What a Deal! Ch. 04

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I lose a bet and become weekend slave.
8.8k words
4.54
96.5k
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Part 4 of the 31 part series

Updated 02/24/2024
Created 03/15/2011
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deadeye_76
deadeye_76
1,685 Followers

From the last story

They put their stuff together and were gone in 30 minutes. Jack promised to let me know what happened and made Louise promise to write down everything that they did, with details, and email it to us. Cindy was ecstatic. She loved reading erotica, and now she was going to have a personal interest and reason for reading it.

After they left we had dinner, talked, and went to bed. Cindy asked me to eat her pussy because she was still worked up. It was a tough job, but I was up to the task!

*

I came home later that week, on a Thursday and found my wife, Cindy, and her friends Diane and Becky at the table, naked and playing cards. I had seen them all naked before and had sex with all of them, but this was something different. I asked what was going on.

"We're playing strip poker." Cindy smiled and giggled. The other two giggled as well.

They were all already naked. "But you are all already naked, so what's the point?"

"Well, now we are betting other things."

"Like what?" Now my interest was peaked.

"Nothing much, just things you have to perform. You missed it when Diane had to eat Becky's ass until she orgasmed. You would have liked that."

My dick was definitely hard now. "Yes, I would have. It's too bad I got home so late."

"Yes, it is, because they both have dates tonight and have to leave in about 15 minutes. Guess you'll just have to settle for fucking your horny wife!" She grinned at me and flashed me her pussy.

Well, sometimes life is really rough and you have to perform your husbandly duties whether you want to or not... yeah, right! Like fucking my tight-bodied little wife was tough! She had turned into a bisexual dynamo and I loved it.

The other two ladies left and my wife and I had pretty hot, but normal sex. When it was over, it was only about 9:30 and I was watching some college football on ESPN. She turned to me and watched for a minute. "Who are you rooting for?"

"I'm rooting for State."

She looked at me. "Wanna bet on the game?"

"Bet? You don't even watch football."

"Yes, but it's tied now and I'll take the other team and we'll make a bet."

"What kind of bet did you have in mind?" I sneered at her, thinking that it would be something trivial.

She grinned at me. "Let's see.... How about this? I have a conference coming up a week from Friday for Friday afternoon thru Sunday morning. If I win you have to go with me and be my slave from the time we arrive at the hotel until we leave."

I stared at her. This was completely unexpected. "What? What made you think of that?"

"It's something that I know a controller like you will have trouble with, so that's what I want. Now what is it you would want if you win?"

I thought long and hard about it, but I was having trouble coming up with anything. I was still too shocked by her desire to make me a slave for two days; something she had never even expressed before. "Well, if I have to spend a weekend as your slave if I lose; I think if I win, it's only fair that you go an entire week wearing skirts and blouses without bras and panties, and you meet me for lunch every day and do whatever I say... in public or private."

She stared at me. "Wow! That's interesting." She stared at me for a second, but seemed to have no trouble making up her mind. "Okay, it's a bet. No welching either. Whatever happens, we have to do it. Agreed?" She put out her hand to shake on it.

"Agreed!" I shook her hand.

We watched the game and it was a close one all the way. When my team went up 3 with 1:45 to play, I started to breathe easier. She knew that I was the type that always had to be in control and that it would be difficult for me to give that up. The thing I bet was probably not as difficult for her, but I didn't have much time to think about it. I knew what she was doing. She was trying to get me out of my comfort zone. I needed to come up with something better next time to push her limits. Unfortunately, my team committed a personal foul on the kickoff return and suddenly her team was 30 yards away from the end zone with two timeouts and 55 seconds on the clock. It was an eternity in football. Sure enough they managed to score a touchdown and send me to defeat. I sat there for a minute, stunned.

Cindy just sat there and grinned. "Wow! I get to have my own personal slave next weekend. It's going to be fun!"

I couldn't really get my mind around what she might do to me, but I was apprehensive anyway.

When the next Friday finally came, I had taken the day off so that we could leave and drive the 300 miles to the conference. Cindy was energized and bouncing around, gloating. "I am going to have so much fun playing with my slave this weekend. I can't wait to see what I come up with." Yeah, like she didn't already have something in mind! "Oh, don't bother packing any underwear. You will not be allowed to wear any this weekend." I stared at her. She had asked me to pack some of my light dress pants. With those on and no underwear, my dick would be plainly visible a lot of the time. She smiled at me. "This is going to be so fun!"

