My name is Ben. I’m eighteen and I live with my parents in a small house in Mercer County. I guess I’m a typical teen, although my friends say I am a bit geeky and far too shy around girls. I’m tall and slim, have short brown hair and brown eyes and I work hard in college as I aim to go to law school eventually.

Right now classes are out for the summer break and I’ve been doing some odd jobs around the neighbourhood to earn a few bucks over the holiday. Last Thursday afternoon I was in my room when Mom called up.

“Hey Ben, Amy’s on the phone. Could you go round and cut the grass for her? You know that she finds it really hard work since Steve left. She will pay you.”

The chance to gain a few more dollars was too good to miss. “Sure Mom, tell her I will be over in half an hour,” I shouted back.

Amy is Mom’s best friend and they go back to their high school days. Steve is, or I should say was, her husband. He walked out a year ago and we have all been very supportive of Amy since. I should also add that Amy is an extremely attractive woman of around forty and she has been my masturbation fantasy for as long as I can remember. I always get tongue-tied whenever she comes over to see Mom and that’s probably why I've gained this reputation of being shy with girls.

I grab my shades and ask Mom if I can borrow her car to drive over. I could have used my bicycle but it is a warm day and I don’t want to be too worn out before setting to work on the lawn. Mom agrees and, before too long, I have driven along the gated drive to Amy’s pretty two-storey farm house and I am ringing the doorbell.

The door opens. “Oh Ben, there you are. It’s so good of you to come and help me out. Come on in,” says Amy enthusiastically. “Can I get you a coffee or anything before you start?” she asks whilst straightening her skirt.

“No thanks, er, Amy, I’m um, er, good,” I splutter.

My usual inability to speak coherently is exacerbated by the fact that as well as Amy’s skirt being rather short, she is wearing a tight white t-shirt and I can clearly make out the material and pattern of her bra underneath. It could easily have been the same bra that I had unclasped many times in my fantasies. She smiles at me, her blue eyes sparkling and her blonde bob framing her round face. Steve must be crazy to have left such a beautiful and sexy woman, I think.

“I’ve got the mower out ready for you,” she says, and then turns and heads for the back yard.

I follow her through the kitchen and out into the heat of the summer afternoon, trying my best not to look like a little lost puppy. She gives me instructions as to what can be cut and what can be left and it is as much as I can do to concentrate without my mind drifting and my fantasies coming to the fore.

After more than two hours of cutting, trimming, sweeping and collecting, I finish the task in hand. Amy’s yard is not big, but she had put a lot of effort into trying to keep it looking nice and I don’t want to let her down. As I turn to go back inside, I catch a glimpse of her standing at the upstairs window. Idly, I wonder if she has been watching me.

“Amy, hi... I’m all done now,” I call out.

In an instant she reappears at the kitchen doorway. “Ben, you are an angel, thank you so, so much. It looks great; I could never have done all that without your help. Tell your Mom that she has the perfect son.”

Again, I blush. “It’s no problem Amy, really it isn’t. Just let me know when it needs doing again”. This time I actually speak without resorting to gibberish.

Amy comes closer and asks, “Now Ben, would you like a cold drink? I know how warm it is and if you want to take a shower, please feel free. You know where it is, don’t you?”

“A shower sounds like a really good idea,” I say, thanking her and heading up to the bathroom.

Once inside I close the door and peel off my rather damp shirt, jeans and boxers before stepping into the shower. I turn the handle; the streaming water is refreshing and all the sweat and grime is soon washed away. I close my eyes and sexual thoughts begin to run through my brain, carrying me away.

In my fantasy, Amy knocks on the door, but there is no answer. She opens the door slightly and can see me masturbating through the textured glass and quickly shuts the door. She's a little shocked yet knows what I am doing is natural. She even wonders if I might be thinking of her and that makes her blush and gives her a tingling feeling between her legs. She gets undressed, steps into the shower with me and starts to stroke my erection whilst kissing my mouth deeply and whispering softly in my ear. I can feel her breasts sliding against my back...

Suddenly, there is a loud rapping on the door and I snap out of my daydream.

