The Sandy and Ashley Jerk off Chronicles
 

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 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 5'7", 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.

34DD.

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.

34DDD.

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

Love it, but have to ask, how did the convo go with you and Ron about jerking together for the first time, I’m dying for that but wouldn’t know how to even start it.

Check ur messages

Well they would later notice there was cum on their breasts, then they'd recall that it was the two of you who had cum on your hands, and you disappeared together. They probably thought you two were gay and were getting it on with each other and too embarrassed to say anything.

yea maybe but there were a lot of guys there besides us so maybe they didn’t notice until after and then it could’ve been anybody who hugged them.

Even if they thought we were gay, worth it lol

Part 2: The Bikini and Tit-fucking Ashley

Pictures Below

A few weeks after the first time jerking off into Sandy and Ashley's bras, a group of us went to the beach for the weekend at one of our friend's vacation house. I had actually never seen Ashley in a bikini before, there was never much on her FB, so I was pretty excited to see what'd she be holding those heavy tits in.

The next few hours were long for me. I noticed Ashley was already wearing a bikini under her shirt, the strings tied around her neck popping up above the collar. It was green and didn't look like it gave those heavy full breasts much support. The jiggle and bounce of her tits every time the car moved was driving me crazy.

After getting to the house and unpacking, we hit the beach. I had my eye on Ashley the entire time and I remember the moment she took her t-shirt off, raising her arms above her head and pulling it upwards.

Her breasts stretched upward with her arms, then jiggled back down as their round bottoms bounced back into place. It was all I could do not to cum right there in my shorts. Her cleavage started low on her chest and was just like I remembered from the party: long, nice space between her tits, curving down into some heavy, full, tits that still managed to round out despite being so heavy.

The best part was that Ashley was really slim and athletic. She wasn't fat so there was no "fat girl boob" syndrome.

Ashley then bent down to grab a football, her tits hanging down from her chest, then she tossed it at me. I was so distracted it bounced off my chest before I could even move my arms up.

"Nice catch," Ashley said laughing.

"Shut up," I said, reaching down for the football. "Go long."

"Are you sure you know how to throw that? You have trouble catching it."

I tried to keep my eyes off the two heavy breasts swinging down in her green bikini top. "Just go long!"

Ashley jogged off down the beach, her back to me. I could see her side tit flaring out as she ran, her breasts swinging back and forth. But the thing I noticed most was how low her middle bikini string sat around her torso. It was almost around her waist. It meant her tits were indeed low, as if anyone needed to be reminded, and what's more, she kept the shoulder strings tied long so her tits could hang, probably for comfort if not support.

We threw the football around with everyone for a while, it was hard to pry my eyes off her tits every time she threw the ball my way. Ashley and some of the girls did some swimming, her tits glistening in the sun off the water running down them.

After the day was done, we were back at the house. We all just spent the night drinking and partying then everyone pretty much went to bed. I of course snuck into Ashley's room while everyone was talking and got a good load off with her still wet bikini.

The next day we hit the boardwalk to shop around. Ashley and I split off to go into one store. Ashley, who has a tendency to buy a lot of clothes, maxed out her credit card at one store trying to buy some shorts and sun glasses.

"Fuck," she said, "That's embarrassing."

"Sucks to be you then!" I said, teasing as I always did.

"Shut up!" she said, shoving me and laughing. "But I really want these."

"Guess you better learn to pay your bills then, dummy."

"Oh my God, I'm going to punch you," she said, making a fist and raising it, her tits swinging underneath her loose t-shirt.

I laughed and turned to go. "Come on, let's go. I'll buy you lunch."

Ashley made a face and said, "I'd rather you buy me these," holding up the four pairs of shorts and sunglasses.

"I'm not fucking buying you clothes," I said.

"Just this once, James!" she said, mock pleading.

"No, fuck off!" I laughed.

"Please?" Ashley said, grabbing my arm.

"Are you going to pay me back?" I asked, yanking my arm away.

"Yah, when we get home I can."

"Nope," I said, turning again.

"James!" Ashley said, laughing embarrassingly. "Please?"

"Forget it, Ashley."

I remember Ashley grabbed my arm again and pulled me close and said, "Okay, look, James....I'll give you head?"

She said it almost like a question. I didn't really know what to do because we were close friends and joked like that all the time. Another smaller example is watching TV at my house and she clasped her two hands together over my crotch and moved it up and down and went, "Yeah, two hands! You ever get that? Like with two hands?" Jokes like that.

But she seemed serious this time so I paused and looked at her.

"Are you kidding," I said, doing my best to seem angry.

"No, James, I'll give you head. I'm really good at it, haha."

I yanked my arm away in mock anger. "No, we're friends, wtf are you doing?"

Ashley looked at me like I was crazy and said, "We'll never talk about it again, we can do it as soon as we get out of here back at the house, it'll be good, I promise."

I grabbed her by her arm and led her to the side of the store. She laughed along the way. I pulled her aside and said, "You don't need to give me head," I said.

"So what do you want then?" Ashley asked. "James, come onnnnn! Hurry up what do you want."

I took a deep breath and thought 'Fuck it'.

"I'd rather do something else," I said.

Ashley pulled her arm away and laughed. "I'm not fucking you."

"I don't want to fuck you," I said, punching her lightly on the arm.

"So then wtf is it?" she asked.

"Look, if you let me TIT-fuck you, I'd settle for that."

I almost laughed. 'Settle for that'. As if that was settling for me. At this point I honestly would rather have fucked her tits than actually fuck her, but I thought I could work my way into fucking her full on. But if that didn't happen, I wanted to at least have fucked those amazing heavy round breasts.

Ashley's eyes widened. "Really?" she asked, smiling.

"What's so funny?" I asked.

"Nothing. I'd prefer that anyway. I don't have to get all your cum in my mouth, haha."

"No, just on your chest. Easier to clean right?"

"Yes!" she said. "Okay, promise?"

"Promise," I said.

After paying for her stuff we met back up with our friends and told them we were going back to the house. After hearing usual jokes about us secretly hooking up and laughing them off, we went back.

We went into the room she was staying in and closed the door behind us. She put her new clothes and sunglasses in her bag and turned around.

"Okay," she said, taking a breath and smiling. "Are you excited?!?!" she said, goofy and teasing.

"Yeah, let's do it!" I said, just as goofy.

Ashley took her t-shirt off, her bikini clad tits swaying. This bikini was black, but that didn't matter now.

She laughed as she reached behind her to untie the strings.

"This is like awkward," she said. "How do we do this?"

"Uhh well first, you take your bikini top off."

Ashley sneered at me. "Well duh," she said, and untied the strings.

Her tits bounced a little lower as the middle string untied meaning they were slightly held up. As she reached behind her head to untie the other strings, her breasts spread apart to the sides. As she untied the strings and took the bikini all the way off, they came back together with a soft "slap".

Her tits were just the way I pictured. They hung low and were heavy, yet still round and full. Her cleavage was wide, the perfect size for any dick, her nipples relatively small and dark pink. Her flat upper chest slowly led down into that cleavage which started low on her chest, which explained why during the winter I could never get a good look at it. Her skin was bumpy from the air conditioned air and she had faint tanlines around the bottom of her tits.

