Timesharing
A Short Story from an Idea by Erin
By Maryanne Peters

“How good is this?” He had only just closed to door behind and cast around his first glance when he had to say the words out loud. It was as if Cherise was standing beside him, wearing something summery, and they were sharing this view. But she was not there. She was in the suitcase – and he could not wait to get her out.

But the apartment was perfect. High enough to be private, low enough to smell the sea and the tropical garden and the view over the ocean and the décor were just as good as the pictures promised – maybe better. There had been so many promotions sent through to his email account, but this one had come into his “SometimesCherise” address. But he applied in his own name as he had to, and the booking was confirmed, and at a very reasonable rate.

It was that time of year. The coming of the fall up north would mean long sleeved shirts buttoned up so that he could do his annual wax and shave down and not have to explain his hairlessness. That meant that he could be a better Cherise at home and have the opportunity to take a holiday like this. To be here and walk among the populace as her.

The destination had to be far enough away so that nobody would know him or care, and somewhere that tolerated crossdressers if he was found out. This was that place. It would be warm. He could wear sundresses and sandals, and the breeze would swirl light skirts around his bare waxed legs and waft up to his lace panties and to the secret they contained, tightly tucked away.

He found the bedroom and lifted his suitcase onto the bed. There was a wardrobe and a chest. He could hang up his dresses and lay out his intimates in the drawer, and make it her home. The only male clothes were what he stood up in. Right now they seemed as if they were on fire – he could barely wait to pull them off fast enough.

He wore panties underneath and for some reason, taped crosses on his nipples, as if marking the spot for the breast forms he could now affix there. But first he needed to get out his dresses and check them for creases, and have an iron ready just in case.

But when he opened the closet, he was surprised to find that there was a garment already hanging there. It was an evening gown, in emerald-green satin crepe, long but slashed to the thigh. Perhaps a little greedily his first thought was how good it would go with his red wig. But it was not his to wear, or Cherise either.

He noticed that there was a note pinned to it. “You must wear this to the ball on Saturday, with the shoes in the box.” Immediately he looked for the box. He found it on the other side. Bronze strap sandals with a 3 inch heel, and amazingly, in Cherise’s rather generous size.

How could anybody leave such beautiful things behind? Had she missed the ball? How sad. He decided to leave the dress hanging. Perhaps somebody would come to collect it. There was unpacking to be done. But he was careful to roll Cherise’s garments. Just a little ironing would put things right.

Next came the wig and stand, and the breast forms. They were new and came with instructions and two types of adhesive – 7 hour fixing or 7 day or “high activity” application which was also waterproof and required a solvent to remove. His chest had been waxed for this – in fact his whole body had been. This was intended to be a glorious two weeks of Cherise.

The trick is to get perfectly aligned. It took some effort. And the loose edges must be smooth so that a little foundation can hide them. Cherise had a one-piece suit for swimming with them, but two bikinis for sunbathing, one with a small skirt to hide an incongruous lump but the other – well that would be another challenge. But at least it was black.

But for an afternoon stroll all that was needed was a good supporting bra and a tight gaff under the panties, and the right dress and shoes. And then on with that red wig and the right makeup – something to take advantage of those lips that an ex-girlfriend had once called: “so wasted on a man”.

It felt good to step out in the sunshine. It was not the first time. There had been night walks at home, and a couple of short walks around the block just to be able to wear day clothes and more understated make up. But they had always been in fear. This was so much better. There was a freedom that was evident in the walk.

There was a coffee to stop at, and whisper for a soy latte, and sit on the street with long shaven legs crossed as a tight gaff could allow, and just pass the time. This was what was needed.

When he got back to the timeshare he felt exhilarated. He would do it again tomorrow. Walk further. Down to the boardwalk. Perhaps stroll on the beach, or head to the marina. Stop for lunch – just a salad as a girl needs to watch her weight. It was good.

But fatigue caught up. The best thing to do was to slip on a robe and order a pizza. There were chick flicks to watch. No sport. He was a girl for two weeks, and girls don’t care about sports. That made him smile.

He kept that wig and the makeup on. He wanted to tip the pizza delivery guy and here him say those magic words: “Thank you Lady.” He had bought a bottle of wine with him and it was chilling. He had a glass, then another and then found that the bottle was empty. Oh well.

It was late. He was just about to retire when he heard a key in the lock. Somebody was at the door and trying to get in! He jumped to his feet.

A man stood in the doorway – tall and good looking. He had a large sports bag slung over his shoulder.

“What are you doing here?” he said, more in surprise than annoyance.

He was about to blurt something out, but he stopped and composed himself, running through the higher scales in his head, so he could be her: “I am staying here. For two weeks. I have the confirmation somewhere. I will find it.”

“Well that is strange, because I am staying here too,” he said, but his look of concern broke into a smile. “Look I am sorry, my name is Milton Staines.” He thrust out a hand.

“Cherise,” she said. She did not add a surname. Until she understood who he was it would be just Cherise. She placed a hand in his, uncertain as to what a woman’s handshake really was, although there had been many received, none had been given before. His was firmer than expected, so she reciprocated.

