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Chapter 1 – Uncharted Territory
Unaware of the curious turn his life was about to take, Matt headed downstairs to the kitchen in search of a snack and a beer, not necessarily in that order. It was a typical Saturday evening. He had been rehearsing a voiceover script while Lisa held her weekly jam session. After grabbing a couple chicken legs and a Heineken, he gravitated toward the living room intent on settling in for the beginning of Saturday Night Live. Instead of the muffled extemporaneous jazz that Matt expected would be emanating from the garage, faint, vaguely sexual sounds drifted toward him from the room to which he was headed.
When he saw that the television was already on and two naked women were embracing in high definition glory, Matt paused at the doorway. A silhouette of his friend was about all that was visible in the room besides the images on the jumbo plasma TV. Apparently the jam session had ended early he noted, not at all displeased with this development. Lisa must have heard him approach or simply sensed his presence.
“Do you like girl-on-girl porn?” she asked conversationally, without turning away from the screen.
“What kind of question is that? I’m a guy. Of course I do.”
“Well then, come on in and enjoy.”
She patted the seat on the leather chair beside her for emphasis. Without hesitation he acquiesced.
Matt was not a connoisseur of x-rated films, but he noticed that this one had better production values than most of the ones he’d seen previously. As they watched one particularly intimate scene it struck him that the performers came through as real lovers instead of actresses. Both women were a little older than is customary in such films, and despite saying very little they projected an air of authenticity often lacking in this genre’s thespians.
The athletic blond was clearly the assertive partner, in a tender and sensual way. She showered her diminutive lover with soft body kisses, slid a moist pussy back and forth along her thigh and ground it into her vulva with gusto. Watching this unfold was extremely arousing for Matt. The dynamic between the women gradually changed and soon each was orally pleasuring the other to an intense near-simultaneous orgasm that precipitated the all-too-soon fade to black.
When the DVD was through, Lisa queued up another one and put it on pause while she went to the wet bar and mixed up a pitcher of her famous high-octane margaritas. Once they each had a drink in hand, she punched the start button and intermission was over.
The second feature was from an amateur series. Although the lighting was spotty and the camera technique was sometimes a bit shaky, it had a raw in-your-face sexuality that was riveting. No doubt the Heineken and Cuervo Gold influenced the resuscitation of Matt’s long-dormant libido, but the raunchy daisy chains and unrestrained lust of the twenty something tatted-up girls would have gotten him worked up on their own. He was particularly appreciative of one interlude that involved extreme close-ups of the consumption of massive amounts of strawberries and whipped cream from a vagina whose labia were adorned by multiple heavy-duty stainless steel rings. Matt could easily understand why Lisa had this film in her naughty DVD stash – it would definitely hold up to repeated viewings.
They sat in companionable silence as the credits scrolled by. The combined buzz from the film’s visuals and the alcohol triggered an intense fantasy cascade. Matt was so entranced by this cerebral movie that Lisa’s question barely registered.
“What do you think about friends with benefits?”
His distraction caused him to have a duh moment.
“Is that a book … or a movie?” he asked hesitantly.
“No silly, it’s an expression. Or, more precisely, a type of relationship.”
Matt slapped his head theatrically.
“Sure, of course. I’ve never given it much thought. Why do you ask?”
“I was thinking that maybe we should try that.”
He didn’t know how to respond, so he remained silent. Had it not been so dark in the room, a skeptical look would have been visible upon his face.
“I’m serious. Think about it, neither of us have a love life and we obviously like each other or we wouldn’t have been roomies for the last three years. It makes a lot of sense.”
“Well … there’s something to what you say … but … you’re a lesbian and I’m not. I’m not even a woman. Just how would friends with benefits work in this situation?”
Lisa smiled mischievously.
“Oh, you’d be the bottom of course.”
His reply was quiet and noncommittal.
Matt mused on the proposal, imagining what might transpire if this was to happen. His current state of excitation caused him to seriously consider becoming a surrogate femme dyke lover for his friend. It was hard to completely wrap his mind around, but at some visceral level the idea was strangely appealing.
“This isn’t as farfetched as it sounds, you know. You are naturally sweet and gentle, attentive to women …and sort of … passive.”
