Just after my twenty-first birthday, I started tending bar a couple nights a week, more for something to do than for the money. In my mind, it was better to be hanging out at the bar making money than hanging out at the bar spending money. I worked Mondays and Tuesdays which were usually pretty slow nights, so I had time to hang out with friends when they came in and still keep up with customers. I also got to know a lot of new people, it was also a good way to meet and flirt with girls.

Randy, an older guy in his mid-fifties, was one of my regulars, he came in almost every Monday and Tuesday night and sat at the same spot at the end of the bar, drinking Wild Turkey on the rocks. I liked Randy almost from the time we met and, despite the difference in our ages, we spent a lot of time talking while I worked and he drank.

Randy was a good-looking guy with dark greying hair, a thick bushy mostly grey mustache, and thoughtful dark eyes. He was a big stocky man, well over six feet, with a slight belly, and enormous hands, toughened by years of working on ranches. It wasn’t unusual to see women flirting, and going home, with him. From what one of the waitresses told me, Randy also had a nice cock and knew how to use it. Apparently, he’d made her see God. Hearing her comments, suddenly changed the way I saw Randy. I’d known for a long time that I was bisexual and had enjoyed the experiences I’d had with a high school friend, but I’d never thought of other men as attractive or saw a man and thought I want him, but now, whenever I talked with Randy, I found myself becoming aroused and wanting him.

Obviously, I knew Randy was straight and nothing would ever happen between us, but that didn’t stop me from thinking about it, stealing glances at the bulge in his tight Wrangler jeans, and feeling myself get semi-hard as I tended bar. I even found myself fantasizing about him as I masturbated. I’d been versatile with my friend, but when it came to Randy, my fantasies were all about having this bigger stronger older man taking control and using me.

It had been three years since I’d been with a man and my yearnings to do it again were already high, these desires for Randy merely sent them into overdrive. I really didn’t know where to go or how to pick up men and I was terrified of what could happen if I approached the wrong man. Home computers weren’t even common at the time so online hookups didn’t even exist yet. I knew of a gay bar in town, but didn’t dare risk being spotted going there. All I could do is go home after a night of chatting with Randy, and stealing glances at his crotch, and stroking myself as I dreamed of him holding my hips and slamming his thick cock into me.

I was working Monday night after the Fourth of July weekend, it was very slow and the waitress went home at around seven and the few other customers were gone by eight, leaving me alone with Randy. We talked and joked for about an hour, I poured him another Wild Turkey and sat next to him at the bar. We continued chatting and as he laughed at one of my jokes, his big hand landed on my thigh. I froze at the unexpected intimate contact, knowing it was just a friendly touch but, wishing it was more. I knew it had just been friendly contact, but my dick didn’t and it instantly began to swell. We continued talking and a few minutes later, Randy’s hand returned to my thigh, this time however, it remained and started lightly rubbing up and down, getting dangerously close to my semi-hard dick.

I knew Randy was straight, but the way he was touching me now, certainly was not. For a minute I wondered if I had somehow drifted off into one of my fantasies and Randy wasn’t actually running his hand up and down my thigh. It seemed like it took forever, but I finally responded to his welcome contact by placing my hand on his thigh and doing the same. My eyes met Randy’s and he leaned in to kiss me as he pulled my hand onto the growing bulge in his jeans.

I kissed him back and stroked him through his tight jeans, feeling a little faint at my fantasy coming true. Randy’s hand left my thigh long enough to undo his belt buckle and open his jeans. My hand was inside fishing his rapidly swelling member out almost before he could get the zipper down. It had been a long time since I’d touched a cock other than my own and I’d almost forgotten how hot and smooth it felt. I hadn’t seen Randy’s cock yet, but I could feel it was thick and now hard as a rock.

Randy stood, leaning down to continue kissing as he undid my jeans and reached in to caress my hard cock and balls. I slid off my barstool and dropped to my knees, unable to wait any longer to taste the hard cock I’d been fantasizing about. Seeing Randy’s cock for the first time, I realized he was uncut, about seven inches long, and thick as a beer can. I licked my lips while stroking the skin back and forth over his wide leaking tip and leaning in to lick his big, low-hanging balls.

“Mmmm that’s good, lick those balls,” Randy moaned, shimmying his jeans lower and widening his stance to give me better access.

Hearing him moan like that caused an erotic shiver to run through me and I opened my mouth wide to suck one of his big nuts as I licked at it. The thought that I was at work and a customer could walk in at any time never entered my mind, the only thing concerning me, was the big hairy balls and hard cock before me. Randy’s thick fingers ran gently through my hair as I mouthed and licked at his scrotum.

“Damn that’s a hot mouth, now let’s see how it feels on my cock,” Randy groaned, pulling back and placing the wet tip of his hard cock on my lips.

I happily licked the tangy cream from the tip before parting my lips and sliding them over the wide flared head and down the thick shaft until it hit the back of my mouth. The taste and feel of a hard cock filling my mouth after such a long time had my own cock drooling precum as I bobbed on Randy’s thick meat. I wanted all of his hard cock deep in my throat. I’d loved deep-throating my friend and his cock was longer, but it had been a long time and Randy was so much thicker, I wasn’t sure that I could. I began sliding my lips up and down his shaft, taking a little more with each stroke.

Randy began moaning as his thick tip began pushing into my throat, making my desire to swallow him even greater. He was so thick, my throat had to stretch every time he slipped in. I increased the speed of my bobbing on his shaft until his entire cock was buried in my throat. Randy gasped as my lips reached the base of his thick cock. I pulled back to the tip of his shaft, took a breath and plunged back down until my nose was buried in his wiry pubic hair. I fondled his heavy balls and held him in my throat as long as I could before pulling off and doing it all again. I began alternating sucking and licking the flared head and swallowing the whole shaft until Randy grabbed my head and pulled back to shoot thick ropes of hot cum over my face as he moaned loudly. Blast after blast landed on my cheeks, nose, and open mouth.

