The First-Time Cougar

Jessica sat nervously sipping her drink in the hotel lobby bar while waiting for Jamie, wondering if she was lining herself up for a rejection by this young attractive guy. They'd met online and built up quite a rapport but then the conversation had moved on to sexual preferences and ultimately a series of heated, erotic conversations which had led to this meeting. Photos had been exchanged early on, but Jessica still had doubts that such a handsome young man would really find her as attractive as he'd previously indicated.

By all means, Jessica looked very attractive and very sexy for her age. She'd kept her curves and was seen as voluptuous by men of her age. Could a young 24 year old hunk really want to do all the things he promised to, during their online conversations? Jessica was about to find out.

They'd chosen that location to meet as it was midway between where they lived in almost opposite sides of the UK. It wasn't that Jamie was late - Jessica had just arrived early, keen that she was to fulfill the online sexual promises that had been made.

Jamie arrived early as well, not too long after Jessica had settled into her hotel bar seat. He looked just as handsome and sexy in person as he had in his picture. Jessica firstly felt relieved that he had indeed turned up and then she had an overwhelming mixture of both nerves and a high sexual 'want' of this strapping well turned out young man with a killer smile walking towards her.

"Jessica, it's a pleasure to meet you finally." Jamie started, with a wicked knowing smile and glint in his eye.

Jessica felt her body tingle as she stood up and Jamie came to her, putting his hands on her hips, kissing her on each cheek like a gentleman, the second kiss of his lips was so soft and lingered slightly. They parted and he held both her hands as they stared longingly at each other, with smiles that showed their delight and pleasure.

"And you Jamie. I'm so glad you turned up. You sometimes never know who you're talking to online but I had a good feeling about you and I'm so pleased you turned out just as you portrayed yourself." Jessica replied enthusiastically.

"Well I can assure you.," Jamie continued. "You look very attractive and I'm so glad we both made the trip."

"Thank you very much. I hope you're just as glad later on." she said, with a wicked smile as she sat back down again.

Jamie winked back at her then offered her another drink, noticing that she'd nearly finished the one she was on. Jessica said she was fine, so Jamie got himself some liquor on the rocks and then sat in the seat next to Jessica.

"You know I've never been with anyone younger before." Jessica said, feeling herself blush.

"I remember you saying. I'm very honoured that you chose me to have this rendezvous with. So this makes you a first time Cougar then?" he said with a small chuckle.

Jessica tried to look surprised that Jamie had mentioned the label of 'Cougar' because he was right and she laughed, nodding her agreement. She'd had fantasies about being a Cougar but in her advanced years, never thought it would ever arise.

Jamie knocked back the liquor, keen to start pleasing this mature, sexy woman. "Shall we?" he asked, standing up and offering Jessica his hand.

"Oh yes please." Jessica replied, immediately rising up, leaving the rest of her drink and feeling much better about the situation as this offer from Jamie was the ultimate acceptance that she was exactly what he wanted.

Jamie walked hand in hand with Jessica over to the reception desk, checked in and taking the key, led her to their hotel room that he'd pre-booked as soon as they'd agreed the location and date the week before. He was lucky to get as lovely a hotel as it was on such short notice. She held his hand firmly, keenly allowing Jamie to lead the way, finding herself almost unnervingly under his spell already, given how strong a woman she is in her normal life.

Jessica finally took the lead and made the first move to kiss Jamie deeply when they got to their room door. He was a few inches taller than Jessica even though she was wearing her killer heels and it felt a very comfortable position, her head slightly angled upwards as their lips met firmly, their hands on each other's backs and then as their tongues met, she felt Jamie's hands roam down, cupping her ass cheeks, pulling her tight against him. She took an intake of breath as she felt his cock grow against her as they continued to kiss, but then he drew away from her, only to open the door and usher Jessica inside.

Jamie led Jessica over to beside the bed, laying their discarded jackets onto a chair on the way. He stepped towards her, their eyes looking deep inside each other's soul as his hands brushed her shoulder length hair away from the sides of her face, cupping her cheeks and returning his lips to hers once again. Jessica felt her nipples harden and her pussy dampen as this strapping young man kissed her so passionately, so sensually than she'd been kissed in a long time.