"Yeah, I can't wait."

"Hey!" She pulled me in front of her. "No welching on the bet. Remember, that I'm your wife of 20 years. I won't do anything that will get you hurt." I would have relaxed, but then her grin turned positively evil. "But I will push your limits this weekend!"

My anxiety grew as I drove and we approached the hotel. Cindy seemed to get more animated and excited, which heightened my anxiety.

Finally, we pulled in front and she smiled at me. "Remember, once you get out of this car, you are mine to do with as I please."

"Okay." I started to turn to open the door and get out.

She put her hand on my arm and I turned to face her. "While we are here, that's 'Yes, ma'am' to you!"

I stared at her. Butterflies were flitting everywhere in my stomach. I hesitated, but finally said it. "Yes, ma'am."

She released my arm and we got out. I went around and opened the trunk and took out our two suitcases. She just started strolling into the hotel, leaving me with them both. Shit! She was definitely going to push my buttons.

I entered the hotel and went up beside her at the front desk. She had already provided her name and the name of the conference since they had reserved a block of rooms. The pretty little receptionist checked everything and handed her a card. She took the card and filled it out. The receptionist handed her the room keycards. She then turned to me, handed me one of the cards, and said so that the young female receptionist could hear. "Dennis, take the suitcases upstairs, unpack them, strip, and then draw me a bath. I'm going to have a drink and will be up in a minute." She grinned at me, waiting for me to answer as the receptionist stood there.

"Yes, ma'am." I blushed.

I looked over and the receptionist's eyes went wide. She had no idea that my wife was playing this up for her.

Cindy turned to her. "If you start when they're young, it's much easier to train them."

I flinched at that, but turned to go upstairs. Fortunately, I would never have to be back to this hotel. Cindy gave me a light smack on the ass and I turned as I walked away. She was grinning and winked at me. The receptionist had her mouth open in shock.

I didn't say anything, but I was shocked that Cindy was being so open about this. I did as she had asked and the bath was filling with water and I was sitting on the bed naked when the door opened. Cindy came around the corner grinning. Then another woman turned the corner and I stared like a deer in the headlights of a car. She was gorgeous, but grinning and giggling at my predicament. I was sitting on the bed, trying to cover my crotch while she stared.

"See. I told you. He lost a bet and is my slave for the weekend. Hey slave, stand up and stop covering the merchandise. This is a friend of mine, Mary, from the last conference and I promised her a free show."

I was fuming, angry, and excited. I slowly rose to my feet and put my hands at my side. I was blushing again.

Cindy walked over and took my dick in her hand. It started firming up. "See, he has a nice dick. It's just the right size for me. What do you think?"

The woman stared for a second and licked her lips. "Nice!"

"Well come over here and check it out before you pass judgment!"

Mary tentatively approached me and put out her hand. Cindy dropped my dick and Mary lightly put her hand around it. It jerked a little and started rising more as the blood flowed in.

Cindy was really enjoying this. "Look at it grow. It's a really nice dick whether you want to suck it or fuck it with your ass or pussy."

Mary looked up at Cindy a little in shock, but didn't remove her hand.

Cindy turned toward the bathroom. "Looks like the tub it almost ready. Slave, come finish getting me ready for my bath."

I slowly removed Mary's hand from my dick as it seemed she didn't want to let it go. I went in and shut off the water. I came back out and they were both sitting on the bed. Cindy stood up.

"Undress me, slave."

I started undressing her and Mary stood. "I'll see you later. The first get together is a social at 7pm."

"Wait!" Cindy stopped her and I stopped for a second. "Not you, slave, finish undressing me." I removed her blouse and she had no bra on. I was working her pants down over her hips. "You can stay, Mary. I want you to see something before you go." I finished stripping her pants off and then I worked on her panties. They came right off.

"Are you sure?" Mary had finished watching me undress Cindy before asking.

"Absolutely. My slave will entertain us while I bathe."

Cindy walked into the bathroom and slowly climbed in the tub. "Mmmm. It's just the right temperature, slave." She settled all the way in and it covered her to her neck. Mary was standing at the doorway watching and I was standing next to the tub.

"I just want to relax in here for a minute and both Mary and I want to see you cum, slave."

