Balling for Charity

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Can Jerry's first impression of a buxom bitch change?
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imhapless
imhapless
3,642 Followers

"They" say first impressions are lasting impressions. "They" also say that the average married couple has sex 58 times a year, that once one is in a marriage that is sexless for 6 months the chance of ever reviving a sexual relationship is minuscule, and that some women can have an orgasm from breast play alone.

I don't know how true any of these things that "they" say are for the general population, but quite honestly I don't give a shit. All I know is that only one turned out to be true in an experience I had.

My wife Justine and I have known a couple named Sybil and Brent for several years. My first and long-lasting impression of them was that Brent was a loud-mouthed tool, and that Sybil was a totally uptight and stuck-up bitch. However, they had basically the same circle of friends we did, and apparently my impression wasn't universal, so we often were at gatherings with them.

I found it hard to talk to Sybil because she always seemed haughty to me. The only reason I ever tried to talk with her was because I enjoyed looking at her big tits. I admit to being attracted by major cleavage more than any other feature, although I like thighs too. Sybil was by no means a beautiful woman, but she wasn't bad looking, and her tits seemed to be perfectly shaped as well as large.

In the summer of 2009, Justine and I had been married for about ten years, and were in our late thirties; Sybil and Brent were a few years older and had been married about fifteen years. While Justine and I had been passionate the first few years of marriage, things slowed down after our first kid, and essentially came to a halt after the second one. While as an "average" we probably had had sex 60 times a year over our first ten years of marriage, by the summer of 2009 I couldn't remember the last time we had had actual intercourse. Our lives revolved around working long hours with all non-work time taken up with the kids.

I got laid off my job at the start of the summer of '09, but was one of the few lucky enough in a bad economy to find another one in less than a month. The new job didn't pay as well, but it wasn't as demanding either, and once I got more free time I really started to miss sex. Justine was hard to rev up, however, so I was getting frustrated.

About a month after I started my new job Justine and I were invited to a party at a country club swimming pool. While we wore cover-ups, we also had swimsuits on, and since I used to dive competitively I enjoyed myself actually diving off the board into, and swimming in, the water, rather than merely lounging around the pool like most other guests. One of the few other people actually diving and swimming was -- to my surprise -- uptight Sybil.

My impression of Sybil started to change that day. Maybe it was forced to change because she was wearing a two piece suit that accentuated those big, firm orbs on her chest, and also revealed to me for the first time that she had thighs that could only be described as "magnificent!" Apparently, I desperately wanted her not to be the uptight, stuck-up bitch I had always considered her.

Once Sybil plopped herself down on a lounge chair and was taking in the sun while chatting with women similarly situated on either side of her, I went and sat at a corner stool at the pool bar. My seat was specifically chosen so that through my mirrored sunglasses I had an excellent view of Sybil's body. I was embarrassed to actually be getting hard just glaring at her, but not embarrassed enough to move and stop ogling her.

Suddenly an almost drunk Brent came up to the bar and sat at the corner stool next to me. His stool was positioned so that I could still easily see Sybil over his shoulder but in view of my sunglasses it would look like I was looking at him while we talked.

Brent was his normal loud-mouthed self, but instead of brushing him off, I plied him with drinks and engaged him in conversation since I had the perfect ogling opportunity and didn't want to relinquish it. After a few more drinks, he was definitely plastered, but unlike most drunks became quieter and more introspective. I thought that this might be the opportunity to talk to him about Sybil.

Since I was 100% sober, worked in sales, and was on a mission, I was easily able to manipulate Brent. I got him to really open up about Sybil.

First Brent complained about how Sybil spent her time. His major time complaint was that she had just become the volunteer chairman (I hate the word "chairperson") of a committee putting on a charity ball -- for leukemia. He thought she should be getting paid instead, although they always seemed to have plenty of money. Then I directed the conversation to sex, first complaining that "I wasn't getting enough."

"Shit, telll me wouldja. Ya know, I use ta fuck her hairy cunt alls the time. But she's nowww the ice prickness. She'll lemme finger her while she -- hiccup -- reads, but I haven poked her with my biig cccock fer a year -- hic," Brent volunteered.

"Do you think you can get back in the saddle again?" I inquired.

