A Tale of Mikey

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This story is dedicated to my dear friend Mikey who inspired it and me. Much of this is based on facts and actual incidents however there has been some embellishing to the actual incident to include one of his favorite fantasies. I hope to deliver more stories of Mikey.


Mikey is my hero.

Sounds impressive doesn’t it?

Well he is impressive to me. Mikey is 73 years young. He is a widower living alone in the cold north.

I met Mikey online in a game room. No one would have believed he was 72 then. He didn’t act it. He was a big flirt but a gentleman about it. He certainly got my attention. After that Mikey and I talked often about a lot of different things. I learned a lot about how Mikey thought too.

After a while Mikey really opened up to me. We found we could talk about anything. Before long we were even talking about sex.

Mikey wanted to meet me but we lived too far away from each other. Even so Mikey felt like he could talk to me about anything. Mikey had been married to a very sweet lady who felt that sex was only for procreation. Needless to say, even though he loved his wife, he didn’t have much of a sex life. After Mikey’s wife passed away, things changed for Mikey, and in a very good way.

And this is where Mikey became my hero.

At 70 years of age, Mikey started over. Oh, not just dating, Mikey started having a sex life! Now at 73 he has more sex than I do (a very sad comment on my life).

First Mikey met a lady close to him from an online dating site. She worked in a hospital emergency room and was not at all afraid of sex. She loved giving him blow jobs and having him go down on her, something he had never been able to do when married. They had a good, full sex life, but that wasn’t all for Mikey. Since he was retired from an airlines he could travel any time he wanted, and he did! Mikey met ladies all over the country and would visit whenever he could. Which brings me to the following story.

One day when Mikey and I were talking, he mentioned to me that he had been seeing a woman named Jane who lived in Wisconsin. She was a widowed grandmother of 68 who was open and down to earth and discussed sex with her 20 something granddaughter, Jill. Jill had told Jane that she really enjoyed anal sex and thought that her grandmother would too. The two women had spent a lot of time talking about it and Jane finally brought the subject up with Mikey. She decided she wanted to try it and wanted Mikey to be the one she did it with the first time.

That is when Mikey came to me. In all his years he had never had anal sex, never really thought about it but Jane had him intrigued too. First, he told me, Jane’s granddaughter, Jill, had gone out and bought Jane a set of butt plugs in different sizes. Jane had started wearing them to stretch herself out to make it easier. Mikey began drilling me for information, advice and tricks to make the first time enjoyable for them both.

One night while we were chatting, Mikey told me that he had plans to visit Jane that weekend and they were ready to try it. We went over all his questions again and discussed what he wanted to do and he was off to visit his lady.

I couldn’t wait for him to return on Monday so I could hear all about his great weekend. I was sure it was going to be one to remember. I was on pins and needles until he finally bursa escort got online and messaged me, but the news was not good. Jane’s son decided to pay his mother an unplanned weekend visit, even though Jill tried to talk him out of it. Poor Mikey didn’t get to experiment with anal sex; in fact they were not able to get alone long enough to have sex at all!

A few weeks later Mikey messaged me online and he was in a very good mood. Jane had called him on Thursday and asked him to come to visit her that weekend. She had told her son in no uncertain terms to stay away that weekend. So Mikey made some fast arrangements and went traveling.

When Mikey got there Friday night they had a nice quiet dinner for two and he quietly popped a cialis tablet. The last thing he wanted was to not be able to perform. They sat down in the living room with a glass of wine and relaxed and then necked for a while. Things advanced along well and then they retired to Jane’s bedroom to continue.

They undressed and climbed into her big bed together and went back to necking. Mikey always enjoyed sucking on breasts and Jane had a very nice full set which he spent a lot of time and attention on. He wanted Jane to be really hot and into the action before he advanced. He wanted her to have a really good first experience too. Soon they turned around and moved into a classic 69 position. Mikey really loved giving women pleasure and Jane had become a very good cock sucker and loved to make Mikey beg for release. Things were progressing quickly and Mikey brought Jane to several orgasms in rapid succession, but every time he tried to finger her ass she tensed up. Mikey didn’t feel like Jane was ready so he let her suck him till he came. When he turned around to snuggle with her she apologized to him.