Her hands roamed over his back, feeling his strong frame, moving down to his ass and then one hand moved round to the front, feeling for his young hard cock. She wasn't disappointed. Jessica felt the base of his cock through his suit trousers and then she slowly ran her hand dowards, outlining his hard shaft. Jamie moaned, feeling his cock start to throb under the delicate attention of Jessica's hand through his suit and the soft touch of her lips against his, so sensual a kisser as she was.

He moved the hair from her neck and started kissing her soft skin, his hands started unbuttoning her blouse. Her hands ran up his back and through his hair, leaning her head back in acceptance of his wonderful kisses down her neck and still moving downwards. Button after button came loose in his fingers until he was then able to slowly move the material off of her shoulders and lay it gently on the chair with an outstretched arm.

The clasp on the back of Jessica's bra was then expertly undone by one of Jamie's hands and that too was also discarded onto the chair. Jessica felt her breasts come free and her nipples becoming hard as his kisses moved down her neck, onto her chest and cupping her left breast, his lips pressed gently against her as his thumb brushed slowly to and fro over her hard nipple. She grasped at his hair tighter as his tongue flicked at her nipple slowly to and fro, then replaced his tongue with his lips, sucking gently and softly at her firm nipple. Jessica felt her pussy dampen further and her clit started to tingle again as Jamie suddenly sucked firmly on her nipple, her eyes closed, her head angled upwards. If this was how good his lips felt on her body, she couldn't wait to have his young hard cock fuck deep inside of her!

Jessica was revelling in the fact that this young man couldn't wait to please her. She felt Jamie unzip her skirt and then it fell to the floor around her ankles. He then leaned back to marvel at the fabulous mature woman standing partially naked in front of him and felt his cock throb so hard when he saw that Jessica was wearing crotchless pantyhose.

"I thought I'd give you a surprise." she said, watching the very excited look on his face.

He'd told her of his fetish for such nylons during their online chats but never imagined Jessica would deliberately go out and buy a pair just for their meeting!

"Oh you certainly did that Jessica - that's just so bloody sexy!"

And with that, Jamie led Jessica over to the bed, laying her down with her legs hanging over the edge, her lovely mature body naked apart from the pantyhose and killer heels.

Jamie undressed himself as he stood before her and she watched. As his shirt gaped open, she saw his young muscled torso, then his shoes and trousers were discarded and she saw his strong firm thighs and then her eyes wandered to his hipster underwear which was straining to hold his obviously hard cock. Jamie kept his underwear on, keeping a certain level of secrecy over his cock which Jessica was so keen to finally now see and feel, skin to skin. She had to wait a short while longer though.

Kneeling astride her on the bed, Jamie leaned down and kissed Jessica deeply, lips meeting firmly, tongues entwining - so much 'want' being conveyed by them both. Jessica took the opportunity to grasp at his cock through his hipsters. She moaned out as he was so hard and felt so thick through the material. She instantly felt the juices starting to flow inside her pussy at the feel of his cock in her soft hands. Jamie pulled back though, his cock still straining to escape his underwear, his lips kissing their way down Jessica's body.

He paused over her right breast to suck at the yet untouched nipple, causing her to moan out and wrap her nylon-clad legs around his back but he moved down further and she had to release him. Jamie kissed down her cleavage onto her stomach, then down further towards the heavenly hole in her nylons and her warm wet pussy. Jessica's hands were once again on the back of Jamie's head, grasping at his hair as she felt his breath on her wet pussy lips. Jamie had stopped to briefly glance at Jessica's inviting haven. Her pussy lips were already wet with her juices. Totally thrilled to see the effect he'd had on her so far, he thought.

With the first feeling of Jamie's tongue on Jessica's wet pussy lips, she felt her whole body was weightless. He ran his tongue slowly around the outside of her lips, tasting her finally, loving the feel of her smooth juices trickling down his throat. His tongue then ran up between her pussy lips, parting them, his hands reaching upwards, caressing Jessica's breasts, her nipples between his fingers, pressing them and pulling at them slightly but enough to have Jessica marvelling in the attention her body was receiving.

