Lady Jane Claremore was traveling in her carriage when she saw him; he was young, in his early twenties perhaps and obviously from a poor family. Begging on the street corner, his head was still held high and proud – which of course meant that he wasn’t doing very well – and he did have quite a lot of muscle on him. Admiring his form and the splendid features of his face, she wondered from what hovel this beautiful young man had crawled from – and why no one had picked him up yet!
She had to admit that she was in a rather unusual position with her husband dead the past 15 years; at age 45 and a widow she had her money as well as her pick of men.
Not at all bad looking, the vestiges of her young beauty were obvious in the graceful lines of her face and the plump curves of her body. Of course her breasts sagged more than they had at a young age, and she was getting lines around her eyes and the corners of her mouth… but she was still an attractive older woman. She was also a very sexually active older woman with a hungry taste for the prowess and stamina of younger men, particularly beautiful younger men.
Her latest young man, having just reached the age of 25, had been released with a pouch full of money and many good wishes from his former patron. Lady Jane was quite sure that he’d do well for himself, and after the past 4 years of good service they’d finally tired of each other. Well, she’d tired of him anyway, she wasn’t sure whether or not he’d tired of her, but it didn’t matter anyway. It was really her desires that directed the whole event.
“Stop!” she ordered her driver, turning to lean out the window with a gracious smile on her face, the curves of her bosom very visible as she spoke to the young man, “Hello there, my name is Lady Jane.”
“Richie Worthing,” said the young man, looking somewhat confused. He had no idea why this elegant carriage with its attractive – if older – occupant had stopped. Especially because she wasn’t holding out any money – not that he’d gotten money often from a carriage as fine as this one.
“How would you like to come and work in my household?” she asked, smiling genially.
“Excuse me?” the poor young man asked, looking extremely flabbergasted. Nothing like this had ever happened to him before… certainly no lady of any standing had even stopped to ask him for more than directions, much less give him a job offer.
“Come on in,” she said, opening the carriage door, “We’ll ride around the square and discuss details, if they’re acceptable you can come home with me, if not then we’ll drop you right back off here.”
Her smile was kind and inviting… and was there something seductive in it? At any rate, Richie couldn’t see what harm he might come to alone in a carriage with an older lady. If the carriage even started the leave the square he would definitely be able to overpower her long enough to jump out.
“Hello Richie,” she said as he settled himself, her eyes wandering over the muscles that were just barely visible under his clothes, “So how old are you?”
“Twenty-two, my Lady.” he said quietly, looking at the luxurious interior of the carriage.
Lady Jane smiled, brazenly she outlined exactly what she needed a young man for. Richie felt quite faint… and rather unsure of himself. He had fooled around females his own age and station of course, even tumbled one or two of the maids at the inn, but he had never been propositioned by someone like Lady Jane. However his nervousness though, she was offering him new clothes, a place to live, pocket money, food… everything a young man in his position could possibly need. While he’d never considered fooling around with an older woman, could it really be that bad? Some of the men that he’d talked to on the street had said that older was better, more experienced and willing to do different acts that some of the younger girls thought they were above.
The promise that he would be taken care of, not only while he was with her but afterwards too, was too much to pass up.
“Good,” she said smiling, Richie gulped as she began to undo the laces at the top of her dress, pale breasts spilling out, topped with rosy nipples. “Now come over here,” she purred.
Richie knelt in front of her, although some of the blue veins were visible in her breasts, they were still round and plump, the hard nipples enticing. Leaning forward he began to mouth one of the nipples as she moaned; his efforts became more vigorous and he reached up with one hand to begin caressing her other breast. Lady Jane encouraged this with more moans, running her hands over his hair. Deftly she began unlacing his breeches, reaching in to feel the length and breadth of her newest young man… she moaned as she could barely fit her hand around his width. Although not the longest young man she’d ever had, he was probably one of the widest… not counting that young man she’d found abroad on the continent last year of course.
Smiling languidly she began to stroke his member as he groaned and suckled at her breasts. The carriage was leaving the city and heading back to her manor, the bumpy road creating a vibrating pleasure for her. Pressing Richie away from her breasts, Lady Jane lifted up her skirts – she was wearing petticoats, but nothing else beneath them.
“Have you ever used your mouth on a woman?” she asked, her legs spreading before him. Richie’s eyes were locked onto her creamy thighs and the pink pussy that was peeking out between them.
