Val's Dilemma

Val was depressed. He was 19 and had come to college from his small town and really felt out of his element. Admittedly he had felt like a fish out of water even at home. He was the moderately bright, slightly nerdy kid, never one of the popular ones. He was far from being some kind of Adonis - being about 5'8" and 140 pounds and no one's idea of handsome or muscular.

He had never really gotten dates even back home, but now in the big city on a major college campus, he was quite ignored. It wasn't that he never tried, but he never seemed to have any luck. Women seemed to find him humorous, and not in a good way. The last woman he asked for a date just laughed and walked away from him with no answer. Most just gave him a weak smile and declined.

His friend Geoff told him the biggest problem was who he seemed to be interested in.

"Look, bruh, you're not going to get anywhere with most of the women you're chasing. Those are the chicks who look for the super slick guys."

"So I'm ugly and I should chase ugly women?"

"There's a lot of nice looking women who just aren't the super hot ones."

The one Val was most fixated on was Casey. She was about 5'6" 115 pounds with a pretty face, nice medium size boobs, a cute ass, and brunette hair in a pixie cut. Val felt like he was really in love with her, but she would barely even speak to him at all. She didn't necessarily dress super sexy, mostly just jeans and a tee, but she had a beautiful smile and eyes that Val wanted to lose himself in.

Casey seemed to hang around with a group of women and there was no way for Val to insinuate himself into that group.

"If I could hang with her and her friends for a while, maybe I could figure out how to get her to like me."

"Group is all women, right?"

"Yeah, it really is."

"Well then, the only way for you to hang with the group is if you're a woman."

"Never work. No one would believe it if I tried to dress in drag."

"I don't mean just dressing like it, I mean actually being a woman."

"You mean a sex change? Doesn't that take a while? Besides, I don't want to spend the rest of my life as a woman."

"This is something very much underground. A pill that can change a man into a woman, and another one to change a woman to a man."

"And that shit works?"

"Seems to."

"And I could change back after?"

"Don't see why not. Just need one pill for each way."

"That would let me hang with her, find out what she likes, and maybe get her to like me as a person."

"Shit is expensive."

"I don't fucking care about that."

"And there is a certain fail rate."

"What do you mean?"

"Works about 90% of the time."

"And the rest of the time?"

"Sometimes nothing at all, sometimes leaves you in between."

"In between?"

"You may have something that's not clearly either a dick or a pussy. Or you might even have both."

"Shit. That could happen?"

"Most of the time either it changes you the way it's supposed to, or doesn't do anything at all."

"Damn. I got to think about this."

"Got a couple of choices - either do this, or find another way to get close to her, or find another girl."

"I can't figure out any other way to get close to her."

"Then either give up on her, or give this a try."

"I'd need both pills, so I can change back to a guy afterwards."

"You get the cash, I'll get the pills."

"Am I making a mistake?"

"Only you can decide that."

Val was torn. He wanted a chance to get close to Casey, but was leery of either being stuck as a woman, or becoming intersex. Mind you, he wasn't all that thrilled about being a woman, but he wasn't horrified, at least as long as it wasn't a permanent condition. He had a trust fund to pay for college and personal expenses. He got the money out of the trust for the pills.

It took about two weeks for Geoff to get the pills. He got one pink pill to change from a man to a woman, and one blue one to change from a woman to a man. Val had a small studio apartment near campus and Geoff took the pills to Val in his apartment.

"Okay, bruh. Here you go."

"These are them?"

"Sure are. Take the pink one now."

"And they work?"

"They work right 90% of the time."

"I'm still not sure about this."

"If you've changed your mind, I can try to find other buyers. Might not get all your money back, but probably most of it."

"I'm just a little scared."

"I know someone who took a pink before. You want to meet her before you decide?"

"Her?"

"She only wanted to go one way. No desire to go back to being a guy."

Geoff took Val to see Justine, over on the other side of town. Justine was 25 and about the same height as Val, but with a nice ass and c-cup boobs. She had a cute face with bright red lipstick and perhaps a little too much eye shadow for Val's taste. She wore a short skirt and a top that let a little midriff peek through. She had shoulder length hair, highly styled.

"You're Justine? It's hard to believe you were ever a guy."

"I was not a guy. I was assigned male at birth, but I grew up knowing I was really a female."

