Teen Tutorial

"Oh fuck, so strange, so dirty," she groaned.

"You want me to stop?"

"Fuck no! More! Do more to me! Fuck, what a feeling!"

I continued probing with my tongue, reaming out her sweet puckered asshole till I was almost inside her. My face was mashed between her buns, pressing her forward. Strange, perverse behavior, but I just couldn't get enough of her. Her pretty little ass was irresistible.

And she whimpered and moaned with pleasure. She spread her thighs even wider for me, giving me more access to her sweet anus. And now there was a catch in her voice, almost a sob. I gave her sphincter a final few pokes and then knelt up.

I'd earlier retrieved a tube of lubricant from the bathroom cabinet and now I began smearing liberal gobs of the stuff up and down the crack of her ass. I used a forefinger to force a wad into the rubbery ring of her anus.

"Oh fuck, you're really going to do it," she groaned softly.

"I am. Would you prefer I didn't?"

"No. I want you to. I want to have the experience."

"You're learning so much, the first day of your new tutorial," I told her, smearing more lube up and down the length of my new hard-on, my second within an hour.

"So dirty. You're so dirty," she muttered.

I planted the head of my cock onto the tight circle of her anus and pressed forward. She began to moan as she felt the pressure from my glans. It took one, two, maybe three seconds before her sphincter relaxed and I could watch it widen and fold over the tip of my prick.

I eased in the first couple of inches of cock then paused, listening for her reaction. Her moans continued but she did not seem in any distress. I pressed another few inches of cock up her ass and paused again.

"So strange! So fucking strange!" she murmured as I eased in the rest of my dick.

I waited, paused with my entire hard-on buried up her ass. Then I began a slow, regular fucking motion, sliding my hard-on back and forth in the lube-slick channel of her anus. The taut twin globes of her ass flexed and trembled as I pumped in and out between them.

"Oh fuck! I can't believe I'm doing this!" she gasped. "Anal sex! Oh fuck!"

In a way I couldn't believe this either. A sweet and willing eighteen year old virgin was sprawled beneath me and I was fucking her up the ass. She'd aroused me to the point where I could sustain a second erection in less than an hour, something I'd never thought myself capable of. And she was doing this so eagerly, almost begging me for it. The notion had me awestruck.

And of course it meant that I wasn't going to last long. The incredible excitement of what we were doing was overpowering. I'd ejaculated all over her face only the hour before but already my balls were tingling, and after a few more strokes I was coming again, pumping out wad after wad of hot spunk up her ass.

My thighs slap-slap-slapped against hers. Her slender body was jerked forward again and again. And my balls emptied for the second time, blasting sperm deep up her colon. What a feeling. Unforgettable.

"And I'm still a virgin!" she moaned as I sank exhausted on top of her, my cock still lodged deep up her ass.

It was true. Technically she was still intact. She was no stranger to sexual activity now, that was for sure, having aroused hard-ons twice in the last hour, having taken a load of cum all over her face and now deep up her ass. But for all intents and purposes she really was still a virgin.

"We'll fix that next time, if you wish," I promised. "Once we're sure of your birth control. For now you've had an introduction. How did you like it?"

"I loved it! I fucking loved it! I can't wait to learn more! I can't wait to get fucked properly!"

* * *

And in truth I couldn't wait to do the honors. For one thing her father might show up any day as part of his partial retirement strategy and I wasn't sure how many more opportunities I'd get with her. And I also had no illusions about my future with a beautiful and precocious eighteen year old. I may have become her tutor in matters academic and erotic, but I had no expectations of our relationship continuing much longer.

I was made very aware of the probable brevity of our arrangement the very next time I visited her, a couple of days later. As I entered the driveway I almost collided with a car just leaving, the driver a handsome young fellow I'd seen out at the college.

"A new boyfriend?" I asked her as she welcomed me in.

"That was Kevin. He's a college freshman who's been interested in me for a while. One of the callow youths I was telling you about. What's in the package?"

"A couple of adult accessories I thought you might like. Part of your training," I said, handing her the small gift bag I'd been toting. "Go ahead. Try them on."

She grinned the mischievous grin I was getting used to and drew from the bag the lacy items I'd bought for her. She seemed to know immediately what they were and gave a little yip of pleasure. Then she took me by the hand and led me down the hall to her bedroom. In seconds she was stripping off her jeans and T-shirt and was standing there naked in front of me, holding up the frilly pieces in admiration.

