The Tutor
Copyright© 2003 by Dorsai
Chapter 2
Coming of Age Sex Story: Chapter 2 - Young James grew up next to Maureen, who got widowed. As James was turning into a man, Maureen was there to guide him in some important ways.
Caution: This Coming of Age Sex Story contains strong sexual content, including mt/Fa Consensual Fiction Anal Sex Oral Sex
Over the course of the next couple of weeks, Maureen casually let Mom and Dad know that she was planning on making a number of changes and improvements to her house - giving them a perfectly good reason why I would be going over there more often and staying longer. She even went so far as to tell Dad that because of all she would be having me do, she was thinking about paying me for some of my efforts; then let Dad talk her out of it. She spent a couple more weeks going about the task of getting some of the materials she needed for the changes she had in mind. Along the way, there were a few times that she asked Mom or Dad to have me stop by, first to help with the planning, then to make sure she had everything - they didn’t have the faintest idea that what really happened when I got over there was that Maureen and I would get into a hot-and-heavy necking session that usually ended with both of us naked, her giving me a blowjob as I fingered her to her own release. It was during my first ‘consultation’ that she let me know she’d seen a doctor and had started taking the Pill - but that she’d been cautioned that it wouldn’t be fully effective until the start of her next cycle.
You can be sure that I was eagerly looking forward to the time that she would call me over to ‘help’ when the end of that first month had gone by - and was then disappointed when she didn’t. It was nearly five weeks from the time that I’d first looked down her blouse before Mom casually let me know that Maureen had asked me to come over that night to help her out. Somehow, I managed not to show the excitement and enthusiasm I felt when I said that I’d go over after supper.
When I got to her door, I was about to ring the bell when the door suddenly opened up, making me jump. Then I saw that it was Maureen, who invited me in, saying “I’ve been waiting for you, James...”
Inside, and the door closed behind me, I saw that she had, indeed, been waiting for me: the snug shirt she was wearing made it clear that she had no bra on underneath it, and that her nipples were hard behind its material.
Taking me in her arms, she told me “I’m sorry it took so long. First, I started my period, and I didn’t think that you were ready to deal with that mess just yet; then I had to wait for a time when we’d be alone. It wasn’t until this afternoon, when Matt asked if he could sleep over at one of his friend’s houses that I knew this was the chance we needed.”
I hugged her back as she was talking, my hands sliding up and down her back as I enjoyed the feeling of her nipples pressing into me.
After a few moments, we released each other and Maureen looked up at me and said “Well, the first order of business is for you to look at the project I have for you.”
Seeing the look of dismay and surprise on my face, she laughed, and said “James! Remember that the whole reason you’re over here is to help me with these projects. We have to spend at least a LITTLE time on them, in case anyone asks how they’re going. It won’t take long, and then we can begin your lessons!”
Reassured, I followed her—delighted by the way her ass moved in the shorts she was wearing—to where the first of her projects was to be: a set of built-in shelves and a desk for Matthew, so that he would have someplace for his ever-increasing book collection, and a place to study and do his homework. We actually did talk over what she—and more to the point, Matthew—wanted, how long it would take (“minus any hanky-panky” she said, knowing full well that wasn’t going to happen), and what we could do to make it take as long as possible while still seeming to be progressing reasonably. It only took a few minutes with us to come up with a scheme that fit all our requirements.
That accomplished, and both of us certain about what we’d tell anyone that asked about it, the next step was Maureen’s: with no warning or hesitation, she peeled off the shirt she was wearing, exposing the upper half of her body to me before asking “See anything you like, James?”
I admitted that I did, and she laughed before saying “I thought you would. Now, let’s go into my room - I think both of us would be more comfortable there”. She took my hand and led me across the hall to her room, where she got a big smile on her face and said “School is now in session. Take off your clothes!”
I didn’t need to be told twice—particularly after she slid her hands inside the waistband of the shorts she was wearing and began sliding them down her legs, revealing that she didn’t have any more under them than she’d had under her blouse. In less than a minute, both of us were as naked as the day we’d been born.
