Author Topic: How I Became Alison (m to f)  (Read 3083 times)

Offline JayneDeviant

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How I Became Alison (m to f)
« on: August 24, 2020, 10:23:10 AM »
How I Became Alison
Part One

I was just getting used to the fact that I was a gay slut, when things really escalated way out of my control, in ways I could have never imagined. It was due to Mister Spandwick, an old man whom I had met through some friends-of-friends.

I was used to the fact that old men found me attractive. They were always buying me drinks, inducing me to come sit on their laps, stick their old hands down my pants and play with me, then sharing me with their septuagenarian friends. I let them have their fun. After all, it was fun for me, too. I enjoy being an object of desire, no matter who it is that's desiring me.

Mr. Spandwick looked at me with a similar hunger in his eyes that evening... but there was something different about it. We were at a fundraiser at a private club, I had been there ostensibly to 'mingle.' He was really inspecting me.

"You have very feminine features," he observed, in his old, hoarse voice.

"Yes," I smiled. "I've heard that."

He ran his hands over my face. "So smooth..." he continued. "How often do you shave?"

"Er... everyday, but nothing ever grows in." This line of questioning was making me a bit uncomfortable... I wasn't used to such a close inspection.

He nodded. "Will you come home with me?"

I laughed. Finally, back on familiar ground. "Sure, old man. You got it."

As we walked out of the club, we passed a party store. "Let' stop in here first!" he said, leading me by the hand.

"Uh, okay..."

Once inside, he scoured the shelves until he found a blonde wig. Without asking, he put it on me, then took a step back. "My God, you look just like her!"

"Like who?" I asked, feeling kind of silly standing there with a girl's wig on.

"Never mind that." He snatched the wig off and paid for it quickly, then grabbed me by the hand to leave.

"Where... where are we going now?" I asked.

He checked his watch. "God damn it, the stores will be closing soon!"

Out next stop turned out to be some high-end teeny-bopper clothing store. "Sir, the store will be closing in five minutes..." said the bored teen who was working that final shift.

"Fine, no problem." Mister Spandwick said, immediately coming over to the rack of T-shirts. "What size do you wear?"

"Uh... I don't know... a medium, I guess. I don't really buy..."

He held up a hot pink T-shirt with a unicorn on the front. "Would that fit you?"

"I guess I could try it on..."

"There's no time!" he shouted. He threw the T-shirt in a basket along with some other clothes. Then he went to a rack of earrings and chose some real big hoops. Finally, he found a makeup display - watermelon flavored lipstick - and paid for it all, grabbed the bag, grabbed my hand, and we were off.

"What is all this?" I asked for the tenth time. "What's going on?"

"You're about to make me a very happy man, Jay," he said.

*****

Maybe you've already figured out what was going on... but not me. I'm fairly slow on the uptake, I suppose. He giggled the whole way back to his house... which was an old mansion behind on iron gate. This old man clearly was very well set-up. He sat me down on his couch and poured me a glass of bourbon.

"Here, I want to show you something..." he said, and brought out a photo album with pictures of his family. This was a first... No one had ever brought me to their home so they could show me pictures of their families before! He flipped through the pages... "Here is my son, and his wife..." His son was a very handsome man and his wife was very beautiful. "...and here is the light of my life, their daughter... Alison!"

It was a very little girl, dolled up. She looked like she was five years old and about to enter a beauty pageant, sitting on her grampa's knee, grinning with dimples.

"She's very cute, but I don't see what this has to do with..."

He flipped pages in the album, and as he did so, I saw little Alison grow up,... one birthday celebration after the next, as a middleschooler, a highschooler... In each picture she grew taller and more beautiful... Finally, he showed me a picture of her on her 18th birthday. She was a gorgeous young woman... Tall and slender with full breasts. She had long, blonde hair, a hot pink T-shirt, bright red lipstick, hoop earrings, and...

Oh my God.

I looked up from the book at him. He was smiling back at me, his eyes wide with desire.

"You... you think I look like her?" I asked.

He nodded eagerly, running his hands along my cheek bones. "Very much," he said, licking his lips.

"But... I'm a boy! I don't do this sort of thing!"

