something. So when she came upon the site titled “30 Days to Jenny” she figured she’d found just the right solution to both of their problems. The program promised to shape the right kind of man into a perfectly pliant, perfectly submissive young woman eager to please.

Alison wasn’t certain if Jeff were the “right kind of man. ,” She hadn’t ever considered Jeff as a girl before she came across the site, but something about it intrigued her. Something about it made perfect sense. She imagined Jeff as a pretty, submissive girl and felt something stir in her. It was worth a try.

Well, she had tried it and she had wasted $69.95, not counting rush shipping and handling.

day two

Usually, Alison had to hound Jeff out of bed in the morning. But he was up and getting ready before she hit the snooze button on the radio for the third time. He seemed to be in an unusually good mood. Alison didn’t think anything in particular of the uncharacteristic behavior. Certainly, she didn’t connect it to the tape she had played Jeff the night before. After all, his getting up early had nothing to do with becoming Jenny.

Later that day, however, she did note that Jeff called her twice from work just to say “hi. ” Jeff never called her at the office. He always claimed he was too busy. Too busy–working at a video store? It’s probably just a coincidence, she figured, as she dialed the number of the video store to return his call.

That evening, he came straight home from work and was waiting for her with take-out from their favorite Chinese place. He gave her a warm romantic kiss at the door.

As they ate together, Jeff actually told her about his day. Another first. He recounted all the oddball characters and goofy requests he’d encountered. Alison had to admit, Jeff was pretty funny and entertaining when he wanted to be. After dinner, Jeff cleaned up the paper plates and cartons, and packed up the leftovers in tupperware containers. Alison was nothing short of thunderstruck. She didn’t even think he knew where the tupperware was! Still, she didn’t make the connection.

Later, feeling tender over his sweet behavior, Alison came into the living room where Jeff was sitting on the couch watching a basketball game. She had brought him a beer. She noticed, however, that the one on the coffee table was untouched.

“Who’s winning?” she asked, trying to seem interested.

Jeff started a bit. “I’m sorry?”

“Who’s winning the game?”

“Umm… I don’t know,” he said. “I guess I’m not really watching. ” He looked at the television as if seeing it for the first time. He shrugged as if dismissing the players running back and forth, throwing balls, all that.

Alison sat down on the couch next to him. She took a sip from the bottle herself and looked him curiously. He seemed different somehow.

Jeff smiled and pulled Alison’s bare feet onto his lap. He started slowly massaging them.

“Hey,” he said, “can I listen to that tape again?”

day three

Alison woke up to the deliciously sensual luxury of having her toes licked. She sighed, stretched, and stared down the length of the bed. At the bottom, Jeff was lying at her feet, slowly and lovingly sucking her toes. He looked up and smiled a little sheepishly.

“That feels so good, sweetheart,” she said.

Encouraged, Jeff resumed his attention to her feet, gently licking her soft soles. Alison closed her eyes and enjoyed the sensations. There was no doubt about it; the tape was having some kind of an effect. Jeff was often in the mood for sex in the mornings, but he never bothered much with foreplay. What he was doing now, it was definitely a welcome surprise. sex hikayeleri

Jeff was kissing her ankles, moving up the insides of her calves, and Alison parted her legs slightly. He spent a wonderful forever between her thighs, teasing and licking and kissing, until Alison was breathing heavily with anticipation. She was never much for morning sex, but Jeff was driving her crazy. She reached down and pulled up the hem of her cotton nightshirt.

“Please don’t stop,” she murmured.

She felt his tongue trace the lips of her vagina and she shuddered with pleasure. He lingeringly licked her, seemingly perfectly content, and Alison enjoyed the sheer sensuality of it all. There was no rush toward a goal, no attempt to do anything else, no expectation of an orgasm. After some time, feeling almost self-conscious, Alison reached down and cupped his face in her hands.

“Honey… that was… wonderful… “

Jeff smiled, proudly this time, his face wet with her.

“Come here,” Alison said.

