Tim's Transforming Weeend

Melanie had moved into the house the day after Tim's 18th Birthday - six months before. Until then she had been living with her boyfriend, but the relationship had come to an end and she did the natural thing: she moved back home with her Father and stepmother. As well as Tim her stepbrother. For Tim at first it had been difficult, sharing a bathroom, having his peace and quiet disrupted, but after a couple of months things had settled down and he had grown to love his stepsister. Perhaps lust would be a better word - she was hot - 22, shapely, sexy. And of course things got more difficult to more comfortable things became - she would walk around the house in her pyjamas, and occasionally underwear. She would leave the underwear lying around, and it was always sexy. Of course she was well beyond Tim, but that didn't stop him dreaming about her, and sometimes jerking off thinking about her.

People would describe Melanie as "out there" and she would sometimes blow up, and express her views freely, but there was never any malice, and as soon as she had blown up she was your best friend again. So it was Friday evening...

"The little pervert is doing it again!" Melanie's voice screamed out through the house, as she stormed down the stairs and burst into the sitting room, pointing her finger at Tim, sat watching the television. "I bet he's wearing them now!"

Tim liked Melanie, but this one of her "explosions" as he called them, but one aimed at him.

"What's the problem?" It was Jean, Tim's mother, Melanie's step-mother who tried to sooth and calm Melanie down.

"I wanted to wear them this evening and can't find them. I bet he's got them on. I found my lacy blue set in his bed on Monday when he was out. Had to wash them. He'd stained them. Kept that quiet. But this is at least the second time..."

"Please Melanie, stop shouting - please just tell us what you're talking about." At that moment Keith, Melanie's Father, Jean's partner, Tim's step-father entered from the garage, drawn in by all the noise.

Melanie sighed. Tim looked at the floor and squirmed. It was the moment he had dreaded, but couldn't stop himself - he was found out, his little "kink" was about to be revealed...

Melanie was in full swing. "You know that pale blue set of bra and panties I have. I couldn't find them on Monday. Wanted to wear them, so searched everywhere. I went into his room to ask if he'd seen them. And they were on his bed, and the panties were stained. Dunno where he had gone. So I just put them in the wash..." Tim went red - he had "used" them, but was really worried when he couldn't find them, but thought as the week went on that whatever had happened was disappearing into the past. Now, it was tea-time Friday, and everything was unravelling. Melanie was still in full flight. "...and then I went to find those white lacy ones I've got, and found the bra but the panties are missing. I bet he's got them."

There was a pause as they all looked at Tim. It was his mother who spoke first. Softly. "Tim, are you wearing Melanie's panties?"

Tim couldn't speak, he was so embarrassed. Anyway, he had passed his eighteenth birthday months before - it's not the sort of question you ask your grown-up son! He should tell them to mind their own business... "There's an easy way to find out." Keith spoke in his deep masculine voice. "Tim, take off your trousers."

Tim was mortified, wanting to run. Jean was ready to step in but Keith raised his hand. "Stand up, Tim, remove them."

Tim slowly rose to his feet, all the others watching. He kept his eyes closed. He felt he had no choice. He undid his trousers and dropped them to the floor. His embarrassment was excruciating. He was wearing the panties. He knew they were lacy and that his cock would show, at least in outline, in them. More than that he was also wearing a pair of Melanie's white stockings and suspender belt.

For what seemed like eternity they all stood around in silence looking at Tim with his eyes closed, his trousers around his ankles, wearing his step-sister's underwear. It was Melanie herself who broke the silence. She giggled! Tim's embarrassment, the ludicrousness of what he was wearing, and his trousers around his ankles. Truth was she did love her younger step-brother - he was really sweet, and somehow the moment was making him even cuter.

It was Keith who made the decision - and when he did make a decision no-one disagreed. It wasn't that he was unpleasant or difficult. The opposite. He was a strong man who made decisions and kept to them. "I think we need a suitable punishment. I know Melanie is going out this evening, but the rest of us are at home. You will take your trousers right off, as well as those socks and shoes. You'll spend the evening wearing those panties and the rest. Think that is enough of a punishment. Anyway, I'm hungry..."

