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Riding in Cars with Shemales Ch. 01

By: lfullback



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.

"What?"

"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? 


Riding in Cars with Shemales Ch. 01



My mind was filled with these questions all week. Terra was a girl, right? But, she didn't even have a pussy. So, she was a guy, right? No. She had tits, and curves, and a pretty face. She didn't look anything like a guy except for the dick. Maybe I was just turned on by dicks. What the hell did that even mean?

At the end of the week, Terra drove up to my house to pick me up again. I was still confused, but a suddenly struck by a sense of clarity as I walked up to the car. It didn't matter what I was. All I knew was that I knew exactly what I wanted. I climbed into Terra's car.

"You ready?" she asked.

I smiled and said, "You bet your ass."



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.

"Yes?"

"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?"

"What?"

"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.



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.




Riding in Cars with Shemales Ch. 03



"Hi," said Terra, as if she had just arrived.

"Hello," I said. "How are you?"

"Very well. And yourself?"

"I'm good. Great, now we're all caught up. That's enough talking." I smiled and kissed Terra, pushing her back on the couch until I was mostly on top of her. Our tongues explored each other's mouths and our hands roamed freely over each other's bodies. I moved my right hand down her chest and grabbed her left breast over her shirt. Having not seen each other for nearly a month made every touch incredibly erotic. Soon, Terra had both of her hands on my ass and I was rubbing the crotch of her jeans. I could feel her giant anaconda stirring inside. We were both getting turned on very quickly.

"Let's go upstairs," I said. Terra smiled and followed me to my room. We both sat on my bed and resumed our makeout session. I started kissing Terra on the neck and rubbing her thigh, my fingertips gently caressing her ass. I started to slide a hand down the front of her pants, but Terra grabbed me by the wrist and pulled it out. Then she broke away and stood up.

"What's wrong?" I asked. Terra bent over at the waist until her face was close to mine and, with a wicked grin, said,

"You just wait right here." Then she kissed me and walked out of my room. She shut the door, but I heard her walk down the hall and enter the guest room. She was gone for a few minutes. I was starting to get anxious, just sitting on my bed, waiting for her to come back. Terra clearly had something planned and I was getting very excited trying to guess at what it was.

My door finally opened again. My face must have looked very surprised because Terra smiled at my reaction. She closed the door behind her as she entered the room. She had changed into a skimpy little cheerleader outfit. Terra definitely didn't seem like the type of girl that would be a cheerleader, but she was undeniably sexy in that outfit. It was a two piece outfit and her flat stomach was exposed, showing off her belly button ring.

I looked her up and down, salivating over her tight, sexy body. She had the complete outfit too. She had the short skirt, the long socks, the... wait. Actually, it seemed that she didn't have the complete outfit. Terra wasn't wearing any panties under her outfit. I could see the head of a giant dick hanging down between her legs. The skirt wasn't long enough to hide Terra's horse cock. Terra noticed my gaze and slowly lifted up her skirt a ways, exposing more of her big dick.

"Isn't it every guy's dream to have a cheerleader in their bedroom?" said Terra.

"That it is," I said, swallowing hard. "Except, normally, the cheerleader isn't the one getting her cock sucked." Terra walked over to the bed. I looked up at her face. I had seen her face like that many times. It was covered with pure lust. I knew I was in for a good, hard fucking. I remained sitting on the edge of the bed. Terra stopped right in front of me, her crotch only a few inches from my face. 

"Well, today, you're going to suck this cheerleader's cock," said Terra. She lifted up her skirt, grabbed her dick and stuffed it into my waiting mouth. I began sucking hard, bringing it to life inside my mouth. Terra let go of her skirt over my head. It was so hot being completely under her skirt, sucking on her fat dick. She was getting hard at an alarming rate.

"Yeah, Matt. You know just how I like it. Suck my dick. I want you to choke on this girl-cock." Terra grabbed my head and forced herself into my throat. I had been getting better at this over time. I took her cock deep with ease, so Terra started bucking her hips, face fucking me. I only gagged a little as her cock violated my mouth. Terra pulled out and uncovered me from beneath her skirt. She pulled my shirt over my head and threw it on the floor. Then I felt her hands on my shoulders, pushing me back until I was on lying on the bed.

Terra took off her skirt, freeing her big dick. I watched as it gently swayed back and forth. Then she climbed on top of me, straddling my chest. She bent forward, putting her arms on the bed somewhere above my head with her cock right above my face. Then she lowered her hips down to me and I opened my mouth wide to take her cock. It filled my mouth. Terra began thrusting in and out with her hips. She started off slow, my lips slurping over her veiny thickness. Then she started to push herself in as far as it would go. I could feel the head of her dick halfway down my throat before I couldn't take any more. Terra stopped pushing; my lips an inch away from her balls. She held herself there for a few seconds before taking it back out again.

I looked up at Terra, as I gasped for air. She was stroking her cock in her hand as she waited for me to catch my breath. Then she stuffed my mouth full again and resumed thrusting with her hips. This time, she quickened her pace. I didn't think I could handle it as she started fucking my face hard. I gagged a couple of times, but she continued to face-fuck me. I was just about at my breaking point when she pulled out of my mouth and started climbing off the bed.

Terra undid my belt and pulled off my pants and underwear. Damn, she was aggressive. Then she shed the rest of her clothing as well, so we were both completely naked. 

"Looks like somebody's already hard," said Terra, kneeling on the floor between my legs. "Did sucking my big cock get you hard? You like it when I face fuck you?"

"Yes, I do," I panted breathlessly. Terra quickly took me into her mouth. Her lips slid down the length of it until they were pressing up against my balls. Terra stuck out her tongue a ways and started licking at my balls. God, she was such a good fucking cocksucker. She started working her mouth up and down quickly, taking the length of my cock every time. I'm pretty sure she didn't even have a gag reflex. Then she stopped sucking on my dick and moved down to my balls, taking one into her mouth and sucking greedily. I had made sure to shave myself for the occasion and Terra seemed to appreciate it.

"Oh, fuck yeah. Oh, Terra. Just like that. Suck on my balls," I said.

