After having broken up with my long term girlfriend, and returning home from the ski trip where I mutually masturbated with my friend's older sister (see my Cabin with a Hot Tub story if you're curious), things had gotten rather mundane for a few months. Working as a software engineer and having recently been promoted, I was working a lot and didn't have much of a social life, spending my evenings and weekends playing games online and getting drunk.
One of our Minecraft servers grew quite large, our largest in fact, which probably due to the game's wide audience appeal. With so many people on it, the game's chat feature quickly became annoying and limited, so a few of us software developers decided to code up a web chat app as a side project. Initially planned it was to be pretty bare bones, but we quickly got a bit competitive with each other (all good natured though) and before we knew it we had spun up a rather feature laden site, with audio/video, different rooms for different games and topics, private messaging, the works. We decided to keep it small though, so it was never indexed for Google or any other search engine results, and the repo was kept private.
One day I logged into the main chat room, and saw maybe 6 other faces. The first 5 were familiar but there was one that was new to me. Her name was Abby. Apparently one of the other developers that worked with her had told her about it. Having never seen her in the room before, I sent a private message welcoming her and just getting to know her.
From those messages, I concluded pretty quickly that she was educated, smart, independent, yet stubborn and somewhat withdrawn. We were the same age (27 at that time), and with me living in Chicago and her in Boston, we shared a similar mentality and love for baseball. I envied the Sox recent success, and she lamented the Cub's persistent failures, though they were looking up and would actually win the World Series the next year. Our conversations were natural and unforced.
Physically, from what I could make out on the small video from her camera, Abby had more of an "average girl next door" attractiveness to her more than she did a magazine cover look. She was overweight but appeared to carry it well enough. She was pretty in her own way - her face wasn't fat but she did have a small double chin. Her nose was rather long, her eyes were dark brown, and her lips weren't small but weren't big either. Her jet black curly hair contrasted her white pale skin, and she had a hint of sideburn in front of her ears which poked through her hair which I found tremendously sexy. And, from the looks of the deep cleavage she occasionally showed, she had an enormous set of tits. My best estimation is that she was a sexy BBW in every sense of the word, which I'd confirm a few months later. This is that story.
As the days, weeks, months went on, we became quite friendly, having exchanged numbers, occasionally texting throughout the day. Our conversations began to border on flirtatious, but with her having a boyfriend in addition to the distance, that's as far as things had gone.
One night in the main room, an interesting topic came up. It was the double standard of grooming expectations between men and women. Apparently one of the regular girls in the room recently went on a date, reporting the guy had "the smallest hairiest penis" as well as the nerve to complain about her self reported closely cropped triangle. Abby was in the room, but not participating in the chat and her camera was off. I just assumed she was away. While it was mostly the girls commiserating with one another, I offered up to the group that I thought a woman's body was her own choice and that I didn't mind the natural look. My comment was mostly ignored, but a few minutes later I received a PM from Abby.
"Wish more guys were like you," she messaged me.
"Huh?" I answered. The conversation in the main room had since shifted, and I was more focused on a game I was playing anyway.
"Not minding a natural girl," she explained.
"Oh, well, I actually prefer it," I clarified, not sure where this was headed.
"Ugh, that's what I mean. Rob wants me to shave, but I hate it," she went on. (Rob was her boyfriend).
"Most guys I know like it shaved. But I think a bush looks womanly," I offered.
"Hypocrites. I think they should consider returning the favor."
"Does Rob return the favor?" I asked, assuming she shaved for him.
"Not really, no. I mean if I'm going to do what he wants, he should do what I want."
"That is a bit of double standard then..." I offered. I didn't get a response for a few minutes. I figured she was away again.
"Yeah. When we met he shaved. I wish he didn't," she eventually replied ten or fifteen minutes later.
"Oh?" I inquired, genuinely surprised.
"I asked him about it eventually. He said he thought it's what girls wanted. And that it made him look bigger. I told him I thought it was more manly not to worry about size or give into others' expectations. It's confident. That's way more important than size."
"Did he stop for you?" I asked timidly, not totally comfortable asking about Abby's boyfriend's pubic hair situation.
"He trims, but still doesn't leave very much," was her quick reply. I hesitated before taking a shot.
"Do you..." I hesitated, nervous how my question would land. "Do you shave for him?" I apprehensively hit send.
"No." she answered quickly. I didn't really know what to say next. I was certainly intrigued, and a little turned on by this information. But we had never come close to this level of intimate conversation until now. While trying to think of how to reply, I removed my shorts, opened a private browser tab, and was quickly searching for some familiar porn favorites.
"That's hot," I replied meagerly.
"Really?"
"Yeah, really," I confirmed.
"What about you?" she followed up with turning the question on me.
"Sometimes. If I'm seeing someone, and that's what they like. My ex preferred that I at least trimmed" I replied.
"What about now? I know you're not dating anyone," she insisted.
