Daddy's Bedtime Taboo Sex Stories

by Kelly Fleming

  "If I don't have my stuff out of there by the end of the month, I have to pay for another whole year! I can't afford it." Jenn sat on the couch and started to cry."

  I sat next to her trying to calm her. Clearly, the move was not going as well as she'd hoped.

  "What can I do to help?" I asked.

  "I don't know. I shouldn't have asked you up here. I'm so sorry." She started sobbing and turned her head into my shoulder. Her tears getting absorbed in my sweaty shirt. I put my arms around her. Damn she felt good. Her soft breasts pressed against me and I could feel my cock get a bit hard.

  "I tell you what," I said, "why don't I get the AC installed and we can sort out stuff and get your bed set up and do all the major stuff. If we hear about the key, I'll drive you and we can get the rest of your stuff."

  "Thank you," she said, her tears disappearing. We both realized I was still holding her.

  "I don't want to start yet. This feels good." She nestled further into my embrace and I kissed the top of her head. I pulled her up to me to whisper into her ear.

  "I like it too. Maybe too much." I said. Our cheeks felt incredible next to each others. I kissed her cheek and we slowly moved our lips closer.

  Our lips met almost accidentally and we kissed. Her thick pouty lips were as soft as petals as we enjoyed the moment.

  "Oh God," Jenn said, "I've wanted to do that for the longest time."

  "Would you think less of me if I said I wanted to also?" I asked.

  "Oh God no. I've wanted to be with you for the longest time. I just never thought it was possible."

  I kissed her again, this time stretching her against the couch as my hand reached up to squeeze her large round breast. Our tongues danced inside each others' mouthes as her hands moved up and down along my back. My cock was now straining against my shorts. Her hand moved down my belly and explored the hardness of my shaft as she traced the outline of my cock over the fabric of my shorts.

  "Mmmm," she moaned, licking the outside of my ear. The soft kissing was now replaced with more hungry urgency. She positioned herself beneath me and I centered my body between her legs. I moved in to kiss her again and my thick, hard cock ground into her. We dry-humped like that for what felt like half an hour. Kissing, moaning into each others ears, our pace quickened and I could feel the wetness of her eager pussy soaking through her shorts - and also mine. I reached around to grab her sumptuous ass and her legs wrapped around me, vice-like. More hurried and frenetic than before we continued dry-fucking each other.

  "Nathan, I'm about ready to explode!" Jenn cried.

  "Jenn, we need to stop," I said.

  "What's wrong? I thought you liked it," jenn looked at me with a disappointed glower.

  "I knew it. We went to fast, now you think I'm a slut. I know I am." she said, a tear streaming from her eye.

  "No honey, it's not that. I just think if we want to take this further we should..." I paused.

  "What is it?" she asked through her tears.

  "I think we should get the AC going. It's so hot."

  "Oh my God, I'm so sorry. I misunderstood. You're so right," she said, brushing her arm over her sweaty tear-streaked face.

  I got up from the couch, opened the window and I don't think I've ever installed an AC so quickly in my life. I plugged it in and after a quick shudder and quake, an icy blast started to fill the room.

  "Now back to the matter at hand." I removed my sweaty shirt and let the air cool me. My hard cock was straining through my shorts and I sat down next to Jenn. We continued kissing and I could see that the new temperature was having an effect on her. Her nipples were hard though her shirt. The sweat had soaked her and the fabric of the skimpy top was practically see-through. Her large dark nipples could dense the change in the air. They were about the size of hershey kisses and I let my finger feel them over the soft fabric of her top. Her hand went to my crotch and she felt my cock twitch with anticipation. With a quick adjustment, it was soon poking through the top of my shorts. The shiny purple head of my cock was just begging to be sucked. She unzipped me and I pulled my shorts down. The full ten inches of my cock was now on display as Jenn's eyes grew wide with astonishment.

  "Oh my God, honey. Your cock is huge! I hope this works." She then got down on her knees before me and let her lips and tongue go wild over my shaft. She took me slowly at first, getting used to the girth by running her tongue up and down the length of my swollen shaft, then allowing her mouth to swallow the head and about five inches of meat before a short gag came from her throat.