"Shit, I donn know ow. I jist whack oft all as the time -- burp -- now."

"Say, Brent; if I can get her back to letting you fuck her, would you care how I did it? Could I do anything I want -- with your permission?"

"Hey, gofer it, bro -- hic -- be my guess ta do whatsoever if it's getting me fukkkin agen -- burp."

With the at least tacit approval of her husband I wanted to get the same from my wife, with the express purpose of at least getting to massage Sybil's mammary glands, if not to fuck her. But first, I needed to find out even more about Sybil and test her responsiveness.

When one of the women sitting next to Sybil vacated her lounge chair, I broke off my conversation with Brent, slapped him on the back, ordered him another drink that I tipped the bartender for, and with what Brent had told me was Sybil's favorite drink -- a Blue Hawaiian -- scurried to occupy the empty chair.

"Hi, Sybil," I said as cheerily as I could while taking my sunglasses off with one hand and holding out the Blue Hawaiian with the other. "A little birdie told me this was your favorite drink and the bartender seemed to specialize in it, so I thought you might want one."

"A Blue Hawaiian? I thought Brent would be too drunk to even remember," she said pleased with the offering, but not doing much to hide her disgust with Brent.

"No actually, he was quite lucid when he told me that, though I can't vouch for him now," I laughed.

"I'll bet," Sybil responded, actually smiling and removing her sunglasses too.

"Say, you must have been a competitive diver. I saw you entering the pool almost splash-less when you sprung off the diving board," I told Sybil to her obvious delight. This wasn't exactly true, but it might help me reach my goal so why not!

"Ha. I didn't know you needed eyeglasses," Sybil chuckled in response to my remark. "I probably looked like a whale flopping into the water."

"Actually, you looked like a sleek dolphin. I was very impressed."

This discussion really got things rolling. Especially after she had consumed the third of the Blue Hawaiians I got for her, she was anything but uptight. She was constantly grinning, giggling, and freely chatting, revealing much about her personality I never knew or even suspected. I had put my sunglasses back on, and was getting wonderful cleavage and thigh views. I couldn't tell if she noticed me raising a flag pole in my swimsuit, but I didn't make any attempt to disguise it.

By the time the party was breaking up, I had volunteered to help her with the charity ball in view of the extra free time my new job had given me, and offered to give her and Brent a ride home to make sure they didn't end up a fun night with a DUI. When I collected Justine she was a little surprised by my offer because she knew Sybil and Brent weren't my favorites, but didn't dwell on it. She and Sybil chatted in the back seat while Brent gurgled in the front seat on the way home.

I helped Sybil get Brent to the door, gave her a hug which I was certain put her on notice of my hard-on, and offered to drive her back to the Club the next day to pick up her car.

Sybil was the loosest I had ever seen her when I drove her back to the Club the next day, and the fact that she was wearing a tight top and short skirt when I picked her up was not lost on me. She went to go shopping after picking up her car (after we exchanged hugs again), and I took the opportunity to call Brent and tell him I was coming over.

Brent was badly hung-over, but completely coherent, when I arrived. I reminded him about our conversation -- he actually remembered it -- and he reiterated his blessing to do anything I could to get him back in the saddle.

That night after the kids were in bed I had a frank talk with Justine -- probably the most direct talk since pre-kids. I told her I hoped we could change our lives so that we were more "romantic," and asked if she wanted that too.

"Yes I would, Jerry. But you know how hard it is with the kids and both of us working," she replied.

"I have a plan to get things rolling. Do you trust me to do whatever I need to do as long as it works out?"

With a quizzical look on her face she responded, "Yeah, I guess. Sure; sure." With the tacit approval of both spouses, I now was on a mission to nail Sybil -- to suck on her breathtaking tits and lick her creamy thighs.

Apparently, with equal parts research and dumb luck, I had pushed all the right buttons with Sybil -- complimenting her on her diving and swimming abilities, paying rapt attention to her, getting her drinks, performing menial tasks for her, and expressing and following through on my offer to help her with the charity ball. She was now always completely open with and friendly toward me and when we had planned meetings was noticeably more provocatively dressed than she ever had been before. By the time I was a month into helping her with the charity ball, taking more and more responsibility for those aspects of the task she didn't enjoy as much (or at all), she started referring to me as her "co-chair." I was now ready to make my move.

