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Another great chapter! Love the mix of masturbation based experience and moments with both women!
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Part 8: Hands Free Tit Fuck

A few weeks later, after Sandy and Ashley got back from their trip, Ashley and I headed to the gym. It was a Saturday, the air was humid and really wet, almost like you could drink it. It was one of those days like when Ashley and I took that walk, her braless in her pink dress, her heavy breasts swaying as she walked, her tits gently clapping into each other. The same weather as when she let me suck her sweaty tits for a few minutes after our walk.

Saturdays were always the days Ashley and I went to the gym together. I usually like to workout alone so I can get stuff done, and with Ashley there, keeping my eyes off those heavy breasts is a bit of a challenge. Especially when they are packed into a sports bra under a tanktop.

After the workout and a long run, Ashley and I headed home to my place to shower before we went to get a bite to eat. I remember being in the car with her, her sweaty scent filling it as the AC blew it all around the interior. Streaks of sweat ran down the tops of her breasts, which swelled in her sports bra, some of them spilling into her deep cleavage, which was now curved from the support of the fabric.

I, on the other hand, for some reason that day was feeling especially turned on. My mind was focused not only on Ashley's sticky, sweaty, breasts in that sports bra, bouncing every time we hit a slight bump, jiggling as if made of water, but also my dick in my shorts, sticky, also sweaty, trapped in some under armour that made the air inside moist and humid around it. I could think of no better than I wanted it to be right then than between Ashley's tits, chaffing the skin on both her breasts and my cock, letting the sweat sooth it.

What's more, the seatbelt sliced diagonally through her tits, or at least tried to bc of they were packeed into a sports bra, squishing them even more against each other. I wondered what they would look like with the belt going through them if she was wearing one of her low cut shirts, her tits fully hanging as she tended to let them.

After I think the 4th time I purposely hit a bump in the road just to get a glimpse of Ashley's tits bounce, she reached over and hit me on the shoulder.

"Are you like purposely hitting bumps in the road?" She asked, laughing.

"Yeah, I said. Because your boobs jiggle every time I do," I said, trying to come off as joking as we always did.

Ashley laughed again and said, "You suck, what is with you and my boobs anyway, that's like literally the only place you EVER cum."

I remember I almost said because I had obsessed over them forever, but I knew that sounded a little creepy and desperate so I just said, "I dont know, I'm a guy, I like tits?"

Ashley rolled her eyes and said, "I don't think I've met a guy more into tits than you though."

"Bullshit, well, every guy is different obviously, but whatever we're into, we're INTO it," I said, almost serious now as if trying to come off as suave.

Ashley then turned to face me slightly, reacing up with her hands to the top of her sports bra that was sticking up above the curving neckline of her tanktop. I remember she accidentally scratched her chest with her nails as she did so because she said, "Ow fuck!" and started laughing.

I laughed along too, but brought it right back to the point. "What were you trying to do?"

Ashley faced me again and pulled the top of her sports bra down, revealing the squished up tops of her breasts, the sports bra so tight, a faint amount of veins appeared, her skin still sticky and shiney with sweat, slightly bumpy now with the AC blowing through the car, her cleavage not a sharp curve in the great amount of support from the sports bra, not a straight line.

Ashley laughed and shook her shoulders side to side, her tits moving with them as they were packed in tight in the sports bra, only made tighter with the top pulled down, squeezing them up.

"Don't crash," she teased.

"You're gonna have to do a little better than that," I said, laughing.

Ashley looked down, put both her hands on the right side of the sports bra and pulled it down even further, her dark pink nipple popping out, just above the top of the fabric.

"Oh, there it is," Ashley said, "Hahaha. I was like where are they?"

She teased me like that the rest of the way home, smirking, and laughing and joking. I gave it right back until we pulled into her driveway. Then I grabbed her by the hand, pulled her towards me, and started making out as passionately as I could. We were in the car for about 5 minutes, my hands groping her breasts, feeling the wetness of the sports bra stained with sweat, the now firmness of her well supported tits.

Minutes later we were in her room both feeling hot, getting more and more intense as we made out. I decided at one moment, that I was going to take control of this time around. I remember thinking what did I really want to do? Did I want to fuck her? Did I want to tit fuck her? What did I want to really do?

I pulled Ashley's white tank top off, she raised her arms above her head as it slid past her, her tightly packed breasts stretching slightly as her arms went high, only to come back down as one when they lowered.

She began to reach for her sports bra but I stopped her.

"Leave it on," I said.

She gave me a weird look and I said, "You'll see."

"Uh okay?" Ashley said, looking at me with weirdly.

