My Wife and Teens

She started changing her responses to me. Instead of saying "No way would I ever do it," she was now saying "It is too risky because the boy could end up telling everyone in town, so that they all knew about what I had done with a teen boy."

So, the next time we role played it, I had us pretend we were out of town and found a teen to play with us at our motel. This way the teen would not know who we were. Afterward, she said "Wow. That was hot. At least doing it that way, the teen would not know us." Then she said "But, I would want to know him well enough to be sure I liked the kid. Plus, I would need it to be a sweet innocent boy. That kind would turn me on the most." Then she caught herself and said "That is, if I would ever do something like that."

I started looking on chat sites that had listings for each city in the United States. I wanted to find a young guy within a few hours of where we live. I ended up finding 3 teens who were all 18 and lived within 3 hours of our house. I made them show me their license on cam to prove their age. I talked to them a lot until I narrowed my selection to down to one teen. I then arranged to go out of town with Cindy to that same area where the teen lived. I was scared to tell her of my arrangements that I had made ahead of time for fear she would back out of it.

We went to the motel and I arranged a time for the teen to meet us at the indoor pool. I told him to tell her that he was a teen from that area who new one of the employees of the motel, and had gotten permission to swim there. The boy's name was Joey.

Joey was 5'8", about 135 lbs. His body had very little hair on it. He had short, brown hair, and a cute, kind-looking face. He was respectful with both of us. He also seemed to be a mixture of nervousness and excitement at the same time. He acted more like he was 12, than 18. My guess is that he hadn't had a lot of experience around women. He had on tight fitting swimming trunks - like a spandex material.

When we came down to the pool, we noticed that no one else was there. It was early afternoon, and typically pools are empty around that time anyway.

Cindy saw him in the pool, and she started teasing him right away, just like she always does with any teenager. All 3 of us exchanged first names with each other, and Joey also told Cindy he was a local kid and had a friend who worked at the motel.

As she talked and teased him, I noticed that she started doing things I had never seen her do, like bending forward so he could see down her bikini top. Her teasing was definitely becoming more and more sexual.

At one point, Joey got out of the water for a moment. When he did so, Cindy said to him "You have a cute little ass."

Joey's head jerked back towards her, and he had a shocked look on his face. Then, he just smiled and said "Thank you, Mam."

Even though he knew that I had set this meeting up for possible sex with my wife, I had told him that she did not know anything about it. I also had told him that she liked to tease with teenagers, so expect that, but she would probably not sexually tease with him. Then I warned him to let her take the lead in the teasing. I said "You just need to be a courteous responder" I am sure this was why Joey was so surprised by her comment about his ass.

I do have to admit, even I thought he had a cute, tight little ass. His swimming trunks made that easy to see. Within a couple of minutes, he returned to the pool, but now you could easily see that his cock was hard.

Cindy saw it and said "I love those swimming trunks, hon. I love how tight they are on your body. They are very hot."

Joey said "Thanks."

Cindy said "Makes me want to see what is under them."

Both Joey and I were shocked at how sexual Cindy's comment was. I would have never guessed she would say something like that. It was probably due to her loosening up from all of our role playing about teen boys. My guess is she wanted to see what would happen in real life if she did some sexual teasing with a nice boy.

Joey looked over at me to see my facial expression, and I said "You can say what you want. She is the one teasing you."

Joey said "Anytime you want to see what's under them, Mam, let me know."

Cindy had been enjoying her sexual teasing because it made the boy look embarrassed, yet excited at the same time. At times you could even see his hands shaking. She loved that innocent response.

I think it really turned her on to be able to create that in this boy. But, with Joey's last comment, I think she didn't know what to say. She was at a turning point of either backing off a little, or taking this further. I think she saw his comment as a challenge to her, to see what she would say back to him. Cindy's gutsy side, decided to take this "up a notch" and put the conversation back to Joey, to see what he would say.

Cindy said "I want to see right now."

There was a silence from all 3 of us as if we were all thinking "What now?" We all looked at each other during the long pause. Then, Joey decided to take her challenge. He said "How do you want to do this?"