“Ben, are you done? Have you finished showering yet?” Without waiting for my answer, Amy enters the bathroom giving me barely enough time to turn off the shower and wrap a towel around myself.

“Oh, just about done, I see,” she giggles, before handing me a large fresh towel. I see her looking first at my damp tussled hair, then at the water droplets glistening on my chest and then at the erection hidden by my towel. Despite my best efforts, my hardness is refusing to subside.

I smile back sheepishly. Her white tee looks different. No, perhaps not different, it is the same shirt but my eyes are not deceiving me, I can no longer make out the silhouette of her bra underneath and her nipples are straining under the thin fabric. The view is not helping my hard on to subside one bit.

Amy looks at me, grinning. “Ben, aren’t you going to show me what you are trying to hide under that towel? It would be rude not to, you know that,” she teases.

Before I can answer, she takes my hand and leads me out of the bathroom, across the hallway and into her bedroom. She tells me to sit on the bed and she stands in front of me. I can hardly believe what is happening. “There’s no need to be shy Ben,” she says, and starts to pull off her shirt.

Her breasts are revealed to me. They are not small but not too large either, probably a 36C and her dark nipples are erect. “Do you like them Ben?” she asks. “I saw you staring at them when you arrived so I thought you might like a better look. Would you like to touch them? You can, in fact I’d really like you to,” she says, invitingly.

Hesitating only for a moment and with my heart racing, I reach out and cup each milky white mound. They are soft, yet firm in my hand. “That’s it Ben, that feels nice doesn’t it?” she whispers as my fingers brush over her areola. I marvel at the sight of the rose-coloured puckered flesh.

She removes my hand, then reaches around to the base of her back and starts to unzip her dark blue skirt. It falls to the floor and she is standing in nothing but a white lace thong. “Do you like my panties as well as my tits Ben?” 

By now, my erection is straining under the towel and I have been unable to utter a single word in response to her questions, but I manage to splutter, “Yes, I do, very nice”.

Swallowing hard I continue, “Amy, what are you doing? I mean we have known each other for years; you are Mom’s best friend. What if she finds out you have just about undressed in front of me?”

Amy smiles back. “Ben, don’t worry. I want to do this for you. I know that you are shy with girls and never had a girlfriend.” She leans in closer and whispers, “I know that teenage boys masturbate all the time and I bet you think about me sometimes, don’t you?”

I blush beet red.

“See, I knew it and it’s quite okay, it’s very natural,” she says, smiling softly.

Her hand reaches for my towel and I am powerless to stop her. Within a split second she has revealed my erection. My hard, circumcised dick has a bead of pre-cum at the tip. Amy stares, saying, “Mmm, you do have a lovely looking cock, Ben. It’s never been inside a girl has it?”

She doesn’t wait to hear my reply as she knows what the answer. “Why don’t I lay back on the bed and we can change that,” she suggests, slipping off her thong and making herself comfortable with her legs parted. "Yes, Ben, this is for you. You can have my pussy for your first time and then I’ll show you how to make me orgasm,” she purrs.

Still thinking that I am going to wake from a dream any moment, I kneel up between Amy’s open legs. Her pussy is shaven bare and I can see that her labia are swollen and glistening. I am breathing fast and hard and it’s difficult to control my excitement. Amy smiles reassuringly and encourages me to guide my throbbing penis to her waiting pussyhole. The tension and my arousal are almost too much to bear and as soon as my sensitive cockhead touches her pussy lips I feel my orgasm start to boil up.

“Ohhh noooo… not yet… oh fuck, I’m cumming. Amy sorry, here it cums,” I mumble.

“Shh Ben… be quiet, just enjoy it sweetheart,” she says as my cock stiffens more and begins to pulsate, spurting jets of hot creamy cum over her pussy, belly and tits. She wraps her arms and legs around me and pulls me against her naked body, the warm slippery semen coating both our bodies. She kisses me gently.

“Don’t you worry about it,” she whispers in my ear. “Many boys are too excited the first time they have sex and cum like that. It will take the edge off things and, in a few minutes when you have recovered, we will do it again. And next time you will cum inside me.” 

