Ilene's Challenge -A Nest Story

Ilene's Challenge

Installment 3

Vern was so kind and loving all he wanted to do was pleasure me. Why couldn't I let him take me. . . take me to that place of real love making I've always wanted but could never let myself visit? I swear, when we get together next time, I'll let him fuck me. I will! And I won't think about mommy's screams and Aunt Bea's laughs.

Ilene had learned the joys of orgasm early in life. The most ecstatic pleasure that she knew was her feeling after beating-off a big, rugged man sporting a huge, thick cock and then watching him cum all over her small breasts. The mere fact that she could jack-off a man at will wasn't enough, however; he had to resist if she was to benefit. And the longer he could keep from coming the more valiant his effort to avoid losing it the better she liked it. Moreover, when she saw that look of hopelessness on his face an instant before ejaculating, the more poignant was her own orgasm. Ilene's proclivity for beating-off guys had directed her sexual life ever since middle school. From her very first encounter at the age of twelve with her two dimwitted step-brothers, she realized that she possessed both the perfect attitude and technique for having things her way: all her men shot their loads when she beat on their shafts no matter how hard they tried not to. Many men had done their best to mount her while they were being stroked into a frenzy, but none had succeeded. Therefore, this young Japanese-American lady who'd played with dozens of cocks was, in the biblical sense, still a virgin.

My history professor has the biggest donkey cock I've ever seen. So now what? Do I just play my sex game with him? Oh, God. What an explosion! When I got him off he must have emptied his balls completely. Look at all that cum on my sheet. But there was more to it than usual. Sure there was. Look at the way he treated me. . . like a real lady! Maybe I can take that gargantuan shaft in my golden gully? After all, Aunt Bea sure laughed a lot when her man tried. . . God, what made me think about that?

After three months of seeing each other socially at least once a week, Vern D'Angelo's attitude toward Ilene began to change. The once happy-go-lucky professor who had ingratiated himself into the hearts and vaginas of so many young students was quickly becoming embittered; frustrated at his inability to screw this little bitch. Try as he might, Ilene would never permit intercourse, and her amazing ability to arouse him, pet him into a frenzy, and finally neutralize him was the major source of Vern's mounting anger. "Maybe I'm too emotionally involved with her?" was the rationalization he lived with, but he really didn't believe so. He was fully aware of the painful truth: Ilene Butrynelle was too much woman for him to handle.

For the past six years Ilene had been a lucky lady. Few women could ever have engaged in such outrageous sexual behavior with so many men and remained unharmed. Maybe the sweet yet perky little girl air she exuded saved her from an occasional beating, or maybe it was the men themselves guided by the hope of getting lucky next time. For whatever reason, no one had ever hurt her in any way; she'd never considered violence as a consequence. This time, however, with her horny Italian Professor as the frustrated suitor, her luck was dangerously close to running out.

Dr. D'Angelo had had enough of Ilene's little sex games. His dilemma was, of course, that being her professor he couldn't become violent by forcing intercourse, nor could he engage in coercion of any form. The slightest hint of sexual misconduct with a student would surly mean his career; too big a price for any piece of ass. In trying to resolve this predicament, he wrestled with several complex solutions, all of which involved conspiring with a third party. Most historians love conspiracies. It's part of the psyche that causes them to enter their fields in the first place digging through old documents while seeking ancient conspirators is ambrosia to these chroniclers of past truths. And the more complex the plot the more unlikely that event A would ever have effected action B thus resolving issue C the more smug they become when boasting about their discovery to colleagues. (The fact that event A may never have occurred at all was irrelevant.) It was with this mind-set that Dr. Vern D'Angelo put into motion a plan that would vindicate his male honor while avenging his shamefully unrewarded phallus.

