Jack's Transformation

by Keeley

  

As much as Jack could see it getting out of hand he was also excited at the prospect of getting dressed up every Thursday although he already knew the knickers would become be more regularly worn.

Trying to keep his cool he replied "In what way will it be in my best interests and apart form the humiliation of me what's in it for you?"

Sally had a glint in her eye as she replied "On your part, I know you enjoyed the show earlier and well a few of the other girls aren't averse to a little bit of girl on girl and they don't mind you watching as long as you're one of the girls. The humiliation isn't in my thoughts, you just turn me on dressed like that. I get to satisfy both sides of my bisexuality in one go."

Trying to appear reluctant Jack answered "As you put it like that I'll say yes".

Sally smiled and mouthed a thank you, Claire was also smiling. "You'll have to go shopping again. You can't wear the same thing every week. Meet me at 5 tomorrow in the lingerie department and I'll sort you out."

The thought of buying more silk or lacey underwear made him feel very aroused and he knew this was going to be something he was going to enjoy.

Last orders were called and it was time to leave. Much to Jack's disappointment Claire got in to a separate taxi to him and Sally although that was soon forgotten as Sally stroked his legs brushing her hand against his lace covered balls.

When they got in to the house he was ready to explode. He slipped out of his dress and started to kiss Sally. She replicated the removal of her dress and they made there way to the bedroom. Leaving his bra on they had the most memorable sex that Jack could remember.

After they'd both climaxed, Sally whispered. I know it was embarrassing but you look like you enjoyed it. Thank you".

The next morning Sally had already left for work when Jack woke up. He was tempted to wear a pair of knickers but decided against it. After all he had his shopping to do later.

As he sat there at work all he could think about was which clothes he was going to choose, specifically the lingerie. The day lagged on until 5 when it was time to meet up with Claire. He didn't want to seem too eager so he deliberately kept her waiting 10 minutes later than the arranged time.

Despite this she greeted him with a smile. As he approached she ushered him into one of the changing rooms. "I've picked out a selection of things. Feel free to look around yourself but I think these should do the trick."

He looked down at the selection and saw a mixture of lingerie, skirts, dresses and tops. This immediately excited him and he thought his arousal would be a bit obvious if he was going round picking his own things so he decided that he'd go with what Claire had selected.

She left him too it but said she'd pop back in a couple of minutes to check he was ok. He had a quick glimpse through and decided to try on a basque. Knowing he'd need help with all the hooks he decided to put the knickers on first. Claire was back in next to no time. "Thought you'd like that. i take it you need a hand". He answered with a yes and she hooked him all up. She turned him around and said "Very nice. Are you enjoying that Amy". Before he could reply she had pulled his knickers down and started to suck his very erect penis. He tried to contain himself but before long he exploded in to her mouth which she swallowed. He didn't know what to say but went for a thank you.

"No problem. I wanted to do that last night and also you can't try on a tight skirt with a big bulge. I'll leave you to it now if that's ok."

He tried on the rest of the items, and decided that Claire had very good taste as he was going to have to buy the lot. As he came out of the cubical he was confronted by Sally who thankfully was smiling. "Don't worry, Claire told me how much she wanted you last night and given how good she is with her tongue I thought it was only fair that you experienced it as I did last night."

"Now lets ho and pay and we'll have a little dressing up session tonight. If you're good then maybe Claire can come too".

As much as Sally enjoyed seeing Jack dressed up as Amy she was annoyed that he was enjoying it a little too much for a punishment. She knew he'd be desperate to show off his new clothes that he'd go straight upstairs when they got back to her place which was why she'd arranged an extra surprise for him.

As they drove back Sally insisted that he tried on his new items for her when they got back - like a little fashion show. Jack could barely contain his excitement. Little did he know what she had in mind for him.

When they got back to the house, Jack dashed straight upstairs. He pulled out the items from the bag ready to select what he would wear first . He was just undressing himself when his message alert came through. "Claire forgot to put in any stockings. There are some in my top left hand drawer." He'd already decided that he was going to wear his new basque so it made sense he wore stockings with it, especially as he loved the feel of them against his legs. Just the thought of putting on his new clothes gave him an erection.

