"Relax," he told her. "It will hurt less if you are relaxed when I put my cock in you." She willed herself to loosen, open up. After all, she had begun fingering her ass in preparation to take him, but it was different with a man's fingers, which were so much thicker than her own. She felt the finger slide past her sphincter and it left her with an odd full sensation. Then she felt him pull his finger out, and insert two fingers at the same time. He was slow, and patient, allowing her to get used to the sensation of her ass being stretched. He pulled his fingers out and she heard him lubing his cock. I don't know if I'm ready for this, she told herself, but it was too late.
She felt the head of his cock at the entrance to her ass. He pushed gently and it popped past her sphincter, lodging just inside her asshole. She sighed.
"How does that feel?" he asked her.
"It feels OK, try going a little deeper," she replied.
He pushed his cock in a little at a time, pausing to give her time to get used to being filled up. It was a little painful but she pushed back against his hips to let him go deeper and sooner than she expected, she felt his balls against the back of her ass, realizing with wonder that he was fully lodged inside her. She wriggled against him, trying to see how it felt, and found that there was no pain. She was astonished.
"God," she said, "that feels fantastic!" He needed no further urging. He started fucking her slowly but the tempo soon increased until he was pounding his cock in and out of her virgin ass. He felt himself close to cumming and the thought of spurting inside her ass made him pound her even harder. Then it was over, he felt the cum drawn from his balls and up through his shaft and felt himself spurting inside her again, groaning loudly as he came. She felt his hot cum shooting into her and started cumming again herself, unable to stop the spasms that racked both her ass and her pussy -- the most incredible orgasm she had ever had, so intense she thought she would faint with pleasure, as she bit her hand to stop from screaming.
He waited until they had both finished cumming before he withdrew his now-softened cock from her ass slowly and smiled at her in the dark. He placed his hands at her asshole and felt his cum dribbling out of her. He knelt down and licked her clean, taking his cum into his mouth, then stood back up and turned her around, kissing her deeply, letting her take his cum into her own mouth. He heard her swallow the sweet cream in the dark, and he smiled again.
"Now your ass is really mine, to take whenever I want," he said. "You're an incredible fuck, you know that?"
"Was that worth waiting for?" she asked, smiling back at him. She knew that she would be sore later, and probably feel worse in the morning, but oh god she loved his incredible cock, and knew that she would make herself available to this man whenever he wanted her. The thought gave her that incredible spasm of pleasure and pain deep in her belly again, and she felt herself getting wet all over again too, and knew that she was lost...
The End.
Punished and Pleasured
I pause by your front door and check myself in a small hand mirror. Nothing stuck in my teeth, just a touch of gloss on my full pink lips. Flaming auburn hair falls in a riotous mass of curls past my curvy hips. The flared skirt of my black knit dress ends just above the knee and the neckline plunges almost low enough to reveal glimpses of my bra when I move.
I knock before I lose my nerve. You open the door and a wave of desire hits me with visceral force. I lick my lips in nervous anticipation and I can see my own lust mirrored in your eyes. You grasp my hand and lead me inside, never breaking eye contact. Your hair is still wet from the shower and I can smell a sexy combination of warm skin and a trace of cologne. You swing the door shut behind me and press me back into the cool wooden surface knowing I love your domination of me. Your big warm hand grasps my hip while you bury the other in my curly hair. I am glad for the support of the door at my back and your strong chest pressed against me. If you kiss me I might just melt into a puddle on the floor.
Almost before the thought crosses my mind your lips brush mine in a feather light caress. Your gentle kisses only tease me and leave me hungry for more. Feeling a little aggressive, I nip your sexy lower lip and sooth the sting with a flick of my tongue. You growl against my mouth and deepen your kiss, giving me what I want. I pour all of my passion into the kiss, meeting your tongue in a duel of lust. I clutch your broad shoulders with trembling fingers. Your hand moves up my ribs to my breast. My nipples harden into tight little points and when you brush one with your thumb my gasp is swallowed by your sensual chuckle. You have such power over me. You break our kiss and step back. The gleam in your eye makes me shudder with both delight and apprehension.
