The MILF Chronicles
The Pool Boy
Evan and my son left a week or so later. I never let my composure down around Evan and never repeated my daring fun. Even watched me with hungry eyes the whole time and always seemed disappointed when I gave him no more attention.
After they left the house got very quiet again, and I was left with my thoughts.
It still excited me to think that young men would find me attractive enough to want to have sex with me. After all, I was well into my 40’s.
One morning after my shower, I stood naked in front of my mirror and appraised myself. I had to admit that I had some nice tits. Not huge, 34 D that still had nipples that at least pointed straight out instead of at the floor. I ran my hands over them and gave them an exploratory squeeze. Firm, but nice and squishy. My half dollar sized areola immediately flushed deep pink and my nipple rose. I gave it a gentle pinch and continued sliding my hand down my body.
My stomach was flat. All of the running and planking I had been doing had taken the softness I once had. It was taut and smooth.
I turned and appraised my ass. Not bad. Not as tight and high as a 20 year old, but not bad for 40 something.
Turning back, I faced the floor length mirror face on. My gaze fell on the last uninspected area, my pussy. Honestly, my bush was something of an untended garden. With no prospect of regular sex, I had let it get a bit wild. I couldn’t even remember the last time I had trimmed it, let alone done some serious work on it.
I wondered. What is the style for a MILF? Wild and woolly, or trimmed and tight? I figured fully shaved was out of the question because that “little girl” look didn’t go with the whole “Mom” image. I was definitely going to have to work on that.
I turned to my dresser and found my hand mirror, comb and scissors. Going into the bathroom, I used the mirror to survey myself a bit closer. Hidden in the dense bush, I could see the line of my labia, the outer lips tightly closed. Although the bush was a bit wild, I wasn’t all that hairy outside of that, so I fluffed my hair and using the comb as a guide, I snipped merrily away, watching my ginger curls falling on the floor.
I checked my work with the mirror again. Not bad, but a few more snips and my labia were covered with only a light fuzz while my mound was still a bit thicker. The perfect compromise, I thought.
Back to the bedroom mirror and another quick appraisal. Definitely fuckable! I laughed at the thought. As I turned away to get dressed, I heard a noise in the back yard and went to the window to see.
Looking down into the back yard, I could see the pool boy working, servicing the pool. I say pool boy, but he was no boy. A young man of about 20, he was blonde, handsome and shirtless in the sun. His body was ripped and I could see his abs were tight and hard.
Almost unconsciously my hand moved to my breasts, finding my nipple as the fantasy swept over me. What would his rough hands feel like on my soft skin. By this time, my other hand had found their way between my thighs and were stroking my outer lips, coaxing my inner lips and clit to come out to play. Wetness was already gathering as I slid my fingers along my slit. My fingers found my clit already swelling and with my juices, I began to roll it between my fingers.
I normally close my eyes while masturbating, indulging in whatever fantasy I was having. But I kept my eyes wide open, staring at him as he went about his work. Here was my fantasy. I imagined his hard body and hard cock on me, in me. With one hand squeezing breasts and nipples and the other working furiously on my pussy, It was not long before I was cumming, hard. A loud moan escaped my lips and I saw him stop and look up at the bedroom window.
I wondered if he could see me through the window sheers and stood there for a minute longer still throbbing. With wobbly knees, I stepped back from the window.
Here was where I was going to test my MILF powers. If this gorgeous young man, who could have any young woman he wanted, lusted after me, I could have any young man I wanted.
Now to lay a plan.
As I only had my pool serviced once a week, it gave me time to consider my strategy.
I wanted to see if I could make him want me, desire me, need me, not just throw myself at him. I wanted him to lust after me until he had to fuck me. Fuck me as though his entire life depended on it. I wanted to own him sexually.
I went shopping for a new swimsuit. After all, the seduction and probably the sex was all going to be centered around the pool. I pondered over whether to choose a bikini or a one piece. I knew that I could carry off either with no problem, but would one look more like I was trying to seduce him? I mean, a thong bikini might be a bit obvious. After looking around, I selected a white, unlined, one piece suit with spaghetti straps, high cut leg openings, and an open back that went down almost to where you could see the cleavage of my ass.
When I got home, I tried it on with a pair of wedge sandals. The suit fitted me perfectly showing off my tits, ass and legs. And yet the suit left something to the imagination. One more test. I stepped into the bathroom, turned the shower on and stepped into the spray. After getting thoroughly wet, I stepped back out, facing the mirror. As I expected, the unlined suit turned almost transparent. I could clearly see my pink areola and hard nipples poking through the thin fabric. Below, there was a hint, more than a hint of my red bush and pouty lips.
So the bait was ready, now to set the trap.
I called the pool service to set a specific time for the pool boy to be there, giving some excuse about scheduling. For the remainder of the summer and fall, I would be scheduled for the last pool on Friday afternoon.
