Tutoring Leads to More

Everything started out innocently enough as it always does. Was just another simple job to help pay the bills. Bills which always seem to go up, and never go away. I have always been a good teacher especially in Math and Chemistry. I can usually connect with students easily and figure out what isn't clicking to help them understand the subject more easily. Some students stand out more than others... some parents even more.

14 years ago, I met a family that I will remember forever. The student was a good kid and a good student, just needed some help getting through Geometry and then Algebra. He did very well in my instruction, but what is more memorable is the connection I had with his mother. She was an extremely attractive woman, maybe 5 or 6 years older than me. She had an amazing personality, incredibly fun to be around, and always just slightly flirty. Nothing over the top, but always enough to keep me interested. I always tried to be professional, but I know I slipped some, flirting back with her, but never too obviously. The problem was, we were both married, both had kids, and both seemingly happy.

When her son graduated, I figured that would be the last time I saw her. I missed the connection I had with her, but figured it was probably safest if we were not around each other. There was definite chemistry though, I am sure she felt it too.

It wasn't a year later when I heard from her again. She was taking classes at the local college to become a nurse and needed help with Chemistry. I readily agreed, relishing the fact that we would be working more intimately with each other than when I was with her son. We would meet 2-3 times a week, during which times I found it very difficult to concentrate on my job, rather than her legs, body, and lips. But more than her physical appearance she was just an amazing person to be around. Always very happy and upbeat, always happy to see me as her face would light up when she saw me at the door. Her hugs of welcome were always welcome and returned eagerly to her delight. Things continued in this fashion for a while, never daring to take things further, never daring to ruin a good friendship and potentially 2 marriages.

Eventually our hugs got longer, a little stronger and more often too. A quick peck on the cheek from her was becoming normal as a welcome and goodbye. Her eyes always very searching while we worked, looking for my approval of her work. Her hand would casually touch my shoulder or knee while talking. My hand often touched her shoulder too, longer than what should have been acceptable, but only felt natural with her.

As our sessions became more intimate, our conversations also became more as well, and learned a great deal about each other. The more I learned, the more I was attracted to her as well, and seemingly, the more she enjoyed talking to me. I could only hope she was enjoying it as much as I was. During these talks I learned her marriage was not all it seemed, and we discussed my marriage as well. While neither of us weren't particularly happy in our marriages, neither of us were willing to stray either. As things progressed though, the flirting was a little more obvious and the conversations were a little more risqué. As my sessions were drawing to a close with her, I took a leap I will never regret. As our last session was finishing, I decided to push my luck some. We had just finished a marathon session of 3 hours of chemistry and she asked if i wanted a drink to relax. I responded without hesitation "YES", eager for the opportunity to be around her more, not eager for our time together to end.

We sat on her back deck, both sipping some wine she provided. A nice dark, full bodied red that I greatly enjoyed. We talked about nothing for an hour or so, finishing a bottle of wine between us. With our inhibitions lowered from the wine our touching became more often, longer, and suggestive. We both could feel the heat between us, our cheeks slightly flushed, our breathing shallower than should be. We were both turned on and could tell, there was no hiding it.

Eventually as I got ready to leave, I leaned in for what she thought was going to be another bone crushing hug, I caught her lips with mine as she turned to peck my cheek. We both hesitated for a moment, unsure how to proceed next. We stood there, our faces inches apart, me looking down into her eyes. I knew there was an attraction between us but wasn't prepared for the look of need in her eyes. As we stood there looking into each other's eyes, neither of us could say a word, the look between us was enough. I leaned down for our second kiss, first real one, and made it count. My lips touched hers, softly at first, being very timid as I was still scared out of my mind, not expecting to ever reach this point with her.

My lips opened, our kissing becoming a little more probing, more passionate, more needful. I probed her lips with my tongue, testing the waters so to speak, and found her responding immediately. Her lips opened to accept my tongue while hers also darted out to fence with mine. Our bodies seemed glued together, my arms wrapped around her, gliding over her back, pulling her even closer. Her arms couldn't seem to be content either staying in one place and slide up and down my back, or snaked its way into my hair, pulling my head down to hers more insistently, the other reaching my ass, grabbing it and pulling me closer with it. Taking this cue from her, my hands reach down, and both grab her ass, pulling it in to me as we continue to kiss deeply.

I realized at this point that it may not have been a coincidence we were alone for this session. My mind is too occupied to grasp this fully though and didn't care. My mind isn't the one running the show anyways. My lips leave hers and snake my way to her neck and earlobe, finding those sensitive spots, nibbling on her ear lobe, sucking on it and doing the same on the nape of her neck. Her back arches and one of my hands move up to cup her breast while I kiss her neck. She gasps in surprise, but doesn't pull away, if anything she seems to get more turned on. Her fingers are racking my back now through my shirt, her breathing was definitely shallower now. I pull away from her... her fingers grudgingly leave me.

