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Tservo96 — The Bet: A TG Story Chapters 4-6 [NSFW]
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Published: 2014-11-25 17:54:21 +0000 UTC; Views: 22412; Favourites: 39; Downloads: 0
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Description Chapter 4

Heather sat down next to Jamie on the sofa. She took her hands in hers and squeezed “You just keep going like you said earlier”

Jamie nodded and said “I think I need to go take a shower” as she kicked off the heels.

Heather kicked back as Jamie left the room. She put her hands behind her head and said “Take your time”

Jamie just smiled over her shoulder as she left the room.

She striped down and made her way into the bathroom, looking at the myriad of new choices that had appeared.

The sight of the boxes of tampons and pads made her heart jump a bit as did the lady Schick razors.

Jamie stepped into the warm water and let it flow over her body. She was surprised at how heavy her hair felt now that it was wet. She began to relax a bit as the water ran down over her and she soon found her hands exploring.

Her fingers gently probed and explored her new anatomy and new feelings exploded inside her in a rush. As her heart fluttered, both of her hands went to work in a way she was powerless to stop. Jamie let her curiosity take over as she realized just how good it felt to her.

Her hands moved faster and faster until she climaxed in an amazing rush of pleasure. Her knees buckled and she felt muscles clenching and tingling that she didn’t even know she possessed. Her left hand shot outward and had to hit the wall to brace her trembling body as her heart raced and her stomach flipped in excitement. She could tell she was sweating even with the constant shower water running.

A sly smile crept across her lips. “Wow” she thought “That was so much more intense than anything I experienced as a guy” as she laughed in spite of herself. Her hands continued to rove and she gently caressed her breasts. The more sensitive nipples gave off their own pleasurable vibe and she realized “Boobs are fun for all of us” and she shook her head at how stupid that remark sounded in her own mind.

After washing her hair and steadying herself for a few minutes, Jamie tried her hand at shaving. Her armpits went fine and so did her legs for the most part.

“Dammit” she said out loud as she nicked her ankle on the outside of her left leg. “I’m not a contortionist for Christ Sake…”

As the water began to cool, Jamie wrapped up her first time caring for her new body and stepped out to dry off. She smiled once more at having to wrap the towel around her top half now and she wrapped her hair up in a separate towel to dry “Just like in a commercial” she said to her reflection in the mirror.

Jamie came out into the living room to find Heather now dressed in a long skirt and white blouse. “Where did you get a new set of clothes?” she asked.

“What’s the point of having a best girlfriend if I can’t borrow from her wardrobe…I raided your closet while you were in there; what do you think?”

“You look fine” Jamie said.

“Thanks…you’ve got some nice stuff in there and our sizes aren’t that different. In fact, we’re the same size in shoes so whenever you want to borrow a pair of mine; be my guest” Heather said.

They both sat down and Heather gave Jamie a knowing glance and a slight tilt of her head. Jamie erupted in laughter and just nodded.

“So: as maybe the only person who has ever had a fully functional male orgasm to compare with a female one…which is better?” Heather asked.

Jamie blushed and said “Female”

“I knew it” Heather yelled.

Jamie just continued to nod and smile.

“So, do you think you’re going to like it on our side?” Heather asked.

“I don’t know yet…it’s my first day and I haven’t done 99.9% of the things I’m going to have to do” Jamie said with a shrug of her shoulders.

“That’s why I’m going to help you get ready and then we are going out to lunch…my treat” Heather said.

Jamie’s eyes widened a bit.

“You don’t think you can hide inside the rest of your life…you’re going to have to go out. Might as well get it over with and start doing it. Besides, no one but us knows or realizes what has happened. If you have cards and licenses in this name with your picture on it, then reality has changed and to everyone else…you are and have always been Jamie Campos” Heather said.

“I know but that’s what’s scary…everyone else knows Jamie, but I don’t yet” Jamie said.

Heather sat silent for a moment before she said “I think you do and I know you will. You can do this; we can do this”

Jamie smiled again and stood up to take her towel off her hair. “Gotta go get dressed…”

Jamie came out in the jeans and green t-shirt combo once again and put her hand up before Heather could say anything “Give me some time before I get more adventurous with my clothes”

Heather simply smiled and pointed to the bathroom and Jamie led the way in.

“Your hair looks like it has some natural wave to it, so with some curling I think we could get it to do some cool long curls” Heather said.

“Maybe later…I just want to brush it first” Jamie said as she began. It brushed out nicely and she put it into a pony tail. “I’ve always wanted to do that” she admitted.

There was a pair of black flats by the door that Jamie stepped into as Heather borrowed a pair of brown sandals from Jamie’s closet. Jamie took a deep breath before she opened the door and stepped out for the first time as a woman.

