Riding in Cars with Shemales Ch. 04

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Part 4 of the 4 part series

Updated 10/26/2022
Created 11/27/2012
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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.

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