Wendy got a new boyfriend, the IT guy from work. He introduced himself to her by “finding” her misplaced hairbrush. He told her he didn't know if she lost it, and he didn't know if it was hers, but he had waited until she arrived before asking someone if it was hers because he liked her and it seemed like the nice type of thing SHE would own.
She was a secretary at a medium sized steel parts factory in Chicago, and they had taken an instant liking to each other the very first day they had met. It was a case of instant mutual attraction, and they never let that moment pass. It was renewed every time their eyes met, too. They both felt it in their hearts and their vitals.
Wendy went out to lunch with him, and found out he was a widower, as they exchanged information, since his wife had passed about a year ago. He had an 18 year old son, who had been fathered on prom night back in high school. The boy had lived with him alone since his wife had died in childbirth, but he had still welcomed the boy into his life and opened his home to him.
“You've never had another woman in your life?” she asked, keeping her voice steady with great effort.
“No.” he replied. “Raising Jason alone took all my time and effort. I never had any time to spare for all of that, anyway.”
“All of that?” she asked, raising one eyebrow in a way she thought looked provocative and sexily desirable, based in the hours she had spent in front of a mirror practicing.
“I'm of the persuasion that the love of one's life is worth every moment of one's waking life. No time should be spent when awake that is not admiring her perfection.” he said, matter of factly.
Her breath caught in her throat for a moment, but she recovered quite quickly and told him that she was a single mother with a daughter, only 18, and recently graduated from high school. She had lived with her parents her whole life because she had gotten pregnant on her prom night and lived with her mother's disappointment her whole adult life.
No matter how much she had debased herself to her father, she could never atone for her sins in the light of her own eyes. She felt she could see it reflected in the way he looked at her, too. Her child was a living testimony to her failure in everyone's eyes but his. She could feel the acceptance and love in his gaze as he radiated heat with his whole being and shined it out of his eyes toward her.
She kept her silence for a long moment. No words needed to be spoken as they poured their own thoughts and emotions into each others eyes through their own. Neither of them could think a lie in that moment that lasted what felt like an eternity as one melded into the next.
The food arrived, breaking the moment temporarily, and they both spent the next ten minutes eating, not talking much until their plates were empty. Then they got back into the conversation they had abandoned when the waiter had showed up with the food.
“One kid. That and my job. That's been my whole boring life.” he said, smiling at her. “He just graduated high school, but he doesn't really have any plans for college. He never even sent any applications!”
“Oh, that's too bad.” Wendy said, commiserating. “I'm afraid Miranda won't be going to college, either. She applied to one, but she didn't get accepted.”
“How old is she?” he asked, curious.
“Eighteen, same as your son.” she replied. “She just graduated, too.”
“Enough about them.” he said, and took her hand in his across the table. “I want to know about this pretty lady right here.”
“Oh.” she said, blushing. “I'm afraid there's not much to tell.”
“How did you get your daughter? Were you married like me?” he asked.
She blushed again and shook her head. “My senior prom date raped me, and left me stranded a few miles outside of town when I wouldn't suck it after he took my virginity.” she admitted, hanging her head in shame and looking at the table, embarrassed. “He's the only man I've ever been with.”
“Really?” he asked. “Nobody since then?”
She shook her head, still looking at the table, still embarrassed. He put a finger under her chin and made her look at him, catching her eyes with his own and not letting her look away.
“I'm going to be the first man you give yourself to.” he said, smiling. “You got taken once, but your going to GIVE yourself to me!”
“I... I am?” she asked, blushing again, even redder than before. “I've never... I've never let a man love me because I'm not worth loving. I'm broken and ruined.”
“Not to me you're not.” he told her, still meeting her eye. “To me, you're a beautiful girl who has never known the love she deserves.
“Come on, let's get out of here.” he said suddenly, throwing down a pile of money onto the table instead of waiting for the check. “That's enough to cover lunch and a pretty generous tip.”
He took her hand as he led her out of the restaurant. “No, wait, I've got to go back to work!” she exclaimed, letting him lead her to his car, parked on the other side of the lot from her own. “Mr. Anderson, my boss, will fire me if I don't show up right after lunch!”
