Finding Himself in Her Ch. 03

Adriana Chechik




“Ummm … Hello?”

“Hi, I’m calling for Mr Jaime Baudelaire?”

“Good morning, this is he.”

“This is Savannah from Dr. Simmons clinic, I’m just calling to confirm your appointment for three o’clock.”

“Oh, right, damn, I forgot about that. Thank you so much for calling!”

“No problem, we’ll see you at three pm, bye!”


What a way to start the day. Jaime started to look around, he vaguely recognised this room. Oh yeah, it was his new apartment. The bed felt strangely empty and as he rolled over Kara wasn’t there, just a note.

Hi Jaime, I wanted to wake you to say goodbye but you looked so peaceful that I didn’t have the heart. Here is my cell number, call me today… 555-2106 PS. I still feel tingly from last night… Love Kara

Jaime smiled at the note, he felt last night as well, his jaw and butt ached slightly and he could still smell her on his lips, he had a sense of well-being he had never felt before. This slowly disappeared as he thought of the clinic he had to go to. Jaime had a phobia about hospitals, it had been bad before his mothers death and after it just got worse, to the point where he got panic attacks as soon as he entered a hospital or medical clinic. He had his last doctors visit when he was 11, squeezing his mother’s hand hard the entire time. Now Jaime had to go to the doctor because of this new job. They wouldn’t hire Jaime without a full medical for insurance purposes. When he had moved in the first batch of stuff last week the private clinic the company used had sent a very nice nurse to his apartment to collect a blood sample after Jaime explained his condition. There was no way of conducting the examination off site however, so Jaime had to bite the bullet. The problem was that he needed an anchor, someone to hang on to, and his father was supposed to be that person, but he had been called away for work. Jaime picked up his cell and dialed the only one he could think of,

“Kara Thorn speaking.”

“Hi, Kara, it’s Jaime.”

“Hi Sweetie! I’m so happy you called, and I’m sorry about leaving without saying good bye, I hate when someone does that to me.”

“Oh, don’t worry about it. Listen, I was wondering if you are free by three o’clock?”

“I’m between projects this week so I can leave when I like. Do you want a little afternoon delight?”

“That would be lovely, but I have a favor to ask you. I have this doctors appointment and I don’t know if I can go alone.”

“Of course I’ll be there! Is it a serious procedure?”

“Thank you so much! And no, just a medical, it’s just that I-I-I have this … fear of hospitals and doctors, and I don’t think I could handle it alone. Dad was supposed to come but he had to work.”

“Of course you shouldn’t have to face your fear alone. Just text me the address and I’ll pick you up and drive you there, OK Honey?”

“Thank you so much, you don’t know how much this means to me, I love you!”

“Love you too honey, but I gotta work now, see you at three. Bye Sweetie!”


Jaime felt like a huge weight had been lifted from his shoulders, but he was still nervous. After a shower and some breakfast he unpacked his books, cleaned the apartment and did anything else to keep from thinking about it.

Suddenly the phone rang, Kara was downstairs in her car, it was time. He got into her car, a beautiful and powerful gunpowder gray Audi RS5 that Kara handled with ease. Kara hugged him and tried to keep their conversation light and fun as they cannoned down the streets, to keep his mind off where they were going. It worked, in no time they pulled into a parking lot outside the small private practice.

Kara got out of the car in her leather high heeled boots, formfitting black slacks and jacket and white silk blouse. When Jaime didn’t follow her out she went around to his side and opened his door. She held his hands as he shakily got out and he looked so scared that she pulled him into a tight hug and whispered into his ear, “Just put everything out of your mind, focus on me instead and just take one step a time.”

Jaime nodded, he felt safe in her arms, with her he felt stronger. Kara led him into the waiting room and they sat holding hands as they waited until his name was called. When he raised his hand the doctor, a fifty something woman with a sturdy build, came over and shook his hand and said, “Hello Jaime, I’m Doctor Simmons, but you can call me Marsha, if you would come with me?”

“Hi Marsha, would it be possible for my, umm, girlfriend Kara to come with me? I have a strong phobia about hospitals and it would really help.”

“Well, yes, if your comfortable with her being present at your examination. It might help us get a more accurate read of your blood pressure if you feel more relaxed with her there.”

