3 comments/ 18329 views/ 0 favorites Loser By: flawed_ethics I look in the mirror. My hair is combed back. The press of my shirt looks strong. I grin at myself, checking my smile. Everyone likes a good set of teeth. There's nothing more embarrassing than chatting it up with someone, only for them to point out you've got something stuck between them. Not tonight though. Everything's falling into place. I dare say, I'm looking damn handsome tonight. I can feel her eyes on me though. Behind me, mocking me. "You don't actually think you're going to get anywhere tonight, do you?" With a flick of the switch, the lights are off. Coat over my shoulder, I grab my keys and make my way out to my car. I've got a double date tonight with a good friend. I kinda like the girl, and I'm riding high on my confidence. Why should I listen to her? "You're going to blow it. Not like I need to tell you. Just try not to make a scene this time, or you'll never get over this." Her words seem shrill to me, but whatever. She's just jealous, I remind myself. Tonight, I'm leaving it all behind me. I meet my friend at the diner's bar. Alex is sporting a look tonight too. It's easier for him though. He's got a nice build. Solid jawline, strong hands, and an agreeable personality to boot. He's everyone's friend at the office. Outside the office, everyone's friends with him. With the ladies, maybe even moreso. My martini helps to relax my nerves, and soon we're making small talk about the office. The new guy at work, as well as some of the new corporate policy changes that some of the higher-ups have been discussing as of recent. It's too easy to talk about work every waking hour, though. Our attention soon turns to the possibilities with and Jenny and Allison. "She's been interested in you," Alex remarks. "She's been asking Aly about you these past couple of days. They know we're good friends, and Aly has been asking what your hobbies are, and what you think about her." "What'd you tell her?" He looks at me, as if he were surprised I would ask such a question. After all these years. "I told her the truth. You're a good guy. I'm telling ya, you two should be able to get something going tonight. I have a sense for these things. You two click well." We both take a swig. No sooner are the drinks down our mouths that we hear the friendly hellos of our dates. We turn to meet them. They look stunning. Allison is wearing a royal blue silk top with a complementing skirt, but I'm not with her. My eyes are on Jenny. She has on a conservative but alluring black dress. The fabric comes down to knees, allowing some of her legs to show. The straps allow for the for her chest to stand a little more prominently. Her coat is folded over her arm, and already I am entranced by her elegance. She's smiling back at me. I can tell she likes what she sees. After greeting each other, we find the headwaiter and let him know our party is ready. We order the girls their drinks at the bar, and soon enough the wait-staff lets us know our table is ready. I cordially let Jenny ahead of me, and help her to her seat. In a genuine voice, she thanks me. I catch a reassuring look from Alex. The ambience is intimate and inviting. I can do this. The conversations quickly take off. We go from how they're doing to how the day has been for them, and soon enough Jenny and I are talking about her cat's misadventures this morning. Alex and Allison are off on their own conversations. It's between us now. We go back and forth, between our similar childhood disasters at piano lessons to our more recent free-time hobbies. Our food arrives. Everyone's ordered modest-sized dishes, which works to our advantage. The conversations keep rolling. Dinner is merely a device for the evening. She has a look in her eyes. Like she's peeling back layers of me, delighted by what she finds as she digs deeper. She's warm and inviting. I feel a resonance with her. It's like she's what I've been looking for all this time. Dinner wraps up. Alex and I split the bill, trying to show chivalry is not yet dead. Plenty of energy still exists within our group, and we head a block down to a little club we know. The band tonight is lively, and we're all eager to dance. Jenny motions deliberately for her coat. I help her, sliding the sleeves over her arms. It brings me closer to her, and she grows happier with my demeanor. We arrive, and the band is underway. The cover paid, we find an open table. The girls head to the bathroom to freshen up, but not before Alex and I get their drink orders. "Going pretty good, from what I can gauge," Alex says to me as we wait at the bar. "I told you - you two would hit it off. Like I said, I have a knack for these types of things." "She is wonderful, isn't she? Do you think there's a chance?" "Dude, don't even think like that," Alex cautions me. "You're having fun, right? Why weigh yourself down? You two are having a great time, so just keep having fun. It'll work itself out. You'll see." We return to the table, and soon enough, the Jenny and Allison return too. Our attempts at conversation are hampered by the loud music, but we did not come here to talk. After a few songs, Jenny head out to the dance floor. A nervous wave crashes over me as mix in with the other dancers. Memories cry out to me that I am not much of a dancer. It doesn't seem like Jenny minds though. She's smiling anyways, keeping her eyes on me. I can't help but keep my eyes on her. Her gaze, new and intriguing twenty minutes ago, is suddenly all-too familiar. Dancing to the music in her black dress, her moves quickly mesmerize and enchant me. Every bounce of her hair, every graze of her arms against mine etch an image in my head. Her hips sway as her arms click to the beat of the music. It's around then reality catches up to me. I start asking myself why I'm up here with her. How does a guy like me end up with a gal like her? I can't measure up to her. Her degrees, her hobbies. I'm in over my head. My rationale reminds me of the problem: she deserves better. After all, She has better. Jenny is even quick to notice that I'm distracted by my own thoughts. She moves in closer to me with the start of the next song. Her chest rests up against mine as our hands clasp. She moves my body with hers, placing my hands alongside her hips. In the dim lighting, she becomes exotic. Forbidding, even. She transcends to another level of intimacy. Her smile, the movements of her body, ask me to follow along with her. I can't. I never could. I don't belong here. If I can't keep up with her, I can't have her. Why torture myself with fleeting success if I'm just going to bomb it in the end? Feeling her body next to mine, I'm slapped with the harsh reality that this is as close to happiness as I'll ever get. I sustain enough courage to finish the song before breaking away from her. "I'm sorry, I have to go." The look on her face pains me. It's a lie, I tell myself. This is all a lie for the big joke later. It's too late now anyway. I must finish what I began. "I just can't keep doing this tonight. I've got other things I should be getting to. I'm sorry. If you'd like a ride home, I'm be more than happy to offer you one." "Oh," she says. Her eyes, new at dinner and familiar here, now capture the absolute shock washing over her. "No, that's, that's fine. I came here