She then reached for her tight gym shorts, but I also stopped her.

"Those too," I said.

Ashley threw her hands up, then reached behind her to retie her hair. I remember because her arms went behind her head, exposing her smooth armpits. I've never had an armpit fetish before, but something about seeing their smoothness and the way the sides of her tits ran into them drove me nuts.

I shoved Ashley to her knees by her shoulders, then I reached down, and pulled the bottom of her green sports bra towards me. With my dick already hard and out, I knelt down slightly and slipped it under her sports bra, poking at the bottom of her right breast, moving my dick slightly to the left until it found the tight gap that was her normally wide, low-hanging cleavage.

It felt amazing. My dick was sweaty and sticky already, and going into the sports bra, between her tightly held tits, both of her heavy breasts squeezing my dick from both sides, the moistness and stickiness almost made me explode right then.

It didn't quite feel like going into a pussy, but it was close. It might have been better because while Ashley had a great one, it was her tits that I always was obsessed with. Probably why I've never jerked off into her panties, just her bras.

Her breasts were incredibly sticky. Her cleavage was so tight around my dick, her skin moist and almost slimey with sweat. The sports bra trapped all the air inside, growing even hotter with the heat of my dick inside.

Ashley laughed and said, "Wow, a tit fuck, who would have guessed you would have wanted a tit fuck. And now I can do it hands free."

I laughed out loud and began thrusting my dick up and down, but this proved hard with me standing.

As quickly as possible, I tried to pull my dick out the bottom of her sports bra but it didn't move. We laughed as she pulled the bottom forward, letting me escape before I sat down on the bed, my legs hanging down.

Ashley walked over on her knees, then pushed my dick back into her sports bra, back between her heavy breasts. She began to move her tits up and down on either side of my dick, her hands on the bed supporting her, the sports bra holding them together. The tip of my dick started coming up the top of her cleavage and she looked down at it as she continued to grind her sweaty tits up and down my dick, grinding on the inside of her smelly cleavage.

At on point she looked up and said, "We smell terrible."

I laughed and didn't say anything but it added to the experience. Having a hot, nasty, sweaty tit fuck, was one of my fantasies. Now I was living it, with Ashley, the girl whose tits I had obsessed over the most out of anybody.

Ashley continued to move her packed rack up and down my shaft, getting to the point where it hurt, my dick was chaffing the inside of her tits, the skin on the upper parts of her inner breasts turning red as my cock kept popping up the top.

The sweat and smell only increased as she continued to push her breasts up and down, up and down, slight pain on her face as her tits chaffed with sweat.

A few minutes later I pulled my dick out of her sports bra and began to take if off her. She was so sweat at that point, she had to do it herself, and struggled out of it, which only made it hotter when her packed in breasts, bounced out the bottom of it. Ashley let the bra go for a second, the elastic band squeezing down on her upper chest, making her heavy, already bolbous breasts swell until she finally pulled the bra off.

Her breasts looked incredible. They hung down as usual, her vast flat upper chest, curving down as always into a long line of cleavage that started low, then gradually curved down into two heavy, full, rounded breasts.

They were sweaty, shiney with the sweat, sticky to the touch, the bumps on her skin only amplified by the moistness of her skin. Her entire cleavage was red and raw, as well as the inner sides of both her breasts.

I immediately stood up and grabbed her arm, I think it was her left one, and raised it above her head.

"What the fuck?" Ashley said.

I didn't say anything, but stood behind her, still holding her arm up, and slid my dick into her armpit, bringing her arm down.

Ashley laughed and almost pulled away saying, "What the actual fuck, James?"

"Shut up," I said, laughing and began thrusting my dick back and forth in her armpit, the head of it slamming into the side of her left breast, jiggling it, causing that water effect, my thrusts causing her body to move back and forth, her right breast swaying, clapping softly back into the left one which was how slightly firmer because of the position of her arm.

After a few minutes, I figured there was enough sweat from her tits, my dick, and from her bare armpits. I pulled out of her armpit, came around front, and pulled her towards me.

Ashley turned her head away, saying, "Uh no, we smell bad, James."

I took her head and firmly but gently pushed her back towards my sweat stained dick, taking a hold of it with my hand, pressing it to her slips and then sliding it into her mouth.

Ashley fought a bit to back off, but I held her head firmly and kept my cock in her wet, hot, mouth. The tip of it touched the back of her throat and she gagged on it, the drool dripping out the side of her mouth. I could see her brow was furrowed, as if she had just eaten something that tasted bad.

