Mrs Henderson

She looked older in person than her photos. That was his first thought, a strange thought to have looking back. They had been chatting for so long online that her appearance wouldn’t have made a lot of difference. In fact, it had taken a few months of exchanging messages with increasing frequency before they had swapped photos. They had swapped many more since of course, which had led to him being here. She didn’t look different, the same figure and features, just with a few more lines. Maybe the photo was an old one, or full of Instagram filters. She smiled and asked him inside, with that voice he was so familiar with putting him at ease. Her smile radiating kindness. Nervously he entered her house.

It had been a long time and a there were a few unusual coincidences for them to get to this stage. They had first chatted on a site about local history, then moved onto other topics. They rarely discussed history now. She had always seemed so easy to talk to about life, despite their age difference. Normally a generation between people will define conversations, likes and dislikes. Especially with the advent of digital technology, she was from an age before the internet and he knew nothing else. This often led to them mocking each other in a playful way. It was mainly him winding her up as he talked her through some IT problem. She liked that he was useful. Eventually she had been able to help him in…other areas.

They had grown closer over time. Most of their chat was about nothing in particular and had been for the vast majority of their conversations. A chance discovery had changed things though, and more recently things had taken an unexpected turn.

He’d found the photo’s accidentally as she was sharing her desktop. There was a pop-up saying she had a virus which her scanner wasn’t clearing. He’d helped out by taking over her desktop and finding how to fix it. He’d talked her through screen sharing, promised not to look at anything he wasn’t supposed to. She was a bit reluctant to say what might have caused the problem. In a folder, not very well hidden, he’d found a selection of photo’s of what first appeared to be attractive women in lace underwear. It hadn’t taken long to find as a few files were flagging the virus detector.

She had gone very quiet as she watched him work. She hadn’t seemed interested in women, she’d occasionally flirted or made some cock based innuendo. As he was deleting files, he realised a few of them were actually men. Men wearing various underwear, tights, stockings. Very well made-up men, but men nonetheless. He didn’t explore further but thinking back he’d wondered if they were all men.

She hadn’t mentioned anything, just kept quiet. He’d sorted the laptop out and made a few jokes about it which had gone down like a fart in a lift. When he realised just how embarrassed she was by it he’d tried playing it down. He hadn’t noticed many, he’d lied. Everyone had those sort of photos, he’d followed up. When she had control of the laptop again she stopped sharing. Her usual cheerful mood dampened. Before they said goodbye she’d apologized, saying she thought she had deleted them. He’d tried to tell her it didn’t matter but wasn’t convinced it made any difference.

Over the next few weeks, she responded to his messages in a rather blunt fashion, seldom initiating any conversation. He began to sense he may have lost his friend. He’d wanted to ask more about it, find out details, he doubted he would get the chance again. He was starting to wonder if they would continue chatting at all.

Eventually she did open up again. There was no mention of the photos. She wasn’t as relaxed as previously, but maybe time would help that. In the end it wasn’t time but a casual question that made them closer in a different way.

She knew about his ex. They had been together for a few years. He’d explained before he missed her and hadn’t found anyone since. They’d discussed how he could find a new “suitor” with her being totally naïve about the modern dating scene. They hadn’t discussed how they had split up, quite deliberately from his point of view but she wasn’t aware of this. He was taken aback when asked, not expecting the question and his usual vague deflective answer had temporarily slipped his memory. As he fumbled his response he realised if he could tell anyone the real reason it was her.

So he explained. She had found her underwear hidden under his bed. He had confessed to stealing it one morning at hers. It was a black lace thong and bra set. He had tried to say she left it there but it was pretty obvious what had really happened. He’d hoped, throughout their relationship, to be able to mention this…habit…at some point. Her reaction was abrupt and decisive. He could keep the underwear now his dirty perverted hands had been all over it.

It was a relief to explain this to someone. He’d lived in fear of his friends finding out, thankfully she didn’t know many of them. He didn’t mind telling it to her now, it was nice to open up about how bad he felt. The truth was, he still wore them. He’d added to them too. She listened to him explaining, and she asked questions. Thankfully they were questions about what they were like, what colours, what type, how did they fit? His mind flashed back to the photos on her laptop. Eventually she asked, “can I see?”

