Riding Bitch

by Cissykay

  

Chapter 9

  

As soon as everyone arrived back at the campsite, I was ordered to Mistress Cheryl's motorhome. There was something exciting going on, but I didn't have time to see what was going on. Mistress Cheryl unlocked collar and told me to sit in the beauty chair. I was in no condition to do anything but comply. Just then there was a Knock at the door. "Enter." The door opened, and Cora appeared. She was dressed in a silk corset, designer silk stockings, and 5" stilettos, the same color as my bondage boots. "Good evening pledge Cora. I trust your day was relaxing." "Oh yes Mistress, it certainly was." Cheryl ordered Cora to help me out of my hobble dress. She unzipped the top and the bottom. Taking care not to be too rough on me, she helped me out of the dress. Mistress Cheryl handed Cora a key, and instructed Cora to remove my chastity belt. When she did, she saw immediately the condition my prick was in. It was now blood red, and still hard as a rock. She examined the steel cock ring. "That must be terrible for you, sissyslut. I'll have to ask Mistress Cheryl to show me how to do that to a slave when we reach Sturgess." Mistress Cheryl then ordered Cora to come to her. She spun Cora around, and cuffed her hands behind her back. "The only way I can remove the ring, is for sissyslut to get relief from her current predicament. That's where you come in. Please relieve her immediately. And, if she gets one drop of her come on my clean floor, I'll have your handler chain whip you. Hurry girl, I don't have all night."

Cora dropped to her knees and grumbled something to me, and began to suck my dick. She could tell that it was painful for me, so she tried to be gentle. As much as she sucked and licked, I couldn't bring myself to come. It was too painful. "Just close your eyes sissyslut and think of all the sexy torment I am going to put you through." I tried to think of myself fucking Melanie, and after what seemed like hours, I finally found myself beginning to get aroused. It wasn't to long after, that I shot the biggest load of my life right into her mouth. Cora was forced to swallow the entire load. I actually felt sorry for her. The moment I finished, I felt my penis begin to shrink. In about two minutes, it was hanging loose again. "Be very careful for the next few days sissyslut. That cockring has broken several blood vessels in your prick, so you will be quite sore until the heel." I let out a deep breath, and slumped in the chair. Cora noticed the ballet boots,as she was recovering from the humiliation she had just been forced to endure. "I see you like those boots Cora." "Mistress, this pledge was just wondering if the were comfortable? They do look wonderful on sissyslut." " Well, I can't have you wondering all night. Sissyslut, please remove your opera boots, and let Cora wear them for one hour only. Then she is required to put them back on you. Am I understood?" Yes Mistress." I unlaced the boots, and relaced them on Cora's feet. She was sitting on the floor. Cheryl then had an idea. "Sissyslut, I've decidied to let your pledgemate enjoy her evening even more. Help her into the pretty new dress that you wore today. After all, you are pledgemates, and you should share pleasure as well as pain. I know that the breasts are a little different, but with her waist being about an inch wider than your new waist, it should compensate. Be sure to put the accessories on her also. Then zip the top zipper only, and be sure to buckle her collar." Cheryl released her handcuffs. I helped Cora into the dress, and with some difficulty, finally got the zipper done. I put the belt and bracelets on her, and waited for Mistress Cheryl to inspect my work. Still seated on the floor, Cora saw herself in the mirror and smiled. "I look wonderful in the outfit." "Yes you do Cora." Cheryl them made a call to Cora's handler. "Hi Janie, this is Cora. I hope you don't mind, but I have Cora here with sissyslut. She commented on the slut's new boots and dress. I hope you won't mind, but since we are having a party this evening, I thought I'd let her wear the outfit. I told her she could only wear it for one hour, but I will leave that up to you." Good, I'll have her and sissyslut report to you immediately. The slut can show you some of the dresses features when they arrive.

Bye bye."