with Ally, after all. I should be able to catch a ride with her." I nod my head. I was just being cordial. It's something guys are supposed to do. "Okay. Thanks for a lovely evening though." I can't bear to be an ass any longer. With a wave goodbye I make haste for the lobby. I think I caught Alex's look of confusion on the way out, but I'm not about to turn around and confirm it. I steadily hurry back to the parking lot where my car waits. I fumble for my keys, not wanting to delay my exit in front of them any longer. I would not be able to face them, if I could. I quickly hop in and head back home. The ride home is excruciating. I try to distract myself from recounting the evening. It is not easy, everything is so fresh. The smell Jenny's perfume, when she pressed her body against mine, lingers still in my nostrils. My heart still leaps when I remember how warm she felt. The question 'why?' surfaces, as it always has. As always, I ignore it. I return home. If I can just put the day behind me, I'll be set. I just need to change and crawl into bed. She's waiting for me there. My sheepish attitude speaks for how I messed up the evening. She knew I was coming home. Smiling, she readies to sink her teeth into me. "Blew it again, didn't you? What did I tell you? You can't escape this." I try to ignore her, entering my home and quickly changing out of my clothes. If I can ignore her nagging, I'll be free. "What was it this time? Her smile? Her femininity? The fact that she's everything you want, and that she can bring you happiness?" I tell her to shut up, but I know it is useless. This is not the first time I've come home to her to hear this. She's been there ever since I've met her. She continues to haunt me, and I can't let her go. She mocks me as I make my way to bed. I crawl under the sheets, but just as I expected, she huddles in with me. "Why do you even try? You cant give me up. You need me. You want me to need you. If you have me here, then don't fight me. Do to me as you always want to do." I can feel her coaxing my cock. She always does this to me. My cock springs to life with it's newfound attention. She wastes no time. The sheets are scattered. I can see her impaled on my cock, her eyes penetrating through me, riding my shaft with a victorious smile gleaming from her face. "Oh, this feels good. You like this, don't you? Mmm yeah, fuck me. Fuck me like you've always wanted to." Her breasts are heaving, calling out to me. Her hands caress her flesh, attending to the demand to be touched. I can see desire manifest in the hardening of her nipples The moans I hear plead me to touch her, to hold her as a lover would. But I can't. Regret flows over me, knowing that I can't. "You still want this, don't you?" she asks, leaning her body on top of mine. Her breasts close in on my chest. I can practically feel them. "It's always so good with you. You enjoy having me, don't you?" My cock continues to be milked by her form. My breathing increases, as does hers. We're working to the same climax, as it has been for every night which I've lusted after her. I can feel my impending release rising within. She cries out to me. Envisioning her body grinding against mine, her breasts bouncing as her face contorts in orgasmic pleasure sends me over the edge. My prick erupts, ejaculating its load. My hand is covered in seed. In my hesitation, the creamy mess trickles down the back of my hand, getting caught in my pubic hairs. She's done it again, fucking with my mind. The seed was planted long ago. Once again, she's reaped her bounty, forgoing my happiness to own me. In cleaning myself off, I reflect on the past. I ask myself how long this has been going on, and how much longer it must continue. I still cannot get her out of my mind. Every day, every thought on my mind is about her. I can hear her laughing at me now, as I wipe the semen off me. She consumes me, as she always has, and forever will. Loser goes down “How dare Eric do this to us?” exclaimed Torrie Wilson. “Putting us in this kind of match.” “I don’t mind,” said Stacy Keibler. “Yeah, we are going to do it later anyway.” giggled Women’s champion Trish Stratus. “But a loser goes down match? That means we’ll be eating each other out in front of millions of people here and on pay-per-view.” “Makes me wet just thinking about it.” Stacy and Trish both exclaimed. Torrie then added, “Well, I do love when you both eat me. And it’s fun when our boyfriends watch. Now that I think about it, I’m a little wet myself. I guess it’s time for the match.” “The following contest is a special Strip your opponent bare, loser must go down triple threat match. First coming down the aisle Torrie Wilson.” Torrie Wilson’s music hits and she walks down the ramp. Wearing a red, white and blue sports top and long blue pants she looked amazing. The top showed off her tits well as her nipples protruded thru the material. And those tight pants made her ass looked spectacular. The crowd cheered loudly as she made it to the ring. “Coming down the aisle next is Stacy Keibler.’ The song “Legs” hit and the long-legged Stacy Keibler made her way down to the ring. She wore short black shorts showing off her forty-one and a half inch legs that made every guy cream in their jeans. A tight baby blue tank top finished off her ensemble. “Finally, making her way down the aisle, the WWE women’s champion Trish Stratus.” L’IL Kim started playing, and the curvy Trish made her way down the aisle. She wore long purple pants that showed off her ass perfectly. An extremely tight purple tank top showed off her tits amazingly. The crowd went wild for all four beautiful ladies. As the match started, all three ladies went at it trying to rip each other’s clothes off. Trish first stripped Torrie of her top revealing a hot pink bra. Then Stacy and Torrie teamed up to remove Trish’s shirt leaving her wearing a barely there black bra. Trish then lost her bra shortly after as it got ripped off by Stacy. This left Stacy as the only one who hasn’t lost any clothing so Trish and Torrie teamed up to get her out of her clothes. All three girls were getting even more excited and horny as the match wore on. Trish and Torrie both got a hold of Stacy’s top and ripped it to shreds leaving her in a skimpy bright yellow bra.. Then Stacy got a hold of Torrie and got her bra off revealing her perfect breasts. Trish got Stacy’s bra off shortly there after, leaving all three girls topless. Since Stacy’s shorts were the easiest to get off, she lost hers first revealing a pair of yellow thongs. Then Stacy got Torrie’s pants and underwear off at the same time leaving the blonde bombshell completely naked. All the guys in the crowd took in her beauty. She was shaved bare and looked incredible. This left Trish and Stacy still in the match with Stacy just a pair of thongs from defeat. Trish then got the victory by ripping Stacy’s thongs off. Again, the men enjoyed the show. Stacy’s bush was trimmed almost bare. “And now as the stipulations state Torrie and Stacy must perform oral sex on the winner Trish.” Trish then slid her pants and thongs off to reveal her wet pussy. Grabbing a chair and the microphone, she proclaimed, “Come on girls. Nice fresh pie for you two.” Stacy came over and shoved her tongue in Trish’s mouth. Torrie dropped to her knees and started kissing the