To me, it was like this had turned into a little competition between the two of them, to see how the other one would respond. Each one was pushing it until the other one withdrew. Conversation had slowed down, I suspected all 3 of our hearts were beating rapidly wondering how far this would go.

Cindy said "Sit on the edge of the pool."

There was almost a sexual nervousness in the air. Joey had not reentered the pool yet, so he just sat down on the edge like Cindy asked. He leaned back a little, and put his hands down to his sides to brace himself. His actions were one more part of the challenge back to Cindy. Now, the "ball was in her court" so to speak.

There was silence as Cindy waded through the water towards the edge of the pool. She saw that Joey's cock was very hard as it pressed against his tight trunks. It was easy to see the shape and size of it in the trunks. It looked to be about 5-6 inches, and not real thick.

When she got to him, she reached her hands up, put her fingers inside of both sides of his trunks, to get ready to pull them down, then she stopped and looked at him. I think she was waiting to see if he would stop her.

Joey just smiled, which became another challenge to Cindy. Cindy said "Lift up your ass", and as Joey did, Cindy pulled the trunks away from his ass, so he could sit back down, but the front of the trunks still barely covered his cock.

She looked at his hard cock pressing on the trunks, then looked up at Joey, then down again at his trunks, then back to Joey again. She was teasing him, making him want her to strip the trunks down.

Then she very slowly started pulling his trunks off his cock. She stopped when half of his cock was exposed to her. She was continuing this challenge, making him wonder if she would take them all the way down to his thighs,or stop what she was doing, and slide them back up. Joey was shaking with innocent excitement as Cindy paused for another 10 seconds.

I am sure that his lack of resistance to her, made Cindy feel the challenge to her was still there. And, she took the challenge. She slid the trunks all the way down to his thighs.

Joey's cock was, just as I thought, about 5 inches, maybe 6. It was light brown in color, but very pink around the head, and about half way down. Precum was starting to flow down the sides. His balls were also adorable. Even though it looked like he did not shave his cock, he had very little hair down there, anyway. If I had a camera, I would have loved to have taken pictures of him sitting like that, fully exposed to her. To be honest, it made me want to play with his cock. It was a very sensual sight.

Cindy just looked at it, then looked up at his face, which had a look of total excitement.

I could only imagine what he was thinking, and hoping for. If that were me at his age, I would want have sat there hoping she would her playing with my cock and balls.

I am betting Cindy loved knowing that she, an older woman, was making this boy's day. She had him trembling with excitement, hoping, waiting for her next move. I am also betting that Cindy loved the control she had over the boy. She could do to him whatever she wanted. She could make him shake with desire for her.

Both Joey and I were waiting to see what would happen next. Cindy then, slid the trunks all the way down his legs and off of his body, then put them on the side of the pool where he was sitting. She grabbed his hips, and pulled him closer to the edge of the pool where she was standing. She said "Lay back further", and she helped slide his ass to where it was hanging off the edge. Cindy was standing in about 3 feet of water, and it was easy for her to play with him. She looked over toward the door, to be sure no one was coming, then pushed Joe's legs up in the air. She massaged his balls with one hand, and lightly started to rub up and down his cock with her other hand. His precum was flowing steadily down his cock.

Joey was frozen somewhat, and afraid to say or do anything wrong that might stop what Cindy was doing. You could see his body trembling with excitement.

Cindy then moved one hand down to his asshole and lightly rubbed her finger across it. My guess is she wanted to see if she could do anything she wanted to him. Joey never flinched.

Cindy said "Honey, you have no idea how much fun this is. My worry is we are going to get caught with someone coming down to the pool. Can you come up to our room for awhile?"

He agreed to do so, as he quickly put his swim trunks back on, grabbed his other clothes. He also grabbed a towel, to use to cover up his hard cock for when we walked down the hallways, to our motel room.

When we got to our room, I told Cindy to change and just put on nothing but a thong and her robe. I think reality and settled in on her by now. She looked at me like she was going to argue and change her mind, but then she looked back at Joey, smiled and said "Yea, I would be more comfortable that way."

