Speranzafox1TSSperanzafox1TS
BeckyTsBeckyTs
molly_hill22molly_hill22
YsabelMillerTSYsabelMillerTS
TSstepsissyTSstepsissy
DianaLilouTSDianaLilouTS
STALLION_COCKTSSTALLION_COCKTS
Swipe to see who's online now!

Dan's dreams come True Ch. 01

Story Info
Dan's adult book store visit ends in his dreams coming true.
6.5k words
4.7
43.3k
52

Part 1 of the 2 part series

Updated 06/09/2023
Created 01/12/2020
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Dan felt the familiar tingle as he walked down the street. First there was the pub, then the little cafe with its pretty tables and the stationery store. And then the green door. The one he'd walked through many times but always got the wonderful, knot of expectation in his stomach. Looking straight ahead, he pushed it open and walked through.

Once inside, the familiar musty smell met him. The shop was old. He'd spotted it as a kid and always wondered what went on behind the door. "Adult bookstore" it said above the painted-out windows. He figured children had their own bookstore so why not adults. But as he grew and his "interests" developed, he became aware, this was the place that might help, that might give him some guidance to the world he wanted to see, to experience and perhaps even to join.

Moving aside the heavy green curtain, Dan walked into the store. Everything seemed so familiar. Except the lady behind the counter. She was new. She was pretty, some would say sexy. Mid-forties maybe, hair scrapped back to show her high cheekbones and expertly made up face. A white satin blouse opened far enough to show an exciting hint of cleavage. Dan smiled to himself, "All that with a glance, I should have been a spy."

It was early evening. This was a stop on the way home from work. Dan planned to entertain himself tonight. The only other customer made his way to the counter and checked out clutching his purchases from one of the seven sections in the store. He'd sauntered through bondage and stopped briefly at the Lesbian magazines before heading out. Dan was only interested in one part of the store.

It was an interest from the age of five, although he didn't really know what it was or what it was called back then. He just knew he found his mother's clothes so much more stimulating than his own but not in the way you'd think. To five-year-old Dan they were simply pretty and soft and comforting.

As he grew older, he'd wait till everyone was out of the house and sneak into his parent's room. He became an expert at removing clothes from drawers and putting them back exactly as he found them. He could take slips and underwear from the wardrobe and put them back in the same place, in the same order, with almost the same folds. He had to learn because he didn't want anyone to know what he did. He became a girl.

Admittedly not a convincing one at first. But as he moved through his teen years, he could see some changes. There were some girly aspects to his changing body. His bottom was rounder than most boys, but helped fill the skirts he wore. His legs were slim and shapely, and looked good in tights (his mother never owned a pair of stockings) and his hair was long enough to sweep into something approaching the trendy wedge shape the girls at school favoured.

He enjoyed the chances to escape into this other world but if he had one complaint it was his mum's taste in clothes. They were old fashioned, very conservative and not very exciting. When Dan flicked through the shared porn mags at school, the pictures that excited him most where the ones where the girls were wearing something sexy; a corset, bras and suspenders; gorgeous miniskirts and ever so tight tops. He loved the girls but loved the clothes more.

In his dreams his glamourous auntie would take control of him and dress him as a school girl and send him off to classes. But when he came home, she'd dress him in much more exciting outfits, A Marilyn Munro dress, the white shift worn by Debbie Harry on the Blondie Album she played all the time, a cheerleader. Even one of her sexy business suits with the tight skirts. Or her lingerie which was delightful. He enjoyed many moments dreaming that could happen.

Dan flicked through the books and wondered which three he'd take today. There were some filled with letters and pictures. A bit like his mum's wardrobe, stimulating but safe. Then there were books like his auntie; wonderful and exotic. Then there were the true fantasy books, where the boys were controlled and coerced and forced into a life of femininity. "Why does that never happen to me?" thought Dan as he picked up one of each

He suddenly caught sight of the sales assistant eyeing him up through the mirror placed to catch shop lifters and worse. She was prettier than he first thought and seemed to be giving him a long lingering look. He wandered past a couple of other sections feigning interest but now with books in hand all he wanted to do was head for the door and get out of the shop.

