A Christmas Wish Realized

A Christmas Wish Realized

For too many years Jean Luc had been out of family get-togethers. His very adventurous lifestyle of sailing the world and living from one adventure to the next never left him in town for the holidays. This year through a twist of fate he will be in his hometown for the holidays. The unlikely event of his schedule and the holidays aligning in the same town at the same time hasn't been possible for ten years.

A quick email to let his family know that he will be in town, is expecting makeup gifts for all the holidays they didn't have to shop for him, and his delight in seeing the family. With trinkets from around the world he is always a very generous gift giver who delights in giving. This year he has a short amount of time to get it all together and head for his hometown of Vail, Colorado.

His crew is off for the month, and they too are happy to spend the holidays off the boat and enjoying family for the first time in quite a while. The crew hurriedly gets the list of tasks done to make secure the boat for the month they will be off.

Their well-tanned and toned skin shimmering with sweat, the cleaning and storing of items is a treat to watch for the local boaters in the harbor. The men on the boat are well endowed sailors hardened by the sea air and ready to sow their seed as soon as they get free from the boat. The women, clad in only the barest of bikinis, attract attention from the men on the nearby boats. Word of their arrival is shared over the marine radio. A steady parade of slow-moving fishing boats, sailors, and pleasure craft finds some reason to drive their boat as slow as possible.

Little did the locals know that half of the women -- used to be men. The other half are lesbians. The view, however, is not to be missed. Regardless of their personal lives, the women are stunning, the men are buff, and their sexual identities are yet to be known.

Jean Luc looks over the list made during the passage from Hawaii to San Diego with a short stop in Seattle. By the day's end, just after sunset, the boat is deserted except for Carina and Jean Luc. The two are double-checking everything that the crew was supposed to do for any lacks that will need to be taken care of before they too leave the boat for a month.

Carina is a beautiful woman of Latin heritage. Her family shunned her ten years ago when she came out as a man who would be transitioning to a woman. After 10 years of surgeries, exercise, hormones, and a full commitment to pass without a question, she has the distinction of being the first mate to Jean Luc, not just on the boat but in life. The two have worked sailing together for 15 years and know the boat inside and out. They also know each other like they do the boat -- inside and out. The recent revelation from Jean Luc that he wants to dress en femme to see what it is like to be a woman, has Carina wondering how she missed any of the signs.

Jean Luc is asking for this as his Christmas present. Because of the family history and the desire not to be a further blight on his family this needs to be done before they head back to Vail. Carina is not too sure of how to work this gift but is willing to do whatever Jean Luc wants. He has always fulfilled all her requests without hesitation and now this ask needs to be returned with the same gusto. He has always presented highly, all guy, and treated her as a natural woman. The revelation of his desire is hard for her to understand. Even harder for her to see the future being the same. Jean Luc assures her he only wants a test drive and just to see what it would be like. Tonight is the night to go out for the first time as two women.

After several clumsy attempts to do his own makeup, he asked Carina to help him. Her first inclination was to make him look so hideous he would not want to go further with his test drive. However, his bone structure was not going to play along with that plan. By the time the foundation was fully blended it was clear to Carina, he is pretty. Not pretty in the cover girl way but pretty in the elegant classic Hollywood movie way. She looks at her handywork and takes a step back while pulling out her phone to take a picture.

"Jean Luc, I want you to see my future girlfriend," she said looking over several shots before she showed the best to Jean Luc.

"Oh my god, I can't believe that is me. Thank you so much for helping me with this. Will you send that to me. I want to have a memory of this," he said still looking over every detail of the picture.

"Sweetie, you are breath taking. How could I not see this. You always look so... well... manly," she said.

"I have never felt all manly. There is a part of me that has always felt highly feminine and did the man stuff largely out of expectation. Looking at this picture I see the real me looking back. I have truth bumps all over my arms. Look," he said showing her the bumps and raised hair.

