The Sandy and Ashley JerkOff Series

Part 1 of a series of stories.

This is a story about my friend Ashley and her MILF, Sandy and my experiences with both (although I only got with one).

This series is all true, and it goes into every time I fucked/titty-fucked and everything else we did.

I will keep writing if enough people like it.

Part 1: The Party and Finding Bras

Ashley Green and I had been friends for a few years and had ended up hanging out together pretty often, almost every other weekend and a few times during the week.

She's 25, about 5 foot 7, fit, with an athletic build, blonde, and some of the greatest tits I have ever seen.

We were always seeing other people and she would start referring to me as being "like a brother".

Now, some guys might disagree with me about her tits, but to me they were amazing.

There was just something about them that drove me crazy...I was always trying to get a glimpse of them and her cleavage, but never could.

All I could really see was that flat upper chest that I knew gradually curved down into some heavy, full, and rounded breasts.

This led me to believe that her tits started pretty low, which drives me crazy.

The first time I actually got a view of her breasts was when it got warm out and I remember being blown away.

Yes, her tits started low on her chest and looked like they hung pretty low.

Her cleavage was on full display that day and was long, curving down into her heavy tits that were firm and round with a wonderful shape.

I jerked off to Ashley''s pictures pretty much all the time and the fact that I would see her often only added to the hotness of it.

I really wanted to get my hands on some of her bras and panties but never got the chance to, but my dream was to wrap those bra straps around my dick and try to fill the cups with as much cum as possible.

The circumstances never seemed to allow me to do it so for a while, I had to make due with her pictures.

Shit, I could even cum just thinking about her not looking at anything

After a few months we were hanging out at a friends house, my friend Ron.

After a while, Ashley left to go home leaving just Ray and I sitting around.

Finally, after watching some more of the movie we were watching, Ray goes to me:

"How come you and Ashley never hooked up?

You guys are always together."

"I dunno, man, just never has happened."

"Would you?"

"Fuck yes I would.

I'd be lying if I said I didn't jerk off to her."

"Haha, really?"

"Yeah, not afraid to say it."

"Well, I've done a fair share of that to her too."

"No shit, really?"

"Yeah."

From then on, Ron and I would jerk off together to Ashley, mostly online looking at her pictures.

We had some great chats and would go into all our fantasies about her.

It got to the point where we were trying to come up with ideas of how to make our jerk off sessions even hotter (without going gay, not my thing).

Ultimately we wanted to go into her room, dump out all her dirty bras, put a slideshow of her up on screen and spend the day jerking into her bra cups.

At this time, Ron came to me and said:

"Have you seen Ashley's m om?"

I had never really thought about her mom or even had seen her, so I said no.

Ray looked at me and said:

"Dude, she's hot.

Her tits?

Now I know where Ashley gets them."

I had never seen her m om in any of the pictures so I had no idea, she didn't do much on FB, so we made up the excuse of Ron having to borrow a drill from them.

When we got to her house, her mom answered the door and the first time I saw her, I felt a huge twinge in my dick.

Her name was Sandy, 44 I think, a little taller than Ashley, blonde hair, and also with an athletic build.

But the thing I noticed the most were her breasts...they were incredible.

They were a lot like Ashley's, low on her chest, heavy, yet round and full....even rounder at the bottom than Ashley's.

She was wearing a sleeveless sweater type shirt and even though she wasn't showing cleavage, it was obvious she still knew how to show them off.

The bulged from under her tight top, two swelling mounds hanging down almost to her middle.

Yet they weren't saggy in the sense that they were flacid and flat like some older women's....they were so full and so regal and she obviously knew it.

From then on, our jerk off sessions revolved around Sandy and Ashley, obviously talking about fucking both of them at the same time, their heavy full tits on display covered in our cum as they rubbed them together.

We would talk about how their tits were shaped the same, Sandy's being a little heavier, but both sets sitting low on their chests.

We knew Ashley would have some heavy hangers like her mom's as time went on.

For a few weeks, my entire jerk off material was just them, nobody else.

Our goal became to get our hands on their bras, some guys go for underwear, but as into both their breasts as we were, we both knew bras were the way to go, at least for the first time.

For weeks all we could think about was wrapping the bra straps around our dicks, feeling the soft fabric on our dicks and jerking off trying to fill the cups with our cum.