He placed all three magazines face down on the counter, embarrassed for some reason while knowing this is what the shop sold. He tingled again, the hairs on the back of his next standing up. It was a frightening feeling but he called it 'the good fear.'

The assistant picked them up one at a time and scanned them, pausing only to flip them round the right way before putting them in the brown paper bag. The last one didn't scan properly. She tried a few times before lifting the cover and entering in the code at the front. Dan felt ashamed but the assistant seemed all to matter of fact about it. "You an admirer or a participant?" she asked.

Dan was shocked and could only blurt out "Whaaat?"

"Do you dress or just like to look at the girls who do?" Her tone was soft, Dan even thought sympathetic. He blushed bright red. He could feel the heat, and the lady smiled. "I'm Caroline" she said "and there's no need to go all bashful." Dan knew the shop was empty but looked around again just to make sure.

"An admirer but would love the chance to do it properly." The words tumbled impulsively from his mouth and even he was shocked about how open and honest he'd been.

"You've never told anyone about this have you?"

"No, you're the first!" said Dan.

"Well I'm honoured sweetheart."

Dan heaved a sigh, not knowing if it was relief or fear but for the moment he was going with relief.

"Any idea how much "Forced Femininity" is?"

"Fifteen" said Dan. Caroline started to flick through the pages and Dan suddenly felt flustered.

"You'd make a much prettier girl than some of these efforts." Again, Dan felt the heat from his face. "It's quite sexy though. Boys dressed as girls." She suddenly fixed Dan with a gaze that made him tingle and stiffen at the same time. "I'm done here in five minutes sweetheart. If you want to wait 'till I cash up and log off, I think I can help you make your dreams come true."

Dan gulped hard; his mouth suddenly drier that a nun's snatch. All sorts of things flew around his head. "Firstly, nun's snatch? Euch, where did that line come from? Secondly how can I tell this woman is serious and thirdly oh my god wouldn't it be brilliant if it was true."

Caroline was still staring at him. He hadn't replied.

"Look I live not far from here. I'm divorced and you can text or email a friend the address. Tell him you got lucky but you thought the woman might be a bit crazy or you'd just watched Fatal Attraction or something. I'm serious. I want to help you out."

Dan smiled and said "If you really mean it, I'd love to. Thank you, Caroline. My name is...."

"No. No, you don't darling" she interrupted. "I'm going to create you, so I get to name you. I can get you a discount of 50 percent on your purchases today, just sign this and sit down while I finish doing what I have to do and just check this magazine for ideas. Oh, by the way, no sex." She then mumbled something that sounded like "We'll not with me anyway" but Dan wasn't sure. He signed and sat down. He was trying hard to stop his heart bursting through his chest and his penis from doing the same to his trousers.

They walked a short distance to a modern apartment block nearby. Dan hung back a couple of times, trying to get a better look at Caroline. She was sexy. Great legs, great wiggle and a gorgeous face. Dan was sure he'd seen her before but couldn't quite place her.

They walked into the apartment. It was modern and sophisticated. So, unlike his bachelor pad. "Right" said Caroline immediately taking control. "Put your stuff in that small room there- and when I say stuff, I mean all your clothes. Then into the bathroom and we'll sort out a few things in there."

"Look Caroline, I'm really sorry but I...." A hard slap stung his face.

"Look buddy boy if you think you're backing out now, forget it." Her tone changed. "You know you want to do it," she purred. "You've waited a lifetime for someone like me, someone to take control and turn you into the gorgeous girl you know you want to be. Are you really going to let a few nerves get in the way of the sexiest night of your life? I don't think so."

She rubbed him provocatively and he responded in the natural way. "That sweetheart is a give-away, now bedroom, clothes off, bathroom and wait."

