tagTranssexuals & CrossdressersRiding in Cars with Shemales Ch. 02

Riding in Cars with Shemales Ch. 02


Note: This is a sequel to my previous story, "Riding in Cars with Shemales." If you would like some back story into how Terra and Matt met, please read it. If not, you can probably still enjoy this one by itself.


It was a wonderful day in May. The sun was shining. The sky was clear. Birds were chirping everywhere and everyone was spending their Friday after class outside. That is, except for me and my shemale friend Terra. I decided to spend my afternoon inside my dorm room, and Terra and her big dick decided to spend the afternoon inside my ass.

It was only about four o'clock and Terra was giving it to me good. Her nine inches of thick girl-cock were pounding away at my ass doggystyle as I stroked myself in my hand. Terra and I had been spending a lot of time fucking each other ever since she had given me a ride home over spring break.

Terra was naturally dominant, so I was usually on the receiving end of her dick. I still couldn't believe that a girl as pretty as Terra could have such a monster of a cock. I never complained though. When her dick was deep in my ass, I was in heaven. It got me so hot taking it up the butt.

At that moment in my dorm room, it was filling me up and I was begging for Terra to give it to me harder. She obliged and picked up her pace, slamming that horse cock of hers deep inside me. We had been fucking so often that my ass could take it fairly easily. It still stretched me good though.

"Yeah, take it like a bitch, Matt," said Terra. "You love it when I fuck you like this, don't you?"

"Yes. Yes, I love it. Give me more. Please give it to me hard," I said.

"You like that, baby? You like taking it in the ass?" Terra slowed down her humping for a moment and started fucking me with long, slow thrusts. Just then, I had a strange thought. I did love taking it in the ass. In fact, it was my ass getting fucked the majority of the time Terra and I fucked. Did Terra not like to get fucked?

"Terra?" I asked.


"Do you... do you like to get fucked in the ass?" I asked and turned my head around to look at her. It felt strange asking her a question like that, especially with her cock inside me. She stopped thrusting and looked down at me strangely.

"Did you really just ask a tranny if she likes to take it in the ass?"

"Well, I mean.... It's just that you're always the one fucking me. I hardly ever fuck you."

"Oh!" said Terra. "Is that a hint? You could have just asked."

"No, no," I said, frantically. "I didn't mean that. I just meant that..."

"Well, it's too late now. You've got me turned on to the idea." Terra pulled herself out of me and bent over onto all fours. I could see that she was committed to changing places, so I slowly got up and positioned myself behind her. I grabbed the lube off of my desk and squirted a good amount onto Terra's ass.

"Now, you better give me a good buttfucking. You're going to give it to me hard, right?" said Terra. I responded by shoving myself into her tight ass. Terra had a slutty little ass, but she could take my cock no problem. "Uuuunnggh," said Terra as her brown pucker swallowed my cock.

I wasted no time and started giving it to her rough. Her ass felt amazing on my cock. It was wrapped around me tight as I slid in and out. Terra's ass shook each time I slammed into her, sending a small ripple across her cheeks. Her ass was hypnotic under my thrusts.

"Yeah, baby. Just like that," said Terra. "Give it to me hard and don't stop."

"Oh god, Terra. Your ass feels so good on my cock." As I continued to fuck her, the lube in her asshole started making squishy, slopping sounds. I picked up my speed a little. Underneath her, I could see Terra's cock had started to become softer without stimulation and it was flopping around freely. It was like a big fucking python, dancing between her legs. Even soft, she had a much bigger cock than me.

I reached underneath her and grabbed ahold of the big snake. I heard her gasp a little and I started jerking her off. It didn't take long before she was hard again. A little more jerking and thrusting, and she seemed close to cumming.

"You like getting fucked like this, Terra?" I said.

"Oh shit. Yes. Yes. Yes! Keep fucking me just like that. Keep jerking my big dick. Fuck my like a whore!" I kept up my pace on her ass and started pumping her dick even harder. It took such long strokes to move the length of her cock. Suddenly, Terra's breathing became erratic and her ass squeezed tight around my cock.

I felt her spasm in my hand as she started shooting her load onto my floor. The tightness of her asshole soon became too much for me and I started cumming too. I pushed into her as deep as I could go. I was balls deep in her round butt and my dick started spewing cum inside of her.

When our orgasms had finally washed over us completely, we remained motionless. My dick started to soften inside of her. Eventually, I pulled out and we sat together on my bed. There was now a large wet spot on my floor where Terra had cum. I couldn't have cared about that if I had tried. I just lay down with Terra and started fondling her naked breasts.

"That was great," I said.

"Yeah. Guess it had been a while since I took up the butt last," said Terra.

"You know, I really wasn't trying to hint at anything. I just really wanted to know. Maybe it was kind of a strange time to ask. I'm sorry, I didn't mean anything by it."