Jessica wrapped her nylon-clad legs around Jamie's head, encouraging his head closer against her pussy, her legs draped over his shoulders and the bottom of her heels resting on his lower back. Jamie wanted to please this wonderful older woman over and over. He wanted to make her cum again and again. He ensured she was well on her way to her first orgasm with him when he started lapping at her clit with this tongue. Jessica let out a loud approving moan, arching her back, her head pushing down backwards against the pillow.

Jamie moved his hands down under Jessica's ass so that he could keep her hips up and her pussy tight against his face. His tongue circled her clit then started flicking at it. Jessica was writhing around, grasping at the bed covers, clenching them in her hands, her breathing was heavy and the feeling on her clit totally amazing as this young man set about pleasing her.

Just as Jessica thought things couldn't feel any better than having Jamie lapping at her clit, he brought a hand round from her pantyhose covered ass and slid one finger slowly and deeply inside of her, making her moan loud as his finger found her g-spot up and behind her clit which he started caressing with the flat of his fingertip insider her, his hand getting wetter and wetter with her delicious pussy juices.

"Oh yes, that's so fucking good. Don't stop!"

Jessica almost begged, but there was no chance of that as Jamie wanted to taste Jessica's first orgasm.

The finger inside her pussy and his tongue lapping at her clit was working Jessica up an absolute treat. Jamie's tongue lapped at her clit faster. His finger rubbing inside her wet pussy firmer and faster as well.

"Fuck, I'm going to cum!" Jessica screamed out.

Jamie as young but experienced as he was, was already fully aware she was close and took her clit between the very tips of his lips and sucked on it firmly, pulling it to and fro between his lips, his finger still fucking her pussy as her juices trickled down his chin and flowed down his hand.

Sucking her clit sent Jessica over the edge. She felt her orgasm start from her clit and then it ripped around her body. She never thought an orgasm could be as intense as this. Her body bucked, her heels digging into Jamie's back while he tried to steady her, continuing to suck at her clit, feeling her pussy tighten around his finger which was now deep inside her pussy fucking her firmly.

Her orgasm fully revealed, Jessica grabbed at Jamie's hair, pulling him off of her clit as it became so sensitive with the orgasm, she couldn't handle the attention on it anymore. His finger fucking slowed to a gentle penetration back and forth as he felt her orgasm come and go in waves, watching Jessica try and catch her breath again as her orgasm subsided.

"That..." Jessica panted, "...was amazing! Now let me see that young cock of yours."

With that, Jamie raised his body up, his face wet with pussy juices from Jessica grinding her pussy against his mouth. He leaned over her and kissed her passionately. She moaned as she tasted her pussy from his lips and his tongue, her tongue almost lapping the pussy taste from his.

Jessica was just about to reach for his cock once again but he got up, causing a slightly disappointed look on her face. That soon changed though as he pulled at his underwear, letting them fall to the ground and Jessica let out a very delightful moan of approval. His cock was just what she'd hoped for - a good length, thick and so very fucking hard for her! His cock head shiny and damp of pre-cum she noticed.

Jamie beckoned Jessica off the bed, turned her round to face away from him then slowly beckoned her to lean forward, eventually leaning on the bed with her outstretched arms.

Without a word from either of them, the only thing to break the silence was the expectant heavier breathing from them both. Jamie was in charge though.

He moved close against Jessica's ass, the top of his young shaft pressing firmly against her pussy lips. He moved his hips away and then towards her a few times, teasing her, her lips giving way and parting for the thickness of his shaft as he pushed his cock against the wet mature pussy he wanted so much.

Then in one firm push Jamie's thick cock slid firmly and tightly deep inside Jessica's wet pussy.

"Oh fuck!" She screamed out as she felt her pussy stretch to accept him.

To Jessica's surprise, Jamie then pulled his cock slowly, right out of her haven, his shaft glistening with the wet pussy juices now encasing it.

"I want you to taste your juices as you suck my cock." Jamie said.

Jessica bounced off the bed with eagerness and excitement, quickly kneeling in front Jamie, her face tantalisingly only a few inches away from the tip of the fantastic cock that stood hard and high before her.

Jessica looked so very sexy to him. Her long dark blonde hair, her full round breasts, her curved body, her lovely nylon clad legs and those stilettos - all packaged up in one very sensual, intelligent, mature woman.

