The Road Trip Pt. 01

Story Info
Gina finds herself on a road trip to New Orleans.
3.2k words
4.33
20.2k
13

Part 1 of the 3 part series

Updated 06/07/2023
Created 03/06/2015
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

As Gina gazed into the mirror and looking back at her was a beautiful redhead with Liberty Curls in a vintage styled purple wiggle dress. It had a black bodice and plunging neckline that highlighted her ample cleavage. Her lips were crimson red and her eye shadow was smoky with a dramatic shade that contrasted her dress. Her eyes were lined in a swept up cat eye style to match her attire and she wore false eyelashes with just enough drama to stand out. Her breasts was pushed up and together from the bra shelf she wore and the corset held her waist in tightly giving her an amazing hour glass figure. She could feel her stockings clinging to her smooth legs held in place by the eight suspenders of her garter belt. On her feet were four inch leopard print pumps that matched her clutch.

Gina still couldn't believe that the bombshell looking back at her was her. Two years ago she was a he and this was all still so surreal to her that she had trouble grasping it. She always knew she was transgender since she learned what that word meant but in her wildest dreams she never thought she would be able be what she knew deep inside she was. She still had a small penis between her legs and yet that seemed okay to her, she was happy in this place in between man and woman and she was going to stay here for awhile.

"Gina... Gina!" Sandra, her closest friend, snapped her out of her daze. Gina turned to her and smiled fighting back tears of joy for fear of ruining all the work that Sandy had done for her.

"It's so perfect lover... I... I... I absolutely adore it!" The redhead stammered as she bent slightly and kissed the blond woman lovingly. Sandy was a make up artist and hair stylist with a specialty in Retro pin up. She had been born a woman so she found it hard to fathom what her friend was going through but she knew that it wasn't healthy for her to be cooped up inside her house for the last nine months since her breast surgery. She looked amazing even if she couldn't see it.

Gina argued when Sandy suggested that they take this road trip to New Orleans but Sandy was having none of it. "Look! I know that all this is strange honey" Sandy Started "finally being what you always dreamed of and it's probably overwhelming but you have to get out and start living your life. Your new life..." Sandy Continued "You are beautiful and I'm going to prove it to you." Gina remembered her friends adamant tone. "I'm going to pack your bag and you get no say in what I pick out for you. I'm going to dress you this entire trip. You can wear whatever you want on the road but once we get to New Orleans you are going to be in my hands... Understood?" Gina grumbled but finally gave in.

Gina was a graphic artist and illustrator who did most of her work out of her house which made it easy for her to become a recluse. She had admitted to Sandy that she was afraid that people would see her as a "man with tits" which terrified her and no matter how much Sandy assured her that this wasn't the case Gina couldn't shake her fears.

Gina knew this trip was what she needed no matter how scared she was. She also knew Sandy wouldn't make her look trashy or cheap, she trusted her friend implicitly. Sandy had worked with numerous alternative models and photographers building up an impressive portfolio, so it was settled, they were taking a road trip to New Orleans. Gina knew it would do her good and who better to spend a couple of weeks with than her best friend?

The morning of their departure when Sandy picked Gina up from her home, she was in baggy pants and a sweatshirt with her red hair hiding her face. Sandy just shook her head and realized she had a lot of work to do to help Gina overcome her lack of self confidence. She was determined that given two weeks with Gina she could help her see what a beautiful feminine person she had become.

As she stood remembering the recent events Gina recalled the first night in the hotel room when she let Sandy play with her hair and in the morning she did her make up sharing all the little tricks she used to get the look she wanted. Something deep inside Gina began to stir at that moment that she had never experienced before. She had butterflies in her stomach as Sandy did her eyes and painted her lips. Gina had shut herself off from the world for almost a year and it seemed that the emotions she was avoiding all that time were starting to froth up to the surface. She knew this woman as her closest friend but this was something more.

