tagTranssexuals & CrossdressersRiding in Cars with Shemales Ch. 03

Riding in Cars with Shemales Ch. 03


It was the last day of classes. All of the finals were finished, and everyone was celebrating. My finals had been particularly rough. It was the last semester of my freshman year and I didn't study as much as I should have. The problem was that I lived next door to a girl that I had been having sex with for most of the semester. Terra could be quite the distraction; just knowing that she was so close whenever I needed her. Together, we had spent a lot of time not studying for finals.

Terra was fantastic. She was everything a guy could want in a girl.... Well, everything plus a giant cock swinging between her legs. Our relationship was a strange one, to say the least. We weren't really dating, and we definitely weren't monogamous. I knew that Terra would sometimes sleep with other people; guys and girls both, I learned. She didn't exactly hide it either. And, I had even had a one night stand with another girl. I guess you could have called us fuck-buddies.

We essentially acted the same way around each other as we had when we were just friends hanging out, except, of course, now we would hang out and fuck the shit out of each other too. Terra seemed perfectly alright with the way our relationship worked. I mean, she was affectionate at times, but she showed no signs of wanting to be more than friends... with a shit load of benefits, of course.

I, on the other hand, was starting to change. I did love what we had together. It was exciting, but I started developing real feelings for Terra. I often considered what it would be like to take our relationship further. These new feelings only added to my confusion about myself. I was still constantly wondering about my sexuality. I still liked pussy and having sex with girls, but this didn't seem to match up with the nights when I would swallow a load of Terra's cum. So, what did that make me? My mind was a puzzle with a missing piece. It was definitely still a confusing time for me, but none of that mattered when I was with Terra. When we were together, I knew exactly what I wanted and nothing else mattered.

After we had both finished all of our exams, we met up in my room to celebrate. This meant a lot to me because I didn't know if I would even be able to see her over the summer. When we got to my room, we both disrobed quickly. Both of us had been looking forward to this all day. My parents were coming the next day to help me move out, and, with classes finished, we had the entire rest of the day to be alone together.

We decided to have a stamina race. This was a game that Terra and I played occasionally. The rules were pretty straight forward. We would put on a porno and sit on my futon. Terra would grab my dick and I would grab hers. Then we would start jacking each other off while watching the porno. The first person to cum was the loser. The winner then got to fuck the loser in the ass. Sometimes we would modify it so that we did a sixty nine instead of giving each other hand jobs.

Terra usually won. She definitely had more stamina than me, and jerking her giant horse cock took a lot of effort. On this particular day, though, I won... barely. Terra was so close to making me cum. I thought I had lost for sure. But, then I felt her thick cock twitch and a fountain of cum sprayed up and landed all over her tits. She sighed with pleasure, scooping up globs of excess cum and licking them off of her fingers, and then got on all fours on my floor. She accepted her loss very graciously.

I took my position behind her. I kept my feet flat on the ground with my legs straddling her and squatted down to mount her lovely ass. Terra loved to get fucked this way. I entered her with a groan of ecstasy and began slowly moving myself in and out of her. I didn't think I would be able to last, but I was going to make it last as long as I could.

Terra began to moan lightly as I lovingly humped her beautiful butt. I continued my slow movements for a couple of minutes then I lowered my upper body down until my chest rested on her back and wrapped my arms around her waist. Our bodies pressed together in a sensual bond, our breathing becoming heavy. I pushed deep into her ass. My head was next to Terra's and I turned in to suck on her ear lobe. Terra then turned her face towards mine and our lips locked as we passionately kissed, our tongues massaging each other. I could taste the faint remnants of Terra's cum on her own lips. We kissed continuously for some time before I broke away. I needed to look at her face when I came.

I pulled out of Terra and told her to turn over onto her back. She quickly turned over, spread her legs and pulled them up towards her stomach, exposing her vulnerable ass for me. I kneeled down, spreading my own legs to lower myself to her level, and pushed back into her. I started fucking her at a steady pace.

Terra was quite the sight on her back in front of me. She was such a feminine looking girl. No one in their right mind would ever guess what was between her legs. Her curves were in all of the right places. Her ass was round and shapely. Her hips were wide and naturally girlish. Her face was beautiful. She could look gorgeous even without make-up. Even her tits looked real as they bounced with my thrusting.