“God damn!” he gasped, pushing the slimy tip of his cock back in my mouth.

I happily slurped the cum off Randy’s withering cock, finally savoring the taste of another man’s cum after going several years without. Randy gazed down upon my cum covered face as I let his now-clean cock slip from between my lips. He wiped his thumb through the slime running down my cheek and pushed it into my mouth.

“You sure know how to suck dick,” he grinned as I sucked his thumb clean.

Wiping more cum from my face, Randy helped me to my feet before pushing it into my mouth, then kissing me so we could pass his cum with our tongues. Randy’s tangy cream coated our tongues as they twisted together bringing me to new heights of passion. Randy’s large hands encompassed the rounded cheeks of my ass, pulling me against him and pressing my hard leaking dick against his spent member. His strong hands squeezed my ass and I felt a thick finger slip into my crack. I moaned into his mouth as it found my puckered entrance.

Randy spun me around and started kissing and nibbling my neck as he held my cock with one hand while gathering more cum from my face with the other. He stroked me slowly and pushed two fingers into my mouth. I sucked and slurped the cum from his fingers greedily and was left wanting when he pulled them from my lips. Soon enough, I felt his thick fingers, wet with my drool, slip between my cheeks and begin teasing my hole. I moaned and pushed my ass out, wanting them inside me. Randy’s rough hand slid slowly over my cock from base to tip as his fingers returned to my mouth to gather more lubricant for my hungry hole. Again, I sucked and licked at his two thick digits while moaning to show my appreciation for what he was doing to me. This time, I wasn’t disappointed when Randy’s fingers left my mouth, I knew where they were going and wanted nothing more at that moment. This time his fingers circled and teased my wet opening before one thick strong digit pushed its way inside. I pushed back, moaning and wanting it deeper.

“Mmmm that’s a nice tight hole you’ve got,” Randy growled, scraping his teeth along my neck.

I rocked my hips back and forth between the large hand gripping my dick and the thick finger stretching my ass, practically trembling with the pleasure I was receiving. I could feel the orgasm building in my loins and concentrated on holding it off as long as possible. I didn’t want this feeling to end, I wanted to find out what else Randy could do to me.

Another thick finger pushed in alongside the first, causing me to groan as I stretched around it. Both fingers pushed in deep and began twisting and wiggling inside me, sending jolts of erotic pleasure through me, causing my body to shudder in bliss. Randy’s fingers began moving faster with his hand on my cock keeping pace. I became a moaning shuddering puppet, controlled entirely by his masterful hands.

“That’s it baby, cum for me. Show me how much you like getting your ass stretched,” his voice rumbled in my ear.

I didn’t know what his fingers were doing inside me, but every time they hit a certain spot deep in my ass, my body convulsed and intense pleasure surged within my body. I reached back to grab his powerful thighs as my legs trembled beneath me, and noises I’d never made before flowed from my gaping mouth.

“Ohhh ohhhh ohhhh uhhh,” I gasped as cum flew from my throbbing cock and my body spasmed uncontrollably with the most powerful orgasm I’d ever experienced.

Randy’s fingers continued working my hole and he maintained his grip on my cock as my orgasm continued in waves, a constant stream of cum dripping from my cock until I could no longer support myself and fell back against his broad chest. His powerful arm held me against him as his lips nuzzled my neck and the hand that had been stroking my cock rose to my lips covered in cum.

“Taste yourself,” he whispered holding his hand to my lips.

Dreamily I licked my own cum from his hand until there was none left. It wasn’t until my breathing slowed and I’d thoroughly licked all of my cum from Randy’s hand that I realized, I was standing naked, in the arms of another man, in the middle of the bar where anyone could walk in on us and may have already done so as I was being jerked off while getting my ass fingered. I jumped and looked around frantically, grabbing for the boxers and jeans puddled around my ankles.

Randy laughed and squeezed my bare ass, “Just remembered where we are huh?”

“Holy shit! What if somebody came in? We’d be in deep shit,” I swore, jerking my pants up.

“Relax, nobody’s come in in hours,” Randy smiled, stuffing his cock back in his boxers. “And that was fun. I want more of that tight ass. Come over to my place Wednesday and we’ll do this right.” He wrapped me in his strong arms and kissed me.

I felt warm and protected in his embrace and never wanted it to end.

“I don’t want to wait that long,” I answered, reaching down to rub him through his jeans.

“Horny little bitch,” he chuckled, squeezing my ass. “You’ll just have to wait, imagine how bad you’ll be wanting it by then. I promise you’ll get all you can handle on Wednesday, so save your energy.” He kissed me again before downing the last of his Wild Turkey and walking out.

I stared after him with my dick already semi hard and thought, there’s no way I can wait til Wednesday. I busied myself wiping down the bar and closing out my till feeling both drained and excited. I’d never experienced such passionate and exciting sex with anyone, man or woman. Something about Randy and the way he’d taken control of my body had brought out previously unknown desires in me and I needed more of that from him.

I slept well that night and woke feeling rejuvenated and amorous. I began stroking my morning wood then decided to hold off and let my desires build until my appointment with Randy the following day. The entire day, people asked why I was in such a good mood and I just smiled in reply, while trying to suppress the inevitable swelling the real answer caused in my jeans. Randy came in and took his usual place at the bar, revealing no sign that anything had changed between us, until he discreetly slipped me a note on his way out.

