Never Bet with your Heart Ch. 02

Story Info
The bet leads to a new discovery.
3.2k words
4.34
101.6k
54

Part 2 of the 5 part series

Updated 10/30/2022
Created 06/23/2013
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We settled in as a tight first half had me nervous with Duke ahead by 2 on Carolina's home court. Ty was his usual calm self while my stomach was in knots, but just because of the game, the bet itself really wasn't in my mind. I wanted Carolina to win and so did my wife.

Fortune was on our side and the Heels put together an incredible second half and ended up cruising to a double-digit victory. Jill and I were pumped up but also tried to be good sports since Ty was with us. He proved to be as gracious a loser as he was a winner and said he'd make the arrangements to pay off his end of the bet.

I did not see Ty at work the next day but that night at home I got an email from him saying that he could not get us a room at the Park Hotel but that he hoped we would accept his alternative arrangements he had made at the Plaza Hotel instead. Needless to say Jill was stunned and more than eager to accept that pay off as a replacement. We replied that would be great and Ty sent back and email saying everything was all set for Saturday night for us and the reservation was attached. He said we'd be well taken care of and that he hoped we had a great time and he'd catch up with us early the next week as he had gone away for business for a couple days.

The Plaza Hotel was beyond what Jill had imagined and more. We were given a suite with a view of Central Park and proceeded to have a great time. The first thing we did was take advantage of that big comfortable bed and had some of the best sex of our lives. For some reason it just feels different in a hotel, let alone an elegant one. After we showered up and hung out in the cushy bath robes for awhile we got dressed for the night and there was a knock at the door. Ty had arranged for some fancy room service for us with some appetizers, snacks and a couple bottles of champagne and a note that said, "Enjoy... Go Duke!"

We laughed and then got a bit buzzed over the next hour as we enjoyed the evening. We had a comped meal in the restaurant that was extravagant and delicious and while on a carriage ride in the park we decided that afterwards we should head back to the hotel to take advantage of our one night instead of enjoying the city. We snuggled tight in the blanket that was given to us as it was a bit chilly out and then Jill looked up to me with those gorgeous eyes and I just stared back at her.

She said, "Am I everything you want?"

"Of course," I replied. "You are everything I want and more than I deserve."

"Then let's make tonight memorable," she answered. "Tell me something you've never told me that would make you happy."

I was kind of taken back and not sure how to reply. Nothing came to my mind. "You already make me happy," I said.

"Is there any fantasy or anything you've ever had that you want? Because tonight has been mine and now I want to make sure you get yours too," Jill said.

I tried to think of something and thought about the pictures I had been showing people of my wife and of the conversations I had with people online about her. I had not told her about any of that and was afraid at that moment that if I shared with her how much I enjoyed that she would be upset. At the same time there may never be a better time to tell her so I decided to go for it.

"I love showing you off," I said. "You are the most beautiful woman I've ever seen."

She looked up at me a bit surprised with a puzzled look. "What do you mean?" she said.

"I mean I love showing you off. Ever since that night we took pictures at Ty's and then started taking our own I can't get enough of that. I hope you won't be mad but I've shared them with people online and they all think you are amazing. It's all anonymous and I've never shared your face with anyone, but them seeing your body in your outfits and sexy lingerie drives them as crazy as it does me for sharing them."

Jill sat up all the way in the carriage. "Why didn't you tell me this before?"

"I don't know, it kind of came out of nowhere and even surprised me how much I liked it and then I wasn't sure how to bring it up to you," I replied. "Are you upset?"

She smiled before answering. "No. It's sweet and a compliment. As long as no one knows who I am I guess it is harmless."

I smiled a bit relieved.

Jill started to talk again, "So do you want to show me off tonight?"

"Yes," came my quick reply.

"How do we do this?" said Jill.

"I just have to set up my computer and get us online and people will come to us," I answered. Jill leaned over and gave me a deep kiss and settled back against me as our carriage ride finished up. It let off across the street from the hotel and it wasn't long before we were back in the room.

"I have a new surprise for you," said Jill. "So go ahead and set up what you need and let me freshen up and I will be back out in a few."

My cock turned into a rock. I got my computer out and started it up, logged on to the website with our profile and was kind of shaking the whole time. A few minutes later I heard my wife come out of the bathroom and turned to see her standing there. If a man could cum from a singular vision, that would have been it. My wife stood there in some of the most intoxicating black lingerie I had ever seen, lacy at points, sheer in others. Her tits were propped together and looked incredible and I as scanned down I saw the garters and panties and a pair of bright red heels that matched her lipstick and nails and whatever blood was not in my cock at that point was fighting to get in there.

