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~The following is entirely fictional and just a fantasy of mine. Any likeness to actual persons or events is unintentional and coincidental. Also, this is just a Pilot. If the story gets enough positive feedback, I’ll continue it on a regular basis.~
My name is Rosalie or just Rose for short. At least it is when I’m dressed up like a 20 year old college girl. My name is Tommy most of the rest of the time. Most would classify me as a crossdresser for the time being. But soon enough, I would realize that I wanted to be more than a part-time woman. Two years ago, after my mother’s death, she left everything to me. Including the house, money, car, and everything in the house. Luckily for me, my mom’s size and frame was nearly identical to my own. I could wear all of her clothes, shoes, jewelry, and whatever other accessories I could find. Being a chemotherapy patient, my mom also kept several different wigs in the house.
Almost every night after work I would come home, take a shower, and pick out a new outfit from my mom’s old wardrobe. I would complete the look with a pair of breast forms I finally worked up the courage to buy off of the internet, and one of my mom’s wigs. This time I had chosen a pair of purple panties with matching bra, a flared denim skirt that came to just about six inches above my knee, and a frilly white blouse. I completed my look with a long brunette wig that framed my face perfectly. I applied enough make-up for a natural femme look and slid into a pair of black calf-boots with 3 inch heels. The heels brought me up to a whopping 5’9. Being short and weighing about 130 pounds made me look exactly like your average 20 year old girl.
Usually, I would just take pictures of myself all dressed up and post them to my crossdresser dating sites, but tonight I was feeling adventurous. I decided to go for a drive. I figured I would go walk around at a rest stop outside of town. It was close enough to where I wouldn’t get myself into too much trouble but far enough away that I didn’t risk seeing anyone I know. However, it ended up being someone that I had never met before that would change my world as I knew it.
I took a break from walking around the rest stop and sat at a nearby picnic table. My feet needed a rest. After all, I was walking Kurtköy Sınırsız Escort around in heeled calf-boots. I crossed my legs as femininely as possible and grabbed my camera out of my purse. I decided to get a picture of myself out in the world to remember this night, though I won’t soon forget what happened right after.
“Hey there, sweet thing. What’s a pretty little thing like you doing out here all alone on a Friday night?” I nearly jumped out of my skin as I heard his voice. But when I turned around, what I saw nearly left me breathless. This guys was about 6’3, muscled, and handsome. My fair white skin was nothing compared to his tanned masterpiece. This man was HOT! His short brown hair glistened in the moonlight as he looked down at me.
“I was just um, out for a walk.” I managed to say between breaths in the most feminine voice I could muster. “My friends bailed on me so I decided to come alone anyway.”
“A cute girl like you shouldn’t be making the kind of friends that would leave her to come out here all alone. A lot worse than me could have found you. I’m David by the way, what’s your name?”
“It’s Rosalie. Or just Rose is fine.”
“Okay Rose. You can call me Dave. I’ve been driving this truck almost five years now. This is the first time I’ve met a sweet young thing like you.”
“This is the first time I’ve met such a gentlemanly trucker like yourself.” I looked up into his big, green eyes and did something I never thought I would actually do, especially since I had a girlfriend who, thankfully, was with her parents on vacation for the next two weeks. I leaned up and kissed Dave square on the lips, my glossed lips meeting his. Surprisingly, he returned the kiss with such force, it sent a surge of lightning through my entire body. He pushed his tongue past my lips and it began to search for mine. It didn’t take long as mine was ready to meet his in a passionate embrace. I had lost all control of myself. I could feel what was left of Tommy’s mind slowly melting away, letting Rose take the reigns. And take the reigns, she did. I broke away from our passionate make-out session to slide off of the picnic bench and I got down on my knees, my face right in Dave’s crotch. I unzipped the fly of his jeans and pulled out Kurtköy Suriyeli Escort his cock. It was a thing of beauty. It was about 2 inches thick, but had to be close to 9 to 10 inches in length. The way it bent made it the perfect instrument for the symphony Rose wanted to conduct tonight. I kissed the head of this masterpiece of a dick and opened my mouth, letting it slide right over my glossed lips and into my waiting mouth. I controlled the urge to gag as my head bobbed down the shaft of his cock, pushing the tip to the back of my throat. I bobbed back up slowly, sliding my tongue all around this lollipop I had in front of me. This continued for nearly twenty minutes until he stopped me.