We took a little time to look each other over before Maureen told me “I think the first thing you should learn about girls is our anatomy. I know you’ve seen breasts—mine, and others. What you need to learn now is the rest of it—the area between our legs. Not just where our vagina is, so you can get into it; but the rest of our parts, too, so you can learn how to arouse us and make us feel good.”
I voiced my understanding, and she went on, “So, what I’m going to do is lie down and let you have a look at me - a GOOD look. I know you got to see all of this when we took our shower together, but that wasn’t the best time for you to actually see and learn everything.”
With that, she did just as she’d said she would: moving to lie down on the bed, her legs spread and her knees up, giving me an unimpeded view of her genitals. I was struck with a sudden bout of nervousness, and was slow in moving to join her. She seemed to understand what the problem was, and waited patiently until I was lying between her feet, my face just a few inches away from her pelvis.
She grabbed a couple of pillows, and used them to prop up the upper half of her body, making it possible for her to see where I was looking. Looking at me, she gently asked, “Feeling a bit nervous?”
I admitted that I was, and she told me, “Don’t be. I’m not much different than any other girl; it’s a pretty safe bet that anything you see on me will be on her. It might look a little different, but it’ll be there. And don’t worry about looking at me like this; it actually kind of turns me on, as you can probably see.”
Once she’d mentioned it, I did notice that the lips around her vagina were separated, the area between them faintly glistening with her moisture. Not as much as I’d seen before we had sex the first time, but still...
She went on to tell me, “James, you need to understand that I want you to look and touch and learn. I’m not embarrassed - not after what we did last month! - and you shouldn’t be, either. Sooner or later, you would learn all this stuff, anyway. All we’re doing is making sure it’s sooner, not later. Please, look and touch and do whatever you want - I’m here so that you can learn. If you do something that’s uncomfortable, or hurts, then I’ll tell you, so that you know not to do it again. But I am most certainly not going to tell you to stop until you’re satisfied that you’ve learned what you want to know. Okay?”
I nodded, and that seemed to satisfy her - she simply rested there, waiting for me to begin my ‘studies’.
Still, it took me a few moments before I was ready to move a little closer so that I could get a better view of her. When I did, I caught the faint scent of her arousal, and that, more than anything else, reassured me that she really was okay with being on display the way she was.
I don’t know how long I was between her legs like that - all I’m really sure of is that she was as patient with my looks and touches and everything else as I’d been with Matt when I was trying to teach HIM something. As I moved from bit to bit of her, she calmly told me what I was looking at or touching - not just the ‘common’ words, but the medical terms, as well. In addition, she went on to explain to me what kind of feelings, sensations, or other things that were involved - such as how her vaginal lips (labia, she called them) would get longer and darker the more aroused she was; how her clitoris would get tingly and how the little cover over it would pull back when she was excited; and so on. She even went so far as to tell me what kinds of things I could do to bring about the changes she was describing to me, and encouraging me to try them to see for myself. Only once did she have to caution me about something, telling me “A woman’s clitoris - yes, that - is very sensitive to pressure. What you’re doing doesn’t hurt, but it’s uncomfortable; if you’re a little more gentle when you do that, you’ll have a girl asking for more very quickly! Yes, that’s it - gently.”
By the time I was satisfied that I’d learned all I could for the time being, it was clear to me that Maureen was more than a little bit aroused by what I’d been doing to her: her labia were clearly longer and more separated, and her opening was visibly wet with her juices. My ‘lesson’ completed, I moved to sit cross-legged between her feet.
I couldn’t help looking at her and asking “You’re ... excited by this?”
She gave me a lopsided grin and answered, “Yes, as I’m sure you can see.”
“Why?”