inside of her thighs. Stacy sucked on Trish’s nipples as Torrie darted her tongue deep into Trish’s wet hole. Trish spun Stacy around so she could enjoy Stacy’s pink taco. Even though she won, she was going to give the fans a real show. She started licking Stacy’s tight asshole while slid her finger deep into her cunt. Meanwhile, Torrie was attacking Trish’s pussy with passion. She licked and sucked Trish’s clit as she finger fucked her. While she ate Trish, Stacy fingered her. Stacy needed to eat someone. So, she lay on the mat under Torrie and started licking her pussy. It didn’t take long until Trish was cumming heavy. She came all over Torrie’s face. As she watched Torrie get ate by Stacy she walked out over to the timekeeper. She bent down, grabbed the strap-on from under the timekeeper’s table, and went back to the ring. She put on the toy, knelt down between Stacy’s long legs, and went to work with the toy. She fucked Stacy’s wet hole as Stacy ate Torrie. Torrie then got a second strap-on and placed it at Trish’s ass. Torrie then slowly entered Trish’s ass as Trish fucked Stacy’s wet pussy. Both Trish and Stacy were screaming in pleasure and delight. Stacy came in a violent flurry coating the ring mat. Stacy then took the strap-on from Torrie and sat on the chair as Torrie straddled her. She fucked Torrie’s ass as Trish fucked Torrie’s wet pussy. They found a rhythm as they went in and out of Torrie making her their little fuck slut. Soon, Torrie was also cumming hard. She loved getting double fucked by these two girls. All three girls smiled and waved to the crowd as they walked back up the ramp. All of them couldn’t wait to get together with their boyfriends for the orgy they were all going to share later that night. Loser Takes All It was my first job out of college and I was determined to make good. I felt I was on the "fast track" when the owner of the company invited me to join him and two important clients on a sport fishing trip to the Louisiana gulf coast. It was made clear that I was to be a "go-fer" with benefits, that is my job was to see that everything went smoothly and do any heavy lifting or dirty work if the need arose. That was fine with me, I would still get a nice vacation and make serious points with the boss. The "Boss" was a bull of a man at least a foot taller than my 5'6" and probably a hundred pounds heavier than my 160, not the least of it in a generous paunch. He was about 55 years old and balding, one of those "comb over" guys. He considered himself quite the ladies man and had a reputation as a skirt chaser. It must have been his money because he was always bragging about how much "tail" he was "nailin". I myself was nearly a virgin, I had "done" it just once, in the back seat of a rented limo on prom night. I had been drunk and not, I'm afraid, very good at it at least according to my date a girl with, apparently, considerably more experience than I. After she had publicly discussed my, uh, "short cummings" I have been a little shy about repeating that debacle. Back to the trip; We met the clients, Bill and Joe, at the airport where we were to board a charter flight to New Orleans. The were pretty much like the boss in age and temperament if not build, one short and heavy the other tall and thin. They left me to take care of the baggage and proceeded to get the party started in the lounge. They were drunk by the time we took off and kept me busy assisting the flight attendant hustling drinks all the way to our destination. What followed was a kaleidoscope of strip clubs, bars and night clubs. It was almost daylight when we finally went back to our hotel. I was exhausted. I awoke and looked at the clock and groaned. It was only noon and the boss was pounding on my door. Time to load up the rented SUV and head out to the fishing cabin he had rented for the week. It was on a remote bayou with only a generator for power. The guide would pick us up every morning in his boat and take us out into the Gulf. Since they were still drunk (and still drinking) I drove. Thank God for GPS or I would have never found the place. It was, as near as I could tell, on an island with only one bridge. The owner met us, showed me how everything worked and the went on his way. We were amply supplied with food and booze (I rarely drink; remember prom night?). There was even a big screen tv with satellite and a pile of porn movies for the dvd. So far I was sure having fun! That's sarcasm if you missed it. By this time it was getting dark and after whipping up a quick meal that nobody ate we turned in. Thank God. We were all up at dawn and out on the Gulf by 8:00. Luckily no sea sickness. and we caught a few fish. It was almost dark by the time we got back. Thankfully the crew of the boat cleaned and cooked our catch before they departed. Boss and cronies were drunk and I was exhausted. This was turning into the most work I had ever done on a "vacation". Before he left the Skipper warned be that a storm might be brewing and that we might have to cancel the next days outing. He would see us in the morning if he thought it was safe to go out. That night it did storm. One hell'uva storm and sometime in the night the generator conked out. No power, no cell coverage and when I got there, no bridge! We were stuck. It rained all day and into the night. All there was to do was play poker by kerosene lamp and drink. I was terrible at both. I think everyone was getting pretty bored and the guys started talking about our night in New Orleans and the various attributes of the strippers they had gotten lap dances from. It was pretty obvious they were getting horny, as the talk got raunchier an raunchier. By now even I was sipping on some scotch and getting kinda lit. Finally the boss said that he couldn't take it anymore He needed some relief, and someone was going to have to "take one for the team". I wasn't sure what he meant but I had a bad feeling. One of the other guys said he felt the same way and looked pointedly at me. The other guy suggested we cut cards to see who would "provide the service" (wink; nudge). I started to sweat and glanced at my boss. He was just leering at me and then I knew. I knew what they were talking about! Everybody agreed (I didn't feel I had a choice) that low card would be the "provider". Boss cut first and drew an eight. Bill next and whooped when he drew a ten. Joe's hand was a little unsteady as he chose and groaned when he cut a five. Boss was smiling now and then he looked at me menacingly. "Your turn" he said and held out the deck. His eyes were boring into mine and I knew what he wanted. "Don't fuck this up" they seemed to be saying. "Remember! The client comes first!" My mouth was dry and my hands were shaking as I reached out. I knew what the boss wanted of me and if I read his eyes right I knew my future hung in the balance. I cut the deck and looked carefully at my card. Three sets of eyes watched as I gently slipped a queen face down back into the deck. My voice shook as I all but whispered "I lose". Three voices whooped loudly as they slapped each other on the back. The tension was broke for them but I thought I was going to be sick. The first thing they had me do was strip. I felt embarrassed to be naked in their presence and it only got worse as they had me scamper around fetching drinks while