Warning: This one has multiple GIF files with sexual content, added to heighten the story and gauge audience response to such additions
Jillian stood there in the living room, almost supremely confident as she and her date, Ryan, prepared to put each other to the test sexually. She wore a form fitting tank top that barely contained her ample cleavage, or more accurately deliberately drew attention to it. She was 5’ 4” tall, fair skinned with dark auburn hair, and curvy in the truest sense of the word. She was blessed with large, firm DDD cup breasts, wide hips and a backside that was not only just large enough to balance out those giant boobs, but looked surprisingly firm in her jeans. She smiled smugly and slipped out of her high heels.
“Don’t tell me the girls already have you all hot and bothered.” She said smugly. Jillian lightly ran her hands up her sides to her breasts, cupping them lightly and pushing them slightly upwards and together. “If my boobs are already this much of a distraction, how are you going to have any chance of lasting long enough to wear me out like you’ve been boasting?” Her tone was right on the borderline of playful teasing and outright mocking… just enough defiance to test Ryan without being totally abrasive.
“Keep up that tone, and you’re going to find yourself over my knee getting that luscious ass spanked.” Ryan replied in a matter of fact tone with just a hint of a smug smile. Ryan was slightly taller than average with a lean, muscular build. He had short, well styled hair that was dark auburn to the point of looking brown in all but the brightest sunlight, and piercing deep blue eyes that held an almost unnatural level of confidence as he studied Jillian.
Jillian laughed. “Promises, promises.” she replied defiantly, crossing her arms on her chest. “Threatening me with a good time isn’t going to help you.” “Besides, I’m a country girl and a redhead…” “It takes a strong man to tame me, so you’d better make that spanking good and hard.”
Ryan stepped toward Jillian and gently but firmly grabbed her wrists, and pinned her hands over her head as he stepped up against her. He leaned his head in and kissed her ear lobe lightly then whispered in her ear.
“That can be arranged.” he whispered in a firm tone. He paused for a second, letting that thought sink in then continued in a more seductive but still firm tone. “It’s what you’re craving anyway, isn’t it?” he demanded. “Not just a good hard spanking, but a man who can totally dominate you in bed…” “That’s why you’re here; you know I can give you what you’ve been hungering for desperately for so long.” He kissed her ear again, then her neck, eliciting just the slightest hint of an aroused moan from under her breath. After taking a moment to savor that, he released her wrists and stepped back.
“Still so sure of yourself.” she said with a return of her smug smile. Her tone was still overconfident, but with a more matter-of-fact ring to it instead of the near mocking tone she had used before. “I’ve heard the talk before…” “Every girl has.” “Every guy out there brags about being some sort of sex god, and always leaves us wanting.” There was a palpable tone of disappointment and frustration in her voice with the last remark.
Ryan started to speak but she cut him off. “I know myself enough to know just how submissive I am deep down too.” “If somebody ever finally was able to make me scream in orgasmic ecstasy for ages, I know I’d completely lose myself… go to sub space and be completely, helplessly obedient.” “So, on the million to one chance there ever is a guy that can finally deliver the goods, I need to know he won’t violate my ass, make me have sex with a horse or God knows what else.”
She looked up at Ryan as her smirk returned. “So yeah, I’m a bit of a bitch when it comes to testing men, but only the very best is going to get all of me.” “You’ve talked a good game, but you’ll fail like every other guy.”
“Now who’s so sure of herself?” Ryan replied in an equally confident tone. “Or are you actually just hiding the fear of being tamed at last?”
“I’ve worn out every man who’s tried to fuck me.” Jillian replied, her tone taking on a very sultry, sexual nature while still maintaining her defiance. “There’s just no way you’re going to not only wear me out, but also make me cum so many times, that you ‘tame’ me.”
“One way to find out, isn’t there?” Ryan replied calmly with a smirk..
Jillian chuckled in amused defiance. “It’s cute that you think you can though.” “Tell you what…” “Admit my boobs have you nearly ready to cum already and I’ll let you fuck me right now.” She pushed her boobs up and together again, this time adding a playful squeeze afterwards. “Otherwise when you fail, you’re not getting any of this.” She added as she waved her hands down the front of her body.
“Are you through stalling?” Ryan asked in a slightly bored tone with a smirk of his own.
“Oh, I’m more than ready.” she responded. “I admit I find the confidence sexy too, but cocky isn’t going to get your cock inside me.”
“OK, so just so we’re clear on the rules of this little bet…”, Ryan said, forcing the conversation forward, “I have to kiss and climax you out of your clothes while respecting your boundaries…” “That means no anal…”
“IF you get that far.”, Jillian retorted.
He gave her a stern “enough” look, and then he continued. “It also means no humiliation or degradation, etcetera, etcetera.”
“And no using toys to cheat.” Jillian said in an insistent tone. “You said this would be all you… No taking a vibrator to me half way through.”
“No worries, toys would cheapen the victory.” Ryan replied calmly. “I want no doubt in your mind it was me that tamed you completely and utterly.”
Jillian tried to interrupt, but this time Ryan cut her off. “Now, as I was saying… Part one; if I can get your nipples hard, your top and bra comes off.”
Jillian nodded quietly.
“Part two…” I continued, “if I can kiss, caress, lick and suck your breasts and bring you to orgasm, those painted on jeans come off.”
“Not possible so my pants are never going to make it off my hips.” Jillian retorted flatly. “I love my boobs sucked on, but an orgasm… come on.”
“You’ll see… and feel.” he replied smugly.
Jillian just shook her skeptically.
“Now,” Ryan continued… “Once your pants come off, my hands get to slide into your panties and see just how tight that little pussy of yours is.”
“Tighter than you can handle.” Jillian replied with another smug smirk.
“Promises, promises.” Ryan replied. “Once I finger you to two more orgasms, those panties come down and you’re going to spread your legs like a good girl for me.”
Jillian let out a derisive snort.
“Then,”, Ryan continued, “I’m going to go down on you… until you cum so many times you scream for mercy and beg to feel me inside you.” “Then I’m going to fuck you silly and cum deep inside you.”
“If you can actually make me beg for it, I’ll happily surrender my pussy to you bareback and let you cum inside me.”, Jillian replied with a skeptical smirk.