The Friday evening meal was strange. Not the food - they all enjoyed the chilli. Melanie was trying not to giggle. Jean was trying to be as normal as possible. Tim desperately trying to think of a way to escape the embarrassment of eating wearing his step-sister's underwear. The only one who seemed not to be phased was Keith, talking about what they were all going to do for the weekend.

Finally the chilli was finished, as was the ice cream. Melanie declared she would have to get ready for her evening out with friends, sarcastically adding that she would have to find some different underwear to put on, disappearing to her room. Tim also waited for Keith to disappear to the garage and for his mother Jean to go to the kitchen to wash up, before running to his room.

Tim slammed the door and lay on his bed. Part of him was mortified, embarrassed, in tears at what had happened, so humiliated. And yet... and yet Melanie, and his mother, and his step-father had seen his cock...or at least a big hint of it in the panties. And in the embarrassment it had gone a bit hard. He desperately wanted to jerk off, but thought he would wait until later. At the moment he just wanted to cry - it had been going well, but suddenly everything had gone wrong... horribly wrong.

Tim was now eighteen, and looking forward to going to college in the autumn. It had been a difficult journey to get to this stage. Until he was fourteen his father Michael had still been with Jean and Tim. It was difficult when his real father was home - they didn't get on, particularly over the last three or four years before he left. Tim was a disappointment to him. Michael was a really masculine type, with muscles, tattoos and shaven head. He worked on building sites. He had played football when younger. He drank Jack Daniels in great volumes straight from the bottle. He had wanted a son to be the same, and Tim wasn't. Tim maybe got most of his genes from his mother - he was slim, average sort of height for his age, and still was. He had blonde curly hair. No-one would call this smooth skinned, freckly kid masculine! Jean - Tim's mother - was also slim, with curly blonde hair. She had been attracted to the masculine man, who had been attracted to the feminine girl - he was 23, she was 19 when they got married. They had settled into a routine, which all came to an end when Tim was 14, and his father left.

To tell the truth, his father was arrested, and was given many years in prison.

For a few years Tim and his mother lived together, Tim receiving the help he needed, his mother trying to make ends meet. Then she had met Keith. Keith and Tim had got on well enough - Tim was now quite wary of men. However in the end Keith - a divorcee - moved in with them. Keith was a strong man of few words, but he was decent, and caring. He worked as a foreman at a local garage, well regarded by both colleagues and workmen - a man of integrity and strength. He liked Tim, and enjoyed spending time with him. Somehow he found Tim complimentary and enjoyed that, unlike Michael who had resented and hated him. The love between Keith and Jean grew, and they were planning on getting married.

Keith had a daughter Melanie. She was away at college, but six months before she had needed a place to stay, and had moved in with Jean and Keith. Melanie was four years older than Tim. And a lot more confident. And outgoing. She was warm-hearted, and quickly became the older sister Tim had never had. She was tall, dark haired and shapely. As well as having her as an older sister, Tim had a crush on her. Dreamt of having sex with her, which was far beyond what he would ever achieve, he was sure in his mind. But it was those dreams that set him to looking for her used underwear.

At first he would just try them on. Then sniff them, then taste them. In the end he liked to wear them when he wouldn't be found out, and like to jerk off in them while reading or watching porn on the computer. It was that which had led to this awful horrible Friday evening. He had been caught. Humiliated. And everything would be different.

For a couple of hours he chatted to friends online, and played games. He heard Melanie go out. He felt like a can of something to drink out of the fridge. But it meant going downstairs and walking through the living room where his parents were watching telly - in the underwear. For ages he didn't, but then came the "what the heck" moment - he'd do it.

It was so difficult, yet he found it strangely exciting. Keith would see him. His mother would see him. People would see his cock, at least encased in the panties. Thinking about it he was getting hard. He just had to do it. He descended the stairs, opened the door and slowly walked through. His mother spoke to him. "Hi honey, what are you doing?"

He was embarrassed, but a woman was seeing his cock. Okay, it was his mother. But it was still a woman - a hot woman, he thought of a sudden. He spoke hesitantly. "Um, just getting a drink mum. Is that okay?"

"Course it is, honey. You look nice dressed like that. Sexy." She didn't know why she said - trying to be funny... It sounded naughty.

