When Allen Met Jill

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Allen sagged against the couch. It seemed like every fiber of his being had been drained. Every part of him was limp - except his stiffie, which was undiminished and truly stupendous. "You've done this before, I take it," he said, smiling lopsidedly.

"Well, let's just say that I experimented with the proverbial 'forbidden fruit,' and what my experiments taught me is that guys are, generally speaking, pricks with legs. And then there's you, Allen. Quiet, gentlemanly, meek you. Always friendly, but more timid than a long tailed cat in a room full of rocking chairs. Always selling yourself short, and as a result never letting yourself give of the tremendous reservoir of goodness and love that you have within you. It was by going away and finding out what else was out there that I realized what a treasure I had in you all along. I love you, Allen, and as shy as you've always been, I knew that if we were ever going to get things started, I would have to be the one to make it happen."

"What do think of my solution?" she asked, waggling her eyebrows.

Amazingly, Jill saw a tear run down Allen's cheek.

Before she could reconsider her chosen course of action, he stood, pulled her tightly against him, and kissed her passionately, all prior restraint gone. His hands roamed her back, finding her buttocks, and then rising back to her flimsy bra, which he began to fumblingly unfasten.

“It clasps in front,” Jill whispered.

Without breaking their lip-lock, Allen moved behind her, hands on her breasts, fingers on the clasp. Still struggling with the confounded thing, she reached up and helped him do the honors, and off it came. Immediately his fingers went to her nipples, caressing and teasing and rolling them until they were the size and rigidity of small erasers.

Suddenly she pushed back against Allen and they fell back on the couch, with her on his lap. “Oh, yes, that’s it, play with my tits, make my nipples hard, suck on them, you punk!” she moaningly exclaimed, squirming in an impromptu lap dance.

“I beg your pardon,” Allen said, stopping momentarily.

“I said bury your face in my tits, put your mouth all over them, make them yours!”

Before he could say anything else she engulfed his face with them, and he sank again into the dizzying rapids of sensation. Reaching around her, he tugged down on her thong, and off it came. Sitting up, Jill tore off Allen’s t-shirt. “Lay down!” she commanded. He obeyed, and she sat on his chest, straddling his face, and hissed, “Lick my pussy, you bastard, stick your tongue inside me, suck on my clit.”

“Excuse mmmmph,” Allen began before Jill began grinding her pussy into his face. Reaching up, he shoved her backwards on the couch, climbed atop her, and stuck his tongue down her throat, relishing the taste of himself that was still in her mouth and the absence of her disconcerting ribald chatter doing so made possible. Moving downward, he put a finger on her lips for emphasis, then reacquainted himself with her neck, her shoulders, her breasts, then continued lower, across her soft midriff, tonguing her navel, leaving a trail of kisses down to the confluence of her legs.

He needed no encouragement for what he planned to do now. Before him lay the promised land. He slowly began exploring the folds of her pussylips, licking the crease up and down, gently probing with his tongue and taking the occasional swab over her bulging clit. Jill began thrashing around with barely repressed squeals, which told Allen that he was doing it right.

Finally she couldn’t contain herself, and she blurted out, “Oh, Gooooood, yes, keep doing that you dirty son of a bitch, suck on my hard clit, make me cum, oh yeeeeeaaahhhh!”

Allen almost choked. “Jill, would you please mmmmph.” She grabbed his head and pulled it hard against herself, completely in the throes of passion. Within seconds, it boiled over as she orgasmed violently. Allen couldn’t breathe, and felt like his nose had been broken.

“Oh my GOD, Allen, where did you learn to suck pussy like that?”

Prudently removing his head from between her thighs, Allen retorted, “Never mind that, why won’t you shut up?”

“What’s that supposed to mean?”

Allen sighed. “Okay, since we’re having carnal knowledge of each other anyway and I’m already probably in huge trouble with at least three different parties, what the hell? As you no doubt surmised, I am – or was – a virgin. And yes, the thought of coming over here and making love to you was on my mind. I just never imagined that it would really happen.”