Dan did as he was bid. He felt a little self-conscious naked but crossed quickly into the bathroom, hands covering his dick. He sat and waited for Caroline, but heard only her voice. "The red lotion in the bottle, rub it over your body from the neck down and wait five minutes. While you're waiting shave your face really closely, then shower."

Dan again did as he was told and was soon standing in the shower watching the hair from his body flow down the plughole. He was working on excuses already. "Taken up swimming or cycling. Prepped for an op that was cancelled." The thing was he was tingling all over before the shower. His stomach and head realised he was reaching the height of excitement, but he knew Caroline was right, this is what he's wanted all his life and he was determined he should now enjoy it.

"Out into the hall darling" purred Caroline.

He stepped out with his new mood and suddenly was confronted with a goddess. Gone was the business attire and tight bun. Caroline now stood before him in knee length leather boots, a tight black leather mini, a black leather halter top and her hair cascading over her bare shoulders.

"I see you like" said Caroline, pointing at his growing erection. Dan did. Very Much. And then it hit him. He knew where he recognised Caroline from. He couldn't believe he didn't see it sooner. Caroline was one of the women in Forced Femininity, one of the "strict bitches" who made boys into girls.

He wondered if he should run, but slowly he realised this was all he ever wanted and Caroline was now in control.

Caroline fixed Dan with a long hard gaze. Her red nail polished index finger went up to her lips and she seemed to be contemplating something. He noticed the shades matched. "Yep, now I know. In there" said Caroline.

Dan meekly followed her finger to the room she was indicating. He walked in to a small dressing room. It was warm and comfortable, with a huge full-length mirror and another surrounded by light bulbs, like you see in theatres. Caroline followed him in. Putting her hand on his shoulder she pushed him down onto the soft bench. "Close your eyes I'm going to work." Dan said nothing as she worked expertly on his face.

He felt foundation and blush and lipstick and eye shadow. It was cool on his face. It took about twenty minutes. "Open your eyes." Dan tried to see what he looked like but there was no mirror, only the impressive form of Caroline in front of him wielding a mascara brush. "Look up." And she did what she had to do. Then from behind her she produced a long dark wig. Dan let out a little gasp.

"Beautiful isn't it?" said Caroline as she brushed it out. "But your eyes are open bitch and you were told to keep them closed." She slapped his face. Hard.

He felt something cold on his forehead, and then the weight of the wig on the top of his head, and the light hairs tickled his shoulders. "Now you can look." Dan opened his eyes and couldn't believe the transformation. He wondered often what he'd look like as a girl with all his makeup done and a proper wig. Now he had his answer. He was gorgeous. And he also knew this was going further than he wanted. He stood up and sat down. He stood up again. He turned to see Caroline carrying clothes into the room.

"I can't. It's..... I don't want..." The look on Caroline's face made Dan feel a cold flush sweep through is body. She grabbed him by the balls and twisted.

"Look. I've had enough of you and perhaps you don't get this but let me explain. I've selected you to be the next photoshoot in Forced Femininity. You can't walk out. You can't leave. You signed an agreement."

Through the pain in his crotch Dan panted "I didn't agree, there was no signature."

"Oh, aren't you precious. This is even better. Suzanna get in here." Suddenly from a door Dan hadn't realised was there, a tall gorgeous blonde entered. No more than twenty, she was dressed in a slick PVC dress, zipped up the front. She wore skyscraper heels and was impeccably made up. Her legs were bare and long and tanned and she carried a sheet of paper and a camera.

"First the sheet. You didn't sign for a discount in the store. You agreed to take part in the photo shoot, to have it published and waived all your rights for us to exploit the pictures. Failure on your part costs you £50,000 penalty. It's legally binding. Tough luck bitch."

"Secondly, we took pics from the wall camera of your transformation but now you're struggling it makes it even better for us. Do you have any idea of the number of trannies who get off on the idea of being forced to dress? Hundreds and they love to see others in the same predicament. It's made me a small fortune."

"Congratulations! Your little resistance is certain to make you an internet hit. So just ignore the gorgeous Suzanne here. She's going to take some pictures while we get you into the outfits for the shoot."