"MmmmMmmmm," Terra hummed with a mouthful of my balls. She stopped sucking to say, "I'm gonna make this cock explode tonight. You're gonna cum for me, and then I'm gonna shoot my load all over your face." She stopped sucking me to spit into her hand. Then she wrapped it around my shaft and started pumping my dick. It felt amazing with the added lubrication of Terra's saliva. "Let me see your ass," said Terra.

I obediently spread my legs, brought them up towards my chest and held onto my knees. This exposed my asshole to Terra. While continuing to pump my dick in her fist, she lowered her face down and started to lick my ass. The sensation of her slick tongue running over my asshole was amazing. Terra had done this a couple of times to me back at school. It took some getting used to. At first, it tickled too much, but I quickly started to enjoy it. Terra continued to lick for thirty seconds or so, then switched back to sucking my balls. She alternated back and forth for a few minutes, all the while continuing to stroke my cock. I was hard as a rock underneath Terra's tight grip.

"I think this ass wants to get fucked," said Terra. I grabbed a bottle of lube from my nightstand and handed it to her. She rubbed some onto her cock, and then smeared a sizable amount onto my ass, working some of it into my asshole with a finger. Then Terra grabbed her dick and aimed it directly at my ass. I looked down between my legs at the massive cock that was about to be shoved up my ass. It seemed unreal. Was that whole thing really going to be inside me? Terra pushed forward, penetrating me with the head of her cock.

"Oh!" I gasped at the sudden intrusion. "Yeeeeesssssss," I hissed as Terra continued to push into me. I had missed how her cock could make me feel so filled up. As she forced herself into my ass, I moaned deeply. She was stretching my ass wide open.

"That's it, baby. Take that cock," said Terra. She would push in a ways, pull out nearly completely, and then push back in, going a little deeper each time. My ass was adjusting to the size quickly and I was thoroughly enjoying the feeling. "Yeah, you're gonna take it balls deep, aren't you?" said Terra. "You're gonna take it deep... unnngh... just like a nice little slut."

"Yeah. Yeah, fuck me," I said between breaths. She could call me whatever degrading thing she wanted. I didn't care, so long as she gave me more of that horse cock. 

Terra slid in deeper. It felt like her cock was somewhere near my stomach by the time her thighs pressed against my ass cheeks. I felt her balls rub up against me. I had taken the whole thing up my ass. Terra smiled down at me and I could tell she was about to fuck me hard. She moved her hips, nearly pulling all the way out, and then forcefully shoved herself back in.

"Unnngh," I grunted with the pain of taking the entire shaft so deep. Terra did this again and again, her balls slapping into my ass and soft "ah" sounds escaping her lips. Then Terra grabbed ahold of my legs, spreading them wide. I braced myself as she started fucking my ass hard. Her thrusts slowly came quicker until the slapping sounds of Terra fucking my ass filled my bedroom.

"Holy shit, I missed this," said Terra. All the muscles in her face and neck were flexed and her teeth were grinding together as she continued to plow into me. Her tits were bobbing up and down with each thrust. I always loved the way she looked while she fucked the shit out of me, and, at that moment, she was laying into me hard. My body was being rocked on top of my bed. I could feel the shockwaves of impacts ripple through my tight ass each time Terra slammed herself into me.

Her cock was hitting something inside of me just the right way, and I wanted desperately to cum. My dick was rock hard, slapping into my stomach. I grabbed ahold of it and started jerking.

"Oh my god. This feels so fucking good. Keep fucking me, Terra. Fuck me harder," I said. Terra obliged, ripping me apart. Suddenly, I felt my cock begin to stir. I was going to cum. "Oh shit, Terra. I'm cumming. I'm cumming. I'm fucking cumming! Ooooooh my god!" My cock erupted into a milky white fountain as my cum shot up into the air. It felt like I was watching in slow motion as it rained back down all over my stomach and chest. I shot stream after stream of hot cum all over myself as Terra continued to fill my ass, my body tightening around her cock.

Seeing me cum must have excited Terra a little, because she tightened her grip on my legs and picked up her speed. She leaned her body over me a little, forcing my legs back towards my head even farther. She thrust so fast and hard. She was actually bouncing my ass up off the bed.

"Oooooh," moaned Terra loudly as she fell into a good rhythm. "That's it. That's it. Just like that. I'm gonna.... Oh yeah.... I'm gonna.... Fuuuuck, I'm gonna cum!" Terra suddenly pulled out. Taking out such a huge cock all at once left me feeling so empty. I could tell my ass was gaping from it. Terra let go of my legs and they fell down to the bed. Then Terra climbed on top of me, straddling my chest again, and furiously pumped her cock in her fist.

"Here it comes, baby," said Terra in an airy voice. "I'm gonna cum so fucking hard." Being wrapped up in the moment, neither Terra nor I even heard my bedroom door open. But, we did hear the gasp come from the doorway. Both of our heads turned quickly to see where it came from. Standing in complete shock at my door, was my mother with a hand clasped over her mouth and eyes as wide as dinner plates.

Terra and I both froze, but I could see from Terra's face that she had already started cumming, and there was no stopping it. A thick glob of cum shot out of Terra's giant cock and landed right on my cheek. She wasn't lying about cumming hard. I later learned that Terra had "saved up" for two weeks before this. Terra continued to spray cum all over my face. She must have shot eight or nine streamers onto me. My mother looked horrified as she confusedly watched me take a monster facial from my girlfriend. 

Terra and I were equally horrified on the bed. Terra couldn't help but moan a little, adding to the perverseness of the situation. I could tell she didn't want to, but just couldn't help herself. Her orgasm was washing over her body. After Terra finished cumming, all three of us remained catatonic for several seconds. It seemed like much longer. Then my mom sort of shrieked and quickly ran out of the room.

Terra and I continued to remain motionless for a while. We looked at each other, unsure of what was going to happen. I was scared out of my mind. My mom now knew that my girlfriend was really a shemale and had caught us in the middle of what most people would probably consider some depraved sex act.

"Well," said Terra, "I think she took that quite well."

TO BE CONTINUED



Riding in Cars with Shemales Ch. 04



Three weeks had passed since I last saw Terra – the night that my own mother had caught us in bed together. That night was one of the hardest I've ever been through. After my mom ran out of my room, Terra and I started cleaning ourselves up and getting dressed. This wasn't exactly how I had pictured "coming out" to my parents, and, being unprepared for it, I was overcome with an incredible sense of shame. Seeing how shocked and repulsed my mom was hit me pretty hard. But, that was nothing compared to how my father took it. I was re-buckling my belt when I heard him yell from downstairs.

