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
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