I've been meaning to write this story for some time. It could have easily happened had I taken the initiative but instead, I chickened out. It remains a favorite fantasy of 'what if' though. I hope you enjoy.
Saturday evening and I'm sitting in the living room of my small mobile home. Nothing to do but cruise the porn sites on-line. The usual buttons are being pushed on my libido and I find myself looking at the strap-on dommes sites, the f***ed crossdressing, f***ed bi, shemales, fucking, sucking, licking. The computer desk sits across the room from the front door, the front door that has the little tiny trailer front window in it. I don't know if anyone can see in but I'm not expecting company so fuck it. Pants pulled down, cock in one hand, mouse in the other.
I'm stroking it slow and enjoying a movie clip. A beautiful black haired shemale is on all fours getting fucked in the ass. Her legs wrap around the stud behind her, high heels pointed up.
I nearly jump out of my skin when there's a knock at the front door. Pants fly up, window closes, boner gets tucked to the side. Who the fuck is this? And does my shirt cover the huge erection jutting out of my left pants pocket?
I go to the door. It's Ron. He's about half in the bag as usual. He waves a DVD case in the air and a bottle of Jack Daniels in the other. "You've GOT to see this movie. It is the funniest thing I've ever seen. And as soon as I saw it, I knew I had to bring it over for you to watch."
My heart was still racing and my erection was subsiding. "Uh, yeah sure." What was I going to say? 'No, I'm busy looking at porn, come back in 20 minutes..'
Ron busied himself loading the DVD player while I fixed us both a cocktail. "Where's everybody else tonight?" I asked Ron.
"Out of town, other stuff, who cares... this movie is fucking hilarious."
Being a small living room in a small mobile home, I only had room for two chairs. Ron took one and I took the other. The movie started and Ron and I sipped our drinks.
The thing I haven't mentioned yet about Ron is that he's one of the few openly gay men that I know. We've worked at the same company for about year and through various bar outings, camping trips, etc, I had gotten to be decent friends with the guy.
The JD warmed my stomach but my mind remained on the porn sites. The thought kept cycling through my head, 'what if I had been wearing my lingerie and playing with my toys when Ron came by? What if he hadn't knocked and just walked right in?'
Ron wasn't attractive or unattractive. He was just a guy that I knew. And for the most part, I just like being with girls. But, here was Ron and it had been too long for me. I also knew that in this small town, he was also pretty desperate for some action... or at least that's all he usually talked about once he was really liquored up.
Several times during the movie we had to stop and freshen up our highballs. They were going down smooth and the movie was entertaining. By the time the movie ended, I had a healthy buzz and the demons were whispering louder in my ear.
The back of my neck felt hot as I spoke. "You know Ron, I've got something in the back of the trailer that I've never shown anyone before. I think you might appreciate it though. If you can keep a secret."
"If it's something i*****l," Ron said as he crunched a piece of ice, "I don't want to know anything about it."
"Nothing i*****l," I promised. "But it will take me some time to dig it out of where I have it hid. Why don't you check out the extra features on the DVD while I go get it."
Ron shrugged alright and started thumbing through the DVD menu.
"But remember, NOBODY can know about this."
Ron made the locking key motion across his mouth and then drained his drink.
My heart felt like it was about to explode. My hands trembled slightly and my brain was working overtime trying to process the risks versus the rewards. The whiskey was working its magic and the hellhounds in my mind were way off the porch.
In the bedroom, I unlocked the storage container with all of my sissy clothes. Quickly I undressed and began picking out what to wear. My rock hard 7 inches throbbed with every heartbeat. This is either going to be incredible or incredibly awful I thought as I began to dress.
First, the garters and black thigh highs with the line up the back. Then the black lace panties over those. Next I slipped on my 5 inch black stilettos with the little black ankle straps. On went my little one piece black dress. I thought about tucking my cock back but decided against it. Instead I let the front of my dress stand at attention and thought this might provide sufficient bait. I knew Ron had said over d***ken conversations that he liked his lays to be manly but given his limited options here in Smalltown, USA and the fact that he had a buzz on... well... I hoped he took me up on my proposal or I'd have to leave town or fake my own death. Or both.