“Well, there’s a pleasant thought.” Ryan said with an amused chuckle. “Admitting the possibility of defeat, are we?”
“No.”, Jillian replied flatly. “I’m just agreeing to play by the rules, so you have no excuses.” Jillian’s smirk grew huge and her eyes lit up with wicked delight. “In fact, I don’t even want any crying about you couldn’t tell my nipples were hard under this boulder holder.” She said in a lascivious tone. She reached behind her, underneath the top of her tank top and unhooked her bra. She slipped free of her bra without exposing herself at all; the tank top stayed almost perfectly in place. She held the bra out in front of her at arm’s length. “Enjoy it, this is as close to naked as you’re going to get me.”, She said with arrogant amusement as she let the dangling lacy bra fall to the floor.
Jillian’s nipples immediately grew firm and erect, demanding to be noticed underneath her top.
“Oh really?”, Ryan replied confidently. He stepped up close to her, trapped her up against the wall and again pinned her wrists above her head.
Jillian let out a light surprised gasp, apparently not expecting such a bold opening move.
Ryan tilted his head in again and whispered softly in her ear. “Your nipples are already hard.” he stated with obvious glee. “You’ve already lost your top.”
Jillian’s eyes went wide as she became fully aware of the combination of light electric tingling in her nipples and the feeling of added pressure against them as they struggled against the constraints of the tight, silky smooth cotton tank top. She struggled to find a retort… some reason to prevent this initial defeat.
“Seems a shame to take it without so much as a single kiss however…” Ryan said with a wicked grin. He put his hand under her chin and gently turned Jillian’s head so that she was looking at him. Jillian didn’t fight the move, but the annoyed look on her face made it clear she was following the rules grudgingly.
Keeping her hands pinned above her head with one hand, Ryan leaned in and kissed Jillian passionately, putting every ounce of passion and desire he had for her into the kiss. Meanwhile, his right hand had slipped down and softly cupped and caressed Jillian’s breast.
Jillian fought the kiss briefly, struggling to free her wrists from the leverage her would be lover had on them, and struggling to escape from how he had her body pinned between his and the wall. As the kiss grew even more passionate, her struggles ceased and her resistance melted. Their tongues danced passionately for minutes, like they were starved for each other. All the while Jillian became more aroused, pushing her breast more firmly into his hand and grinding her hips against Ryan. By the time they broke the kiss, she was fighting for breath and weak in the knees. Still defiant and determined not to let any man be better than her in bed, she tried to hide it with false bravado.
“Well, if your other skills are on par with your kissing, this could be fun.” Jillian remarked with a playful smirk. “There’s still no way you’re getting my pussy, and NO man has ever lasted more than a couple minutes inside me.”
“Then you’ve been letting boys bed you, not men.” Ryan replied bluntly. He released her wrists and took a step back, keeping his hand on her ample breast. “I’ve already won the first part of this little challenge.” He gently took her firm nipple between his thumb and finger to emphasize the point.
Jillian stifled a slight moan as he teasingly twirled the nipple between his fingers.
“Now, I could just tear open your top and claim those luscious huge tits of yours…” Ryan said in an amused tone.
“Don’t you dare!” Jillian glared, covering her breasts with her hands.
“I thought about it.”, he replied matter-of-factly. Ryan paused for a moment, letting Jillian dwell on her predicament. “I think it would emphasize the point more if you slid down those tank top straps yourself and personally offered me your breasts though.”
Jillian’s mouth fell open at the sheer audacity of his demand. “You expect me to just serve them up to you on a silver platter?” she asked, incredulous.
“I expect you to be a big girl and play by the rules you agreed to.” Ryan replied flatly.
Jillian wavered. Her face was awash with a mixture of defiance and humiliation as she struggled with her situation. Finally, her head fell in defeat and her hands moved up from her breasts to the straps. Slowly she slid them off her shoulders and down her arms. As the straps reached half way down her upper arms, her mammoth jugs spilled out of the top. They were a magnificent sight to behold; surprisingly firm for their size and their lily white skin was even fairer than the rest of Jillian’s body. Her nipples were equally impressive. Dark in color, they were as big as a penny and stood out nearly a half inch, and they were surrounded by equally large, impressive areolas. Goosebumps raced across the newly exposed flesh as the cool climate controlled air brushed lightly against her breasts.
“Happy?” Jillian asked in an annoyed tone, slightly cocking her head. Her hands still lingered on the straps of the tank top, unready to release them and finalize her surrender.
“Almost.”, Ryan replied in an almost bored tone. He gazed affectionately at the freshly exposed pale, soft mounds of flesh. “Mmmmm… Very… very… nice.” he said appreciatively. “Doesn’t look like your poor girls get much sunlight though.” he added with yet another smirk. “We’ll have to change that after I unleash your inner slut and collar you tonight.”
“Dream on.”, Jillian replied defiantly.
Ryan walked behind Jillian, eliciting a confused and slightly nervous look from her. He wrapped my arms around her, cupping her breasts in his hands and pulling her close. He traced a path of soft kisses along her shoulder and her neck as he gently kneaded and massaged her breasts.
Jillian let out a long soft moan and unconsciously tilted her head, surrendering her neck to Ryan. A moment later she jutted her chest out, pushing her breasts more firmly into his hands.
“Having an inner slut is a good thing.” he whispered into her ear. “Every woman should fully embrace her sexuality.” “A true lady is just discerning about when she lets that inner slut out.”
Ryan moved his kisses along Jillian’s neck and cheek, teasing the corner of her mouth a few times. All the while Jillian’s breathing became more and more labored.
“You want this.” he whispered in a sultry but firm tone. “I see it in your eyes, the slight tremble in your body, your breath…” “Your body is on fire, craving to be taken and given the release you hunger for.”
“M… maybe…” Jillian managed, struggling to escape the fog of erotic desire that was clouding her mind. She turned around in Ryan’s arms as she regained enough composure to speak. “But if you want my body, you’re going to have to finish this little bet and earn it… if you can.”
With that, Jillian kissed Ryan passionately and moved his hands from her back to her breasts again. Keeping her hands on his, she encouraged Ryan to knead and massage them. Jillian’s breathing had turned into soft but highly erotic moans of pleasure.
