The Honeymoon
by JackRabbit308
Raven was a woman that knew what she wanted and demanded she get it. She had become an office assistant just to hunt down an executive husband. She was 5’4”, black wavy hair, and milk white skin. She could play the evil queen role in any fairytale. But Raven didn’t want power. She wanted the life of luxury that only one of these buffoons could afford.
Raven had had plenty of offers for dates and sugar daddys. But they required her to actually have sex with them. No, Raven deserved someone that required nothing but her presence. A servant with a 6 figure income. That’s when she found David. David was a timid looking guy who everyone in the office loved. He wasn’t a threat to any of the other executives due to his meekness and he got to where he was with honest hard work. Raven watched her prey and learned everything she could about him. He only owned 3 suits from what she had seen and they all looked like they were off the clearance rack. He drove a standard sedan and brought his own lunch. She knew David could afford luxury but he had no interest. That was perfect for Raven since she knew he had money just waiting for her. When it came to a sex life he was at a zero. His shyness had prevented any workplace relations and she knew he wasn’t getting any outside of work. She had snuck into David’s office and found his “special drawer” full of bottles of lotion and extra boxes of tissue. A trashcan full of used kleenex and a few white stains splattered under the desk let her know David was only fucking himself.
The hunt was easy. She started approaching David at lunch, laughing at his jokes, smiling at him, and giving his arm a squeeze now and again. He’d leave the lunch room trying to hide a massive hard on and lock his office for 20 minutes. She could imagine him furiously pumping his fist to the thought of her giving him attention. He was becoming quite the good boy.
Raven mentioned she always wanted to try this expensive restaurant downtown and David took the bait faster than expected. Their first date was a booth at the most expensive place in the city and David gave her no restrictions. He wasn’t trying to impress her either. He just didn’t see money as a big deal and this enticed Raven more. When he took her home, he opened her car door and walked her up the steps to her apartment. He was brave enough to go in for a kiss and she moved at the last minute to make sure it was only a peck on the cheek. She saw disappointment in his eyes but it disappeared after she returned the favor and left a big red lip mark on his cheek. His face was flushed and his pants had a tent.
He proposed a month later. She instructed him on how to do it and made sure he bought the right ring. She was ready to enact phase 2.
“Oh I wish I could say Yes, David.” she edged him on.
“Bu-but what?” David wasn’t sure what he did wrong.
“Well I worry you will change and become a brute! How can I trust you won’t become another jerk like the other men at the office?”
He looked at her desperately, “Whatever you need Raven, just name it!”
Now she had him, “I need you to allow me to make you the best David you can be. I will take you far David but you have to trust me. Trust me so I can trust you!”
“Of course Raven!”
“And there is another thing… I know about your perverseness. I have been trying to ignore it but David it is too much!”
“What do you mean?” David looked at her quizzically.
“Well I appreciate you never pushing me to have sex. But I know about your fun at the office.” She made a masturbation gesture with her fist. “I worry you just want me for base pleasures and I just can’t get that out of my mind”
David’s face was red. “Oh well…I don’t do it a lot.”
“David, you lock your office door 3 times a day.”
“I..well…umm..” David was sweating.
“David. Honey. I need you to prove you have self control. Take a vow of celibacy for me. For us! No sex or masturbation until we get married. Please?”
She placed her head and hand on his chest. Her fingertips strategically brushed his nipple as she waited for a response.
“Anything for you Raven. How long do you need?”
Just until our wedding night! Yes, David! I will marry you.
One year. She spent a whole year training David. She had him buy a new car, new clothes, and exercise religiously. When she was done with him he looked like a rich playboy. She “allowed” David to spoil her for helping him. The lived in a luxurious apartment, she wore the finest designers she could find, and never had to lift a finger for anything. She kept David to his word. She installed a camera in his office, would barge into his showers, and even put parental blocks on their tv and internet.ALthough he looked desperate to touch himself, he was a man of his word.
Their wedding was so lavish and everyone came. Everyone told her how good David looked and how marvelous her dress was. Raven was so happy to get the dream wedding she always wanted. She was even more happy about her new servant-husband. Now phase 3: the wedding night.
Raven exited the bathroom in a white, short nightgown that had deep cleavage and was almost transparent. David was wearing his black designer boxer-briefs with an angry looking erection. Raven teased him by standing by the bed and applying lotion all over her body ever so slowly.
She hopped into bed and kissed David good night.
David sat there in shock. He had let Raven control his life so he was unable to make a move and ask for his year long reward. He put his hand on her shoulder. Raven smiled knowing what would transcend.
“Yes David?” She looked up sleepily.
“Umm so tonight is…our wedding night.”
“I know honey. It is so exciting!” She patted David’s erection pretending she didn’t notice the throbbing from under the sheets.
