Finding Himself in Her Ch. 04

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I would like to thank CambriaRose for her swift editing.


Jaime woke on Tuesday morning, disoriented and desperately needing to pee. He gently extricated himself from Kara’s sleeping form and walked naked to the bathroom. As he walked, only half-awake, he felt a bit of weight on his chest and an ache in his ass. He looked down on himself and it took a few steps before he noticed his new breasts as they looked so natural on his- no her, slender chest.

Yesterday came crashing back at her; the doctor’s visit, the sex shop, the salon, the dress and heels, the club, being noticed in a positive way and the feeling of belonging. As she continued walking she fell naturally into a feminine, swaying gait, and felt so naughty as she walked naked through her lover’s house. Her smile broadened as she remembered the feeling of making love to Kara, first gently then roughly. Jaime ran her fingers over her new assets and ass, even in between her cheeks, while she sat on the toilet peeing. She was a bit sore but had a silly smile plastered on her face as she relived last night’s events in her mind. She knew she wanted that feeling again so she cleaned herself out in hopeful preparation.

She finished on the toilet and stood naked in front of the mirror and really looked at herself. Because she didn’t really recognize herself on one level, she could take in all her attributes almost objectively, like an outsider. What she saw was a pretty brunette with ruffled, wavy hair and big green eyes with a few mascara tear streaks underneath. A cute little button nose and plump pink lips. She had pale skin, slender shoulders, perky breasts that looked big on her small frame, big pink nipples, and a flat stomach and a narrow waist that flowed into wide hips and shapely legs. Her entire body was hairless and that made the only thing that should have been familiar look different, her half-stiff penis looked at the same time bigger and less manly without its hair.

When she was a he, he had always seen someone unattractive, someone plain, someone weak in the mirror. But she, she saw how beautiful and wonderful she was. She felt at home in her tight little body, and little wasn’t something bad anymore. Well, at least not when she was still big where it counted, she giggled and hefted her cock. She hadn’t really known she was above average before, she hadn’t really seen any stiff ones besides in what little straight porn she had seen, but according to Kara her thick eight inches more than measured up.

She was suddenly struck by how incredibly much she looked like her late mother. It was like looking at photos of her from her youth, as she was in Jamie’s earliest memories. The thought brought tears to her eyes and steeled her resolve to stay a girl even more; it would be another way to carry on her memory.

She finished in the bathroom and headed back to the bedroom where Kara laid sleeping peacefully on her back. Kara shifted in her sleep and revealed a big, soft, brown breast, making Jaime catch her breath. That such an incredibly beautiful woman would be interested in her amazed her just as much as yesterday’s transformation. Jaime couldn’t help but run her fingers along Kara’s face and down her neck as she committed every detail to memory. Kara stirred but didn’t wake and Jaime felt her own excitement rise, so she decided to wake her brown skinned lover with her tongue. She looked over at the clock and noticed that it was only half past seven; she hoped that Kara hadn’t planned on sleeping in.

She lifted the covers at the bottom of the bed and crawled up under them, slightly hindered by her own stiff cock. She carefully nudged Kara’s legs apart and continued upwards until her nose touched the slightly moist folds of her beloved’s bare pussy. The slender brunette ran her tongue gently over the folds, teased around the opening, fluttered over the clit and teased the inner lips apart. She was rewarded with the deliciousness of Kara’s flowing juices and her gentle moans filtering through the covers.

Jaime worked her long tongue in circles around the opening, getting deeper and deeper until her tongue felt like was being milked by Kara’s tunnel. Jaime worked her way up to the clit which was now peeking out from its hood and sucked it between her lips. She let her tongue flutter over it as she sucked with more and more intensity. Suddenly, hands grabbed her hair and held her hard against the now orgasmic pussy. Jaime lapped up all the delicious juices she could get as she listened to the sounds of Kara cumming.

Kara woke in a state of high arousal, first she thought it was a wet dream, and then she felt Jaime’s long and agile tongue slithering over her clit and her hands resting on her thighs. Her arousal rose and rose and then, suddenly, she felt herself cumming and grabbed hold of Jaime’s head as she climaxed. She held on hard and rode Jaime’s face to prolong her orgasm, grinding her hips against his face as her pussy quivered. Jaime must have worked on her for a while because she was cumming really hard.