The note had his address and time he wanted me there. Reading the note made my knees weak and my dick swell. I wasn’t sure I could continue to resist fulfilling my needs until then.

My workday on Wednesday was pure torture, I’d been successful in postponing my sexual release the night before, but it was impossible to focus on anything except what lay in store for me that night and I walked around with a half-hard dick all day. The clock seemed to stop completely as I waited for the day to come to an end. When quitting time finally arrived, I practically sprinted home to get ready.

Somehow, I managed to keep my hands off myself as I showered and dressed, by the time I knocked at Randy’s front door, I was basically a walking erection prepared for an epic release. He answered the door wearing his usual boots, tight Wrangler jeans, and western-style white shirt, looking every bit the strong masculine man he was. He greeted me with a broad smile and welcomed me into his home with a wave of his arm. As the door closed behind me, Randy’s large hand squeezed my ass and he lead me into the living room.

“Have a seat, What’re ya drinkin?” he asked, filling his glass with Wild Turkey.

“Turkey’s fine,” I answered, looking around the tidy room at its comfortable dated furnishings. From the bronze statues of bull and bronc riders to the National Finals Rodeo Posters on the walls, there was no doubt this was the home of a cowboy. In one corner, sat a tooled leather saddle Randy had won for steer wrestling.

“You never mentioned you were a champion steer wrestler,” I said admiring the saddle.

“That was a long time ago, back when I was young and dumb,” Randy chuckled, handing me a Wild Turkey on the rocks. “Come sit down.” He guided me to sit beside him on the sofa.

This felt weird to me. The times I’d been with Phil, we’d just met and got right to having sex, we’d never sat, had drinks and chatted beforehand. I’d expected things would go pretty much the same with Randy, but this felt more like a proper date. Randy sipped his drink and put his arm around me, which felt nice and I moved closer to him, liking the feel of his warm solid body against me. I took a drink and let my hand fall on his thigh. It was nice sitting with him like that as we chatted about his rodeo days, ranching, and our sexual histories. I confessed to having fantasies about him after being told of his sexual prowess. He divulged that he caught me checking out his package and to purposely creating opportunities for me to get a better look.

As we talked, I stroked my hand over his thigh and occasionally his concealed cock. While I enjoyed sitting and chatting with Randy, being so close to him was driving me mad with need and the crotch of my jeans was soaking wet from my cock drooling constantly. Finally, I couldn’t wait any longer and moved my hand to the bulge in his jeans as I turned and started kissing him. He wrapped me in his arms and me made out like horny teenagers, feasting on each other's mouths as we groped one another’s warm body.

“Let’s move this to the bedroom,” Randy said, breaking contact with my lips and pulling me up off the sofa.

He pointed the way and followed me down the hall to his bedroom. As we entered, his big hands slipped under the back of my shirt, around and up over my chest, pulling me back into his solid body. His fingers pinched at my nipples as his hot mouth found my neck, lightly biting and kissing my warm flesh. I ground back against him as I undid my belt and jeans. One large hand slid down my abdomen to push my jeans and boxers to the floor while the other pulled my shirt over my head. Once again, I was totally under Randy’s control, tingling with excitement, and waiting for him do whatever he wanted with my overheated naked body. A hand on my back pushed me to bend over the bed as another slipped between my legs to grip my slick overexcited cock.

“Spread that cute little ass for me, I want to see your tight little hole,”

Immediately, I reached back with both hands and pulled my ass cheeks wide apart for my commanding lover.

“Mmmm ain’t that pretty?” he said, circling his thumb around my twitching hole.

I couldn’t help arching my back and whimpering as he teased me open. When his thumb left, I expected it to return with some lubrication and enter me, instead, I suddenly felt Randy’s hot breath and then his tongue on my rosebud. I gasped at the feel of his wet tongue on my puckered hole. I’d never heard of nor imagined anyone doing such a thing but, I was rapidly becoming a fan of rimming. Randy’s tongue darted over around, up and down, driving me wild, all the while his strong hand stroked the length of my hard dripping cock. He was rapidly turning me into a moaning trembling drooling mess. Then, I felt his tongue pressing at the center of my wet eager hole and wiggling its way into me.

“Ohhhh God yesss,” I gasped as he began fucking me with his hot tongue.

Randy’s hand on my cock managed to keep me right on the verge of orgasm without tipping me over the edge. He was creating sensations in me that I never knew possible. With his slick tongue on my hole and his strong hand on my cock he was turning me into a quivering lump of desire. I pulled my cheeks as wide as I could and pushed back on his relentless tongue, greedy for more of what he was doing to me. His mouth left my ass and travelled up my spine, leaving love bites all the way to my neck.

“Is your tight little hole ready for some real stretching?” he growled, nibbling my ear and slipping a finger deep into my wet hole.

“Yes, please, I need it,” I panted.

“Get up on the bed,” he directed.

I crawled up on the bed, looking back over my shoulder to see Randy standing naked and stroking his thick hard cock. The sight was stunning, the thick nest of graying hair thinned and darkened as it lead down to his slightly rounded belly and his big balls swung freely between thick powerful thighs as his hand stroked the foreskin back and forth over the wide leaking tip of his thick hard cock. He was a mouth-watering bear of a man.

Randy easily flipped me onto my back and crawled over me, stroking my cock and biting my nipples as he moved up until he was straddling my chest and touching his cock to my lips. I slid my hands up and over his chest as I licked the precum from the tip before parting my lips and pulling him into my mouth. Being pinned under him with his thick cock filling my mouth, was thrilling. It felt like that was where I was meant to be. Pleasing him and pleasuring his hard cock.