“No, he won't.” Bill said, matter of factly. “I let them know at your front office that I was taking you to Armando's. They know what that means. My company is several order's of magnitude above yours, but trust me, mine and yours have done business before, and both have profited from the relationship! This relationship between the two of us that's developing is 100% corporate approved.”
“But we just had lunch at Brian's Deli.” she said, confused, ignoring a little niggle of a suspicion that his words had inspired. “What's Armando's?”
“It's a restaurant in Los Angeles.” he said, smiling as he opened the door for her and helped her sit down.
“But we're in Chicago.” she said, confused. “Are we going to L.A?”
“No, we're going to my place, and we'll be there until tomorrow morning.”
“But... what does that mean?” she asked, sitting down in his car as he opened the door for her, then sat there looking puzzled as he walked around and got in the driver's seat. “I'm spending the night at your house?”
He smiled at her gently and started the car. “You don't mind, do you?”
“I don't know.” she admitted. “Nobody has ever taken me to their home without inviting me first.”
“There's a first time for everything.” he smiled at her. “Will this be the first time you have given yourself to a man willingly? I am inviting to my bed; not just my home.”
“This will be my first time in a bed.” she said, blushing. “I've never shared a man's bed before. I got pregnant in the back seat of a car.”
He looked at her as she looked down, blushing.
“I marry you.” he said solemnly. “I marry you. I marry you.”
She smiled at him, and repeated his words, taking both his hands in hers. “I marry you, I marry you, I marry you.” She looked at him. “In the oldest cultures we know about, that is the ceremony for marriage. It is done between to people alone, because that marriage is between those two people and nobody else.”
“I know.” he smiled. “Wife.”
Her smile faltered. “Are you taking me home to enjoy your marital rights?”
He grinned even more broadly. “You guessed it!”
She swallowed nervously. “I hope you're not disappointed.” she said softly.
“Get naked once we're in the house, and I'll let you know. Wife.” he smiled.
“As you command, husband.” she said, meeting his eyes with a hesitant smile.
“Tell me the truth, wife...” he said. “Have you ever had one in your mouth? Have you ever tasted a man's seed?”
“Oh my God!” she whispered, then shook her head. “I've never even seen one.” she admitted. “When Miranda was conceived, he just pulled my dress up and shoved it inside me, then kicked me out of his car when he was done.”
“Well, that's not what I'm going to do.” he told her. “You're going to see mine, up close and VERY intimately.”
“In my mouth?” she asked, sounding curious and frightened, both at the same time.
He smiled and nodded, and she returned his smile nervously. “Is it okay? I've never done it before, and I've heard from some of my friends that it's a little gross, especially the end part, where you finish and expect me to swallow your stuff.”
He smiled at her. “None of your friends liked it? Not one?”
“Well, one of them liked it. She liked it a lot, I guess. She even liked swallowing the stuff that ends the whole experience, too.” she told him, looking down shyly and breaking their connection.
“Well, I would like it better if you liked it, too.” he told her, and she made up her mind to like it, no matter what. She really wanted this to work out with him because she could tell in her heart that he was kind.
They pulled into his driveway, so he shut the car off, then hurried around to open her door for her and took her hand, helping her out.
“Thank you.” she said, flattered, and got out of the car. “Such a gentleman!”
“You haven't seen anything yet.” he said. “I'm going to make you come three times before I get a load out.”
“Good luck with that.” she said dryly. “I've never even had one, not even doing it myself.”
“Really?” he asked, with a small smile. She liked the way it touched his eyes, so she returned it. “I'll get to watch you have your very first orgasm, ever?”
She nodded. “I don't think I can even do it, though. I've heard my friends describe them before, but I've never even felt anything close to what they described. I think I'm broken or something.”
He led her upstairs to his bedroom and had her sit down. “Take your clothes off.” he told her. “All of them; right down to your skin. Do it sexy; turn me on as you reveal yourself to me. Striptease.”
She blushed and shook her head. “Nobody has ever seen me all the way naked before.”
“Good.” he smiled. “Another first for me. Take all the time you need, but in the end, I want you naked on my bed with your legs wide open, ass on the edge of the bed, and both hands holding you pussy open for my tongue.”
