Lessons from Sadie Ch. 03

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He tests his skills on Jan.
3.5k words
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Part 3 of the 5 part series

Updated 10/25/2022
Created 11/02/2004
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Rex Siter
Rex Siter
287 Followers

In the five days before the Thursday High School dance when I was to test my abilities on Jan Vickley, I had two more sessions with Sadie in which, as well as the anticipated joys of her body, she schooled me further in small details. A load of time on bra-unfastening---with one hand!

"The other hand could be busy" she pointed out, bathing me in that knowing smile. She also gave me advice on what to say and what not to say "This girl you've suggested might have reputation among the boys but there's no greater turn off than showing that you expect her favours. Act grateful---always." I think I followed that piece of advice for the rest of my life.

So, equipped, and much more confident than I had ever been before I attended the Thursday dance. The school hall was always crowded and there was a rich array of nubile girls to view, most of them professional virgins, I guessed. Saving it for one lucky man. I could look forward to that kind of challenge at a later date. When I finally spotted Jan Vickley, she was, not surprisingly, in a group consisting of her friend, Mandy Summers, and a gaggle of wide eyed guys. From time to time she would be up swaying provocatively, on the dance floor with one of them.

Clothed in a bright red flowing skirt and a low cut black blouse Jan's voluptuous body was certainly eye catching, if not breath catching. But getting near her was going to be the challenge.

However at one point she and her friend slipped away to the toilets and I lingered near enough at that end of the hall to ask her for a dance as they returned. Her face showed some surprise.

"Asking me to dance, Jack? I thought you were too good for the likes of us."

"No, I've never been a good dancer." A small white lie. "I've been learning."

On the dance floor Jan certainly knew how to project her sexuality, coming in close her thighs meshing against mine until the natural happened, and her eyes widened as she said with a wicked smile, "Am I making it hard for you?"

We danced a second time later in the evening and that's when I quietly asked if we could take a walk afterwards. She frowned, "I've already promised Jake Regis." And as my disappointment showed she quickly added, "But meet me outside anyway" And with a flick of her skirt she walked away.

At the end of the evening, after risking one or two dances with other girls and finding them insipid in comparison to Jan, I waited among the dispersing crowds outside. Jake Regis was hanging around too. Jake was one of the big talkers about his conquests, tall and, I suppose, fairly good looking with his fair hair and blue eyes.

Jan came down the stairs, with all the swagger of a female who knows the effect her movements had on men. Jake moved towards her. So did I. Her green eyes viewed us together before she said, "I suppose I can handle you both. Come on."

And like a pair of sheep we followed her provocative sway down to the river bank, which was always a popular courting area.

"Since there's two of you I'm just doing hand jobs tonight, but you can have a breast viewing."

And as she kneeled on the grass she unbuttoned her blouse to reveal two melon sized breasts, all brown tipped and snuggly looking.

We kneeled on either side of her, "I'm first," Jake said scowling at me. I shrugged at Jan and she proceeded to open Jakes flies to reveal an only semi-erect penis. "Needs work," she commented and proceeded to stroke it with some vigour. It must have done the trick for in less than a minute Jake was groaning and Jan had released him to spurt his load into the grass. He lay back with a satisfied sigh.

Anticipation had given me a lift so that when Jan turned her attention to undoing my flies my erection lunged out solidly to her view and I could tell by the look on her face that she was surprised and impressed. Her hand grasped it firmly and she began tugging.

I reached out my hand and stroked down the side of her face. Her eyes flashed to my face and there was a little frown of uncertainty on her brow. As she pumped away at my cock I allowed my fingers to glide down her neck and under her open blouse onto the start of the hillock of her breasts.

"I said, just for looking."

"You're giving me pleasure, " I replied. "I'd like to return the compliment." Always be grateful, that's what Sadie had advised.

My index finger was tracing over one of her nipples and I felt it rising under my touch. Spreading my hand over the ample breast I applied all of Sadie's tutoring to the movement of my fingers and hand, and knew from Jan's breathing that I was getting results.

Encouraged I lowered my mouth to her breast and began gently tonguing her nipple while my fingers continued to flutter over the other breast. She didn't stop me.

Jake had sat up, "You didn't let me do that," he grumbled.