As Friday approached, I began to get nervous. I didn’t want to just throw myself at him, but I wanted him to know that I was available. This was a difficult line to walk. How to seem attainable, without being too easy. I figured a little teasing was the way to go.
On Friday, just before 4 pm when he was expected, I slipped into my new swimsuit and made my way to the pool. Kicking off my sandals and placing my towel on one of the chaise longues, I slipped into the cool water as I heard the truck pull up in front of the house.
I swam a couple of laps and I could hear him coming through the back gate with his equipment. He was as I remembered him: blonde, tan and tight. As he approached the pool, I slowly climbed the steps, dripping with water, effectively naked in my suit. He stopped dead in his tracks. His expression ran through a series of surprise, admiration and hunger before he set his professional face.
I reached over and grabbed the towel from the chaise.
“Oh Hi”, I said, dabbing myself with the towel.
“I was just trying to get a few more laps in before you came to work on the pool. I hope you don’t mind.” I held my hand out.
He hesitated as though his mind were trying to process what to do and he didn’t trust his mouth to say the right thing.
He took my hand in his, shaking it. “Yes Ma’am, er I mean no Ma’am. It’s your pool, I’m just here to service you, um I mean the pool!” He blushed through his tan. “I’m Dave”, he said.
“Liz”, I replied. “Well, I’ll let you get down to business”, I said, flashing him my best smile. I turned and walked to the chaise lounge, bending over to lay the towel out. I knew he was getting the best view of my ass that I could offer. I turned quickly and caught his eyes still on me.
He quickly turned away and began to clean the pool. I lay back in the chaise longue and grabbed the tanning oil. Generously applying it to my skin, I was soon glistening, lying there in my still semi-transparent suit. I watched Dave trying to do his work while slipping furtive glances my way. He was so distracted that he almost fell into the pool and there was no hiding the tightness in his shorts. I laughed to myself. “Hooked”, I thought. Now to reel him in.
I rose from the longue and slipped my sandals on, carelessly flipping the towel across my shoulder as I walked towards the back door. I could feel his eyes on me and could feel the lust radiating from him.
“See you next week”, I said before opening the sliding door and stepping inside the house.
“Oh yes Ma’am”, he said, a bit too eagerly.
The next Friday, I repeated the scene exactly as before. Dave again showed signs of distraction as he tried to do his work. Finally, I called him.
“Dave, can you be a dear and help me with this?”, I said, holding the bottle of oil up. “I just can’t get my back by myself.”
“Um, I’m not sure that would be appropriate”, he said, though he approached the longue where I lay.
“Be a sport”, I said, flipping the bottle towards him and then flipping myself over. I could feel the fabric of the suit slip between my butt cheeks effectively forming a thong and I knew he could see me virtually naked through the still wet suit.
“Um, Ok”, he said, and I could hear him fumbling with the top of the oil container. He poured the oil into his hands and began to move them down and across my shoulder.
“Lower”, I said. More oil and his hand slid down to my lower back, just above the hem of my suit.
“Legs too”. More oil and his hands slid up and down my long legs. I will admit that his touch was getting me excited. Even though I was drying off from being in the pool, the crotch of my suit was still wet.
He finished with my legs and stopped. I could hear his breath, rapid, obviously excited.
“Well,” I said, “you don’t want my ass to burn do you?”
“Um, no Ma’am” he stuttered, pouring more oil on his hands.
I pulled the back of the suit up so that what little fabric was not already wedged between my cheeks slit neatly between, completely uncovering my ass.
His hands were gentle at first, rubbing the oil in, but I could detect the gentlest squeeze as his hands passed over the round globes of my butt. A few minutes later, he stopped.
I turned over, sliding into a sitting position with my knees raised. He was getting a perfect view of my inner thighs and mound as I handed him the towel to wipe his hands.
“Thank you”, I said. “Tell me Dave, do you find me attractive?” By this time the lump in his shorts was very obvious. “Looks like you do”, I said pointing.
He stood staring at me, as though unsure of what to say. He made a move to cover his crotch with his hands.
“That’s OK sweetie”, I said. “It’s a perfectly natural reaction. I bet you would like to fuck me wouldn’t you?”
Dave went completely red in the face, but his eyes were glittering with an unhidden lust. He nodded.
“Oh, you can fuck me”, I said while I reached down, hooked the crotch of my suit with a finger and sliding it to one side, baring my ginger bush and pussy lips. “But first, you have to lick me!’
In all my years of marriage, I had never asked to have my pussy licked. My husband would sometimes do it as if performing a chore that he didn’t really enjoy. But there was a young man standing in front of me, obviously eager to lick my pussy.