Randy leaned forward, pushing his cock further into my mouth and throat. I gagged a little at first but, was able to get my reflexes under control and allow him to slip into my throat. He held my head and slowly pumped his hard shaft in and out of my throat. I was powerless to move as he fucked my mouth and enjoying every second of it. I gripped his ass and urged him to go deeper, wanting his entire length down my throat. Tears poured from my eyes as his heavy balls slapped my drool-covered chin. Randy moaned and grunted as his thick meat surged in and out of my stretched throat until he suddenly withdrew and sat back on my chest.

“Mmmm that mouth is good but, you’re not drinking my cum tonight,” he growled, breathing heavily and squeezing his thick member. “Now, turn over.”

Randy moved back so I could roll onto my stomach and present my hungry ass. Cold lube trickled between my spread cheeks and a thick finger began working it into my willing hole. I moaned, lifting my ass as Randy’s slick fingers plunged in and out, preparing my hole for his thick tool. I squeezed my eyes shut and prepared for the initial discomfort of penetration as his flared tip touched my eager opening. Considering the thickness of Randy’s cock and the vast length of time since I had been penetrated, I expected the discomfort to be significant but, Randy took his time easing into me. There was only slight discomfort as I stretched to accommodate his wide flared tip and then his hard shaft was sliding smoothly into me. I moaned quietly at the sensation of being filled again as Randy’s hips pressed against me.

“Oh yeah, that’s a hot tight hole you’ve got,” Randy grunted as he ground his hips against me.

I gasped at the feel of his thick hard shaft shifting inside me and pushed back, taking him even deeper. His big rough hands roamed across my warm flesh as he began sliding his cock slowly in and out of my stretched hole.

I’d only ever experienced the fucking of an eager inexperienced boy, but now, I was being fucked by a man. A man who knew what he was doing, and the feeling was unbelievable. I found myself moaning quietly with each long slow thrust as his fingers found my nipples and began lightly pinching and tugging. With every smooth stroke, I was experiencing sensations I’d never felt before and I hoped they would go on forever.

Randy’s big hand slid down my belly to fondle my cock and balls. As he grasped my cock I realized, I was leaking precum like a fountain.

“Mmmm that big cock is really making you wet,” he grunted, picking up the pace of his thrusts into my backside. “I knew you were a real slut,” he laughed, slamming himself hard into me.

I didn’t immediately realize, the high-pitched noises I was hearing, were coming from me as Randy held my hips in his rough hands and pounded his cock into me hard and fast. I was experiencing feelings I’d never imagined possible. Giving my body to this powerful older sexy man to use as he wished was a lustfully intoxicating experience. One that I wanted to go on, and on. My whole body began to tremble and quake as a steady stream poured from my wildly swinging cock.

My trembling arms gave out and I collapsed onto the mattress below. I felt Randy’s full weight on top of me as he began kissing and nibbling at my neck as his wonderful cock continued pumping slowly into me, grinding my own cock into the soaked bedding beneath.

“Mmmm, that’s such a hot little hole you’ve got. I’m gonna fuck you all night long,” he growled into my ear and continued grinding his cock into me.

I could only moan in response and happily receive his unrelenting thrusts. I thought of the waitress and wondered if she’d had this same experience, pinned under Randy’s warm body his thick solid cock pumping into her. Suddenly, I wasn’t just thinking of her, I was picturing myself as her, moaning away as Randy’s cock plundered my wet pussy. These thoughts set off another full-body orgasm. My fists clenched the sheets and I moaned loudly as my ass gripped the cock impaling me. Randy’s weight lifted off of me and his cock withdrew, leaving me feeling empty and craving its return.

“Hot little bitch,” he said, slapping my quivering ass, then flipping me onto my back. “I knew you’d be a good little slut, but look at all this cum,” he said, running his fingers through the slick cream coating my belly.

Randy pushed his cum coated fingers into my mouth, at the same time, sliding three fingers into my used gaping ass. I spread my legs further, welcoming his thick digits as I moaned and sucked at his thick slimy digits.

“You cum hungry little slut. You like that, don’t you?” he growled, twisting his fingers within my stretched ass.

I moaned my agreement around the thick fingers filling my mouth and sucked even more eagerly.

“Your ass is hungry for cum too, isn’t it? You want me to fuck your hot little ass until I fill it with cum too, don’t you?”

I nodded, reaching for his still hard cock and stroking it.

“Say it. Tell me what you want and I’ll let you have it, slut,” Randy grinned, pumping his fingers in and out of my needy hole.

“Fuck me, please. Fuck my ass and fill me with hot cum,” I begged.

With a devilish smile, Randy lifted my legs onto his broad shoulders and lined his stiff cock up with my hungry waiting hole. Leaning over me and pushing my knees back almost until they touched my chest, he entered me roughly, slamming his full-length home in one rapid thrust. I gasped at the suddenness of his entry and clutched onto his strong arms. His thrusts came hard and fast, causing me to wail and moan as he pounded me into the mattress. He began kissing me as hips continued pumping, slamming his thick shaft into me. My fingertips dug into his biceps as my tongue met his and I moaned into his mouth as the fucking went on.

I felt the tremors of another orgasm begin to build as Randy rose up and drove himself deep into me. His head went back and he grunted loudly, as I felt his cock twitching inside me. His twitching inside me was enough to push me over the edge as well. My whole body shook with the most intense pleasure I had ever felt. As the twitchings of orgasm subsided, Randy stroked his cock slowly in and out a few times before withdrawing and falling on the bed alongside me. His still-warm cum flowed from my used hole, soaking the bed beneath me. I don’t know that I’ve ever felt so satisfied in all my life.

