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Just Another Pathetic Humiliated Loserby: Cissy Gaye
Nancy knew about my submissive desires and my cross dressing and we had experimented with her humiliating me in various ways, but it was always private. Then one night when we were at a pool hall shooting a game, she began to subtly humiliate me. We were playing straight poolfirst one to sink fifty balls was the winner.
There were three high-school-age girls playing at the table next to us. As we played, Nancy began teasing me about how she was going to beat me in the pool game. She started saying things that indicated we had made a bet over the game, but we hadnt. She would laugh and say how she couldnt wait to punish me for being a loser.
Im not a great pool player but Im okay. Nancy wasnt usually as good as me, but this night she was really on top of her game. And I was not on top of mine. In fact, the more she pulled ahead, the worse I got. Her teasing had me really hard. So did her outfit. She was wearing a frilly cream-colored blouse with billowy sleeves and a tight brown suede miniskirt and boots. She knew how much I liked her blouse and as she would pass by me, shed rub it against me.
Eventually, the girls at the next table picked up on the stuff she was saying and started to watch us play out of the corners of their eyes.
Then she sank a really tough shot and laughed out loud and said, loud enough for them to hear, that she couldnt wait to see how silly and humiliated I was going to look when I had to comply with her wishes as winner. One of the girls said, "Excuse me, but I couldnt help overhearing. What are you going to do to him if he loses?"
Nancy looked at me with an evil grin and told the girl, "Im going to dress him up in my mothers clothes every day for a week and make him walk my dog around the block twice a day."
The girls all started cracking up. "What if you lose?" the first girl said.
"Well, I wont," said Nancy, "but if I did, Id have to give him a blowjob in the ticket booth at the movie
theater where we both work, while he sold tickets to customers." Well, the girls were really interested now. They stopped playing their game and took seats on a raised bench that looked over our table. Theyd cheer when Nancy made a shot or when I missed one.
It was Nancy 49 to me 38, when Nancy walked around in front of me to line up what might be her winning shot. I was sort of in the way, but I thought I was standing back far enough to not interfere and, trying to be cool and restore some small shred of my dignity in front of these girls, I didnt want to move. She looked back at where I was and lined up her shot.
I did not realize what shot she was lining up, though. Suddenly, she pulled the stick back fast and hard and the end smashed into my balls. I made a noise and doubled over. All I could hear was the sound of the girls laughing their asses off and congratulating Nancy on the best shot of the night.
Nancy said, "If you dont move out of my way, Ill give you another."
Totally embarrassed and in considerable pain, I meekly moved aside and Nancy sank her last shot.
The girls all cheered and chanted "Loser, loser, loser!".
Nancy walked over to me and laughed in my face. She slapped me across the face. "Looks like youre going to be prancing around the block twice a day in my mothers lingerie," she said. She started to turn back to the girls then spun back towards me and brought the cue stick up between my legs again, hitting me right in the balls even harder than the first time. I crumpled with a high-pitched cry and sat on the bench, doubled over. The girls couldnt believe I just took it like that. They started saying what a wimp I was. Then they started teasing me about how stupid I was going to look in Nancys mothers clothes.
"Get me a Coke, slaveboy," she ordered and I kind of crab-walked over to the machines, trying to relive the ache in my balls, and bought her a Coke. When I returned, Nancy was sitting on the bench, telling the girls about the various humiliating outfits she was going to make me wear the following week for dog walking duty.
"...then Ill make him do it in just a slip and stockings and high heels and his hair tied up in a scarf..."
The girls were laughing and teasing me as I was made to gather up the pool balls and cues and return them. They asked if they could come watch me walk the dog in drag, but Nancy told them that she didnt want people set up to see me. It had to be spontaneous, so that I would have the hope that I could get through it undetected and if I was seen, it was just my bad luck. They were disappointed until she asked one of them for her address and promised to mail her a picture of me performing my dog walking duties in drag. This was fine with them and she got all three addresses. They each told me how much they were looking forward to seeing my pictures and they hoped Id be seen by lots of people.
