6 comments/ 48848 views/ 16 favorites The Super By: gimmie_your_load I had just moved into my new place in a large apartment complex. What with the moving expenses, new furniture, and some minor repair costs, I was living fairly low budget. The building was in good repair, but not exactly upscale. There were a few damaged walls and a slight odour, but nothing I couldn't fix myself. I had just moved in a week before and had yet to meet any neighbours or my super, although that was soon to change. I was only about half unpacked, with a vague idea where my furniture was going to end up, but boxes were still littered around the apartment. Although the plumbing had been fine the first few days I had started to notice a drop-off in the water pressure in all the fixtures. I wasn't overly concerned, it was a big building, but I figured I should call down to the super and ask about it. I spoke to him on the phone, and he said he was busy but would make a trip up to my 9th floor apartment later in the day. Well, as I should have guessed, he didn't show up that day. I was a bit peeved, but figured he'd get to it the next day and went to bed. I awoke, unhappily, to realize that my water was now totally off, and I wasn't able to have a morning shower. Unwilling to show my face in public, and increasingly unimpressed with the super, I sat near the door drumming my fingers waiting for him to show up and fix it. Three phone calls and 2 messages I left went unanswered. As I waited impatiently, I heard heavy footsteps in the hallway. I rushed to the door and peered through the peephole, spying a large, burly man in a blue shirt that said 'Joe's Plumbing' on it. My temper now flaring as he meandered his way down the hall past my room, I yanked the door open, and he turned around to face me with a start. "In here!" I exclaimed, "You're supposed to be fixing my plumbing! How long do I have to wait for you to get around to it?" I was being more of a bitch than usual, but the stress of moving, and waking up to no washing water really ticked me off. The big guy just stared at me in confusion for a moment and I saw his eyes drift up and down, taking in my body. Oops. I had forgotten to get dressed for public since I didn't shower that day. I was just in my sleeping clothes, a tight little pink t-shirt and some fuzzy red booty shorts. While somewhat revealing since my 36 D's weren't strapped down with a bra, I hardly thought I looked very sexy, my unwashed hair a mess, and what I consider to be my too big thighs and butt awfully evident. My anger began to fade and I blushed under his scrutiny. He finally spoke and broke the silence. "Well okay little lady, lead the way." I turned and led him into my apartment, very aware of his imposing size. He looked tall and powerful, like a strongman rather than a sculpted bodybuilder. His mere presence exuded a manliness that I found both attractive and in this case, a bit disconcerting as he entered right be hind me. He was very close and I could smell his manly scent; the scent of a working man. I was very aware of his close proximity and could almost feel his eyes follow my butt as it wiggled a bit while I walked. I got very self conscious and grabbed a robe as I passed my bedroom door. As I started to wrap the warm thick robe around me, I was startled by a very strong hand on my wrist. I gasped slightly and turned to face the man who was now gently but forcefully pulling the robe from my grasp. "What are you doing?" I demanded, my voice cracking a bit with my anxiety. "I wanted to see more of the bitch who thinks she can order me around!" was his reply. He casually tossed my robe to the floor and pulled me closer to him, leering now at my body. I tried to push him away, but he was far to strong, and my feeble shoves actually brought a smile to his lips. He pushed me back against the wall, and held me there. Again he didn't hurt me, but he was forceful enough to let me know what would happen if I tried to struggle too hard. I whimpered slightly and asked what he wanted from me. "Whatever I want" was his reply, and he took a step back for a better view of my body. Despite my precarious situation, I found his rugged manliness somehow arousing, and against my will my nipples were hard enough to cut glass. He smiled and reached for them, fondling them through my thin shirt. I trembled and as much as I wanted to scream for help, all that escaped my lips was a groan, and not one of protest. What was wrong with me that this turned me on? "Lets see what you have underneath." he said gruffly. Somehow I didn't think it was merely a request. Thinking it best to give him what he wanted, and a little turned on at the thought, I lifted my shirt, exposing my very round, well developed chest. My breasts bounced down into position as I released them from their prison, my nipples rock hard. I looked up at him with a bland expression on my face and asked bravely, "Happy now? Can you get to fixing my sink yet or what?" He grunted and half chuckled at my question, then suddenly grabbed me by the throat, shocking me, but not hurting me. He didn't choke me, but I knew he could if he wanted to. I almost wanted him to try, much to my own surprise. He used his free hand to fondle my large breasts and I couldn't contain my pleasure, hard as I tried. It had been a long time since I had been touched by a man, and I had to admit I missed their strong yet gentle hands on my boobs. I let out a low moan of appreciation as he tweaked my nipples, and pushed my breasts together. "I'm going to have you, you know." he grunted at me. I knew that I did not want him inside me, in my most vulnerable sanctuary of womanhood. As turned on as I was, I wasn't about to drop on all fours and let some random plumber insert himself into me. I had an alternate plan that I would enjoy, however. Looking into his eyes, I licked my lips and gently peeled his hand off my throat. I smiled at him and slowly sank to my knees, my hands trailing and running down his powerful torso to his thighs. "Wouldn't you rather I give you the best blowjob of your life?" I asked huskily. He grunted in response. "Not a very articulate one is he?" I pondered to myself. Oh well, I thought, I might as well enjoy it at least. I began to rub my hand up and down his thighs and watched his thick bulge grow in his pants. He moaned and closed his eyes. I smiled to myself, marvelling at how quickly I had taken back control of the situation. I unbuckled his belt with one hand, my other lightly tracing lines around his package with my fingertips. I slid the belt off and undid the top button of his jeans, now rubbing the flat of my palm on his throbbing treasure. I gave it one firm squeeze and giggled as he grunted with pleasure. I paused and arched my neck up to bite onto his zipper. Sliding it slowly downwards, I looked up into his eyes and winked. He smiled down at me. I used both hands to grip the inside of his pants and tugged then down over his hips, boxers and all. I let out a small yelp of delight as his cock sprang up into my face, hitting me under the chin. He stared down at me expectantly, and took his cock by the base. I knew what he wanted and presented my left cheek to him, a small smile on my full lips. My now free hands made their way to my booty shorts, and I slid one hand inside to tease my already drenched pussy. I shuddered at the first loud *thwack* as his cock slapped off my cheek heavily. He continued to smack it on my face, and I moved around, presenting him my cheeks, lips and forehead to hit. His dick continued to get harder as he did so, till it reached its full, thick, peak. He groaned aloud and I heard his breathing increase in intensity. As a matter of fact, so had mine as I flicked my wet clit. He had already begun to leak precum, I realized with his last wet-sounding slap on my cheek. I could smell it on my face and I smiled and shook slightly. The memories that smell evoked heightened my arousal and I gyrated as I had a small orgasm. Closing my eyes, I felt him begin to rub himself on my lips, which I pursed for him. His cock rubbed back and forth slowly on my lips and when he paused I kissed it, looking up into his eyes. As my quick orgasm subsided, I began to kiss him more with my now slick lips, and as they parted slightly I could taste him on me. That was all I needed and that flavour sent me into a frenzy. My tongue darted out with the dual purpose of licking his juices off my lips, and teasing the underside of the tip of his penis. I reached up and cupped his balls in my palm, my fingers wrapping lightly around the base of his dick, holding it in place. I flicked and licked, feeling more precum run down into my tongue as I licked him. It tasted delicious and I furiously rubbed my clit as I approached a second orgasm. He groaned aloud as the shuddering of my body in the throes of pleasure made my head lurch forward and take his head partially into my mouth. That was all the invitation he needed apparently, and I felt two strong hand grip a handful of hair on each side of my head. Foreseeing what was to come, I loosened my throat and mouth, letting my jaw go slack as he pushed his cock slowly in and out of my mouth. Wet slurping noises filled the room as he slid his engorged member past