Pleasure Upon Request

It was at this moment that our waitress arrived, a beautiful, fresh-faced brunette with bright brown eyes. If all the waitresses at the Apple Dish looked like this girl, I thought, I would definitely become a repeat customer.

"Hi," she said cheerfully, her voice markedly southern. "What would y'all like to drink?"

I heard some Tennessee in her voice and might have pursued asking the girl about it, if the conversation I was currently involved in did not seem so serious. Still, I filed it away for later; perhaps I would circle back around to the Apple Dish another time.

Sadie smiled. "Iced tea, please," she requested, to which I added, "I'm fine, thanks."

The girl smiled and scurried away, and after watching her go for a moment, my eyes returned to Sadie, who was looking at me intently, gauging my reaction to her words from a moment ago. I nodded, urging her to continue, and so she did.

"Doug has several sexual fetishes," she went on, "and most of them are unusual. We've had normal sex plenty of times and he's very good, and we have a lot of fun, but there are some things he likes that sort of . . . take him to a new level of enjoyment. We've tried some of them and it's been incredible, but . . . some of his fetishes are difficult for the two of us to fulfill."

The waitress returned with Sadie's iced tea and took our lunch orders, although this time I hardly even looked at the girl; my eyes were focused on my lunch companion. She was telling me some of her marital secrets for a reason that, I hoped, would soon become clear; I owed her my complete attention.

"I'm a sexual person," Sadie said once the girl was gone, her voice hardly above a whisper, and despite my best efforts to contain it, I felt a familiar stirring in my loins. I did not blame myself entirely; hearing a beautiful woman speak in such a way was bound to cause such things.

"Doug has mentioned that," I said, trying to put her at ease with a little smile.

She blushed, then smiled. "I'm a sexual person," she said again, "and I've never had a problem with some of the things he's asked me to do, and believe me, kinky is an understatement. He is honest with me about everything and always treats me with respect, even when . . . well, even when respect is not the goal of what we're doing."

I'll just come right out and admit it: by this point in the conversation, I was rock hard.

She sighed. "We both wondered where his desires and fetishes came from. We saw a sexual therapist together and discovered much of it has to do with things from his childhood, some of which he remembers and some of which has been repressed. The therapist told me the best thing I can do as his wife is fulfill his desires, as long as I am comfortable myself with them. We've been married for two years and our sex life is still very strong." She chuckled, and added, "A little weird sometimes, but at least it never gets boring."

She was gaining strength with each word. Her voice, while quiet, no longer wavered and her face held none of its earlier nervousness. Her blue eyes were intense, but also soft around the edges.

I took a shot. "Which brings you to why you're telling me all this," I said.

She looked at the table and blushed again, which made her look absolutely adorable. Sadie was a strong woman and very rarely exhibited shyness, and seeing her blush, multiple times no less, was an unmitigated treat. After a moment, she raised her head.

"Doug has several fetishes that involve other people," she stated bluntly, "but we have never had the courage to travel down that road. I have never had the courage to travel down that road. We have decided it might be time to give it a try, and Doug is going to ask you about it."

"Ask me about it?" I asked suddenly, needing clarification.

Sadie met my gaze point blank. "He is going to ask you to sleep with me."

A series of interesting thoughts and emotions coursed through me at that time: first, a part of me was shocked and stunned at what Sadie was saying, both about Doug's personal sexual likes and the fact that he might actually want me to be involved; second, a part of me was not surprised at all, as if I knew something like this was coming; third, a very specific part of me was twitching and throbbing at the sudden and un-asked-for image of Sadie naked and writhing beneath me in sexual bliss; fourth, a part of me felt an extreme sense of honor and appreciation for being considered enough of a friend to be entrusted with this information, and responsibility; and, fifth and lastly, a part of me was utterly concerned about my friendship with Doug and Sadie, and what would happen if we, as Sadie put it, traveled down that road.

Apparently, again, it all played out on my face, which was another thing that was unusual for me; I was usually very good at keeping the cards very close to my vest.

Sadie smiled soothingly. "I know this is a lot to take in," she said gently. It seemed her own trepidation and concern had decreased as exponentially as mine had increased. "I know how unbelievable this all must seem. Our therapist calls it a cuckold fetish, meaning Doug will receive extreme sexual gratification from watching me with another man, but not participating himself. It took me a long time to wrap my head around the idea, but apparently this is a way for Doug to prove himself to me, as well as live vicariously through me. His pleasure, from what I understand, is tied to my own pleasure, and without having to think about pleasuring me himself, his pleasure increases. It's complicated; our therapist could do a better job explaining it."

"He's going to ask me to have sex with you," I said slowly, "while he watches."

She nodded and said simply, quietly, "Yes."

"Why are you telling me this? If Doug is going to ask me, why meet me before?"

"Doug has been trying to ask you for some time now, but he has no idea how to get there. I thought it was important for you to know everything ahead of time, so you can help guide him in the right direction, not to mention already having been able to think about your answer."

I thought for a long moment. "You're right, good thinking," I told her, then stopped and thought about asking the one big question rattling around my brain, and did. "Why me, Sadie?"