He handed me the wig and the items he had bought at the store. "Put them on," he said.

"Listen... I'll gladly suck your cock for you, if you want, but this is kind of nuts, I'm not..."

"I'll give you five hundred dollars to put them on."

*****

I came out a few minutes later. I have to admit, I did look like a hot, teenage girl.

What do you think?" I asked.

"Call me gramppa."

"What do you think, grammpa?

"It's missing something..." He reached into his pocket, "Here chew on this!" He threw me a pack of gum. "She's always chewing gum," he explained.

I have to admit, I felt like I was getting into character. I came over and sat down next to him, smacking the gum loudly.

"Alison?" he said.

"Yes, gramppa?" I replied.

"Come... come..." He breathed heavy, and for a moment I thought the old coot was going to have a heart attack. "...come sit on grampa's lap, like you used to..."

I blew a big, pink bubble, then did as I was told. I could feel his cock through his pants, of course, it was long and hard and ready to blow at any moment. I shifted my ass on his lap a bit. He put an arm around me and pulled me into him.

We kissed, long and hard. I'm used to sucking lots of cock, as I said, but really haven't spent that much time just kissing men. But this was something different. I did feel that I was transformed into someone else. He stuck his tongue into my mouth, and I did likewise. We we kissing deeply and passionately when I could feel him coming in his pants.

"Ah... ah... ah...!" he called out, as he moved his hips. When I finally got up, I could see his entire lap was wet with cum. It had been a super soaker.

"That was... amazing... That was... the best..." he breathed. "Oh my God..."

"Glad you liked it, grampa" I said, standing up, and going to collect my things.

"Wait, don't go!" he pleaded. He reached for the remote control and turned on the teevee. There was a Disney XD show on about kids in high school. "Alison loves this show!" he said. "Come sit beside me and watch it. Please!"

I shrugged.

"Alison loves Macaroni and Cheese. Can I make you some?"

"Sure, sounds good," I said, and settled in to watch the program.

*****

I had thought this was going to be a one-off experience. Something that happens once that you talk about years later when you're exchanging stories with your friends.

I had no idea the roller-coaster I was in for. I had no idea all of the ideas that Mister Spandwick was planning. I had no idea how intense and surreal things were about to become.

...but that's a tale for another day.
« Last Edit: May 12, 2023, 06:14:53 AM by JayneDeviant »
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oh2bedesired
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Re: How I Became Alison (m to f)
« Reply #1 on: August 24, 2020, 10:34:12 AM »
 I really like this,sounds like something I'd like to do,except my tshirt would be  long enough to cover my tush and my panties would be bikini

Offline JayneDeviant

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Re: How I Became Alison (m to f)
« Reply #2 on: May 12, 2023, 06:17:21 AM »
Part Two

I had told you about how I had met old Mr. Spandwick and how he had insisted on dressing me up like his granddaughter, Alison, before having his way with me. Pretty hot, right? I thought so too, but it did freak me out a bit... It just wasn't the kind of thing I had ever done before, no cross-dressing, nothing like that, so that was all new territory... acting as a kind of sexual surrogate between an aging grampa and his young, vivacious granddaughter.

Of course, at that point, I hadn't actually met Alison. She'd just been a girl in a photo album. Well, that was about to change.


He let me keep the wig and the clothes... in fact, he insisted, so that I could 'practice,' but warned me to keep them nice. "Alison always keeps her clothes nice!" he'd said. It was pretty late when I finally got changed into my normal clothes and caught an Uber home. All things must come to an end, unfortunately, and now that I was nearly home, that became all too apparent.

"Is this really where you want to go?" asked the Uber driver. It was a strange trip for him, picking me up at fucking Buckingham Palace, and then dropping me off in the slums.

"Yup, this is home," I told him, getting out and standing on the street. In the distance, police sirens wailed and glass bottles shattered.

My "real" life is not nearly as glamorous as my fantasy life. I don't think any of the CEOs and hedge fund managers whose cocks I've serviced over the years would ever imagine that I was from the wrong side of the tracks. Not that any of them give two fucks about what my life is like outside of sucking their cocks.

