I have just graduated from college and need to get away for the summer before settling down and finding a job. My girlfriend has just left me for my best friend and a cross country road trip is the perfect way to spend some time alone and get over it. I am 21, 6'2" and 190 pounds, all muscle. On the weekend after graduation, I pack my things into my restored Corvette, a car my dad had originally purchased in the 60s, and set out on my trip. I have some money saved up so I can stay in some small hotels over the course of my trip and buy some food. Nothing fancy of course, I am just out of college and most of the money is a gift from my dad for my graduation.
On the first day of the trip, I make my way from Los Angeles to Nevada, stopping briefly in Las Vegas. I still have a lot of the country to see, so I don't want to blow all my money in Vegas on the first day. As I am driving through the desert a while after leaving Vegas, I happen upon a woman looking quite frantic on the side of the road. I normally don't stop to pick up people on the side of the road, but this girl looks like she is in trouble and has been in the desert for quite some time. She looks to be about 5'6" with long legs and an amazing body. She is wearing a pair of cowgirl boots, a pair of short low-cut denim shorts, and a black tank top that has been soaked through with sweat. Her long blonde hair is blowing all over her face and she has three suitcases with her.
"Are you OK?" I ask as I pull over, "Did your car break down?"
"No, I have no car," she says in a dry raspy voice, "Could I get a ride. I'm afraid I have no money, but I need to get back home."
"Sure," I say getting out of the car and putting her luggage in the car.
I get back in and offer her a bottle of water. She gulps the entire bottle down in less than a minute. She crosses her legs and sits uncomfortably trying to cover her breasts with her arms. How did she get out here and how long had she been in the desert before I found her?
"My name is Dave," I finally say to break the silence, "What's yours?"
"It's Lindsey," she replies softly, "It's a family name."
"Well, it's nice to meet you Lindsey," I continue, "That's a very pretty name."
"Oh, hey," Lindsey says perking up, "I don't want you to get the wrong idea about me. I'm a guy."
"Wow," I respond in surprise, "I would have never guessed. You're very convincing as a girl. How long have you been cross-dressing?"
"Hey," she says defensively, "It wasn't my idea to dress like this. I was on vacation in Vegas with some people I thought were my friends. Apparently they drugged me one night and this was their idea of a prank. The next thing I knew I was waking up in the desert dressed like this with no money and no phone. Luckily they left me some food and water, but after a couple days I was starting to run out. That was when you came along."
"Why don't you just change?" I ask confused.
"Believe me," Lindsey continues, "I would like nothing more, but these boobs and vagina are glued on, my ears and naval are pierced, and those suitcases are filled with chick stuff. They didn't exactly leave me with anything to get the glue off."
"Well, I would lend you some of my clothes," I offer, "but they'd probably be too big on you."
We continue driving in silence. Even though I know Lindsey was a guy, dressed like that I continue to think of him as a girl. As we continue to drive, she eventually opens up and tells me how she too recently went through a break up with a girl she had been dating for 3 years. Despite the fact she is a guy, she has a voice that is a little higher and more feminine than most guys our age. After driving through the desert for a while, we spot a small diner. Both feeling very hungry, I decide to pull over for a quick bite to eat. She is afraid to get out of the car, so I go in and order us some food to go.
We continue on our way and I watch in shock as she scarfs down her burger. Wow, where does she put all that food? After driving a while longer, I pull over to get some gas. I ask her if there is someone she'd like to call, but all her numbers were on her phone and she doesn't have them memorized. I guess that's one of the problems with technology today. We become too reliant on it and it's hard to function when we lose it. Lindsey nervously gets out of the car and goes inside to use the women's rest room. I give her some money to buy some things while she's inside. When I finish filling the tank, she comes back out with some snacks and water.
We leave the gas station and drive a little longer until it gets late. I find a small hotel, nothing too expensive, and decide to stop for the night. Unfortunately, needing to make my money last the entire trip, I can only afford a room with one bed. I grab our luggage from the car and carry it inside.
"You can take the bed," I say, "I'll sleep on the chair."
"Thank you," she says as she begins looking through her suitcase for something to wear to bed.
Unfortunately, they left her only very short revealing things to sleep in, so she grabs a pair of tiny pink shorts, a tooth brush and tooth paste, and some makeup remover and goes to the bathroom. She comes out a while later with her makeup gone and her hair in a ponytail, but still looking as beautiful as ever. She has removed her bra, but still wears the tank top from before with the little pink shorts. Looking at her, it is clear her eyebrows have been thinned and shaped and I can spot a tattoo on her lower back that she probably does not know about. She glances nervously at me as she climbs into bed.
"I'm sorry for all this," she says, "I can find another way back to New York in the morning."
"Don't be silly," I reply, "I'm headed there anyway and I feel responsible for you now. It's no trouble at all."
