Time to Payoff the Bet

With fifteen years of marriage behind us and having tried a few threesomes with two male friends of mine, Cindi seemed finally convinced that she could have fun sexually with other men and it would not cause a problem but would be exciting to both of us. She slowly began to be more receptive to some of my "wild" suggestions. First, we had a threesome with my old college roommate, then a business acquaintance of mine. We would see my old college roommate only a couple of times a year because he lived quite a distance away. The business acquaintance, we got in the habit of seeing every couple of months. It was fun and we all enjoyed it. But I had a plan and was working towards fulfilling Cindi's ultimate fantasy she had shared with me, a gangbang. This story isn't about that yet, we were still working towards it.

When Cindi confessed her fantasy to me it really wasn't a surprise. I could tell when we were in bed together watching x-rated movies together, scenes with one woman and multiple men would always get her pussy wet. I may be slow, but even I could figure that out. I wasn't sure we would ever get to that point but it became as much of my fantasy as hers. When we talked about it she admitted the fantasy was exciting but repeatedly said she could never really do it.

I have given more than a fair amount of thought to why watching my wife please other men excites me so much. Not being a psychiatrist, or really caring that much why I didn't really come to any conclusion. I just know what I like.

When Cindi and I were dating and the early years of our marriage I was extremely jealous of any attention other men would give her. Now I just love watching her suck or fuck friends of mine, as long as I am present. If she did it without me being there we would have problems.

As beautiful as she is, it is little wonder she garners so much attention. That long dark hair and those baby blue eyes are a stunning combination and I know every writer goes on and on about how sexy their wife or girlfriend's body is, being no different I will just say she could always attract almost any man she ever wanted and leave the rest to your imagination. I was first attracted to her because of her beautiful face and her sexy legs. As she has aged her breasts have filled out so I have changed from a leg man to a boob man. Yeah, I am all about being flexible.

This story is about our third experience with another man. Having tried threesomes with two other men both of which went so well we continue to this day to see them on occasion, Cindi was much more receptive to trying to seduce another man and much less worried about being turned down. Our first two lucky guys did a lot to boost her ego, although I still cannot understand why she needed it.

Mike is a friend of mine through work. My employment keeps me in contact with many people throughout the business community. We chose him because he is close to our age, possible a few years younger. Whenever we were in social settings he always seemed to flirt a lot with Cindi so we were pretty certain he would be interested. He is married but we are not close friends so it didn't cause a huge conflict for Cindi. Ever since I remodeled my basement into a home theater and sports bar theme I would often entertain business clients with small gatherings at our house providing plenty of food and drinks whenever some major sporting event was occurring.

The night I invited Mike over Cindi was very nervous but excited too. When Mike arrived we went straight to the basement to watch a game. Mike was surprised he was the only one there. I explained I had invited a couple of other guys over as well but both had cancelled and joked about that just leaving more food and drinks for us. We settled in to watch the game and drink.

By arrangement Cindi had not been home when he arrived. About an hour into the game she came home and made an appearance to say hello and let us know she was back. She was dressed in a modest skirt and blouse but as always looked very feminine and sexy. The blouse was a sexy shear white that showed the lacy camisole she had on underneath. I was certain when she bent over to kiss me hello she purposely did it in a way that gave Mike a good look down her blouse. As I glanced over at him he had a guilty look on his face and looked away quickly like a kid getting caught doing something they shouldn't.

We watched the game for another hour or so and kept up the drinking and the conversation. I kept a lot of the conversation around good looking women and whenever I could I would talk about Cindi. I made a comment about how good she looked tonight and Mike readily agreed and I said one of the things I always liked about her was how she would dress so professionally but still look feminine and sexy. I especially liked how she made the effort to dress sexy when we went to bed. That topic seemed to interest Mike so I went into more detail about how that was always her signal to me that she was ready for some fun. When Cindi wanted to play she would put on a sexy nightgown, negligee, or babydoll nightie and it never failed to excite me. Mike just laughed and said I was a lucky guy and I responded by telling him how well I knew.