On the third morning Sandy laid out Retro styled jeans with a high waist, a pair of cute flats and a pink and white striped top that buttoned in the back. Along with her new outfit Sandy supplied a cute bra and pantie set that matched the period cut of her outer clothes. Gina remembered being hesitant but went along with it even though they had clearly not arrived at their destination yet.

When Gina had gotten dressed Sandy sat her in front of the mirror and did her hair and make up making it a little bolder than the day before and tying a Leopard print scarf around her head to keep her doo in place while they drove. The weather was nice and Sandy planned to put the top down on the car. As a final touch Sandy handed Gina a pair of Cat Eye sunglasses and a cute little pink and black bowling ball bag purse. Gina rolled her eyes but her friend just smiled. Sandy saw Gina stop in front of the mirror on the way out the door and stare a good thirty seconds. She didn't stop her, she just smiled too herself "Maybe this will work" She thought.

Sandy had always admired Gina for taking her life in her hands and she had vowed a long time ago to support her in any way she could, even if it meant giving her a swift kick in the butt. After all, isn't that what friends do? She wasn't about to see Gina come all this way and get stalled by some fear.

They pulled into New Orleans late that night and Sandra found their Hotel. She pulled up to valet which was on the street and the young man opened Gina's door and smiled at her "Good Evening Ma'am, welcome to the Hotel Royal." Sandra drove a 1958 Cadillac convertible in Candy Apple red. The door was enormous which caused the valet attendant to make a grand gesture of opening it and as Gina placed her foot on the curb something magical happened. Suddenly she felt like a movie starlet as the attendant offered her his hand. She noticed his eyes glance down at her cleavage. She was between a C and a D cup and had about a thirty eight inch chest. It sent shivers through her body as she delicately reached for his hand allowing him to help her out of the car.

Gina had begun to notice the changes in people around her after had she allowed Sandy to make her over and then the cute little outfit. People began to look at her differently, not just people that were paid to be polite. Men filling their cars in gas stations had lingered just a little longer than normal and their wives or girlfriends chastised them when they got back in the driver's seat. The boys buying candy in the convenience stores and then whispering about the hot redhead. The girls in the diners they stopped at that wanted to know about her look, hair and make up.

Suddenly all the emotions that had been pent up in the last months came crashing in on her and she began to cry right there at the valet stand. She broke down, everything that had happened over the past few days came in on her all at once. She realized that she wasn't a "man with tits" and that if it weren't for her best friend she would still be sitting at home afraid of her own shadow. Sandy had shown her that she was beautiful and feminine and she realized that she loved her.

The poor young man was confused and Gina tried to convince him that she was just overwhelmed by the beauty of his city through her sobs. Sandy knew it was more than that. Rushing around the front of the car she took her friend into her arms and consoled her "It's okay baby, I'm here, I understand, let it all out."

Sandy helped Gina into the lobby and got their keys. Gina whispered in her ear "I want to go to our room right now. I need to show you how much you mean to me." Gina nipped at Sandy's earlobe causing the petite blonde's nipples to stir in her blouse.

Sandy was surprised, she wasn't sure what had come over Gina but she was sure she liked it. The bellman took their luggage and followed them up to their room. Once the man left Gina threw her arms around her friends neck and kissed her lips greedily. Gina her tightly to her body cradling her head. "Oh God I love you" Gina breathed across Sandy's ear. They had never made love before but that would change after tonight.

They fell into the bed together and Gina's lips caressed Sandra's neck fluttering over the sensitive spot where it met her shoulder. They had known each other since middle school and had shared all their little secret places with the other. Sandra had unbuttoned Gina's top and pulled it off her shoulders. Gina sat up cradling her lover's face as Sandra brought the top down the redhead's arms, slipping it from her body only to vanished onto the hardwood floor someplace. Sandra slipped her hands back around Gina and pulled her back down on top of her, their tongues intertwined as the both whimpered and cooed in each others arms. Sandy managed to unclasp Gina's bra then rolled her over on her back tugging it free.

