As Todd was listening to Cindy's voice, he was playing with the Helix. He slid it into his ass, relaxing just as she was telling him to. When she said she was all the way in, he pushed the Helix all the way in, shouting out with pleasure as he did. When she said she was going to fuck his ass a few times, he did the same with the Helix, enjoying every stroke. He was moaning out loud now and was, as his wife described, pushing back against the pleasurable intrusion.
"Don't forget about my hand gliding up and down your shaft, just the way you like it. Kind of twisting at the tip and rubbing my palm over the head. I know that you love this and with me fucking your ass you're getting so very turned on. Don't cum yet baby. Hold out for a bit. I want you to really want to cum. I want you to beg me to let you cum. Oh that's a nice glob of precum you have on the tip of your beautiful cock. You know how much I'd love to lick that off, but tonight I'm going to work that into your shaft so my hand glides up and down so much smoother. Feel my fingers pounding harder and deeper into your ass? God baby, you want to cum, don't you? You can feel the pressure building up. Let me just grab your cock right here under the head to keep you from cumming too soon.
Todd had been moving his hand up and down his shaft right along with his wife's narration. His other hand had been moving the Helix in and out of his ass. He did want to cum. Badly. He grabbed his cock just as Cindy described and held off cumming. God she was such a tease sometimes.
"I'm slamming my fingers in deeper Todd. I'm fucking your ass hard. I'm cupping your balls with my other hand and feel how full your balls are. Holy hell baby, your balls are so full of cum. It drives you crazy when I squeeze them like this doesn't it? Can you still feel my nipples pressing into your back? Can you feel my tongue darting in and out of your ear? Can you feel my breath in your ear as I tell you how much I like fucking your ass? I'm moving my hands from your balls and back to your cock now. Oh honey, your cock is so hard and thick. It feels like it's ready to explode. Does it feel that way to you? Does it feel good when I jack you off like this? When I rub the very tip of your head against the palm of my hand? You like that so much, I know. Go ahead baby, moan my name out right now. Let me hear you call my name out as I jack you off and fuck your ass. Let me know how much you like what I'm doing."
"Cindy!" Todd cried out "God baby, let me cum! I need to cum baby. Please, you're driving me crazy!"
"That's what I like to hear. I think you deserve to cum now, don't you? You do? You think so? Should I keep stroking then? Maybe get my fingers so deep into your ass and find your prostate and send you right over the edge? Or maybe I'll just stop. Yes, stop. My fingers inside you ass, but still. My hand wrapped around your shaft, but still. My body pressed up against your back. I hear you whimper in frustration. Tell me again Todd. Tell me what you want to do."
Todd's eyes still shut, still lost in the moment; his hand still on his cock and the Helix perfectly still in his ass. "Cindy, I need to cum. Please baby, I'm begging you, let me cum. I'll do anything if you just let me cum. Fuck, I'm about to explode!"
"Let's do it baby. Let's make you cum harder than you have in a long time. Feel my hand stroking your shaft faster now. Feel how my fingers are finding your prostate? Let go baby, let yourself go. Cum now. Cum hard for me. Show me how much cum you have in there."
Todd screamed out in pleasure as he finally came, his cum spraying all over the bathroom tiles. He kept stroking as he nudged the Helix in further and felt it massaging his prostate. He came again with another low grown, his body shuddering in pleasure and exhaustion. Todd held on to the walls for support as he breathed deep, trying to get his breathing back to normal.
He finally settled down again, removed the Helix from his ass, and washed up. He thought the tape his wife made for him was over, but he heard her speak again "Now take your Nyquil and go to bed. I love you."
The End.
Cougar Hunting
Damian paused at the edge of their territory and took a quick survey of the area. The conditions were right for the kind of prey he was after. The lighting was dim; the music gave a feeling of class. There were drinks being sold but nobody was uncultured enough to be drinking beer. A slower detailed look revealed that while there was a group of four sitting around a table lightly chattering most of the crowd was sitting alone or in pairs and all of the singles had roving eyes. It was time to throw out a little bait and see what happened.
