Lex Luthor's Girlfriend, Jimmy Olsen
Groomed to be a Slut!
by Mistress Tawny Suede
Chapter 4 - First Date
"We are going out tonight, to dinner." Felicity Bascombe said as she entered the room. Jimmy stared at the beautiful older woman, who was wearing only her undergarments - bra, panties, hose and heels. "I'm pleased to see you still find me attractive." she smirked as she lightly grasped his rigid prick in his pants. "We'll deal with this later!" she said.
She had him undress completely and then showed him where the shower was. She handed him a special soap to use on his body and Jimmy found that all of his scant body hair was washed away. When he was dried off, she sat him down at the makeup table in his room and slowly applied makeup to his face, starting with foundation to cover his freckles. She made sure that he paid attention to what she was doing so that he could do this himself in the future. She told him he must practise at home.
He watched as his face was transformed from that of a drab ordinary boy into a quite pretty, almost beautiful girl. He was sitting naked, other than a towel that had mostly fallen to the floor and his prick got hard. Mrs. Bascombe's hand would occasionally brush against it, leaving a precum trail along her wrist and also spilling down his length.
When she was satisfied with her efforts, she grasped his dick in her hand and began to fist him. "You were such a good girl, so patient. You deserve a reward, sweetie." She knelt between his spread legs and took his cock in her mouth. "Watch your pretty face in the mirror!" she told him, and Jimmy did watch the pretty girl pant and moan as she expertly sucked his cock. Finally he groaned and lifted his ass as he shot his cum into her mouth!
When she was done sucking she kissed him and her tongue pushed his own cum into his mouth! Yuck! But she was forceful and shortly had his entire load in his mouth. She lifted her head from his and said, "Good girls never make a mess, sweetie! Swallow my gift, and show me." Reluctantly he swallowed the cum then opened his mouth to show her that his mouth was empty.
"You need to repair your lipstick!" she told him. "I'm going to take a shower and get ready. Fix your makeup and look through your closet for something you would like to wear tonight. We are just going for dinner and drinks. Nothing fancy. Don't put the dress on yet. I might choose something different. In twenty minutes come to my room, but put on a bra and panties. We don't want that thing waggling around!" she laughed as she swatted his rising dick playfully.
It took Jimmy almost the full twenty minutes to make up his mind about what to wear. He had no desire to go out in public dressed as a girl, but if he had to, then he wanted to wear something that would draw the eye to his clothing and not to his face. He would absolutely die if anyone recognized him while dressed! He did put on the bra and panties as asked, and even pulled on a pair of stockings and a garter belt, and then some heels. As he walked down the hallway his ass wiggled and he had to giggle at how sexy he felt.
Felicity Bascombe was naked when he entered her room, sitting at her makeup table. He instantly got hard and started leaking a wet spot into his panties. She motioned him to sit beside her table. She leaned in and kissed him hard, then resumed applying her makeup, telling Jimmy to pay attention and learn. He had no desire to wear makeup, but he knew that the more adept he became, then the less likely that observers out in public would clock him as a man in a dress.
Finished, she had him dress her. He handled each piece of lingerie, even rolling the stockings up her legs. As he did he caught the heady scent of her cunt. As he knelt in front of her, pulling her panties up, he could not resist trying to lick her pussy, but she restrained him, telling him he would mess up his makeup, but also promising that he would get to enjoy her pussy when they returned after dinner, but only if he was a good girl.
Once she was dressed, they returned to Jimmy's room. She approved of his choice of clothing except she made him remove his stockings and replace them with a different colour, and she chose a different pair of heels for him. She chose earrings for him and selected a few bracelets for his left wrist. He repaired his lipstick and put the tube and a compact and some tissues into a small clutch purse that she handed to him.
There were a couple of condoms in the purse as well. He looked at Mrs. Bascombe in puzzlement and she said, "A girl should always be prepared, because men seldom are!"