As Gina laid there looking up at her closest friend, confidant and now lover as Sandy nearly tore her own blouse from her body and undid her bra tossing it on the growing pile of clothes. She was straddling Gina now and bent down lovingly taking a nipple into her mouth, her tongue running circles over it. To Sandra's delight Gina let out a low moan, her back arched as she grabbed at the bedspread.

Ever since her HRT Gina's nipples had become ultra sensitive. She could feel something stirring inside her, the same something that she had felt yesterday morning only this was much more intense. She began to tingle in her belly and she felt her little cock begin to stir. Sandy felt it too and she began to grind her hips against Gina's as she pulled on the nipple with her teeth. Gina wailed before she grabbed a pillow and screamed into it with all the lust that had built up over the last months. Sandra had begun to awaken things inside her friend that Gina didn't know existed.

The petite blond shimmied down Gina's body and plucked off her shoes tossing them with the other things and yanked her tight jeans and panties free in one smooth motion. She had known a long time ago that she loved this redhead and she couldn't believe this was happening.

With all that Gina had been through Sandra didn't know if her friend felt the same toward her and now Gina was in her bed and they were making love. Sandra was so excited that she could barely catch her breath. Her nipples stood erect on her perky breasts and her pussy had grown warm and wet.

She slipped off of Gina for a moment and removed the rest of her clothes before she yanked the pillow from the panting beauty's face and kissed her full and hard on her lips. "Let me show you how much I love you baby" Sandra wiped the hair from Gina's face with one hand while her other explored the transgendered woman's cock which had grown stiff for the first time in many months. Gina cooed and squirmed.

"I don't know if I can.." Gina Started but Sandra cut her lover off with a finger to her lips.

"Shush, you just let me take care of you..." Sandra cooed into Gina's ear.

With that Sandra slipped down Gina's body nibbling at her full breasts and circling her aureole with her tongue, then she placed small kisses along her belly that sent shivers up Gina's spine. The next thing that the buxom redhead felt were warm lips around her cock, Sandra's mouth sucking at it as her tongue circled it. Nobody had done that for her in a very long time, in fact she couldn't really remember any time. In middle school Gina had experimented as a boy with the girls but that was so awkward. This was so different, so much better. Her erections were rare and she had not had a orgasm in years due to the medication, or so she thought.

Sandra began to swing her body around until her wet pussy was in front of Gina's lips. Her tongue darted out and flicked over Sandra's folds then suddenly the blond dropped her hips and her pussy was at Gina's mouth. The redhead tongued her slit and her best friend in the whole world moaned around her cock sending vibrations through Gina's entire body.

Gina found Sandra's clit and sucked it gently past her teeth, her tongue flicking up and down as fast as she could. Sandra arched her back and shivered moaning again across her lovers hard cock.

Then, there was something new. Gina felt Sandy's lubed finger circling her tight little star. Instinctively Gina tensed pulling her muscles tight. "Relax baby, I'm not going to hurt you, I would never hurt you, you mean too much to me. I promise, this will feel very, very good."

Sandra had done quite a bit of reading when Gina told her that she was going to start HRT. Gina meant the world to her and she wanted to understand what was about to happen to her. She had read someplace that "While the person's penis may loose it's ability to become erect that the prostrate remained highly sensitive and if given the proper stimulation that it was possible to induce orgasm."

It was all very clinical but she was about to put it to the test. Gina relaxed her bottom hearing Sandy's soothing tone and Sandy's slim digit slipped past her tight muscles. Sandra found the little walnut sized nub and began to stroke it while her lips, tongue, and mouth sucked Gina's hard cock.

Gina's whole body was suddenly on fire and the heat was rising. She wrapped her arms around the blonds hips and pulled her tightly against her mouth her moans vibrating against Sandra's sex. Gina's tongue dove into her lover's slit and fucked her like a little cock rocking against her clit at every stroke. Sandra's body responded and they were both moaning constantly now.