they took turns smacking my ass and commenting on how hairless my body was. Comments such as "Hell he even looks like a girl from behind", "Even from the front!" and "You sure have a pretty mouth" brought roars of laughter Next they cut cards to see what order I would "service" them. It was to be Bill then Joe then Boss. Bill stepped up and motioned me over. My head was swimming as he put his hands on my shoulders and gently forced me to my knees in front of him. "Come on son, you know what to do" he said and placed my hands on his belt buckle. "I want you to look into my eyes the whole time" he said softly "I want to see your eyes as you suck my big cock. Now take it out!" It felt like I was outside my body as I undid his pants an pulled them down. I couldn't help but glance at his cock as it came into view. "Look at ME!" I looked back up. That one glance had told me it was long and thin much like Bill himself and only semi-hard. He flexed his hips forward with a grin and bumped my lips with his cock. "Give it a kiss, son. Kiss it real nice." I leaned forward and kissed the shaft. The texture was smooth and there was a musky scent in my nostrils. It twitched slightly and I jumped like I was bee stung. He laughed and said "It won't bite you, son. Just make damn sure you don't bite it! Now get on with it. Take it in your mouth and suck". I noticed the room was quiet and I wanted to look around to see what the others were doing but my eyes stayed locked on Bill's as I leaned in again and took the head of his cock into my mouth. He groaned and somehow that pleased me. Leaning farther in I tried to work up some spit as I took more of him into my mouth. He pulled back slightly and then flexed his hip again forcing more of his cock into my mouth. This time I groaned. Then he rested his hands on my head and started to fuck his long, slim cock into my mouth, each stroke going a little deeper than the last, all the while looking into my eyes. He soon reached the back of my throat making me retch. That brought a chuckle from behind me. Bill backed off slightly so I didn't choke and I was grateful for that. I realized that I now had one hand stroking his shaft and one on my own cock. "Oh my God! I was hard and I was jerking off while a man fucked my face!" I thought as I blushed with shame. Bill saw the emotions sweep over me and smiled. Slowly he put more pressure on my head and steadily forced his cock deeper and deeper down my throat. He was good at sensing when I was about to gag and withdrawing. With wonder, I realized that he was teaching me how to deep throat cock as he went along. It seemed like an hour, but probably wasn't, when I managed to take him all the way down. I could feel his pubic hair tickle my nose and saw his eyes sparkle as I slowly withdrew off his cock. I had a strange sense of pride and slipped back until just the head remained in my mouth. Then sucking as hard as I could I started back down. His eyes were starting to get a glassy look to them as I swallowed his big dick over and over, faster and faster. With a groan he started sinking to his knees pulling away from me. I panicked and used both hand on his ass to try to keep his dick in my mouth. I was confused. "Why was he taking his cock away from me" But he wasn't. He was just re-positioning so that now I was on my hands and knees between his legs as he lay back on the floor. It had the effect of forcing my ass up and I became aware with a start that Joe was behind me. I started to panic again and I heard Joe tell him to hold me. Bill grabbed my ears and forced his cock down my throat and Joe smacked my ass hard and told me to "behave". I felt a cool liquid being pored over my ass and then a hand gently massaging my buttocks. It actually felt pretty good and I started to relax a bit. I heard Joe murmur "He does have a nice ass" he mused, "Hell I think it's better than my wife's! " That brought a chuckle from Bill who relaxed his grip on my ears and allowed me to continue sucking him off. I felt a finger start to probe my asshole. Luckily it was well lubed and before I knew it it was sliding in and out. Just as I was getting used to it it was joined by another. That was uncomfortable but Joe was taking his time and I was slowly stretching to accommodate them. By now I was trying to concentrate on Bill's blowjob to take my mind off what Joe was doing to my ass. The term "sloppy" could certainly be applied. For some reason I was drooling like a faucet. With little nudges from Bill I would vary my pace, sometimes short and quick, sometimes deep and slow. I thought Bill had amazing staying power. He was obviously enjoying my "services"and I could hear him moaning as I lost myself in the moment. My whole world seemed to be that cock . That changed the second I felt the tip of Joe's cock touch my asshole. I felt a stab of pain and stopped sucking as I tensed up. "Just relax" someone whispered. The cock in my mouth twitched and I went back to sucking to try to take my focus off my ass as Joe's big cock pressed harder and harder against my poor sphincter. Sweat broke out on my forehead and I could hear an agonized wail that I realized was mine. Then, with what I can only describe as a "pop", the head of Joe's cock entered me. Luckily he stopped to allow me time to adjust. After a few moments Bill nudged me to continue and then Joe slowly started to shove what felt like a telephone pole up my ass. The deeper he went the harder I sucked, trying desperately to take my mind off my ass. Just when I thought he must be all in and it couldn't get any worse he started to pull out. I thought he was taking my insides with him. Now tears were mixing with my drool on Bill's cock. With only the head still in me, Joe reversed course and started back in, slow but firm and steady. This went on forever and it came as some surprise to me when I realized that the pain was greatly diminished and what I was now feeling was alternately the sensations of full then empty, full then empty. Before long Bill got back up on his knees and with his long thin cock in my mouth and Joe's shorter, fat cock in my ass I had the sensation of one huge cock running clear through me. Bill would pull me forward burying his cock down my throat then Joe would pull me back burying his cock in my ass. Over and over until finally I was throwing myself back and forth on that huge single cock. Faster and faster I went until Bill and Joe were just holding on for dear life. My cock was as hard as glass and I could feel myself close to cumming. By the sounds of the moans coming from Bill and Joe they were close too. Finally Joe reached around and grabbed my dick between his thumb and forefinger and gave it a little tug. That was all it took. I shot off like a geyser. With a mighty shove by both Bill and Joe, they too started to cum. Bill was groaning as he shot spurt after spurt of cum down my gullet. I didn't even have to swallow, he was that deep. I felt a little disappointed that I wasn't able to taste my first load of cum but he pulled out enough that the last couple of spurts landed squarely on my tongue. Perversely, I savored the taste. Simultaneously I could hear Joe snarling like a pit bull as he slammed into me and dumped what felt like a quart of cum in my ass. Spurt after spurt of deliciously warm cum flooded my hole