“I don’t know how you think you’re going to get past the next part.”, Jillian chuckled with a slightly sarcastic tone. “There’s no such thing as a boobgasm.” She added dryly. She let out a fairly loud moan as Ryan continued fondling her massive breasts and kissed her neck. “You certainly know how to handle my girls.” She added in an almost gasp. “But an orgasm… Just can’t happen.” “Trust me, I know my body better than you ever will.”
“Oh, is that right?” Ryan challenged in a tone that was more playful than anything else. He put his hand under her shapely rear, and lifted her up to where her breasts were in his face, then turned around and pinned her against the wall as he covered her breasts with kisses and suckled her nipples.
Jillian let out a short, startled gasp as Ryan picked her up. As he twirled her around and pinned her up against the wall her eyes filled with a wild desire. She wrapped her legs around his waist and leaned back against the wall, jutting her chest out and offering her breasts to him. She moaned passionately as he covered her breasts with kisses, and when Ryan first suckled her nipples, her entire body shivered as a bolt of erotic electricity raced from her breasts to her clit.
They continued that way for a good 20 minutes… Ryan softly caressing, kissing and suckling her breasts. Occasionally he’d lightly circle her nipples with his tongue and gently blow on them, eliciting an erotic shiver from her. The longer it went on, the louder and shorter Jillian’s gasps of pleasure became. Finally, she wrapped her arms tightly around him and tightened her grip with her legs as her whole body shuddered sharply 4 or 5 times. All that escaped her mouth for those moments was a low trembling gasp of ecstasy.
Afterwards, Jillian was gasping lightly, trying to catch her breath as Ryan lowered her half nude form back to the ground. She was weak in the knees and it took her a moment to fully regain her footing.
“H… H… how…” Jillian struggled to get out in a completely bewildered tone. “Wha… what did you do to me?”.
“I gave your luscious body the attention it so richly deserved.” Ryan replied in a satisfied tone. “With exactly the result I said I’d get.”
“But…”, Jillian injected, still overwhelmed and confused that her body had reacted the way it had.
“Yes,” Ryan replied. “You have a large, shapely and very luscious ass.” “It’s time to show me a little more of it too.”
“Wha…” Jillian stammered.
Ryan wrapped an arm around Jillian’s waist, keeping her close and deftly unzipped her jeans in one fluid quick movement.
Jillian struggled to escape my grasp. “Nooo…” she objected. “This isn’t fair.”
Ryan turned Jillian around and gently but firmly pinned her against the wall, squishing her giant breasts against it. “Quit being a brat.” he commanded sternly. “You lost your pants fair and square.”
Jillian whimpered and squirmed as Ryan undid her belt and the top button of her pants. She let out another ‘noo’ as he pulled the pants down to her knees. Then he wrapped his arms around her, one around her chest, placing his hand on her breast, and the other one he wrapped around her waist, placing his hand just above the waistband of her midnight blue satin panties. Ryan could feel Jillian’s heart racing and her breath was shallow and fast.
Jillian let out an aroused whimper and squirmed as she felt Ryan’s hand begin to slip down inside the front of her panties. “No… This isn’t right.” she whimpered. “I can’t give up my pussy this easy.”
“Should have thought of that before you made the bet and taunted me.” Ryan replied. He pushed his right leg between Jillian’s legs and nudged them apart as far as the jeans (which had already slipped down around her ankles) would allow. “That’s better.” he said with a satisfied tone as his fingertips slipped down to her pussy. He glided his fingertips across her nether lips with a feather light touch, eliciting a shiver and deep, erotic moan from Jillian.
Ryan continued lightly teasing and caressing the surface of Jillian’s pussy, using as light a touch as possible an eliciting a steady stream of erotic shivers accompanied by low erotic moans of pleasure. Despite her growing arousal, Jillian continued to struggle against her seduction. It was an odd alternating of rocking her hips with Ryan’s teasing caresses, and outright squirming to escape his grasp. This continued even after her panties were wet with her juices.
“OK, enough of this.”, Ryan said, letting his displeasure clearly show. He moved Jillian’s hands behind her as if she was handcuffed and lead her to the end of the couch. She struggled for the first step or two before she was able to kick off her jeans. When they got there, he bent Jillian over the arm of the couch, which was heavily padded and over a foot wide. With her stomach resting on the arm of the couch and her boobs dangling over the cushion, he kept her hands at the small of her back.
“It’s pretty clear you’re pushing for that spanking we discussed earlier.”, Ryan said flatly. “Since that’s clearly what it’s going to take for you to respect me and follow the rules, you’re going to get it.”.
“You wouldn’t dare.”. Jillian retorted defiantly as she struggled against her position.
“Really?!?” Ryan laughed. “You think you’re going to escape from this position?” “I’ve been a dom long enough to know how to control an unruly sub.” With that, he pulled Jillian’s panties down, exposing her plump, lily white ass. He left the panties half way down her thighs, knowing that would increase her feeling of vulnerability.
Ryan grabbed Jillian’s ass with his free hand and gave her butt cheek a firm squeeze. “Very nice.” he said admiringly, but trying to keep the firm edge in his voice.
“You can’t handle it… or me.” Jillian spat defiantly. She thrashed for a moment trying to escape her bent over position then let out a frustrated growl.
“Seems to me I’m already handling it.” Ryan replied flatly. He grabbed her ass firmly to emphasize the point and Jillian let out a small yelp. She started to struggle again and he brought his hand down across her bare ass.
Jillian stifled another yelp. “Was that supposed to impress me?” she asked in an angry, defiant tone? “You hit like a little girl.”
“Careful what you ask for.” Ryan retorted, bringing his hand down hard on her ass in a stroke that moved upward along her ass. He cupped his hand slightly as well. The result was a stinging smack on the ass that made jiggle provocatively with the impact.
“Owww!” Jillian cried out. “Stop!”
“You’ve done everything you could to earn this, and you’re going to get it.” Ryan replied in a firm tone. Jillian struggled weakly, knowing she was trapped but wanting to escape. He brought his hand down hard across her ass again, leaving another light red hand print on the lily white skin and getting another cry of pain from Jillian.