As Cindy was changing in the bathroom, I told Joey that he and I should strip down to just our undies and a button up shirt, but leave the shirts unbuttoned. I said "It's okay. We can all get into bed and just watch tv, and be comfortable, then see what happens."

I then turned on the tv and found the movie channels, and quickly found the kind of movie that would not distract us too much and left it on that channel.

I had already told Joey, ahead of time, to not get pushy with my wife, but to just let things happen. We had already seen a lot happen at the pool. I was hoping, by moving up to our motel room that Cindy would not chicken out. I was hoping that the level of excitement she had at the pool would come back in our room, but I really did not know. I suggested to Joey that he needed to follow her lead, and do what she wanted to do, just like he had already been doing.

When Cindy came back into the room she was a little startled to see both Joey and I dressed like we were dressed, leaning against the headboard of the bed. Joey's cock was already pressing hard against his underwear. I think the sight of it brought Cindy quickly back to the feelings she had at the pool. I said "I just thought we could watch some tv, and you could have the privilege of having two good looking guys sit by you."

Since she didn't tell me 'No', I then pushed it even further by saying to Cindy "Actually, why don't you lean against the headboard, and let Joey see what it is like to sit in front of a grown woman, and lean back against you? Bet he has never gotten to do that with an older woman before. Then you can put your arms around him and maybe, rub his belly and chest."

Cindy gave me a hesitant look as if she still hadn't totally made up her mind how far she was going to go, but I could also tell she was getting too excited to say 'no.' She got on the bed, leaned against the headboard, but then realized Joey would end up sitting on part of her robe. I saw the awkwardness, so I reached over to her robe and said "Here, let's just move the robe away from your legs," as I moved it off her legs. It exposed her red thong panties. Then I said "It is still covering your tits."

She still had not stopped me yet. I think at this point she had just, pretty much, given in to see what would happen. Her breathing definitely told me she was getting very turned on.

After the robe was pushed off of her legs, she helped Joey sit in between her spread legs. Then, as he leaned back against her chest, she reached her hands around to his shirt, made sure it was pushed open and out of the way, then she began rubbing his belly and chest for him. I could easily tell that his cock was very hard inside of his undies.

I could tell that Cindy was enjoying this. The boy had practically melted into her. She had control over his body, and he was nervous, and shaking a little. She was getting very turned on by how she was effecting him.

After about 5 minutes of rubbing his chest and belly, her hands started moving, lower and lower, down his belly. She looked over at me as if she was wanting approval. I smiled and nodded my head yes, and I even motioned my mouth with words that said "Go for it."

She started sliding her hand about 2 inches under the top of his undies, then across his belly. She kept repeating this over and over again, each time going lower and lower into his underwear. Then she said to me "Honey, do you mind me doing this for Joey?"

I said "Not at all. I can tell that Joey loves it, and I can imagine myself at his age, getting the privilege of having an older woman play with me. So, do whatever you want. It won't bother me at all."

Cindy said "Well honey, maybe you ought to come over here and take off his undies for me."

Cindy and I had played in a role play once, where I stripped the boy for her as she told me what to do. She knew that it turned me on a lot.

I crawled on the bed over to the boy, grabbed both sides of his undies and pulled them down his legs and off of his body. Joey was looking at me in disbelief, obviously thinking it was his lucky day. I then took it further than what Cindy asked me to do, by helping Joey take off his shirt. Now he was totally naked. Precum was flowing down his dick.

While I was doing all of this, Cindy slid off the robe so her tits were totally exposed. She was now sitting there wearing only her red thong panties.

As joey started to lean his head back against her chest I said to him "No, Suck her titties for her and massage them really good. I want to watch a young boy with her titties for at least 5 minutes."

Joey immediately turned to her and started playing with her tits. She leaned back and just let him grope them and suck on them. His hard cock was resting on her leg. I loved every minute of watching this. It was so hot to watch. Cindy breathing was very hard and she was panting from the excitement. She then said to me "I love getting attention from him. This is so hot. Honey, strip naked for us and stroke while you watch us."