As she was coming down from her high Kara pulled Jaime’s şahinbey escort pretty face up towards her and tasted herself as they shared the first kiss of the morning. It was a strange thing to feel Jaime’s thick cock throbbing against her lower belly while her smooth skin and perky, if fake, breasts rubbed against the rest of her. Their kiss was deep and languid and as Jaime ran one hand through her hair and the other along her flank, Kara slowly explored down the little brunette’s back. She reached her target, a perfect bubble butt that easily overflowed her hands, and massaged and caressed the supple flesh.

Kara snaked one hand down to her own opening to lubricate her fingers before returning to Jaime’s ass. Jaime moaned into her mouth as she rubbed her wet fingertips around her pucker and then broke their kiss to gasp as she pushed her index finger in deep. Jaime kissed along her jawline to her ear as she worked her ass open. When Kara pushed a second finger inside Jaime moaned into her ear and whispered, “That feels so good! Can you please take me like you did last night?”

Kara smiled and hugged her lithe lover tightly with one arm, the other still busy with Jaime’s ass, and replied, “Oh, you liked that did you? Do you want the medium one or the giant, sweetie?”

Jaime blushed hotly but managed to whisper, “Umm, the giant one, it felt so intense last night.”

Kara giggled and said, “I think we might have a little size queen on our hands! One giant strap-on fucking coming right up!”

Kara laughed and after another quick kiss Jaime felt herself being rolled off Kara before she got out of the bed. She watched with anticipation as the tall, raven haired beauty donned the harness, attached the huge dildo, and climbed back in bed. The size of it scared her, she hadn’t really seen it last night and now, in the morning light she really couldn’t understand how something so big could fit inside her. Kara grabbed a bottle of lube from the nightstand and squeezed out a sizable dollop on the faux cock. As she rubbed it in Jaime became entranced by the glistening black silicone, she simply couldn’t take her eyes off it!

Kara lubed her fingers and started working on expanding Jaime’s sphincter as she asked, “Do you want to try being on top this time?”

“Yeah, that sounds like fuUUUN!” Kara had deftly pushed three fingers to the last knuckle, making Jaime moan loudly.

Kara giggled at her reaction and started moving her fingers in and out, slowly building speed until she felt Jaime was sufficiently loose around her fingers, then she removed her fingers and with a smack to Jaime’s ass she said, “Giddy up, Cowgirl!” and got down on her back in the middle of the bed, half sitting against the headboard.

Jaime straddled Kara at the waist and let her pucker ease back against the big head of the dildo. She closed her eyes, reached back and held the silicon column steady while pushing back with her body and pushing out and relaxing her ass. Suddenly the head popped through her opening and made her groan with pleasure and pain. She started nudging the big shaft deeper and deeper, taking it much more slowly than Kara had last night.

The pain and feeling of submission that came with it wasn’t nearly as palpable, but the pleasure of being filled certainly was. Jaime let go of the dildo when it was halfway in and moved her hands up Kara’s body. She raised herself until the flared head caught on the rim of her ass and then pushed slowly down again, taking about two thirds with a moan and a gasp. Jaime felt full to bursting and so much pleasure she thought she could cum from just one touch to her extremely engorged cock. She stopped and let her body adjust to the dildo and tried to calm down, she wanted this to last as long as possible. She felt Kara’s hands trace along her arms and cup her face and slowly opened her eyes to look straight into Kara’s as she slowly leaned down for a kiss. As they kissed, she started slowly rolling her hips, stirring her insides with the huge dildo until she found what she was looking for, that cluster of intense pleasure, her prostate.

Jaime rode the silicone cock faster and faster as they kissed and Kara’s hands roamed her body. She felt them on her nipples, their caress along her spine, on her hips, encouraging her, and up her spine again until they tangled in her hair. It felt wonderful to have sex being on top like this but Jaime missed that sense of security and submission she had felt last night with Kara’s bigger body over her. She wanted Kara’s body to envelope her again, so she pulled on Kara’s shoulder and leaned to the other side. Kara took the hint and without breaking the kiss, they rolled over.

Kara got up on her arms and placed Jaime’s legs on her shoulders; she grabbed her hands in one of hers and held them over the brunette’s head. As she started moving in and out again she smiled down at Jaime and said, “God, you look so sexy! I love how those breasts jiggle with every thrust, I can’t get over how real they look!”

“Yeah, Fuu-uck, I love how they feel, it’s like they are a part of me. It feels sooo good when you hit, mmMM-my prostate, it’s like AAAH miniature, UHHN, orgasm each time!”

