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Babysitting For A MILF, How A Young Lad Learns So Many Lessons, And Answers To His Questions

"The story of a young lad who babysits for a MILF, She gives him so much more than he ever hoped for."

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Author's Notes

"This is a MILF story, from the viewpoint of the young man who has been babysitting for her. He is obsessed and after a brief sexual moment earlier awaits her return with so many questions in his mind. Maggie has decided that having been let down recently by men she is going to show her babysitter the time of his young life. He learns and experiences an evening of true passion and embarks on a sexual adventure."

Maggie arrived home just a little after ten thirty, the earliest since I had been babysitting. She went through her usual checks before returning to the lounge. I was still sitting on the sofa when she spoke.

“You said you don’t have a girlfriend?”

“No.” I went to say more, but Maggie raised one hand.

“And your sister has not told you anything about me?”

“No.” I left it at that.

“Can you keep a secret as well as your sister does?”

“Yes, yes, I can keep a secret.”

“Have you ever had a proper girlfriend?”

I shook my head, feeling ashamed at my complete lack of experience.

Maggie stood before me, and I found myself staring at her body wrapped so tightly in a black leotard. She put out a hand to stop me from standing up and knelt on the sofa facing me, straddling my legs. Her skirt covered her legs and mine as she shuffled closer and placed my trembling hands on her waist. She leaned forward and kissed me differently than before; I parted my lips when I felt her tongue pressing. I was on a crash course in kissing and loving every second of it. I hoped my lack of practice was not too obvious. I also hoped my cock, rock hard in my jeans, was not going to give me away and spoil things.

I slid my hands around Maggie, and she shuffled even closer to me. I moved my hands up her back like I had seen in movies. Maggie broke the kiss and leaned back a little, sitting on my legs with her hands still cupping my face as she smiled down at me.

“Do you think it is time we let him out to play?” She said as her hands dropped into my lap.

For a second, I was not sure what she meant until I felt her squeeze my cock through my jeans. Though I desperately wanted to go further, I had no idea what to say. I managed to nod as deft fingers swiftly unbuttoned and unzipped my jeans and pulled my aching cock free. Her warm hands wrapped around it, and those first few strokes were completely heavenly.

“It looks like someone is pleased to see me,” Maggie said as she smeared precum over the head of my cock.

I was unable to move or speak; it felt like a dream, but so much better than the dreams I had been having of her lately. In my dreams we are close, and I’m so happy, but nothing actually happens—probably because I have no experience to add to my dreams.

Maggie lifted one hand to her lips and licked my shiny precum from her fingers. She was looking intently at me the whole time; I was staring open-mouthed, trying to memorise every second. She lifted herself slightly, and I feared the whole experience was about to end. She untied something at the edge of her skirt, unwound it from her waist, and dropped it onto the seat beside me. I looked down to see what she was doing and stared at the leotard, stretched tight across where I knew her vagina would be.

Maggie tensed her legs and moved forward again. I saw her leg muscles tight against the leotard, flexing the material. My cock was as hard as I had ever known it; I could see Maggie's hands wrapped around it again, stroking slowly. I watched her pull my cock down and point it towards her... Vagina, Minge, Pussy—what should I call it? There was no more than two inches between that strip of material and my cock. I knew I would cum very soon. I was trembling all over. I wanted to move my hands and feel her breasts; I wanted to touch and feel her everywhere, but I did not dare break the magical spell I was caught up in.

“You are shaking. Are you sure you are OK?”

“I’m, yes. I’m going to…” I closed my eyes in embarrassment; I did not have the words to tell her how I felt.

I felt Maggie lift up and was no longer sitting on my legs; I knew I had blown it. I opened my eyes, preparing to make my excuses and run away, only to realise Maggie still had hold of my cock. I watched in utter amazement as she leaned forward and then kissed the tip. I made a noise but could not form a word. Seconds later, Maggie began to slowly slide her mouth down the full length of me. The feeling was indescribable, warm, and wet, enveloping my whole cock in a way I had never known. She moved slowly up and down; the feelings were too intense to even watch. My head rolled back while fireworks exploded in my mind.

“I’m, I’m… Aaahhhhh.” I tried to speak before I felt cum rush through my cock and pump, seemingly endlessly, into Maggie’s warm mouth. I knew it was going to get me in trouble, but that feeling and release were the best thing I had ever, ever known.

Maggie did not move for a while until she released my still-hard cock and sat back on her heels. She was smiling, beaming at me. I saw her swallow, and then she spoke.

“That’s one you owe me.”

I had no idea what she meant and would have given her anything at that moment. I’d just experienced my first blowjob; it had lasted less than ten seconds, but it had happened. Maggie stood up and peeled the leotard off of her shoulders. The material clung to her like a second skin. She knelt astride my legs as before and slid towards me. I put my hands back on her waist. Maggie held my cock and slid closer until my cock was touching and then pressing against the material covering her fanny. She rocked her pelvis to and fro, pressing herself against my cock. I could see the material becoming wet and shiny with my precum.

