Marilyn Goes to Hollywood

May 1, 2024 // By:analsex // No Comment

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Marilyn goes to Hollywood

As soon as the door closed behind them, James grabbed Gillian and hugged her tight. He found her lips and gave her a soft kiss, thrusting his tongue gently into her mouth. Gillian pressed herself to him as he ran his hands over her breast feeling the growing bulge at his crotch.

“James, stop. I’ll take care of you, but stop.” Gillian dropped to her knees and unzipped his jeans. She took him into her mouth and sucked at him furiously.

This was not the slow loving caress James was used to and he looked down at her.

“You don’t have to do that. What’s wrong?” he asked concerned.

Gillian stopped, removed his saliva-coated penis from her mouth and looked at him. “Let me finish and I’ll tell you.” She took him back into her mouth and sucked hard. It didn’t take long for James to erupt down her throat. She swallowed, licked him clean and stood up.

“Sorry, babe, I know you wanted that.”

James hugged her. “What’s the matter? You’ve been preoccupied all through dinner. Is it the exams?”

“Yes. Let me change and please get us something to drink. I’ll explain.”

Gillian left James with his pants and underwear by the door. He struggled out of his outerwear and stood in boxers and T-shirt. He went to the kitchen and poured two glasses of wine. That was all that was left in the bottle. He took the glasses to the small living room and sat on the couch.

James and Gillian had been an item for several months now. They were both in the final stages of their respective courses. Jack wanted to be an engineer; Gillian a cosmetologist. They had met at a party and hit it off. Gillian was a mere 5’5″ and 115 lbs. with firm 36B breasts, a great figure and shapely legs.

She was beautiful, always well made up and a great personality with a good sense of humor. James was 5′ 7″ a little taller than Gillian, with bright blue eyes and short, dark blonde hair. He had a very slim figure and worked out daily. He was a grade-A student and had just completed his Final exams.

Gillian’s were coming up and then they planned a journey in their car to a big National Park with no particular agenda in mind. After that, they would be looking for jobs.

Gillian came back in her robe which did nothing to hide that she was just wearing a bra and panties. She sat on the couch beside James, took a sip of

wine and laid down with her head on his lap. She looked worried. James leaned down and kissed her tenderly. His hand wandered gently to her open robe and breast. He rubbed the breast gently, more as therapy than or sexual excitement. “So, what’s up? I thought you did well in the exams.” He asked kissing her lightly again.

“Yes, that isn’t the problem. Ms. Elizabeth, our course instructor, told us some days ago that next week they are having important guests from Hollywood. He is the Director and Chief Makeup artist for a new film about Marilyn Monroe. Ms. Elizabeth has selected three of her best students to present models to him. They must be dressed and made up to look like Monroe. The winner gets to work in Hollywood for six weeks as an assistant to the Makeup director and will get film credits.”

“Sounds great and you’ll win it. Can I come to Hollywood too? Never been there,” James stated lightly tweaking Gillian’s nipple.

“Not so easy. Tanya and Millie are the other two and they are great. So, it’ll need to be fantastic.”

“Babe, you have the skills and I don’t know why you are worried. Just to be selected is already good.”

“Yes, but think of what will happen if I win. There may be other studios out there that may hire me permanently. Would be a fantastic opportunity.”

James leaned down and kissed Gillian tenderly. “You’ll make it and if you need someone to carry your cases to Hollywood, I’m your man. I am sure they need good engineers in LA.”

“I’d love that but I have to win first.”

“If that is all that is worrying you, then I can think of ways to make you relax. You’ll ace it.” James’s fingers trailed down to Gillian’s crotch and under her panties. He looked for that spot he knew would excite her. Unusually, she appeared to be dry down there. Normally he would find it moist and waiting for further stimulation.

“That’s the problem. I have to find a model that can reasonably pass for Marilyn. I asked all the girls in class who came close to Marilyn’s measurements and nobody is available. Do you know anyone from your class or friends?”

“No, babe, can’t think of anyone. What are you looking for?”

“Well, Marilyn was about 5′ 6″, about 120 lbs. and a 37-23-36 size. All curves in the right places.”

“Wow. You are about that weight but a little shorter. Your sizes are different but I assume there are many tricks to get you bigger up top.”

“That won’t work. I have to demonstrate that I can create that look on other people.”

