Here's a story that woulda, coulda, SHOULDA happened when I was much younger. But alas, it has only happened here and now in my filthy little mind. Enjoy it and please... vote! And feel free to send me feedback. I love all of your filthy little letters.
I was just horny. All of the time. I just wanted to fuck someone in the worst way. 18 years old, never had a date. Too skinny, too weird. I wore my hair long, not a very hairy body, not very athletic. Just a skinny kid who didn't get any attention. Lot of church girls in the bible belt but they weren't very interested in me. I guess. It didn't seem like anyone was very interested in me at any level.
Sundays were long boring church services. I sat in the back and tried to stay awake. Tried to stay out of trouble. Every once in a while, this older guy Mike would come sit in the back pew with all of the teenagers. He always wanted to talk cars or guns. He was about half deaf so he talked loud enough to get shitty looks from the rest of the congregation. But he didn't care. Mike was in his early 40's, on the chubby side. Not a good looking man by anyone's figuring. Never married, never had a girlfriend. Just as socially retarded as I was except I was only 18.
Some days after church, I'd head over to Mike's house. We'd shoot stuff in his backyard or hang out in his machine shop or if the weather was bad, we'd hang out in the basement of his house and watch movies. Cool shit like the old spaghetti westerns and war flicks. These were back in the Betamax and VHS days. All of his movies were recorded by some friend of his on satellite television. We'd sit around, shoot the shit, watch some movies. I sure as hell didn't fit in with anyone my age. It was just cool to be able to hang out with somebody.
Some of the movies had nudity in them. Just flashes of stuff, like in 'Enter the Dragon'. He'd look at me and smile. It was all good. I wasn't going to rat him out for letting me watch stuff that good little Christian boys weren't supposed to see.
Besides, I had way worse under the mattress of my bed. Cheri, Oui, Swank... all the good shit. All kinds of crazy articles in there. S&M stuff, cuckolding, chicks with strap-ons sometimes. I read one article about by this woman talking about her male slave. It was all interesting. It was all exciting.
I hadn't done anything with anyone else ever. Well, not really. I had a male cousin who would come over and we'd dare each other to touch the other one's dick. I was so fucking horny, it didn't matter who was touching my dick just so long as someone was touching it. Neither of us knew how to cum so every time I saw my cousin, it would just leave me all worked up and in a state. Then I'd mine the back of the cock mags for the fine print in the ads at the back, the stuff that had the almost hardcore stuff.
After church one day, I headed over to Mike's and although we were having a good time watching a movie, I ended up getting one of my many ill-timed erections. It wasn't like Mike could see it though; he usually propped himself up in his bed and I sat in an easy chair beside it and we watched the television up on his dresser. I was trying to concentrate on the plot to the movie but all of these images from the magazine kept coming to mind. Especially the story about the domme and her slave. She'd dressed him up in female clothes, made him eat her ass and then whore'd him out all dressed up as a woman. Made him suck her toes while some guy fucked his ass. I couldn't get the idea of being fucked from behind out of my head.
The movie ended and Mike and I were talking about the holes in the plot. The credits rolled by and then the big static covered screen of white snow that you'd see when a video tape ran out. It played through the end of another movie and another, maybe only a couple of minutes of each one. And then...
As the stripe of snow rolled down the screen, an image popped up of a naked woman on all fours sucking a cock while a guy behind her was lubing up his cock to fuck her in the ass. Mike jumped up to grab the remote but couldn't find it right away. "Whoops," he said as he fumbled through the blankets and pillows for the missing remote. "My buddy records these. Sometimes you find this stuff on the end of his tapes."
I smiled and raised an eyebrow, "Well hell, don't shut it off on my account."
Mike continued to look for the remote but he was now watching the screen quietly with me. The woman's head bobbed up and down on the big, sloppy fat white cock and winced as the guy behind her drove deep into her asshole with one big shove. All of the dialogue was in French. "That's the French for ya," Mike said. "They like to stick it in the backdoor."
"Whatever makes them happy," I said not looking over at him. "I'd stick it in about any hole I could get a hold of at this point."
He laughed and nodded in agreement. "Yeah, it's been a long time for me too. But most women are just more trouble than it's worth. A couple hours of fun turns into several weeks of misery. And that's if you're lucky!"
