Phyllis: Part Sixteen

This is the sixteenth part of a fiction serial, in 814 words.

Terence didn’t dwell on his concerns for too long. After all, he had the best part of a hundred grand in his bank account. That might attract the attention of the tax man at some stage, but he could say it was a gift. Geoffrey and Clive were unlikely to argue. If they didn’t believe him, he would worry about that when it happened.

In the meantime, he could afford to move out of his dingy flat, buy a small car, and live in a part of England less grungy than Nottingham. A look around a map online left him deciding on Horncastle, in Lincolnshire. Off the tourist trail, but still close to the coast, he would be anonymous there as Terence. He found a nice two-bed bungalow to rent, and it came with a garage and small garden. That might be just what he needed, at his time of life.

Before he gave notice on the flat and had a moving date, he checked in with his contacts on the website. Someone had caught his eye, and it had to be worth a final throw of the dice before moving.

Alan was forty-six, probably not using his real name. He wanted to know if Phyllis was available to help him dress as a woman, show him how to do make-up, and behave in a feminine manner. He was supposedly straight otherwise; not interested in sex, simply had a desire to dress as a woman for a few hours. As he was willing to pay, Terence could see some easy money. And he might not have to get involved in any blackmail attempt. He replied that he could easily help him, at five hundred a session.

The reply arrived very quickly. Could Phyllis manage two sessions this week, as he had some time off work. Terence saw an easy thousand, and sent him the address. They settled on two consecutive days, Thursday and Friday, with Alan stopping over and sleeping on the sofa. He said he would bring his own shoes, clothes and wig, but would arrive as a man. Terence decided to stick with his identity as Phyllis while he was there, and carefully hid any post relating to Terence.

Obviously keen, Alan arrived an hour early. “Sorry, it didn’t take too long, I live quite near here”. Terence showed him into the bedroom to change, reassuring him. “You get dressed up and then I will show you where you went wrong, okay?” Alan looked nervous, but he also seemed to be genuine. He looked like his photo, and had brought a suit-carrier with various dresses and underwear crammed inside. He also had a smaller bag full of toiletries.

When he came out of the bedroom, he looked a fright. One of the very worst crossdressers Terence had ever seen. His legs were unshaved, his wig was plonked on his head, and his idea of looking like a normal woman was to wear a too-short dress and a pair of fishnet tights. Terence kept a straight face when he spoke to the man. “Oh no, that won’t do at all my dear. You are not a twenty-year old punk, far from it. Let’s go in the bedroom, and we will start again. But you should really shave your legs first, dear”.

Shaking his head, Alan was firm. “No that can’t happen. It will have to be with unshaved legs, sorry”. That told Terence all he needed to know. Alan might have taken off his wedding ring, or might not be married. But he was definitely living with a woman. Shaving his legs would require an explanation, and he wouldn’t have one that would convince any female lover. Terence was kind. “No problem, I will do my best, and have you looking convincing in no time”. He had his fingers crossed when he said that.

After over an hour in the bedroom, Terence had his new friend kitted out in one of the better dresses. Black opaque tights sorted the issue with the hairy legs, and a first-rate make-up job made him look almost female. Okay, almost might be a stretch. He looked like a man dressed up as a woman, but as far as Alan was concerned, he looked amazing.

“Oh wow, you have done a great job. Can we order in a takeaway for dinner? I will pay”.

Before the meal arrived, Alan was shown how to sit like a woman. How to moderate his voice, slip a shoe on and off, and occasionally recross his legs as they chatted. He seemed very happy, and Terence was relaxed enough to open a decent bottle of red wine for them to share over dinner.

Later, Alan rambled on about how he wasn’t gay, but had always wanted to wear women’s clothes.

After two hours of that, Terence was checking his watch, praying for bedtime.

31 thoughts on “Phyllis: Part Sixteen

  1. (1) According to Wiki…, “Horncastle was once a centre for cockfighting and bull-baiting.” This serial adds new context to that sentence.
    (2) Is Alan’s last name Mulvaney? (If so, does he drink a light beer? And does he fancy wearing a woman’s sports bra?)
    (3) I’m sure you won’t go into any details right now about the relationship that is going to develop between Alan and Terence, but is it fair to assume that you’ll phyllis in later?
    (4) With the fishnet tights and unshaven legs, Alan resembled a fur-bearing trout.
    (5) Perhaps Alan should wear a replica of Jeanne d’Arc’s suit of armor? That way, he wouldn’t have to wear a wig, and no one would notice his flat chest and unshaven legs.

    Liked by 1 person

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