He began to protest, but said, "You won't need those tonight, darling. But some time you might. So. Always. Be. Prepared." He still wanted to protest, but she put a finger to his lips to silence him. They returned to her room for just a few moments. She applied perfume to herself, the same delectable tantalizing scent which always bewitched Jimmy, and then sprayed Jimmy with a different delicate scent which also captivated him.
Moments later they were in her red convertible and driving to a fancy restaurant in the fashionable part of Metropolis. "Light a cigarette for me, please dearie." She asked Jimmy who was enjoying the breeze as they drove.
"I don't smoke!" Jimmy said. But she gave him a stern look. He fumbled in her purse for a cigarette and pushed in the car lighter. Moments later he put the cigarette to his lips and inhaled as he touched the bright metal to the tip. He coughed at the smoke in his mouth, but he got it lit.
Taking the cigarette from him, Mrs. Bascome said, "You should really start smoking dearie. A girl can to so many things with a cigarette to make her more attractive to a man!"
"But I don't want to be...." he stammered.
"Hush dear. Your voice is too harsh! Slow down, speak softly, or not at all. You need to practise your voice! And learn when to let your eyes do the talking instead!"
They pulled up at the restaurant and a valet took the car away. Jimmy was very nervous. He was sure that everyone would point at him, laugh at him, for being a boy in a dress. But no one did. In fact, no one paid any attention to him at all. Which made him a bit angry. "Good evening, Francois! My usual table please. And may I introduce my young friend, Jenny!"
The were shown to a table for four, but it was just the two of them. In a very nice restaurant. Very very nice, thought Jimmy. "Jenny?" he asked.
"Well, it would not due to call you Jimmy when you look so pretty. So for tonight you are Jenny. Hmmm... you need a last name too. Jimmy Olsen.... Jenny Nelson! Yes, when we are together your name will be Jenny Nelson!"
Jimmy did not object. He did not plan to be outside dressed as Jenny ever again. He was doing this once, just once, to please Felicity Bascombe. He so wanted to fuck her again. He would do anything for her, tonight. But after tonight, no..
"Light another cigarette for me, Jenny. And one for yourself as well!" They were in a restaurant that permitted smoking and Jimmy had found the odour disturbing. Reluctantly he lit two cigarettes and wondered how he could get out of smoking one of them, but he could not. So for the next ten minutes, he tried to carry on a polite conversation with the gorgeous woman, interspersed with coughs. She critiqued his smoking, telling him how to hold the cigarette and how to inhale, all in a ladylike fashion. He finally finished the foul thing, only for her to order him to enjoy another. Not just smoke it, but enjoy it.
After one shared bottle of wine their food arrived and a second bottle appeared. Jimmy was not focussing fully but was becoming frustrated as Mrs. Bascombe now told him how to eat. Goddamn he knew how to cut and eat his food, but evidently this was not good enough for her. As he got more angry he was just about to get up and stalk out, then he felt the woman's toes work their way under the bottom of his skirt and caress his cock in his panties. He gulped and calmed down. And got anxious instead.
As dinner was winding down and Jimmy was longing to have this embarrassing evening finish, Felicity looked beyond him and her eyes lit up. Then two large men set themselves down in the empty chairs at their table. "I'm so glad you could come!" Mrs. Bascombe said. And then to Jimmy she said, "Jenny, these are my friends Marcus and Lionel. Gentlemen, this is the young lady I mentioned to you, Miss Jenny Nelson."
Jimmy was caught off guard as the two black men engaged the women in conversation for the next half hour. At first he was nervous but then relaxed when he realized that they had not seen through his clothing and detected he was a male in drag. He took encouragement from his earlier brief training and modulated his voice so that it was more feminine.
Shortly into the conversation, a deep male voice boomed out saying "Felicity!" Jimmy looked up and found Lex Luthor standing at their table, three bodyguards standing in the background.
"Lex!" Mrs Bascombe stood and the two hugged. "It is so nice to see you! You know Marcus and Lionel of course!" Lex nodded to Lionel and shook Marcus' hand.
"And this young lady?" Lex asked.
"My dear friend Jenny. Jenny Nelson. She is new in town. Jenny, get up and let Mr. Luthor get a good look at you!"
