Cindy n Steve


Cindy n Steve

By: MiamiMark

When Cindy and I had moved into our new home, it didn't take long to meet all the neighbors. It was a fairly new community and everyone was interested in getting to know everyone else so they would have BBQ at different homes and get-togethers.

By this point in our relationship Cindy had already been with a few different men and our adventures were becoming slightly more casual. Rick would come over once in a while and it wasn't long before they would get into it. I would, of course, run and get the camcorder and record it for viewing later. Besides Rick, Cindy hadn't been with any other guy for several months and we were spending most of our time getting the house the way we wanted it.

I always told Cindy I would love it if one day she were to confess to me that she had an affair with someone that we had not pre-planned her sleeping with. It was just something about that feeling of nervousness and excitement that really got me going. But after all this time nothing had ever happened like that and I was getting used to it. After all, I had nothing to complain about. But I do have a confession and that is that I started to fantasize about setting up different scenarios without her knowing about them and seeing her reaction to them.

My sister lived not too far from our new place and this was a great opportunity for us to spend more time with our families. I have two nephews and one of them is in his second year in college. I always had a good relationship with him and now that we lived closer to her we would often come by the house after classes and even bring over a friend or two I think it is because I didn't care if they had a beer or two where I knew his mom would not approve. The way I saw it, it was safer at home than out on the streets.

One day he was over with his friend Steve playing Playstation. Steve needed to go the bathroom but my nephew was using it so I told him he could use the master bedroom's bathroom and pointed to the hallway.

Later that afternoon after they had left I had to use the bathroom myself and realized that right there on the vanity sink was Cindy's purple lingerie and garter belt that she had used the night before with Rick. At first I was slightly embarrassed for her thinking that Steve saw it when he used the bathroom but then it got me a little excited thinking that this kid was probably thinking of Cindy in the outfit or at least I was hoping he was.

A few days later they both came over again and I had purposely left her vibrator and a pair of panties on the countertop. I wasn't sure how I was going to assure Steve would have to go back in there. After all, how do I get him to use that bathroom while making sure my nephew uses only the other one. To my surprise he waited until my nephew did use the bathroom to ask me if he could use ours.

After he went in I stood by the door at the hallway and just wondered what he was doing and then I heard the quick switch on and off of the vibrator. My heart was racing. I quickly jumped away and ran to the living room so as to not get caught.

This went on for about 3 weeks. I wouldn't always have something planned or sitting out and he wouldn't always go to the bathroom but it happened more often than not. The whole time I wanted to tell Cindy but I really didn't know how to do it or if she would even think that a 18-19 year old guy looking at her stuff was right so I waited.

I even had my nephew bring his friend over a couple of times for dinner just to watch him eye my wife. I give him credit for being discreet but he would always try to catch a glimpse of her breasts whenever she was sitting down by walking behind her and asking her if she wanted a refill on her water and then grabbing her glass. Cindy thought he was the most polite young man while all the time he was just eye-fucking her. Perspectives can be so different.

About 2 months later the opportunity finally came during one afternoon when my nephew and he were talking about how the school was going to fumigate his dorm building for termites next weekend and where he was going to stay. My nephew said he could stay at his place but would have to crash on the floor in his room of the sofa. I pretended I wasn't listening and asked why he was spending the weekend there and they explained it to me. I made a comment about my sister's couch not being the most comfortable and then casually threw out the option to crash the weekend at my house since we do have 2 spare bedrooms (one waiting to become a den). He jumped at the offer and it was set.

I asked Cindy about it that night and she seemed completely unaware of anything and said it would be fine and asked if my nephew would be staying over too. I quickly said he wasn't and changed the subject. My mind was racing as to how I could pull anything off.


That Friday, Steve came over in the afternoon and my nephew not long after. We had a few beers and watched television. I had purposely disconnected the water supply hose to the guest bathroom toilet a couple of days before so that it would not be used under the pretense it needed to be fixed. Steve and my nephew had both been using the master bathroom.

