tagTranssexuals & CrossdressersRiding in Cars with Shemales Ch. 01

Riding in Cars with Shemales Ch. 01


I'm going go ahead and get this out of the way. During my freshman year of college, I was confused about my sexuality. It sounds strange saying this right after calling myself confused, but I loved girls. I really did. I loved all of their shapes and curves. I loved tits, pussy and ass.

Now, I know what you're thinking. You're thinking that I'm just some gay guy that doesn't want to come out of the closet and is overcompensating. I honestly don't care what you call me. Up until freshman year, I considered myself one hundred percent straight. However, I quickly learned that sexuality is not always black and white.

I made a fairly startling realization that year. I enjoyed putting things in my ass. It started off as a curiosity thing. I had always heard, "How do you know if you haven't tried?" Plus, I learned that the equivalent of the male g-spot could be stimulated through the ass. So, I stuck my middle finger up there while I masturbated once.

I really enjoyed the sensation and it made my orgasm stronger. Just like that, I was hooked. Soon, I was putting all kinds of things up my butt. I would go to the store and buy a pack of Sharpie markers or a hairbrush to fuck myself with the handle.

I watched a lot of porn at that age.... Who am I kidding? I still watch a lot of porn. Anyways, I started watching these videos of girls fucking guys with strap-ons. I was dating a girl named Tina at the time, and I would imagine her fucking me with a strap-on while I masturbated. It was a huge turn on for me.

So, one day I gathered up my courage and confided in Tina my secret fetish. I asked her if she would be into using a strap-on on me. Her reaction was not the desired effect. She was repulsed by the idea. More than that, she was repulsed by me. In fact, she broke up with me over it, telling me, "I don't date faggots, Matt."

This struck a nerve. Up until that point, I only thought of my desire as a fetish. What if she was right? What if I really was gay? So, I tested it out. I looked up some gay porn and watched it. I watched several videos, in fact, with all different kinds of guys fucking all different kinds of other guys. I gave jacking off to it a good try, but nothing worked. I wasn't turned on by any of it.

Luckily, this didn't stop me from fucking my own ass. After a while, I got more daring and bought a dildo from a sex shop. It was a natural, flesh colored dildo with a suction cup on the bottom so you could attach it to things. It was the best purchase I ever made. I would spend hours alone in my dorm room fucking my ass with the dildo attached to my dresser.

I was incredibly horny whenever I decided to use my dildo, but I always felt a sense of shame when I finished. I was still very confused. But, a sense of clarity finally came to me in the form of Terra.

Terra was this amazing girl that lived next door to me. I lived in a single room in a co-ed dorm. The dorm was divided into sections for girls and boys, but my room was on the dividing line, right next to Terra's. She also lived in a single. Since neither of us had any roommates, we ended up hanging out together all the time.

She was incredible. She liked to do girly stuff just like any other college girl, but she also liked doing things that I liked. She was always hanging out in my room watching movies or playing video games with me. She was really attractive too. Terra was short; not like 4 foot or anything, but, you know, short. She had long hair that was originally dark, but had streaks of highlights running through it.

Terra had dark blue eyes and a pretty smile. Her tits were that perfect size that I like. Not too big or too small, just the perfect size for grabbing onto. And, her ass... oh my god. She had such a mouthwatering, round ass. It stuck out from her backside so wonderfully. It was shapely and firm. Every time she would walk out of my room, my eyes would wander all over her.

Tina broke up with me in February, and Terra and I had started hanging out a couple of weeks after. She was always so nice to me and made me feel better about my recent break up.

Spring break was coming up, and all of my friends back home were going to get together and party. Sadly, I didn't have a way to get home. My parents were originally going to drive up and pick me up, but their work schedules ended up getting in the way. It looked like I was doomed to spend spring break alone in the dorms, but Terra offered to drive me. She had her own car and was going home too. Apparently, my home town wasn't too far out of the way for her.

So, I gladly accepted and we hit the road. Terra had a really nice car. It was a four-door sedan, but it was a very new model. I figured her parents must be rich if she could afford to have a car like that in college.

The trip was fairly generic. We played a few road trip games, stopped for snacks at a gas station, you know, pretty normal stuff. I lived about four hours from college and Terra lived about six hours away. After nearly four hours, we saw a sign for Stanbury, my hometown. The sign said we were just under twenty miles away.