At six foot four and a solid two sixty five Damian was used to being a lot of things. Bait was a recent addition to the list but he'd found that there was no more effective way to trap his prey. He'd taken all of the steps he knew to ensure a successful venture. He hadn't shaven in two days giving him a rough scragle but not a beard. His hair had the unkempt look that only a half hour in front of the mirror could possible accomplish. He owned better shirts than the black button up, but none that had the combination of middle class and sexy he was trying his best to exude. The same could be said for the black slacks and shoes wore.
Behavior is vital to any kind of hunt. Predators are especially sensitive to any change in their prey and will walk away from easy targets if they are acting strangely. That makes it important that you keep up your normal act no matter what your intentions. For Damian that meant searching out the hottest fox in the room.
She couldn't have been older than twenty five and probably was only barely old enough to drink. Blonde hair, blue eyes, big tits and a dress that did everything it could to accentuate her figure. If she'd been nude it would have called less attention to her figure. Then she wouldn't have had the wide white belt on the red dress. "Hey. I'm Damian and you are?" Damian drawled in his southern Hispanic dialect.
The woman looked at him only once before twisting away from him. The look of disgust on in her face was both obvious and manufactured. Just like him she was hunting for a specific kind of prey and this was a part of her cover. Well either that of she wasn't interested but that thought never entered Damian's mind. Of course she was interested in him. She had a vagina and that meant she wanted him. What woman honestly didn't?
Tonight though Damian wasn't trying to seem as confident as he usually would. Normally after a rejection he'd just scan for another lone damsel and try again. This time he wandered to the bar and ordered a beer.
Damian felt the moment she walked into the room. There is just a vibe prey gets when it's been spotted, a tingle at the base of the spine warning them to the immediate threat. Careful not to let the cougar know it had been noticed Damian tilted his beer to his lips and casually turned to face the crowd.
She was standing in the middle of the dance floor, surrounded by men but completely alone. Her golden dress's neckline plunged well beneath her likely enhanced cleavage. She wasn't even trying to be subtle. The moment he was facing her she locked her eyes on his and she was dancing for him. Dipping down, running her hands up her lithe legs lifting her dress up dangerously high before letting it drop back to her thighs. Even when she turned her back to him there was no doubt who she was dancing for, not when she bent over to grab her own ankle and flipped her hair so it partially concealed her face and then walked over to the bar.
This was the hardest part for Damian. He wanted nothing more than to spring a trap on her. She was in her forties judging by the wrinkles around her eyes and the slight lines around her mouth but she'd had a body a girl half her age would kill for. In Damian's assessment parts of her body weren't half as old as a woman half her age but the last time he checked two year old implants didn't make a woman underage. When she approached Damian turned his back in mock shyness.
She did exactly what she was supposed to do. She sat down beside him flipping her hair away from her face and spoke. "Hello. I noticed you watching me out there."
"Su-sorry." Damian responded finishing his beer. He hadn't meant to do that and it shown on his face. "I didn't mean to stare it's just-"
She was a quick one cutting him off midsentence so he didn't find someway to escape his fate. "Don't apologi
ze. Makes an old lady feel great to know she can still get your attention." Her eye turned quickly to his beer. It was the most likely route of escape so she cut it off. "Bartender. I'll have a strawberry daiquiri and my friend here will have a Long Island Ice Tea." She paid for the drinks when the game and Damian stared at his for a moment before smiling and nodding. "My name is Jessica, yours?" She extended her hand to his.
Unsure of himself Damian took her hand gently. "Damian. Thanks for the drink Jessica." He lightly shook her hand and released it. It was intentional that his eyes wandered around careful only to brush against her gaze. If she knew she was being hunted not hunting she might spook. "You're incredible."
It was Jessica's turn to feign surprise with a suppressed giggle. "I just got carried away. I could feel it. You were watching me weren't you?" Jessica captured her lower lips between her teeth and smiled coyly. "It just made me hot to know you were watching me. I didn't mean to get so carried away."
"I just didn't mean to stare." Damian confessed turning slightly away from her. It was difficult to suppress the smile yanking at the edges of his mouth. Everything so far was working according to his plan. This was what he wanted. She thought she'd captured him. "I'm sorry."