As we left, she said to me, "You know how hot it made me to humiliate you like that?"
"Im very glad you enjoyed yourself." I said truthfully. "I really liked it too."
"Not as much as youre going to," she teased. "After all, I cant disappoint those girls, now, can I? So starting this weekend, youre going to walk my dog in my mothers clothes and Im going to take lots of pictures to send to them. I cant wait to tell my Mother, shes going to get a kick out of this."
Id only gone out in drag a few times, mostly on Halloween, and my experiences had not always been good. Since Nancy wanted to use her Mothers clothes instead of my own pitifully small wardrobe to complete the punishment, she decided that one day was enough punishment, but that her Mom would have to be in on it.
Nancys Mom Gloria was a sweet lady but she was the opposite of Nancy, who was fun-loving but serious about her future and not a big party animal. By contrast, Gloria was a recent divorcee who was making up for lost time like crazy. She spent her days with her divorcee friends in a mad whirl of shopping, drinking, country clubbing and chasing men. One night about two weeks after the pool hall incident, I was having dinner with Nancy and Gloria when Nancy brought up the subject of my losing the bet. She said that as loser I had to be her slave for the day and do whatever she wanted and I couldnt complain or refuse anything no matter how humiliating it was. This seemed a few steps up from what wed discussed, but Nancy just gave me a smile and I fell right in line. Then she told her Mom about me dressing in drag for the day.
Well, Gloria howled. Immediately after dinner, she went through her basement closets, looking for "old" clothes I could wear for my punishment. Whenever she stopped pulling things out, saying that should be enough, Nancy would encourage her to find more. She told Gloria about the photos she wanted to send to the girls from the pool hall and she said, "The more outfits we have to choose from, the better. Besides he has to spend the whole day in dresses, so I think he should give us a fashion show of lots of different looks."
"Are you really going to make him walk the dog in a dress?" asked Gloria.
"Absolutely," said Nancy. "You think hes have let me off the hook if Id lost the bet?"
"What were you supposed to do if you lost?" Gloria wanted to know.
"He expected me to get down on my knees in the ticket booth at work and give him a blowjob while he was selling tickets."
We worked together in a movie theater near her home.
"My God, Nancy, what were you doing agreeing to a bet like that?" Gloria wanted to know. The look she gave me showed that I was on her shit list for thinking I could degrade her daughter that way. I was helpless to argue, but the truth was that Nancy had thought that part of the bet up too, to answer one of the girls in the pool hall. Not that I would have said no to such an experience.
"Simple, Mom, I knew there was no way I was going to lose. Hes a lousy pool player. The first time we played, I had a terrible time letting him win so he wouldnt feel all humiliated losing to a girl."
"So, you set him up for this?"
"Just like a pool hustler."
They both had a good laugh as I stood there filled with shame, my arms full of the clothes I was going to wear.
It was decided that the following day, a Saturday, would be my day of punishment. And to prepare me, Nancy spent the evening plucking my eyebrows, shaving my legs, my chest and my back, and washing and curling my hair. She had me dress in a pair of her Moms panties and one of her bras, then she had me put on pantyhose and a slip. Next, she did a dry run of my makeup and got me into a pair of Glorias old sandals that had only two-inch heels and were just a little too small. These were all the kinds of things wed done before but always in private. This time Gloria stuck around to watch the whole thing. She made comments continually, teasing me and belittling me. And Nancy egged her on, knowing it was driving me wild. She made me walk around to practice in the heels and they thought of a lot of little errands to send me on around the house.
Finally, they put me into red satin blouse and a tight black knee-length skirt and Nancy tied a silk scarf over the curlers in my hair.
"Whats that for?" I asked.
"To cover your curlers while youre out," she said. "Ive decided I want you to walk the dog tonight as a warm-up."
I opened my mouth to protest, but she slapped my face. Just then, Gloria came back from making tea.
