Fun on Yahoo


This whole true story was all done through Yahoo Messenger. It all started with Joni. I found her on a jackoff site. Joni is 70, married, but her hubby's cock doesn't work too well so she had set up a network of guys who would jerk off for her on Yahoo. She only watched and every time they came, she would cum. She wanted to watch me jack off but I wouldn't unless she got online and masturbated with me. She wouldn't do that so I wouldn't.

But she was very cock hungry and ended up getting really out of control and did something that, while was extremely erotic and hot, I can't share on Literotica. She came to her senses and realized that all that had to stop. Part of it was that her hubby had a mild heart attack the day after her wild escapades and she was hit with guilt.

Joni had a down-the-street friend by the name of Fran. Fran was 50 years old and her ex had cheated on her and they divorced. But she was a smart one and really took him to the cleaners and so did not have to work anymore. But Joni knew that after nine years of being divorced, she had never been with another man and she was frustrated and probably did not think she had anything to offer to a guy. Joni knew she was wrong and just needed some encouragement. So she told her about me and told me to put her in my contacts.

Well Fran and I had hit it off quite well. Joni thought that Fran would enjoy talking to me and she was right. Somehow our conversation got around to sexy things, but I think that was because we began talking about Joni and her VERY sexy escapades. Fran was so envious that Joni came so easy. Fran told me that she had to work very hard to cum and that sometimes she could cum three times in a row but that was rare.

But Fran was also cock hungry. She had not had a cock for about nine years, after she found out her hubby, now ex, was cheating on her. But she was lonely...and bored.

So when I shared some big cock videos with her she was hooked. And she would masturbate while online with me. No, we never got on cam together...I think it's because her hubby cheated on her and she didn't want to make me cheat, but she would masturbate and share with me while online what she was doing and when she was cumming.

Fran also seemed to enjoy being dared to do something sexy. So I had her stand at her front window naked for one minute. She enjoyed it. She said she "felt tingly", but we both knew that her pussy got wet.

I began to escalate her dares a little. She walked out onto her back porch and settled into her lounge and masturbated while watching big cock videos. She actually came twice. A rarity. And I challenged her to walk around her yard naked at night, which she did the next night, and masturbated to another orgasm.

So where should we go from her? The next day there were some boys playing across the street so I challenged her to stand naked at the door for two minutes. She didn't stand at the door for two minutes. She stood at the door for TEN minutes until she thought the boys saw her and then she chickened out.

The next day the boys weren't there but I escalated the dare again. This time I had her sit naked at the door with her feet spread on the door frame exposing her pussy and tits to the whole world if they happened to come by. No one did, but Fran masturbated to a massive and satisfying orgasm.

She was gone for a few days and I had time to think about her next step. She kidded about letting the boys come up to her door and watch her masturbate so I took that as her next dare. But the boys never showed up again. So that was out.

When she returned (she had visited her sister) she said she had told her sister about me. That surprised me but she asked if I would want to talk to her sister. Of course, being the nice guy I am, I said sure. So she gave me Linda's Yahoo and I added her as a contact. Linda is the little sister, 47.

The next day I heard from Linda. Not knowing what Fran had told Linda I treaded very carefully but pretty quickly it because obvious that Fran had told her about our escapades with orgasms. Fran had told me that Linda's hubby had a very short cock and she thought that Linda could use some stimulation watching some videos of big cocks.

Now I knew that Linda dearly loved her hubby, but was not getting satisfied like she wanted with his cock. His cock was small, probably three inches when hard. Poor girl. They tended to engage in 69 sessions but we all know that women need a nice cock in their pussy, right?

Having been exposed to a smaller cock for her whole marriage, 22 years, she was shocked when I showed her some big cock guys masturbating. She was hooked. And she came very easily. Our first time online she came six times...always typing "cumming" into yahoo. She loved the videos, but like Fran, she was open to dares...which I was pleased to offer.

The first dare was to stand at her front window like Fran, stark naked for one minute. It turned out that her across-the-street neighbor was out working in his yard, but he never looked, much to her disappointment. So I challenged her to stand there for two minutes. This time she thought he glanced her way. This made her very wet.

So I had her stand there and wait. She was so excited. This time he glanced twice and the second time he smiled. She came back to her chair and masturbated to a massive orgasm. She LOVED the excitement to the possibility to be seen, and to actually BE seen, well, that put her over the top.

I then had her go out to her back patio and masturbate to a few more good orgasms. Our first day was a success. I was sure she would come back, and I worked up a plan for her also.

The next day it was Fran's turn. Joni had already shown off for the mailman, so that gave me an idea. Fran was a whole lot younger and had a much better body. For a 50 year old woman, Fran was hot! Now, the only pictures I had seen of her, she was fully clothed, but it was obvious she had a nice body.

So I teased her about showing off for the mailman. But he's married! she wrote.

So what? A married man would love to see a naked woman anytime!

You think?

I know!!

I don't know about that.

I knew about her problem of tempting married men. She wouldn't send me any naked pictures of even talk on the phone because I was also married. So I backed off on that.