She reached between his legs and felt him, hard in his pajama bottoms. She had expected that. She wasn’t in the mood for penetration but she wanted to reward him. To her surprise, Jeff got out of bed, seemingly completely oblivious to his state of arousal. He pulled of his pajama bottoms and his painfully hard erection was standing almost flat against his tummy. He looked around a moment, as if a little dazed, and then walked over to the laundry pile. He picked up a pair of blue silk panties which Alison had worn the day before.

“Can I wear these today,” he said, a little shyly. “To remind me of you?”

Alison could hardly conceal her excitement. “Oh how sweet,” she said, keeping her tone as matter-of-fact as possible. “Of course you can wear my panties darling. Put them on. “

Jeff looked vaguely relieved. He stepped into the panties and pulled them up over his straining erection. The panties were bikini-cut and very skimpy. They barely contained him; in fact, they seemed to be making his situation worse. Jeff didn’t seem to notice.

“Do they look okay?”

“You look perfect darling,” Alison said.

“Do you really think so?”

“Definitely. “

Inside, Alison was doing mental cartwheels of joy. Could it be—could it really be working? She didn’t dare believe it… but…

day four

The next evening Alison came from work to find the table set. There was a bottle of Chianti at the center flanked by two burning red candles. Jeff came out of the kitchen in jeans and one of her t-shirts. She noticed the apron with the frilly hem tied around his waist. He smiled, happy to see Alison, and ran over to give her a kiss. Barefoot, he was about an inch shorter than Alison in her dress pumps and had to go up a little on tiptoe to reach her lips.

“Hi honey,” he said, a little breathlessly.

Alison took a look around, the set table, the sound and smell of simmering, boiling pots coming from the kitchen. Apparently, Jeff decided to take care of dinner again. Only this time he was cooking. Alison was hard-pressed to remember when he last made a bowl of cereal for himself. “What’s cooking, sweetheart?”

“Spaghetti,” he said. He shrugged apologetically. I’m afraid it’s all I know how to make. “

“That’s okay, sweetie. I could go for Italian. “

“Really?” Jeff beamed. “I bought some cookbooks from the place next to the videostore. I thought maybe I could learn how to, you know, cook a little better. “

Alison couldn’t resist. He looked so cute standing there, barefoot in an apron. She touched his cheek affectionately.

“I’d like that. “

At dinner, Jeff served the food and poured the wine. He fussed over Alison, clearly nervous if she would like the dinner or not. His behavior was a far cry from all the times she’d come home dead-tired from work, put something together for dinner, and have him complain that he didn’t feel like eating leftovers again!

“Would you like a little more cheese?” he offered. “More sauce. It just from the bottle, but I tried to add some of the spices you add. At least I think I put the right ones in. “

“Relax honey,” Alison said, amused. She had never seen him so adorably flustered. “Dinner is perfectly delicious. Thank you. “

Jeff sighed with relief.

For the first time, Alison noticed her boyfriend’s plate.

“That’s all your eating?”

“Oh god Ally. I caught a look at how I looked in your panties today. I have to go on a diet! I was at the checkout line at the supermarket this afternoon and found one of those little lose weight fast booklets by the register. I thought I’d give it a try. I think maybe I’ll even start running. Rafe, you know, the surfer dude at the video store, he runs all the time. He said he’d go with me. “

Alison listened with sheer fascination. She poured herself more wine. She needed to distract herself from her own excitement. “That’s just wonderful darling,” she managed to say. “Just wonderful. “

A moment later, she had gotten enough control of herself to ask: “Do you like wearing my panties, honey?”

Jeff porno hikayeleri looked down.

“It’s okay,” Alison smiled, encouragingly. “You can tell. I’d love to hear what you think. “

“Well, I really like the way they fit, so snug and skimpy. It’s like being exposed or something. They make me feel kinda sexy all day long. ” He seemed to catch himself and added quickly, “You know, they make me think of you. “

“That’s nice sweetie. Really nice. “

That evening Jeff sat in the kitchen after cleaning up and looked through his new cookbooks. Alison was down the hall, surfing the internet. She visited the testimonials on the 30 Days to Jenny bulletin board once again. She could hardly believe the claims left their by women who claimed that their husbands, boyfriends, nephews, sons, and fathers had been totally transformed into her pretty, submissive, girls. But she couldn’t deny the incredible change that had come over Jeff. And it had only been, what, four days?

