tagTranssexuals & CrossdressersNobody Rides For Free

Nobody Rides For Free


My name is Jerri, I ended up in this predicament in a hilarious way, I was just heading home from my girlfriends house when I got a flat tire. Getting out my cell phone, I tried to call a tow truck. I wasn't really surprised when there was no signal, I lived out in the country. I didn't want to get out of the car, it was cold and windy, but that wasn't the reason. The reason was, I was wearing a dress. My girlfriend and I had been exploring playing dress up, I did it as a dare, now I was regretting wearing the cute red lace mini skirt, it made my long legs look like they went on forever. The push up bra gave me the illusion of breasts, I felt so....naked.

I couldn't sit in the car all night, I reasoned. Getting out of the car, I decided to walk for help. I wobbled on my 4" stiletto heels, gaining new appreciate of the price of beauty. I hadn't gone far when I heard a car, I quickly raised my arms to flag the person down. A pickup truck drew abreast of me and the window rolled down, I was so nervous. No one had ever seem me dressed as a women, my girlfriend was going to have a laugh at this.

"Mighty cold day to go gallivanting around in a mini skirt dress, young lady." The sound reached my ears, I was so startled I jumped. The woman behind the wheel was a full figured lady, she was attractive and had a nice smile.

"My car broke down just around the curve, Ma'am. I had a flat, dummy me, I have no spare. Can I have a ride into town?" Maybe this wasn't going to be such a bad experience, I thought.

"Climb in, young lady." She smiled at me. I climbed in, she grabbed my leg and used it to pull me towards her. "don't sit too close to the door, it doesn't latch properly." Her hand remained on my lap, stroking up and down my silk stocking legged.

"You look very nice, young lady. Where is my manners, I cant keep calling you young lady. What is your name? I am Rachael." She chucked, her hand sliding up my leg higher, settling in between my legs and just resting there.

"Jerri," I said, my voice high and squeaky, "My name is Jerri, it is nice to meet you Rachael." I grabbed her hand and tried to push it lower, back down on my knee.

"A mighty fine name, Jerri." She made a right turn, and I opened my mouth to ask her where she was going. "Just taking a short cut, this will get us into town faster."

I smiled, I really didn't know the area that well, so I took her word. Ten minutes later, I started to get nervous as it got darker outside. Rachael pulled the truck over.

"How much money you got, Jerri?" She asked, "its a long drive into town and I expect to be compensated for my time."

I jumped, her voice startled me in the now total darkness except for the illumination of the dash lights. I dumped my purse out, counting the change, I came up with $5 and some pocket change.

"That isn't enough." I heard, now sweating, I said. "When we get into town, take me by an ATM. I got a debit card and I can get cash out."

"Debit card?!" I heard asked incredulously, "Where would you like me to swipe your debit card, my asscheeks?" Grabbing my crumpled $5 bill, Rachal threw it out the window.

Her hand was now pushing my skirt up, she grabbed my bulge, starting to tease it with her hands.

"I am sure we can work this out, Jerri. You don't seem like a bad girl, just not very bright." She slapped me across the face when I didn't respond to her satisfaction, got a handful of my hair and used it to pull it down in between her chubby thighs. "Lick me bitch, NOW."

My tongue flicked out, I pushed her jean skirt up and I started to eat her out. Her hand fisted in my hair controlled the movements forcing my tongue in and out of her tight quim. Soon she orgasm, squirting all over my face. I thought it was finished, boy was I wrong.

"You made a mess, lookit what you did!" She snapped, getting on her knees, she turned around and stuck her ass up in the air. See, you made a mess now clean it up."

I licked her messy ass, it was good and wet, I buried my tongue in between her round chubby ass cheeks, reaming her out. My clit was rock hard and I had to stroke it. I took my clit out and started to stroke it, my other hand had two fingers inserted in her aching cunt, banging her hard.

She eyed my big 7 inch clit, now that her asshole was nice and wet and clean, she straddled me and slipped her tight ass right onto my big hard 7 aching length. She was so fucking tight, obviously an anal virgin, she was so riding me like a pro. She came them, squirting all over my cock. She made me clean myself and her up with my coat. My hips were jerking, she didn't let me come after taking her pleasure. Sliding two fingers into her cunt, she rammed them up my ass as she licked me, deep threading me as she bobbed her head up and down.

"I love when a guy shaves his balls, you fucking slut. Lookit, your girlfriend even shaved your asshole!" A third finger joined the other two, her fingers filled me up so good, I moaned. Keeping her fingers in my ass, she straddled me and rode me, her tight wet cunt milking me. After three or four more orgasms, she stopped, climbing off of me she pulled her skirt down. My cock was standing straight up, I ached to come.

"Thank you Jerri, that was a lot better then money. Ass, grass or ass, nobody rides for free."

Climbing behind the wheel, she restarted the truck. We were in town within minutes, I was so horny my eyes were crossed. I needed to come. I figured she was taking me to her place, I was startled when we pulled up in front of a public telephone booth. Leaning across me, she pushed open the passenger side door.

"Have a nice night." She put my hand on my thigh and pushed me out the door. I stood in the cold, my 7" clit standing to attention, watching her taillights disappear. Then I picked up the phone and called my girlfriend, I had a lot of explaining to do.

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