Cindy came home from work, we had dinner, and my nephew ended up taking off to spend time with his girlfriend. The three of us spent the rest of the evening watching TV and drinking; beer for Steve and wine for us. On Fridays Cindy always relaxes after a tough week by drinking a couple of glasses of wine. Cindy was asking Steve if he didn't have a girlfriend and he said not at the moment. So she was giving him the 3rd degree to find out if she knew anyone who might be perfect for him. All I kept thinking was he wants you right now.

By 11pm Cindy was falling asleep and the wine wasn't helping. I was hoping she might last a bit longer but I ended up tucking her in and going back to watch TV. At about midnight I went to 'use the bathroom' and went to see if Cindy was still sleeping and she was. She was laying on your stomach, leaning over to the side slightly and I pulled down the sheet revealing her back, part of her ass, and the side of her breast. It was beautiful.

When I went back I kept hoping that Steve would need to use the bathroom by offering him some more beer and it worked. He asked if he could go since Cindy was sleeping and I said of course, she won't wake up. I couldn't wait to see his face when he came back.

After about 10 minutes I wondered what was taking him so long so I actually walked into the bedroom expecting him to be in the bathroom and when I turned the corner to the bathroom he was sitting on the toilet seat with a direct view to Cindy, jacking off. They guy was startled and pulled up his pants in a flash. I just laughed quietly and left the room.

He didn't come out for another 20 minutes from being so embarrassed but when he did he was red like a tomato and just sat down without saying a word. At this point I was quite empowered so I pushed play on the VCR and started to show a tape of Cindy teasing me in one of her outfits and then giving me a blowjob. Steve was quiet and kept looking at me. I started to ask him if he found her attractive and he just nodded. I asked him if wanted to do something to her and he didn't do anything.

I tried to calm him down by telling him I knew he had been looking at Cindy over the past few months and wanted to know what he thought of her. After a bit he started to say things like she was hot, etc. etc.

This is when I told him that I wanted him to fuck my wife but that she couldn't know I had told him anything. I lied to him and said she had been fantasizing about him and that this was her ultimate fantasy. I said that Cindy, who was now 29, had wanted to fuck a college guy for some time and I was determined to make it happen. He was all about it.

Since all of that was a lie, and Cindy has a thing for much, much older men I didn't have the details on how I was going to pull it off.

Anyways, Steve and I had it all planned out to try and have her get excited by catching him. The next part takes place over another month of carefully planned events. I felt like I was planning the consipiracy of the century.

On Saturday I made sure to tell Steve to take a shower while she was gardening and that I would leave to go to the supermarket. When the time came, he jumped into the master shower since the other one was 'broken' but Cindy didn't have a clue that the toilet water and shower water are not connected. When I got back Steve told me that he saw her come into the bathroom, lookup at the shower to notice him behind the glass enclosure, and then go back out but not before giving him a complete look over. He was pretending to wash his hair and not be looking.

The next day he helped her do some gardening while only wearing jeans. That had her attention and she loved that someone was helping her landscape which had taken longer than she hoped for.

He left that night back to his dorm and she told me all about how helpful he was in the yard but never mentioned having seen him in the shower. I suggested that we could give him some spending cash to come over and help her next weekend finish the yard and she thought it was a great idea. I called Steve that night and told him what was happening and he was getting all excited.

I had to work that Saturday but Steve told me all the details over the phone that evening. He had arrived around 9am in the morning and Cindy answered the door and offered him some breakfast. They started to work in the yard right after and he was once again only wearing his jeans. Steve was in pretty good shape for an 18-19 year old. Not that he was Mr. six-pack but he kept in shape. As it got closer to noon, Cindy told him she had to go in and change into something cooler because her jeans were killing her. It was August and the Florida sun is quite brutal. She came back out in her bikini which in and of itself isn't that strange here but he told me it was the orange bikini I knew she was trying to catch his eye. This bikini is fairly conservative on the top part, covering everything but giving a great curved view, but the bottom part was high on the sided and slightly lower on the back. It definitely had a sexual appeal and I asked 20 questions about how he was feeling and what he liked the most. I was learning that I loved to hear what guys thought about her almost as much as watching them with her.

