How To Be a Good Mentor

"Mmm!" She pulled back again, staring at me with a wild, challenging look in her wide eyes. "That was interesting, Dave. Nice little move, there." She looked straight down, and even though I'd guessed she'd know I was hard, and I knew she'd have to find out eventually, the moment when she bowed her head and searched greedily for my cock had me so self-conscious I nearly looked away.

It didn't take her long. It couldn't have; my penis is not terribly small. She knew immediately what she was looking at. "Why Dave," she cooed. "You do like me."

There's no way for a man to be nonchalant about a hard-on. Not a man like me. "Well, uh, I told you so," I replied, subdued. My throat had gone dry, my body shivering with the reality of what was happening here.

"You did indeed," she went on absently. I finally looked down at her; with her legs spread wide, the yoga pants might as well have been shrink-wrapped on. She wasn't hiding anything more than I was; her labia were clearly outlined, the slit between them just a hand's breadth from where my cock surged obscenely down my leg. We paused a moment, the two of us breathing hard but calming down after trading tongues; our hands rested lightly on each other's hips. At length, Shannon cleared her throat again, but her voice was still smoky as she spoke up.

"So, here's the deal," she said slowly. "As your mentor, I think it's my duty to look out for your well-being. And I'm afraid that, with all the alcohol you've consumed tonight, I really do feel it'd be irresponsible for me to let you drive anywhere."

"Huh." My own voice was strained. I couldn't stop looking at her mound. "As my mentor."

"Right. I'm just being professional."

"Sure." Her skin was trembling under my fingers, and I couldn't believe it: she was nervous. Or excited; either way, it wasn't anything I'd expected. I looked to the left, past the TV as it continued droning relentlessly on, to a couch against the wall. "I appreciate it, Shannon," I croaked. "I'll be fine on the sofa."

"Bullshit," she snapped at once, still staring hard at my dick. "No way. You're my guest. I insist that you take the bed." And then she was blinking, a crafty grin flashing past her teeth as she swept her eyes up to my face. "Well, part of the bed, anyway. You're not a student anymore, Dave. We can be adults about this, I'm sure. I'd trust you to be a gentleman if we go upstairs."

"Now why would you do that?" I held my breath; I was becoming pretty confident that my flirting was going well here, but this was such an unbelievable development that I couldn't trust my own mind.

"Well," she said pompously, her fingers nibbling at another shirt button, "surely trust lies at the base of any mentor-mentee relationship, I would think."

"Ah." I couldn't stop my fingers from flickering up her sides under the sweatshirt, feeling the muscles there, and she sighed. "And so I take it you'll be a perfectly respectable lady."

She laughed breathlessly, really more of a snort. "You'll find I'm an excellent hostess," she murmured, her finger running rhythmically up and down my stomach above my belly button. "Remember: full service is something I pride myself on." She dragged herself backward, her feet finding the floor as she got to her feet. The forgotten drinks and the hockey game might as well not have existed. "I never did give you the full tour of my house, Dave. If you'd like, I can show you where you'll be spending the night."

I swallowed, my cock rampant now, my brain finally realizing this was actually going to happen, amazingly enough. I was dazed. "Just in the interest of safety, of course. To keep me out of trouble."

"Of course." She stood there, legs spread, her hands on her hips, and I saw her eyes waver back down to my crotch. "I insist."

"Well then." She stepped back until the coffee table halted her, and when I got up I was a mess: my shirt most of the way undone, a huge tent in my khakis, my mouth smeared with her spit and lipstick. "Lead on, Shannon."

"Yes sir," she winked, the grin tightening in self-congratulation, and then she was moving around the loveseat toward the stairs. I followed, my eyes glued to where the yoga pants outlined the smooth, muscled curve of her ass; I guessed she hadn't bothered with underwear. She passed the kitchen, skirted the corner of the dining room, and was on her way up the stairs without a backward glance.

She obviously knew I'd be staring at her butt the entire way up the stairs. Why wouldn't I? After what we'd been doing on the couch and what seemed to be coming up next, there was no reason not to. So I took it all in; from where I walked behind her, her thighs were just barely narrow enough for me to make out her pussy from behind. I felt my mouth fall open, the glory of her ass staring me right in the face; certainly no underwear, not even a thong that I could detect. Each cheek was a perfect, rounded bubble, muscular but not too lean, enough in itself to stir the penis of any man not already hard as fuck.