And with that, Caroline twisted Dan's balls one more time and as he grimaced in real pain, a series of flashes went off.

This was awful. Dan felt his breathing quicken. He looked at his balls, they were red and swollen and there was a nick where Caroline's nails had drawn blood.

He knew forced transformations were exciting. He loved them too but he never thought he'd be in this position. He wanted to cry. Suzanna moved round getting some more pictures. Dan could only stare blankly in front of him.

"Suzanna, get some life in those pictures, they're pathetic." Dan wondered what Caroline meant, and suddenly he found out. Suzanna dropped to her knees and took Dan's cock in her mouth. She slowly sucked and licked it. Dan thought it was wonderful, even with the pain from his balls. He felt himself growing inside her mouth. Suzanne looked up at him and smiled while still sucking. Dan knew what would happen if she continued and felt himself tense. This was amazing. And suddenly she stopped, stood up and fired off some more pictures.

"Better" said Caroline. "It looks like the little sissy is enjoying herself now." Caroline stepped forward. "Right, turn around and let me get this on you. Look as if you're not keen but keep that hard-on going." Dan didn't need direction. Inside he was terrified where this was going, but he was so turned on. He saw a red vinyl corset being placed around his middle and pulled hard. Dan gave out a little gasp. Caroline smacked his butt. "Shut up. It's going to get even tighter before we're done sweetheart."

She started to lace the corset and Dan felt his waist being pulled in tighter and tighter. Just when he thought it couldn't go any tighter, Caroline started tying it off. "Sit." Dan did as he was bid. "Point your toe." Caroline then started rolling black fishnet stockings up his legs. First left then right. "Stand up." Dan did all he was asked. Caroline then expertly attached the stocking tops to the suspender straps dangling down.

She slapped his penis and it sprung to attention once more. "Good girl" said Caroline. "That bodes well for the shoot." Dan swallowed hard. He'd tried to forget this was just the start of the process. He swallowed hard.

Hadn't Caroline said outfits? "Shit" thought Dan; he was way in over his head.

"Pretty legs bitch. I think we're getting close to naming you. And I've got a lovely one picked out." Dan felt nervous and excited. Caroline produced a pair of black silky panties. "Don't these feel nice" she said as she rubbed the cool soft material across his made-up face. "Get them on and tuck but not too well, we like the bulgy panties shots."

Dan pulled them up as Caroline produced a matching bra and placed it on his chest and strapped him in.

"Last step." Caroline smiled at her little joke as she produced thigh length black leather boots with a five-inch heel. She zipped them up slowly. They were a perfect fit.

"Suzanna, come get a shot of the gorgeous Jennifer." So, Dan was no more. Now he was Jennifer and his evening was just about to begin.

"Right bitch, follow me" said Caroline. Jennifer swallowed hard. She had no idea what lay in front of her, only that she now regretted going to the book store this evening. "In" ordered Caroline motioning into another room with her head. Jennifer felt a cold wave sweep through her body and her legs began shaking and it had nothing to do with the five-inch thigh high boots she was wearing.

She froze in the door frame. There, in front of her was a dungeon. A very kinky dungeon. There was a St Andrew's Cross and a horse like she'd seen in school and a frame where there were places for hands and legs to be strapped. There were various straps and canes and things hanging on the walls. And a pole, from floor to ceiling, surrounded by lights, sitting in the centre of a small wooden dance floor. Jennifer wanted to run but felt a hard push on her back.

"Look sweetheart. You're here now. You're all dressed up and very excited. Look at your little clit poking through your panties. You want to do this. We want you to do this. And if you don't you can fork out the £50,000 penalty you signed for."

Suddenly getting more menacing, Caroline got right into Jennifer's face "And I haven't wasted half the night on a cowardly little sissy. So, get the fuck in the room, do what you have to do, model the outfits, take your punishment like a sissy bitch or else!" Jennifer had no idea what or else meant, but she didn't want to find out.

