Slut Tails - The Adventures of Pussi

I grew up in a small Midwestern town of about five thousand people. It wasn't a good place to be different, and I was definitely different. I always had been. Even when I was younger I liked more girly things. I didn't like to play sports, or cars and I didn't like to get dirty. After puberty, I was really different. I had absolutely nothing in common with other guys my age. Instead of becoming muscular and strong, I stayed thin, and became even more swishy, with a feminine walk and high pitched voice. I did make friends with a goth girl named Jessica, and began hanging with that crowd, and adopted their style. I grew my hair long, dyed it black, and wore skinny jeans and t-shirts that were a size too small. I also got my ears pierced, and occasionally wore make-up and painted my nails. This of course brought much ridicule from the jocks and the rednecks, and they all assumed I was queer. My new nicknames became Pussy, and Faggot.

They were correct about my sexuality. I did like girls, and found them attractive, but I also liked guys. I liked watching gay porn, and found myself curious to bottom. Something about it was very arousing. I began to touch my ass while jerking off, then began fingering myself. I really wanted to act on my desires, to be with a guy and feel him inside of me, but I had no idea how to meet a guy. I didn't even tell anyone about my desires, except for Jessica. So I just kept my thoughts to myself, fantasizing and hoping I would meet a guy soon. Then, between my Sophomore and Junior year, a hot skater with shaggy blonde hair named Nathan moved to town.

Nathan was from Dallas, where he had been getting into some trouble, so unfortunately for him, his mother had sent him here to live with his Dad. We quickly hit it off, and Him, Me, And Jessica soon became best friends. Jessica's brother would buy us beer, and we would all three sneak off into the woods to drink and smoke weed. He was a cool guy, and we loved his stories about the scene in Dallas.

One night, after a few beers, Nathan confessed that he was bisexual, and I sucked his cock. It felt wonderful, better than I imagined. I loved pleasing him, and making him cum, and I started doing it often. At first he would return the favor, but after a while it was just me sucking him. I didn't mind that at all. I loved giving, but wasn't all that into receiving. Soon after that, we fucked for the first time. It hurt bad, but I did really enjoy having him inside of me, and making him cum. We did it more often, and it became very pleasurable for me. It felt so natural, getting fucked by him. He was muscular and masculine, and I was weak and feminine. He began to get a little more dominant, talking dirty and slapping my ass like the studs did in porn. I began borrowing Jessica's lingerie, and dressing sexy for him. I loved looking sexy, especially in stockings and panties. And when we were together, I loved the dynamic between us. He was the man in the relationship, and I was the woman. It felt right to me, and so natural, as if this was what I was meant to be. I was extremely happy when he was giving me his long, skinny cock.

Then one day, our senior year, his father came home, and caught us in the basement. Needless to say, he wasn't very happy catching his son fucking a boy who was dressed in purple stockings,and freaked out. He told my parents, who weren't happy, but weren't at all surprised. We continued to see each other, but it became difficult, as Nathan's Dad didn't allow me in their house anymore.

One evening, we snuck off to the lake, with a twelve pack of beer and a little weed. It was spring, just a month away from graduation, and we were both eighteen. After some skinny dipping in the cold water, we decided we needed to warm up. We built a fire, sat around it but naked, and shared a joint. Nathan sat on a stump, and in the fire light his long, skinny cock looked delicious. Soon I was on my knees, moving my head up and down as he sat back and enjoyed my mouth. "Fuck, that feels so good!" He said, making me feel proud. I sucked him for awhile, then he bent me over the picnic table, and took my ass. It had been awhile since we had fucked, and his long cock felt awesome sliding into me. While he pounded away at me, I jerked off, cumming very quickly. Then I grabbed the sides of the table, and held on, enjoying the feeling of my man's dick. He didn't last long, and with a deep groan, he came inside of me, then pulled out. I stood up and he pushed me against the table, and gave me a deep kiss.

"Fuck I love you." I said when our lips parted.

"I love you too." He replied. But his frown told me something was wrong. "Um, there's something I have to tell you."

Oh no, I thought to myself. "What's up?" I asked.

"Um, well, um, I joined the Army."

"You did what?" I yelled. This was in the mid 2000s, and both wars were going full blast. "Are you crazy? You're gonna get yourself killed!"

"Look, my Dad told me after graduation, I had to get out. He is still pissed about catching us. You know how conservative he is. And Mom is a Jesus freak, so she's pissed that I fuck guys. So I can't go there either. I really don't have much of a choice."