She gives me a shy smile as she settles in and falls asleep. I go to the bathroom and change into a t-shirt and a pair of pajama pants. Normally I would sleep in must my boxers, but I don't want to make Lindsey feel uncomfortable. I brush my teeth and try to make myself as comfortable as I can on the chair. I look up one last time at Lindsey before turning off the lights and going to sleep.
When I wake up the next morning, she is already in the shower. I decide to leave the room to get us some breakfast at the diner and to give her some privacy. When I return with the food, she is dressed in another pair of short shorts and another tank top. Apparently, they didn't leave her any pants or t-shirts to wear and she didn't feel comfortable wearing the heels, skirts, or dresses. She stands in the bathroom doing her makeup. She doesn't put on much, but she seems to know what she's doing.
"You're pretty good at that," I say.
"You pick up some things when you grow up with a single mom and three sisters," she replies.
When she finishes her makeup, I go in the bathroom to take a shower and get ready. Not long after, we are back on the road and it isn't long before we are in Texas. I make some stops along the way, but each time Lindsey decides to wait in the car. For the first couple days, things continue much the same. I feel bad for Lindsey and stop to get her some jeans and t-shirts at a store in Texas.
"You bought these for me?" she asks in surprise as I return to the car.
"Yes," I say, "I thought you'd like something more comfortable to wear."
"Thanks," she says, "Don't worry. I will pay you back as soon as we get to New York."
"No need," I say, "Think of it as a gift."
I notice a slight smile on her face as she takes off her shorts and puts on a pair of jeans right there in the car. That night when we stop at the next hotel, she does something that takes me by surprise.
"Would you like to share the bed tonight?" she asks shyly, "One of us would have to sleep over the covers of course, but sleeping in a chair can't be too comfortable."
"If it doesn't make you too uncomfortable," I say.
"Don't worry," she responds, "I can manage."
We get into bed and I watch as she settles in on top of the covers. She is wearing the same thing she has worn the past few nights and I can't help but admire how hot her long tan legs look. Her skin is so smooth and hairless and her toenails are still painted in a bright red. I feel a twinge in my pants, and not wanting to make the situation more awkward I turn off the lights and go to sleep.
The next morning, I open my eyes and find Lindsey still asleep. She has rolled over and her face is inches away from my own. How I wish I could kiss those lips. I quietly slip out of bed and go to the bathroom to relieve myself. Am I falling for Lindsey? That is crazy, we're both guys. I have to forget this before I do something to make her even more uncomfortable than she already is. I finish getting ready and when I come out Lindsey is awake and watching TV. She smiles at me as she stretches and gets out of bed.
"How did you sleep last night?" she asks.
"Much better, thank you," I reply.
"You're welcome," she says, "It's the least I could do after all you've done for me."
She grabs her things and goes into the bathroom to get ready while I get us some breakfast. Surprisingly, when I get back she is wearing a skirt. She has also swapped out the boots for a pair of heels.
"Wow," I say, "What's with the skirt?"
"I don't know," she replies, "I guess I was feeling curious. These past few days I've been feeling more and more like a girl. At first I hated it, but now I think I'm starting to like it. As long as I'm stuck like this, I might as well make the best of it."
When we make our way back down the road, I notice a change in her. She seems happier and isn't constantly brooding like she was before. She even gets out of the car with me when I stop to sightsee. We also have lunch together for the first time in a restaurant and she doesn't even seem bothered when the waitress refers to her as a woman or as my girlfriend.
After spending several days in Texas, one of the states I wanted to explore on my trip, we make our way into New Orleans. As we walk around the city, Lindsey catches me by surprise and grabs my hand. As we walk around the city hand in hand, I begin to wonder if Lindsey is falling for me too. A band is playing nearby and there are some people dancing. She pulls me over and begs me to dance with her. As we dance, I can't help but notice how beautiful she looks in her short summer dress.
As we continue our trip and make our way north towards Chicago, this behavior continues. While I wouldn't describe our relationship as a romantic one, I notice Lindsey becoming more comfortable as a woman. She holds my hand whenever we go out and asks me to buy her more female clothing. She even starts sleeping in more feminine attire and allows us both to sleep under the covers. I am able to get more money from my dad when he finds out I have met a girl and I give some money to Lindsey to spend at her discretion.
When we finally get to Chicago, we are able to stay at a nicer hotel. As I go to check in, Lindsey asks for a room with one bed. I look at her in surprise and she just smiles at me. When we get to our room, I ask her why she wanted a room with one bed and she tells me it is better for appearances. She grabs some things and goes into the bathroom to get ready to explore the city. She is in the bathroom for a very long time and I begin to get worried. Finally, she emerges wearing a little red mini-dress and 5" heels. Her hair is styled and her makeup is expertly done.
"Wow," I say, "Why so dressed up?"