We laughed and went back to watching. The woman on the screen was really moaning now and tears were leaking out of the corners of her eyes. The shot panned over to someone else walking into the scene. It was a tall woman wearing black thigh highs, heels and a short satin robe. She placed her hand on the back of the woman's head and pushed her deeper onto the cock in her mouth while kissing the guy fucking the woman's ass.
"Huh," Mike grunted. His face had gone as beet red as mine. "This could get good. Only thing better than one naked chick is two."
I caught a string of saliva that was trying to leak over my bottom lip and swallowed hard. Everything that I had ever wanted to see was right in front of me. The woman in the lingerie and robe stood on the bed and lowered her panties. To both Mike and I's surprise, beneath her big hairy late 70's bush, a big uncircumcised cock bounced up, hard as a rock. The woman guided her cock to the buttfucker's mouth and began pumping his face.
"Nah, we can't have that," Mike grunted and went into a frenzy looking for the missing remote.
I should have said something like, "Holy shit, it's two dudes. Fucking turn it off." But I didn't. I remained transfixed, face red, and cock leaking cum down my leg inside my blue jeans. I didn't care if she was a guy, she was hot. Hotter than the chick with two dicks in her. Hotter than any woman I'd ever seen.
"God damn it," Mike grunted and began digging in the space between the wall and the bed. He looked over his shoulder and said, "Can you get up and hit the stop button on the VCR?"
I looked over, mouth slightly open, heart racing and simply said, "Why?"
Mike sat up for a moment and looked at me funny. "This doesn't bother you?"
I shrugged. "No. She's hot. I don't care if she's got a dick or what. I've seen worse," I lied.
Mike turned his attention back to the television. The woman getting her dick sucked was now on all fours where the other woman had been. Her black high heels prodded the buttfucker along as she slurped on the already wet cock of the guy sitting down. The woman who had been getting fucked, was laying under the tranny sucking her cock. I felt a twinge in the head of my dick and snapped out of my trance quickly. Jesus. I couldn't cum right now. Not in front of Mike.
I did everything I could to stop it and just narrowly missed blowing a massive load into my pants. As I struggled not to cum, my hand slid over to my cock and pinched the end. Mike was watching. "If you need to let the pressure off, the bathroom's just down the hall there."
"Umm, nah," I swallowed. I hung my head down slightly ashamed. "I uh, I don't really know how to do that very well yet. Be nice if I did but I haven't quite figured it out yet."
"Well," Mike said and turned the French dialogue down with the remote control that he had now located. "You just jack it. Put your hand around it and pump it up and down." He made a crude kind of jerking off motion.
"Oh," is all I could manage to say. "I uh, well sometimes I get it to go off but sometimes I just make it sore."
"Ain't nobody ever told you how to do it?" Mike asked.
I shook my head no.
"Well," Mike said and sat up. "Let me fast-forward through this a little, see if we can find somebody doin that."
The figures on the screen sped into fast fucking, fast licking, fast sucking. Heads bounced and legs flipped around like some kind of crazy acrobatic show. Every once in a while Mike would hit play to see exactly what was going on. Every time he did, the chick with a dick was back on. "Gonna have ta talk ta ma buddy about what he's been record'n." The tranny was now stroking her cock back and forth faster and faster until big globs of white cum shot all over the woman's face in front of her.
I swallowed hard and tried to be cool. It was really weird sitting there with Mike watching this. I tried to say something witty: "So, you mean I gotta dress like that to jack off properly?" I joked.
Mike's expression changed slightly. He smiled but it was weird. He paused for a moment. "Well, you do have long hair. Pretty skinny and not very hairy. Hell, you'd probably look alright in those clothes."
My heart skipped a beat and the head of my dick spasmed again. My hand moved to control it but it managed to get off a full pump before I could stop it. A small wet spot appeared on my jeans and Mike craned his neck forward. "Well, hell. I guess you like that idea."
I did. The idea of becoming what I was obsessed with seemed to be a problem solver. Mike's attention was adding an exhilarating weirdness to it all. I blushed so hard that I just wanted to die.