"A slut's outfit! Perfect! I've seen this stuff in lingerie stores," she gushed.

She drew on what was essentially a string bra with no cups. As she clasped it in back her beautiful ripe breasts were thrust through the loops, totally naked.

Then she was hooking the lacy black garter belt in back of her and adjusting the dangling straps into place along each thigh. She sat on her bed and began hauling a black silk stocking up her leg. She snapped a garter onto the stocking top and repeated the process with the other stocking.

"I love it!" she grinned, standing up and pirouetting for me in the lewd outfit. "I look like a porn star or a whore. I feel so dirty!"

"You look fabulous," I commented, my erection growing in my pants. "Fuck, you look good enough to eat."

She laughed, lay back on the bed and spread her legs wide. Her pretty shaved pussy winked at me, the pulpy lips parting already, a tell-tale pearl of fluid glinting a the apex.

"Go to it. I want it," she murmured, suddenly calmer, her eyes heavy-lidded as she gazed at me.

I stripped off quickly, knelt down and ran my hands up and down the silky tautness of her black stockings. Then I was dipping my head between her legs, licking up the pearl of fluid and scraping my tongue up and down on the pulpy pink slabs of her labia. A quiver of pleasure rippled up the entire length of her body.

"Yes! Oh yes!" she muttered, her hand caressing the back of my head. "I love this! I just love it!"

I'd barely begun but she was trembling with pleasure already. She may well be a virgin, I thought, but she was already well on her way to enjoying a full and deeply satisfying sex life. She didn't really need any coaching from me. She was a natural, excited and curious about sex and totally at ease with her feelings.

I licked her sweet pussy the way I had a few days earlier, probing with my tongue, prying her labia wider and wider and soon enough teasing and taunting her budding clitoris. Within seconds she seemed on the verge of orgasm, and I paused to glance up into her face.

"Your cock," she murmured, a strange hungry look in her eyes. "I want to come with your cock inside me. Please fuck me."

"You're taking your pills?" I grinned at her, standing up with my hard-on blazing in my fist.

"Of course. I'm safe. Do it to me please. I've been a virgin long enough."

I knelt between her legs and nudged the head of my cock between her gaping pussy lips. Then I gently slid inside her, watching her face the whole time. She gazed up at me and gave off a deep sigh of pleasure as I sank down on top of her. She was so slick and wet the penetration was easy, and I began a steady fucking motion, leaning down to kiss her at the same time.

Her arms clutched me to her, her legs curled over the backs of my thighs. And when our kiss ended she grinned up at me, her eyes alight with pleasure.

"We're fucking," she laughed. "Your cock's inside me and we're fucking and I'm going to come!"

I sensed her vagina clenching and unclenching around my cock and she began her tell-tale series of whimpers as she climaxed. She thrust her crotch up at me, sucking my prick deep as she came.

And I didn't last much longer myself. Within seconds I was spurting jet after jet of creamy cum up her pussy, my emptying balls slapping time and again in the crook of her thighs. What an amazing sensation, to be fucking and ejaculating inside this stunning eighteen-year-old. What a privilege, to be taking her virginity.

"I'm so glad we did this," she whispered as we settled down, my cock still oozing deep inside her. "We may not have many more chances. My father is due back next weekend."

"So soon?"

"I'm afraid so. This house will be off-limits."

"Maybe I could have you over to my place. I'm all alone there."

"I'd like that. But before the weekend, could you come over one last time? I'm planning a little celebration. The partial end of my freedom."

That had such an ominous sound. But it was probably close to the truth. This amazing adventure had to come to an end at some point. And when I thought more deeply about it, maybe it was just as well. I was showing signs of becoming obsessive over the sexy teenager, thinking of her just a bit more than was healthy. How long could I keep up a sexual relationship with someone so much younger?

There were certainly more contemporary contenders waiting in the wings, as I was to discover when I showed up a day or so later for what would apparently be our farewell celebration.

Tess was cavorting in the pool again in her tiny bikini, but she wasn't alone. There were two athletic young men splashing around in there with her. One of them I recognized as the fellow I'd seen driving away so recently, one Kevin.

