Asian Sex Story: My wife, Cindy, has always been buddies with teenage boys. She just seems to get along with them very well. She teases them in humorous ways, and they love it, then they tease her back. Sometimes, if she likes one of them exceptionally well, I have seen her go a little further with the teasing to the point of definitely being flirty, although not to the point that it was sexual flirting.
Cindy is fairly conservative and has never talked much about fantasies, as much as I would love for her to do so. Our sex life is okay. I have talked with her many times about changing what we do, but after we talk there may be slight change, but for the most part within a couple of weeks it goes back to the same sex life we had before.
But, I have to admit that even though our sex life is not as often as I want it, nor as adventurous as I want, it is definitely enjoyable. If I was rating our entire sex life, here is how I would rate it. I would give it a “D” on how often we have sex (about once a week), an “F” on how sex starts with us (no adventure at all. It is more or less, “Okay, now its time for sex, get naked.”) I guess that is better than what many guys get. Last of all, I would grade how satisfying things are when we have sex as a “A minus.” She does know how to turn me on very well. So, how can I complain too much? At least she we have hot times. Some guys don’t even get that.
The problem for me is that my mind is very sensual, and I can think of many things I would love to do sexually that I may never get to do with her. So, I found my mind wondering while watching her with the teen boys, if she were a more sexually open person, would she love to play with one? My guess is “Yes.” I base that on how she teases them when she is around them.
So, I started thinking I would see what I could do to maybe make that happen, or at least find out if my theory was right. So, I started talking to her about doing role play in our sex life. I was surprised that she was open to that idea. However, her ideas of role play always involved just us, mostly as 2 single people, or something similar to that. It never involved other people. So, I told myself that her willingness to role play was, at least, making her a little more “open” to try new things.
Over the course of about 4 months I introduced a role play fantasy idea to her at least once every couple of weeks, when we had sex. At first I did ideas that were centered around 2 single people, since she was open to that. I did one with a strip poker theme between 2 single people. Then eventually, I took the strip poker theme to a new level, saying I wanted it to be a game between her and a teenage boy (legal age) who convinces her (the older woman) to do strip poker.
When I first mentioned it, she gave me a look that told me she wasn’t so sure about that fantasy. Then, as I continued to watch her facial expressions, I saw it change to where I could tell the idea turned her on, but at the same time, she was wrestling wit
I quickly told her I would play the innocent neighbor boy, and we would be playing a regular card game, while laying on the carpet in the living room. I wanted to move forward quickly with this idea before she thought to much about it. She agreed, and we started the role play. Then after about 3-4 minutes, as I continued playing the innocent neighbor boy, I said “How about we up the ante by playing strip poker.”
Cindy, snapped out of the role play at that point and said “Michael, I am still not so sure about doing this.”
I chose to stay in my role play as the neighbor boy, by saying “Oh, yea, you are afraid you will lose, to this young boy?”
Somehow it worked. Cindy switched back to her role play character again, and said “No, I know I will whip your butt so bad that I’m afraid you will be the embarrassed neighbor boy sitting there naked in front of the older neighbor.”
I quickly tried tried to keep her in this role by saying “Oh, does my older woman neighbor think she’s actually that good?”
Cindy said “I know I am that good, and you don’t want to be a young boy who is naked in front of your older neighbor.”
I thought to myself “I got her now. She is getting deeper into the role play.”
I continued playing the teen boy, and said “No way I will be the one who is naked. My beautiful, mature neighbor lady will be topless in no time. I am going to be able to see her tits because you are about to see the best of me.”
Cindy said “Oh, I will see the best of you, alright. It will be the best of you sitting there naked.”
I laughed at that point, knowing that I was like the fisherman, reeling her into my game. I was trying to tap into the side of her that got flirty with teens, in order to get her to open up and get past her conservative side. I continued my role play “We will see who loses their clothes first.”
Before Cindy and I started this role play, I had asked Cindy to wear thigh highs, thong panties, a short skirt, and a button up top with a sexy bra. So, she had 5 pieces of clothing. She had me wear undies, jeans, and a button up shirt. She said that I could make up the difference in the amount of clothes so that when I lost a hand I would have to put on a pair of her lace thong panties to wear. Then when I lost another hand of cards, I would have to push my panties down to my knees and sit that way, fully exposed. We made it to where the winner of each hand, picks which piece of clothing that comes off the other person.
I shuffled the cards and handed them out. I lost the first hand and Cindy immediately got gutsy, and made me take off my jeans. I was sitting there with a hard cock pushing against my undies.
Cindy’s fun teasing side came out as she said “You will be in trouble in no time.” Then she paused and taunted the boy I was role playing by saying “You sure you want to do this? You sure you want me to see you naked?”