"Look, we're almost there," I said and stretched my arms. The long hours stuck in the car had done its toll.

"Cool," said Terra. "I didn't know your town was the set of a 50's television show." Terra laughed. The name was incredibly amusing to her.

"Ok, Stanbury might be a lame name, but it's home. It's not as lame as you think actually. You could stay for a while if you want. My friends are throwing a party tonight."

"I would, but I promised I'd be home by evening. So, do you want to pay me now or wait until we stop?" said Terra casually. I almost didn't notice what she had said.


"I asked if you wanted to pay me now or later. For the gas."

"You... you want me to pay?" I said, not fully understanding. I had never gone on a road trip with anyone but my parents.

"Are you serious?" Terra said, a little agitated. "You expected me to drive you all this way and not split the gas? Come on, it's not even that much."

"Sorry, I didn't know," I said. "I mean I would, except... I kind of don't have any money."

Terra turned her head towards me and I could see that she was pretty angry.

"You don't have any money? Are you fucking kidding me, Matt?"

"I'm sorry, I didn't know," I said.

"How could you not know? It's common fucking courtesy."

"I'm sorry, Terra. I really didn't know. I'll make it up to you. I swear." Terra's mouth turned into a wicked smile and she looked me up and down.

"You're right about that, Matt. You are going to make it up to me. In fact, you're going to make it up to me right now." Terra turned off of the two lane highway we were driving on and took a dirt road. We went over two hills and then pulled over to the side of the road. We were out in the middle of nowhere.

Terra put the car in park and turned off the engine. She looked over at me and gently licked her bottom lip as she looked me up and down. The lust in her eyes was very apparent. I was starting to get a little excited. Was I going to have sex with Terra? I had fantasized about it a lot. Now, it seemed like it was actually going to happen.

"Get out of the car," said Terra. I obediently got out and stood next to the passenger side door. Terra got out too and walked around the front of the car towards me. She looked very sexy that day. She was wearing a black tank top and tight jeans that were tucked into a pair of black boots. She walked up to me and gently pushed me backwards.

I started walking backwards. When I had almost reached the trunk, Terra stopped pushing me and opened up the back door. Then she sat down on the seat, facing the door, her feet still on the ground. She motioned for me to come over.

"Get on your knees," she said. I was getting really turned on by this. I liked a girl to take control. I kneeled beside the car, right between her spread legs. Terra unzipped her pants and slid her hand deep down into her panties, staring at me the whole time. It looked like she was going to start fingering herself.

However, she brought her hand back out and a big dick suddenly flopped out. Terra smiled at my reaction. My jaw dropped and my eyes went wide. Right in front of me was one of the biggest cocks I had ever seen, and it happened to be attached to my friend Terra. I was very much in disbelief. Terra was a shemale. How could I not have known this? Terra continued to smile and wiggled her hips a little, shaking her dick from side to side.

I couldn't believe that Terra's cock was so big. It was completely limp, but still put my own cock to shame. I continued to stare, speechless. Terra hooked her thumbs into her waistband, raised her ass off the car seat and slid her jeans and panties down. I watched as she struggled a little getting her tight pants over her big butt then slid them down to her ankles. Her cock was now completely free, a monster hanging down between her legs.

"Well, what are you waiting for?" said Terra. "Suck it." I couldn't believe what she was saying to me.

"Suck it? Terra, I've never... never done... that... before."

"You've never sucked a dick before? Then it looks like I'll be your first," said Terra. She smiled again.

It seemed that I was in a bit of a dilemma. We were in the middle of nowhere, and I was twenty minutes from home. It's not like I could just walk away from this. Also, there was the realization that I was still horny.

Seeing Terra's dick had not reduced my lust, much to my surprise. In fact, I felt myself getting even more turned on while looking at her Terra's horse cock, swinging between her legs. So, after only a moment of considering, I put all my inhibitions aside and lowered my head towards her crotch.

We had been in the car for a long time, and it was a fairly warm day. I could feel a steamy warmth radiating off of her meaty dick. She must have had it tucked back all day in the hot car. As I got closer, I could smell the hot, pungent scent of it. I looked up again and made eye contact with Terra. She was the nicest, prettiest girl I knew, and I suddenly wanted nothing more than to suck her big cock.

