It had been over a year since my last dressing. As I enter my mid-60s, the phrase "mutton dressed as lamb" has extinguished any urges that I've had to dress en-femme. My legs were always my best feature, and I loved to show them off with a mini-skirt or dress. Alas, not befitting for a woman of my age these days. My face when made up, was passable back in the day, but now there are a few more wrinkles to conceal. Any hoot...

Last week while my wife was out on the town with an old friend, I wondered if I still had "it". Don't get me wrong, my wife has supported my crossdressing for over thirty years, and the time was when I could have joined them on their night out on the town, but I wanted to see for myself if I could still carry off the illusion of an attractive MILF.

Over the last thirty years, I've shared my secret with a few close friends. Whether in the flesh or in a photo on my PC. the response has always been positive. The gals expressed their leg envy, and the guys, their sheer astonishment at my transformation. Bob was one of those guys. His ex-wife has even accused him and me of having a sexual relationship back in the day.

Up until only a few years ago, sex with a guy has never crossed my mind. My "lesbian trapped in a man's body" mantra, had been the best explanation for my quirk, and the one that sits best with my wife. More recently, I have entertained the thought of sucking a cock. Not just any cock! Bob's cock. 90% of my solo pleasuring has been imagining sucking Bob's "huge cock", according to my wife. And she knew, from first-hand experience.

My wife had been gone almost an hour, and I was showered, shaved, dressed and made up, and parading myself in front of the wardrobe door mirror.

"Not too shabby!" was my thought, as I admired my reflection. "I would certainly fuck me!"

From my blonde wig down to my open-toe black stilettos, I looked every bit like a woman fifteen years my junior, holding on to her hay-day, evident by the hem on my little black dress. Due to the COVID lockdown, I'd gained a few pounds around my midriff, but my latex high-waist pants helped with the illusion of a slimmer figure. My light tan pantyhose complimented my legs. They had maintained their classic shape in spite of my years.

I strutted my stuff through to the bathroom mirror to apply the finishing touches to my face. I glued the false lashes to my upper lids and completed my eye work with a couple of careful smooth strokes with the eyeliner pencil. I was happy with the result. I applied a few squirts around my neck from my wife's Chanel No 19 bottle and clipped on my gold tear-drop earrings. I picked up an unopened pack of pink false nails and laboriously fixed each one, giving my once dull fingers a splash of colour. I was, at last, ready for my mandatory photo shoot.

I'd taken a few selfies on my phone and was preparing to take a dancing vid when a couple of pings emitted from my laptop. My social media account was still open from earlier and it was apparent that I had received a message. My phone confirmed this a few seconds later.

"Fifi" (my pet name for Fiona) appeared on the caller display. Fiona is Bob's ex-wife and she'd played her turn on Scrabble. Bob and Fiona's acrimonious split made it awkward, as we had remained friends with both parties. Due to the recent ménage à trois my wife and I had enjoyed with Fifi, we were probably closer to her. I sat down at the dining table to operate my laptop. I could see on the list of "friends" that Bob was also online, and signed in.

My mind was doing cartwheels. I knew my crossdressing clock was ticking into its latter stages, and if I wanted to fulfil another fantasy I'd have to act sooner rather than later. It was a scenario that I'd imagined many times, so I was aware of the script. It wasn't unusual for me to chat with Bob via this medium but never dressed as Michelle. And it was Michelle that typed and sent, "Hiya you," into the chat box. I waited for a reply.

I didn't have to wait long. "Hey, bud," was Bob's reply, followed by, "How's it hanging?"

Probably one of the most inappropriate gambits to greet a cross-dresser, but he was ignorant of my current state of dress. "Oh well! Nothing ventured," and all that.

"LOL. Actually, it's not hanging at all. It's currently tucked inside my panties." I knew Bob would know now.

"hahaha." When Bob reverted to hahaha instead of LOL, I knew he was genuinely laughing. "Well let's see you then."

On numerous nights out Linda, Fiona and Michelle would play the part of Bob's bitches. He would hold my hand and 'jokingly' flirt with me. It had been over a decade since those days but he knew what to expect.

I keyed the video call function.

Bob appeared on my laptop screen. I could see what he could see of me, in a small square in the bottom right-hand corner of my screen.

"Hey! Meeshell my bell!" He appeared delighted to see me.

As guys go, Bob's not a bad-looking bloke. Like everyone he's ageing, but still maintains a physique that the ladies admire and men of his age envy. His grey-speckled hair was wet and he had grey stubble on his chin. He was wearing a white T-shirt. For all I could see, he could have been naked from the waist down.

