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Everyone in this story is 18 or over.
If you are a guy growing up in perhaps any age, there was always a MILF (or if you are older, a Mrs. Robinson) that you lusted after. Mine was Sharon. I’d huddle away in my room alone and fantasize of her taking me and teaching me but I had no idea how much of my fantasies would someday come true.
She was in her early 40’s but didn’t look it. She was much older than my mom at the time. My mom hadn’t gone through the divorce diet yet so while I still had some fantasies about my mom on occasion, the majority of my time was thinking about next door neighbor Sharon.
She was lean and well proportioned. She had dazzling blue almost grey eyes. She was a bottled blonde that leaned more toward the platinum side rather than the honey side. Her skin was very fair and almost white. She couldn’t stay long in the sun and capturing her in a bathing suit at our pool was a rare treat. Her breasts were on the small side but I imagined grasping and fondling her beautiful B cup breasts almost every night. Her hips were wide and her ass a beautiful heart shape.
I’ll never forget the first time I caught her getting out of our pool in a black one piece swimsuit. I wanted to be the water dripping off her. I am sure I was staring and her heart shaped ass. She was also tall with long legs. She was around 5′ 9″ and I remember her flirting with me when I was finally taller than her.
She always would mention to my mom how handsome I was and would joke that we should date even in front of her then husband. Yes, I fantasized about those dates and how I would make my move. I did what I could though with what I did have. I stared at her body by the pool.
She always looked stunning as her hair and face seemed always to be well done. In the late ’80’s when I knew her, she had a beautiful “feathered” look that was popular longer than it should have been in the Midwest. I would have hung her picture on my wall. She looked like a next door Linda Evans.
Of course, there were celebrities at the time that were younger and hotter than her. But Sharon was the one that swam in our pool and was good friends with my mom. Mom never had an older sister but she may have found one in Sharon. She was the one that would sun with my mom by the pool. She was the one I would stare at when she would get out of the pool with her black one-piece swimsuit clinging to her. It did her no favors, and she hid more than she showed.
I may have been disappointed at first because what you anticipate touching doesn’t exactly match what you imagine seeing in Playboy. Plus, she was easily twice their age.
She was the one who’s lawn I mowed after she divorced her husband. I imagined an entire scene that would repeat as often and if I wanted. I would think this little fantasy of her doing my bidding as I jacked off on my bed. I’d imagine the scenes we would have and how she would show this 18-year-old virgin the ropes of how to be a proper lover.
In return, I’d give her the stamina, the drive, and the hunger that only an 18-year-old young man could give. Deep in my fantasy, I’d cum hard only to squirt my load all over my stomach and chest. Left with wiping up my own cum with a tissue, I had to do something. But I was 18 with no game. I was painfully shy and simply tongue tied.
I had started mowing her lawn in high school for the extra cash. Our house was next door so often I’d do both at the same time. Our lawn was smaller than Sharon’s since we had the pool. There was almost enough room for another house to go on the lot next to hers, but that’s the way the neighborhood was created. Big Midwestern lawns, unlike the newer homes that have smaller lots.
Even on a riding mower, completing mowing her lawn would take time. Then the hard part came when I had to trim and be careful not to run over any flowers. Sharon wouldn’t like that. Their lawn wasn’t exactly landscaped so simply just mowing the grass was good enough.
I knew there would be something different with today’s work though. Turn after turn, I would plan my advance on her. I’d make sure she knows that I wanted her somehow. She was all alone in that big house. She would always flirt with me in front of my parents and say how handsome I had become after graduating high school. It was time to see what she really thought.
After I finished mowing, I would knock on her door and get paid. Sometimes, she would invite me in for lemonade. Today, after finishing I put away my trimmer and mower and walked over to her house to collect. I cleaned up a little bit in our garage sink, but I was still kind of sweaty. But at least my hands and face were sort of clean.
I was determined to make something happen today. This virgin had a plan. The plan was to end my virginity and begin a crash course run by Sharon. I had no idea how right I would be. I had so much to learn.
I knocked on her door and in a short bit she answered. “That’s it. All done,” was all I could manage gaziantep escort before staring at her.