I live with my parents, who are basically drunks and get by on welfare. There are often homeless people hanging out front of our home, begging for change. The roof leaks whenever it rains, and even when it doesn't. They have no idea what their only son does for a living. Three years ago or so I'd told them I worked at Wal-Mart, and that lie satisfied them and they never asked me about it again.

If they knew I was gay... let alone fucking old men for money... they'd totally freak out. I shudder to think about it. My dad would probably beat the living shit out of me. He's one of those old-school dudes, you know, extremely "manly", hates all gays and girly boys. He's always talking about how God should just wipe out all the fags, shit like that.

"Where the fuck you been?" he shouted. He was sitting in his favorite armchair, smoking and drinking beer, watching sports.

"Just working late..." I mumbled, running in to my room.

I quickly took out the blonde wig and shirt and skirt and shoved them into the back of my closet, then breathed a sigh of relief. That had been my biggest fear, that they would have caught me with them and I would have had to have come up with some crazy lie. Now I could relax. I plopped in bed and checked my messages. There were a few men requesting to see pics of my cock... Quickly, I pulled my pants down, rubbed it until it got nice and hard, then snapped a pic and sent it out. All in a day's work.

The next morning, I got up and went down to make myself some breakfast. Hopefully the milk hadn't turned. My dad was still in his armchair, beer still in hand, still watching television. I don't think he'd moved all night. Flies buzzed around him.

"Where the fuck're you going, you little twat?" he shouted.

"To work, dad," I said, adding, "It's morning."

"What? Don't you fucking jerk me around, you little..." Then he turned his head slightly so that he could see out the window. "Well, I'll be, it is fucking morning!"

My mom came out of the bathroom, her hair in curlers, smoking a cigarette of her own. "Pick me up some scratch-offs on your way home," she told me, a voice like sandpaper.

"Sure, mom, you got it."

I was barely out the door when my phone buzzed. It was one of the men I had texted my cock pic to last night. He wanted to get together and was willing to pay my asking rate. I texted him back, told him I'd be right there.

He worked in a tall building downtown. His text said I should just tell the receptionist that I was his 9 o'clock.

When I got there, he told me he had just fired a bunch of people that morning, and it had gotten him so worked up he just had to fuck something. So I got down and sucked him off as he fired someone else over the phone, then came in my mouth.

I swallowed it all when my phone buzzed. It was Mr. Spandwick. He said he needed to see me right away, that it was urgent.

I went into the elevator. There was a man crying, holding a box full of his personal effects. He'd clearly just been fired. "Tough break, pal," I said, smiling to myself, and licking the cum from the corner of my mouth.

******

Spandwick's limousine picked me up from outside the office building almost immediately.

"Where are we going?" I asked, climbing in.

"Good to see you, too, Jay!" Spandwick smiled at me. Then, "Okay, driver!" he called out.

The limo took off at a brisk pace. We were clearly trying to get somewhere quickly. "Uh... you didn't want me to have the wig, did you? Because I left it at home and..."

"No, no... Not now. This is just a little... research expedition, you might say!"

Research? We were headed down one of the more affluent shopping districts, where a cup of coffee cost more than the mortgage on our home, and everyone looked like models and actors. Mr. Spandwick was looking out the windows with a pair of binoculars. "Damn it, I just saw her before I called you... There! Driver, slow down and pull over!" He handed me a pair of binoculars. "Look, you see her?"

"See who? Who am I looking for?"

"Alison, of course! My granddaughter! She's out shopping!"

There were tons of beautiful women out shopping that morning... All gorgeous. But one of them sure stood out, and in that moment, my breath caught.

I put the binoculars down, doubting my eyes, then looked again.

She was the most beautiful woman I'd ever seen.

I know you're thinking, but wait a minute, Jay, aren't you gay? Yes, Sherlock, I am gay, but I'm a gay man who can recognize and appreciate a beautiful woman when I see one. She was tall, had long, blonde hair, and a perfect body. I had to wonder if her breasts were implants, because they just didn't seem like they could have been natural. They bounced as she walked, and the bright red dress she wore revealed plenty of cleavage. In one hand she carried two large bags with the names of designer labels on them. Clearly she'd been out shopping and had expensive taste. In her other hand, she held a Danish which she nibbled on.