“I’m sure you can find someone. I mean those are fairly normal height and weight. Even I would fit that Kartal Grup Escort statistic. I am sure you’ll find somebody and I’ll look around too. I’m sorry I can’t help.” James’ fingers were getting moist and he could see Gillian’s eyes closed and gentle movements as she reacted to his fingers. James leaned down again and gave her a deep kiss, working his fingers deeper. Gillian’s began to move faster and he continued for the pending James hand. She pulled his head down and pushed her tongue into his mouth.

“See, now you are a little more relaxed. I know you’ll figure it out,” James said. “Let’s go to bed.” He gave her his hand and pulled her up, kissing her lightly.

“Thanks,” she said a little more relaxed.

In bed they made slow love and both reach a climax together. They stayed like that and dozed off. Gillian appeared to be less tense as they slept entwined. It was almost mid-morning when James awoke to feel a moist mouth slowly sucking his now erect tool. Gillian had slid down and had her feet over the end. James was not large down there, perhaps a full 6″ when erect, but he never had complaints. He made sure his girlfriends were satisfied with his attention through penis, hands and mouth. Gillian certainly had no complaints. She had even once remarked that she liked his size as it fit well in her mouth. She looked up at him.

“Good morning,” she said with a smile. “I thought this might be a nice way to wake you up after you helped me relax last night.”

“Any time, babe,” he said as she licked, sucked, took each ball into her mouth. She was in no hurry and neither was James. After erupting several times, he was glad it would take longer for his first explosion of the morning.

“Would you come with me to LA?” Gillian asked poised with James’ very hard cock at her lips.

James looked at her holding his very hard cock to her lips. He didn’t want her to stop now. “Yes, are you asking?”

“Yes, I would like that. We can share an apartment. It would be fun. Would you like that too?”

“I’ve never been to California. It would be fun. And if you are going to wake me up like this every morning, I am in”. James was trying hard to keep his erection and pushed against Gillian’s mouth.

“That’s great but I would need your help.”

“Of course. What do I need to do?”

Gillian took the head back into her mouth, eyes never wavering from James’. After slurping it and soaking it in spittle and looked up.

“I was thinking about what you said and think you would make the perfect model for Marilyn.” Gillian took the whole penis into her mouth as James yelled an indistinguishable sound and came deep in her mouth. After letting it deflate, Gillian looked at James.

“I assume that was a ‘yes’, she said with a big smile. “And yes, I don’t mind waking you up like this every morning, Marilyn.”

After the intensity of his orgasm, James was amazed at Gillian’s request. “That’s stupid. How can you even suggest that?”

Gillian smiled. “You said yourself that you were not far off Marilyn’s height and weight. You have less on top and that can easily be fixed. I can make you look the perfect Marilyn but need your co-operation.”

“I don’t want to let you down, Gill. Much as I would like to go to LA with you, I don’t want you to lose because of me.”

Gillian looked at James, the deflated penis still at her mouth. “If you don’t do this for me, I will withdraw. I don’t have time to find someone and practice to make sure I have it right. We’ll have to forget LA.”

James stared at Gillian for a long moment confusion in his face. He had no idea what was expected of him but he didn’t want Gillian to regret their relationship down the road.

“What does Marilyn have to do?” he asked quietly.

“Well, you’ll have to dress and then go through the makeover. That will take some hours. You’ll have to stand inspection, of course. But nothing more. Say Hello and Goodbye in a sultry voice but nothing more.”

James took a few moments more to think about it. “So what will I do? When do you need to start?”

“Immediately. The more practice I get, the better on the day. I have about a week to get you perfect. You will need to wear heels and a bra. We’ll have to go shopping now. I already picked the store that has most of what we will need.” Gillian crawled up James’s body and kissed him. His taste was in her mouth but he had not disliked it before. “Thanks. I won’t forget this.” She helped him up.

“Do you really think this will work?” James asked now conscious of his decision. “I have no idea what to do.”

Gillian smiled. “We don’t have much time but I am sure I can turn you into an authentic and realistic Marilyn. If you can get into it with attitude, smile at the Director and walk a few steps in the heels, it’ll work. Won’t be easy but I know you can do it. Don’t forget, it’s my career so it needs to be good.”

Gillian went to her small desk and came back with a tape. James had pulled up his boxers. “Let’s get your Kartal Manken Escort measurements. Need to get the right outfits.”