I reach the bottom of her shirt, slowly lifting it, giving her a chance to stop me. When she raises her hands to make it easier, I know I have nothing to worry about. With her shirt gone, her breasts are only contained by her white lace bra. The hidden flesh arouses me even more, always has. I have always been a sucker for lingerie. She reaches behind her and unclasps her bra letting it fall, exposing her breasts for the first time to me. Although I like a nice firm ass, I have always been a tit guy. Her tits seem like a nice C cup, chest size, probably about a 34. They are surprisingly perky for being slightly older and she can see I appreciate them. I reach out and cup her breasts in my hands, feeling their firmness, teasing her nipples with my fingers, feeling them harden from the attention. My mouth moves down, seemingly of its own accord, and starts to pay attention to her breasts, licking them, kissing them, avoiding her nipples as long as possible. I can see goosebumps form around her nipples as I kiss all around them and lightly blow on them. My tongue slowly tests a nipple, feeling its hardness drawing a gasp from her. I move my mouth to her other breast, this time drawing her entire nipple into my mouth, sucking on it and lightly nibbling on it, making her shudder and her knees start to buckle. I realize at this point, we are still on her back deck. But as she lives further out of the city there is literally no one around for at least 100 yards or so. I guide her to a chaise lounge on the deck and encourage her to lay down.

Her eyes get wide with anticipation as she lays back. I realize at this point that I am fully clothed, while she is now half naked. I smirk at her as I pull my own shirt over my head, exposing my bare chest. At this point we are each only wearing shorts as it was a warm autumn day. As I lean down to better pay attention to her she runs her finger tips up my chest through my chest hair, moving up to my neck to pull me down for another long kiss. As our tongues meet, her free hand moves down to my crotch, feeling my hardness through my khaki shorts. My hands move back to her tits, pinching her nipples and lightly pulling on them, making her moan into my mouth and rub my cock more insistently.

My mouth leaves hers and leaves a trail of kisses down to her tits, circling each nipple before sucking on it, making them even harder than they were. My lips then form a trail of kisses leading down to her stomach, her belly button, and continue further down. My hands pull down her shorts as lips continue further down. They encounter a pair of white lacy panties that I realize match the discarded bra from earlier. I pull them down next while my lips continue to kiss further down, finding a neatly trimmed pussy, gushing in her wetness. Her body seems to undulate on the lounge while I kiss all around her pussy, never touching it. She smells sweet, and fresh and oh so inviting.

I have always loved to give oral sex to my partners, feeling the power to make them reach multiple orgasms with only my tongue, nose and occasional finger to get her there. She is starting to whimper now, practically begging me to touch her, to lick her. My fingers reach up and cautiously spread her pussy, eliciting a moan from her as my tongue gently licks inside her pussy, slowly sliding up to her clit. Her clit is partially hidden in its hood as I lick the underside of it making her gasp and moan. I take my time, not wanting to rush things, wanting this to last, as this may be the last time I get to see her. My tongue works its way back down and up repeatedly, drawing her clit out of its hiding spot more and more with each pass. Every few times I pause and push my tongue into her pussy, penetrating her with it, fucking her with it. Her juices flow onto my face each time I do this, and I savor the taste. I wiggle my tongue up and down while buried deep within her, making her moan even more. This time while sliding my tongue up, I replace my tongue with a finger sliding into her pussy so my mouth can focus on her clit. Careful not to over stimulate her I cautiously flick her clit with my tongue, making her moan even more. The more she moans, the wetter she gets, enough to slide in another finger into her pussy with my first. My lips move down now to her clit, sucking on it, drawing it into my mouth, feeling how hard it is in its arousal.

My tongue begins to flick it up and down raising her arousal even further. My fingers are still sliding into her pussy and her body is heaving in its arousal. As she seems to reach a peak, I reach up with my free hand and pinch her nipple, sending her clearly over the peak, making her climax with tremendous force. Her pussy clamps down on my fingers as she lets out a long-drawn-out moan as she pulls my face even closer to her pussy with her hands on my head.

As she comes down from her high, I move my body up hers, kissing and licking my way up. My lips find hers again and we kiss deeply, feeling the passion in the kiss. The long-awaited release. We kiss for a few minutes before she breaks this kiss with a wicked grin saying, "Your turn".

She gets up, and encourages me to lay down on the lounge, while removing my shorts and boxers. My cock by this point is rock hard, eagerly awaiting some attention. I don't need this attention, I am ready to go now, but love the feeling of a warm mouth on my cock. Her hand reaches down and starts to stroke my hard cock, sliding along its full length. She leans down and kisses me at the same time, letting our tongues dance with each other. She can feel the precum that already moistens the tip of my cock, adding lubrication to her hand as she strokes me.