"What do you mean she's a boy?!" He was so angry. His voice shattered the near silence that had taken over the house, and my hand started shaking a little. Things got pretty heavy after that. I helped Terra sneak out the back door. She asked me to come with her, but I had to stay. I figured there was no use in me running from it. So, I kissed her goodbye, watched her drive away and slowly walked back into the house.

I saw a very ugly side of my father that night. Things were said. The words "queer" and "fag" were thrown around like parade candy, but I got through it. Honestly, I didn't listen to most of what my dad was saying. I just thought of Terra the whole time to bear through it. The next three weeks were tense. Whenever my mom talked to me, she spoke as if I was recently diagnosed with some unfortunate sickness; like I wouldn't have slept with Terra if not for a sudden breakout of gayness. She told me she was praying for me a lot. That infuriated me. On the flip side, my dad didn't really speak to me at all. He sure as hell drank though.

By the time mid-June came around, I had actually become comfortable with the situation at home. That false sense of shame I had felt right after being discovered had dissipated rather quickly, and I soon adopted a "fuck-what-you-think" attitude towards my parents. If they couldn't deal with it, that was their problem. As for me, I hadn't seen my girlfriend in three weeks, and really wanted to get back to living my life.

So, I asked Terra if I might come visit her. She was more than happy to agree, and even offered to pick me up. A few days later, I packed a bag, told my parents I was staying at a friend's house and took a walk three blocks down the street to a park. When I got there, there was an incredibly attractive girl wearing tiny shorts, a tank top and large sunglasses, sitting on the trunk of her car, waiting for me. When she saw me, Terra climbed down, ran towards me and jumped up, wrapping her legs around me. Her tongue was in my mouth quickly. Guess I wasn't the only one who thought it had been too long.

I threw my bag into the car and climbed into the passenger seat. Then we were quickly off. I was going to spend the weekend at Terra's house in the city. Well, the suburbs technically, but everything is a city when you live in a small town like me. I was very excited to spend some time with Terra. Very. Excited. Before we even reached the highway, I had reached down Terra's pants, pulled out her fat cock, and was sucking her off while she drove.

'Just like old times,' I thought. 'Terra and I on a road trip.... Terra's dick filling my mouth....' Yep. It was a good trip. 

We arrived at Terra's place around 5:00. It was a very nice house. Her dad did something with real estate. I'm not sure exactly what he did, but he sure made enough money to keep him happy. I met Terra's parents right away. They were definitely different than my parents. I guess that's obvious since they had a t-girl daughter who was only 19 living with them. They really took a liking to me right away. It was nice being around such open-minded people.

We all had dinner together. Neither of Terra's parents was especially good at cooking, so we ordered out. While we ate, I was bombarded with questions about myself. They really wanted to know everything about me – where I grew up, what I was studying in college, what my favorite flavor of ice cream was, the list went on and on. It was about halfway through the meal and nearly two thousand questions later when I realized that they didn't know about what had happened at my house when Terra had come to visit.

Apparently, Terra had not driven straight home that night. She had stayed with a friend for the rest of the weekend so her parents wouldn't ask why she had come home early. I don't know why she kept it from her parents, but I was grateful for it. I didn't want her parents taking any pity on me or anything. That would just make it awkward.

After dinner, Terra and I went up to her room for a little while. Her parents were letting us sleep in the same room, something my parents would find unfathomable. Terra was going to take me to a party at a friend's place in the city. So, after about an hour of Terra getting ready and deciding what to wear, we left for the party. Terra ended up wearing some tight jeans and a black top. Her outfit showed off her curvy hips, making her look very sexy. I couldn't help checking out her ass every chance I got.

The party was great. It was at a house that two of Terra's friends shared together. They were both 23, so it was a slightly older crowd than I was used to. I'm pretty sure Terra and I were the youngest people there. Despite that, everyone I met was very nice. They all knew Terra, and they had all heard about me, apparently. Everyone I met would say, "Oh, so yooooou're Matt. I've been dying to meet you." It was nice to know that Terra had talked to her friends about me. I think I literally felt warm and fuzzy inside.

Then a strange thought occurred to me. All of these people I was meeting were friends of Terra's. They all must have known that Terra was a t-girl. That meant that they all knew that I was having sex with a t-girl. For a second, I instinctively panicked. But, then I realized that none of them cared. All of them knew, and none of them cared. I had never felt like this. Here, I didn't have to hide the fact that my girlfriend had a dick. I was accepted. I suddenly felt extremely relaxed; like a tremendous weight had been lifted off of my shoulders. 

"Your friends are great," I said to Terra. She smiled and gave me a quick kiss.

After spending so much time at my parent's house, it was great to unwind, have a few drinks, and just hang out. The party was in a large basement which had been furnished with several couches and large rugs all over the floor. There were people playing drinking games, an impromptu dance floor and several large coolers full of ice and drinks. It was like I was back on campus again.

A few hours into the party, I had a good buzz going. Terra and I had claimed a spot on one of the couches. I was finishing off my fifth beer, and Terra was sipping on some vodka drink while sitting on my lap. I playfully moved my hips up against her ass and she subtly grinded against my crotch. Jesus, I was so fucking horny. I just wanted to get her alone and devour her. I was just about to stand up to get another beer when two more of Terra's girlfriends approached us.

"Terra!" screeched one of them excitedly. "How are you?!"

"I'm great," said Terra. "You sound drunk."

"I am drunk!" She suddenly took notice of me. "Oh my God! Is this Matt?!"

"Hi," I said, reaching out to shake her hand. She grabbed it with both of her hands and shook it a little too much.

"Oh my God! I am so excited to finally meet you!"

"Matt, this is Laura and her girlfriend Erin," said Terra. Cool, I thought. I had never met lesbians before. They were both very attractive girls, and, as horny as I was, I immediately gave them a thorough once-over. Laura, the excited one, was about 5'8" with blonde hair. She had an excellent pair of hefty but natural-looking tits and some thick thighs. Her girlfriend, who had yet to say anything, was a sharp contrast. She had a petite yet toned body with light brown hair. Her breasts were small, but she had a wonderfully shaped ass. It actually reminded me quite a lot of Terra's juicy, round butt. I'm not ashamed to admit that I imagined Terra's friends going at it in my mind less than a minute after meeting them.