The Reverend Peter Bode was an itinerant Evangelist preacher who years earlier had been Vern's roommate and closest college friend. Peter "Longfellow" Bode as he had been aptly called (although usually, simply the Poet) soon dropped-out of school, the Pittsburgh Institute for the Social Sciences. Stern administrative restrictions on the Poet's social freedoms had been imposed by the Dean after charges of sodomy (filed by the college president's thirteen-year-old daughter) became known. This unwarranted attack on his persona convinced Peter that a degree just wasn't worth the hassle, so he quit school to take a stab at the real world. Later, after dozens of different career starts, the Poet fell into tent-circuit preaching where he thrived for many years convincing rich widows to donate everything they owned to his church and anything else they had to his cock named Longfellow.

More about Peter's nickname. The first time Vern met him was in their dormitory. Peter was strutting back from the showers with a towel draped over his shoulders and his penis, adorned with a little yellow ribbon, swaying like a pendulum between two skinny legs. Most men adopt at least a modicum of modesty when stark naked, but on this night Vern D'Angelo understood why Peter Bode enjoyed drawing attention to himself. Longfellow, by the most conservative measurement taken by the most skeptical student, possessed a prick that hung fourteen inches. Limp. It was by far the longest shaft in Sears Hall, most certainly at the university, and quite probably in the state. But as strikingly awesome as this pussy-probe was by virtue of its length, it was equally unique in its girth. String Man would have been just as good a nickname as Longfellow, since Peter's phallus was a mere five-eighths inch in diameter. And if this wasn't weird enough, the head of his schlong was no more than a little bulge at the end, making the entire apparatus look like a length of hemp rope dangling from a furry crotch.

Whereas in total bulk gross size, if you will Vern's monstrous, thick cock was larger than Peter's mutation, in a crowded locker room it was Longfellow that garnered all the sightseers' admiration. Additionally, Longfellow's shaft possessed yet another less obvious quality, and it was this entire "genital package" that prompted Vern to seek out the good Reverend Bode after all these years. Reaching a hard-on length of nearly seventeen inches, the Poet's cock remained surprisingly limp at erection. This incredible combination of length and flexibility led to some very interesting sexual possibilities. He could, for instance, slip into a throbbing, wet cunt so easily and from virtually any position, that with only the first couple of inches inserted some women never realized that they'd been entered. This was especially likely while he and his partner were in the midst of passionate petting, all wrapped up in a tangle of tit-sucking and body-licking. Thus, Peter's unusual ability was exactly what Vern D'Angelo needed when he prevailed upon his old friend to deflower the lovely Ilene. Vern's logical, conspiratorial thinking had led him to formulate a bizarre plan shortly after his last defeat by Ilene's dexterous fingers. Although he'd improved a bit when it came to holding off during their bedroom encounters, she had learned much faster than he; she was now able to bring him to climax within five minutes, every time. He now fully understood what he was up against: her skill at turning men on and controlling their passions. Vern knew he couldn't overcome her without help.

"A new man, that's what I need. Charm the panties off a nun. Yeah, Longfellow, he'll do it," were the thoughts racing through Vern's mind as he drove his old buddy to the "chance meeting" with Ilene. "That's right, he'll get her drunk then play around in bed a while and before she knows what happens, bam, she gets fucked." Vern's scheme was based on a simple assumption: Once Ilene had experienced the incredibly heightened orgasm resulting from real intercourse, she'd be so thrilled that she'd ardently seek more. From Vern. And Peter "Longfellow" Bode was the perfect man to get the ball rolling.

As they drove, the men laughed and reminisced about joys shared years ago. Like the time they double dated to a movie, and after the girls left to piss the boys cut holes in the bottoms of their popcorn boxes which they then placed squarely over their open zippers. Later, when screams filled the theater (after the ladies reached for a kernel but grabbed something else) the young men remained stoically silent while two raving bimbos scrambled for coats and purses. The laughter ended as Vern's Porsche stopped a block away from Northeastern University's library. The "visiting scholar," Peter Bode, got out carrying a tattered old book given to him by Professor D'Angelo.