As I lay there beside Randy, my breathing slowly returning to normal, I wasn’t quite sure what had just happened to me, but I was sure, I wanted it to happen again. Though I’d sucked cock and been fucked before, what I had just experienced with Randy was an entirely new experience. I’d never felt the things I had felt with him. I had certainly never cum without any direct stimulation of my dick before, and the orgasms had been so much more intense than ever before. I was both satiated and wanting to do it again.

“You might be the best piece of ass I’ve ever had,” Randy said, tweaking my nipple and kissing me softly. “Clean yourself up, while I make us another drink,” he added, leaving me alone with my thoughts.

My legs felt weak as I made my way to the shower, Randy’s cum still leaking from my battered hole and running down my legs. Staring at myself in the mirror while I waited for the shower to warm up, there was something different about me. I didn’t know what, but I felt like I was looking at a different person. I found myself pushing my chest together to make it look like I had tits and, even stranger, I felt a twinge of excitement as I did so. I suddenly wondered if Randy would like it if I wore sexy lingerie for him. I had worn pantyhose and panties once with Phil, but he wasn’t into it. Just the thought of dressing sexy for Randy had my dick coming back to life as I stepped into the shower. I felt rejuvenated after a hot shower. I had made up my mind to bring up the possibility of me dressing sexy for Randy. Even if he wasn’t into, thinking about it had me ready for another taste of his thick cock.

I found Randy sipping bourbon on the sofa where our night had begun. He picked up a second glass and offered it to me as I sat close beside him. The warmth of his flesh touching me was more intoxicating than the bourbon in my glass. I placed a hand on his firm thigh, near where his soft cock lay.

“In the shower, I was thinking,” I paused, unsure how to inform him of my Desires, “Would you…How would you feel about me…uh…wearing…dressing like a girl for you?” I stammered, losing confidence by the second.

Randy tilted his head to look at me and sipped his bourbon before answering. Even after what we had just done, I felt totally exposed and vulnerable. My heart was pounding in my chest and I was suddenly afraid of how he was going to react.

“Stand up, give us a little spin,” he said, twirling his finger.

“What…you want me to…”

“Just stand up and do a little turn so I can get a good look at ya,” he grinned, appearing quite amused by my hesitation.

I slowly got to my feet, feeling the flush creeping up into my cheeks, and stepped to the middle of the room.

“There ya go. Now, just slowly turn around for me,” he instructed, his dark eyes roaming over my naked flesh with a hungry stare.

I turned in place, giving him a full 360 degree view of my body. Strangely, though I could feel my cheeks growing hot with embarrassment, I could also feel myself becoming aroused.

“Slower, take your time and shake that cute little ass for me,” he smiled, obviously enjoying himself.

I turned slower, running my hands over my flesh the way I’d seen strippers do. When my back was turned to Randy, I pushed my hips back and gyrated for him. Showing myself like that, had me fully aroused, my cock even began leaking a little. I was overcome with the desire to display myself for him and make him want me. I bent over as far as I could, reaching back between my legs to run a finger over my exposed puckered hole.

“That’s my dirty little slut, let me see you finger your little pussy,” Randy growled behind me.

His words sent a shiver through me. I liked him calling me a slut and referring to my pussy. After the fucking he had given me, my finger slid easily into my hole and I made a show of plunging it in and out while moaning for him.

“Oh yeah, you’re gonna look good all dolled up like the dirty little slut you are,” he said, stepping behind me. “But first, I think I’m gonna have to fuck you again.”

A surge of precum fell from my swollen cock as I felt his big hands on my splayed ass. His soft cock flopped between my spread cheeks and began sliding through my crack. His hands roaming over my flesh, caused my body to tingle everywhere he touched. I could wait no longer, I needed his hard throbbing cock inside me. I turned while dropping to my knees and inhaled the entirety of his member in one gulp. I fed on his cock like it was my last meal and had him hard in no time.

“Impatient little slut aren’t you?” he said, his big hands taking control of my head. “Let’s find out  how much you can handle.”

Randy held my head firmly in place and began fucking my hungry mouth with gusto. Ramming his solid member straight down my willing throat. Faster and Faster he pumped his turgid shaft through my lips and down my throat. Tears streamed down my face, mixing with the drool running down my chin. All I could do was concentrate on relaxing my throat muscles and breathing through my nose. When Randy finally withdrew from my mouth, I was a gasping drool-covered mess. I was also disappointed that he’d stopped.

“On your feet slut,” he ordered, helping me up and bending me over his saddle.

With the thick coating of drool I’d left on Randy’s cock, there was no need for additional lube as he filled my ass once again. There was no gentle entry or slow stroking this time. He shoved his way in and began thrusting hard and fast. His rough treatment took my breath away and had me whining and moaning like a whore. It didn’t take long for my muscles to begin twitching as an endless stream of cum poured from my cock. I gripped the legs of the saddle horse and hung on for dear life as he hammered into me relentlessly. Everything around me became a blur I was only conscious of the hard cock reaming me and the pleasure it created with every hard thrust.

“Ohhh, fuck yeah, take it, you little slut! Take my cum,” Randy bellowed, as his cock twitched deep inside me.

I could feel his cum running down my legs as he slowly stroked his withering cock in my battered hole as I lay limply over the saddle, too exhausted to move.

“Mmm look at that sloppy pussy,” he said, withdrawing from my hole and spreading my ass wide.

I murmured slightly as he ran his fingers through the cum dripping from my hole and pushed it back inside me.

“Is that what you wanted baby?” He whispered in my ear as his fingers continued twisting inside me.

“Uh huh,” I managed, too tired to form words.

“Let’s go to bed and get some rest,” he said, kissing my neck and lifting me off the saddle.