I began moving her mouth up and down, feeling the sliminess of her drool drip out her mouth, running down her chin and into the top of her breasts. Ashley put her hands on my thighs and kept moving her head up and down, more and more willingly, twisting her head side to side slightly as she moved her tongue and lips up and down my shaft. Her breasts swayed side to side, back and forth as she aggressively began ramming her mouth down to the base of my dick, choking each time.

"Mmmmph, mmmmph, mmmmph," were the noises she made before letting out a loud "Gawk" when her mouth reached the base of my dick.

My pre-cum began leaking out of her mouth mixed with her saliva, dripping down and splattering the tops of her hanging breasts, some of it flying off as they clapped together. Looking down, she was a mess. She was covered in a thin sheen of sweat, her skin was sticky, her breasts red and raw, her saliva running in streaks down her full, heavy tits, my precum mixing with it. Her make up was running, her hair was a mess, she smelled bad, but so did I. And she had never looked sexier.

The smell of our body odor wafted over us, the stench of her breasts and my dick, all of which had been trapped inside tightly fitting under armour gym clothes was finally released, only to be mixed in with the smell of cum, pre-cum at least, saliva, and sweat. It was ripe, it was almost rancid, but we were both lost in it.

After a few more minutes, I could feel myself starting to explode so I made Ashley stop sucking my saliva drenched, sweat stained dick, and reached for her sports bra. Breathlessly I said, "Put this back on."

Ashley didn't say anything, but wormed her way back into her sports bra, pulling it down tightly over her breasts, one after the other (left after right, I remember) then letting the bottom of it snap into place, bringing them up slightly, the long line of cleavage shortening into a slightly curved line.

I sat back on the bed as Ashley put my dick back under her sports bra between her now sweaty, stinking, saliva and pre-cum stained breasts, which not also soaked the inside of her sports bra. She began moving her breasts up and down again, using her arms to push herself, almost like pushups.

A few seconds later I exploded inside her sports bra. I remember I came then my dick was at the bottom have of the movement and I quickly thrust up, the head of my dick poking between the top of her tits with my cum shooting out. Some of it hit her on the chin, with the rest spilling over onto the top of breasts, running down them, staining the outter part of her sports bra.

A few more thrusts and I pulled my dick out. It was now that I actually felt it hurt because it was just as red and raw from the chaffing as Ashley's tits and her cleavage were.

Ashley began laughing as she looked down at her cum covered sports bra, squeezing her shoulders together to mash her breasts closer.

"That feels sooooooo nasty," she said, laughing. "Your cum is hot and sticky and gross, and I just look like a wreck."

"You look so hot right now," I said, laughing. "Thanks for that."

Ashley gave my gradually softening dick a little slap, and said, "Anytime."

She got up, her sports bra covered in dark spots and drips of cum, the tops of her breasts glistening with her saliva, cum, and sweat. She reached up behind her and let her hair fall, looking at her left armpit as she did.

She turned around and made her way towards the bathroom before saying, "Okay, now can I shower?"

"Yeah," I said, laughing.

"I think next time we should just be clean before we fuck, tit fuck, or whatever weird thing you want to do next, but this was hot," she said. She walked out of the room, leaving me to clean myself up, then head to the guest shower.
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creamyking Novice Jackinchatter

45 posts since 2018-03-07
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so hot maaannnnnn!!!!!

again, if you could add some photos to this ....would be awesome cockcockcockcockcockstrokestrokestrokestrokestroke
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Again, wow!!! As I slowly edged my slowly engorging penis, there was so much from this story I loved, and which quickly got me to wonderful edge: the descriptions of the little things about her tits, their shape, the movement of them, how she teased you in the car journey (I have an ex who did something simila in the way she moved that teased the hell out of me, and I loved it so I could really imagine that!), the descriptions of the smells, the rough play you two did, how sexy you found her when she was at her rawest... all so, so good! I am truly worked up now! cockcockcockcock strokestrokestroke
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Thanks for the feedback!!! If people keep letting me know they like them, I'll keep writing as much as I can remember.
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maximillion_16 Amateur Jackinchatter

406 posts since 2013-01-20
33 year old bisexual male from UK
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Love these stories! I've been stroking cock while reading them stroke
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creamyking Novice Jackinchatter

45 posts since 2018-03-07
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some photos pls strokestrokestrokestroke
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maximillion_16 Amateur Jackinchatter

406 posts since 2013-01-20
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strokeCan't wait for the next installment stroke
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Been busy for a bit, working on the latest chapter, coming soon!
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maximillion_16 Amateur Jackinchatter

406 posts since 2013-01-20
33 year old bisexual male from UK
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Love the stories! Looking forward to jerking my cock to the next chapter!
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sdmattfreeman Amateur Jackinchatter