"Yeah you do!" I cried. "Let's just leave together. We're eighteen! We can do whatever we want!"

"Dude, I would love to, but we couldn't afford it. We don't have any money. Besides, I've already signed the papers. Two weeks after graduation, I leave."

I was bawling now. I couldn't believe it. I was so in love with this guy, and he was leaving me.

After graduating, we went and got tattoos together. I got three hearts on my ribcage, in rainbow colors, for me, him and Jessica. We fucked a few more times, and then he was gone. I would see him again for several years.

Jessica had received an art scholarship, and at the end of the summer she left for school. So I was now alone, in this hick town. Fortunately, Jessica's school was just a few hours away. Knowing that I would love the judgemental atmosphere, and the alternative music, she invited me to visit. I had a blast, and liked that I could be myself, and nobody cared. On my first visit, I saw a couple of gay guys, and hoped I could soon meet someone. I wanted to move there, but of course I couldn't afford to. But one of Jessica's roommates was moving out in the spring, and her other roommate was ok with me moving in. I just had to hang on for a few awhile.

At home, life had become unbearable. Word had got out that I really did take it in the ass, wore panties, and the rednecks constantly harassed me. "I've got to get out of here!" I cried to Jessica on the phone.

"You should come visit this weekend." She said. "One of the bars is doing a drag show, amd it's all ages. You'll love it."

"Ok!" I agreed. It sounded awesome. I was fascinated with drag, and hoped to one day perform. I couldn't wait to check it out.

Friday finally rolled around, and I was stressing about what to wear. I fussed around, and put on a black and purple thong. Then a pair of very tight skinny jeans, and a tight t-shirt that exposed my stomach, and my belly button, that I had recently pierced. I accessorized with a studded belt, studded bracelet and red Doc Marten boots. Then I hit the highway, with the music blasting. About an hour into the trip, I had to pee, and pulled into a rest stop. As I walked to the restroom door, a large black man came walking out. As we passed each other, I heard him say, "Damn boy!" It didn't sound malicious or threatening at all, and it dawned on me that he was checking me out. I smiled, enjoying the attention. As I was doing my business, the door opened and I heard someone walk in. I finished and zipped up, then turned around to see the man standing there smiling.

"Wassup?" He said. I began to feel nervous, he was a big guy, built like a NFL player. His head was bald, and he had a graying goatee. He had obviously followed me in here, and I wasn't sure what his intentions were. I had no idea what to do. If he attacked me, I knew I didn't have a chance. I only weighed about 130#, and I couldn't fight at all. But his smile didn't seem threatening, and he seemed friendly.

"Um, nothing." I replied.

"Oh I see. So are you tricking, or cruising?"

"Huh?" I asked. I had no idea what he meant.

"Are you tricking or just looking for some fun?" He asked again. "Because you're fine as hell. Either way I'm down."

It dawned on me that he was hitting on me, and thought maybe I was a prostitute. Honestly, I was flattered, and a bit excited by the idea. "Oh, no, I'm just using the bathroom." I said softly. I wasn't sure what to say.

"Oh I see!" He said, with another big smile. "Well anyway, you are sexy as hell boy. I'd love to hit that."

"Really?" I asked, amazed.

"Hell yeah. If you're up for a little fun, I'm down. If you're hustlin tell me how much."

My heart beat fast as my brain worked to comprehend what was happening. I had never been hit on before, much less by a stranger. I had only been with one guy. I was clueless to how this stuff worked. I looked the man over, and started thinking about it. He was sexy, big and manly, and in his early fifties. I had fantasized about older men, black men, and he was both. It had been months since I had been with a guy, and I was seriously horny for some dick. I had been hoping to meet a guy, and here was one right here, hitting on me. But the idea of going off with a stranger was terrifying. I couldn't do that. But, then I nervously said, "I could be up for some fun." And his smile got really big. What in the hell did I just say? I thought to myself. The man stepped close to me, and ran a finger down my stomach.

"Hell yeah, baby." He said, his face inches from mine. "Well I can be lot's of fun. I love showing a hot, pretty boy with a fine ass a good time."

I blushed at his compliment and his touch gave me chills. I felt my body quiver with fear and excitement. Part of my mind was telling me to run, but the other part was telling me to stay. I had no idea what to do, or what to say. He looked into my eyes, and his finger slid up my side. I felt my whole body tingle. I had been craving a man's touch, and here was a man touching me. I knew I was all his. I tried to think of something to say, but my brain was going a thousand different directions. "So do you live around here?" I said finally.

