Miss Keven Jeanne Sissyfag
- 2 years ago
- 68
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My wife and I get together with our neighbors to play cards to play cards about once a month. We generally have a good time but there are no stakes involved. For a poker player like me who is accustomed to gambling for large amounts of money playing just for fun is a little, well… boring. One night about a month ago, I tried to make the game a little interesting by including some drinking. We started the night playing pitch, with the loser required to drink a shot of Jack Daniels.
With the whiskey flowing, I became a little boisterous and suggested we raise the stakes. I proposed the loser of the next game be required to serve as a maid for a week. The room got quiet as everyone pondered the proposal. Our neighbors, Jim and Judy, said they were a little too drunk to play for such high stakes. My wife, Amy, said I had a good idea.
Jim said to me, “I bet you are picturing Amy in a little French maid’s outfit right now.”
I quipped, “The thought had crossed my mind.”
Judy said, “Um, what does Amy get if she wins?”
Amy jumped in with a quick response. “I get the same thing, right? Joe has to be the maid for the week.”
Everyone chuckled Amy’s comment.
“I am serious. The deal is whoever loses serves as the maid in any capacity the other wants.”
I said, “Sure.”
We stuck with pitch as the game of choice and Jim and Judy served as impartial judges just to make sure all the rules were followed. The game was close the whole way but in the end, I got lucky by getting dealt a strong hand and I won. Of course, the Jack Daniels had taken over all of the common sense I usually have, and I began chiding Amy about how hot she was going to look in her maid outfit.
“I can’t wait to have dinner served to me with you in a short skirt and fuck me pumps.
Judy said, “Just be careful there Joe, payback can be a bitch.”
It was late so we called it a night but as our guests left to return to their home I continued to tease Amy about how great it was going to be to have her wait on me all week. I told her I would order her maid outfit so I could make sure she had a nice low cut top and short skirt. Amy took all of my ribbing quietly. I expected her to protest but she did not utter one complaint. I told Amy she might have to take the week off from work to be able to serve me properly but in retrospect that was not a good suggestion.
The card game took place on Thursday so we agreed to start the payoff to the bet after the weekend on Monday. I did not say much more about what Amy would be required to do to fulfill the bet but I had a lot planned in my mind. We had a fun weekend and Amy did not seem to be too worried about starting her week of servitude on Monday.
Sunday night I laid out the outfit Amy was to wear for the week. I had purchased a very sexy black maid’s outfit. I knew the skirt would barely cover her ass and I bought her a pair of five-inch platform pumps just in case she told me she didn’t have any to wear with the outfit. I typed out a list of chores I expected Amy to do for me each day. In addition to everyday cleaning I expected her to make all of my meals and to serve them to me in the place of my choice. I spelled out that Amy was to always be completely made up and to always wear my favorite perfume. Amy read the list but did not show any negative reaction to it. She was actually very compliant and agreed to everything on the list. Of course, I expected some sexual relief too but I figured I would get to that later.
I woke up Monday to Amy standing next to me holding a cup of coffee and a fresh towel for my shower. She was wearing the maid outfit and looked quite hot. I thought about requesting some head for my morning wood but I knew there would be more time for that later.
Amy greeted me with, “Good morning, Master.” I hope you slept well. Here is your morning coffee and a fresh towel for your shower. Shall I start the water for you?”
Amy was certainly being a good sport about losing the bet and paying up. I said it would be nice to have the shower started.
“Yes, Sir. I will then go prepare your breakfast.”
As I got out of bed to go to the bathroom I thought to myself this was going to be a great week. After a nice shower I dressed in the clothes Amy had put out for me and then Amy served me a terrific omelet for breakfast. She asked me if I would like her to do anything extra that was not already on the list I had given her.
“No, but I would like to have a chicken dish for dinner. But don’t you have to get ready for work today?”
“Oh, no. I took the week off as you requested so I could serve you.”
I knew this must have been very hard for Amy to give up a week of vacation to be my servant. I remembered I had suggested that she might need to take time off to fulfill my desires but I was kidding. I did not expect her to follow though with my bombastic request.
“Anything in particular?”
“What?”
“Would you like a specific chicken dish made for you tonight?”
“No, surprise me.”
