We recently moved into a completely new area. It was a new housing development and there were loads of young families and child-free couples who had taken advantage of the widely available quality housing. Suffice to say there was plenty of eye candy for my late thirties eyes to feast on. I'm Bill, I'm married with a couple of kids. I'm tall, with short grey hair, dark brown eyes, a little overweight and a bit bored of my sex life at home.
We'd been in around a week and it was evidently bin day coming up as everyone was putting their stuff out the front for collection. We had no idea what was expected in terms of separating stuff out for recycling or what have you so I decided to go and quiz a neighbour on protocol. I knocked on a couple of doors but folks were out.
Eventually I found someone in. She introduced herself as Ellie. She would be in her mid twenties at a guess, around 5 and half feet tall with dark hair, dark eyes, a pretty smile and thick fashionable glasses. She had a pretty trim looking figure but what I noticed straight away was the swell of her breasts. I'm definitely a boobs man and these looked pretty awesome. She was wearing a relatively low cut vest top and I could see the swell of her cleavage from her push up bra. I'm guessing they would be around a D cup.
Ellie filled me in on the protocol for recycling. As she did so she bent over to put some stuff in a recycling box and I got a great view down her top of her cleavage, all the way down to the little red bow on the front of her black and red bra: delightful. As she stood up again I was fairly sure she caught me checking her out but she didn't let on.
We chatted about a few things as she continued fiddling around with the contents of her boxes which allowed me a few more flashes of her boobs. I told her about my job and the fact that I work from home most days. She told he about her husband who worked away from home a lot. Soon though, having found the information I was after, and had a bonus lech session I had to get back home to sort out our bins. Later, after my wife was in bed I jacked myself off to the memory of Ellie's cleavage.
The next day my wife had to go out to take the kids to an activity. I was busy working when there was a knock at the door. It was Ellie. She was wearing jeans and a similar top to the day before, although if anything it was slightly lower cut. She smiled at me and asked if she could step inside as she had to ask me a question.
I welcomed her in and asked her if she wanted a drink or anything. She said no as she launched straight into what she had come to say.
"Bill, I'm sorry if this is a little forward, but I really have to know, and please don't lie. Yesterday, when I was putting stuff in my bins, did you take a look down my top? I'm sorry it's so personal. I just really have to know."
She blushed as she was talking. My head started whirring. I couldn't decide what the best course of action was. Do I confess and end up alienating a neighbour already? Do I lie, and risk alienating her even more? Eventually I had to make a decision and answer her.
"Yes," I said carefully. "Yes I did steal a couple of glances down your top. To be honest it was hard not to."
"I thought so!" she continued. "I was pretty sure I'd seen you looking. You're right it was hard not to. My top was pretty low, and you're a guy. I'm glad I was right. Do you mind me asking, did you like what you saw?"
This was turning into an interesting conversation and I decided to be a little more open with her.
"Yes, very much, Ellie," I replied. "In fact, I'll let you in on a secret, after my wife was asleep I had a wank whilst thinking about what I saw. I hope that's ok!"
"Ummm," Ellie said, blushing again. "Well yes I suppose that's ok. It's just that, well, I'm very conscious about these big lumps in front of me. They're so much bigger than when I married my husband. I'm guessing I was a late developer. Anyhow, he doesn't like how big they are and keeps telling me I should have reduction surgery. As a result I hate them. They come between us, literally. I can't see how anyone could like them or like looking at them."
She had started crying. I really didn't know what to do. She was practically a stranger. In the end the softie in me took over and I put my arms round her and held her as she sobbed, letting it all out. After a while she calmed down and I handed her a box of tissues.
"Thanks," she said shyly. "I'm really sorry about this, Bill. I hardly know you. I shouldn't be breaking down like this in front of you. At the same time it feels loads better!"
We sat in silence whilst she dried her face and pulled herself together a bit more.
"I've had an idea!" she suddenly exclaimed. "You like the look of my boobs. Why don't you help me come to terms with them and help me feel better about them?"
"I'm not sure I understand how I can help really, Ellie."
"I'm sure you'll work it out, Bill. Basically, I've spent so much time and effort trying to make them seem smaller and hiding them away when my husband is around. When he's not around, like last night, I tend to be a bit more relaxed otherwise I'd do myself in. That's why I was wearing what you saw. But at most times I wear boring frumpy clothes in an attempt to hide what's there. It's obviously paid a heavy toll on my self image. Why don't you help me by telling me what you like and don't like and I'll try things out. Maybe that way my confidence will grow. As for you, well you'll get to stare at my boobs without having to shy away. What do you say?"