Jan was shuffling from the kneeling position without stopping her hand action on my erection. Now her legs were splayed out in front of her and the invitation was just irresistible. Without checking my mouth's pampering of her breast I allowed my hand to trail down over her belly to the waistband of her skirt. It was elasticated and my hand slipped easily underneath and over the swell of her lower belly and under her panties.

"Steady," she gasped.

"Should I stop?" I asked, raising my head from her breast.

In the dark our eyes held for a moment. Then she moved her face closer and our mouths came together, tongues searching. I took this as a positive sign and my hand continued its journey to romp through her pubic hair, which felt particularly thick and bushy compared with Sadie's.

"Hey, I didn't get that?" Jake protested, getting to his feet.

Jan broke away from my lips to growl, "Oh, just fuck off, Jake."

I saw Jake drift away in the gloom but fancy he lingered on the edge of the clearing.

The tips of my fingers began gliding into that mellow groove, when she shuffled again and said, "Just a minute." She hoisted up her skirt and almost in the same movement slipped her panties off and even in the evening darkness I could see that her thick dark bush was indeed expansive.

"Lie back," I told her, without comment she did as she was told and I immediately stooped my head to that dark furriness and my tongue searched into the open crevice, already moistening. Back and forwards along the swelling labia I operated the very tip of my tongue until she was gasping.

With just another deeper flick my tongue encountered her hard little button and I concentrated on that, enjoying the sounds of her laboured breathing. Then I moved my fingers ahead of my tongue so that they could probe for that secret place and it was no problem. Two fingers sank deep into her vagina and she began make squeaking noises, hips lifting to meet the ministrations of my tongue.

"Oh, God I'm cumming," she almost yelled and the next second she was bumping and heaving so much that I lost my place and could only sit back and watch her ecstatic movements.

As she quietened she raised her head, "I'm sorry. I didn't think it could be so quick. And I haven't made you cum."

I lay over her, "It's not over," I whispered, mentally thanking Sadie for this level of confidence. "The best is yet to come."

And lying between her thighs I placed my cock head against her vaginal lips, "I've never come twice," she said apologetically, and gave a little gasp as I slid easily into her moistened depths, allowing my rod to plunge right to her upper reaches. Very slowly I retracted, then plunged. And continued like that for a while, slow retraction, swift plunge, slow retraction, swift deep plunge. I listened for her breathing, heard it quicken. Then raising my body slightly I made sure that each forward stroke, faster now, was riding over her clit. Her vaginal walls began drawing at me and her breaths became low grunts as our rhythms merged.

When I felt the timing was right I changed to a series of rapid hard thrusts and felt myself close to climax and knew from the tossing of her head and her gasps and moans of delight that she was almost into her second cumming.

As I felt my balls about to explode her hips heaved up from the ground and a strangled scream escaped her lips as with two final hefty strokes I allowed myself to burst inside her, sure that my cock head struck against her cervix as we heaved and grunted in those final ecstatic throes.

As we lay cooling down she said, "I know I have a reputation, but I've only ever gone all the way twice before tonight. But it was nothing like that. Why haven't I heard about you before?"

What could I say? I'm just a learner? Hardly. Secretly elated, I just said tactfully, "I save myself for the best."

After we'd lain there for a short while she murmured, "Could we do it again sometime?"

I placed my hand over her pubic mound, "What about now?"

She sat up in some surprise, "You could do it again?"

I nodded towards my flickering penis, "He looks interested."

"Oh, God, this is terrific."

And second time around it was.

When we parted she was still rambling about how wonderful it had all been and I was feeling pretty pleased myself about this first 'trial' encounter. I just longed to tell Sadie about how well it had gone but knew it was too late to see her that night.

Then the next day at school I discovered how quickly reputations can be formed. Quite a few girls treated me to long lowered lashes looks or turned away giggling. A couple of the guys in my year came up to me and one of them said, "Jake tells me you really qualified big with Jan Vickley"

When I went into class, there were a couple of whistles and, did I imagine it, or did Miss Orry, our class tutor, give me a long hard stare? I'd had a secret passion for her, with her trim little figure and curling blonde hair, since she'd arrived at the school three years earlier.

But that was pushed from my mind that afternoon when Mandy Summers, Jan's friend approached me as we changed sessions. "I know this sounds awful," she began tentatively." But Jan's told me about---well, you know." She licked her lips and I waited, admiring the swell in her sweater and her long hair, same colour as Sadie's. "It's just that---Oh, well, Jack, I'm sick of being a virgin."

