3 comments/ 35347 views/ 6 favorites The Dictator and the Waitress By: Trimpostinger It is a different experience being married and in college at the same time. My name is Allison Derringer. Last year it was Allison Pinster. My husband, Derrick (yes, Derrick Derringer), and I started dating when I was a freshman. We met because of the swim team. I tried out freshman year, but didn't make it. He was a 5th year senior. He was on the swim team, and since he also hadn't made it his freshman year, he still had a year of eligibility left after his senior year, and he had taken a light course load the previous 4 so swimming wouldn't get in the way. He needed the fifth year to graduate. Over the past two years we made up a lot of reasons why we had started dated. He insisted it was that he wanted to give me encouragement to try out again my sophomore year like he did. I said it was because I needed help in accounting, which was one of his majors. But as far as I am concerned, it was because as soon as we saw each other in a bathing suit, we fell in love. My friends tried to tell me that I was too young, but when you meet the right guy, why wait. Yes, I am only 20, and he is 24 but we are very compatible. We dated sparingly my sophomore year, since he was busy working in the real world. A bunch of his finance friends from college had started a business that specialized in investment plans for some of the local celebrities and specialized mortgages and so forth. I don't really understand it, but I do know he makes a ton of money and bought me a killer ring. And now that we live off campus I don't have to worry about all of the silly housing rules that the college enforces on us. It worked out well for my friends at college too. Four of us were close friends after freshman year and then sophomore year we picked up a fifth. The juniors had access to suites that allowed four to a room, so it was a question as to what to do with one of us until I moved off campus. I miss the camaraderie of dorm life, so I still spend most nights in their room studying and talking. The one thing we really liked doing as a group was to make crazy bets with ourselves. Invariably the bets turned lewd in some way. Who could go the longest without wearing underwear? Who could last longest naked outside when the temp dropped below 50? Go skinny dipping in the college pool after hours. You get the idea. As junior year stared, it took a while for us to get used to our new classes, and by the end of October we still hadn't tried any crazy bets yet. I figured Halloween was as good a chance as any to get a new one. "I assume you are all going to the Halloween party this year," Cassie said, "and taking dates?" Cassie was the only loyal dater in our group besides me. She had been dating the same guy for almost as long as I had known Derrick. The other three changed boyfriends with the seasons. "Yes," I added, "when are we going to meet the latest guys in your lives?" Tanya shrugged. "I guess I could get him to go. We've only been on a couple dates but Halloween is fun." Betty was also nodding her head, but Kelly looked skeptical. "I'm not a real big fan of Halloween," she complained. "It's just a chance for women to dress up like sluts." It was a typical comment from her. She was a good friend, but she was also drew the least attention from the guys. She was the shortest, yet other than Betty who was 5'10'' and very athletic, she was the heaviest. She didn't have it in her chest, either, sporting a 36A bra size. We all told her she was still pretty, and she got enough guys (probably because she was very easy), but when trips to the beach, or laying out in the sun to get a tan, or anything else that would magnify her body compared to ours came up, she usually fought it. Betty actually came to her defense. "I know what you're talking about. Just because I can fill out a Wonder Woman costume doesn't mean I should have bare myself for everyone." And she could fill it out too. I figured that when she graduated from college, if she couldn't get a real job, she should be a sports bra spokes person because how she kept those 36C's from bouncing all over the court when she played basketball was a mystery to me. "Last year," Betty continued her rant. "I wore it and that jerk Gary wore the loosest fitting Batman costume I ever saw. It looked like his pajamas. Last I checked, Batman wore a skin tight costume with his crotch on display for everyone. It's a lousy double standard." Tanya, Cassie, and I usually liked dressing up. We were all about the same size, 5'6'' to 5'8'', 120-140 lbs, 34B with differing hair colors. I had had been blonde, red, and black in the last three years, but Derrick liked my natural brunette the best, and the natural color had finally gown out to shoulder length. Cassie kept her auburn hair half way down her back in a variety of braids, while Tanya's natural dirty blonde was usually bleached platinum. None of us had a problem