my lips. I gave up on any suction, and let him fuck my mouth like a pussy, letting the saliva that pooled in my mouth to run out and down my chin. I felt droplets of it splash onto my breasts and thighs as he continued to feed me his cock. He pushed deeper with each thrust, causing me to gag when he reached my throat. His cock was thick and I had trouble maintaining my composure. Slowly but forcefully, he managed to break past my gag reflex as I tried to swallow the thick, soupy saliva that formed in my throat. I suddenly couldn't breathe as his cock filled my airway, past my throat now, choking me. Although desperate for air, I was extremely excited by this; I finally knew how to deepthroat! He removed his dick from my throat and my nostrils flared as I gasped in oxygen. I immediately jutted my head forward again, taking him into my throat once more, and purposely gagging on him to contract my throat muscles on the head of his cock. My chest was soaked now with my saliva, and his balls were dripping onto the floor. As he gyrated his hips into my face I began to quiver with my third orgasm. I can't take much more of this, I thought as the feeling finally subsided. I could still hear him grunting over me as he fucked my face, the wet slurping noises of my mouth complimenting the slapping of his balls on my chin. I realized he was entering my throat with ease now; I was still gagging on him, but the resistance was gone. "I'll have a sore throat tomorrow." I thought. My clit was now pulsing and far to sensitive to touch, so I removed my wet hand and decided it was time to take control of the blowjob back. Gripping his ass cheeks with both hands, I suddenly dug in my nails, and pulled him deep into my throat. He gasped and gladly gave me his length as I gagged for his pleasure. My eyes watered a bit with the exertion and lack of air. He tried to pull out as I convulsed for air, but I held him deep and let him out only when I was satisfied. His cock fell out of my mouth with a *pop* as I sucked on it the last couple inches. I reached up now and pulled his cock up, stroking its slick length with my left hand while I used my mouth on his soaking balls. He moaned with pleasure as I licked and sucked each ball and rolled his sack around with my tongue. His cock pulsed an I could tell he was getting near cumming. I squeezed the base of his cock with my hand and took him back into my mouth, my head boobing in a slow rhythm, my hand moving to stroke him in unison. I slurped and sucked at his cock, jerking him in my mouth. His breathing came in laboured gasps as he groaned and moaned, staring down as I sucked his dick. As his balls began to tighten in their sack, I leaned back slightly and opened my mouth wide. Curling in the edges of my tongue, I stroked him now with two hands, pointing it at my waiting cavern. My hands started in the middle of his cock and slid both up and down, in opposite directions, twisting as they stroked. He growled as I jerked his cock and threw his head back, releasing a primal sound of a man in ecstasy. I felt his first monstrous shot of jism rocket into my top lip, falling from there onto my outstretched tongue. It seemed like a constant stream of hot cum was shooting out of him as the first shot lasted for a long time. As the pressure of it waned, it flooded onto my tongue, overflowing it into my mouth and some of it leaked out to dribble down my chin. I closed my mouth to swallow this fantastic load, thinking by its quantity that it had to be all of his cum. I was therefore shocked when a second shot, harder than the first, smacked my left cheek, just below my eye. This jet flowed like a line across my face, from my left cheek across to my upper lip and into my chin. Realizing he was far from done, I opened my mouth, which was already nearly filled with his seed. His third shot lacked the speed of the first two, but still managed to drain itself into my mouth as I leaned forward. My large mouth began to overflow slightly so I tilted my head back to keep from losing his precious commodity. I now needed to empty my mouth and closed it to swallow, aware that he had more to go yet. I rubbed his cock on my lips as I gulped down his massive load, and he spurted smaller amounts onto my lips, enough to cause it to run down my chin and into my breasts and lap. I let out a yelp of surprise, as a final spurt shot out at the end, hitting my forehead and drooling down my right eyebrow onto my nose. I took him gently into my mouth and milked the remaining cum from his cock, swallowing it and savouring the taste of him. He shuddered and his legs gave out as he stumbled back to collapse onto my bed. "Oh... my... god..." he muttered. Suddenly a knock of the door cause me to jump, and the door swung open quickly. There was a small older man in a brown jumpsuit labelled 'superintendent'. "Hello, I'm here to fix the..." he paused, in shock at my appearance. Here I was, on my knees on the hardwood floor with obvious lines of cum dangling from my face, and a thick coat of shiny saliva on my tits. I quickly covered my nipples as he turned around in embarrassment. All the guy on my bed could moan was: "Oh yeah, I forgot to mention I don't work here, I'm your next door neighbour." And funny enough... I wasn't even mad. The Super Bowl Bet It was the Friday night before the Super Bowl, and I was riding high. My favorite team was playing and I was certain they would win. What made it more interesting was my buddies favorite team was also playing and as you can imagine...we were trash talking all week long. That Friday night, we were out at a local bar pounding a few and getting loud and drunk with each beer. The conversation turned to the big game and we decided to watch it at his place. It was then that the wager was made.... We drank to near closing time, and kept trash talking all night long. Each of us was convinced out team would win and we took turns letting each other know it. Finally my buddy chimed in, "I know we will win. I'm so sure that if they do lose - I'll suck your dick." Now we have both had our share of women, some we have even shared so I laughed it off. He brought it up a few more times prompting me to say, "I'll take that bet and up it. If my team loses - I'll let you fuck my ass!" We shook hands on it and laughed it up both convinced we would not lose, and not really sure where things would go. I showed up on time for the big game that Sunday. Both of us were wearing our favorite teams jerseys and tight jeans. The game began and his team jumped out to an early big lead. My nerves started to kick in and he could see it. He seemed nervous too but kept promising to take his prize. My ass tensed up scared of what would happen to it. Half time came and when he got up to use the bathroom (only ahead by a touchdown) I checked him out. I have never done that before and he was in fact attractive and well built. I started to think about if I won, and wondered if he would really suck my cock. I started getting really hard thinking about it. He returned to the living room carrying a jar of Vaseline. He placed it on top of the TV and laughed walking back to his chair. The game was close up until the end but my team could not pull it off. I was upset to watch him celebrate but really became quite nervous not knowing what would happen. It was then that he remembered the bet and got quiet. He sat in his chair and we sat in silence until he finally spoke up. "You know, I feel bad for your loss. Bet's off!" I was upset but really turned on. I took off my jersey and started to twist and play with my hardening nipples. He sat there quietly watching when I noticed him rubbing his cock through his jeans. I got up and walked towards the TV. I picked up the jar off Vaseline and tossed it to him saying, "A bet is a bet". I dropped my pants and boxers causing my hard cock to bounce out and up. I stroked it a few times and headed down the hall towards his bedroom. I climbed on all fours on his bed, ass up, waiting to see if he would go through with it. It was then I heard him enter the room and approach me. Scared as hell, and not sure if this would happen, I waited trembling. Then I heard him remove his clothes. My cock got even harder knowing he was naked and right behind me. He leaned in to place the jar on the edge of the bed, and it was then that I felt his cock brush my ass. He then started to rub his hands all over my hips and ass and I knew then that the time was at hand. I needed to see him before he plunged deep inside my ass, so I got up and turned towards him. He had a great body. I noticed then how long and wide his cock was. We stared at each other for a few seconds before I dropped to my knees before him. His nerves got the best of him and he tried to pull me to my feet. I took his cock into my hand and stroked it slowly at first building up speed. He let out a moan and allowed me to lean in and begin to lick his heavy balls. I licked them for several minutes taking each in my mouth before letting them spill out. I ran my tongue up the fat shaft slowly tasting his sweet man sweat. I got to the head and slowly ran my tongue over and around it circling it. I wasn't sure if I could go further but pondered how far I already went. I didn't have a