A Body Like Hers: Day Five

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She dresses him like a French maid and pegs him.
4.7k words
4.81
11.6k
14

Part 5 of the 10 part series

Updated 03/08/2024
Created 03/01/2024
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Day five (Tuesday):

Jimmy woke in the early hours of the morning and felt hot. He pushed the bed-covers off his chest. He felt his nipples and was happy to find the nipple suckers still attached and under the bra cups. He wondered why he was having these hot flushes during the night until he fell back to sleep.

Jimmy woke to the sound of Serena in the en suite. He got up, wandered into the en suite and sat down to pee. Serena said, "Looking good, Jimmy."

Jimmy looked at his body and saw that he was still wearing the black sports-bra and period panties. He smiled and said, "The nipple suckers are still attached."

"Well done, Jimmy," said Serena. She then asked, "Are you looking forward to going to the gym?"

"No," answered Jimmy.

Serena laughed and said, "Your so funny, Jimmy." Jimmy felt happy that Serena thought that he had a sense of humour.

Serena asked, as she posed like an Amazonian warrior, "Do you still want a body liked mine?"

Jimmy sighed. He knew that he should get fitter so he answered, "Yes please."

"Great," said Serena. "Then we need to go to the gym, Jimmy. Shall we get ready?"

Jimmy sighed again and answered, "I suppose so."

"Come on, Jimmy. Don't you feel better?" asked Serena.

Jimmy thought about how he felt. Although the High Intensity Interval Training was exhausting, he did feel better once he'd recovered. He answered, "I do, a bit."

"Good," said Serena with a smile. "It looks like the HIIT and supplements are starting to work.

"I don't want you to dirty the compression wear with the lip moisturiser on you nipples, so keep your bra on and wear the pink compression wear that you wore yesterday."

"Okay," said Jimmy, "Should I keep wearing the nipple suckers?"

"Why not?" answered Serena. "It won't hurt and it'll make up for the time that they fell off while you were asleep."

Jimmy put the pink compression wear on over his bra and period panties. He looked at his body in the full length mirror. His shoes and socks were the only clothes that he was wearing which were his.

They went to the gym and immediately started on the elliptical stepping-machine. Jimmy remembered to roll his hips and noticed Serena watching him. She smiled. He was glad that she seemed pleased with him. He looked at the reflection of the garden behind him. He hadn't noticed how beautiful it was. It was just greenery, but it blended together in a natural, beautiful way. In fact, he recently noticed that many things seemed more beautiful. He wondered why he hadn't noticed that before?

Jimmy looked back at their reflections. God Serena's body looked beautiful, but did she have a bit of a roll of fat on her belly? He then realised that he was looking at his own reflection. He was confused. The nipple suckers were pushing out his bra which in turn pushed out the compression top to make him look like he had small breasts. He looked so feminine, so much like Serena, except for his midriff. He looked at his belly and was determined to get rid of that spare tyre.

Jimmy watched his reflection. He exaggerated his hip rolling and he looked better. In fact, if he lost that extra fat, he would have a beautiful body. He watched his reflection as he put more effort into rolling his hips and working his muscles.

Jimmy looked at Serena in the mirror. She was grinning at him and said, with a Scottish accent, "Looking good, Jimmy."

Jimmy agreed. He was looking good. He wasn't yet looking great, but we was starting to look good.

Serena pushed them through the HIIT. Jimmy was absolutely exhausted by the end of the session. He'd thrown all he had into the HIIT and he was completely spent.

Jimmy clasped onto one of the elliptical machine's levers to support himself and looked at Serena. Serena was smiling and said, "Well done, Jimmy. I think it's all starting to work for you now." Jimmy only manage to nod, but he did agree with her. He was determined to get a body like hers.

Serena helped Jimmy walk to her home. She sat him down on her bed. She grabbed a hair on Jimmy's compression leggings and pulled it.

"Ow!" said Jimmy.

"They're still ugly, Jimmy," said Serena and she tugged at another hair.

"Alright," said Jimmy, as he rubbed his leg where Serena had pulled out another hair.

Serena smiled and said, "Shall I pull them out one by one or use the epilator?"

"EPILATOR," yelled Jimmy as another hair was ripped from his leg.

"Good," said Serena. "Off with your clothes."

Jimmy peeled off his compression wear while Serena prepared the epilator. She started zapping his body from the tips of his toes right up to his groin. Serena said, "We'd better do the rest."

Jimmy didn't think that was necessary. None of his hairs that were previously epilated showed any signs of growing back, but he didn't want to displease Serena. He took off his bra and panties and let Serena zap his whole body.