"No. I'm glad you did. Besides, I really did like taking you in my ass."

"So, you really do like getting fucked in the ass?" I asked.

"Well, I used to think I liked it more than anyone. But, then I met you." Terra laughed and kissed me on the cheek. I turned on the TV and we started watching some action movie they had playing on basic cable. We didn't make it far into the movie before we both got turned on.

Terra pushed me onto my back on the bed and climbed on top of me. She moved herself up my body until her legs were around my head. Then she lowered her ass onto my face. I started licking her ass as she stroked her cock back to life.

"Open your mouth," said Terra, and I obediently obeyed. With her asshole directly over my mouth she used the muscles in her ass to push. A couple of seconds later, she was forcing the load of cum I had shot into her ass earlier into my mouth. I swallowed it and started lapping at her ass, cleaning it of my cum.

Terra smiled and moved her way back down my body towards my now hard cock. She grabbed it with her right hand, guided it up into her asshole, and we started fucking again, her dick bouncing up and down on my stomach.

We continued to fuck for the rest of the day. Around midnight, Terra decided to go back to her room to sleep. We had been having sex for a couple of months, but we never actually slept together. We were both sort of reluctant to start getting serious with each other. The sex we had was so dirty and we didn't want to complicate it by getting serious.

The next day was Saturday and a bunch of people on my floor were going to the lake. It had been much warmer than normal, so they were opening the swimming area earlier than usual. There were a lot of us going, so we all piled into several different cars. We got to the lake, and we all spilled out of the cars like a bunch of clowns.

There were a lot of people from my floor there. I didn't even know some of them. I looked around, seeing which faces I recognized. Suddenly, I felt a hard smack on my ass. I jumped a little at the surprise. I turned my head and saw Terra standing beside me with a wicked grin on her face. Then she walked away towards the beach.

I didn't even know that Terra was coming. I had mentioned it to her the other day, but she didn't say that she was going. Maybe she had decided last minute. Anyways, I was quite surprised to see her. I was even more surprised to see that she was wearing a little, pink bikini. Was she fucking crazy? The girl had a god damn horse cock and she was walking around in a bikini? How was she even....

Just then a couple of my friends came up to me.

"Holy shit, dude. Was that Terra?" It was my friend Jim. "Are you and her... you know." Terra and I had been keeping our relationship secret. It just seemed easier that way. Now, though, she had kind of backed me into a corner. Jim wasn't about to believe that Terra had just randomly slapped my ass for no reason.

"Ummmm... kind of," I said.

"Terra? That girl that lives next to you?" That was Jim's roommate, Craig. "Holy shit, you lucky dog, Matt. Are you hitting that? God, I would do anything to get a piece of that ass." We all watched Terra as she made her way towards the beach. Her ass swayed with each step and there was a little bounce in her cheeks whenever her foot hit the ground.

"Trust me, Craig," I said. "You couldn't handle it." I started walking down to the beach. Jim, Craig and I all went straight into the water, with several of the others. From the water, I could see Terra laying out on her towel.

I couldn't believe she was so daring to wear a bikini in public. I also couldn't believe that I saw absolutely no sign of a bulge when she walked by earlier. You don't just make a nine inch cock disappear. After a long time of puzzling over how she was doing it, I finally went over to talk to her.

I sat down next to her on the sand. She was lying face down on her towel and suntan lotion was glistening on her soft skin. She looked amazing, just laying there, the very bottom of her ass cheeks hanging out of her bikini.

"You're in my light," said Terra casually. I lay down beside her and leaned in close so only she could hear me speak.

"How are you doing it?" I said.

"How am I doing what?" said Terra.

"Come on, don't play games with me. How are you doing it?"

"You're going to have to be a little more specific, Matt. How am I making my ass look so tasty right now? How am I always so awesome? How did I lose those three pounds this week, which you still haven't said anything about by the way?"

I laughed a little. "Ok, you're right. You look great," I said. "Speaking of, I can't help but notice that I can't see a rather large part of you. How are you hiding it so well?" Normally, Terra would just tuck her penis back underneath her. However, she was normally wearing pants. Her dick was so long that it would be pressed between her ass cheeks but her head would be poking out the back a little. I just didn't see how she could be doing that in a bikini.

Even if she had managed to do that, gravity would be pulling it down and her dick would be pressing against the bottom of her bikini. But, that wasn't the case. Had she taped it?

"Do you really want to know?" said Terra.

"Yes, I do," I said.

"How badly do you want to know?" teased Terra.

"You're being cruel now. Can I please know? It's going to drive me crazy."

"Ah, you're no fun. Fine, I'll tell you." Terra moved her lips real close to my ear and whispered so that only I could hear. "It's in my ass."

I wasn't sure I had heard her right. "It's what?" I said. Terra just tilted her head and raised her eyebrows. Then she put her head back down.

