Young Simon & His Older Teacher

Simon found that he was still shaking long after Mrs Connor had left his side. His mouth was dry and his chest felt tight. His pulse throbbed when he recalled the older lady’s gentle stroking of his firm young cock and he wondered at the way his fear and trepidation had simply melted away under her experienced hand.

His mind whirled as he remembered her praise when he’d finally ejaculated. He hadn’t been expecting anything except disgust at his youthful enthusiasm but instead, she’d seemed surprisingly impressed. “What did she mean ………..are my reactions really perfectly normal, like she said... would she have gone further and sucked me off?”

He also thought about Mrs Brady next door, dressed only in her bikini, who first prompted him to masturbate himself in front of his mirror. He’d often wished that she would go further one day, maybe going topless thinking that she wouldn’t be seen. Images of a less careful Mrs Brady reclining totally nude outdoors made his heart skip a beat and an erotic combination of images flashed through his mind.

This time he didn’t have to imagine having his first intimate experience with a woman. A brief reminder of the soft feminine hand on his member earlier that day started Simon attempting to re-capture that special feeling. It wasn’t quite the same but he tried his best to imagine it was Mrs Connor as he stroked himself off to another, though this time less spectacular ejaculation.

Later, having showered, Simon thought about the forthcoming evening’s arrangements. He came very close to calling it off but, swallowing hard, he steeled himself to the fact that this was something he really wanted to do. He had often wondered what he should do if ever confronted by just such a situation and he wondered if he could persuade Mrs Connor to actually get naked with him this time.

The tension continued to grow as he waited and several times he almost made the call to cancel, once actually getting as far as dialling the number before quickly aborting the call. He had to go through with it. Did she really mean what she said about giving him more experience?

Finally he heard the sound of a key in the door and the familiar sound of Mrs Connor’s voice calling out to greet him. Now it was too late to cancel and he swallowed hard as he rose to meet her.

At first, he found it difficult to look at her, but when he did he saw that she had really made an effort. He couldn’t remember ever seeing her in full makeup before and he found it exciting that she was wearing it just for him. He recognised the perfume she was wearing as being the same one his Mother wore whenever she was going out on a special occasion and this, in turn, made him feel both grown-up and special.

As he stepped back from pecking her on the cheek he saw that she was also wearing a white, silk blouse that accentuated the huge swell of her breasts and made his heart leap. He observed also that she was carrying a small plastic shopping bag and his curiosity immediately arose as he noticed a few leather items inside it, up near the brim. Mrs Connor noticed Simon’s interested look and, before he could speak, she changed the subject. “Do I look okay to you dear, dressed the way I am?”

Simon grinned happily. Somehow her smile had made him feel more at ease. He allowed himself to take a proper look at her outfit and noticed she was wearing a tight black skirt with a long split up the side and high heel shoes. Her nylon clad legs looked more enticing than he had ever remembered from before.

Mrs Connor was not a slim lady, but not exactly fat either. Well-endowed or full-figured would be kinder ways of describing her. She was, however, slightly taller than average and despite being somewhere in her sixties; she looked fit, healthy and full of life.

The reason Simon had never considered her body in the same light as he had with, say, Mrs Brady was, he realised, probably due to the way the two ladies normally dressed. Today, Mrs Connor had dressed how the younger Mrs Brady normally would and Simon had to admit that he found the effect amazing. “You look lovely” he breathed, “I never realised….” his voice trailed.

“Oooh come here” Mrs Connor responded girlishly, “I’ve wanted to give you a big hug all afternoon” and taking the youth into her arms she squeezed him tightly to her in a huge embrace. Simon grinned, but could think of nothing to say and so he just returned the hug, enjoying the warm clean smell of her neck and the fragrance of her perfume.

As they hugged, he could feel her breasts pressing against his chest and the inside of his arms. They felt much larger and firmer than he had thought they were and he realised all at once that he really didn’t know too much at all about Eileen Connor, in spite having lived right next door to her for the majority of his life.

