Spying on Anthony's Mom was HotbyJRob©
My friend Melissa gave me the idea for this story from a story her friend Bill told her about his younger years. Enjoy.
It has been said that some of the best things we learn are the situations that occur by accident.
Oh, there is book learning and a wealth of other places to get to know about this or that. For me, a great learning experience late in my teenage years was totally by chance.
But I am getting a little ahead of myself.
A bookworm in high school, I got strong grades and easily earned a scholarship into State U. Yet as strong as I was with the books, I was equally the opposite with the girls. I only had several "real" dates in high school, only one that lasted more than a couple dates.
My best friend Anthony was equally inept with them women, and each of us struggled to get dates for the senior prom. Point is that when you spent all your time at the library or studying at home, you don't have a lot of time to blissfully interact with the other sex in anything other than a classroom environment.
That didn't mean I didn't have a favorite girl. Oh, there were some movie and television female leads that I liked, but the one woman I was in lust with was Anthony's mother, Mrs. Easterly. Oh, I would call her Carol, but, well I mean she was Mrs. E to me.
She was a real estate agent and worked out of the home when not at the office or showing a house. Always dressed to perfection, prim and proper, the woman didn't have to dress provocatively to get my juices flowing. I mean, well, I admit, more than once I'd fantasized about being with her sexually, sending my man sauce into a sock thinking about her fantastic ass and especially her long legs.
Mrs. E. had a way of looking sexy while still in what others would call work clothing. But it was on weekends when she's sun in her bikini that I'd spy and soak in the look. I think a couple times she caught a glimpse of me, why once I swear she covered a smile after catching me looking.
Couldn't help myself because the view, especially when she was wearing a business suit, was awesome. She wore it so well, tight but not too tight, lots of leg but not too much leg. She must have known I was spying on her when she wasn't looking, but she never said a word.
Maybe she was embarrassed, but she didn't cover up when sunbathing. I mean, she was in a bikini not naked. And heck, she was fully clothed in a business suit yet I was entranced. But in my fantasies I'd do all kinds of things to her sexy 39-year-old body that was sans clothing.
It helped that, looking back, Anthony's mom would flirt a little with me when I'd visit. Oh, nothing terribly overt, but little things. I think she knew when I was following her around the room with my eyes, and deliberately drop something so I'd get a view of her behind. And every once in a while there's be a little innuendo, like when she asked if girls thought I was big enough.
I thought in the equipment department, but of course she meant tall enough, right?
Once I mentioned to Anthony that his mother was a hot MILF and we almost got into a fight. Never again did that happen, as I am not stupid!
Clearly I was lustful with his mom, but that didn't mean I acted crazy when over their house. She was always nice to me, smiling, and Anthony didn't have to know my lust.
Which brings me to our attic, a small area where my parents stored odds and ends at the top of our house. By accident one day I looked toward out neighbor's house, the one on the side away from Anthony's house, and my eyes nearly popped out.
On the floor below, in her bedroom, but my neighbor's 18-year-old daughter....she was walking between the bathroom and her bedroom in her underwear. Hip hugging panties and a bra never looked so good, and that night I had a new naughty fantasy. I sleuthed up to the attic every day after school and caught Michelle several times in various stages of undress.
Accidental voyeur would have become my job title if anyone knew, or pervert. But that little knowledge --- seeing into my neighbor's hallway --- was quite exciting. It sure gave me a different view of the young girl!
I stacked some boxes so it would be hard to be seen if my accident Michelle looked up. It was a secure, secluded spot, and my mind wandered. I moved back toward the other wall, sat in a beanbag chair, and began stroking myself thinking of the next-door girl.
Looking to the side, toward Anthony's parents home, I almost choked.
The dream mom from next door was home from work and undressing. I've never been to a strip club, but this show had to be a heck of a lot better. She removed her blouse, displaying a white bra that fit perfect.... until it was removed. Bare were her bountiful sweet breasts, on display for me.
She sat on the bed, and had already removed her pumps. Off came her skirt, and soon her pantyhose as well. She then walked to another room in only her blue panties and my dick wanted to chase her.
When she came back into the room she was wearing a flowing white robe, hair in a towel, and she sat at a table and began to do her nails. I couldn't help imagine myself in the room with her.... she wouldn't be doing her nails.
It was like watching a movie, and I couldn't take my eyes away from her. Once I though she might have looked into the mirror and seen me, but other than a little bit of a head flick she was concentrating on other things.
Done with her nails, she reached into her drawer and reached around before settling on some pretty pink panties. I was disappointed in that she slipped them on under the robe and I didn't get a view of her naked, but soon I was thrilled when she took off the robe and lay down on the bed in just those flimsy panties.
I watched as she began reading a book, and I felt like such a naughty voyeur. But naughty wasn't merely me after a while, because the woman held the book in one hand while sliding the other down to play first with her thighs then patiently creeping upward until she slipped her fingers into her panties.
First I wondered what she was reading, and then I realized who cared? She was playing between her legs, the woman I'd often fantasized about was working her pussy under those flimsy panties. Soon the book was put down and she began fondling her ample breasts. Unbelievable!