and I wiggled my hips like a bitch in heat to get it all! We all collapsed in a pile, me on the bottom laying in a puddle of my own cum. I slowly became aware of my surroundings. I was still nursing on the head of Bill's cock like it was a baby bottle. With a chuckle he slowly disengaged and patted me on the head like I was his favorite puppy. He actually said "Good boy!" as he got slowly to his feet. I groaned with humiliation. Joe and I were still tangled up and even though he was still buried in my ass I could tell his cock mad shrunk. I was not nearly as full. With a moan he pulled out and I could feel his warm sticky cum run out of my gaping asshole. I instinctively reached down as if to stop the flow and was shocked when I could stick my index finger in without touching the walls of my sphincter. I scooped up some of the mess and brought it too my lips catching myself just in time before licking it off. Joe caught the gesture and I blushed. He rolled over on his back and, grabbing me by a hand full of hair, he pulled my face over to his cock. "I'll give you a taste, you little faggot!. Get your lips around it and clean me off!" he snarled. Burning with shame and humiliation I did just that. In fact once I got started he had to finally push me away. I don't know what came over me. I just couldn't stop sucking, I know it was disgusting, I mean his cock had just come out of my ass but I couldn't help myself. He finally got up and left me, joining Bill at the bar for a tall scotch. I lay where I was in a puddle of my own spunk.I heard a growl and looked over to where Boss was sitting in an overstuffed chair. He was completely naked. I took one look and knew it wasn't "just" his money that attracted women. Standing up from between his hairy legs was a huge cock. It looked at least a foot long (its actually 11", I've measured it!) and as big around as my wrist. The veins stood out from the shaft and the head, the size of a lemon, was an angry purple color, in fact, angry was the way I would describe the whole thing. His body was practically covered in thick hair which made his baldness ironic. In spite of his gut he was powerfully built. I found myself both intimidated and strangely thrilled when he held out his hand and crooked a finger at me to come. I crawled (it just seemed "right" to crawl) over to him and kneeled between his thighs when he spread them. I assumed he wanted me there but he surprised me by gesturing me up onto his lap. It was like sitting on Santa's lap when I was a child except of course this Santa was naked with a huge hard on. He wrapped his big arms around me and drew me in in a hug. He was very gentle and as he hugged me to him I felt very warm and secure. He murmured how proud he was of me and how he was going to take "good care" of me and I was going to be his little "slut" boy. He said he had known from the start what kind of a boy I was and that he would see to it that I got all the "yummy" cock I could handle. Then he kissed me. A deep soulful tongue down my throat kiss that left me breathless and my "little dickie" (his description) throbbing. Telling me to go pour him a scotch and get him a Havana, he gave me a swat on the ass to get me started. I don't know what came over me but I squealed like a little girl and I couldn't help wiggling my hips a little as I scampered off to do his bidding. Bill and Joe just smirked at me. Returning, he sent me off to clean up while he waited. I just took a bar of soap and stood under the eaves to shower off in the rain water. I toweled off as I padded back to my Boss, falling to my knees between his wide spread thighs. His cock had softened and was laying across his thigh. Without being told I started to nuzzle, then gently suck on the head, to bring the monster back to life. I didn't understand it at the time but somehow I knew that I had found my place in the world. I was where I belonged. What a sight Bill and Joe must have had as they went off to bed that night. There was the Boss, sitting back in his chair, sipping fine scotch and smoking his huge Havana while I slowly and languidly made love to the biggest cock I've ever seen. Loser To Lauren This story contains content including strap on play, cross dressing, and general anal play. If this content is not what you are looking for then you can click away now, I promise not to get offended. This story aims to get away from the dominant woman forcing the guy to do it and then he secretly wants it anyway sort of story and looks to get into the more mutual side of things and how wonderful it can be if you find someone who is willing to give themselves over to you entirely. All work is fictional and as such is not taken from anyone else, If there are similarities to other writers then I sincerely apologize but chalk it up to great minds thinking alike. I just want to thank Trixter for all their help with editing. You have been a great help and I could not have gotten this story finished without you. This is my first story so go easy on me ok guys! ***** Hi, my name is Chris and I am an 18 year old guy. I was not popular at school as I was predominantly interested in playing computer games and reading comic books. This inherently caused my other interest, girls, to completely ignore the fact that I existed. When I moved into Sixth Form College I took my interest in PC hardware a step further and became a freelance IT support guy around or town in order to pocket some extra cash. This basically meant that I would get a call from my mum to tell me that one of her friends was having issues and they needed someone "Techy" to come and figure it out for them. A lot of the time this involved me going to their place of residence and applying the old turn it off and on again trick to fix their issues. Every time she would call to tell me that someone was having issues I would always hope beyond hope that it would be Mrs Clark that needed help and that I could go to her large home at the edge of our town. This was an unlikely event as they had a lot of money and they would more often than not just buy new stuff but on one fateful blustery October day, I finally got that wish. "Chris, I have one of those IT thingys that needs doing again" my mum called up the stairs at 9am. I had the day off from sixth form and was hoping to lie in, drink some cold Lemonade and play my PC til my fingers hurt. "If this is Mr Anderson calling again to find out if his home telephone can connect to his Wi-Fi then I might just throw the damn thing at him" I yelled down to her. She could sense the irritation in my voice at being woken up but she couldn't stifle the giggle at knowing that Mr Anderson wouldn't know his arse from his elbow if his wife didn't remind him. "Actually..." she cooed in that voice that mums do when they want you to do something and they know there is no way that you won't bail out of doing it, "It's Mrs Clark, you know Amy's mother?" she continued and I could hear in her voice that she was openly grinning now. "Are you serious?, surely she could have a million guys come over and do that, she probably even owns her own IT guy" I shouted down the stairs in a reflex, not really meaning it and processing that I might be in Amy's house at the same time as her. "She tells me that they sent the guy away because he was talking down to