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James lay in bed stroking his erect young cock as he recounted his experience with Olivia. He had often imagined losing his virginity, but never imagined being seduced and pleasured with such a hot and sexy older woman. Compared with some rushed encounter with someone equally inexperienced, he had to pinch himself at the thought of Olivia's nubile body, skillful techniques, her willingness to suck his cock and make him cum, before getting him hard again and taking his cock in her lovely tight wet pussy.
He also found himself imagining Mrs Tyler the neighbour, and how turned on he was seeing her in her tight dresses and skirts and heels as she left for work and returned.
The following morning, the weather was cooler and it was cloudy and grey as he rode his bike up to Brian and Jan's house which was around a mile from the village. Olivia had said to be there for 9am and he made his way around to the kitchen where she was waiting wearing a skimpy silk nighty with spaghetti straps and lace edging.
"Good morning James"
James replied and she sat on the sofa in the large kitchen/diner/lounge area and patted the seat, inviting him to join her. Her tanned legs caught his eye, as did her gorgeous breasts, with semi erect nipples visible through her nightie.
James sat down and she started kissing him, as she had done the day before.
In between the erotic kisses and her sensual hand movements, she started probing into his sexual likes... "So what is it about Mrs Tyler that turns you on.... tell me about her and what you imagine doing to her"
James felt a little embarrassed but also very aroused, as Olivia kissed his neck and whispered in his ear, with her hand brushing over his cock. She told his not to be shy and asked again...
"Well she's in her early 30's, slim with shoulder length brown hair, always looks smart going to work"
"What does she do and what kind of outfits does she wear James?"
James by now had a very hard cock and Olivia was squeezing it though his shorts... "She wears dresses and skirts, high heels, I have seen her in her bikini in the garden.."
"So you like ladies in heels and dresses James?" Does that look turn you on?"
Olivia asked again and she moved his hand to her swollen breast and erect nipple.
"I worked in a marketing agency... I spent my working week in dresses and heels... sometimes short skirts with black tights, sometimes longer dresses with holdups... always sexy lingerie... nice perfume... I liked to charm our male clients - looking good is good for business!" Do you think you'd fancy me if I was dressed like Mrs Tyler...?
James was now in a very aroused state and he replied "Yes" as Olivia released his cock, and he felt her warm lips around it. As she started to suck, she looked up, stopped momentarily and said "Good..."
The sensation of her licking and sucking his hard young cock was as amazing as the previous days, and he knew that he would soon end up cumming in her mouth again.
Olivia stopped after taking him deep in her mouth, and moved up to kiss him... "It's forecasting rain this afternoon.... you'd better get on with that fence - come in for lunch at 12.30, I'm going into town but I'll be back before then... we will continue."
James was bemused at the sudden stop, his cock soon lost its rigidity as he put it away, Olivia gave him another playful kiss, before slipping her middle finger between her engorged and wet pussy lips, and cheekily licked it as her young lover prepared to head off to do his jobs.
Olivia had a plan, and once James was on his way, she headed into the master bedroom and her mothers wardrobe. Jan was in fantastic shape as she approached 50, and her and Olivia were both size 10 in dresses and size 5 in shoes. Having being Brian's PA, she had a great selection of very nice shift dresses, pencil skirts and tops (he funded her shopping trips long before they were officially a couple).
Olivia picked out a fitted grey dress, with buttons down the front, just above the knee, and also took out a paid of black heels. Her own suitcase contained a limited selection of her lingerie since she'd only packed a few basic items, with a view of spending most of her time in her bikini or topless! Having put the dress and heels in her own room, Olivia then pulled on some jeans and a T shirt and drove into Stratford and headed straight into M&S and their lingerie department. Within a few minutes she had selected a suitably sexy lacy black bra and knickers set, and picked up a pair of sheer black holdup stockings... smiling to herself at the thought of young James lusting after his neighbour. Olivia paid for her items and picked up a few items in the food hall, before heading home.
Olivia lay in the lovely spacious bath, her calves draped over the sides as she carefully and thoroughly shaved her pussy. Once it felt totally smooth, she did indulge in a little "me time" teasing her swollen clitoris and labia, but stopping short of climaxing... saving that moment until James' finger, tongue, or cock took her over the edge. She got out and dried off, moisturised and dried her hair, before lying naked on the bed browsing on her iPhone. Soon after midday, she got dressed, adjusting the bra straps to show her breasts off and pulling on the sheer holdups, smiling wryly at the thought of James...
12.30 arrived and James appeared at the door. Olivia appeared and his eyes were on stalks. She closed the door behind him and pressed him against the wall, kissing him on the lips, only stopping to say "Is this what Mrs Tyler looks like when she goes to work...? Is this what you imagine when you're wanking off in bed?... How do I look?"