Jimmy felt relaxed. It kind-of felt nice to have Serena paying so much attention to his body. The epilator did sting a bit, but it also felt stimulating. He was a bit worried when Serena zapped his eyelids or eyebrows. They didn't need epilating, did they? He laid there until Serena had finished and she said, "Shower."

Jimmy slowly stood up and forced himself to walk to the shower. Serena slapped his buttock and Jimmy jumped. Serena laughed and said, "You've got a nice bum, Jimmy. Many women would be jealous of that bum."

Jimmy was still fatigued after his shower. He dried himself and flopped down onto the bed. Serena pushed him over, pinched his buttock and gave him his injection of supplements. She then held each of his testes and injected more supplements into those.

Jimmy didn't notice the injection into his buttock, but he did notice the injections into his balls. It kind-of hurt but it also felt nice. He imagined the supplements attacking his testosterone and allowing his body to loose all that extra fat.

Serena playfully slapped his buttock that she didn't inject and said, "Douche, Jimmy."

Jimmy forced himself up and douched. He cleaned up, lubricated his rectum and put on the black period panties. He returned to the bedroom and put on the pink, sheer dressing gown and slip-ons.

Serena pointed to the seat in front of her dressing table. She asked, "Do you want to cover up your clown face?"

Jimmy looked at his face in the mirror. Although the redness was going away, it was still noticeable, so he answered, "Yes please."

Serena smiled and said, "Okay, do it. Let's see how much better you are at putting on makeup today."

Jimmy remembered what Serena had taught him and applied the makeup. He looked at his face when he'd finished. It wasn't too bad. In fact, he was quite proud of what he'd done. He looked at Serena who smiled and said, "Getting better, Jimmy. Let me just fix a little bit here and there."

Jimmy watched Serena touch up the makeup in a few spots on his face. He realised what he'd done wrong and was determined to get it right the next day.

Serena said, "You'll get faster at putting on makeup with more practise."

Jimmy prepared breakfast and sat down to eat. Serena held out her finger. Jimmy looked at the blue pill and sucked it off her finger. He continued to seductively suckle her finger and she smiled. Jimmy knew what they were going to do after breakfast.

"Get up lazy bones," said Serena, straight after breakfast. "There are things to do. Today is washing day and we've got a lot of washing to do."

Jimmy rose and put on the French maid apron. He followed Serena into the en suite. She pointed to a laundry basket and said, "Bring that please."

Jimmy carried the basket of dirty clothes into the laundry. Serena showed Jimmy the different settings on the washing machine. She showed him how to separate the items into different colours and types, making sure to read the washing labels. Some delicates, such as, undies, brassieres, negligees and compression wear, went into laundry bags to protect them from damage during the wash.

It wasn't hard, in fact, it was fairly easy and Jimmy enjoyed the work. The material was mostly easy to identify without reading the labels but Jimmy still read them. Under Serena's supervision he washed the different loads and hung them out on the washing line.

In-between loads Jimmy prepared lunch and they sat together to eat. Jimmy rinsed and placed the dirty dishes in the dishwasher. He noticed Serena watching him as he did his chores.

When he'd hung out the last load of washing, Serena stroked his French maid apron and said, "This has served you well, Jimmy, but I think that you need an upgrade. I saw something when I was shopping and I thought of you." She walked into her bedroom and Jimmy followed. "I bought you these."

Serena pulled some pink compression wear out of a shopping bag and handed them to Jimmy. Jimmy was ecstatic. He now had three pairs of compression wear that he could wash and rotate during the week: the black pair with pink seams, the old pink pair and now a brand new brighter pink pair.

Jimmy looked at Serena, for some reason he had tears welling in his eyes. He asked, "Are you sure? ...You didn't have to buy these for me... They must have been expensive..."

Serena said, "Shush... The cost doesn't matter, Jimmy. I've bought them for you so that you can wear them. Okay?"

"Thank you, Serena," said Jimmy. "You're so kind." He held the compression wear up against his body to see what they looked like in the mirror.

Tears started to flow from Jimmy's eyes. He wiped away the tears but they kept coming. Jimmy wondered why he was crying? He was happy with Serena's gift but for some reason he was very emotional.

Serena hugged Jimmy and Jimmy started sobbing. Jimmy cried on Serena's shoulder. Serena said, "It's all right, Jimmy."

Jimmy pushed Serena away to look into her eyes. He said, "I don't know why I'm crying. I'm happy but I'm crying?"

