A Body Like Hers: Day Three

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She puts makeup on him and plays with his anus.
5.1k words
4.76
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12

Part 3 of the 10 part series

Updated 03/08/2024
Created 03/01/2024
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Day three (Sunday):

Jimmy was awoken when the toilet flushed, so he got up to wee. Serena was drying her face and Jimmy sat down to wee.

Serena smiled and Jimmy said, "My dick's too hard to stand up to wee."

Serena said, "That's alright Jimmy. You're showing your feminine side.

"Where are the nipple suckers that I gave you to wear?"

"Oh, ah..." said Jimmy. "I think that they're still in the bed. They must have come off while I was sleeping."

Serena seemed annoyed and said, "They're supposed to stay on all night, Jim. That's how they make your nipples bigger and more sensitive."

"Okay," said Jimmy. "I'll try to keep them on tonight."

"Good," said Serena.

"Are you ready to go to the gym?"

Jimmy was hoping that he could avoid the gym, but he knew that Serena was right in getting him fitter. He said, "I suppose so."

Serena laughed and said, "Come on, Jimmy. It's good for you and you need to go to the gym if you still want a body like mine.

"Are you going to wear compression wear today?"

"I don't have any," answered Jimmy.

"I've got some old ones that may fit you," said Serena.

Serena used a dressmakers, measuring tape to measure Jimmy's chest. She used an app to record the measurement. She then measured around his waist. She looked at the measurement and tried not to smile.

Jimmy asked, "A bit big?"

Serena smiled and said, "Don't worry, Jimmy. This will disappear," as she pinched the roll of fat on his belly.

Serena measured his hips and entered the value into her app. She said, "I may as well take all the other measurements that this app is prompting me to enter." She measured and recorded several of Jimmy's attributes.

Serena gave Jimmy a pair of compression leggings and a long-sleeve, compression top.

The seams were highlighted with pink. Jimmy struggled to get them on and then said, "They're a bit tight."

Serena said, as she was putting on black compression wear with red highlighted seams, "They're supposed to be tight, Jimmy. They push the blood from your skin back into your circulatory system for your muscles to use, which helps you recover more quickly."

Serena then looked at Jimmy and burst out laughing. She said, "Well Jimmy, I can tell that you're circumcised."

Jimmy looked at the bulge in his groin and said, "Yeah, it's a bit obvious isn't it."

"I'd say a LOT obvious," laughed Serena. She ran her fingertips along Jimmy's shaft and said, "I can also see the outline of your urethra and this vein over here."

Jimmy pulled away from Serena's teasing and said, "Yeah, maybe I'd better go back to my gym shorts?"

"No, Jimmy," said Serena. "I can help you with that and the compression wear will help you to recover.

"Pull down your leggings."

Jimmy pulled down his leggings to release his penis. Serena grabbed his testicles and rolled them in the palm of her hand. Jimmy said, "I think that's going to make it worse."

"Trust me," said Serena, as she pulled his penis backwards.

Serena then squeezed Jimmy's balls and they popped up into his belly. At the same time, she pulled his penis back against his perineum.

Jimmy buckled forwards and groaned. Serena said, "Pull up your leggings, Jimmy."

Jimmy pulled up his leggings trapping his penis against his perineum and asked, "My balls! What did you do to my balls?"

"They've gone back into their inguinal canals," answered Serena.

"My what?" asked Jimmy.

"You're inguinal canals," answered Serena. "That's where they descended from when you were an infant."

"They'll come back out, won't they?" asked Jimmy.

"Of course," reassured Serena. "You just release your penis and push your testes down and out.

"How does that feel? Does it hurt?" asked Serena.

"No," answered Jimmy. "It feels... nice... It feels... comforting."

Serena smiled and asked, "Does your penis hurt?"

"No," answered Jimmy. "It's quite comfortable."

"Good," said Serena. "We can now go to the gym."

At the gym, Serena said, "We'd better not do rowing today. You might get uncomfortable sitting on your penis. Let's use these," and she stepped onto the elliptical machine.

"I'm not used to doing steps," said Jimmy. "Couldn't we just run?"

"No, Jimmy," answered Serena. "Running doesn't exercise your arms as much. Come on, it'll be a new experience for you."

Jimmy stood on the elliptical and started to step. He held the levers and pulled them as he took each step. Serena said, "Pull AND push, Jimmy. You need to work your biceps and triceps."

Jimmy did as he was told and he had to admit, it helped with his balance on the elliptical.

Serena watched Jimmy's reflection and said, "Jimmy." Jimmy looked at her reflection. "Roll your hips, Jimmy. Like me."

Jimmy watched Serena and tried to imitate how she rolled her hips. Serena said, "That's it, Jimmy. Roll them more."