Then I looked down and watched my cock sliding in and out of her asshole. Just above was Terra's huge cock. It was limp, resting on her stomach. Even soft, her dick was probably bigger than any other on campus. I could feel her large balls pressing against my stomach with each thrust. Terra kept herself completely shaved and her balls were soft against my skin. I had to concentrate on not cumming. I wanted to make this last a little while longer.

I grabbed Terra's legs and moved them onto my shoulders. In this position, I drove myself even deeper into Terra's ass. I saw Terra's face react to this new depth. Her mouth hung open and silent moans were coming out of her. She was definitely enjoying this. Her dick was beginning to harden as I continued to fuck her. I fell into a good rhythm and began fucking her harder. I loved the sounds of my thighs smacking against her soft ass, causing a ripple to move through her body.

Terra began stroking herself in her hand and was very quickly fully hard again. Good god, the girl was an animal. I spread her legs out wide, keeping them up in the air. I stared down at her hard cock and watched her furiously pump her hand up and down the length of it. Then my eyes traveled up her body, taking every inch of it in, until I was looking at her face. Our eyes met and locked onto each other. Her gaze was soft and full of ecstasy, with a hint of something that looked loving. Could that be? As I stared into her eyes, the feelings I had for her all flooded my mind. I wanted her desperately, and no one else.

"Oh god, Matt. Fuck me. Fuck me hard and cum for me," said Terra. I slammed myself into her, and started fucking her hard. Terra let out a scream as I rocked her body. Anyone outside in the hall surely heard us. In no time, I could feel my balls contract as my orgasm began. I pulled out of Terra's ass and pumped my dick hard in my fist. I shot a thick stream onto her stomach and another landed right on her cock as she continued to jack herself off. I shot four more streamers onto her before I stopped cumming. I then wasted no time and lowered my mouth onto her dick, wrapping my lips around her thickness. Terra stopped stroking herself to let me finish her with my mouth.

Her big cock filled my mouth and I slurped up and down it, sucking hard. I licked up the sizable glob of cum I had shot onto her before and swallowed it. Then Terra was frantically panting that she was going to cum. Terra must have been close to orgasm before I started sucking her because, after only thirty seconds or so of taking her into my mouth, she was cumming down my throat. She put a hand on the back of my head, pushed me down, and I swallowed the entire load, making sure not to lose a drop.

After I gulped down the last drops of cum, I released her cock, lifted my head, letting her dick slap down against her stomach, and looked up at Terra. She was looking down at me tenderly and I knew that she was all that I wanted. We lay on the floor together awhile, breathing heavily as we recovered from our orgasms. Terra put her head on my chest and I gently stroked her long, silky hair.

"What time is it?" said Terra. I craned my neck to look at my alarm clock.

"About 4:30," I said. "And, we have all night to do whatever we want." I wrapped an arm around her and brought her in close. Terra sort of nuzzled into me a little. I always thought it was strange whenever she did things like that. I mean, the first time we ever had sex was when she fucked me on the side of the road. She was so forceful and dominating then. Yet, here, lying on my dorm room floor, she was vulnerable and warm. With my arm wrapped around her, it felt like she really was my girl.

Just then, there was a knocking on my door that startled both of us. Even though you know they can't see you, it's unnerving having someone knock on your door when you're naked.

"Shit," I whispered to Terra in a mischievous tone. "Do you think somebody complained about the noise to an RA?" We both quietly laughed. I stood up and walked across the room.

"Yeah?" I called out through the door. "Who is it?"

"Matty, it's us!" I froze in my tracks at the sound of my mother's voice. I quickly turned my head towards Terra, panic written across my face. Terra took notice and put two and two together. Then her face matched mine as she scrambled around finding her clothes.

"Uhhh... ok... just a minute," I said. I was not doing a good job at suppressing my sudden attack of anxiety. There I was, completely naked in my dorm room with my shemale fuck-buddy, her massive cock flopping around as she frantically tried to stuff it into her tight jeans, and my parents were standing on the other side of the door.

I raced over to the futon and found my clothes. It took me three tries to properly buckle my belt - my hands were shaking so much from the sudden adrenaline. I put my shirt on inside out and had to take it off and put it on again. I looked over at Terra. She had her bra on now and was slipping her shirt over her head.