I challenged her to walk in her back yard totally naked. Her back yard is fenced but the house next door had a second floor that overlooked her fence. But she was game.

So she slowly strolled out into her back yard. When she came back she told me that the window curtain in one of the upstairs bedrooms moved while she was out there. I told her that she needed to see if it was just her imagination or if there was someone there. So she went out again.

She came back all excited. Someone WAS there!

Someone had seen her naked! She immediately started masturbating and brought herself to two great orgasms, Yahoo saying "cumming". I SO wished I could watch her cum, or at least listen, but that wasn't going to happen.

The next morning Linda got on. She was ready for some orgasms. I told her about Fran and she was amazed at her big sis. And it seemed to spur her on. I gave her the mailman dare. She was excited about trying that.

I told her when the mailman came to be naked in front of her front window "talking on the phone." The mailman was on the other side of the street and didn't look her way when he came by that way. She was SO disappointed. So I told her when he came by on her side of the street to be animated, moving her arms, as if she was angry at whoever was on the phone, oblivious that she was naked in front of the window. That should get his attention.

She was dripping when he approached her house. She said he glanced. She was excited. But he just sat at the mailbox. Didn't look back. Finally he glanced again. And then he was just watching her. I told her she just made a man's fantasy come true.

So I told her to "notice" him. Look a little shocked, then smile. He smiled back. I told her to wave. He waved back. Then I told her to point to the front door and then move to the front door so he could see her whole body. I told her to give him a good view, turning around, letting him see her ass.

She told me he was rubbing his crotch! I told her to assume the position at the door, seated with her feet on the doorframe and start to masturbate. Of course she did.

He's rubbing his crotch!

Motion for him to take it out.

He did it!

Is it nice?

I think so.

Do you want to see it closer?


Motion for him to come to the door.

She did. He laughed. She motioned again, but he wasn''t coming...the fool!

So I just told her to masturbate for him which she did. She had a massive orgasm...Cumming!

He was really stroking. She came again.

I think he just came! she wrote.

You can't tell?

Yes, I think he did. Now he's cleaning himself up.

Get up and open the door and tell him same time tomorrow.

She did. She walked out on the porch, stark naked, her body still flushed from two orgasms. He gave her a thumbs up.

Linda was so excited. She came another two times...with my encouragement, lol.

But tomorrow didn't come. Tomorrow was Friday and her hubby decided to take the day off. Spoil sport!

But tomorrow DID come for Fran. She logged on right around the time that the mailman was to come, so I asked if she had changed her mind about the mailman. She said...maybe. I knew she was hooked. She asked how she could do it so I outlined how Linda had done it. She was shocked what little sis had done but it also seemed to motivate her. But the mailman was late.

So as she watched for the mailman I helped her prepare her pussy for her show. She came once, but the mailman still hadn't come.

Maybe she missed him. So she called Joni to see if he had already come. He hadn't but Joni figured out very quickly what Fran had in mind. She wished her good luck.

She was so excited she had to masturbate again to a nice orgasm. She couldn't believe how excited and wet she was. She was ready. And then the phone rang. Dang! Was something going to interrupt this? No, it was Joni. The mailman was on his way. Time for the show.

There he was. But it wasn't the normal guy! I guess that's why he was late. It was a much younger guy! Maybe he was single!

So I had her pose at the window. Her window reached almost to the floor, so he would get a full view. Oh, I wish she'd turn on her camera!

There he was. He glanced. He glanced again! Now he was just looking! I told her to notice him and wave. He waved back. I told her to show off her body to him. He gave her a thumbs up. She pointed to the door and assumed the position at the door and began to masturbate. He started rubbing his crotch.

I asked if she wanted him to come closer. She said yes. I told her to wave him up. He kept rubbing. She kept rubbing.

I told her to wave for him to come closer again. This time he did. He came right up to her front door. I had told her to lock it. She was so nervous and so excited at him watching her masturbate. I told her to tell him to take out his cock which he immediately did.

They masturbated together for a bit, with Fran cumming (cumming) once, then working very quickly toward her second orgasm.

HIS COCK IS BEAUTIFUL she wrote. He wants to come in!

I wrote back, do you want him to come in?

I don't know, she wrote back.

Then you're not ready for that. Tell him no.

She did but redoubled her stroking action. So did he. She said I think he's gonna cum!

And then he shot, all over her door. CUMMING AGAIN! She wrote.

He asked if he could come in again. She told him no.

Show's over I wrote. So when she told him he zipped up and went back to his truck.

I want his cock! Fran wrote.

I thought you said no! I wrote back.

I made a mistake. I want him to fuck me. And he wants to fuck me. I can tell!

OK, then get some clothes on and track him down and invite him back!

OK she wrote back, and was gone.

She didn't write back for over an hour. I was figuring that he must have come back and she was getting her brains fucked out. I sure wished I could watch.

Finally she came back online. Back

Well, did he fuck you good?

Oh, we just talked at his truck. He was such a nice guy! He asked if I wanted to take it to the next step.

And what did you say?

I said sure, lol. He's coming back right after he finishes his route. But there's something else.


As I was coming into my house my neighbor's 18 year old son came up to me.