“But when I fantasized about it, somehow I never pictured you with porn and a potty mouth. I envisioned…” he stopped, beginning to blush.

“Envisioned what?,” Jill prompted.

“I pictured…oh, I can’t.”

“Allen, I’ve sucked your cock, you’ve eaten my pussy, and we’re entangled on this couch totally nude. What could possibly be embarrassing to you now?”

“Well, um...oh, alright.” Averting his eyes and taking a deep breath, he dove right in. “I envisioned us on our wedding night. Both as virgins.” Looking up sheepishly, he grinned crookedly again.

“Come with me,” Jill commanded.

Leading him down the side hall, they entered the master bedroom, beyond which was a balcony that contained the Jacuzzi she had mentioned earlier. Turning it on, she climbed in and drew him in with her. Then she moved to the opposite end of the tub, bent over, and looked back at him searchingly.

Again, nature took over. Rock-hard cock in hand, Allen found the opening to her pussy and slowly slid it inside. “Ahhhhhhhh,” he sighed. It was an incredible feeling. Incendiary warmth, overflowing with her juices, amazingly tight. When he was buried to the hilt, he held still, enjoying the sensation of complete ensheathment.

Then Jill did it again. “C’mon, Allen, fuck me, fuck my pussy, fuck me hard, bang my boobs off, do it now!”

Growling in irritation at the despoiling of the moment, Allen grabbed her hips and began slamming into her, his belly smacking against her asscheeks much like ol’ Jack Hammer in Jill’s videotape. And still the salacious commentary continued. “Yeah, that’s it, hammer my pussy, fill me up with your big, long, hard cock.” He reached for her mouth, but found her swaying breasts instead, and then they both felt the approach of release. Jill’s hit first, her fluttering vaginal walls squeezing Allen’s cock mercilessly and triggering another gonadal gusher deep into her belly.

And still his erection wouldn’t diminish. Jill was astonished. It was like he hadn’t even had a wet dream in twenty-one years, and it had all been saved for her. “Don’t pull out, keep it inside me,” she ordered. Allen was still gasping, but managed to answer, “I wish I had two cocks so that I could be inside you and keep your mouth shut at the same time.”

Jill smiled enigmatically and replied, “Pick me up and take me to the bedroom.”

Allen wearily did as he was told. He knew that much about this situation wasn’t right, but he was too horny to think beyond the realization that this was the chance of a lifetime and he wanted to sample everything Jill had to offer.

Setting her down on her back on the bed, she lifted her legs up and put them against his shoulders. Before she could start cussing again, he once more plundered her mouth, and began thrusting into her missionary style. After a few minutes of this she grabbed him and rolled them over so she was on top and began riding him like a rabid bull. She came again. Then again. And still the thrusting continued. It was like Allen had become a sex machine.

Rolling back onto her back, Jill said, “Come here.” Allen crawled forward, straddling her as she had him earlier, and she captured his cock between her breasts. “Fuck my tits you prick, fuck them long and fmmmph.” Her monologue was interrupted by his dickhead as he smoothly and rapidly tit-fucked her into her mouth in a rising tide of now-undistracted lust. Jill reached up and started pinching his nipples, and he came explosively, showering her with surge after surge of his seed, all over her face, hair, and neck.

“Wow, my big stud, looks like I’m going to need another shower,” Jill purred.

Into the shower they padded, where the sexual calisthenics continued. Before the night was out they had done it in every room of the house, in both their cars, and even in the middle of the backyard after it got dark. He had no idea how many times he had cum, she had cum, or he had cum inside her. He vaguely remembered her saying that she was on the pill, but even the risk of pregnancy wasn’t registering in his brain on this night. Finally, long about 3AM, he was used up. They happened to be reclining on the dining room table at the time.

“Allen, you are a wonder of nature,” Jill giggled softly.

“Well,” he murmured, “if you say so. My thinking – to the degree that you allowed me to think,” he chuckled, “was that I’ve probably had more sex tonight than I will for the entire rest of my life, and that’s why I didn’t want it to stop.”