"There are two bedrooms up here," she was saying calmly over her shoulder, "but we just use one of them for storing shit. And for Leon's fishtank." I caught an eyeroll. "So there's only the one bed, I'm afraid."

"Gee." I reached the landing and followed her down a short hallway that overlooked the living room, the hockey game still mindlessly on. "However shall we manage that?"

"It's a problem," she agreed with faux seriousness as she turned abruptly through a doorway to the left. "The only thing I can think to do," she pondered, "would be to share the bed. Being careful, of course, to stay on our proper sides."

"Always." I was lightheaded as I passed into Shannon Boyle's bedroom, with its huge windows overlooking the salt marsh; dizzy, and not from the stair climb. The place was airy, high-ceilinged, with a bathroom opening to the right; she'd left the light on in there. The place smelled like washed sheets and a faint scent I'd noticed in other feminine bedrooms, a mix of soap and powder and body odor and perfume. Her tight white dress lay on the floor near the bathroom, with a matching grey bra and panty set nearby.

"Sorry the place is such a mess," she breezed; that night's clothes on the floor were the only items out of place, and she made no effort to pick them up. "When Leon's away, I tend to get... dirty." She turned to face me as she reached the corner of the bed, her eyes sparkling in the dim light. She stood poised, breathing evenly as she stared at me. "You ought to just go ahead and take your shirt the rest of the way off, Dave," she advised with a faint smile. "You seem to be a bit disheveled."

"Can't have that, can we?" In response to her studied calm, I could feel my heart trying to hammer out of my chest, my skin flushed and sweating. "I'm not sure I brought proper, uh, sleeping attire," I blundered on, forcing my hand to stay steady as I undid the last few buttons and started to shrug my shirt from my shoulders.

"I can find something of Leon's," she shrugged, then cocked her head and grinned. "I usually sleep naked, Dave. Are you okay with that?"

"Well, uh, customs of the house..." She was already lifting the sweatshirt, and I stopped talking as she exposed her lean, smooth abs, her ribcage, and finally the breasts I'd been waiting more than six years to see, never having any kind of realistic idea I would ever, ever do so. They were what I'd always hoped: nicely sized round handfuls of firm flesh, bobbing now as the sweatshirt scraped up over them, with small dark nipples that drew a gasp out of me as they settled back into place, high on her chest as the sweatshirt came sweeping the rest of the way off. I felt myself gaping as she stood there proudly, her back straight, and smiled at me with that conquering smile women get when they know they've got you. She let me squirm awhile longer.

"Oh, I'm sorry. Am I distracting you?" Her smile was wide and content; she was very satisfied with my reaction, as well she should be. I felt like a novice monk facing the Second Coming. She looked at my upper body, pursing her lips critically. "You're a little scrawny, Dave, if I'm being honest. You always were, you know." She took one very deliberate step toward me. "I'd love to get you into the gym; I'd whip you into shape tout suite. I'd consider it another kind of mentoring." And then she was right before me, nearly a head shorter, the two of us half-naked and looking seriously at each other as though trying to memorize every detail. "Which side of the bed do you want, Dave?"

I swallowed. Her nipples, a red so deep and mysterious as to be almost purple, reached out for me. I stared helplessly. "I, uh, I guess the side by the door?"

"Sure thing." She reached nonchalantly up to brush back her heavy hair, the nipples dancing again like windchimes. "Eyes up here, Dave. You're not being the respectful gentleman you promised you'd be, you know." She was grinning. "Do I need to put my shirt back on?"

"No! Jesus fuck, no!"

She laughed her rich, bell-like laugh. "Go sit down on the bed, Dave. You seem a little tense, but I've got an idea." Her dimples were in full effect in the soft light from the bathroom, and I moved as if in a trance to take my seat, my legs hanging over the edge of the bed. It was a king-size; I'd never been on a bed to large, even in hotels. It felt like sitting on an aircraft carrier.