"Boobies!" Ashley said. I remember because it almost killed the moment.

"Wow those are nice," I said, "I'm impressed."

Ashley laughed and jiggled her tits side to side. "You didn't think I had nice boobs?"

"Guess I never really thought about it," I said, lying.

"Uh huh," Ashley said. "Okay, let's see what I'm working with. Shorts off bud."

My dick was already filling with blood so I knew it would come out thick and ready to jump into a full on hard on so I wasn't worried. I took my shorts off, then my boxers, tossing them to the side.

Alex gave me an approving look and nodded, laughing. "Not bad at all lol. Thick. Girls like thick, did ya kno that?"

"Uh yeah, I've been around a few times."

"Well I don't know," she said laughing. "K, now what?"

"Just get on your knees, I'll do the work," I said.

Ashley got on her knees and I came up to her. I rubbed my dick on her flat upper chest first, then moved the head down to her right tit, feeling the soft breast give way. Then I moved it to the left, softly slapping it and watching it jiggle as if made of water. My pre-cum left streaks across her chest as I moved my cock around, enjoying the warmth of those heavy tits the underside of it. It was quiet in the room but I didn't care if it seemed awkward or not.

I put my cock into her cleavage, moving it up and down slowly.

"Hold them up, you've seen porn right?" We laughed.

Ashley held her heavy tits up and pushed them together, her nipples thrusting towards me. Her tits wrapped around the sides of my dick, smothering them in warm tit flesh. The pre-cum began to ooze even more.

I slowly began to thrust my hips up and down, moving my dick up and down in her cleavage. The bottom of my dick chaffed against her cleavage, the sides of my dick rubbing the inner sides of her heavy full hangers. I began moving so fast and hard it almost hurt.

"Hold on," Ashley said, letting her breasts drop. They were already red. She reached up and grabbed my dick and squeezed it.

"Ow," I said, "What?"

"Don't move!" she said. She scooped up the flow of pre-cum from my head between her two fingers and smeared it into her cleavage. She did it 2-3 more times, I can't remember how much, but then pushed her tits back together, now better lubricated.

"Okay, go," she said.

I laughed and said, "Good idea. I feel like you've done this before."

I continued my thrusts between her tits, the tip of my dick coming out the top of her cleavage. Ashley kept looking down at it as I fucked her tits as red and raw as I could. A few minutes later, I felt I was about to cum so I stopped.

"Okay, lie down," I said. I slipped my dick out from her cleavage.

Ashley lay down on the bed, still holding her tits together.

"Okay, let them go a sec," I said.

Ashley did and let her tits fall to either side of her body slightly. They were glistening with pre-cum, red, and already chaffed.

"Oh my God," she laughed looking down. "I look sun burnt!"

I got on the bed and straddled her. Ashley pushed her tits together, her elbows flaring to the side as she reached to each side of her both to collect each heavy hanging breasts to bring together around my dick.

The warmth of her tits around my dick grew into an all out heat as I continued to fuck her breasts, my dick grinding into her cleavage. I reached down and moved her hands away and fondled her heavy tits, feeling the weight in my hands, the bulk of the round bottoms, my thumbs rubbing her nipples. I pushed them together and continued to ram my dick up and down between her tits

Ashley looked down at one point and spit a huge wad of saliva into her cleavage, made me stop for a second, and rubbed it into her cleavage for more lube.

A few more minutes went by before I felt ready to explode.

I slide my dick out from her cleavage, a string of pre-cum following.

"Okay, let go," I said quickly. Ashley let her tits fall to the side again and raised her arms above her head.

"Uh oh, here it comes," she said laughing.

I exploded a second later, shooting a huge rope of cum right into her cleavage which was now completely flattened out due to her tits hanging to the side. Another pump of cum shot out over her left tit, moved my dick to the right, and shot another rope of cum on the right. Two more pumps of cum were shot out onto her tits but I don't remember where exactly on them.

After I was finally done, I took my dick and rubbed it around on her tits, covering his nipples in thick, slimy, white cum. It was like my dick didn't want to leave her breasts, they were its home it was almost like.

Ashley finally pushed me off and sat up. "Well, that was that," she said laughing. "You cum a lot."

"I know, sorry," I said, grabbing a tissue to wipe myself off.

Ashley got up, her tits swaying back and forth, red and raw, glistening with shiny white streaks of semen. Some globs of it started to run down her long heavy tits as she stood up.

"I'm gonna shower," she said, heading towards the bathroom.

"You need me to buy you anything tomorrow?" I asked jokingly.

Ashley laughed and turned around. "Same deal?"

"Depends on what you want to buy."

"Why, what happens if I want something expensive."

"Then we get nastier and nastier."

She laughed. "James, it was a tit-fuck. There's nothing nasty about it, chill."

"We can make it interesting. Depends on what you want."

"Haha, how? Let's hear it sicko."

"I don't know, we'll see!"

Ashley stood there with her hands on her hips, her tits still out and covered in my semen, showing no signs of embarrassment whatsoever which made her even sexier.

"Okay," she said. "Well, I saw a watch I wanted yesterday but didn't get. And it's a Citizen."

She said it like a challenge, waiting to see how I'd react.

"Wow, okay, that's a lot," I said, looking down to avoid eye contact and avoid laughing as I finished wiping myself off.

"Yah, so what do you want in return?" Ashley asked again.

"You pick," I said.

"For that? I'd fuck you for that."

"Does that include a tit fuck?"

Ashley threw her hands up in mock annoyance, her breasts swinging as she moved.

"What is with you and my tits?!" she said, laughing.

"They're hot, I love them," I said, "I dunno. If it includes that, fine, deal, we'll fuck."

"Okay but no anal," Ashley said, actually serious.

"No way," I said. "That's where poop comes from."

Ashley and I cracked up.

Ashley turned around and walked into the bathroom. I went back to my room to shower. There was a bottle of sleeping pills in my bag and I was sorely tempted to take a few just to go to sleep so tomorrow would be here.

Next: Fucking Ashley

Great story, but where's the pictures?

PM me and I can show u. I figured i'd leave it up to the reader's imagination to see what they look like, but if u wanna see the real deal, u got it. They're nothing too great, they don't post much on FB

Part 3: Fucking Ashley

The next day everyone hit the beach again and then the boardwalk for food and more shopping. As we were walking about, Ashley grabbed my hand when we came to the store that sold the watches, among other things.

"We'll be right back," she said to everyone else.

She led me into the store and took me up to the glass counter where the luxury stuff was and pointed to a silver Citizen with a pink face.

"That's the one," she said. "Isn't it cool?!"

"Yeah, really nice," I said.

"Remember our deeeeeeaaaaal," she said teasingly tugging my arm.

I laughed and looked for a price tag. It was only $250, which was better than I thought because I was expecting $400 and up. I guess Ashley really didn't know her watches.

"Well, I dunno," I said, seeing what kind of reaction I'd get.

Ashley rolled her eyes and grabbed my hand and put it between her breasts, bikini clad again but covered in a t-shirt as yesterday. She was wearing a pink and white checkered bikini top and white shorts.

"Remember these?" she asked. "You want these again?"