It was the little things that Jamie would remember about her first day out. Being called Ma’am by the hostess at the restaurant, not being able to eat nearly as much before she got full and the feeling of smallness she got as she passed a very tall man coming back from the restroom.

It seemed like every guy looked at her that day. Maybe it was her imagination or maybe it was true; she would never really be sure if she was paranoid that day. She knew she caught several sets of eyes wandering down to her chest as they walked around town; she could only imagine if they were staring at her ass as well.

After a few hours, Jamie was done and begged to go back to her apartment.

Jamie retreated into her room and collapsed on the bed. She lay flat on her back listening to Heather shower. She suddenly felt overwhelmed by her life and tears formed anew in her eyes “Who am I?” she asked herself.

The tears had dried by the time a nude Heather walked into her room.

“Staying with you another night to make sure you’re okay with all this” Heather said as she rooted through the drawers and took out a pair of panties. “I love that my wardrobe just doubled last night”

Jamie smirked a bit and sat up. Heather helped herself to a pair of lounge pants and a baggy t-shirt along with some fuzzy socks. “I think I’ll join you” Jamie said as she disrobed. She too put on a baggy shirt, lounge pants and fuzzy socks. “Just when I get used to walking around with a bra…” she added as they exited the bedroom and settled in on the couch for a night of movies.

Sitting next each other under a blanket, drinking tea and watching movies all night, Jamie had to admit that their friendship had already changed; especially after both of them dozed off and Jamie woke up at 1 in the morning with her head on Heather’s thigh. She left Heather on the couch and retreated to her bedroom where she slept deep and long into the next day.

Chapter 5

Jamie woke up and looked at the clock; it was well past 11 in the morning. She wasn’t shocked at waking up as a woman that morning and she simply already expected her hair to be wild and all over her head. She lay there for a moment and tried to remember her dream. She was a she in it and she remembered a voice saying “It’s up to you” but she couldn’t remember much else.

Her feet were sweating so she peeled off her fuzzy socks and padded her way into the bathroom. She brushed her hair and teeth while taking in her reflection in the mirror. “Is this what I’m going to see from now on?” she asked it and remembered the line from her dream once again…”it’s up to you” and freaked herself out a bit.

As she went out and sat on the couch, she found Heather up and watching TV. Jamie checked her phone and saw she had a text message from her co-worker, Josh. Josh always texted shit to James on Sunday morning about the day’s football games as James was a Cowboys fan and Josh was an Eagles fan. When Jamie read the text though, the tone was drastically different.

Jamie read it out loud to Heather “Your boys will still be behind my Eagles no matter what…see you tomorrow” Jamie dropped the phone into her lap and stared wide mouthed.

“I’m guessing that his texts weren’t like that before…” Heather said.

“No; usually it was Cowboys are a bunch of pussies and then he’d call me a term for a homosexual” Jamie said.

“So is he cute?” Heather asked.

Jamie’s mind took off at the question. Her first reaction would have been no, but now, she was seeing Josh in a different light already. She gave herself away by blushing.

“He is!” Heather yelled.

“Well, I guess now he is…” Jamie said sheepishly.

Jamie still enjoyed watching the game but after it was over, Heather made her practice putting on makeup.

Jamie got the hang of it eventually but decided that eyeliner would never be her friend.
After asking if she was okay at least 20 times, Heather headed out that evening and left Jamie alone for the first time as a woman. Jamie paced a bit, nervous for the next day at work before she decided to shower and just relax.

The shower and her hands worked their magic again and she was much more relaxed and quite tired as she climbed into bed.

When the alarm blared at 6 AM, Jamie’s eyes popped open. “Holy Shit” she thought “I have to get ready for work”

She knew that she had to dress up a bit more today because there would be clients in the office so she got right up and headed in to shower.

Jamie got ready quickly and after blow drying her hair, she simply brushed it out and let her natural waves go. She picked out a basic black bra and panties to go under a black blouse and a knee length gray skirt. After she was dressed, she put on a light touch of makeup before she slipped into a pair of black boots. She grabbed a jacket and her purse and went out the door.

Driving for the first time in this body went fine, but wearing boots with heels on them took a bit of getting used to around the pedals.

With her stomach in full flutter, Jamie used her badge and opened the door to her office building.

Everyone acted as if Jamie had always been there and nothing was different which put her slightly more at ease. Her office was virtually unchanged as were her passwords. She dug right into work as if it were any other day.

She went to go get coffee and saw Josh with his back turned in the break room already. Her heart skipped a beat as she approached him. She got up behind him and said “Cardinals 27…Eagles 14; what happened Josh?” in her most innocent voice.