“What do you mean by outfits? I thought this was a one day deal.”

Gillian smiled. “If you think you’re going to be a realistic Marilyn with big boobs, bra and dress walking in heels in one day, you misunderstand the project. We need to win. This means you practice in a dress and heels. Not the iconic Marilyn dress but something similar. Want to change your mind? I don’t want to spend time and money for you to back off.”

“No, no, I said I’ll do it. But I need your help.”

“Of course. I have a lot to lose. But you have to do everything I say and get into it. Then, we’ll be sipping Mojitos in Hollywood.” Gillian reached up and gave him a quick kiss. “And I’ll be giving you a special Good Morning’ kiss down there every day.”

Gillian measured James at bust, waist, and hips and from shoulder to knee. “Not bad. I think we can make this work. You’ll need a tight corset. Into the bathroom and wait for me.”

A bemused James walked into the bathroom in his boxers. He didn’t understand what he had promised. But his doubts were overcome with the thought of Mojitos in Hollywood. Gillian rubbed a cream all over his body up to his neck and embarrassingly even between his nether cheeks.

“Why do we need to do this? He asked.

Gillian smiled. “We’ll have to glue down those big hooters to your chest. Pulling them off with hair could be painful. In fact, we might start gluing them today so you get used to the weight and need to change your posture,” Gillian paused for a moment. “You realize that they expect me to transform an ordinary girl into Marilyn. What do you think the Director will say if he thinks my model is a boy?”

“How long….?” he began

“Trust me. You need to be perfect on Friday. We don’t want to come second. So getting used to acting and walking normally with that bust and in heels is key.”


“Yes, maybe not far but you would need to be as realistic as possible. I am sure just within the hall but you need to be ready.”

He didn’t ask why as he had to wait a few minutes and then was pushed into the shower. He felt good as he watched his sparse hair drain away and admired his smooth skin. Gillian pulled him out of the shower as he was beginning to feel his smooth skin.

“Until this is over, we will need to depilate you every couple of days. It’ll make the breast forms stay correctly too.” Gillian rubbed some lotion all over his body giving his cock a couple of strokes.

They returned to the bedroom and Gillian asked James to dress casually. She needed to make a call. James complied running his hands over his smooth skin which felt different. Even though he only had sparse hair before, he felt the difference.

“Do you have anything planned for the next week?” Gillian asked as she returned to the bedroom.

“No, just have to clear out my stuff from the flat. But that’ll only take a few hours as I don’t have much. I was hoping we could leave on that trip after your final so I didn’t renew the room. Why?” James shared an apartment with two guys. Since he didn’t have a job; his plans were to go on vacation with Gillian and then find a place to stay on his return.

“Now that is very convenient,” Gillian replied. “Let’s go help pack your stuff and then you’ll spend the next week here practicing to be Marilyn. Great!”

“But what about my stuff? My friends?”

“Well, you can put your stuff here if there isn’t much. You can go out with your friends as Marilyn and show off your boobs. Or you can help me win this competition and we can then move to California. I am sure Marilyn will make many friends there,”

“Very funny. So no vacation trip then?”

“If I don’t win, I’ll have time. Like you, I have no job to go to so we can travel and see the country. I have the apartment for another two months.”

James smiled at the thought. 24/7 with Gillian, driving along the highway deciding from day to day where they would go. He couldn’t lose. And when they returned, he wouldn’t have a room so moving in with Gillian would be a natural development. He smiled. Either way, for a short period of discomfort and even humiliation, he would be set in Hollywood or with Gillian.

It took them less than 90 minutes to pack James’ books, laptop and clothes. He lived in T-shirts and Jeans with a winter coat. Forty-five minutes later they had stored away his stuff in Gillian’s modest apartment.

“OK, now for the serious stuff. Till next Friday night, you’re going to be Marilyn. But since I can’t show you off too early, you’ll wear a bra, dress, and heels all day. We’ll practice your Marilyn looks in the apartment with a wig and accessories. If we have to go out, you’ll just be a regular everyday Marilyn. On Friday, you’ll be the Marilyn. No arguments or discussions. Agreed? I can’t afford the money to fail.”

James nodded unsure of how he could live up to Gillian’s Kartal Masöz Escort expectations. He had to try else he knew his relationship with Gillian would end. She was determined to make this a success. Hollywood was the place for her to reach the peak of her profession.