I looked over at the women behind the counter who was looking at us funny and I shrugged at her. She gave me a smile back and pretended to ignore us.

"Yeah, I do. Okay."

Ashley clapped her hands and jumped up and down. "Yay!!!"

After paying for the watch, we left. Our friends were nowhere to be found outside so Ashley said, "Okay, let's go back."

On the way back, Ashley took off her t-shirt exposing her bikini-clad breasts, the cups of this one a little smaller since her tan lines just peeked out on the bottom of her tits.

Five minutes later we were back in the house and back in her room. I think Ashley was pretty horny because she immediately dropped to her knees, untying my shorts.

"What's gotten into you?" I asked, pretending to push her away, pushing her onto the bed. She laughed as my phone went off. I reached down to check the text but instead snapped a picture.

"What was that?" she said.

"Smile," I said, holding my phone up.

"You're so weird, come here," Ashley said.

"Smile stupid."

Ashley laughed and I snapped a picture (below).

"Oh is that for later?" she asked. "Like in the bathroom, later?"

"Hey, I just bought you a watch, I think I at least can take a picture," I said, trying to come off as joking.

Ashley got off the bed, turned me around and pushed me down onto it.

"What's gotten into you?" I asked again

"Nothing, shut up," she said, pulling my shorts down.

She took my dick in her hand and stroked it up and down with a firm grip. "You really do have a nice penis," she said. "It's pretty."

"Um thanks?" I said.

"You do."

"I thought you didn't want cum in your mouth."

Ashley gave my dick a little slap. "Who says you're cumming in my mouth? Does that mean I can't suck it? Watch."

Ashley opened her mouth wide and slowly brought it down over my dick. But she didn't let it touch her lips or the insides of her mouth. All I could feel was her hot breath as she breathed on my cock over and over. Then she slowly closed her mouth and lips around it, the hot breath turning into a warm, wet, almost slimy feeling.

I let out a deep breath and Ashley began moving up and down, slowly at first, but then more rapidly. She took my whole dick into her mouth, the saliva dripping out of her lips and dripping down my shaft, mixing with pre-cum leaking into her mouth. She came back up and one point and started sucking hard on the head of my dick, using her hand to jerk the rest of my dick off faster and faster.

I reached down to take off her shirt. She came up for a second to take her bikini top off, her heavy breasts swaying as they always did.

Back down on my dick. Sucking hard, using her hand at different intervals. Her saliva continued to saturate my cock, my pre-cum mixing with it and leaking down her chin. At one point she stopped and went down and started licking my balls, fingering them as she did.

"Don't you love just feeling balls?" she asked, laughing. Her face was slick with saliva and pre-cum, her mouth looking like I had already cum in it.

"I guess?" I said.

"So?" she asked, wiping her mouth.

"So what?"

"Was I right? Told ya I'm good at it."

"You are, amazing."

Ashley stood up and pushed me down on the bed, unbuttoned her shorts then pulled them down. She untied her bikini bottom and threw it aside, her pussy completely smooth and obviously just waxed. I knew it was shaved from before when her bottoms were wet from the water. The outline of it was very visible.

She started rubbing it with her fingers to get the moisture going and laughed. "Good, she said. Glad ya like it because that's all you get. Now you get this."

Ashley got on the bed and straddled me with her legs on either side. She pushed my hard dick right up against my stomach and slowly lowered her pussy onto the bottom of it. She started rubbing her pussy lips up and down the shaft slowly, her juices started to mix with her saliva that was on it.

Ashley's breath got harder as she continued to grind on my dick, her hips moving fluidly back and forth as she ground her warm wet pussy onto it. The smell of her pussy wafted around me; it didn't smell bad at all, but like one that is obviously taken care of.

Finally, Ashley stopped and slowly pushed the tip of my dick into her, slowly lowering herself all the way down to the bottom.

"Ohhhhhh, fuck," she whispered, her head back.

"Feel good?" I asked.

Ashley looked back and began slowly riding up and down. "James, your dick feels so good, seriously, where the fuck have you been"

"Um, right here having to jerk off thinking about your tits," I said, trying to come off jokingly.

She stopped and looked at me. "Seriously?"

"Yeah, a few times," I lied. Actually it was probably hundreds of times.

"So like, seeing me in a bikini was insane for you?"

"You have no idea," I told her. "In all this time I've known you, I've never seen them in a bikini."

Ashley laughed and started moving her hips up and down again, occasionally stopping to move front and back, grinding down into my dick and moving it around inside her.

"Fuck," she breathed, her breath coming in pants.

I sat up and flipped her onto her back, her tits jiggling insanely and falling to the sides as she laid down. I pushed them together and sucked her nipple into my mouth, then the other one, and buried my face in her tits, smothering in her cleavage.

Ashley laughed and pushed me away. "Get back inside me," she said.

I squeezed my cock back into her smooth pussy and began thrusting in long deep motions. Ashley started panting faster and faster.

"Oh fuck, fuck, fuck me, baby, fuck me," she whispered as I continued to try to smash my hips through hers, her breasts flopping in front of me, only making fucking her easier as I stared at her heavy tits.

"Huh huh huh huh," Ashley panted over and over again as I started going faster and shorter, then longer and deeper, then faster again. I leaned down and took her right tit into my mouth and sucked her nipple, then moved to the left, then to her flattened out cleavage (since she was on her back) and ran my tongue up it, tasting her tits, trying to cover every inch of them.

Ashley was breathing so hard now that she began short little audible groans as I fucked her, staring at her tits, trying to make them jiggle and sway and flop as much as possible by ramming my dick into her as hard as I could.

Ashley raised her arms above her head, her tits stretching upwards, her eyes closed, mouth open, panting and panting. Her tits looked like they were made out of water, with waves moving up and down under her skin, shaking and jiggling.

Finally I stopped, pulled out and flipped her onto her stomach. She got up on all fours and I again started fucking her from behind. After a few minutes I stopped and got up.

"Hey, I have an idea, get on the floor."

Ashley's body was covered in a thin layer of sweat by now, her heavy hanging breasts and tight stomach glistening. She still had saliva dripping from the her mouth, a long strand of it leading down to upper chest.

"From behind?" she asked, pointing to the floor.

"Yeah, but right here," I said. I pointed to a spot on the floor in front of a mirror on the ground.

Ashley got it and laughed. "Omg, you like them THAT much?"

"Oh yeah," I said as she got down on all fours in front of the mirror.

Looking into it, her tits hung straight down, swaying with every little movement she made. The tops of her tits were long as the hung and they slapped against each other as I began fucking her bare amazingly smooth pussy from the back.

Her heavy tits slapped together over and over again with every thrust. *Clap clap clap clap clap*. I kept my eyes on them while I fucked Ashley, her pants growing so loud and aggressive.

I leaned forward and reached under her and cupped both her tits, feeling them jiggle and bounce in my hands. After a few minutes, she pushed me away and turned over onto her back on the floor.

"My knees hurt," she said.

After a few more minutes of the best fuck of my life (probably only because it was with Ashley who I had been fantasizing about for so long, not necessarily the best I've had ever), Ashley gripped my arms hard.

"I'm gonna cum," she breathed between her pants. "Don't stop, don't stop baby, come on..."

