Cindy Pays a Bill

One of the advantages (or curses) of being a bit of a writer and story teller is that people, well, tell me stories. Sometimes the story is so personal that I have to wonder if the teller really wants me to pass it on. I always ask permission to use a story and I respect any wishes to change names and identities. So it comes to pass that I tell you about ‘Cindy’, her sister and their unusual way of paying a certain bill. I can tell you girls that the basic facts of this story are true. I’ve taken some liberties in creating a ‘dramatic re-enactment.’

Cindy is a late 40-something crossdresser who is embracing her interest in all things TG with the gusto of someone who has suppressed that interest for many years. In day-to-day life she is a school teacher. The last time we talked Cindy was about to spend part of her long summer holiday in Vancouver, Canada taking care of her sister’s home and living 24/7 as Cindy.

One evening I had no sooner prettied myself up and logged on to Skype than I got a request to talk from Cindy. “How is Vancouver going?” I asked.

“Awesome,” came the reply, “However, I’ve not taken your advice to seek out gentlemen using Craig’s List. I think I’m just not ready to be with a man. I have chatted with your friend Raymond and he wants to see me but so far I’m holding him off.”

“But I want to tell you,” burst Cindy, “my sister has a really nice place.”

“Your sister? The one that knows about Cindy?”

“Yes and yes. She is and always has been pretty free-spirited. She doesn’t deny herself any pleasure and she doesn’t want to see me denied any either. You know she prepared a booklet for me listing and rating all the best night clubs and shopping places in Van.”

Some time ago Cindy had filled me in on some of the details of her early life. She and her sister, Sandra (or Sandi), had grown up in a rural area near Brockville, Ontario. When the boy that was to become Cindy was 12 years old the older sister, Sandra, took him in to a wooded area on their family farm and explained that she wanted to find out what it was like to give oral sex. Here I should insert that it was common in that somewhat remote area of Canada at that time for a boy to insist on having sex with a girl if he was going to take her out. The girls’ common belief was that oral sex was a pretty effective method of birth control. (My experience was that they were right)

Cindy had reluctantly agreed to the experiment. One thing led to another and soon Cindy was the model of choice as Sandra taught many of her friends how to ‘give head’. Move forward a year of two and Sandra was getting Cindy to try more things including crossdressing. But I’ll leave it at that before this starts to sound too much like a Sandy Thomas novel on forced feminization.

As Cindy told me this I thought that I’d never tolerated incest because usually it involves a brother or father or ‘kind uncle’ dominating a vulnerable girl. Somehow what Cindy and Sandi had together seemed alright to me.

Sandra and Cindy eventually outgrew each other and found more normal relationships. Sandra moved to Vancouver and got involved in the large industry supporting movie productions. The temptation to get involved with visiting Hollywood types was too great and too tough on her own relationship. She found herself happily single. She also stayed in touch with Cindy and knew of the emerging beauty that was her brother turning sister. In return Cindy had chosen her fem name to be as close as she could to what she called Sandra — Sandi.

From time to time Sandra even encouraged Cindy to seek out a male friend and to put in to practice some of those lessons she helped teach some years ago. To date Cindy had resisted the advice.

So it came to pass that Sandra got an assignment that would take her to Hawaii for a month. One of her first calls was to Cindy, “Hey girl, I’m going to Hawaii. How would you like to come out here to take care of my place, feed my cats and live the life you want to lead?”

“I’ll be there tomorrow,” said Cindy.

“It’s okay. Give yourself some time to get ready and come out when you are ready. I’ll pick you up at the airport.”

A week later the siblings were greeting each other as a cool Vancouver rain shrouded the mountains. “We’re going straight home,” said Sandi, “I want to cuddle with my new baby sister.”

The two spent the next few days getting Sandra ready for her trip and Cindy ready for her first solid month en femme. That meant visits to a salon for nail extensions, a wig boutique and some of Sandra’s favourite clothing shops. Cindy also helped Sandra pick out a new bikini to wear in Hawaii. Of course the two girls had to step out to gay clubs on Davie Street and straight clubs on Granville Island.

