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My First Time, Part I

"A babysitting job is not what I thought it was supposed to be."

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When I was in my early twenties, I worked as a school-age teacher in child care. I dealt with all kinds of parents, including some hot moms. This one mom in particular was especially hot. She was of modest height, a nice tight body with a nice round, fit ass and perfectly sized breasts. She had blonde hair and blue-green eyes. Her name was Tracy and she was in her mid-thirties. She had two daughters, one in her late teens, the other around six. I was under the impression when talking to Tracy that she was attracted to me as well. It left me with such a thrill because I had never had an older woman show any kind of attraction towards me and yet, here she was, looking at me with such an intensity every time we spoke that it made my heart race.

One Thursday afternoon, she asked me if I could come over to babysit that weekend from Friday evening until Sunday afternoon. She would pay me and make it worth my while. There was nothing saying that this couldn't be done so I agreed. She gave me her address and her phone number told me she was looking forward to seeing me then.

Friday evening arrives and I show up at the townhouse where she lives. She greets me at the door and I'm blown away by the tight, form-fitting dress that she's wearing. It has major cleavage and really accentuates her tight ass and only goes down to just above her knees. She welcomes me in and leads me to the living room where she tells me to go ahead and get comfortable while she heads into the kitchen.

"What are your plans with your husband this weekend?" I ask her.

"Oh, he's out of town for the weekend," she replies from the kitchen.

I get a little nervous. "So, you're going away with some friends?"

"No. You're over twenty-one, right?"

"I am."

It dawns on me that I have yet to see Tracy's youngest daughter. When she returns, Tracy brings me a glass of champagne while holding her own. I hesitate as I take it. "To new adventures," she says, clinking our glasses together. She takes a small sip of her champagne while I take a large nervous swig of mine.

We sit down on the couch, me facing nervously ahead while she's turned towards me, one arm draped upon the back of the couch while one leg is bent across the couch. I find myself eyeing her leg that's resting mere inches from me. She starts making chitchat, asking me how I got started with teaching and what it is that's drawn me to working with children. My answers are honest, but short and stiff.

At last, I asked her, "Is your daughter not home?"

Tracy shakes her head. "No. They both have sleepovers for the weekend."

"I thought you said you needed a babysitter for the weekend," I say, following a big gulp.

"I do," says Tracy, her voice taking an alluring tone as she places both our glasses on the coffee table. She scoots closer, her hand touching my shoulder, sending shivers down my spine. "You see, I don't like being home alone and want someone to stay with me this weekend to help take care of me."

I gulp again. Sweat glistens upon my forehead. Her hand moves to the back of my neck, her fingers twirl the hair there. I can feel a bulge rapidly growing within my khaki shorts.

"Do you think you can take care of me?" she asks, moving even closer, her face inches from mine.

"Mrs--"

"Ahh....call me Tracy."

She gently takes my face in her hands, turning me towards her as she plants her large, luscious lips upon mine. She tastes like strawberries. Her tongue moves into my mouth, swirling around as it explores my own, her one hand holds me close while her either drops to my bare knee.

"Mrs....Tracy...." I say as we pause to take a breath. "I think you should know....I'm a virgin."

What I thought would be a turn-off has the opposite effect--her face brightens up, her smile grows even bigger. "Perfect," she says. "Then let me be your teacher."

She kisses me again, this time with even more passion and vigor. She climbs on top of me, straddling me, pulling at my shirt, her hips grinding into my bulge as it presses against her crotch. Even through my shorts, I can feel the warmth of her erogenous zone. I rub my hands across her back, but she takes them and places them firmly on her butt.

“Don’t be shy,” she tells me, “let your hands roam freely to wherever you want. My body is yours.”

I give her ass a good squeeze, drawing a slight squeal from her as we resume kissing. I squeeze again, amazed at the tightness of her ass. Our passion grows, her lifting away my polo shirt to kiss my neck. I quiver and moan. I grab hold of her breasts through her dress, feeling her nipples harden under my touch. I kiss the bare skin just above her cleavage and make my way down.

She laughs. “Now you’re getting the idea!”

As I lick her cleavage, she unzips the back of her dress and lowers it to reveal a beautiful black lace bra. She guides my hands to the back of her bra where she leads me through unclasping it.

“Better learn that one real quick,” she tells me, dropping away her bra to reveal perfect breasts and erect nipples, the first pair of breasts I have ever seen before.

I take them in my hands, squeezing them, flicking the nipples, before I take them in my mouth. I swirl my tongue around her nipples, drawing moans of delight from Tracy. She presses against my bulging manhood, her hips settling into a gentle rocking motion. She pulls my face to her and kisses it deeply before giving me a sly, lustful grin.