I began thrusting as hard as I could, careful not to adjust the angle in which I was fucking her so that I continued to hit the right spot.

"I'm gonna cum," Ashley panted, "Oh God, here I go, here I go, here I g----Ohhhhhhhhhhhhhhhh."

Ashley groaned loudly as she came, her body shuddering slightly, her pussy dripping. She gripped her tits hard as she squirmed, her pussy pulsating on my dick as her juices made slight sucking sounds as she moved.

She laid there for a minute, her head back, and her eyes closed. "Ohhhh fuck....." she whispered, opening her eyes. "Holy fuck, that was crazy."

I began fucking again, but she jerked her hand down and stopped me.

"It's sensitive!" she said. "I can't keep going after I cum."

"Well what am I going to do then?" I asked.

Ashley rolled her eyes and laid back down. "Ugh okay, if you're close, I can suck it up."

I pushed my dick back into her pussy and began fucking harder and harder, Ashley kept her eyes shut tight and bit her lip, the panting beginning again. She was so sensitive she couldn't help but squeal a every now and then, her body shuddering, her breasts flopping.

After a few more minutes I felt myself getting closer.

"Fuck, I'm gonna cum," I said.

"Don't cum inside me," Ashley panted.

At the last minute, I pulled out and quickly moved up to her tits, the cum shooting out before I could even grip with my hand. I jerked stream after stream of semen onto her tits, turning her cleavage into a river of cum. After 4-5 pumps, I was spent and rolled over. We both laid on the floor panting, our bodies covered in sweat, her pussy soaking wet, my dick shiny with her juices and cum, her tits glistening with sweat and spit and cum, the semen running slowly down from her cleavage onto both tits.

Ashley took a deep breath and said, "That was crazy."

"You already said that," I laughed.

"Yeah but that was crazy crazy," she replied, wiping the sweat from her fore head. "I haven't been fucked like that in a while."

"Not even by Dan? You were obsessed with that guy."

"Yah he was hot but...kind of a small dick. And we don't do that around here," she said.

She looked down at her chest and began swirling my cum around on her tits with her finger lazily, the other hand behind her head, resting it.

"I forgot that you cum a lot," she said.

"You can thank your tits for that one," I said, motioning towards her cum-covered, full, heavy hangers.

"What about this?" Ashley asked, patting her pussy.

"It's really fucking nice," I said.

Ashley made a face and said, "You didn't even taste it, loser."

"Well, next time," I said, sitting up. "Guess that means I got to buy you more shit then."

Ashley sat up, her tits hanging down to her left as she leaned on her left arm, the streaks of cum and spit changing direction, dripping off them towards the floor.

"Uhhhh, no," she said, "You don't have to. Seriously, how come we've never hooked up before though?"

"Because we've both been with other people," I said. "Until now I guess."

"Cuz honestly, that was really good..."

"So what're you saying?"

"I'm saying we should keep doing it."

"Just fucking?" I asked.

"Yah," she said, "Just fucking."

"Deal." I said, holding out my hand.

Ashley laughed and shook it, her tits of course bouncing as she did. She leaned over and kissed me, her fingers tracing over my dick again. "I know, I suck," Ashley laughed and headed into the bathroom, her ass swaying side to side, the sides of her tits poking out from in front of her as they swung with her steps.

Next: The Sandy's Tits Experience

Part 4: The Sandy's Tits Experience


This story might be boring to some people, but I'm just telling it like it happened.

A few weeks later after fucking Ashley for the first time and seeing her heavy breasts flopping beneath me, I went over to her house to spend some time in the pool with friends. Ashley was wearing a blue strapless bikini top with a white design on it, the lack of shoulder strings only enhancing the heaviness and lowness of her breasts. Her flat upper chest was on full display, seemingly going on forever before her sweeping cleavage started, curving down as usual into her round heavy breasts. She wore it low around her middle, again probably for comfort as not to push her breasts up too much, something she had told me she did earlier.

After a few hours, Ashley and her friend ran out to grab more drinks and ice to bring back. A few minutes later, my friend got a call from his girlfriend and had to run out to pick her up because her car was in the shop. Since he was my other friend's ride, they had to leave together, leaving just me.

I remember taking a seat on the first step leading down into the pool, sitting in the water my my chest and relaxing. I almost dozed off, I don't know for how long, but at one point the back door opened and Sandy walked through wearing a black one-piece bathing suit. While it was a one piece fully covering her middle, the top of it was wide open exposing her tanned, low and hanging full breasts, her skin bronzed by the sun and well-aged with sun spots. Her cleavage, as usual, started low on her chest, leaving a vast wide upper chest on top and heavy round tits on the bottom, much like Ashley's.

She gave me a big smile and waved at me, tossing her towel on the chair and walking towards the pool, dipping her foot in to test it, then slowly taking a seat on the step next to me.

"Hi James," she said, "I'm going to join you here for a second. I just got back from tennis so I need to cool off, so forgive me if I'm a little ripe."

I laughed and tried to keep my eyes off her weighty breasts and almost foot-long cleavage. It was hard because they kept moving up and down with every breath as she leaned back on her elbows.

"No problem," I said. "So what's going on?"

Sandy shrugged, her cleavage stretching upwards slightly as her shoulders raised, then extended fully again as they came back. "Ohh just the usual stuff. Seems like my life is taking care of the house, bills, and...I don't know, tennis? Cooking? I'm a boring old lady, you know."

She laughed and I laughed along with her, her hanging tits swaying and jiggly slightly as she did, her nipples hard and poking slightly through the black bathing suit top.

After a few more minutes of chatting about nothing, Sandy sat up and shivered. I remember she said, "Do you know the worst part about not having a hot tub? You have to sit in this cold water to stay warm because if you get out of it, the cold is even worse."

"So don't get out," I said.

I remember Sandy shifted closer to me and leaned against me, her massive left breast squishing up against her side. She put her arm around me motherly and said, "But you'll keep an old woman warn, right James?"

I could feel myself starting to get hard but tried to ignore the surge of blood that was entering my dick at the touch of her left tit, squishing the tanned, aged, top of it up towards my chin, the right one hanging low as normal, providing contrast to her left one that was pressed up against me.

"Uh, sure," I said, looking at her purposely in the face and making a futile attempt to smile and sound nonchalant.

Sandy kept her arm around me and said, "You know, I'm really glad Alex has someone like you, you keep her well grounded, I think. In all the years I've known you, I've almost considering you like a son."

"Thanks," I said. "She's a awesome girl."

Sandy nodded and gave me a motherly-type squeeze of affection. I looked down at her the top of her chest, her left tit still squeezed up against my side, her right one still hanging deliciously. The top down view of her cleavage made my dick hard, seeing the one long line of her right breast stretch down into the her swimsuit with the line of her left breast curved and pushed upward as it was squished against the side of my chest.

We talked about for a few minutes later, her mostly telling me about Alex and how much she appreciated my friendship, talked about the weather, her playing tennis, running, everything and anything, I don't even remember.

I do remember at one point she looked at me and said, "Well, you're a good guy, keep up the good work."