them and making them feel stupid, she asked for you by name and everything. I told her you could be there at 11:00, hope that fits around your schedule." I sat there for a minute completely dumfounded, a million scenarios going around in my head. Maybe my mum put her up to this, maybe Amy did and they were planning to embarrass me somehow. Finally I settled on the fact that she would pay good money and it would be worth the embarrassment, after all it couldn't be worse than most of my days. I jumped up and went for a shower, I had barely any hair on my body and I shaved what little I did have on a fairly regular basis as I liked the feel of the cool air on my body and the way my clothes felt as I pulled them over my smooth skin. I showered and shaved the little stubble on my face and brushed my long hair tying it up in a ponytail as I did most days. I brushed my teeth and dressed in a plain white T-shirt and Combat Trousers before I sauntered downstairs to grab some things I thought I might need (screwdrivers, portable hard drive reader etc) and headed out the door. As I closed it my mum called after me "Say hi to Amy for me" in a sickly sweet voice. I headed out to my car, mum and dad had bought me an old style fiesta for a first car and it was doing well for an old thing. I drove up to the Clark's house and pulled into their driveway. The area for parking cars was bigger than most of the rooms in our house combined and parking my little dinky fiesta so close to their shiny new Audi and Jaguar seemed like a crime. As I walked up the large front door and rang the doorbell I felt a flutter in my stomach. I don't know if I was overwhelmed by the size of the house but I certainly felt uneasy. I pulled myself together reminding myself that if I could solve the issues they were having then just maybe I would get a nod or a hello from Amy at college and feel like a normal kid for once. No such luck, their PC was outdated which surprised me and they only wanted to recover some data before they replaced it. "We just wanted to get our pictures of our beloved pets off of their before we buy a newer model." Mrs Clark had told me. "I understand, we lost our dog too and pictures are all we have left of him." I got a bit choked up as Buster had been my best pal and always cheered me up when I had a bad day at school. The hard drive reader was pulling the data off and to my surprise Mrs Clark pulled me into an embrace as she saw I was fighting back tears about my old buddy. "They are more like family than we realise aren't they?" she soothed as she stroked the top of my head. The reader finally finished pulling the data and using my laptop I put all of her data onto an external hard drive. "If you keep hold of this til you get your new PC then I will pop by and put all of the new data on it for you." I said as I held out the hard drive. "You are very sweet." Mrs Clark beamed a smile at me; she was a beautiful woman, in her 40's but still a knockout. "If you could not tell Amy about the whole me being a wuss and you having to hug me, I'd appreciate that." She laughed heartily but then with a semi-serious scowl said "Don't be afraid to show emotion Chris, there are too many enhancements in technology and we don't need emotionless 18 year old robots roaming around." She chuckled. "On that note actually, why is it that my daughter does not hang around with guys like you? all the guys she brings home are rude." "People like me don't get to be in the same circles as girls like your daughter Mrs Clark." I said rather sheepishly. "Are you saying that my daughter is mean to you at college Chris?" she seemed hurt. "Not at all Mrs Clark", I reassured her, "but Amy is popular and I am...a geek." She looked at me quizzically and then it seemed to click "well I will have none of that nonsense around my house, go out back and see if she is sitting in the garden, say hi and hang around for a bit. I'm pretty sure she has Kat over." It would be an absolute shock if she didn't; they had been attached at the hip for almost their entire lives. Where one went the other went and they were inseparable during any break and lunch time. They were super close too, which means what one of them knew the other knew which was bad for me. I had asked Kat out once, back when I had any sort of confidence, and she had turned me down. She was polite enough but she informed me that I was "Not her type". I had seen the two of them pointing at me and giggling for a following number of months and a small glimmer of hope had me believe that Kat was trying to get Amy to notice me. These hopes were dashed when one of the popular guys informed me that they had spread rumours about me having a small dick. I didn't hate them for it but I was disappointed that they were like all the other girls I knew (I later found out this rumour was a lie made up by the boy because Amy had rejected him). I approached the back door and neither of them was out there so I turned to leave, Mrs Clark had other ideas and ushered me towards the stairs. "I'm sending Chris up to you girls to say hi she shouted" and pushed me up the stairs, there was no answer but the music was very loud coming from their room. I knocked on the door but no one answered, I could hear muffled voices but the music was drowning everything out. I knocked a second time "Amy, its Chris, Your mum said to come up and say hi". They didn't answer so I pushed the door, it wasn't completely closed and it slowly swung open and I could see Kat sat on the edge of the bed with her hair in bun and Amy giggling as she applied make up to her face. Kat looked around Amy at me and Amy, who had straddled Kat at the waist, craned her neck to look at me. "Chris Right?" Amy started "Did I forget homework or something?" she asked. I felt a twang of pain as if the only reason I would ever be at a girl's room would be to bring homework. "No I was just fixing the PC and your mum insisted I come up and say hi, I was going to leave you in peace but she wouldn't let me leave." "That's mum." Amy said with a giggle "I'll see you around then." I said hurriedly as I turned to leave. "Wait!" yelled Amy as she leapt off of Kat's lap and grabbed my arm "As you are here you can hang with us if you like, we were going to have a girly day and then hit a party later, are you going?" she asked me with a hint of excitement in her voice. "I didn't know there was a party and I probably would not have gotten an invite anyway." I said dejected. I was sad but I was at least a realist. "You can still hang with us if you like?" Kat encouraged. I wasn't sure if it was out of pity or if it was genuine but I took the offer. "If you guys don't mind then I would love to hang around." I smiled, I couldn't help it, pity or not this was awesome. I took a seat on an armchair in the corner of the room. "Hey if you don't mind us messing around and doing all our girly bits, you never know we might even give you a makeover." She winked as she turned to her doll to carry on. Now before we get on to the next part, I think I should give you a bit of a back story. I had always liked girly things. I was jealous that girls all had so many things to choose from. So many pretty things, with accessories and make up. I had always wondered what it would be like to get all dressed up in some sexy heels, with my