Both of them pulled up chairs and sat with us. They made great company. Laura was extremely talkative, but she was funny. Erin seemed to be a bit shy, but she smiled and laughed at jokes with us. The four of us hung out for the remainder of the party.

Around 2:30, Laura got a text that made her really excited.

"Ooooo, looks like the after party is at Brian's place," she said in a strangely insinuating way. "And, Katie is already there. Erin, you feeling up for it?" Erin smiled and nodded yes. Then Laura turned to Terra and me. "How about you two? You want to come?" I looked at Terra to see if she wanted to go. She seemed to be looking at me the same way.

"Uuummmm...." said Terra.

"Uhhh, yeah. Sure," I said.

"Awesome!" said Laura. "Katie's already there, so let's just go now. We'll get a cab." Laura and Erin stood up and walked upstairs to call a cab. After they were out of earshot, Terra pulled me close to say something to me.

"Matt, I don't know if we should go," she said.

"What? Why not?"

"Well...." Terra started, hesitant to say. "After parties at Brian's aren't exactly your typical after party. They tend to get... a little wild." Terra paused and looked at me to see if I understood what she was getting at. I didn't. "As in... hardcore wild."

"You make it sound like we just got invited to an orgy or something," I said, laughing. Terra silently stared back at me for a few seconds. "....Did we?"

"Kind of. Yes," said Terra. "We don't have to go if that makes you uncomfortable."

"Holy shit," I said. "Wait. Does this mean you've done this sort of thing before?"

"Well... yeah, you know? I mean, not since we started dating, but yeah. Does.... Are you ok with that?"

"Yeah," I said, and was a little surprised to discover that that was the truth. "It's just a little new for me. Kind of still taking it all in."

"So, does this mean you want to do it?" I thought it over for a few seconds. I was entirely out of my element, but I finally said,

"OK. Let's do it." Terra smiled and we went upstairs after Laura and Erin. About ten minutes later, we all piled into a taxi and headed for Brian's place. I was excited, but, at the same time, thought I might have an anxiety attack.

Terra sat in the front seat, leaving me in the back with Laura and Erin. Laura sat in the middle, next to me. After a few minutes, Laura leaned over to me and said,

"I assume Terra told you what type of party this is?" There was something very seductive in her voice.

"Yeah," I said. I was a bit short on words at that moment.

"Good," said Laura, and she gently placed her hand on the inside of my thigh. It stayed there for the rest of the ride, slowly moving back and forth, inches from my crotch. So, she doesn't just go for girls then, I thought. I brought back up that image of Laura and Erin going at it from earlier and added myself to the picture. Then I realized that that was basically what I might have been getting myself into already.

Soon, we pulled up to a very nice looking apartment building. We had to be buzzed in at the front door, and then we took an elevator up to the tenth floor. As we walked down the hall, I could feel every muscle in my body tense up with anticipation. Everything seemed to be happening very fast. We stopped in front of a door and Laura knocked on it. A few seconds later, a girl answered and let us in.

"Katie!" said Laura, and they hugged each other.

"Hi, everybody," said Katie.

"Hey, Katie," said Terra. "This is Matt." I said hello and shook her hand. Katie turned back to Terra.

 "Cute," said Katie and winked. "Come in. Brian's in the living room." Katie turned around and walked us into the living room. Katie was wearing an extremely skimpy dress that left very little to the imagination. My first impression of her was that she was a bit of a whore. It turned out that I was right, but she really was a sweet girl. She always stood in a way that showed off her big, fake tits while still pushing out her round ass. Her ass was pretty incredible actually. I don't know how something so big could be so perfectly round. It seemed to defy physics, but I sure as hell wasn't complaining.

The apartment we were in was very large and clearly was decorated by somebody who had never stepped foot in a Kmart in their life. Brian must be pretty well off, I thought. We walked into the living room and I finally got a look at Brian. Katie walked across the room and joined him sitting on a couch. To my surprise, he was only about twenty-four. With how nice the apartment was, I imagined him to be some creepy, graying fifty year old. But, instead, he was young with jet-black hair. 

Right away, there was something I didn't like about him. Maybe it was because he kind of looked like some stereotypical yuppie straight out of the eighties. Maybe it was because I started wondering if he and Terra had ever had sex. Why is it that I wasn't bothered by the fact that Terra had possibly fucked every other person in the room, but the idea of her fucking another guy was tearing me apart?

"Ah, there you all are," said Brian. "You can fix yourself a drink in the kitchen; whatever you like. But, if you don't mind, I've waited all night, so I'm starting things right now." Katie laughed and straddled him on the couch. Brian shoved his face into her sizable cleavage then kissed his way up to her lips. 'Wow,' I thought, 'things kind of just start up like that.'

"Typical," said Laura. "He never has had any patience." Laura and Erin walked over to a different couch than Brian and Katie and sat together. Laura pulled Erin towards her and they started kissing passionately. Very quickly, Erin had a handful of Laura's big tits. I looked at Terra, half expecting her to tell me what to do. She looked back at me in a way that asked, "What do you want to do?"

"I think I might need another drink," I said. Terra and I went into the kitchen and found Brian's liquor – top shelf stuff, of course. I poured myself a Crown and Coke. Terra said she was still doing ok from the drinks at the party, so she just sipped on a glass of water. I must have looked very nervous, taking large gulps of my drink a little too quickly.

"Hey," said Terra tenderly. "You sure you want to do this? If you'd rather just go back to my place, we can do that." I didn't say anything because I genuinely wasn't sure at that moment. There was a small silence for a few seconds. Then Terra just said, "Matt." I turned and looked at her. She looked back at me, then leaned in and kissed me softly on the lips. Suddenly, I wasn't nervous anymore. I downed the last of my drink and left the empty glass on the counter.

"Ok, I'm ready," I said. Terra and I walked back into the living room. We had only been gone for about five minutes, but it was a very different room that we entered. Katie and Brian were both completely naked. She was down on her knees between his legs giving him a blowjob. I took a moment to admire her naked body. Her big ass was sitting on top of her feet tucked underneath her, and she was really working Brian's cock in and out of her mouth, bobbing up and down using only her neck.