She reached her hand down under the water to give me a few pats on the knee, but her hand brushed against the head of my hard, upright dick which I was trying to hide. I remember her hand hesitated for a split second as if trying to figure out what it was, then when I thought she would quickly move it, she kept it there, her thumb passing over it. Then she quickly moved it down to my knee and patted it. She gave me a knowing smile, at least I think it was, then took her arm off me and stood up, leaning forward to splash some water on her legs. She turned slightly as she did so, giving me a direct close-up look over her heavy breasts hanging down beneath her, the tops swaying as her arms moved the water.

She cupped some water with her hands and threw it on her shoulders then on her face and on her neck and finally her chest. She stood back up, the sun catching her bronzed skin, drops of water streaking down her tanned, aged, cleavage and the top of her heavy breasts.

She looked up at me, gave me another smile and said, "Be good, James."

Then she walked off towards the house. From that point on, we never discussed it, but I felt that there was some underlying current we both had but never talked about. I think she knew she touched the head of my dick, and I think she purposely kept her hand there for longer than it had to be. And I think she knew I knew.

All I knew was that it made jerking off to her heavy, low-hanging MILF breasts that much better.

Next: Braless in Public

To be clear, I don’t have pics of her bare tits, I meant “them” as in Ashley and her mom. Sorry if that confused some of the guys messaging me, but still will share the pics if it’s interested. PM me or hit me up on skype

Part 5: Braless in Public

This part may be boring to some people, but again, these are just the memorable experiences I've had with these big breasts. I will keep writing them down when people give me feedback so I know they're liked :)

During the summer, Sandy and Ashley invited me down to their house in Florida for a week. I had to keep reminding Sandy that Ashley and I were not dating, just hooking up, because she seemed to be treating me like her daughter's serious boyfriend already. Going to Florida didn't really appeal to me when I heard it because I had a lot to do and very little time to get away. But after thinking about it, I decided I could get away for a week if it meant I could see Sandy and Ashley's heavy, low, and pendulous breasts in bikinis and tight tops.

A few days after arriving and a few fucks and tit fucks of Ashley later, we went to the beach in the afternoon. After watching Ashley run around in the green bikini she wore the first day I fucked her breasts, you know, the one whose strings she kept tied long to let her low-sitting, heavy, weighty tits hang low and comfortable, we came back to the house.

We decided to go on a walk around the neighborhood before showering and
going to dinner, so Ashley went into her room to change. I remember her calling to me from inside saying, "Hey James, we're just coming right back, right?"

"Yeah," I said. "I'm just gonna throw on a t-shirt."

"Okay," Ashley said, "I'm gonna bum it then, it's so humid out there."

Ashley came out of the room wearing a light pink summer dress type outfit. It was ridiculously thin, almost sheer, her weighty hanging tits swinging beneath it as she walked, the dress so loose that the front of it slid down lower as she took her steps, exposing her low cleavage and the tops of her heavy rounded tits that were not supported by a thing. If you can remember how low her cleavage started on her chest, you can imagine how much the front had to slide down. Ashley had to pull the dress back up from the strings at least twice before she got to me.

Ashley laughed and said, "I know, I'm not wearing a bra, deal with it even though you love it."

"Oh I do, but you sure you're not going to accidentally flash everybody? Your dress keeps sliding down, wtf, pull it back up!" I said, laughing.

"I know, I'm just lazy. Let's go."

The walk was pretty boring and I don't even remember what we talked about. All I remember is giving sidelong glances at Ashley's swinging breasts, counting the times her dress started to slip down and when she had to pull it back up. It was about every 8 steps that she had to bring her hands up to the strings and pull them back. But 8 steps later, it would be back down, exposing the first half of her low-starting cleavage and all of that weirdly sexy, vast flat upper chest that finally slopped into her heavy hanging tits. With every step, I could see them beneath the thing fabric, swinging slightly from side to side, the left one slightly clapping into the right, then swinging back as the right slightly clapped into the left.

It was very humid out and very sticky to the point where both of us were covered in sweat after a while. My t-shirt stuck to me and I had to keep pulling it away from me and back to let the air in. It was pretty gross until I realized Ashley was also sweaty and sticky because her dress started clinging to her. Those heavy slightly sagging breasts were molded by the thin fabric, every movement they made shown to the world. Her dark pink nipples began to poke through, then eventually show through. Her breasts gleamed under the layer of sweat covering them, a few small drops of sweat disappearing into her cleavage. The sun shown off her slightly sun-burned upper chest before the dress slid down exposing her the paleness of her low set hefty tits.

On our way back, Ashley asked me to take a picture of her on her phone of her standing next to a huge plant. She leaned slightly down to her left, her cleavage dropping at a slight left angle as her left shoulder dipped. Her left breast hung straight down, swinging slightly beneath her top, the right one seeming to chase after it as both of her heavy tits fell to the side.

When we got back to the house and back into the air conditioning, we both went into Ashley's room to cool off. Ashley sat back on her bed, leaning back on her arms, her breasts sliding towards either side of her body as they parted, her cleavage flattening out as her tits spread.

Ashley blew air upwards onto her face. "Oh my God, it is so hot," she said.

"Yeah, it's nasty out there. I'm so gross right now."

"Me too, yuck. I'm all sticky, I need a shower so bad but I'm so lazy right now." Ashley sat back up, her breasts coming back together as they hung down again as the top half of her body straightened.

I kept finding myself staring at her weighty unsupported breasts, their movement only made more seducing under the thin dress. It was as if you could see everything....but not everything at the same time.

Ashley looked at me and laughed. "What are you looking at?"

"Your tits, obviously," I said.

Ashley looked down at her glistening chest, her skin sticky. "Yeah but they're gross right now, you don't know what it's like to have to deal with sweaty boobs."

"I have to deal with sweaty balls," I said.

"Yeah, but I like balls," Ashley said, "Probably cuz I don't have them, I think they're neat."

"Well I like tits," I said.

Ashley opened her mouth in fake shock. "Oh wow, really?! Yeah but would you suck on sweaty boobs? Cuz I wouldn't suck on sweaty balls."

"You're a real lady, you know that?" I laughed.

I remember Ashley threw a pillow at me, her tits swinging and jiggling as her arm came back, then forward, the force launching the pillow and her heavy breasts at the same time.

"Actually, I probably would," I said.

Ashley said, smiling, "Oh really?" She reached up and took off the shoulder straps of her dress and slide the top of it down.

Her heavy tits jiggled slightly as the top brushed past them, shining under the light, her skin sticky and moist with a thin layer of sweat. I had seen her breasts countless times up until then, but every time I saw them, it was always an experience.

Ashley let the top of her dress fall around her waist as she sat upright on the bed. "Actually, that feels a lot better," I remember her saying. "So come here boob-man. You said you'd lick sweat boobs, so lick. Back it up boooooy."

"Actually I said suck," I said, walking up to her.

Ashley rolled her eyes and put her arms around my shoulders as I bent down. "Same thing, who cares, dummy," she said. "Bet you won't like it though."