"Matt?" I heard my mother calling from my door.

"Just a second," I called back. I finally got all of my clothes on and flung myself across the room to the door. I waited for Terra to finish pulling back her hair into a pony tail then unlocked and opened the door. My parents were standing in the hallway, a huge smile on my mom's face.

"Surprise, Matt!" said my mom as she spread her arms out wide. She was always way more enthusiastic than the moment called for. My mom hugged me, and my dad gave me a pat on the shoulder.

"How ya doing, Matt?" said my dad. "We decided to come up a day early to surprise you." Perfect. It's not like I had plans or anything. My mom, still hugging me, looked over my shoulder and saw Terra standing in my room.

"Oh! Oh my. We aren't... interrupting, are we?" said my mom.

"No, no. You're fine," said Terra, walking towards my mom. "Hi. I'm Terra." She shook my parents' hands and smiled.

"Oh! Bill, this is that girl. Matt's girlfriend, Terra," my mom said to my dad. Oh no. I couldn't believe my mom just said "girlfriend."

"I see. Nice to meet you," said my dad.

"Matt's... Matt's... girlfriend," said Terra as if she wanted to make sure she had heard that right.

"Matty has told us all about you!" said my mom excitedly. Terra glanced over at me then smiled slyly.

"Has he now?" she said.

"Oh, gosh yes! Matt talks about you all the time," said my mom. I started to turn bright red as Terra looked at me. She seemed amused by the whole thing. It was true. I had talked about Terra a few times when my mom had called me. I guess my mom assumed she was my girlfriend by the way I talked about her. As far as my parents knew, though, Terra was just a regular girl. My parents were both very conservative. So conservative that I would probably be disowned if they ever found out I was having sex with a shemale, even if that shemale was someone as beautiful as Terra.

"Well, jeez," said my mom. "Matt said you were pretty, but my gosh!"

"Wow, thank you," said Terra. The forwardness of my parents must have surely surprised her, but she seemed to be adjusting to it quickly.

"Hate to hurry things up here, but I haven't eaten since this morning," said my dad. He wasn't big on chit chat or being overly pleasant. "We saw a place just off the highway, and we figured we'd take you out to eat."

"Oh, and Terra, you are invited too, of course," said my mom. She seemed absolutely thrilled to have met her. I, on the other hand, was a bit mortified. Terra and I weren't even a couple and now she had to meet my parents just because they decided to show up? Terra was probably freaking out. I must have seemed like such a creep, talking about her to my parents. This night was supposed to be all about Terra and me getting hot and sweaty together. Why did my parents have to be here?

"Uhh, well actually...." I started.

"Actually, I was just leaving," said Terra. "I need to pack all of my stuff tonight. But, it was great meeting both of you."

"And, it was so nice meeting you!" said my mom. "You'll have to come by for a visit over the summer." Great. Yes, please make this more awkward.

"Uhhh, yeah. Of course," said Terra. At least she didn't seem too horrified. In fact, she still seemed a bit amused by all of this. She turned towards me, and, with the most stereotypical cutesy girlfriend voice said, "Bye, sweetie. See you later." Perfect. Now she was mocking me. Terra gave me a quick kiss, walked into her room and closed the door.

My mom nudged me with her elbow. "She seems like a keeper," she said. My brain was working overtime trying to evaluate what was happening. All through dinner, I just kept wondering what Terra must be thinking. Did she think I was creepy? Did meeting my parents scare her? What if she didn't want to see me anymore? There was no end to my what-if scenarios.

My parents had gotten a hotel room, but they wanted to hang out with me for the rest of the night. I was their unwilling tour guide around the entire town until around 11:00 when they finally decided to drive back to their hotel. I got back to my dorm as quickly as I could and went straight to Terra's door. I timidly knocked. A few seconds later, Terra answered, wearing pajama pants and a thin top held up with spaghetti straps. Upon seeing me, Terra smiled slyly and leaned against her door frame.

"What is it, lover-boy?" Terra said in a mock tone.

"I... am so sorry," I said. "I know we aren't a couple or anything. My parents are just kind of crazy I never said you were my girlfriend I understand if you think I'm insane it's just that I really like you and I guess I just kind of..." Terra interrupted me by wrapping her arms around me and kissing me hard on the lips.

