Chapter 03 - My Demanding MILF Neighbors
Author's Notes
The plot thickens and our erotic adventures grow.
Sharing our experiences allows readers to
vicariously live our sexual growth and experiences
from young adult to today; including my marriage to Jill, and our marriage to Jana. Highlights of our lifestyle include size queens, big thick cocks, threesomes, moresomes, double-breasted mattress thrashers, large breasts, private sex clubs, and plenty of carnal knowledge!
All characters and partners are at least eighteen years old. Comments are welcome.
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Until college I lived with my parents and my two sisters. We lived in a very promiscuous and engaging neighborhood that vacationed together and held frequent dinner events through the years. At eighteen-years-old I was discovered by two MILF neighbors. From their perspective, I was the TWWF (teenager we will fuck) that they frequently requested my help to do 'chores'.
I carefully and methodically learned how to use my thick strong cock. I got some great teaching and training from two married women and threesomes. They would talk me through and encourage me while I fucked the other. They made sure I understood a potentially jaw and pussy ripping cock could really hurt, and they loved the hurt! My cock was not to punish, but to sooth and satisfy by massaging and touching every imaginal spot inside their pussy: Places most men never reach and some women would discover unexplored sensitive spots deep inside their body. Women that did know about the deep sensations used big black dildos that they lubed up and crammed into their holes.
With me they had a warm pulsing cock with just the right flexibility to handle their movements to wiggle everything into just the 'right spots'. I learned while I am stroking in, they are moving around to take it right where they need it on each stroke. They are not just lying there like some girls 'learned' to do.
Nyla - Sixteen Years Older with Far More Experience
Months before I met Daniella, my first girlfriend, I was coveted by Nyla who lived on the other side of town and was married to my dad's best friend: I was eighteen and she was thirty-four when she wanted to start doing 'chores' together. She was a stunning tall Dutch blond with massive 44EEE/G tits that demanded a great deal of attention. Her cleavage was incredible and I often jerked off to the vision of her at our lake house in a red bikini. I would image her pressing her tits into my face and wrapping her long blond hair around my cock.
I remember my dad always admiring her rack as she walked around, and seeing him adjust his crotch to be more comfortable while around her.
I learned later through pictures on her dresser she was a playmate in the original Chicago Playboy Club. In her bunny outfit, she is appetizing with her tits displayed even bigger pushed up and out - served on a bra platter.
One warm summer morning she called the house and asked if I was available to come over and do a few chores in the yard. "Absolutely, yes!" I was excited to see her big tits. She met me at her front door and I liked the fact she was wearing a thin tank top, no bra, and her tits hypnotically jiggled when she walked.
We went to the backyard and she wanted me to start by raking up some leaves. I was happy to be there and enjoying the scenery up close. After about ten minutes she came out and suggested I take a break and offered me a cool drink. Her tits jiggled toward me and she handed me a tall glass. I took a long sip and started coughing: I thought it was Pepsi, but it was a rum and coke - my first cocktail. She smiled, "You look old enough and I assumed you have had alcohol before. How do you like your first drink with a beautiful woman?"
With a hungry look and in her sexy Dutch accent, "Blake, I notice you are always staring at my 'G girls'. They like the attention and they love to be touched. Do you want to see them and touch them?" She took my glass, put her arms around my neck for full access to her breasts, started aggressively kissing me and pulled my hands to her breasts. It was a lot to take in - her tongue probing my mouth and the heat of her big tits and hard nipple in my hands. I thought I was dreaming and kept aggressively fondling her 'G girls'.
I realized what my chore for the day was when she went for the waist band of my jams—I shuddered and erupted in my jams and stood there mortified. "Very impressive load. It's my fault; I have that effect on men. Let me get you a towel and a pair of my husband's shorts. I will be right back."
As promised, she returned and we sat for a few minutes in silence and drank our cocktails. Then she moved in front of me and pulled her tank top off over her head. "Blake, you naughty boy. See what you did, you made my tank top fall off and made my nipples swell to hard grape-size niblets. Come over here and fondle, kiss, and suck them." Hell yea! I remember how she squirmed when I pinched her straining nipples. It was the first time I had felt a tit and the amazing reaction of a stimulated horny woman.
She moaned and my cock instantly grew up and out of the top of my jams. "How beautiful the head of your cock looks sneaking out of your shorts. It appears to be happy to see me." rubbing the head of my straining cock. She gasped when she pulled down the shorts: I thought I had done something wrong like hurt her niblets. She wrapped both fists around my shaft and gave it one strong squeeze and stroke and I shot a rope of cum about four feet high onto her arm and the patio deck. The sensation was amazing!
She bent down to put the head of my leaking cock in her mouth. "Very impressive, I want more. Let momma clean the sweet cum off my boy's huge cock. Let's get your next load where momma likes to have it on her chest for great protein moisturizer. Put your cock between my big warm tits and let momma give you a nice titty-fuck." What an amazing sensation of the heat of her big tits, her hot mouth, and strong tongue licking my cockhead as she grabbed my ass to pull me in. It was a memorable day of firsts!
I will never forget the feeling of a stranger's fist wrapped around my shaft strongly stroking me, sucking on the sensitive head, and fondling my tight balls. Within minutes, I was again engorged and anxious, and she was able to have we last for a few minutes and gulp and swallow my next load.
With a naughty hungry smile, she laid back on the lounge and spread her strong legs wide. "Now you are ready to feel my MILF pussy and fuck me. You need to take it slow; your cock is very thick and my pussy is very tight". And fuck her I did—I forgot the slow part! This was my first pussy and I was amazed how much better it felt than my fist. I never got it more than half way in on any stroke and only lasted about twenty strokes before I came again. I had no idea how incredible a feeling it was to shoot a load into a hot wet oven.
I thought I was hurting her from her moans and facial wincing, but she kept pulling my hips into her for more. I was going strong on top of her and easily could cum on any stroke with this sexy tall woman taking me like a champ. I asked her why she hadn't cum yet and she said, "My husband only lets me cum after he does!" I said, "Forget that, I want to feel how your body reacts to my stroking. I am not your husband and you should cum anytime." With that, she released and flooded the patio chase with her cum.
I learned some great lessons from her and she experienced all of me for the four years we were together. I gave her huge ropes of endless fresh cum that she had never experienced with her husband nor her past partners.
That first day, I got stronger with each stroke and like an animal I reacted to the feeling of her strong pussy gripping me tighter as she repeatedly peaked with her loud tremors. No way she wanted more, but she did. She got on top of me for two orgasms by me and one long exhaustive orgasm for her. She rolled off and collapsed to my side. She thanked me, wrapped her arms around me, kissed me very lovingly, and fell asleep with my warm cum-covered cock against her stomach.
I was unaware that the thickness of my cock caused extreme stretching of her mouth and vagina; and required practice, patience, and lust to adapt. That made me curious as to how a baby could pass through it - I learned more about that in my Health class the next quarter.
It was near dinner time and we were awakened by her phone ringing. It was my mom calling to see if I was coming home for dinner. "Yes, Blake is on his way, he just finished trimming my bushes." She hung up with a smile, "I will let you go home to dinner when I am finished with you!" She mounted me again for another shared orgasm that flooded the lounge.
I dressed, pinched myself, and realized dreams could come true. With a sly knowing smirk and a tender kiss, she opened the front door, "We will do this every Saturday if you want. Say 'hi' to your folks and have a nice dinner." Starting that night, I jerked off twice in bed with a visualization of her to build up my stamina for 'next time'. My endurance training worked as I performed non-stop for a string of 'Saturday chores' for Nyla.