What If?

This is the second in a [potential] series of stories that I’m working on. They’re based on reflecting about some “what if” situations—situations where I made a more conservative decision and, perhaps, just missed a once-in-a-lifetime (for me, at least) opportunity. That said, they’re based, at least loosely, on people that I’ve known (and either admired or lusted after) over the years. My apologies regarding the first one, What If Ch. 1; I had intended for it to have this preface but in my first submittal, I managed to completely botch it.

I enjoy writing, and hopefully I’ve written something that you enjoy reading. I’d love to hear your feedback and constructive comments. And please remember to vote when you’ve finished the story.

I hope you enjoy it!

“Are my tits the only thing you think about when you look at me?”

I have to confess, that’s the first time I was asked that question and I immediately paused. Now, mind you, it’s not the first time that the thought had occurred to me where Jackie was concerned (and the answer was: “Yes, most of the time they are the only thing I think about.”). But it was the first time it was actually voiced. And sitting directly across from Jackie, you can probably guess where I immediately looked. Come to think of it, you can probably guess what my immediate reaction was (my shorts began an obvious tenting).

But maybe I should back up a bit…

* * * * *

Jackie was a neighborhood friend of mine. She was two years older than I was, going into her senior year at our high school while I would be starting my sophomore year, but in spite of the age difference she didn’t ignore me or treat me as if I were significantly lower on the evolutionary ladder. I wasn’t her best friend or anything; however, she actually said “hello” and chatted with me when she saw me. It probably had as much to do with the size of our high school and neighborhood (both were tiny) as it did with the way she treated most everyone (friendly and accommodating). In fact, it was precisely that attitude that would get her into trouble, but more on that later.

As far as I knew, Jackie didn’t date regularly. Part of it was that, in some respects, she was unremarkable. She was quite short, only five feet tall. She was a little on the plump side, with an oval face that some would say still had a trace of “baby fat.” Personally, I thought she was extremely cute and looked kind of pixie-ish. Her hair was unremarkable as well, a blondish-brown that she wore for at shoulder-length for most of her life. Recently, she’d gotten it cut very short (further emphasizing the pixie look in my mind) and it really looked good on her.

The remarkable part about her was her breasts. They were huge. They were big and firm and they stress they had to put on her bras would have given any engineer a nightmare. Or a hard-on. Most likely both. And they weren’t the soft, floppy tits that many well-endowed women have. These looked gravity straight in the eye and said: “Piss off.” Wow.

Not surprisingly, these local landmarks garnered the attention of nearly every male in the neighborhood. And more than one of us had attempted to get a look at them. Or better yet, a handful of them. For a number of my fellows, that was the primary activity of that particularly boring summer—trying to get a good look at Jackie’s tits.

Our neighborhood was much like any Midwestern small town. There were plenty of aging houses, standing shoulder-to-shoulder and facing the street, with an alley in the back to provide access to the garage and the back yards. The back yards were separated from each other by the regulation, waist-high, chain-link fence, while the back of the yard, where the detached garages were located in most of them, was filled with shrubbery and other greenery. This was the part that we boys truly relished—the backyard shrubbery.

Like most boys, we were always on the lookout for places to hide; places that could be our own. Where we could think and talk about all those thoughts that we were certain no one else had ever thought. And like most boys, we found more than one of those places (you had to have a few spares, they were kind of like “safe houses”). Many of those places were in the local “woods.” What we thought were wilderness areas—populated by a mix of wild animals and wilder natives—were really just undeveloped and overgrown areas. One or two of those areas were in the middle of the neighborhood, within the overgrown and untended shrubbery that had been allowed to grow wild over the years. And in one of these, the shrubs had grown up next to a low wall so that that there was a hollow inside, large enough for several of us to sit comfortably inside and be completely invisible to a passerby. This particular hidey-hole quickly became our favorite, partly because of its close proximity and partly because of the danger of being so close to potential discovery.

As we got older, the nature of the activities and the discussions inside our hidey-hole changed. We stopped talking about how icky and disgusting girls were and started talking more about what they might be like under all those clothes. A couple of the boys would regale us with their extensive knowledge about the detailed anatomy of women in general (and a few, like Jackie, in particular). Usually, these were the ones with older brothers who had tried to impress them at one point with their superior knowledge. Rarely, very rarely, they had some sort of first-hand experience of a glimpse here or a feel there that they’d expand into a truly epic tale.