Alison got up and went into the kitchen for a glass of lemonade. She stopped in the doorway for an instant and looked at Jeff sitting at the table. His head was cocked to one side, a finger to his lips, jotting down the recipe he’d found in the cookbook open in front of him. He was wearing headphones, humming along pleasantly to the tape, as he read.

day five

Feeling sexy, Alison lay in bed in a black negligee and watched Jeff undressing. He was wearing another of her panties, a pretty little pink silk pair, and there was very little to conceal the huge bulge Jeff’s hard cock was making.

“Come here Jeff. “

Jeff walked over, wearing nothing but the panties and, of course, the erection. Alison traced the outline of the hard, silk-encased cock.

“I think we should take care of this, don’t you?”

Jeff seemed suddenly very embarrassed. “Oh, Ally… I… dunno… I guess it will go away… “

Jesus, will wonders never cease, Alison thought. The rest of it, up to now, had been pretty damn amazing. But the idea that her oversexed boyfriend would actually turn down sex… it was, well, impossible! She slowly traced a long-nailed finger along his swollen shaft and ended tickled his glans. A tiny drop of precum spread into the silk.

“Now look,” Alison said playfully. “You’re getting wet. Come on, get your panties off. We have to take care of that. “

Jeff hesitated, looking around the room. Good grief, was he actually blushing?

“What’s the matter, sweetie?”

“Ummm… could I have like something… something, you know, cover myself?”

Alison could hardly believe her ears. This was a guy who thought nothing of sitting around in a pair of underwear or strolling down to the kitchen in the buff for a can of beer.

“Sure darling… ” Alison wondered, if–maybe. It was worth a try. “You can throw on my robe. Its right behind the door. “

Jeff looked relieved. He walked to the door, which gave Alison a chance to check out his ass looked in the panties. Not bad, she thought, not bad at all. If he sticks to his diet and running regimen…

Once inside the short silk kimono, Jeff slowly stripped off the panties. He stood in front of Alison seeming a little bewildered. The kimono was so short that it hardly covered anything at all.

“Climb on the bed silly,” Alison said.

“Okay. “

To her surprise, Jeff immediately lay on his back, this legs slightly spread, assuming the submissive female position. Alison tried not to show any surprise as she straddled his hips. She lowered her pussy over his hard flat cock and rubbed up and down its smooth, hot length. Jeff seemed uncharacteristically composed. She ducked her head and kissed him warmly on the mouth and Jeff responded with a deep, open kiss of his own.

Hmm, Alison thought, that’s more like it. She kissed him some more and Jeff became more animated beneath her. She could feel his body undulating but restrained. On a hunch, she reached down and squeezed his left nipple. This elicited a clearly pleasurable little moan from her boyfriend, so she did it again. His movement became more urgent now; he wriggled around sensually beneath her.

Alison could tell from long familiarity that Jeff was ready. But curiously, he made no move to penetrate her, in spite of the fact that he was rock-hard and that her own hot, wet pussy was sliding up and down against him. It suddenly occurred what he was waiting for.

Propping herself up, she pulled herself slightly ahead of the tip of his swollen glans and then slowly, inch by inch, slid herself onto his cock. Jeff moaned with pleasure. He reached up and played lightly with Alison’s nipples. No hard squeezing or twisting… just a light sensual touch, a brush with his fingernails, a playful pinch between his fingers.

Jeff usually finished rather quickly. It wasn’t exactly a case of premature ejaculation… more like he just didn’t have the discipline to wait for her to come. But this he was in no rush to come. Fact was, he was so engrossed in the pleasurable sensations of Alison’s love-making that he seemed unconcerned seks hikayeleri about coming at all. Alison reached three leisurely orgasms before she figured it was time Jeff found relief.

“I’m going to finish you now honey,” Alison whispered, sweaty, happy, sated. “I don’t want you to fight it, okay?”

Jeff nodded, biting his lip.