I could smell her scent, it wasn't bad, just a sickly sweet odor of sweat mixed with whatever body spray she liked. I reached up and gently placed my hands over her soft, heavy, low-hanging, full breasts. They definitely felt sticky to the touch, I remember, almost moist. I ran my thumbs over her dark pink nipples, squeezing her tits, feeling them give way under my hands feeling like they were almost made of water. Every time I squeezed and moved one, it was like ripples moving under her skin, her entire breast, right or left, jiggling with the slightest contact.

I bought her two soft heavy tits together, her nipples pointing straight out at me, and put the right one (my right, I think) in my mouth. Her left breast tasted salty with sweat, her nipples hardening in my mouth as I ran my tongue over it and the surrounding breast that I managed to get into my mouth. It was very sticky, very sweaty, and very ripe, but also amazing as I can remember.

I came up for air and began licking her left breast, tasting the sweat, trying to lick it off of her, coming back to suck on it every now and then. I moved to her right breast and did the same, trying to lick every inch of sticky sweat off of her massive chest. My tongue eventually moved to her deep cleavage, the flavor of her sweat intensifying as I licked her low-starting cleavage dry. Then I moved up to her massive, flat upper chest, then back down to her breasts.

The silence in the room dragged on as Ashley watched her breasts getting cleaned. She didn't make a noise; she never faked anything if she didn't feel anything.

She did say, "Wow, that feels good," at one point. After a while she pushed me away and looked down at her hanging tits, swinging low on her chest, now a mixture of sweat and saliva. They were even more slick now, shining brighter under the lights.

She brought her hands up and pointed to her tits; they, of course, swayed as her arms moved as they always did. "Well?"

I shrugged. "Not bad, I'd do it again."

Ashley laughed. "Well now I have spit and sweat on me so I definitely need to shower. And no, I won't be sucking your balls."

Ashley stood up from the bed and began walking to the bathroom, the top half of her dress hanging down from her waist, her breasts swinging from the side to side, gently clapping into one another as she walked.

"What about after we shower?" I asked, jokingly.

Ashley turned around, her breasts following, then colliding into one another with a soft "clap" as she stopped. She put her hands on her hips, her tits spreading apart slightly, her cleavage widening as her arms flared out to her sides.

"I was gonna fuck you anyway so fine." She laughed and turned back around. I made a point of watching her to see one of my favorite sights: the sides of her heavy tits swinging out to her sides with every step as she walked away from me. I headed to shower myself, counting down the minutes until that night.

Next: Overhearing Sandy's Bra Conversation

Part 6: Housesitting for Sandy

Week 1, Sandy's Room:

A few months later, Sandy called me telling me that she and Ashley were going on vacation for two weeks up in Maine and asked if I would housesit for them. Of course, you can imagine the first thought in my head was that this would be two weeks of jerking off into Sandy's DDD cup bras, Ashley's DD cup bras, sweat-stained sports bras, and...well, whatever else I felt like.

I went over to their house that afternoon to so Sandy could show me around and tell me what exactly she wanted done. I remember she opened the door wearing black kapris shorts and a white tank top, her heavy, full, sun-spotted breasts swelling low on her chest beneath the fabric. It was nice and cool in their house and the tiny bumps on the skin of her upper tits stood out to me under the lights, only accenuating the fullness and realness of her regal rack.

As she led me around the house pointing out things that needed to be done (I don't think I heard some of them), my eyes kept locking in on her bra clasp on the band. I noticed it before, but everytime I saw this, I got turned on like crazy.

Her bra clasp consisted of 4 widely spaced hooks it looked like from under her tight, white tank top. The band was massive, incredibly wide, which of course was the only way that those heavy, hanging breasts could be supported. The thing that got me though, was how low her bra band sat around her middle, in fact it was almost AT the middle of the torso. Again, I wondered if she purposely wore the band that low and extended the straps longer so her tits would sit more comfortably. After all, on the chances I did get to see her low-starting, massive, almost foot-long cleavage, it always hung straight before that amazing curve into the bottom of her rounded breasts.

After she finished taking me around downstairs, she led me upstairs to the bedrooms.

"Not really any reason anything should be done up here," she said, looking at her room and down at Ashley's door.

Right, I thought to myself. Except dump out all your dirty bras from your and Ashley's laundry hamper, wrap the straps around my dick, and try to fill your massive bra cups that have been holding your swelling, heavy, hanging tits with cum. Two weeks worth too.

"Okay," I said, my dick already twitching at the thought.

After that I went home, but I would be back in a few days when Sandy and Ashley left. When I got home, Sandy and Ashley's saved FB pics beckoned me, but I resisted, telling myself to save up bc the first load into those bras would have to be a big one to start the two weeks off right.

As stupid as it sounds, that night I had trouble sleeping. I couldn't stop thinking about the next two weeks, plus the few extra days I had to wait to even start housesitting! I remember looking at the clock and it said 4 AM, which I remember very well because I picked up the phone and called my buddy Ron.

If you remember Ron, he and I had been jerk buddies over Sandy and Ashley for some time now. Until I posted these stories on here, he was the only one who was reading them. Ron was the one who I first jerked into Sandy and Ashley's bras with at the part at their house, watching them from the window above, their heavy pendulous breasts swinging, jiggling, and shaking with every movement they made.

*Note: I have notated the parts of this story Ron has recollected that I had forgotten, or in my excitement of reliving this, overlooked. A few texts were made to him in the process of writing this to get some things straight*

Ron picked up after a few rings and of course sounded pissed off.

"What the fuck," he said sleepily.

"Dude, it's me," I replied.

Ron paused on the other end and came back with, "Yeah, I fucking know dude, it's like 4 AM, so what the fuck?"

I almost laughed out loud but said, "Dude, Sandy asked me to housesit for them in a few days when they're going to Maine. I have a key and everything, you know what that means, right."

There was another pause before Ron said, sounding awake now, "Oh damn, that's like one of our fantasies right out of our minds!"

I could feel my heart beating faster as the thoughts of us in the house of Sandy and Ashley, their dirty bras scattered everywhere, with out dicks out trying to fill the cups with as much cum as we could.

I even said, "I know, my heart is like racing just thinking about it."

"Shut the hell up," Ron said laughing. "You actually get to FUCK Ashley AND her tits, AND cum on them in PERSON."

I knew that was coming at some point so I told him, "One, true, two, I don't get to do that with Sandy and you know I have a thing for MILFs....especially ones of people I know.....and three, doing this kind of stuff is almost better than Ashley's tits in person bc it's so fucking naughty."

Ron laughed and said, "That's actually a good point. Okay so what's the plan?"

"Two days, they leave at 2 P.M. Meet me there at 4 P.M," I said.

"You're on dude. I owe you."

We hung up and I went to the bathroom for some melatonin to see if I could actually fall asleep. I had a feeling I'd be using it a lot the next two nights.

Two days later I went over to Sandy and Ashley's place to start the two weeks of bra jerking. Ron met me there a few minutes later and together we went inside.

I remember turning the key in the lock of the front door and hearing it click open, the door opening, and the scent of Sandy and Ashley that wafted around the house hit us dead on.

"Dude," Ron said. "Something about you unlocking that door has me hard already."

I looked down at the key and saw my fingers were shaking slightly with the adrenaline.

"Me too,", I said. "It's so hot knowing we have full access."

"And they have no idea what we're doing in here with their bras," Ron said.