“Big-time! You’re deferential to everyone, but doubly so with women. Between your personality type and growing up the only boy in a house full of bossy older sisters, it was destiny, pure and simple.”
The aha moment finally arrived, prompting Matt to ask:
“You’ve been giving this a lot of thought, haven’t you? How long have you been planning this?”
Lisa grinned broadly.
“A couple weeks.”
“So how does the rest of the script play out?”
“First, I ask for the sale. And then you say, ‘where do I sign?’”
“Just like that?”
“Just like that.”
“And what’s my motivation?”
“You’re a horny little toad and this is the best offer you’ve had in a long time.”
“Bravo! You can’t argue with superior logic like that. So ask.”
Assuming a fake formal manner.
“Well Mathew, do you wish to avail yourself of this once-in-a-lifetime opportunity?”
Replying in like fashion.
“Why yes, Lisa, I believe I would. Where do I sign?”
“Since I’m familiar with your good character and other admirable attributes, a handshake will be sufficient.”
With mock good fellowship she extended her right hand, which Matt shook then kissed grandly. The fateful deal was struck. A few seconds later Lisa pushed a button on the remote and the section of the room where they were seated was immediately illuminated by track lights.
“Well, there’s no time to get started like the present,” she said. “Let’s get out of these clothes and go skinny dipping.”
Matt stood up and, affecting an exaggerated bump and grind, began peeling off his T-shirt, finally letting it drop with a seductive flourish. Next he stepped out of his sandals and struck a coquettish pose while running both hands through his auburn shoulder length hair and licking his lips. Then he slowly unzipped his pants. With Lisa hooting her approval, Matt continued vamping it up and eased his pants down and off. Suddenly feeling a little shy, he stopped.
Lisa inspected him closely as he stood there nearly naked under the lights.
“You know, Matt, in my inebriated state, standing there in just your bikini briefs you look more like a small-breasted woman than a thirty-year-old man. Your soft undefined torso and long and nearly hairless legs, slender ankles, and delicate feet scream tomboy.” Winking playfully, she added: “Which, by good fortune, just happens to be my type.”
Eager to cut short Lisa’s analysis of his physical characteristics, Matt announced:
Obligingly, she joined him under the lights, kicked off her espadrilles and began unbuttoning her blouse. Soon the garment fell open just enough to offer a peek at the sides of her breasts, and in a toned down imitation of his performance she wiggled out of it and thrust her chest forward. Seeing her naked breasts for the first time was a curious experience for Matt, considering the nature of their relationship to this point. He couldn’t help but think, “Son-of-a-bitch, my best friend has killer tits and I never even noticed before!”
Using her best Marilyn Monroe voice Lisa cooed: “I need some help with this, Matty … it seems to be …stuck,” thrusting her hip provocatively in his direction as she tugged at the zipper of her skirt.
This parry surprised him, causing a fleeting awkward moment before he went to her side. After Matt guided the zipper open, she encouraged him to remove her skirt. She enjoyed the startled look on his face when he realized she was in commando mode underneath. Standing there nude, Lisa’s body bordered on being voluptuous, but her closely cropped blond hair lent a boyish quality to her overall appearance. Without warning she slid his underpants off, exposing his flaccid penis and a sparse patch of pubic hair, before taking his hand and leading him outside to the pool.
. . . . . . . . . . .
The multicolored bougainvilleas lining the yard were mostly hidden in shadows. Even though it was past midnight, the temperature was still in the mid eighties – normal for late summer in southern California. And after being exposed to the sun all day, the water was warm, although it looked cool and inviting as it shimmered from the pool lights.
They started out swimming aimlessly, but after a few minutes lounged in the shallow end of the pool enjoying the moonlight and the sounds of the night. To a casual observer they would have appeared oblivious to each other’s nudity as their conversation resumed and drifted from topic to topic. But there was a sexual tension lurking below the surface that they both pretended didn’t exist. Eventually Lisa climbed up on the side of the pool and sat directly in front of Matt with her legs spread apart. Perhaps ten seconds passed quietly as they gazed into the beckoning abyss.