“Thank you so much!”

The doctor smiled and led the way into a small room with a padded bench and medical equipment and şahinbey escort a few chairs. She told Jaime to strip and put on a hospital gown while she fetched his chart. Jaime undressed quickly and stepped into the gown, his hand holding on to Kara again as soon as his hands were free. The examination went smoothly, the doctor checked his blood pressure, his breathing, his height and weight, his testicles for growths, she was a bit surprised by his complete lack of hair but Kara explained as Jaime blushed. Then it was over and he could get dressed. Dr. Marsha invited them to sit on two of the chairs and she took the third as she spoke, “OK, Jaime you are completely healthy, but, there is something that came up with your test. At first we thought we had gotten the wrong blood sample but after we took a closer look we realised it was yours, not a woman’s. It seems you have a hormonal imbalance, and from what I have seen today I would say you have had this imbalance since puberty at least. What we discovered is that you have abnormally high estrogen and female growth hormone levels combined with a low testosterone level.”

“OK, is-is-is it d-dangerous?”

“No, not at all, but it has probably affected your body’s development greatly. If I’m right about this condition being present since the onset of puberty it would explain your feminine bone structure, your lack of facial hair, your voice, your lack of muscle definition despite working out and the places fat stores in your body. I’m surprised you don’t show some of the other signs of excess estrogen, you haven’t grown breasts and you haven’t mentioned problems getting an erection. Do you get emotional easily?”

“Yeah I guess I do. So what are my options?”

“Well, I would like to run some more tests, but I think you can stay as you are, there is nothing dangerous to your health about your condition. You could get testosterone injections to become more manly, but those can affect your mood and even your personality along with your health, make you more aggressive and so on, and lastly you could go the other way, get breast implants and maybe a sex change operation.”

“OK, that’s a big decision!”

“Of course it is, and it is one that should be considered over a long time. I’ll sign your clean bill of health for the insurance company and give you some literature on the subject. Now, I’m sorry to do this but I have another patient waiting so you will have to leave, but you can have my phone number, feel free to call anytime.”


They shook hands and Kara led an unsteady Jaime out to the car. Jaime was staring out the window, deep in thought, so Kara drove them in silence towards their apartment building, using the time to think as well. She actually felt happy about Jaime’s condition, it played into her fantasy of feminization perfectly. When she parked in the garage Jaime spoke for the first time, “Are you hungry? I could eat a horse!”

“Haha, yes, let’s go to Maria’s.”

They walked hand in hand to the coffee shop and grabbed the same secluded corner table as yesterday after they ordered. As they waited for the food Jaime asked, “So, what do you think?”

“Well, I don’t like the testosterone option, she said there were health risks and a risk that your personality changes, and I really like your personality as it is. From what you have told me you don’t really like being you, for the most part, so I think you should try seeing how the other side feels. I don’t want you to have a sex change, I like your cock to much for that, but we could dress you up this week and see how you like it. I could take the week off from work and help you, my next project doesn’t start until next week anyway so it wouldn’t be a problem.”

Jaime opened his mouth to answer but was interrupted by the waitress delivering their food. He considered his answer as they ate, he knew he liked the way Kara made him feel feminine and submissive in the privacy of the bedroom but he was uncertain of acting like a woman in public. He thought of when he saw himself in the mirror in those panties, and how exciting and right it had felt and he said, “I think it would be nice to see if the grass is greener on the other side, at least with you by my side. It’s so great of you to help me with this!”

“Yes! I’m so happy you agree! It will be so much fun to dress you up. And I must confess, it is kind of a big turn on for me, but maybe you guessed that when I got you into those panties?”

“Yeah, I loved wearing those, they felt really sensual against my skin and, it was strange, but I really liked how I looked in them when we stood in front of the mirror. How do we do this?”

“Well, the first step is getting you some nice tits! I know a woman who runs a sex toy shop, well, she calls it an adult literature store. I think they have breast forms and it’s walking distance.” Kara saw Jaime’s questioning look and continued, “Fake breasts that you glue on, the more expensive ones look totally real. We could get them now if you like so we can practise and play tonight, it’s only five o’clock so the stores are open for a few hours more.”

“Um, Okay, this is moving really fast but it’s kind of exciting. Yes, I think I want to get started tonight.”