“What makes you think it stops tonight?” Jill asked. “As the Carpenters sang, ‘We’ve only just begun.’”

“For starters,” he began, “We’ll be going back to school in a couple of weeks. And long distance relationships are a lot more difficult to maintain. Plus…” he hesitated.

“Would you stop doing that?” Jill demanded, smacking playfully at him. “Just spit it out, along with what remains of my pubic hair.”

“Well…I guess the way I’d put it is that there’s a difference between reality and fantasy. Don’t get me wrong, you were unbelievable,” he added hastily, “but what does this do to our friendship? I mean, we went from pals and bosom companions to a one-couple orgy all at once. And the fact that you had, um, previous experience changes things. I know that might sound dumb, but it matters to me in how I look at us.”

Jill began to feel cold all over. “But, but, why, Allen? What has changed except that we’ve taken our relationship to a more intimate level?”

Allen looked pensive, as if he realized he was bursting the bubble – on a lot of things. “It isn’t being intimate. It’s that you’ve changed. Or maybe you never were entirely as how I thought you were. Admiring a woman from afar can lead a guy to develop idealistic impressions that I’m learning are impossible for her to live up to. Like the idea of her is almost more important to him than the actual woman herself.”

“I’ve loved you for years, Jill. Or at least I thought I did. And that may have colored how I perceived and approached you. The truth may be that I was in love with the idea of being in love with you more than I actually loved you yourself.”

For the first time all night, Jill was speechless. Allen glanced at her apprehensively, as if he was killing his life’s dream, and maybe hers as well. He pulled her into a body-to-body embrace, her head on his shoulder and gently stroking her left breast. “I’m not saying I don’t love you. Just that this has happened very quickly, and I think we both need some time to assimilate all these changes.”

Rolling on top of him on the table, she put her arms around him and kissed him with slow, determined deliberation. But this time his hands didn’t make a beeline for her bottom. He just held her for a while longer. Then he got up, dressed, and left.

Two weeks later Allen and Jill returned to their respective colleges. Three weeks after that he met another beautiful brunette named Deatra, who wasn’t experienced, and indeed was resistant to any attempt at courting on his part. But he was patient, and within a couple of months she had let him kiss her. They became a couple. He brought her home to meet his family the following March. In May he proposed, and she accepted. A year and a half later, they were married.

The next time Allen saw Jill was at their ten-year high school reunion. He no longer stammered or had difficulty making small talk, what with pictures of and stories about his baby daughter, Elaine, to tell.

Jill just listened. She was still single; it seemed that every other guy, for her at least, really was a prick with legs. The one guy who wasn’t, in the end, hadn't wanted her. And the irony was that where Allen had once considered her to be off-limits, now he really was off-limits to her.

“Deatra?”

Allen’s wife turned, saw Jill’s approach, and smiled. “Hi, Jill. Are you leaving for the evening already? The night is still young, especially when you have your in-laws to baby-sit for you,” she chuckled.

“Yes, I think. Some of us are going to a club a little later. But I’ll see you and Allen and little Elaine at the picnic tomorrow.”

“Great. See you then.”

On impulse, Jill embraced Deatra and said, rather wistfully, “You’re a lucky gal, Dee. A lucky gal indeed.” Then she walked out the door.

Seeing Allen coming over with her drink, Mrs. Grosserhahn asked him, “What was that all about?”

Looking after where Jill had departed, Allen felt a little sad. “Growing up. And paths not taken. C’mon, the slide show is about to begin.”

12
Please rate this story
The author would appreciate your feedback.
Share this Story

READ MORE OF THIS SERIES

Similar Stories

HOT SHOTS: M.I.L.F Spring Break Loses his virginity to his girlfriend's mom.in Mature
Party with the Neighbor MILFs A teen joins his four mature women neighbors.in Mature
Poolboy Benefits She's desperate for help. The question is, how desperate?in Romance
Son's Best Friend Sunbathing mom is surprised by her son's black friend.in Interracial Love
Hell... What are Friends For? Ashley discovers virgin friend has a miracle cock.in First Time
More Stories