I think the question surprised her, but she didn’t hesitate to tell me, “It’s a number of different things - and I’m not sure I could explain some of them to you; and another woman wouldn’t need the explanation. Part of it is simply the idea of having you look at me so intimately. Another part is because of the way you’ve been touching me, and learning how to use your hands to arouse me. Then there’s the knowledge that when you’re done, I’m going to have you inside me - the anticipation of it. Finally, and I guess the biggest part of it, is simply the fact that you’re a young, virile man, and I can see that you find me desirable” - that last part with a significant look toward where my erect penis was waving in the air in time with my heartbeat.
To my surprise, I wasn’t embarrassed in the slightest when she noticed and mentioned my aroused state - I could only figure that some of her matter-of-fact attitude about bodies and sexuality was starting to rub off on me.
What did get my attention though was something she’d said.
“You said that when I was done, you would have me inside you?” I asked.
She smiled, and said, “I figured you’d hear that part. Yes, when you’re done, you’ll be inside me.”
“Well, I’m done,” I told her, grinning.
She just grinned back, saying, “Are you now? Well, I guess the next part is up to me, then”, her words confusing me a little.
She must have seen the effect on my face because she went on to tell me, “What I want to do this time is something that I’ve always enjoyed, although you might not have experienced it yet.”
My curiosity got the better of me, and I asked, “What’s that?”
“This time, you’re going to be on the bottom, and I’m going to be on top!”
Thinking back to the few porno magazines I’d seen, I knew what she was talking about - and she was right, I hadn’t been able to try that position before.
“What do I need to do?” I asked, “Besides lay down, I mean.”
She gave me a mischievous grin and said, “That’s about it - that, and enjoy it!”
I grinned back and moved up to lie next to her, my hand reaching for her breast. Cupping it, I slowly ran my thumb across her nipple, marveling again at how her areolas would pucker and her nipple would get longer and harder in response. When the one nipple was standing tall and proud, I moved my hand to give the other the same treatment and got the same response as Maureen’s breathing slowly increased and she released a soft moan, deep in her throat.
I soon replaced my hand with my mouth, licking and sucking on her breasts and nipples, causing them to stand out even more as she gasped her pleasure at what I was doing. I soon detected the unique scent that told me she was becoming more and more aroused; I let my hand drift down her body to begin a new exploration between her thighs. She readily spread them for me, inviting my touch on her most intimate places.
My first touch was to softly run my finger between her vaginal lips several times, coating it with her oils, before pressing against her opening. She moaned softly and lifted her hips in welcome to my soft probe. Gently, I pressed my finger against her entrance, nudging the tight ring of her opening apart to allow me to enter her. She was very wet inside, and I didn’t have any trouble sliding my rigid digit inside her, all the way to the base of my finger. My palm was cupped around her mons, and I got the idea to begin softly massaging her clitoris as I slid my finger in and out of her tight opening. When I did that, she groaned deep in her throat before telling me, “Oh, James - that feels so good!”
After a bit, I could feel that she had loosened up a bit inside; remembering how tight she’d been before, I thought I should try opening her up a bit more by adding a second finger to the first. In short order, I had both my ring and middle fingers deep inside her, both of them well-coated with the ample lubrication she was producing.
Even as I was slowly finger-fucking her, my mouth was still busy - softly sucking on her breasts, my lips tenderly pulling on her nipples. By that time, she was moaning almost continuously, her breath coming in short pants as her arousal continued to grow. I could hear and feel her getting closer and closer to an orgasm, so I wasn’t surprised when she finally released a soft cry before her body froze as a series of waves rippled through her vagina, clamping down on my fingers. I continued to suck on her nipples and massage her clitoris even as I heard and felt it as she cycled through the sexual release I’d managed to bring her.
After she finally relaxed, I carefully withdrew my fingers from her still-twitching vagina; she surprised the hell out of me by reaching down to take my hand and bring it up to her mouth, where she went about licking her juices from her fingers, her eyes locked on mine as she did it. I felt my penis twitch when she took each of my fingers in her mouth and sucked on it to make sure she’d gotten all of her oils off of it.