“Stop, this isn’t fair.” Jillian whimpered.
“After you learn your place.” Ryan demanded. He spanked her several more times, covering her butt with hand prints and making Jillian cry out in pain each time. Jillian struggled less and less with each spank as her defiant spirit drained away. Ryan only stopped when she stopped struggling and only whimpered after the last spank.
“Please stop…” Jillian whimpered weakly.
“Say ‘Please stop sir, I’ll be an obedient girl.’” Ryan demanded.
Despite a pitiful look in her eyes, Jillian remained silent and almost started to shake her head ‘no’.
Ryan brought his hand down across her ass again, this time even harder. Jillian cried out again. Tears ran down her cheeks as she fought back crying. She sobbed once but remained otherwise quiet and he raised his hand again.
“No!” Jillian blurted out. “Please…” she sobbed. “Please stop… sir.” She choked out the last word. “I… I promise I’ll be an obedient girl.” The defeat in her voice was clear, but there was a hint of desire as well. Her juices were trickling down her inner thighs, providing further evidence of her desire.
Ryan put his hands under Jillian’s arms and gently helped her up, then turned her to face him and held her close. Jillian’s eyes searched his, seeking some sign of approval. Ryan wiped a tear from her cheek and kissed her passionately. This time she quickly melted into the kiss and returned it hungrily.
Ryan’s right hand glided lightly down her side, then he slipped it between them. Jillian let out a low guttural moan as he ran his fingertips lightly through the wispy patch of neatly trimmed pubic hair on her mons. Jillian spread her legs as much as the panties half way down her thighs would allow, and rocked her hips forward, urging his hand onward.
Ryan smiled wickedly. “Good girl.” “Being spanked made you a horny thing, didn’t it?” he asked, still keeping a firm tone.
Jillian nodded quietly, her face flush with embarrassment.
Ryan turned Jillian around and guided her upper body forward. She placed her palms on the arm of the couch, ending up in a slightly bent over position. Ryan moved up against Jillian, wrapping his arms around her as he’d done before her spanking. His left hand cupped and kneaded her right breast, teasing her nipple between his fingers. His right hand slipped between Jillian’s legs and began massaging her wetness.
Jillian out a long, deep ‘fuck me’ moan as her knees slightly buckled and her hips began to rock against Ryan’s hand. He glided the tip of his tongue lightly along the edge of her ear, softly kissing it twice. Jillian slightly tilted her head backwards and to the side, closing her eyes and letting out another soft moan.
Ryan gently probing her slit with one finger as Jillian continued to moan and whimper with desire and rock her hips.
Content that Jillian was firmly under his control, and her responses filling Ryan with desire, he leaned in and softly whispered into the ear he’d been teasing and kissing. “You were partially right earlier.”, he said. “I want you.” “You’re one of the most beautiful women I’ve seen and I’ve wanted your body since the first time I saw you.”
Jillian’s body shivered lightly in response to the words and she let out another, more urgent moan. She tried to turn her head, her lips desperately seeking his.
Ryan’s voice took on a firmer tone, mixing with the desire he had already displayed as he continued to whisper sensually in her ear. “We’re clearly going to have to fully tame that vixen in you to make that happen though.” Jillian let out another moan in response, this one still full of desire but there was a hint of ‘prove it, make me yours’ there as well.
“So, here’s how the rest of this is going to go…” he continued in a firm but sensual tone. “I’m going to play with your pussy, and make you cum… hard.” “Maybe more than once… if you’re a good girl.” Ryan paused for a moment letting the reality of his words sink in. “Then… I’m going to take you to bed, spread those luscious legs, cover your inner thighs with kisses, and then I’m going to go down on you.” “Not just go down on you, but devour your pussy until you orgasm so many times your thighs are soaked with your juices, your body won’t stop shaking, and you call me master and beg me to fuck you.”
The look in Jillian’s eyes was one of ravenous desire. “Oh God, I want that soooo bad.” She moaned. “Claim me, fuck me, make me yours.” “Show me you can be the man I’ve been craving and make my body yours.” She continued with a gasp. “I won’t give in easily though… I can’t.” she added with a whimper.
“It wouldn’t be worth it if I didn’t earn it.” Ryan replied. “After you beg me to fuck you though, I’m going to claim that tight, wet pussy and take you the way a goddess like you deserves to be fucked.” “I’m going to give you orgasm after orgasm until you can’t take it anymore and then you’re going to feel the wet warmth of my cum fill your womanhood as I cum deep inside you and fully claim your body as my own.”
“Prove it… earn my pussy.” Jillian said in a low husky voice that was a mix of primal lust and defiant need.
Ryan pulled Jillian up, standing her up straight again, holding her close as he wrapped his arms around her. She let out a soft sigh and nuzzled him, rubbing her cheek against his.
Ryan’s right hand returned to probing and teasing Jillian’s sopping wet womanhood. Jillian’s moans became loud and urgent, her hips gently bucking in time to them as she desperately tried to urge him deeper into her.
Fully understanding the value of letting the fire of a woman’s desire grow white hot, Ryan continued to take it slow. He covered Jillian’s neck, shoulder and cheek with kisses as he teased and caressed her pussy’s inner lips with his fingers.
Jillian moaned and gasped almost non-stop, each moan becoming even more urgent than the last. She moved her arms backwards and wrapped them around Ryan as he maintained his position behind her. Jillian’s entire body was now flush with desire and she was grinding her rear hungrily against Ryan’s crotch. He now had her clit between two fingers and was gently sliding them up and down, caressing her clit and teasing her hole with the tips of his fingers.
Over the next five minutes, Jillian’s moans turned to soft cries of pleasure as she moved in unison with Ryan’s fingers. Finally, her body shook and trembled as her knees buckled, her head fell back against his shoulder and she loud out a long, screaming cry of orgasmic ecstasy.
Jillian’s body spasmed and trembled for a good ten seconds and it took another 20 more before she could stand without Ryan’s help. When she could, she turned and wrapped her arms around his neck and kissed him passionately.
“I have… never… cum that hard from somebody else fingering me.” She said between gasping breaths. “You… owe me… at least one more that way… per our bet though.”