choice! While licking the head of that hot cock, he grabbed the back of my head and worked his cock deep into my mouth. He let out a loud moan and held my head while I eagerly sucked his cock. "Ohhhhhh...that's it man. Fuck yes...." he whispered. I couldn't believe my best friend was fucking my mouth and that I was so eager to take it. "It's time to pay up buddy" he said lifting me up from the ground. He turned me around and helped me down on all fours again on the edge of the bed, my ass hanging off. He was behind me and I felt him reach for the jar of Vaseline. I felt him take a finger and rub my asshole thoroughly sliding it inside prepping me for what was to come. I could hear him stroke the lube all over his cock letting out a squishing sound. We were both ready and this would change things forever. He climbed between my legs behind me pushing my knees wider apart really spreading me open. I leaned face first into the blanket grasping it preparing for my ass to get abused. I could feel the head right up against my hole. He then said, "Man if you tell anyone about this, I'll kill you and ruin your life." I mumbled out that my life would be as destroyed as his if anyone found out. It was then that I felt the head of his cock push its way into my tight hole. It stretched me open and start to hurt. I had no time to react or beg for mercy. Before I knew it, he pushed it in deep. I felt his pubic hair tickle my ass and his balls rest against mine as he grabbed my hips. Slowly he pulled out half way and plunged deep inside me again. He picked up a rhythm and fucked my ass for all it was worth. The pain quickly passed and I felt my cock start to throb. I knew that feeling well and could tell I was about to come. He put his weight down on my back and really buried himself inside me. I came all over his sheets. After a few minutes, he pulled out. He rolled me onto my back spreading my legs open. He put my ankles on his shoulders and positioned himself to take me some more. His hard thick cock slid in easier this time and he resumed the pounding once more fucking me deeply in my stretched ass. He reached forward grabbing each of my nipples. He played with them and twisted them while fucking me hard. His breathing picked up and his fucking picked up speed and I knew he was about to cum. Just then, he pulled out and shot a heavy warm load all over my cock and stomach and chest. He climbed up on top of me pressing his cum between our hot sweaty wet bodies. We laid there a while longer before I dressed and left. Football season starts again in a few months and according to the schedule, our teams will meet again! The Super Bowl Bet Pt. 01 Part 1: Introduction Isn't it funny how a single event or two can change your whole world? That's how it was for me when I lost my dad to a heart attack about a year ago. My name is Dean and I'm a 35 year old account executive for a large real estate firm in Virginia. I've worked at the firm as a sales associate since college and have been told I'm a born salesman. Translated, that means I've got a lot of 'BS' with me. People can't help but like me due to my personality which is outgoing, funny and just a bit flirtatious. If I have one fault, it is that I am a "player" when it comes to women and relationships. I am not looking for a long term relationship and tend to play the field whenever and wherever I can. I have even hooked up with some of my co-workers and clients. The big "M" word is definitely not in my vocabulary. This all changed when my father died last year. I became depressed and turned to work as therapy. I stopped going out and dating. I would spend 12 to 14 hours a day working in the office and would even show houses on weekends and nights. While work helped me to forget about my loss, it was evident that I was going to burn myself out and probably end up having a heart attack myself. About 3 months ago I was called into the boss's office for a chat. The owner of the company, Ms. Williams is a bit older than me. She appears to be about 55 years old, but well preserved. She always dresses smartly in business attire that complements her ample body. I know she is a widow and has several children, but know little else about her. When I entered her office she smiled and asked me to sit down. "I am very impressed with your work over the past six months" she said. "As you know, the real estate market is recovering from the recent economic slowdown and I have been considering expanding the business. I am looking for someone to take over a new residential sales team. The team will be in charge of promoting and selling homes in two new developments. I have contracted with the developer to be the exclusive agent for these developments and she wants an aggressive sales team to promote them as she needs to maintain her cash flow during the building process. The position will provide you with a substantial raise and you will get a commission for each sale your team makes. Are you interested?" It didn't take me long to agree to her proposal. I would have three sales agents under me, plus a loan specialist who would assist in procuring any financing the buyers would need, and a secretary who would complete most of the paperwork for the real estate transactions. Best of all, I could pick and choose which properties I wanted to show, picking the ones with the best commissions and leaving the less desirable properties to the other members of the sales team. The following Monday I arrived at work a little early in preparation for my first meeting with my new sales team. As I walked in and scanned the conference room I recognized several of the members of my team while others appeared to be new employees with the firm. Unfortunately for me, two of the team members were sexual conquests of mine from my earlier days. The other observation that I made was that all the team members were female. I made a mental note that this was definitely not the right time or place to think with my "other head". I certainly did not need a sexual harassment lawsuit now that my life was heading in the right direction. I had been in my new position for about three months when my step mom invited me over for dinner. I arrived at her house, the one she inherited from my dad on his death, to find both of my step sisters were also there. "Looks like this is going to be one of those family get-togethers" I thought as I knocked on the door. My step mom opened the door and gave me a big hug as she invited me into the house. Both of my step sisters were helping her prepare dinner and I offered to set the table. I was never really close to my step family while growing up, but one thing I had to admit, her cooking was far superior to the fast food and frozen dinners I had been eating lately. We talked about our jobs and what was going on in our lives during dinner, but I sensed that my step mom had a hidden agenda which I was sure she would spring on me before the night was through. Sure enough, when we were finished with dessert and I was getting ready to leave, my step mom said "Dean, you have been working entirely too much lately and not getting on with your life since your father died. If you don't ease up a bit you are going to end up just like your father. Are you seeing anyone now? Maybe Sarah can hook you up with one of her friends". Sarah was one of my step sisters. She was a year older than me and worked in the emergency department at the local hospital as a nurse. I had been to a couple of parties with her several years ago, and knew that some of her friends were pretty hot, and they certainly knew how to party. Sarah gave her mom the "death stare" for a few minutes and then smiled. "I'm not sure that my friends would be a good fit for Dean. You know we work a lot of odd hours, and besides, I'd be a little concerned about hooking him up with one of my friends giving his history with women." After a brief pause she continued. "I'll tell you what... My best friend Allison is having a small party next Saturday. It's a birthday party for one of the nurses in the unit. If Dean wants to come, I'll check and see if it is OK. If it is, I'll call later this week with the details. Just so you know, if you screw over any of my friends, I'll be real pissed". I was not too thrilled with the prospect of going to a party with my step sister and spending a Saturday night with a bunch of people I didn't know. However, I agreed to go since I knew my step mom would keep pestering me until I did. Saturday night arrived and at 8 pm I was at the address that Sarah had given me. I knocked on the door and was met by Allison. We made our introductions and she invited me in. Allison was one of those women that men dream about. She was about 5' 9" and 130 lbs. She had strawberry blond hair that was neither too long nor too short. The styling fit her to a tee. Her breasts looked to be about a 38D and her hips were well proportioned to the rest of her body. She had a fine ass and it was apparent she worked out daily to maintain a fine figure. She introduced me to some of the guests then slipped away to mingle like hosts do. I ended up talking to the one or two people I knew and then sat down on the couch and tried to look entertained. About 11 pm the party was starting to wind down. I