After an uneventful day at work, I returned home to a clean house that had the smell of roast chicken wafting through it. In retrospect, I should have complimented her on all the work she had completed but I didn’t even acknowledge it. Instead, I had Amy give me a back massage. I should have been more appreciative of all the hard work she put in today but I played the part of the insensitive master instead. She served me a cocktail and I watched some television before dinner. I invited Amy to sit with me for dinner and after a little cajoling, she agreed to since the “master” approved it. Amy’s chicken was awesome. She wasted no time cleaning up right after we ate. I got a little caught up in the power differential we had through our bet payoff and I told Amy I could use a blowjob. She walked me into the bedroom and did just what I asked. Again, I should have been appreciative but I wasn’t. Had I known my actions were going to come back and haunt me I certainly would have been nicer.
The remainder of the week went pretty much the same. Amy took care of everything that needed to be done in the house, cooking, cleaning, sexual favors etc…She did look so hot in her outfit it was hard for me to keep my hands off her. Jim and Judy came by one night and Amy served drinks. Judy was uncomfortable having Amy wait on us in her provocative uniform. She told me I was being insensitive and was taking the bet too far. Jim smartly stayed out of the conversation.
I told Judy, “It’s not big deal. It’s just payoff on a bet.”
Judy countered back and said, “You are lucky. I don’t think you could handle for one day what you are putting Amy through. Do you have any idea how hard it is to walk in heels like those all day?”
“She’s used to it. It can’t be that bad.”
“Now you are just being a jerk. The least you could do is offer Judy a rematch.”
“I will be happy to but I doubt she would want to lose again.”
Judy walked into the kitchen to speak with Amy. They spoke for a few minutes then Judy walked over to me.
“Okay. Amy said she would make the same bet with you again.”
I replied, “I don’t know. I seem to be taking a lot of shit for making her pay up on this bet.”
“I thought you would chicken out. She was even willing to change the game to hold ‘em and play a one on one tournament against you.”
This was too much for me to resist. I played Texas hold ‘em much more than any other card game and I knew Amy was inexperienced at that game… so I took the bet.
“Okay. If she wants to play for the same stakes in a one on one tournament of hold ‘em I guess I will have a servant for another week.”
Amy only had one more day of servitude to settle the bet so I offered to be a nice guy and play the game tonight. I also said I would let her stop paying off the bet one day early if she wanted to play for the new stakes right away. At the time I made this offer I did not take into account I had a few drinks in me and that tends to make me a little more reckless when I gamble.
Jim could see no way that this could end up good for him so he told Judy that they should go home and let us play the game. Judy said she wanted to watch a little bit of the game but she told Jim it was okay for him to go home. So Jim left and we set up the game. Amy and I sat down to an equal stack of chips in front of us. The winner would be the one who ended up with all the chips in front of him or her. Judy offered to be the dealer for us and we got started.
I knew I could take advantage of Amy’s inexperience playing this form of poker and I bet aggressively right from the start. This strategy worked initially and I took a decent amount of Amy chips over the course of the first few hands. We then got involved in a hand in which the pot built up quickly. My aggressive betting was called pre-flop, on the fourth street, and on the river. Amy had flopped a set of sevens so there was no way she was folding and she took the hand and the big pot. That hand gave her a small chip advantage. Judy took note of the momentum swing.
“Oh, oh, Joe. Don’t look now but Amy has more chips than you. Are you wondering what you might look like in her skirt?”
I laughed loudly. “I am not worried. And I am guessing Amy will have some type of butler uniform for me if I did lose.”
After that comment, Amy simply smiled but Judy laughed out loud.
“Ha! Yeah, right.”
I knew Judy was trying to get into my head and cause me to make a silly mistake that would cost me all my chips. As it turned out it all came down to a matter of luck…bad luck for me. On the next hand, I flopped a ten high straight but I wanted to disguise it and let Amy bet into me. The plan worked perfectly until the river card paired the board. I thought this gave Amy two pair that made it perfect for me to call her all in bet. When she flipped over pocket tens I realized she had a full house and I had lost! Amy did not even realize she had won until I sunk my head and Judy broke out in a cheer for Amy.