"OK, so you deserve to go all the way tonight and enjoy all the truth you can live. We are going to start over and do the full deal," she said.

"But you just finished the make -up," he said.

"Don't worry honey, we will get you looking even better. We are going to tart you up royally. Let's start with a shower and a shave. I will get you so smooth that you can enjoy the feeling of not having all that nasty fur. I love it on a man but you girl are in need of a shave," she said pulling his hand toward the bathroom.

"Strip," she said.

"Yes, ma'am," he said as he tossed his clothes into a pile in the corner of the bathroom.

"Hop in and do a thorough scrub with this loofa. We need to get the dead skin off and you will love what is coming. The feeling of a smooth leg rubbing new sheets is as close to ecstasy as you can get to without sex," she said.

She took shaving cream and three razors to do the transformation from Chewbacca to a gorgeous woman.

"OK, done with the shescaping, let's move on to the main event. Skin care and your signature scent. Smelling good, as you know from what you have told me about how I smell to you, is part of the allure of being a woman. Close your eyes and I am going to hold several perfumes in front of your nose. Tell me which one you like best," she said as she took the first of several perfumes and wafted them in front of Jean Luc's nose.

"There that one. It's me. No doubt about it", he said.

"I'll have to put a very neutral scented lotion on you. This perfume is called Poison and is very strong so it would clash with a scented lotion.

"You're the boss. I know I haven't said it yet, but I love you so much for doing this with me. I have wanted to do this for years and have always been afraid of losing you as well as having you think I am weird. This means the world to me," he said as he leans in to kiss Carina.

"Careful there girly, I'm straight. At least for now, "she said.

"See that is what I have always worried about. That doing this would change what we have. Do you want to stop before we go any further?" he said with a look of utter shame and pulling a towel over his naked body.

"Don't be silly. This is so hot I can hardly stand it. I have been wet since I picked up the razor. You may be having your moment of being all girly and that is great, but you have awakened something in me that I didn't know was there. My lesbian side. And I like it. Now drop that towel and let's get you into full tart mode and get out of here. I want to show you off as my date," she said turning to get a brush to start his hair style.

For the next half hour Jean Luc was in the beauty salon of his dreams. Naked, smooth soft, slippery wet skin that had never felt this way as an adult, smelling amazing and getting all dolled up by the love of his life. Every nook and cranny of his body was being touched, shaved, checked for smoothness, and then given the final approval of a nearly tickle level of touch to see if any stubble remained. The final test was running a silk scarf all over his body to see if there was a stray spot that needed further attention. Jean Luc was at a heightened level of arousal not just from the touch but the whole process concluding with him being dressed up in public - as a woman -- for the evening.

Carina remembers the feelings of coming out for the first time to loved ones. Her initial outing was to her family, it didn't go well. She was ridiculed and told to leave at once. She wanted to make this so special for Jean Luc if for no other reason than to make up for the disappointment she felt.

"Let's get you dressed and get out of here. I am going to take only a few moments to finish my outfit and touchup my makeup, then we can go," she said running a brush through her hair and a minor touch up on her face.

Oh my god, you look beautiful, and I hate to say it you have no doubt thought about passing, and baby you are more female looking than any guy has the right to do. Crap, I am going to have to find something nicer to wear, can't have you going out with an ugly cow," she said.

The two left the house arm and arm dressed to slay. The smell of their femininity in perfume form lingers in the wave of energy they leave behind them and they sashay across the parking area to climb into their car.

The restaurant was nothing spectacular. Just a chain restaurant filled with after work folks trying to shake off the workday and brace for whatever they were running to or from.

The entrance they make is breath taking. Carina, in a little black dress and Jeana, her name for the night, in a very swishy flowing pleated skirt and loose-fitting white blouse with a Hermes scarf tied loosely around her neck. Lowish heels and legs that would stop traffic. The two were glamourous, in love and showing a glow that only two women have in the company of an equal.