wearing revealing clothes. In fact, we usually enjoyed getting stares. Cassie and I were confident enough with our men to do it, and Tanya was just an overall flirt. Of course, she usually attracted the jealous types as she was the most "Cover Girl" worthy of the group. That was why she rotated boyfriends. "What if we made it different this year?" I offered. "What if we make the guys wear the skimpy outfits?" "And how would we do that?" Kelly asked. "Why don't we make it a bet?" Cassie offered. This had the desired reaction. All the girls got in closer. We were sitting on beds, chairs, or bean bags and we all leaned in now. We all loved our bets. They made our lives more exciting. "What kind of bet?" Betty asked. If the bet was physical in nature, she almost always won. "The girl who can convince her guy to wear the skimpiest costume wins," I said. "What is skimpy for a guy?" Tanya asked. "That wench outfit you wore last year had your breasts practically spilling out, but you were covered with several layers down to your ankles." "Which ever guy shows the most skin," Cassie clarified. "And it has to be a costume with a theme. Don't just put a sock over his dick and drag him to the party." I could see the three girls with new boyfriends mentally calculating how they could convince their guys to dress skimpy for a Halloween party. It was a party put on by our hall, not a school-wide thing, so they wouldn't necessarily run into people they went to class with. "What does the winner get?" Betty asked. We all sat and thought for a while. "What about the sex tapes?" I asked. "What about them?" Tanya replied. One of our bets last year was that we each hade to make a sex tape with the guy we were seeing at the time. We never really discussed what the loser would have to do, but since we were all successful, it didn't come up. We each watched the first minute of the tape to verify it existed, and that was it. We were each required to keep it for future use. "The winner gets to watch the tapes," I suggested. That was met with resounding "No"s. At least I tried. Kelly actually came up with it. "Okay, so we can't watch each other's sex tapes, but if the winner shows off her guy, then the losers have to show off their guy even more. The four losers have to provide a naked picture of their man to the winner." "How naked?" Cassie asked. "All the way," Kelly said. "You either strip him down as much as possible for the party or you go the whole way later on. We can decide on a time frame for how long you have to produce the pictures, assuming you don't already have them." Kelly was looking at me as she spoke, and I was pretty sure why. All the girls liked Derrick. He was a swimmer and a long distance runner. He looked really good without his shirt on, and the size 15 feet that gave him an advantage in the pool led my friends to assume other parts of his body were largely proportioned. Kelly wanted naked pictures of my husband. And yes, I already had them. But I didn't plan on losing. "What if we can't get the pictures?" Tanya asked. "You mean what if you break up with the guy after the party?" Betty chided. "No, I mean what if you can't get them. Not every guy is going to pose for pictures." She turned to Betty. "And you had more guys last year than I did." "Easy," I said, trying to stop a fight. "If you don't get a picture of your guy for the winner, then a naked picture of you goes in the vault for future use." The vault was a memory stick we kept in a safe that we each had one number of the combination too. On that stick was a bunch of incriminating evidence from our sex tapes, to erotic stories we each had to write, to a bunch of other things. "It needs to be stiffer than that," Cassie argued. "We've already got our sex tapes in there." "Then make it the tape. If you can't get a picture of your guy, the rest of us who did and the winner get to watch your tape." Tanya looked hesitant at this, but the rest of us looked like we agreed. It was put to a vote, and it was finalized. It was Wednesday, and the Halloween party was next week Friday. We had planning to do. The Dictator and the Waitress This was how my night went. I was practically dressed like a man, in German attire which was made up of a baggy gray shirt and boots with a green coat and mid calf boots. With the cleavagy or skin tight (or both) outfits worn by the other girls, I didn't get too many dance offers. Instead I watched my husband's ass get slapped, his washboard abs get felt up, and his potato get so abused, that by the end of the night it was barely hanging on by a few threads. I wouldn't be surprised if in 9 months several girls at the party gave birth to a baked potato. I decided to survive by eying up the boyfriends of my friends knowing that I was going to see naked pics of them soon. Betty's boy was the best catch, and I got hot thinking of him posing for my athletic friend and then the raucous sex they would have afterwards. At the night's