  I'd had fantasies before about me and Jenn, but I must say that this was way better than anything my imagination could have dreamed up. She tried to swallow my meat as much as she could while her small hand, barely fitting around the base pumped me like a pro.

  I could see her other hand was between her legs, rubbing at her own crotch.

  Jenn lifted up her head, "I can't keep on doing this, my jaw is beginning to ache. Come here."

  She pulled me further down on the couch and took my cock in her hand. She then lifted up her sweat-soaked tank top and put my cock between her enormous tits. She grabbed her breasts from both sides squeezing as my cock rose up through her cleavage and over the top of her shirt.

  Her heaving tits were smooth and sweaty, "Do you like that babe?"

  I moaned in approval.

  "I've never done this before. I hope you like it," she said as her hands picked up the pace.

  I moaned again in satisfaction as her hands increased the pace of her tit-fucking. She lowered her head and took about three inches, then four, then five in her mouth. My cock felt engulfed in hot, wet sweaty sex when I felt a twitch coming from my balls and the base of my cock.

  "Jenn, I think I'm going to...."

  "Oh yes babe. I want you to. Cum all over my tits," Jenn moaned.

  I couldn't control myself. I felt the tightness in the base of my balls erupt into a blast of hot cum. She kept pumping with her tits as sticky shot after shot of cock juice shot out my cock and onto her face, neck and tits. Her sweaty tank-top was also covered in ribbons of pearly cum. Truthfully, I didn't know I could cum so much. After my last spasm of seed, Jenn leaned forward and held me close.

  "That felt incredible, honey," I said trying to regain my breath.

  "It did for me too," she moaned, her hand still stroking my cock, coating it with my own cum. She once again took my shaft in her mouth, coaxing out the last drops of cum.

  Quickly she pulled away and stood up. Pulling down her tight black spandex shorts, she threw them aside and straddled my still hard, cum-covered pole.

  "Go slow," she whimpered as she guided my cock head to her sopping pussy. She lowered herself down on me taking inch by inch until she was full of my cock-meat.

  "Is that Ok?" I asked. I was about ready to cum again since she didn't let me "recharge."

  "Baby, it feels incredible! " Slow grinding rhythm changed to pounding thrusts as she quickly increased her pace. My nails were digging into the meat of her curves as she rode my shaft. Her sweaty cum-soaked shirt was in my face and she lifted her arms to let me take it off. Her gorgeous tits now released, I took her nipple in my mouth as my nails dug into the meat of her ass. The solid muscles of her rear were working hard and I knew I wouldn't last much longer. I arched up allowing as much length as possible to fill her cunt.

  "Oh Nathan! That's it! Fuck me with that huge cock! I'm so close to cumming! Oh God! Pound me! Tear me up with that shaft. Make me your little cock-whore!" Jenn panted.

  "Jenn. Honey, Where do you want me to cum?" I asked. I wasn't going to be able to hold off.

  "Inside me babe! Fill my cunt up with your hot cock juice. Oh my God!!! I'm cumming!!! Oh Fuck yeah." Her pussy gripped me like a vice as she heaved and bucked on top of me, slamming herself onto my cock repeatedly until she claimed her release. She finished her orgasm in a collapse on top of me as I shot another creamy load inside her.

  We regained our breath and looked
into each others eyes. We kissed slowly.

  "I think I could fall in love with you honey." I whispered.

  "Me too. I know it." Jenn sighed as her head fell to my shoulder

  "Maybe now we should put together the bed?" I asked. Jenn laughed.

  "Only after a shower," she whispered.

  Later I shall tell you about that shower.

  The End.

  The Ring

  Diana Summers was at a crossroad in her life. Fired from her high-powered job due to a political shakeup, recently out of a bad relationship, and exhausted from the circumstances, she had to shake herself from her doldrums. After weeks of hunting for work, during which her meager savings were nearly depleted, she was thrilled to hear from an employment agency that a job was available if she wanted it. Personal assistant to a somewhat reclusive painter was a live-in position that required her to move to the coast. The wages seemed generous, particularly since she would also receive room and board. "The employer's home is fairly isolated," she'd been told. And the gentleman was very selective. He required detailed background information on job candidates, and he was prepared to pay an appropriate wage to the right one.