I waved at him like a girl.

"Hahaha!" His laugh boomed from my speaker. "So you're still... doing it then!"

I try to keep my verbals to a minimum when I'm Michelle, so I smiled coyly, fluttered my eyes and nodded. When I had to speak, it was in a loud whisper.

"Hiya you! Just out of the shower?"

"What! Yeh! Am I turning you on? Hahaha."

This was going better than I'd expected. It was typical of Bob to be introducing a sexual reference as soon as an opportunity arose.

"Hmmm!" It wasn't a 'no'. "I'd have to see more!"

"Oh, really! What would you like to see babe?" He called me babe! This was going better than I had ever imagined. There was a tin of Stella Artois on his table. He picked it up and took several swigs of the strong lager.

"Ahha! How many of them have you had?" This would explain Bob's high spirits.

Bob laughed and raised his tin towards the screen. "I'm on my third." He had a cheeky grin on his face. "Don't change the subject... girl. What would you like to see?"

I wondered if he was testing me. 'Your huge cock... that's been inside my wife!' was what I wanted to say. "Dunno! What have you got worth seeing?" The ball was back in Bob's end of the court.

"OK! Where's Linda?" He smiled as if he'd cottoned on to a clandestine set-up.

"No one! I'm home alone. Linda's out with a chum."

"So what's with the 'Have you got anything worth seeing' nonsense? Not what I'd expect from a lesbian." Bob remembered my 'lesbian stuck in a guy's body' in defence of my quirky habit.

"Yes. About that." Things had moved along swimmingly. I felt the time was right to drop my bombshell. "Well, the thing is... I think I could be bi."

"Oh! Okaaay!" He was being cautious. "And?"

"OK, here it is. I've been thinking about taking my femininity to the next level." My throat was drying up. I poured a glass of Rioja from the bottle Linda and I had opened earlier and swallowed a mouthful. Before I could continue, Bob interrupted.

"Hmm, interesting." I waited for more, but none came.

"If you didn't know... would you fuck me?" There I said it.

"I do know... and I would still fuck you! Hahahaha."

I suppressed my blokey laugh and attempted to disguise it with a nervous girly giggle.

"NOW you ARE turning me on!" The ever-increasing swelling in my lycra pants was a testament to that. I shuffled in my chair and did a bit of adjustment under my dress.

I noticed Bob glancing down under his table.

"Anything interesting down there?" I took another gulp from my wine glass.

"Hahahaha! Fuck Meesh! It appears you've got me a little excited."

Without asking for any evidence of how excited he was, Bob aimed his phone under the table. He was wearing only boxer shorts, and there was twitching going on under the white fabric, causing me to choke on my mouthful of wine.

"Wow, Bobby! Is that a python in your shorts, or are you just pleased to see me!"

We both laughed out loud. Bob returned his phone to its original place on his kitchen table.

"Is that all I'm getting?" I exaggerated feigned disappointment.

"Quid quo pro, as they say."

"Hahaha. I think you'll find it's 'quid pro quo' they say, babe!" I laughed at his failed attempt at Latin. "OK!" I positioned the laptop's camera and gave Bob a view of my crossed legs. In true Sharon Stone style, I uncrossed and crossed them in the other direction.

Bob shook his head in disbelief. "You're something else."

"OK, now it's your turn." I was aching to see that legendary cock.

Bob's cock had been the subject of many an after-dinner conversation when the four of us got together for a social gathering and the free-flowing wine had kicked in.

As if to ward off Linda from getting too close to Bob in her flirtatious moments, Fiona would tell her that her husband's cock would hurt. Little did she know that the two of them had already got together on a number of occasions. I knew because Linda told me.

Oh did I mention that that was another one of my sexual quirks? I loved hearing about my wife's sexual liaisons. A couple of work colleagues, and of course Bob, all had carnal knowledge of her.

"Why don't you pop over? We can continue this game face-to-face." It appeared Bob was as eager as I was to explore our sexual deviances.

"You could give me a preview." I didn't think it was too much to ask.

Bob stood up from his seat. His top torso was out of view. My screen was filled with a view of his white shorts. I could see the outline of his twitching cock, and it was impressive.

"Drumroll!" It was my way of letting him know that I wanted to see more.

"Tarraaa!" Bob whipped his shorts down to reveal what can only be described as a magnificent specimen of un-cut manhood. And it was still only a semi!

I gasped at the sight before me. His cock drooped halfway down his thigh.

"Oh fuck! Wow!" ... "I'm on my way."

(to be continued...)