Daddy's Bedtime Taboo Sex Stories

by Kelly Fleming

  Told the truth.

  She was right. He was a people-pleaser, had been all his life. It was such a default mode to him, he did it without thinking. He did anything and everything to fit in, to be liked. One time, on a trip to South Carolina, he'd even taken it upon himself to speak in a southern drawl. The funny thing was, he wasn't even aware of it until someone he was with pointed it out to him. Even now, that he was out West, he felt an urge to go buy himself a cowboy hat.

  Well, what did it matter? He'd have fun tonight. If he could just focus on having fun, that was. Too often, when he had a chance at an attractive woman, he blew it. Performance anxiety, he supposed. He tried so hard to please her, to be the lover of her dreams, that all he ended up doing was cumming too soon, deflating too soon. One time, when he had a sexy Italian woman on her knees before him, her lips on his cock, he felt his manhood shrink, grow soft. He was worried that she might not like his dick, that he wasn't big enough, wasn't handsome enough.

  The Italian woman slapped him, stormed away. She was insulted, and told him so. No man had ever gone soft while she sucked him before. He tried to stop her, tell her it was his fault, it had nothing to do with her. He was just nervous, insecure.

  But it was too late. She was already gone.

  ¦

  "So, how was your day, Brian?" she asked. It was seven thirty. They were sitting at the little round table by the window, which overlooked downtown. There was still a lot of activity on the streets below, but things were starting to mellow, at least momentarily—another workday having come and gone. Time for the residents to go home to their families for a quiet evening, or change into something more comfortable for a night on the town, or go to some bar and get plastered, bemoaning their mistakes, their rejections, their choices, their lost opportunities.

  "Good," he said. She had bought a bottle of wine, and it stood there, between them, on the table. He poured himself a glass of it, offered to pour some for her. She nodded, held out her glass. "How about you?"

  "Jesus," she said. "I must have spent about two thousand dollars today. I never realized Denver was such a great shopping town. I'll probably spend twice that much tomorrow."

  Yeah. He'd kind of guessed she was rich. She had that feel to her. He looked out the window again. In the distance, to the west, the high peaks of the Front Range glistened like diamonds under the setting sun. He wondered if he'd get a chance to drive up into the mountains before he needed to head back East. He hoped so.

  "So," she said, and stood up. She had downed her glass of wine already. "You ready to fuck?"

  She wasn't one to beat around the bush, was she?

  He should have just said yes, gotten lost in the moment, let her have her way with him, this luscious blonde whom he'd met by chance on his trip to the West. And all because he was afraid to fly. His boss had scoffed. "Flying is the safest way to go," he'd said, but he didn't mind sending Brian on the train. "Enjoy the ride," he'd said with a laugh.

  But he wasn't able to get lost in the moment. He wasn't able to forget the things she had said to him on the train.

  "How did you . . . how did you know?" he asked her. "I mean, how could you tell? You know, I mean . . ."

  "How could I tell that you're a spineless people-pleaser, a phony, a fake?" she asked. He winced at her words. Why the hell did she want to fuck him? And what's more, why did he want to fuck her?

  She took off her blouse, revealing a white lace bra. Her tits looked great, encased in that bra. D-cups. Well, okay—so there were good reasons why he wanted to fuck her. . . . But that still didn't answer the first question.

  "Let's just say I have a knack," she went on, as she unzipped her slacks, pulled them down her long, toned legs. She had the legs of a colt—she had to be close to six feet tall, nearly as tall as he was. "I'm able to recognize people who are conflicted, who don't allow themselves to be real. I saw it in you right away, Brian."

  "But . ."

  She went to him, motioned for him to raise his arms above his head. He did. She took his shirt off, flung it onto the floor. She leaned in to kiss him. He wanted to push her away, talk some more. His whole life suddenly felt like a joke to him, a stage play, a facade.

  But her lips were so soft and insistent. Her tongue so lively and skilled. How could he resist? They kissed for a long while, and she ran her long, manicured fingernails along his chest, scraping his nipples, twirling what little chest hair he had. She tasted so good, much better than the wine. And she smelled good, too. What was that perfume she was wearing? It was intoxicating, heightening his arousal.