  Diana wondered why she was the "right one" but a job was a job. Between her earnings and the room and board, she would be able to save quite a bit so even if she didn't stay, she'd be a better position when she left than when she started. So packing her practical wardrobe, she jumped into her old but reliable car and headed for the coast.

  After driving a few hours, Diana found herself in a beautiful, secluded part of the country. "Diana," she said to herself wryly, "meet rustic America. Let's just hope the cabin has a new roof." But when she finally found the turn into a magnificent gated driveway, she realized that rustic wasn't quite the word for her new home.

  Her surprise grew when she reached the huge stone house and was greeted at the door by a genuine butler. A dignified and attractive middle-aged man, he introduced himself at once. "Miss Summers, welcome. I am Julius. Mr. Darlington will be delighted that you've arrived on time. Please follow me." He led her into a formal living room, where a man stood at the window, his back to her. He turned to greet her and she was suddenly self-conscious, a state to which the confident young woman was unaccustomed.

  While Diana had been used to dealing with captains of industry and government leaders, she found herself unprepared for Oliver Darlington. Aside from being extremely attractive, his commanding presence could have put the most arrogant politician to shame. Not that he himself was arrogant; it was just that he was aware of his dominance and comfortable with using it. Nevertheless, he went out of his way to make Diana feel welcome.

  "Please sit," he said, offering her a very comfortable chair. "Julius, please bring refreshments for Miss Summers. She's had a long drive." Diana started to protest, but he reassured her. "It's no trouble at all, and I take tea this time of day, anyway. Relax after what was probably a tedious trip."

  Diana smiled in acknowledgement. "Well, it did seem as if I was heading straight for the drop off the face of the earth at one point."

  Immediately, concern registered on Darlington's face. "I hope you won't find it too isolated here. I plan on keeping you busy, but you will have time to yourself and civilization isn't too far a drive."

  "Mr. Darlington," she replied with a smile, "it's beautiful here, and I know I'm going to appreciate the peace and quiet. It's not what I'm used to, but I'd like to change that."

  "First, it's not Mr. Darlington, it's Oliver. And I appreciate your attitude. I understand that your last employment could be rather contentious, and you're wise to appreciate the beauty and opportunities that my home has to offer."

  As they had a light tea, Oliver explained Diana's new responsibilities in more detail than she'd received from the employment agencies. As a highly successful painter, he was very sought after and there was a great deal of correspondence, including requests for commissions (he didn't do them, insisting on painting only what he chose to paint), charity appeals (he was generous with his money but not with his paintings, which weren't trifles to be bid on by socialites), and solicitations from galleries who wanted to represent him (look into it, do due diligence, then we'll discuss it). And then there were those who sought personal appearances or face-to-face meetings. The media weren't the least of them, but there were also celebrity hounds, undiscovered artists, and would-be models. ("I'm single, wealthy, and under 75. You can imagine.")

  "You'll learn that my family has a reputation for mystery and eccentricity. And I'm known for wanting my privacy. Some people don't give a rat's tail about my art – they just want to say that they rubbed elbows with the weirdo. You are here to deal with them, to cover my back. And then there's the book project, but we can go over that tomorrow."

  He told Diana that unless they were traveling or he had visitors at the house, she should dress as comfortably as she wished. Being somewhat conservative by nature, her casual clothes consisted mostly of khaki slacks, jeans, and knee-length skirts, together with button-down or polo shirts, so that worked well for her.

  Oliver stood and said "I'm sure you'd like to see your rooms, get organized, and perhaps take a bit of a rest."

  Diana nodded gratefully. "That would be wonderful. I would like to unpack and freshen up."

  "Oh, there is one more thing," Oliver added casually as Diana started to rise. He took a box from his pocket and opened it to show her a delicately carved bloodstone ring. "I'd like you to wear this at all times while you're in my employment."