He came over on Sunday again and then the next weekend until it was finished. When it was done, I was working on the crown molding and they both came in and sat in the kitchen chairs since they didn't want to sit on the couches all sticky and wet.

I walked from the living room to the den just to get a peak in the kitchen and there was Steve standing behind Cindy giving her a neck massage. Her head was leaning all the way forward and he was just pressing into her bare shoulders and rubbing down her arms. I stopped for a brief moment just enough to have him see me and I smiled and kept going.

For the next couple of weeks Steve would come over in the afternoons with my nephew but Cindy and him would not cross paths. She would ask me more than before if he had come over and how he was doing but that was it. I didn't even want to ask or insinuate anything. He would ask me when he could see her again and I couldn't tell him because I didn't know what else to do at this point.

He came up with the next idea which was perfect. One day he stayed until Cindy came home and made up some excuse that I was helping him with a college paper. He was talking with her for awhile and then I heard her ask me if I was up for going out tonight. It seems that Steve and some of his friends were going out on the town and he invited us to join him if we weren't too old. That is all she needed to prove we were still hip.

Steve came over later that evening and I drove to the Grove (lots of bars and a couple of clubs). Cindy was dressed in her flirty skirt which wraps around and is tied in the back, her matching top, and short heeled shoes. I could see she was trying to dress younger by using her older clothes and the shirt was a bit tight but nicely tight.


We met his friends, had a few drinks, and went to a couple of different places. Nothing much happened but hey spent most of the night talking and I know that is a great sign for Cindy since she gets more comfortable. His friends also spent a great deal of time and attention on Cindy and I know she was enjoying it because she was all smile and laughs the entire night.

On the way home, and me being designated driver, I suggested we hit Old Cutler Oyster Bar which is one of my favorite places and they a pretty secluded and dark dance floor. Steve said he had never been there and Cindy quickly mentioned how he had to go and for us to go. So off we went.

We got there and sat at the bar and had a few beers (they did at least). Pretty soon they were playing some techno music which is sort of unusual there but it was college night (Thursday) so it probably made sense. Steve got up and asked me if he could dance with Cindy and I said sure. They took off and were dancing. Now, Cindy LOVES and I mean LOVES dancing which is one thing I'm not big into so this was heaven for her. The only time they ever came back was to order a couple of shots which he was recommending she should try and I knew they were pretty strong.

I could see that they were dancing pretty close but maybe it was just the crowded dance floor. But then there were moments when I looked and she had her back to him and he was pressed up against her dancing rhythmically and gyrating. I was ready to explode and hated the fact I couldn't really see.

They came back and they were both drenched after all that dancing. Maybe it is just me but nothing turns me on more than a women who perspires and is all flushed. We ended up leaving and had offered Steve to spend the night since it was so late but he only stayed to drink some water and then took off. Cindy passed out and I called his cell phone. He said that while they were dancing she had leaned her head on his shoulder at one point as if she was exhausted and he put his arms around her back and moved down she never stopped him when he squeezed her ass for at least a minute. Then, after the last shot they took, he said he got the balls to pull her to him and put one hand on her breast and slip into her top and cop a feel. He said she didn't even look up at him or move away.

I told him he had to come over tomorrow, Friday, and make his move but he said he couldn't but could come over on Saturday. I would set it up.

The next day Cindy never mentioned anything he did. I asked her if she had fun and she loved it. I mentioned that Steve would probably be coming over on Saturday for me to help him finish his paper and if we had any plans so I could make other arrangements if we did. She said Saturday was free and that she would take advantage of him being over and maybe have him help her plant her two new palm trees and give him some more spending money. I said it was great.

Saturday I called Steve and told him the whole story about the paper, etc., and that she would be home but I was going to call her and say I was still stuck at the tire store waiting for my tires to be changed and it would take at least another 2 hours. And the plan was set. Steve was on his way when I called Cindy and told her and asked her to go ahead and tell him to do the planting now and I would do the paper later when I got home.

I'll tell you what happened but it was from what Steve told me later.