Needless to say I'd never seen a girl masturbate before, so the view was spectacular. Once I thought she was looking toward my perch, but she looked away and I chalked it up to her being lost in the sensation of her fingering her wet slit.
Stroking myself in tune with her fingers dancing in her honey pit I was lost in the action below. Suddenly, Mrs. Easterly moved up and reached over and pulled the covers over her body.
Quickly I realized what was going on. Her husband arrived home early and walked into the bedroom and caught her in the act. He pulled the covers back and was clearly saying something to his wife. She shook her head no, but the man was insistent on something he was acting.
Soon he was unbuckling his trousers and kicking off his pants as he pushed his wife back onto the bed. Down came his underwear and he slid on top of her. Rubbing his dick up and down her slit, he quickly entered her without any foreplay and began rutting like a dog in heat.
In and out he went, holding her legs up high on his shoulders as be insistently and emphatically banged his wife. Like a flash it was over, as he rocked in her, pounded her, and then held the pose as he came inside his wife.
He didn't even kiss her as he arose, saying something, and then walked toward the bathroom where I imagined he was hitting the shower. He must have been, as the woman arose, slipped toward the bathroom almost as if to listen then back to the bed. She reached into the nightstand and pulled out a submarine shaped object that, when she laid back on the bed, she turned on and began fucking herself with.
Quickly and sans prep, in and out it went, fucking herself with the dildo. She moved it around her clit, in and out of her pussy, and soon her head was way back and her knees were up and she was shaking in obvious ecstasy. As quick as her husband humped her and ran to the shower, she humped herself with the vibrator and got herself off. She did, her eyes were back in her head and she was shaking.
And all that action got me off as well, as I spurted volley after volley of pent up desire onto the attic floor.
When I looked back down I swear Mrs. Easterly was under the covers again looking up at me. I pulled back, then had to look back down, and I believe she had indeed caught me. But, surprise of surprises, she was smiling. That smile soon left as her husband came back into the room.
The two spoke, then he strode out of the room soon followed by his wife.
The next afternoon I entered the Easterly house right behind Anthony. We dropped our books on the floor and slipped down to the basement to shoot some pool. Later, I heard someone enter the floor above, and when Anthony slipped into the bathroom I said I'd grab us a couple soft drinks.
Upstairs I went, walking into the kitchen as his mother was walking out. She smiled at me, told me the fridge had a good selection of drinks and began to walk upstairs. She stopped quickly, turned, and whispered to me a question.
"Did you like the show," said the woman. "I thought your eyes were going to pop out. You are pretty forward sitting up there and watching out bedroom!"
Stammering something about that not being the case, that I knew nothing of what she was speaking about, she smiled and told me it was all right. "Just don't get caught by your mom. Sometimes mom's don't understand the naughty nature of their sons."
With that she strode upstairs, and I only wished I were upstairs watching her room. I think she gave me her approval to look.
I tried over the next few days to get a show, but it wasn't to be. On Friday I stopped over the Easterly's house in the early evening to see what Anthony was up to, but Mrs. Easterly said my friend and his father went over to the mall to pick up a couple gifts. She led me into the kitchen, and we sat across from each other, each not wanting to be the first to speak.
Mrs. Easterly spoke with kindness and authority. "That was wrong, what happened the other day, I should have pulled the shades closed," said the woman. "And you, young man, should have been a gentleman and looked away."
She looked at me and smiled, her mind whirling. "I guess a horny guy like you isn't going to look away, right?" she said with a laugh. I could swear she was blushing. "Actually, it was kind of hot. I don't know that I've never been spied on that way."
Apologizing, I told the woman it was a beautiful view. I'd stop looking if she asked, and it was a total secret. I'd never tell anyone.
"You are so sweet.... are you sure? You won't tell anyone? Ever?"
No mam, it was the hottest thing ever.
"You know I'm not some kind of floosy, right. I would never cheat on my husband, although he's given me reason.... I mean, you can look, just not touch, right? That's so very, very erotic to me."
"And me too, Mrs. Easterly."
She quietly asked me a question. "Did you, err, did you masturbate?"
Nodding my head, I told her I did and left a whole lot of sticky stuff on the floor.
Just then we heard the garage door opening, and she shooed me out of the house. But she left me with a couple hints.
"Richard has a tee time tomorrow morning at 10. If you were, ah, looking, maybe at 7:30 or so you might get another show. He likes to do it Saturday morning and then brag about doing it to his foursome," said the woman with a laugh. "Oh, and clean up your mess up there. Mothers have special eyes you know. Be careful."
In a jiffy I was gone and that night I did my best not to whack off because I wanted to save myself for the morning quickie next door. I slept well, though, setting the phone alarm for 7. With some quiet walking, I made my way upstairs.
At first I was worried, because the shades were totally close in the Easterly bedroom. Checking around, all was quiet in my house, so I sat on my perch and attempted to stay out of sight from below.