"I'm sorry. I didn't mean - "

Justine turned to Geoff. "She is taking one of the pills?"

"She is - I mean he is."

"Okay, guy, you get out of here and I'll take care of our little friend here."

"But I drove him over here."

"I'll get her home safely. She needs a woman to guide her through this. She doesn't need you. Out!"

"I'll talk to you later, Val."

With that, Geoff turned and left. He looked puzzled and unhappy as he went. Val was kind of puzzled by it all.

"Why did you make him go?"

"Some guys have been known to decide they needed to check out the changes by fucking the woman after she changes - whether or not she wants that."

"I don't think he'd do that."

"Better safe than sorry, baby."

"So you'll supervise me through my change?"

"Yeah, though honey, you are one of the least likely prospects for this that I could imagine."

"I... I have my reasons."

"I could be wrong, but I'd guess you have no idea what it's like growing up trans."

"I'm trying to get close to a woman that I'm interested in."

"By becoming a woman? Got to be one of the worst reasons I've ever heard for doing this."

"May not be a good reason to you, but it's my reason."

"You look like a bit of a nerd, and I'm sure you caught some crap over it."

"Yeah, some."

"Doesn't compare to years of people calling me a faggot, a sissy, saying I'm perverted and going against God's plan, telling me I'm going to hell, beating the shit out of me when they thought I was being too effeminate."

"I'm sorry for that."

"All because I knew I wasn't what they said I was. I thought about suicide before I found there was a pill that gave me a chance to have a body that truly matched who I was inside."

"Now you do."

"Do I ever, and I love it."

"So how does it work?"

"It doesn't just give you boobs and change a cock to a pussy. It goes a lot farther than that."

"Oh, what else?"

"Your hips get wider, your waist gets narrower, your skin changes, your face changes."

"Face changes?"

"You've never noticed the difference between female and male faces? The nose, the jaw, the cheeks, the eyes all look different."

"And this will change all that in me?"

"If you go through with it, yes. If you change your mind, you can stay as you are."

"No, I want to do it."

"Before you have second thoughts and change your mind?"

"That's part of it."

"Out of curiosity, are you more interested in men or women?"

"Women, why?"

"You don't identify more strongly with women. You aren't sexually interested in men. Are you really sure you want to do this?"

"I... I do."

"Fine, then. Do you want to watch what's happening to you as it happens?"

"I suppose."

"Come with me."

Justine led Val into her bedroom, where there was a full length mirror on a closet door. She dragged a chair over in front of the mirror.

"Take off your clothes and sit down here."

"Why do..."

"Honey, I like men, not women, and I like my men tall, dark, and handsome, not short, pale, and ordinary - no offense intended. If you want to see what's happening then you need to take your clothes off."

Val started to take off his clothes, then turned to Justine. "Then after?"

"After, we'll use some combination of my stuff and yours, then we'll go shopping for better clothes."

Val stripped down to his jockey shorts, then paused and took a deep breath before pulling them down and kicking them off. He looked nervously at Justine before sitting down in the chair. Justine lifted Val's arm, smiled and shook her head.

"Honey, I was shaving my legs and underarms even before I changed. We'll get you fixed up later."

Justine gave Val a glass of water. He got his pink pill, looked at it, then looked at Justine, took a deep breath, shook his head, then put the pill in his mouth and drank the water, washing down the pill.

"Just relax, honey. It will take a few minutes to begin to have an effect."

After a few minutes, Val began to feel a tingling throughout his body. As he looked in the mirror, then first thing he noticed was his body hair changing and becoming lighter. He felt something in his groin and watched his penis and testes withdraw into his body. As they did, they began to form a vagina. Val then felt a weight in the chest as breasts began to form.

As the breasts grew, the nipples got larger and became darker and more pronounced. Val's head felt funny and she watched as the nose became shorter and narrower, then the chin narrowed and the top of the head seemed to become rounder. Her eyes seemed not to be as deeply set. Her eyebrows thinned out and her Adam's apple disappeared.

Val was surprised but not entirely displeased with how her face looked. Val felt something around her middle as she watched her waist get narrower and her hips grow wider. Val no longer recognized herself, and she was now definitely female, though it took 15 to 20 minutes for all the changes to take effect.

