Philip was a pretty normal boy at school. He was bright enough but not exceptional, good at art but with no desire to be Tracy Emin or Banksy, competent at English and Maths. On leaving school he had joined the Civil Service and earned a decent salary. He would never be rich, but at least it was regular, guaranteed money.

He had had a girlfriend when he was 14 and 15, but that was nothing to get excited about, and she had been stolen by an older, more dynamic boy. Philip was quiet and reserved and he couldn't and wouldn't compete in that aggressive market. He played video games and watched TV and went out for a drink with his friends once a week.

At 23, he lived with his mother, because after all, why shouldn't he? She was his best friend and his father had left the family and the country a long time ago. She was also a Civil Servant, in a different department, but the same building.

She wanted Philip to get married, so he could have the stable life he clearly needed, and she didn't like the fashionable condemnation of young people who lived with their parents. It may have been an old-fashioned arrangement, but he world changed and it was now a sensible option, the way property prices were. Plus, it meant she had company and the small amount of rent she charged him came in handy.

One Saturday morning she was cleaning the house and he was in the back garden, digging up the vegetable patch. She was grateful for having this strong young man to perform such duties, and as she watched him through the kitchen window she daydreamed about his future, digging the garden for his wife while she, his mother, sat with the young woman, enjoying tea and biscuits.

A mobile hone rang and she looked at hers, on the kitchen table, but it wasn't that. Then he saw Philip's phone on top of his shirt and jumper on a chair. She had seen this before, how people answered other people's phones, so she picked it up. Congratulating herself on making the right movement to take the call, she said breezily, "Philip's phone?" She did it with that raised note at the end that suggests the question mark, although the modern inability to differentiate between questions and statements was a private bugbear of hers.

"Oh," said the surprised male voice. "Mrs Lawrence. Is he there? It's Max." She recognised Max's voice. He was the landscape gardener who had come round to measure up for laying a patio in what was currently a barren former flower garden at the front.

"Oh, hi Max," he said, slipping all too easily into the slightly flirty older-woman tone that she found herself doing these days. "How are you? When am I going to get my quotation?"

"Working on it right now," he said. "Call you Monday, okay?"

"Just bring it round," she said. "I've got the week off."

"Okay," he said, trying to load his voice with respect and professionalism to disguise the fact that he didn't fancy her.

"I'll just get him," she said, moving to the back door and calling her son.

Philip came into the kitchen sweating and panting.

Mrs Lawrence hung around, keen to stay involved in the conversation with Max, even by just being nearby.

It didn't last long. She heard her son say yes and no and sound surprised, then okay and he hung up.

"Well?" she asked.

"Well what?"

"Why did he want to speak to you?"

"Cos he's in that theater group I joined. We were discussing the play we're doing."

"Oh, yes?" said his mother. "You didn't tell me you were in a play."

"I'm a detective," he said. "I use disguises."

"Oh," she said.

"Yeah, in one scene I'm disguised as a woman."

"Really?"

"Yeah, and we have to bring our own costumes. I don't suppose you've got anything that would fit me, have you?"

"Like what?"

"I don't know. A dress?"

"Well," she said. "Funny thing for a man to ask his mother, but I suppose I might have something. Come and have a look." They went to her bedroom and she opened a big wardrobe.

"You're not much taller than me," she said. "But you're broader. So the chest and shoulders are going to be a problem. Ah, here's one." She took out a pale yellow sleeveless dress, the kind that is elasticated at the top and just sits on the chest.

"Well take off your shirt and try it," she said. Philip did so, uncomfortable and embarrassed.

"Perfect," his mother said. "I can't help you with shoes, but I could go down the Red Cross shop and see. What about a bra?"

"Nah, I don't know..." Philip began, but she insisted.

"If you want to look realistic, a woman would be wearing a bra, even a strapless one if she wasn't too big, but to be honest, men like to see a bra strap. It just reminds them that there's something interesting in there. Don't look at me like that, Philip. I might be your mother, but even I had my day. Anyway, you're a man; you should know what I'm talking about. Don't you like to see a woman's bare shoulder with a bra strap? Anyway, same as the dress, you might not have breasts, but your back is broader than mine. I'll pick one up in town later. Black. Lacy."