Terra put a hand on the back of my head and pushed it down. I opened my mouth and took in a couple inches of her smelly cock. Tentatively, I started to lick my tongue around her head. Terra started to moan. It was strange hearing such a feminine moan from her while her massive cock was in my mouth. I brought up my right hand and wrapped it around Terra's dick while I continued to lick.

I started gently stroking. My hand glided across her cock, reaching her balls. I realized that she was completely clean shaven. I could feel Terra start to grow inside my mouth as she slowly became hard. I started stroking harder. Soon, her cock was fully hard. I stopped licking and raised my head so I could get a good look at it.

Fully hard, Terra's cock was quite the sight. It was an unbelievable 9 inches long. As she sat in the car, her erect cock almost reached the bottom of her breasts. Terra's cock was unique in that the head was not the biggest part. About two thirds of the way up her dick, the shaft bulged a little then tapered back down as it neared the head. It sort of reminded me of a spear head.

I lowered my head back down, taking several inches of Terra into my mouth. I locked my lips around her shaft and started dipping my head up and down. Terra really seemed to enjoy that and she moaned deeply.

"That's it, Matt. Suck my cock," said Terra. Hearing her say that increased my passion and I sucked harder, slurping on her big meat stick.

"Yeah, baby. Suck that big girl-cock." Terra moaned deeply again. "For never having sucked a dick before you're doing a hell of a job." I took a little pride in knowing that. I guess it came easy to me because I just did it how I would want someone to suck me.

"Take all of my cock, Matt. Take it all you filthy cock-whore." Terra grabbed my head with both of her hands and pushed me down hard, shoving her dick into the back of my throat and holding it there. My eyes shot open and panic was all over my face as I started to gag. Terra pulled out and pushed me deep onto her cock two more times.

I gagged as the head of her dick hit the back of my throat each time. She pulled me off her cock again and aimed my head up towards her face. She put one hand in front of me and made it into a fist.

"Put your thumb underneath all of your other fingers like this and squeeze hard." I did it just like she showed me. "Good. Now you won't gag so easily." Terra pushed my head back down onto her cock and shoved it deep down my throat. To my surprise, I didn't gag on it this time. Her little trick worked.

Terra then started bucking her hips, bringing her cock back a few inches before ramming it back down my throat. She took complete control of me, roughly fucking my face for the next twenty seconds or so. Then she pushed me off of her cock.

"Stand up," she said. I gasped for air, but stood up. Terra also stood up beside the car. Her cock was slick from my saliva and I wanted to kneel back down and suck on it some more. Terra shuffled her way behind me, her pants still down around her ankles. She undid my pants and pulled them down as well. Then she pushed my head down a little and forced me into the car. My legs were still outside and I was lying face down on her back seat. My ass was completely exposed on the edge of the seat, and I realized what Terra was going to do.

Terra moved between my legs and spread my ass cheeks with her hands. She spit a big glob of saliva that landed right on my exposed asshole. She worked the spit around my anus a little bit and then I felt her cock pressing against it.

I grit my teeth together as I prepared to get penetrated for the first time by a real cock. As Terra split me open, I felt a sense of panic. Nothing I had ever shoved up my ass had been as big as Terra's monster cock. Terra gave a small thrust and several inches of her were suddenly buried in my ass. My mouth opened and a loud "Uuuunnngh" escaped my lips.

"Well, well," said Terra. "That was easier than I expected. Looks like somebody's done this before." Terra giggled to herself. "Maybe it's from all those nights of fucking that dildo you keep in your sock drawer."

"What? You... you.... How do you know about that?"

"I found it after you passed out while we were watching 'Office Space' a few weeks ago. That, and the fact that I share a wall with you. I knew you didn't have any girls over." I was a little embarrassed realizing that Terra had been listening to me fucking myself. Thoughts started racing through my head, but then Terra pushed a few more inches into me.

My ass felt so stretched. It hurt a little bit, but the sensation was also making me hard. Terra allowed me to adjust to the size of her cock, gently moving it an inch in or out every ten seconds or so. Then she started humping me at a regular pace. My ass was greedily taking in her fat cock and I was loving it. I started moaning lowly.