This was to be a pool party apparently, as Tess explained as she came dripping from the water to welcome me. And it was clearly well underway, with both young men and Tess herself already slightly tipsy. A poolside table had several empty bottles on it.

Introductions were made quickly and then Tess was leading me to one side to hand me a beer and whisper to me.

"I want your opinion about the callow youths," she murmured. "Which one you like better, Kevin or Ryan. Or neither. Maybe you think they're both assholes."

"Isn't your opinion the only one that matters? I assume you're checking them as boyfriend material?"

"Maybe. We'll see. Tell me later what you think."

After half an hour, which I spent sipping my beer poolside rather than joining in the playful water sports, I could tell neither one of the young guys was an asshole, or a callow youth for that matter. They chatted amiably with me, clearly aware that Tess and I had something going on. They were polite and respectful, knowing I had connections to the college they both attended.

They were awesome physical specimens, tall and muscular and so good-looking. And they were clearly not just college jocks. Kevin was in the Commerce Faculty and Ryan was hoping to get into pre-med. What was obvious mostly was how enamored both of them were with the beautiful Tess. They seemed to take turns playfully caressing her and at one point she was sandwiched between the two of them, Ryan in front and Kevin behind her.

Up until then she'd been laughing and joking with them, a typical teenager at a pool party. But suddenly there was a quiet pause and a moment of awareness for all three of them. They were momentarily frozen in a pose of incredible eroticism. Ryan leaned down to kiss her and I saw Kevin's hand snake around to cup one of her luscious breasts. Then the pose was broken and the three of them separated with laughter and more jokes.

I had a sudden premonition of where this was heading and I had to ask myself how I felt about it. I had a pang of jealousy as I watched Tess and her two friends. They were all so young and alive, their educations and careers, their whole lives ahead of them. But then I knew that whatever futures they had in store, I probably wasn't going to be part of it.

And I didn't mind. I certainly had had my share of awesome erotic fun with her. Probably much more than I deserved. Maybe I would get to see more of her, maybe I wouldn't, but if I had to bow out, let the young studs take over, I could live with that. What mattered were the choices Tess was about to make. She had brains and beauty, and a pretty decent amount of sexual experience, which was what she wanted. I had a feeling she would know what to do with all that.

"What do you think of them?" she whispered to me at one point, while both young guys were grabbing yet another drink.

"I like them. They're nice guys. And they're crazy about you."

"Do you have a preference?"

"Either one will do for you. Maybe both, for now," I answered.

And off she strode to grab a drink for herself.

The splashing in the pool continued. The drinking continued. And at the end of an hour, as all three of them stood dripping by the drinks table just in front of me, laughing and sipping their beers, there was a sudden silence.

"I'm so drunk," Tess finally announced, her awesome body gleaming in its tiny bikini. "And I'm so horny. I think I'd like to suck you all off."

She glanced over at me as she said this. And then, almost in slow motion, she was stepping closer to both young men, stroking a hand up and down the healthy bulges swelling each of their bathing suits.

"Tess, there are three of us," I cautioned.

"I know. Isn't it exciting? Three of my favorite men. Three lovely cocks. Let's do it. Just give me a few minutes to get ready."

And with another quick glance in my direction she was picking up a towel and striding into the house, leaving three horny males gazing raptly at the flexing of her perfect little ass. None of us said a word as she disappeared and I had a sudden vision of all three of us staring after her with jaws agape.

"Do you think she's serious?" Ryan said at last. "She was just kidding, right?"

"I don't think she was kidding," I offered. "I think she was perfectly serious."

"But all three of us? I mean one at a time or all three of us together?" Kevin wondered.

"I think all three of us together," I continued. "She's blossoming sexually. Willing to explore. Test her limits. I think we have an erotic adventuress on our hands."

Both guys were suddenly thoughtful. And it didn't take a genius to figure out what they were thinking about. The bulges in their bathing suits seemed to have swelled further in the past few minutes.

"I don't believe it. I just don't believe it," Ryan muttered. "It's too much like a fantasy."

A few minutes later I was thinking exactly the same thing, as Tess appeared in the glass doorway dressed in nothing but a light see-through wrap and the lewd erotic underwear I'd given her at our last meeting. Her beautiful shaved pussy gleamed between the taut straps of her garters.