It was then we realized we had just been standing outside looking in for that entire conversation and we laughed.

"We suck, dude," Ron said.

I laughed and went inside, "I know, but who cares. We need to relish it."

We took another moment and stood quietly in the front hallway, listening to the silence. I think we both were trying to soak in the eroticness of it all, being alone in the house of Ashley and her mom, both of whose breasts we had obsessed over together for months, almost a year now.

Eventually we made out way upstairs and stood in the hall. *Ron remembered this moment very well*

"Sandy or Ashley's room?" I asked.

Ron took a few seconds then said, "Sandy. You haven't seen Sandy's tits in person so lets start with the one you never had."

I laughed and said, "Good idea."

We went down the hall to the last door and went through into Sandy's room. It looked exactly like it did months ago when Ron and I snuck up to it during the party at their house and jerked into her bras then leaving faint traces of our cum on Sandy and Ashley's shirts after we hugged them at the end of the night.

The smell and sight of her room turned me on and my heart began beating even faster. Just being in it and being able to take your time and enjoy it was amazing. The last time we were in here, we were so built up I don't think we really took the time to appreciate it. This was definitely a place we were not supposed to be in, and we were going through her private things without her knowing. Right now, Sandy was on a plane somewhere, reading a book or watching a movie, probably with her full, round, heavy-hanging breasts stretching her t-shirt, drawing looks from whatever guys were around here. Maybe her nipples were showing through the thin fabric in the air-conditioned plane. Maybe she was napping, maybe she was talking to Ashley, eating lunch, who knows. The only thing Ron and I did know was that she had no idea what was going on back at her house, where Ron and I were right now, and what we were about to do to her bras.....things she probably never gave much more of a second thought to other than they were underwear and part of her every day routine.

But to us, they were much more. So much more. This was no disprespect to Sandy, or Ashley. This was to honor them and to flatter them.

Thinking of Sandy somewhere far off doing whatever she was doing on that plane and then looking at us in her bedroom at that very moment made the pre-cum start leaking from my dick. I remember because I hate the feeling of it staining my boxers. Even after I jerk off, I have to wait a while to be sure to get all the cum out of my dick or else once I get soft again, some residue always stains my boxers. Annoying to me, but this time I didn't care.

Sandy's laundry hamper was in her closet which in turn led into her bathroom. Her hamper was a green color *Ron remembers this* and pretty big. The lid was closed and I went to open it, but Ron stopped me. *Ron definitely remembers stopping me*.

"Let's take it out into the bedroom," he said.

"Good idea."

We took the hamper out into the bedroom and turned it over, the lid swinging down, and her dirty laundry spilling into a pile on the floor. The smell of her scent wafted over us as the clothes caused a breeze into our faces.

I remember the first thing on top was a green v-neck t-shirt, the same one she wore that night of the party. I reached down and picked it up, noticing the lines on the front of it where her heavy hanging tits had strained the fabric. I lifted the shirt to my nose and smelled it, Sandy's scent overwhelming me.

Across from me, Ron was doing the same with a brown tank top, obviously putting the part of the top where her breasts had strained the fabric right up to his face.

We didn't say a word for the next few minutes but began picking out the bras. All were underwire bras, their massive cups wrinkled from wear and being crumpled up in the hamper. We began checking tags just for the hell of it, even though the size "34DDD" had been in our minds for all the time we've known. And I think we both knew hot how it was that Sandy had no idea that we knew what her bra size was.

We piled up Sandy's dirty bras, there were eight total, including two sports bras, one of which was almost stiff with dried sweat, right where her under arms would have fallen under, and two large spots on the inner part where her tits would have been squished together.

I could feel my cock hardening in my pants, the pre-cum almost oozing out at this point. I took four of Sandy's bras, Ron taking the other, then set them aside. Without speaking a word, we knew what do do next.

We made out way out into the hallway and into Ashley's room, finding her hamper, this one was also green, and dumping it out. Again, mostly t-shirts, some tanktops, collared shirts and finally, 4 bras. We took those and brought them back into Sandy's room and dumped them in the piles we had made with Sandy's. Two of Ashley's bras each to go with the 4 each for Sandy's.

I was in the middle of unbuttoning my pants when Ron snapped his fingers and said, "Fuck, I completely fucking forgot!"

"What?" I asked. I remember there was nothing more than I wanted to do than spew my cum into the bras in front of me.

Ron jumped up and ran out of the room. I heard him run down the stairs and out the front door. I remember thinking, wtf is he doing as I took my pants off, then my boxers, my dick fully hard and erect, the head glistening with pre-cum from where my boxers had smeared it.

Ron came back in a second, running back up the stairs carrying a laptop and a projector in his arms.

"What the fuck is that," I asked.

Ron glanced at my dick and said, "Started already huh? Should have waited."

Ron proceeded to turn his laptop on, then looked around the room while it booted up. He plugged it into the projector and positioned it on Sandy's dressor, facing the wall at the head of her bed. He got up at one point and took a large picture of some landscape off the wall and then all of a sudden, his desktop popped up on the cream-colored wallpaper.

Ron looked over and said, "Okay turn around, this is a surprise."

I rolled my eyes and turned around, although I had a feeling I knew what he was doing. In a few seconds, he said, "Okay, turn back around."

I turned around to find a FB picture of Sandy in the green v-neck t-shirt blown up on the wall behind her bed. It was just like I remembered, I had the same picture on my computer. Nicely cropped to focus just on Sandy, she was wearing the green t-shirt with white pants. The v-neck was deep, revealing that massive flat upper chest that she had that Ashley had also inherited. It only accentuated how low her cleavage started on her chest bc the v-neck was so steep, yet you could still see no cleavage. Just the hint of the top of it before her two heavy, rounded full, breasts strained the shirt out and to the sides.

I was so pumped up I barely manged to say without my voice shaking slightly, "You are the man, that is amazing."

Ron already had his pants and boxers off, his dick also fully hard as he reached for one of Sandy's bras. I ran out at one point to get some folding chairs from the deck (longest few minutes of my life) and brought them back up.

We put the chairs at the foot of her bed, dumping the pile of 34DDD and 34DD cup bras on Sandy's sheets in front of us. Sitting in the chairs, we faced the wall at the head of her bed, staring at Sandy in her green t-shirt, with her mature, regal rack almost pushing out to us as if calling is to suck on her breasts.

For the next few hours, we edged like crazy, almost driving ourselves nuts. We stared at Sandy's tits in that green t-shirt, her smiling right back at us, as if watching us, knowing what we were doing. Her bed lay in front of us covered in her and Ashley's dirty bras and sweat-stained sports bras providing extra scenery to add to the experience of jerking to her massive MILF tits.

I don't know about Ron, but I alternated bras randomly, leaving some hanging around the bottom of my dick by the shoulder strap, wrapping my dick in one cup, then the other, sliding it up and down, then stopping before cumming to switch to another bra, letting the last one fall to the bottom of my dick with the others. Pretty soon, I had 3-4 bras hanging down from my dick with a 5th's DDD cups around my cock, the straps wound tightly around my shaft. I even put one of her sweaty sports bras in my mouth (LOL), tasting her tit sweat, the saltiness of it, turning that crusty sweat spot back into a wet one.