Tracy makes her way down my body, kissing every inch of it—my chin, my neck, my neckline, my shoulders, my chest and nipples. She swirls her tongue around my nipples, causing me to quiver and gasp at how good it feels. As she progresses low to my abdomen, she starts undoing my belt and zipper. I tremble as she kisses my belly button while—with one quick and hard tug—she pulls down my shorts and boxers. My hard, throbbing cock springs upward. She grins at the sight of it. She takes hold of my shaft with one hand, stroking it, while cupping my balls with the other, caressing them.

Then, she kisses the tip of my mushroom head. I tremble. Then, she kisses it again, this time dropping her lips a little further down the shaft. Again, I tremble. Then, finally, she takes the whole of my shaft into her mouth, slurping up and down, her tongue running marathons around the entire length of it, teasing the mushroom head. I quake, throwing my head back with a loud moan of delight that fills the room. She continues bobbing her head up and down on my cock, giving me an amazing blowjob that sends my head spinning! Time almost seems to freeze, the moment stretching for an eternity as waves of pleasure flow through me. I can feel myself building, my entire body tensing. Tracy, sensing my impending climax, picks up her pace, increases her suction, trying to draw me out. I grab her head, holding her in place, my fingers burying themselves into her.

And then, with one massive moan, I unleash a massive load down Tracy’s mouth. She keeps sucking, stretching out my pleasure, indulging herself in every last drop of my homemade man cream as it pumps down her throat.

At least, she lifts her head, smiling brightly, not one drop visible anywhere on her lips.

“Holy shit,” I breathe, panting. “Holy fucking shit!”

“You like that?” she asks.

“Holy shit, yes!”

“Good.” She stands up and allows her dress to drop to the floor, revealing matching black lace panties. “You know the great thing about fucking a virgin?”

“What?”

She looks at my cock, still hard as rock, throbbing with anticipation. “You’re immediately ready for more.”

I take in the sight of her body, the curve of her waist, the smoothness of her skin. My eyes linger on her panties, the wet spot on her crotch. She takes my hands, places them upon her hips, guides me through feeling around to her ass. I grab hold of her cheeks and squeeze them tight, pulling her closer to me. She gasps at being manhandled. I kiss along her stomach, my hands moving across her back, her hips, her sides, to her breasts. My lips wander downwards to the top of her panties, using my thumb to edge them down ever so slightly to reveal nothing but bare skin, recently shaved.

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As I kiss the very top of her panty area, I feel her tremble. Her hands grasp my hair as she breathes, “That’s it, just like that.”

I kiss some more, then, using my thumb to lower her panties just a little bit more, lick just beneath her panties. She gasps, her fingers tug at my hair, press me closer. I guide her to the other side of the couch, lay her down across it and promptly remove her panties to remove the beautiful nakedness of her pussy, already wet with anticipation. She stares at me across her beautiful body, her eyes filled with hunger and lust.

She opens her legs, one hanging off the couch as she welcomes me to delight in the feast she has been saving for me. I get down on my knees on the floor at the side of the couch and lean in, my arms wrapped around her upper legs as I hold her close. I can smell the scent of sex permeating from her pussy as I lean in, kissing her thighs, drawing moans of pleasure and excitement from Tracy. Her fingers weave gently through my hair. I drift closer to between her legs, her moans building, her hips lifting off the couch, pressing against my face as she tried to bring her pussy to my lips. I pull back, see the disappointment starting to form on her face, her hips dropping back onto the couch.

Her lips part, ready to give me instruction, but before she can speak, I dive in. I take her clit in my mouth and suck on it. She gasps, bucks her hips against my face, grabs my hair tightly with one hand while the other grabs the side of the couch. I slide my tongue across her pussy lips, tasting her delicious juices as they spill across my mouth, dribble down my chin. I flick my tongue across her clit, causing her moans to grow, her breathing to quicken. Her chest heaves with each motion of my tongue, her pleasure intoxicating to watch. The rising and falling of her glorious breasts, her nipples hard, calls to me. I reach up and grab hold of her breasts, squeeze them, caress them, fondle her nipples.

“Oh god, yes,” she gasps, “yes, yes, YES!!!”

Her cries grow louder as the action of my tongue and the motion of my hands and fingers grows in intensity, her body withering at my touch. Tracy grinds her hips against my face, smearing her juices across my chin which is now dripping with her cum. She grabs my hair with both hands now, pressing me deeper against her pussy. I can feel her pulse through her pussy, feel it throbbing, her cum increasing. She gets louder, her gasps and cries turning into screams.