Josh spun and smiled a smile that Jamie had never seen before. It was so much more open and welcome and yet a bit nervous than what he had seen before. “Oh my God” she thought “He’s got a crush on me”

“Hey Jamie” he said “I didn’t see you come in…but yeah…let me hear about it”

“Oh, you mean that the Cowboys destroyed the Giants 31 to 10” and she touched him gently on the shoulder just to mess with his head. She filled her mug and poured in her usual too much sugar. “Are you in any of the meetings today?” she asked him.

“Yeah, I’m in the one at 10” he replied.

“Hmm…I’m in the budget meeting with them at 2…can’t wait” she said with a raise of her eyebrows. “See you later”

She walked back to her office with a slight smile on her lips that she couldn’t suppress knowing that he was watching her walk away and what was running through his mind at the sight.

The workday passed as did the week like most work weeks. Just routine for Jamie as she got more comfortable each passing day with her new self; it wasn’t until Friday’s afternoon break that she got her next round of nerves.

Jamie was taking a short walk outside on a nice sunny day when Josh caught up to her.

Jamie was still getting used to having to look up in all conversations with men. “Hey Josh…how’s it going?”

“Good…how are you doing?”

“Fine…glad it’s Friday” Jamie replied.

Josh took a deep breath and looked very nervous. “So; I was wondering if you were busy this weekend?”

Jamie stopped walking and turned to him “Uh…no…no real plans” she replied.

Josh stammered a second before asking “Because if you aren’t…I’d like to see if I could take you out for dinner tomorrow night?”

“Are you asking me out on a date?” Jamie asked a bit shocked.

Josh grinned “Yeah” was all he said.

Jamie smiled and realized what she was about to do “Okay; sure” she said and saw relief come across Josh’s visage. “I’d like that”

“Great” Josh said.

“Where do you want to go…I’ll meet you there” Jamie said as she started to walk back to the building.

Josh kept stride “I was thinking about Antonio’s; how about 6?”

“Sure; that will be fine” Jamie said blushing a bit “I’ll see you then” she said as she got to her desk.

“Yeah…see you then” Josh said as he stumbled just a bit as he walked past her office and headed for his own.

Chapter 6

“Heather” Jamie said into her phone that night once she got home. “You’re not going to believe this”

“What” Heather replied warily.

“I have a date tomorrow” Jamie said bluntly.

“No shit” she replied “Is it with Josh?”

Jamie blushed even though no one was around her. “Yes…it’s tomorrow at 6”

“I’ll be there to help you get ready” Heather announced “Are you nervous”

“Nervous as hell” Jamie replied “I didn’t date much as a guy…this is unchartered territory we’re going into here”

After they talked for a while and Jamie had calmed down a bit, she said “It’s been a week since I changed”

“And how are you doing with it…like you really have a choice” Heather said.

“It’s strange: I know who I was and what I lived like, yet this body and version of me seems comfortable and even normal for me now. Sometimes, it’s hard to think I was a guy for 27 years even though I’ve only been a girl for 7 days”

“Now what if you change back in another 3 weeks?” Heather asked.

Jamie sighed “I don’t know…I know that’s what we joked about that night; spending a month as a woman but I really don’t know now”

“Know what?” Heather prodded.

Jamie paused again “I don’t know if I want to go back to being James” she said quietly.

“What?” Heather spit out.

“Listen Heather; I was never really happy in my life. It was going fine I guess, but I was already in a rut and I wasn’t even 30 yet. I don’t know what it is, but I feel freer as Jamie…better almost than before…happy”

“Um…okay, I mean I’m happy for you if you want to be Jamie from now on but are you sure?”

“I don’t know yet. And I don’t know if I get a say in it any way…I might just go right back to being James again, like none of this happened…like it was all a dream” Jamie said. “But I’ll make the best of it I guess and go out on a date tomorrow and see if he actually pays”

“All guys pay…it’s just if they pay in money or in pride” Heather concluded.

The clock said 5:13 as Jamie awoke with a start, the vivid dream still played in her mind. She got up and got a drink of water as she remembered the dream…she was in her room and she could feel herself growing taller. She was changing back into her original body and she was mad about it as she screamed, she heard a voice say “it’s your choice…it’s your body…it’s up to you” and that was when she woke up. She lay back down and tossed and turned for quite a while before she fell back to sleep.

Jamie was fairly nervous most of the day on Saturday until Heather showed up around 3 to help her get ready. Heather did her hair and supervised her makeup and approved of her choice of a blue dress with black heels. She was gone by 5:30 and Jamie headed for her car to drive across town.



Heather Kennedy heard the knock on her front door at 9:44 on Saturday night. She peered through the peephole and saw her best friend Jamie Campos looking pissed off on the other side. She quickly opened the door “What’s wrong honey?” Heather asked as she backed up to let Jamie in.

“Everything is wrong” Jamie said as she flung her purse down and started to cry. “What a jerk! What an Asshole!” she started to yell. “Son of a bitch just wanted to get in my pants…motherfucker!”