We also really wanted to know what their bra size was.

A month later, we got what we wanted.

Ashley was having a party at her house and invited both of us since we were all in the same group of friends.

When Ashley greeted us, my dick twitched in the same way it did when I saw her m om...she was wearing a super low-cut white top, her heavy breasts on full display, her cleavage long just like I thought it would be, arching down into a delicious curve and swell of her lower tits.

When I saw Sandy in the back yard, I think I almost cummed right there...she was wearing a VERY low-cut green t-shirt, her breasts swelling, stretching the fabric until it looked like it would burst.

Her cleavage looked just like Ashley's, long and gradually arching into some full, round, tits.

Her flat upper chest was tanned, slightly freckled like some older women get, aged skin, yet smooth.

We spent the entire time out on the deck with everybody, but we were focused on Ashley and Sandy's cleavage as they moved around.

At one point Sandy bent over a cooler to get a drink and I almost came as I saw her heavy hangers hanging inside her shirt, hanging down so low from her chest.

Ron and I kept looking at one another until finally he sent me a text:

"Won't get a better time", it said.

I knew instantly what he was talking about.

I got up, said I had to take a call, pulled out my phone and headed inside.

A few minutes later, Ron followed and we made our way upstairs.

The first stop was Ashley's room where we checked in her closet and found the dirty laundry hamper.

We dumped it out and immediately came upon a few pairs of bras, simple plain t-shirt bras, and a sports bra.

I put the sports bra up and sniffed it, the scent of stale tit sweat making my dick hard.

I gave it to Ray who did the same.

"Holy fuck, man," he said.

"Her sweaty tits have been IN this!"

"Fuck yes," I said.

"You want it?"

"I'll be nice, you can have it.

I want this one."

Ron picked up a black bra I had no scene.

It was lacy with a thick middle strap.

It had a faint odor of stale sweat too, just not as strong.

We were so pumped, we forgot to check the tag, but luckily Ron remembered.

34 double D.

About what we expected, but seeing it there in front of us made it so much better.

I put the dirty sports bra in my pocket for later.

"I'm taking this with me," I said.

"Your new cum rag?" Ron asked.

"Nothing else will get my cum for a long time with this around," I said.

I also took a plain white striped bra that also smelled slightly of faint sweat.

We put the dirty bras back in the hamper and went down the hallway into Sandy's room.

Her hamper was a little harder to find, but we did eventually in the closet between her bedroom and bathroom.

We dumped it out on the floor and again, immediately found a few dirty bras.

The straps were thick as well and this time I checked the tag of a blue and white bra with a flowery design on it.

34 triple D

We were so pumped, our hearts racing, it was almost like we were drunk.

Ron took up a plain white one, which I totally got right away: sometimes the simple things are hotter.

We put the bras back in the hamper then put it back into the closet space.

I was about the head downstairs when Ron said

"Hold up, do you know how we're always trying to figure out a way to make jerking off to Sandy and Ashley hotter?" He pointed back into Ashley's room.

"Dude, those two windows look directly out over the deck..."

I knew what he was thinking and said, "Oh fuck yeah, man.

Better than jerking off back home to pics over Skype."

We went into the room and made sure that all the lights were off, it was dark outside by this time so nobody would be able to see us with the lights off.

We hoped.

The deck lights were already on and pretty bright so it would be hard for anyone down there to see us, even if they chose to look up for some reason...

Ron took the left window and I took the right.

Ron had to lower the blinds on his a bit and I had to raise mine a bit.

We had them just above eye level if we were on our knees, but the view was surprisingly perfect.

Sandy and Ashley were easy to spot, even from the top down, their tits bulged in their shirts.

What was awesome was that now with almost top down views of their cleavage, we could see every little jiggle and sway their tits made as they moved around.

I took off everything from the bottom down and found myself already hard and oozing pre cum.

I d****d the strap of Ashley's bra over my dick and let it hand off it, enjoying the feel of the fabric head.

Then I did the same with Sandy's floral bra.

First I took the middle strap of Sandy's bra and wrapped it tightly around my dick, wrapping one of the cups around it like a glove.

I began to jerk up and down with the cool fabric of Sandy's 36DD bra...a bra that had held those heavy hanging tits, soaked up her tit sweat, and was now around my dick.

