Sandy Transforms Her Lover

Sandy was tired, she had a good life, her kids were grown and out on their own. She worked only because she wanted to, she was financially secure as her husband had provided her, Bill had been taken from her by a fatal automobile accident.

Sandy was finally over grieving the loss of her husband, she was getting on with her life. She enjoyed working out at the local fitness centre. The classes she was taking there were helping her transition into her new life. She noticed the men checking her out as she went through her exercise routine.

They were mostly middle aged guys with their small beer guts, but she did notice one guy who looked fit,he was about the same height as her, which being a tall woman was not easy to find. This guy seemed different than the others he was shy but had a sexy quality about him.

Sandy decided she wanted to meet this mysterious gentleman. So she accidentally bumped into him while going to her next machine, his face flushed slightly as he thought he had bumped into her, she smiled sweetly and introduced herself.

His name was Jack, and he was a senior partner of a successful investment firm. Jack was single as well, having been divorced for a few years he too was looking to get on with his life. Sandy chatted with him for a while and then went on her way.

She couldn't stop thinking of him when she got home. He was in her thoughts constantly. So the next time they were at the fitness centre together, again they ended up chatting together. Sandy liked his calm demeanour and his charming ways. He was so down to earth, Jack was so easy to talk too.

They started meeting for drinks outside of workouts and soon Jack asked her if she would like to go out. Sandy accepted and was thrilled to have a reason to go shopping for that prefect first date dress. She went to her favourite boutique, and was trying on a few dresses, she couldn't make up her mind on a nicely cut black dress or a much more risqué low cut purple dress.

She finally bought the black dress as she would feel better in it. She then purchased a new black bra and panties, next was time to pick out her hosiery she chose a garter belt and black seamed stockings. Sandy decided she also needed a pair of new heels to go with her outfit. She found a pair with a nice 3" heel they had nice steel tips on the heels.

Sandy was thinking about the relationship she had with her late husband, and she wasn't all that satisfied with it. She wanted things to be different with Jack, so she went online to check things out, as she was searching different sites she came across some she-male sites.

This really turned her on a chick with a big dick, looking so feminine but having a cock. She was getting wet just looking at the photos. Right then she decided one way or the other Jack would be her playmate.

Sandy met Jack for their first date and they had a wonderful time and hit it off very well. They ended up back at Jack's penthouse condo, and he treated her to a very nice wine and some jazz music. Sandy was so happy to be with him things were going so well. They ended up kissing and making out, next thing she knew they were in his bedroom, he seduced her like she had never been before he was so seductive and thoughtful. They had very good sex but she was left dreaming about how Jack would look in a dress.

Things were turning out so very well, Sandy was very happy with Jack but she still had this desire to turn him into her sweet she-male. Sandy decided to try turning him gradually and she devised a plan to make him her perfect she-male.

Her first course of action was too get him used to going for pedicures with her, she told him lots of men did it which was true. Sandy told him she liked longer hair on a guy and had him start to grow his longer.

She was careful to keep it all innocent and then in the bedroom she started her next plan, when they would make out she would wear sexy lingerie and make sure to rub up against his body, she would always wear a garter belt and stockings and run her sexy clad legs against his. She would then take her panties off and stroke his cock with them until he came. She wanted him to get used to the feeling of the soft material around his cock.

She made sure too keep up her plan,soon if she didn't use her panties while jerking him off he couldn't come.

Sandy then moved on to her next step she had Jack over one night and they were in bed she grabbed his cock and started giving him a hand job, he was excited but just couldn't seem to cum, so she said I have a ideas here put my panties on, well he did and almost immediately came. His orgasm was like nothing he had experienced before it was so amazing he said.

She made a big deal about it telling him how hot he looked in her panties and how much it turned her on. She made him wear them the rest of the night. Things were progressing well soon she had him wearing her panties all the time,telling him only she would know and it turned her on. He liked the way they felt so no harm done. Sandy next moved her plan forward by getting him a few nighties that were very sexy, she got him to wear them by withholding sex for a few days and wearing one herself.

Soon when they were in bed Sandy became the aggressor, calling him sweetie and darling anything too make him more feminine. She next added stockings to his list of things he needed to wear to bed. She bought him some garter belts in different colours and some very nice stockings. Jack didn't seem to care too much as he was having great sex every time he dressed up for her. He didn't see what she was doing or he just liked it.

When Sandy added the stockings to his wardrobe she made him start shaving his body hair she told him no one wears stockings with hairy legs, she also took to painting his toenails. Soon she was cleaning his closets out and replacing all his male underwear with female underwear. Next his sock drawers went from socks to stockings and pantyhose.

At each step she let him get used to wearing these items and complimented him all the time. Sandy next introduced him too a skirt and a blouse just for playing in the bedroom. She also bought him a couple pairs of high heels to wear around the house. She made sure to make a big fuss whenever he wore them telling him how great he looked.

Sandy started Jack on a diet to help him get better curves, she secretly started giving him her birth control pills to help change his body more to her liking. She even got her doctor to give her hormones which she gave to Jack without his knowledge. She started taking him to her salon and had her beautician start cutting his hair in more feminine ways he was really starting to look like a woman, she also had his ears pierced so she could have him wear earrings.

After a couple months she started noticing the changes in him his skin was getting soft he started to develop breasts, he was moody but that was to be expected, she started buying him dresses and skirts and blouses.

It was easy to get him to wear them around the condo as she complimented him on how pretty he was, she started teaching him how to do his makeup. Taking the time to show him how to properly apply and use each product. Sandy was very patient with Jack letting him get used to each little step along this journey of his transformation into the she- male she so desperately wanted. It really only took time and soon Jack was craving the changes just as much as Sandy, he was loving all the new sensations and sense of camaraderie with Sandy.

She also got rid of any male casual clothes he had and replaced them with beautiful blouses and skirts, no pants allowed she had him in heels and hose all the time. The only time he was dressing like a guy was when he went to work and even then all his underwear was women's. She started calling him Jackie to get him used to being feminine.

Sandy started him with small short trips out to get him used to being seen wearing dresses and skirts when they went out. She took him out to restaurants and would order for both of them. She made it both exciting and easy for him to enjoy his newfound femininity. She always praised him for looking good and treated him like a princess whenever they would go out.

One day when they were making love she started playing with his breasts and telling him how much she loved them, he was moaning and getting so aroused she asked him about what he thought of getting bigger ones, he was so turned on by her foreplay he told her he wanted bigger breasts. Sandy wasted no time in scheduling him into see a surgeon for breast implants, she had him wear a beautiful blue blouse and knee length black skirt for his appointment she also styled his long hair into a very feminine look.

The next day they went and had his implants done now he had nice D sized breasts. He needed two weeks recovery so she had a nice vacation getaway where they could just relax. When his breasts were healed and before he was supposed to go back to work he was nervous because now everyone would be able too see the changes that he had. Sandy set up a meeting with his work and told them he was transitioning and everyone was to support him. She took care of all the paperwork needed and she finished tossing out his male clothes. Now Jackie only has skirts and dresses to wear everyday. Sandy finally has her perfect she-male.

Jackie loves wearing sexy clothes and all the different styles and colours available to her now. She was never a great looking guy but she makes a beautiful woman and she has a great partner with Sandy who loves her so much. When Sandy asked her to marry her she was so ecstatic, they both went shopping together for bridal gowns and found matching dresses. They now have the best of both worlds as Sandy has her she-male lover and Jackie loves being her woman.