“Yes,” James voiced his assent. “I’ve never done anything like this before. You know that. I even avoided Halloween because I didn’t like dressing up and going around.”

“I know, babe. But this could mean a lot for both of us. This is not a public event. And after all the time and trouble to do this, this Director will probably decide in less than an hour if we win or not. So it is a big deal and I can’t thank you enough for agreeing. I promise to make it exciting for you,” Gillian said rubbing his crotch.

They arrived at a strip mall and a shop that had opaque windows. Except for some crowded dresses in the window, nothing inside was visible. James walked nervously, his hand in Gillian’s. “Don’t worry, try to have fun with this. You won’t be seen by the public. But you will look great I promise.”

The lady that greeted them in the sore welcomed them warmly. She was quite tall and had broad shoulders. Her face was heavy with makeup: a startling red mouth and very large heavy eyelashes. Her hair was big and blonde. Large hoop earrings hung from her pierced ears. The overall look was OTT glamor.

“OK,” she said coming to see them. “So, this is going to be Marilyn? His size is great and I think I have everything you wanted. If he is going home dressed, he’ll need another couple of outfits too,”

“OK, Clarisse, you know my budget. So please get him ready. I’ll pick out the other outfits, but I’d like the breasts glued on and then see him in the Marilyn dress and wig. We need to get close to the 37-23-36. Boobs won’t be an issue, waist and hips will present problems. See how close you can get and we can adjust.”

“I said I’ll give you a good discount if you keep your side of the bargain. We’ll try different sizes before we glue them on. So let’s see what I can do. Come along Marilyn,” Clarisse said and took James by the arm and led him to the back of the store. James had no idea about any deal. He was too absorbed by what was going to happen to him.

Clarisse asked James to remove all his clothing and gave him a panty to wear for modesty Clarisse measured his waist which was just under 30 inches. “Don’t worry, I have seen it all before and that panty is only for your modesty. I’ll be back in a minute.” Clarisse was smiling at James’ discomfort. He undressed and pulled up the panty. It was plain and without frills.

Clarisse returned with a series of items. They appeared to be corsets or some other restrictive garment. “We’ll have to try several before we get it right,” she said as she wrapped a garment around his mid-section. Hooking the section in front, Clarisse tightened the laces constricting his waist. James was startled at the sudden constriction as the laces were tightened. Seeing Clarisse’s size, James could feel her strength. The tape went around his waist. A moment later he was able to breathe as the laces were loosened and the corset removed.

“Well, you were down to 28″ but I think we can do a little better. You’ll learn to adjust your breathing. After a few hours, you’ll not know you’re wearing it. Because of the size of the bust, we have to use a special corset and then use the right sized bra. The waist cinchers won’t generally hold that size of bust in their cups. We’ll see.” Clarisse said this in a matter-of-fact manner as if this was a daily event. James didn’t understand then, but this was Clarisse’s business turning men into presentable women.

The next corset was placed around his waist and tightened. James could hardly breathe. Clarisse coached him how to breathe and tightened it until James almost fainted. “26 inches. Soon you’ll adjust to it,” Clarisse said knowingly. “Just breathe slowly… I’ll get a bra and forms.” James was left to ponder what was happening when Clarisse returned with several boxes with Gillian behind her.

Clarisse strapped a large bra on James pulling his arms through the straps. Gillian looked serious as Clarisse inserted two large breast forms into the bra cups and then tightened the straps.

“Bend forward, hand on knees like the iconic Marilyn pose,” Gillian commanded.

James did as requested. Clarisse and Gillian closely observed the pose.

“What size are those forms?” Gillian asked.

“38C which would be about normal for James’ size,” Clarisse replied.

“That is not James that is going to be Marilyn. Whilst we can’t get the wait to the 23″ Marilyn had, we can increase the bust to be proportionate to the 26″ waist. How big can you go?”

“Oh dear, Gillian, that is not a question for this salon. We have up to 42 EE and could get higher with a week’s notice. Let’s try 38DD which would be as big as I recommend. Then perhaps we can come down as required.”

“OK, let’s try that,” Gillian replied.

Clarisse replaced the forms on James’ slim frame who was still having trouble adjusting his breathing to his now narrow waist. They looked grotesque and Gillian decided in an instant that those were not going to work. After several trials, Clarisse and Gillian decided that a 38C would be best.

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