Judy chuckled, “Oh, you are so screwed now. I can’t wait to see how you look in heels!”
Amy just smiled a devilish smile. Would she really make me wear the same outfit I had her wear? I did not think she would but I was beginning to wonder. I had really belittled her at times this past week and made a lot of sexist comments. If she wanted revenge she
was going to have a perfect opportunity to do so now. I also knew that Judy would be happy to egg Amy on to embarrass me like I had embarrassed her. Amy and Judy had a celebratory drink then Amy went home but not before she took one last shot at me.
“I sure hope you get a chance to serve Jim and I drinks sometime next week just like Amy did tonight.”
Amy said, “What a good idea. Let’s plan on that.”
Amy and Judy said goodbye to each other and I began to start worrying just what Amy might have in store for me. I am sure she had some ideas but she wasn’t willing to tell me any of them just yet. She simply said it had been a long night and suggested we get some sleep. She also said we both had some prep work to do tomorrow to get ready for my week of servitude which started in two days. Before I could fall asleep I had to ask what she was expecting of me when my week of service started.
“Pretty much everything you had me do,” Amy replied before rolling over and drifting off to sleep with a sly smile on her face.
Amy was up early the next day. As we were sharing a morning pot of coffee she flitted about the kitchen. She told me she was working on my list. I knew she meant she was preparing a list of expectations as I had created for her. She finished her coffee and said she had some errands to do and a uniform to buy. I didn’t inquire any further as to what the uniform might look like. At least she wasn’t making me wear her outfit. I don’t think it would have fit. We are close in size but Amy is definitely smaller than me.
As she was leaving she said, “When you get in the shower use my shower gel and then make sure you shave off all of that ugly body hair.”
“Excuse me?”
“Well, I guess you can wait a day until your servitude actually starts but I am asking you nicely to do it now.”
“To do what?”
“I want you to shave your entire body smooth.”
This should have been my first clue that I would be wearing the same sort of outfit I had Amy wear during her service time. I knew by the tone of Amy’s voice she was serious and I also figured I had better comply or things might get worse for me. So after she left I showered and shaved off all my body hair. I am not a very hairy person but there was a noticeable difference in how my clothes felt on my skin with my hair gone. I found it felt quite nice, almost erotic. I went about the rest of the morning doing some writing and trying not to wonder what Amy had planned for me but it was hard to focus on anything with those thoughts creeping into my consciousness.
Amy came home toting some bags and boxes in her arms. I asked if she needed help and she said she had everything under control and that I would see tomorrow most of the items she had bought. After she got her bags put away Amy handed me her list of expectations for the upcoming seven days. At the top of the list above my actual chores, she had written that I was expected to be in uniform and full makeup from the time I got up until I went to bed.
I inquired, “Full makeup?”
“Oh, yes. You will have help with that the first day but it is your job thereafter.”
“Um, what do you mean?”
“Tomorrow morning you have two appointments. You have a corset fitting and a salon appointment. At the salon you are getting your nails done. Also, your hair is going to be cut and styled into an acceptable style for a maid. The makeup artist will do your makeup and give you a lesson so you can do it the rest of the week. Then when you get home I have a sexy little maid outfit for you, just like the one you had me wear.”
I did not need to ask if she was serious. The look on her face told me she meant every word. The revengeful little smile coupled with the slight lift of her eyebrows told me Amy was thinking, What do you think of your bet now? I know I was very demeaning at times during Amy’s week of service but Any seemed to be ready to make things much worse for me.
End, Chapter One.
Don’t forget to check out my bio for info on more stories. Or go to Amazon and search erotic crossing-dressing by JNBPUB.
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Hey everyone, this is SB sorry for the delay in this episode. I have been busy with life, and lost interest in this story and many others. Had a writers blocked. But thanks for reading this, sorry took forever to put up, but someone convinced me to keep writing. Thank you SB Episode Three: The Passion Faith looked at him. She felt her love for him. She always loved him. And just maybe this was the beginning to something amazing. ‘I love you.’ Faith whispered, as she lean into kiss Steven’s...