Jimmy rolled his hips more. He felt like he was exaggerating his hip rolling but he had to admit, it did feel better.

After too short a time, Serena asked, "Are you ready to step as fast as you can, Jimmy?"

"No," answered Jimmy.

Serena laughed and said, "Get ready... set... GO!

"Come on, Jimmy. Faster...

"Rolls your hips, Jimmy... Faster... Rolls your hips!...

"and... wait for it... slow."

Jimmy felt as if he may be able to survive the elliptical HIIT. He was breathing hard but rolling his hips did make the steps easier; he felt that he wasn't lifting his body as much during each step.

Jimmy had almost caught his breath when Serena said, "Get ready to step as fast as you can go... ready... set... GO!

"Come on, Jimmy... faster...

"That's it Jimmy... a bit faster...

"Keep pushing and pulling... roll your hips...

"That's it, Jimmy... You're doing really well... and... slow."

Jimmy was breathing as hard as he could. He didn't seem to get enough air into his lungs, but he couldn't breath any faster. He thought he was going to pass out but just managed to keep stepping.

Serena encouraged Jimmy alternately through more intense stepping and then slow steps. She said, "Okay Jimmy. We can stop now."

Jimmy wrapped himself around one of the levers. He was gasping for breath. He felt Serena gently prise his hands away from the lever and guide him to a bench, set up in the sitting position. She eased him down onto the seat.

Jimmy tensed up and said, "Oh!"

"What? What's wrong?" asked Serena.

"My dick," gasped Jimmy.

"Did you hurt it?" asked Serena.

"No," answered Jimmy. "I'm... sitting on it."

Serena laughed and said, "That's a bit obvious, Jimmy. Does it feel good?"

Jimmy nodded. He was embarrassed that sitting on his tucked penis felt good.

Serena laughed and said, as she tugged his arm, "Come on. It's time to shower, unless you want to sit on your dick all day?" She raised her eyebrows.

Jimmy let Serena manoeuvre him into her home. He laid on the bed while Serena showered.

Serena said, when she returned to the bedroom and saw Jimmy still laying on the bed, "How are you feeling, Jimmy?"

"Exhausted," answered Jimmy.

Serena checked Jimmy's blood pressure, pulse and heart. She said, "Hmm..."

"What's wrong?" asked Jimmy.

"You seem to be less fit than I thought," answered Serena. She asked, "Do you still want a body like mine?"

Jimmy looked at Serena's naked body. He could see her six pack abdominal muscles, her muscled legs and arms, her perfectly curved body and breasts. He felt his penis twitch and stopped looking at her. He looked down at his body. A small roll of fat escaped between the compression top and the leggings. He felt embarrassed of his body. He said, "Yes please."

"Okay," said Serena and returned with a syringe. She said, "Roll over onto your belly, Jimmy."

"What's that?" asked Jimmy.

"The same supplements but stronger," answered Serena.

Jimmy rolled into his belly. He felt Serena pull down his leggings and pinch his left buttock. She said, "You've got a nice bum, Jimmy."

"Thanks," said Jimmy, waiting for the sting of the needle.

Serena released Jimmy's buttock and said, "All done."

"I didn't feel a thing," said Jimmy as he rolled over on the bed.

"I've been doing this for a long time, Jimmy and I'm not a sadist," said Serena.

Jimmy saw Serena frowning.

"What's wrong?" asked Jimmy.

"You're still not recovering as quickly as I thought you should be," answered Serena. "I'm wondering if I should give you another injection."

"More supplements?" asked Jimmy.

"Sort of," answered Serena. "Do you know what your testes produce, Jimmy?"

"Hopefully sperm?" suggested Jimmy.

Serena laughed and said, "I thought that you didn't want children, well, that's what the information from Charlotte led me to believe?"

"No I don't," answered Jimmy. "I've never had an urge to have children. They... they seem like an inconvenience to me."

Serena laughed and said, "I'm with you there. Children take up so much of one's time and, although I don't begrudge people having children, they're certainly not what I want."

"Me neither," agree Jimmy.

"So besides useless sperm, what else do your testes make?" asked Serena.

"Um... testosterone?" suggested Jimmy.

"Very good, Jimmy," said Serena. "Testosterone is probably interfering with the supplements that I'm giving you, so... I'm thinking that another injection, to counteract the testosterone, might be necessary."

"But... isn't testosterone good for building up muscle?" asked Jimmy.

"It is, Jimmy," answered Serena, "but we're not interested in bulking muscle, at this stage. We want to fight the fat and fatigue and develop well-toned muscles." She pinched a roll of fat around his waist.

"Oh..." said Jimmy. "So, another needle in the bum."

"No Jimmy," said Serena. "We need to go right to the source. Injections into your testes."

"My balls?" asked Jimmy. Serena nodded. Jimmy asked, "Won't that hurt?"

