The Tutor
Copyright© 2003 by Dorsai
Chapter 1
Coming of Age Sex Story: Chapter 1 - 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
I was only six years old when the young couple moved into the house next door. We lived in a small town just outside a military base, and it was clear to everyone that he was a G.I. - even me, because I can remember saluting him whenever I saw him in uniform, and how delighted I was when he saluted back, laughing. I knew his name was Sergeant Mike Gifford, and his wife’s name was Maureen. Next to my mom, she was the most beautiful woman I’d ever seen, with her wavy red hair and light complexion. I remember how Dad laughed and Mom didn’t know what to say when I asked her why Mrs. Gifford was rounder at the top and bottom than she (my mom) was.
A few years went by, and I remember when Maureen went to the hospital, and came home a few days later with a baby boy. Everyone in the neighborhood did what they could to help the couple out; me, I was charged with making sure their grass was mowed every Saturday. Mom took food over, and Dad helped the young man fix his car, along with a few other helping-hand kinds of chores. By that time, I wasn’t saluting him anymore, but he was still friendly and helpful to me - even taking me onto the nearby military base to teach me how to use a gun, with Dad’s permission.
Then, a few months later, he went away and never came back. I heard Mom and Dad talking about some kind of training accident, but really didn’t understand about it - even when I heard on the news a few days later that there was something called a ‘class action lawsuit’ against a company that made helicopters for the military, and how some of the parts they’d used weren’t as good as they were supposed to be. Only later did I learn that she’d gotten a piece of the settlement from that lawsuit - enough to let her buy the house, as opposed to just renting it as they’d started out doing, and giving her enough regular income that she only had to work part-time.
Anyway, after that happened, Mom and Dad made sure that any time Mrs. Gifford needed help with anything, she got it. Sometimes, it was Dad going over to work on her car; other times, Mom would take care of their baby. Me, I was still in charge of making sure the grass in the yard didn’t get too high or helping her carry and move stuff. I didn’t mind doing that for her - she was pretty and nice to me by giving me something to eat and drink after I helped her. Along the way, I kind of ‘adopted’ her young son, Matthew, teaching him the kinds of kid stuff a boy needed to learn - like spitting, making body noises, baseball, and all the rest.
As the next few years went by, and I started to grow up and out (it seemed that I was outgrowing my clothes on a daily basis), I continued to help Mrs. Gifford - or as she asked me to call her, Maureen. In addition to mowing the yard for her, I was also asked to come over and do the odd bit of handyman work: hanging a picture, fixing a leaky pipe, putting up a shelf, and so on. None of it was particularly hard, and Maureen was always willing to act as my ‘go-fer’ and try to help me as much as she could. When I noticed how nice girls were and started going out with them, I used Maureen as a kind of sounding board for questions that I couldn’t ask Mom: trying to find out what the hell girls were thinking —if they even WERE thinking— and so on. Maureen never laughed at me, or made me feel bad; she just tried to answer my questions as best she could, tried to give me advice (which I actually listened to - Maureen did better in that respect than Mom and Dad ever did) every so often, and generally tried to do what she could to keep me ‘in line’ with the girls. Maureen was a confidante that I could say almost anything to - even some of the kinds of stuff that went on between me and the girls I went out with. It was even Maureen that provided me with the first package of condoms that I ever had, telling me “James, I know that things sometimes get kind of ... busy when you go out with a girl. I want you to promise me that any time you and her are going to ... be intimate, you’ll use one of these so that there isn’t any trouble. Will you promise me?”
A promise to Maureen was a serious point of honor with me - she’d never lied to me or misled me, and I was scrupulous about keeping my promises to her. I tried to wriggle out of promising, but she wasn’t having any; I only got the condoms after she had my word of honor that I’d do as she said. You can bet I was damn surprised when the time finally did come that I lost my virginity that I actually remembered my promise to her, and wore one for that special occasion - and every time after that, though I bought my own when the package she’d given me ran out. Despite the bond of trust I had with her, I still wasn’t any too enthusiastic about having her know much or little sexual activity I was engaged in.