I want to catch everyone up. I had just watched my wife have sexual relations with her black minister on a movie camera I had installed in our home and I watched the whole scene. The following is what my next move will be. My wife was supposed to go down to her friend Ellen's apartment who lived fifty miles away from our city. She was going to stay until I got back from LA. I had my friend Mike put a GPS on her car. Now, it was time to check my computer and see how far she had gone. When I ran...
Cheating WifesThis is a story about how I made an innocent bedroom fantasy into a reality in Las Vegas.My wife and I have been married now for 5 years. We are in our early 30s. She's sexy 5'6 with double dd's and an ass that literally swallows up her thongs/g-strings. Anyways so we went to Las Vegas 2 years ago to celebrate her birthday. We have both expressed fantasies and scenarios about having a 3rd person join in but never thought it would actually happen. On our 2nd night we went to this club called XS....
My mother got sick on her Asian Simmered Halibut with Rice Wine in May, 2002. Because of that, Bradley and I didn't have sex that Friday night. We didn't get it on until a Saturday night in June, 2012, ten years after college and five years into my marriage. When that Saturday night finally came I think I was certain I was going to do it, but if there was any smidgen of doubt left in me then it had to be the wedding that pushed me those last few inches. You know about women and weddings? They...
Wife LoversWhen you have been going into chat rooms from earlier than the age you are allowed, you develop a lust for different and more extreme, so by 29 I would admit online to desires for older men, black guys and rough gang bangs and dogs!. Jerry was black, 64 and had a silky tongue for role plays and sex fantasy chats. Over three months I don’t know how many chats we had and he had got me off (and vis versa). I sent him pictures initially of me clothed and then topless holiday shots and finally...
Jerry also had an idea, coming from a boast that I could still fit into my wedding dress, I had made during our conversations. Jerry always wanted to fuck a white bride and I still had my wedding dress. “You’ll do as my bride, we will collect you at 4 tomorrow afternoon.” And they shipped me home in an Uber, freshly showered, still slightly high, very horny and naked except for shoes, my long blouse and Jerry’s belt. For the Uber driver this was an added benefit as I knelt in the passenger...
I smile an approving grin as you bend over the pool table to take your shot. I had chosen your outfit for the night, and in my opinion, I had chosen very wisely...It was our second night out on this hastily planned weekend getaway. A weekend away in Lake Tahoe sounded like just the thing to escape the blistering hot weather we'd been having. I found a good deal on a nice hotel in south Lake Tahoe and off we went. Last night, weary from driving, we had a nice dinner and a few drinks at the plush...
Wife Swappers Revenge by Diana Kimberly Heche Part 1: Ideas The poker game had long since died out, nothing left on the table but potato chip crumbs and the smell of stale cigars and beer in the air. Nothing left that is, if you didn't count Jake and me. We had raided the pantry for whiskey a full two hours ago and could only be described as drunk. Very drunk. An hour ago we sung sloppy tunes like some stereo-typical depiction of an Irish souse. And only half an hour...
or Yo Quiero Ren Stevens - a depraved parody of the episode "Shutterbug" - Note: in case you were wondering, the alternate title owes its origin to the fact that the actor who portrays Doctor Paz is, apparently, the same person who does the voice-over for Taco Bell's chihuahua. Fourteen-year-old Ren Stevens could not help but beam at her own reflection in the mirror. Thanks to her mom's eleventh-hour arrangements, she was going to have her braces removed in time for her 8th grade photo...
HotwifeI woke up during the night with Marcus cuddling me and playing with my pierced nipples, which once again was making me wet.I climbed on top of him and proceeded to rub my pussy all over his hard cock. It wasn't long after that I pushed myself down him which caused us both to orgasm again and then we fell back to sleep.We woke up about ten. We both needed a shower. Marcus proceeded to wash me paying special attention to my pierced nipples and pussy. I decided, 'Two can play this game.'I...
Wife LoversI guess I have always been a pussy hound, I always liked to spread myself about and when I got married I saw no reason to change, that was until my wife found out and decided to teach me a lesson!I had been at a local sports bar having a few beers with some buddies on Saturday afternoon and got home at about 6.00, to my surprise and joy I was met at the door by my wife and she was wearing the short short checkered mini skirt that didn't even cover her butt cheeks and a lacy push up bra that...