"It won't hurt me at all, Jimmy," said Serena and laughed.

"I mean me," said Jimmy, seriously.

"I know you meant you. I was joking... It might hurt a little bit," said Serena. "Let's see how you are feeling tomorrow before we make a decision. You might step off the elliptical all bright and bushy tailed."

"Yeah, let's," said Jimmy.

"Off to the shower with you," said Serena, as she slapped his thigh.

Jimmy showered. He used Serena's pretty smelling shampoo and body lotion. He was getting used to the pretty smell.

Jimmy returned to the bedroom after drying himself.

He felt his face and asked, "Do you have a razor I could borrow?"

"No I don't, Jimmy," answered Serena. "I only have this."

"That's an IPL isn't it?" asked Jimmy.

"Something like that," answered Serena. "You know what an IPL is, do you?"

"Yes," answered Jimmy. "It's Intensely Pulsed Light, isn't it."

"Close enough," answered Serena with a smile. "How do you know that?"

"Oh... Um..." hesitated Jimmy.

"Does Charlotte have one?" asked Serena.

"Yes," answered Jimmy, embarrassed about mentioning his ex.

"Jimmy," said Serena with a smile. "Don't worry about mentioning Charlotte. I'm not worried about competing with your ex. Besides, I've known Charlotte longer than you have."

Jimmy was relieved and then Serena asked, "Shall we use this on your face?" as she plugged the epilator into the power point.

"Um... will it hurt?" asked Jimmy.

Serena pouted her lips and said, "It's alright for a woman to go through pain to look beautiful but a, so called, big, strong man can't put up with the same pain as a woman?"

Jimmy felt that he had to represent men so he said, "I only asked."

Serena held out her hand and said, "Give me your hand."

Jimmy held out his hand and Serena held it palm up. She pressed the epilator against his palm and Jimmy felt a slight shock, like an elastic band hitting him. He pulled his hand away and Serena glared at him.

Jimmy said, "I... I wasn't prepared for it."

Serena pouted again and repeated the process. Jimmy didn't flinch so Serena zapped the hairs on the back of his hand.

Jimmy said, "That's alright."

Serena smiled, raised her eyebrows and said, "Shall I?" as she held up the epilator.

"Yes please," answered Jimmy meekly.

Serena used bobby pins to hold back Jimmy's long hair. She held the epilator against Jimmy's sideburns and commenced to epilate his face.

Jimmy wasn't prepared for the slight sting that his face felt but took the treatment like a man.

Serena continued to epilate Jimmy's face, chin and upper-chest. She progressed towards Jimmy's nipples and Jimmy said, "That's not my face."

Serena stopped the machine and asked, "Do you like sucking hairy nipples, Jim?" Jimmy knew Serena wasn't happy because she called him 'Jim' instead of 'Jimmy'.

"No," answered Jimmy, knowing where this conversation was leading.

"Neither do I," said Serena with a smile and continued to epilate Jimmy's chest.

Serena epilated closer and closer to Jimmy's groin. He almost panicked and asked, "How far are you going with that?"

Serena asked, "Do you like getting hairs in your mouth when you perform cunnilingus?"

"No," answered Jimmy. He knew what was coming so he said, "Do it."

Serena smiled and epilated Jimmy's groin, right around to his anus.

Serena stopped the epilator and said, "There, go rinse off, Jimmy," apparently pleased with her work.

Jimmy showered and as he was drying himself, he looked at himself in the mirror. His face was red as if he had eczema. He called out, "Serena, my face is all red."

Serena entered the en suite, looked at Jimmy's face and said, "It looks like you've had a reaction to the epilator. Don't worry, it's temporary. It'll go away."

"I look like a clown," said Jimmy.

Serena tried to suppress a smile but didn't succeed.

Jimmy said, "It's not funny Serena."

"And I agree, Jimmy," said Serena. "It wasn't funny until you brought my attention to how your face resembles a clown.

"If you're that worried about it I can conceal it."

"Conceal it?" asked Jimmy. "What, with a paper bag."

That was too much for Serena and she laughed out loud. She said, when she finished laughing, "With makeup, Jimmy."

"That'll look worse," said Jimmy.

"Trust me, Jimmy," said Serena seriously. "I can cover that up and you won't look like you're wearing makeup. Besides, you're not going out so no-one will see you."

Jimmy looked at Serena and felt that he could trust her. He said, "I can wash it off of I don't like it, can't I?"

"Of course, Jimmy," answered Serena, "but I think that you'll be pleasantly surprised."

"Okay," said Jimmy as he looked at his reflection in the mirror. "It can't be any worse than this."

Serena sat Jimmy down at her dressing table and applied concealer and other makeup products. She finished and said, "What do you think?"