“Oh, I know.” Ryan replied with a mischievous grin. He sat on the arm of the couch, took Jillian by the wrist and pulled her onto his lap. She landed on his left leg with her legs between his, and draped her arms around Ryan’s shoulders. Jillian looked down with annoyance at the panties still tangled around her thighs.
“This is almost cheating,” she said “but these damned things are getting annoying.” Jillian took one hand from my neck, placed them on the front of her panties and pushed them past her knees, where they promptly fell to the floor around her ankles. She stepped out of them with one foot and playfully kicked them away with the other, sending them flying across the room.
Jillian spread her legs wider with a wicked gleam in her eyes. “Now make me cum.” She demanded playfully. She draped her arms around Ryan again and kissed him passionately, their tongues dancing together.
Ryan kept his left arm wrapped around Jillian, supporting her on his leg, and his right hand slipped once again between her legs. Jillian let out a whimper as his fingertips brushed lightly against her swollen clit, but they never broke the deep, sensual kiss they were sharing. Ryan lightly circled her hole with his fingertips, using an almost ghost-like touch. Jillian squirmed in arousal, clearly wanting more.
Satisfied that Jillian’s body was still primed with desire, Ryan placed his palm on her mons, and gently slipped his middle finger into her. Jillian’s body shook as a jolt of erotic lightning raced through her and she cried out in pleasure into Ryan’s mouth mid-kiss. He smiled inside feeling Jillian deepen the kiss instead of pull away when she cried out.
Robert moved his finger in and out of her pussy, his hand lightly rubbing her mons and clit at the same time. Jillian broke the kiss and began gasping and moaning loudly. Her eyes closed and her head gently rolled around. Ryan watched Jillian’s stomach rise and fall with each panting gasp, enjoying how responsive her body was. Jillian’s stomach and impressive breasts were already covered with a light sheen of sweat.
As Jillian’s cries of pleasure grew louder and higher pitched, she took her hands from around Ryan and began playing with her breasts and tweaking her nipples. Moments later, she screamed in pleasure, and pushed her breasts upwards and together as her body spasmed and jolted with an intense orgasm. Jillian’s head fell straight back as it happened.
For Ryan, the most exciting part of Jillian’s explosive orgasm was feeling her pussy tighten and clench his finger inside her tightly. Jillian’s orgasm lasted a good 30 seconds and her pussy stayed tightly wrapped around his finger and quivering the entire time. This woman was clearly a rare sexual jewel.
Jillian gasped and panted after her orgasm subsided, catching her breath. Her body shivered once afterwards. Whether it was another orgasm or an ‘aftershock’ was hard to say, but the reaction was intoxicating. Before she had a chance to fully catch her breath, Robert slipped a second finger into Jillian and began quickly pumping in and out.
Jillian’s reaction was electric. She threw her head back and let out a wild-eyed scream that was a mix of surprise and ecstasy. She gasped and tried to pull her hips away, but Ryan’s arm was firmly around her waist.
“Nn.. n… nooo!” Jillian gasped. “T.. too soon…” Jillian panted, gasped and cried out as Ryan continued quickly plunging his fingers in and out of her tight, dripping wet hole. All the while her hips squirmed wildly. He smiled wickedly at Jillian’s reaction. Noticing that Jillian’s already massive breasts had swelled even more, and that her nipples were achingly hard, he leaned in and took her nipple in my mouth; kissing, licking and suckling her breasts.
Jillian let out a loud, sharp scream of pleasure as she felt the heat of his mouth on her breast, wrapping her arms around Ryan’s head. She tightened her grip around his head as her body began to tremble and shake.
“Nooooooo!” Jillian cried out, tossing her head back. “Too… much…” Jillian began panting loudly, trying to catch her breath. “No no no no no no no no no no no no no no!” Jillian’s last ‘no’ turned into a loud wailing cry of pleasure that lasted over 30 seconds as body bucked, shook and convulsed in orgasmic release. Again, her pussy tightened around Ryan’s fingers, but this time it throbbed and pulsed instead of being able to keep a tight grip.
This time, Ryan gave her no relief at all… He kept pumping away, making sure her clit and mons were also stimulated. Jillian’s previous orgasm had barely begun to subside when a new one ripped through her defenseless body. She shook like a rag doll and continued to shriek in orgasmic rapture.
Ryan continued his merciless assault on Jillian’s defenseless womanhood, intent on leaving no doubt in her mind that he was the master of her voluptuous body. He crossed his fingers and added a twisting motion to his thrusts in and out of her.
The response was even more electric. Jillian sat bolt upright and arched her back as her entire body tensed up. Ryan pumped in and out her over and over, bringing her to two more back to back, increasingly intense orgasms. Jillian panted and gasped, trying to catch her breath for a moment when one final orgasm exploded from the very core of her being. She tried to scream, but Jillian only had the strength for a nearly 40 second long incoherent moan as her body rag dolled uncontrollably in Ryan’s arms.
Ryan stopped this time, giving Jillian a desperately needed rest, but he left his fingers inside her. Jillian collapsed weakly against him, softly moaning incoherently. Ryan kissed her breast and Jillian’s body convulsed for a moment from the jolt of erotic electricity that shot through her. Jillian tried move her head, but it only fell weakly back. Her mouth remained partially open as she continued to moan incoherently. Ryan removed his fingers from inside of her and brought them to Jillian’s mouth. Jillian almost reflexively took them into her mouth, sucking her own juices from them as her tongue licked artfully licked the fingers. As Jillian recovered more fully, her sucking became more deliberate and sensual. The look in Jillian’s eyes clearly said that she was doing her best to tempt Ryan with her clearly impressive oral skills.
“Don’t worry.” Ryan said with a smile. “We’ll put that mouth to use soon enough.”
Jillian’s body was covered with sweat after the 5 machine gun orgasms. Ryan picked her up and sat her gently on the couch, then went to the kitchen to get her a glass of ice water. Jillian rested quietly on the couch for the brief time he was gone, but started to get up as he returned with the water.
“Rest there for a moment.” Ryan said as he handed her the water. His tone was a sensual mix of firm command and tenderness. It made Jillian involuntarily shiver with arousal. “That took a lot out of you.” He added.
“It made me horny is what it did.” Jillian replied with a lascivious grin. “I need more… much more after that.” She added, taking a sip of the water.
