Clothes Maketh The Man – Part 6.

The next couple of weeks past without incident. I will admit that when I did have a quiet jerk, I found myself slipping into panties and enjoying the sensation. Really, what harm could there be in such a discrete and private game.

I also found myself from time to time gazing longingly at a woman on the bus, or in the queue at the store and thinking, ‘I could wear that differently… Why doesn’t she…” But each time I would catch myself and I’d pull myself back to the here and now.

‘How ridiculous,’ I thought. I am a man. Like most men I have my little fantasies, but I remain a man!

I did notice myself looking at men occasionally, a fact I found mildly disturbing. I found myself doing what I can only describe as ‘sizing them up’. I wondered how they might feel against me. On the subway I found myself allowing people to stand very close, in the hopes I would feel them brush against me, and I confess on more than one occasion I found myself going into the increasing number of meetings I was involved in, wearing panties rather than my usual conservative boxers.

I put this down to the idea of allowing myself to enjoy what was becoming a great pleasure to me, and saying to myself “If no one knows about it, why not?” I enjoyed the secret pleasure and felt I had a private joke all of my own.

I should explain something at this point, in case you’ve missed anything. My good friend and former colleague Steve, and I, had decided to set up our own advertising agency, after both being let go from a Chicago company that had lost a couple of large accounts. After unsuccessfully trying to find position in a San Francisco agency, here I was back in Chicago gradually putting together a few clients and building a fledgling agency with Steve. We were a good team, rarely actually saw each other, but worked well together. I covered much of the creative side, and he was involved in the account management side.

We knew we’d need someone on the accounts side soon, but having a few clients that actually paid was the first priority. Now, with all this stress, you’d think I’d be at my wits end. Oddly enough, nothing could be further from the truth.

Since a rather unsettling series of events at my sisters place  in San Francisco which you can learn about here:    I’d been experimenting with occasional dressing and wearing panties. The most remarkable thing was that, as I explored more and enjoyed finding this side of myself increasingly comfortable, I found I could handle stress, deal with even the most troubling people and generally see life in a rather different way to anything I’d experienced before. The magnitude of this change in myself was not lost on me.

Increasingly I felt as though I had found a new direction in life. How I had come to this I had no idea. In fact, there were aspects of the San Francisco trip I found quite troubling, and yet no one could deny, I was more comfortable with myself than ever before. I was also better able to handle the day to day stresses of life. A part of me reflected that perhaps this was just me being my ‘authentic self’.

The phrase sent shivers down my spine. I’d written enough advertising copy over the years to be able to smell bullshit a mile away. Yet nothing else seemed to ring true in quite the same way. Perhaps I really was tapping into a side of myself that was entirely new. I accepted the change quietly and with private satisfaction. After all, who could I tell?

Certainly not Mandy, my go-to girl for sex and my sometime partner. She would never understand this kind of thing. Mandy was the kind of girl who liked her man to be there when she wanted it, and out of sight the rest of the time. Her career came first, she came second and I rarely got to come at all. I didn’t really have a problem with this, as I was using her every bit as much as she was using me. If I needed a girl on my arm at a party Mandy was perfect. She was polished, knew I was there to satisfy her needs and that I liked the arrangement. Having said all that, I’m not sure she actually liked me. None of this mattered much as she was in Europe for six weeks training with the company she worked for.

My mind had drifted to this thought as I drove to meet with a client Steve had secured for our tiny, but growing agency.

“Oh, Mandy, d’you mind if I borrow your panties today,” I imagined myself saying. No.That wasn’t going to go down well. She wouldn’t be back for a while anyway. Best not to think about it.

As I pulled into the office parking lot I received a text from Steve, saying he was running five minutes late, and to wait for him as he would be along shortly and we had time in hand.

As I waited in the car, a second text came in.

“You owe me a lunch. Sylvia”

At first I didn’t recognize the name, then it came back to me in horrible clarity. Sylvia had interviewed me in San Francisco. I shuddered. She had shown me the pictures (now thankfully removed) from Instagram. My private life was not as private as I had hoped, which you know if you’ve been following this story. Mental note – ‘Kill Devina at earliest opportunity.’

I waited for Steve, and passed the time watching a young man changing a tire across the road.  It was a warm day and I watched the sweat spread on his tee shirt. He obviously worked out, I couldn’t help but notice.  He had strong arms, the forearms hairy and muscular.