Amy eases me off her body so that I am lying beside her. She takes my hand and plays with the fresh cum over her breasts. She puts my hand down between her legs and with her fingers, guides mine all over her soft, smooth mound, encouraging me to slide one finger into her. As my finger enters, she lets out a soft moan and pushes her hips back against me. Then she tells me to work my finger along her pussy slit so as to discover the sweet sensitive nub that it is her clitoris. I touch it lightly and feel her hips writhe.

“Yes Ben, that’s the right place. Keep doing that darling, same place, same pressure… mmmm… that feels wonderful,” she groans.

I try my best to do as she says and I can feel her pussy getting a lot wetter. As my confidence grows I lean across her naked body and plant a small kiss on each of her breasts. She smiles, so I do it again and then place my mouth over her left nipple, kissing and sucking and licking.

“Oh yes, please, do it Ben, suck harder and bite on them a little… I love that.” 

Her nipples are little rocks in my mouth and, as I do as Amy asks, she squeals in pleasure. Her hips thrust and gyrate and I do my best to keep my finger working on her clit. Suddenly she moans loudly, her hips buck, her back arches and she calls out my name over and over as her orgasm grips her body.

She opens her eyes and looks up at me. I’m biting my lip, but she smiles warmly. “Ben, that was just perfect. Thankyou. I haven’t had a man’s body next to me since Steve left.” 

She reaches down over my torso and wraps a hand around my hardening cock. Expertly she begins to stroke and squeeze my shaft, milking a few drops of precum and using it as lubrication so that her hand slides effortlessly up and down.

When I am fully erect, she straddles me, holds my cock, and positions it at the entrance to her very moist pussy. I watch transfixed as she lowers herself down on to me, feeling my dick penetrate her until I am fully embedded within her welcoming pussy. She begins to rock her hips, encouraging me to thrust and grind back against her. Her full, round breasts are bouncing gently and I am in heaven.

For the first time I am sliding my dick in and out of a woman’s pussy instead of rubbing it in my hand. The excitement of actually fucking the woman who has been the subject of a thousand fantasies is thrilling and I want it to last. I can see my cock, glistening wet, sliding in and out of her and the feeling of her squeezing her vaginal muscles as we fuck makes her pussy feel exquisitely tight.

My breathing become faster and deeper. Amy grinds down hard against me and grips my hand, demanding, “Yes Ben, do it, cum inside me. I want all your sweet jizz inside me. Let it go. Now!”

The pleasure is too much to bear and in a moment I groan loudly and feel my balls draining. Amy’s pussy floods with my cum and for the first time I have spurted inside a woman instead of all over my bedsheets.

After a few moments of reflective silence and warm smiles, Amy extracts herself from my softening cock and stands at the side of the bed. I can see my cum starting to dribble from her freshly fucked pussy. “I think it’s about time we both got ourselves cleaned up, don’t you?” she says and leads me back to the bathroom. “Your Mom will be wondering where you are.”

She turns on the shower and steps inside, pulling me in alongside her. Her warm, shapely, slippery body feels sensual against me as she washes the remaining traces of cum from my cock. She turns the water off and I watch as the rivulets slowly disappear from her inner thighs and the last few water droplets fall from her nipples.

I step out of the shower, no longer shy about my nakedness in the presence of the opposite sex; in fact, it feels natural and liberating. I wait and watch while Amy finds a fresh pair of panties and we both dress, but I notice that she does not bother with her bra.

We return downstairs to the kitchen and she presses two twenty dollar bills into my hand. “That’s for your work getting the lawn cut,” she says, grinning.

She walks me to the front door and stops, turning to face me, placing a soft kiss on my lips. We embrace again, a little deeper this time but, after a few moments, she breaks our kiss and says warmly, “Ben, you had best get home. I hope you enjoyed it as much as I did. Please drive carefully and give my love to your mother. Next time you come over I’ll teach you all about oral sex and how you can pleasure me with your tongue.”

Her eyes shine and she gives me a knowing wink before I walk down the path to my car.

*****

Author’s note. My thanks to Ciara1997 for her help, suggestions, inspiration and feedback regarding this story.