A Lost Bet Ch. 04

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"Now, I want to show you guys something really special," said Lisa. "Since you've already gotten her ass warmed up, I'm going to cool it down with a little ice before bringing out the next toy." A muffled yelped came out of through the ball gag as she ran a couple of ice cubes over my sensitive skin. When she took the ice away, my rear felt tingly...a cross between feeling numb and overly stimulated. I looked up into the mirror to see what she was doing and I heard the crowd mumble and "ooh" and "aah" and say "that's pretty cool" as she wheeled a device up behind me. All I could see was that it looked like a bicycle wheel mounted on its side.

Lisa started her spiel. "This is our newest spanking device. It's been affectionately named 'Sir Spanks-A-Lot." The crowd laughed. "What you see is a bicycle wheel mounted on a small electric motor with adjustable speeds. You can position the wheel horizontally or vertically or anywhere in-between thanks to the adjustable mount. On the wheel, you can mount up to 6 attachments that are included in with the machine. If you want to use the harder spanking tools, we recommend that you position the spank-ee in a way that allows the machine to move them as they are spanked. For now, we'll just use the leather straps. Once the straps are attached, you plug in the machine and then adjust the speed by turning this knob here. We're working on a wireless remote for the motor, and that model should be available in the next few months. Once you set the speed though, just relax and watch the machine do all the work of spanking and discipline for you." With that she turned the motor on low and I felt my ass being spanked anew. My yelps and moans were in time with the slaps from the leather straps.

"Do it faster," I heard a few people in the crowd call out. "Faster...faster...faster." A chant had broken out as the crowd watched me get spanked by the machine.

"Okay. Now be aware that the faster the machine goes, the harder some of the lashes will be. We've got a built in governor to keep it from going fast enough and hard enough to break the skin." Lisa explained. "Do you all want to see the highest setting?" She called out. "Yeah!" responded the crowd.

"Is that all right with you gentleman?" Frank and Tom nodded. And Lisa turned the speed on the motor up to high.

"MMMHHHMMPPH!!!..." was all I could get out as the leather straps bombarded my cheeks. There was no more moaning with the beat. The licks came quick with no breaks to catch my breath. My ass was so sore and tender that each slap sent a spark through my body. I wanted the spanking to be over more than I'd wanted anything else in my life. Tears started to run down my cheeks and my sobs could be heard through the gag. Finally, Lisa turned off the machine and Frank came around in front of me.

"Jo, Jo...are you finally ready to stop resisting and do what's being asked of you?" He asked these words while cupping my face with his hand and slowly wiping some of the tears away.

I nodded.

"Do you promise to do whatever we ask you to do?"

I sniffed...and nodded.

"Let her up Tom." And Tom started untying my arms from the hanging chain.

"Lisa," Tom said, "make sure we have your card and a brochure because I know we'll want to order one of these."

"Oh, most definitely," Lisa responded with a million-dollar grin. "Thank you for helping out with the demonstration. I think that worked much better than just displaying the products."

And indeed it had, because the line of people touching and examining the machine was long.

Frank helped me stand up after Tom finished releasing my feet, and he cradled me to his side while I shed the remaining tears. Tom came by and slowly ran his hands over my ass and I squirmed. Everything was so tender that the slightest touch felt like fire on my cheeks. The guys guided me away from that particular corner and headed over to a wall. There they removed the butt plug from my ass and I stood there shivering and shaking as I got used to the empty feeling.

"Okay Jo. Are you ready for your first test?"

I nodded.

The guys led me to another corner where there was a huge array of dildos and vibrators. Some were hand-held, but others were attached to a board jutting from the wall just high enough that someone could get on their hands and knees and fuck themselves with it. I knew what they were going to ask me to do because I could see a woman on her knees fucking herself against the mounted dildo with another one in her ass. Her eyes were glossy as she reveled in the self-induced pleasure while a group of people looked on. She continued to fuck herself while a man came up to her and started teasing her breasts. She moaned in apparent ecstasy. Then, someone who had apparently been at the other booth watching my "demonstration" called out, "let's see the Black tranny fuck herself!"

Tom and Frank looked at me as I shrunk. But knowing I had no choice, I hung my head while they untied my hands from behind me and retied them in front of me. "Jo," said Tom, "you can pick the first dildo to use. But before you cum, you have to use 'the big one' and you have to use the one on the wall." I looked up to see what "the big one" was and nearly froze as I saw a dildo that must have been 5 inches in diameter and 11 inches long. I couldn't stop staring at it...whether it was out of fear or desire, I couldn't tell. I'd never had anything that big in my ass and I wasn't sure about trying it in front of a large group of people.