  Next thing he knew, she was undoing his belt, unbuttoning his dress pants, pulling them down. Before he could get his bearings, his briefs were down at his ankles and Susan was squatting before him, his cock in her hand, as she smiled up at him.

  "I love giving head," she said.

  He swallowed, took a deep breath. He was only five and a half inches. He had always been ashamed of that. Would she disapprove? Maybe she figured he was only half-erect, and when she played with him more, he'd grow and grow and grow.

  But he wouldn't! He was fully erect now!

  He felt her lips embrace his shaft. God! It felt good, too good. But she was too beautiful, she had probably fucked guys twice his size. She could easily walk into any bar in LoDo, right now, and get any guy she wanted. Why the fuck was she with him? He couldn't compete with those guys. He couldn't—

  He felt himself deflate, as though someone had stuck a pin in his shaft, letting out all the air and blood and hormones. His cock shriveled up in her mouth.

  "I'm . . . I'm sorry, Susan. I just got, um, a little nervous. I . . ."

  She stood up, silenced him with a kiss. A good kiss, with a lot of tongue.

  "It's okay," she said. "Don't worry about it."

  How could she be so nice, so understanding? He guessed she'd put her blouse and slacks back on, race out of the room, and go find some other guy, some better guy, with whom to spend the night. And besides, she'd belittled him already, on the train. Why the turnabout now?

  "Lie down, on the bed," she said. He did. She reached behind her, unhooked her bra, let it fall away. Her breasts were magnificent. And they were as tanned and bronzed as the rest of her. Next, she slid her panties down her legs. Her mound was shaved, hair-free. She was perfect, really. But all this knowledge did was make him even more nervous, made him feel even more unworthy of her.

  He felt her hand on his dick, then her lips. Surprisingly, he became good and stiff again. Yeah, all five-plus inches. But her lips felt so good on his shaft. If he could just lose himself in the sensations, let himself give in. That's what she wanted of him, wasn't it? To let go? Not to worry so much about pleasing others? To just be himself?

  He moaned as she licked his balls, and squeezed his shaft with her hand at the same time. Then she let go, scraped her fingernails along his underside, teasing, tantalizing. Suddenly he felt a surge, a rushing river, deep inside him. No! Not this. Not now. He'd let himself go, gave into the pleasure, and this was the result?

  "Shit! I'm cumming," he said.

  She stopped fondling him, leaned forward, put her mouth over his cock, and drank him in as he squirted into her mouth.

  "Mmm, you taste good," she said when he had finished. She licked her lips.

  "You're not mad?"

  "Mad? Why should I be? Besides, we've only just started. I'll get you hard again in no time, trust me. Want me to show you?"

  "Yes, please." God, he was pathetic. He really was.

  Again she sucked him, again her fingers and her lips worked their magic on him. He loved the way her long blonde hair looked, loose, unencumbered, as it hung low over her face and tickled his stomach, his thighs, his groin. A blonde waterfall.

  Sure enough, he was hard again.

  She got up, went to her handbag, pulled out a condom. She bit into the wrapper, freeing the condom, and then draped it over his dick. He felt so stupid. He felt like a child, a boy—his dick
was too fucking small to fill out the condom. It was made for a man, with a real dick, not a damn mini joystick. He was sure it wouldn't fit properly. But it did fit, and once again, she gave no hint, no sign, of disapproval with him.

  She lowered herself onto him, and even through the condom he felt how moist she was, how warm and aroused her pussy. She was ready for a good fucking, wanting him to pleasure her, to bring her over the top. But could he? How did she like it? Slow or fast? Soft or hard? Should he thrust into her, or just lie back and let her ride him?

  He felt conflicted—there were so many options! So many ways to screw this up. And if he screwed this up, he doubted she'd remain patient with him. He had to do his part, had to give her what she wanted.

  But then she was pulling out of him. No. That wasn't accurate. He had shriveled out of her. She had been riding him, rubbing her clit against his shaft, but now, there was no shaft left. He had deflated again, his cock turning to Jell-O. It had turtled up, gone back into its shell.