Jessica smiled and finished taking a deep drought of her drink before leaning forward. "I told you. Don't be sorry. I'm flattered." She smiled. At the same time she leaned closer running her fingers up along his thigh until she reached his hand and clasped it. "I haven't seen you before. Do you live around here?"
"Not really." Damian lied. The bartender set their drinks and Jessica slipped him a twenty, easily double what the drinks and tip would have come out to.
"Would you like to get out of here? It's just so loud that it's hard to have a conversation."
Damian paused slightly smiling as he brought his light blue eyes up to meat her baby blues for the very first time. There was an instant connection. The game would continue but both of them were aware of the steps they were meant to take at that point. He'd already made contact and other than him screwing up there was nothing left. "Yeah sure." He replied after the pause.
"C'mon." She finished her drink. Getting the hint Damian tilted his head back downing the liquor in a single quaff that would have impressed his college friends. As soon as it was finished she hooked her arm into his and pulled him to his feet. That close he could smell her perfume, a sweet cinnamon scent that hooked him even more than he'd already been. Jessica was anything but subtle when she squeezed the two of them through a couple narrow openings in the crowd. First brushing her breasts against his chest and then letting him brush against her ass. "Did you drive?"
"Nah. Took a cab. Figured I probably wouldn't be good to drive by the time I got out of here." Damian smiled weakly. "You?" Jessica answered by pulling her keys from her purse and jingling them in front of him.
A click on her keys was answered by the lights flashing on a convertible Corvette. A moment later they were both in the car and Jessica was doing her best to impress Damian with her driving. It was working pretty well. She was like a fighter pilot pulling her car close between two cars so close that she had to wiggle to keep from hitting either of their side view mirrors as when she sped past them. It wasn't Damian's first time with a fast driver and she had the steady control that kept him from doubting for a single second that he was safe even when the needle started pushing past one thirty. "You seem to be enjoying yourself." Jessica purred. Damian was hanging his head over the side of the car whooping at the top of his lungs.
He stopped when he felt Jessica's cool digits wrap around his still flaccid cock and begin massaging it to life. Splitting her attention between her steering wheel and his gear stick Jessica slowed to a mere eighty miles per hour. "Such a big boy." She cooed as Damian's cock started to come to life. Damian froze in place for the first time honestly trapped by the cougar. He couldn't escape if he'd wanted to. Part of him wanted just to give in he'd never had an orgasm at eighty miles per hour, not in a car anyway and he hadn't been fucking the pilot of the plane! The other half of him was completely terrified that she was going to miss something and he'd end up plastered all over the pavement. The end result was his hips made the decision for him and thrust up to meet her hand. "How old are you Damian?"
"Twenty three." Damian gasped. It was a lie; he was actually twenty four and would be twenty five in less than a month.
"Twenty three." She squeezed his cock. "You know I'm almost twice as old as you are?" She bit down on her lip. "You're younger than my son." She purred. "Bet you didn't know that when you saw me moving on the dance floor."
Damian didn't have time to give her any response before they started pulling into her driveway. He'd known that he'd gotten a higher end cougar but he hadn't expected the nearly palatial house. The driveway was an arch that could easily handle a half dozen cars before the pull off for the five car garage. It was probably a five bedroom house from the look of it. "Holy shit." Damian muttered. At the same time Jessica practically hauled him across the center console by his cock and led him up the walkway. "Your husband?"
"Away on business for a week." Jessica answered pushing the front door open. As soon as it had closed behind them she shoved him against the wall and smashed her lips to his. "Even if he was home he wouldn't care." Her hand was still wrapped around his cock stroking him. "That's okay with you right?" Damian nodded. It occurred to him for a moment that he was the prey here. At some point that he wasn't aware of he'd lost control of the situation. He nodded.
"Now what would you like to do with me?" Jessica was gently kneading his cock. A salacious smile crawled across her face. "Maybe you want to see my tits." Jessica only needed to shrug to bring the top of her dress down from her shoulders to upper arms revealing her full breasts in the process. He'd been wrong earlier, she was all natural. He could tell by the way her full ripe breasts hung like tear drops. The sight of her light pink nipples sent a rush of blood to his already engorged cock. You'd like that wouldn't you?" Jessica squeezed firmly to enhance her point.