Things were warming up on the other couch as well. Erin and Laura were down to their underwear. Erin was wearing a white bra with a matching lacey thong, but Laura was down to just her purple bra. Laura was watching Katie and Brian, and Erin was down between Laura's legs, sucking on her dick.

Wait. What?

I blinked several times to make sure I was seeing this correctly. I was right. Erin was between Laura's legs with a mouthful of Laura's cock. Laura turned to look at Terra and me. She noticed me looking down at her big dick and smiled. I couldn't believe I didn't know she was a t-girl until just then. She did have a very nice looking dick; not as big as Terra's, but still rather big with bulging veins. Laura did have bigger balls than Terra. In fact, her balls were huge. I had never been particularly turned on by balls before, but looking at Laura's made me want to suck on them. She continued to stare back at me while moving Erin's head up and down with her hands. Laura wasn't the only one to notice us enter. 

Across the room, I heard Brian say, "Katie, why don't you go see what Terra's new guy can do." Katie stopped blowing Brian and stood up. Then she turned around and started walking over to me. The surprises continued to come. Hanging between Katie's legs was a small cock. 'Jesus, does everybody here have a dick?' I thought.

At least it was easy to see why Katie was so passable as a girl – she had a tiny fucking cock. This thing couldn't have been more than two inches. She walked across the room, stopping right in front of me. There was a wicked smile on her face, and she was just radiating sexuality.

"Do you mind if I borrow him for a little bit?" Katie said to Terra.

"Be my guest," said Terra with a smile. Terra winked at me and stepped aside. Katie grabbed the bottom of my shirt and pulled it up over my head. She looked over my abs and chest and licked her lips. I don't have a very muscular body, but I suppose I'm pretty lean. I mean, I had never considered my body all that sexy. But, what the hell do I know anyways?

"Erin! Bring that pussy over here," said Brian. Erin giggled a little. She took Laura's cock out of her mouth and stood up. Then she quickly took off her bra and panties. As it turns out, Erin really was a girl. 'Strange,' I thought. 'One of the girls I thought was a lesbian turns out to be the straightest one in the room.' Well, I suppose that was true. Sexuality seemed to be taking some strange turns in that living room.

Erin joined Brian on his couch. He lay down on his back and had Erin climb on top of him, sitting on his face. Her soft ass cheeks hid Brian from the chin up and he started eating her pussy.

"So," Katie said to me. "You've been sucking Terra's dick for quite a while now?"

"Uhhh, yeah," I said nervously. Katie laughed. I think she found my nervousness cute.

"Good," she said. "Then you won't have any problem taking on my little bitch-dick." Katie put a hand on the top of my head and started pushing me down. I got down on my knees in front of her, staring at the soft, tiny dick less than a foot from me. I glanced to the side and saw that Terra and Laura were both watching, waiting for me to suck it. Laura was slowly stroking the length of her cock in anticipation. I made eye contact with Terra. I found myself wanting to suck Katie, but still needed that last ok from Terra. She nodded at me, letting me know she really was alright with it. That's all that I needed.

I turned back to Katie, opened my mouth and took her soft dick between my lips. I started sucking the entire shaft in my mouth. Katie moaned as my tongue circled around the head. I was so used to Terra's monster of a cock filling my mouth that this was no problem for me. Even with Katie's entire shaft in my mouth, she wasn't even close to reaching my throat. So, after a while, I decided I would try something. 

I opened my mouth even wider, grabbed Katie's shaved balls in my hand and put them in my mouth as well. Katie gasped in surprise. I used my tongue to lick the underside of her balls as I sucked her entire package in my mouth.

"Holy shit," Katie said. "Terra, your boyfriend is... ambitious." Terra and Laura both laughed.

"Terra," I heard Laura say, "why don't you come over here and give me some of that big dick?" Terra moved over to Laura and stood in front of her on the couch. Laura reached up and started unbuttoning Terra's pants. She slid her jeans down to her ankles, releasing Terra's giant cock. I hadn't realized that Terra wasn't wearing any underwear that night. Laura remained sitting on the couch and started sucking on Terra's cock. I could hear Laura's lips smacking as she sucked. She must have been an expert at sucking cock because Terra was getting hard very quickly. But, when Terra was about ¾ erect, Laura stopped sucking.




Riding in Cars with Shemales Ch. 04



"Can we do that one position?" Laura asked Terra. "You know which one I'm talking about." Terra smiled back at her and they both took off the rest of their clothes. Then Terra did something I had never seen her do before. Laura got down on the ground on all fours with her ass sticking up in the air. Terra stood with her legs on either side of Laura, as if she was about to mount her ass... except, Terra was facing the wrong way. She grabbed a bottle of lube (Terra always had one in her purse) and spread a large amount on her cock. Terra then squatted down and pushed her mostly-hard cock down between her legs. She lined up her cock, aiming for Laura's asshole, and began forcing her way in.

Laura had a little trouble at first, but was quickly able to relax her ass to accept Terra's girth. Terra slowly slid in until she was nearly balls deep in Laura's butt. Then, very carefully, Terra began to bend over towards the ground. I was a bit lost as to what was even happening, to tell you the truth. Then, when Terra reached the ground on all fours, I finally realized what she was doing. Terra was now ass to ass with Laura. Her cock was facing backwards between her legs, chaining the two sexy t-girls together. Once they were both in position, Terra and Laura began moving back and forth, slapping their soft cheeks together, fucking ass to ass.

I could only watch out of the corner of my eye, but it was still an incredible sight to see. I intensified my sucking on Katie's cock as I tried my best to watch. After a lengthy time in my mouth, Katie was finally becoming hard, so I released her balls and concentrated on her tiny, hard shaft. Katie put her middle finger in her mouth and sucked on it, getting it slick with her saliva. Then she reached behind her and slipped her finger into her ass. She started fingering herself while I sucked hard on her little dick.

"Oh, fuck yeah," said Katie as her finger penetrated her asshole. "Suck my little clitty. Suck it hard while I fuck my ass." She was really fingering herself hard now. She was all the way up to her first knuckle and was slamming her finger very quickly into herself. Her big cheeks shook violently as her frenzied hand split them apart.