"No, haven't had any reason to. I'm back to being natural," I answered honestly, looking down at the bushy forest surrounding my cock, growing a little up the shaft and covering my balls.
"Hot," was all she said. Again, not really knowing how to respond, I eventually replied.
"Thanks"
I switched back to my private window, watching a classic scene where Christy Canyon is sucking and fucking some guy on a large brown leather couch, gently massaging my cock and balls. Five or ten minutes pass before she sends another message.
"Sorry, that was a little personal," she had typed.
"No, not at all. It actually... well..."
"What?" she asked.
"It was exciting. Surprising, but exciting."
"Exciting?" she asked.
"Yeah, I don't know. Especially since you can basically assume most girls are basically bare, it's exciting knowing there's some full bushes out there."
"I guess lol. Exciting as in.... are you hard?"
"Umm... yeah," I confessed.
"Really?"
"Yes."
"Prove it." I was a bit shocked.
"What?"
"Prove it - show me!" She dared me.
"Really? What about Rob?" I replied and regretted it. I'd love to show Abby my cock, but worried bringing up her boyfriend would change her mind.
"He's not here. And he doesn't check my phone anyway" she said. I was not quite sure how that made things more ok but whatever. I wouldn't really want anyone I was dating soliciting dick pics from other guys.
"What do I get out of it?" I pushed.
"You get to show me your penis."
"Are you gonna show me something too?"
"Oh yeah? Like what?" she teased.
"Well, considering what you just told me, your bush," I didn't want to leave any room for ambiguity.
"We'll see. I'm shy. Maybe I'll show you."
"Ok, I'll show you. One sec," I relented, hoping that maybe would turn into a definitely. I reached for my phone, opened the camera and aimed it at erect cock, intending to snap a picture and text it to her. But then I had a better idea.
Having been one of the "founders" of the site, I had permission to some admin-only features that weren't available for regular users. I navigated to the admin panel, created a password protected room, setting the password as "thiswasyouridea." I messaged Abby the url and login details. I turned my camera off and left the main room. She entered the private room just moments after I did.
"One rule, we each cam on," I typed into the chat. Since it was just the two of us, there was no reason to use private messaging. Her video appeared almost immediately. She was reclined on her couch as usual, but it was clear she was nude from at least the waist up. The angle of her screen was aimed too high to see much, but clearly showed her naked shoulders, devoid of any bra straps, and the beginning of her substantial cleavage. Abby unmuted herself and I did too. The audio feature wasn't used very often, since the more crowded rooms it just resulted in incoherent clashing conversation. But it made sense now that it was just us two.
"How did you make this?" She asked me. It was the first time I had heard her voice. It was cute, higher pitched, and daintier than I was expecting.
"Oh, I don't know if I told you. I helped code this chat. I can do admin stuff regular users can't."
"Oh, showing off now, are we?" She mocked me slightly.
"Not yet," I smirked, knowing exactly how to respond.
I aimed my laptop screen at an angle I knew the built-in camera would do me the most justice. I quickly leaned back on the couch, the screen showing a fairly close shot of my hard cock standing proud, protruding from its dark, wild bush. My hairy balls rested comfortably on the couch cushion underneath. She just looked at her screen in silence.
"Well, what do you think?" I edged the conversation on.
"That's a beautiful cock," she answered. I gave it a few slow strokes.
"Thank you," I replied, coyly displaying to her the underside of my upwardly curved banana. I knew this view made it look the biggest. After a couple seconds of this, I resumed my casual stroking.
"You're circumcised," she noted. From the way her arm was moving slightly I figured she started working on herself too.
"Yeah. Is that a good thing?"
"Honestly, yes. I know it shouldn't matter. Rob isn't. I don't know, I'm Jewish. It's what I'm used to. I think it looks nicer."
"Yeah, I know what you mean. I mean, I'm glad I am, but I wouldn't do it now if I wasn't."
"It looks kinda big. Is it?"
"What are you drinking?" I asked, though I was fairly sure I knew the answer. She held up her usual 16oz Bud Light can. I knew she was in the habit of picking up a couple from the corner store on her way home from work.
"Hang on, I'll show you," I said, and got up and went to my refrigerator, where I had a Monster Energy drink of the same sized can. I returned with it standing sideways, angled my camera up a bit, and placed the can on top of my dick. The head protruded about half an inch from the end of the 7 inch long can.
"Jesus!" she blurted out, looking at her Bud Light, then taking a sip.
"I thought you were Jewish!" I retorted with a bit of laughter, putting the can on the coffee table next to my laptop.
"Yeah, but not religiously." I didn't quite get what she meant but didn't dwell on it.
"Wait, show me again. With the can" I oblige and bring the can back up.
"That's gotta be like 9 inches," she estimated, her head tilted and contemplating the beer in her hand.
"Haha, no not quite. A little more than 7," I answered honestly.