"Be a dear and move out of my sunlight, Matt." I stood up and walked back to my friends in the water. I contemplated what Terra had told me. It's in her ass? What does that even mean? My mind just wasn't able to understand. I started swimming around, trying to get my mind off of Terra.

After about an hour, I saw Terra get up and start to walk up the beach. There was a big building in the swimming area with bathrooms, a little restaurant, and a c-store. She was headed right for it and I followed her.

She was getting close to the door when I finally caught up with her. I grabbed her arm and pulled her around the side of the building. I checked to make sure no one was around us, but everyone was still down at the beach. I brought Terra to the back of the concrete building.

"Ok," I said. "Tell me how you're able to wear such a tiny bikini out in public."

"I already did, you fucking goof. Didn't you hear me?"


"It's. In. My. Ass."

"I don't get it, what's in your ass?"

"Are you fucking dense? My cock! My cock is in my ass!" I guess I probably should have understood that that's really what she had meant, but my mind had trouble contemplating something like that. Could Terra really put her own cock up her ass?

"Are you serious?" I said. "Show me."

"Uggh," said Terra and she turned around and pulled down her bikini. There before me was the most amazing thing I had ever seen. Terra had her penis pulled back, except several inches of it were buried in her asshole. I guess that explained why there was no bulge -- a large portion of her cock was stuck up her ass. This was beyond hot to me.

"Holy shit, Terra. You can fuck your own ass?"

"Yeah," said Terra. "I can suck it too, you know?"

"You can suck it too?!" I said. I was very excited about this. I reached out and started to rub her cock. "Do you do this a lot?" I asked.

"Every now and then," said Terra. "I used to do it a lot more before we started fucking each other. I used to cum in my own ass every now and then. Ooooooh." Terra started to moan as I continued to rub her cock, stuck in her own ass.

"Can I see how much is in your ass?" I said.

"Ok," she said. "If you want." I pulled on her dick and watched as the monster slid its way out of Terra's ass. It finally flopped out and dangled down between her legs. I wrapped my hand around it and stroked it slowly. I couldn't believe how much of it had been inside her asshole. She must have had it inside her all day, because her ass continued to gape open after it slid out.

I pressed my head into Terra's ass and started licking her gaping butthole. I had come to love the taste of her ass, and this was the perfect opportunity to get a taste. Terra started to breath heavily and we both lost ourselves for a minute. Terra was the first to snap back to reality.

"Matt! Stop! Oh fuck."

"What? What's wrong?" I said.

"You got me hard!" said Terra. "I'm too hard to put my cock back into my ass. It won't bend like this."

"Umm... umm... ok. We'll just wait until you soften up a bit."

"No. I can't. I'm too fucking horny right now. It's going to take too long," said Terra. She seemed very worried, and rightfully so. If she couldn't get her cock back into her asshole, she would have to walk around with a bulge in her bikini until we left.

"You're going to have to suck me off," said Terra. She pushed her cock down between her legs and bent over a little, aiming the head at me, directly behind her. I was intrigued. I had never sucked her dick like this before. Also, the idea of doing ass to mouth with Terra's cock after it had been in her own ass made my own cock start to throb.

I took Terra's cock into my mouth and began to suck. She let go and pressed against the building in front of her, the side of her face pressing against cool concrete with her hands on either side of her head.

I slid my lips over her cock and took it into my mouth until my face was smashing into her ass. Sucking her cock from behind was something new and it was making me very excited. I passionately started slurping on her long member, my nose pushing into her ass crack each time I moved in.

Terra moaned deeply and started moving her hips back to meet my lips. I could taste the bittersweet flavor of her ass on her cock and it was driving me crazy. I pulled down my swimming trunks with one hand and pulled out my own cock, already hard from all the excitement. I started stoking myself as I kneeled behind Terra.

I pushed myself as far onto her cock as I could, deepthroating it, and held it there. The aroma of her ass filled my nostrils as her cock filled my throat. I pulled back so I could breath and gave Terra's left ass cheek a slap. I watched it jiggle and started sucking her again. I sucked as fast as I could and I could feel her getting close.

Her moans became raspier and I felt her meaty cock start to twitch inside my mouth. She shot a big load into my mouth and I swallowed as it streamed down my throat. Only a little escaped my mouth, otherwise I managed to swallow it all.

When Terra had stopped cumming I stood up and she turned around, kneeling in front of me. I continued to stroke myself furiously until I was about to cum. I let go and Terra took me into her mouth, sucking hard. I exploded in her mouth and she swallowed my cum with ease. I helped her to her feet and we kissed each other passionately.

"Come on," she said. "Help me get my cock back into my ass before it goes completely soft." I helped her push her dick back into her ass and pulled her bikini bottom back up. She left, then I left a couple of minutes later.

When I got back to the beach, Terra was lying on her towel again. As I walked past her, she winked at me then lowered her head again.

Hell of a day at the beach.

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