So he’d shown her. The first time anyone had seen. He hadn’t even taken a photo for himself before. He spent time making sure he was showered and waxed in the important places, enjoying preparing himself. It was only a photo from the neck down, he wasn’t ready for more than that. She had seemed to like it, complimenting him on the choice of colour. She pointed out a few things he could improve to look more feminine. After that the conversations had been more frequent again, and often about one thing in particular.

It was still a few months from those initial conversations and confessions to standing on her doorstep. He’d confessed a great deal more about his thoughts and desires since. She too, had been explicit about what exactly she wanted, what she liked in those photos. When she asked him to come over so she could help he’d jumped at the chance. He knew she was married, her husband would probably be in, but he was assured they wouldn’t be disturbed.

Her husband was in, he’d noticed immediately. There were 2 cars on the drive for a start, and they were obviously a family not short of money. The house was impressive, with a large gravel driveway leading up to it. He felt like a trespasser as his feet crunched on the gravel walking up to the front door. He had a strange fear her husband would look out and shout something at him. Should he have made up an excuse in case he did?

Upon entering he’d heard football on the television in the open plan area beyond the hallway but couldn’t see who was in there. She ushered him through another door and upstairs. As he climbed, he heard a shout at the TV from below.

She led him into a bedroom, which was tidy to the point of not being used, then through a door on the opposite side to a dressing room. How grand it seemed, to have a room dedicated to such a purpose. Against one wall there were racks and drawers of clothes. The opposite wall had a large dressing table with drawers and shelves of makeup. There was a large mirror surrounded by lights in front of a pair of stools. He sat on one as she shut the door behind her. In the corner there was a large comfortable looking armchair. It was like a dressing room from backstage at a theatre, or at least the version of one he held in his mind from watching TV.

“Don’t worry about him he’s a pussycat really” she announced, sensing he was nervous. “He won’t come up here if the footy is on” she continued. He couldn’t imagine him allowing her to be alone upstairs with another man but had to take her word for it.

She offered him a drink, poured them both wine before sitting in the armchair. He perched on a stool, putting his wine on the dressing table. He probably shouldn’t drink too quickly although he felt like it to calm his nerves. It didn’t help that she was just sat watching him, looking him over. She was very rarely short of words, but she seemed to be calmly scrutinising him tonight.

“So what did you bring?” she asked eventually. He reached for his bag from where he’d left it on the floor. He unzipped it and passed it to her. She reached inside, pulling out underwear, smiling. She found the ones she had first seen him in. “I remember these” she said with a cheeky look in her eye. She laid each item down on the arms of the chair, careful to match items together.

“You said you were going to do some manscaping?” she asked, reaching for her glass again. He nodded. She would ask to see next, he was aware of this. Was he really ready for this? In some ways it seemed so alien, but he was aware that the situation was turning him on too. There was no reason not too, assuming her husband stayed downstairs.

He stood up, kicked his shoes off. She leaned back in the armchair. She looked at him over the glass as he took his top off, his t-shirt too. She nodded and he continued, loosening his belt to remove his jeans. He slipped his socks off with them. Standing before her in his boxers felt strange, he was starting to worry he would get hard which might seem inappropriate.

“Those aren’t very feminine” she stated, nodding at his boxers. He reached for them, then looked at the door, still worried. “I locked it” she said, “don’t worry about him”. He hooked his thumbs into them and pulled them down.

She looked over him, he wouldn’t pass as a woman but looked very smooth. She couldn’t tell what was shaved or waxed and what was natural. “Let me feel?” she asked. He walked over and turned around slowly as she ran her hand up his legs, over his bum, over his chest. He felt himself start to stiffen, and as he turned around it showed considerably. “that’s definitely not very ladylike” she said, taking her hands away.

He stood back, embarrassed. She started picking up underwear and holding it against him, checking which colour looked good, what felt nice. She settled on 2 sets. “I want you to try these on for me” she asked. He nodded, pleased he was getting softer again.