I arranged for us to meet in the middle of the day at the most likely venue for the ball -- we had previously narrowed the search to three locations. I had purposely planned the visit so that the only person at the venue -- the director -- could be with us only for the first ten minutes or so since he had an appointment out of the office. He had no problem with us looking around after he left.

Once the director left, as Sybil and I toured the facility I shepherded her to the cloakroom. Once we were inside it, I blocked her passage out, and closed the Dutch Doors to the room, and glared at her. There was no fear or trepidation in her eyes when I did that; nor did she say "what the hell are you doing;" her only expression was one of anticipation.

I slowly crept up to her and gently started massaging both of her tits with my hands, all the while staring into her eyes. After massaging her in complete silence for at least three minutes, with the best enticing voice I could muster I went for it! Without breaking my cobra-like stare I declared:

"You have the most alluring breasts I have ever seen. I need to get a good look and feel."

"What about our spouses?" Sybil asked, though with more curiosity than concern in her tone.

"I can honestly tell you I have the tacit approval of both -- which I will explain to you some other time," I replied with what I am sure was a twinkle in my eye.

With that I grabbed the bottom of her pull-on top, she raised her arms to let me easily lift it off of her, and I placed it on a table. Then I unhooked her front clasp bra. She literally beamed at my expression of awe and wonder as her mammoth tits were released from confinement, her oversized nipples and light colored areola glistening as her tits bobbed up and down for a few seconds.

I was very pleasantly surprised at how compliant Sybil was. When I started lightly twisting her nipples between my thumbs and forefingers she closed her eyes as she stood almost motionless. When I started sucking one nipple while continuing to twist the other and caress the side of the sucked boob with my free hand she started moaning. Within three minutes she had her hands on my shoulders, was groaning and muttering encouragement, and was getting a more and more blissful expression on her face.

I had come prepared. I took a small bottle of baby oil out of my pocket, and started rubbing it between her pleasure mounds. At first this startled her slightly, and she opened her eyes. But her surprise quickly turned into a knowing smile -- how she so quickly figured out what was to happen, I don't know, but it was clear that she wanted it.

As I rubbed the oil in her valley, she got a devilish grin and started undoing my pants. When they dropped to the floor, I quickly stepped out of them, and she obligingly yanked off my boxers too. Then she took some of the oil from her tits and worked it onto my now harder-than-ever-in-my-life cock.

I gave Sybil a passionate two minute kiss, rubbing my hands on her tits while she stroked my dick, then broke our embrace quickly, threw some tablecloths from a pile in the cloak room onto one of the tables, laid her down onto her back on the tablecloths, straddled her, and then started moving my hips to stroke my cock between her boobs. She squeezed her boobs together pressing them into full contact with my cock as I caressed those parts of her tits she wasn't squeezing. Each time I moved the head of my dick up toward her face she licked its slit, until I increased my pace to the extent that she no longer could. It wasn't four minutes before she was shuddering in orgasm and I was spraying cream all over the bottom of her chin and her chest.

We were both drained by the intensity of our climaxes, as I collapsed on the table next to her and she continuously moaned. I stroked the sides of her tits while looking appreciatively into her eyes, and she was virtually giddy.

"Until a few minutes ago, I never believed that a woman could have an orgasm from breast contact alone. WOW! Was I pleasantly surprised."

"I've only had one once before. Brent doesn't seem interested in that. Hey -- I totally and completely loved it! WOW right back at you."

We chit-chatted for another ten minutes, before I got off the table, got hankies out of my pockets, and deliberately wiped my cum off, or rubbed it into, her skin, as she giggled. When she got off the table, we hugged each other tightly. When we finally broke contact she smiled and said "I trust this is not a one-time-only event co-chair."

"Wild horses couldn't keep me away," was my emphatic response as I planted an intense French kiss on her.

Planning the charity ball over the next few months was about the most fun I've ever had. It required many meetings in many different places. It required lots of creativity to find out how many different positions and venues we could tit fuck in. After one particularly passionate tit fuck in -- believe it or not an actual bed -- I exposed Sybil's glorious thighs.