  Diana reached for the ring, then hesitated. She gave him a quizzical look and he continued "The ring has been a part of this house for generations. It needs someone to wear it."

  Okay, this is pretty strange, she thought, but she needed the job and what harm could it do, right? She made a joke of it, saying "Well, it is one of the stranger job requirements I've had, but it's certainly one of the more pleasant ones. It's beautiful, and I'll take good care of it."

  "Good. Now Julius will show you to your rooms."

  After slipping the ring onto her finger, Diana followed Julius as he gave her a brief tour of the house. At one point, Diana started to feel somewhat odd. Not ill, or even uncomfortable, just odd. She brushed the feeling aside as fatigue and stress from wanting to succeed in her new position. Finally, they arrived at a suite of rooms that were beautifully decorated, with a stunning view of wooded hills.

  "Dinner will be at 7:30, Miss." And Julius left Diana to prganize herself in her new quarters.

  After putting away her clothing and belongings, Diana took a nap. When she woke near seven o'clock, she had faint recollections of a dream that left her vaguely disturbed. The odd sensation she'd felt earlier was still with her, perhaps even intensified a bit. Noting the time, though, she brushed it aside and dressed for dinner. Not knowing how formal the meal would be, she settled on a simple shift dress and sandals.

  Arriving at the dining room, she saw that the small table was set for two, and she heard Oliver's step behind her. As he held the chair out for her before taking his own seat, he smiled and gave her a wink. "Arriving a step before your employer will always earn you points."

  Julius served a delicious meal. (He'd also prepared it, making him more than worth his weight in gold, Oliver told Diana). Although Oliver's lighthearted stories about the house and his ancestors should have put her at east, it seemed to Diana that their close proximity intensified the odd sensation that she'd had since before her nap. That was ridiculous, though, she reassured herself. It surely was just nerves and a new environment.

  After dinner, Diana still fell a bit off. A little lightheaded, a bit tingly, she couldn't quite put a finger on it. But while Oliver spoke, rather than focusing on his words she found her mind drifting to extremely intimate thoughts involving him. Her eyes fell on Oliver's strong looking hands, and she imagined them traveling up the insides of her thighs. Forcing that thought away, she looked into his eyes, only to imagine a hungry look in them a
s he watched her strip for him. Irritated with herself, she lowered her gaze to his mouth, which did no good whatsoever. All she could think of now was how his lips would feel on her now stiff nipples.

  She forced her lust away, unaccustomed to not being in control. Granted, Oliver was an extremely attractive man. Okay, attractive was an understatement. Make that magnificent. But Diana had never been a slave to passion before, and the strong, distracting pull she felt toward Oliver was uncharacteristic.

  "Get a grip!" she silently ordered herself. "The last thing you need is to get involved with another man right away, particularly if he's your boss!"

  With great effort, she managed to subdue the strange feelings. However, when she again met Oliver's eyes, equally strange was the look of knowing satisfaction that she found there. It was as if he had deliberately incited her lust and was pleased at her response. Shaking off that thought as impossible, she turned the conversation to his art, mentioning a few pieces she had seen in museums.

  Oliver suggested that they move to the library to enjoy an after dinner drink. She followed him to an impeccably furnished room that seemed to invite one to relax. The decoration was masculine enough for a man's private retreat, inviting enough to make a woman feel comfortable, but definitely a male domain.

  Diana took a seat on a sumptuous leather sofa and Oliver sat facing her on a generously proportioned chair that seemed to have been made for him. In fact, she thought, he looked rather like a pasha in his throne. She was very aware of his air of authority and imagined that he frequently, if not always, took the upper hand in his dealings with others.

  The discussion turned to their mutual love of reading, Oliver having offered Diana the free run of the library, when she suddenly became appalled at the posture that she had unconsciously taken. Leaning back onto the sofa with one hand behind her head, and sitting on one bent leg with the other stretched out to the side was inappropriate enough. She realized, though, that her skirt had crept up and that she was giving Oliver a view, obstructed only by her panties, of her crotch.