"Let me see again!" said Spandwick, grabbing the binoculars and staring out the window. "Oh God, I love that dress. Jesus fucking Christ, she drives me crazy. I just want to fuck her. I want to grab those boobs and squeeze em until they burst, oh yeah..." He had his other hand down his pants as he spoke, licking his lips.

"How... how long have you felt this way about her?" I asked, half-afraid to hear the answer.

He put down the binoculars, and I could see that his eyes were full of mad, hard-on lust. "Quite some time, and we'll leave it at that."

I looked down at his pants. He had a major hard-on which didn't look like it was going away.

He handed me the binoculars again. "Now look at her," he said. "I want you to really pay attention to her... to her body language, the way she walks..."

"Uh, okay, why?"

"Why? So you can act more like her, of course!"

She was walking toward the corner, where a homeless person sat out, begging for change. It was so incongruous, this woman of such beauty beside this creature of filth. I wondered how she'd act.

She came to the homeless man and smiled at him. For his part, his eyes were wide with lust. I'm sure he'd been ignored all morning, and now not only was there someone paying attention to him, but someone who looked like they'd just walked out of an issue of Playboy magazine.

She still had half the Danish. She reached out to hand it to the homeless man, who grabbed at it greedily. He didn't look like he'd eaten anything in a long while... But then, at the last moment, Oopsie! She dropped the Danish on the ground.

Not that he'd care, he wasn't about to let it go to waste... But then her high heel came down and smooshed what was left into the sidewalk. She laughed when he looked up at her, not fully comprehending what had happened, and she spit in his face.

That's right. She spit in the face of a starving homeless man.

Oh my God, she was one royal bitch! I couldn't believe my eyes, I'd never seen anything so incredibly cruel before!

"Did you see what she just..."

"Jay, quick, suck me off... suck me off... Please..."

Spandwick had his meatstick in his hand, jerking himself off rapidly.

I went over to where he sat, and he grabbed the back of my head roughly, forced me down. I took his entire cock in my mouth and down my throat... which was considerable.

He did not let me up for air, not until he was done. He moved my head up and down, up and down, and I could tell he was just stating at his granddaughter the entire time. "...oh my god, come to grampa darling, come to grampa... Those tits, those perfect... oh... huge... oh... tits... I just wanna suck on em... Here I come baby, here I... Shit! She sees us!"

"What?!" And I sat up just as a huge glob of cum came shooting out of his cock.

"Lick it up, quickly! She's coming over!"

Like a hungry dog licking at his master's leftovers, I licked up as much cum as I could, swallowed it all with a gulp just as he zipped up his pants.

There was a rapping at the tinted window. "Is that you, grampa?"

Quickly, he rolled down the window. "Well, yes! Hi, Alison! How good to see you! We were just driving by and I said, why that looks like my beautiful granddaughter! Can we give you a ride anywhere, sweetie?"

She sighed deeply. "I guess."

She came and got in, sat down, crossed her legs. "Hi," she greeted me.

"Alison, darling, this is my friend Jay! Jay is my new, er, personal assistant!"

"Very pleased to meet you," I said.

"Yeah, whatever." She put in a stick of gum and began chewing it. "I'm meeting my friends down at the Palace. You can drop me off there if you want, gramps."

"Sure, sure, my pleasure! I see you went shopping!"

"Yeah, I got a few things."

I saw now that it was a Victoria's Secret bag. She pulled out a skimpy lingerie set. "Think my boyfriend will like it?"

"Haha! Yes, I daresay he would... Ha, oh my... You know, I'm just going to hop out here and use the bathroom at that café. I'll be right back." Spandwick got out and went into the café. I was sure he was going into their bathroom just so he could finish jerking off properly.

Alison put the lingerie back in the bag, then looked at me with an amused glance. "Personal assistant, huh?"

"Uh..yeah, that's right," I said, embarrassed.

"You don't fool me. I know what's going on."

"I don't..? I mean, you do..?"