When she was done, she gave me a wicked grin before saying “Now, James, it’s MY turn!”
With a gentle nudge, she eased me over onto my back before sitting up herself. Looking down at me, she said “That felt very good - but I still need to have you inside me.”
From being next to me, she moved down until she was hovering over where my erect and throbbing penis was waving in the air. A brief glance at me, and she lowered her head to take me into her mouth, sucking on me as though my penis was a particularly tasty lollipop. As she was doing that, she began twisting her head to bring a whole new set of sensations to my saliva-slick member.
Once she was satisfied that I was fully erect (!!) and well-lubricated with her saliva, she rose up again and moved to straddle my waist. I could only look up at her, her passion clear on her face as she reached down between her legs to grasp my penis. She rose up again; then moved back slightly, positioning the tip of my erection against her opening. Holding me steady, she looked deep into my eyes as she slowly began to impale herself on my pole. The way she was spread, I could easily see the entrance to her vagina, and watched, mesmerized, as her hot, wet sheath slowly enveloped my erection in a single slow, steady motion.
With my full length buried in her, she closed her eyes and paused a few moments as though savoring —as I was— the sensation of having me inside her again. Then I felt her vagina tighten slightly, and saw that she was raising herself up again, letting nearly half my length slip free before lowering herself again. A moment later, she did it again, then again. Each time she settled back onto me, it was a little easier for me to slide into her.
A few more such cycles — each a little longer and faster — went by before she switched over to something different: getting her legs under her, she moved to squat over me and begin slowly bouncing up and down, raising herself nearly all the way off of me before coming back down again. That went on for a couple of minutes before her legs apparently began to tire; then she switched back to straddling me again, leaned forward — her breasts were just out of reach of my lips — and began an arching of her back that only moved her along about a quarter of my penis; but it was the LAST quarter, meaning that each downward thrust of her hips brought her fully against my pelvis, taking as much of me inside as she could manage. I wasn’t the best-hung guy in any of my physical education classes, but I was definitely at the ‘gifted’ end of normal - and I could feel the head of my penis lightly touching the deepest part of her with each arching of her hips, accompanied by her soft groan of pleasure at the penetration.
The sensation was incredible, and I fought to try and maintain some sense of control over my approaching climax. But the feelings she was creating were intense; I managed to gasp out “Maureen! I’m getting close!”
She opened her eyes at my words, and stopped her movement over me, saying “Fight it, James! Think about something else - something to distract you!”
With the sensations around my penis gone, it was a lot easier for me to do as she said; still, even as I was trying to remember my stats on the baseball team, I could feel her clenching her vaginal muscles around me. After a little bit, the urge to empty myself into her had passed, and I looked up to see her watching me carefully. I nodded that I was ready, and she leaned forward to put her hands on either side of me and begin rocking back and forth to slide herself along my length - something that left her doing almost the exact opposite of what she’d been doing before: sliding herself on and off the three quarters of my penis that had stayed inside her previously.
The feeling of it was tremendous - and nowhere near as stimulating as feeling myself ‘bottoming out’ in her vagina. Apparently, though, it worked for her - it took only a minute or two of rocking back and forth on my dick before she pushed herself back on it as she cried out “Oh, God, I’m cumming!”
I could feel her vagina clenching around me, and it felt wonderful - but I had been able to get a little more control over myself with the change in her movements on me, so I wasn’t in any ‘danger’ of climaxing myself. Still, I have to admit that it not only felt good, but was fun to watch, as she went through a fairly serious orgasm. I’d never really had the chance to watch a woman before as she had an orgasm - Maureen being the first female that I’d ever knowingly brought to orgasm, and I’d been a little ‘distracted’ the first/last time - and it was fun, interesting, and informative to watch.
Even as I was watching her face, I could feel her body - and more to the point, her vagina - as spasm after spasm passed through her between her gasps and moans of pleasure.
When most of it was over for her, I felt her start moving over me again - slowly at first, sliding herself almost completely off of me before pushing back again until the tight ring of her opening was around the base of my penis.