I laughed, as I played the boy, and said “You are awfully gutsy, aren’t you?”
Cindy said “I have beaten you in regular cards all evening. Yep, you will be showing me that little boy body in no time. And, tonight when you go home, you will only be dreaming and wishing you had seen me naked.”
I dealt the next hand, and Cindy won again. She had an ornery smile on her face as she said “Let’s see, do I want to see you in my panties, or do I want your shirt off, hmmmm?”
I said “Or, maybe you just ought to skip the panties idea and just see my boy dick. That way I find out if you really like looking at a young, naked body.”
Cindy said “Oooo, someone doesn’t mind showing their goods?”
I said “Tell you what, if I show it to you, you have to call it by a sexual name.”
Cindy said “Wow, we are really getting into this, aren’t we?”
I said “Only makes it more fun,” as I responded in my gutsy challenge.
Cindy said “Let’s see that coccckkk of yours.”
I was actually stunned with the fact that she called it a cock, and drug out the word in a very sensual manner. It was was a huge turn on to me. I responded with a gutsy comment of “If you want to see my young cock, then come over here and slide my undies down, yourself, Miss Older woman.”
She responded in her gutsy manner back to me “I can’t wait to see your young dick.”
She came over to me and slid my undies down to my knees. My cock was very hard and sticking up in the air. Then she got away from her role play for a second and said “Gosh, I hate to admit this, but this is very sexy fantasizing about this. I love this little role play of yours. It is very hot. We may have to do this one again.”
I knew I “had her hooked” at that point. I knew, right then, that I had tapped into that side of her that loved to get flirty with teens. So, I decided I would make sure that I did this teenage role play game with her, again and again, doing many different sexual things each time we did it. My plan was to do it a lot over the next couple of months, until I got her wanting it in real life.
I returned to my role play by saying “Does Cindy like seeing my young boy cock so hard, and sticking up in the air? Is this a privilege for you to see it?”
Cindy said “I love seeing it, hon.”
I said “Tell me what you are thinking. Tell me in a dirty way. ”
Cindy said “I love seeing your young, hard cock. I love seeing you exposed to this older woman. And, I can tell that you love exposing yourself to me.”
I said “Mmmmm. Okay, let’s play another hand. It is time for me to see some tits.”
I dealt the cards, and my luck was good this time. I won. I told Cindy to take off her bra underneath her button up shirt. So, Cindy turned her back, took the bra off and then put the shirt back on. The nice thing about the shirt she was wearing was it was a see through, black material. You could make out the shape of her tits, and it gave a slight view of her nipples.
I dealt the cards again, and the luck went my way again. I told Cindy to take off the shirt. She said “Come and take it off yourself.”
I loved this new horny, gutsy attitude. It told me she was very turned on in our role play. I crawled over to her, unbuttoned her top, and then while taking it off of her, I accidentally (on purpose) brushed my hands across her large, 36 D, slightly sagging, tits. I then sat there looking at her as if I was the boy in our role play who was very turned on by seeing her tits. I could tell that it turned Cindy on a lot with me staring at her. There was complete silence, and I could almost see a facial change that said she wanted to fuck the boy. After about a minute, I returned to where I was previously sitting.
I lost the next hand. Cindy got up, and went into her bedroom, and came back with a pair of her lace panties. Then, she said “I hate to cover up that cute little boy cock, but I want to see if you like wearing my panties. I want to see if it turns my neighbor boy on. Now, put them on.”
I got up from the floor to stand up, then slid off my underwear, and then slipped on the thong panty. My hard cock was pressing against the lace material, and you could easily see my cock through the material. Then she said “Now turn around and let me see that boy ass of yours in my thong panties.”
I did what she asked. Then she said “You like wearing your older neighbor’s panties, don’t you, boy? You like knowing that what you are wearing was on my pussy at one time. I bet if I sent a pair of my panties home with you, and asked you to wear them under your clothes to school tomorrow, you would do that for me, wouldn’t you?”
I was stunned at how horny Cindy was getting with our role play story. I was guessing, at that point, that what Cindy loved about teen boys was that they were horny for her, and that they would do whatever she asked them to do. I really think that deep down inside of her, she wanted to seduce one of them and enjoy turning them on. But, I am betting she never acknowledged these thoughts because of the conservative side of her personality.
I acted like a nervous boy, and said “Um, if you wanted me to wear them at school, well, I guess I would do that for you.”
She said “Mmmmm. Good boy. But, why would you do that for me?”
I thought, at that point, that I would see if my theory was right, so I said “Because you make me horny and excited. I love how hot you look, and it makes me want to do whatever you ask me to do so you will show me more of your body again.”
She smiled, then got a strange look on her face like she knew she had mixed feelings about tapping into her hidden thoughts. Fortunately, her horniness over rode her hesitancy, and she said “That is what I was hoping to hear you say.”