"Just one thing for you sissy, and then you can guide Cora to her handler." "Cheryl had me sit in the beauty chair, and stick out my tongue. She instructed Cora to remain seated on the floor. She took a tool and with a twist, removed to ball that was pierced to my tongue. She replaced it with a gold ball about three times the size of the first one. She twisted it again with the tool, and it was screwed on tight. Then she took a tube and applied something around the edges of my tits. In seconds, the glue disolved. She took a knife and with the skill of an artist cut the inside of each tit. She removed the weights from inside the breasts, and glued them back on. Then she touched up the outside again, and I looked like nothing had happened. I was instructed to bring Cora to her handler. As I got off the chair, my tits began to jiggle. No pain. I began to squeel with delight. My tits didn't hurt. I immediately took one in each hand and felt how real they actually felt. I closed my eyes for a minute, and savored my new freedom. I was instructed to show Mistress Janie all the features of the dress, and we were dismissed. On the way down to the party, I tried to tell Cora that the boots would be fine for a few minutes. Then the pain would hit. Mistress Cheryl was very smart and quite evil. Because of the larger ball in my mouth, every word I tried to speak just came out as one big lisp. I couldn't communicate with my pledgemate to tell her that she had taled herself into a night of extreme agony. In all the excitement, I didn't even notice that I was now totally naked.

When we arrived at Mistress Janie's seat under one of the big oak trees, Cora was smiling broadly. Mistress Janie liked the look. I knelt on the ground, and brought Cora's feet very close together. Then I pulled to the zipper down to the ankles of the boots. I knew her corset would prevent her from bending far enough to unzip herself. "Cora, you look fantastic in that outfit. You really look good enough to eat. How would you like to model the outfit for the ladies?" "Yes Mistress, this worthless pledge would love that." Well, I can't have you running around all night unattended, so sissyslut, attach that chain hanging from the tree to her collar. I clipped the chain to Cora's collar, and knew she was in trouble. Even without the bracelets, she wouldn't be getting out of this prison until Mistress had made her suffer. I also knew that if I didn't hook her wrists up, I would be in trouble. I inserted her wrists into the holes in the belt. Two clicks and she was completely immobilized. She just didn't know it. "Are you comfortable Cora." "Oh yes Mistress." "Good. Everyone will want one of these before the evening is over. Sissyslut, you are to report to the barn to get an outfit for yourself." I turned and walked away.

I had total freedom for the first time since this started, and I enjoyed every minute of it. When I entered the barn, Mistress Judy was busy doing something to a female chastity belt. "Good here you are. First, put your ankle on the block. I did as I was ordered. With one blow to a pin the she held, the rivet popped out of the manacle. Then the other one. She pulled them off and looked for any marks. I was really smiling now. "Don't get to excited my pet, the joy you are experiencing now will be the same joy I feel when you fuck up, and I get to weld something onto you, so it'll never come off. And you will, believe me. There is a box on the table over there. Put on the outfit. You have five minutes. I'm in a hurry to enjoy what's going to happen." I opened the box, and it contained a corset, bra, garter belt, panties, and seamed stockings, all in black. I was now pretty adept at getting dressed, so I had the underwear on in record time. Then I put on the black 5" stilettos. These would be a breeze after this afternoon. Last was a satin maid's outfit. I slid the dress over my head, and slipped the petticoats under the skirt. I was done in less than three minutes. Mistress Judy zipped me up, and pinned the cap on my head. "There, you are ready to serve. I wasn't even embarrassed by the maid's outfit. I felt wonderful, and the feel of the silk underwear, felt wonderful. I was in so much pain before, I never noticed how women's lingerie felt. I was told to inform you that you get a demerit for not having your purse. It's on the table. Mistress Cheryl took the liberty of putting a pad and pen in it for you. You will have each woman sign the book after you satisfy them. Fifteen, correct?" "Yssssssssstttth Mmmttttthhrrrs." "On your knees slut." I dropped to my knees, and she spread her legs wider. "Well slut, if you don't remove my panties, how are you going to eat me?"

I pulled her pants down and stuck the gold ball right inside her pussy. I tickeled her clit for a few minutes, and she was groaning. Then, a loud scream, and My face was wet. She took the book from my purse and signed it. Only fourteen left slut. You are good, so I want at least two more tonight, understand?" I nodded. "Now be on your way. Bring you purse, and I want you to carry the chair by the door to the oak trees." I headed for the door, and picked up the chair. I was definately made to bind someone in it. I brought it to the oak tree and set it down.