make up on and hanging out with the girls. It was something that I masturbated too often and was a fantasy that I would not dare to bring to reality. Now with that said and all these feelings floating around my head, I have no idea why my inside, wishful stupid voice was actually saying aloud. "Yes please." Total deathly silence, followed by a slow head turn of both girls looking at me with shocked faces, and it dawned on me that I had said it out loud. "Pass it off as a joke, leave, do something!" I willed myself. Kat beat me to the punch but I was at least thankful of her to break the silence. "Wait, Chris, are you gay?" Amy turned and scowled at her so hard "Kat!" She yelled, "Don't be so insensitive, If he wants to do that sort of thing then it's his business. Doesn't mean he is gay." "Sorry." Kat mumbled, but you could see she was genuinely concerned. "I'm not gay." I plucked up the courage to say, although very quietly. "Tell me about it" Amy's tone had changed; she led me by the arm to the bed in between them. "You can trust us, right Kat?." "Of course" Kat was a few things, but a liar she was not, she took that very seriously. "I'm not sure.", I began, "It's just something I was always interested in, something I looked for online if you know what I mean, and I just get bored with guy clothes you know? It's all T-shirts, jeans, combat trousers, whereas girls get to wear all these pretty things, and heels..." I trailed off as I notice a stirring in my trousers; I was not the only one. Kat nodded to it, Amy followed her glance and turned back to face her. They nodded to each other and looked back to me. "I understand that it was difficult for you to tell us that, and we are very happy you could confide in us." she smiled and touched my arm "and so that you can feel safe that we will keep it to ourselves, we wanted to share a secret with you." she turned to Kat to continue. "Everyone knows we are good friends." Kat began "and we have always been close. As we got to 17 and a lot of people in School were having sex, we felt pressured into joining the culture but neither of us was ready." I felt a pang of guilt, that I saw these girls as all the rest but not stopped to think that they might have peer pressure to deal with too. "So we came up with an agreement." Amy continued "Where we would both be ready when the time came." they sat next to each other and locked hands. "Do you know what a strap on is?" Kat asked. I nodded. My trousers did too. "We prepared each other for sex." Amy stated matter of factly. "We aren't Lesbians" Kat answered my mental question that I dare not ask. "We trusted one another and why do it with a stranger when we could help each other out?." I suddenly understood these girls better than I ever thought I could. "Truth be told no sex has been better since." Kat said, for the first time it would seem because tears formed in Amy's eyes. "Same for me" she said and Kat beamed a smile at her. "But we promised never to do it again; we don't want to threaten our friendship by going down that road." "So...where do we go from here?" said Kat to the room in general. Amy looked at me, then down to the brush in her hand, to Kat and finally back to me and smiled a broad smile. "Her first" she motioned toward me and Kat agreed with excitement. "First things first, kiss me" Amy said out of the blue "Kiss...You...On the lips?" I couldn't stop my voice from shaking as I said it. "Whenever you are ready." Amy just stood there, inches from my face. I took a deep breath, I'd imagined this moment a million times as I shot my load into a tissue, but here it was right in front of me and I was determined to make it worthwhile. I caressed her cheek with the outside of my hand and rested my other hand on her neck gently. I pulled her face to mine and kissed her softly for a slightly longer than normal time and gently let go of her neck and pulled away. She had her eyes closed and suddenly shook herself out of a stupor. "Wow" she said. "For a first kiss that was pretty damn impressive." Kat had a stunned look on her face "I said no, to that, because you weren't 'my type'" she stared at the ceiling, "I'm an idiot". That made me smile. Amy had recovered at this point and looked into my eyes, she assumed the position on my lap that she had occupied when I first entered the room on Kat's lap, but this time I was the lucky one. "We can do the full works, make up, clothes, shoes or anything you want." she put her fingers to my lips to stop me talking "But it has to be what you want and I don't want you to say no just because you think we will be weird about it, if you want it then we will make it happen for you." "I don't think I have wanted anything more." I said with complete conviction. The girls squealed, whispered something to one another and nodded enthusiastically. I would later find out that this was them discussing how I might one day become the third person into their inner circle, that I was a loner and that I would provide the one thing neither of them had in this relationship. That thing was male company and more specifically male parts. Amy began by plucking at my eyebrows whilst Kat took her talent to my fingers and began manicuring, shaping and painting my nails a deep purple colour. I know that having your eyebrows plucked hurts but so lost in the moment was I, that I didn't feel one ounce of pain. Amy maintained eye contact throughout the whole process, only was our gaze broken when she asked me to close my eyes to apply the eye shadow to give me the smokey look. They worked for a good 2 hours before I was told to walk to the wardrobe. Kat kept some of her clothes here and we were roughly the same height. I wasn't tall but she was tall for a girl and we were both slightly higher than Amy. She compensated by wearing larger heels but I was thankful to be Kat's size looking at Amy's shoes. They had me step into panties and a suspender belt before pulling me to sit down in the armchair. I was instructed to point my toes out towards Kat as she rolled a pair of hold up stockings up each leg. I stood up and she attached them to the garter belt. Amy lifted something over my head and positioned it at my chest. She placed some rolled up stockings in the cups and pulled it tight to my chest before doing it up at the back. It was a black Corset and the stockings were to give me some sort of 'bust'. They felt electric against my nipples and I knew my figure must look very feminine. I stood like this looking down at what seemed to be this beautiful woman's long legs encased in silk as my hair was taken out of my ponytail and curled for what seemed like forever until it framed my face. Whilst Amy was doing my hair, Kat had slipped into an identical outfit to mine. She looked incredible. They both moved in front of me and smiled as they looked at their handiwork. "Now Heels!" Kat shouted excitedly as she went straight back to the closet and picked out a pair of 4 inch black patent high heels. Amy helped steady me as I stepped into them. Kat stepped into an identical pair. "Walk around and get comfortable." encouraged Kat "Wait" screamed Amy as she threw a cloth over the mirror. "I want her to get the full effect." I smiled and began to walk around the room, I wobbled at first and they had to balance me. Then as I got more comfortable they were