Another minute or two, and she was moving more quickly; as hot and tight she was inside, I could feel myself begin to approach the point where I knew I would empty my balls in her. I looked up at her and said, “I’m getting close again”; she responded by looking into my eyes and nodding her understanding before slowing her self-impalement on me. Rocking forward a bit, she managed to get her breasts within range of my lips; I eagerly took advantage of the situation to wrap my lips around each of her nipples, taking turns sucking on each of them before moving my attention to the other. It was only a minute before both of them were standing at attention, her areolas tight and puckered, the peaks of her breasts glistening with my saliva. With a soft moan, she raised up, pulling her nipple from between my lips before taking a squatting position over me with my penis still inside her.
Again, I could clearly see the lips of her vagina; they, and my penis, fairly shined with her fragrant oils. I looked up to see that she was watching me, a lusty grin on her face. She gestured with her head that I should look again; when I did, she moved to lift herself off of me slightly - an action that caused her labia to extend even farther, as though trying to hold on to my penis. When only the head of my dick was inside her, she paused a moment, then began to lower herself; I watched as her glistening lips first disappeared inside her before more and more of my penis followed them until her russet pubic hair was blended with my own dark curls. I had two simultaneous sensations: the clenching ring of her vaginal opening at the very base of my erection, and the faint pressure of the head of it pressing against the deepest part of her. It was a sensation I’ve felt only a few times since; then, with her, it was the first time, and it was an experience that served only to make me even harder inside her.
I looked up into her face, and clearly saw her combined pleasure, desire, and what I can only describe as pure, unadulterated lust.
I felt her press herself down against me even more, gaining only a tiny fraction of an inch more of my penis inside - but it was apparently enough, since she moaned loudly when she was done. We stayed like that for several seconds before she moved to lift herself up again - slowly and with great deliberation. I watched again as my penis slowly reappeared from the depths of her womanhood; only when her upward movement stopped did I notice that the hood of her clitoris had pulled back, exposing her pea-sized clitoris.
Without even thinking about it, I reached between us and collected a sample of her oils on my fingertip, then gently ran it across her erect clitoris - drawing a loud groan from Maureen in reply. I did it again, with similar results; then again and again. With each caress of her sensitive nubbin, her groans became louder and her breath came faster and faster. After a minute or so, though, she started moving on top of me again - first slowly lowering herself back onto my penis, and then lifting herself up again.
Because of the way she was positioned over me, the only contact between us was the slight pressure of her ankles next to my waist, her hands on my chest, and —to our mutual delight— the sensation of her tight sheath around my manhood. It was only a few moments before the only feeling I was aware of was how her hot, wet channel enveloped and released my sensitive penis as she started moving herself up and down on it more and more quickly - and with more and more force, almost slamming herself onto me on the downward strokes.
The sensation was entirely unlike —and infinitely more intense— anything I’d experienced before then, and it wasn’t long before I could feel myself getting close to emptying my balls in her.
It must have been having a similar effect on Maureen. Even as I heard her release a loud cry, she impaled herself on me one more time, pressing herself downward to take as much of me inside as she could as she threw her head back. I felt the walls of her vagina clenching at me - and much to my surprise, it felt as though the deepest part of her was almost ... well, sucking on me. Between the clenching around the rest of me, and the faint, but distinct, pulling around the head of my penis, that was all I needed to begin squirting jet after jet of my cum deep inside her. I managed a brief look to where we were joined, and saw that the lips of her vagina were pulsing slightly in time with the spasms I could feel going through the rest of her; that sight was enough to make my second shot of cum erupt nearly as strongly as the first had.
My hands somehow found her breasts, and I gently pulled and pinched her nipples in time with the clenching of her vagina around my erupting penis - something that only seemed to make her inner muscles grasp at me that much harder.
Still, as all good things must, our respective climaxes eventually slowed and faded. I think that mine ended first: I can remember looking up at her as I panted my release and watching as she first let her head drop, then her eyes open.