“It’s alright,” he told her “it’ll happen; you’re just not ready yet.”

They snuggled up spoon fashioned and went to sleep. Some time around 5 am Mikey realized that Jane was pushing her ass up against his cock over and over. He could feel himself getting hard, and reached around and began playing with Jane’s boobs. Before long, Jane’s nipples were rock hard and she was pressing her ass harder against Mikey. Jane reached over onto the bedside table and picked up the tube of lube they had placed there the night before. Mikey took it and set it back down, rolling Jane onto her stomach, he pulled some pillows over and moved her on top of them. He spread her legs a bit and began licking on her pussy from behind. Jane was soon moaning her pleasure to Mikey. He moved up and began licking around her ass hole while he slid a couple of fingers into her wet pussy and used them to keep her on the edge. He had never imagined licking a woman’s ass before, but he was getting into it more and more as he went. Soon he had his tongue shoved as far into Jane’s asshole as he could go.

Jane was shoving her ass back at him as much as she was able, trying to force his tongue farther in. Without taking his mouth from Jane’s ass, Mikey reached into the drawer and pulled out a dildo and lubed it up. He reluctantly pulled his tongue out of Jane’s ass and started working the dildo into her ass hole in its place. The farther in he worked it, the more Jane wiggled her ass and moaned. It was obvious she was now ready to try his cock and even though no one had touched it for some time, it bursa escort bayan was rock hard and leaking pre cum.

While rotating the dildo slightly in Jane’s ass, Mikey stood up and worked a glob of lube onto his cock. With one hand he rubbed the lube all over his cock and with the other he continued to rotate the dildo in Jane’s ass, using it to spread out her hole more. Finally he was ready. He shoved the dildo as far into Jane’s ass as it would go and pulled her by her hips and the pillows to the edge of the bed. Standing between her wide spread legs, he pulled the dildo out and positioned his cock at her open hole. Jane turned her head sideways so that she could watch in the dresser mirror. Reaching back with both hands she pulled her cheeks apart to give him more room. Mikey grasp Jane’s hips, pulling her a bit closer and to an angle so that she would have a better view. He gently pushed the head of his cock against her hole watching intently as it slowly slid into her backdoor. Jane shuddered and moaned as he pushed more into her. His cock was a bit wider than the dildo he had been using and he waited for her to relax for him, never relenting in his gentle pressure. With one last push, Mikey imbedded the last inch of his cock into Jane’s ass. Looking down Mikey too in the site of his cock buried to the hilt in Jane’s hole.

“What a site!” he exclaimed.

Mikey began pulling back out of Jane’s ass slowly until only the head remained. Grabbing her hips he began pushing back in. Jane was moaning under him. The feeling of her hot tunnel gripping his cock was amazing. Mikey had never felt anything like it. He could tell Jane was enjoying it too. After a few slow gentle strokes, Jane started shoving her ass back to meet his strokes.

“Harder” Jane called out.

Mikey pulled back and slammed his cock back into Jane as hard as he could. Reaching under Jane, Mikey shoved 3 fingers into her pussy and began frigging them in and out of her soppy wet cunt. Jane bent her back as she grabbed her boobs and began pulling on her nipples. She was mumbling as she shoved back against Mikey’s pistioning cock.

For minutes the only sounds were of moans and skin slapping skin. Jane’s moans were almost continuous as she neared climax. Mikey was trying to hold back his own cum to co-inside with Jane’s. With a shudder Jane cried out her release. Mikey gave a last pounding thrust and ejected his pent up cum into Jane’s ass, feeling her muscles contracting around his cock.