“Oh my God Jamie; I am so sorry…I thought Josh was a nice…”

“Don’t even say it” Jamie cut her off “I should have known” she said shaking her head. “How long have I been listening to you and your bad dates. I even said on the last one that not all guys are like that; not every guy just wants to take advantage of you…how stupid am I?”

“You’re not stupid” Heather said as she came over to give Jamie a hug “You’re just a girl”

“I can’t wait to turn back into a guy” Jamie said suddenly. “Just when I thought it was going to be better and I was going to be happy, even it was in a different version of me: Nope, not going to happen. Well I just want to get through this month now; I’ve lived as a woman and I think I’ve won whatever our bet was and now I’m just counting down the days”

Heather just sighed “I was really rooting for you. I want you to be happy, no matter what you look like or what your name is; so tell me all the gory details”

Jamie kicked off her heels and headed to the couch to sit down as Heather poured drinks for both of them before coming over to join her.

“So I get to the restaurant and he was already there and I’m thinking it’s a good start. He greets me, asks how I am and gets us our table. So I order Ice Tea and he orders wine and tells the waiter to bring me a glass as well…”

Heather’s eyebrows shot up.

“…so anyway, he tries to ask a few small talk questions and when the waiter comes back with our drinks, he says to the waiter…’keep the wine coming for both of us, she’s going to need it’”

“Oh Dude” Heather said “Red Flag”

“But we go back to talking politely and all but it’s about halfway through dinner when he says to me ‘I’ve waited so long to get to be with you alone like this. I think we both know where tonight is heading…’ and I say ‘uh…not so fast’”

Jamie took a long drink before she continued “And he gets this look on his face; pure anger. It was just for a flash but I definitely saw it. Then he looked embarrassed almost and I told him ‘we might know each other from work, but I’m not that type of girl that one dinner gets you that’”

“Good for you” Heather said.

“I’m not quite ready for sex in this body yet” Jamie said. “I’ve thought about it and I’ve played a few times by myself but I really wasn’t expecting that. Are all guys ready for sex after one date these days?”

“Some are” Heather said. “The three date rule does still exist for a reason and most guys will abide by that rule, but obviously he thought you were putting off signs that you weren’t a three date girl”

“So after that, he got real quiet and concentrated on his food for a while. He tried to pick up the conversation again with some football talk and work talk but he was done with the night and so was I at that point” Jamie said.

“So that was it?” Heather asked.

“For the most part: I didn’t touch my wine and we talked for a while after dinner was over but it was over. At the end, we walked out to our cars and he said he’d see me on Monday” Jamie sighed and took another drink. “So now work gets to be all awkward too. Now I know why they say don’t dip your pen in the company ink…”

They both sat in silence for a few moments. Heather knew to let it simmer for a while and Jamie was still processing what had happened and what had gone wrong.

“All those nights I showed up at your doorstep and told you these types of stories…I never thought the roles would be reversed like this” Heather finally said.

Jamie just laughed “Yup…it’s my turn” she said. “I just want to cry”

“Cry all you want but it doesn’t change the fact that guys are the worst” Heather added. “Shower is that way and you know where my clothes are; you’re spending the night here tonight. Finally I get to repay you for so many times I’ve done it to you”

Jamie got up and stretched out her back. She just shook her head as she headed out of the room.
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Comments: 7

TomBrans1 [2015-02-05 09:09:19 +0000 UTC]

I really love this story - this friendship is so genuine and pure .... . Are you sure it did not happen in real life?! This fantastic story is so convincing!

👍: 0 ⏩: 0

TomBrans1 [2015-01-02 14:27:22 +0000 UTC]

I love this continuation ... . Curious to find out how everything developes .... .

👍: 0 ⏩: 0

halfpint51 [2014-11-25 19:16:24 +0000 UTC]

Well that was quite interesting. I expected Josh and Jamie to work out and I'm glad you went the opposite direction.

Out of curiosity, how many chapters do you have planned for this story?

👍: 0 ⏩: 2

carsonblue In reply to halfpint51 [2014-11-26 02:14:14 +0000 UTC]

Great story

👍: 0 ⏩: 0

Tservo96 In reply to halfpint51 [2014-11-25 20:22:33 +0000 UTC]

Thanks...as of right now it looks to be either 9 or 10 chapters plus an epilogue.

👍: 0 ⏩: 1

halfpint51 In reply to Tservo96 [2014-11-25 22:50:43 +0000 UTC]

Nice. I'm assuming Jamie isn't ever going to return to being James, right?

👍: 0 ⏩: 1

Tservo96 In reply to halfpint51 [2014-11-26 15:34:31 +0000 UTC]

Spoiler Alert...I do enjoy the twists and turns that get her to decide her fate.

👍: 0 ⏩: 0