“Right there, right there,” she shouts, “oh, god you’re gonna make me….CUUUUMMMM!!! I’m cumming!!!”

Her cum splashes across her face as her hips lift off the couch, her legs squeezing the sides of my head. I don’t ease up, continuing to suck and lick her pussy, her breathing stops as her face contorts, her entire body twists, she grabs hold of the couch and releases a massive gasp and sigh as she collapses onto the couch. She breathlessly grasps her chest, a look of pure ecstasy on her face as she comes back down from her incredible high. She opens her eyes and looks at me and smiles.

“Wow, you’re good at that.” She beams. “I didn’t need to teach you that. I haven’t cum that hard in months.”

She sits up and takes hold of my face, covered in cum, and kisses it deeply, passionately. Her tongue swirls through my mouth and across my lips. She leans back and smiles. “I taste good,” she says.

“Yes, you do,” I agree.

She pushes me back onto the other side of the couch, stroking my cock as she brings her body over mine. “Saddle up, you’re about to get the ride of your life.”

My heart is racing, my cock throbbing with anticipation to the point that it hurts as I stare up at this beautiful woman hovering naked over me. Her pussy is open, wet and dripping, hungry for me as she lowers herself towards my cock. She takes hold of my shaft and rubs the tip across her pussy lips, lathering it with her juices. It feels so incredible. My eyes roll into the back of my head as the anticipation builds.

Then a thought occurs. I look at her. "Shouldn't I get a....?"

Tracy shakes her head. "Don't worry, baby. I'm on the pill."

She slides her pussy onto my cock, taking it all the way to the hilt. I moan loudly at how incredible it feels, those pussy lips hugging me, the inside of her pussy warm, wet and welcoming. She trembles as she takes it in, straddling me on the couch. She leans across my body, her breasts hanging right before my face.

She brings her lips close to mine and says, "That means, you can cum inside me as many times as you want."

"Oh, god," I breathe. I take hold of her, passionately and lustfully kissing her lips with mine, running my hands across her back and hips, grabbing hold of her ass.

She begins riding me, her hips rocking gently at first. I feel the inside of her pussy as it moves about my cock with every movement of her body. It feels so amazing! Placing her hands on the arm rest behind him, she lifts herself up and quickens her pace. Her breasts right in front of me, I bury my face in them, slurping across them with my tongue, teasing at her hard nipples. Her moans fill the room, she switches to swirling her hips around my cock. She sits upright and begins bouncing upon my cock, her breasts bouncing gloriously along with her. I grab her ass and hold on tight, spreading her cheeks so that I can feel deeper inside of her. She runs her hands through her hair, across her body, pulling at her own breasts.

"Oh, god, right there," she moans as she starts gyrating rapidly. I grab her breasts and pinch her nipples, sending waves of euphoria through her. "Yes, baby, yes, baby, yes!"

Her legs squeeze my sides, her body trembling. She drops herself upon me, our chests pressed together, her face buried against my neck. Her lips suck on my neck, driving me crazy. I wrap my arms around her and start pounding her, her entire body shaking with each thrust. She screams. I can feel her juices covering my shaft more and more, dripping down my balls. She's so tight, so warm, she feels so incredible!

I hold her tight and lift her up, drawing a squeal of both surprise and delight as I move her across the couch, my cocking staying inside her the whole way as we assume missionary. "Yes, baby," she says, her smile wide, "take me! Use my pussy! I want your cock so badly!"

Now in control, I hold myself up and start pounding her hard, her legs spread wide to welcome me in. The sweat is dripping off of both of us. Her breasts bounce with each thrust. I grab hold of one while holding her hip with the other. I pound harder, harder! She screams, I can see her juices pouring across my cock, feel her pussy convulsing around it.

"Harder, harder!" she screams.

She pulls me in, wraps her arms around me, wraps her legs around my waist, holding me in close. We kiss passionately as our bodies frantically move together, both meeting each other's thrusts. She gets louder and louder. Her lips pull away from mine as she screams louder and louder. With one hard, swift thrust, she lets out one long, loud scream of ecstasy as she climaxes, her pussy throbbing around my cock.

We hold one another, trembling. I look at her, her eyes closed, her breathing heavy as she comes down from her last orgasm. She grasps her chest and smiles at me, her eyes opening. She takes my lips into hers.

"I don't need to teach you anything," she says. She looks down at my cock, still deep inside of her. "You ready for more?"

I nod.

She pushes me off of her, standing me up as she sits. She licks her cum from my cock, cleaning it of every last drop she has covered me in. She stops and stands, her hand still grasping my cock. "Let's take this upstairs."

Leading me by the cock, she takes me to the stairs.

Published 
Written by Tommyman86
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