“Looked like you were pretty close to your limit there to me.” Ryan said in a teasing tone, unable to hide the pleased smirk on his face.
Jillian licked her lips seductively and then stood up, cradling the glass of ice water in her hands. “Trust me, I’m every bit as insatiable as I told you.” She replied in an erotic but challenging tone.
“Good.” Ryan replied in an unaffected tone, walking away from her. Then he turned around and gave her a wicked grin. “Because we’re just getting warmed up.”
“Is that right?” Jillian asked with a wicked smile. She followed after Ryan, adding a little extra sway to her hips to appear even more seductive. Her sultry walk had the added bonus of adding a little extra sway and bounce to her ample breasts as well. Jillian noticed the way his eyes were roving all over her nude body. “Like what you see?” She asked as she stepped close to him.
“Yes to both.” Ryan answered with a smile. He dipped his fingers into the glass of ice water and then dripped a couple of drops onto Jillian’s breasts. Jillian shivered strongly and gasped as her nipples hardened and her entire upper body was covered with goose bumps.
“That was mean.” Jillian pouted.
“Awww…” Ryan mocked. “Poor baby.” “Let me kiss it and make it better.” He took the glass from Jillian, and put it on a nearby end table. Then he turned back to her, put his hands on her shoulders and backed her up against the nearby wall. The move was fluid and gentle. Immediately he followed up by taking her in his arms and covering the side of Jillian’s neck with kisses. Jillian tilted her head, offering her neck while letting out an aroused moan. Smiling, he traced trail of soft, sensual kisses down her shoulder. Between each kiss, he lightly glided his tongue over her skin. Jillian responded with a soft moan.
Ryan continued his trail of kisses, moving slowly downward. When he reached her breasts, his hands slid down to them. He lightly ran his fingertips along the undersides of her breasts and covered them with kisses. Jillian moaned loudly, tilting her head back and jutting her chest forward. Ryan spent several minutes covering her breasts with kisses as his hands caressed, massaged and kneaded them. By the time he moved on, Jillian was moaning heavily and her hips were ever so slightly rocking with a mind of their own.
Move on Ryan did though, slowly kissing his way down Jillian’s chest and stomach. Her stomach trembled with each kiss, and her breathing became increasingly labored and excited. He covered Jillian’s mound with kisses, then lightly traced his tongue along the ‘v’ formed where her legs ended and hips began. Jillian trembled and let out a low moan as Ryan slowly advanced lower. Her reaction only doubled in intensity when he blew lightly on her mons and across her pussy.
Jillian let out another moan of wanton desire. “God, you’re driving me crazy” she protested in an equally wanton tone.
‘Not yet,” Ryan replied with a lascivious grin. “Soon though… very soon.”
Jillian moaned again and rested her hands on Ryan’s shoulders to steady herself. He continued to kiss lower, slowly and teasingly working his way down the top portion of Jillian’s left thigh. Goose bumps raced down Jillian’s legs and she began softly gasping. Jillian tightened her grip on Ryan’s shoulders and lifted her left leg, moving it outward as well. He hooked his arm under her leg, supporting it, and then leaned in and began kissing and licking his way up her inner thigh.
As her hips fell back to the bed, Robert kissed his way back up Jillian’s leg, this time working his way up her inner thigh. It turned out Jillian’s inner thighs ere delightfully responsive; more so than most women’s. Jillian moaned hungrily and had a wild, wanton look in her eyes. She swung her leg wide and upward, draping it over Ryan’s shoulder and leaving herself spread wide for him. With every kiss up her thigh, her body trembled more and more, and her moaning grew loader and deeper. Ryan reached Jillian’s crotch, and glided the tip of his tongue softly along the length of her nether lips.
A gasping moan escaped Jillian as she arched her back and moved her hips forward to meet Ryan’s tongue. The look on her face was one of almost pure wanton lust, with just a hint of something more wild and primal lingering in her eyes. It was clear she was already burning with desire. Ryan smiled knowingly and teased Jillian with his tongue and lips for a while, provoking an aroused squirming from her. When she began moaning softly, he finally pleasured her fully, enjoying the taste of her wetness as his tongue danced all over and into it. Softly sucking on her clit pushed Jillian over the edge the first time. She let out a sharp cry as her back arched and her entire body shook heavily from the electric orgasm shooting through her. All the while she kept a death grip on Ryan’s shoulders.
Ryan continued ravishing Jillian with his tongue and feasting on her juices, bringing her to two more intense climaxes. All the while her body shook almost violently with pleasure and she struggled to keep her balance. She tossed her head back and forth, moaning loudly and digging her nails into his shoulders as held on for dear life. Her body was covered with a light sheen of sweat and she was panting by that third orgasm hit. At that point, Ryan stood up, put his hands under her butt and lifted her up. Jillian let out a delighted little squeal and wrapped her arms and legs around him as he carried her to the bedroom.
Ryan laid Jillian down on the middle of the bed, then stood back up and pulled off his shirt.
“Aren’t you getting ahead of yourself?” Jillian asked in a sultry tone with a hint of defiance. “You haven’t made me beg to feel your cock inside me yet.”
“Mmmm, that’s beside the point.” Jillian purred as she ran her hand up his inner thigh and over the crotch of his jeans. “You promised you were going to go down on me so long and so good that I would become your submissive little slut and beg for your cock.”
“You want to be my little slut, don’t you?” Ryan asked in a firm but lewd tone.
Jillian smiled as if recalling a highly erotic daydream. “I want to see if you’re man enough to make me be.” she replied.
“There’s the defiant streak again.” Ryan said. “We can fix that.”
Jillian looked worried for a moment, apparently fearful that he was going to spank her still tender ass again. Ryan climbed on top of her, straddling her stomach without putting much of his weight on her.
“Now what?” Jillian asked in a wantonly lewd tone.
Without saying a word, Ryan pinned her arms above her head, bringing her wrists together near the head of the bed. Jillian looked both confuse and aroused until she felt the handcuffs wrap around her wrists.
“Hey!” she objected. “This wasn’t part of the bet!”
“It wasn’t excluded either.” Ryan replied matter-of-factly. “Only sex toys were.”