Embarrassed, Philip left the room and went upstairs, his mother calling after him, "You're welcome. Phyllis."

True to her word, she came back from town later with a black bra and a pair of hold-up nylons. "Unless you'd like suspenders," she said. "Honestly, Philip, it's only dressing up for a play, and you want to be convincing, don't you?"

Then she took from another bag a pair of secondhand burgundy women's shoes with small heels.

"There," she said. "Not too high or you'll fall off and hurt yourself."

He went out that night to the theater group, clutching a plastic bag in which lurked his disguise. But he didn't tell anyone.

After the rehearsal he went for a drink with Max, then back to Max's flat, a modest, pleasant, two-bedroom place in smart new block. They watched football for a while before Max turned it off and turned to Philip.

"So you know what we were talking about?" he said. "What do you think?"

"I don't know," Philip mumbled. "You may be right, but I think maybe you just are what you are and no amount of dressing up is going to change it."

"What's in that bag?" Max asked.

"Costume," Philip said. "I won't need it till the dress rehearsal, but..."

"Show me," Max said, reaching for the bag. Philip gave it to him and Max took out the dress and whistled. "Wow," he said appreciatively.

"It's my Mum's," Philip explained.

"And a bra. And stockings," Max drooled. "And shoes. I need to see you in this lot. You can't leave it till the dress rehearsal, I need to check it out, make sure you look okay. And you need to make sure you're comfortable. Go on... you can change in the spare room."

"Don't think this changes anything," Philip said.

"Okay, okay," Max replied, holding his hands up. "Purely professional. Go on."

Philip went into the little room and closed the door. He took off his shirt and shoes, then his jeans. He wrestled with the bra before finally getting it right, then pulled the dress over his head. He looked at himself in the mirror and thought he actually looked okay. With his shoulder-length hair he wasn''t entirely unfeminine. He sat on the bed and got to work on the stockings, clumsily pulling them up and smoothing them where he hadn't done it properly. The shoes were okay: not exactly comfortable, but he could get used to them. He stood up unsteadily and the mirror showed him the difference that the heels made to his posture. Suddenly he was quite sexy. He liked it.

Then he was embarrassed and slightly worried. How was Max going to react? He had already told Philip that he was bisexual and the conversation he had referred to had been about everybody being potentially that way. Everyone was a latent homosexual, he reckoned. Philip felt he shouldn't be doing this dressing-up thing for him.

But on the face of it, it was all about amateur dramatics, putting on a play, and Max was probably right: authenticity was important, so he should make sure the costume looked right before parading it in front of the whole cast and the director, Desmond - now he was gay if ever anyone was. Max was just a normal guy.

Max didn't even look up when Philip entered the room. he was on the settee, looking at an invoice or something. Philip was disappointed and rather annoyed. He stood and posed as he thought he was supposed to, but got no reaction. He walked over to the settee, a slight wiggle coming automatically, much to his surprise. He felt vulnerable, as though he were naked, while in fact he was fully clothed, just not in clothes he was used to.

He stood right in front of Max, who muttered something about the paperwork and then looked in front of him and noticed a yellow dress from which nylon-clad legs emerged and plunged down into women's shoes.

"Wow," Max said. "Nice."

Philip was flattered and a wave of titillation flowed through him. He moved his hips from side to side and it made him conscious of the relatively exposed nature of his legs. He felt a draught up the skirt - his skirt - that in turn drew his attention to his ass. He was wearing women's underwear; he had sneaked into his mother's room and taken an old pair of black knickers with enough room for his equipment, but with a thin strip up the back which nestled in his crack.

"Turn around," Max said encouragingly, and he did so. He turned all the way round and then sat next to Max, pulling the hem of the skirt down as it rode up.

"Man," said Max. "Is that comfortable? Looks great." He ran his hand over Philip's artificially silky thigh. Philip tensed a little, then relaxed. "You're just like a real woman," Max said, and ran his hand up inside the skirt until he reached the lacy bulge at the top. "Except this part," Max added, removing his hand. "Now you know how women feel when you put your hand up their skirt."

Philip laughed uncomfortably. He liked the feeling of a hand up his skirt. He wanted it again. He took Max's hand and put it back up the yellow tunnel. Max leaned over and kissed him and he didn't flinch. He kissed him back.