And for the truly lucky ones, these places became the focus of the exploration of Playboy and group masturbation activities, which I never was fortunate enough to participate in. (For years, I had mixed feelings about this. Partly nervous about whether I could do that in front of everyone, and partly envious that I never got the chance.)

One day, three of us, Greg, Corey, and I, were sitting in the hidey-hole, shooting the shit, and trying to stay out of the hot summer sun. We had just finished an exhaustive comparison of the breast sizes of all the girls in our small borough and had lapsed into a brief silence while we individually entertained deep thoughts about a sea of local breasts (we hadn’t progressed quite far enough to discuss nipple sizes yet). In the middle of this brief silence, Jackie poked her head into the hidey-hole.

“Hey! Mind if I join you?”

Jackie was one of the few girls who know about the location of the hidey-hole. However, I doubt she had even a vague idea of what went on in there or she would never have risked coming in.

“Nah” Corey said. “Come on in.”

Jackie squeezed through the opening and joined us in the circle between Greg and I. We all swallowed as she twisted and ducked through the opening. Jackie was wearing a pair of extremely tight and short white shorts and a very snug yellow, sleeve-less, v-neck top. As she bent forward coming through the opening, we got the most perfect shot of the huge valley between her boobs.

“So, what were you talking about?”

Silence.

“Come on, what were you talking about?”

“Nothing, really” I said.

“Bullshit. I could hear your voices as I was walking around the outside. I know you were talking about something.”

Greg looked across at Corey and winked. “Well,” he said, “we were talking about something…”

“I thought so! What was it?” Jackie asked, leaning forward to rest her elbows on her knees, simultaneously giving us another heart-stopping view of her cleavage.

Greg looked directly at her chest, looked up into her face, and leered: “Your tits.”

Turning beet red, Jackie continued to look at Greg for a second as if she couldn’t actually believe she’d heard him right.

“What did you say?”

“I said,” Greg reiterated, slowly and deliberately, “we were discussing your tits before you walked in.”

With that, Jackie sat straight up and looked directly at her feet. Clearly, Greg’s answer wasn’t anywhere near what she imagined we’d been talking about, and she was getting more than a little nervous.

“Well,” she began in quiet voice, “maybe I’ll just head back out and let you continue talking.”

“No. Don’t go on our account.” Greg placed his right hand firmly on her knee and Jackie got a decidedly scared expression on her face. As she leaned forward to try to get up, Greg’s left hand went straight to one of Jackie’s tits. A whole host of emotions, mostly centering on fear and anger crossed Jackie’s face.

“No. Please don’t do that. I’m leaving.”

With his hand still firmly on Jackie’s knee, Greg tried to quickly snake his left hand up under her blouse for a better grab at her tit. And at that point in time, everything began to happen in slow motion. Jackie twisted to try to get away from Greg. Corey leaned forward as if he was going to help Greg and then looked as if he thought better of it. Greg leaned in towards Jackie trying to get a better grip on the tit he was mauling. As Jackie turned, you could see the fabric stretch and deform; nearly tearing it off her back. Corey sat back down just as Jackie spun away from Greg; her bra slipping slightly out of place and her top yanked nearly halfway around her torso. As she broke free, she stumbled back towards the entrance. Standing there, chest heaving, she roughly adjusted her clothes and stormed out.

Corey, still sitting there, smirked and said “Well, that was fun,” and silence settled over the three of us, each left to our own interpretation of what had just happened.

Perversely, it was kind of fun. While I felt awful for Jackie, I had to admit that the entire affair had given me a massive hard-on. The near glimpse of Jackie’s awesome tits was something that I thought I’d never get to see, and in spite of the way that Greg had humiliated her, my desire to see her uncovered chest greatly outweighed my concern over how Jackie felt about all that. Not that any of that made any difference; I couldn’t have told her how sorry I was about that if I wanted to. I’d have done what I normally did in those situations. Thought lots of deep and caring thoughts while keeping my mouth shut.