“Yes Ma’am!” he said, kneeling beside the lounge. I shifted my hips slightly to one side, dangling one leg off the chair. He immediately thrust his face between my legs, tugging the suit further to the side, and plunged his tongue between the lips of my pussy.
I don’t really know if he was a talented cunnilinguist, but he literally licked me everywhere! Up and down my slit his tongue moved. Circling my clit, poking at my little pee hole and entering my vagina with his tongue. Up, down, in and out, he licked me for all he was worth, not wanting to leave any of my pink untouched. I could feel the heat growing in my loins and when his mouth and tongue reached my clit again, I grabbed his head and said “There!”.
He gently sucked my hard nub between his lips and flicked it with his tongue. It was like lighting a fuse on a skyrocket. I exploded in orgasm while I pushed his head harder into my crotch. I humped against his face as it built to a crescendo and I fell quivering back on the lounge, my eyes closed while the waves of pleasure receded.
When I opened my eyes, Dave was standing next to the lounge looking down at me. I could see the lust written over his face still smeared with my juices. His erection was now an obvious bulge in his shorts, straining against the zipper.
I reached out and grabbed his shorts by the waistband and pulled him closer. I rested my hand on the large lump and said “Let’s see what else you have for me”.
I unbuttoned his shorts, slowly slid the zipper down and pulled his underwear down. His cock literally lept out at me. It was not long, but big around. Thick and girthy, a huge mushroom head at the tip. I circled a hand around it as I pulled his shorts down around his ankles. I could barely get my fingers around his fat cock.
I stroked his penis softly, feeling him thrust forward.
I looked up at him. Matter of factly I said, “I’m going to suck your dick now, but you are not allowed to cum. Do you understand?”
“Yes Ma’am”, he said.
As I approached his cock with my face, I marveled at the power I had over this young man, but I wondered if I could fit this fat cock in my mouth. I licked the head until it swelled beneath my tongue. When it was dripping with my saliva, I opened my mouth wide and slid my lips over it until the mushroom head was inside my mouth. I paused as I heard him take a deep breath. My tongue began to dance around his cock as I slowly slid down his shaft, my mouth opening wider to accommodate him. I felt his glans touch the back of my mouth and stopped again.
His breathing was ragged and I knew what he wanted more than anything at that moment was to spurt his cum in my mouth. I could feel his cock throb and I knew what was next. In a flash, I withdrew my mouth from his cock and grabbed him by the balls, squeezing hard while I also squeezed with my other hand wrapped around the base of his cock.
“I said you are not allowed to cum”, I said sternly while giving his ball sack another hard squeeze.
“I’m sorry”, he said. “It just felt so amazing, all I could think about was cumming”.
“Oh you’ll cum”, I said, “but only when I say”.
Again I worked his cock into my mouth, this time sliding all the way down until my nose was nestled in his pubic hair, the head trying to force its way into my throat. At that point I wanted this thick cock in my pussy more than anything.
His cock came out of my mouth with a pop as I drew back. I stood and pulled the straps off of my shoulders, I slid my suit down my body until I stood naked in front of him.
I took his hands and guided them to my breasts and he began to gently squeeze them.
After a few moments, I pulled him towards the lounge. “Lie down”, I commanded.
He lay back on the lounge, his cock pointed skyward. I straddled the chair, aiming his cock at my pussy. I had never had such a thick cock in me before and I was a bit concerned. butI realized that I was so wet with excitement, anticipation and leftover juices from my orgasm that there should be plenty of lubrication. I placed his fat head at my opening and slid slowly down, stretching my vagina until I was sitting on him, his cock buried in my pussy, my ass resting on his balls.
I began to rock slowly back and forth, relishing the thickness of his cock in me, feeling fuller than I ever had before. I leaned forward and dangled my tits in his face all the while crushing my clit against his hard pubic bone. I slid back and forth, not up and down because I didn’t want this big cock to leave my pussy.
I could feel another orgasm growing inside me and I knew that Dave was on the verge also. I lifted my hips until only the head of his cock remained inside.
“You can cum now”, I said and slammed myself hard down on his cock. His cock bottomed out against my cervix as my clit smashed against him. I began to shudder uncontrollably as my orgasm seized me. My pussy was constricting and squeezing his cock and I could feel it throbbing and spurting his cum in me. I fell against his hard chest as our orgasms began to fade, his arms wrapped around me.
We lay there for a few minutes as his cock deflated slowly inside me. I could feel our commingled juices leaking out of me and puddling around his balls under my butt. I rose off of him and a gush of cum followed his cock, wet and sticky.
I grabbed my suit and the towel, gave myself a quick wipe between my thighs and tossed it at him.
I had cum harder than I ever had and more than that, I felt powerful, in control. This man had done everything I wanted, exactly how I wanted. That feeling was almost as fulfilling as my orgasms.
“Don’t forget to finish the pool”, I said as I turned and walked into the house.