This month's special assignment for Ilene had been to research an obscure historical personality for her professor, a task with which she was getting nowhere. She'd traveled all over Boston to various bookstores and private collections seeking one particular book, and she was about to tell Vern that her quest was hopeless. Leaning back in her library chair to stretch, she glanced at the tall man sitting next to her. He smiled through his slick handle-bar mustache, and turned back to his reading, John Honeyman: Portrait of a Spy. Ilene nearly tipped over backward as she gasped with disbelief; he was reading the very book which had eluded her for so long. One hesitant query led to another, and before long she was nearly on top of the man grilling him with dozens of questions, all of which he graciously answered. An hour later, she and Peter Bode were walking side by side toward the Bent Elbow Cafe, a popular watering hole. After a few drinks, Peter "reluctantly" agreed to allow Ilene to review his arcane book and take whatever notes she wished. He wasn't willing to let the book out of sight though, and her research would have to be done at his hotel. To this the young graduate assistant eagerly agreed.

Two hours later, notes taken and work done, Ilene felt totally at ease and very proud of herself as they sipped brandy on the Poet's balcony. Satisfied with her work she now turned her attention to this wonderfully helpful and perfectly charming man who had come to her rescue. They happily chatted about life in general, but when the conversation turned to sex, as it often does, he seemed to freeze. At Ilene's urging, however, the Poet relayed a sad tale of sorrow and betrayal caused by a bitter, vindictive ex-wife and her greedy lawyer. Unashamed, Peter let streams of tears run down his cheeks and flow into golden whiskers. Ilene moved closer to comfort the poor, distraught man, and ten minutes later he was being further comforted by this grateful and compassionate lady, in his bed. Feeling terrible about his shattered life, Ilene had decided to thank this wonderful man for being so kind and generous. She undressed him slowly, heaping tender kisses upon each newly exposed patch of flesh. As she reached for the strangely baggy boxer shorts he seemed to tense up, but Ilene, touched by this refreshing display of shyness, whispered that she'd love to release all his tensions and make him feel good.

The Poet just smiled while the final garment slid down his legs, stopping abruptly at his ankles. Until this moment, Ilene Butrynelle's greatest feat of conquest had been successfully jacking-off her history professor. Bringing that monstrous member to climax over Vern's dogged resistance had made her own orgasms so intense that she swooned. But now, an even greater challenge lay neatly coiled right under her nose. Regaining her composure, she hesitantly extended her fingers toward this living whip, and as she grasped Peter's manhood she felt the muscle tighten slightly and flex a bit under her tenuous grip. In a flash, this calm, charitable man was upon her. Ilene began to stroke, but for all her efforts his silken shaft would not get very hard. As she sucked on the end of Longfellow she felt it stiffen a bit more, but taking him in her mouth only made her gag. A sword-swallower might have succeeded, but Ilene wasn't built for such a piece of work. Peter was methodical in his duty. Having far more experience than his little partner, he slowly positioned himself for a quick thrust into her pristine pussy. Entry would be easy, for her sweet juices were flowing so copiously that his thin shaft would quickly penetrate her golden gully.

The moment arrived. Ilene's mind had been racing from the moment she saw and felt this highly unusual prick. She knew intuitively what to expect from him, and she was trying to devise an effective counter measure. But what? How could she side-step tonight what she'd so skillfully avoided since age twelve? While exploring the entire length of his stately stick she noticed a slight dimple-like depression several inches behind its tiny head. "Could this be his joy spot?" she wondered. "Since he must masturbate, is this where he likes to hold himself?" Time was running out and she knew it. Without the opportunity to slowly and carefully work over every inch of the Poet's phallus (learning everything possible about his preferences, and, therefore, his weaknesses) she made a quick, calculated guess. Lightly grasping his long probe between two thin fingers, right at the dimple, Ilene resumed her stroking. Drawing his mouth to caramel nipples protruding from her small, beautiful breasts Ilene slowly massaged his inner thighs while simultaneously increasing the speed of her stroke. She was now moving her hand only four inches or so, total travel: two up and two down, instead of trying to run it along the entire length of Peter's cock which she had done at first. She gently removed an erect nipple from his mouth and planted a warm, tender kiss on his lips while moving her free hand from his thighs to his belly. With firm, gentle pressure Ilene pushed her fingernails into his stomach, snuggled her little head into his neck, and whispered, "Cum now, big guy, cum now."