Once it was done, Justine helped Val to her feet, and she was surprised to find herself a bit weak in the knees. Justine led Val into the bathroom, where she proceeded to brush Val's hair into something closer to a pixie style. Val's hair hadn't been super short anyhow, and had grown a bit from the pill. Then Justine proceeded to shave Val's legs and underarms.

"Would you like me to shave around your pussy, too?"

"It looks a bit bushy."

"We don't have to go completely hairless, if you don't want."

"What do you think?"

"I'm hairless down there, but I'm more femme than you're likely to be."

"Shave it. That's what I see in most pix I see online."

"Porn is a different world, but we'll shave it. It'll always grow back if you want."

Justine had Val lean back and spread her legs wider. She got some clippers and trimmed the hair shorter before shaving the rest off. Justine led Val back into the bedroom, then over to a dresser, where she pulled out a pair of panties. They were definitely feminine but not super frilly. Val looked at Justine, then looked at the panties, took a deep breath, then stepped into them and put them on.

"Honey, you're a b-cup, so my current bras won't fit you, but I have some from before that might work for you."

Justine pulled out a pretty pink bra from another drawer and held it out for Val to put her arms through. Val bit her lower lip then stuck her arms through the straps and Justine fastened it behind her.

"We may need to get you some front snap bras until you learn to handle regular ones."

Justine took Val's hand and walked her over to the closet.

"I don't guess that you're quite ready for skirts or dresses."

Val looked pained and shook her head. Justine smiled and pulled a pair of jeans out of the closet. She held them up in front of Val.

"I can't just wear what I wore here?"

"Men's jeans are cut with a larger waist and smaller hips. These will fit better."

Val slipped the jeans on, then went to zip them up. She fumbled a bit since the zipper was on the other side, then managed to get them zipped.

"You want to see how your tee shirt fits now?"

Val walked over to where her old clothes were and pulled on her tee, which was a lot more snug and seemed to emphasize her boobs.

"Well, I - "

"As long as you don't mind advertising the goods."

Val blushed, then sat down to put on her socks and sneakers. Her feet were close enough to the same size for the shoes to work. After she finished, Justine helped her up and led toward the front door.

"Okay, girl, now we need to buy you a few more clothes of your own."

"What did you have in mind?"

"I'm guessing you're going to be a jeans and slacks kind of girl, but you'll need some more along with more bras and panties. Might want a pair or two of flats, as well."

"It's going to be more complicated than I realized."

"Do you work out at all?"

"I jog a little."

"You'll need a sports bra, and you may want to find a jogging partner."

"Never thought about that."

"You can't take safety for granted anymore."

"This may be more challenging than I expected."

"You're starting to catch on, girl."

"It feels weird having you call me 'girl'."

"Honey, you've got a lot more weird to go."

"That's not reassuring."

"But true. Now let's go shopping, girl."

Justine drove them first to a discount store, where she helped Val select some bras and panties, then picked up a few pair of jeans and slacks. Justine made Val buy one nice blouse, along with a sports bra. Then they went to a thrift shop, when they got a couple pair of nice flats.

"You sure you don't want at least one skirt, girl?"

"I don't know."

"Unless you're going for the butch dyke look, you ought to have one skirt for dress up."

"I suppose so, then."

Justine took Val over and they found a nice black skirt that came to just above the knee. Justine made Val try it on, and it fit well. Val looked uncomfortable in a skirt, but bought it anyhow. Justine took Val to a hair salon where they did a light trim and style to make Val's hair more feminine. Then Justine took Val to a nail salon for a mani-pedi.

"I don't know how I feel about nail polish."

"We could clear coat, or put some very light color on it. Besides they need to make those nails and feet look a little nicer."

"Are you sure?"

"Go with it, and trust me honey."

Justine also took Val to get some subtle makeup. Val was leery about that, but after the person put it on her, she was amazed at how she looked. After shopping, they went to dinner on Val's treat. They just hit a nice little Italian place that wasn't some chain restaurant. Justine had a glass of wine, but Val was under the drinking age.

"Your friend said you were planning to change back to a guy later."

"Yeah. I don't plan to stay this way. No offense."

"It isn't for everyone. I don't know how long you planned on this but I've gotten word from some folks who switched back. You don't want to do it too soon."