After that, I didn’t see Jackie for a while. I assumed that she was intentionally avoiding all of us, but I honestly didn’t know. She could have been out with family or traveling or any number of things. Whatever it was we didn’t see her at all for a couple of weeks. I couldn’t have blamed her for avoiding us. Greg and Corey clearly weren’t concerned at all that she might have been upset at all that. Even if I was concerned about her feelings, I didn’t do or say anything. So things gradually settled down among us, to the normal level of tension anyway, and we got on with the summer. And in all that time, none of us went back to the hidey-hole.

It was about three weeks after the episode with Jackie that I headed back there. I had been sitting around the house reading and had gradually gotten bored with the sitting part. Not having anything else to do, I decided to grab my bike and head out to see if anyone was out doing anything (none of us ever called each other for that, and this was way before internet chat). I gradually made the rounds of all the usual hangouts without discovering a any of the usual crowd. On a whim, I decided to check the hidey-hole in the offhand chance that someone was finally going there again.

As I pulled up close to the shrubbery that enclosed our space, I looked around for evidence of anyone else being there. But there was no indication of anyone; no bikes, no skateboards, nothing. I dropped down next to the short wall, lifted my bike down next to it, and ducked in through the door. Inside it was cool, shady, and completely empty. “Batting a thousand,” I thought to myself as I sat down and leaned back. Sighing, I began to wonder where everyone was and, if they were doing something really interesting (or stupid), why I wasn’t invited. After a few minutes of pointless reflection on that, I remembered the last time I was in the hidey-hole; three weeks ago when Jackie got her tits mauled by Greg. Closing my eyes, I began to fantasize about just what I might have seen if Greg had managed to get a better grip on her tits. Predictably, my cock began to swell in the tight confines of my cutoffs.

Shortly into this speculation, I heard a quiet sound outside as someone dropped down next to the wall. I sat up quickly and tried to minimize the bulge in my crotch just as Jackie stuck her head through the entrance. She paused for a second looking at me before evidently deciding that, if I was the only person in there, it was probably pretty safe. At least it was safer than the last time she was in there. She ducked inside and sat across from me.

“Hi,” she said quietly as she looked at the ground between us.

“Hi.” My confused glance shifted back and forth between a very conflicted-looking Jackie and my feet before deciding on my feet as the safest location. Particularly given what she was wearing, the same type of v-neck top as a few weeks ago only this time in white. After a few quiet moments, I said, “So, haven’t seen you around for the last few weeks.” God, was I sensitive when I wanted to be!

“Yeah. My parents took us on a bit of a vacation to the shore. And after that, I just didn’t feel like seeing anybody.”

I smirked at that comment. “I can understand that. I guess that under the circumstances I wouldn’t either.” She looked up at me and smiled briefly before returning her gaze to the ground. “So what brings you out today?”

She sighed deeply before answering. “I got stir-crazy. I’ve been sitting in the house by myself moping for too long. And besides, I’ll have to face those insensitive jerks eventually; I might as well get it over with sooner than later.” She sighed again. “They can really be pricks sometimes.” Bad choice of words, with her use of the word “pricks,” my shorts began to tighten a bit.

Trying to get my thoughts, and my crotch, back on track a bit, I replied, “They pretty much treat everyone that way. I have no idea why they act that way, but they’re quite good at it. Comes from all that practice, I guess.”

Jackie snickered at that and rewarded me with another brief smile. After a moment she sighed again. “But it’s not just them and their attitude…it’s everyone.”

“Everyone?”

She paused briefly before answering, “Well, everyone with a penis…I swear that everyone that looks at me looks straight to my chest. It’s like I don’t have a head, just a body with these,” looking down directly at her own mammoth chest. For once, I didn’t look there as well. She went on, “I mean, I understand that most men are interested in breasts.” Interested? She had no idea what kind of understatement was embodied in that simple pronouncement. “But in my case it seems like there’s no interest in anything but my breasts.”

“Are my tits the only thing you think about when you look at me?”

* * * * *

As I said, I paused before intelligently replying, “Well…umm…that is…no, I certainly don’t…” Meanwhile, my gaze was alternating between her eyes, her tits, and nearly anywhere else I could look.