Waking up the next morning, wrapped in Randy’s strong arms, was a new and incredible experience for me. The feel of his big warm body pressing against me felt comforting and safe. Of all the things I’d imagined would happen during my date with Randy, this wasn’t one of them but, it was amazing nonetheless.

Randy’s morning wood nestled between my cheeks was tempting but, I really needed to get home and change before work. I crawled out of bed doing my best not to disturb him and began to search for my clothes.

“What's the matter, too wore out for a morning quickie?” Randy chuckled.

“I really wish I could but, I’ve got to get to work,” I explained, pulling on my jeans.

Randy got out of bed and walked toward me with his hard cock in his hand. “All right but, I’m leaving town today and you can’t have another taste of this until I get back on Monday,” he smiled shaking his cock at me.

However tempting his thick shaft was, I couldn’t chance losing my job just to get my ass pummeled one more time. “I guess you’ll just have to wait til Monday for another taste of this,” I retorted wiggling my ass at him.

“Okay but, you’d better be wearing something sexy for me,” he grinned.

It wasn’t until a day or so later that I thought about Randy’s words. Had he forgotten that I would be tending bar on Monday night or did he want me to wear something sexy for him while I was tending bar? I really did want to dress like a sexy girl for him but, I certainly couldn’t do that while I was working. Though, the thought of wearing sexy lingerie and being his sexy little slut had me practically trembling with excitement. That excitement only grew more intense as Monday drew nearer.

By Saturday, I was getting extremely horny imagining Randy bending me over the pool table or fucking me in the storage room while customers at the bar waited for their drinks. I retrieved my box of lingerie, at the time I only had two pairs of panties and one pair of pantyhose with several runs in them, from the closet and laid them out on the bed. I looked at the meager collection in dismay, I had nothing sexy enough to wear for my man.

The thought of walking into a store and buying lingerie was daunting. I just knew the clerks would see by the size I was buying that it was for me and I would be outed as a cross-dressing weirdo right there in the store. Nevertheless, I sat in the mall parking lot mustering up the courage to walk in and buy something sexy to wear for Randy. However, my newly found courage quickly dissipated upon seeing a girl I went to school with working in the lingerie section. I slipped away without being noticed and wandered through the mall for a bit before trying again at a different store.

This time, I scanned the whole store for people I knew before making my way to my desired objective. I couldn’t help feeling a little embarrassed and awkward browsing through the racks of bras and panties. I was tempted to just grab something and get out as quickly as possible but, I desperately wanted something that would make me look and feel sexy and feminine. There were so many colors, styles, fabrics, panties, teddies, bras, nighties, so many choices, it was overwhelming. I was about to give up when I saw it, just what I had in mind, right there on a mannequin torso at the end of the aisle a sheer pink teddy trimmed with white lace. I reached out to touch it, it felt so smooth a sensuous, I had to have it. After a bit of searching,I found, what I hoped, was the right size and headed for the register so happy with my find that all trace of embarrassment and awkwardness was forgotten.

The clerk smiled politely as she removed the tags and carefully boxed my prize. “I loved this one the minute it came in. It would look really sexy with white stockings. Does she have some?”

I was so distracted with thoughts of Randy seeing me in the teddy, her words barely registered. “What, sorry, I didn’t hear what you said,” I apologized, embarrassment creeping back in.

“Does your girlfriend have white stockings to wear with this?” she repeated.

“I… oh I don’t know,” I stammered in reply.

“We have some right over there, if you want to get those too. White would go well with this but, pink would work too,” she explained, indicating a hosiery rack nearby.

I nodded, stepping toward the rack and the clerk followed. “These are my favorite, they’re more expensive but, they don’t snag and run as easily as the cheaper ones,” she said, taking a package from the rack.

“Oh okay these ones then,” I answered, my dick starting to leak a little as I imagined the smooth stockings sliding up my legs.

Frankly, I was shocked when she told me the total for my purchase. I had absolutely no idea how much it cost to be a sexy girl. I handed over the money and hurried home with my gift wrapped package. After opening the package, I carefully laid its contents out on the bed. Just looking at my first girl clothes had me in a highly aroused state. Removing the stockings from their packaging and feeling the silky smoothness on my skin, I decided sliding them up hairy unshaven legs just wouldn’t be right.

I ran myself a warm bath and prepared to shave my legs for the very first time. I quickly discovered, shaving one’s legs wasn’t nearly as simple as television commercials would lead you to believe. I was quickly learning just how complicated being a girl could be. It took four tries with the razor to get my legs completely hair free, every time I thought I was done, I’d find another spot or two that I had missed and would have to give it another go. Finally finished with my legs, I considered the nest of curly hair surrounding my cock and thought I’d give it a little trim as well. Another endeavor that turned out to be more complicated than I ever would have thought. I could never quite get trimmed evenly into the nice little landing strip I’d planned and before I was done, my whole pubic area, including my balls, was shaved smooth. Not quite what I had planned at the beginning but, oh how sexy and smooth it felt. Just perfect to go with my new lingerie.

I’d always loved the feel of pantyhose but, I was not prepared for how good it felt sliding my new stockings up smooth freshly shaven legs. The stockings the clerk had recommended were so silky smooth sliding over my smooth skin, it was the most sensual feeling I’d ever experienced. Getting the teddy on and arranged properly took a bit of fussing and the thong back pulled up between my cheeks was another first. When I finally had everything in place and looked at myself in the mirror, all of the struggles and fussing had paid off and I loved the way I looked. Of course, I needed a little makeup, my hair needed some styling, and there wasn’t much to fill out the cups of the teddy but I was still quite happy with what I saw. Seeing myself like that only heightened my arousal and Randy wouldn’t be back for another two days.