  He couldn't look at her. He turned his face away. He desperately wanted to cover up his nakedness, too.

  But as he sat up, ready to make a beeline for his pants, she held him in place.

  "Huh-uh," she said. "You're not gonna run from this one, Brian."

  She was looking at him the way she had in the train, her eyes probing, searching, scanning. His physical nakedness felt like nothing under the weight of that stare. She was seeing way past his skin, his floppy failure of a cock. She was seeing straight through to his heart.

  "You're gonna talk to me, Brian. I told you earlier that I think I can help you, remember?"

  He just sat there.

  "Remember?"

  Yes. He remembered.

  "How old are you?"

  "Thirty-two," he said. He was ashamed to admit it. Shouldn't he have accomplished something of real value by now, by the age of thirty-two? But what had he accomplished, really?

  "How old do you think I am?" she said.

  Shit. He hated when women asked him that. You could never give the right answer. If you guessed too old, they were insulted. If you guessed too young, they might be flattered. But they might be pissed, too—for a whole host of reasons. What could he say?

  "I'm forty-six," she said.

  Forty-six? No way! She looked his age. How could she be forty-six?

  "I used to be like you," she said. "Always wanting people to like me, to like what they saw when they looked at me. I wanted to walk into a room and see all the guys' heads turn. I wanted to see tents in the crotches of their jeans and know I was the one who had put them there. So you see? We're really a lot alike."

  "But I . . ."

  "You need to get your head out of your ass is what you need, Brian," she said. "You're actually a cute guy, do you know that? And I know what your problem with your cock is. But it's not too small, Brian. It'd work just fine if you'd let it."

  He was speechless. But underneath it all, he felt redeemed. She had given him a compliment. She had even complimented his cock. Maybe he wasn't so bad, after all.

  She shook her head, sighed. Had she noticed the slight change in him, the turn his thoughts had taken? Was he really so transparent?

  "It shouldn't make a fucking difference, one way or the other, what I think of you, don't you know that?"

  No. He didn't. He really didn't know that.

  "You have to like yourself, Brian. The fuck with me or anybody else. But first, you have to know yourself. It's kind of hard to like someone if you don't know them first. You spend so much time worrying about measuring up to everyone else's expectations, trying to fit in with whoever you're with . . . how can you even know what you want?"

  Yeah. Like the way he wanted to buy a cowboy hat today, the way he spoke "southern" while in Carolina. The way he said words like "yo" and "cool" when he was around people who talked that way. He normally did not, but if the people he was with did . . .

  He suddenly felt like he needed to share something. It was mind-boggling that he hadn't even noticed these qualities about himself before. He felt them, maybe, suspected them. But he hadn't ever taken a step back and looked at himself objectively.

  He laughed—not out of joy, but out of something else—regret. Longing. Wistfulness.

  "When I was in high school," he said, " I really wanted to join the tennis team. I hadn't really played tennis much, but I always liked it when I watched it, y'know? The angles of the game, the symmetry, they appealed to me somehow. But when I told my dad about it, he told me I couldn't. He said tennis was a sissy sport, and if I wanted to go out for a team it should be football or basketball—something like that."

  "So what'd you do?" Susan asked. But her expression told him she already knew the answer.

  He shrugged. "I didn't go out for the team. Didn't go out for anything."

  He expected her to flame him again, tell him he was a sorry excuse of a man. But she just sidled in beside him, snuggled up to him, and kissed his cheek. He couldn't figure her out. As soon as he thought he had her pegged, she did something to throw his entire picture of her out of whack.

  "What was that for?" he wanted to know. He liked the feel of her body pressed firmly against his. Damn, she was beautiful. He still couldn't wrap his head around the fact that she was pushing fifty years old.

  "Like I said, you remind me a lot of myself."

  He snorted. She seemed as different from him as anyone he'd ever met. She was confident, assertive, went after what she wanted. She was real, not a phony like him. Not someone who changed her speech patters to fit in with the crowd, or listened to counsel she didn't agree with.

  "I want to show you something," she said.

  She slid away from him, stood up, padded across the floor to her handbag. He admired her nakedness, the way her tits didn't sag, the firm roundness of her butt cheeks. He wondered if she'd perhaps been a model when she was younger.