“Do you mind if I leave my bag here, just until we sought this out?” he asked politely. What could Cherise do?

“Sure. I have the confirmation email on my phone,” she said.

He put down his bag against the wall and reached for his phone. He said: “So do I.”

They were both looking at the screens that each of them had thrust in front of the other. They were identical in every respect, except the addressee. They stood beside one another to confirm.

“What a mess!” she said. “I will make a call.” Which is what she did. There was no answer. Just a voice message from some mechanical sounding voice, suggesting that a call should be made during business hours. Those hours were long past.

“We both have keys so I guess we are both staying,” he said.

“There is only one bedroom and one bed,” she said. “And I have already settled in. You can sleep in her. I think that the couch folds out.”

“It does,” he said. “I have stayed here before. That makes this doubly infuriating.” He was looking around to see how well established she was when he saw the empty wine bottle. “I see you have had a drink already but would you like to share a drink with me? I brought a bottle of Armagnac with me, just for emergencies like this one.”

“I am not sure that I have ever had Armagnac before,” she said.

“Then find a couple of glasses and I will introduce to one of the finest things in life,” he said.

So she did. It was a small bottle like a half-size wine bottle. It tasted like brandy, but with a bouquet of fresh flowers in your face while you drink it.

They had raised a toast to “happy accidents”. It was his idea.

As he unfolded the bed from the sofa she said: “Don’t get any ideas that you are moving in. Once we make contract with the agency or the owner they will have to find you some alternative place to stay.”

“I have to agree, although I am used to this place and I do love it here,” he said. “You were first in possession so I am here at your invitation, and I thank you for that.” And in evident gratitude he poured out another glass of the wonderful liquor, and she drank that too – slowly because she could feel the effects and needed to take care.

But she was well past that point by the time that glass was empty.

“What the fuck!” Even before she opened her eyes she could feel his hairy arm across her, and she pushed it away. But the light was blinding, as if a torturer was shing a light directly in her eyes to disorient her.

But the light was the sun, and it was streaming in the bedroom window.

“I am sorry,” he said. She turned her head, and his face was right there, so close that she could feel his breath. They were lying in the bed. He looked concerned. He said: “Things got out of hand last night, but I can assure that I did not take advantage of you.”

She looked at the ceiling to collect her thoughts. Before she did anything she needed to remember what had happened. What had she told him about herself?

The she realized that she was wearing a nightie. When they had been drinking she was fully clothed, and now she was basically naked. The breasts were there. She had been looking forward to seeing herself in the mirror wearing just that nightie over the breasts. But she had seen that! Last night, she had paraded in front of the mirror and she looked great. He said so. He had been sitting on the bed watching her, naked and with an erection.

“What did we do?” she croaked, still looking up.

“We just slept together,” he said. “You said that it was as much my bed as yours and the sofa bed is not folding out right in any case. We just slept. You wanted to cuddle and so did I. So we did.”

She reached up to her head. There was no wig, but she had not removed her makeup.

“I must look awful,” she said. It was Cherise’s voice, even if the first words of that day had not been.

“I like your natural hair,” he said. “Although it could do with some styling. If you are still interested in lunch then perhaps I could arrange for you to go to the salon downstairs first?”

Lunch? She turned to his face. It was smiling. His eyes seemed far too inviting – almost sinful. His lips too – sensual for a man, and soft. She knew that because she had kissed them – last night.

A man! She had kissed a man! What else? For some reason her hand went down to her crotch in a flash.

She was naked under the nightie. Her penis lay there, like a slug on a rock, seemingly smaller than ever. But it was hardly hidden.

“I barely noticed it,” he said. “I hope you are not offended by me saying so.”

She was not offended. In fact, she was rather pleased. Perhaps she should not have been but she was. She found herself smiling. A strange man had entered her rented apartment; had mistaken her for being a woman; had gone to bed with her and treated her as a woman; had seen that she wore a wig and fake tits, and that she had a penis, and was still offering to take her to lunch.

Regardless of any sexual orientation issues, that was worth a smile.

But on the issue of orientation there was that kiss to consider. She remembered it now, with a clarity denied of other events of the evening.

“I hope that I was not too forward, last night,” said Cherise, in one of her Cherisiest smiling whispers.

“If apologies for that are due, then they should come from me,” he said. “But I don’t think they are. It was a wonderful evening and a wonderful night. Let’s forget apologies and talk about today. My offer stands. A makeover downstairs and then lunch at the Marina. What do you say?”

There may have been a moment of doubt. There may have been just an inkling that this was out of control – that Cherise was just an occasional dalliance into a personality that was not real. But it was just a moment. It seemed too tempting – too wonderful.

She just smiled, and he knew it was a yes.

He said that he had some business to attend to, so she took some tie to compose herself. Not just coffee but electrolytes, and a shower that was deliberately cold to have her metabolism clear her body of any residual alcohol. When she put on her sundress she felt invigorated and ready for adventure. He head was clear and focussed on seeing just how far Cherise would go.

