Maybe My Last Rodeo (Part Two)

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Creampie

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 şişman gaziantep escort 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 gaziantep şişman escort 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 gaziantep şişman escort bayan 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.

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