“For... for your tongue?” she asked.
“Oh yes.” he smiled at her. “I want to taste you. I bet you taste nice!”
She blushed when she realized what he meant. “Nobody has ever... they've never tasted me before.”
“Another first!” he crowed gleefully, grinning enthusiastically at her. “Come on, do a strip tease for me! You can start with that blouse, okay?”
“Oh, God.” she whispered, blanching to pale as all the blood rushed from her face. “Nobody has ever seen me naked before, either. Do I have to?”
“Yes.” he said. “Because I know what you really want. I know you want to be forced. Just like the first time.”
“How... how do you know about that?” she asked, fearfully.
“Because I know Jared Miller.” he replied, smiling at her shocked expression.
“What?!” she exclaimed. “How do you know him?”
“He works for me.” he said, smiling. Seeing her confusion, he explained. “I'm the controlling interest in MacElroy Associates.”
“You are?” she asked. “I thought you just did the IT.”
“Oh, I do work in the IT department, but I also own several companies.” he told her. “You can start taking your clothes off any time now.”
“You own MacElroy Associates?” she asked, her voice full of awe and wonder. “AND you work there, too?”
“That's right.” he said, and then he added, “I believe you're stalling. You can start stripping any time now.”
“No-nobody has ever seen me naked before.” she admitted, swallowing nervously. “What if I don't pass your approval?”
“Hmm, I never thought of that.” he mused, then looked at her brightly. “Take off all your clothes and we'll see if you do or not. A chance I'm willing to take, okay? I'll let you know if I don't approve, and you can get dressed again, okay?”
“Really?” she asked, an earnest expression in her eyes. “You promise to tell me the truth? No lying?”
He raised his right hand and met her gaze steadily. “I promise, no lying.” he swore. “Let's see what you've been hiding under those button up sweaters at work!”
“Oh!” she said, blushing, crossing her arms protectively in front of herself.
“Come on, pretty girl!” he smiled. “Let me see them!”
“I'm shy.” she whispered, blushing. She kept her arms crossed protectively across her bosom, hiding her breasts from his view.
“I know.” he said softly, smiling at her gently. She saw it and returned it, gratefully. “Let me help you.”
He reached out and began unbuttoning the top button of her blouse, but she pulled back, shying away from his hands.
“What are you doing?” she demanded. “I can do it myself!”
“Okay.” he said, agreeably. “I just thought it would help you feel less like a slut if I helped you get undressed, instead of making you take all your clothes off yourself so a man could watch you do it in front of him, like you were some sort of hussy or something. If I help you, you aren't doing it all yourself, right?”
“Oh.” she said quietly, and looked at him thoughtfully. “You can help. I don't want you to think of me as a slut!”
“You're not a slut Wendy.” he said, smiling at her again, the same simple smile he'd given her before. He got the button open and moved his hands down to the next one as she looked into his eyes and returned it. He began opening the third, then the fourth, and pulled the material apart to expose her bra before going to the fifth. “You're a good girl.”
She cleared her throat and stopped his hands from moving down to the last button that wasn't tucked into her skirt and pulled the material closed again.
He put one finger under her chin and lifted her head, capturing her eyes with his own and smiled gently again. She looked nervous.
“Wendy.” he said softly “Take your blouse off the rest of the way all by yourself, then put your arms to the side and let me look at you.”
“Oh!” she said softly. “Oh no! I can't do that!”
“You will do this because I told you to.” he said. “You will do it to prove that you are a good girl who knows how to obey orders.”
She swallowed hard, extremely nervous now, but it was easier to obey than to think, so her hands moved of their own accord.
“See how easy it is to be a good girl?” he smiled. “All you have to do is what I tell you to do.”
“Tell me to do something else!” she said eagerly, smiling. “It's sort of fun giving up control like that! The naughtier it is; the more fun it is!”
“Good, you'll like this, then!” he said, grinning evilly and leering at her. “You have a choice; take off your skirt and let me see your panties, or take off your bra and let me see your tits.”
“No, oh no!” she moaned. “If I do that, I'll be a slut!”
“No, you won't.” he told her, looking right at her. It seemed to her he was looking right at he soul, such was the intensity of his gaze. “You'll be my good girl, because you'll be obeying my order. Which will it be, panties or tits first?”