Not having a full-length mirror, I set up my video camera and connected it to my television in order to get a better look at myself in my girly new outfit. Of course, it didn’t take long for my posing to get more and more explicit. It also got harder and harder to hide my excitement as it wouldn’t remain within the confines of my teddy. I came hard, fingering my pussy for the camera while jerking my swollen member. As I lay panting, and looking at myself on the screen, I couldn’t believe how turned on seeing myself dressed like this had made me. I couldn’t wait to see what it did for Randy.

The following day, encouraged by the success of my previous mission, I returned to the mall. Before I had sheepishly run out of the first store, something had caught my eye. I could only hope a different clerk was on duty today. A different girl was at the counter when I arrived and I quickly made my way to the display I’d noticed along the back wall. I could feel myself becoming aroused as I stood there ogling the object of my desire, a sheer, crotchless, full body stocking. I reached out to feel the silky smooth material stretched over the mannequin. I trembled a little at the thought of my whole body ensconced in such heavenly silkiness. I had to have it. The only question was which of the four available colors. Just as I plucked the black version from the display, I heard a familiar voice beside me.

“Dan, I haven’t seen you since graduation. How are you?” Cindy Frandsen asked.

“Cindy, hey where’d you come from?” I answered, with a knot forming in the pit of my stomach.

“I work here. What are you doing here? Getting something sexy for your girlfriend?” she asked eyeing the package in my hand. “Oh these are sooo sexy, I have a black one and a blue one,” she winked. “So who’s the lucky girl, you’re not still with Camille are you?”

“Uhh no, we didn’t last very long after graduation,” I answered, feeling awkward and wanting nothing more than to get out of there.

“Oh, that’s good. She always such a B I T C H. Must be serious with this girl if you’re buying lingerie for her. Is she someone I know?”

“I doubt it, we met at the bar where I work,” I replied, not knowing what else to say.

“You work at a bar? Which one? Maybe me and Heather will come see you. You remember Heather, don’t you?

“Of course I remember Heather, we went to prom together.”

“That’s right! I forgot about that. We had so much fun that night and I know you and Heather had fun,” she giggled and winked.

“Uh yeah, you two should come by some night. I work Mondays and Tuesdays, it’d be good to catch up with both of you,” I answered, conveniently leaving out the name of the bar.

“Oh yeah, it’ll be so fun getting together, what bar was it again?”

I had to tell where I worked but, she helped me pick out a matching G string and give me her employee discount so it wasn’t all bad. Since Cindy naturally assumed I was buying a gift for a girlfriend, I went ahead and asked her to recommend a nice perfume as well. I wasn’t thrilled about telling Cindy where I could be found, not because I had anything against her, but because I was concerned about my lie being exposed. Even so, seeing Heather again might be fun, as long as I didn’t have to explain who I had been buying lingerie for.

The body stocking looked and felt every bit as good as I had imagined it would as I posed before the video camera once again. Strangely, as I teased my hole and stroked my cock, memories of Heather’s soft skin interrupted my thoughts of Randy’s hard cock. I recalled the taste of her sweet juices as I sucked them from my fingers and the taste of Randy’s thick cum shooting into my mouth as I sucked him. I imagined her sucking me while I sucked him and him fucking her as she sucked me while I licked her. I came hard to the thought of fucking her while he fucked me. I’d never had thoughts of being with a man and a woman at the same time. For some reason, I’d always kept the two separate in my fantasies. Suddenly here I was in women’s clothing fingering my ass and stroking my cock while fantasizing about both Heather and Randy. This became my new favorite fantasy. I loved imagining all of the possible combinations, including me and Cindy wearing our matching body stockings while Randy fucked us both.

Excitement began to build as I got ready for my shift at the bar Monday night, I just hoped this wouldn’t be the night Cindy and Heather dropped by to see me. It was busy with the Monday Night Football crowd and Randy strolled in at eight o’clock, as usual. I had to calm myself and try to act normal when I saw him, even though what I really wanted to do was grab his dick and stuff it in my mouth. Though I managed to maintain the appearance of normalcy, my level of arousal continued to climb with every passing minute. When the game ended and customers began to filter out, I was able to spend more time with Randy and it became harder and harder to hide my desires.

As far as Randy was concerned, he gave no hint whatsoever that anything had changed or happened between us. However, he did occasionally throw in a suggestive comment or two, I think just to see if I would react. I did not react, outwardly at least. The last customer, other than Randy, left shortly after eleven o’clock and we could finally talk without censoring ourselves. Randy wasted no time, telling me he’d been waiting all night to get my lips wrapped around his cock. I laughed it off asking if he thought I was that easy. He only smiled as he knew that I was.

It was too early to lock up so I busied myself restocking the bar and washing glasses until midnight. I hurried to lock the door at exactly midnight then slipped into the storage room where I stripped off my clothes to reveal my body stocking and black G-string and spritzed myself with perfume. Stepping out of the storage room, I called to Randy with a slight tremble in my voice. The few seconds it took for him to turn and look at me seemed to last forever as I nervously awaited his reaction.

“Well, look what we have here,” he said with a devilish smile. “What’s your name, darlin?” he asked as I approached.

“I’m Danielle,” I answered as his hands settled on my hips and pulled me in for a kiss.

I melted into his warm body as his big hands encompassed my ass and squeezed. He feasted on my mouth as his hands roamed over my body. The feel of his big warm hands caressing me through the thin silky material was exquisite. Wrapped in his hungry embrace, I was feeling more feminine by the moment. I found his thick member and stroked him through his jeans feeling him thicken as I did.

Randy scooped me up in his arms, carried me to the pool table, where he set me down. Our tongues continued to duel as I spread my legs and his fingers slipped into my panties.