"You have been a very naughty girl this week." Your voice is low and sinister. I trust you with my life but the dangerous look you give me is intense and my punishment will be difficult. "You sent me lots of naughty messages while I was trying to work." I remain silent knowing that if you want me to say anything you will ask. You walk to the couch and sit down on the center cushion. "Come here." You pat your lap and my already wet little pussy weeps with helpless moisture. This is my favorite punishment.
I walk toward you and raise my flared skirt up to my hips revealing black lace panties. I drape myself across your lap and I know you like my panties. They are boy-cut and my plump cheeks peek out at the bottom. You caress my full rounded ass and run your fingers up and down the soaked crotch of my panties. My breath comes quicker when you slip a finger inside to slowly rub my clit. You slide your finger up and press the now wet tip against my asshole. I moan a little and move my hips trying to make you push your finger in but just when I feel my tight little hole relax to accept your entry you pull back.
"Not yet my naughty little slut, first we have to take care of your punishment. I think fifty should be enough to teach you to behave yourself." I shiver and try to prepare myself. You have never made me take fifty before and I am just a little frightened and even more turned on at the same time. I feel you pull my panties down to my knees, leaving my creamy round cheeks bared to your hungry gaze. When the first slap falls my breath catches in my throat and you quickly follow up with four more hard swats to my right cheek. My eyes water but I remain still and silent. I want make you happy so I have to take my punishment like a good slave. Five more stinging slaps and my right cheek is a bright flaming red in contrast with the left one, still a cool creamy white. You caress the hot flesh letting me know you are pleased with me. Ten hard, fast slaps land on my left cheek and I strain to keep quiet. You like it when I cry but not too soon. My arms erupt in goose flesh and I whimper low in my throat when you deliver ten more sharp slaps to the right side. Tears fill my eyes and the next ten swats land with sharp cracks on my left cheek. I cry out softly but I don't try to squirm away. With your free hand you reach inside the top of my dress and into my bra. The last five slaps are delivered slowly, harder than any you have given before and you punctuate each with a rough pinch to my right nipple. Tears trickle down my cheeks and I am quietly crying in earnest now. You find my left nipple with your large blunt fingers and I finally break and cry out loud as you administer the final five swats and pinches.
"Good girl. Good girl." You murmur quietly, caressing my flaming ass. You guide me off your lap and then to my feet. I am still trembling so you draw my panties the rest of the way to the floor and help me step out of them, leaving my sexy stilettos on my feet. You strip my dress over my head to better admire your work. Dropping kisses on my shoulders you guide me ahead of you into the bedroom. I lean forward to pull back the fluffy comforter and sheet, careful to present you with the best view of my sore ass and wet pussy.
You softly kiss the places you so recently abused. I moan a little at the soothing pleasure of your actions. You unhook my bra and turn me to face you. You love my breasts. They are very large with big sensitive nipples. You slip the straps off my shoulders and follow the receding lacy fabric with your hungry lips. The bra hits the floor at the same moment you throw me back onto your big
bed and devour my tight aching nipples. You suck and bite and soothe with your tongue in devastating combinations. I am panting and I can feel the slick moisture from my throbbing pussy run down the crack of my ass. You kiss slowly down my heaving torso.
"Oh god! Please lick me!" I squeal in a hoarse voice. You chuckle against the soft skin of my belly, loving how badly I need you. Your strong hands guide my knees high up to my chest. I grasp my thighs and you look at me. I am spread open and exposed to your view, folded nearly double with my knees on either side of my big breasts. I love this feeling of being helpless and exposed to you.
You strip off your clothes and open the bedside drawer. You retrieve a bottle of lube and place it on the bed next to me. I close my eyes and pluck at my nipples as you lick slowly all over my pussy. You spear your tongue into me and swirl it around, caressing me deep inside. Your fingers dig into my still stinging ass. I start to babble incoherently when you trap my clit between your lips and batter it with the tip of your tongue. Just when I am about to cum you pull back leaving me panting.