She pulls away from the kiss with that evil grin that I have just recently come to love and moves her mouth down to my waiting cock. It seems to quiver with anticipation. As she bends down to suck it, she first extends her tongue out to lick the underside of my head up to the tip to taste my precum. My body seems to jump with the contact, eagerly wanting more.

She smirks at me before opening her mouth and accepting me into it. As her head slowly lowers onto my cock, I tip my head back and moan with the sheer pleasure of it. She seemed to enjoy this very much, as her head bobbed up and down on my cock. She would pause at the tip to look up at me while she swirled her tongue around the head of my cock. This was a side of her I never thought I would see, this malicious look in her eye as she devoured me. Her hand reached up and massaged my balls as her tongue and mouth expertly pleasured my cock.

And while I love my cock sucked on as much as any guy, I didn't want to cum yet. I wanted to feel her on my cock, wanted to fuck her badly. I pushed her up off my cock, and she did so hesitantly. I sat up, and pulled her to me for another amazing kiss, another tongue dance. I had us switch positions, with her on her back on the lounge, me between her legs, both of us knowing what was coming.

It seemed as if this moment had been building for years, which it had, but only realized these past 6 months of so. I looked deep into her eyes as I positioned my cock at the entrance to her pussy. I slowly pushed in and see the pleasure on her face as her body arches up. Once I am completely in, I pause for a moment to help become accustomed to this new feeling. I slowly pull out, not daring to go fast, if I give in now, I will never get back into control and I want this to last as long as possible. When all that remains in her pussy is the head of my cock, I pause and push back in again. I push in until my cock is fully in her pussy again. I repeat this for as long as I can bear it, I am hoping for a couple of minutes, but I have lost all sense of time. The slow agonizing pace is enough to drive both of us insane. Inevitably my resolve fails, and the pace picks up, seems with each thrust my pace becomes faster and faster or stronger and stronger. Our pleasure is seeming to reach a peak, but I don't want it to end. Hesitantly I stop, to rest, to build more stamina.

After I catch my breath and come down from the edge I pull out. She takes control and pushes be down onto the lounge on my back, my cock standing at attention as she steps over me to straddle me. She reaches down and grasps my hard cock, positioning it at the entrance to her pussy before sliding down its length, embedding it deep into her pussy.

She leans forward to kiss me, a long probing kiss as she starts to rock on my cock, sliding it in and out. As she rocks, she is grinding her clit against me at the same time, giving herself much more pleasure, making her pussy grip me even tighter. We continue like this for a few minutes, my hands on her ass, pulling her onto me even harder in sync with her motions. My lips glued to hers, savoring the sensation. She leans back and breaks the kiss, sitting upright on me and starts to bounce up and down on me. Her tits bouncing as she fucks me. My hands seem to reach up of their own accord and grab her tits. My fingers find her hard nipples and pinch them, rolling them between my finger and thumb. I can feel her pussy clamp down on me again while she rides me, for what feels like the 4th time.

As she comes down from her orgasm I sit up and lean her back. I pull her legs up over my shoulders as I try desperately not to let my cock come out of her pussy. Now leaning over her with her legs held way up, my cock has direct access to her pussy, inviting me in even more. I start to piston my cock into her pussy over and over again. I have been denying my own orgasm now for so long that I can feel it building very quickly. I start to move faster and faster, slamming into her repeatedly. I can feel my orgasm building quickly now. I keep fucking hard now, faster and faster with each thrust. I can see her tits bouncing with my motion and she grabs them with her hands and pinch her nipples while I fuck her. We both know it won't be much longer, both can feel each other reach this coming orgasm.

As I push in 1 last time, we both seemingly explode in our orgasm. Months of pent-up feelings, months of pent-up sexual frustration released in that one moment. My orgasm feels huge as I release several thick streams of cum into her pussy. Her pussy grips my cock so hard in its own orgasm it seems as if it is trying to milk the orgasm from me. We both are motionless for what feels like minutes, but probably no more than 30 seconds, and try to make our hearts slow down.

Grudgingly I pull out, my cum spills out with my cock, evidence of just how big my orgasm truly was. I collapse on to the lounge with her, breathing deeply. She turns around and kisses me, long hard, a wanting yet exhausted kiss. We take comfort in each others company for a short period but realized it has been hours since I showed up and really should get home.

We clean up and get dressed. We agree that while this was fantastic, we really shouldn't continue, we both would like to work on our marriages, and we both have kids to think about as well. We parted good friends and have kept in touch sporadically through the years. Eventually only talking once a year or so.

Then, out of the blue, I get a message from her. Wondering if I am still tutoring, of course I told her yes. Turns out her youngest is now in need of a tutor. I didn't know what to expect... it has been years since I had seen her in person. Years since that day on the deck. What could I expect?