I looked down and focused in on Sandy.

She was sitting in a chair talking with someone, her heavy hanging tits in her t-shirt moving up and down as she breathed.

Whenever she used her hands to make motions to illustrate her points, her tits jiggled and swayed.

Every time she moved, they looked like they were made of water, her long cleavage curving down into a black hole that was her t-shirt.

My strokes became faster but I knew I had to balance my time.

I dropped Sandy's bra and let it hang from the strap around my dick again then took up Ashley's bra and wrapped it around my dick.

I looked down at Ashley, she was standing talking to a few people.

I could see straight down her top, her tits also moving and jiggling every time she moved.

Even from the top down, her tits were the same as Sandy's, both sat very low on their chests, both sets heavy, both had long cleavage that teased by revealing itself for a few inches before finally hiding beneath their shirts.

Ron was also jerking fast, focused in on Ashley and Sandy.

I said, "I want to cum out the window and let it drip down their shirts.

Make a river of cum in their cleavage."

"Oh my God, their tits are so crazy," he said.

"Look how fucking heavy Sandy's are...and how Ashley's are shaped the same but not quite as heavy.

Not yet."

"They will be."

We continued to jerk off into the bras, alternating between both sets.

My pre cum was leaking everywhere, soaked up by the fabric of the bra cups, staining them.

Sandy and Ashley continued to move around, their tits swaying as they did.

At one point, Sandy laughed out loud and clapped her hands a few times, her tits jiggling like crazy, her left tit swinging into her right, her cleavage closing and opening over and over again.

Ashley even jumped up and down at one point, her hangers following her up, then hanging there as she came down, bouncing crazily as she stopped, returning to their normal set position.

"I would suck on Sandy's tits all day," Ron said.

"I'd breast feed off those things while she just watches TV."

"I'll suck on one of them and you get the other," I said.

"I'd even fuck her armpits from the back so the tip of my dick poked the side of her heavy tit."

"Fuck yea, I'd use her breast milk as lube."

"I'd use her tit sweat as lube."

"We should fuck her when she gets back from working out, all sweaty and smelly."

"Oh fuck yes," I said, "I would LUV to get those sweaty MILF hanging tits around my dick and reak it up."

"Then piss all over her to clean her off."

"If she was covered in piss and cum, I'd probably have to fuck her again."

"What about Ashley?"

"Same for her.

Have them both live with us, have everything they need, just have to walk around naked all day covered in our cum.

Days old cum too, no showering.

We just cum on their tits whenever we walk by, then wash them off with piss."

At this point I could feel myself about to cum.

It was a pretty hard choice deciding which one would get my cum, but I ended up exploding into Ashley's white bra, soaking the cup.

My dick pumped load after load of cum into the bra fabric where her breast had been.

I quickly switched to Sandy's bra and finished off into her cup, not getting as much into it as Ashley's but still a good amount.

Ron came a few seconds later, filling Sandy's bra cup with a few loads of cum before switching to Ashley's and doing the same.

We wiped the excess cum off with the bras, I used the middle strap since the cups were so full of cum.

Ron did too.

After we were ready, I said:

"I have an idea."

"What?"

I scooped up some of the cum from Sandy's bra cup and some from Ashley's and held it in my hand.

"What are you doing?"

"Just do it."

Then we put the bras back in their hampers, knowing and maybe hoping they would find them crusted in cum when they did laundry.

The sports bra stayed in my pocket and Ron took another one of Sandy's dirty bras from the hamper and put it in his.

We made our way downstairs and back out onto the deck.

Ashley came up to me right away and said,

"Where have you been?"

"I had to take a call."

"Oh okay, loser."

She laughed and gave me a quick hug.

I couldn't believe my luck.

As we parted, I let my hand with the cum in it slightly brush her right tit.

It was one of those "accidental" brushes that girls are probably used to because she didn't say anything.

But I saw that my cum had stuck.

Ron saw me and got it immediately.

He made his way to Sandy and said that we had to get going but thanks for having us.

She got up to give him a hug and he did the same, only this was on her left breast.

I couldn't believe she didn't say anything as we left, but I came again when I got home, jerking off into Ashley's sweaty sports bra thinking about how she and her m om were walking around with our cum on their tits.

Next: The Bikini and Tit-fucking Ashley