Out of the corner of his eye he noticed a wispy black satin garment that trailed into his view from the very top part of her bag. It looked like she might even be considering staying overnight he thought and his mind raced. He really didn’t have a clue just what her intentions were but then, as if reading his mind she whispered into his ear, “I promised I’d make dinner didn’t I?.... but, do you know….I’m really not that hungry at the moment, are you?”

“Not really” Simon replied cautiously, more curious than ever both about the bag’s contents and the evening’s activities to follow but too timid to ask.

“Maybe we need to work up an appetite” she murmured, “What do you think?”

Simon shrugged and, as Mrs Connor laughed and turned her face up towards his their lips met and they kissed gently, just holding their lips and their bodies tightly together. After a moment, Mrs Connor’s firm hand dropped to Simon’s bottom and she gently squeezed it. His cock reacted immediately and she broke free of the kiss, smiling at him with an all-knowing facial expression.

“Well, I can see you’re getting rather anxious to start your first lesson” she grinned, moving her hand to lightly squeeze the growing bulge in his pants. “Why don’t we go upstairs to your room and make ourselves more comfortable?” she continued and, without waiting for a response, she took his hand and led him to the stairway.

At the foot of the stairs she glanced back and suggested he follow her from three steps behind. “My husband always insisted on following me up the stairs for some reason” she giggled, “I wonder if you will be able to tell me why later on?”

As they climbed the stairs and Simon took a longer look at Mrs Connor’s body, he already knew the answer to the question; from the light grey, wavy hair, down to her ankles which, in her high heels, looked more feminine than he had ever seen them, Mrs Connor looked gorgeous.

His eager eyes focused on her bottom, which was noticeably wider than the girls from his school but much, much sexier and a million times more inviting. His heart beat louder as he realised that she was putting on a show and wobbling her hips just for him. He pictured her naked body next to his, the anticipation of which made his erection twitch as it pumped up to maximum hardness.

Upon reaching the top, Mrs Connor turned briefly to give him a smile before entering his bedroom and approaching Simon’s bed. Her bag was tossed unceremoniously onto the corner of it and, placing her hands on her hips as she did so, she turned to face him.

The old lady now appraised him far more critically. “Simon!” she said firmly, “before we go any further I want to talk to you”

He felt momentary panic at the prospect of her changing her mind but, as her words sank home, he realised she had already said they would be going further and so he listened carefully to the rest of what she had to say.

“I am 64 years old and you are 19. Many people would think that what we are doing is wrong, ---but I don’t really have a problem with that. I think you and I could have fun together and I can teach you what you need to know but--” she paused for a moment, “I want to make sure that you clearly understand two things first.”

Simon nodded, without quite knowing why, but having acknowledged the young man’s eagerness to start his lessons Mrs Connor particularised the two preconditions anyway; “One; that tonight is just for fun and neither of us is to become so involved in it that this little encounter of ours causes any problems to either of us.”

“Oh yes!” Simon nodded his head furiously “of course”

“Two;” she continued, “You never, ever, discuss what happens between us with anybody at all Simon. That means anybody, including your best friends” She stared at him hard. “Do you understand what I’m saying?” Simon nodded his agreement once again and, with that condition firmly understood Mrs Connor smiled, sat down on the edge of the bed and began to unbutton her silken blouse.

Simon now realised that all his fantasies about having sex were going to come true, albeit with a lady he had previously paid only scant attention to, and he watched intently as her fingers got to work on her buttons. Mrs Connor, however, stopped undressing and gave him a withering stare. “Well?” she enquired, “Would you like to get yourself undressed for me then? I want you totally naked so that I can have a good look at you.”

Her voice had taken on renewed authority, yet almost immediately her eyes softened. “You’re not afraid of getting undressed in front of me are you my dear?” she whispered, with a twinkle of mock concern in her voice.

“No way!” Simon croaked, goaded into action and now almost falling over in his haste to get his gear off. Eileen smiled and continued to watch with growing interest, as first his trousers fell around his ankles and were kicked aside and then as his shirt and shoes disappeared in a flurry of movement leaving him standing before her clad only in a pair of shorts and looking distinctly apprehensive.