“Okay, great! Let’s go get you some boobs and then maybe some clothes.”

Jaime laughed and Kara joined in as they left the coffee shop. They walked hand in hand as Kara navigated among galleries, second hand shops, restaurants and bars, clothes stores and apartment buildings until they stopped in front of shopfront with the name Secret Desires written in a swirling and elegant font. There were mostly books on display in the window and very little to hint at what kind of shop this was unless you read the titles of the books.

They entered the shop and Jaime looked around at the books, magazines and DVD racks of the front room as Kara led the way towards the back room. Next to the beaded curtains that hid the back room was the check-out counter with a young woman displaying an extraordinary amount of cleavage manning the register. She smiled towards them and Kara said, “Hi, could you tell Moira that Kara is in the back room and would like some help?”

The young girl nodded and Kara and Jaime moved past the beaded curtains. Jaime was shocked by the amount of sex paraphernalia that could fit into a room. At first he just saw a blur of latex, rubber, lace, leather and silk then it all became individual shapes; sex toys, whips, outfits and anything else you could need to fulfill any depraved need you could think of. A redhead, dressed in a sexy yet professional gray pencil skirt and a white blouse entered from a side door and hugged Kara as she said, “Hi Kara, it’s been a few months, how are you?”

Kara smiled and answered, “Hi Moira, I’m just peachy, I was wondering if you could help us? Jaime here needs some breast forms, the best you’ve got.”

“Well, where are my manners? Good evening Jaime. My, you are a pretty one, I can see why Kara likes you!” Jaime blushed and shook Moira’s proffered hand. She led them over to a display shelf as she continued, “Yes, we have a few models, these here are the absolute top of the line. They look and feel incredibly real, and they connect the fake nipples with your own so you feel when they are pulled and pinched, and they can stay on for five days and only comes off with the glue solvent that is included. What cup size were you thinking of?”

Kara answered before Jaime could open his mouth, “I think a full B or a small C, anything bigger would look out of proportion, she has such a slender chest, don’t you sweetie?”

Jaime could only nod. He felt a bit lost and like everything was moving so fast. Kara seemed to have everything under control and he trusted her, much more than he thought possible with someone he had just known a few days. He was excited about getting breasts and trying on dresses and other girly things. When he read the lesbian stories that were the main part of his fuel for masturbation he often fantasised that he was one of the characters and now he would actually be one. As he thought this Moira said, “I have just the perfect pair, they are just her complexion, and they have lovely big pink stiff nipples!”

Kara responded, “Great! Could we maybe get some help with applying them? I want to take her shopping afterwards.”

“It would be my pleasure. Follow me.”

Moira led them both through the door she came through. It led into a comfortable looking staff room with a big leather couch and two recliners. Moira asked Jaime to take off his tee and Kara nodded reassuringly when he looked over at her. He reluctantly pulled it over his head and dropped it on the couch. Moira took out some cotton swabs as she started her instruction, “First you clean the area with alcohol, then you apply the glue to the back of the breast form, then you get the nipple stiff and into the hole at the back of the breast form, and then you massage the breast and run your finger along the edge to smooth out the glue and make the edge disappear. Then you repeat for the other side, being careful with the alignment and lastly you apply a concealer along the edges to hide the transition and Voilá!”

Jaime looked down and whispered, “Wow!” He had breasts! Beautiful, perky, round, pale tits with big pink nipples standing at attention. The girls led him to a mirror and as he moved they swayed just right. As he took in the person in the mirror he breathed out, “I’m a girl.” Kara came up behind him, no, HER, and hugged her and said, “Yep, but your my girl and I love you!” Jaime kissed her cheek and whispered in her ear, “I love you OOOHH God!” Kara had pinched and pulled her fake nipples and it felt almost real as the clamps worked her real nipples. Jaime suddenly blushed furiously as she remembered that Moira was still in the room. She turned around and buried her face against Kara to hide her embarrassment as well as her swelling cock as she squealed out, “I can’t believe you just did that in front of someone!”

Kara laughed out loud and hugged Jaime tight for a while as she kissed her head and then she said, “Oh, you are so damn adorable! Please don’t be so shy, it’s only us girls here and Moira is a good friend, and believe you me, she has seen helluva lot more in this shop.” She hugged Jaime tightly and turned to Moira, “Do have a measuring tape? I don’t know what size she is.”