Jimmy looked at himself in the mirror. The redness was gone. He moved his face to within a few centimetres of the mirror and said, "That's amazing. I can't see the makeup unless I'm this close."

"You're not supposed to look that close, Jimmy," said Serena. "That's the secret to using makeup, which a lot of cross-dressers don't know. You apply the makeup to look like you're not wearing makeup."

Jimmy saw an errant eyebrow hair. He grabbed it and tried to pull it out as he said, "Can you conceal these things? I keep getting these hairs that grow longer than they should be and out of weird places."

Jimmy's effort had curled the hair like running scissors along one side of curling ribbon.

Serena tried to suppress a smile and said, "I can zap those too."

Jimmy was hesitant but then thought that Serena could conceal any redness caused by the epilator with makeup. He said, "Okay, please do this one and, I think there're a couple on this side."

Serena plugged in the epilator, attached something to it and held Jimmy's face still. She said, "Close your eyes," which Jimmy did, and Serena zapped his errant eyebrow hairs. She then used makeup to conceal any redness.

Serena looked at Jimmy's face. Jimmy asked, "What's wrong?"

"Nothing," answered Serena.

"No, tell me," said Jimmy, as he looked at his face in the mirror.

Serena stood close to Jimmy and looked at his refection. She said, "Your skin looks flawless where the makeup is on your chin and cheeks, but your nose and forehead are..."

Jimmy looked closer and finished Serena's sentence, "blemished."

"Yes," said Serena. "It looks... a bit funny. Do you want me to touch up your whole face?"

"Will it look okay?" asked Jimmy.

"I can make you look like anything you want to look like, Jimmy," answered Serena. She held his chin and moved his face from side to side in the light. She said, "You have such beautiful bone structure. I could do wonders with you."

"Maybe just the concealer to start with," said Jimmy, worried that this was going too far.

Serena applied more makeup to Jimmy's face. She said, "I'll just try something," and held Jimmy's face still.

Jimmy looked at himself in the mirror when Serena had finished. He said, "My eyes, they're so... blue."

"Yes," said Serena, pleased with herself and the makeup results.

Jimmy moved his face to within centimetres of the mirror and then slowly moved back. He did this a couple of times and said, "It's like an impressionist painting: up close, one can see the brushstrokes and paint, but as you move away you can see a beautiful landscape. Your makeup is like that: up close, I can see the makeup but as I move away it blends into a flawless face. You're the Claude Monet of makeup, Serena."

"Claude Monet?" asked Serena.

"Claudia Monet?" suggested Jimmy.

Serena laughed and said, "Thank you, Jimmy. You should see what the professionals can do.

"But first, breakfast," and she walked out of the bedroom.

Jimmy wore the pink negligee and slip-ons.

Serena said, with a Scottish accent, "Looking good, Jimmy," when she saw him. They both laughed.

They sat down to eat their breakfast: of natural yoghurt, Serena's special seed and nut mix, berries and some sort of fermented yoghurt drink. Serena held out her finger and Jimmy eagerly sucked the Sildenafil tablet off her finger.

After breakfast Serena led Jimmy, by his penis, into her bedroom. She eased off Jimmy's negligee and took off her own. Jimmy kicked off his pink slip-ons and Serena pushed him back onto the bed. She gently scraped her fingernails over Jimmy's chest. She pinched his nipples and Jimmy squirmed. She asked, "Do you like your sensitive nipples being playing with?"

"Yes," answered Jimmy.

"It seems the nipple suckers are working," said Serena. "Shall we continue using them?"

"Yes, please," sighed Jimmy.

Serena kissed Jimmy's nipples. She kissed down his body and stopped when her chin touched Jimmy's glans. She said, "I really like your smooth skin. Do you?"

"Yes," sighed Jimmy as Serena licked his glans.

Serena kissed her way along Jimmy's shaft and down to his scrotum. She gently kissed his testes, nestled in their sac.

Jimmy groaned, so Serena licked his scrotum. She said, "They feel so smooth. Do you like being smooth down here?"

"Yes," gasped Jimmy. "Yes I do. Please don't stop."

Serena lifted Jimmy's shaft, which resisted. She continued to kiss his scrotum. Jimmy's mind was going crazy but then Serena stopped what she was doing and reached into her bedside drawer for something. Jimmy was very disappointed. He wanted Serena to continue turning him on.

Serena put on a surgical glove and spread lubricant over her fingers. She used her other hand to lift Jimmy's penis and kissed his glans.

Jimmy knew what the glove and lubricant meant and he was very excited. He wanted Serena to finger his prostate, but Serena teased him.

Serena used her gloved hand to manipulate his testes. Jimmy loved the way her slippery fingers slid over his scrotum. His hairless skin felt silky smooth. She rolled and squeezed his balls, but also eased off her manipulations that just made Jimmy more excited.

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