I walked carefully down the hallway, holding on to the sides of the wall so that I didn't stumble in my fuck me pumps. I was tall and thin and many women had told me over the years that I had a nice ass. My face wasn't quite passable but I figured that would work to my advantage tonight.
As I rounded the corner into the living room, I stopped and leaned against the corner, cocking my ass off to the side. Ron looked up and froze in mid sip. His eyes were wide and his breathing stopped for a second. "Here's the deal," I said, trying not to let my voice waiver. "If you tell ANYBODY about this, I'll flat out deny it and tell everyone you're a liar. And then I'll probably have to kick your ass later." Ron remained motionless.
"However," I said as I walked closer to him, "if you accept my terms, you're probably in for a very fun night."
"What are the terms?" Ron said quickly.
"Well," I began, "it's a pretty simple deal. You tell no one. There is no kissing. I do not want you to suck my dick, I do not want to fuck your ass. This is a one time deal unless I approach you again. Other than that," I said with a smile, "you can pretty much have what you want."
Ron swallowed hard. "Uh... sure. I had no idea... "
"And we're going to keep it that way for everyone else," I said as I cut him off. "Also, since we all just signed up for life insurance at work... and had to take an AIDS test... which you passed, yes?"
Ron nodded yes.
"Then tonight, you can fuck me bareback."
Ron's mind was working so hard to keep up that I thought that I actually saw smoke come from his ears."
"But I would prefer that you cum in my mouth. I've always fantasized about what it would be like to have a big hard cock shooting wad after wad into my mouth."
Ron didn't move. He didn't know what to do next. I continued to 'top from the bottom'.
I sank to my knees and then said softly in a more effeminate voice, "While you're processing all of this, why don't you go ahead and take off your clothes."
Ron was up like a shot and shucking clothes like he was on fire. In less than a minute, he stood before me buck naked with a throbbing erection. I was hoping that he had a huge cock but one that wasn't so big that it would tear me in half. His cock was roughly the size of mine except maybe an inch bigger and a little more wider. I patted the seat cushion and Ron sat back down. I scooted closer and put a hand on each of his knees.
"I want you to fuck my mouth. I want you to fuck my ass. I want you to pull it out of my ass and stick it in my mouth when you cum. Make me lick it off. Clean it for you. I want you to spank me. First over your knee, then with your belt. I want to feel your hands on the back of my head pushing me down when I suck you. I'll lick your balls. I'll lick your ass. I am your filthy little slut tonight Master. And for the rest of the evening, the only thing I plan on saying is, 'Yes sir.'"
With that I leaned forward and engulfed as much of his cock into my mouth as I could. I had planned on being seductive about it and licking the head and nibbling the shaft... but when it came time to do it, I just wanted to know what it was like to have a mouthful of dick.
Ron's hands immediately found the back of my head and his hips began to writhe up and down. I had never sucked a cock before so I concentrated on keeping my lips pulled over my teeth. With one hand I stroked the shaft and with the other one, I played with his overloaded balls. Every so often, he would push hard on the back of my head and I would go all the way down. His cock wasn't long enough to choke me but it did go all the way to the back of my throat.
My head bobbed up and down and his cock continued to get harder in my mouth. One hand continued to work the shaft and the balls in my other hand started to contract. As they loaded up approaching orgasm, I slid the tip of one finger back and ran it across the outside of his asshole. The hand on the back of my head pushed hard again, I felt his legs tighten and soon shot after shot of semen flew into my throat.
"Holy shit," was all Ron could manage to say.
I remained kneeling in front of him with his cock in my mouth. I had hoped to actually taste the cum but in his exuberance, he had dumped his entire load down my throat. I licked at some of the cum remnants near the tip.
Ron stood up suddenly and walked quickly to the bathroom. There I could hear him peeing. I remained on my knees and looked around the living room. Nothing seemed real. Nothing seemed relevant.
Ron returned and sat down heavily in the chair. "Wow," he finally exhaled. "That was fucking amazing."
Having just sucked my first cock, I wasn't sure what to do next. But Ron was becoming more comfortable with the whole situation.
"Well," he said and spread his legs apart, "get your little slut ass up here over my knee."
"Yes sir," I smiled.