Having established a comfort level I walked back to the bar from our chairs to get a couple of more beers. Mike followed me since he was on his way to the bathroom but I stopped him by saying, "Hey want to see something you might enjoy?"

I reached under a box behind the bar and pulled out a photo album and said, "If you hear Cindi coming hide this quickly!"

As I tossed it on the bar he slowly opened the cover and was greeted with a picture of Cindi laying on our bed wearing a very sexy and revealing long nightgown that revealed more cleavage than she would ever reveal in public and a big smile but otherwise a pretty tame picture. Mike grinned and said, "She looks pretty hot!"

I told him the pictures get more revealing and if that offended him he should stop knowing full well he was anxious to see more. "Go ahead, take a look. Just don't get caught."

Mike started browsing through the pictures slow enough to enjoy them but anxious to see the next one. The pictures were purposely arranged in an order form less revealing to more revealing. As soon as he figured that out he grabbed the back cover and flipped to the last picture to see a nice picture of Cindi sucking my cock with a little cum dripping out of the corner of her mouth while smiling at the camera.

"Holy shit! How did you get her to let you take these?" he asked.

"Oh, we like playing with the camera. We have these and videos too." I told him. "She likes being watched at times. I discovered this one time when I asked her to let me video her masturbating so I could take the video with me on a trip."

"Are you serious?" he said as he still was browsing through the pictures, some for the second time.

"Yeah, if you want I could probably play one on the big screen if you wanted. I have several now."

"Unbelievable! What if she comes downstairs? She will throw us both out of here." He said seeming only a little concerned but clearly interested.

"Okay, as soon as the game is over I'll play one. I'll go upstairs and check to see where she is and what she is doing first to make sure it is safe."

Mike laughed, "Fuck the game!"

"Okay," I also laughed, "I'll go check now."

I went upstairs to let Cindi know Mike was clearly interested so she could quit worrying and that she should just play along since our plan was working. I told her to give us about fifteen minutes and come downstairs.

I returned to the basement with a video and put the tape in and turned the volume low. The video started with Cindi walking in front of the camera wearing a very short black skirt, a silky blouse and high heels. She sat on a couch in front of the camera smiled and said, "Are you ready?"

Next she stood up and pulled her panties down and took them off. You could see she was wearing black thigh-high stocking as she was removing her panties. She sat back down and teasingly pulled up her skirt until you could almost see her pussy. Everything was in slow motion, she was doing a great job of working up the anticipation.

Cindi then put her feet up on the edge of the coffee table and spread her legs to show off her pussy. At that time she still had a neatly trimmed bush. She slid her hand down her body and using two fingers started slowly rotating them around her clit. The entire time she never took her eyes off of the camera so it looked like she was looking right at us.

Then she took her hand and put it in her mouth for some saliva and returned it to rubbing her pussy. First small circles then a finger went inside briefly as she continued to flash that big smile.

She then said something that couldn't be heard on the video as she reached behind the pillow and retrieved a dildo she had put there. She put the dildo in her mouth for lubrication then started rubbing her pussy with it, plunging it in and out of her and very visibly working herself towards an orgasm.

I looked over at Mike and saw him shifting in his chair trying to hide his erection. I laughed to myself and said out loud, "Fuck! This always gets my dick hard." as I made no effort to conceal adjusting my dick in my pants. "She is sexy isn't she?

Mike just laughed and I think was still a little embarrassed but he said, "Unbelievable!"

We watched the rest of the video with Cindi exploding into a climax that became very loud so I adjusted the volume even lower. Then I said to Mike, "Hey want to have some fun with Cindi?"

"What do you mean? He said with a puzzled look on his face.

"Well, I have an idea and I have no idea what might happen but if it goes like I think it will you will enjoy it. Trust me, okay?" I said as I got up to remove the tape.

He pressed me for more details and I avoided answering his questions until I heard Cindi coming down the stairs. She entered the room and had changed into a pair of very short shorts and a tank top without any bra. She looked beautiful.