The moaning filling the room by this time was pretty intense. Erin, the petite, shy girl, was practically screaming, still on top of Brian's face, and Terra and Laura were sensually sighing together with Terra's big cock between them. With on last loud "uuunnngh," Terra pulled herself all the way out of Laura. Laura collapsed forward onto her stomach, her asshole winking from the gaping that Terra's cock had just given it. Terra turned around, bent over to Laura's face and kissed her.

"I'm going to go help your girlfriend cum," said Terra. Then she stood up and moved over to Erin and Brian. While Brian continued to eat Erin's pussy, Terra positioned herself behind Erin and shoved her face into her ass. Erin shifted her hips a little so Brian's tongue concentrated on her clit, while allowing Terra to stick her tongue into her asshole. Erin's mouth immediately shot open in pleasure.

Laura got up and moved over to Katie and me. She watched me suck Katie off and stroked herself until she was hard.

"Is it Laura's turn?" Katie said.

"Take your pants off," Laura said to me. I obediently obeyed, quickly stripping the rest of my clothes off. "Get down on all fours," Laura said. I liked the way she was speaking to me. It reminded me of the first time Terra had fucked me. Maybe I was just a sucker for a dominant girl with a big cock. Either way, I got down on all fours like she told me to, my ass exposed and vulnerable. 

"You too, you fucking slut," Laura said to Katie, slapping her hard on her thick ass. Katie giggled and got down beside me in the same position. With one hand, Laura stroked herself to keep her big dick hard, while she lubed up Katie and me with the other. Then Laura straddled my ass, keeping her feet flat on the ground. She squatted down a little and bent forward at the waist until I could feel her large tits pressing against my back. I don't know how she had such big tits that looked and felt so natural. It seemed impossible, but I wasn't one to complain. They felt great. Laura leaned down to me and quietly said,

"I've been wanting to fuck your ass since I first saw you at the party." Her breathing was strained and I could tell that she was incredibly turned on. I felt the tip of her penis press against my hole and slowly penetrate me. My ass had been getting pretty used to this by then and it accepted Laura's cock with general ease. With one long, steady push, Laura had most of her cock in my ass. She slid about half of it back out and pushed herself back in, this time burying the entirety of herself in me. I sighed at the sensation as Laura slowly increased her humping.

Laura's was the second dick I ever took up the ass. I had only ever been fucked by Terra before, so it was strange to suddenly have this other cock inside of me. It was different, not just in size, but in the overall feeling. It's hard to describe exactly; sort of like the sensation of stepping off an airplane into another state. In many ways it's the same, but there's something inherently different about it.

As far as size goes, Laura couldn't compete with Terra. But, she was still rather large – a full inch bigger than me at least. She had started fucking me at a nice pace, and I was thoroughly enjoying it. I could feel a couple particularly large veins in her shaft as they slid in and out of my ass, and her balls.... Like I said, I've never been turned on by balls, but Laura's were something special. I could feel the heavy things slapping against me, and it was really getting me hot.

"Fuck yeah," I heard Laura mutter. "Take it in that little fuck-hole. Ooooh God. You're so fucking tight." Laura gripped my waist and started fucking me harder. Then suddenly a little harder. 'Oh, shit,' I thought. 'This bitch isn't fucking around.' Soon, she was practically slamming herself into me. Her thighs slapped against my ass, filling the room with the sound of us fucking. But, then it quickly stopped. She pulled all the way out of my ass and didn't stick it back in.

I looked behind me to see what was going on. Laura had pulled out of me and quickly moved behind Katie. I turned my head straight to the side and watched Katie's face as Laura forcefully shoved her cock into Katie's asshole. Her balls slapped against Katie's big butt with one hard thrust. I was shocked at how hard Laura had entered her. Aside from a small wince, though, Katie barely reacted. 

What I didn't know at the time was that Katie's ass was thoroughly used. An incredibly submissive girl, Katie had been getting fucked hard for many years, and her asshole had become stretched wide. She had the kind of asshole that you could look at and just tell that she loved buttfucking. Apparently, she couldn't even cum without something in her ass. Terra once told me that Katie could even fist herself.

Laura immediately began pounding Katie, driving her face down into the carpet. Katie was loving it, talking dirty to Laura, begging for more. It was quite a sight. I felt myself getting hard just being so close to something like that. I watched Katie's big butt shake under the force of Laura's hips and lost myself in the hypnotic effect it had on me. 

But, I was quickly brought back by the sound of Erin cumming on the other side of the room. She started bucking her hips wildly, basically fucking Brian's face. Terra wasn't licking her ass anymore, but instead had replaced her tongue with her middle finger. Erin's high pitched squeals lasted a long time and her legs shook beyond her control. Terra wrapped her arms around her to keep her from falling over, soothingly kissing her neck.

Just then I felt a hand on my back and Laura shoved herself back into me. She continued right where she had left off, roughly fucking my ass. Brian, Erin, and Terra untangled themselves and sat together on their couch, watching Laura, Katie, and me. Erin was still recuperating from her recent orgasm and slowly stroked Terra's cock while they sat. I thought Brian might join us and start fucking Katie, but he just sat on the couch and stroked himself. Terra told me later that he liked to watch.

This continued for a little while. Laura moved back and forth between Katie and I a few times while the other three sat on the couch, watching. Then Terra stood up and walked over to us. Erin had been stroking her the entire time and she was sporting a massive erection sticking out in front of her. Laura was fucking Katie at the time, but she stopped when she saw Terra approaching. Terra got Katie up onto her feet and kissed her hard on the lips, grabbing a handful of both of her ass cheeks. 

"Matt, stand up," said Terra, and I did. "How would you like to fuck this ass?" Terra gave Katie's ass a slap. Without waiting for me to answer, Katie bent straight over at the waist, her ass staring right at me. I took position behind her and Terra moved in front of her, quickly stuffing Katie's face with her cock. Katie slurped on Terra's dick loudly. I looked down at Katie's ass, still gaping from the relentless pounding Laura had given her. I lubed up my cock and entered her.

I slid in easily, and began thrusting in and out of her. I thought that fucking Katie might not be as satisfying because of how loose she seemed, but Katie knew a few tricks. Once I was all the way inside her, her ass seemed to tighten around my cock a little. She must have practiced this a lot because it was the perfect tightness.