I stared at her.

"Well, c'mon. Get to jerking that thing. We want to see you spurt into my bathwater, right Mary?"

I looked over and Mary was a little stunned. "Uh... yeah... sure."

I looked back at my wife and she smiled and winked at me. Fuck! I was going to jack off in front of this stranger and we had only been in the hotel for about 30 minutes. I had very seldom jacked off in front of my wife and never in front of another woman.

I took my dick in my hand and tried to think of fucking Becky in the ass. I wanted to think of something far away from this and my wife right now. It was a good image and I was hard and starting to feel good about cumming.

"Open your eyes!" Cindy spoke firmly. She looked over at Mary. "Mary, have you ever held a dick when it shoots off?"

Mary looked at my dick and back at Cindy. "No."

"Well, come over here." Mary advanced the last couple of steps up next to me. "I want you to finish him off. Just jack off his dick, I'm sure you know how to do that, and reach up under his ass and play with his balls. He loves that."

Mary did just that and I started thrusting into her hand. Her had was smooth, soft, and firm.

I looked at her face and she gave me a sheepish grin. I was getting close and she could tell. I looked down at Cindy and she winked at me again. I was thrusting and May was jacking me and playing with my balls. Oh, fuck! I grunted and shot my spunk all the way across the tub onto the far wall, the second and third shots landed in the water and then the rest just flowed out all over Mary's hand. She didn't seem to care.

"Nice, slave. Thanks for the hand, Mary." Cindy giggled at her pun.

Mary grinned at both of us and finally released my dick. "It was fun. I don't think my husband would ever do that."

I looked up at her suddenly, realizing that she was married. She stared back.

"Shhh." She put her cum covered fingers to her mouth and shushed me. "We don't have to tell him, right, Cindy?"

"That's right."

Mary then made a show of licking her fingers. Cindy watched closely. When Mary was done she looked down at Cindy and then at my shrinking dick. "Thanks. See you later." She left.

Cindy smiled up at me. "You did very well, my husband. I know this surprised you and that you have never had a woman just jack you off like that, but it was very interesting. The rest of the conference will be even better, I assure you."

"Well, that was definitely different."

Cindy laughed. "And you don't know Mary at all. She has the biggest mouth at the conference!"

I stared at her. "You mean you think she's going to tell everyone about this?!?" I was incredulous.

"At least her close friends. We may have some more ladies come over tonight." She smiled. "Now go into the other room and relax and watch some TV. I'll be out in a minute and we can get dressed for the happy hour."

I went and did that, wondering what was next.

We arrived at the happy hour at 7:30 and it was in full force. My wife worked at a makeup company, so probably 90% of the people at the conference were women. She had dressed me in some light dress pants and a polo. Any stirring at all in my groin was going to be obvious. Cindy was wearing a pretty short skirt, dress shirt, and some nice heels, which she had made me put on her, and nothing else. She looked divine and I wanted to jump her bones.

"Cindy!" I heard Mary over the din of the room. Oh, shit, here we go.

Cindy grabbed my hand and led me over there. Mary was standing by a small back booth. "I got a back circular booth like you said. Nobody else I know is here yet."

Cindy turned to me. "Sit in the back of the booth." I did.

We had drinks and Cindy and Mary talked and laughed and didn't include me in any of the conversation. Finally, about 8:30 several more women that they knew from these conferences had joined us. I was in the back of the booth and they were all standing in front of it so it was like I wasn't even there. I felt like a mushroom, being kept in the dark. Since it was so loud by now, I couldn't hear a thing that was being said, but suddenly I felt eyes on me and I looked up. Mary and Cindy were talking into the ears of a couple of other women and they were staring at me. Shit! Here we go....

Cindy put her hand out and leaned down so that I could hear her. I took her hand and she spoke to me. "Go up to the room, strip, and lay on the bed. We'll be up in a minute."

I stared at her for a second and she just waited for me to move. Finally, I stood up and made my way thru the crowd. She had said 'we'. Fuck, she was bringing at least Mary along.