"We're spending the night in Chicago," she says, "I have your suit ready for you to wear too."
I get ready and we head out arm in arm to explore the Chicago nightlife. We are able to get into a pretty nice restaurant and Lindsey is even confident enough to order some wine and show the waiter her ID. With the name Lindsey and her feminine facial features, the waiter doesn't even think to check the gender as he reads the birthdate. We enjoy a nice dinner then explore the city some more before going back to the hotel.
"Is it OK if we spend another night here?" Lindsey asks.
"I suppose," I say, "but don't you want to get back home?"
"Home can wait," she replies, "Besides I'm having fun."
She gives me a kiss on the cheek and goes to the bathroom to change. The kiss lasts less than a second, but it leaves me with a mix of emotions. Lindsey is an amazing woman, but she is still a guy. Can I really be falling for a guy? I notice Lindsey's purse had fallen and when I go to pick it up, I see a used adhesive tube. It seems the adhesive had worn off days ago and Lindsey had glued everything back in place. Also, I've noticed that she must be shaving her legs since I haven't seen any stubble the entire trip. Does she want to stay a girl?
Lindsey comes out of the bathroom wearing a tiny baby doll and matching panties. She gets into bed and tells me it is OK if I want to sleep in boxers tonight. Having run out of clean sleeping clothes, I strip down to my boxers and get in bed. I feel her smooth leg against my own and she doesn't pull away. I turn off the lights and go to sleep.
When I wake up, I hear Lindsey in the bathroom taking a shower. The water stops, and instead of getting dressed in the bathroom as she has done before, she exits the bathroom wrapped in a towel.
"Good morning," she says smiling at me.
"Morning," I say as she drops her towel and begins to get dressed right in front of me.
I stare at her in disbelief. It is the first time I've seen her naked, and she is more girl than I could possibly imagine. Even her breasts and vagina look surprisingly real. There is no sign of the guy hiding underneath. Maybe she was joking before when she said she was a guy. I take a glance at her ID when she isn't looking and it clearly says male. She catches me staring and only smiles.
"Do you like what you see?" she asks turning around.
"Um, I guess," I reply not wanting to sound creepy.
She just laughs as she finishes getting dressed and goes to the bathroom to do her hair and makeup. As I watch her, I notice her movements have even become more feminine. Also, it has been several days since she has worn shorts, pants, or any shoes without a heel. She invites me to take a shower while she does her makeup and I reluctantly take her up on the offer.
When we are both ready, we go downstairs to have breakfast and spend the day doing more sightseeing. We walk together arm in arm with her head resting against me. We decide to go to a White Sox game, and at one point we appear on the screen during the kiss cam. I sit awkwardly not knowing what to do, but without hesitation Lindsey kisses me on the lips. It isn't a passionate kiss, but it feels amazing nonetheless. She breaks the kiss and we return to watching the game.
After the game we return to the hotel and get ready for dinner. Lindsey puts on another sexy dress and really plays up her femininity by waiting for me to pull her chair out for her and open the door for her when we go out. After dinner we go for another walk before going back to the hotel. Once in our room, Lindsey turns on some music and asks me to dance with her. It is clear she is a little drunk, but I dance with her the same. We fall on the bed laughing and turn to each other as we lie in bed. We both stop laughing and stare into each other's eyes. Soon we are embraced in a passionate kiss. Our tongues moving around each other's mouths as my hand creeps up her bare thigh. Soon my hand is under her dress and is dangerously close to her panties. She pulls my hand away and breaks the kiss with a frightened look on her face.
"Oh my god," she shouts jumping out of bed, "I'm becoming a woman. I should have changed back into a guy a long time ago, but I started enjoying being a girl too much and I think I've started falling for you. This has to stop now."
"Maybe I should sleep on the couch tonight," I suggest.
"That's probably a good idea," she replies.
She goes to the bathroom and changes for bed. Unlike this morning, she dresses and undresses in the bathroom. She comes out wearing a tank top and a pair of sweats I had bought for her several days before. Without saying anything, she gets into bed and falls asleep. I change for bed and go to sleep on the couch. Tonight I am fully clothed so as not to make the situation more uncomfortable.
The next day we quietly pack up and head back out on the road. Today Lindsey is wearing jeans and a t-shirt. Her hair is in a ponytail and she has not worn any makeup and has removed her nail polish. Even without makeup she still looks so beautiful. Unfortunately, since she reapplied the glue so recently, she was stuck with the breasts and vagina. We drive in silence as we make our way to New York. I pass several places I would like to see, but decide it's best not to make any stops.
Unfortunately, the car breaks down when we get to Philadelphia and we are forced to spend the night. The only room available at the hotel is the honeymoon suite, so we reluctantly grab our things and go up to the suite. Inside, flowers and champagne have been prepared for us and there is a hot tub on the balcony. We stare at each other and Lindsey breaks down in tears. I hold her close to comfort her.