“Oh, goodness, Jason, you caught me just out of the shower,” Sharon said excitedly. She was dressed only in a short white fluffy bathrobe that barely covered her upper legs. There were beads of water still clinging to her legs. It was tied tight up to her neck so I couldn’t see her breasts. Her arms were crossed, and her hair was dry and all up on the top of her head in a clip.
“Please come inside and get something to drink,” she added as she ushered me inside.
We walked through her darkened living room while I followed her, I admired her legs. For a woman in her early 40’s, she never lost the knack for fitness.
She led me to the kitchen and motioned for me to have a seat. Sunlight streamed through her windows as we sat at the small glass breakfast table. She sat down and faced me as I sat. My plans had all but vanished. I was gifted with this vision of a woman in a small white robe barely covering her body. My plans to seduce her were no more likely than her mowing our lawn.
“Ok, here’s the thing,” Sharon began. She looked at the table and played with a matchbook cover. She squirmed on her seat. Her legs parted and through the glass I could look up her leg and almost see her pussy. “I don’t have your money,” she admitted. “I can’t afford to pay you this week. I’m sorry.” She looked down at her hands.
I didn’t know what to say. Without knowing, by not saying anything, I made her uncomfortable and she caught my eye looking at her parted legs. She shut them quickly and tried to pull the short robe down.
“Can we arrange another means of payment for services?” she asked while looking me up and down.
“Yeah,” is all I could muster. The blood was flowing from my brain and down to my cock. I couldn’t think. All I knew is that my fantasies were about to come true or were they?
What is going on?
I couldn’t move but I could feel my cock harden and get uncomfortable in my shorts. I moved myself to arrange free my cock. Again, my silence made her uneasy and afraid of what I might do.
“Let me get you that drink,” Sharon added quickly. She jumped up and pulled her robe down. I watched her flit through the kitchen like a bird to get me a glass of ice water. I was able to see the bottom of her ass cheeks when when she got up. I hungered to shove my hand between her legs and stared at her.
She sat down while noticing my stare and started talking to me. I took the ice water and drank a large drink. The water overflowed a bit around my mouth and dripped down my face and onto my sweaty shirt. She took my other hand.
With her eyes wide and innocent like she almost whispered, “I think there’s lots of things I could do for you in payment. Don’t you think?”
I nodded. Just completely dumbfounded at my luck but I was frozen. What is wrong with me? Make your move, dude! My cock was throbbing hard like it always did in my first period class my senior year. I always struggled with a rock-hard cock every day during that time. It needed to be released.
She continued, “I could suck your cock if you want. Maybe you would like to fondle my breasts. Or maybe you would like to cum on my chest,” she stuck her chest out and emphasized her breasts. “I’d even let you cum in my mouth if you wanted, but only if you don’t think all that is gross. I’m twice your age and old enough to be your mother,” she added with a slight smile.
My mind was racing. I wanted all of her.
But she kept talking, “I’m sorry. You think I’m an old woman who is gross and you prefer someone younger. I bet you already have a girlfriend. I’m sure you make all the girls wet.”
I gave her a puzzled look and she asked with wide eyes, “Wait. Do you even know what wet is?”
I was caught off guard. The Playboys only educated me so far but of course I had never felt a woman’s wet pussy. I was confused.
She stood up. “I get it. You are a virgin. That’s ok, I’d be honored to teach you if it’s ok.” She stood in front of me in her short white robe.
She took my right hand and gently brought it toward her. She put it under her robe and had my fingers and palm cup her pussy. It was shaved bare, and it was warm and soft.
I had dreamed about that. I was sure that she kept it natural but I was thrilled she was shaved. Shaving was kind of new in the Playboy world and I loved it.
She pushed my middle finger between her folds. I felt her wetness engulf my fingers. She led me in rubbing her and guided me to her vagina. I found her opening and pushed my middle finger inside her. It was nothing like I had imagined.
She gasped, closed her eyes, and looked at the ceiling in bliss. I was fingering Sharon’s pussy, I thought. She rode my hand for a little while I marveled at what I was feeling. She didn’t take her robe off so I could only glimpse at her beautiful little mound of a pussy and my palm cupping her. After a short while, she took my hand away while I felt hypnotized. She sat back down.
“Oh, my. My knees are weak. You certainly have the touch,” she said as she sat back and crossed her legs. I was disappointed. I wanted to see her. “Maybe you aren’t interested. You tell me,” she said.