I removed her panty hose -- no panties with them -- and started licking, massaging, and nibbling on her inner thighs, as she ran her fingers through my hair and scratched my scalp. Of course I had to check out her pussy; she had a full bush, just like Brent said. As full as it was, though, her plush pussy lips stood proudly near the top of the tallest hair. I started devouring it but Sybil stopped me.

"Hey, I'm not ready for you to sample my cunt yet big boy."

Did she really say "cunt?"

"You'll need to do something really special to lick it, let alone fuck it."

While continuing to stroke and kiss her thighs I asked "Oh yeah, what?"

"If we raise $250,000 by the time we count the receipts from the raffle at the ball, then I'll fuck your brains out."

"Nice," was my only response as I continued to enjoy her lush thighs.

I wasn't experienced at charity fundraising. But I was in sales, and I found out that motivation is the most important criteria in getting pledges for worthy causes, and I was REALLY motivated. By the night of the ball we had raised $241,200. We just needed $8,800 from the raffle and I was "in!"

If it was possible that my motivation had peaked (it hadn't) it went over-the-top when I saw Sybil the night of the ball. Her red-and-black dress emphasized every desirable aspect of her sexy body, and her hair and makeup made her look radiant, if not beautiful. I worked the raffle volunteers into a frenzy, and had brought $500 in cash with me in case we came up short.

Everyone seemed to have a great time. The band was rocking, the food was great, the atmosphere festive. Even Brent and Justine -- who seemed less than thrilled to come -- loved it. After Sybil and I danced the kick-off waltz (we kept our distance to the extent possible), Justine and I danced at least ten dances together, and Brent and Sybil did too. As the party ended at midnight, we sent all the help home, had Brent drop Justine off as he drove home, and started counting the raffle proceeds.

I was as excited as a kid waiting for Santa during the count; but when we were done -- even with the $500 I threw in -- we only had $8,550. I was crestfallen as Sybil started gathering her stuff and said "Gee, that's really too bad Jerry, but a deal's a deal. But we'll still be able to tit fuck."

I started pleading. Slobbering, pathetic, hapless, wretched begging. Holding her hands; stroking her hair; on my knees. After about three minutes of this humiliation I was ready to give up, got off my knees, and started to shuffle toward the door.

"You pitiful wimp," Sybil chided from in back of me, "you apparently aren't as interested in fucking me as you say."

When I turned around, Sybil was fishing into her purse. With a wicked smile on her face, she pulled out a wad of cash, counted out $250, and threw it into the raffle strong box.

"You bitch," I laughingly screamed, "you'll pay for that," as I ran around a desk trying to get to her. She ran around the other side of the desk, and out the door, squealing the entire time.

The vamp knew what she was doing -- she ran to the location of one of the best memories of my life, the cloakroom. I closed and locked the Dutch Doors just like the first time, but by the time I had turned around from doing that her dress and bra were already off, and her panties were being removed. As she stood naked, making playful provocative poses, I got out of my tux as quickly as I could then smashed my lips against hers while squeezing a tit with one hand, and running my fingers through her hairy bush with the other.

After a couple of minutes of tonsil-tickling and squeezing, I dropped to my knees. With her four inch heels still on, her pussy was at the perfect height as I pulled her lips apart and drove my tongue into the pink chasm. As she groaned and panted while running her fingers through my hair I exposed her clit, and licked and sucked on it as I buried two fingers from one hand into her cunt, and stroked one of her magnificent inner thighs with the other.

Sybil stumbled back against a wall as a volcanic orgasm wracked her body, with me shuffling along on my knees right after her. I'm sure she would have fallen over if she hadn't braced herself with her back against a wall. While she was still in the throws of her orgasm I again spied the happy pile of tablecloths stored in the cloakroom, spread several on the floor with one hand while fingers from the other remained buried in her snatch, and then pulled her down on top of me.

She was so wet and I was so hard and excited, my cock was up her cunt within seconds of her tits impacting my chest. I grabbed her ass and locked her into our spike-up-channel position as I started vigorously bucking my hips. I wanted to go slowly at first, I really did. But I couldn't. Lust overwhelmed me as I pumped harder and harder and she groaned louder and louder. It wasn't long before she was being overtaken by another orgasm, and I vulgarly grunted each time I discharged a wad of seminal fluid into her.

imhapless
imhapless
3,642 Followers
12