Gina tensed as Sandra found "the spot" and suddenly they both began to buck causing the box spring to creak. Gina exploded into Sandra's mouth and Sandra flooded Gina's throat with her sweet nectar at the same time. Their orgasms hit simultaneously and they doubled their efforts as they rode the waves.

While Sandra had had orgasms like this before Gina had never felt anything like what was happening to her now. The sensation filled her body and wave after wave of pure pleasure washed over her. She began to realize through her orgasm induced haze that this could go on forever. Sandra's finger was sending electric jolts through her whole body and they just kept coming.

Sandra finally began to come down off her sexual high and withdrew her finger from Gina's bottom and they both began to relax, slumped there in that sixty nine, the bedspread damp from their lust. It seemed like an eternity when Sandy turned and looked her lover in the eye and kissed her warmly then took her by the hand and lead her to the bathroom. Without a word between them Gina started the shower and they climbed in letting the warm water wash over their bodies. After they cleaned and explored each other for a while longer they tumbled out of the shower and into bed. They slept a deep and peaceful sleep in each others arms.

When morning came they were both still cradled together and as their eyes opened they kissed lovingly. Gina propped herself up on an elbow and looked fondly into Sandra's eyes "Why did we wait so long to do that?"€ she asked her lover softly.

Sandra smiled back at the redhead and replied "Somethings can't be rushed baby. It wasn't time until last night and then it was amazing."€ Gina nodded in agreement cradling Sandra's face kissing her lips deeply.

They laid that way for quite a long time until Sandra wiggled out from under Gina "We have a lot to see today sweetheart. I would love to lay in your arms and make love all day long but this city is amazing and who knows what is waiting out there for us." Sandra pulled Gina up out of the bed and into her arms kissing her on her perfect lips then they headed for the bathroom.

They both wore pretty sun dresses with floral patterns and boldly colored petticoats. They had light colored stockings with Cuban heels and seams running up the back of their legs. On their feet they wore low heeled black and white saddle shoes that weren't quiet period but very retro. Around the top of the shoes the white lace of frilly socks surrounded their ankles.

The two of them could have been girls right out of the fifties taking in the sights. Gina was getting used to letting Sandra doll her up to the point that she thought she might miss it when the trip was over. As the girls were eating breakfast Sandra announced to Gina that she had a surprise for her that night and that they needed to be back to the room about five.

By six thirty Gina was standing in front of the mirror with the redheaded bombshell gazing back at her. Her purple and black dress clung to her body in all the right places while her black satin opera gloves and vintage Silver Fox stole gave her more than a touch of elegance. As she felt her tears begin to well up for the untold time that day Sandra's arms wormed their way around her waist. Gina saw the blonde's Cheshire smile in the mirror peeking out from behind her. Gina turned around and kissed her before turning to leave the room. Gina wasn't sure what was in store for the evening but she was sure she wouldn't soon forget it.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
JoJoJuddJoJoJuddalmost 9 years ago
Encore !

The author's descriptions from the characters' passions to the hotel in a romantic city, made this story become so genuine, that I had to do a reality check. Sure enough, a quick google search and the place is exactly as described. Brilliant. Jasmine, you really have a talent for putting the jazz in a story.

braingasmssbraingasmssabout 9 years ago
Love it!

Great storytelling great command about what makes sissies so damn hot!

AnonymousAnonymousabout 9 years ago
MORE

MORE, MORE,TELL MORE...............PLEASE

AvidSmutReaderAvidSmutReaderabout 9 years ago
Nice beginning

Looking forward to the series :)

Share this Story

READ MORE OF THIS SERIES

Similar Stories

My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
The Big Mature Shemale Next Door Little guy is fed cum and seduced.in Transgender & Crossdressers
She Has a What?! Teaching his roommate how to use her assets.in Transgender & Crossdressers
The Best Prom Ever A senior takes the girl of his dreams to the prom.in Transgender & Crossdressers
My New Job A college kid undergoes a transformation at his new job.in Transgender & Crossdressers
More Stories