end, Derrick was damp with sweat from the dancing and alcohol he had consumed. I was a good underage partier (I turned 21 in January) and stayed sober. I wasn't a big beer drinker anyway, and they weren't serving martinis. "Did you have a good time?" I asked him, not sure how upset I should be with him. If I wanted to strip him down to show off, and then all the girls liked him, how mad can I be with him? "It was good," he replied. He got his coat from Bo Peep, who by now must have heard the dictator joke and giggled as she ogled his spud. The potato was still in one piece, but the threads had ripped a bit was it hung lower and almost on its side. His natural bulge was now clearly visible and it was tough for me to know which one the shepherd girl was grinning at. Either way I helped him with his coat to cover up and we left. "So I assume we won the bet," he said once we were in the car headed home. As I drove I explained the bet and confirmed with him that we did win. He was a bit disappointed that by winning I got to see naked pictures of their guys -- something he wasn't interested in seeing. But I told him that the way he danced with some of my friends, they might be breaking up with their boyfriends, in which case I'll get to see the sex tapes. That he was interested in. When we got home Derrick needed a shower and I changed out of my costume into some PJs and sat reading on the bed to wait for him. Even though I was thinking about naked men, sex tapes, and my husband humping every girl at the party, I wasn't feeling like sex. My mind was too scattered on how I should feel about winning the bet, since I did it by pimping out my husband. What was he going to make me wear tomorrow night? Did he enjoy tonight enough not to take revenge? Derrick interpreted my mood enough to know that I wasn't up for a romp in the sack that night and probably relieved his sexual tension by jerking off in the shower. He came into the room in the boxers her wore to bed, we kissed goodnight, and fell asleep. The Dictator and the Waitress Half of me wanted them to, though, and it gave me a thrill as I felt them creep lower and lower down my hips. Eventually, you could see the white of the thong join together in the front. I guess Derrick thought that was enough, because as I delivered drinks to a table next to the pool, he walked up to me. I flashed him a smile. "Yes, dear?" "Having fun?" he asked as he began to pull the money out of my thong. "Actually, yes," I replied. After he pulled out all but his original $5 he adjusted my shorts back up. "Am I showing too much skin?" I asked, not realizing what he was actually doing. He was really just stalling, which I didn't realize until a minute later. "I've got it!" some yelled behind him. Derrick turned slightly to see someone catching a toy football out of the air and take two more steps toward us. "Woa!" Derrick cried putting up his arms to catch the receiver before he bowled us over. He took two quick steps back as the guy came into him. Derrick bumped me back too, and I had to take two quick steps back. My second step didn't find the pebbled patio surface where I thought it should be, and I turned to look. In horror I eyed up the placid surface of the pool as my left foot frantically tried to pull back. It was too late though and my center of balance was already over the edge of the pool. I screamed like a little girl and tossed the platter to the ground as I measured my length in the pool and splashed down. The water was pleasantly warm, but I got up in a flash anyway, more startled and shocked than anything else. The sudden unexpectedness of it took my breath away, and I quickly pushed my head out of the water. I was only waist deep, as my hands when up to pull my hair back. Derrick was leaning over the edge with his toward me. "Honey, I'm sorry, let me pull you out." He betrayed me with his eyes. He looked directly at my face instead of where he should have been looking. I thoughtlessly extended my hand to him, and he yanked me out of the pool in a smooth, strong motion. I stood there, still very much in shock as the water ran off me. I was breathing heavily and still pulling my hair back to keep the water from running in my face. It took me a moment to notice how quiet it had suddenly become. My scream and splash had drawn a crowd of eyes. I suddenly realized that everyone was staring at me, and unlike Derrick, they weren't looking at my face. My eyes went down in sudden realization to see that my thin tank top as now as transparent as a wet tissue. I might as well have been topless. And even worse, as Derrick had yanked me out of the water, my loose shorts had stayed behind, and my cotton panties were also completely transparent, showing off my trimmed bush and bare pussy lips. I did the only thing I could think of and jumped back into the pool. Despite the waist deep water, I squatted down so only my head was above the surface. Derrick squatted down by the side of