“Are you just going to look, or are you going to do something?”

I wanted to do everything, but other than knowing I would die to put my cock inside her, I did not know what ‘everything’ was. I looked up, and she kissed me more passionately than before. I felt her tongue exploring my mouth and did my best to mimic what she was doing. She leaned back, breaking the kiss and smiling. I was sure I was in love with Maggie.

“I don’t know how; I mean, I have never, you know, done it.” I felt my face go crimson and felt helpless confessing my complete lack of experience.

“I thought so; are you sure you want this?”

I nodded eagerly, “Yes, yes definitely. I’m, I’m ready. I’ll do anything you want, anything.” I threw myself on her mercy and hoped I had not blown everything by confessing. I held back from saying I was in love with her. Maggie gave me one last kiss before she moved away and stood in front of me. Her leotard was still covering her breasts; the material covering her pussy was shiny and wet. She began to sway and move; her body was so flexible, much more than mine. She peeled the material down, tantalisingly close to exposing her nipples, and turned away. She gyrated her hips and pulled the material lower, down to her waist.

I sat frozen on the sofa; I did not think she meant me to join her. I was mesmerised by the display in front of me. She turned to face me, one hand across her chest, the other sliding up and down her lithe body. Her fingers traced the edges of her leotard around her pussy; she smiled at me the whole time. This was the first and most erotic strip tease I had ever seen and would ever see. She rubbed her nipples as she exposed them; they were pink and standing out a little. The hand that had been outside now slipped down inside the tight material. I watched the outline of her fingers covering her pussy.

Maggie stepped close and traced the fingers that had been inside her leotard across my lips. I inhaled that same scent that had driven me wild before on her panties. Maggie pressed two fingers between my lips, and I tasted her for the first time. I was in danger of cumming and realised I had been stroking my cock. I stopped and concentrated on sucking the fingers. I watched her other hand delve under the material, much deeper than before, her fingers moving quickly. It looked like her nipples were growing; I thought I was imagining it. Maggie swapped the fingers in my mouth with the ones I had just watched touching her pussy. They were wetter this time and delicious; I sucked them clean, savouring the taste.

Stepping back again, Maggie slowly teased the material down past her hips. I stared at every freshly revealed inch of her amazing body, eagerly anticipating a glimpse of pubes. The material inched lower, a hypnotic experience that I wished could last forever. The crease at the top of her legs appeared, and then the material dropped to the floor. Maggie was totally bald and smooth, with no trace of any hair at all down there. I stared open-mouthed as Maggie slid a finger up and down her narrow pussy opening and then pushed it up inside. She slowly withdrew her shiny finger and offered it to me. I opened my willing mouth and tasted her again; I was already addicted and craving her.

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“You like that taste?” It was as much a statement as a question the way she said it.

I nodded as she withdrew her finger from my mouth.

“Good, you had better get out of those clothes then, if you want some more.”

I was up off the sofa in a heartbeat, yanking my clothes over my head and dropping my jeans and pants. Maggie sat on the very edge of the sofa and watched me stripping as fast as I could. With my socks thrown on the pile of clothes, I turned to face her, my cock bobbing in front of me. Maggie laid back and spread her legs, and I stared at her pussy. She instructed me, and I found myself kneeling between her legs, licking and probing with my tongue. I loved the taste and greedily lapped at her. Maggie guided me and taught me where to focus my tongue; she also asked me to insert two fingers into her. I alternated between long, deep licks of her pussy lips and little flicks and sucking her clit. I learnt all the right words from her this evening.

Maggie encouraged me all the time until she held my head close to her and urged me on faster and faster. The taste of her juices changed, and her body began trembling and shaking. I could feel my whole face wet and slippery. The quivering reached a crescendo, and suddenly Maggie pushed me away, still shuddering. I looked up to see her nipples standing much larger than before and Maggie breathing hard. I knelt, staring at her beautiful body until she finally spoke again.

“Thank you; that was not bad for your first time. We're even now.”

I was genuinely so pleased to be thanked and hoped I’d get the chance to do it many more times. Maggie put her arms out to me, beckoning me to her. I shuffled forward on my knees. She reached down and pulled me closer with my cock and held the tip just touching her pussy. She rubbed the head up and down her lips, just inside, parting them as my cock moved up and down. I was staring at her pussy and then her nipples and perfect boobs; they stood up so firmly. I moved my hips and watched an inch of my cock slide so easily inside and back out; the feeling was indescribable. I did it again, slightly deeper this time, and Maggie let go of my cock. The next movement had half of my seven-inch virgin cock inside her; it shone wet as I pulled slowly back.