"Now then," she purred, sliding around to stand before me. I caught my breath as I raised my eyes to her face, skipping over her symmetrical lycra-covered pussy, past where the yoga pants became smooth muscular flesh with just the barest hint of softness, past where the bathroom light picked out her sternum, flanked by those two perfect breasts; her face, radiant and with freckles chasing themselves across both cheeks, looked serious. "I'm going to suck your dick, Dave. I want you to relax and enjoy it. When you feel like cumming, just go ahead and do it; I won't mind." She licked her lips slightly, her fingers flexing. "The goal here is to calm you down and get you nice and mellow. You want to feel nice and mellow, Dave?"

Her teasing little grin encouraged me. "Hell yes." She knew I was nervous; there was no point in pretending. We were way past any of that.

"Good." And then my dreams moved into a higher gear, her big gorgeous eyes sinking down as she went to her knees. Her hands found a comfortable spot on my thighs as she rubbed my legs slightly. I let them part as she forced her way gently between them, and then she craned her neck to maintain eye contact. "Might want to lean back, Dave. I like to have full access to my men." She giggled.

My God. I'd thought I couldn't get any harder; I'd been wrong, seeing the passion spread slowly up and over her face from her flushed chest to the eyes so firmly skewering mine. I felt like half my blood volume was charging toward my dick. The passion, I knew with a sudden flash of insight, came from power: she knew I was hard, and she knew she was the reason, and it was getting her off.

I let my head drop back onto the mattress; I knew I'd benefit profoundly from her arousal, and in a sudden surge of excitement I wondered what I'd done to deserve this. The ceiling was distant, full of weird angles and shadows from way out in the harbor, but now was hardly the time for nautical speculations. She was yanking with businesslike greed at my fly. And when I tipped my head up to look down my hollow chest at the longed-for sex goddess crouching between my legs, I saw nothing but a thorough professional: a genuine prostitute could not have undressed me more efficiently. And I mean that as a compliment.

Though I was careful not to tell her.

My belt came whisking out of its loops, her left hand coolly holding my cock through the pants to keep it out of the way as her right maneuvered the buttons holding the pants together. With no wasted motion, both hands then made the short trip to my waistband, hooking both pants and underwear out of the way. Her expression had been neutral, almost clinical, but now she glanced up to see whether I was watching her; once we made eye contact, she grinned with her mouth open, and arched one eyebrow. "So let's see if you're just as scrawny everywhere," she joked, already knowing the answer; her left hand had been firm on my junk. She knew what she was getting.

I debated about whether I should let my head flop back and wait for Shannon to work her magic, but in the end I decided to keep my head propped up: you only get one chance to see a woman react to your naked cock, and this was a night I wanted to remember forever. Her experienced fingers prepared me for the unveiling, a couple of them digging slightly into my boxers to pull out my cockhead; she let it rest against my belly, then tightened her grip, arched her back to get her body out of the way, and stared intently at where she was about to free me to the cool air of her bedroom. She examined the rubber duckies on my boxers. "Very manly choice of underwear, Dave. You ready?"

"I think you can probably tell," I managed, my voice sounding strangled in my ears. She winked, which I was starting to get used to, and then she had my clothes most of the way down my legs in a single brisk motion, pushing them down past my knees and then raising her body to kneel on the mass of boxers and khakis. I was locked into place.

Her smile and her eyes both widened as she looked down at my dick in the shadows. "Why Dave!" she gushed quietly, her face twisting into a mischievous smirk as her fingers came to rest on my hairy thighs. "I didn't know you cared." Truly, the penis before her was obscenely, even hideously extended, as long and firm as I could ever remember it being, vibrating like a guitar string as it stretched up from my lank little nest of pubic hair. It looked like an artillery piece, pointing ready for war, waiting impatiently. She examined it indulgently, dipping low to study my scrotum. "I'm not even sure where to begin."

I felt something was called for here other than me gasping theatrically; time to get in the game. There was clearly no point in letting myself be awkward any longer. So I drew my elbows back and propped myself up and, at last, allowed myself to smile. "I'm sure you can figure something out, Shannon."

"I'm sure I can." She hadn't even touched it yet, and already the sensations were overwhelming; in particular, I was nearly shivering as I felt the smooth skin of the sides of her breasts rub dryly against my inner thighs. "Don't you worry about me, kiddo. I'm game."

Then it happened.