After a while both Ron and I exploded all over which ever bra we currently were jerking with. On mine, I filled one of the cups a pretty good amount, getting good coverage for all the fabric that held a DDD breast.

I used the other cup to clean up the rest of my cum that still leaked out of my cock. Ron did the same to his while I also used some of the shoulder straps and the bands to completely dry my dick, trying to cover as much of the bras as possible.

A few seconds later Ron and I hit the bathroom to wash our hands, then high-fived.

"Dude, that was amazing," I said. "That was a great fucking call getting the projector."

Ron went to put his clothes back on and said, "Yeah, I thought of it yesterday."

"Up for another round in a few?" I asked.

"Oh yea," he said. "Let's get recharged."

"This time in Ashley's room?"

"Oh yea," Ron said with a grin.

We ordered a pizza in the meantime and plopped down on the couch downstairs to watch TV and eat while we waited for our cum to regenerate for the next round of bra jerking. Covering 34DDD and 34DD bras is no easy task and we had two weeks to go.

The next week we only went home a few hours total. We spent the nights and days at Sandy's house, cumming into her bras at least 4-5 times a day, sometimes more. By the end of the first week, all of Sandy and Ashley's dirty bras were crusty with our dried cum and we still had a week to go.

What to do then?

Next:

Week 2, Ashley's Room

Week 2, Ashley's Room...Sort of:

The next week after immersing Sandy and Ashley's worn bras in loads and loads of cum in Sandy's room, Ron and I moved the chairs and projector into Ashley's room. Ashley's room was smaller but plenty of wall space to put her pictures up while we did our work.

Right now, we had a bunch of Sandy's 34DDD bras and Ashley's 34DD bras that were absolutely crusted with a week's worth of dry cum. They were unusable at this point and we knew they would probably hurt more than feel good.

We decided to toss them in the washing machine with no soap, at least we could wash some of the dry cum away and get them fresh without actually fully cleansing them. That way, some of the "tit residue" as we called it, would still be in the cups.

After they washed, we let them air dry.

"Think we should just go it with clean ones?" I asked.

"No," Ron said, "the dirty bras is almost the whole point, right?" *Ron was actually going through her clean bras at the time*

He had a point so we waited a few hours to let those amazing DDD and DD cups dry out. We got them from Sandy's bathroom and went into Ashley's room, the chairs already set up next to her bed, this time on the side bc of the way her room was laid out. Ron had the projector on with a picture of her wearing low cut white top covering a large portion of the wall.

I won't go into the details of jerking with the bras again, but it was just as hot as it always was. The feeling of those cups encircling our dicks, the thick straps hanging down, sometimes wrapped around the shafts, the taste of their scent left over from Sandy and Ashley's heavy hanging breasts that had once been slightly squished against the cups.

I know I came at least 5 times in those bras that day over 8-10 hours. By that time, Ron and I knew we had to come up with a new idea to last the rest of the week. Being alone in Sandy and Ashley's house needed to be fully taken advantage of so we had to come up with something creative.

Ron and I sat on the couch in the living room trying to figure something, the TV was on and we had our feet up. We had all the time in the world, so there was no rush anyway.

"So what do you think?", Ron asked.

"I don't know, we need something to make an impression."

Finally, I said, "You know, that one time back in the day when we left the party here and we put some of our cum on their shirts when we hugged and then left? I thought about that every day and it turned me on so much knowing our cum was just staining those tits the entire evening."

Ron said, "That was amazing. What are you thinking?"

I remember I said, "Let's do it on a larger scale."

I stood up, took my shirt off, then my boxers (that's all we were wearing). Ron laughed and said, "Wtf are u doing?"

I wasn't ashamed to be naked in front of him, we played on the same varsity teams for multiple sports. What was good about Ron was that we were both strictly straight, no touching, but no discomfort with seeing the other naked.

I picked up one of Sandy's 34DDD bras and one of Ashley's DD cupped ones, left them hang down from the shoulder straps from my dick as always and began to walk naked out of the room.

"Dude, what are you doing?" Ron said again.

I remember I turned back, the bras hanging down from my erect, already leaking dick from the thought I had, and said, "I'm going to walk around this house, jerking into these bras and I'm going to cum on something in whatever room I'm in."

I checked my watch. "And I'm going to do it until I can't go anymore".

Ron stood up and did the same as I did and we split up, walking naked around Sandy and Ashley's house, their bras wrapped around our dicks, jerking as we went. A little while later, Ron and I both walked into the kitchen and laughed when we saw one another.

"We think a like," Ron said, heading for the fridge.

I laughed, "Oh yea, first stop is definitely the kitchen."

A few minutes later we were jerking in front of the open fridge and then both exploded into the bra cups, saturating the inside of the fabric.

We were about two minutes apart but both our loads were still pretty big, even after a full weeks worth of jerking off 4-5 times a day.

I remember scooping that first load out of the bra cup, reaching for the gallon of 2% milk in the fridge, taking the cap off, and scrapping my cum into the opening. Then I put the cap back on and shook the jug, mixing my cum with the milk. I have to tell you, I almost got right back in the mood to jerk again with the thought of them pouring that milk into their cereal when they were back, unknowingly devouring my cum that was now evenly saturated in the milk.

Hilariously, Ron was smearing his cum on the inner part of the door handle to the fridge. He said, "You stole my idea.....guess first cummer gets first choice."

I laughed and said, "The door handle, wtf?"

Ron shrugged. "It'll be dry and I'll know they've been touching it."

We spent the rest of the week doing the same routine, walking around the house, jerking into their bras and cumming on whatever we could. We didn't try to make it obvious. I personally dumped cum on Ashley's toothbrush, checking later to see what it felt like. The brush was stiff like it normally is when not being used or wet. Perfect.

I also left a load for Sandy in her bodywash bottle in the shower, knowing she would be rubbing my cum all over her massive, heavy, hanging round breasts and foot long cleavage with her first shower back home.

More of my cum from that week I put on the underside of Ashley and Sandy's sheets, knowing they wouldn't see it, but they'd be touching it. It would definitely be crusty, and it might have a little risk, but at the time I was so pumped up at the thought, I wiped my hand clean on both sheets, pulling them back in place after.

Ron and I left our cum in many of the same places where we knew they'd be touching and/or touching themselves after. Ron left a nice sized load (according to him ) in one of Ashley's hand lotion bottles, Sandy's tooth brush, and in a box of cereal, knowing his cum would be dry and unoticable on the stiff, sugary cereal when in a few hours.

The next week, we covered many objects with our loads, put cum in lotion bottles, shampoo, on soap, in food, everywhere we could. It was our way of leaving a mark of thanks, honoring them for the two weeks, for their sets of low-starting, heavy breasts, for the massive loads, for the bras, and just for being the m other - d aughter pair we'd been jerking to for almost a year.

They haven't said a word since, and if they did notice, they haven't brought it up. But I still know, Sandy and Ashley's house will always been decorated with loads and loads of our cum, cum that Sandy and Ashley had rubbed on their pendulous breasts, cum that they had eaten or drank, cum that they had rubbed on their hands and bodies, cum that they had slept in and covered their teeth in from brushing.