Maggie wrapped her legs around me and pulled me as close as she could, and I used my arms to hold my weight on the sofa. The feeling of my cock buried inside of Maggie was even better than when she had sucked me so recently. The warmth and all the enveloping wetness were like nothing I had even dreamed of. Maggie began rocking her hips, moving my cock inside her, but not sliding in and out as I had expected having sex would be. My cock was pressed tight against her clit, and then more deeply inside with each rock.

“Rock inside me, like that,” she said.

I tried my best, and as before, she guided and encouraged me. With my arms out straight, I could watch my body grinding against her pubic mound. The feeling in my cock spread through my whole groin and into my spine. I could not stop it from spreading and growing. It was the best orgasm I had ever experienced; it built slowly and hit so hard. I could feel cum jetting out of me, into Maggie, so much cum. I had sudden fears she would be pregnant, but they did not stop me from holding myself deep inside. I backed away, but Maggie wrapped her legs around me, keeping me inside.

“I hope you are not done already. That’s another one you owe me.”

Maggie put her arms around my body and pulled me close. I could feel her hard nipples pressing into my chest. I wished I had eight arms and hands to be able to touch and feel her everywhere. My cock was still inside Maggie's tight and wet pussy; I could feel muscles rippling along my cock, nursing it back to fully hard already. Maggie encouraged me to nibble her ear and kiss her neck; she was teaching me things the whole time, and I was an eager student. I began to grind myself tight against her clit, urged on and directed by Maggie, who gripped my bum with her hands. I got into a rhythm, safe in the knowledge I would not cum so quickly a third time.

Maggie became quite vocal, urging me on—faster, faster, harder. I was worried she might wake the kids; I was always so careful not to disturb. She unwound her legs and spread them wide on the sofa; there was no danger of me trying to move away now. I felt her fingers digging into me as she pulled me ever closer to her. Her body started to quiver and twitch like before. I wanted to look down, but we were entwined so closely. Maggie drove me on while her body trembled and shuddered continually. Finally, with a shriek and some almost violent spasms, Maggie begged me to stop. I could feel my cock being squeezed and gripped so tightly, tight like a hand but all inside of her pussy.

We lay still for a while, Maggie catching her breath and my heart banging in my chest.

“That was just what I needed,” she said softly to me.

I was so proud of my amateur efforts. So proud that this beautiful, sexy woman had allowed me to do these things. Maggie freed her arms and twisted her body; she told me to hold on and roll with her. Moments later, with my cock still tightly inside her, I was lying on my back. Maggie was so flexible she was able to gather her legs up and kneel astride me. I looked up and drank in the sight of her perfectly lithe and muscly body. Her nipples were pointing up and enlarged, and her breasts stood proud with no sagging at all. Her hair was loose, and falling around her shoulders, I was definitely, completely in love.

Maggie began to rock forwards and backwards on my cock again. The feeling was more intense than before, plus now I could watch her body all the time. I reached out to hold a breast in each hand—another first for me. I gently squeezed and weighed her breasts in my hands, marvelling at their firmness and softness at the same time. I rolled her nipples, often guided by Maggie. I was learning fast. Maggie stopped rocking and began to rise and fall on my cock, lifting nearly clear and then slamming back down. I watched her pussy release and swallow my shining member over and over.

I could feel the urge to cum building inside me, and I started to raise my hips to meet her thrusts. Maggie held her pussy still just a few inches above me, and I took over the fucking. God, yes, I was fucking her. I bucked and pounded my cock faster and faster. I watched Maggie's fingers almost in a blur rubbing her clit so hard. Maggie was urging me on again, louder and more urgent than before. Her skin was becoming patchy, covered in goosebumps. Her nipples were hard and swollen under my fingers. Suddenly I felt her pussy contracting and squeezing me, and she ground down hard onto me. Maggie was quivering again, and I knew now this was how she orgasmed; her pussy milked my cock, and I felt my cum jetting for the third time this evening.

I lay exhausted, and Maggie slumped forward, kissing me deeply. We did not move for a while, and I was thrilled to be so close to her. Eventually, Maggie moved, and my softening cock slipped out of her. She sat forward onto my stomach, and I watched a flood of cum puddle on my body. I knew I would have greedily licked her pussy again had she asked or offered it to me.

“Wait there,” Maggie said as she went to get a flannel and towel to clean me up.

“I would offer to shower you, but it is late.”

I looked at the clock to see it was already past midnight. I reluctantly dressed and made my way to the back door to leave. Maggie followed me and wrapped her arms around my neck as she kissed me; she was still naked.

“See you next Saturday,” she called as she closed the door behind me.

I felt like I floated home; I was in love and could not have been happier. I did not have a fiver today but had something much more precious. I’d lost my virginity, had a blowjob, kissed and touched breasts. I’d given a woman three orgasms, and she has said she wanted to see me again. The world was a far happier place than it had ever been for me.

I never told any of my friends about my time with Maggie. It seemed like a private thing between us and not something to boast about.

 

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Written by john456berry
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