Just a little shaken I tried to remain calm, "You think there's something I can do about that?"

"From what Jan's told me---yes. Would you, Jack?"

Would I? Was it always going to drop into my lap like this? In no time we'd agreed to meet that night. And it became a question of where. The comfort of houses was out so in the end we agreed on a trip to the coast. The nights had been warm and to my mind the sand dunes were high, wide and as private as you could get. And I was about to try my hand with a virgin. I could hardly wait.

We met just after seven, and strolled through the funfair over the beach. We bought ice creams and strolled, hand in hand, towards the dunes, talking about anything but what was about to transpire.

As we moved in among the hills and hollows of the dunes I sensed Mandy becoming more nervous. Her hand tightened and slackened on mine. At last we came to a deep, well grassed hollow, and I spread the coat I'd brought for the purpose and she sat down nervously.

Nestling beside her I kissed her neck and whispered, "What's the furthest you've gone?"

In the fading light her eyes reminded me of a trapped rabbit. "Touching---down there."

"Did you cum?" I hoped I wasn't being tactless.

"No, but he did." Her eyes met mine as she added quickly, "Onto the ground."

Without further ado I kissed her, allowing my tongue to probe along her closed lips, pleased to find they parted without too much pressure and the tip of her tongue touched mine. I let it go on like that for a while, my fingers gently massaging the side of her neck. Eventually my hand slid to the open neck of her blouse, slipped the button there and my fingers teased the beginnings of her neat bosom.

I was going to make this nice and slow, because it seemed, that's what was needed. Gradually I moved down the buttons of her blouse until they were all undone and I held a breast that fit nicely into my cupped hand, although still encased in a lacy bra. And there was my next challenge---unhooking the bra, one handed. First attempt I was clumsy but at second try it came away nicely, and she flexed herself out of it and her blouse.

Now I laid her back and began gently kissing each breast in turn, licking at the tiny nipples, the smallest I had encountered in my brief sexual career. But soon they were responding to my stimulus, and as my lips sucked gently at them she gave out a little moan of pleasure and began unfastening my shirt.

We stayed like that for quite some time, me pleasuring her breasts while she stroked my chest, tugging at my own nipples which was surprisingly pleasurable. I would have liked her to be more adventurous and put her hands where my trousers were being strained painfully. But i wasn't going to do any pushing.

My hand moved down her flat belly to her skirt which I had noticed was a button up type. With just a little more urgency I quickly undid the buttons, parted the skirt and let my fingers roam over her thighs and pubic mound over her panties. It was then that her own hand moved to my groin and as her fingers felt along the length encased there I heard her gasp, and I like to think it was shock rather than passion.

Through the thin silk of her panties I traced the edge of her labia, and her thighs immediately parted, so Islid my hand under her panties and stroked through the warm fuzz to the fleshy welcome spot.. With just a suggestion of movement from my hands she raised her hips so that I could push her clothing down and away. Then my mouth was moving down over her belly and into her light pubic bush where my tongue instantly flicked at the labia corner and I felt her jerk as her fingers fumbled to undo my belt.

Moving my tongue slowly up and down those swelling lower lips I was surprised how quickly she moistened. I placed my fingers over her vaginal opening rubbing only gently but making each movement a gradual deeper entry. Her whole body began jerking and shaking, while her hands finally came into contact with my bared engorged cock.

I slid my tongue back to where my fingers had played and probed what felt like a tiny hole. The tip of my tongue circled it, before sliding back to her clit .

I became aware of her lips running along the length of my cock, backward and forwards, faster and faster as her breathing quickened. Her lips remained closed and I guessed she had never taken a boy in her mouth before. I was not intending to force her, in my mind now was that moment when I would be claiming my first virginity. The thought was almost exciting by itself. But her wetness, her trembling and her own ministrations to my erection suggested that it was time to perform the very necessary deed.

I sat up and moved my body round to cover her. "You think you're ready?" I asked.

"Yes, oh, yes---but don't hurt me."

I was raw enough myself not to make too many promises about that. I rolled between her open thighs and placed the head of my cock at her vaginal lips. Now I reminded myself what Sadie had said about this in one of her most recent lessons. "Never be too fierce. No matter how desperate you are yourself. Always respect the virgin and what she is giving you."