He picked up the lace green set first. He poked his feet into the knickers before pulling them up. He attempted to tuck himself down between his legs, but it didn’t easily fit with him still being a little hard. He arranged them so there was nothing showing. “I’ll help you with that” she stated as he reached for the bra. Both sets had padding in the cups, so whilst he didn’t look buxom, he looked more feminine, from the neck down at least.

He put his arms through the straps. It was so much easier with help, at home he struggled alone to clip it at the front and twist it around. He turned around as she reached up and clipped the back together. He straitened up after she had adjusted the straps. “Go and look in the mirror” she asked. He walked over and looked. He felt good standing there and was pleased with them, but once again he felt himself stirring as he looked in the mirror. He adjusted himself again but couldn’t conceal it. She shook her head as he walked back to her.

He tried the next set at her request. These were black and more see through. They were slightly wider at the front of the knickers. Everything fitted easier. He felt excited looking in the mirror, but the effect was less obvious. He walked back to her. “I prefer these” she declared excitedly. She reached up and adjusted his straps again. Then she ran her hands down over his chest. It was a slow lingering touch that he suspected she was enjoying. Her hands reached his knickers and she adjusted them, making the elastic straight. Again, he felt himself getting stiff in them as her fingers moved over him. She looked up at him. “If this keeps happening, I’ll have to cage you” she declared. He nodded. He was aware that it was going to keep happening, especially if she kept touching him.

She stood up, walked to the door and came back with a gown that was hanging there, handing it to him. He put it on. She sat on one of the stools by the mirror, patting the one next to her. He moved over and sat.

She started gathering make up, chatting as she did. He’d worn eyeliner once at a fancy-dress party where he’d been a pirate. Not a sexual experience. He had no idea where to start with this, which was why he was here. The sexual tension eased as he was all wrapped up in her gown and she was talking about life. She wiped his face with cotton wipes and cleanser, holding his chin up as she did. He could see her in the mirror but not his own reflection.

She reached for another bottle and applied something else to his skin with a fresh cotton wool ball. She worked her way over his face once, before selecting another bottle and repeating the process. Still she talked, frowning as she worked around his eyes trying to concentrate on getting an even coverage. Next, she used a brush and some powder, he closed his eyes as it swept over him, tickling his cheeks. She laughed as she worked.

She worked her way around his face with another pad from a small flat pot, then another similar shaped but different pot. She concentrated more at this, sitting back several times after straightening him to look at her. Once she had finished with these, she selected another brush and powder set from behind her, tickling him again.

She cleared the dressing table again, replacing all the bottles and creams with different shaped brushed and bottles. She settled down in front of him again, starting work on his eyes. It was difficult to keep them open as she worked around them with various shaped brushed and pencils. He looked up as she did under them, down as she worked above. She occasionally reminded him to open them wide, look ahead or look up. It was a more delicate operation, which she seemed to enjoy. She occasionally sat back to admire her work sipping her wine.

“Just the lips then” she said as she tidied again. He reached for his wine, conscious he wouldn’t get chance as she sorted his lips. She held up various coloured lipsticks to his face before selecting one. She held his chin again, trying to manipulate his lips as she worked. It didn’t take long before she was finished. She sat back, smiling. He still hadn’t seen. She walked over to the shelves at the back of the room and retrieved a long dark brown wig. She placed it carefully on him, walking around him to make sure it was adjusted correctly. She smiled as she sat down, tidying again.

She reached into a drawer on the dresser, taking something out and holding it out of sight as she turned around. “You’re going to look in the mirror in a minute and feel all excited again” she stated, looking in his eyes. “Open your gown and lower your knickers” she demanded, looking stern. He did as he was asked, and she showed him a pink plastic gage with a padlock attached. She reached forward, gripping him in a clinical manner and pushing the loop over his balls. She guided the tip of his cock through the loop and to the cage as he felt himself stiffening. She was quick though; he was inside and tucked up before he became very aroused. She had clearly lubricated the cage before he arrived as it slipped inside easily but was very tight. She pushed the padlock through the catch and locked it. He felt himself bulging against it, could feel the cage twitch. “Knickers on again” she ordered. As he lifted them his cage fitted into the thicker material between the legs, leaving him and his cage hidden, just a bulge.