James stammered a reply - this was beyond his wildest dream and fantasy. "You look amazing Olivia".
She walked across the kitchen and bent over, her shapely buttocks facing James. "Is this how she looks when you see her bend over at the car when she's going to work..?"
James replied, again completely mesmerised "Yes... you look so sexy".
Olivia faced him, running her hands over her breasts and down to her thighs. "Why don't you have a quick shower and meet me in my bedroom young man... I think you might like what's under this dress... you bad boy!"
James didn't need asking twice... his confidence had quadrupled in the short few days since Olivia set about educating him!
He stood in the spacious shower, soaping his armpits, and paying particular attention to his semi erect cock. Showers at home usually meant having a sneaky wank, spurting his cum towards the plughole as he imagined Mrs Tyler, or one of the other ladies who featured in his lustful young mind. This time he was showering ready to join the incredible Olivia in her sexy dress, heels and lingerie. He dried off and wrapped a towel around his waist before heading for her bedroom.
As he walked into the bedroom, Olivia told him to sit on the bed, before standing before him, and undoing a couple of top buttons on the dress to reveal the lacy black bra that barely covered her full firm breasts. Her hand slipped inside her bra and she teased her nipple, maintaining eye contact with James. Before moving closer, kissing him and undoing his towel and running her hand over his rapidly stiffening young cock. She then took his hand and placed it inside her dress and bra, licking her lips as he caressed and squeezed her erect nipple. Olivia's nipples were incredibly sensitive and became very prominent when aroused. In fact there had been several occasions when she had managed to climax totally from nipple play. As James sat naked, playing with her breast and nipples inside her lacy black bra, she could feel her pussy get wet... very wet in fact. He was gently stroking his cock which looked bigger and harder that the previous day.
Olivia moved back a little, giving James full view of her as she seductively bent over the end of the bed, lifting the rear of her dress as her naked young lover sat watching from the chair. The tension in the air was broken when she heard James say "Oh My God" as she revealed her lace topped stockings and the tanned bare thighs above them.
"You like?" She asked as she writhed before him.
"You are amazing... so sexy, I love it" James replied, his cock now rock hard at the sight before him. He clearly had a couple of fantasies or maybe fetishes, one being older women, the other being the classic sexy secretary look. This may have been fuelled by the frequent after school visits to the solicitors offices where his mother worked as he waited for a lift home from her. He was always very polite and well behaved, and would generally sit in reception and wait, enjoying the sight of the receptionists, secretaries and female solicitors who walked past him as they delivered and collected files. Heels, skirts, tights or maybe stockings, wafts of perfume, immaculate hair nails and makeup.
The sight of Olivia as she touched and exposed herself before him was like a pure fantasy come true. Part of him could not believe this was happening, part of him could not wait to touch her, taste her and basically fuck her!
Olivia then stood facing him, ran her hands up her nylon covered thighs and started touching herself through her transparent black knickers. She had learnt long ago that most men loved seeing a woman touch herself, and by the look of James face and his cock, he was clearly enjoying the show.
"Do you want to run your hands over my stockings James?"
James nodded... Olivia moved forward and felt his hands running over the sheer stockings, and up her thighs, as her dress lifted. He then unbuttoned two buttons on her dress, she parted her legs as James pushed her dress up, and she felt his fingers on the bare skin above her stocking tops and then they brushed over her soaking wet knickers, his touch electrifying against her engorged, wet, throbbing lips. His earlier lesson paid off and he took his time, and then she felt his fingers move inside her sodden knickers and they slipped over her swollen wet lips and clitoris.
Olivia was in a totally horny, erotic and sluttish mood. Yesterday was about gently taking his virginity, today was about fulfilling his fantasies and teaching him to really know how to excite a woman. She beckoned him to his feet, kissed his lips and told he she wanted him to lick her pussy and make her cum. She pulled up her dress (or technically her mothers dress - which made it all the naughtier!), sat back in the chair, pulling her tiny knickers aside to reveal her swollen, and very wet pussy, instructing James to kneel and lick her. He needed no persuading and soon had his tongue exploring her wanton pussy as she ran her fingers though his hair, guiding his head as she told him exactly how she wanted to be be pleasured.
James was in heaven, Olivia's stockinged legs around him as he licked her, tasting her sweet juices, his cock throbbing as she moaned and writhed before wailing and pulling his head tight against her as she climaxed loudly.
"That was very very good James.... You are a fast learner..." Olivia stood, pulling him to his feet before kissing him on the lips. She then manoeuvred him to the wall, before crouching and taking his cock in her hand and slowly wanking it before taking him in her mouth.