"Please fuck me! Please! I need to feel your big cock stretch me open." The words are barely audible whispers of desperation and trail off into nothing when you rest my ankles on your shoulders. I can feel you forcing the broad head of your huge cock against my very aroused pussy. I am slick and dripping wet but still you have to work hard to get it in. I make little whimpers of pleasure and pain as my tight little cunt stretches to accommodate your incredible girth. You feel so good. I finally feel your pubic bone bump my clit and my hips twist and roll uncontrollably, needing you to fuck me faster.
You move slowly, fucking me at your own pace with long smooth strokes. Every time I get close to climax you stop. You hold my hips still and kiss me deeply or suck my tingling nipples. I can feel the muscles of my pussy ripple up and down the shaft of your dick. Just when I am sure I will go crazy if you don't let me cum you slide all the way out. When I hear the little snick of the cap on the lube I know what you plan to do next and I could almost cum just imagining it. You apply the slippery liquid liberally both to your rock hard dick and my very tight asshole. I feel you slide the tip of your dick over my asshole but you don't try to push inside yet.
"Tell me you want me to fuck your ass. I want to hear you beg for it." You bump a little harder against my tightly closed asshole but I know you won't fuck me yet, not until I give you what you want. I want it so bad. You have never tried to fuck my ass and I am frightened and aroused at the same time.
"Please fuck my ass! I-I need your big cock inside me! Please! I need to cum so bad! Please fuck me! Aaaahhhh!" With each desperate word that falls from my panting lips you push harder against my asshole. My scream of combined pleasure and pain echoes off the walls when you finally force the head of your dick into my ass. "Oh shit! You feel so big! You are splitting me apart! Oh God! Please don't stop!" You lower my legs to your waist and I wrap them around you tightly. Your entry seems never-ending but finally you have your huge cock buried fully in my asshole. It feels so good and in my passion I bite the corded muscle where your shoulder meets your neck. You growl and hold yourself still above me.
"Now fuck me! I want you to cum on my big dick." Your words spur me to even greater heights of passion. I fuck you hard and fast working my tightly stretched asshole over your thick shaft. My squeals ring in our ears. I reach down and rub my slippery clit, desperate to cum. I force your cock full length into my ass and scream out loud when my orgasm hits me. You begin moving again, full-length powerful strokes. You slam deep in my ass and my orgasms chain together in incredible waves. You throw your head back and roar as your hot cum shoots up inside me. The pleasure is so intense that my vision goes gray at the edges and my body flashes hot and cold. You collapse on top of me, slowing your strokes, letting my body calm and come to a stop. Finally we are still and we lay there for a moment with your still thick but softening dick in my ass.
"So how naughty do I have to be to get you to do that again?" I whisper mischievously in your ear once I can find the words to speak. Your exhausted chuckle against the side of my neck tells me we will be doing this again very soon.
The End.
Perfect Assistant
Frank was getting ready for his annual 3 day trade show in Chicago. Usually he had his salesman, Brian, go with him but this year he is down with a bad cold. Frank decided he would ask Amanda, his executive assistant to go with him and help him out.
Amanda came to work for him about 2 years ago, soon after she got married when they realized they would need 2 incomes to make ends meet, She has silky long dark brown hair that she would let hang loose, and she looked so beautiful when her hair swirled around her turned up nose and pouty mouth. Frank had come on to her a couple times but he got nowhere. She let everyone in the office know she was a happily married woman.
She had a picture of her husband on her desk and he looked like a nerd. Frank thought if he could just get to fuck her hot pussy he could show her a much better time than her wimpy husband.
"Amanda, I need you to do the trade show with me in Chicago. You know our products as well as Brian does, and you would add a little glamour to our sales booth."
He could see a slight blush. "Now Frank, you know I'm a married woman and it would not be proper to spend 3 days out of town with you."