was also thinking about leaving when Allison came over and sat down with me on the couch. "Need some company?" she said. "Looks like you've been sitting here alone most of the night." We started talking and any thoughts of leaving were history. After talking for an hour or so we realized most of the guests had left. I told her I probably should be going as well, but asked her if I could see her again. She said that would be great and gave me her number. "I'll definitely give you a call" I said as I made my way to the door. As I opened it she grabbed my arm, pulled me close and gave me one of those hugs to die for while whispering in my ear "I hope it will be soon". The Bet Allison and I had been dating for about three months. I was quickly falling for her, even though I had not been able to get her into bed with me. Whenever I would suggest escalating the relationship, she would always say "That is something you will have to earn, but when it happens I'm sure it will blow your mind". She constantly teased me through our months of dating. It certainly kept me interested, but a little frustrated as well. I was determined to keep up the attack doing things that I thought would please her like buying her flowers, doing things with her that she wanted to do rather than things I enjoyed doing, and giving her massages and back rubs. I knew what she wanted. The big "M" word and she was using sex, or more accurately "no sex" to drive me to it. It was the Friday before the Super Bowl when I came up with an idea that I thought might work. We were having dinner at our favorite restaurant. I thought for a moment on how to best to proceed. It was after several glasses of wine that I finally came out with it. "Allison, how about we make a bet on the Super Bowl?" She looked at me with a quizzical expression on her face, but didn't say anything. I continued. "The odds makers have it as a toss-up. So, you can pick either team. If your team wins, I will do whatever you say for a week. If your team loses, you have to have sex with me as often as I like for a week". I sat there and waited for the shoe to drop. At least she didn't immediately get up and leave or slap me across the face. She sat there and stared at me for a few minutes and then smiled. "I'll tell you what, Give me 10 points and I'll take the Seahawks". Wow, was I surprised. I knew the Seahawks didn't have much of an offense, and the Broncos, with Peyton Manning throwing TD after TD this year were sure to score a ton. I figured that this was a sure thing. I agreed immediately. After all, if I lost I would have to do some chores around her house, stuff I would probably do anyway. If I won, I would enjoy a week of sex, something that I had not experienced in over a year due to my self-imposed celibacy. It seemed like Sunday would never come. I was like a kid waiting for Christmas day so I could unwrap my presents. The only difference was the present I was going to unwrap was Allison, and boy was I going to play with her. I could only imagine all the positions and sex we would experiment with when she paid up. She called me on Sunday morning and suggested I come over to her place to watch the game. She had a great media room with a large HDTV and sound system. I thought that was a great idea and offered to bring some pizza and beer. She said she would prefer wine, and bring enough for four as her two sisters would be there as well. I was a little disappointed in hearing this, as I had hoped for some pre-game groping, but since I had already agreed, I felt obligated to go. "OK" I said. I'll be there about 4 pm." When I arrived we put the pizza in the oven to keep warm and went into the media room to watch the pre-game activities. Ann and Ashley, Allison's sisters were already there kicked back in recliners watching the show. I had met both of them previously. Both were fine looking women. Ann was a little older than Allison and worked as a para-legal at a law firm in the D.C. area. She was about 5'10", 150 lbs and had auburn hair. Although she was a little heavier than Allison, she wore her weight well. The biggest difference between her and Allison was her attitude. I guess it was partially due to her job, working in a profession that was dominated by men, but I got the impression that she was a true feminist and had a bit of a chip on her shoulder. Ashley was younger than Allison and had a model's body. She was tall, in fact she was nearly as tall as me. She was probably 6' tall and 120 lbs. She had long blonde hair which she kept tied back and seemed to be more outgoing and fun-loving than her sisters. She was an aspiring artist and worked as a receptionist in a doctor's office when not painting. It was obvious that she loved to flirt and began doing so the minute I entered the room. I sat down on the couch with Allison and we began drinking and watching the show. We talked about our jobs, the upcoming game and the commercials that were sure to be as entertaining as the game. After about an hour we got the pizza out and started pigging out. After a few more beers I was ready for the game to start. The game started out badly for the Broncos and they were soon down by a couple of touchdowns. Allison looked over at me and said "I going to enjoy winning this bet and having you do whatever I want for a week." As soon as she said that, Ashley chimed in. "What bet? Come on Allison, clue us in. Did you make one of your wild-assed bets with Dean? Let us in on the details!" Ashley continued to prod for several minutes and finally Allison spilled the beans. "Yes, we made a bet on the game. If I win he has to do anything I want for a week. If he wins I have to have sex with him as much as he wants for a week. I took the Seahawks and 10 points. The way things are going so far it looks like he's going to have to pay up". "Not so fast there Allison. There is still a lot of game left to play". I sounded like one of those commentators who tried to keep the fans interested even though the outcome looked pretty well decided. "The Broncos had some bad luck so far, but there is still plenty of time left. Don't count your chickens before their hatched." Ann was beside herself. "How could you sell your body like that? What if you lose the bet? I can't believe you did that!!" "Come on, Ann" Ashley said. "They've been dating for three months now. She's probably already let him have it once or twice just to keep him interested. Besides, giving the circumstances, she probably has a pretty good chance of winning this bet. I think it would be fun having a boy toy around here for a week. I wouldn't mind getting in on the action too. How about you?" Ann thought about it for a bit, looked at the score and time remaining in the first half and then smiled. "OK, if he's willing, I'm in, but let's make this real interesting. I think the bet should be a week with each of us. That's a total of three weeks. Three weeks of sex for him or three weeks of service for us. What do you say? You up for it?" I couldn't believe what I was hearing. I looked at Allison for guidance, but she simply smiled and said. "The ball's in your court. You don't often get a chance to have sex with three sisters. Especially three as hot as us. It's your decision." Well I guess I was thinking with the wrong head. My good head was buzzing from the alcohol, and if I had been smart, I would have been paying closer attention to the game. "OK" I said. You're on. I win I get a week of sex with each of you. You win, I'll do what each of you want for a week". The girls got up and huddled, then Allison turn to me and said "OK, but I want to make this official. No backing out on either side. Ann is going to type up the agreement for each of us to sign". By the time Ann got back with the document halftime was almost over. We all signed the agreement and she filed it away for safe keeping. As the final seconds ticked off the clock the girls counted them down together. I couldn't bear to watch as the final gun sounded ending one of the worst super bowls in history, at least as far as I was concerned. Allison looked at me and then at the other girls. "I know you cannot take off three consecutive weeks from work to serve us, so we will space this out a little. Tell your boss that you would like to take a week off since you just closed on that big deal last week. I am sure she will agree. You've been putting in too many hours lately anyway. It's time you took a little time off. Report here next Friday at 6 pm and be prepared to stay the week." After a brief pause, Allison added "Just so that you know, although you will be serving me beginning Friday night, both Ann and Ashley will be staying here for the week. There won't be a time that you are left alone, and they have my permission to punish you for any disobedience or failure to do as you are told". As I left her house following the game, I began wondering what was going on. I had thought I would be doing a few chores around the house, but the way Allison talked, I would be supervised by one or all of them for the entire week and punished if I didn't perform well. I began to get a little nervous, but my "other head" became excited as well. The Super Bowl Bet Pt. 02 Part 2: It's going to be a long week I arrived at Allison's house on