"What do you mean?"

"People who took a pill to change back in less than two weeks were more likely to get fucked up by it."

"I didn't figure I'd be doing this overnight."

"The risks drop off as you stay on longer - at least up to about a month. After that it doesn't change much."

"So a month gives me my best chance for no problems?"

"A month, or more - more doesn't hurt, if you want to stretch it out."

"That's good to know."

"You want to do a little girl's night out, or would you rather go home?"

"I've had enough fun for one day. What about tomorrow?"

"I have a hot date tomorrow night, honey. I'd offer to set you up, but I don't think you're looking for a guy."

"I think I'll pass on that. Maybe we could do a rain check though."

"Okay. By the way, you might also want to pick up some tampons or pads just in case you have a period before you take that second pill."

"Okay, but I've got no idea - "

"I can help when the time comes - unless you have an in with your girl then."

........................

Val began to put away her new clothes when she got home. She looked at herself in the mirror, which she seemed to have little chance to do during the whirlwind earlier with Justine. She was surprised at how different she looked, and yet so similar. She could easily see herself as the sister of the guy who had taken that pill.

Val wasn't quite sure how she should feel about all this. She'd done it to get closer to Casey but was having some second thoughts. Then again, from what Justine told her, she should hold off on any thoughts about taking the other pill. Maybe it would change her back just fine, but she'd rather not take the chance.

Val decided she needed to set up an online presence for her new self, even if it was temporary. She set up an email account under Valentina instead of Valentin, then set up some social media accounts as Valentina as well. She used her phone to shoot a selfie of herself which she put on the accounts. She sent friend requests to Justine, Geoff, and her old self.

As she was sitting around the flat, she heard knocking at the door. She wondered who exactly might be coming by. She looked through the peephole to see Geoff. Val unlocked the door and opened it slightly. Geoff seemed upbeat and friendly and was carrying a twelve pack of beer.

"What's up, Geoff?"

"I wanted to see how you were doing and help you lighten the mood and get more used to the new you."

"Okay."

"Can I come in?"

Val opened the door and Geoff walked in carrying the beer. They put it in the fridge and each got a bottle and opened it. Val's studio apartment had a sofa in addition to the bed and a table that Val studied at where she had her computer. Val decidedly did not want to sit on the bed, so she sat on one end of the sofa. Geoff sat in the middle of the sofa, putting him closer to Val.

"You're really getting into this chick thing - hair style, nail polish, makeup. I'll bet you even have a skirt now."

"Justine wanted me to do this."

"Didn't fight it too hard though."

"Doesn't mean I'll continue it though."

"You should. It looks good on you."

Geoff didn't seem to make any moves on her, but was chatty and friendly. They sat drinking beer, having several more after the first one. Val found herself getting a bit drunk just from the beer. She went to the bathroom and as she came out, staggered a bit and fell over onto the bed. She lay there a moment thinking how restful it felt when she found Geoff beside her on the bed.

"Geoff, I think - "

"I think so too. You're a woman now and a very pretty one. You deserve a chance to know what that means with someone who wants you."

Before Val could protest, Geoff began to kiss her. Val was drunk and conflicted and very confused. Geoff brought a hand up and began to caress one of her boobs. She didn't think she wanted him to do that, but it did feel good. As he kissed her, he slid his hand down, then up under her top and unhooked her bra.

Val squirmed and moaned in protest as Geoff continued to kiss her. He brought his hand back around and began to fondle her boobs directly. Val didn't want him to do that, but it felt so good, she couldn't protest too much. He lifted up on her top to expose her boobs then quit kissing her to begin to lick and kiss her breasts.

Val's nipples got very hard and she moaned both in protest and in pleasure. As Geoff sucked on her boobs, he moved his hands down to unbutton and unzip Val's jeans. Then he snuck his hand inside her jeans and panties to stroke her pussy. Val really began to squirm and Geoff took advantage of that to pull down her pants.

Val was naked from the waist down and had her top bunched up above her breasts. Geoff lifted her slightly and pulled off Val's shirt and bra, then swung Val over so she was lying full on the bed. He resumed kissing her boobs and fingering her pussy, even as he began to shed his own clothes. Val didn't feel like she wanted to do this, but it felt so good, she couldn't make him stop.