"It's alright," comforted Serena.

Jimmy nodded, smiled and slowly stopped crying.

Serena put another shopping bag on the bed and said, "I also bought you this." She pulled out some clothes that were mostly black but with some white lace. Jimmy didn't know what they were until Serena held up the top and bottom against his body.

Jimmy laughed and said, "A French maid outfit."

"Yes," said Serena. "I saw it and thought, 'That'll look better on Jimmy than the French maid apron.'"

Jimmy laughed and took the outfit, held it up against his body and looked at himself in the mirror. He said, "It does look better than the apron."

Serena laughed with Jimmy and said, "Try it on."

Jimmy unzipped the skirt and put it on with Serena's help. He said, "What's this petticoat made out of?"

"It's crinoline," answered Serena. "It holds out the skirt."

"It certainly does. It almost exposes my buttocks," said Jimmy. "The waist band is very clever. It has elastic to expand and contract but you can't noticed it."

"That's right, Jimmy," said Serena. "It'll still fit you when you lose that extra weight and your body changes.

"Put your nipple suckers and your bra on before the blouse."

Jimmy did as requested. The blouse had white lace around the neck and armholes. Serena adjusted the blouse so that it wasn't tight but didn't overhang the skirt waistband too much.

"Take off your panties and put these on," said Serena as she held up a black, lace, suspender belt and a pair of black bloomers.

Jimmy took off his panties and lifted the skirt but couldn't put on the suspender belt. He said, "I should have put the suspenders on first."

"Yes," said Serena with a smile.

Jimmy dropped the skirt to the floor and wrapped the suspender belt around his waist. Serena hooked it up and said, "Next time you can hook it up at the front and then turn it around."

Jimmy nodded and pulled on the bloomers. They didn't feel secure like the period panties but the material felt sensual. They had frilly white lace at the leg openings. They also protected his penis from being scratched by the crinoline petticoat. He wasn't likely to get an erection and spoil the look unless he had taken a Viagra beforehand.

"And now these," said Serena as she handed Jimmy a package.

Jimmy opened the package to find fishnet stockings. He looked at Serena and laughed, saying, "You've gone all out, haven't you?"

"Yes," answered Serena. "I want you to look your best."

Jimmy laughed, and under Serena's guidance, rolled the stockings up his legs and attached them to the suspender belt. She said, "The straps go under the bloomers so that one can pull down her undies to go to the toilet or do other more exciting things."

Jimmy laughed. He stepped into the skirt, lifted and secured it in place. He adjusted the blouse just as Serena had.

Serena passed something made of white to Jimmy and said, "Now this."

Jimmy unfolded it and realised it was an apron made of satin and edged with white lace. He wrapped it around his waist and tied it with a bow at the back.

Serena placed a plastic tiara on his head. It looked like a head band with a plastic tiara attached, something meant for a child, but Jimmy didn't care. It was all part of the outfit and the head band did keep his long hair in place. He slipped on his pink slip-ons.

"Let's have a look at you," said Serena, as she guided Jimmy in front of the full length mirror.

Jimmy laughed. The outfit was perfect for a fancy dress party.

Serena said, "Oh my god."

"What?" asked Jimmy, still looking at the outfit as he turned from side to side.

"You... You look... beautiful," said Serena.

Jimmy paused to look at himself. He was shocked. It was true. He did look beautiful... He almost, didn't recognise himself. The outfit, makeup and long hair, held back by the tiara, did make him look beautiful.

Serena said, "Except for the slippers."

Jimmy looked at his pink slip-ons. They were too casual for the outfit and they were the wrong colour.

Serena said, "Let me make a phone call."

Jimmy continued to look at his reflection as he slowly turned from side to side. He was a bit stunned at how pretty he looked. Serena returned and said, "We'll sort out the shoes tomorrow, but for now, my sexy French maid, I think I'll have to take advantage of you."

"Oh my," said Jimmy with a falsetto voice, "What is a girl to do?" They both laughed.

Serena said, "Your going to wait here while I get changed into something more appropriate."

Serena called out, "Close your eyes, Jimmy."

Jimmy closed his eyes and Serena put a sleeping mask over his eyes. She pushed him backwards and he fell onto the bed. He felt his petticoat flick up his skirt as he landed, exposing his bloomers. He felt Serena climb onto the bed and knew he was going to have sex.

Serena said, "Roll over." Apparently Jimmy wasn't rolling over quickly enough because Serena flicked him over. She was so strong.