He closed his eyes and moaned as his experienced and skilful lover started licking and sucking his throbbing cock. He desperately wanted to make sure he didn't cum as fast as yesterday, and as he warned Olivia, she giggled and stopped sucking, looking up at him, she smiled.
"I'm not expecting you to last long, but I want your lovely cock inside me... what position do you want your sexy office lady in young man... On my back with my dress puled up, bent over with my dress pulled up... my dress off?"
James had imagined fucking women in a variety of positions, Mrs Tyler was a regular wank fantasy bent over, with a dress and heels on, being fucked from behind. Olivia's offer was too good to miss... she looked so hot and inviting when she bent over and revealed her stockingtops earlier. "Can I fuck you from behind... please".
Olivia smiled..."My favourite..... enjoy, fuck me hard and let me feel your cum... knickers on or pulled aside?"
She then hitched up her dress, bent over the side of the bed, one heeled foot on the floor and one knee on the bed, she then reached between her legs, pulling her knickers aside. Mark always told her this was the horniest, sluttiest sight on earth... he too loved taking her from behind, and whilst enjoying most positions, this was so raw and animalistic, it was pure fucking.
James held his cock in his hand and positioned his knob against her slippery lips, and they both moaned in unison as he penetrated her. He instinctively held her hips as he started slowly fucking her, loving the feeling, but desperately wanting to make it last as long as possible! The sight of Olivia's gorgeous body with her dress pulled up to reveal her stockinged heels and bare arse was enough to make him erupt, the combination of this and the sensation of having his cock buried in her tight wet pussy made it incredibly difficult to pace himself.
Olivia's moans of pleasure and encouragement ramped his excitement up to another level, and within a few more seconds he reached that all familiar point of no return! Olivia sensed the same familiar feeling, that feeling when an already hard cock seems to get harder and longer and the inevitable is about to happen. James was certainly not holding back and she decided to help him along, and reached between her legs to take his sac in her hand and massage his scrotum as his semen started to spurt deep inside her, each grunt signifying another pulse of his cock and another deposit of his creamy cum in her hungry pussy.
James' head was spinning, the intensity of that orgasm, fuelled by the build up from the minute he arrived at the house was off the scale. He withdrew his cum covered cock and grabbed some tissues from Olivia's strategically placed box by the bed. He suddenly felt awkward for a moment, which passed as soon as Olivia spoke.
"Pass me some tissues quick or you'll end up having to explain to my mother why one of her expensive dresses needs dry cleaning!" Olivia giggled as she wiped the copious amounts of his semen which was now gravitating out of her freshly fucked pussy!
"So, how was that.... did I live up to your fantasy fuck? Did you imagine that you were fucking Mrs Tyler when you came?" Olivia teased him.
"No, no of course not, that was incredible, I have never been so turned on!" James replied.
"Well you were still a virgin yesterday morning so i should hope so!"
Olivia giggled again, she had always had a mischievous streak and this was virgin territory as she she lay back dressed to fuck in her mothers Karen Millen dress and stockings, with a young playmate naked before her.
"It's not really your mothers dress is it?" James asked, sure that she was teasing him.
"Yes, and the heels... the lingerie and stockings are mine and new - just imagine if you ever see my mother around town in this dress, you will have to compliment her... and remember the sight of it pulled up over my bum as you fucked me!"
James blushed at the thought, and had a fleeting thought about Mrs Adkins, who was a very attractive lady in this same dress, and wondered if she too was as sexy as her daughter!
Olivia decided that the dress ought to come off, it had done its job and escaped the need for the dry cleaner thus far, so she stood up, and seductively undid the buttons, one by one to reveal her new lingerie. She slipped the dress off and placed it on the chair, James marvelled at the sight of her in her heels and holdups... she then peeled off her knickers and moved closer. "you'd better practice undoing bra's.... it's an important skill..."
James did as he was told and proceeded to start caressing and squeezing her breasts and pinching her erect nipples.
"Suck them..." Olivia instructed as she lay back and James' naked body was pressed against her.
James loved the feel of her full breasts and happily sucked her hard nipples as she moaned and her hand reached down to his cock which soon responded to her expert touch. Olivia loved the feeling of a cock hardening in her hand... the thrill never failed to excite her, and she reflected on the fact that she had in fact, wrapped her perfectly manicured fingers around quite a selection of cocks, and her technique clearly pleased. James was soon fully erect and they kissed, and his fingers started to probe her pussy. She was certainly wet enough for round two, with the remains of his earlier ejaculation, and her own juices. As James lay back with his erection fully ready for another lesson, Olivia moved to straddle him and gripped his cock, rubbing the tip against her wet lips and swollen clit.
James looked up in awe at Olivia's naked breasts and erect nipples as she writhed against his cock. His hands ran up her stockinged thighs and she made eye contact before speaking...