426 posts since 2015-11-30
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Keep it going! Loving this!
Fun group on Wickr: [email protected]. 21+ only, all the time.
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sdmattfreeman Amateur Jackinchatter

426 posts since 2015-11-30
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Any more?
Fun group on Wickr: [email protected]. 21+ only, all the time.
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Sorry guys, had to delete for a while. Back and will continue writing
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Part 9: Overhearing Sandy's Bra Conversation

This chapter might be boring for some people, but I'm just telling you how it happened. This wasn't really a big deal, but something I will always remember and wish I had recorded bc I would luv to have jerked off to it over and over again. But I do remember very vividly what was said. It's a short one, but would luv feedback. And as usual, if u want to have a chat and see pics of Sandy and Ashley, skype me!

A while ago, I went over to Sandy and Ashley's house to pick Ashley up to go to one of our friend's houses. Ashley was still on her run when I got there apparently bc the door was opened by Sandy.

"Hi James, Ashley's still out running but come on in," she said. She was wearing a white button up shirt with a aqua tank top underneath. As usual, her heavy breasts hung low on her chest, straining the fabric of the tank top and the thin white button shit. She kept the first four buttons of it unbuttoned revealed her massive flat upper chest area, bronzed by the sun, slightly freckled with a hint of age spots. As usual, that massive flat upper chest sloped gently down to the beginnings of her long cleavage which was just peeking up above the tank top before finally curving down into those wonderful heavy, bulbous tits.

I followed her into the kitchen where her friend Debra was sitting. Now Debra was also a MILF, not quite as hot as Sandy, but fit like her, heavy breasts, only a brunette. She was wearing a plain grey t-shirt and the first thing I noticed were that her breasts sat higher than Sandy's, which was not surprising. They were having drinks at the kitchen table so Sandy sat back down.

"You can wait in the living room if you want," she said, bending forward slightly as she sat, giving a look into the deep cavern that was her cleavage. "Or you can sit here with us, but we're talking about lady things," she laughed.

I laughed as well and said, "That's okay, I won't intrude on the secret club meeting."

Both women laughed and I went into the living room.

After a few minutes, I was on my phone, listening to their conversation in the next room but not really registering it. I remember hearing the word "bra" and was immediately drawn into their talking, straining to hear. I remember this conversation very very well.

Debra: Well we're just so busty, and I'm sure you have this issue to, but mine just ache at the end of the day. Sometimes I don't even want to wear a bra, maybe I'm just old.

Sandy: I have my secrets on how to handle it.

Debra: Secrets?

Sandy: You have yours constantly pushed up, Deb. If you want more comfort, you need to let them sit more naturally.

Debra: So, what, not wear a bra? You're wearing a bra right now!

Sandy: Yes, but you have to consider the band size. What are you, a 36?

Debra: Yupp.

Sandy: So my band size is a 36 as well, my cup size is DDD. Most of the time I lengthen the shoulder straps almost as far as they can go and I wear the band lower around my torso.

Debra: Ohhh, okay, so you hear it below your ribcage?

Sandy: Well at the bottom half, below my rib cage would be at my stomach. I'm not trying to have the grandma breasts just YET.

*Both laugh*

Debra: Your breasts do always sit rather low, I've noticed.

Sandy: And they feel fine at the end of the day; give it a shot sometime.

Debra: I will, mine are packed into a sports bra right now.

Sandy: Well, I don't have an secrets with sports bras, but with regular bras, try wearing the band lower and lengthening the shoulder straps.

At this point I noticed that pre-cum was leaking and staining my boxers. It was such a simple conversation, but the topic made my dick leak and harden like crazy. I was half tempted during it to whip it out right there in their living room and jerk off listening to them. It's not like I hadn't jerked off in Sandy's house before grin. Just picturing Sandy sitting in her bedroom, where Ron and I had jerked off to her photos, adjusting the clasps on her thick bra straps to lengthen them....the very same bras Ron and I had wrapped around our dicks, whose bra cups we had filled (or attempted to fill, DDD is pretty big) with our cum, drove me nuts.

Ashley got home a few minutes later, and to be honest, I don't think I heard half of what she said that night. Just thinking about Sandy's voice talking about her own bras and breasts drained all the blood from my body and sent it right to my dick. I actually couldn't wait to get home and have a good long jerk thinking of Sandy's voice talking about her heavy hanging tits and how she kept them comfortable with her bra adjustments.
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A perfect, teasing conversation, leaving lots to the imagination, and as always lovely descriptions of the two women! That really turned me on!
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