I started to shuffle forward to some of the dildos lying around, trying to see which ones looked manageable. Finally, I found one that was about 6 inches long, and about an inch in diameter. I picked it up, then looked at Tom and Frank for approval. They nodded that it was okay. I knelt down, then had to reach through my legs to insert the dildo into my ass. My hands felt delicate as I eased it in with a small whimper. Slowly, I started to fuck myself with it, moving it around until I found a spot where it actually started to feel good. For the first time since the night before with Frank, my ass felt good being invaded. I started to moan in pleasure and my hips started to writhe. My eyes were half-closed and I didn't see Tom approaching me. It wasn't until I felt his hands on my chest that I looked up. He'd gotten some weighted nipple clamps from somewhere and he put them on my nipples one at a time. I gasped at each pinch and started to squirm even more. As I continued fucking myself, Frank appeared and handed me a larger dildo. It had to have been about the same length, but it was wider, probably 2-3 inches around. I slid the first one out and slid the second one in. My moan was louder as the feelings were more intense this time. Still, I continued to enjoy the erotic feelings that were waking inside me. I started to surrender to the pleasure...feeling my ass full, my nipples taut, and my cheeks tingling. It was an extremely exotic and erotic moment. The minutes passed and I could tell people were still watching me because I could hear their comments, but I started not to care. I did, however, attend to Tom's voice when he said "use the one on the wall." I pulled out the dildo I had been fucking myself with and got on my hands and knees facing away from the dildo that was sticking, almost obscenely, out from the wall. Slowly, I eased myself back onto it, relishing the feeling of having my ass filled. I started to want it, and I moved faster. The change in positions brought different sensations, different feelings, and sent me to a new level. I rocked faster and faster. But the crowd wasn't satisfied.

"Give her 'the big one.'"

"We want to see her ride 'the big one.'"

I opened my eyes to look around and see what Tom and Frank wanted me to do. I hoped they would let me stay here because I was so close to cumming. But they didn't. They motioned to the large dildo on the rack and I crawled forward towards it, hearing a small pop as my friend on the wall exited my rear.

"Jo, stop right there for a minute." I turned to see Frank heading towards me. I wondered what he was planning to do. "You're going to need both hands for that one," he said as he untied my wrists. Then, he surprised me by taking out the ball gag. "The crowd wants to hear your unadulterated pleasure." He stepped back and let me continue on my path towards climax. I reached the rack and took down 'the big one.' I positioned myself on my knees over the huge dildo and aimed it at my ass. I started to force myself down onto it, trying to hold it steady with both hands, but was only moderately successful. I tried again and again, until I was panting from the exertion and pressure. I'd never felt that stretched before and it was taking awhile to get comfortable.

"Frank...Tom...please help me." The words came out of my mouth before I could realize what was happening. They both smiled at me and came over.

"Get on your hands and knees," Tom instructed. Frank took hold of the dildo and started to push it in while Tom dribbled more lubricant down my ass crack. Slowly, inch by inch, it went in. I was gasping and moaning and mewing, and the crowd was eating it up. Frank stayed behind me and started to fuck me with the dildo. My eyes closed. Then Tom started playing with my nipples and caressing my ass. I was in another world. This continued on for a couple of minutes and the crowd was appreciating the show. The last straw came when I felt Frank reach around me and grab my dick and start to caress it. My mouth opened as my breathing got ragged. He started stroking me in time with the pushes of the dildo. I think I started calling out "yes...more...please fuck me...don't stop..." but I'm not sure. My body was convulsing and my legs were shaking and I was so gone by that point that I didn't know what I was doing.

Until finally...I came. I spurted jet after jet of cum onto the floor in front of me, getting the release that had eluded me all day. I collapsed onto the floor to rousing applause from the crowd. "Oh my God," I thought to myself as I started regaining control of my senses. "What did I just do? What just happened?"

I opened my eyes to see Frank and Tom standing there like proud parents. "That's our girl. We always knew you could do it." I continued to lie there trying to catch my breath. Other people that had been watching stopped to congratulate Tom and Frank on having such a wonderful girl to play with. I saw them exchange information with a few people and heard mumbled words about a private party at a cabin by the lake in a couple of days. But I wasn't focusing on much. My body was wired and I could feel everything. The stickiness of the cum underneath me. The dildo still lodged in my ass which I was afraid to remove without help. The nipple clamps pulling. The twitching in my dick that was always there after climaxing.

Finally, Frank and Tom turned their attention back to me. They removed the dildo from my rear, then took off the nipple clamps. They helped me stand up as Frank handed me my panties and skirt. "Jo, you are turning into quite the amazing lady," he said with a proud smile.

"That she is," Tom added as he helped me put on my coat. "That she is. Are you ready to go or was there more stuff in here that you wanted to see?"

Before Frank could respond, I interjected "could we PLEASE go home?"

Frank laughed at my response. "Sure, sure. After all, we can see some of the things that were in here another time." He winked at Tom. At least I thought he did. I couldn't really be sure because I was so exhausted that it took all my concentration to hold onto his arm as I tried to put one foot in front of the other.