Jaime continued to moan and gasp as Kara pounded her harder and harder. With each inward thrust she hit that special place and a small jet of precum shot onto her belly as a wave of pleasure ran through her body. Jaime was moaning uncontrollably as she said, “UHHN, I, UHHN, never, UHHN, want, UHHN, this, UHHN, to, UHHN, end!”

Being buried beneath Kara’s stronger, taller body, her shoulders pinning Jaime’s legs, her hand pinning hers, her long jet black hair surrounding them, it all made Jaime feel so powerless yet safe, vulnerable yet protected. Kara looked so incredibly beautiful above Jaime; her caramel skin glistening with perspiration, Jaime’s own pale legs in stark contrast on her shoulders. Kara’s big almond shaped hazel eyes locked on Jaime’s face and a look of joy, lust, and concentration on her face as she increased the pace even more.

Kara felt her own orgasm building as the strap-on rubbed her clit on every inward thrust and her g-spot each time she pulled out. Just watching Jaime take her big fake cock was such a turn on that she would have been right on the edge anyway. Kara felt some added friction and knew that Jaime’s ass was clenching before cumming so she moaned out, “Cum for me sweetie, cum with meee!”

She grabbed Jaime’s cock and just as the first jet shot out, they screamed, “I’m CUUUMMMING!”

Jaime came like crazy from the combination of the giant silicone cock moving in and out of her ass and Kara’s hand stroking her cock. That along with the visual of Kara throwing her hair back in ecstasy, her big brown tits bouncing as she plowed Jaime senseless, it all culminated in an orgasm that went on and on, making her toes curl, her legs shake and her back arch. She came for so long that the last jets of cum were almost clear, every last bit of sperm had escaped her balls.

Kara came really hard as well, but she tried to focus through her own orgasm and really hit Jaime’s prostate to prolong her orgasm. Her arm started to shake from holding herself up, and just as her orgasm ended she collapsed on to Jaime in a messy heap, her strap-on buried to the hilt.

She kissed Jaime along the neck to her ear and whispered, “Good morning, sweetie.”


They walked along the street hand in hand, heading towards the shops to get Jaime the beginnings of a feminine wardrobe. Jaime had wanted to wear her little black dress and her high heels again but Kara had made the point that it was evening wear. She also made the point that Jaime’s feet would be destroyed if she walked around shopping in those four inch heels. Instead Jaime wore her old Converse sneakers, her tightest jeans, though they really weren’t that tight, and one of Kara’s tops. The top was a light pink tee with a bit of cleavage; it was made in a stretch material but hung a bit loosely on her smaller frame, especially over the chest. The top and her fake breasts left little doubt that Jaime was anything but a girl.

Her secret was tucked away in her lacy green panties and this morning’s draining orgasm should make sure no unfortunate bulges gave her secret away. The panties slid erotically against her ass and cock, and was a constant reminder to keep her mind on the fact that she should act like a woman, walk like a woman, talk like a woman. Jaime’s auburn hair was loosely held by a tortoise clip and she had clip-on earrings dangling from her ears. Her makeup was subtle, just a bit of pink lip gloss, some mascara and eye shadow. As she walked she remembered to take shorter steps and place her feet straight in front of one another to give her hips that alluring feminine sway.

Jaime looked over at Kara, she was as beautiful as ever; dressed in a knee length maroon pencil skirt, knee high leather boots with a three inch heel and a white shirt that made her caramel skin stand out beautifully. Her hair hung loosely around her face which was as subtly made up as Jaime’s own.

Kara was so happy as she walked hand in hand with Jaime that she almost skipped down the street. Not only did it turn out that Jaime’s new form turned her on more than her hottest girlfriend and boyfriend combined, she felt more complete with Jaime than she ever had before. She knew this was moving extremely fast but it was so exciting and felt so right that she didn’t want to slow down. Jaime was so sweet to her, she made her waffles from scratch after they showered together and she truly listened as they talked, she didn’t just nod along. They had talked about Kara’s work and her family and then moved on to discussing how Jaime wanted to proceed with their little experiment. They decided that Jaime should experience as much as possible of what it felt like to be a woman so Jaime could make an informed choice. They also decided that they really needed to know what Kara’s best friend, Jaime’s boss, would think about all of this. Kara called Melissa and invited her and her wife Maria to dinner the next day, saying she wanted them to meet her new girlfriend.