"You're grampa's boytoy, aren't you?"

"What? No, that's ridiculous! I'm his assistant, just like he said. I just... make him coffee and, you know, stuff like that."

She leaned forward, revealing much more of her immense cleavage. "Can I tell you something, Mr. Personal Assistant? I have a boyfriend who likes to kick the shit out of spineless faggots like you just for fun, and sometimes I watch him do it. I love it. I love watching faggots get beaten up. They're all crying and bloody... It's amazing. He's amazing. It's even better than when he beats up homeless turds."

I seethed with a sudden anger. "Well, I hope you tell your boyfriend that it's 2018 and gay acceptance is..."

She took out her phone and snapped a picture of me. "Thanks," she said.

"What did you do?"

"I just thought my friends might get a kick out of seeing the piece of shit faggot that's sucking my perv of a grampa's cock. And I'll show it to my boyfriend, too, so if he ever sees you, it's lights out, boytoy."

"Now, listen here! You tell your boyfriend..!"

But just then the limo door reopened and in stepped Mr. Spandwick. "There, told you I wouldn't be long! Now, did you two get to know each other?"

I crossed my arms. "Yes, I'll say."

Alison laughed. "You can let me off here," she said, after we had driven another block. "Thanks for the ride, gramps. And very nice to meet you, Mr. Personal Assistant." She winked at me and got out of the limo.

Spandwick watched her walk away. "Oh my, that ass... Just perfect. She is a perfect piece of ass, is she not?"

"Her personality leaves a little to be desired, don't you think?"

"Her personality?" He looked at me like I had just spoken in a foreign language. "You pay attention to that personality. Because that's how I want you to act, get it?" He reached into his jacket and pulled out a stack if hundred dollar bills, handed them to me. "From now on, you're my Alison. So any criticism you have of her personality, you're just criticizing yourself. You understand me?"

"Sure, I understand you."

"Good. Now see that homeless man over there? I want you to go over there and spit on him."

"What? That's crazy!"

"This is the most lucrative job you'll ever have, Jay, but I told you to pay attention to how she acted. Now do it!"

I got out, walked over to the homeless man. My, he looked pitiful. He looked up at me, like I was going to help him.

"Change? You got change?" he asked.

I looked over at the limo, then back at the homeless man. I gathered a mouthful of spit and let him have it.

"You son of a bitch!" he yelled, wiping it away. "God damn you! You think I'm just a piece of trash? An animal! Well fuck..."

"What seems to be the trouble here?" It was a cop who had just walked onto the scene.

"He just spit on me!" yelled the homeless man, pointing at me. "I wasn't doing anything, and he just fucking spit on me!"

The cop smiled. "Listen, buddy, vagrancy is against the posted rules of this shopping district. Panhandling is a crime. I could lock you up right now if I wanted to."

"But I wasn't doing anything!" the homeless man pleaded. "It was him! He just spit on me for no reason!"

"All right, that does it!" And I watched as the cop immediately shoved the homeless man to the ground and slapped handcuffs on. "Sorry about that, sir," he said to me as he dragged the poor vagrant away. "Enjoy the rest of your day."

Stunned, I got back in the limo. I couldn't believe what had just happened. I'd spit on a homeless man, and the homeless man had gotten arrested.

"You see?" said Spandwick, slapping me on the back. "That's your lesson of the day! More important than any dresses or wigs. To be a beautiful person, you have to truly act like one! You have to know that you're better than everyone else! You have to know that they're all beneath you! That's the attitude Alison has that I find so intoxicating, and that's the attitude I want you to have. Got me?"

I nodded my head.

"Good. Now come over tonight, around 8 o'clock. And wear the wig and the dress and be sure to put on lipstick. I plan on fucking the shit out of you... Alison."

"Y-yes, sir," I said.

Everything was so crazy and happening so fast. I thought back to that morning, when I'd smirked at the man in the elevator who had just gotten fired... There was a cruel streak in me, deep down, a certain sadistic glee. I did like the idea of being one of the beautiful people. I liked the idea of being above the rest of them... And maybe this transformation was just what I needed to get more fully in touch with that side of myself.

...to be continued!
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