“I want all of you. I want all of you as many times as possible. Every which way. I want you to teach me how to be your lover,” I blurted without thinking.
“Well, then. Let’s get started,” she said with a smirk on her face.
She got back up and took off her robe letting it drop to the floor of the kitchen. Sunlight danced on her legs and hips as it shown through the trees outside. I took her body in and when I thought my lust couldn’t get stronger, I felt it deep inside as she walked over to me.
I stared at her bare body. I got my first look at a real woman in my life. No airbrushes, no posing. Just a natural older beautiful woman. She had wrinkles and stretch marks where she gained and lost weight. She had a little belly from her one and only child over 18 or so years ago. I got up and embraced her.
My hands wrapped around her body, and I felt her for the first time. She was softer than I imagined. I had no idea what age did to a body. My reality was based in fiction of Playboy.
My hands started on her back and made their way up her back and I dared to touch her ass. I grabbed her ass as I kissed her deeply. I tasted her mouth. It tasted sweet but with some alcohol. I felt her ass and it too was softer than I imagined those Playboy bunnies being. Just the same, I could grab her ass and hold her ass in my hands while going back to grab more. She loved being handled roughly and that’s all I knew. Her hands were at the back of my neck and on my shoulders rubbing my muscles.
She whispered, “Grab my ass, pull my cheeks apart, that’s it, baby. Mommy likes.”
“Mommy?” I thought. I didn’t care. I’d call her mommy, auntie, grandma, whatever.
My cock was pressing into her belly. Her belly was also not flat like those models I looked at. She had a pooch of a tummy but she had a waist. Just the same, it felt wonderful pressed against my cock still in my shorts. She pushed me away. She reached for my buckle and undid my belt. With another quick move, she looked at me and undid my shorts. She pulled them down around my ankles. I kicked off my shoes, threw off my socks and threw my shorts across the kitchen. We locked eyes and embraced again. My bare cock was pressed against her belly. Precum oozed out of my cock and onto her stomach.
She smiled and giggled, “You are making a mess on mommy!”
My hands rushed over her body in a fury. I was probably more like a swarm of bees rather than a caring lover, but I would learn. I was almost disappointed that she didn’t look like some Playboy bunny, but that feeling passed instantly as I came to appreciate her body. It was how she felt under my hands that turned me on. She was still a goddess to look at but not “perfect” like women half her age have the luxury of being. She knew how to be sexy.
She pulled on my t-shirt and threw it across the room. At last, my chest was pressed up against her breasts. Her small breasts were smashed into my chest, and I enjoyed their feeling. They weren’t the pert breasts of a twenty something but beautiful older mature breasts. I touched her breast and loved the soft feeling. Not as hard as I thought they would be but soft and comforting. Her long hard nipples still stood straight out and pressed into my chest. I couldn’t wait to take her nipples into my mouth.
My hands were getting braver and were rubbing her thighs. She pushed me away again and looked down at my cock. My rock-hard cock was facing up at her. She gazed at it. It throbbed in the dappled sunlight from the windows. She looked up at me with her blue gray eyes and then down at my cock. She dropped to her knees.
I had never had a blowjob. Most of my experience was cumming into a paper towel on my bed or toilet paper while in the bathroom. I was an only child so getting time alone wasn’t too hard. I usually jacked off twice a day. But when I was bored or just plain horny from seeing Sharon in the pool, I could easily jack off four times a day or more. I finally had an outlet for that lust and rock-hard cock.
I was getting ahead of myself. I didn’t want this to end. I wanted Sharon in the morning and at night. How could I make that happen. Ideas swirled in my head as Sharon got on her knees and took my cock in her right hand.
“Time for mommy to take care of her big boy,” she said with a grin.
She put my cock in her mouth. The head of my cock touched her tongue as she lightly swirled around my head. Her lips wrapped around my shaft. She pulled me inside her mouth. Slowly my cock entered her throat. I started fucking her mouth. I swore that I was in love and I wanted to marry her then and there. Whatever this goddess needed, I would provide. This can never end.
“Oh, Sharon, I want you so bad,” I managed to grunt.