“Awesome!” he sighed as he leaned over Jane’s back and kissed her neck. He slid his arms under her and held her close, his cock buried in her ass until it shrunk and slipped out on its own.

He pulled the pillows out from under Jane and they rolled into the middle of the bed and fell back to sleep in each others arms.

Several hours later, Mikey woke up alone in bed. He could smell coffee brewing in the kitchen. Mikey picked up his robe and went into the bathroom to shower. He stepped under the hot spray and lathered up. Thinking over the events of the early morning hours he began stroking his cock. Soon he was hard again. He was going to jack off quickly in the shower, but suddenly thought of Jane downstairs in the kitchen and changed his mind. He rinsed off the soap and stepped out of the shower. Toweling dry quickly, he wrapped his robe around him escort bursa and went downstairs.

He followed the sounds of Jane fixing breakfast into the kitchen. Jane was setting the table wearing a short night gown. When she leaned forward the bottom of her cheeks showed and Mikey knew she was naked under it. Walking up behind Jane, Mikey slid his hands under her gown and began massaging her breasts.

Joan moaned and Mikey pushed gently against her back. Joan leaned forward and Mikey flipped the bottom of the gown up revealing her naked ass to his eyes. His fingers soon found that she was already wet. He gripped his hard cock and rubbed it against her wet slit. Jane spread her legs a bit and Mikey pushed his cock into her pussy. He stroked a few times before pulling back out of her.

Jane reached back and pulled her cheeks apart as Mikey lined up with her asshole. It was still loose from the earlier action and he was able to slide in easily. As soon as the head slipped inside Jane shoved back and buried Mikey’s cock deep into her ass. He could feel her muscles clutching his cock as he started pulling back out. Mikey gripped Jane’s hips and maintained a steady pace as he drilled her back passage.

Suddenly, Mikey felt hair brush his legs. Looking down, he saw the top of Jane’s granddaughter, Jill’s head between his legs. She leaned forward and began licking Jane’s pussy as Mikey’s balls bounced off the back of her head. Mikey couldn’t believe his eyes or his luck. He had fantasized many times about watching 2 women pleasing each other but never thought he would witness it in person.

Jane looked back when Jill began sucking on her clit. Mikey was watching with just the head of his cock in her hole. Jane wiggled her ass and shoved back onto his cock again. Then she winked at Mikey and suggested they go somewhere more comfortable.

The three of them went into the family room. Mikey sat down on a comfy arm chair. Jane and Jill laid down on the floor and began sucking each others pussies. Mikey slowly stroked his cock as he watched the two of them eating each other. He had suspected that they were intimate but he had never quite expected to see this.

Mikey watched as the two women shuddered through an orgasm. Then Jane got up and walked over to him. Turning her back to him, Jane pulled her cheeks apart and backed onto his cock. Once she was sitting fully on his lap, his hands found her breasts and began tweaking her nipples. Jill squatted in front of them and inserted a dildo into Jane’s pussy. Jane began bouncing on Mikey’s cock as Jill pumped the dildo in and out of her pussy. When Mikey looked down, he saw that Jill had a stuck a massive dildo with a suction base to the floor under her. She was bouncing on that dildo, matching stroke for stroke with Jane on Mikey’s cock. For once, Mikey was not in control as he watched Jill around Jane’s bouncing form. Jane set her own pace, faster and harder as she neared a mind blowing orgasm. Her excitement transmitted to Jill and Mikey.

Bodies slapped against each other. Moans filled the air. Voices cried out as all three reached their peaks and crashed over in waves of pleasure. Mikey leaned back in the chair pulling Jane against his chest. Jill slumped on top of her toy, the dildo falling out of Jane’s pussy as Jill used her hands to prop herself up, all three exhausted.

When they had composed themselves, they went to the kitchen and ate a hearty breakfast. After breakfast they went up to Jane’s bedroom and crawled into bed together.

The weekend, Mikey told me, was a great success.

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