As soon as she walked in she said, "What are you two up to? Are you drunk yet? Am I going to have to take you home Mike?"

I said "we had a few drinks but we have been watching something that got us a little excited and wondered if you could help us out."

"What does that mean?" she asked.

"Cindi, do you remember that bet we made a week ago?"

"Yes, why?" she looked hesitating a little.

"Well I think tonight is a good night to collect on that bet?" I said.

Cindi's face turned red as she stood there looking at me then looking at the floor. "Are you sure?" she said, "Tonight?"

"Yes. Definitely tonight." I smiled. "Mike, I think you are going to like this!"

"What do you want me to do?" she said with a look of resignation.

"Go put on a very sexy negligee and come back here." I ordered her, "and bring your vibrator."

Her face turned even darker red before she turned to leave the room.

"Mike, how would you like a live reenactment of the video you watch?" I asked knowing the answer.

"Oh shit man, are you serious?" Is she really going to do that?" he was shifting in his chair again.

"Yes," I replied, "for the rest of the evening she will do everything I tell her to do, so if you can think of something fun, tell me."

"I can't believe this." he mumbled.

"Maybe we will get lucky and push the envelope a little tonight." I said.

"What does that mean?" he asked.

"Be patient and let's see what happens," I told him.

After what seemed like forever Cindi returned. She was wearing a sexy red babydoll gown that barely covered her ass with a matching red thong. The top had a built in bra that pushed her breasts together showing off ample cleavage and just barely covering her nipples. It looked like her breasts were on a shelf to be admired. And we did. She was also carrying what looked like a purse.

I had moved a chair to the center of the room for Cindi's performance. We sat in our chairs as if we were looking at the big screen but instead were looking at her waiting for the show. Cindi sat in the chair with her head slightly down. "What do you want me to do?" she asked.

"First, we want you to take your panties off." I said.

Cindi reached down and without exposing much slid her panties down her legs and kicked them off of her feet. Her legs were still close together so we really couldn't see much.

"You know what we want Cindi. We want to see that pretty pussy of yours. We want to see it again." I told her.

"What do you mean again?" she asked still not looking directly at either of us but I thought I caught her looking at Mike's crotch. "A while ago I played one of my favorite videos of you masturbating for Mike. I think he enjoyed it quite a bit, didn't you Mike?"

"Uh, yeah," he muttered still seeming a little unsure of where this was headed.

A little shudder took over her body when I said that, almost like a mini-orgasm. I told her we both thought she was very beautiful and she should be proud of her body and pleased to show it to us. "Put your legs over the arms of the chair" I ordered.

Cindi obeyed, her face red but more likely from excitement rather than embarrassment. "Now, play with yourself and use the dildo." I told her.

Cindi didn't waste much time. She put her fingers on her pussy and we could already see the wetness. She didn't have to lick her fingers first this time. At first she rubbed slowly in a circular motion, then up and down occasionally letting one finger penetrate inside. She was dripping wet. She stopped long enough to reach into her bag and retrieve the dildo I had told her to bring. It was a vibrator shaped like a nine inch cock, flesh colored with a speed switch on the bottom to adjust the vibration. Cindi turned it to a low speed and started moving it up and down her juicy cunt. We watched as she kept her eyes closed most of the time as she was building herself to a climax.

I waited until I thought she was beginning to get close and told her to stop. She stopped and looked at me and asked why. I really wasn't trying to be cruel. I knew she was getting close but I wanted her to wait because I thought the anticipation might make the experience greater.

"Cindi, you look incredible tonight and you have my cock as hard as a rock and I am guessing Mike's as well", I said without even looking at him. "I need some relief and I bet Mike does too." I want you to come over here and suck my cock."

Cindi truly loves sucking cock and she seems to enjoy it even more when she has an audience. She very quickly got out of the chair and came to me, kneeled in front of my chair and started unbuckle my pants and pull them down. She grabbed my pants and underwear pulled them both down at the same time after carefully freeing my cock. Then she went to work on my cock. She started kissing it and licking it and just before she took it in her mouth I saw her look over at Mike and smile.