After I became sexually active, I finally noticed that Maureen was a pretty darn good-looking woman, even if she WAS in her late twenties: the same wavy dark red hair and the same fair complexion; what I really noticed about her was the fact that she was, as I’d heard my dad say, ‘built like a brick outhouse’: I was approaching six feet, and she only came up to about nipple level on me; but the shape of her was amazingly curvy, and compact at the same time. I doubt she weighed a hundred pounds, but what there was of her was very neatly packaged - trim legs and waist, an ass that simply wouldn’t quit, and a pair of breasts that made her look somewhat buxom. Once I noticed her, it was all I could do to take my eyes off of her anytime she was in sight - she was simply that nice to look at, with a dusting of freckles that started across her nose and cheeks and slowly thinned out as they disappeared into the tops of her blouses.
It was a month into the summer after my sophomore year that the relationship between us changed forever. In some ways, it was for the better; in other ways, not. But it was definitely changed.
It started out easily enough: I was over at her house, in my handyman role. She’d decided that she needed to organize the garage storage; I was there to cut and fit some lumber she’d bought, and turn it into shelving. Matt was off somewhere with his friends; he’d left with his baseball glove, telling Maureen that he’d been home in time for supper.
Talking it over with Maureen, we’d decided that the best bet was to build the shelves from the bottom toward the top - that way, they wouldn’t be too high for her (something she laughingly ‘complained’ about). I’d gotten the first few rows of shelves done, and was up on a stepladder putting in another one when I looked down to see if Maureen had the hardware I needed to make sure it didn’t fall down. Maureen was right there, her self-appointed task being to get me stuff so I didn’t have to keep climbing up and down the ladder, holding the ladder steady, and just being around if I needed any help. Any thoughts of hardware left my mind when I looked down at her and realized that I had a pretty damn good view down the front of the blouse she was wearing: I could readily make out the top halves of her full, creamy breasts; I could see nearly all the way down to her nipples, since it was patently obvious to me that she wasn’t wearing a bra. I could feel myself starting to respond to the view I had, and it took her a couple of times calling my name before I responded. She looked up at me in concern and asked if I was okay. I answered that I’d just gotten distracted for a moment (‘distracted’ was better than admitting I’d been eyeballing her tits), and that I was okay. She didn’t look entirely certain about that, but let it go in favor of lowering her head again.
I saw her start to blush a few moments later, and knew immediately that she’d seen my stiffening dick tenting the front of my jeans shorts - and had probably realized what had gotten me that way. She stammered out that there was something in the house that she had to do, handed me the screws and things that she’d been holding, and all but ran inside. I finished getting the shelf fastened into place, and was standing on the garage floor again when she reappeared about five minutes later, noticeably more calm and relaxed - though a bit flushed.
As we put up the last shelf, I realized that Maureen was standing in almost the perfect place and position for me to be able to keep looking down her blouse. At the same time, I could tell that she was deliberately not looking up at me as she usually did. I started to wonder if she wasn’t giving me a look at her tits on purpose, and not looking up at me so that she wouldn’t embarrass me - looking down at her, I just knew she couldn’t help but see how the front of my shorts was tented out from the view she was giving me. By the time I got the shelf secured, I was seriously confused about the situation.
After I climbed down off the ladder, Maureen asked if I’d like something to eat and drink, just as she usually did. Being a teenage boy - that is, a sneaker-shod appetite - I was more than happy to accept her offer. Together, the two of us put away the tools and leftovers from the shelving project and went into the house. There, I took a seat at the little ‘lunch counter’ between the kitchen and dining area while she went about making me a sandwich, putting it on a plate with some potato chips, and bringing it over to me, along with a soda. As I started to eat, she took a seat on the other side of the counter from me.
We chatted about a couple of other things that she’d wanted to do to the house while I ate. I told her what I thought she would need in the way of materials, and she carefully wrote them down on a small notepad. When I was done with the food, she took the plate and set it next to the sink before coming back to the counter and sitting down again. I watched as she started to speak a couple of times before she stunned me by asking, “James, do you think I’m pretty?”
It took me a couple of seconds before I could answer, “Uh, yeah, I do, Maureen.”
She gave me a strange smile and said, “Even though you’re only sixteen, and I’m nearly thirty?”
“Well, uh, yeah.”
She went on to ask, “Have you looked down my blouse before you were doing it out in the garage today?”
I could only sit there for several long seconds before I felt myself blushing as I answered, “Um, no.”
“Have you been looking at me any other ways? Have you thought about me ... sexually?”
I was getting distinctly uncomfortable about the questions she was asking, but didn’t dare lie to her - she was even better than Mom and Dad about knowing when I was ‘fudging’ things. “I ... Yeah, I have”, I finally admitted.
“Yeah, you have to which? Or both?”
“Both” I grudgingly conceded.