She took my cock out of her mouth and with her left hand squeezing my cock, she said, “Call me mommy,”. Confused. I hesitated. She grabbed my balls. Tenderly at first and I enjoyed the feeling. Then she squeezed them slightly to get my attention.
She looking up at me and said sternly, “Call – me – mommy.” I felt like I was being scolded like a child and that’s exactly what was happening.
“Yes mommy. I love when mommy sucks my cock,” I said. Where did that come from? It’s amazing how the brain figures out things faster than we can think sometimes. The blood may all be in my cock but some part of my brain was working that day. “I can’t wait to suck on mommy’s titties,” I added. I wasn’t lying.
Between slurps of my cock she said, “Mommy can’t wait to nurse you. And call them breasts, please. I can’t wait until you can suckle them too.” She was stroking my balls with her right hand and her left held my cock.
“I love my mommy’s breasts,” I said looking down at her blonde hair. My hand stroked her head.
“Tell mommy when you are going to cum. That’s a good boy,” she said as her mouth again engulfed my cock and swallowed it down.
I really don’t know how I lasted more than 4 seconds inside her mouth. I guess it was the instruction of her wanting to be called mommy. Also, I didn’t know it yet, but she was hinting at adult nursing which I had no clue about. I’d come to enjoy and love that routine later. But today, I was about to lose my virginity.
I felt that wave of the point of no return coming and remembered that she wanted me to tell her when I was about to blow my load. I was surprised I lasted as long as I did. She took me deep down her throat and traded off swirling the head of my cock with her tongue.
I grunted, “Mommy, I’m going to cum.”
I heard her shift her body as she got ready. I expected her to pull my cock out and jack me off or leave me to fend for myself, but she kept letting me fuck her face. I was about to cum in her mouth. I felt the first load of cum flow out of my cock and into the back of her mouth.
An orgasm radiated throughout my body as I filled her mouth with my hot white cum. A spasm took over my cock as I pushed cum inside with every spasm. I felt like it wasn’t going to stop. I felt the second load almost as big as the first but she hadn’t swallowed the first. She pulled me out slightly to drain my cock of cum. Her lips and tongue working my cock to pull out all of my cum. I felt a third and fourth spurt of cum from my cock. I felt her swallow. She didn’t choke or gag. She simply hummed with delight as the cum went down her throat and into her stomach. I loved her humming on my cock as well. It was like watching and hearing some one eat cheesecake the way she loved swallowing my cum.
After swallowing my huge first load, she said, “Such a big load of sweet cum. I’m so proud of you. Such a good boy.”
My cock was back in her mouth and still hard. I could tell that some cum was still yet to be pulled out. My orgasm had subsided, and I couldn’t believe I was still standing. If I were jacking off I would have moved a finger at the base of my shaft and up to the head to push out all the cum. She positioned herself and started slowly sucking and did the same with her tongue. She pulled out a large glop of cum from licking from the base of my shaft.
She took her mouth off of me again. She looked up at me.. She opened her mouth to show me the little pool of cum dancing on her tongue. She looked at me, closed her mouth and swallowed, never breaking eye contact. She gave my cock one more little suck and put her hands on my ass. She felt up my ass and pulled away from my cock. She looked as though she was about to get up.
“Have a seat,” Sharon said. I did what she said. Then she asked, “Will that be ok for payment?”
I caught my breath and admitted, “Yes! That was unbelievable. I never want this to end.” She wiped the sides of her mouth with her hand.
“What is it that you want?” she asked. With the honesty and openness of having just had my cock emptied of a large load of cum, I could only tell the truth.
“I want you again in a few minutes and I want you every day from now on,” I blurted. No imagination in this one. Well, give it time. Maybe someday I’ll write about this. I had just lost my virginity and I was ready to construct a temple in her honor.
She looked at me level eyed straight into my eye and asked, “Are you sure you about this? You can change your mind right now and walk out that door and we can forget about this. But if you stay you will have to do what I say.”
My mind swirling, I talked as fast as I could, “Yes, I want you. I’ll do what you want just don’t let this end.”
“Well then, first we need to have a little talk. But I needed to hear it,” she said almost like making a grocery list.
Like a true submissive, I pledged, “I’ll do anything you ask.”
“Yes, you will, and mommy will teach you,” she replied. I had no idea what I was getting into.
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