"What was that?" asked Gloria.
"I had to slap this little girly," said Nancy. "Shes trying to get out of her punishment."
"Oh dear," said Gloria. "Thats very naughty. Perhaps she needs a spanking. Should I get you a hairbrush or would you rather use one of the ping-pong paddles?"
"Ping-pong paddle, I think," said Nancy, "unless youd rather be a good girl."
"Okay," I said. "Ill walk the dog."
"Oh, youre no fun. You could have let me spank you for a while first."
Turned out walking the dog was not that simple. First they had to take my picture, then give me all sorts of instructions on whose house not to let the dog pee in front of, and finally I was sent off with the dog and a baggie in case the dog pooped.
The walk down her driveway was so thrilling. It was a cool night with a mild breeze and the feeling of the slip rubbing against my thighs was making me very horny. They had the driveway lights on and were watching me from the front door. Id been given quick instructions on how to walk in a ladylike fashion, but it was hard when a 80 pound Irish Setter is pulling you along. The walk around the block was pretty uneventful, except for the fear that flooded through me every time a car went by. At the end of the opposite side of her block, right after the dog took his dump and I was leaning over to pick it up, Glorias car suddenly glided up next to me and Nancy leaned out with the camera. FLASH!! She took my picture as I straightened up with the baggie full of dogshit in my hand. I was so humiliated. I just knew I was going to look like a total asshole in that picture.
When I got back, Nancy decided that I should also take out the garbage in drag, but before I went, she made me take off the blouse and skirt. Then she photographed me in the driveway carrying the garbage can in just a slip and a headscarf. A car went by as I was out at the curb and I was terrified of who might be seeing me in this state, but whoever it was just kept driving. When I got back to the house, Nancy had locked me out. I rang the doorbell a few tmes, but when there was no answer, I sat down on deck chair to wait for her to take pity on me.
She left me outside for about 20 minutes, then she let me in. She had me change into a negligee and peignoir set and we went through to have a last cup of tea with Gloria before going to bed.
At that point, Nancy announced that the following day, I would be their servant, doing housework and cooking so that she and her Mom could have a well-deserved day off. Since I already did some cooking and lots of chores around the house, this was no big deal to me, but the chance to do it while dressed in drag was delicious.
Nancy decided that servants couldnt sleep with the mistress of the house, so I was plunked down on an air mattress in the basement.
I was awoken the next morning when Nancy poured a pitcher of ice cold water on me with Gloria watching and laughing. "Oh Nancy," she said, "youre going to drown the poor thing."
I was hustled upstairs to get my hair combed out and then fresh makeup was applied. I remember the first outfit they put me in. It was a soft, pink, crepe blouse with big ruffles at the cuffs and around the neck paired with a silky gray floral skirt. Under it, I wore a pink bra and panty set and a pink slip with a lot of lace trim. Ive always had a slip fetish and, knowing this, Nancy made me walk around in just the slip to start fixing the breakfast, before they put me in the blouse and skirt for my first dog walking expedition of the day.
Again, I was photographed several times with and without the dog and then I was sent off to do my duty.
This was a much scarier walk as the sun was coming up and there were people out and about, including a paperboy who kept circling me and two little girls who wanted to pet the dog. I guess I looked okay, since they didnt pay any attention to me, but I was shaking by the time I returned to Nancys house. She and Gloria were just getting out of the car so I knew theyd been following me taking pictures.
"Arent you just adorable in that outfit," said Gloria. "You know, I never wear it anymore, so its yours if you like. I insist."
One look at Nancy told me Id better be gracious, so I curtsied and thanked Gloria and assured her I would wear it often. This got them both howling again. I was changed into an old housedress for breakfast, which I was not allowed to eat. Then it was a skirt and sweater combination for pictures in the backyard. I went through a half-dozen changes in outfit before lunch, which I served on the deck in the closest thing they had to a French maid outfit, a black slip, a ruffled white blouse, black stockings and heels, and a large white lace handkerchief folded and pinned to my hair.