“Why don’t you drop those panties for me, Rose? Don’t worry. I know who you are. I’ve seen your profile.” I did as my new lover asked without even thinking. At this he hoisted me up off the ground, and positioned me right over his dick, still wet from my own saliva. I knew that as soon as he got that beautiful tool inside of my body, I would be lost to the feminine side forever. If I hadn’t practiced this almost every night for the past month and a half with a dildo I had hidden away in my mom’s room, this pain would have been excruciating. Dave slowly lowered me onto his fully erect member, and the spasm of pure pleasure I felt was enough to make me moan louder than any girl, crossdresser, or t-girl I had ever seen in any porno I’ve watched. I began to bounce myself up and down on Dave’s cock with him guiding my hips. It was the most exhilarating feeling I had ever experienced. Before I knew it, I had stained the front of my skirt with my own semen. After about 30 minutes of bouncing me up and down on his cock, Dave then stood up, holding me up by my legs, still positioned firmly on his dick and laid me down on the table. He pulled back just enough to start pumping my now-stretched hole like there was no tomorrow. I was getting the brains fucked out of me now, and loving every second. Is this what all women felt the first time a man was inside of them.
Dave leaned forward and kissed me passionately again while still pumping my ass faster and faster. His tongue explored my mouth again, as his dick was still exploring my eager ass. He stopped kissing me Kurtköy İranlı Escort and slowed down his pumping. He backed further out of my ass then before and then pushed all the way back in slowly. This continued for another 20 minutes until he started pumping me again, faster and faster, harder and harder. All I could do was push back against him and scream in a mix of pleasure, lust, and pure ecstasy. I even caught myself asking Dave to fuck me harder, faster, deeper. Finally after another 30 minutes, Dave pushed his whole 9 inch cock into my ass, and he hit something. My whole body quivered and spasmed with delight. I had never experienced anything like this before, but I was sure Dave had just hit my g-spot. And what made it even better, he shot jet after jet of warm, hot semen into my hole. It had to have been almost a full cup of cum spilling into my ass.
“Wow! Rose, this was amazing.” He said to me as he pulled the plug out of the socket it belonged in.
“You can say that again,” I gasped, “I’ve never been fucked like that before. It was the best time I’ve had in 20 years of life. No wonder I’ve never been able to have sex with my girlfriend. I need a boyfriend, pronto.”
“Well I can volunteer my services,” He smiled, “I don’t leave until the day after tomorrow.” With this I tried to stand, but wobbled and almost fell. Dave caught me and scooped me up like a groom holding his bride. I wrapped my arms around his shoulder and neck and just leaned my head against his warm chest.
“Take me, Mr. Truck Driver. I need you more than I’ve ever needed anything in my life.” With that, Dave smiled and held me closer to him, as he walked over to his truck. he put me in the cab and then walked over to his side.
“I’ll take you home. You’re in no condition to drive, babe. You can’t even walk. Just tell me how to get there.” I hit the button on my keys to lock my car and lead Dave to my house. He got out of the truck, and pulled me out, carrying me through the door of my house and up to my mom’s bedroom where he laid me down on the bed.
“Dave…” I said, kind of dazed, “Don’t leave. Stay with me. I’ll make you breakfast tomorrow if you want.”
“I’d like that.” With that, he laid down on the bed next to me, wrapped his arms around my waist, and we laid there quickly falling asleep. I had dreams all night about Dave fucking me over and over, at the rest stop, in my mom’s room, on my kitchen table, in a hotel, in his truck even. It always ended with me asleep in his arms. And you know what? There was nowhere else in the world that I would rather be.
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