Friday night as required. Both Ann and Ashley were there as well. Allison began by asking for my car keys, wallet and cell phone. "You won't be needing these this week, and as long as I have them, you will think twice about leaving." She took the items to her car and locked them inside so I could not get to them. When she returned she let me know what to expect during the coming week. "This week you will be our boy toy. You will remain naked and serve any woman who enters this house. Failure to perform an assigned task properly will result in punishment. Failure to address any woman with respect will result in punishment. Failure to achieve an erection on demand will result in punishment. Do you understand your responsibilities?" "Yes Allison." "That's Miss Allison. You will address all women as Ma'am or by their name preceded by Miss or Mistress." You have earned your first punishment for disrespect, Strip and bend over." Miss Allison proceeded to administer 10 strokes with a leather paddle to my naked bottom. Following the punishment I was order to crawl to each of the women present, kiss her feet and ass, and beg to be allowed to serve her during the week. I went from Miss Allison to Miss Ashley and finally Miss Ann; begging each of them to allow me to serve them. When I had completed my task I heard laughter coming from behind me. I turned to see Sarah, my step sister and Samantha, her sister. Both were looking at me with amusement. Let me tell you a little about my step sisters. Sarah is a year older than me. She has always been a little plump, and I would always tease her about it when growing up. I would play tricks on her and basically try to make her life miserable. Today, she stands about 5'10" and weighs about 160 lbs. She's what one would call a "full figured" lady, although I would not call her fat. She has brown hair which she keeps cut short. Samantha is 6 years older than me, making her 41. She has been married once which ended in divorce. As she has gotten older she has put on a few extra pounds and could be considered a BBW. We never really saw much of each other growing up as she was away at college when her mom came to live with us, but I remember her as having a bossy attitude which is probably why her marriage failed. Anyway, I quickly got the impression that their being here would not be good for me. Sarah was the first to speak. "Well Dean, I guess you thought I was doing you a favor in setting you up with Allison. In reality, I was paying you back for all the heartache you caused me growing up. You see Allison and I have been lovers for 2 years. No, we're not lesbians, we are both bisexual. The thing is, when we have sex with men, we always take the dominant role. Allison is ready to settle down. She wants to experience a Female Led Marriage and has been looking for the right male to dominate. I told her about you, your history with women, and your treatment of me during childhood. She thought you would be the perfect challenge to convert into a submissive husband. Looks like your training will start this week, and guess what? Sam and I will be here to help her out. Won't that be fun?" Samantha walked up to me a put her boot in my face. "Go ahead and kiss it, then my ass. Beg me to allow you to serve me this week. When you finish, go do the same for Sarah." I couldn't believe what I was hearing. I had been set up by my own step sister and now had to serve these women for a week, maybe more. Friday night was a blur, no matter what I did, I couldn't avoid being punished over and over. They would create new rules throughout the night just to give themselves an opportunity to punish me for breaking them. They would humiliate me as often as possible, and constantly kept my cock erect through teasing. If I dripped pre-come or worse yet, ejaculated without permission I was forced to eat my semen and then was spanked, paddled or whipped for my transgression. I was required to orally service them for hours at a time. I ate more pussy, kissed more ass, and worshipped more feet than I had done in my entire life. Around 2 AM they finally got too tired to continue. Miss Allison brought out a bag of ice and wrapped it around my cock causing it to shrink. Once soft she placed a chastity device on me and locked it with a key. "You will not be getting any relief tonight. Tomorrow your real training starts. Go up to the spare bedroom and get some rest. You will sleep on the floor next to Samantha's bed. Wake us at 8 am." I tried to sleep that night, but the pain in my cock from the inferno chastity device as well as the pain to my ass and back from the countless paddling and whippings made sleep difficult. I must have dozed some because I was awakened at 7 o'clock by Samantha, who then rolled over and went back to sleep. I cleaned myself up as best I could, and at 8 am went into Miss Allison's room to wake her. "Get down and give my pussy a nice wakeup call" she demanded. "When finished, wake each of the other ladies in a similar fashion starting with your step sister Sarah. Then, go and make us breakfast. I will be down shortly to supervise." Waking each of the ladies took longer than expected, and several required a long session of pussy worship. Miss Allison was waiting for me when I arrived in the kitchen. "You have earned another punishment for keeping me waiting" she said. "I will put it on my to-do list for today since I am hungry. Fix my breakfast, and make it good or risk additional punishment." As I started preparing breakfast she sat at the table writing down a list of chores and duties I was to perform that day. The other ladies soon accompanied her at the table and made further suggestions to add to her list. When breakfast was ready I served it in the dining room. All of the ladies ate and complemented my on my cooking. "At least there is something you can do right" one of them commented. "At least we will eat well this week." I looked at the list that they had compiled and I realized that there was no way I would be able to complete it. Miss Allison had to go to work and Miss Ashley was heading out to the gym and to run some errands. This left me with Miss Ann and my two step sisters. I wasn't looking forward to the rest of the day. I began with cleaning up the kitchen from breakfast. I was able to eat what the ladies had left, but I was still hungry when I finished. After finishing in the kitchen I was off to straighten each of the bedrooms the ladies had slept in last night. It was obvious that Sarah and Allison had slept together in her king sized bed. The second bedroom was Ann's and it appeared she had slept alone. Ashley slept in a third bedroom and Samantha had the guest bedroom with me on the floor. After straightening each of the rooms, changing their bed linens and tidying up their bathrooms, I went back downstairs to see what was next on the list. There was laundry to do, floors to scrub, furniture to dust and vacuuming to do. The ladies supervised with paddles and made comments on how things should be done, deficiencies in performance, and on two occasions how I disrespected them by getting an erection without permission. All in all I earned 10 punishments in addition to the one Miss Allison had bestowed upon me that morning. I was told I would receive them tonight after dinner. Dinner was served at 6 pm. I prepared chicken parmesan and salad and made sure I prepared enough so that I would have plenty of left overs since I was famished from serving Ann and my step sisters all day. Once dinner was over and the kitchen straightened, I was summoned to the dining room where the ladies were enjoying the last of a bottle of wine. Allison said. "I understand you were less than stellar in your performance today, and were disrespectful as well by obtaining an erection without permission. You will now be punished for your actions. In fact, there is a punishment waiting for you for keeping me waiting this morning isn't there?" "Yes, Miss Allison" I replied "Very well. We will proceed to the basement. You have not seen this part of the house, and it will be a little frightening to you when you first see it. However, you will become quite familiar with it before you are allowed to leave." As we proceeded down the stairs into the basement, me crawling behind Miss Allison and the other ladies following with crop in hand, I was becoming more and more nervous of what was about to take place. Miss Ann occasionally swatted my butt when I did not move fast enough and Miss Allison would pull on the chain attached to the collar around my neck. Miss Allison opened the basement door and what I saw did indeed frighten me. Before me was what could only be described as a fully equipped dungeon. There was a rack full of paddles and whips, a cross, a device that looked like a stocks, a pillory and several pieces of furniture I didn't understand at the time. I was sure I would be acquainted with each before the week was through. Various rope and chains hung from the walls. There was even a winch attached to the ceiling. Miss Allison dragged me over to the rack and attached me spread eagle to it with my butt fully exposed. "Punishments are designed to modify undesirable behaviors and mold the individual into performing in an acceptable manner. In order