“A couple times,” he said, “but not very often.”
“Well, you’ll get plenty of practice with me,” she informed him, pulling his shirt to bring him down between her thighs. She moaned as his lips crept up her leg and to her pussy, his tongue making soft circles on her flesh before it delved into the rich nectar that was collecting at her center.
It was hot beneath her skirt, but Richie was also turned on by the fact that she was having him perform such a deviant behavior as they rode down the road. Licking at her wet slit, his nose was filled with the scent of her musk, he started to lick harder, nibbling on her pussy lips and sucking them into his mouth. Lady Jane moaned and humped at his questing mouth, feeling his tongue pressing against her hole. Letting go of her skirts she began to caress her own breasts, playing with her nipples and tugging on the rosy buds. Pleasure spurted through from her nipples to her pussy where Richie was insistently licking… oh how she’d missed having a young man, even though she’d only been without for a week.
His teeth closed over her clit and she cried out her passion, her fingers pinching down hard on her nipples as she came. Richie lapped at her juices as she writhed with orgasm on the seat in front of him, her face flushed with ecstacy.
Richie’s face was flushed too when he came out from under her skirts, the heat beneath there and his own arousal causing his face to redden. Lady Jane smiled at him seductively, her voice was husky as she said, “Lie down…”
The carriage was big enough that he was able to lie on the floor, and as he marveled at the comfort of the carpeted surface beneath him, he realized that she must have had it specially made. The evident lengths to which the Lady went to for her pleasures both astounded and excited him, she was so much more demanding and controlling than any other woman he’d ever been with. Looking at her he saw in her face both lust and experience… so she older, he was starting to find that more exciting than anything else. Already she was introducing him to new wonders and pleasures, her pussy sliding down his shaft as the carriage bumped and rolled along.
The motion of their ride only increased the erotic quality as she began riding him steadily… both of them were still fully clothed – and he realized that it only made sense to be since they’d be at her estate eventually. Lady Jane moaned happily as his thickness split open her pussy, her muscles clamping down on him in an experienced massage. Richie gasped as her pussy convulsed and rippled, doing things to his dick that he’d never felt before… she rubbed against his crotch, making his balls ache.
Her breasts were still out in the open, bobbling outside of her dress as she went up and down on him, her face ecstatic. Reaching backwards, she managed to get her hands under the many layers of skirts to his balls, squeezing them and tugging them gently away from his body as she ground down on his shaft. Richie moaned and his hands went to her waist, holding her down against him… both the view and the sensations were fantastic. She seemed to know exactly where to touch him – and how – in order to elicit the most exciting responses.
The carriage began to bump and vibrate continuously and Richie realized that they were on a stone road.
“We’re almost home!” Lady Jane gasped, her face ecstatic with the erratic thrusts and vibrations that the carriage caused. Richie realized that the stone road was hers, and he wondered if she had put it in just for this reason… but he didn’t have to much time to wonder as her efforts on top of him increased and his gripped her waist even harder.
Riding him fast and hard, she plunged his dick in and out of her body, joyously crying out as she shivered on top of him. Although he wanted to hold out, the intense feelings of her hand squeezing and tugging on his balls while she buried his dick in her elastic and convulsing pussy was too much. He came, just before she did, groaning as his seed shot up into her body; her pussy clamped down on him as he did so, her entire body tightening above him. Throwing her head back Lady Jane screamed her erotic pleasure, her crotch rubbing tightly against his and stimulating her pussy so that her orgasm continued.
Gasping, Richie’s dick was trapped in her orgasmic pussy and the sensations of his orgasm continued even though he didn’t have any more cum left to send into her. Instead he was left thrashing beneath her as his dick continued to be massaged and squeezed, giving him the sensation of an unending orgasm that went on for as long as hers did. When she finally relaxed on top of him, he gasped with both relief and disappointment.
A moment later the carriage rolled to a stop.
Lady Jane smiled, “We’re here,” she began lacing up her dress over her bosom as she pulled herself off of him, “Make yourself presentable – although it’s not as if the others won’t know what we’ve been doing.” her laugh was light and merry.
Richie hastily re-laced his breeches, covering his sticky groin that was coated in both of their juices. He followed her out and looked at the large and elegant house in front of him, and the surprisingly erotic and sensual woman that was walking towards it.
For a chance at a new life, he didn’t think he could have picked a better route.