  She pulled something out of her bag, came back to the bed. Again she cozied up beside him.

  "Look at this picture," she said. It was clearly an older picture—it had an old-school look about it. It was a photo of a young woman, homely, with a bulbous nose, glasses, stringy brown hair, and crooked teeth. Her breasts were small, and she was skinny. Tall and skinny.

  "So?" he said. "Who's that supposed to be?"

  She smiled. "Me."

  He blinked, once, twice, several times. He looked at the photo again, then at the beautiful blonde beside him. How . . .?

  "That picture was taken of me when I was going to college. I was twenty-one. Not so easy on the eyes, was I?"

  He coughed, and she laughed.

  "Exactly," she said. "Remember how I told you I wanted to be pretty, wanted the guys to be attracted to me, wanted people to like me? Well, I felt like those were just pipe dreams. I mean, I was ugly. So I just applied myself. Got a 4.0 GPA, and made a success of myself. I wanted to make a lot of money, and I did. You know why?"

  He just sat there, waiting for her to go on.

  "So I could save enough to get my face worked on, to get my tits worked on. These aren't real, you know." She squeezed her tits.

  "They look real enough," he said lamely. They had felt real, too, when he'd touched them. At least he'd thought they had.

  "Thank you," she said. "Like I said, I earned a lot of money. Went to the best surgeons. These aren't real, either," she said, and smiled, showing off her mouthful of white, perfect teeth. "This mouth cost me a fortune, Brian. And you already know I'm not a natural blonde."

  So it seemed, yes . . .

  "And I had my nose done. They made it too pointy, but it's better than what I had, don't you think? And of course the fingernails are fake. And I've had work done on my face, and my ass . . . So you see, Brian, there's not much real about me, is there?"

  He said nothing. What could he say?

  "You know, I don't usually show this picture to my lovers." She looked away from him. "I just let them think I'm genuine, that it's their lucky n
ight, y'know? Maybe that's why I haven't had a serious relationship with anyone, all these years. I'm too afraid to let them see me. The real me."

  "But you showed me," he said.

  "Yeah." She looked at him again. "So . . . do you want me to leave? I wouldn't blame you if you did."

  He swallowed. No. He didn't want her to leave, and he told her that. He also said: "Besides, you remind me a lot of me."

  She laughed, gave him a nudge. But it was a good nudge, a friendly nudge.

  He kissed her cheek, her pointed, surgically-repaired nose, her forehead, her lips. At first she was nonresponsive, just letting him kiss her. But then she kissed him back, and there was a hunger in her, a passion. It radiated through her, through her lips, which, like a conduit, passed it on to him.

  He kissed her neck, worked his way down to her fake breasts—which looked and felt so real. Imitation to mimic reality. A show to look good, to fit in with what society wanted, to get the approval of others. He felt a wave of compassion for this woman, and, for the first time in years, for himself.

  He stuck out his tongue, licked her stomach, down to her belly button. He inserted his tongue into it, and she giggled, reached down, ran her fingers through his hair.

  He kissed her hips; her smooth, hairless, mound; her inner thighs; and then licked the lips of her vagina. She was wet, so wet.

  "Mmmm," she purred. And he realized, he wanted her more than he had ever wanted anyone. He wanted to fuck her like there was no tomorrow, to let loose as he never had before.

  "Fuck me, Brian," she said, as if reading his thoughts.

  And he did fuck her. He fucked her deep into the night. They fucked missionary style, then she rode him, then he took her doggy style, then standing up. And not once did he worry about his dick, his shortcomings as a lover, his old insecurities that had always risen up in the past, stripping him of pleasure. He just fucked her, pleasured her, loved her.

  And when it was through, when the fire and lust of lovemaking had been replaced by the easy, pleasurable glow of post-coitus, they snuggled together on the bed, the first, shy hints of dawn streaming through the window, the city slowly waking up, coming to life, like a great, giant organism recovering from a restless nap. Voices rang out from the street, rising, filtering into the room. Car horns honked. Another day. Another beginning. Another chance.