for a punishment to be effective, the individual must learn there will be consequences for their undesirable actions. You will learn this tonight. You have earned 11 separate punishments which is a lot, even for an experienced slave. You had better learn how to minimize these punishments in the future or its going to be a painful three weeks for you." As I looked over at the other ladies staring at me I saw each had a smile on her face. It was evident that they enjoyed administering pain, and that I was probably not the first person to endure their wrath. The first punishment was a paddling from each of the ladies with a sorority paddle that Ann had kept from college. It was a typical wooden paddle with holes drilled in the business end and the Greek letters sigma-sigma-sigma engraved into it. Ann took the paddle and said. "This is for failing to properly make my bed this morning. You will receive 20 swats from each of us. If you should get an erection at any time during the paddling, I will whip it off of you and start over. Is that clear?" "Yes Ma'am I replied," and from the very first stoke I was sure that I didn't have to worry about an erection. Each swing of the paddle ended with a painful "thud" on my ass and by the time Miss Ann was through my ass was as red as the red thong panties I was made to wear. Samantha was next, and if anything, her swats were more vicious than Ann's. Each woman proceeded to bust my butt. Ashley, the free spirit was last to go. I thought that maybe she would have some pity on me, given her happy-go-lucky attitude, but unfortunately for me, she proved to me as stern a disciplinarian as each of the other ladies, and the leverage she produced using her long arms to swing the paddle reminded me of a professional tennis player making a forehand return. By the time they were done I was crying like never before and begging for them to stop. I was given a few minutes to recover while they went to get another bottle of wine. When they returned they released me from the cross only to reattach me facing outward. This time it was Sarah who spoke. "Your second offense was to disrespect me by getting an erection in front of me while washing my panties this morning. I even caught you sniffing them once. You will learn that you are to achieve erection only when ordered to. Failure to do so, or obtaining one without permission will result in punishment. You should be doubly ashamed of getting an erection in front of your step sister. For this punishment, each lady will stroke your cock until hard. She will not stop until you are ready to explode. If you cum without permission, the paddling you just received will be repeated. The lady will then take this penis whip and whip your cock until you are soft again. Off course, she is free to stroke you some more to try to prolong the whipping. I looked at the penis whip and saw a whip with a short braided handle which ended in a number of leather strips. It looked like a miniature cat-o-nine tails I had seen pictures of. Sarah began stroking me and after a while my cock responded to her touch. She continued long after I had become erect and soon I was begging her to stop, fearful of cumming. Finally, she picked up the whip and began. After about 20 strokes she was satisfied with the results. Allison went next. My cock was still hurting from the previous whipping so it was difficult for her to get me hard. She stopped her stroking, bent down and took my cock into her mouth. It was like nothing I had ever felt before. She was an expert in teasing my cock and finally it was as hard as ever. She picked up the whip and smiled. "Sarah gave you 20 strokes before she was satisfied. You had better allow me at least that number of strokes or I will be extremely unhappy, and remember I get to select your next punishment." Thirty strokes later she was satisfied I had been sufficiently chastised. "Next" she said and Ann stepped forward. By the time each of them had a turn my penis was raw and my balls blue. The rest of the evening followed suit. I was beaten, teased, restrained and humiliated by each of my five mistresses. I licked pussy and ass, sucked on toes and feet, and massaged their bodies until each was satisfied. The final humiliation I had to endure was having a plug inserted into my anus and locked in place when my chastity belt was reattached for the night. I was then sent to Ashley's room to sleep on the floor next to her bed. The Super Bowl Bet Pt. 03 Part 3: The week continues Sunday went much like Saturday. I woke early and orally serviced each of the women before making breakfast. They slept in later than on Saturday. I guess they were tired from all the activity of the preceding night. Sarah and Allison left for work together following breakfast and Samantha left to visit my step mom for the day. The list of chores for today involved a lot of outdoor activities. I was to work in the garden, do some landscaping and mow the lawn. I also had to wash and wax the three sister's cars. I worked while wearing a bra and thong panties. Allison's yard was fairly well protected by shrubs. She had neighbors on both sides of her house and I could hear them working away in their yards. Her neighbor to the east had a two story house, and I swore I saw shadows in the second floor windows staring down into Allison's yard as I worked. The street she lived on was fairly quiet with only an occasional car passing by. Her front lawn wasn't large, but still would take a half hour or more to mow with her push mower. Even though I would be exposed, wearing only women's underwear, I was not given any additional clothing while I did the mowing. I practically ran with the mower trying to get done before being seen by one of her neighbors or anyone passing by. Ann and Ashley lounged on the porch watching me work and teasing me with comments about how nice my tan lines would be, and how they would need to buy me a training bra with padding since I didn't fill the one I was wearing out properly. Occasionally I would hear a horn sound as a car passed by. Once I head some cat calls and saw Ann waving to an older lady walking her dog on the sidewalk across the street. "If you run out of things for him to do, just send him my way. I definitely know how to treat bad boys, and he certainly looks like he has been bad to me" she said as she made her way down the street. Occasionally she would turn and laugh at what she had seen. By the end of the day I was again ready to drop. I had managed not to earn any additional punishments, but my ass was still sore from Saturday's activities in the basement and the butt plug I was forced to wear all day. When Allison got home she said she wanted a steak and baked potatoes for dinner. She gave me a pair of woman's pants and a ladies blouse that she had purchased in my size and told me to put them on over the underwear I was wearing. "Here is enough cash to purchase what we need for diner. Although you are dressed in women's clothing, you should be able to pass as a man unless you draw unwanted attention on yourself. Go to the local grocery store and pick up what we need. If you don't have enough money, then you will have to figure out how to make up the difference. I am sure there will be a few ladies there who might like a quickie in exchange for a handout. Hurry back because I am hungry and you don't want to keep me waiting. Remember yesterday morning! By the way, don't even think about trying to skip out. Your chastity device has an integrated shocking device that will start shocking your balls should you travel more than a mile from this house. Fortunately there is a grocery store about half a mile from here. They have really good prices and is owned by a friend of the family. Now get going." I got dressed and got in my car. Although I was dressed in female attire, I agreed that it wouldn't show unless I had to stop and have a conversation with someone. It felt good to be away from the ladies, even for a short time. I thought about running, but figured the consequences were not worth the risk. I just had to endure this week, and then a week with Ann and another with Ashley then I would be free. I'd go back to work and never think of getting in another relationship like this. There definitely wouldn't be any more bets like the one I was foolish enough to make. The grocery store was easy enough to find. I parked the car and went inside. They were not real busy for a Sunday evening, in fact I think they were getting ready to close. I picked out some steaks, a bag of potatoes and some salad and started for the checkout. I only purchased enough for the girls as I wanted to be sure I had enough money for everything. As I got up to the cashier, I noticed her staring at me more than normal. I started to become more self-conscious. Could she see the bra under my blouse? Did I appear overly nervous, or was I just imagining things? When she finished ringing up my purchases she said it would be $43.54. I panicked. Allison had only given me $40.00. "I'm afraid my girlfriend only gave me $40.00. I guess I will have to put something back" "Wait a minute" she said. "Is that a bra you're wearing under your blouse? I bet you even have panties on under those pants. I noticed the panty lines as you