Cindy knew that I loved being told, sexually, what to do. Plus, I head told her numerous times when we played the young boy role play that I wanted to stroke while watching them. So, now she wanted me to do it in real life.

After a few minutes of watching this teen boy sucking and massaging her tits, I had the boy return to where he was previously sitting between her legs, leaning back into her chest. Cindy then reached down and started playing with his dick. It was sooooo hot to watch this grown woman playing with this boy's dick. I reached over and grabbed my phone camera and took several pictures of it.

Joey was squirming from her touch, and was very close to cumming. I told them to stop before he came. I then said "Joey, lay on your belly between Cindy's legs and eat her pussy. I will teach you how to do it so that it makes her feel really, really good.

Joey quickly moved to his belly, as I leaned down bend her legs up to where her feet were flat on the bed, but her legs were spread very wide. Then I slid between her legs, by Joey, and told him what to do. I moved his hand onto her pussy, and taught him how to finger fuck her pussy, while he licked her. Cindy orgasmed immediately.

I think the thought of a young boy doing this to her was just too much of a turn on. When Cindy had her orgasm, I pushed Joey's head back and whispered in his ear "Let her enjoy the feelings, while you lightly rub on her legs." Then I asked him "Are you having fun?"

He said "Thank you so much for all of this, I love it. I feel privileged to play with her, and it is fun having you here helping, too."

Cindy loved my involvement with teaching the boy what to do to her. He helped her orgasm a total of 3 times, as I taught him how important it was for him to take care of the woman. I had also taught him to let her body shake after each orgasm, so that she can enjoy the feelings for a minute, or so, after each time.

After the third orgasm, she was still hot to the point that she moved down to his dick and started sucking him. She only did this for about 30 seconds because of how excited he was. She could tell he was about to cum. Then she said to him "Fuck me. Stick your young boy dick inside my pussy and squirt your cum in me. I want your young dick to fuucccckkk this older woman's pussy.."

Her language was such a turn on to me that I almost exploded my cum, right then, but, I was able to stop myself in time.

The boy was on top of her in seconds, and pushed his dick inside of her pussy, and started fucking her hard. As he fucked her, she grabbed his ass and started squeezing it. I got the impression she liked his young, little ass. That seemed to do it for him, he could not last any longer. He shot his cum into her pussy.

Afterward, he laid his head on her breasts and snuggled her. After about 15 minutes, the boy finally said "Thank you guys so much for letting me do this. I will do this anytime you want me to. I really did consider it a privilege. And, I won't tell anyone about this."

He started to get up to leave and Cindy said "Hon, you don't have to leave yet. I would love to play with you some more, and I definitely want to suck your dick some more and see if I can make you cum again."

I had previously told Joey, when we talked online, that I wanted to try sucking his dick, but she would never agree to me doing that. I said "Get her excited and then ask her if she would let you experience that. Tell her that it is your fantasy that you have always been curious to try." I told Joey that he needs get her very turned on in order for her to agree with it. I said "Even then, she may say 'no.' If she does say 'no,' beg her in a cute boy manner, then if she persists in saying 'no', then just drop it and we will do other things."

Joey then said "Mam, I hope this doesn't bother you, but can I ask you to allow me to experience something I have always wanted to try?"

Cindy, thinking it was something with her, said "Sure, hon, what do you want to try?"

Joey said "Mam, I doubt you will do this for me, but I would sure appreciate it if you would."

Cindy said "Just tell me what it is."

Joey said "Well, Mam, I want you to please ask your husband to suck my dick, while you watch us."

Cindy was stunned. She has never been open to anything that sounded gay. You could tell that his question really surprised her, and there was this long pause, and a lot of deep breaths. She finally said "Hon, even if I did say okay, that would be up to my husband, and I don't believe he would ever do that for you, would you, Mike?"

I said "Cindy, I know it isn't what we would normally ever do, but to be honest, I am so turned on right now from watching all of this, and watching the boy get so excited. I absolutely love watching him shake from excitement. If that would highly turn him on, I would do it for the boy."