Alison increased her strokes, her boyfriend sheathed tightly inside her. She could see Jeff’s excitement building. He was trying to hold back, for some reason… modesty, perhaps? But Alison could see he was losing the battle. He was so close, she could sense it, his penis swollen inside her feeling bigger than it ever had. He needed one last thing to bring him over the edge. Alison reached down and pinched his hard little nipple.

Jeff’s body moved in rhythm with hers, his eyes closed, at the end of his outstretched arms his hands balled up in fists. His brow furrowed with sensual concentration. Alison bent forward and whispered,

“I love you in panties. “

Jeff gave a little cry and his body bucked beneath her.

“Oh, oh, oh… “

“It’s okay honey come,” Alison said, smiling down at her sexy boyfriend as he shuddered to climax.

She let him go to the bathroom first to “wash up. ” She noticed, with satisfaction, that he slipped on the short little kimono the moment he got out of bed.

day six

Off from work, Jeff volunteered to do the grocery shopping. He had made a little list after going through the refrigerator and kitchen cabinets. There were also some ingredients he needed for the new recipe he wanted to try.

Hmmm, Alison thought, even if it ends right here, I could get used to this.

At the door, she kissed her boyfriend warmly on the mouth. He was wearing a pair of sweat-shorts and an oversized football jersey, but underneath Alison knew Jeff had on a pair of her black lace panties. There hadn’t been any further discussion after that first time. Jeff was wearing panties every day now. It seemed perfectly ordinary that he do so.

On the way into the office, Alison remembered the folder she had forgot to bring with her. She had an early meeting and couldn’t turn back to get it, so she waited until lunch time to drive back home. She called him on her cell phone but there was no answer. She figured he must be at the supermarket.

Jeff’s car was still in the parking lot when she pulled up. Odd, she thought. She let herself into the apartment and heard the music turned up loud enough to swallow the sound of the ringing phone. He must have brought the boom-box into the bathroom. He was playing one of her old Madonna cd’s, of all things!

Alison walked down the hall. The door was partially open and she could hear him humming along to the music. But it wasn’t the Madonna song he was humming.


Alison pushed the door open and there was her boyfriend in the bathtub, one foot propped up on the faucet, shaving his leg with her pink razor. He had the headphones on and was listening to the tape on his walkman which sat on the edge of the tub. She stood there for a moment, stunned, and Jeff looked up at the same time, mistaking the look on her face entirely.

“Oh god, Ally… I can explain… I… “

He sat up and fumbled for the tub drain. The poor darling was frantic. He almost pulled his walkman into the water with him.

“It’s okay, sweetie,” Alison said, forcing herself to appear composed. She didn’t want to scare him.

Jeff still thought it necessary to come up with a plausible explanation. She let him try.

“Ally I just thought with me running and all, my legs would just look better, you know, without the hair… “

“Jeff I think they look just wonderful. “

She did, too. His legs looked long and sexy like this. Alison smiled and her boyfriend looked somewhat relieved. She knelt down by the side of the tub and picked up the pink razor floating in the soapy water.

He looked up at her shyly.

“You’re not mad?”

“Mad? Why would I be mad?”

“Or think its weird or anything… “

“Ssssh… don’t be silly sweetheart. ” She pushed him gently back into the tub. “Here let me finish for you. “

He had pulled his headphones off trying to get out of the tub and now Alison replaced them. She told him to lean back, close his eyes, and relax to the pretty music. She then slowly and carefully finished shaving her boyfriend’s legs.

day seven

After the first night, Jeff no longer watched sports on television. If he happened to click passed some kind of game with the remote, he didn’t even pause to show the least interest. Instead, he and Alison watched television together, mostly the situation drams and trendy relationship-oriented comedies that Alison enjoyed.

Fresh from the shower, Jeff sat on the couch in a pair of green silk panties and Alison’s pale green bathrobe. Alison’s feet were in his lap and he was happily giving her the best foot massage she’d had since forever. That evening he’d brought home a bag of videos after his shift at the store. In spite of the progress made over the last week Alison expected her boyfriend ad brought home the usual fare of action-adventure, horror, and crudely sophomoric “comedies” he usually watched. She was shocked when after dinner he asked her if she wanted to watch Pretty Woman with him.

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