walked in. What's your girlfriend's name? I know most of the people in the neighborhood, maybe I could give her a call?" I told her what she wanted to know and she whipped out her cell phone and called Allison. After a brief conversation she turn back to me. "Allison is a dear friend of mine. I've known her family for years. I think we can work something out here. Let me just close up and lock the door. I have an office in the back and you can work off the balance of what you owe. What was it, $3.54?" We headed to her office. What choice did I have? She was older than me, probably in her early 50's. Her hair was starting to grey a little. She had large, sagging breasts and an ass that would tax any seat and hang over on both sides. I guessed she tipped the scales at well over 300 lbs. "Let's see. For $3.54 I think I should be entitled to a couple of orgasms. Since I know you have on a chastity belt, I guess I will have to settle for your mouth. Lay down on this bench, face up. I'm going to sit on you face until I've had my fill, and it's been a long time since I've sampled any oral from a white boy." Oh. Did I forget to mention, she was an African American and she enjoyed having white boys under her. She put all of her weight on my face, shifting every so often to allow me to get a gasp of air. First she sat facing my feet, placing her pussy over my mouth and wiggling her ass so my nose was embedded between her ample ass cheeks. She rode me like that through an earth shattering orgasm and then turned so that her ass now was over my mouth and my nose rubbed her cunt. She rode me like that to a second orgasm, rubbing her cunt on my nose and forcing me to stick my tongue up her ass, licking her rosebud and occasionally penetrating it. After about 45 minutes she was done. She refused to let me wipe my face and sent me on my way. I arrived at Allison's a few minutes later to find her furious. "That's two punishments for you. One for keeping me waiting, and the second for not figuring out how to pay for dinner on your own. Emily had to call here instead of you confessing you were my slave and offering to service her in exchange for your purchases. From now on, you will be buying all the groceries we need for the rest of the week at her store, and I will not be giving you any money to make your purchases. Now go fix dinner, your punishments can wait until after we eat." I was getting more and more worried. More women were using me every day. I had now served six different women, and it was only Sunday. No telling what the rest of the week, or the two additional weeks of service had in store for me. This was also the first time that Allison had called me her slave, and that scared me even more. I had to find a way out of this predicament. The punishment session following dinner was not as severe as the previous night's. I received a paddling and a whipping from each of the ladies. The butt plug was removed and I was told to go clean it. "You're lucky she doesn't make you clean it with your mouth" Sarah said as I went to wash the plug. When I returned I saw that Allison had a larger plug in her hand. This one was metal and had a large head which narrowed to a slim neck. "This one is designed to stay in place without the need of a strap. You will wear it until tomorrow night when I replace it with a larger version. If it should fall out, you will ask the first woman you see to replace it for you. You will also receive a punishment for losing it. If you need to use the bathroom, you will have to ask someone to remove it for you and reinsert it when you are finished. Again you will receive punishment for its removal. Now off to bed. I want to make love to Sarah and you will just be in the way." The rest of the week followed in much the same manner. Ann and Ashley had to go to work each day. Ann seemed to be more of a sadist than the rest of the ladies, so her absence was a relief. Allison or Sarah were there to supervise when not working and the step sisters were in and out. Most of the ladies were present at night, but since all were busy with their jobs, the amount of punishment I received was minimal. I did housekeeping, odd jobs around the house and in the yard, and of course, made my daily trip to the grocery store. On Friday morning Allison announced that tonight would end my week of service to her. I still would have a week of service to Ann and Ashley to perform, but those would be scheduled at a later date. Tonight there would be a party and I would be the guest of honor. Allison would not tell me more but stressed that I should be sure that the house was immaculate, that I prepare refreshments for those attending, and that I should be prepared for a long night. "How many should I prepare for?" I asked. I'm expecting around twenty or so.... Give or take. You never know whose going to bring a friend to my parties. They're the talk of the town you know. By the way, since your week is up tonight I have decided that if you please me during the party tonight I am going to give you a little reward" "Reward" I thought, "If her rewards are anything like her punishments, I think I might pass." "If you please me, I am going to let you have sex with me, as much as you like, for the next week, Just remember, I wouldn't plan any pay backs for this week, as you still have two additional weeks of servitude to fulfill. I can guarantee you that my sisters will be glad to punish any inappropriate behavior. But just so you know, when it comes to sex, I am insatiable. You already know of my cock sucking ability, and I love vaginal and anal sex just as much, so if you're interested, you better stock up on those little blue pills because you're going to need them." The Super Bowl Bet Pt. 04 Chapter 4- The Party I was totally confused all morning. Allison had as much as told me she was going to screw my brains out next week. If she had told me this last week, I'd be the happiest man alive. After the week of hell I had just endured, I wasn't sure I wanted to take her up on the idea. I also still had two weeks of hell to endure, one with the sadist Ann and the other with Ashley. I wasn't looking forward to either. By noon I had the house in order. It really wasn't that dirty as I had spent most of the week cleaning this or that. I still had to make refreshments for the party which meant heading down to the grocery store once more, a task I wasn't looking forward to. As I drove to the store I began wondering about the party. Was this going to be some of Allison's co-workers coming over for a get together like the party where I first met Allison, or was this going to be something a little more exotic with me serving a bunch of horny women? I wasn't in any real hurry to find out. I arrived at the grocery store about 12:30. Emily was there with a grin on her face as she saw me approach. "What can I do for you today?" Emily asked. "Need some supplies for the party tonight?" My stomach immediately started doing summersaults. "Ah, yes ma'am. I need some stuff for snacks, and I guess I better buy some wine and beer. Do you know what Miss Allison normally serves at her parties?" "Sure" she said. "I go to them all the time. She has these things about once a month, but it's been awhile since she's had any special entertainment for us. Tonight should be special. I'll get one of the girls to get everything you need. Come on back to the office and we'll arrange for payment. It'll be a pretty big bill so I hope you can pay." Well the bill for all the party supplies was over 200.00. Since I didn't have any money, I had to agree to serve Ms. Emily for a week to pay the debt. She said I didn't have to serve her now as she knew I would be busy all afternoon, but she would be getting some freebies tonight at the party. As I left the store I had little doubt that tonight was not going to be a fun night for me. Little did I know how right I would be. By 6 pm the sisters were all there. Allison, Ann and Ashley were getting ready upstairs as I was putting the finishing touches on the refreshments. Allison came down and said it was time for me to get ready. She handed me a thong and told me to put it on. I could wear what I wanted over top of it. "Maybe this won't be so bad" I thought. "At least she's letting me wear normal clothes over my panties." My step sisters were the first to arrive. To my surprise, entering behind them was Jane, my Step mother. I blushed a little and hoped that Samantha and Sarah had not told her too much about my week. A few other ladies arrived over the next 15 minutes. Three or four I recognized from the previous party I attended. Allison greeted them and I assumed they were co-workers. Around 7 pm Emily appeared along with two of her employees I recognized from the grocery stores. "These are my daughters Rachel and Cecilia" she told Allison. "Hope you don't mind me bringing them. They've never been to a party like this, and I thought it would be a good learning experience for them." "Not at all" Allison said. "We're all one big happy family at these events and tonight will prove to be a special night, just you wait and see." I went to work serving drinks and greeting women as they arrived. I could see that this was to be a hen party, as I was the only male in attendance. By 