Those big, shining brown eyes met mine one more time, she made a very Lucy-looking kissy face, and then she kept watching me as her mouth dropped open toward my ballsack. I felt stillness, then her warm moist breath, then finally her tongue, reaching delicately out to plant its tip right up into my crotch, just shy of my asshole. Then she swept, wet and graceful, up around my balls, her tongue flattening, moving slowly enough not to outrun her supply of spit; she finally arrived around the top, where shaft met sack, and then she was gliding deliberately up and over every vein, every tendon, every nook and cranny, her shoulders rising, her hands trembling with excitement.

I finally let my head fall back again, sighing in disbelief, when I saw her tongue arrive at my head, then pause while she crawled up over my groin to bring her lips down over my straining dick, and so I lay there and felt like I was melting into the comforter as, with a slick slithery noise, I entered her mouth and the sucking began.

It felt like heaven. I mean, I've had blowjobs before, but... I'll never know whether she was just really good at it, or whether it was me: I'd been so invested in Shannon Boyle for so long. She was my oldest crush, and having her sucking my cock could have been a disappointment that would never live up to my dreams. Or it could have been the most profoundly breathtaking experience of my life.

And, so far, it was the second one. I lay there like a victim of a bomb blast: stunned to insensibility; shocked to be in that situation; profoundly grateful, too. The smacking and slurping of Shannon's steady mouth, the ticklish whisper of her wavy hair across my skin, the gentle tightening of her fingernails over thighs or balls or stomach; she was letting out occasional moans, too, and they sounded genuine. I was gone, lost on a red-pink cloud, my senses operating at their highest pitch.

But not for long; there was a painful sense of dilation, the ceiling seeming to stretch away from me, and I felt my orgasm come looming toward me like the monster out of some child's closet, and just as menacing. Good Christ, it had probably only been, what, three or four minutes? There was no way I could even think of cumming so early. "Gahh," I grunted, curling myself upward as I shook myself out of the intensity of Shannon's skilled tongue, and as I twisted off the bed I saw her: my dick snaking firmly past her dark lips as she looked hard at me, her eyes now blazing as her nimble fingers plucked at my scrotum, then dipped playfully lower to play near my asshole.

"Shit, Shannon," I gasped, trying to dig my butt into her bed so that I could pull my dick out and maybe, possibly, preserve myself for even three or four more minutes, salvaging a little of my pride. She wasn't having any, though; she knew at once what was happening to me, and I saw her distended mouth twitch out into a smile as she bore down on me, slurping and gagging as my head nudged the back of her throat, the nasty choking sounds to out of character coming from the serene, ever-cool woman I'd been so in love with for so long.

I was not a high school student anymore; I had no business cumming so early, but as I felt her tongue lap insistently at my balls, her nose leaking snot into my pubes as she clamped one of her hands around my ass with all her wiry, gym-toned strength, the pleasure peaked and peaked and peaked again, the wave of semen threatening like the growing pressure behind a breached dam, and when at last I heard her laugh wickedly around my dick, my tightening scrotum telling her fingers all they needed to know, it was game over.

"Jesus Christ!" I cried, flopping back against the sheets, shaking like a rattlesnake's tail as I shot my sperm helplessly down Shannon's throat. She'd been swaying, but now she crouched still and tense, one hand on my shaft while her lips pulsed steadily just behind my head; those eyes of hers still pierced me, and I remember thinking that in that moment, there was nothing in the world I wouldn't do for her.

We don't really ever know what kind of people our coworkers are in their private lives; still less our teachers, but even allowing for that uncertainty and my own youthful crush I never would have dreamed of Shannon's competence as a dicksucker. She'd known precisely how to get my load, and now she was taking it down with no more difficulty than she'd have squashing a cockroach. I even got an impression of slight boredom from her, like she was already thinking ahead to the next way in which she could toy with me; an impressive amount of self-control, actually, given the quantity of semen she was currently processing.

I lost count, but there had to have been four or five full loads, even before the inevitable trickly ones that come out at the end. My hips, tense and heavy, now eased back down onto the bed, the stringy muscles of my legs relaxing under her caress. Shannon waited, still sucking gently, and then she backed slowly off my slimy dick, letting me see every inch as it emerged shiny from her luscious mouth, before planting a soft kiss on the head and rocking back on her heels.

For a moment we both just breathed; panted, rather, but she recovered faster. A maniacal fitness routine will do that for you. "So," she said hoarsely, "I guess that'll take the edge off a bit, hmm?"