Timothy’s loving Grandma

Everyone in school was almost too tired of Timothy’s grandma stories. He would always keep talking about the things he did with his loving grandma. At first, everyone found it sweet how he doted on his old lady but now it has kind of become boring for them. His idea of conversation starter was talking about his granny. Even on dates, he would tell stories about his loving Grandma so much that the girls eventually refused to go out with him anymore. Some even joked that Timmy would call random strangers on road to listen to his tales.

Megan is considered another weirdo in the class. It is just recently she opened up about being a lesbian. In such a small town, a bold confession like that only made her the official freak, second to timothy. It did not help much either that they wee neighbours too. Other kids were soon bullying them calling their locality the “freak colony”. It was not like Megan or Timmy were even friends.

Though they lived next to each other, their parents were always fighting cats and dogs about something or the other. Someday its about parking space while on other days its about garbage bags. Even the kids of each family were told to stay way from each other. It did not bother Megan much for she did not find anything interesting about Timmy to try and make friends. Little did she know something was about to change things for both of them and forever.

Timmy’s window and Megan’s balcony were opposite each other. It was a hot summer night and Megan decided to stroll on the balcony a bit before she sleeps. As she was walking around on the balcony, her eyes shifted to Timmy’s room. To her horror, she saw Timmy dressing up as an old lady and talking to himself. He was tall and bulky. Over that, he wore fake breasts and bum underneath a granny dress and completed the look with a wig. He looked much like Mrs. Doubtfire but not as innocent.

Megan thought she will throw up. Right then, she saw Timmy looking straight at her. He looked equally shocked. Megan ran to her room and closed the balcony door. The next day in school they barely looked at each other. A week went by quietly and neither mentioned to the other the strange encounter they had. One fine Sunday morning, almost two weeks after the incident, both their parents were out of town for some reason. Megan was in her room when she saw Timmy dressing up again. This time, she decided to confront him, maybe bully him a bit and let out some steam even. She has been on swinger websites and similar kinky spaces but this was something way beyond what she would have imagined Timmy to be capable of.

She went over to his place and walked into his room. She taunted him how she will tell everyone who the granny really was if he did not stop doing this charade every day for it bothered her. Timmy was angry and upset. He had no bad feelings towards Megan till date. If anything, he was sympathetic to her for being singled out as freak only because she was honest. But now he felt angry. As Megan kept taunting, he suddenly lunged towards her and pushed her on the bed. then he climbed over her and tightly held her mouth. With his other hand, he pulled down her pants and started spanking her ass.

He would press down his fake breasts on her back at the same time. Megan could not believe what was happening but some parts of her was getting turned on by all of it. Timmy was in no mood to stop. While he was dressed as a loving grandma, he took off the panty and exposed his rock hard dick. Then he gave a mighty push and penetrated Megan’s dry pussy. She let out a cry of pain and could not believe she was getting fucked by a guy after all. It does not matter he was dressed like a very old lady but he was a guy after all. Timmy kept going deeper and deeper inside her for the next thirty minutes. When he finally stopped, he climaxed deep in her pussy and filled her up with warm juices. But he was not yet done. Once he pulled out, he started spanking her ass left and right. He kept spanking hard till they looked red and raw.

Megan was feeling repulsed now by everything when Timmy flipped her over and then shoved his dick in her mouth. She was in half-mind to bite him but he seemed to guess her intent and slapped her hard. Then he held her by the hair and started fucking her mouth. She felt the dick going down her throat and gagging her. Saliva dripped down her chin while Timmy kept fucking her mouth. With the other hand, he inserted a small vibrator inside her pussy.

Megan was surprised what was that for because it was completely still. Suddenly Timmy turned it on with a remote in his other hand. He continued to increase the vibration speed till Megan was begging him to slow it down. It was so obvious that she would climax soon. Timmy shoved the fake breasts on her face and squeezed them hard on her. She was nearly choking between them when she climaxed and the vibrator kept going on and on.

Once she had orgasmed, Timmy pulled out the vibrator and let Megan go. She was weak at the knees and could not believe what just happened. Timid back-bencher Timothy turned out to be kinkier than any person she ever knew. But more than anything Megan realised; she was looking forward to the assaults again. She never felt such passion before and somehow, Timmy in granny clothes turned her on more than any real girl she has ever met. Now she has a better idea about the tales of his loving grandma.

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