Cindy decided she loved seeing the boy in her panties so much, that she did not want to play another hand quite yet. She said “Let’s take a break, hon, I want to see my neighbor boy walk around in my panties awhile.”
Cindy had him (me) go to the kitchen and get us both some soda to drink. You could tell that Cindy was really caught up in this fantasy now. It was like she was actually imagining a neighbor boy walking around in her panties. My cock was hard inside the panties as I played this neighbor boy role, and it was leaking precum through the lace part of the panties.
Cindy continued the role play by saying “My little boy’s cock is so hard in my panties. I am betting he loves wearing them for me. Tell me, son, do you like wearing my panties?”
I said “Yes, Mam, I love wearing these for you.”
She said “Mmmmm. Good boy. If I invite you back over to the house, will you put my panties on and walk around the house all day with them on?”
I could tell Cindy loved the sexual control she had over me in this role play. I said “Yes, Mam. I would do that anytime you ask me to, as long as you let me see your tits.”
She said “I will do that for you, hon.” Then she said “It’s time to play another hand.”
I lost the next hand, and Cindy said “Slide those panties down to your thighs, hon.”
I said “Mam, would you do it for me?”
She smiled and said “Sure, dear.”
Cindy slid my panties down my legs. My cock was sticking up in the air and precum was running down my cock. She said “Mmmmm. You are very excited aren’t you?” Then she reached over and stroked my cock up and down about 4 times. Then she said “Very nice dick, son. I like seeing it.”
I said “Thank you, Mam. Whatever you want.”
I made sure I lost the next hand as well. This time Cindy told me to take off my panties and spread my legs real wide for her. She smiled as she looked at my cock, balls, and legs. I then broke away from the role play to say to her “In real life, if we really did this, you know this would turn you on a lot.”
Her head snapped quickly my direction as if she was totally surprised by my comment. She paused a moment, as if she was thinking about what I said, then she said “You know, it might just be a huge turn on to me. I guess there is something about an older woman, being able to turn on a young guy. I think it is flattering, plus it would be nice to see his young naked body. I also would enjoy watching his hands tremble from the excitement. And, then enjoy him doing whatever I asked him to do. But, I really should not be thinking this kind of stuff.”
I smiled back at her and said “Well, if the role play involved a young teen girl, I would have all the same feelings too.” Then I said “Can I be truthful with you?”
Cindy said “Sure.”
I said “In real life it would definitely turn me on to watch you playing with a teen boy. I wouldn’t mind it at all. I would even let you tell me to get naked while I watched you guys.”
Cindy was startled and said “Mike! I can’t believe you said that!”
I said “Well, I asked if I could be honest with you about what I was thinking. And, I am just telling you that it would be a huge turn on to me.”
Cindy said “Well, that isn’t ever going to happen. But, I do have to admit that all of this is really hot to fantasize about.”
I said “Good. Let’s finish the game.” I dealt the next set of cards, and I won. I had Cindy, take off her skirt so I could see her thong and stockings. I then had her stand, and turn around slowly, so I could see how her ass looked. She looked awesome.
I said “Mmmm. You have a very hot ass, Mam. I love looking at it.”
I then won the next hand, too. I said “The panties are coming off babe.”
Cindy said “If you want them off, then come and take them off of me.”
I smiled as I went over to her. I helped her to her feet, then knelt down in front of her and grabbed each side of her panties, and slid them all the way down her legs. I watched her step out of them. Then I stayed in a kneeling position in front of her with my face about 6 inches from her pussy. I started rubbing the sides of her legs as if I was a teen that didn’t want to stop. Cindy smiled and just watched me. I finally moved my hands around behind her and started feeling her ass. She let me do it for about a minute, or two without saying a word. Then I started touching her pussy very lightly. I could see Cindy getting hornier and hornier. She was almost panting. Finally she said “My boy is taking more liberties than just seeing my pussy. It is time for me to win the next round and win this game.”
I said “Once each of us gets naked, let’s turn it up a notch and say the loser of each hand has to do what the winner says for 5 minutes. And, just because you look so hot in those stockings, let’s just say we are out of clothes already, and this game change starts right now. I will take off my shirt and let’s see what happens.”
Cindy’s pussy looked very wet. This role play had turned her on as much as I have ever seen her turned on. She said “Let’s do it.”
I won the next hand. I came over to her, laid her down, lifted her legs up in the air, spread them wide and started eating her pussy. Her slick, wet pussy, felt good on my tongue.
After a few minutes of her squirming around from my licking her, I then started teasing her with my comments “Does Cindy like the young neighbor boy eating her pussy in front of her husband? Do you like the neighbor boy playing with your body while your husband watches?”