Then it came time for Sandra to catch the flight to Hawaii. Her parting advice to Cindy was, ‘take care of the cats, have fun, don’t do anything I wouldn’t do and be sure to be home the fourth Saturday of the month.’

“That’s this coming Saturday,” I told Cindy, “what does she mean by that?”

“I don’t know but she’s mentioned it several times and she wants me to be home all Saturday afternoon, to look my prettiest and be ready to Skpe with her about 5 p.m. Vancouver time.”

“You must be curious?” I commented.

“Of course I am. I looked in her day planner by the phone but all it has written is ’Landscaper’ and that appears the second and fourth Saturday of every month, sometimes with a heart after it.”

We left it at that. As our conversation ended, my curiosity got the better of me. “Can I Skype you on Sunday?”

“Make it Saturday evening,” she replied.

That Saturday promptly at midnight local time, 9 p.m. in Vancouver I was on the computer looking for Cindy and she was waiting for me. “Linda, have I got a story for you!”

“Why? What happened? You seem pretty up, even for you.”

“My sister wanted me to be ready and pretty for her Skype call at 5 p.m. I was at my computer as she made contact. I had to adjust the volume because a couple of guys were mowing the lawn and trimming the hedge outside. Their machines were not quiet.”

“Were they the landscapers you mentioned,” I asked.

“Yes they were.”

“Did you find out what the hearts meant? Were they cute? Did your sister have a thing for one of them?” I sensed something was up so I was full of questions.

Cindy continued, “Sandi told me that is why I had to be there Saturday afternoon. I had to pay the landscape guys. I said I hope they take credit cards because I don’t have much cash. No problem, she said, it doesn’t work that way.” Cindy said that Sandi asked her to remember how their parents used to trade some of their vegetables and eggs for services in town. They called it the barter system. She had the same arrangement with the landscapers.

“I asked what she meant.”

Sandi then had said, “they cut the grass and hedges and blow the leaves and I, I mean we, blow them’.”

“No way!” Cindy had exclaimed. She went on to tell me that Sandi said it was all arranged. The ’boys’ made her their last call of the day and she would take care of them off the books. It had been going on for about a year. Sandi had said, ‘I’ve already told them that my friend Cindy would be paying them today. They know that Cindy is a special lady and they are all up for it. Just have beer ready for them and let them have showers. If you are any good it won’t take you long. And remember you had a great teacher. Now is the time to put that learning in to practice.’

“Did you go through with it?” I asked Cindy.

“Well I did and at Sandi’s request I set up the laptop so she could watch.”

Cindy went on to describe with some delight how the young men came to the almost apologetically to ask if Cindy knew of the payment arrangement, how she had invited them in to make themselves comfortable, how they had accepted the beers and asked to take a shower. She also described in some detail how she carried out Sandra’s instructions all the while with her sister looking on through the computer and sending encouragement to her and kisses to the boys. “Did I tell you that Sandi was wearing that new very skimpy bikini we’d bought just before she left for Hawaii?” said Cindy, “ As I went down on each boy I was aware they were watching Sandi do a sexy dance on the computer screen.”

In the end Cindy got the initiation she had long feared. She learned the thrill of arousing another person and even got to experience the results. After the boys had received their payment in full and left the house Cindy and Sandra had talked for a while. Cindy found herself giggling a bit like Sandra’s friends had done many years earlier. In the end the siblings concluded that one act would not define Cindy for the rest of her life. She was still Cindy.

As she concluded her story I said, “hey Cindy I probably shouldn’t say this but remember the old saying that if you build a thousand great bridges they won’t call you John the great bridge builder but suck one …” and I let it drift off. Well it’s not true. You are still the same great person you were this morning.

“I may be,” concluded Cindy, “but I’m still going to contact Raymond tomorrow.”

Tags: crossdressing, featured

Category: Transgender Fun & Entertainment