Steve came over with his books in hand and Cindy told him how I was stuck and would be back in a couple of hours. The talked a bit about Thursday night and how much fun it was and how she wanted to do it again. Then she asked him if he minded helping her plant the palms while they waited for me and he said it would not be a problem.

She went to change and he waited in the living room. When she came out she was wearing a pair of white shorts and a halter top. He said he was a bit nervous but after Thursday he was feeling a little cockier so he asked her 'what, no little bathing suit today?' She giggled and said she should probably hit the gym a few more weeks before she wore it again and then rubbed her exposed belly as if she was fat or something.

Steve laughed and walked over to her and rubbed his belly and said that he had a belly not her. Then he reached over to pat her belly as if to confirm and made a comment as to her not having any fat at all and how women all were paranoid. She told him thanks and continued 'but I do have lots of fat on my waist and my ass' and pinched her waist to show him.


Steve put his hands on her waist and told her she was in better shape than most girls he goes out with. I thought that was a genius line and I know it got her. She just laughed and that was when he slipped his hands down the sides of her shorts and grabbed her ass. The shorts were now slightly lower as he squeezed her ass and then he went in for the kiss and she didn't even hesitate.

After a few minutes he put his hands on her shoulders and pushed her to the floor where he unbuckled his pants and let her do the rest. She pulled the zipper down and pulled the jeans to the floor. He wasn't wearing any underwear and she began to suck the tip of cock slowly and then began to kiss it and lick it all around. He says he had never had someone take their time like Cindy did.

After that they went over to the guest bedroom since it was closer to where they were, and he pulled up her halter top and had her tits just hang out while he sucked on them and played with her nipples. He mentioned that she had very sensitive nipples and I told him it was one of her favorite things to have pinched.

He didn't really have much foreplay and had her bend over on the bed and was about to go in when he said she stopped him and told him to put a condom. He pulled one out but said he just wanted to go in a couple of times to feel how we she was and that he never cums early so not to worry although I think he was telling me this so I didn't worry.

He did it a few times and then put on the condom. He had her doggy style most of the time and then pulled her down to the floor when he lifted her legs and went at. I asked him if he was slow or fast and he said he loves to do it hard and fast because he loves the stuttering sighs of a women every time he thrusts. Never heard that before but it did sound awesome.

When it was over she asked him if he still wanted her to wear the bikini and he said yes so she went to change. She said they had to plant the palms before I came back or I would get suspicious so they did it and she rushed him. When they finished was probably the time I got a call from her to see where I was and when I was coming over because they were done. I was already finished but I wasn't sure if anything was happening yet since she sounded pretty calm so I said I was at least an hour left and that they just started to change them.

After she hung up she went back outside to clean up the ropes and took them to the garage where he followed her with the shovel. He said they were both dirty, sweaty, and sticky and as soon as she dropped the rope she turned to him, squatted down, and pulled his pants down again. He almost came within minutes because she was sucking fast and stroking him at the same time. This is my favorite part. He picked her up, pulled aside the bathing suit and started to fuck her with one leg wrapped around him. I asked him if he wore a condom and he paused realizing he never put one on. But it gets better. While he was thrusting his 19 year old cock into her, he was asking her if she liked it and she would scream 'yes I love it yes'. Then he remembers her at one point telling him she was about to cum and to not stop. Then she told him he could fuck her whenever he wanted anywhere, anytime.

I love that because as of today, 6 months after, she has never told me anything about it. I got home and she was taking a shower and Steve was eating a Pizza Pocket in the kitchen. He gave me the thumbs up and I said I would call him later at night.



So Embarrassed ... She Turns Red

*** An introvert. VERY shy and sensitive, easily embarrassed, this losing girl accepts bets for consequences she can barely tolerate psychologically. Her way of letting off steam.

What's happening?? ...

"She Lost - While playing she had second thoughts and desperately tried to win."

"I won - Not only did she pay up but I put her on display, AND played with her emotions, exposing her more."


Loser Must Masturbate for the Other 2 ...

Their First Time Playing Strip High Card ...

Loser has to Submit to 'Anything' the other wants ...


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