A barely audible “Pleasure me, Baby” finally broke the silence.
Normally Matt would have indulged in some manner of foreplay before engaging in oral sex, but it was pretty clear that Lisa wasn’t interested in any preliminary activities on this occasion, so he got right to it. Not before taking a moment to visually drink in the delicate beauty of her delta, however.
Tentatively Matt licked her inner labia, savoring the juices generated by her arousal, before inserting his tongue inside of her and lapping cat-like with ever increasing zeal. She shuddered involuntarily at the first touch of his tongue on her clitoris. Between the x-rated DVDs and sheer anticipation, Lisa’s libido was on fire. Only a short time passed before a prolonged moan of pleasure signaled her orgasm. Hearing her cry out in that way thrilled Matt. He secretly hoped that his oral skills measured up to those of Lisa’s past female paramours.
Matt waited patiently while she recovered, but soon enough continued laving her center passionately with his lips and tongue, doing his best to tease as many climaxes from her as possible. He enjoyed making love in this fashion – it had always been his favorite. By its very nature cunnilingus is a somewhat submissive act, but knowing that it was not a prelude to coitus or reciprocal oral pleasuring accentuated the submissive aspect of it for Matt. He found himself slipping further and further into subservience and to his surprise, relishing the descent.
After the final la petite mort Lisa leaned back and lay spent and limp, her legs dangling in the water. As he rested his head on her thigh, the tantalizing scent of arousal exuding from her loins engulfed Matt and reinforced the feeling of total abandon that had washed over him. Finally, Lisa sat up, displaying a dreamy smile on her face. Without a word being spoken, she struggled to her feet and headed into the house, beckoning him to follow with a lazy motion of her hand.
. . . . . . . . . . .
Lisa directed Matt to lie face down on the bed after she retrieved a blindfold from her nightstand and tied it in place over his eyes. While he waited in darkness, he heard her moving about and tried to deduce what she was doing. The first thing she did was light a massage candle with a sensual fragrance and let it burn long enough to produce a pool of warm scented oil. During the melting process she slipped her harness on and fastened a modest-sized attachment to it. As she climbed onto the bed she activated her iPod and soon the improvisational piano music from Keith Jarrett’s Koln Concert filled the room.
Matt shivered with anticipation when she poured some of the melted shea butter in the small of his back and began spreading it in all directions with the tips of her fingers. She lingered on his upper body, working in the oil with firm, tender strokes. But by no means did she ignore his lower extremities. Matt would have been hard pressed to walk without assistance after she finished massaging first his legs and then his feet.
Eventually she arrived at her ultimate destination. Savoring the moment, she hesitated briefly before pouring warm oil onto his butt and slathering it generously between his cheeks. In no particular hurry, she lay down on top of Matt and began slithering from side to side.
Matt’s skin tingled as Lisa slid her breasts along the oily contour of his back. As she pleasured him with skin-to-skin sensations, she also began teasing his anus with her dildo. At first she rested its length between his ass cheeks and slowly slid it up and down. Progressively she positioned herself lower on his body until the up and down movements resulted in the tip of the dildo nudging Matt’s opening on the upstroke.
“Your life is about to change forever,” she whispered as she gently eased her well-lubricated phallus past his sphincter.
Her prediction would prove to be prescient. As she continued to penetrate Matt he was startled by the pleasurable sensations it caused, unlike any he had ever experienced. When she thrust deeply he felt a satisfying fullness and a warmth reminiscent of the glow he sometimes felt just prior to ejaculating.
Lisa took him slowly at first, but gradually increased her pace. And as she did so the dildo began stimulating his prostate, effectively milking him and causing semen to ooze from his still-limp penis. The longer and harder she penetrated Matt the more he succumbed to the submissive sexuality of a bottom. By the time she was finished, he was well acquainted with his true sexual nature.
They both remained on the bed without talking, completely sated, in an odd post sex daze. They were friends, not lovers. They had no frame of reference for this situation. Matt couldn’t know what was going through Lisa’s mind, but he was thinking that finding a sexually compatible permanent mate just got more complicated for him, he seriously doubted that there were many women looking for a newly minted bottom.
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