whispering to each other again. Whilst I walked around, Amy had dressed into the same outfit as us, but in white and with white heels to match. "Big reveal time!" now Amy's turn to be excited. They positioned me in front of the mirror and prepared to pull off the sheet. "If you don't like it I promise we can help you take it all off and we will just pretend this never happened" she said looking deeply into my eyes. "Thank you" I said to them both and held my breath, what little I had left from the tight corset, and waited. When she removed the sheet, for a few moments, I felt like I was looking at someone completely different. I just stared for a while, then I started to run my fingers over the corset and the beautiful girl started to do the same. I touched my legs and the jolt up my spine was incredible. I felt a twinge and looked embarrassingly at the girls. My dead giveaway was there jutting out above the panties and Amy's eyes met with mine once more. "How do you feel?" She asked genuinely. She and Kat hung with baited breath for my answer. "I feel incredible, I love you guys so much" I was overcome with emotion. They both hugged me tightly until Kat began to giggle. "What's so funny?" Amy asked. "We have to do something about THAT." she said pointing at my rock solid cock. "Would you like us to?" Amy asked, slight hope creeping into her voice. I pondered this question for a moment. Until today these two girls had barely spoken a word to me and now they were offering to do 'something' about my hard cock. I nodded with trepidation. First kiss, first time fully dressed, first time anyone else was going to touch my dick. "Do you trust us?" Kat asked. "Unequivocally." I replied instantly. Loser To Lauren Puzzled looks between the two made me smile. "Means with all my heart." Kat placed two pillows on the bed and had me lay with my back down, the pillows pushing my arse into the air. Each of them grabbed some latex gloves from a box in the dresser and coated some fingers in lubrication. Kat turned to Amy "You should get his cock, I want his arse." I took in a deep breath as I felt Kat's fingers at my opening. I desperately wanted this and it seemed like they both did too. Amy made a fist around my cock and I shuddered against the cold. "Sorry, just let me know if you want us to stop at any time." "I don't think I will need to." I answered back with assurance. Kat began to push gently with one finger until it popped past my sphincter. I felt a dash a pain but this was soon overtaken by the pleasure as Amy had started stroking my cock in a slow rhythm. Kat thrusted in and out with her finger as Amy picked up the pace. Kat removed her finger and I felt emptiness until she returned with two fingers and began at a faster rhythm. At the same time Amy wrapped her beautiful painted lips around my cock and began long lengths up and down my shaft. I was close to cumming and let out a small moan without meaning to. "She's close!!" Kat exclaimed moving up to a furious pace. Amy redoubled her effort to show her willingness to take my load into her mouth. I came over and over as an earth shattering orgasm overtook my body. My cock had spasm after spasm shooting load after load into Amy's willing mouth. Finally I stopped and she cleaned me up from the cum that had dribbled out of her mouth. Kat finally removed her fingers from my arsehole and I felt sadness that it was no longer full as my mind tried to comprehend what had just happened. "Ready to go one step further?" was the question from Amy's lips. "I'm not sure." I gulped. "The fingers felt good but I don't know if I could take it..." I said looking at the strap on Kat had retrieved from their chest of goodies. "It's ok" she cooed "you don't have to do anything you don't want to". "I want to, you have no idea how much, but I heard it hurts." "Honey I will be so gentle." she said stroking my face. "OK" was all I could manage. Kat had me stand up and bend over the desk exposing my arse to the sky. Amy had removed her panties and stepped into the harness. Kat helped her do up all of the straps. She returned to my head and bent down showing me another of her goodies. "If the pain gets too much before the pleasure kicks in, bite this." Kat offered me a ball gag. I opened my mouth and let the ball slip between my painted lips gratefully. "If it gets too much we can stop." Amy corrected. "Yeah but just in case." Kat winked at me as she fastened the straps behind my head. Amy coated the dildo in generous amounts of lube and applied some to my arse to ease with the entry. She placed the head and my ring and rubbed my back encouragingly. I nodded and felt pressure; I relaxed and felt it slip in easy for the first couple of inches. Then it felt like it hit a wall. "Ok ready to take more?" Amy asked. I responded by pushing back and meeting her forward momentum. The dildo popped all the way in and it felt wonderful. I felt pressure like I desperately needed the toilet. Sensing my agitated state Kat jumped in eye level with me. "That's just your prostate, like a G-spot but on a man." I settled and Amy got into a rhythm of thrusts some quick and short and some slow and long. She repeated and changed up the tempo driving me absolutely wild. Kat had two of her still gloved fingers now buried in her own slit. I started involuntarily moaning into my ball gag as thrust after thrust rocked my entire body. Amy's breath had becoming ragged and she was grinding her mound into the strap on over and over again causing it to push on my prostate. Kat came first with two fingers in her slit and her thumb making furious circles on her clit. I was close, I could feel it, and no one was touching my cock. I had no idea it was even possible and then all of a sudden it got better. Kat had got off the bed and had wrapped her mouth around my cock that was leaking precum everywhere. She began working the shaft with her tongue and the balls with her fingers. Amy and I came at the same time, Kat almost couldn't take it all but she doubled her efforts to make sure that there was no waste. Amy was thrusting like she was no longer in control of her body and I was bucking and pushing back as shot after shot went into Kat's mouth. Amy pulled out and collapsed onto the bed, and I slumped down next to her. Kat came and laid the other side of me. Kat and I in our matching outfits and Amy in her white set minus her panties she had shed in order to don the strap on. "So..." Amy started. "So?" I prodded. "What do we call you now?" enquired Kat. "I hadn't thought about it." I answered honestly. "You look like a Lauren." posed Amy. "I like Lauren for her." beamed Kat. "Lauren it is" I agreed. "I love you guys and thank you so much for today." "That's ok Lauren, thanks for letting us be part of it" Kat returned tracing circles on my thigh. "We love you too and welcome to our group Lauren" Amy enthused with a deep and passionate kiss. As we broke away from one another Kat dragged me into an equally passionate but desperate kiss. "Damn, I almost missed out." she sighed. I smiled as I drifted off to sleep, spent and overwhelmed. Kat dragged a duvet over all three of us as we settled for a nap. ***** Thanks for reading this story. I welcome all feedback and any ideas would be great to hear. If people enjoy this story then I will continue into a series.