8 pm there were over 20 women present ranging in age from about 20 to over 60. Some were well dressed, as if coming straight from an office somewhere while others were obviously dressed more casual and ready to party. At about 8 pm I went to answer the doorbell. When I opened the door I gasped and took a step back. "Is that any way to greet your boss" said Ms. Williams. Entering with her was the human resources manager of the firm, Ms. Reynolds and Mary, the loan manager from my team. "I think you know Robin and Mary. Please take our jackets and bring us a glass of wine. By the way, I hope you enjoyed your vacation this week, you'll have a lot of catching up to do when you come back to work Monday." I was shocked to say the least. Here was my boss, the HR director and a co-worker of mine at a party where I was sure to be the entertainment before the night was through. My step sisters and step mother were here also, along with about 20 other women I didn't know or barely knew. I had a feeling something bad was about to happen. After I had served everyone drinks, some were on their second or third by now, Allison got up to speak. "Can I have everyone's attention? Several months ago I met Dean here at a party. We have been seeing each other since. Dean was foolish enough to make a Super Bowl bet with me which he lost. He has been forced to serve me for the past week in any way I wish. He was also told that he must serve any woman who enters this house. Therefore, tonight he will serve any of you in any way you desire. Feel free to punish him if he fails to meet your needs. I have also told him that if he performs well tonight, that I will reward him for his efforts. At the end of the party I will take a vote to see if he will be rewarded or not. Have fun and let the party begin." I was told to strip to my thong and the ladies went wild. Allison sat back and watched as several of the women came up to me and started rubbing their hands over my body. The Alcohol was making the women lose any inhibitions they had and soon I was orally pleasing one after the other. My thong was ripped from my body and there I was naked in a room with over 20 women. I lost track of how many pussies and asses I serviced and how many women rode my cock. I remembered Emily sitting her large ass on my face followed by her two daughters. My step mom mounted my face and rode it like she hadn't had sex forever. After a while, I was no longer able to maintain an erection and my cock was so raw I couldn't stand anyone even touching it. My tongue was numb and I could no longer differentiate the taste of pussy from ass. I was nearly ready to pass out when Allison stopped the action. "I think we have succeeded in wearing him out sexually. Is everyone satisfied?" A chorus of "NO! WE WANT MORE" repeated over and over again. "Very well then, since he has failed to satisfy you he must be punished. Ann, would you go to the basement and get a variety of paddles and whips so these ladies can show this boy what happens when they are left unfulfilled?" In the meantime, Allison continued. "OK. I have been training his ass for the last week, let's see what he's learned." I was tied face down over a padded bench with a spreader bar attached between my ankles. Wrist restraints were attached to my wrists and a rope tied from my hands to my ankles. The rope was pulled tight bending me over and totally exposing my asshole to the crowd. Several strap on harnesses were produced. A variety of strap on dildos laid out on the table. Some were smaller than the anal plugs I had been wearing all week while several were much larger. I started to cry as I realized what was about to happen. I was lubed up and the first lady stepped up to plunge her weapon into my ass. After three or four of the women had their way with me Allison came up to me with Ms. Williams by her side. Both were wearing harnesses with an extra-large dildo attached. I guessed them to be at least 10 inches in length and over 2 inches in diameter. I was sure it was larger than anything I had taken to this point. Allison began. "Tonight I will ask Dean to marry me. He will have until next Friday at this time to decide. If he accepts, he can expect many more days and nights of serving women. All women will be his superiors. He will be subjected to weekly play parties such as this, and he will be loaned to any of my friends upon request. Now, I think it's time I fucked him right." Allison mounted Dean and thrust her dildo in with a single stroke. She waited a moment before brutally raping his ass with her phallus. After about 20 minutes she withdrew and Ms. Williams stepped up. "I hope you accept my daughter's offer of marriage" Ms. Williams said. "It will be good having a man, I mean boy, around the house again. I'm sure we can find some additional duties for you at work as well. Since you'll be marrying into the family, I'm sure you won't mind the added responsibilities. Of course, if you decline her offer, you will have to find a new job as well. There's no way I could continue to employ a pervert like you in an office full of women unless I was sure you were under the control of someone like my daughter." I looked up at her and couldn't believe what I had just heard. My boss was Allison's mom. And if I didn't agree to marry Allison, I would lose my job. I think this is known as a no-win situation. Ms. Williams continued. "Just so you know, I have copies of all the pictures that were taken this week including those taken tonight. I have made a copy of your contact list on your phone which includes many clients and business contacts. If I should send them a copy of these pictures, I am sure finding another job anywhere within a hundred miles of here will be next to impossible. If I post them to the internet, you might as well apply for bankruptcy and look for a job digging ditches somewhere. Maybe Emily would hire you." With that Ms. Williams grabbed my hips and thrust with all her might sinking her massive rod balls deep into my rectum. She withdrew completely and thrust again. This time she got into a rhythm and rammed my ass for what seemed like 30 minutes. I cried the entire time. By 1 AM the women had lost their enthusiasm to play. They continued to drink wine and beer and talk about the night's activities. Allison realized that there would soon be a problem given the number of women present, the amount of alcohol consumed and the number of bathrooms available for use, so she came up with one last indignity for me to endure. She went down to the basement and soon returned with what looked like a portable potty that looked similar to one that would be use while camping. She gave me the toilet and told me to place it in the corner of the room with a piece of plastic under it to prevent spills from messing her floor. As I placed the toilet I noticed an opening between the legs. Miss Allison told me to stick my head into the opening face up. She attached my wrists to the toilet's legs and placed a plate around my neck which locked me into place underneath the toilet seat. She lifted the lid and inserted a funnel in my mouth that ensured anything deposited into the toilet would end up in my mouth. As she was doing this several of the women gathered around to watch. They made comments like "No, she's not going to make him a toilet" and "Oh, I think I feel a pee coming on." The comment I feared most was from one lady whose name I didn't know who said "I think I'm going to be sick, I shouldn't have drank so much." Fortunately for me, she got sick before Miss Allison had me ready for use, so the woman rushed to the bathroom rather than vomit in my mouth. While she was gone, the other women got the urge to pee, and one after the other they sat on the portable toilet to do their business. The party broke up about 8 am Saturday morning. A vote was taken to see if I had passed the test of the party and should be rewarded. The vote was close, but I passed. I noticed that Ms. Williams both my step sisters, and my Step mother voted against me. Still, I was to be rewarded with a week of unconditional sex. The last of the guests didn't leave until noon. I was kept as a toilet until that time. When I was released, I was given my clothes, car key, phone and wallet and told I could go home. Allison said "I agreed to have sex with you anytime you like this week, whenever you're ready just give me a call. Right now you better get some rest, you look kind of tired; and you smell like piss too." So now I sit here on Sunday afternoon. I slept for 16 hours straight. I've cleaned myself up and look like nothing unusual has happened. When I return to work tomorrow, I am sure most of my co-workers will know of my ordeal, I'm not sure how I will face them. I need to decide if and when I will have sex with Allison this week, and more importantly if I will accept her offer of marriage. I don't know how I will cope with a life where I have to submit to her at home, and most likely her mother at work. What's worse, I don't know what I'll do if I reject her offer and my experiences are exposed to the world. All my friends and co-workers and even my step family will abandon me. I'll have no job, no way to pay my bills, and in reality, no life. All because of a silly little bet.