It took a few moments before she was able to focus on me; when she did, she gave me a broad smile, her pleasure and satisfaction clear on her face as she told me “Thank you, James - that was wonderful!”
I could only grin back up at her - she clearly knew that I’d enjoyed it, too.
After what she’d told me the first time, about wanting me to stay inside her, I wasn’t surprised when she didn’t do anything to get off of me right away - I could feel that I was still mostly hard, due mostly to the way her internal muscles would tighten around my penis every so often.
Still, I could see that she was tired, too, and I had an idea. I thought it through for a moment, the suggested “Maureen? If I bend my legs up a little, I think you could kind of use them as a backrest, so you could sit on me, instead of sitting over me like that.”
She thought about what I said for a few moments, and nodded, saying “Yes, I think I’d like that...”
She leaned forward again —her breasts swayed ever so slightly in front of me— and she moved to reposition her legs as I brought my feet up, bending my legs behind her. She hesitated a moment, and then said “While I’m at it, why don’t I grab a couple of pillows so you can sit up, too?”
I voiced my agreement, and when she stretched out for them, managed to get my lips around one of her nipples. She hesitated, looked down at me with a smile on her face, and went on to pull a couple of pillows next to me. With the necessary materials at hand, she had me sit up and quickly positioned the pillows so that they would support me before leaning back —pulling her nipple from my mouth— to rest against my legs. At no point during the process had she lifted herself off of me enough to let even a little bit of my penis slip out.
With the two of us facing each other (well, mostly), she surprised the hell out of me by asking “So, James, how’s your summer going?” - then laughing when I answered “Pretty darn good, so far!”
From there, the next several minutes were spent simply talking to each other - her asking me about school and so on, and me answering. The whole time, her vagina continued to twitch around my penis, greatly increasing the time it took for me to soften inside of her. It was probably a good ten minutes before she finally told me “Well, I think it’s time for us to get cleaned up, don’t you?” - and even then, I was still half-hard inside her.
I reluctantly agreed, but brightened considerably when she asked “Of course, you’ll be taking a shower with me, right?”
The prospect of another shower with her perked me right up. Even so, I still had the presence of mind to watch — with Maureen fully aware that I was doing so — as she slowly lifted herself up, letting my penis pull free of her, releasing a small flood of our juices to first drip out onto my pubic thatch, then slowly start trickling down the inside of one of her thighs. Again, the sight of it flipped some switch in my head, and I could feel myself start to get hard again. Maureen just laughed and said, “James, you are never going to have trouble convincing a girl that you think she’s sexy, even after she’s made love with you!”
I felt myself blush a little; Maureen just smiled and took my hand to lead me into her bathroom.
Some time later - after the hot water ran out, in fact - we were dried and dressed, facing each other just inside her front door as we said our goodbyes before I went back home.
The following weekend, I actually got started on the desk and bookshelves for Matt - both because Maureen and I agreed that there had to be some discernible progress on her projects, and (mostly) because Dad came over to do some ‘regular maintenance’ on her car: changing the oil, and a couple of other relatively minor things. Neither one of us was willing to risk doing anything more than do a little groping and fondling when no one was looking.
Dad came up to see what I was doing, and seemed to understand when I told him that I was taking my time on the project so that it would look as good as possible. With it being a ‘built-in’, he understood, and told me to take my time and do it right. What he didn’t know was that I was actually ‘padding’ the job as much as I could, so that I could have ‘lessons’ with Maureen and still work on it enough to make the progress seem reasonable. It was something Maureen and I had worked out to cover the amount of time I spent over at her place, as compared to the visible progress on her projects.
It was another week before there was another chance for Maureen and me to have a ‘lesson’. Once in her bedroom, I had a brief ‘refresher’ on female anatomy (I’d actually had a couple of questions come to mind, and Maureen was more than willing to let me ‘backtrack’ a bit) before the next lesson.
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