And suddenly they were in business. A man and a woman, in role if not in fact. A taker and a giver, an instigator and an enabler. Philip wasn't thinking straight. He knew that if he thought about it objectively he would interrupt the flow, and he wanted the flow to continue to its inevitable conclusion, or one of several possible conclusions. The conclusions all involved orgasms, that was all he was sure of, and that seemed to be a good thing.

Max's hand was now inside Philip's knickers - Philip's mother's knickers - and he was feeling Philip's balls as his tongue continued its merry, naughty dance with Philip's own licking instrument.

Max pulled Philip's knickers down and off, and pulled the skirt up, so Philip's cock and balls were exposed to both of them. Philip could now not deny that he was aroused, that he was fully involved in this sexual exercise. He was clearly, blatantly excited and open to anything. His legs were apart; he must have parted them but he didn't remember doing it. His mouth was open, but he didn't remember doing that, either. It was just a natural reaction to what Max was doing. He was kissing Max because it was simply part of the process, this process of having sex.

Max unzipped his jeans and pulled out his cock. It was long and thin but hard. Max put a hand behind Philip's head to clarify what he wanted. Philip knew already, because it was what he wanted too. He got down there and took Max's penis in his mouth. He had thought about doing this to men ever since he was at school. Now the moment was here. He was on his friend's settee, dressed as a woman, going down on a man. He didn't know if he would be any good at blowjobs, but everybody did it, so how hard could it be? Suddenly he loved Max's cock. Suddenly he loved Max and wanted to be in bed with him.

"Can we go in there?" he asked, nodding at the main bedroom. The master bedroom. That was what he wanted: to be mastered.

Standing alongside the inviting double bed, he allowed himself to be embraced and kissed and to have his cock squeezed and stroked, and then Max's fingers were in Philip's crack, then there was a big finger pushing at his ring, then the finger was inside him, pushing in and out and it felt great and he wanted more. Then he was pushed onto the bed in a kneeling position and Max was slapping his buttocks and then Max was licking Philip's ass. He still couldn't think straight, in fact things were getting worse on the thinking front. He was being overwhelmed by this sexual torrent, this raging river of lust that was sweeping him away to who knows where.

"Take the dress off," Max commanded. "And the bra. Where did you get all this stuff?"

Philip was in no mood for talking. He removed the clothes as instructed and rolled the stockings down, looking at Max for approval. Then he lay on his back and watched as Max revealed his body. He was fit and muscular, a patch of hair in the middle of his chest and plenty under his arms. That long, slim cock looked both daunting and thrilling when he thought about what might be about to happen.

Max took a tube of cream and squeezed some onto his fingers.

"Lift your legs," he said simply. "Higher." When Philip was almost rolling over backwards he had achieved the position his master wanted. Max smeared cream in Philips's crack and on the head of his own cock. Then he knelt between Philip's legs and pushed his cock between Philip's buttocks.

"Relax," Max said. "It's okay." He was so comforting, so kind, so confident. Philip did relax and when Max pushed further and his cock head popped into Philips anus, it was the most beautiful feeling he had ever known. It was even more beautiful than the previous best, which had been a minute or two ago, when Max was licking his ass . This new development had some of the beauty of that sensation in his ass's nerve endings, but now there was the added element of a strange, alien feeling of being invaded. There was a stiff penis inside him and he loved it. Reality and the outside world could not touch him because this was the new reality. He knew he would never be the same. He was at least bisexual. Time would tell if he was solely homosexual, but if being homosexual meant having this incredible feeling, that was okay with him. He knew he had submitted to this man and he had not thought of himself as submissive before. He was assertive enough, he stood up for himself and made sure he got at least partly what he wanted. But what he wanted right now was to be Max's sex toy, his sex slave, the recipient of his masculine urges.

"I'm going to cum," Max whispered. "Want me to pull out?"

"No, no," Philip assured him. "Cum inside me."

Max let himself go and delivered his load of semen, that stuff designed for reproduction, into the entirely unreproductive environs of Philip's ass. Philip loved it. He pulled Max's head down and they kissed and Philip thought maybe he really did love this guy. He loved being fucked by him, that was for sure. Time would tell about the rest.
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Pub: Feb 07 2021 10:12 UTC
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