Eileen suppressed a grin and, straightening her face, looked at him inquisitively. When the only response she received to this raising of the eyebrow was a brief, nervous shuffling of each foot, she made her intentions clearer by pointing at his shorts and adopting a sterner tone of voice. “Off!” she commanded. “Now!”

The order had the desired effect and Simon gingerly eased the front of his shorts away from his body before he let them drop to the floor and stepped out of them. Suddenly, there he was. Standing naked as a jay-bird in front of her. With a fully erect penis bobbing, slightly ridiculously, in front of him.

Simon felt incredibly turned on and just couldn’t help touching himself while he waited for his elderly instructor to take her own clothing off. He tried not to, but his cock had begun to twitch of its own accord and an embarrassing trail of clear fluid had now begun forming on the end of it. He pulled his foreskin back and forwards a couple of times, stopping only as he noticed Eileen looking him straight in the eye.

“Well…” she murmured slowly, “very impressive indeed!” simultaneously dropping her level of view and confirming to herself her earlier opinion that, although possibly slightly smaller than her deceased husband, the cock in front of her was a good five inches long and plenty thick enough to have some fun with.

“We are going to have some fun with that, my eager young friend” she continued, and without raising her eye level from her seated position, undid the final button on her blouse. Simon gasped and licked his lips nervously as a black lacy bra, only barely containing her quivering white breasts was revealed.

Slowly, and still staring intently at his penis as she did so, Mrs Connor reached back and unclasped her bra, finally releasing both heavy breasts to full view as she pulled the bra away from her and dropped it to the floor. She noticed, with satisfaction, that Simon’s cock had visibly moved at the sight of her breasts and now she looked up at him as he stood transfixed before her and gently guided his hands to her breasts.

He had never experienced anything like this and he almost sobbed with emotion as he took each wobbling breast in the palms of his hands. At her guidance he rubbed his thumbs slowly against each nipple.

Eileen noticed that he was constantly checking her face for any sign of disapproval or displeasure and she smiled to him, reassuringly, but also as a genuine reflection of the pleasure she was feeling. ‘Would she feel guilty tomorrow?’ she thought. ‘No, she hadn’t planned any of this but it felt right and, by golly, she was going to enjoy it.’

She was semi-surprised to hear a low moan emit from her own throat, as if in confirmation of her thoughts, and she looked up at him coyly as the tingling sensation began to build within her body. “Do you like the way I look without my bra on Simon?” she whispered.

“Oh yes” he breathlessly replied. “I love your boobs….they’re so…. big!”

It was true, and Simon couldn’t believe their weight as he held, fondled and squeezed them or the feeling that just being allowed to do this was giving him. He shuddered with pleasure as she reached forward to take his dick in her hand but then winced slightly, as in one firm movement she forcefully pulled his foreskin back, revealing the entire purple head of his virgin erection glimmering wetly just inches from her mouth.

Teasingly, she looked up at him and licked her lips, causing him both to forget the momentary flash of pain and to realise, that for the very first time in his young life he was experiencing the pleasure of intimate contact with an adult member of the opposite sex.

He also understood that in addition to an enjoyable time he was going to receive a very good education from Mrs Connor who, instead of taking him into her mouth as he had hoped, was now easing herself away from him, moving further back onto the bed and slipping her shoes and skirt off as she went.

Simon moved forward with her but had to release her breasts as he climbed up onto the bed on his knees. His mind was racing with excitement as he knelt beside her. “Would you take off your panties as well?” he asked, “or can I...please?” he added shyly.

Without speaking she just looked at him and smiled, raising her hips as she did so. Simon took his cue immediately and, quickly finding the waistband of her black, silky panties with his shaking fingers, he pulled her knickers down in two swift movements; first to past her knees and then, as she raised her feet for him, completely off and on to the floor.

Without the slightest reservation or hesitation, Mrs Connor lay back on the bed and opened up her thighs to let Simon feast his eyes upon her. The old lady fully understood that this was uncharted territory for him and, after allowing him a few seconds to stare, she took control of the situation.