Peter was shaking: he'd missed his opportunity. Earlier, when Ilene was stroking its entire length, it would have been easy to slip the hungry Longfellow into her moist cunt when her hand was at the base of his cock. But now, as she gleefully worked near the head of his slender slammer, there was no room in which to maneuver. Ilene was quickly bringing him to new heights of arousal, and he too was running out of time. Then she heard it. In a momentary lapse of concentration, Peter drew a short breath of air a little too quickly. He was fully aware of this tell-tale sign which told a woman that a man was about to lose it. He'd tried to muffle the gasp, but failed. It was a costly mistake, and when he looked into Ilene's face she was beaming. As she continued to beat on his shaft she now did so with confidence. Her "You don't stand a chance!" grin sealed his fate, and Peter Bode prepared himself to lose. Employing every technique she knew, Ilene brought the Poet to an incredible state of frenzy. Writhing and squirming, he made one last Herculean effort to regain control, but his gasps belied his hopes and he lost it.

Longfellow's awesome length produced a sort of pipeline effect, with each spasm acting like a little pumping station every few inches along the route. As each new contraction shook his quivering body, the thick, white fluid was propelled through his potent pipe at an ever increasing speed. He shuddered, cried out "You got me, you got me!", and shot a dozen mighty bursts of semen like a stream from a fire hose. Ilene flinched as these hot gobs of cum slammed against her small breasts, but the pain was her badge of courage and she reveled in it. Her own orgasm followed immediately, which was one of the strongest and most delirious she'd ever felt. Bringing such a man to his downfall by totally overwhelming the longest cock that most women would never see drove Ilene to glorious abandon as she basked in the hot, tingling sensations deep within her loins. Panting and heaving, winding down like marathon runners at the finish line, the sweaty couple fell back to their pillows, spent and speechless.

It wasn't real sex this time either and I've almost given up trying. Mommy and Aunt Bea. . . didn't they enjoy sex the same way?

Vern D'Angelo sat quietly behind the steering wheel and listened as the crestfallen Poet faithfully relayed a blow-by-blow account of his session with Ilene. "I'm sorry, Vern, I tried my best. If you want me to take her out again and try. . . ."

"No, forget it, Peter, I'll handle her another way (the only other way left, he thought). Thanks for being a good friend." The two old buddies parted company and Vern drove alone to a seedy commercial area on Atlantic Avenue near the docks. He parked under a broken street light, bare bulb glistening in the fog, and entered a converted warehouse-apartment. Pausing at unit 6B and shaking his head at the coincidence of that particular number, he steadied himself against the jamb before knocking. For the first time in his life, the entire two hundred thirty-five pounds of Dr. Vern D'Angelo was frightened.

The door swung open and Vern was greeted by an impeccably smooth, pure Jamaican accent, "Good evening Dr. D'Angelo. I've been waiting for you. Do-oo come in."

Ilene never knew that her meeting and subsequent communion with Peter Bode had been orchestrated by Vern. The next morning, as she sat on her kitchen table by the big window, wearing only a bra and panties and swinging her beautiful legs, neither did she know that across the street a man with a telephoto lens was taking pictures of her. She hopped down, dressed, and left for class. Ilene strolled into History 101, perched herself in 6B, and was more dumbfounded than anyone else when a short Jamaican man wearing white on white strode to the podium. "Good morning class, my name is Dexter Dojkasawyer. Professor D'Angelo is gone and I am your new teacher. Do-oo sit down."