"Nah, baby, but my truck is out back. I have a great big sleeper cab, with a nice comfy bed."

"Oh." I said, unsure of what to do next. "That sounds fun!"

"Oh it will be!" He said, then he moved his mouth to mine, and gave me an aggressive kiss. While he licked the inside of my mouth, his other hand grabbed my ass and squeezed tightly. I felt myself tremble with fear, then overwhelming excitement. I couldn't believe this was happening. He quit kissing me, and motioned with his head towards the door. "Come on!" He said enthusiastically, and I followed him outside. He looked around appearing a little nervous, and then walked towards the row of trucks. I followed, scared out of my mind. I almost turned around and ran for my car, but something inside of me pushed me forward. I could not believe I was actually doing this. I followed him to a red truck, and he unlocked the door then held it for me. I climbed up into the spacious cab, looking around. It was bug enough to stand up in, and had all the comforts of home. A microwave, a huge tv, and a good sized bed that was neatly made. He stepped in behind me, and closed the door, then pulled some curtains around the windshield. His CB crackled and I heard a voice say, "Send that hot ass down here when you're done with it!" And another make whistling noises. He smiled, then shut it off. "I'm James by the way." He said, smiling again.

"I'm Kyle."

"So Kyle, are you ready for some fun?" He asked, then got really close to me. He kissed me again, and one hand groped my butt, while the other rubbed one of my nipples through my shirt. I had never had my nipples played with before, and it felt amazing. My whole body felt limp, and I let out an involuntary moan. "Like those titties played with do ya?" He said, teasing it harder.

"Yes!" I moaned. I felt my shirt being pulled up, then lifted over my head. He moved his head down, and licked my nipple, then gently bit it. "Oh fuck that feels good!" I cried, as he moved to the other one. His other hand fumbled with my belt, then the button on my jeans, and I reached down to push them off. They were extremely tight, and it was a struggle, but after a bit they fell down around my ankles. James kept licking and nibbling my nips, while both hands squeezed my ass. This was nothing like it had been with Nathan. This was being taken by a grown man. And it felt amazing.

"Oh, hot little panties!" James said, rubbing the waistband on my thong. "I like that!" He stepped back and looked me over. "Turn around, let me see that ass!" He instructed. I did, and heard him say "Fuck yes, boy! That is one hot little ass!" When I turned back around, his shirt was gone, revealing a thick muscular chest and a bit of a beer belly. Then he undid his jeans. They dropped to the floor, and I stared at his fully erect, giant cock. We had measured Nathan's once and it was six and a half inches, and James's was longer than that. It was also much, much thicker, almost as thick as a pop can. And while Nathan's balls were smaller and tight, James's hung low, several inches below his cock. I stared for a minute, marveling at the size. "Like that do ya?" He said, snapping me out of my stupor.

"It's so big!" I said.

"It sure is baby." He said proudly. "Now I know you want to suck it don't you?" I was speechless so I just nodded. He grinned, then laid down on the bed, grinning at me with his massive meat standing straight up, waiting for me. "Come on baby. Take off those jeans and boots and come to bed. Leave those panties on though. Daddy's nice and hard for you."

I quickly took off my boots, and stepped out of my jeans, then crawled onto the bed. On all fours, I put my face down towards his crotch, opened up and wrapped my lips around his dick. I may have only sucked one cock up until today, but I had sucked it often and knew just what to do. I slowly worked it down my throat, trying to take it all. This dick was much thicker, and it filled my mouth. It took a little effort, but I was able to swallow it all, and enjoyed hearing James's satisfied groan. I slowly went back up, and then took him deep again.

"Damn boy, you're a talented cocksucker aren't you?" He hissed, as his dick touched the back of my throat again. His hand was on the back of my head, and pulling my hair. He thrust himself up a little bit, going deeper in my throat.This was completely different than sucking Nathan. James was far more aggressive, saying nasty things and holding my head to control my speed. While one hand held my head, the other gripped my ass, squeezing it hard. James smelled different as well, it wasn't unpleasant at all, just more masculine. With his hand squeezing my butt, and his dick throbbing in my mouth, I was completely turned on. He kept telling me I was a "good cocksucker" and calling me a bitch, as he jammed his cock deep down my throat and that just got me even more excited. James was a real man, and he was using my mouth. This was what I had always wanted.

"Does that feel good?" I asked, when I came up for air.