Jillian let out a ‘grrr’ and struggled against the now closed handcuffs keeping her arms together directly over her head. Ryan let her struggle against the ropes for a few minutes while he massaged her boobs with one hand and caressed various other parts of her body with the other. All the while, Jillian glared at him with a mixture of lust and annoyance.
When she finally collapsed against the bed and let out a frustrated sigh of resignation, Ryan reached under the pillow and pulled out a long piece of red silk. He teased Jillian’s nipples with it for a moment, lightly dragging the silk cloth in slow, sensual circles around each nipple. Jillian’s nipples grew achingly hard and she arched her back with a soft moan. He pondered continuing to tease her naked body with the fabric, but didn’t want to give her any more time to cool down from the plateau of desire she had hit in the living room. With that thought in mind, he took the silk cloth and blindfolded Jillian.
She allowed it, but almost as if out of a sense of uncertainty over what was happening. When the blindfold was secure, the increased sense of vulnerability, of not knowing, washed over Jillian. She let out a series of whimpering moans and struggled against the handcuffs around her wrists.
“Naughty, naughty.” Ryan said. “You’re going to lie there like a good little girl while I eat that sweet pussy and make you cum over and over again.” He let out a faint evil chuckle. “And while you lie there, bound, blindfolded and completely helpless, I want you to dwell on that vulnerability you’re feeling right now…” He leaned down and whispered in Jillian’s ear in his most seductive voice. “…How your body is completely vulnerable and exposed, and I can have my way with you any way I want.”
Jillian let out a sharp gasp and trembled with a mixture of arousal and nervousness. Ryan laid down next to her and ran his fingertips down Jillian’s stomach, eliciting a shiver from her. At the same time, he kissed her along her ear and then whispered again. “When I’m done, you’re going to know to the very depths of your soul that I’m the absolute master of your body.”
Jillian’s breath quickened and goose bumps raced across her entire body. Ryan climbed on top of Jillian, keeping his weight primarily on his hands and knees, but putting enough weight on Jillian to add to her feeling trapped and to feel those luscious breasts pressed up against him.
“Yet.” Ryan emphasized, stepping back to the edge of the bed. “I can see in your eyes you want it though, badly.”
From there, he gave Jillian’s lower lip a faint kiss, and then his tongue glided across her lips. Jillian let out two ragged gasps of arousal and lifted her head, silently pleading for more. She opened her mouth as if in invitation to be kissed deeply. Ryan responded with a light kiss to her upper lip. Jillian let out a hungry, yearning moan, and he softly kissed her upper lip again. Then he pressed himself even more firmly against her body, letting Jillian feel the length of his hard-on through his pants against her bare body. He squeezed her breasts as his tongue glided across her lips one more time, and then he kissed her passionately. Jillian returned the kiss desperately, seeking some release… any release… for the fire building inside of her.
“Hungry…” Ryan remarked with wicked glee. “Good, that’s what I want.”
Jillian let out a lust filled moan of desire as he broke the kiss to speak.
Ryan lightly kissed her lower lip, teasing her with the possibility of something more intensely passionate. Jillian let out a soft gasp and tilted her head slightly back, her body softly trembling with desire beneath me. He kissed his way along her cheek to her ear.
“Don’t worry…” he whispered. “What your body is craving is coming.”
Jillian moaned hungrily and struggled against her bonds as he slowly kissed his way down her neck and along her shoulder. Ryan began slowly sliding down her and tracing a trail of sensual kisses down her chest. He took his time, placing a dozen soft kisses along the way down to Jillian’s luscious, full breasts. Reaching them, he covered them with kisses and took them in his hands and began firmly kneading and massaging them. Jillian began moaning loudly in response. When Ryan began kissing and suckling Jillian’s nipples, her moaning became more urgent, and she began grinding her hips against him. He continued working his magic on Jillian’s breasts, and the longer he sucked on and massaged them, the louder she moaned, gasped and cried out. Her hips gyrated and bucked against Ryan’s stomach and he felt her pussy getting wetter and wetter. After a few minutes, Jillian’s back arched and her body shuddered slightly with a mild orgasm. Ryan smiled as he felt her pussy quivering against his stomach.
“Now that you’re properly warmed back up, I guess we can have another taste of that sweet honey between your legs.” Ryan said with clear wicked delight.
Jillian let out a long moan that was a mix of frustration and primal, animal lust.
Ryan kissed his way down the center of Jillian’s stomach, feeling her body tremble lightly with each kiss. When he reached her naval, he circled it lightly with the tip of his tongue then kissed once just below it. Looking back up with a wicked grin, he blew lightly on the trail of kisses down Jillian’s stomach. Jillian’s back arched as she let out a deep gasp. She stayed in that position for a few seconds then crashed back down the bed. Her body was trembling and covered with goose bumps, and she was panting lightly.
Satisfied that his efforts had the desired results, Ryan continued to trail his kisses downward. He kissed all around the wispy patch of dark red pubic hair, covering the rest of Jillian’s mons with soft kisses and licks. Jillian’s panting and moaning became louder and almost ragged with arousal as he ran his tongue along the borders of her legs and mound.
Jillian squeezed her thighs together, squirming and panting as Robert kissed his way down the front of her left thigh. She shook her head ‘no’ desperately… almost wildly, and tried to manage a ‘no’. Unable to fully form the word though, it only escaped from her as a ragged series of panting moans. Ryan kissed half way down her thigh, delighting as goose bumps ran down Jillian’s legs. Jillian squirmed, trying to keep from being completely overwhelmed by the desire consuming her.
Ryan put his hands partially between Jillian’s thighs and pushed her legs open. She offered a faint resistance, her thighs trembling as they spread apart. He lifted her legs up under her knees, raising her calves into the air and bringing Jillian’s thighs straight vertical, then he finished spreading her legs. Jillian proved quite flexible too; her knees almost completely touching the mattress as she was spread wide.
Ryan kept his hands just above the insides of Jillian’s knees and began slowly kissing his way up her inner thighs, alternating between her legs every few kisses. As he got within a few inches of Jillian’s womanhood, he added light licking, tracing circles and figure eights on her inner thighs between kisses. Jillian’s moans turned into wails of pleasure as she struggled and fought frantically against her bonds. With her thighs pinned against the mattress, all she could do was wiggle her lower body slightly as she struggled.