"I've got some things back in the closet. My sister's storing a bunch of stuff here. She always dresses slutty as all hell. I'm sure we could find you something if you want." He talked with his hands and I noticed a big bulge sticking up in his cotton sweatpants.
I shrugged again. I could see him push his cock down as he got up and walked past me. A few minutes later he walked into the room carrying several big cardboard boxes that said 'Laura' on the side. I'm not very big or tall. My feet are unusually small, which is odd because I have a decent sized cock.
Mike dumped the contents of the box on the bed and I had to clench the muscle at the base of my balls to keep from pumping the rest of my load out. Bras, panties, stockings, garters, teddies, corsets all spilled onto the bed. Mike found a white garter belt with white thigh highs already attached to the suspenders. The stockings were lace across the top with little black bows at the front. He tossed them back to me without looking at me. He dumped the next box on the bed. A short red dress and matching heels fell out. He threw these to me as well. He wouldn't look at me or turn around but I could see why he wasn't turning around; there was no concealing his hard on. "You know where the bathroom is. Go try'em on if you like, we'll see if we can't teach ya how to release some pressure."
I didn't say anything. I took the clothes, got up and left the room. My legs shook, my breathing was shallow, my eyes burned and I felt like I was going to cry just from the overwhelming intensity of it all. I flipped on the light to the bathroom and began undressing. There was no mirror in the bathroom except for the one over the sink. Which was just as well. I don't think I could have handled seeing myself that way right at that moment.
I fumbled with the garters and hose. Put them on backwards first, then took them off and put them on forwards being careful not to put a run in the fragile fabric. The dress was short, tight and pulled straight on over my head. The front of the dress stood straight up. I tried to wiggle into the panties but they only managed to corral one nut.
The shoes were tight but they fit. The heels were at least 4 inches tall. I wobbled unsteadily in them and used the sink to steady myself. The feeling of the stockings on my legs was almost too much. I just wanted to jack off while wearing them and then run from Mike's as fast as possible. But something deep inside me put my hand on the bathroom door handle and push it open.
The basement hallway between the bathroom and Mike's bedroom was dark and narrow. Outside rain was falling against the short basement windows. It was late evening and I used the stuff stacked into the makeshift hallway to guide myself down the path. As I walked, I started rubbing my thighs together to feel that magical material. This just caused my cock to throb more and my ass to sway from side to side.
At the end of the hall, I could hear that Mike had resumed the porn film as nonsensical French poured out of the television. I gulped down hard and felt a shortness of breath turn hot and suffocating in my chest.
As I walked through the doorway, a flash went off. And then another. Mike had his fucking camera out! He wasn't a big guy or in shape or anything but there was no way I was going to be able to take it away from him. He looked up from behind the lens and smiled broadly.
"Ha, ha," I said. "Very funny." The blue spots cleared from my vision and I saw that Mike wasn't wearing a stitch. His round hairy belly hung like a wooden keg over a healthy size cock that was pointing straight at me.
"It's insurance," Mike said and put the camera into his gun safe and closed the door. "I don't want this silly shit coming back on me later."
"That makes sense, I guess," I said. We'd both be run out of town if people found out about this. That is, if we weren't just strung up first.
Mike scooted to the far side of the bed and patted the spot next to him. "Have a seat."
I sashayed over to the bed and sat down at the edge. On the television, it was a close up of the tranny blowing one of the guys. Her tongue swirled around the bloated purple head and occasionally she looked up and smiled with the big dick in her mouth.
I jumped slightly when I felt Mike's hand on my leg. It landed at the knee and slid smoothly back and forth up my stockinged thigh. Every so often, the back of his knuckles would touch my dick or balls sending a jolt through me. I reached down to start jacking myself off. "Stop that," Mike said in a low, menacing voice. "You'll get to cum. But not yet."
His hand reached up into my panties and began caressing my nuts. I moved my hips back and forth trying to get off by his touch alone. I needed to cum worse than I needed to breathe.
"You wanna cum, right?" Mike asked. His breathing was faster also.
I nodded yes.
He pointed to the screen, "You see what she's doing, right?"
I nodded again.