"Oh hell yeah baby! You know how to suck a dick boy!" He praised. I smiled, then went down to lick his balls. Nathan loved that, and apparently James did too. He moaned, and wiggled around, spreading his muscular legs to give me easy access. His balls were very big, but tasted delicious. "Oh, damn boy, suck those balls you slut!" He said, twisting a handful of my hair. "Damn boy, you know what Daddy likes!" I liked hearing that, and sucked his balls for a while, before returning to his dick. I quickly bobbed my head up and down on him, until he said, "Fuck baby, you're about to make me cum. And I still need to fuck that ass. You better stop."

The next thing I knew I was positioned with my face in a pillow, and my ass high in the air. I began getting scared again, thinking about how bad that big dick was going to hurt. It had been months since I had been fucked, and I knew I was really tight. As I lay there waiting for his dick, I felt something else. After he pulled my thong aside, his hands gripped my cheeks, then I felt his goatee between them, and his tongue licking my hole. I screamed with pleasure into the pillow, pushing myself back towards his face.I had never experienced anything like this. Nathan would never eat my ass, but James did it as if I was his last meal. It was the most amazing thing I had ever experienced. I thought dick felt good, but this was unreal. "Oh my God James, that is amazing!" I cried, feeling his tongue press inside my hole.

"Yeah baby. Daddy likes to eat that ass before he fucks it!" He said, then went back for more. "Damn that is one pretty pussy! It tastes sweet too!" He licked me some more, then bit me gently on the ass. Then he went back for thirds, slurping and sucking on my hole while rubbing my dick. I moaned and squirmed. "Fuck baby, can I take a picture of this pretty pussy?"

"Sure." I said, trying to catch my breath.

"Damn boy, that is one nice little hole you have!"

I lay there, ass in air and really turned on as this stranger snapped pictures of my asshole. It occurred to me that I didn't know him, and he could post them anywhere. But I didn't care. "Thanks!" I said, enjoying the compliment. He rubbed it with a finger, then got it wet with lube, and slid his finger inside me. It was a big finger, and I felt myself clench around it.

"Damn that's tight!" He said. "Fuck. That's gonna feel really good!" He wiggled his finger around inside of me, then slipped it back out. It was time for dick. "I hope you don't mind a condom. I don't do raw on hookups."

"Not at all." I said. Shit. I hadn't even thought of that.

I waited for him to put on the rubber, face down and ready to be taken. I wanted him so bad, but I was really nervous. I didn't know what to expect. I felt him squirt some more lube on me, then his dick touched my hole. As he slowly penetrated me, I squeezed the pillow and tried to relax. The pain was intense, as he spread me open, and I began to try to wiggle away. "Open up for me baby and give me that sweet pussy!" He said in a soothing voice, and pushed himself against me.

"Ffffuuuucck!" I whined, panting into the pillow.

"Come on baby, open up that ass." He said, pushing some more. He went in a few inches, and I moaned in pain, feeling my ass being ripped open. "There we go!" He said triumphantly, as he was now in, and he slowly pushed deeper, until he was completely inside of me. "There it is baby. You have it all now!"

"Fuck you're so big!" I cried, squirming around. "Oh my God you are huge!" I pushed myself up on all fours, trying to find a more comfortable position.

"Yeah baby, but I have that good dick." He said, slowly pulling it out. "Daddy's gonna fuck you so good, boy. You'll be wanting more. You'll be begging to be Daddy's bitch." He pushed it back in again, then pulled back out. He slapped my ass, then slammed himself in me. His hands gripped my hips, and he began fucking me, hard and fast, and soon his giant cock felt great in my hungry pussy. I put my face back down onto the pillow.

"Oh fuck me James!" I moaned. "Oh fuck yes!"

"Yeah baby. Take that dick!" He barked, slapping my ass again.

"Oh yeah. Give it to me! Harder harder!"

"Fuck boy, that ass is tight! Damn you feel good!"

"Ooooooo fuck Daddy! Fuck meeee!" I screamed.

"That's right baby. Take that dick!"

He slapped my ass hard, and soon he was simply pounding me, drilling away at my insides, as I moaned like a bitch. He was going really deep, and it hurt again, but I liked it. I had only thought Nathan had fucked me. I had no idea. James was truly fucking me, beating me up like a trashy whore. And I liked it. He held my waist tightly, and pulled me back towards him, slamming his pelvis into me. I moaned into the wet pillow, which was soaked with my drool. I felt like such a bitch, getting railed by a real man while wearing purple panties. He was having his way with me, and there was nothing I could do about it. Not that I wanted to. I was loving this. "Oh fuck me hard Daddy!" I screamed, and he slapped my ass hard again.