This whole thing took no more than fifteen minutes, and when I was told to bring beers to everyone that was ready, I passed Cora. She already knew that she was in trouble. The boots had started to do their job, and because she was chained up, she couldn't sit. She had the constant torture of the boot on her feet. She tried shifting from one to the other, but it was no use. She was crying loudly already. I was busy for the next few minutes serving drinks. I was actually enjoying myself. I had serviced two more women, and word got around about the tongue ball. The fifteen wouldn't be a problem. Wanda had arrived, and she was still being introduced to everyone. She seemed to relish in Cora's plight. I was ordered to sit at the feet of Mistress Melanie. She put her right foot on my lap. Her polish was clearly visible through her nyloned stocking. "You have shown that you are pretty good at massaging a pussy with that tongue, let's see if you are as good at toe sucking. I took her foot in my hand and began to lick and suck her toes through the stocking. When I sat on the ground at her feet, I made sure to straighten my uniform like a proper lady, so I knew she couldn't see that even though my dick had been tortured all day, it was hard as a rock. Her foot tasted like heaven. As I worked on her foot, I could hear Cora. She was now screaming from the pain.

There was another pledge that was strapped into the chair that I was instructed to bring. She had her eyes closed, and was enjoying herself as much as I had ever seen. As I finished with Melanie's foot, she explained to me that the pledge had been caught earlier trying to have an orgasm under her chastity belt. I could see that it had been removed. The pledge got today's black mark, which made her even with me. She also received three demerits for next weekend. Well, at least I wasn't alone. The woman was in heaven, as she orgasmed right in the chair. Her punishment for tonight was ride the wave of pleasure, and then ride the pony. If the second part was as enjoyable as the first, I might volounteer to replace her. "You see sissyslut, she has an electrical device called a voilet wand inserted in her pussy. It massages her for five minutes, and then shuts down for three. As you can see, by the smile on her face, she orgasms during the five minutes. She can't wait for the vibrations to begin again. Just watch the show sissy." The machine began to mumble again, and before the five minutes were up, she came to orgasm again. This time it wasn't as strong as the last. The machine shut down, and then started again three minutes later. Again an orgasm. "You see slut, it is impossible not to cum for the machine. It won't stop until she does. The wires are controled by the muscle contraction when the orgasm happens." This time she just moaned a little. "Would you like to take a pony ride with her sissyslut?" I am smarter than the average bear. I said no. I noticed that the spreader bar that had been locked to her thighs prevented her from closing her legs. As the machine shut down, Melanie continued to educate me. "The female body can not reproduce the fluid that it exudes during ejaculation in three minutes. She is drying up now. Every time she has an orgasm, it dries a little more. We women need lubrication to perform, just as men do." The machine started again, and before long the pledge was brought to orgasm again. This time she fought it a little. "Now it's what is known by women as a dry fuck. Just watch." As the machine started again three minutes later, it took a shorter time for her to climax. This time she let out a scream. "It gets worse slut. I bet she won't make it the full two hours. It had been less than thirty minutes, and she was already screaming in pain. Coupled with the more frequent screams coming from Cora, we had stereo.

I was ordered to tend to the guests. I brought beer for everyone who was not being tortured. When I was through, I saw that Cora was about to pass out from the pain. Mistress Melanie then made an announcement. "Since pledge Cora is not being punished for an infraction, she may request that someone take her place. If the person agrees, she will be freed. The new bondage slut will be allowed to try to convince someone to replace her after the 45 minute training period. With any luck, we will have many pledges who will learn to tolerate life in ballet boots before the night is over." I knew nobody else was going to take her place. Two of the other pledges talked to her, but I assumed from the whaling Cora was doing that they didn't agree to replace her in the bondage dress. I excused myself and went to her. I unhooked her from the chain and gently placed her on the ground. I unzipped the dress, began to loosen the boots. The key to the collar lock was there along with the key to the lock on her neck chain. Since nobody was gagged in any way yet, Cora was able to say thank you to me. After she brought some life back into her feet, she helped me into the dress. I had already encased myself in the boots. We heard a voice from somewhere telling her to be sure that she hooked me to the tree, and lock all the locks. I stood up, and Cora locked me up. "Thank you again sissyslut. Now I can go eat while I have some time." Since the club members were taking turns cooking, there were plenty of steaks for all.