“I have one right here, why don’t you measure her bust line and I’ll fetch a bra while you measure the rest?”

“Okay,” Kara grabbed the tape and measured Jaime’s chest just below her newly acquired tits, she checked the length and said, “She’s a 32, could you get a green bra and matching panties? She has incredibly green eyes and it’s always nice to match.”

Moira nodded and Kara placed the tape around Jaime’s waist, “Wow, a 23 inch waist, a lot of girls would kill for that!” Jaime smiled and blushed. Kara undid Jaime’s jeans and measured around her hips, “Jesus, 37 inch hips! 32C-23-37 and what, 5′ 2″? You are quite the little package!”

Moira came back with the bra and panties and after Kara helped Jaime on with her bra Kara left with Moira to pay for everything. Jaime slipped on the panties, a lace and satin thong. It felt a bit strange having a string between her cheeks, a bit like a constant wedgie, but when she looked over her shoulder she couldn’t deny how incredibly sexy it looked. She pushed her balls inside her body and tucked away her half stiff cock as best she could. She slipped on her jeans and tee shirt and looked in the mirror. She didn’t see an effeminate and shy guy with fake breasts, she saw a beautiful girl without makeup dressed in tom-boy clothes. She put her discarded boxers in a bag with the breast form kit and headed out to Kara. Kara had already paid and after they said thank you and good bye to Moira they walked hand in hand out into the night.


Kara led the way and they soon found themselves in a small salon greeted by a perky blonde whom Kara asked, “Hi, my girlfriend Jaime here needs a makeover, she just moved here and she wants to look her best for her new job. If you could fix her up and teach her a bit about makeup and hair and so on that would be great!”

“Okay! Hi, Jaime, I’m Kimberly.” She wrapped an arm around Jaime’s shoulders and led her to a styling station, “So, what kind of style are we looking for, Jaime?”

Jaime felt at a loss for words but decided for something close to the truth. “I don’t know. I haven’t really cared about my looks that much before, now that I have Kara I want to look pretty for her but I have this new job and I want to be taken seriously there as well.”

“I think I know a perfect style for you. Just sit back and you will see a new and improved you in no time.”

Over the next hour Kimberly cut Jaime’s hair, just the tips, plucked her eye brows and taught her how to apply make-up and fix her long auburn hair in a few different styles while Kara sat next to them, coming with the occasional pointer. They chitchatted and laughed and gossiped and Jaime felt just like one of the girls. When they were done Jaime felt and looked beautiful. Her formerly straight auburn hair fell in waves around her shoulders and framed her face perfectly. Her lips were a pretty pink and glistened seductively, her cheeks were made to stand out with some blush, her eyebrows now a perfect arc and her big eyes looked seductive with their long lashes curled and some subtle eye shadow. Her nails were the same pink as her lips and made her hands look really feminine. There was a sort of silent agreement that since Kara and Jaime obviously were lesbians her nails probably should be kept short.

Kara was amazed at how wonderful Jaime looked. She had known there was a lot of potential but she was still surprised with the result. Kara wanted the clothes to match the face so after they thanked Kimberly and Jaime paid for her hair and make-up Kara led the two of them to an upscale boutique that sold both clothes and shoes. She knew it was getting late and planned on doing a lot more shopping with Jaime tomorrow, but she wanted to take Jaime to a soul bar she loved and get an evening snack and a few drinks. She led Jaime over to the dresses and said, “Every woman should have a little black dress in her wardrobe and we need to find one that does your sexy little body justice.” Kara grabbed her ass and watched Jaime blush prettily as she shot her a surprised and embarrassed glance. Kara said, “Oh, I’m sorry sweetie, I didn’t mean to embarrass you but that ass is so damn delectable!”

“It’s okay, I’m just not used to all this. I thought I would be found out by someone but no one has given me a second glance. Well, I saw a guy looking at my breasts but that felt more like he was checking me out, it was kinda exciting!”

“And why wouldn’t he? Even in those clothes you look pretty damn hot! Now, how about this dress?” Kara indicated a cowlneck dress on a manikin.

“It’s beautiful! It looks a bit revealing though.”