Mike pulled his hand out from under my skirt and grabbed the back of my neck. He began pushing me towards his dick which throbbed up and down with the beat of his heart. I stole a look back at the television as my head was being pushed down. The tranny on the screen had the cock all the way in her mouth and was bobbing back and forth furiously. Mike's hand straightened my head and I opened my mouth. I'd had my cousin's dick in my mouth before for a couple of seconds. It wasn't a big deal. Right?
It felt strange having Mike's dick in my mouth. I made my lips into an 'O' and began to run them from the top to the bottom. Well, as far to the bottom as I could get. For a fat, ugly, nerdy guy, he kind of had a big dick. It was soft on my tongue and hard at the center. I licked the shaft. I tongued the piss hole. I lapped at his balls. Mike had wadded up my hair into his hand and was directing my pace. I looked up at the television and saw the tranny playing with the guy's balls as she sucked. I brought my free hand around and held Mike's shrunken balls in my hand as I swallowed his dick over and over again.. I did as she did and ran my fingertips over the puckered skin. Mike began pushing my head faster and faster.
"Oh yeah," he said through gr
itted teeth and pulled my head up to the tip of his dick and held it there. I felt it twitch in my mouth several times as something salty and warm filled my mouth. I swallowed some back but a small amount leaked from the corner of my mouth and ran down my chin.
Mike pulled me off and lay breathing heavily for a while. I was in a trance. Even though his hand had let go of my head, I continued to lick and suck the head of his cock. I pulled one of his balls into my mouth and rolled it around. Mike's hand came back and pulled me off his sensitive, shrinking member. "Jesus Christ," he said disgustedly and sat up.
He buried his face in his hand and shook his head back and forth. "What the hell have I done?" he asked himself without looking at me. "I'm sorry..." he started.
I didn't know what to say. I still needed to cum, my mouth was full of cum and I suddenly felt as though I had done something worse than anyone in the history of mankind. Mike's pause extended and finally I blurted out, "I liked it."
Mike looked up at me slowly and took me in from head to toe. The French porno was still on in the background and the whole situation seemed even more ridiculous as I took it all in. In the basement of an older man from church, dressed in his sister's clothes, mouthful of cum and a French porno on. The tranny on the screen was laying across one guy's lap and getting spanked while she sucked the guy next to him. I stood slowly from the bed on the high heels and removed my panties. I left them hanging around the ankle of one shoe and waited for a second. Beside Mike's bed, a hairbrush was laying on the dresser. I picked it up and presented him the handle. "I guess I've been bad."
I saw Mike swallow hard and his soft cock jump. His breathing was picking up again as he moved to the edge of the bed. He didn't say anything, he just put his feet on the concrete floor and sat there. I moved to his side, hiked my skirt up and leaned over his lap.
For a moment, nothing happened. I half expected him to throw me on the floor, then throw me out. I started to get a very nervous, horrible feeling in the pit of my stomach. But then I felt his fingers glide over one of my exposed ass cheeks. It crept towards my crack and I felt a finger push on my asshole. I arched my back inwards to rock my hips forward and the back out, beckoning him to finger me.
He tapped his finger on my asshole and then withdrew that hand from my ass. I felt his free hand come up and hold my back down. The room exploded in the noise of the back of the hairbrush coming down hard on my ass. He didn't speak. He just kept on spanking my ass. He would stop every so often and run his hand over the heat coming from my ass. It burned like fire but I started humping his leg with my leaking cock. As he spanked my sissy ass, I reached under me and found his stiffening prick and freshly emptied balls. I started stroking him under me.
I heard the brush land back on the table but wasn't sure what to do until Mike said, "Get on your knees. Suck it again." I slid to the floor and put my hands on the tops of his knees. Both of his hands came to the side of my head and guided my open and wet mouth back onto his dick. I figured I had done alright the first time I let him mouth fuck me so I started doing that again.
He was hard again and very sensitive. He guided me at a slower pace this time. Long strokes up and down his shaft. When he would hold my head at the tip, I would swirl my tongue all over it like a starving dog on a popsicle. When he rocked onto his back, I'd dart my tongue in and out of his hairy asshole. Mike began to moan and breath heavier. His prick was rock hard now and I thought he was going to cum in my mouth again but instead he pulled me off it. I moved back as he stood and pointed at the bed. "On all fours, legs apart."