I gave the impression I was thinking it over carefully, but how could I turn her down? "Alright," I eventually said, "I'll give it a go!"
She beamed at me and asked if I would like to get started right away. I agreed and so we went back to her house as she had all her clothes there.
She started by pulling out loads of sports bras and tight camisole tight things explaining that this is what she wears normally when her husband is around to try and reduce the size of things and to keep things well hidden.
"You see my predicament. Help me!" she pleaded.
"OK," I said, "first of all you need to feel comfortable in all areas, as well as feeling good about your general look. You said you tend to dress frumpily. I'm guessing that includes wearing jeans and so on?" She nodded, so I continued. "No problem, jeans are good, but you need to feel better about the way you look, so I want you to select a skirt you like wearing and put that on. Don't change anything else."
She rummaged around in the wardrobe and pulled out a short looking number and headed off to the bathroom to change. She explained that she had to shave her legs so might be some time. She invited me to have a look through her clothes and see what sorts of things she could try on.
I started by looking at the underwear drawer. I made a mental note that she tended to favour tiny thongs. Something for my masturbation session later! In terms of bras, she had the horrible things she'd shown me earlier, and a small selection of pretty looking push up bras. They were all 32D. In terms of clothes, she had a lot of frumpy stuff as she'd explained, like t-shirts and hoodies and so on, but there was a small collection of nicer stuff as well. This included some short skirts, some more of those vest tops, some blouses and a couple of little black dresses that looked like they might have been from the smaller breast days.
After around twenty minutes Ellie came back in. She was now wearing her skirt. It was a pretty short one, finishing just above mid thigh. It was pleated and quite loose. Her legs were nicely tanned and very shapely.
"You're right," she exclaimed as she walked in. "I do feel better already. I've not worn a skirt like this for ages, hence the unshaven legs. Have you had a look through my clothes? Anything we can work with?"
"Yes definitely," I replied. "Not a massive amount, but there's stuff to be going on with. Can I say though, you look delightful in that skirt."
She beamed at me and bent over affording me a great view down her top.
"Let's get to work then," she bubbled. "I'm actually feeling quite excited, and definitely a little naughty as you're practically a stranger! What do you have in mind?" She winked at me as she said this and I felt a slight stirring in my loins. I wondered where this would go.
"Ok Ellie, let's get started, but if I ask you to try anything you don't feel comfortable with then please say. I think part of the problem is that you have two extremes of underwear. You've got the flattening type for your husband, and then the push up type. The latter must feel really odd in comparison to the former. In the absence of anything in between though, do you ever, or have you ever considered going braless?"
"No not these days, Bill. I used to quite a bit, but don't you think these are too big for it? Won't they just sag or look funny? What if my nipples poke through?"
"I can't say if they'll sag, but you're young so I doubt it. As for looking funny, anyone who says that is clearly stupid. And nipples poking out is half the fun of going braless in my book. I love the sight of braless breasts. I love the way they bounce. It's really enticing and exciting to watch. I completely understand if you don't want to try it. At the same time, I think these push up bras are making mountains out of molehills in your mind by accentuating the cleavage. There's nothing wrong with that and you look great. I just think it will help your mind if there's some middle ground."
Ellie looked at me for a while. She started plucking on her bra strap absent-mindedly. Eventually she nodded, turned on her heal and went back to the bathroom. When she returned a couple of minutes later she was carrying her black and red bra in her hand and looked a little embarrassed. Nevertheless she strutted over to me and dropped the bra in my lap. The change had certainly reduced the volume of the cleavage, but she looked even more enticing, particularly as her top didn't cover much of her braless breasts. She looked ravishing and there was a lovely amount of jiggle as she walked. I didn't want to blow it, but I was sorely tempted to give her a squeeze.
"Does that feel better, Ellie?" I asked.
"It's strange," she answered. "It does actually feel pretty good. I think you were right about the extremes. I certainly wouldn't go out like this for fear someone might see what they're not welcome to, but for around the house this would be great when hubby's not here at least. What do you think? Is it an improvement?"
"Yes a major improvement in my book, although I can't give a full assessment yet as you haven't given me the same angled views as you have before yet," I replied with a cheeky glint in my eye.