She gave an exasperated sigh and said, “See! That’s exactly what I’m talking about.” As she finished, she glanced down at my slowly expanding crotch and giggled. “And your other head gives you away as well!”

I turned beet-red and began squirming under her gaze, trying to reposition my growing erection while not making it obvious that that was exactly what I was doing. “Geez, Jackie, I’m sorry. It’s just that between talking about your ti…I mean, breasts, and the snug top you’re wearing.” I sighed. “I mean, I try not to, but your breasts are the first thing I think about whenever I think about you,” I said as I thought about the times I beat off thinking about sliding my dick between her tits.

“

Whenever?

” she said with the same inflection that I’d just used. “That sounds like a bit of a loaded statement. And when would that be?” She smirked as she looked directly at me. “And you can call them ‘tits’ if you like.”

“You know…whenever,” I replied without too much conviction.

“Might it be when you do something?” she asked with a hint of a smile in her voice. “Do you jack off and think about my tits?” If anything, I turned a deeper shade of red. “You do! . . . Wow. . . I kind of like that.” She slid over beside me and placed her hand on my knee.

Did I hear that right? “You kind of like that? Really?” I traced my gaze slowly up from my feet towards her face. As my sight passed her breasts, I noticed that her nipples had started growing noticeably erect. They were as impressively large as her huge tits were.

“Yeah, I kind of like that you fantasize about me. Especially that you’re not forward about it either.” My cock was rock hard by this point in the conversation. She looked down at the tent in my shorts and slowly ran her hand up my leg stopping just as she grazed my bulge. She sighed again, but this one sounded less like frustration and more like lust. She placed her palm on my imprisoned dick and slowly rubbed it. “Although something feels pretty forward right now. Tell me, what do you think about when you think of me?”

“Honestly?” I croaked.

“Honestly.”

I licked my lips and swallowed. “I think about tit-fucking you.”

She purred in the back of her throat and the pace and pressure of her hand increased. My dick got a notch harder and twitched slightly to go with that. She looked down at her hand and back up at me. “Are you thinking of that right now? Are you thinking of sliding this cock of yours between my tits? Would you like that?”

Would I? I couldn’t believe this was actually happening. I’d gone through the fantasy of tit-fucking Jackie many times while I was beating off…this was too good to be true and I hoped I wouldn’t screw it up at this point. “Oh, man! I’d love that. Your tits are the most magnificent I’ve ever seen.”

“And just how many have you seen?”

“A lot.”

“For real? Or just in magazines?”

I look sheepishly at my feed. “Umm…magazines really…”

“Well, you’re about to see these for real.” With that, she took both hands, pulled her sleeveless shirt over her head, and tossed it to the side, exposing the industrial-strength bra she was wearing. It barely covered her huge breasts and was clearly having a difficult time holding them in place. Looking directly at me, she reached both hands behind her and began unfastening her bra, bringing her arms forward and pushing her massive tits together to pull her bra off. She tossed her bra on top of her shirt and cupped a breast in each hand, rubbing them slowly and sensuously. As her huge tits came free, I realized that I’d hadn’t been breathing and gasped at the sight of my frequent fantasies finally revealed in all their fleshy glory.

She smirked at my gasp. “So, you like them then,” she stated obviously.

“My God! They are magnificent.” And they were. She was at least a 38DD with very little sag, surprisingly firm for their size. Her areolas were not as large as I expected, a little under two inches across and more like a deep tan than brown. Her nipples though were round and hard, about the size of my pinky and as hard as pencil erasers. I could have hung my house keys on them. I licked my lips as I thought about sucking them deep into my mouth.

My expression must have told her exactly what I was thinking as Jackie smiled and voiced my thoughts, “You’d like to suck on them, wouldn’t you? I’d like that too. They really like a good sucking.” With that, she grasped her right breast and aimed her nipple right at my face. “Go on…suck on it…I know you want to.” She squeezed her tit more firmly and it bulged between her fingers. “And maybe I’ll let you fuck them too.” With that, she let go of her breast and squeezed the bulge in my pants. “We’ll have to ask him if he’d like to,” she said while looking meaningfully at my tented shorts.