I stripped and lay on the bed. I turned on the TV and was watching sports when, about 45 minutes later, the women entered. I sat up suddenly and made sure I looked decent (covering my dick) as six women filed into the room. Cindy led them all over to the bed. "Ladies, meet my slave. Slave, these are my friends." She pointed to each woman. "Mary, Louise, Roberta, Jenny, and Sarah." I checked them out. Mary was about 5'5", nicely built, auburn hair. Louise was about 5'9", a tall, willowy brunette. Roberta was short at about 5'1" and probably weighed about 140. She was a little heavy, with big tits. Jenny was small and tight, like my Cindy. Sarah was the bad girl. She was about 5'8", very skinny, goth-like in all black clothes, dark makeup, short cropped hair, and several piercings in each ear and one in her eyebrow.

I didn't say anything at first, and then Cindy reached over and smacked me on the thigh very hard. "Hey, slave, get up and greet each of these ladies with a kiss!"

I stood up tentatively and started with Mary. I said hello and gave each a little peck. When I got to Sarah, she reached down and grabbed my dangling dick. "Looks pretty good." She grinned. I blushed and lowered my head.

Mary was carrying a bag and put it on the counter. "Okay, ladies, tonight its scotch night. I have a good bottle of Macallans that we can drink." I wondered how drunk they were going to get. They all appeared to already be flushed from drinking in the lounge.

Cindy turned to me. "Slave, we need some ice for our scotch. Run to the ice machine and get some ice."

I stared at her. I looked down at my nakedness and back up at her.

She grinned. "Better hurry!"

I looked at all the women and they were grinning at me. I grabbed the ice bucket and headed for the door. Fuck! I didn't know how I was going to do this. I was embarrassed already, my dick was semi-hard from Sarah's grope, and I had to get to the ice machine and back without getting caught by some hotel security guard. I had never been naked in public in my life. It was not my thing.

I started to turn back toward the room, but Cindy was right there. "C'mon honey." She was whispering in my ear. "Honor the bet!"

I shot daggers at her with my look, opened the door, and stepped out. It was still early, so maybe everyone would stay in the lounge a little longer. I raced to the right where I had seen the sign for the ice machine. I stepped into a little room to fill the bucket. So far, so good. I filled the bucket and was heading back to the room when a door just past our room opened and two women stepped out. They turned to walk my direction and froze. I walked as fast as I could to our room. They were two doors further up and just stood there. My dick, still a little chubby, was slapping back and forth on my thighs and I cringed at them seeing me like this. I was never an exhibitionist, so I knew I was turning bright red. I tried not to look up. I reached our door and looked at it. Fuck! I was naked and had no key. I knocked on the door and waited. I glanced to the right, seeing their feet approaching and the two ladies were coming my way. I could feel their eyes on me, but I couldn't look up at them.

"Looks like someone left something in his room." One of them spoke.

"Yeah, but it's good for us. I haven't seen a naked man in a hallway in... well... never!" They both laughed.

I knocked again and finally the door opened. Cindy grinned at me and looked out. The two women were just even with me. She waved. "Hi, ladies. Just having a party with my little slave here."

They laughed as they passed behind me. One of them turned. "Not too little, though, huh?"

"Nope, just right." She stepped back and I entered. I was so embarrassed that I'm sure I was completely red. I put the bucket on the dresser and sat on the bed. I tried not to look at anyone. Cindy was recounting the story to the other ladies and they loved it. I was so humiliation at being forced to do this. This had never been done to me before and I wasn't really a fan of it.

Cindy came over and kneeled down in front of me, grinning rudely. When she saw the humiliation in my eyes and that I wouldn't look at her, she softened. She leaned forward and whispered in my ear. "I love you dearly. This is all in good fun. Please don't quit now. Honor the bet."

She knew that my friends and I never welched on a bet and she was counting on me here. I nodded.

She stood up and returned to being the dominate bitch. "Okay, slave, lay flat on the bed on your back." I did, trying to remember that this was my wife of 20 years and that she had just told me that she loved me. She went to her suitcase while the women all ogled me. They were drinking and talking and I could hear comments about their boyfriends or husbands and how they compared to me. I could almost feel their eyes on my body and I closed my eyes to shut it all out. Cindy came back and I opened my eyes when I felt the bed move. She had two spreader bars. I stared at her and she grinned and climbed up over me. She put the first one between my wrists. She then crawled off and put the second between my legs. I could raise and move my hands and legs, but they were locked about three feet apart each. She turned to the others, who had quieted during this. "Okay, ladies. The slave's face is open for business. Who wants to ride first?"

deadeye_76
deadeye_76
1,685 Followers