"Yeah, take that dick, Matt. You love my cock in your ass don't you?" said Terra.

"Yes. Keep fucking me with that big cock," I said. I was so turned on that I felt deranged. I couldn't believe how easily I had taken Terra's horse cock. But, then I looked over my shoulder so I could watch as Terra drove herself into me. I saw that her cock wasn't even all the way inside me. That soon changed.

"Are you ready, Matt? Are you ready to get your ass fucked nice and deep?" Terra didn't wait for me to answer. She plunged the rest of her dick all the way into me. Her balls slapped against my ass as her cock ripped me open. I let out a small scream, but immediately suppressed it. I grabbed the side of the car seat to brace myself as Terra started wildly fucking my ass.

Each thrust shook me as she drove her huge cock deep into my asshole. Her pace was quick and I thought I was starting to have trouble breathing. It felt like she was inside my stomach.

I turned my head to the side and the passenger side mirror caught my eye. From the angle I was at, I could see Terra outside the car fucking me. Her beautiful ass shook with each thrust and her teeth were clenched together. I stared at her body and marveled at how such a beautiful girl could have such a big cock underneath her panties.

Her pace suddenly quickened. She was fucking me as fast and as hard as she could. The pain I was feeling was becoming pleasure. My mouth opened, apparently of its own will, and I started moaning like a bitch.

"Yeeeeeesssss," said Terra through clenched teeth. "Take it. Take my dick you filthy boy. Let me fuck your man-pussy until I cum inside you." It was a good thing that we were in the middle of nowhere. The sound of Terra's thighs and balls slapping against my ass was loud enough for anyone nearby to hear. I was in complete ecstasy as Terra slammed into me over and over. Suddenly, she stopped though.

"Sit up," ordered Terra. She climbed off of me and I turned over. She was still standing just outside the car door so I sat on the edge of the seat. My cock had become completely hard and was now fully exposed.

Terra grabbed her dick and shoved it into my mouth. I was now sucking her cock right after it had fucked my ass. My instincts told me to be grossed out, but there was a strange, bitter-sweet taste to her cock now and I was enjoying how slutty it made me feel. I started sucking on it passionately, slurping it up and down as far as I could go.

"Jerk yourself off," said Terra. My cock was nearly pulsing it was so hard. I started pumping away at my cock and increased the speed of my sucking. The bulging veins of Terra's horse cock felt great as they glided over my lips.

Terra was rock hard and she was squeezing with her right breast with her hand. I could tell she was close to cumming. However, it seemed that I was closer. I was jerking my cock so fast that I started cumming in no time. I shot a big load up into the air that sprayed across the inside of Terra's left thigh.

A few seconds later, Terra's cock twitched a little. She moaned loudly and started to cum into my mouth. Her balls tucked themselves up a little as a flood of cum shot into my mouth. I swallowed the first load, gulping down the hot liquid, but it was coming faster than I could handle. I tried to keep it all in my mouth, but a lot of it started pouring out the sides, streaming its way down my chin.

I couldn't believe how much cum Terra was shooting into me. It was like a fire hose had suddenly been turned on. Terra was going crazy, swearing loudly as her dick spasmed again and again.

After I had swallowed almost as much as I thought I could take, she finally stopped cumming. Terra looked down at me, a satisfied expression on her face. Then her face became stern again as she looked at my cum dribbling down her thigh.

"Lick it up," she ordered and pressed my face into it. I lapped at her soft thigh until all my cum was gone. Then she got bent down close to my face.

"Good boy," she whispered to me. "You've been a very good little cumslut for me." Then she smiled and pulled up her pants, tucking her dick underneath again. I got dressed too and we both got back in the car.

We didn't really say much the rest of the way. Now that I wasn't caught up in the moment anymore, I felt a bit embarrassed, even ashamed of myself. Terra dropped me off at my parents place and got back on the road. I walked in the front door and my mom was waiting for me.

"Matt, I saw you get dropped off. Who was that? Is that your girlfriend? She was pretty. She looked like a keeper." I mostly just brushed off these questions and went up to my room. The rest of the time I was home, I just kept thinking about what had happened. I mean, did this make me gay? If it did, why wasn't I attracted to guys?

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