It took about fifteen minutes before I was realized that I could take the pain of the boots this time. I struggled against the chain and the wrist locks, but I knew I could make the forty five minutes. I noticed that Cora was now wearing my maid's outfit, and was serving. She looked nowhere as sexy in it as I did. The pledge who got caught fingering herself earlier was just about to lose it. She was screaming every time the machine started, and every time she imagined it was going to start. It was just about then that the other team of pledges were led out. They also had their chastity belts removed, and their arms were strapped behind their backs. An "O" ring was strapped on each of the mouth, so they couldn't close. One of their sponsors announced that her pledge, and the other pledge had earned no black marks, and no demerits, so they were going to be rewarded for good behavior. They were led to the center of the group. Both were crying. First, a strap was buckled around each of their waists. The straps were tethered together, which brought them within six inches of each other. Then the handler produced the weirdest looking dildo ever. It was shaped like a double dildo, only it was shaped like a "V". The thing had to be a foot and a half long. The handler smeared it with lubricant. The look on the pledges faces showed terror. The handler inserted one end into each of their pussies. When she pushed the two girls at the waist, they each leaned forward. The dildo went a little deeper into each of them. She then produced another bright red dildo about eight inches long. She held it up to her nose and smelled it. "Wild Cherry, I believe. She told each girl to open their mouth. She inserted the candy dildo between their in the rings and told them to hold onto it. They did. Then she tethered their legs closer together with thigh straps. The dildo in the pussies was now pinned inside. Lastly, a long chain was produced. It had a nipple clamp on each end. One chain was attached each of the tits, effectively attaching it loosely to the other girls tit. A large chocolate kiss was placed so as to rest on each nipple clamp.

"Ladies, may I have your attention please. This game is called Lesbian Lovers. The contest consists of three stages. First, one contestant must bring the other to orgasm. Next, the lollipop must be totally consumed, and last, but not least, the chocolate must be comsumed by placing the lips on it, and letting it melt in the mouth.As soon as we start the contest, if we see any red showing between the contestants, the challange is lost by both contestants. The first one to consume both pieces of chocolate will be declared the winner. Everyone cheered. Ladies, begin." They immediately pressed their lips tightly together, so no red could be seen. They tried as hard as they could to pump the dildos in and out. By now they were both laughing. I could see that they kept turning their heads from side to side to get their tongues working on the lollipop. It appeared that two lesbian lovers were french kissing and fucking each other.

I had been in bondage for about an hour before I yelled to Cora. She just pretended not to hear me. She went on serving everybody. I called to the other pledge and she came over. She gave me a big drink of beer. "Will you wear the dress and boots, so I can rest?" I promise I will come back as soon as your time is up." "Sissyslut, I don't think I could take the pain. I'm sorry. I can't do it." "I understand." About ten minutes later, Cora came over. "Please Cora release me. I went for over an hour this time, and believe me, it is much easier. I have to pee, and I am starved." Cora refused at first, but said she would when I told her I had a plan. She let me down and we traded uniforms again. After she was totally inside the dress, I told her my plan. I dug two very small holes about eight inches apart in the dirt in front of the tree limb. I helped Cora up. I fastened her to the tree and zipped her dress almost all the way down. "The dress was made for me. You are taller than I am. Watch this." I slid one boot, up her leg, but it was outside. I rested the heel in the hole. Then I did the other. "Now the dress hangs just about to the ground. The front of the boots show. If you just stand still, nobody will know that you're not wearing them." She smiled at how devious I was. I walked off in my stilettos, and sat down the eat. As soon as I was through, I went to the ladies room. It wasn't until I was inside, that I remembered that I could stand up to pee. I lifted the seat, and aimed right for the center. I was laughing like an idiot. I started to massage my aching dick, and it was responding. I began to moan, and before I knew it, I had exploded all over the wall in back of the toilet. I pulled some paper off the wall and cleaned the mess. I quickly went to the sink to wash myself up, and get back to the party. I was whistling a happy tune.

"Don't you think you should lower the seat before you go sissyslut?" The voice was unmistakeable. It was Melanie. All she said was, see you outside. I knew I had gotten myself into a mess this time. I was ready to cry. "Mmmssssttthhhsss, I can esssshhhhplain." "Just shut your whore mouth, and get out of here. I ran out, and started for the road. I had to get away. After all, I had no chastity belt on, and no shackles. I could try to figure out a way to get the makeup off and the breasts removed later. I was still dressed like a maid, but it was better than being in that outfit or worse yet, naked. As I ran past the club members, I could see that most of them were were having a good time and drinking up a storm. Someone was just now unstrapping my sister pledge from her punishment chair. I noticed that when she tried to walk, she looked like she was the most bow legged woman in the world. She was obviously in alot of pain. Maybe we could escape together. I slowed to a walk before anyone noticed that I was leaving. I knew that I could never outrun a motorcycle gang if they all wanted to chase me down. That's when I saw Cora. She was out of my dress, and watching the show still being put on by the two pledges that were strapped together. There was something inside of me that said run away fast, and then there was something that said I made a wager and lost. I turned toward the crowd, and walked toward them. I knew I would find out my punishment shortly.