I looked up from Katie's ass and saw that Terra was slowly thrusting in and out of her mouth. I had never double teamed a girl before, least of all with my own girlfriend. I liked the feeling. Every time I thrust into Katie it felt like I was pushing her farther onto Terra's cock; almost like I was using Katie's mouth to fuck Terra. This encouraged me to fuck her harder.

I suddenly realized that I had lost track of the others as I had gotten pretty caught up in Terra and I skewering Katie together. I looked to my side to see what they were up to. Brian was still sitting on the couch, jerking himself. It kind of made me uneasy knowing that he was watching. 

Laura and Erin had joined back up and found a spot on the floor. Watching them at first, I was confused as to why Erin seemed to be dry humping Laura's ass. I had missed it, but Erin had grabbed a strap-on dildo from her purse. She had one of those strapless strap-ons where a girl puts one end inside herself. I think they're called feeldoes. Anyway, Erin was now going to town on Laura's ass while Laura was stroking a rock hard erection.

I had definitely pegged Erin as the shy, submissive type, but now I was watching her talk dirty to Laura and fuck her ass with a dildo. Every preconception I had had that night seemed to have been crushed. I turned my attention back to Terra and Katie. Terra made eye contact with me.

"Switch?" she said.

"What?" I said. Katie suddenly stood up, taking both cocks out of her holes, turned around, and bent over again. She took my cock into her mouth and Terra started fucking her up the ass, smiling from the sensation.

I looked down at Katie as she wantonly sucked my cock, which had just recently been fucking her ass. That seemed to only make her want to suck it all the more. Katie definitely was a slut, but that didn't make her mouth feel any less amazing. Terra was fucking her nice and hard from the other side. I could feel Katie jolt a little with every thrust from Terra's big dick. I watched Terra as she thrust her hips into Katie again and again. Terra noticed I was watching and our eyes met.

We stared at each other and continued to fuck Katie from both ends. Terra's breathing was becoming heavy. She looked like she might cum at any second. I was beginning to feel close to cumming as well. Our eyes never looked away from each other's. We both began fucking Katie harder, Terra deep in her ass and me fucking her face.

I leaned forward and Terra followed suit. We met in the middle. I grabbed the back of Terra's head with one hand and pulled her lips to mine. We kissed each other as if we were making up for the three weeks apart with a single act. Our tongues ravished each other, neither wanting to let the other one leave. We nearly forgot about poor Katie underneath us as we thrust wildly into her. Katie made a few garbled pleas, but we continued to fuck her. 

Then, nearly simultaneously, Terra and I were cumming. We both thrust as deep as we could, my balls resting on Katie's lips, Terra buried to the hilt in her ass. We moaned into each other's opened mouths and filled Katie with our hot cum. I shot my load straight down her throat as Terra filled her ass.

We both came for what seemed like an extraordinary long time. When we finished, I suddenly became aware of Katie choking on my cock underneath us. I quickly pulled my cock out of her mouth and she gasped for air. I felt very guilty about how we had just fucked her. She collapsed onto the floor, sweaty and tired.

"That... was so... fucking... hot," gasped Katie. Well, that sure helped the guilt. I looked up from her just in time to see Terra wrap her body around me and begin savagely making out with me. I lost my balance from the surprise of it, and we both fell to the floor. We continued to kiss and grope each other for quite some time, ignoring the others in the room.

Even though both of us had just cum, we were both very turned on. For nearly six minutes, we were tangled in each other. I don't even remember if either of our cocks went soft after we came. I just remember looking down after we stopped making out and realizing that we were both fully hard.

Terra and I looked around the room to see what the others were doing. Katie was passed out, lying on her side where she had collapsed earlier. A stream of Terra's cum was leaking down her big ass towards the carpet. I had never seen someone as oversexed as she was. Laura and Erin were still in the same spot as before. Laura was still down on all fours taking the dildo from Erin. Except, Brian had finally jumped into the mix. He was on his back underneath Laura in a sixty-nine position. He was craning his neck upwards to suck on Laura's cock while she had lowered her own head down onto his.

I watched as Laura released Brian's cock for a second. 'Yep,' I thought. 'It's smaller than mine.' The morale booster I got from that was very nice.

"Looks like we're both still hard," said Terra. "They say it's bad luck to leave an orgy with a hard cock. You want to jump back in there?"

"Fuck yeah," I said.

"Good," she said. "I've been staring at Erin's ass all night. I think I'm going to go have a piece of it." Terra smiled and moved over behind Erin. Erin stopped thrusting into Laura so Terra could get her cock in her ass. I watched as Erin's asshole stretched to its limit. Her face strained as Terra pushed into her, but it was clearly pleasurable to her. About halfway in, Terra stopped. It seemed that was all that Erin could take. Her ass was insanely tight around Terra's cock. She did make a hell of an effort to take more though.

Terra's cock was now in Erin, whose dildo was in Laura, whose cock was in Brian's mouth, whose cock was back in Laura's mouth. It was a true train of sin in front of me. It also presented a problem for me. I wasn't really sure where I should go. I knelt down next to them, deciding what to do. I considered just adding onto the train and getting behind Terra, but I thought that might make it too complicated as far as thrusting goes.

My second thought was to stand over Laura and have Erin suck my cock. I was just about to stand up and do that, though, when I felt a hand start to jerk me off. At first, I thought it was Laura, but then I realized that I was on the wrong end for her to even do that. I looked down and realized that Brian had actually reached up and was stroking my cock.

I will admit that there was a moment when I considered just letting it happen. I had always wanted to know for sure if I was gay. I was dating a t-girl, after all. I did let her fuck me with her giant cock. I did suck her off and swallow her cum. But, only three seconds after I realized that Brian was stroking my dick, I wanted it to stop. I just couldn't be aroused by a man doing something like that with me.

However, I had no idea how to deal with this problem. I'm sort of a non-confrontational person by nature, and I definitely didn't want to piss off Brian by rejecting him. He was the host, after all. And.... (Jesus, a guy had his hand around my cock and I was thinking about manners.) So, instead of just slapping his hand away, I basically just stayed there with an uncomfortable look on my face. However, Terra and Erin both saw what was happening, and Terra, knowing I wasn't liking it, decided to spare me some discomfort. I saw her whisper something into Erin's ear and Erin nodded as if she understood.