the pool and looked at me to make sure I was all right. "You did that on purpose!" I scolded him. I kept my voice down, but firm. The people behind him realized the show was over so they were going back to their food and drink. Derrick didn't deny the accusation. "So you have a wet T-shirt. There are several women here in string bikini tops." "But they at least cover themselves," I argued. "You can't see anything through your shirt." "What?" I scoffed. "You can see everything." "Really?" he questioned. "Stand up a little." I walked closer to the edge of the pool so that Derrick blocked the view of anyone else and stood up slightly. He didn't need to explain what he meant, and I'm sure what he intended all along. With "Hooters" written boldly across my chest, that portion of the shirt was not transparent. Still, you could see the complete top, side, and bottom of my breasts and the entire rest of my torso. "You showed more skin last year," he tried. I didn't, but I got his point. I showed everything except nipple last year, and now the letters on my shirt covered half of the front of my breasts. "But they saw my thong," I said weakly. "When I came up to you, you were proudly showing that off yourself. Which way do you want it? Do you want to flaunt in front of their implanted bimbos, or do you want to hide in the pool?" His logic was grating. Yes, I had proudly flaunted my body around just minutes ago, playing with the idea that my shorts would drop at any second and becoming thrilled with the idea. Now that it had happened, I was playing coy. "If you really want to show up these fake women out there, let them and their husbands see what a real female body looks like and we'll see who they ogle." "Can you at least get me another shirt?" I asked. "You agreed to wear this outfit all night," he said. "Should I tell your friends you went back on the deal that you used to get me to wear the potato? I'm sure that violates some 'Bet' code." He had me. And the more I thought about strutting around in my wet tank top, the more the idea excited me. I saw the red shorts floating next to me and stepped back into them. I walked over to the steps out of the pool this time, not wanting another sudden jerk to take the shorts down again. When I got out of the water, I realized that it wouldn't take sudden movement to get them down. They were so water logged they were falling off on their own. Derrick gave me room as I got out, but I later guessed he was just giving his friends another view. They weren't crowded around me anymore, but they hadn't gone far. And while before they had openly stared, now they looked at me sideways, pretending to pay attention to what their wives and girlfriends were saying. I quickly realized that unless I got some duct tape, these shorts weren't staying up. In full control this time, I let the shorts drop to the ground and stepped out of them, glad I had worn sandals tonight. I watched the men watch me, their eyes focused on my pussy and the tuft of hair above it. I squatted to pick up the shorts to maintain their great view of my crotch. I rang out the soggy shorts several times, becoming more and more confident in front of these guys. I mean what were they really seeing, anyway? They could see the clear outline of my body beneath my wet clothes. That was it. The skin tight outfits their wives wore showed the same thing. Every year I look at the painted swimsuit models and wonder what it must be like to be viewed wearing only the illusion of clothes. Now I knew, and it was thrilling. I almost didn't want to put the shorts back on, but as I stepped into them, it gave me an opportunity to spread my legs as I lifted them into each leg hole. I heard a few gasps as I did this. I was happy to find that the shorts stayed up this time, but rode extremely low. The back of the waist band rested on the full curve of my ass, revealing a couple inches of bare cheek in the back. In the front, an inch or two of my thong was visible, showing off a sliver of dark hair and basically only covering my clit and below. It was perfect. I stood up straight, throwing my shoulders back as I did. My boobs still bounced, but they no longer did so under my shirt. Instead, my shirt moved with them as it followed my every curve. I walked over to where I had tossed my platter, and then walked back to the table I had just served. "Can I get you gentleman anything else?" I offered as if nothing had happened. Derrick's original five dollar bill was soaking wet and still secured on my hip, and the slack jawed guys eyes started there, roamed all over my body, and ended up back at the money. "She deserves something for that show," one of the women dressed as the Tomb Raider chick said. The guys agreed and each pulled out a twenty. One guy was across the table, and I pushed my hip against the edge, half sitting on it as my shorts were pulled down another couple inches showing him almost all of one butt check. He reached over