Soon I saw a rustling of the shades, and soon I saw the woman of my dreams, Mrs. Easterly sliding open the shades. She was dressed in a blue baby doll nightie that left little to the imagination. Sexy panties to the set, the short nightie above, she looked adorable.
She was talking to her husband, who was still lying on the bed, then left the room. I pulled back so as not to be conspicuous, and waited while peering over from time to time to see what was happening.
It was worth the wait. Soon Mrs. Easterly brought a cup of coffee and handed it to her husband, who took a slow belt while eyeing his wife. She did look adorable, and while she was brushing her hair he said something to her that brought a smile to her face.
While I wished I had a microphone in the room, my eyes heard what was going on. Mr. Easterly needed his pipe cleaned! And his wife was just the one to do it. His cock started rustling the sheet, as Mrs. Easterly spoke to him. Soon, she did more than talk.
She walked over, set the hairbrush down on the nightstand, and then slid off the sheet. Mr. Easterly was in the mood, as his cock was three quarters erect. That wasn't good enough for his wife though as she knelt on the bed and slowly lowered her head.
There, with my eyes bulging, she started licking her husband's cock. Up and down, around, from stem to stern. When she paid close attention to his balls his dick powered itself into overdrive. She still hadn't sucked him, but his dick was pulsating against her face. He rubbed that dick against her face, and circled her long hair around it, jerking himself off in the air while she licked his balls.
I loved the way her ass was high in the air as she was bent over her man. She worked her lips, then pushed his hands away and removed his dick from her hair. She said something to him, then bent back over and began sucking his dick.
First she worked the tip, moving maybe an inch in and out of her mouth before she ate nearly the whole enchilada. Up and down she went with his hands moving over to guide the blowjob. He was thrusting in and out of her mouth.
The woman was totally immersed in her husband's cock, and I had to wonder if it was a show for me or an act of kindness for him. Either way, I loved watching as he guided her head up and down his throbbing cock.
Her head was moving like a blur, and his head was thrown back as he pounded his midsection against her head. All of a sudden he reached down and started stroking his cock while she moved off his dick. Within seconds he began jerking off and shooting his cum wildly all over. Some hit her in the face, but a lot hit her hair and even more up and down onto the sheets.
Mrs. Easterly quickly lowered her head back onto his cock after the initial volleys were complete, and she finishing him off in her hot sucking mouth. She kept bobbing her head as he cock began to shrink, and soon she had the whole thing in her mouth as she rested her head on his loins.
For a minute he stroked her face and hair, rubbing the cum around. For her part, Mrs. Easterly just kept still, savoring the cock in her mouth while cum dangled off he chin.
And then, as quickly as it started, Mr. Easterly pushed his wife away and bounded into the bathroom, presumably for a morning pre-golf shower.
Mrs. Easterly merely stood and took off the stained sheets and put them at the foot of the bed for cleaning. In the middle of that, though, she looked up toward my perch and reached over and took a piece of the sheet and dried her face. Damn, that was so very hot.
It wasn't long before Mr. Easterly slipped out of the bathroom and dressed. Before he left he kissed his wife on the forehead and then gave her behind an easy smack before he left the room. She looked out the window, and after his car left she looked at me and smiled.
She gave me a naughty, naughty stroking of her fingers before turning and slipping back on top of the bed. With her knees slightly bent she reached up her hands and began playing over the nightie, tweaking her breasts. I wished she'd have taken off the nightie, but it was so very erotic watching her as it was.
After a bit she slipped down her panties, kicking them off, before beginning to slip her fingers over, under, and around her pussy. She was obviously turned on by the earlier blowjob, because I could swear I could see the wetness. Her fingers easily slipped in and out of her cunt, playing with it like a porno star.
Her eyes were closed as she worked herself, but I noticed she opened them and looked toward the nightstand. She reached over and grasp her hairbrush, with she turned around and began working the handle against her womanhood. Up and down the slit it went, working the outside of her pussy.
She was actually swaying in tune to her stroking and I wished I had a closer view. I told myself to bring up some binoculars for future use!
In an instant she inserted the hairbrush handle into her pussy, and the fucking began. She began rutting herself with the wooden tube, pushing it in and out of her slimy hole as her butt began bucking in tune to her thrusts. She was obviously enjoying the action, as I saw her tremble, grimace, shake and saw her lips oval into a moan as she fucked herself.
Eyes closed, muscles tensed and soon the woman was climaxing on her bed right in front of my eyes. She wasn't faking either, as I swear I heard the cry of relief from below. She held the pose for about a minute, with her hands by her side and the hairbrush in her pussy.
I watched enthralled as the hairbrush began moving by itself or propelled by her pussy muscles until it popped out of her snatch. She lies there totally satisfied for about another minute before her eyes opened and she looked directly up at me.
She shook her head, put a finger to her mouth as if to shush me, and then smiled an embarrassed smile.
Without question this was so very much better than any porno I'd ever seen, and I swore off looking at them in favor of looking at my best friend's mom at whatever opportunity I had that entire year.