Her tongue was the first thing to touch Jamie's cock. It ran slowly from the base of his shaft slowly upwards, her eyes transfixed on his reaction. All the way up his shaft her tongue collected her own juices. Juices that so often in the past she has licked from her fingers upon orgasm, just for that added bit of excitement when pleasing herself.

On reaching the head of his thick cock, Jessica's tongue ran up the underside, the tip of her tongue taking one long lap at the head of his cock, wet with a delicious mixture of his pre-cum and her pussy juice. Jessica drew her tongue inside her mouth and for a moment savoured the taste of their mixed juices.

Jessica gripped Jamie's impressive cock at the base with one hand, the other hand cupping his testicles. His hands grasped at her dark blonde hair as she started sucking his thick cock firmly, then bit by bit sucking his throbbing warm shaft further and further into her mouth. She was all but giving him a deep throat with that initial engulfing of his cock between her red painted lips.

With her piercing eyes, Jessica all the time strained to look up at Jamie's very favourable reaction as she drew her head back, her lips smoothly releasing his shaft, up to the ridge of the base of his cock head and she then sucked his thick shaft deep inside her mouth, her lips open wide.

She was allowing their juices to trickle down her throat, her moaning on par with his ecstatic short grunts as he started moving his hips to and fro, pushing his cock deep into her mouth again each time. The way he then grasped at her hair, holding her head close, his thick cock pushing deep inside her mouth... he was fucking her mouth so eagerly, keen to have his juices pouring down the back of her throat.

Jessica was so fucking turned on, she could feel her pussy juices running down her smooth inner thighs, her clit pulsating as was the effect this young man with the cock deep in her mouth was causing.

Jamie's thrusts forward increased in speed and determination. Jessica had a perfect grip on the base of his thick shaft, her lips keeping as tight around his cock as she could muster, given that he was fucking between her lips, his balls slapping against the underside of her chin.

Jamie then panted out loudly "I'm cummmmming!"

Jessica didn't need told and she wasn't disappointed as with one firm grasp of her hair, he made her stop the mouth fucking and she wanked him hard and fast, her mouth sucking on his thick throbbing cock head as his cum then shot out in waves towards the back of her throat. Jessica moaned out loud as she took one gulp after another, her mouth engulfing his cock head as it exploded in her mouth, his juices almost too much for her, to her surprise and delight.

As Jamie's orgasm subsided, Jessica's grip loosened until she was gently lapping at the eye of his cock with the tip of her tongue, catching the last drips of his warm cum from his now semi-hard cock. Looking up at him, Jessica continued to slowly lick and suck him, so keen she was to have him hard and fucking deep inside her. He wasn't to start disappointing her in any way.

After a short while of Jamie running his hands through her hair, then feeling the contours of her neck while Jessica continued working him up again (not that he needed much persuasion), he ushered Jessica up onto her feet and then led her back onto the bed, He had her kneel near the edge of the bed, facing away from him and he leant her forward, now marvelling at the once again fabulous sight before him.

Jessica, now kneeling with her legs apart, looked around behind her, moving her ass side to side slowly, teasing Jamie, spreading her wet pussy lips, her inner thighs glistening with pussy juices, her pantyhose wet, her killer heels pointing behind them both. Jamie slowly moved towards her, his cock in hand, he was looking at her open cunt as he firmly gave his young thick cock long meaningful strokes.

First, the palm on his right hand smoothed over her right hand side ass cheek, then his left hand followed suit on the other side. He massaged Jessica's ass, making sure that part of the motion pulled her ass cheeks apart, stretching her ass and her pussy. With each such movement came an agreeing moan from Jessica, who was by now caressing her clit with two of her red finger-nailed digits.

Jamie, fully hard again, then took the erotic feelings to another level once more. Jessica felt him press his cock against her open wet pussy and before she could steady or prepare herself, he fucked deep, oh so very deep inside of her, causing her to scream out in ecstasy, trying to catch her breath at the same time.

It felt so fucking good having his cock once again so hard and so deep inside her wet tight mature cunt. They both wanted this so much and had waited what seemed so long to meet up and have this happen. Jamie didn't let Jessica catch her breath much before he then withdrew his cock from deep inside, pulling back so that her hole entrance was just at the ridge of his cock head and holding tightly onto her hips, he once again drove his cock high inside her soaking wet pussy.