Tim dashed to the kitchen, then walked back to the sitting room. He stopped for a moment. "Um, I'm going to bed. I'll put these in the wash. Goodnight." But it was strange - not only was his mother smiling, looking at him, he was aware the Keith was "looking" at him as well.

"Goodnight, honey. Sleep well."

Tim ran upstairs, he went to his room. Jerked off in the panties. Put the panties in the wash and got ready for bed...

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Breakfast next morning was remarkable for its ordinariness, as if the previous evening had not happened. Even Melanie, when she appeared, said nothing, simply chatting about where she had been the previous evening. That afternoon Jean and her step-daughter Melanie decided to shop, and have a coffee, maybe later taking in a "chickflic" - they both enjoyed a good "girly" film. They ended up late afternoon on a corner table in the restaurant of a department store before going on to the cinema later. After chatting a bit about what they had bought, it was Jean who approached the subject of the previous evening. "I'm really sorry about Tim wearing your stuff, and, um, doing what boys do in, um... I hope you don't mind..."

Melanie smiled. "No, Timmy's sweet, but I hope he doesn't break things, you know. I'm sorry I embarrassed him so much yesterday."

"Sweet? Dunno about that - he has a real crush on you!" Jean smiled.

Melanie smiled back. "Even sweeter!"

Suddenly Jean looked serious. "Mel, I'm sorry I'm so careful. I just don't want Timmy hurt again. He has had a terrible time. I need to tell you his story. I'd do anything to make him happy - I feel so guilty about what happened. Please let me tell you so you know. And can understand."

For the next few minutes Jean told the story. She told how her ex-husband Michael drank more and more, and how, when Tim was 10 he started hitting him, physically abusing him, but in a way that didn't show. She told how for the next 4 years he subjected Tim to a continuous time of hitting and physical abuse. She told how she just thought Tim's unhappiness was puberty, nothing more. She told about the time when her husband had kicked him in the testicles, and he had run away, but after being taken to the police station and trying to tell what had happened, the police had not listened and simply returned him to the family and more punishment. She told Melanie about how sometimes there were bruises on his face, and sometimes the school asked about them, but Tim wouldn't say anything, and Michael denied everything. Jean described some of the awful things that he had done to Tim over 4 years, how she had not read the signs, had ignored all the signs.

Finally Jean told Melanie about the night Michael was arrested. He had been drinking all day, even more than normal, but she had still gone to a friend's for the evening. When she got home around midnight Michael was drunk asleep in bed. Tim was semi-conscious, bleeding, lying on the kitchen floor. He had several broken bones, cuts. He had been badly beaten.

Over the coming days as he lay in hospital Tim began to tell the tale of what had happened. A policewoman had believed him. It went to court, and although Michael had a really vicious lawyer who attacked Tim for hours in the witness stand, leaving him crying and shaking in fear, in the end the evidence was overwhelming, and Michael was put away for a long time. He would be an old man when he came out, and prison doesn't treat child-beaters kindly.

Jean told her about the long counselling Tim had received, the physiotherapy he needed, the nightmares he had, screaming out every night. She also proudly spoke about he had continued to study and was top of his class in exams, such that he was off to a top university. She told how Tim had his confidence completely destroyed, such that he was the nervous person he was now, frightened, feeling it was his fault his father had hated him, feeling he would never have any future. Jean told Melanie about how she knew he played with her own underwear as well as Melanie's, the nearest he thought he would ever get to a woman.

Mostly Jean told her about how she felt totally guilty for what had happened, that she hadn't listened or picked up his torture for four years. Jean told how she would do anything - absolutely anything for Tim, just to make up for how she had failed him.

At the end Melanie was also in tears - such a good lad, cute lad. Maybe she could help...

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"Think the two women will be gone a long time. Won't see them before ten." Keith and Tim were in the kitchen, Keith drinking a can of beer, Tim a coke. Keith continued. "Why don't we watch that video you got the other day from Sean?" Sean was one of Tim's friends, and had lent him "Die another day," - the James Bond film. Often when they were home on their own they watched a video together. They both enjoyed the time together, and enjoyed movies. Tim agreed - he needed to take the video back on the Monday.

"Tim, can I ask you something?" For the first time Tim could remember Keith was hesitant - he was normally quietly confident.

"Sure Keith, anything." Tim was pleased to be asked.

"Will you dress up this afternoon as you did yesterday evening?" Tim was stunned.