Nancy decided that since there was a servant to handle the dog walking, old Beau would be treated to three walks today. That allowed her to send me out in the middle of the afternoon in a peasant blouse and a long floral skirt. That was the worst part of the whole day as there were people everywhere and I was sure they could all tell I was a guy in drag. But no one shouted or pointed or chased me, so I guess I did okay.
The rest of the afternoon was spent shooting pictures of me in different outfits walking the dog up and down the driveway. As dusk approached, the wind picked up and dark clouds moved in. Before long, the rain started and as we came through the garage to shoot what was supposed to be the last set of dog walking pictures, the sky opened up and the deluge began. I was wearing a creamy satin blouse with long puffy sleeves that ended in cuffs with large black buttons and a pair of silky brown long culotte type things that Nancy called palazzo pants. I stopped at the edge of the garage. But Nancy insisted I go on. "Beau loves the rain and this will make it look like the photos were taken on different days," she reasoned. "So you take him down to the end of the driveway, wait about a minute to make sure youre good and soaked, then come back and pose right there by the car."
I told her she was cruel and beautiful and, after giving her a long kiss, I went out to be drenched for her amusement. By the time I got back, Gloria was standing there too, laughing at my drowned rat appearance. Nancy insisted I turn this way and that until she got the perfect pose. Gloria remarked on how cruel she was being and then said, if it was up to her, Id suffer far greater humiliations for daring to think I could force Nancy to blow me at work.
"Like what, Mom?" asked Nancy, fanning the flames with a wicked grin.
"Like that ping-pong paddle spanking for one thing."
"Okay." She turned to me and said, "Slave, I order you to submit to Mistress Gloria for forty whacks on your ass with a ping-pong paddle. Now!" I curtsied and came into the garage, dripping.
She pulled the blouse and pants off me and made me bend over a sofa in the basement, soaking wet in just a bra and panties. When Glorias first couple of whacks seemed too timid, Nancy grabbed the paddle and gave her a ten stroke demonstration, which was not deducted from the total. Gloria did much better after that.
After my ass gleamed red, even through the yellow panties I was wearing, Nancy asked her Mom what else she would recommend for my punishment. "Well, he should give you a blowjob."
"Mom, I dont have a dick."
"No, but you have a dildo dont you?"
So, the next thing I knew, I was dressed in an old green chiffon cocktail dress and was down on my knees in front of Nancy, sucking her dildo through the fly of her jeans as Gloria watched and commented on my cock sucking technique. When it came time for Nancy to "cum", Gloria took a jar of mayo from the fridge and flung spoonfuls of it in my face to simulate the jism. I sat there and let them laugh for a good long time. The humiliation was absolutely incredible.
Finally, it was late enough for my final dog walk. Making good on the promise shed made to the girls, Nancy made me do the honors in a slip and a headscarf. This time I was really terrified because I wasnt just in drag, I was in lingerie, which wasnt only embarrassing, but might have been illegal for all I knew.
Fortunately, although the rain had stopped, the late hour and weather kept the streets pretty clear and the only really embarrassing moment was when Nancy popped up out of a bush a couple of houses down from her own and took my picture.
It was late, when we sat down in our negligees and peignoirs for late night tea and Gloria congratulated me on being such a good sport. I told her honestly that I had lost the bet, fair and square, and I loved Nancy, so Id had no choice but to sacrifice my dignity for their amusement. I told her that I had deserved the ridicule that had been heaped upon me and I would never again be foolish enough to make a bet against Nancy over a pool game. It was only then that Gloria realized she could have made my day even more humiliating by inviting over some of her girlfriends, in particular Margie, a blonde bombshell with an incredibly abrasive personality who delighted in emasculating any man in her path. I was glad I had escaped having her see me the way Id been tormented today.
"Thats okay, Mom," said Nancy. "Ill get him to make another bet before long and well have the whole gang over to watch the fun."
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