She sucked me like she loves to do. Licking around the head first, putting it part way in then swirling her tongue around the tip, then slowly going as deep as she can. Cindi has never been able to deep throat but she comes damn close. I let her do it for a few minutes before I stopped her.

"Cindi, it's Mike's turn," I said. "Mike, get your pants down if you want her to suck it for you." I think that was all he was waiting for because as soon as Cindi moved in his direction he stood up and got his pants and underwear not down but off before she could get there. He sat back down as Cindi reached for his cock and began to stroke it.

"Honey, give him one of your best blowjobs okay? Show him what I get all the time."

Cindi just nodded her head as she was already licking up and down his hard shaft. She licked and got his cock wet so she could jack it a few times with her hand, Then she put her lips on the very tip and it looked like slow motion as she tipped her head back, looked him in the eye and took it in as deep as she could in one motion. Sometimes when she does that, she will go until she gags. I barely heard that little sound from her throat over the sound of Mike groaning. I thought for a minute he was going to cum right then.

She backed off a bit taking it out of her mouth and licking his balls for a while but continuing to slowly stroke him. She alternated between licking a while and an occasional deep suck. She was trying to get him right on the edge and keep him there. I have been there many time with her, it's a great place to be.

"Mike", I said, "you need to know Cindi loves to suck cock and she will swallow your cum if you want. If you prefer to cum somewhere else so say. But feel free to empty you load into her mouth, she will not mind, right baby? Tell him what you like."

"Mmmmm,uh" she mumbled keeping her mouth occupied with his dick. She paused long enough to say, "You can cum in my mouth, I really do love it. Do you like that when a woman swallows your cum? I hope you have a nice big load for me." Then she went back to work. Mike was straining to hold back but it wasn't working. Cindi was jacking his cock, playing with his balls and licking and sucking like crazy. I have to admit I hadn't seen her this worked up in a while.

It didn't take long before Mike gave it up. His body stiffened and he arched his back trying to shove his entire cock down her throat as he shot spurt after spurt into her mouth. Cindi never took his cock out of her mouth. She kept her lips locked and swallowed as fast as she could. At one point she opened her lips to take in some air and I saw a small dribble of cum leak out but otherwise she took it all.

"Fuck! That was incredible!" Mike said after he calmed down.

"Mmmmmm, that was tasty," Cindi smiled as she replied. "Hopefully there will be more later."

I was about to lose it myself and I wanted her pussy so I went over to where she was kneeling and got behind her and quickly slid my cock into her soaking wet cunt. I have known for years that sucking cock for Cindi isn't something she does just to please men, it excites her very much. She says it gives her a feeling of control over men which is probably true but it always excites her. I cannot remember the last time we had sex that she didn't suck me at least for a little while.

I went nice and slow wanting to enjoy that feeling for as long as possible. Cindi kept her head resting in Mike's lap playing with his now soft cock and moaning as I fucked her. I had a change of mind as my climax built up and as I got close I pulled out and told her to suck me off.

Cindi quickly turned around as I lay back on the floor and took my very wet and very stiff dick in her mouth. I was close enough and I wanted to cum so bad I didn't even try to hold back any more. I wanted release and I wanted it now. Just as in any other time we had other with us I was ready and let it go shooting spurt after spurt of my cum into her mouth. She was sucking so hard I had to have her back off a little but she never stopped and took it all as she will whenever I ask.

Mike and I were spent. Cindi unfortunately had still never had her release. I reached over and handed her the dildo and said, "Do it while we watch you."

There was no hesitation. She turned the vibrator on and started rubbing it on her clit looking to cum as quickly as she could. This wasn't for show, she had a purpose and it didn't take long.

I have always loved watching Cindi climax. She liked us watching which added to her fun and she can be very loud at times. There was no reason to hold back now. Her body went into convulsions and she was groaning and moaning loud enough I was glad we were in the basement where the neighbors couldn't hear us. Finally, she stopped and lay back like us, catching her breath.