I made sure that I added the “in front of your husband” comment to try to stir up a future, real life event.
After I made my comments, I went back to eating her pussy. I noticed Cindy was extremely turned on and as a result, she had her first orgasm in less than a minute. I actually had never seen her cum from just her pussy eaten. Don’t get me wrong, she enjoys it when I eat her pussy, but she cums when she mainly cums when I use a vibrator on her. So, I knew this role play game had highly excited her. I ended up giving her 2 more orgasms, as if I was the neighbor boy.
After the third orgasm, she shoved me onto my back and sucked my dick for just a couple of minutes and then boldly said “Fuck this older woman. Stick your boy dick in me and fuuuccckkk me really good.”
She then climbed on top of me, grabbed my cock, and slid her body down on it. Then she leaned forward so her tits were hanging down in my face, as she started rocking herself on my cock as we fucked. I sucked on her big tits as they hung down in my face. I became very excited from watching her totally lose control, and consequently I exploded my cum into her pussy in about 2 minutes.
Afterward, we snuggled, and as she calmed down she said “I am sorry. I am still not sure we should have role played that story. I hope I didn’t offend you with what I said, and did.”
I said “I told you earlier that I wish we could do this in real life. I would let you fuck the boy in front of me. It would really, really turn me on to sit there and watch it.”
Cindy said “Hmmmm. I know it would be fun, and I know I would love it. I am just not sure I could get myself to do it without feeling bad. But, if I did do it, we have to know he wouldn’t tell his friends or his parents, and we would also have to know that he is a legal age, so we don’t get into trouble.”
Then Cindy caught herself and said “What am I saying? I would never do something like that. It is fun to fantasize about, but no way would I ever do that.”
I continued introducing this teen boy role playing into our sex life over the next 2 months. I would change the story slightly each time, but she would end up always fucking a teenager. And, each time, she was as highly turned on as I have ever seen her. Then I would tell her again that I wouldn’t mind seeing it happen in real life, that it would turn me on a lot to watch it.
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.”
Cindy, totally shocked, said “What? Are you serious?”
Cindy looked at me, then over at the boy, then back at me again. There was a long pause, as she stared away in another direction. She finally said “Whew! Well, to be honest, I love seeing the boy excited. It has turned me on a lot. I am not sure I want to see you suck him, but I do want to see him shake with excitement. It really turns me on. So, Mike, if you want to do it for him, that is up to you. But, I don’t think I can watch it. All I ask is that you not let him cum. I want to fuck him again.”
Then Cindy looked at Joey and said “Hon, will it turn you on a lot?”
Joey said “Yes, Mam it would.”
Cindy said to me “Well, Mike if you don’t mind doing it, go ahead. Can you do it just for about 5 minutes, then let me fuck him again?”
I said “Sure, that is fine.”
Cindy turned away to look the other direction, as I grabbed the boy’s dick, lowered my mouth down on it, and started sucking him. To be honest, I loved it. I loved how his cock felt in my mouth. Plus, I could feel the tremble in his body. I guess I had the same feelings that Cindy had when she played with him. It was a huge turn on to play with this boy and have him shaking from the excitement.
Joey started squirming all around, obviously enjoying the pleasure of my mouth on his dick. I then reached down and started massaging his balls with one of my hands. After about 2 minutes of me sucking the boy, Cindy actually started watching me. I also noticed she was now rubbing her pussy. I looked over at her, and she acted embarrassed, as she said “I cannot help it. This is actually turning me on. I just love watching him get so excited. And, I actually don’t mind seeing his dick in your mouth. It is all a lot hotter than I ever thought it would be.”
After another minute the boy was about to cum in my mouth, so Cindy pulled my head off of his cock.
She said “Fuck me, boy. Stick your dick in me.”
I had never heard Cindy talk the way she had talked on this day. She was turned on today more than I had ever seen her. Cindy laid down on her back, spread her legs wide, and the boy climbed on top of her. He had his cock in her for no more than 2 minutes before he was cumming again.
After he came in her, she grabbed his ass, and was squeezing it, as she held his body close to her. I really think Cindy liked his cute little ass, and loved squeezing and playing with it.
I slid down to the side of them and rubbed my hands on both of their bodies. She smiled at me and whispered “Thank you.”
I said “Thank you, too. I loved it all. It was the hottest day of our lives.”
She said “You may have started something that now I cannot live without. I am going to want to fuck more boys in the future.”
Joey heard her say that, and said “I will meet you guys any time.”
We both laughed.
We snuggled each other another 30 minutes, then Joey headed home. Afterward, Cindy fucked the shit out of me like a whore in heat.
It had taken awhile to get Cindy to the point that she would do this, but now she knew she loved it. Will she ever do it again? We will just have to wait and see …
Category: Sexy Stories