"Matt," said Terra during the moments our lips weren't completely covering each other, "shut up and come inside." Terra grabbed my shirt and pulled me into her room.

The next day, I couldn't stop smiling. I spent most of the day in the car with my parents, but my mind kept wandering back to the previous night in Terra's room. While my mom was singing along with the shitty country music on the radio and my dad was complaining about the price of gas at each exit we passed, I was lost in my own head. Terra had real feelings for me! I was living on a fucking cloud.

After making out for an incredibly long time last night, Terra and I had moved to the bed. Our bodies seemed to be in perfect sync as we took turns giving and receiving. It was so sensual, both of us more concerned with making the other cum first. But, the sex wasn't even my favorite part, surprisingly, though sex with Terra is always amazing. Afterwards, we both lay on her bed completely naked. I put my arms around Terra and she wriggled her backside into me. I held her for the rest of the night, both of us completely content.

In the morning, I had to pack my things. I wasn't ready to leave yet though. Things had just started getting good for me here. What if my relationship with Terra didn't make it through the summer? What if she changed her mind? What if that was the last time I ever got to see her? It seemed I was worrying for nothing though. Terra showed up just before we finished loading everything into my parent's trailer. She told my parents that she would love to take my mom up on her offer to come visit. My mom was absolutely thrilled about this. Right before we left, Terra gave me a kiss. I guess I was thrilled as well.

The next month could not have gone by any slower. Terra was going to visit in June and I was counting the days. We weren't completely out of contact with each other, though. Sometimes we would play video games online together and chat, and we usually sent texts to each other every day. Some nights we would send each other naked pictures. My first ever sexting experience and I was getting pictures of some girl's massive cock. I didn't know the first thing about making myself look sexy on camera, so my pictures weren't as good, but Terra always sent me the hottest pictures. She knew how to pose like a pro. Must not have been her first time.

Finally, after nearly thirty days of jerking it to pictures, Terra came for a visit. This was a big deal for me. It was the first real thing that we did as a couple, and I wanted it to be perfect. I saw her car pull up (Yeah, I may have been waiting by the window) and met her outside. I had told her to dress casually, so she was wearing jeans and a black top. She giggled as I wrapped my arms under her butt and lifted her up, kissing her hard on the lips. God I had missed her touch so much.

I carried her bag inside and my mom quickly stole her away to show her the guest room. My parents wouldn't allow us to stay in the same room, so Terra was going to be sleeping in the guest room for the night. I watched as my mom herded Terra upstairs, bombarding her with questions. I think my mom may have been just as excited for Terra's visit as I was. I didn't go out with many girls in high school so she hardly ever got to meet my girlfriends. When they finally came back downstairs, Terra gave me a funny little "save me" look.

We spent most of the rest of the day with my parents. It wasn't bad actually. We put on baseball game (everyone in my family is a hardcore Cardinals fan) and mostly sat around talking. Then we had dinner. I helped my dad grill and Terra helped my mom make a dessert. She hid the fact that she knew absolutely nothing about cooking. Yes, our entire day had turned into a made for TV chick flick. But, it wasn't so bad. There was one point while we were eating when my dad made some homophobic comment that was pretty off-putting, but, other than that, the rest of the evening went smoothly.

No, I still hadn't told my parents about Terra. I suppose I didn't think they would understand. That and, like I said, they would most likely disown me if they ever found out. Luckily, Terra was completely ok with keeping it a secret from them. She understood that it would be difficult for my parents. Their worldview wasn't the most well-rounded. It wouldn't just be difficult for them though. It would also be extremely hard for me. All of this was still fairly new to me and I didn't think I was ready to tell my parents something like that. Thankfully, this didn't offend Terra.

After dinner, we all watched a movie together. It seemed my parents were set on not giving Terra and I any alone time. I don't think they were doing it on purpose, but it was starting to drive me crazy. Terra was finally here and I had to share her with my parents all day. The movie was some shitty DVD that my parents had rented from the movie store. My mom talked through the entire thing, as she always does and my dad fell asleep about halfway through. The movie finished around 10:00 and my parents went to bed. Their bedroom was on the main floor and I listened until I heard the sound of their door closing. Finally, alone time with Terra. We both turned towards each other on the couch.

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