We walked out of the "show" and back to garage. I gingerly sat down in the truck feeling both empty and sore. "Please, no more tonight. I just can't do anything else. All I want to do is go home and crawl into bed."

"Okay Jo. We'll give you a break, at least as far as sex goes. Just...take a bath when we get home, then you can go to sleep," Frank reassured me.

"Thank you. I promise, tomorrow, we'll do what you want. I just really want to sleep."

Tom turned on the radio and I nodded off on the way home. Once we got there, Frank roused me and helped me inside and then into the bathroom where he started running the bath for me. "Just strip off your clothes and leave them in here. I'll take care of them for you. And I'll be back with a nightgown for you." He left me to get undressed and it felt so good to take off the jacket...the boots...the stockings...the skirt...the panties...and the bustier. My nipples and ass were still tender, and as I slid into the tub, I felt the water start to massage away some of the pain. I also felt it slip into my still stretched ass. "I guess I'll have to wear a tampon tonight anyway," I thought to myself before closing my eyes and relaxing in the tub.

About 30 minutes later, Frank came in with a pink cotton nightgown. "Here you go. Get some rest tonight, okay Jo? Don't forget, we're still going skiing tomorrow." I groaned as he winked at me and left. "Can't a sistah catch a break?" I thought before getting out of the tub and toweling off. I got dressed in the nightgown, waved goodnight to the guys, and crawled into bed. I passed out with unrecalled thoughts and dreams about what the next couple of days would bring.

To be continued...

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SissyBoy1WarszawaSissyBoy1Warszawa8 months ago

I was captivated by the plot of this story/story, and I liked the person of Jo the most, I would like to be like him and cross individual borders. I really like Jo dressing up in appropriate, beautiful, sexy lingerie or clothes. I am quietly changing into women's underwear and clothes alone, but I miss someone like Frank in the previous part, gentle, emotional and very nice. I understand Tom in part, but I don't like his brutal treatment of Jo. Will the lesson from the casino and individual playrooms and the punishments Jo received turn him completely into a submissive Sissy? What else awaits Jo? Will Frank and Tom become more for Jo than people humiliating him, forcing him to have sex and turning him into Sissy by force, and maybe a friendship or maybe love will develop between them? I am thinking about the future of Jo, Frank and Tom with great interest and impatience. 📖❤️🧒🏻👸🏻💋💦🍦💦👅👗👙🧑🏻👱🏻‍♂️.

ps. Sorry for grammatical errors and inaccuracies, but I don't speak English.

SissyBoy from Warsaw, Poland. 📖👩🏻‍🦳👩🏻❤️🧒🏻.

❤️

Porwała Mnie fabuła tej historii/opowiadania a najbardziej przypadła Mi do serca osoba Jo, chciał/a bym być jak On/a i przekraczać poszczególne granice. Bardzo Mi odpowiada przebieranie się Jo w odpowiednią, piękną, seksowną bieliznę czy ubrania. Sam/a po cichu w samotności przebieram się w damską bieliznę i ubrania, ale brak Mi kogoś takiego jak Frank w poprzedniej części, delikatny, uczuciowy i bardzo miły. Rozumiem po części Toma ale nie podoba Mi się takie brutalne traktowanie Jo przez niego. Czy nauczka z kasyna i poszczególnych sal zabaw oraz kar jakie otrzymał/a Jo zmienią go całkowicie w uległą Sissy? Co jeszcze czeka Jo? Czy Frank i Tom staną się dla Jo kimś więcej niż osobami go upokarzającymi, zmuszającymi do seksu i zmieniającymi siłą w Sissy, a może rozwinie się między nimi przyjaźń a może miłość? Z wielkim zainteresowaniem i ogromną niecierpliwością myślę o dalszych losach Jo, Franka i Toma. 📖❤️ 🧒🏻👸🏻💋💦🍦💦👅👗👙🧑🏻👱🏻‍♂️.

ps. Przepraszam za błędy i niedokładności językowe ale nie znam języka angielskiego.

SissyBoy z Warszawy, Polska. 📖👩🏻‍🦳👩🏻❤️🧒🏻.

KingflintKingflintover 4 years ago
Soo

Jo is black who knew

AnonymousAnonymousalmost 14 years ago
it's its, not its'

The word it's is the contraction of "it is" or "it was" (or "it has").

Its is the possessive form (no apostrophy).

The fact that something with a 5" diameter is bigger around than the cover on a 100-count spindle of CDs, I'll leave to someone else. :-)~

AnonymousAnonymousover 14 years ago
.

well done story although the color of jo bothers me... i wish you wouldn't emphasize so much on that but overall good story... probably one of the best I've read so far and i have read a lot of them

AnonymousAnonymousover 17 years ago
Naughty Girl

I love stories with girls in stiletto heeled boots and leather skirts. I am still wondering how far this will go. Will Jo sleep with strangers? Take hormones? Get the operation? Just be a sex toy once a month?

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