"Right, tell me how you're dressed."

"What?" Jennifer didn't understand the question. Caroline slapped her hard on the face, drawing tears.

"Look, tears are great for us. You look more like you're being forced and that gets the little trannies wanking furiously wishing it was them. Keep playing dumb and I'll keep slapping you silly. Your mascara is waterproof too. How are you dressed? Sunday school teacher?"

Jennifer didn't want another slap. Dressed as she was, she felt vulnerable and alone and terribly girly. "Like a hooker, a stripper?"

"Bingo bitch! Stripper or maybe even......." Caroline pointed at the dance floor.

"A pole dancer" ventured Jennifer timidly.

"Oh, what a clever girl! Start working it Jennifer. And look like you're loving it." As she issued her instructions, she rubbed the silky panties hiding Jennifer's dick, bringing it to instant hardness. "Lovely. Get to work."

Jennifer wobbled over to the pole and grabbed it. Suddenly music started up, a familiar brass intro. Caroline looked at Suzanne and arched her eyebrow while giving what Jennifer thought was a playful giggle. "Really? Every time?" Suzanne smiled a shy smile as "Man, I feel like a Woman" poured out of the speakers.

Jennifer felt very self-conscious as she grabbed the pole and tried to work it. She didn't feel sexy and was aware Suzanne was snapping away, enjoying her discomfort. She dipped and swung and posed and pouted but she knew it was rubbish. And she was worried. She didn't want Caroline to get upset with her again.

"Great. Your awkwardness is delightful and makes it look like you're being forced. Actually, I suppose you are being forced." Caroline moved closer. Jennifer who still thought Caroline was gorgeous visibly flinched thinking another slap was coming. She never knew what was next, praise or teasing or a slap.

12


"sleazy dreams"mr logan stories ezhibitionistluckiest son taboo sexstoriestwo mums two laps car sex confessionpreist non comsent literotocahuge black cock,ohhh fuck me hard,my slutmom ,asstr,incest"liter otica"/s/a-company-affair-ch-02"literotica girlfriend""mother and son sex stories"literotica trickinh naieve coworkerdaddy daughter missy literotica"thick alpha cock" ficrionliterotica stories familiensau"free sex"Literotica wife at church feteliterotica taming the bossMature tranny surprise sex storiesIncest stories: How i seduced my lonely motherMother inlow in Kitchen Incest litroticaparadise mom litarotica incestUSLMAN stories sexbought her dress sex story no bra voyeur/s/hot-times-at-a-campgrounderotic gangbang rape the lactating mother by intruder sexstoriesfindomliterioica marathiAphrodite Predator Guide"i straddled his chest"small shannon literotic"literotica shemale"/s/family-road-trip-2/comment/2119944Abel and eve taboo sexstories Brother fucks sister in backseat while parents drive laroticaLerotica Sex Stories Pussy Being Pushed To Its Alastic LimitPatreon tefler 150spanking boys bondage dildo stories literoticaLitirotica_the nymph's gifteroticaliteraticaTop 60 transexual juicy literotica storiesExpanding foam literotica"bbw literotica""family incest stories"அம்மாவும் சளைத்தவளில்லை litroticamother lick my daughters pussy lesbian incest confessionXxx stories of the wonderful adventure of miss kbeth raines nudeliterotica betagtIncest story. My older sister's big tits. Ch 01bus ride incest literotica"literotica app""gay sex stories""gay sex stories"cssa celebrities raped asstranalliterotica knotJulie's mistake chapter 15abandoned incest sexstoriesliterotica son magnum xxlbeach nudism literotica.comAsstr / enfwife first time lesbian pool party stories"literotica search""literotica incest"truck stop non consent literlticagiantess college dorm story"nifty erotic stories""big booty bitches"erin the office literotic/s/summer-with-trashy-slut-and-her-momwife boss party sex xxx lettersSTORY OF HEMA MALINI AND SERVANT RAMUliterociasoul calibur ivy literotica"dreams of desire"