A waiter came to take their orders and made note of the way they looked.

"Don't take this the wrong way, but if I could look as good as you two, I would transition immediately. You are so pretty," he said.

"Thank you darling. And why don't you give it a try and see how it goes," said Carina.

"Oh, what would people think, I have so many people that know me as Jessie, a man. I am sure I would have to move away and never see my family again," he said as he dropped his head to reflect in great disappointment.

"Chin up, life can bring you the most amazing surprises. Just a few days ago I would not have guessed that I could even tell her that I wanted to dress en femme and look at me today," he said.

"Wait, what, you're a man. Oh my god, no way, "said Jessie in amazement.

"See you never know what life will bring. If you want to try things out just go for it, she said.

"I'll keep that in mind. But for now, I get to dress up occasionally, between roommates, work, and family it isn't very often. I wish I could just be me every now and then and enjoy a night out," he said.

"Why don't you join us one evening. I have a feeling this may be a regular thing. We would love the company," said Carina.

"I would love to. Can I give you my number? "he said as he pulled out his phone and handed it to Carina.

Taking the phone and tapping the digits quickly, while sending a text to his phone, Carina smiled and said, Jessie, I look forward to seeing you dressed. We would love to be your safe space,"

"Thank you, I'll be in touch with you soon," he said.

This whole time of the waiter interaction, Carina had been rubbing Jeana's leg and playing with his member. With each volley of conversation, more effort was put into the massage confirming how much Carina wanted to play with Jessie. The conclusion to place just before Jessie turned over the phone. Feigning the need to wipe her hands, Carina took a picture of Jeana having just made a mess on the dark red napkin. She sent it along with the text to Jessie. He didn't immediately look at the text, assuming it was just the number, but returned several minutes later with a new napkin.

"I think you will need this," he said as he handed over a new napkin.

"Thank you," said Carina as she exchanged the new napkin for the very soggy used one.

"I will definitely be in touch with you - both," said Jessie as he left with the souvenir.

"Some people are so naughty," said Jeana noting the couple from across the aisle who were now matching their playfulness by a more open stroking from the young girl and her somewhat senior date.

"I see that. Are you good for another round maybe a little less secret?" said Carina.

"Go for it girl," said Jeana taking his cock out from its prison in the panties.

Carina took to slowly stroking Jeana's cock. Playing particular attention to the visual impact she could make. The phone once again came out and the flashlight feature was turned on to highlight the show. The new napkin was placed to protect the skirt of Jeana and the dress of Carina.

From across the aisle the couple, not to be outdone, took it one step further and bared the pussy of the young girl and he fingered her to a very quick orgasm. His own took a bit longer but was worth the wait. His seed was massive and shot out into the aisle, just missing a patron who was returning from the bathroom.

Carina held off bringing Jeana to his orgasm until he saw the massive explosion from across the aisle. The contest was on. She did all steps necessary to build Jeana into a monumental flow and release. More than just getting to the aisle, the strings made a puddle on the floor.

Jessie came over to the table again. This time to see if any additional service was required. He could smell the two loads and could see the puddle on the carpeted floor. Not missing a beat, he rubbed the stain into the carpet, his cock now at full attention. Offering it up for the two diners to feel, he leaned onto the table.

"I just knew this was going to be a good day, He said as his cock was massaged by both Jeana and Carina. He stood with his bulge just above the height of the table. Feeling he was about to release; Carina quickened the pace and Jeana fell for his balls and began to squeeze the juice right out of him.

"Oh lord," said Jessie as he came in his own panties.

The couple from across the aisle was watching with great interest but were not able to see the whole event. The young girl took matters into her own hands, literally, and pulled another orgasm out of her date and she got off with a bit of a spray herself.

"I will be getting in touch very soon. This has been a dream come true," said Jessie

As he took the bill folder, removing the card, he said," dinner and the show is on me. Thank you, oh,...I almost forgot, Merry Christmas."