Much to my surprise, she didn’t get upset with me or say anything about telling Mom and Dad what I’d done and said. Instead, she just sat there for a minute or two, looking at me as though she hadn’t really seen me before. After what I’d just said to her, I suppose she figured she hadn’t. Still, I wasn’t anywhere NEAR ready for the next question she had for me: “I expect that you’ve been having sex with some of the girls that you’ve gone out with, haven’t you?”
Again, I knew I couldn’t lie, and quietly answered, “Yeah, some of them.”
“I don’t doubt that you’ve enjoyed it - but do you think they have?”
I could feel myself blushing, but still answered, “I dunno. I guess so.”
She looked at me strangely for a few seconds, then said, “If you ‘dunno’ and ‘guess so’, then I figure that they haven’t, really. What do you think?”
“I guess maybe not as much”, I admitted.
“I guess maybe you’re right”, she said, then added, “What —if anything— do you figure to do about that?”
The questions she was asking were making me very uncomfortable, making it even harder for me to think about what she’d just asked. I finally answered, “I don’t know - it’s not like there’s a course in school about it or anything.”
“Do you want to make the girls feel as good as you do?”
“Uh, well, sure.”
“If you had the chance, would you be willing to have sex with someone else to learn how to make the girls happier? Even if that someone was older than you are, and you would have to let HER be in charge about what you do and how you do it?”
I couldn’t see where any of this was going, but said, “Sure I would. But where am I going to find someone like that?”
Maureen gave me another strange smile, and said, “Right here.”
I still wasn’t getting it, and looked around to see who she could be talking about before asking, “Where?”
She laughed, and said, “Here, James. Sitting right across from you. ME.”
As much as I had thought about Maureen in a physical way, I was still a long way from being able to make the jump from eyeballing her body, and facing the possibility of actually being able to do anything with her. All I could do was stammer out, “How ... why ... what...” as my mental circuit breakers tripped.
She sat there patiently as I tried to stop my mind from going around in circles. When I was finally able to give her my full attention, she told me, “The ‘what’ is that I am going to teach you how to properly have sex —even make love— with your girlfriends. The ‘how’ is that you’re going to come over here every several days to help me with the projects that we were just talking about; they’ll take longer than expected because when you come over here, the two of us will go up to the bedroom, where I will teach you how to please a woman. The ‘why’ is simple: it’s been all too long since I had sex with anyone except myself, and I’m damn well going to correct that little oversight - with your help.”
That comment about having sex with herself rang in my ears, and I couldn’t help asking, “You ... You, uh, touch yourself? Girls do that, too?”
She laughed before answering, “Yes, James, I touch myself. Didn’t you wonder why I was still a little red when I came back out into the garage? When I realized that you had gotten hard - just from looking down my blouse, I figured - it was more than I could stand. I HAD to go into the bathroom and get myself off - it took only a minute when I started thinking about what you might look like. And yes, girls do that, too - maybe even more than guys!”
It was almost more than I could handle: the idea that Maureen not only had sexual desires, AND that girls were able/willing to take care of those desires by themselves. The image of Maureen masturbating in the bathroom had me sprouting a full-blown erection in nothing flat. Then I realized that she was still sitting right there in front of me, and felt my ears getting hot.
She looked at me in curiosity for a moment before she brightened and asked, “You’re hard now, aren’t you? Thinking about me?”
I didn’t trust myself to speak; I could only nod my head just a little bit to confirm what she’d just asked.
To my surprise, she got a pleased look on her face and said, “Good. Because what I want right now, more than anything else in the world, is to have a nice, hard, dick inside me!”
I found myself stunned yet again, not only at the language she’d just used, but by her open admission of her desires.
I was still sitting there, my mind on overload, when she got up and came around to my side of the counter - where she quietly went about the business of taking off the blouse she’d been wearing. I could only sit there as she unbuttoned her blouse to reveal the creamy flesh of her cleavage before opening it completely, exposing herself to me. My body was still frozen in place, but my eyes and mind took over as I looked over the view she was offering me. To this day, I’m still amazed that my first thought was to look to see where the freckles on her faded out under her blouse - and on seeing that they disappeared on the upper slopes of her breasts, found myself with a new task: trying to memorize the wondrous orbs that were her breasts. I’d seen my girlfriends’ tits, of course, but hers were somehow ... different.