Before bending over his knee, I pulled my panties down to my knees and my dress up around the small of my back. Ron grabbed the back of my hair as I leaned over and before I could even get settled, blows were beginning to reign down on my ass cheeks. As each loud pop filled the air, my own throbbing hard on drove down between his clenched thighs. "Count'm slut, you're getting twenty."
I counted aloud but was so amped by the whole experience I didn't really feel any of them. At the end of 20, the heat was spreading through my ass and his rough callused hand began to caress each cheek. Moving my ass back and forth and grinding against his hand with my ass and against his crotch with mine, I soon felt a finger begin to explore my back door.
"You're a tight little bitch," he said and rammed one home dry. I groaned in pleasure as he began to dry fuck me with his finger. "We better get some lube though or I'll make a mess of you."
Standing quickly I tottered into the kitchen on my high heels and retrieved a small bottle of vegetable oil. Without saying a word, I poured a small amount in to my hand and began to massage it into his returning erection.
Ron closed his eyes and sighed heavily. His dick was now fully erect again and his hips were grinding up to meet each stroke of my hand. "I think I'll fuck you right here on the floor, " he said. "Get on all fours cunt."
Kicking off my panties, I immediately got on all fours and arched my ass in the air as high as it would go. Lowering my head gave him even more access and the cool air of the room swirled around my red hot ass.
Ron got behind me and put both hands on my hips. I curled both feet around his legs and pulled at him, beckoning him to take my sissy cherry. His oily hard dick found its target and he began pushing into me. I had used dildos many times before and knew the best thing to do was to relax and take it all in one shot.
As Ron's dick lined up against my asshole, I took a deep breath, relaxed and shoved back. The whole length of it hit home and his balls slapped against mine. Ron let out a deep grunt and mumbled something about 'so much for taking it easy the first time' and then began to slowly ease back out of me. The pain was already subsiding and as he shoved forward again, the tip of his cock began its long massage of my prostate.
His paced quickened and I could hear him breathing heavily. When I could, I would clinch my sissy ass lips down on his cock and give him an extra squeeze. Every time I did, it was spurring on a horse as his pace quickened and the thrusts became more violent.
He lasted much longer this time but after a good hard fucking, he announced that he was going to cum and pulled out. I quickly spun around and began jacking his cock towards my open mouth. I was going to taste it this time. Rope after rope of jism exploded into my mouth and his hand held onto a clump of my sweaty hair. After the last dribble of cum fell, Ron collapsed into the chair behind him and I crawled forward with my open mouth leaking cum and drool.
Grabbing his spent tool, I spit the cum back onto it and began licking it off, swirling it around in my mouth. Gathering it all up at the head, I swallowed it all and then deep throated him, tasting my own ass mixed with his cum.
My ass was sore in all of the right ways and the taste in my mouth had my own cock leaking. "I don' think I can cum again right now," Ron said. "But I have an idea for you. Stand up and turn around."
"Yes sir," I replied and did as I was told.
Ron came up behind me and stuck two fingers in my oily ass. I jumped slightly but took them both all the way to the last knuckle. "Jerk off into my hand," he said holding his other hand in front of my own straining cock. "And then I'm going to make you eat that too."
I began jerking my own cock quickly and within seconds, I dumped the biggest load I had ever blown into his hand. "Now, lick it up," he said.
Having cum, the demons had subsided and I no longer felt quite as unhinged. I stared at the handful of cum and hesitated.
"Bend over," he said, and I bent over putting my face closer to the pile of jizz.
I hesitated still.
I heard clothes rustling behind me and then heard a whooshing sound right before the belt made contact with my poor abused ass.
"I said lick it up you fucking cum slut," he said. The belt fell again and I yelped.
But still I didn't.
The next blow landed harder and the next one harder than that. Finally, as the fire on my cheeks reached too high a temperature, I sobbed, "Yes, sir" and began eating my cum out of his hand. The whole time my tongue dug through the calluses in his hand, the belt continued to fly.
After I had swallowed the last of my own spunk, the hand was pulled away from my face, and I collapsed spent into the other chair.
I looked up at Ron who was again sitting with a broad grin across his face.
"Remember," I said seriously now and with a hint of menace, "not one fucking word to anyone. Ever."
Ron nodded and continued smiling. "Yes sir," he said with a laugh, "yes sir.".