"But I need you Amanda. Brian is too sick and I can't do it alone."
"I don't trust you Frank. You have tried to get fresh with me several times."
"This would be strictly business."
"If I went with you, there are a few things I would insist on."
"What are they?"
"First we would have separate rooms on different floors."
"No problem."
"And no socializing. We could have dinner together to discuss the day's events, but after that we would each go back to our separate rooms."
"I agree."
"Also, no sexy stuff during the day; no touching or flirting with me."
"Scouts honor."
"OK I'll go with you but only because Brian is sick." Frank turned his back before she could see his satisfied smile.
On the plane to Chicago Frank was the perfect gentleman. He found out a little more about her but mainly they talked business. A little while later the stewardess came bye asking them if either one wanted a blanket. Amanda said no we don't. That little bitch still doesn't trust me, Frank thought.
When they arrived at the hotel, Frank went directly to the hotel check in clerk while Amanda waited for the cab driver to unload the luggage. Frank offered the clerk a hundred dollars to go along with his little scheme. Frank then paid off the taxi driver and they went to the check in counter.
"We have reservations for 2 rooms; I'm Frank Hawkins and the other room is for Amanda Collins.
"I'm sorry sir; there has been a slight mix up. We have both of you booked in the same room and the hotel is full because of the trade show. To compensate we have given you a one bedroom suite at the same price, and again I apologize for the mix up."
"I'm not staying in the same room with you Frank."
"It's OK Amanda, I'll sleep on the sofa and you can have the bedroom to yourself." That seemed to put her a little more at ease.
They unpacked and had dinner, with a bottle of wine, in the hotel restaurant. After that they went to the hotel bar and had a couple drinks and discussed their marketing plan.
"It's getting late Frank; I think it's time we left."
"Let's have another drink first."
"No Frank; I know what you are trying to do. You're trying to get me drunk so that you can have sex with me. Well, that's not going to happen."
Frank didn't think he had been that obvious. They went back to the room and got ready for bed. She changed in the bedroom into her nightie and Frank stripped down to his boxer shorts in the living area. She had the bedroom door closed.
"Amanda, I'm coming in, I have to use the bathroom." She was sitting at the vanity brushing her ha
ir. "You are so beautiful Amanda; how about a little goodnight kiss?"
"If I kiss you, will you go away and leave me alone?"
"Yes Amanda."
She stood up intending to give him a quick kiss. Frank grabbed her by the waist pulling her body tight against him. He knew she could feel his hard-on. He kissed her hard forcing his tongue in her mouth. She squirmed against him trying to break free. All that accomplished was his cock was now sticking out of his boxer shorts and probing her nightie, looking for her pussy. He held her close massaging her ass.
"Frank, you sex maniac, let go of me and get out of my room."
He continued to kiss her and brought one hand around to massage her breast. He could feel her hard nipple pushing into his hand.
"Frank, I'm warning you, stop touching me or I'll call hotel security.
Now he brought his hand down to massage her pussy. The nightie over her pussy was a little wet from his precum, but there was more moisture than just that. Her pussy was also adding to the moisture. He was able to get maybe an inch of his finger into her pussy through her nightie and started finger fucking her.
"Frank let go of me, I mean it."
He gently pushed her back against the bed, and when she fell backwards, her short nightie slid up higher allowing Frank to get his cock underneath it. He pushed it up to her pussy but he didn't try and penetrate her. He teased her by rubbing his cock head against her pussy lips.
"Frank, quit that, get off me."
Her pussy was very wet and he slid into her easily. She might be saying no but her body was saying yes.
Frank fucked her slowly but deeply, letting her relax and get used to his cock. Her pussy was very wet and she started pushing back every time he pushed in. He didn't think she was even aware of it but she started thrusting against him faster and faster as her orgasm built. She groaned and dug her fingernails into his back as her orgasm hit. Once her breathing returned to normal she said, "You raped me, you bastard; now get out of my room."
Daddy's Bedtime Taboo Sex Stories Page 12