She wasn’t much larger than most of the girls that I’d gone out with - it was just that on her petite body, they looked larger. Each was a cone of pale pink flesh, capped with small, dark pink areolas and nipples that looked to be a half-inch long; her areolas were tight and puckered, her nipples visibly erect and hard. I watched her breasts sway slightly as she moved to slip her blouse off and toss it to the side. She continued to stand there in front of me, giving me a full, unimpeded view of the most obvious symbols of her womanhood.
My eyes stayed on her breasts - at least, until I realized that she’d moved her hands to her waist and was unfastening the jeans that she was wearing. My breath caught in my throat when I watched her unfasten, then unzip her jeans and slowly peel them down her legs - underneath, I could see that she had on a pair of small, sheer panties that made it possible for me to make out not only the general size and shape of her pubic hair, but its color, as well: red, just a few shades darker than what was on her head. When she’d kicked her jeans loose of her feet, she stood up again - but only long enough to begin sliding her panties off. I heard myself gasp when her panties dropped below the level of her pelvis, exposing her fully to my gaze.
Under my eyes, I could see that she had a small wedge of curly red hair that extended just barely past her pubic bone, forming a narrow ‘vee’ of somewhat sparse curly red hair. Looking closer, I could make out what I knew must be the edges of her vaginal lips among the curls between her thighs - and felt myself getting even longer and harder in response.
I lost my view of her as she slid her panties past her ankles before kicking them over next to where her jeans were. That done, she stood before me again for a bit, giving me the chance to look at her in all her loveliness. When she was satisfied that I’d had enough of a look, she stepped forward so that she was right in front of me. Without saying a word, she took my hands in hers and moved them to her breasts - which I began squeezing and caressing without further invitation. As I did, she let her eyes close and her head tilt back, moaning softly in the back of her throat. I marveled at the soft/firm texture of her breasts, and how smooth her skin was for a couple of minutes before I got up the nerve to lean forward and take one of her nipples between my lips. When I did, she moaned again, louder, before putting her hands in my hair and guiding my eagerly sucking mouth from one breast to the other, and back again.
It was only a few moments before I could detect the scent of aroused female in the air around us, and it comforted me to know that what I was doing excited her. As I continued nursing at each of her breasts, the aroma of her became stronger and stronger, until she finally all but pushed my head back and said, “That feels good, James. But I want - no, need - more. Stand up.”
I did as she asked, and wasn’t surprised in the slightest when she latched onto the waistband of my pants, fighting to get them undone. I was more than ready, and as she unzipped me and slid my jeans, shorts, and underwear down my legs, I pulled my T-shirt off, leaving me standing there as naked as she was, my erect penis pointed toward the ceiling. When she saw it, Maureen paused only a moment, saying, “Dear god, how I need that!” as she finished sliding my clothes down around my ankles. After I’d stepped out of them, Maureen dropped to her knees in front of me and did something that I’d never been able to get any of my girlfriends to do: take my penis in her mouth and begin sucking on it.
Much to my dismay, she didn’t keep it up for long; stopping when she’d left it with a coating of her saliva. Taking my hips in her hands, she knee-walked backwards a little bit as she guided me to my own knees in front of her. Looking up into my face, she said, “This time, James, I just want you to fuck me - just stick it in me and have at it!”
By that point, I was too engrossed in the idea of doing just as she said to give any thought to the language she was using. She sat back on her heels, and then moved to lie on her back. Raising her knees, she went on to spread her legs, opening herself to me in clear invitation. Without hesitation, I leaned forward and positioned myself between her parted thighs; a moment’s adjustment and I could feel the head of my penis pressing against her wet opening. She was much shorter than I was: on top of her that way, I all but covered her body with mine; the top of her head just reached my chin.
She reached down to take my hips in her hands and pulled on them, letting me know that she wanted me inside her right now. I pressed forward with my hips, and felt myself begin to slip into her - but she was incredibly tight inside, and I barely managed to get the head of my penis past her entrance, accompanied by a soft groan of pleasure from her. I eased back a little bit, and pushed forward again, harder - and felt nearly half my erection slide into her as she groaned again, even louder. I backed out a little and thrust in again; stopping only when I felt her pubic hair brushing against mine.
I could barely believe how incredibly hot and wet she was inside - and she was even tighter around me than any of the girls I’d had sex with before. I paused a few moments to savor the sensation of having her wrapped around me that way; my reverie was interrupted by the feeling of her hunching her hips up at me, trying to get me moving inside her. That was all the reminder I needed to start doing that very thing.