Jaime felt a bit nervous about meeting her new boss dressed as a woman; she would be the first person outside of Kara who really mattered in Jaime’s life that would see him/her like this. As she was his new boss it could determine a great deal about her future, because she was becoming really attached to herself as a woman. Jaime didn’t even know if she wanted to go back or if she could now that she knew what was on the other side.

She was pulled from her thoughts as Kara steered them into a big mall. Jaime was a bit amazed at the variety of all the people and stores. She saw the stores in a completely different light now, she had always seen shopping for clothes as a chore but now it felt exciting. She looked up at Kara with a big grin on her face and said, “Wow, I want to go to all the stores! Where do we start?”

Kara smiled back down on her and answered, “Well, how about we start with the shoes and work our way up?”

“Okay, which store should we go to? I see like five shoe stores from here!”

“Well, a lot of girls are kind of shoe crazy, I really never got that obsessed myself. I think we should try the Ecco store first, they sell shoes that are made both for comfort and looks.”

Jaime nodded and they made their way hand in hand through the throng to the store. Inside the store it was a much calmer atmosphere and as they browsed a mousy, polite saleswoman approached them and speedily fetched any shoes they asked for. Jaime liked the ones with a higher heel because she felt taller, more confident with them on. After a bit of trial and error she walked out of the store in a pair of woven leather wedge sandals, a pair of grey suede boots and her old Converse’s in a bag. She had been a bit surprised by the price tag but decided that as her work would pay nicely she could afford to rack up a bit of credit. Kara had been right, the shoes were very comfortable, much better than the sexy stiletto sandals from last night, and the wider heel was easier to walk with.

Next stop was Victoria’s Secret. There was so much sexy lingerie that Jaime felt a twitch between her legs despite the incredibly draining orgasm earlier. Since they already knew Jaime’s measurements and cup size, it was just a matter of picking out colors and models. They started with a few sports bras and some plainer undies, and then moved on to the nicer things. They picked out hiphuggers, cheekies, thongs and boyshorts, all lacy and in bright colors, mostly green. They picked out matching bras; pushups, demi-cups, some so lacy they did more to accentuate the nipples than cover them.

Kara picked out some sexy babydolls, Jaime picked out some stay-up stockings, one white pair, one tan pair, one dark pair and one pair that were more like grey, thin thigh-high socks. Jaime was so excited, she couldn’t wait to try on all the different lingerie and see the hunger in Kara’s eyes as she modeled them for her.

Jaime really wanted to start swimming laps again to keep her workout going, so she picked out a nice green bikini as well. Kara said she did Yoga three times a week and that she wanted Jaime to join her, so she picked out some yoga pants and a nice top as well.

Jaime put another dent in her credit card at the checkout and then they decided to stop at a café before continuing shopping. Jaime got a hot chocolate and a Danish, and Kara got a cappuccino and a big chocolate muffin, she also picked up a style magazine while Jaime found a table.

After she sat down and took the first sip of her coffee she opened the magazine and asked, “So, cutie, what kind of style do you think you want?”

“I don’t know, I really like skirts and dresses and that would help with, umm, you know, hiding my secret. I really like the feeling I get by being all girly so I think I want to be really feminine.” Jaime blushed at saying this, just a few days ago the thought would have been so foreign to him/her but now she knew that this was what she wanted.

“Great! I really like girly girls as well and I would love to dress you up all pretty. I would really like to see you in some tight jeans though; your butt would look spectacular in a good pair.”

Jaime nodded and smiled but blushed a bit, she was still not used to getting compliments about her body. They looked over the magazine and pointed out things they liked and disliked, and to Jaime it felt so great and so girly to talk like this, it felt like she belonged.


When Jaime exited the mall she looked very different. Gone were her ill-fitting jeans and top, ticked away in a bag on her arm. Instead she wore a thin green blouse that showed just a hint of cleavage, a brown suede jacket that ended at the waist, a pleated grey skirt that ended a few inches above the knee. She had a wide woven leather belt with a big brass buckle to tie it all together and the grey thigh high socks covering her sexy legs. She had on the woven leather wedges that went with the belt and a nice wooden necklace that went well with the jacket. Silver earrings dangled from slightly sore holes in her pretty ears. Jaime felt so incredibly pretty, last night she had felt really sexy for the first time but now for the first time she felt pretty and really at home in her body.

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