The add in the swinger magazine read:Wife: 352My wife April is 25, and at 5' 11" she is very tall and curvy. When she wears a pair of 4-inch heels she turns heads from across any room. Her hard tipped breasts are smooth, soft and perfectly shaped. She swims and works out regularly which gives her a hard flat tummy and trim figure. April's long blonde hair, beautiful blue eyes and long sexy legs make her look a little like the blonde model in the Victoria's Secret catalog she always gets. She...
Jane spread the tools of her new therapy program before her. There was a pill, her iPod nano, and a vibrator. Jane stripped off her baggy sweater and sweat pants. It was 2pm and she had just come from work where she spent most mornings as the part-time floor manager for a small, independent bookstore. Fortunately, they didn't care what she wore, and so Jane was able to dress for comfort. Following Dr. Susan's instructions, Jane took the pill ("a mild sedative, to help you relax", Dr....
The next morning Steven went back to Anna's. They went up to her room and talked about Steven's conversation with his dad the night before. No longer was Steven just entering this to fulfill his desire to crossdress. He was also doing this to honor his mother. He stripped down to his boxers, and they went to work on practicing his makeup. When Anna was satisfied with his makeup, she put a wig on him. This time when he saw his reflection he smiled. Seeing his mother's face smiling...
WIFE GETS BANGED MY A UNION IRONWORKER My wife Annie and I live in the suburbs of New York City. We are in our late forties, kids are all grown and gone, we each have decent jobs and are starting to enjoy life without worrying about pets or children. A few weeks back we decided to visit the Hamptons for a long weekend. We love the beach and since it was the off-season, the motel rates were reasonable and the weather was fantastic. So we left on Thursday and had until Sunday to enjoy our...
Understanding Our Man’s Hotwife Fantasy and How to Use That to Our AdvantageThe fantasy of having a “Hotwife” is growing, in fact, research shows it is growing at a higher rate than a good majority of the other lifestyle alternatives, including the old staple of “swinging” and the modern “open relationship”. Why is it that a fantasy that revolves around only one part of a relationship – the woman – going out and finding pleasure from another man more intriguing to an increasing number of men...
Finally, I thought. Some schooldays never end. Until the bell rings that is. I packed my things and headed for the door into the hall, hurriedly passing the other classrooms before the hall filled itself with fugitive homesick students. When outside I made a dash for it until I heard the only voice in the school with stopping power over me. “Girt, Girt. Wait for me.” I would always wait for Vicky. She was the most beautiful thing on two legs to walk around Juneau. Even more beautiful than...
Loss Prevention By Alyssa Davis 8/96 The Help Wanted ad said, "Retail security position open at Macy's Department Store. Experience necessary." Tommy was ready for a change and this job interested him, so he proceeded to the personnel department, now referred to as Human Resources, at Macy's where he filled out an application and was immediately scheduled for an interview with Louise Clark, the manager of the Loss Prevention Department. "Hello Ms. Clark, I'm Tommy Andrews. I'm...
Andrea stepped down off the bus, feeling self-conscious. She shifted her daybag to the other hand, and hurried away from the stop, positive that everyone on the bus knew exactly what she was doing. The feeling was silly, but it hadn't stopped her from worrying through the entire ride across town. In a block or two, she would be safely inside, and she could forget all about it. Andrea turned her thoughts to the weekend. She didn't have much in the bag – just one change of clothes, and a few...
Straight SexI had my husband tied to the bed, as he claimed he loved to be. I timed mybobs to correspond with his thrusting hips. John's cock, purple with need,slid in and out of my wet, red-lipsticked lips effortlessly. My fingersencircled his shaft, stroking in time with my mouth and urging him to cum."Oh God!" he cried. "I am gonna cum!" My response wasn't spoken, becausethat would require me to break suction from his cock. Instead, I hummed apleasurable sound that conveyed my willingness to accept...
Wife's Revenge - Part OneBy billy69boy and Nora91"What the fuck were you thinking?" Victoria yelled, "Did you think I wouldn't find out? I can't fucking believe it! Why did you even bother to marry me?"With that she walked out, slamming the door behind her. She discovered that her husband had been having an affair behind her back, and she couldn't bear to consider the consequences right now. All she knew was that she was hurt and furious, and she needed to get away from him.She sought...