“It's going to be both before we're done tonight, won't it?” she asked, her voice sounding dejected.
“Yes.” he told her. “That, and a lot more. Everything.”
“Oh my God.” she whispered, then looked at him beseechingly. “Please help me?”
“I'll help you.” he said kindly, and she looked at him gratefully. “Show me your tits first. I've been curious about the color and size of your nipples for a while now.”
“Oh.” she sighed, and the light in her eyes died. “I thought you were going to help me.”
“Oh, I am helping you.” he told her, smiling. “I'm telling you what to do.” He looked at her and smiled at her again. “A good girl does what she is told.”
“Oh God.” she whispered. “You want to see my breasts? You've wanted to see them for a while?”
“Oh, yes. Both of them.” he smiled, his eyes looking at her in a very friendly manner. “Show them to me, good girl.”
She swallowed hard, with a nervous look in her eyes as she reached behind herself to unhook the clasp. She hesitated a long moment as she held the cups tightly against her chest and looked at him ashamed. “Sluts show them both at the same time. Can I just show you one of them? That's what a good girl would do.”
“You're right; that's what a good girl would do.” he said to her. “But I don't want my future bride to BE a good girl. I want her to be a good slut.”
“I don't know how to be a slut.” she told him truthfully. Her voice told him she was truly repentant about it, too.
“Sorry, they're not big enough.” she said. “I was hoping that breast feeding my daughter would make them bigger, but it didn't.” She ignored his last comment and changed the subject of their conversation entirely.
“Well, let me see them.” he said. “I'll tell you if they are big enough or not.” He chose to go along with her subject change and turned it to his advantage.
“Okay.” she said, smiling, and dropped her hands, taking the bra away with them and dropping it on the floor next to her blouse. It took all of her courage, but she bravely accepted his challenge and let him see her eyes blazing at him.
“Hmm.” he said, considering. “I can't really tell; not without checking something...” He wasn't looking at her eyes at all and missed the firestorm brewing there. This angered her even more; that she was feeling all this emotion and as far as she could tell, he felt nothing. His eyes were fixated on her nipples and nowhere and nothing else.
“What?” she asked, concerned. “What do you need to check?”
“I need to see if my cock fits between them.” he said, smiling at her shocked expression. “That will give you a chance to see it up close.” He paused. “And, to taste it!”
She stood there, frozen in fear, covering her naked breasts with both hands, and watched him open his pants and take his semi hard cock out, which was already longer than her fully extended hand. It was easily three inches around and over seven inches long, and it wasn't even all the way hard yet!
She looked up at his face and saw his gentle smile. “I have to put THAT in my mouth?”
“As far as it'll go.” he said agreeably, and his smile widened at the dismayed look in her eyes as his words registered. “I've heard that swallowing the head if it makes it easier to deep-throat “You can start by putting it between your breasts and licking the tip of my cock.”
She looked at him gratefully and smiled with relief as she dropped the bra, then pushed her breaths together and shuffled over to him, going to her knees and proffering the bare melons to him. Then she took in her mouth and went as far on it as far as she could. When she was done, his pubic hair was tickling her nose.
“That DOES help. I like being told what to do. Especially when tell me to do something naughty. That makes you a bad boy, in my mother's eyes. A bad boy has taken control oh her little girl.” she said simply, smiling up at him. “Well, guess what, Mother, your little girl is growing up! Just because you never had to do it doesn't mean I don't want to do it. I'm ready to become a woman!”
“Yes, you are.” he agreed. “Your tits look good, too. They're big enough, too. Have no more worries on that score, okay?”
“Thanks.” she said, gratefully, then bent her head and looked at the top of his cock as it appeared from the tops of her breasts. “Should I start sucking it now? I've never done it before, so please forgive me if I do it wrong, okay?”
“Do whatever you think will feel good for me.” he suggested. “Don't worry about doing it wrong, okay? Just have fun with it.”
She thought about it for a little minute, considering. Have fun with it? She'd never even thought about what fun she herself could have during sex; it had always been about HIS pleasure, not her own. She opened her mouth and took his cock in, tasting something brand new to her, and found she actually DID enjoy the feel of him filling her mouth with his manhood as it slid in deeper and deeper each second.