Erin then tapped Laura on the shoulder and got her to look back at her. Through some strange non-verbal communication, Erin told Laura what she was going to do. It was like watching a S.W.A.T. team communicate. I didn't know what was going on, but they seemed to understand it. Laura went back to sucking on Brian. Then Erin thrust into Laura strongly, causing Laura's hips to move forward and her cock to go deep into Brian's mouth. He gagged on it and released my cock so that he could push Laura up off of him a little. As soon as he let go of me, Erin quickly wrapped her hand around my cock and took over stroking me. 

After he stopped gagging, Brian reached for my cock again, but, when he found that Erin's hand had replaced his, he put it back on Laura's hip, none the wiser about the girls' plan. My jaw fell open in astonishment. Such an intricately thought out plan just to get a guy to stop jerking me without directly asking him to. I felt like it was definitely an overly complicated way to go about doing something that could have been accomplished by me just growing a pair, but it was fun to watch it all happen; like a weird, sexual Rube Goldberg machine.

Erin winked at me and pumped away at my cock. Her soft hand felt wonderful sliding up and down my shaft. She would sometimes stop just under the head and give a few quick jerks, working the sensitive area. Watching everyone was turning me on greatly. I knew it wouldn't take as long for me to cum as it did last time.

"Stand up," Erin said to me. I did as she asked and she continued to jerk my cock. Then she had me move closer to her and she took me into her mouth. She sucked me for a little while, then went back to just using her hand again. She continued alternating like that at odd intervals. I was pretty impressed at Erin's motor skills considering she was still fucking Laura with a dildo and taking Terra up her ass.

Brian was the first of us to cum. It came as a bit of a surprise to Laura since he gave no warning. She tried her best to swallow it all, but some if it leaked out of her lips and streamed down her chin. Laura came shortly after. Brian released her cock just as she was cumming and she covered his chest with a huge load. Brian and Laura climbed off of each other and cleared out of the way.

Laura returned though, taking the dildo out of Erin. It slid out of her with a slurp. Erin's hot cunt was dripping wet. Laura shoved her face into Erin's pussy and began eating her out. She really seemed to like that, because she started moaning louder and stroking me harder. She even pushed back into Terra harder. Erin took me into her mouth one more time and sucked on my cock like a fucking machine. 

"Oh God! I'm going to cum!" I said. Erin took me out of her mouth and pumped my dick fast in her fist.




Riding in Cars with Shemales Ch. 04



"Cum on my titties," Erin gasped. The sensation of Terra and Laura working on her at the same time was overwhelming her. Erin continued to furiously jerk my cock, aiming the head towards her chest. I felt my orgasm build up until it reached the breaking point. Then my cock was twitching under her grip. I shot several streams through the air, splattering onto her soft tits.

After I stopped cumming, Erin licked the remaining cum off of the tip of my penis, and then let go of my cock. I took a step back and watched the rest. My cum had streamed all the way down the front of Erin by now. Some of it had even gotten in Laura's hair. See didn't seem to notice or care though. Erin had both of her hands on Laura's head and was shoving her face up into her pussy, and Terra was continuing to gently fuck Erin's tight asshole.

It was clear that Erin was going to be the next to cum. Her pussy was dripping juices and her moaning had become more urgent as Laura's tongue continued to attack her clit. Sure enough, she was soon cumming. Terra held her from behind as she had done earlier while Erin's body shook beyond her control from the very powerful orgasm that had taken over her. She was cumming much harder than she had earlier. I can only imagine it was because of the sensation of Terra's huge cock stretching her ass.

After Erin's orgasm finally began to subside, Laura lifted her head from her pussy and kissed her on the lips. She made sure not to wipe her mouth so that Erin could taste herself on her lips.

Terra then pulled all the way out of Erin's ass and started jerking her rock hard horse-cock. She was pumping away at her big cock with clear intent – she wanted to cum, and she wanted to cum right then. Erin and Laura saw her and they both got down on their knees in front of Terra.

Terra's teeth clenched together as she stroked herself as hard and fast as she could. I had never actually seen Terra jerk herself off before, but I found myself enjoying it. It was a turn on to watch her giving herself pleasure. Soon, Terra let out a soft sigh followed by a grunt as she drained her balls onto Erin and Laura's waiting faces. They opened their mouths, trying to catch as much of the hot cum as they could. I always loved watching Terra cum. The look of total ecstasy on her face was always a pleasure to see. After, shooting many hot streamers onto both of them, Terra was completely spent. Everyone sort of collapsed after that, catching their breath and regaining their strength.

And then, just like that, it was time to leave. Everyone put their clothes back on and the girls cleaned themselves up a bit. I watched as Brian, tiredly made his way over to Katie on the floor. She must have been pretty drunk earlier, because she was still out. As we were all putting our shoes back on, I saw Brian move his face towards Katie's ass and lick up some of the excess cum leaking out of her. Then he moved into a spooning position with her and seemed to pass out as well. 'What a strange, weird little man,' I thought.

Laura, Erin, Terra, and I all walked out of the apartment and piled into a cab on the street. Just as quickly as we had come, we were off. We must have been quite a sight, the state we were in – I'm sure that Erin still smelled like booze and cum. We were all exhausted and longing for sleep. Terra sat next to me with her head on my shoulder the whole way home.





To this day, that night was probably the wildest thing I've ever been a part of. For a guy who considered himself one hundred percent straight less than a year before, I never imagined I would ever even be a part of something like that in my life. Looking back, I probably wouldn't have even done some of the things I did at Brian's place if I hadn't had that much to drink. But, I still don't regret it. Instead of making things complicated with Terra, like I thought it might, we were completely fine afterwards. We didn't treat it like a big deal, and so it wasn't.

True, we had sex with other people. But, at the end of the night, we left together with big smiles on our faces. There certainly were many memorable moments that night. But, the one I always remember didn't happen at Brian's. It happened when we got back to Terra's. Terra and I stumbled up to her room. We took off our clothes and practically fell into her bed. I put my arms around her and held her like that all night.

Nothing spectacular happened; nothing somebody might find particularly interesting. We just slowly drifted off to sleep in her quiet house, and she was finally mine alone.

TO BE CONTINUED