Jimmy was hoping that he'd be as strong as her with all this exercise, when Serena said, "Knees up." She lifted Jimmy's hips so Jimmy supported himself on his hands and knees.

Serena tugged at the waistband of Jimmy's new bloomers and pulled them down Jimmy's thighs. Jimmy felt something press against his anus. At first he thought it was Serena's finger but he realised that it was too thick. He asked, "What's that?"

"This is a Realdoe More, Jimmy," answered Serena. "A strapless, strap-on dildo and I'm going to treat my beautiful French maid to a REAL good pegging. But the best thing is, Jimmy, that the pony end of the Realdoe is up inside my vagina and I'm going to fuck myself as I fuck you."

Jimmy was a bit worried but also excited. Serena sounded a bit animalistic. He was hoping that the Realdoe would feel as good as the dildo, that Serena used on him the previous day. He wasn't disappointed.

Serena slowly pushed the tip of the Realdoe at Jimmy's anus. There was slight resistance but it slipped in when Jimmy relaxed his sphincter. He felt the shaft slowly enter his rectum, dilating it as it went. It felt so good. He was now glad that Serena had been stretching his sphincter because the Realdoe felt much bigger than Serena's fingers or the other dildo.

Jimmy sighed as the shaft kept stretching his rectum, wider than it's ever been. Deeper and deeper went the shaft, deeper than anything before it. He sighed as the dildo stretched wide his rectum as it went deeper and deeper. Jimmy felt Serena's thighs press against his. He was a bit relieved that the penetration had stopped. He was worried that the shaft would go too deep, if that was possible.

Serena held still with her hands grasping his hips and her thighs pressed against his. She slowly pulled back and Jimmy groaned. He felt empty where the shaft had once been. He buried his head into the pillow to stifle his groans.

Serena kept pulling the shaft out of Jimmy's bum until it was almost out. She then pushed all the in with one smooth motion. Jimmy shrieked into the pillow as his rectum was suddenly distended.

Serena thrust in and out of Jimmy's arse and it felt so good. The shaft rubbed on his prostate and his ring was distended, but the most enjoyable feeling, was the full length of his rectum being dilated to, what he thought was, its limits.

Serena pegged Jimmy hard and fast. Jimmy was in heaven. His arse felt fantastic. He squeaked into his pillow on each thrust. He felt his rectum was completely aroused. His body was stirred up into the most blissful feeling.

Jimmy felt his rectum give in to the pounding that Serena was giving him. His prostate was stimulated beyond belief. He felt pre-ejaculate streaming out of his penis onto his bloomers. His sphincter was no longer resisting. It was open for the invader and was completely relaxed. It was a massive bundle of nerves that were being totally stimulated. He wondered if it would ever contract again.

Jimmy felt heat spreading from his arse to the rest of his body. His thighs were hot. His belly was on fire. Even his nipples were painfully burning. He felt his neck and face burn and then... he came... and came... and came again.

It was relentless. He couldn't control himself. He shrieked on each thrust. His ears were ringing. He passed out in blissful ecstasy...

Jimmy gained consciousness. Serena had stopped thrusting. She was bent over Jimmy and she shuddered. Her breasts rubbed Jimmy's back through the silky material of the blouse. He felt her hard nipples pressing against his back.

Serena slowly pulled out of Jimmy in one slow movement. Jimmy groaned as he felt the shaft slide out of his rectum. His anus twitched as it contracted.

There was a sucking sound as Serena took the dildo out of her vagina. She laid down next to Jimmy. Jimmy let his body fall to the side onto the bed.

Serena asked, "Did you enjoy that?"

"Yes," whispered Jimmy.

"It was great, wasn't it?" asked Serena.

"Yes," sighed Jimmy.

"I think that I like fucking my French maid," said Serena. "Do you like being my French maid?"

"Yes," answered Jimmy.

"Good," said Serena, "What's for dinner?"

"Oh... um..." hesitated Jimmy.

"What about a quick salad?" suggested Serena.

"Okay," answered Jimmy.

Jimmy pulled up his bloomers, eased himself out of bed and prepared a salad for dinner. He felt his juices, that were captured by his bloomers, press against his belly. He felt those juices slowly drying and it somehow felt erotic.

After dinner, Jimmy cleared the table while Serena went to her bedroom. Jimmy stacked the dishwasher and washed the cooking utensils.

Jimmy felt so much better doing the housework in his French maid costume. Any water, that he accidentally splashed onto his apron, would mostly run off, but if anything did soak through the satin material, it wouldn't get past his crinoline petticoat. The material felt so much better than the plastic apron with the French maid print.

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