She didn't gag or fight him when it reached the back of her mouth and tickled the beginning of her throat. She felt his pubic hair tickle the tip of her nose, and grabbed both cheeks of his ass, pulling him the rest of the way into her throat
Then she swallowed, letting the action work on the head of his cock. He came convulsively, three large pumps of sperm that went right down her throat and into her stomach.
“Mmm, you're good at this.” he said, stroking the hair on the back of her head as he let her up to breathe. “I bet you didn't even know you could do the deep throat, but you're not choking at all!”
She let it go out of her mouth as she looked up at him, surprise evident in her eyes. “Is this not normal?” she asked. “Am I doing it wrong?”
“Not at all.” he told her, smiling down at her. She could see how proud he was of her written all over his face, and felt relieved. She had been worried she had disappointed him somehow, but she saw that that wasn't the case at all. “You should be proud, Wendy. Most women can't do it at all, even after years of trying, and you did it the very first time you ever had one in your mouth!”
“It feels good for you when I do it?” she asked, taking him I her mouth once more and allowing it to enter her throat.
“It's the second best thing in the world.” he said. She took her mouth away again and looked up.
“What's the best?” she asked.
“Pussy.” he said simply, then looked at her and winked. “Are you on birth control? Can you get pregnant if I come inside you?”
She looked at him, shocked as she realized what he was asking.
“I can get pregnant.” she said shyly. “I've never been on birth control; never in my life.” She looked at him questioningly. “Are you going to get me pregnant?”
“I might.” he said. “When did your last period end?”
She thought for a moment, considering. “It ended two weeks ago tomorrow. Why?”
“You're your fertile phase right now.” he told her. “Would you prefer to swallow my come, or should I fuck you in the ass?”
“In my ass? I've never done it there!” she asked, reaching back with both hands and holding her but closed. “I guess I'd rather see what it tastes like. Do it in my mouth, okay?”
“Sure.” he agreed. “But I'm going to fuck you first. Ready for some cock in that pussy of yours?”
She giggled, smiling guiltily. “You make it sound so dirty!”
“It's only dirty if you do it right.” he joked, and she smiled.
“Let's do it dirty, then. I want you to fuck me right!” she said. “I've never been fucked before. I got impregnated.”
“You're going to enjoy it this time; I guarantee it!” he said, smiling at her gently. “I'm going to make you come at least three times.”
She scoffed a little laugh at that. “Good luck!” she told him. “I've heard my girlfriends talk about such things, but I seriously doubt anyone could feel THAT good!”
“It's better than you can imagine.” he said slyly. “Take off your jeans and panties and I will show you.”
“Yeah, right!” she scoffed, but he gestured for her to begin stripping off, so she unbuckled her jeans. She stepped out of her shoes, then pushed her pants down and stepped out of them while she was bent over at the waist.
“Damn nice body you got there!” he said admiringly. “I bet you'll be the best fuck I ever had.”
“You bet?” she asked looking to change the subject for as long as possible. “How much?” she asked, a thoughtful look in her eye.
He saw her look, and decided on the spot to play a game with her. One which she would win, but he would claim the prize.
“How much does 'a substantial amount' mean to you?” he asked.
“Hmm.” she said thoughtfully. “It could mean ten dollars, but it could mean ten thousand dollars, too.”
He smiled broadly at her. “For ten thousand dollars, I would expect something significant as a return on my investment. Such as a virginity.”
Her face fell. “I don't have that anymore. It was stolen from me, but I got my daughter instead!”
“Is she still a virgin?” he asked, making it a joke with the look in his eyes. “My son would enjoy that. I demonstrated the proper way to introduce a young lady to the pleasures of sex two summers ago, and he had practiced what I taught him twice since then, and he is still very good friends with both of those young ladies today, even though they are no longer intimate.”
“You want... you want my daughter... for your son?” she asked, stunned to her core.
“Yes, I do.” he replied. “I'm going to use her as a bargaining chip to get him into a college of MY choosing. None of the party schools he was looking at before.”