“Mr Staines has already been in touch,” said the lady at the salon counter. “He has paid for a complete package. It is up to you but I would recommend that you just lie back and let us deliver.”

The complete package sounded interesting, and Cherise was of a mind to lie back. This was her first trip to a salon.

“You should not be wearing so much makeup on a summer’s day like this,” said one of the attendants. Concealer like this will not be necessary after our follicle treatment on your face. May we proceed with that? Cherise just waved her approval. She was lying back.

“You have enough hair for us to add extensions,” said another. “I understand that you prefer to be a redhead? Shall we go in that direction?’ She was lying back and receiving the complete package.

Eyebrows were shaped too. And a manicure. And a pedicure. She was lying back.

“All done,” the lady said. “I am sure that Mr Staines will be pleased, but what about you. Are you happy with it?"

Cherise looked in the mirror and could not quite believe what she was looking at. A young flame-haired girl looked back at her. Her face was totally smooth and appeared soft and pale. Her eyes and lips were delicately made up, her eyebrows now in a shape that would be hard to hide. Her heart fluttered. She felt a little faint. These were feelings that she loved. She loved being Cherise. How could she possibly consider being anybody else?

“I love it,” she said. “Thank you so much. I feel … complete at last.”

The lady in charge took her hand and said:
“My dear girl. We have done as much as we possibly can to the outside. Now it is just the inside that needs to adapt. And that is up to you.”

Cheris barely heard it but was to remember those words later. For now she basked in the joy beauty can bring.

Milton was waiting for her. She was ready to make an impact. There was a mirror near the entrance as there always should be. She was happy that she could not look better. The dress and the heels looked great too.

He saw her almost immediately. She drew him out of his chair as she approached. She had wanted to hold a supermodel pout all the way to his table, but she could not help but break into a smile as he did. They were both thinking the same thing.

“Cherise,” he said. On his lips is sounded almost indecent – a name describing a sexual act. Cherise.

He kissed her on both cheeks drinking in the perfume that the salon lady had offered at the last minute. “Mysterieuse”. Cherise had been told that it would drive a man crazy. He lingered over her as he pushed in her chair.

“You are so beautiful,” he said. “You are like a dream.”

“I feel like one,” she said. “I must be in one.”

“Mine,” he said.

The truth is that he could barely take his eyes off her for that hour. And in his face she saw his desire and wanted him. They talked and laughed, but it was just killing time. They both knew what had to follow. He could not pay the bill fast enough for either of them.

He had an Italian sports car brought around. She was not surprised. But if it had been a two person skateboard, she would not have cared. It just needed to get them back to the timeshare apartment as fast as possible.

They seemed to have avoided physical contact through lunch, but the moment that the door closed they were upon one another like wild animals. His hand was in her long red hair, his tongue deep inside her mouth. He was Milton and she was Cherise – a man and a woman.

“I have bought so lubrication,” he said. “I hope you don’t think it presumptuous of me, but I am not sure whether you have done this before.”

“You will be my first,” she said. “But I want you inside me. I really do. I have cleaned myself thoroughly. I hope you don’t think it presumptuous of me.”

But nothing could seem more natural. He put a pillow under her butt so that he could make love to her as she should. He had lubrication and thrust a couple of fingers insider her first, to relax her and to insert the first hormone releasing suppository as well, although she did not feel that. Then he entered her slowly with his huge cock, whispering to her, and making sure that she was in no pain.

But she was in ecstasy, even before he started to pump her.

The shared orgasm was exquisite.

He collapsed on the bed and she snuggled up beside him.

“I hope that you have not found another timeshare apartment,” she said. “I was hoping that we might share this one. So I can forgive the owner for his mistake.”

“He pushed aside a lock of her pretty hair. He said: “I have a confession to make. I am the owner.”

He leaned up, to look him in his face. Should she be angry with him for deceiving her. Could she be angry with him? She did not sound as if she was when she asked: “You set this whole thing up?”

I have seen somethings written by ‘Sometimes Cherise’. You always covered your face, but I knew that you would be beautiful … just not as beautiful. But it was your feminine soul that first attracted me. I think that I fell in love with you even before I ever met you, but when you opened the door as Cherise, I knew that I did. Promise me that you will never go back to whoever you were. Stay with me, here.”

“Here in this apartment?” Her dream home.

“Well actually I own just about the whole building, so you have your choice. It was all time sharing but I have been buying it back. The only time sharing I am interested in is with you.”

The End

© Maryanne Peters 2021

Author's Notes
This is a story from my latest collection of short stories on Amazon (plus other platforms).
The link is: https://books2read.com/u/mgpMnq
This time my theme for these 21 stories is the mind, deranged or manipulated, or other afflicted.
The publisher is Doppler, so BCTS benefits from any purchase.
Also, this particular story comes from this seed sent in by Erin’s: "A crossdresser takes a timeshare in a resort town for a two week vacation but it's been double booked so she has to share with a hunky roommate".