"Maybe you'd rather I got down on my knees." Jessica lowered herself to the floor so her head was level with Damian's cock. Her bright blue eyes locked with his. It was a weakness of Damian's to look down at a woman. It never failed to send shivers up his spine and Jessica somehow knew. That was why she was batting her eyes slightly and leaning close to press her cheek against his hardening cock. "And suck you off." Her full lips pouted slightly. "I like sucking dick." She purred gently biting him through the fabric of his pants.
Careful to keep his eyes locked on hers Jessica reached between her legs and lifted her dress. She was nude beneath the dress. The only thing covering her at all was a trimmed patch of brunette curls proving she wasn't a natural blonde. "Maybe you just want to fuck me." Jessica's two middle fingers slid easily into her slick cunt. Damian's moan answered her question. "That's it isn't it? You just want to skip to main event?"
Jessica rose back to her feet and kissed along Damian's throat then traced his jaw line. "I want to hear you say it Damian. Tell me you want to fuck me." Jessica kicked her heels off and wrapped on of her legs around his waist. Some how she managed to get his pants off at the same time so her wet pussy was rubbing directly against the tip of his cock with every move either of them made. "Say it."
"I want to fuck you." Damian snarled and kissed her. He penetrated her twice at the same time his tongue pushing past her lips to twist with hers in a tawdry kiss. Lower another set of equally greedy lips engulfed his cock. Jessica purred lustily into the kiss and started grinding her hips against him. She hopped up wrapping her other leg around his waist and braced herself against the wall. Just her hips were moving, churning his cock inside her buttery nethers. "Oh God." Damian gasped between kisses.
Jessica broke the kiss dragging her lips along his cheek to his ear. "Do you know what I'm going to do? I'm going to ride you at a gallop until you knees buckles." She lowered her voice until she was just breathing her words into his e
ar. "I'm going to squeeze you and make you pop like warm champagne." Her pussy clenched down around his cock as she spoke. "And then I'm going to do it again and again and again." She bit down on his ear lobe and tugged playfully punctuating each word with a squeeze of a tug. Damian moved his hands to her ass gripping her rump and forcing her up and down the length of his shaft.
It only took a few minutes for Jessica to make good on her two of her promises. She was fucking him hard enough that the sound of her ass bouncing off his thighs was louder than any of the whimpers, moans or cries escaping their lips. One good squeeze that made him aware of every single inch of his cock and his legs went soft sliding the two of them down the wall to the floor. Jessica didn't break stride. She just kept riding him as fast as she could manage. Her breasts bounced up and down with each thrust until she cradled them in on arm holding them up in Damian's face.
Damian opened his mouth and wrapped his lips around one of Jessica's nipples and started licking and sucking on her flesh. Every time his tongue flickered over her flesh she cooed lightly and pushed her chest towards him silently begging for more. It wasn't something she needed to beg for; he hungrily suckled at her tits moving from one to the other, occasionally lightly nibbling on her flesh.
Suddenly there was a slight flash in his head and the world narrowed. Jessica captured his face in her hands and hauled him back into the kiss that completed the circuit. The energy cycling through him, through them, was electric starting at his hips and sparking inside her. It traveled the length of her spine and she returned it via the kiss. It only needed a few repetitions before they both came. "Oh my fucking God." Damian whispered letting his head slump over her shoulder.
Jessica let him stay like that for a moment before picking up his head and kissing him again. "You know that's the best part of young men." She squeezed down again. "You're still hard." She smiled and just to show off how flexible she was she lifted one leg over his head and rotated so her back was to him and slowly started to rise and fall against the length of his cock. "I bet I can get you to come at least twice more." She whispered guiding his hands to her breasts. This time instead of the fast pounding she kept an agonizingly slow pace each time rising until only the tip of his cock remained then slowly sitting down until she was completely impaled. Once she was there her hips wriggled for a moment and started again.
The Dirtiest Daddy's Taboo Page 81