Moving her legs so they were spread on either side of his kneeling body, she addressed him in a firm, no-nonsense tone. “Now, young man” she demanded, “you are going to lick my pussy for all you’re worth.”

She registered the expression of shock on his young face without displaying any change of emotion although she almost spoiled it by laughing as she caught sight of his young dick, throbbing and twitching with anticipation all on its own. The young “so and so” had probably thought this situation was purely for his benefit but now she had made it crystal clear who was in charge and, seconds later, Simon obediently lowered his head forward and lay down between her legs.

He paused briefly, his mouth inches away from her pussy, fascinated to be this close and to be allowed such a detailed view. He saw immediately that it was covered in a silky, light brown hair, almost silver in places and through which her thick outer lips and the dark divide between were clearly visible to him. The smell of her perfume was slightly stronger down here and yet it smelt somehow different too. More earthy or musky he thought. Sexy.

The scene before him was impossible to resist any longer and he slipped his tongue into the crevice between her lips and began to explore. The heat and the wetness of her almost immediately guided him towards the entrance he was seeking and, as Mrs Connor felt his tongue slip inside her she moved her hips involuntarily. “Use your fingers” she ordered, “use your fingers to hold me open.”

Simon did as he was told; trying several movements before finding the one that afforded him the clearest view inside Mrs Connor’s pussy. He was fascinated at the pink inner lips and longed to slide his hard dick into those velvety folds. As if on auto-response he began to raise himself but was abruptly halted by her hands firmly pressing him down and holding him in position. “Now” she instructed “flick at my clitoris with your tongue.”

Simon looked closely for a moment. He didn’t have a clue where it was and so moved his tongue around hesitantly. Mrs Connor had predicted this however, and very quickly her fingers appeared in front of him, two on each side, lifting the folds of her flesh upward and exposing the little hood of skin from which her clitoris appeared. “There!” she soothed, “just flick away at it softly with your tongue”

For the next 5 minutes Simon gently licked, kissed and sucked Eileen Connor’s pussy in line with her instructions. Once, he spontaneously lifted her bottom off the bed and buried his face into her, an action which was rewarded with a squeal of pleasure slightly louder than the others she was making, but which he did not repeat because he thought he should stick closely to the directions he was being given.

A minute or so later, just as his tongue was beginning to ache badly and he was thinking about having a rest, he suddenly felt her began to come alive with movement. The pain under his inexperienced tongue diminished as the young pupil increased his efforts and he could sense a growing wetness forming. He wondered momentarily if it was just saliva forming on his chin that was causing it, but subconsciously he understood that he was about to create his first orgasm within another person.

At first the only noticeable signs were a couple of moans which were slightly louder than the others. Then, she began to move her hips more forcibly and the sounds began to increase in frequency and volume. She gripped his head firmly and at one stage pulled his face into her so tightly he thought he would drown in her wetness, but still he carried on licking and finally, as she climaxed, he felt a torrent of power build within her and, as it broke, turn rapidly into such a surge of pride within himself that he was sure it would burst from his cock if he allowed it to.

Mrs Connor emitted one final grunt and slumped, motionless onto the bed. Simon took this as his cue to rise, and as he did, he surveyed the scene in front of him. Mrs Eileen Connor, his 64 year old, silver haired, next door neighbour was lying naked in front of him covered in sweat, her eyes closed, her hair ruffled and a very contented smile on her face. She moaned her approval to him softly between deep, contented breaths.

For a second Simon thought she was drifting off to sleep but gradually her eyes opened partially and a sly, lustful look appeared on her face. “That was just terrific, darling” she breathed, “and now, I’d like you to fuck me.”

Simon swallowed, looked down at her body and took a good look at her ample breasts with their erect nipples. He saw the firm condition of her body, despite the 64 years and the few extra pounds she carried and he knew that he did want to fuck her, a need more powerful than anything he had ever known.

He glanced down at his manhood, so hard and so deeply purple that he almost didn’t recognise it and he knew that he was ready. Lifting himself on the palms of his hands he straightened his arms, bringing his glistening erection closer both to the entrance of his lover’s pussy and to the losing of his virginity.