Jill sauntered towards me slowly, letting me take all of her in as my eyes continued to bug out. She stopped in front of me and said, "How do I look? Do you think your friends will approve?" I couldn't answer her verbally and just kind of nodded as she approached and kissed me. She reached down and felt my cock and giggled a bit as we kissed.

"I guess I have my answer," she said.

For the next 10-15 minutes I showed her the website and our profile and how everything worked. She read all the comments people had left her about her pictures and I could tell she was very flattered and a bit turned on. Every once in awhile she would ask to see the profile of the person who left a comment and I began to pick up on a pattern that it was when the small image of the profiler had a nice looking body. I guess I couldn't blame her.

She made a few comments here and there in response to some.

"He's hot!"

"God that is huge!"

"Is that even real?"

Each comment sent shivers up my spine and turned me on more and more. Finally my wife asked me how I was going to show her off and I told her I could turn on the web cam. She could dance, strip, do whatever she wanted.

"I'll dance first," she said.

I turned on some music and told her where to stand so that her body could be seen but not her face and then turned on the webcam. It did not take long for us to have an audience and the incoming beeps and messages were overwhelming as people watched my beautiful wife dance seductively just feet away from me. I would try to read the comments to her as they came in and they were both complimentary and vulgar which only turned us both on even more.

Everyone wanted her to strip so she asked me what I wanted and I told her it was up to her. She told me this was my fantasy so it was up to me but I had to tell her.

"Do you want your friends to see more of your wife?" she said with a smile.

"Yes," was all I could muster.

She approached me and closer to the computer and turned her ass to the camera and shook it as she reached down and rubbed my cock and told me to lose all my clothes. I did not have to be asked twice. I stripped down and she asked me to stand up and she would dance around me as she stripped. My head was spinning as I heard the beeps start exploding from the computer as more and more people were watching and sending comments. My wife started dancing for me and stripping slowly starting with her bra. First her tits were on display for everyone as she had me fondle them as she faced the camera with me positioned behind her. She reached back to tug on my cock and I was doing everything I could not to cum. We both were watching the computer screen the whole time and my wife moved towards it and I heard her moan a bit under her breath. She clicked on a message and a video cam popped up with a man on the other end of it who had his own cam going. My wife just purred as she saw him in all his glory. He was a pretty built white guy with a pretty big dick, but like us, not showing his face. She stared at the screen as she backed back up to me watching him jerk off to her.

She leaned her head back into me and whispered over her shoulder, "Rub my pussy for him baby."

I did as I was told and rubbed her pussy over her sheer panties and they were soaked. My wife moaned as I kept up my work on her. A few moments later we watched as the man on the other end erupted, his cum shooting out of his cock with force. He shut down his cam moments after.

"God that was hot," my wife said.

She went back to the computer and clicked on another one. This time it was a black guy with another great body and another huge dick which was limp as he lay on his bed. If that was what it looked like limp who knew what it was going to look like after getting revved up. I had to admit his body looked like a damn Adonis. His volume was up and we could hear his voice and he was telling my wife how great she looked which was turning her on by the second. He finally told her he wanted to see that pussy of hers.

My wife leaned to me again and said, "Show him my pussy baby."

So I unhooked the garter belts and then hooked my thumbs into her panties and started to slowly slide them down her gorgeous legs. I had to give an extra tug to pull them away as they were caught up a bit in her glorious triangle. My wife was dripping wet and I could smell her sex taking over the room. It was enough to make me dizzy with lust. The man on the other end approved.

"That is a beautiful pussy baby," he said. "Look what it is doing to my cock."

We both stared as we watched his cock start to grow to an obscene size. My wife was stunned. He told us to come closer to the screen and so we did.

"You think you could handle this cock baby?" he asked my wife.

I didn't know if we were supposed to answer or not, it seemed kind of rhetorical. But the man continued.

"Lean down and tell me," he said.

And Jill did just that. She leaned in towards the cam and I could see that the bottom part of her face was now on the screen and her pussy and tits were showing and the beeps were going off like firecrackers on the fourth of July. I was brought back to the present when I heard my wife talk. "It's beautiful but I don't think I could handle it," she said.

"Why not baby?" came a quick response.

"It's so big and I've never been with a cock that big," she said.

Jill had been stroking my cock slowly as she chatted by reaching her hand back around and I was having serious trouble holding back.