Accordingly I allowed myself to push into her just one inch, what had seemed like a small hole to my fingers, now seemed to grow as I entered, an accommodating growth. Two inches in now, then back. I heard her breath catching. Three inches and back, forward, but gentle. "That's so nice," she gasped.

And I kissed her as the head of my cock encountered obstruction. Just as Sadie said it would. "At this point," she had said. "Don't hesitate. Go through it. Her pain should only be momentary. But you have to ensure immediate pleasure to supplant it." A tall order, it seemed. But here we were. I looked down at Mandy, smiled at her, and she gave a nervous impassioned smile back. Then I drew back inside her before thrusting forward, feeling the obstruction briefly hold, then vanish, and I was plunging up inside her, as she squealed her anguish which quickly lapsed into a gentle moan---of pleasure. I kept the thrusts going deep into her. Now she felt pliant and giving and almost automatically her vaginal walls began their independent pulling at my shaft. I shifted slightly so that my movement brushed her clit and in no time she was heaving against my thrust, gasping, moaning, squeaking, almost every noise possible as she came for the first time in her life. And I had done it. I don't know whether it was that feeling of triumph alone which brought me to my own vigorous climax and I was the one grunting madly as I plunged into the newly opened depths of her.

On the way home she told me it was a moment she would remember for the rest of her life, and could we do it again sometime. Without being too positive I told her I was sure we could. But with the hour being reasonably early I was eager to recount my experiences to Sadie.

I saw Mandy home and then hurried home myself. As I approached her back door it suddenly opened and a tall man came out, fastening up his shirt. He did not look my way and as I began moving forward again, another man came out, breathed deeply at the night air and moved away without seeing me.

What was happening here? Had Sadie been harmed? The back door being opened I stepped inside and made my way to the bedroom. Sadie was sitting on the edge of the bed, totally naked, calmly brushing her hair.

Her face showed surprise, then regret, as she noticed me. "Jack, I wasn't expecting you."

"Who were those men?"I asked her, like some possessive husband.

She held out her arms to me, "Come here, Jack. Please."

I could never have resisted her in spite of my present uncertainties. I went and sat beside her on the bed where she took my head and drew it to her wonderful breasts. "Jack, I said I wouldn't be jealous of you with girls of your age. You must understand my needs. They are massive Jack. More than any one man can hope to satisfy."

"But two men--"

"Yes, two---at once. I won't hide that from you. You need to hear my story---someday. But for now--what have you been up to?"

Disappointed as I was at not being the one and only I went on to tell her about Jan and the spread of my reputation at school, highlighted by the taking of Mandy's virginity.

"A virgin? Well done, I'm so proud of you, Jack. Oh, you're going to have such a life."

How could she have been such a prophet?

"Now, have you got anything left for me?" she asked, as her hand slid down to my groin. "Oh, I think yes."

And she led me into that dark and wondrous path once again, showing me just how much pleasure there was in the world.

Just before I left she asked me if I had any plans for future conquests, "You could become more ambitious now."

How could I know that it would be school that would bring me a sexual conquest that I could have only dreamt about.

End of part three.

Rex Siter
Rex Siter
287 Followers
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AnonymousAnonymousabout 2 years ago

Very good, shows a lot of imagination

AnonymousAnonymousover 4 years ago
HYMEN LOCATION ERROR

The hymen is over the mouth of the vagina. A penis can not penetrate 2 or 3 inches before hitting the hymen -- as it is depicted in this story.

Google: hymen location.

Encountering this anatomical aberration, rattled me out of the flow, taking a bit to return, and even then, making it seem less real and enticing.

Am enjoying this series. Reminds me of a favorite sex education story, the beautiful and heartwarming Educating Dustin Rhodes by Mindventure. Both tales have what too many sex education stories lack -- the aftermath/results with his peers and/or other partners.

Paul in Oklahoma

AnonymousAnonymousover 19 years ago
Two First Timers, Wow!

I loved how you took care of Jan and were better than the other two who had gone this far...I am so glad you did her again, not waiting until another time...And then to get to really teach a Virgin, Mandy, about real Love making. And she just loved you...Quite a jock...WOW Hot Stud 1000, Bob

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