When I finally reached the club, I didn't know how to act, so I just started making sure that everyone had a fresh beer. Mistress Melanie joined us shortly thereafter. I could see that she was no longer in a festive mood. She paid no attention to me. As the announcement that the pony rides were about to start, everyone gathered at the oak trees. I noticed that Mistress Melanie was in conference with the other sponsors and handlers. There was no doubt in my mind that the conversation had to do with me. I watched as the pony ride demonstration was being set up. It was quite simple. A piece of two by four was hung by a chain that was attached to a hook. It had been plained to a perfect 45 degree angle on the top. The pledge that was being punished was summoned forward. At least she was still walking, although still not very well. I would think a woman would run out of tears from all the crying she had done earlier. She was beginning to tear up again. Her wrists were cuffed with the familiar punishment globes. A chain was then attached to her globes and her arms were raised over her head and locked in that position. A spreader bar was then attached to her ankles. She was now standing with her legs spread, and her arms over her head. Then one end of the wooden plank was unhooked from the tree, and it was pulled between her legs. It was reattached to the tree branch, and after a few minor adjustments, it hung freely about about one inch below her crotch. My first thought was some pony ride. Here was a woman standing with her legs forced apart in her five inch heels, with a plank between her legs. Her arms were chained over her head. She kept looking down at the plank between her legs in wonderment. She began to smile a little. There was no pain involved in this. The handler just said to her, There you go honey. Are you enjoying your ride?"

The announcer, who was one of the club members members, was making comments as everything was being done, so everyone could understand the goings on. Then, as one woman stood on each side of the pledge, the announcer signaled to the ladies. All at once, they bent down and removed her shoes. This forced her to either stand on her tiptoes, or sit on the sharpened board. She chose to stand. In a few minutes her legs began to cramp, and she could no longer stand on her tiptoes. This forced her to sit on the board, and the point was directly on her pussy. After a few minutes, the pain of the sharp point worked it's magic, and she was forced back on her toes. Of course she couldn't last quite as long this time, and before long she was seated again. The more she squirmed to get comfortable, the more it dug into her pussy. "This will be going on for two hours, so everybody stop by from time to time to see the fun this pledge is having." The screams were starting again.

I noticed that the sponsors and handlers hadn't returned yet, so I made busy serving drinks. Wanda was the only one who asked me to service her, so I did it as fast as I could. I had forgotten that I was required to service the fifteen women. To this point, I had done six. I then realized that I didn't have my purse again, and that would mean another demerit. I was really doing good. It was at that time I resigned myself to a punishment, and popped a beer for myself. It was my first one. When Melanie and the others returned, I was ordered to get her a beer, and another for myself. I retrieved the drinks, and Melanie just snapped her fingers an pointed for me to sit. I did. "I guess I was wrong about you this morning sissyslut. I honestly thought you were going to try to become a willing pledge. Tonight you proved that you can't be trusted. Would you like to end the bet, and in the morning I will return your clothes and bike to you. I just don't have the time or the energy to try to train you. I guess this whole idea was a huge mistake, and I will accept the blame." I told Mistress that I really did want to please her. I was having a hard time adapting to the pain and humiliation of the initiation ritual. After all, I lost, and I wanted to pay the bet. I was sure that word would get back to South Dakota that I couldn't even handle a woman's bike club initiation. They didn't know what type of woman's club this was. I asked her for one more chance, and she dismissed me while she considered it. When I asked if I was to get back into my bondage boots, she just shook her head and said later, if I was to be allowed to finish the iniation. I went to find my purse. For the rest of the evening I drank, serviced anyone who was horny, and occassionally played the humble waitress. As the party was winding down, Mistress Carol and Wanda were laughing together. I saw Carol hand something to her. I was summoned to join them. When I arrived, Wanda removed her panties from under her skirt, and threw them on the ground. She then slid a pair of heavy black rubber panties up her legs. These had something rubber protruding from the front. I was ordered to kneel in front of Wanda. I was told that even though I was fantastic with my tongue, I brought them to climax too fast. Carol cuffed my hands behind my back, and my ankles together. Wanda then stood and showed me what was attached to the panties. It had a rubber hood sewn into the front. Wanda stretched the rubber, and placed the hood over my head. The panties were crotchless. My head was now trapped in the hood, and my nose and tongue were buried on her pussy. "Let's see if a few hours of pussy training will teach her to be more patient." I spent the rest of the night buried in Wanda's pussy.

  

  

  

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