“Mmmm all wet for me already, little slut,” he growled feeling the pre cum soaking my panties.

I simply moaned in reply and reached for his belt. I had his jeans open and down to his knees in a flash and wrapped my fingers around his hot hard cock. The heat of his flesh in my hand caused me to tremble with desire and passion. I kissed him harder wanting him to consume me entirely with passion.

Randy lubed my puckered hole using my own precum and pushed a finger in. I moaned into his hungry mouth and stroked his cock as he repeatedly gathered precum from my leaking dick and pushed it into my waiting rosebud. I lay back on the table, lifting my legs high and spreading them wide, offering myself to him.

“Fuck me, I need you inside me,” I breathed, pulling my knees back toward my chest.

Randy half smiled, pulling my G-string aside and lining his cock up with my waiting hole, “Little slut wants my big cock in her tight little pussy?”

“Yes, please, please fuck your little slut,” I begged.

As his flared tip began stretching my eager opening, his warm lips descended on mine resuming passionate kissing. Our tongues twisted together as his thick shaft pushed steadily into me. I sighed into the warmth of his kiss at the feeling of being filled once again. I’d been longing for this since the last time we were together and now, wrapped in a silky smooth cocoon, it was even better than before. With every move of our joined bodies I felt the silky caress of the thin stocking against my smooth flesh. I was in ecstasy, moaning with every thrust of Randy’s strong hips. I could feel myself becoming more feminine with each stroke of his steely cock.

Randy was in no hurry, kissing and caressing me as his thick member pumped steadily in my willing boipussy. He caressed my smooth legs, pinched my hardened nipples, and stroked my leaking clitty all while maintaining contact between our joined lips and stroking in and out of my heated hole.

“Mmm Your tight little pussy feels so good, I’m going to fuck you all night, you little slut,” Randy growled, picking up the pace of his thrusting and gripping my legs to push them further back.

“Yes, Daddy, please never stop fucking my pussy,” I moaned and began tweaking my own nipples as he thrust into me.

Randy began pounding his cock into me hard and fast making me moan louder as I felt the contractions of orgasm beginning in my belly. He kept pounding my clenching hole as I trembled and shook in ecstasy. I cried out, if I could have formed words, I would have said, "Oh God, I’m cumming, I love your cock, keep fucking me, I’m cumming." However, what actually came out of my mouth was an entirely unintelligible string of guttural moans.

Randy suddenly withdrew his throbbing cock, pulling me off of the pool table and placing me on my knees before him. “Taste your hot pussy on my cock,” he ordered, sliding his hot wet cock into my mouth.

I clung to his hips for support as I eagerly bobbed my mouth on his hard cock, tasting myself on his manhood. I slurped the length of his cock, wanting to please him and feel his hot cum shooting onto my tongue once again. He grabbed my head and started fucking my mouth, the same as he’d just fucked my ass. I was helpless to do anything but, take the length of his hard shaft as it pushed into my throat over, and over again.

“There you go, little slut, there’s the cock you wanted,” he grunted.

Suddenly, he jerked away and grasped his throbbing shaft, “Oh no, this load's going in your pussy. Get up and show me that hot little cunt,” he ordered.

I slowly stood on unsteady legs and bent over the pool table, reaching back to spread my ass wide for him. “Fuck me, Daddy.”

The words were barely out of my mouth before his full length was buried in me once again. There was no slow stroking this time, he grabbed my hips and began hammering into me immediately. He pounded me without let up, my stretched hole gripping his hard cock on each demanding stroke. The sound of our flesh colliding drowned our passionate moans and grunts. I pushed back to meet Randy’s eager thrusts wanting him deeper in me and soon I was trembling in orgasm yet again. I cried out as my hips shook and Randy bellowed as he slammed hard into me. I moaned at the feel of his thick member pulsing inside me, filling me with his hot seed. His cock remained inside me as he bent to kiss my neck and catch his breath.

“You are one hot fuck,” he murmured in my ear.

I wiggled my ass on his slowly softening cock and felt his cum begin to trickle out around it.

“Mmmm you can fuck me anytime you want,” I smiled, loving the feel of his big warm body pressing down on me.

“Then let’s get cleaned up and go to my place so we can do it again,” he said, kissing my neck and letting his cock slip from my used hole.

A flood of cum ran down my legs as I dropped to my knees and took his cock in my hand.

“Better start with this,” I grinned and ran my tongue up the length of his soft cock.

I took my time licking and sucking Randy’s cock clean and he was beginning to swell again when he stopped me.

“You keep doing that and we’re not going to make it to my place,” he said, pulling from my mouth.

Hurriedly, I cleaned up the mess we’d left on the pool table and hoped no one figured out what the stains on the felt actually were then pulled on my pants and dashed out the door.

On arriving at Randy’s, I quickly changed into my teddy and stockings and modeled them for him. He must have liked what he saw, because he pulled out his cock and slowly stroked it while watching me. I couldn’t resist and was soon on my knees before him, sucking the cock I loved so much. I loved the sound of his quiet moans as I sucked his cock and large hairy balls. As his cock began to twitch and I prepared to taste his cum, he scooped me up in his arms and carried me to his bed for another long slow fucking.

Over the next six months, I expanded my lingerie collection and hooked up with Randy at least once a week. Randy bought a bigger ranch and moved to Montana. We hooked up a few times when he came back to town and I visited him at his ranch once but, our regular fuck sessions were over.

Our affair was short-lived but, had long-lasting effects on me. It left a lasting attraction for older burly men and cemented my desire for wearing sexy silky lingerie. Though Randy wasn’t my first, he did show me how amazing sex with another man can be.