“Ohh…umm so I thought that meant we would. You know…do things?”
She turned and looked back at him suspiciously, “David, I am very tired from today. Just because it’s our wedding night you think I owe you sex?”
“No darling! Not at all! It’s just that I have been celibate a whole year.” Raven heard the desperation in his voice.
“Well, you have been quite a good boy. I guess I can give you a reward.”
David almost ripped his underwear off as he got ready.
“Now now David, I want to make this night special. I have this kink that I have been dying to do with you. You’re not the only one waiting a year for this.” Raven of course had been masturbating all day long while David was at work and even had a few men she used regularly for their bodies. But she couldn’t have David feel he got the short end of the stick.
David was, of course, compliant. “What is your kink??”
“David, do you find me beautiful?”
“Oh my god yes Raven!”
“Do you find me sexy?
“100% yes!”
“Good. I have this…fantasy. A man sneaks into my bedroom late at night while I sleep. I have no clue he is there and he tries super hard not to wake me. He goes into my closet and picks out a nightgown. He strips completely naked and puts it on. As I sleep this man is wearing my clothing and lays next to me. As I sleep he pleasures himself all night. And I mean all night. As much as physically possible he masturbates himself while looking at me.”
David looked puzzled, “So I masturbate while you sleep? Then what?”
“That’s it! God, the thought turns me on so much! It drives me crazy just thinking about it! Please honey. For me?”
“Umm.. ok sweetie. So what do I do?”
“Go to the bathroom and wait 10 minutes. I will pretend to be asleep when you come back. Find the girliest night gown in my closet and put it on. Come lay next to me and go to town on yourself. I want to see how much you adore me. But don’t make a mess.” She hands him a box of tissues from the night stand. “Use these because the sheets are so silky and I would hate to ruin them.”
Raven turned away from David and went to sleep. David wanted to ask if they would have sex later but he didn’t want to ruin any chance he might have. He went to the bathroom and became excited. On the bathroom counter was a note with his name. “He opened it and Raven had made some instructions for him.
“Hello honey,
I hope you are ready to pleasure yourself like you’ve ever done before. Make yourself pretty for your big show.
-Raven Xoxo”
There was a box next to the note. In it was a tube of bright red lipstick. David hesitated but went ahead and applied it. He went to the closet and found a pink babydoll nightgown hanging for him. A note saying “My pretty boy” was attached. The night gown barely fit. David’s penis poked out from underneath. He glanced at the mirror and couldn’t believe what he saw. A 30 year old man, wealthy, beautiful wife, physically fit was wearing a pink nightie and red lipstick for his masturbation marathon next to his sleeping partner.
He walked over to the bed and looked at Raven. She must be really good at faking because he could swear she was fast asleep. He laid down and grasped his rock hard member. His penis eagerly leaked precum that David used to lube up his penis. He lifted the hem of his nightgown to get a better stroking pace. He bit his lip and could feel the lipstick smear. It may not be the sex he wanted but he was happy just to jerk off again!
All of a sudden Raven turned to look at him. He was so exited! This must be one of her tests! Would he be willing to humiliate himself for her and he would! Now what? Maybe he could finally have sex with his wife!
“David, sweetie, you’re really shaking the bed.” She yawned. “Can you lay on the floor while you beat it? It will make it more sexy to act like you don’t want to wake me.”
“Oh…” David shuffled out of bed and laid down. “Like this?”
No response. Raven was already back to her “fake sleep”
If Raven had been awake she wouldv’e heard David break down as he fucked his fist. Tears went down his cheeks as he stroked. David knew this was it for him. All the hard work and changes he made and for what? Jerking himself off in a dress after a year of abstinence. But he couldn’t stop. It felt so good to finally touch himself again and he needed to cum so bad. He reached for a tissue and decided to grab a few more just in case.
Raven awoke the next morning to a beautiful sunrise coming in through their window. She stretched and looked over to an empty bedside. She quietly crawled to the other side. She had to hold her hand over her mouth to stop her laughter. David was splayed out on the floor. His nightgown was rolled up to his chest, his lipstick was smeared all over his mouth, and there must have been 10 tissue wads all around him. His penis looked sore from all the self love it got last night. She rolled back into bed and started pleasuring herself. She ran her fingers around her clit as she thought about all the money she had, all the clothes, the jewelry. She wondered how far she could take David. Maybe get him a wig. More lingerie. She would let him masturbate as much as he wanted (But would take that privilege away whenever she felt like it.)
Her fingers moved faster as she reached her climax. Maybe she wouldn’t need to hide her adultery and have David listen to her fuck as many men as she wanted. Right here, in her wedding bed she would have a train run through her as her sissy husband beat his meat in the closet. For now she would shower and let her little masturbator boy rest. He had a lot more wanking to do before he had the privilegeof taking his wife shopping.