After a bit of a struggle he put on the basque and the matching knickers and went to get the stockings. All he could find was a new box. After opening he found a note - "there's an item in my wardrobe that I want you to try first. It's the black frilly one". He rushed to the wardrobe and saw a French Maid's uniform. This was the only black item he could see so guessed this was the one. As he felt the softness of the material his erection grew harder against his lacy knickers.

He carefully put on the stockings and then got in to the uniform. Wanting to look female, he went and got the wig from the night before and went to the bathroom to apply some make up trying to remember how Claire and Sally did it. Eventually he was ready, and except for the bulge at the front of the dress he felt he looked almost female.

Slowly he walked downstairs and in to the living room expecting to see Sally. Instead he saw all the girls from last night sitting around the dining table.

"Amy, are you ready to serve?"

Although all the girls had seen him the night before they hadn't seen how happy he was to be Amy quite so obviously as when he walked through the door. He was about to turn and go back when he heard the door slam behind him. He turned round and saw Claire. She was dressed in a tight knee length black skirt, white blouse, black gloves, knee high boots and was holding a whip.

"Well, Amy are you ready to serve, or do you need to be coerced?" she asked.

"I'm ready" he tentatively replied. He suddenly felt a burning sensation on his arse as Claire gave him a quick whipping just to ensure he was ready.

He looked up and saw Sally smiling. What did she have planned for Amy tonight he thought to himself.

Sally beckoned him towards the table. Slowly he made his way forward. As soon as he reached the girl nearest to him knocked her mobile off the table. "Pick that up for me".

Fearing the whip he bent over to pick the phone up. As soon as he was bent over his dress was lifted and he received a short spank to his behind. This game was repeated as he made his way around the table until he reached Sally. Sally simply lifted his dress and showed everyone his still full erection bulging through his knickers.

"That isn't very feminine Amy is it? Claire, see if you can whip her into shape". Immediately he felt the whip slash across his lace covered behind. Sally lifted the dress up again and although his erection had gone down a little a quick stroke from Sally brought it back to life. "Looks like he has another fetish. It's unfair that Claire has all the fun. Does anyone else want to whip Amy's behind?"

Over the next 10 minutes he was whipped another 10 times and his behind was burning. What Jack thought was going to be a great night had turned in to a nightmare, a painful one as well. After everyone had had their turn Sally asked him to poor everyone a glass of wine. He was relieved to do something normal. After topping everyone's glass up Sally decided that he'd done enough serving. "Thank you Amy. As you've been such a good little girl maybe you'd like to join us. Go and get changed in to something more suitable."

As he made his way upstairs he was tempted to stay there but as much as he hated being dominated he was afraid of the consequences if he didn't do as he was told. Once in the bedroom, he started to go through the collection of clothes that Claire had selected. After a little deliberation he decided on a long red dress. After zipping it up, he started to feel aroused again. He was about to pleasure himself but thought they'd wonder where he was. Despite his erection still being evident he made his way downstairs and back in to the living room.

Where he expected to see all the girls waiting, instead he saw only Sally and Claire, both stripped down to their bra and knickers fondling and kissing each other. Sally saw him come in and said, "All the girls had to leave and as you've done as you've asked it's now your turn to enjoy yourself."

Sally beckoned Jack towards her and unzipped the dress. As it fell to the ground Claire started to turn her attention towards his very erect penis. The earlier humiliation was long forgotten. He started to kiss Sally who moved her hands around his basque which just turned him on more. Claire took her mouth off his penis and went back to Sally's mouth. He could barely contain himself which Sally knew. Pushing him to the sofa she straddled him and started to gyrate. With her back towards him he moved his hands on to her lace covered breasts. At the same time Claire stood on the sofa with her wet pussy right in front of his face. Immediately the excitement he'd been feeling was released. Sally let out a gentle groan of pleasure. She slowly released herself from his shaft and beckoned Claire on. "You need to feel that". Jack certainly didn't mind and was quite happy to oblige.

After what Jack could only describe as the most memorable sex he'd ever had, claire left him alone with Sally. After kissing each other goodbye Sally said. "how about the fashion show you promised, but leave the lingerie show until last and we'll see if we can have a bit more fun. Oh and thank you for being a good sport tonight. I know it was humiliating but may be we'll keep the cross dressing between us from now on and if you're a good boy I'll occasionally ask Claire to join us".

  

  

  

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