She beckoned him to the mirror. He stood and looked. It took his breath away. It was the same figure, but the face was unrecognisable. She had created high cheek bones where he hadn’t noticed he had them. The eyes were large and alluring, blue green eyeshadow with a black border exaggerated them. The hair was luxurious, flowing over his shoulders. He felt a disconnection to the image in the mirror but as he moved his face from side to side and the hair touched his shoulders in time with the reflection it came back with a bump. He was that gorgeous girl in the mirror. He ran his hands over himself. She was right to ask him to wear the cage, he would be hard by now, shattering the illusion.

As he stood admiring himself, she was busy selecting clothes. She appeared behind him again with a knee length blue dress. She placed it on the stool then retrieved a suspender belt and stockings. “These first” she said. He slipped into them as she bunched up the stockings and passed them over. He teased his toes into the feet and worked them up his legs. She tutted as they got above his knees and took over. She worked them evenly up his legs until the tops were level in the right place. She attached the suspender clips. As he stood and lifted his arms, she lifted the dress over his head. She adjusted. It fitted snugly against him, tight around the bum and tummy.

Again he looked in the mirror in disbelief. He turned slowly, looking over his shoulder. “You look very sexy” she declared. He turned to where she was sat, back in her chair drinking wine. She looked him up and down again, smiling. “Are you ready to meet my husband?” she asked, with a wicked glint in her eye.

He froze. He wasn’t expecting this and didn’t know how to respond. He’d discussed what he might like to do if he was dressed in a convincing manner but never in any detail. Did her husband know about him? If not, was he convincing enough? How would he react when he realised he was a man in a drag? Judging by the swearing at the TV he’d heard earlier it wouldn’t be positive. He didn’t want to end the night getting a kicking from a guy who’s found a transvestite in his house.

“It will be alright, you look very convincing” she purred at him from the armchair. She sensed he was apprehensive but was enjoying teasing. He still didn’t know how to respond, formulating excuses while being slightly aroused by the idea. Maybe he wouldn’t notice? He turned to look in the mirror again, giving himself a more critical appraisal. Maybe.

She stood, taking him by the hand. Swiftly she led him downstairs, back through the hallway. Once in the lounge he stood in the doorway taking in the room. On the TV there were 2 ex footballers giving their expert analysis of the match in front of an empty stadium. He hadn’t realised it had been that long since he arrived, he must have been upstairs for hours.

His gaze moved to her husband. He sat on a sofa with a half pint of beer in front of him. He looked as he’d expected, stocky and handsome. Slightly younger than her.

He turned to look at his wife as she introduced him as her friend. He gave him a cursory look up and down then grunted hello before shifting himself into a less slouched position on the sofa and returning his eyes to the telly.

“Good match?” she asked, settling down in a chair on the opposite site of the room. He grunted again, looking slightly frustrated, clearly football wasn’t something his wife was into and he couldn’t be bothered to explain. His gaze shifted to her new friend though, and he became more talkative, explaining the score and some brief facts about the match.

“Do you watch footy?” he asked, looking at him, eyes drifting down over the dress and back up again noticeably. He felt himself redden, not remembering the makeup might cover it. He shook his head slightly, his hair flicking his shoulders, reminding him it was there. He didn’t want to say anything and have his voice give him away. He looked at Mrs Henderson again who motioned for him to sit on the chair next to her.

She looked at him and raised her eyebrows as her husband’s eyes returned to the TV again. He felt slightly more relaxed in his presence, so far he hadn’t noticed. Maybe they had already discussed it, although by his response if they had he wasn’t listening. The football commentators finished up and the program credits rolled up. He sat back and picked up his beer, had a sip before picking up his phone. The slightly awkward situation was beginning to feel more comfortable. It wasn’t to last.