He told me he saw me walking in my yard!

So it was him in the window?

Yep. He said he liked what he saw.

WOW! Is he cute?

YESSSSSS!! you have TWO guys who want to fuck you!

YEAH!! After nine years!

I've been telling you that you still have it!

Yes you have J

So we talked for a couple more hours on Yahoo, with me helping her through two more orgasms. She was so excited about finally getting laid.

Finally she said He's HERE!!

Are you gonna answer the door naked?

OF COURSE!! And then she was gone.

And so all weekend I couldn't sleep thinking about Fran getting her brains fucked out. Remembering her masturbating for him at the door. It was a rough weekend.

Finally Monday came around. I was hoping I would hear from Fran first thing Monday morning but she waited until after lunch to contact me. Dang her!

So how did it go? I asked.

OMG!! We fucked and sucked each other for four hours!

How many times did you cum?

MANY!! Many many! I lost count

That's wonderful. When is he coming back?

Oh, I think it's a one and done.

How come?

He said he had a girlfriend and he wouldn't give me his contact info. Afraid she would find out.

Oh well, you at least have Boy Toy #2.

Yeah Maybe.

So I went a few days without hearing from her.

But I heard from Linda. She was ready for the mailman again. She said that she really enjoyed him seeing her naked, but when she heard the success that Fran had, she wanted to have her mailman do that for her.

So we tried it again. And she also had success. He masturbated along with her and came all over her front door also. But then he REALLY wanted to come in and while she also wanted him to come in, she had never cheated on her husband and was not ready to start now.

But her mailman got really aggressive and was banging on the door. "I want to fuck you! Let me in so I can fuck you!"

It scared her. I told her to close the door and then had to talk her down. I told her she made the right decision.

But what should I do now? She asked

I'll tell you what, tomorrow you meet him at the mailbox fully clothed and talk to him. Tell him you're married and you can't fuck him. But if he wants to do that again you will, at your convenience but no demands.


So the next day she got on.

I talked to him like you told me to. He apologized and said that just wasn't him. He got out of control.

So, are you going to do it again?

I guess J

We watched some videos together and she had some amazing orgasms. She LOVED big cocks, especially the black ones. I felt so sorry for her, stuck with a tiny cock. But she loved him.

When I finally heard from Fran I asked her, Have you fucked Boy Toy #2 yet?


Why not?

I have not seen him out.

Well, let's try to lure him out. Go outside for another walk. If you see him peeking stop and look at him and wave. Then touch your body and wave for him to come over.


In a few minutes she came back. HIS curtains didn't move, but the window next to his did!

He could be at the other window. Did you wave?


Go out again and if it moves again, wave.


In a few minutes she came back. The curtains moved again!

Did you wave?

Yes. But no one showed themselves. Who do you think it was???

Hmmmm...maybe his dad? Or little sister? Or his MOM????

OMG!! Do you think??

I don't know

Then I had an idea. How does your bedroom window line up with his window?

It's not quite straight across

Could he see into your room?


OK, tonight, I want you to leave your curtains open and do a nice striptease for him. Maybe masturbate on the bed or something.


Boy, she was easy, I thought to myself.

Then if you think he was watching, leave a note on your window "tomorrow night...your turn"

OH!! I like that! Do you think he has a nice cock?

How would I know, lol.

It took more than a week for Fran to get back with me. In fact it was Linda who told me that my idea had worked and Fran was masturbating with Boy Toy #2 every night.

When Fran finally got online she shared that my idea worked and she masturbated with him, her in her room, him in his room, every night. I asked if she had invited him over to her house.

Not yet

Why not?

I don't know how

OK...another sign tonight. Give him your phone number. I'm sure he would love to listen to you cum also. And then you can listen to him. Then you can invite him over.

Do you think he'll come?

He'd be a fool if he did, lol


So I gave her some more instructions: You have an opportunity to teach a young man how to treat a woman, how to please a woman. You can teach him right.

How do I do that?

Well, first of all, invite him over and tell him your door will be open and to come right up to your bedroom.


Then be laying on the bed naked. Have him come to the side of your bed and tell him not to touch, just look. Can you do that?

Maybe...but I might want to grab him, lol

Well, just let him look first. You can grab later


Then explain to him how your tits are very sensitive and you like them to be touched and licked, and then touch and rub your tits for him. Then let your hands wander down your body and eventually to your pussy

Oooooo! Mmmmmmm

Show him your pussy lips, how they get puffy when you get excited. Do you think they will be puffy by then?

Probably, lol

Then spread your lips and let him see your cunt. Show him how your pussy is so wet. Do you think it will be wet?


Tell him how your pussy likes to be licked. How he should lick your lips and then lick your slit. Then show him your clit and tell him how sensitive it is. Show him how to lick your clit, to suck on it, to pull on it.

OMG! I will cum when I do that!

He's already seen you cum, hasn't he? Now he'll get a close-up!


Then continue to his education, lol. Roll over and let him examine your ass. Let him rub your ass.

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bysecret_admirer72116© 2 comments/ 7457 views/ 6 favorites

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