Phyllis: Part Three

This is the third part of a fiction serial, in 798 words.

It was easy enough for Terence to whittle out the unsuitable contacts. Some sent unsolicited photos of their private parts with lurid messages about what they would like to do to Phyllis. They were all rejected out of hand. Others were far too young, even though he had stated 65-75, nine of them were under forty. He presumed they were looking for an older woman who might be grateful for sex.

Only one of the messages was from someone who suspected he was not female, but even that was positive. ‘Are you a man dressed as a woman? That doesn’t matter to me, I would still love to meet you’. He was blocked too. The whole point was to convince as a female, not to indulge the sexual fantasies of someone who liked crossdressers.

Although Terence had no real interest in sex, he had certainly had his fair share of it over the years. The casting couch was a reality in his younger days, and he had quickly learned to please both male and female producers and directors to stay in their good books. He considered himself to be a consummate actor, and his skill extended to being able to convince as a willing participant in whatever turned them on. But a long term physical relationship with someone of either gender held no interest for him.

He was a loner, in the real sense of the word.

After a long evening at the laptop, there were four particular persons of interest for him. Even as he re-read their profiles, more messages were arriving. Over sixty by the time he logged off and climbed into bed. He would explore his main choices the next morning.

Some of the profile photos were hilarious, and obviously taken years ago. One man who was seventy-two used a photo of himself on a golf course when he must have been around forty-five. By lunchtime, he had chosen his first target, the one he would get in touch with showing some serious intent to meet.

Geoffrey Lawson described hmself as a ‘Fit and active 74 year old with an outgoing personality, keen to meet the right lady for outings, holidays, and hopefully much more’. His photo was seemingly genuine, showing him sitting on a boat with a drink in his hand. He looked his age, was slightly overweight, and had not tried to change his full head of white hair by using dye. Googling the name, it took a while to find the right person. Retired from one of the major banks, widowed with two grown up children and five grandchildren, and living in an affluent part of Surrey, in the Home Counties near London.


There was no reply to the contact message until almost six that evening. It came with profuse apologies.

‘So sorry to get back to you so late, dear Phyllis. I was at the golf club this afternoon. Please do not think for a moment I was ignoring you. I am not used to this at all, my children suggested I join a dating website, and you are only the second lady I have tried to contact. The first one did not reply, so I hadn’t checked again before I left home earlier. I would very much like to meet you at a place of your choosing. Perhaps a nice dinner in London? I will let you decide. If you have other photos, I would love to see them’.

Terence had no shortage of photos, and scrolled though some that were just that little bit sexier. He sent Geoffrey three photos of himself wearing a short black cocktail dress and black stockings. One front view standing, one rear view standing, and then one sitting down with his legs crossed showing a little too much thigh. He kept the message short. ‘A meal in London would be lovely, Geoffrey. If you want to go ahead with a meeting I am free this coming weekend’.

The reply was almost immediate.

‘Wow, you are gorgeous! I have heard good things about The Oxo Tower restaurant in London. I could meet you there on Friday at seven, if that suits. Let me know, and I will book a table. Here are some recent photos of me on holiday last summer’.

No less than six photos were attached, all showing him wearing very small swimming briefs on what appeared to be an exotic beach, judging by the palm trees and powdery white sand. No doubt he thought his suntanned hairy chest would be enticing to Phyllis. But he had suggested a very good restaurant that was reasonably expensive. So Terence replied that would be ideal. Again, the reply was very fast.

‘Fantastic. I am so excited to meet you, dear Phyllis. I can’t wait for Friday!’

38 thoughts on “Phyllis: Part Three

  1. (1) “It was easy enough for Terence to whittle out the unsuitable contacts.”
    Two things…
    First, don’t buy super-adhesive contact lenses.
    And second, using a knife is dangerous, as it can slip and stab the eye.
    (2) In praise of older women: Young men are not only looking for an older woman who might be grateful for sex , but they also hope to learn the fine art of lovemaking that an older woman presumably can teach them.
    (3) “Are you a man dressed as a woman? That doesn’t matter to me, I would still love to meet you.” Apparently, some like it hot…
    Daphne/Jerry, whipping off his wig: “But you don’t understand, Osgood! I’m a man!”
    Osgood: “Well, nobody’s perfect!”
    (4) Speaking of cross-dressers… Once upon a time, there was a holy man from Nazareth who bared himself to dress a naked cross.
    (5) Terence, who is over the Hill, once played a cowboy in a spaghetti western. To prep for the role, he watched a Geico commercial:
    “I’m sorry, Daisy. But I’m a loner. And a loner’s gotta be alone!”
    Ever since then, Terence has considered himself a loner. But, of course, everybody knows that…
    (6) Geoffrey Lawson’s photo showed him sitting on a boat with a drink in his hand. He’s old, but he’s not very wise. As his age, he should know better than to drink seawater!
    (7) Terence made a mistake. One of his photos showed “Phyllis” taking a bubble bath and holding a can of beer. The photo’s caption read: “This bud’s for you!”
    (8) Geoffrey was able to arrange a date quickly. Perhaps the photos of him wearing a Speedo helped?

    Liked by 1 person

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