I had a sudden flashback to a few days earlier, when Tess the coy teenager talked to me of deprivation and lack of sexual experience. And now here she was decked out like a porno star, urging multiple men to join her in what would at least be a lewd blowbang, or maybe a full-blown orgy. Her days of deprivation were clearly over.

"I'm ready, gentlemen," she smiled. "Come inside and join me."

Ryan and Kevin stood gaping at her in disbelief and to break the spell I stood up and moved toward her, removing my shirt as I did so. She took my hand and led me back toward the divan. Then she was sinking to her knees and fumbling with my belt. In seconds my pants and shorts were on the floor and my cock was swaying out heavily in a state of semi-erection.

It was in her hand and in her mouth before I had time to react. She began to suck, urging me to hardness while her eyes rolled toward Kevin and Ryan. They had suddenly appeared on either side of me, and while she sucked she stroked her hands up and down on the now monstrous bulges in their bathing suits.

She let my growing hard-on slip free of her mouth and turned to hook her fingers into Kevin's bathing suit. She tugged down and as his suit slid to the floor his huge cock bounced free to smack her under the chin. It was a thick shaft of engorged meat, one of the biggest dicks I'd ever seen, and Tess laughed out loud as she gripped it and shucked it up and down in her fist.

"Wow, look at this thing!" she grinned. And she planted a kiss on the purple glans by way of welcome.

Then she was turning to Ryan, hauling his bathing suit down and smiling all over again as yet another humungous prick sprang free and jutted out at her. This was even bigger than Kevin's, a huge, throbbing pole of man-meat that seemed too thick and cumbersome to erect upwards. It angled down like some heavy curved log.

Tess glanced up at him, her eyes wide. For the moment she was speechless, and I sensed her wondering just what she'd let herself in for. But then she was grinning, licking up a pearl of fluid oozing from its tip.

"This is amazing! So huge!" she sighed. "I didn't know there were cocks this big and beautiful."

She dipped her head, lowered her face to nudge the monstrous prick to one side. Till suddenly her pretty features were beneath the throbbing shaft and it lay pulsing and oozing up the entire left side of her face.

And slowly Kevin and I moved in closer, laying the weight of our cocks on the other side of her face till her features were entirely obliterated beneath the three heavy shafts. She was laughing beneath the trio of dicks, moving her face from side to side so that they rolled and shifted in a weird facial cock-massage.

"I love this! I'm in cock heaven!" she cooed. "Fuck, what a dirty little slut I am!"

Suddenly her head was turning, and her mouth folded once more over my throbbing cock. Her fingers clutched at the two dicks on either side and while she sucked me her hands began shucking each of them up and down. All three cocks were in a state of massive, pulsing erection in a matter of seconds.

"Fuck, Tess, this is some first date!" Kevin grunted, his prick soaring through her pumping fist.

"Not quite what you were expecting, huh?" she grinned, slopping her mouth off my cock and turning to suck in Kevin's swollen glans.

She drove her mouth up and down steadily for the better part of a minute, taking in as much as she could of the engorged shaft. Then she was turning to Ryan and forcing her mouth down over his pulsing prick. The sheer thickness of the thing stretched her lips to the limit and she could only absorb the glans and an inch or two of shaft. But she gamely began an up and down motion with her nostrils flaring.

She sucked us for quite some time, growing more and more excited all the while. She moved with more and more urgency between the three of us, plowing her mouth down as deep as she could, on me, on Kevin, on Ryan, twisting and turning on her knees, her rasping breaths growing louder and louder. From time to time she paused for breath, and when she did she clutched a cock in each hand and rubbed them both harshly into her face, smearing her glowing skin with sticky trails of pre-cum goo.

At some point I took her by the shoulders and urged her onto the divan. She lay across it with her legs spread wide, her head tilted back over the edge. And while Ryan and Kevin stood on either side of her face, taking turns to stuff their cocks deep into her inverted mouth, I crawled between her thighs and began licking and teasing her sweet pussy.

It was wet with syrup already, a gaping oval of pink tissue obviously ready to be penetrated. But for now I just used my tongue to pry it wider, to tease the swelling bud of her clit. Her thighs immediately began to quiver and quake in their silk stockings, and her groans of pleasure increased around Kevin's thick cock, until he was plowing back and forth deep into her mouth.