"What?"

Having said it once, Keith was now more confident again. "I would love you to go up to our room and put on the clothes I've put on our bed. I've put a bra there as well. Come and watch the video with me dressed like that."

It took Tim a few moments to process what he had been asked. But there was no doubts in the end - something within him had leapt in excitement at the thought. Tim went upstairs, went to his mother and Keith's bedroom and saw a pair of pink lacy panties, suspenders, stockings and bra. He recognised the stockings as some his mother wore on sunny Saturdays when she went shopping. He struggle a bit with the bra and suspenders, but eventually got them on. Then in a pause he realised - panties that had been against his mother's pussy were now encasing his cock. His cock leapt in response to the thought.

Tim returned timidly to the sitting room and went to sit on the arm chair furthest from the settee where Keith was sat. Keith smiled. "You don't need to sit over there, come and sit here." He pointed to the settee next to where he was sat. Tim shyly did, sitting 6 inches from Keith. Keith fiddled with the gizmo and got the film working, and they sat back to relax.

Before the movie started there were some adverts for other films. Keith looked to Tim. He whispered softly just so Tim could hear: "you look so hot and gorgeous and sexy dressed like that." As he did he put an arm around Tim's shoulder and pulled him to himself so he was leaning into his side. He pulled a bit more so that Tim turned in to him, then Keith kissed him on the forehead, then let his lips touch Tim's. Tim was so shocked. It felt so wonderful, to be in the strong arms of another man.

As the film started they pulled apart slightly to watch, but within a couple of minutes Tim felt Keith's fingers wandering up and down his back, caressing, rubbing softly, exploring. Tim relaxed - it felt so nice, but found it difficult to watch the film.

For a few moments Keith's hand caressed the small of Tim's back, then went lower, and was cupping Tim's ass. Tim tensed, but as Keith's hand gently squeezed, he relaxed again. For a few minutes he enjoyed Keith resting his hand on his ass, aware his cock was tingling at the what was happening to him.

Suddenly Tim felt Keith moving his hand. He had moved it up Tim's back, then back down inside the panties he was wearing. This time Keith's hand was against Tim's bear flesh. And he was aware of Keith moving his fingers, so that his forefinger was squeezing between the cheeks of Tim's ass. Tim tried to relax but it felt so frightening, risky. Fantastic. His body jerked as Keith's finger found Tim's asshole and began to caress and explore Tim's most private place. For Tim, it was the most exciting thing he had ever experienced, and his cock was as hard as rock.

Then after a couple of minutes something even more exciting happened. Keith's finger pushed through the ring of his ass. At first it hurt a little, but his muscles quickly grew used to it, and even allowed Keith to push his finger in even further, until it was almost in to the knuckle.

Tim looked up towards Keith, to see Keith smiling, then moving in to kiss Tim on the lips. It was so good to Tim. He felt Keith thrust his tongue into his mouth, and tentatively responded. His response made Keith thrust his finger hard into Tim, then out, in again. Tim had seen the phrase "finger - fucked" - he was being finger fucked. It was the most amazing thing that had happened to him. Ever. His cock was throbbing, his body totally submitting to Keith as they cuddled together on the sofa.

Suddenly Keith let go the kiss, removed his finger from Tim's ass. He pushed Tim over his lap. Tim felt Keith tickle his asshole for a few moments - he loved that someone could see it. Then he felt Keith put his arm under him and lift him. He lifted him so that Tim felt precarious, but felt Keith's tongue caressing his asshole, swirling, causing Tim to twitch involuntarily. As he did, he felt Keith catch hold of his cock and squeeze.

Tim was completely in Keith's control and was loving it. He loved it when Keith said to him "wow, nice cock, gorgeous cock," then quickly returning his tongue to Tim's asshole, his hand now jerking Tim's cock. Tim was happy - he had once measured his cock and it was over 6 inches, but to be told... Tim had abandoned himself to what Keith was doing, moaning loudly and in abandon.

It didn't take Tim long before his body was jerking, his voice crying out, shooting cum all over Keith's hand which had been jerking him off. Tim's body seemed to twitch and pump for ever - the first time someone else had ever made him cum. At last there was no more, and Keith removed his hand and lowered Tim onto his lap.