"So do you want to fuck me again?"
"Yes... please..." James was desperate to feel Olivia impale herself on his cock, knowing he would be able to resist the urge to cum too soon.
No sooner than he had spoken, Olivia positioned herself and slid down his cock, and watched his facial expression as his cock disappeared into her hungry pussy.
Olivia loved being on top, being in control of each movement, moving position to feel every sensation possible. she could lean forward to get maximum penetration, or lean back to put pressure on the G spot, slide up and down its length, slowly, quickly. She rode him slowly and ran her hands over her naked breasts, and then invited James to pinch her nipples as she rode him.
James was rock hard, and loving the fact that he could enjoy the sensation without worrying about cumming too soon. Olivia then leant forward and lowered a nipple to James' mouth as she slid down his cock. He sucked and licked her hard nipples in turn for a while before she suggested he go on top.
Olivia rolled onto her back and spread her legs wide. James mounted her and penetrated her again. She wrapped her stockinged legs around him and pulled him deep inside her. Her heels dug into his back as he fucked her enthusiastically, clearly building up to another orgasm. Olivia kissed and bit his shoulder and neck as he fucked her, and she kissed and licked his earlobe, whispering in his ear.
"Fuck me hard and cum for me.... don't stop, just fill my pussy, think of me bent over in that dress... just fuck me!"
This tipped James over the edge, and within seconds, for the fourth time in 24 hours, he was ejaculating in this gorgeous young woman. He kept thrusting as he released wave after wave of cum deep inside her as she moaned loudly, gripping him with her stockinged legs, her heels digging into his back as she simultaneously climaxed with her young lover. She kissed him and held him inside her as her orgasm subsided and his spent cock slowly subsided and slipped out of her.
Olivia moved her hand down and started massaging the leaking cum over her pussy lips and hairless mound. Her finger slipping over her clitoris as she smeared James' cum into her skin. James lay back exhausted, processing what the past 24 hours had delivered. When Mr Adkins asked him if he'd come and paint the fence while they were away, who could ever have imagined that he would end up having the most unbelievable sexual encounters with his beautiful stepdaughter!
"Come on, we'd better get you showered and respectable before your mother comes looking for you!" Olivia giggled and got up, kicked off her heels and peeled off her holdups before heading for the bathroom. Olivia then put the shower on, before sitting on the loo for a wee. James appeared at the door and she pulled him into the shower, kissing him and encouraged him to soap her breasts and buttocks as she lathered her hand and washed his cock which soon started to get hard again. She kissed his lips, neck and shoulders as she rubbed and squeezed his cock which was soon hard. She dropped to her knees and as she gripped his shaft, she took it back in her mouth again. She sucked and wanked him as he leant against the shower wall, moaning, meanwhile Olivia had her other hand between her legs masturbating.
Her horniness was nothing new, and the thrill of wanking and sucking this hard young cock as the warm water cascaded over them was exhilarating. She could feel his cum leaking from her fucked pussy and plunged her fingers inside herself as she took his young cock deep in her mouth. While James was enjoying the thrill of yet another Olivia encounter, she wryly smiled at the fact that she had in fact assumed this position in this same shower with around 5 different guys, including one while Brian and her mother were downstairs having breakfast!
James had so far enjoyed the sensation of cumming in her mouth, in her pussy in several positions, so she decided that this would be the time to give him another little special memory to take to Uni. As she felt his cock stiffen, she increased the intensity of her wrist action whilst pulling her head away, closing her eyes and opening her mouth. Right on cue she felt him release another load of his virile semen which landed on her face, lips, in her open mouth and on her chin. He moaned and uncharacteristically swore as he looked down at her beautiful face covered in his creamy cum, just like he'd seen in some porn clips he'd secretly watched on his phone. Olivia took him back in her mouth and sucked the last drops of his cum from his cock, before standing, and letting the shower wash the remains of his orgasm off her face before kissing him. They dried off and James got dressed... Olivia lay naked on the bed...
"Remember... this is our secret... and by the way... today was a big improvement on yesterday..... I may well teach you some more before Mum and Brian get back!"
James replied "You are amazing, and of course it's our secret - I promise never to tell anyone"
They shared a kiss before he headed off to do an hours painting before heading home on his bike, wondering what else she had in mind!
Olivia lay on her bed relaxing, reflecting on the fact that her first week of garden leave had been memorable.... the fact that Gemstone were technically paying her to sunbathe, and fuck was rather amusing... James, despite his inexperience had made her cum multiple times and the orgasms were good... in fact she looked forward to more fun with him in the days before Brian and Jan returned.
Olivia then put her lingerie and stockings in the wash, and returned Jan's dress and heels to her wardrobe, safely stowed after their raunchy adventure.
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