As I watched him I found myself absorbed in his physique. Gradually I realized I was becoming aroused watching him, and wondered what he would be like in bed. Such a powerful body. He was bigger than me, and I couldn’t hep but think that if he pushed me down, he could do anything he wished. Anything!

I caught my breathing a gasp as I once more realized I was having a fantasy that was completely out of character and yet tantalizingly exciting. I forced myself to look away and adjusted my pants, my erection giving away my secret interest. At that moment Steve pulled up next to me and I was forced to keep my mind focused on the business at hand.

Nonetheless, as I stepped out of my car I took a last look. When I got home I knew exactly what I’d be slipping into.


It was the last long weekend of the summer. We’d had a successful meeting, and by the time I got back to my office at home, I knew most people would be already starting to celebrate their long weekend.

I had no plans, but I was finding those times when I had no plans were usefully spent experimenting with a little makeup now and then. Yes, I’ll admit it. I would just play with it, you know.

So, the time I was spending alone was far from lonely. It was time to experiment and feel even more comfortable in my increasingly frequent dalliances into dressing up. I had added a few modest items to my wardrobe, too.

I had experimented with pantyhose, yoga pants and a couple of sports tops that gave me a little extra shape. I am naturally quite slight, though I did feel I have a bit of belly that I wanted to hide. I had no idea how to, though. What was most surprising was the fun I was having doing this.

I looked forward to a weekend of private experimentation, and decided to take a last look at any work email that may have come in, before relaxing for the evening.

To my surprise there was an email from Devina. This was not something I felt very happy about, having done my best to banish her from my mind since returning from San Francisco. When I opened it, I saw it had three attachments and was just a short note.

“Just thought you should have these. Glad you had so much fun on your visit. I plan to be in Chicago next week, Luv Devina.”

Typical. Sloppy spelling really irritates me. Not as much as Devina does, admittedly.

I expected to see the snap she’d taken of me wearing the white panties. When I opened the first image I was almost shocked into a state of apoplexy. Instead of an embarrassed man in white panties, there was a ‘man’, or I should say ‘person’ dressed in a sexy pink teddy, pink panties and nylons. What was most disturbing was that it looked like me.

No, it wasn’t that. It looked like me made up, really thoroughly. As I looked more closely I could see it really was me, though I was damned near passable, in a blonde wig and with eye make up that most women would die for.

My mind raced. How had she done it? When had she done it? Was it really me?

Yes, it really was me. There could be no doubting it.

Even in that moment of shock and outrage I remember thinking, ‘damn I look hot!’

I stared at the image. My heart was pounding.

‘Wait a moment,’ I told myself. ‘Maybe this isn’t as bad as it looks.’

With that thought I opened the second image. Now, I want to make it plain that modest prevents me describing the detail of this image, however I can tell you this; I was clearly enjoying using an adult toy on myself, and it was deep within me. What was most disturbing of all was the look of excited glee on my face as I this implement had penetrated me to the very core.

My hand held it in place, and it looked as though I was looking at someone out of the image frame. I was clearly not alone.

‘Oh, my god.’ I thought. ‘I am going to be blackmailed.’ How could it possibly get worse.

Then I remembered the last image.

With a sense of trepidation I clicked on the image. If I was expecting the worst I surprised myself. It was even more dire than I could possibly have imagined.

I will do my best to describe the image without betraying what little modesty remained. I was on my knees, my legs wide apart, the pink panties, which were quite exquisite, showing my shaved manhood, in front of a man. His head was cut off by the frame of the picture, but I can assure you  no one would have been looking at his head.

It was my head they would have noticed. I was greedily devouring the man’s shaft, which was deep in my throat. On the side of my face was what looked suspiciously like semen, dribbling down my cheek and chin.

I looked at the image aghast. I was struck by two equally overwhelming thoughts. First of all, Devina was obviously going to blackmail me to bankruptcy and penury. Secondly, I was hopelessly turned on by what I was looking at.


The next instalment can be found here:

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3 Replies to “Clothes Maketh The Man – Part 6.”

  1. Although I’ve been crossdressing for many many years. I’ve never ever been with a man. I’ve had fun playing with toys of various sizes and even had my wife using a strap-on to take me from one end or the other. Unfortunately, I think it may have bothered her that I enjoyed being taken in such a manner sooo very much. We stopped playing like that a long long time ago.

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