“But, your son?” she asked, confused. “You want her to give her virginity... to your son?” She looked at him, surprised to her core. “I thought you, well, men in general, I mean...”
“You thought I would want it for myself?” He looked at her with an amused glance. “I'm afraid a pretty little thing like her would have no interest in an old fossil like me.”
“That's not true!” Wendy said impulsively, then clapped her hand over her mouth to prevent herself from saying anything else.
“Really?” he asked, amused. “What does that mean?”
“It means she likes older men. Sam needs a father figure, and if her “father” was interested in her, in “that way,” well, I don't think she'd be too embarrassed to stop him. I think it figures prominently in her fantasies.” Wendy said, blushing from embarrassment. “She'd be REALLY mad if she knew I told you that.
“Hmm... That brings up interesting thoughts in my head.” he said softly, looking off into the distance for a moment. Then his eyes met hers again and focused laser tight. “All that is for after, though.” He smiled at her, letting her know with his eyes that SHE was his entire focus. “It's time for you to experience a few firsts.”
She looked at him, her eyes widening as he slid down, kissing her breasts and her belly in between them. He looked up at her once more as her wispy pubes tickled his chin.
“I get some firsts, too.” he smiled at her. “I'm the first guy to ever taste you.” He immediately put his whole mouth over her pussy, and began flicking her clit with his tongue while collecting the beaded moisture dotting her lips. “And the first one to touch you -HERE- (he let his index finger slip onto her asshole, applying very gentle pressure to test it tightness) right?”
She gasped and tried to wiggle her butt away from his finger, but he just smiled up at her and kept it in place.
“Oh my God!” she gasped aloud. “Don't touch me THERE!” she said frantically. “It's dirty!”
He moved up along side her and looked directly into her eyes. “I'm a dirty boy.” he said, then pushed his finger into her asshole to the first knuckle. “Are you a dirty girl?”
She thought about a long moment, not speaking, as she looked back into his eyes as well.
“Is that what you want?” she finally asked, her voice so quiet he could barely hear it. She was looking down at her lap. He out a finger under her head and lifted her head and made her look into his eyes. “You want me to be a dirty girl?|
“I want you to be what you are.” he said. “Be true to yourself.” He looked her right in the eye as he said it, letting her see the depth and truth of his words.
She was silent another long moment, trying to read his thoughts to see what he wanted through looking at him alone. She couldn't; his unwavering gaze staring back as her. He was unfathomable.
She thought about what he had made her feel with his touch, and decided in her mind she wanted more of it, but she knew what her mother thought about such girls who wanted such things.
“Is it okay if I...” Her voice trailed off, and she looked down again, but then quickly looked up once more. “Will you still like me if it turns out that I'm a slut?”
His face began smiling, his grin broadening long after she had seen the thought in his eyes. “I only want to be a slut for you!” she said quickly, then tried to look down again.
“I like you better as a slut.” he told her, catching her eye again. “MY slut!”
“I love you.” she blurted, then hugged him tightly. A long moment later, she leaned back and looked him in the once more. “You can fuck me any way you want. You want my asshole? It's yours. I'll even help you take Sam's cherry. You can give her to your son after, but I want you to be her first. You deserve a young girl as pure as she is.”
“Wendy, I...” he said, looking at her helplessly. “I don't know what to say.”
“Don't say anything.” she told him, then winked. “I'm going to be a slut for you right now. Don't spoil everything by talking.”
“You're willing to be MY slut? You'll do everything I tell you to do? EVERYTHING?” he asked, still not moving. “You're willing to do everything I asked of my late wife? She was a willing slut, too, and I took every advantage of that fact while she was here.” He looked at her again. “Your first act as my willing slut will be to give me your cherry asshole.”
“Oh God.” she whispered, closing her eyes. Then she looked him right in the eye. “Fuck my ass.” she whispered, then kissed him. “I give myself to you. Fuck me in any way you wish.”
He smiled at that. “I'm going to fuck in every single way I wish.” he told her. “I also want you to fuck me in every way that YOU wish, too!”
She smiled in response to that. “Okay!” she agreed happily. “Tonight, we do as YOU wish, and tomorrow night we do as I wish!” She looked at him and winked. “You'll get to see how much of a slut I REALLY am!”