"Your man must love to show you off baby and I don't blame him, you are gorgeous and the best looking thing on here," said the man. "Please thank him for all of us."

My wife giggled as she continued to stroke me and it was less than a minute and I knew it was all over and I tried so hard not to cum but there was no holding back and I splashed my load onto the floor in front of me.

"Well it looks like someone is out of commission for a few minutes so why don't you pull up a chair and play with that pussy of yours for me as you watch me stroke my cock and pretend I am there giving you the fucking of your life. I think we all would like that."

Jill grabbed a chair and wasted no time as she started to furiously finger herself and did whatever the man on the other end of the screen told her to do. I sat and watched in amazement, looking at her and looking at him. My wife was lost mentally, I could tell, she was just in a trance as she masturbated and watched the scene on the screen. All told it had been about 10 minutes when I heard my wife start to make strange noises. I knew she was close and so did her new friend.

"Here it comes baby. This is for you," he said.

Then we watched as his cum erupted from his cock, stream after stream of thick white cum landing on his chiseled black body, at least 6-7 huge spurts. This sent my wife over the edge and her orgasm wracked her entire body as she thrashed about on the chair. It was nothing like I had ever seen before. When she came to it was like she had seen a ghost.

"See you soon baby," came the voice before the screen went dark.

The beeps and messages were still flooding us as everyone watching had just seen my wife have an incredible orgasm through her vigorous masturbation. If they only knew what set her off I thought to myself. The sounds of the beeps must have jolted my wife to realize what had just happened as she snapped her head and looked at me.

"Turn it off, please," she said.

I jumped up and turned off the camera and logged us off. I looked back at her, totally spent, still sitting on the chair, her juices soaked all down her legs, on the chair and her pussy looking totally spent.

"Are you okay," I asked.

"I don't know," she replied.

"Are you upset we did that?" I asked with concern. She didn't answer.

"I'm sorry sweetie. I should never have asked you to do that. I guess I got carried away," I told her.

"It's not that. I've never had an orgasm like that in my life. It was exciting to show off for you and make your fantasy come true. I was having fun. I got into it because it was anonymous and no one knew me and I didn't know them," said Jill. "Okay so what's wrong then?" I asked.

"I think a line got crossed at the end," she said.

"What do you mean?" I questioned. "You had a great orgasm and I got to watch it and it was amazing to see how beautiful you looked and so what if some other random guy got to watch and was the reason for it. Sometimes other people can enhance the fantasy."

"Sweetie," my wife started. "I don't think that was some random guy that just watched me."

"Huh? " I asked.

"I think we both know who that last man was. The question is does he know that was us."

"What are you saying babe?" I replied.

"Don't freak out, but I am almost 100% positive that was Ty," she said.

My eyes got big as saucers and I instantly felt my head spin as I considered what my wife said. It hadn't dawned on me at all and I was trying to run it all back in my head.

"There's no way it was Ty," I finally said. "What are the odds of that? That would be nearly impossible."

"Sweetie," my wife paused. "That was him. I just know it."

I went back to the computer and opened up the website again.

"What are you doing?" my wife asked.

"Well I am going to see if I can find that profile. I remember the screen name and we'll see if you might be right," I said.

I entered the name in the search and the profile popped up. The main profile picture had no face so that was no help. My wife joined me as we looked over the details. The profile said the person lived in New York City, the physical description was pretty accurate for Ty as well and I started to get nervous. We clicked on the pictures and started to go through them one by one. They were all various body shots, of which we had seen the real thing and they each had some description -- chest, abs, cock -- etc. and then the last picture we clicked on made both of our hearts stop. It was a picture of a woman in a tiny blue g-string with a Duke logo over her pussy and the caption to the picture said -- "My dream woman... too bad she's taken."

Well we didn't need to wonder any longer as we both stared at the picture of Jill on the screen. The question was now answered. My wife had just put on a show for Ty. We looked at each other with somewhat blank expressions. The only question that remained was did he know that his dream woman had just put on a show for him.

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21 Comments
HighBrowHighBrow23 days ago

This series is a little more fantasy than I expect from this author.

26thNC26thNCover 2 years ago

More monkeyass special cuck story.

TopcityloversTopcityloversalmost 3 years ago

Love this story! My fantasy is to show off my wife just like that. Have her hot and bothered on a web cam and cumming for guys with big cocks!

B_CouricB_Couricabout 3 years ago

I imagine Ty being a Boston College fan and all he does is call in favors for hotel rooms. /s Great story so far!

texxmantexxmanabout 5 years ago
This guy is an idiot

Can he save his marriage?

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