Simon's Mistake Pt. 02

It had been an hour since a happy Simon had left Kelly's apartment, since that moment she had sat behind her door sobbing. 'Why, why now?' she cried out. 'After 6 years why do I feel like this? He's only another screwed up man'.

Kelly saw Simon's discarded jockey shorts and fished them out of the bin. She stroked her cheek with them and sighed as she took in Simon's scent.

She wiped a tear from her face as she tried to make sense of what was happening to her.

Ten years ago, she had been a gender confused youth called Keith. Keith had a great upbringing but when in his teens instead of chasing chicks he found a thrill in makeup and wearing women's clothes. By the time Keith left collage he had enough courage to wear panties and hose full time and had almost mastered wearing makeup in public.

Soon his flamboyant style drew the attention of a local gang calling themselves 'The Hot-Rods'.

Keith was coming home from a local gay club when they cornered him near his home. After teasing and mocking they set about him, forcing him into an alley where he was brutally gang raped.

Each one rammed their cock into Keith's virgin ass. They were rough and not interested with Keith's cries of pain as his ass burned.

It was strange, but when they pumped into Keith instead of hatred, he felt fulfilled and orgasmed, his first real orgasm forcing his ass to squeeze onto the invading cock. He also found himself moving slowly back and forth to milk more cum into his body and quietly sighed.

Keith took 3 massive loads, once the fourth cock was satisfied, he could take no more, his whole body shook uncontrollably as cum flowed freely from his ass and he had a massive orgasm, which made him fall to the ground, weak and helpless.

As a final insult the gang stood over Keith and wanked hard. Four squirts of cum landed on him, his clothes, face and hair dripped white liquid.

'Cya Faggot' they chorused, leaving Keith alone in the alleyway.

They left him bleeding and sobbing in the gutter and it was an hour before Keith staggered home. Of course, his parents were horrified at the attack, but then told him 'What did you expect dressed like that?'

Keith went to his room crying, undressed, and tried to wash the shame away by taking a long shower. It was then he felt a change, as he stood in the cascading water, he could feel the Hot-Rods cum slowly sliding down his thigh. He reached round and ran his fingertip through the white cream and rimmed his ass.

His cock sprang to attention, he hated the rape but found that he loved the feel of hot cum dripping from his ass. Slowly he stroked his huge erection, never had his cock been so long and he began moaning loudly.

Several bangs on the Bathroom door and his mother calling out 'What are you doing in there, are you alright?' snapped Keith out of his ecstasy.

'I'm Ok' he cried, 'I just stubbed my toe.'

Keith switched off the shower and wrapped a towel around his waist. He opened the door and bumped straight into his mother. He blushed as he realised that his towel barely hid his erection, and he pushed past her into his bedroom.

Once he lay down, he found the more he thought of what happened, again the harder his cock became. This time there was no interruption as Keith stroked and rubbed his full length until the tip became fully exposed and glistened with precum.

Using his palm Keith smeared his own sticky goo over his penis, all the time he was getting increasingly aroused. Slowly his back arched, head thrown back, and he had an enormous orgasm. Cum shot high from his cock and bathed his tummy with his hot essence.

Breathless he slowed his strokes until he had milked himself dry and his cock finally began to soften. Keith relaxed for the first time since the attack and knew from that moment what he wanted. He had become a cumslut and had those thugs to thank for showing him his way forward.

Keith decided to leave home, he got a crummy job, but it paid enough for him to rent an apartment. For months, between long work shifts, Keith perfected make up, walking in heels, bought wigs and conservative women's clothing. He also changed his name to Kelly and from then on thought only of himself as a female.

If you spoke to Kelly's neighbours, they would tell you that 'a shy, polite young lady lives there.' They accepted her for who she wanted to be. Kelly managed to get a better job working in an office. By now her hormone treatment had given her small, but firm breasts and no one in the office suspected a thing.

That was until Greg arrived, he thought he was God's gift to women and made a play for every girl in the place. When he tried for Kelly he became so angry at her rejection that he pushed her into the copier room, bending her over the photocopier.

Kelly knew what was coming and tensed at the thought of being raped again, but she didn't fight back as she was wanting Greg 's hot cum to be pumped into her ass, satisfying her perverse need.

She was held firmly against the machine and heard Greg unzip his trousers. She bit her lower lip.

Greg rammed his cock against Kelly's panties. She cried out 'STOP' but really it was just a gesture as she waited for his assault. He ripped her panties down and stared. 'What are you, some kind of freak?' he wailed and left Kelly lying face down with her ass exposed and a very hard cock.

By the time she got back to the office everyone stared at her, obviously Greg had been there first. Kelly gathered her things and, staring at nobody, left forever.

That was when Kelly decided that all men were scum and if she had her way every one of them should made to feel the way she was feeling.

Her hard work had been worth it, and she had raised enough cash to start her new life. She moved away from her hometown and found the place that she now lived in. Again, she hid in the shadows but slowly an idea came to her for revenge.

Kelly decided that men, all men, had a weakness sometime in their lives. She bought herself an erotic wardrobe, loads of sex toys and advertised herself in sex mags as 'The Chick That Will Broaden Your Mind'. She installed hidden cameras and waited for her first client.

One by one in her clients trooped for their unique experience. Every one of them loved the way she teased and edged them, the way she used her strap on made their cocks swell and drip.

Kelly recalled their reaction when she squirted her cum and watched as their flooded ass flowed.

She did have clients who loved the way she had abused them; however, most became angry once they realised what had happened, but one look at the cameras and Kelly asking, 'to whom would they like a copy of their sex exploits sent to?', made sure of a swift departure. Of course she made sure she took their money first.

After a couple of years Kelly had her regular client based and changed her ad so that none could complain about the cross dressing. It was that ad which accidentally snared Simon.

And that is how she had lived for the last 6 years, she had sworn never to get close to her clients, a rule which she had stuck to, until now. 'What have you done Simon? I hate you' she shouted at the walls. She took another long smell of Simon's jockey's, how she was missing him.

Simon had been so different. He had no realisation of what, or who she was, but that was nothing strange as by now Kelly had undertaken breast implants and only thought and acted like a woman. But when she abused his skin and squirted into his ass he smiled, wanting more. He accepted Kelly for who she was and wanted to be like her.

For the first time since Simon had left, she smiled and kissed the jockeys. After taking a long, hot bath Kelly went to her bedroom. She removed her make up, found herself a pair of silk PJs and sighed as the material caressed her skin.

She curled up in her bed and tucked the jockeys under her pillow. Through the night she woke, caught Simon's scent, and found herself stroking her cock through the silken threads.

Kelly could not stop herself thinking of being with Simon, moaning whenever she pumped and was thrilled as her sticky fluid squeezed through the silk. 'You're the one' she mumbled to herself.

By morning she felt that she had not slept. All night she could not get Simon from her mind or nostrils and each time she woke she played with herself until it hurt to orgasm.

She was fixing herself breakfast when it dawned on her that she had no way of contacting Simon and spent the day just staring at the phone, hoping he would call.