Ryan kissed along Jillian’s slit, letting his tongue tease her opening as well. He made sure she could feel the heat of his breath against her wetness. When he exhaled lightly on it, Jillian nearly jumped out of her skin and let out a scream of passion. Moaning and panting, she squirmed… desperately seeking relief. Ryan circled Jillian’s pussy again with his tongue and smiled as it began to open up like a flower.
Ryan opened his mouth and placed it over Jillian’s pussy, then began running his tongue quickly but lightly along her slit, slowly probing it deeper and deeper. Jillian was panting like an overheated dog at this point and she clutched the sheets above her head in her clenched fists. She began lightly bucking her hips, urging more. Ryan gave her a few seconds of rest, then he placed his mouth over Jillian’s clit and, after giving it a light kiss that sent a shiver racing through her, began to tease and circle it with his tongue while gently sucking on it.
The result was electric. Jillian let out a scream of orgasmic ecstasy at the top of her lungs, her hips and back came off the bed, only her head, shoulders and feet were still on the bed, and her body shook almost violently from the orgasm ripping through her defenseless body. Ryan kept up the tongue lashing of Jillian’s clit and turned her climax into a rolling orgasm that peaked four more times. All the while Jillian screamed and wailed in rapture as her body spasmed intensely. After the fifth peak of her orgasm, Ryan withdrew his mouth and Jillian crashed back down onto the bed like a rag doll. She lay there gasping and moaning, an occasional shiver racing through her body.
Placing his hands under Jillian’s curvaceous rear, Ryan lifted her hips into the air. Jillian weakly draped her legs over his shoulders as he leaned in and resumed his oral ravishing of her womanhood. Jillian’s body, still primed near its orgasmic peak, exploded again. Orgasm after orgasm racked her body. All the while, she screamed and wailed; repeatedly crying out in pleasure. Somehow despite the way her body shook from the orgasms rocking her, Jillian managed to buck her hips with Ryan’s technique.
After what was easily another dozen intense full body orgasm, Jillian’s head was thrashing back and forth. She was obviously trying to say “no” also, but all she was able to muster was a loud wailing “Nnnnnn…” She repeated it between gasps for breath four times before Ryan decided to have mercy on her.
Jillian’s butt plopped back down onto the bed as he released it, her legs sliding off his shoulders to the side. Her entire body glistened with sweat, and she gasped and moaned incoherently.
“Ready to surrender your body to me completely?” Ryan asked in a firm tone.
Jillian let out another soft moan in reply.
Moving up beside her, Ryan leaned in and whispered into Jillian’s ear. “Say I surrender. My pussy belongs to you, sir.”
Jillian was unable to find her voice, but managed to weakly shake her head no.
“Fun” Ryan replied in a wicked tone.
He slid back down and put his head between Jillian’s legs again. He kissed and licked her pussy, his tongue dancing over and around her clit. Jillian cried out in pleasure and her body tensed from another impending orgasm. This time, Ryan decided to up the intensity yet again. He slid two fingers into Jillian’s soaking wet womanhood. Jillian’s pussy instinctively tightened around his fingers and he began caressing her g spot. He alternated between a “come here” movement with his fingers and a semi-circular caressing movement with light pressure.
Jillian’s hips shot up in the air, trying to escape the erotic sensations overwhelming her. When Ryan kept up the moves, Jillian’s airborne hips began to buck and her pussy quivered. A low moan from her quickly grew into a full blown orgasmic scream of pleasure at the top of her lungs. Her body shook rapidly and she squirted her juices all over Ryan’s hand. As her orgasm subsided, Ryan stopped, but left his fingers still inside Jillian.
“Ohhhhh…” Jillian moaned weakly. “Ohgod ohgod ohgod.” She gasped.
“Surrender your pussy to me.” Ryan demanded flatly.
Jillian just whimpered weakly.
Ryan returned to fingering her g spot with vigor and going down on her clit. Jillian immediately had another explosive squirting orgasm, then after a few moments, five more followed in rapid-fire succession.
“STOP!” Jillian managed to scream out as the orgasms rocked her body. “Please!” she begged. “No more…” she managed to whimper between gasps. “I can’t take it.” “Y… You win, please… no more.” She whimpered pleadingly.
“That’s more like it.” Ryan replied smugly. “Now tell me who this pussy belongs to.” he demanded, wiggling his fingers inside her.
Jillian looked half conscious; exhausted and soaked in sweat. She weakly gasped over and over, trying to catch her breath. Her wild, orgasmic thrashing had dislodged the blindfold also. She barely managed to lift her head and gave him a humiliated & defeated look. “Y… you.” She whimpered.
“Say my pussy belongs to you, sir.” Ryan commanded.
Jillian gasped for a few moments, trying to catch her breath after the orgasmic roller coaster that had broken her will. “M.. my pussy belongs to you, sir.” She said in a humbled, submissive tone.
“Good girl.” Ryan said with a satisfied smirk. He stroked Jillian’s hair affectionately. He snuggled up next to her and began kissing her ear neck and ear lobe, prompting a series of weak but clearly aroused moans from Jillian. “Now be a good girl and tell me you belong to, body and soul.”
Jillian continued to moan softly, a doe eyed submissive expression on her face. “You, sir.” she replied in a submissive, but aroused tone.
“Good girl.” Ryan replied, caressing Jillian’s cheek and kissing her forehead. “Now what do you owe daddy?” he demanded gently.
“M.. my…” Jillian started, then abruptly paused. “I owe sir his pussy like I promised.”
“Good girl.” Ryan said again, kissing softly along Jillian’s neck as she cooed at both the erotic pleasure and the praise she was now hungry for. “And what do you want now?” he whispered into her ear.
Jillian looked pleadingly into Ryan’s eyes. “I… want sir to fuck me.” she said in an awkward, hungry tone. “I want to feel you inside me, making me scream.” “I want to hear you cry out in pleasure as I prove I’m a good girl.” She gasped. “Then I want you to fill your pussy with your cum.. feel it spreading inside me and know that you’ve claimed me as yours, sir.”