and paid me. The other guy was on my side and I stood right next to him, my left breast one inch from his face as he stuffed his money under my wet thong. I was nothing short of a spectacular hit at the party. It lasted 4 more hours, and by the end of it, I was dry again, but I got no less attention. While I was still wet, several of the guys asked to have their picture taken with me. It was funny to see them hand their camera to their wives and then smile back at them as they stood beside me with their hands on me. I could also see Derrick getting a lot of respect from his co-workers and friends. It would be unfair to say that EVERY woman in the place had fake breasts or lipo done, but a large percentage of them had, and the others looked just as superficial. Derrick had managed to land himself a hot, outgoing wife (me) without having to manufacture one. Unlike last night, when we were ready to go home, I was incredibly turned on. I had finally felt dry about an hour ago, and I had considered jumping back in the pool. Who knows, I might have even left the shorts in the pool this time. I didn't, and the guys were all sad to see us go. Derrick had had one too many beers (okay, 10 too many) so I drove home, which was too bad, because if he had I was prepared to go down on him in the car. He was apparently thinking the same thing, because he was all over me as soon as we pulled out of the driveway. His hands reached under my shirt and he quickly pulled it up to release one of my breasts. He leaned over and began sucking on it hard. I helped him out by releasing one arm from the steering wheel so he could pull the shirt up over my shoulder, and then released the other arm from the wheel so the shirt could come off. It went to the back seat as he licked and sucked at my right tit while the left one got a strong massage. I bit my lip as I tried to concentrate on my driving, wondering how many traffic lights we were going to need to stop at. His right hand dropped into my lap and I began to squirm. I put on cruise so I could lift my ass out of the chair a bit and soon my shorts and thong were around my ankles and I was driving through North San Diego naked. Derrick's fingers were soon inside me as he continued to suck on my breasts. As I felt the familiar tingling sensation rush through me I wondered what impaired a driver more, alcohol or an orgasm. All I knew was I was about to find out. My vision went blurry as I fought through the two drinks I had had that night as all the blood I had quickly raced back and forth from my brain to my clit. Derrick's fingers played me like a banjo as he plunged deep inside me with each strum. He could feel I was getting close and began to whisper into my ear. "Come on you sexy thing, cum all over my driver's seat." He reached over to my door to roll down the automatic window. "I want you to scream into the night air." It was too much. "Fuck yes!" I cried, the wind from the open window blowing my hair back as I exploded between my legs. I bounced up and down in the seat swerving the car across the center lane several times. I heard car horns, but they sounded distant as my mind and body was consumed by my orgasm. I sensed Derrick's leg thrust past mine and him grabbing the wheel but I continued to gyrate in my seat as the orgasm flooded through me and I flooded onto the driver's seat. I was jolted back to reality as the car skidded to a stop, turning 180 degrees as he spun out onto a shoulder and cars screamed past. I opened my eyes, not realizing that they had been closed. We were parked backwards on a scenic lookout pull off along the cliffs. The ocean crashed beneath us and Derrick had a frightened look on his face. I was still flush with excitement and popped out of me seat to climb over the center consol and sit on his lap. His fear was quickly replaced with passion as I pressed my breasts in his face and pulled at the button of his pants. Soon his cock was out and I sat down hard on it. He moaned as my well lubed hole swallowed his dick and I rode him hard, the aftershocks of my orgasm still coursing through me. Traffic slowed to regard our unique parking technique and we got several more honks as people witnessed the action inside. I didn't pay any attention to them and fucked my husband hard. He responded in kind, his hands on my hips while he thrust up. I felt another orgasm building (I usually got them in bunches) and as I heard him grunt and release inside me, I came again, adding fuel to the burning fire in our laps. The orgasm lasted a full minute and I think I passed out because the next thing I remember was sitting in the passenger seat, still naked and sticky, while Derrick was driving. My hands went looking for my clothes, rubbing over my body. When they found my pussy, I didn't look any further and began to play with myself. I only half noticed Derrick looking down at me as he feverishly raced to try to get us home. It had been a good Halloween weekend.