"Last night, I broke the kiss not because I didn't like it," she says, "It was because I was afraid I was enjoying being a woman. After having some time to think, I know I am meant to be a woman and I'd like to be your girlfriend if you'll accept me."
"Of course I will," I say as I dry her tears.
She smiles at me and we begin to kiss passionately. This time none of us hold back and soon we are removing each other's clothes. Her hair falls loose and soon we are in bed in just our underwear. She still isn't wearing any makeup and her hair is a mess, but I love her just the same. I don't care if she is a guy, I love her more than any woman I have ever been with. This is her first time being with a guy, and it is clear she is very nervous. We continue to kiss as I remove her bra. I stare down at her magnificent breasts and she smiles back at me.
"Teach me how to be a woman," she purrs seductively.
I begin to kiss her softly on her stomach as she lets out a soft moan. Slowly I make my way up her chest and gently suck on her nipple. While her breasts are fake, she seems to be enjoying it just the same. We kiss again before she whisper in my ear that it's her turn. I find myself lying on the bed as she pulls my boxer off and throws them aside. She stares at my penis and kisses the tip. Slowly, she begins to lick the shaft and soon takes it into her mouth. Being new at this, she is not very good, but she seems to enjoy it just the same. She isn't able to swallow all my semen and it gets all over her face.
"Practice makes perfect," she says as she cleans herself up.
She takes off her panties and pulls me to the hot tub. We begin making out again and soon she has climbed on top of me. I begin pumping her slowly as she lets out soft girly moans. Her moaning gets louder as my movements become faster and more vigorous. After we climax, we roll off each other and lie in the tub catching our breath.
"Oh my god," Lindsey exclaims, "Sex as a girl is so much better than sex as a guy."
We kiss again before going to the bathroom together to get ready for bed. We take a shower together and Lindsey changes into her sexiest nightie while I put on a pair of boxers. We get into bed together and kiss each other again.
"I love you so much baby," she whispers.
"I love you too," I say kissing her again.
We decide to prolong our trip, even after the car is fixed, and have sex several more times. Lindsey is getting much more comfortable as a woman and her most recent blow job was incredible. When I finally get her to New York, Lindsey the guy has disappeared completely. When we get to her apartment, her friends are outside waiting for her. They watch in surprise as we get out of the car and walk hand in hand inside the building. She gives them a slight wave as we walk inside. Almost immediately, she starts removing everything from her previous life and replacing it with her new female identity.
"Are you sure about this?" I ask.
"More than anything," she replies as we throw all her old stuff out, although I secretly put her stuff into storage should she change her mind.
It's been a ten years since that day and I have to say, Lindsey's friends and parents did not take the news too well that she was becoming a woman, although her sisters and ex-girlfriend were very quick to support her. My parents were also surprised, but upon meeting Lindsey they took her in as one of the family. Unfortunately, Lindsey's parents, who were divorced, disowned her and refused to ever see her again. Lindsey was upset, but quickly moved on and soon she was living with me in California.
For a brief period she questioned whether she was making the right decision and began living as a guy again. She thought she may have rushed into this and wanted to make sure it was what she really wanted. At the time, she still had feelings for her ex, and to this day identifies as bisexual. She began consulting a therapist and speaking with sisters and ex before realizing this was the path she was always meant to be on. She soon began HRT and in a few years completed her transition into a woman. Now her breasts and vagina are entirely her own and she's updated her ID to reflect this change.
Not long after her operation, she began law school and I started medical school. She is now an attorney at a Beverly Hills law firm and I recently complete my residency at the hospital. We are both making good money and Lindsey's parents even made an attempt to reconnect with her. It will take some time, but Lindsey has made steps to reconcile with them.
A few years after our trip, I proposed to her and we were married not long after. While her parents did not attend the ceremony, her sisters and ex-girlfriend were her bridesmaids and maid of honor. Since her father wasn't present, my father agreed to walk her down the aisle. By that time, he had become more of a father to her than her real dad. Even before her transition, her dad had been absent for most of her life. For our honeymoon we took a road trip to commemorate the first time we met. Soon after we were able to use a surrogate to have children and using my sperm and the sperm Lindsey had frozen before her transition, we are now the parents of a 4 year old boy, using my sperm, and a 2 year old girl, using Lindsey's.
As I think back to that road trip all those years ago, I remember how much I wanted to be alone at the time. Instead, I met the woman who changed my life forever. I have a great job, a loving wife, and two amazing children. What more could a man ask for?
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Dave is traveling alone on a summer trip across country when he picks up a beautiful hitchhiker. The hitchhiker turns out to be a guy who is stuck as a girl after an elaborate prank on vacation with his friends. Needing to get back across country, and with no other options, the hitchhiker joins Dave on his trip.