She smiled sweetly. "The short answer is we both like you very much, and respect who you are as a person, and know you will treat this with all the seriousness it deserves. The long answer is we compiled a list of every man we knew, and by process of elimination across a variety of factors, whittled it down to you, someone we both approve of."

The image of Sadie with a list of names of men she could potentially have sex with, and slowly narrowing the list down to me, was enough to push the throbbing to near painful levels.

"I suppose I should take that as a compliment," I said with a sly smile.

Sadie grinned, and nodded. "A big one," she agreed.

The waitress returned with our food at that point and set the plates in front of us, and it was clear to both of us that the business end of our lunch was concluded. I smiled and asked Sadie about work, and she did the same, and for the rest of the lunch we chatted in a manner more befitting a pair of old friends, not a man and woman who might soon find themselves in carnal congress.

* * *

It was Friday morning when Doug called to schedule a golf game for Sunday. He mentioned nothing of my lunch with Sadie, which probably meant he still did not know about it.

The thought of joining Doug and Sadie had rattled around my head for three days. It was good Sadie had given me warning, since there is no way I could have realistically given Doug an answer in the moment and felt fine with it.

I called Alyssa after speaking with Doug and was happy to find her free for the night, and after calling off my working day early and hitting the gym, freshly shaved and showered, I picked her up at her place at seven o'clock for an easy night of dinner and a movie.

Alyssa was always fun to be with and the night progressed swiftly. Dinner was a low-key affair at a tasty little gourmet French place in Brentwood, followed by a run down to the theatres in Century City, which was a great spot to see and be seen. My date was simply attired but smoking hot in black Ugg boots, black mid-thigh mini-skirt, and a dark red three-quarter-sleeve, scoop neck top. Needless to say, Alyssa was seen by many people that night.

There were a couple of high-profile films opening seeking to get a jump on the labor day weekend box office business of the next weekend, one of which Alyssa really wanted to see. It was called The Summer of Loving, starring a young Spanish actor whose name I cannot pronounce and a young American actress named Josephine Belle, who was quite attractive. It was heavy on the drama and romance, but also featured a surprising amount of humor, which satisfied me, although it ended on a bit of a downer and Alyssa was dabbing her beautiful green eyes as we left.

I pulled into a parking space outside Alyssa's apartment complex and turned to find her looking at me with a twinkle in her eye. "Want to come up?" she asked with a sly smile, both of us understanding where things would lead if I did.

"Of course," I replied, grinning back.

We uncorked a bottle of wine, thinking about enjoying each others' company before the real action began, but Alyssa and I are sexual people, to borrow a phrase from Sadie Stillman, and it did not take long for us to throw back a couple of glasses and get down to business.

Which is how I found myself several minutes later with my hands on the woman's exquisite ass, both of us naked -- although to be totally clear, she was still wearing that black mini-skirt, just nothing else -- her bent over the dining room table with me squatting behind her, the skirt flipped up, my face buried deep in her hairless pussy.

My fingers were spreading her ass cheeks as my tongue delved inside her precious pink folds, and she squealed as it plunged inside her as deep as it could go. I lapped at the puffy lips, so swollen with desire, relishing the heat and juicy wetness I found there, my nose nestled snugly against her anus. I licked and tasted and teased as she ground her bottom back into my face, urging me deeper, and so I changed my plan and assaulted her clitoris with the tip of my tongue before wrapping my lips around it and suckling.

She squealed again, and louder.

I spread the cheeks of her ass further then, almost painfully stretching them apart, and without a word of warning moved higher to lap at the wrinkled pink plot above her pussy, and she squealed a third time as my tongue flittered over her asshole, swirling and tasting in time with the grinding of her hips.

I grinned, considering, and then stuck my tongue up her ass, and the reaction and effect was utterly instantaneous: Alyssa screamed at the top of her lungs. The words were unintelligible, but the sound said it all.

And yet as much as I enjoy the opportunity to feast on the ass of a beautiful woman, analingus on Alyssa was not new for me and I was eager to speed things along.

I thrust my tongue as deep inside her anus as it would go, eliciting another smaller squeal, then withdrew and rose to a standing position behind her. It was time for the main course.

I traced a finger down the sleek line of her back, the pale flesh smooth and soft, before it came to rest at the small of her back where her black skirt was scrunched up, my palm flat against the cool surface of her skin. She was breathing heavily, panting, and her back was rising and falling.

With one hand between her shoulder blades I held her down, pinned against the dining room table, her pert breasts squashed into the surface. Her ass quivered with anticipation and she gasped out loud as I guided my cock between her thighs.

I could feel the heat from between her legs and raised the head of my cock to brush ever-so-gently against the pink folds, and her breath caught in her throat, waiting for the finish. I manipulated my cock, rubbing the engorged head back and forth across her clit, wedging the shaft between her lips, her juices trickling down over my testicles. This was just the warm-up, of course, and soon my mushroom crown found the opening of her sex.

And so I pushed the head of my cock inside her, where it belonged.

Alyssa's pussy was tight and wet as always, and burning hot, and I was forced to breathe deeply in that first moment to restrain myself. Once controlled, my hands trailed down her back and came to rest upon her heart-shaped bottom, and spread her cheeks wide to watch as slowly, ever slowly, I fed my cock inch by solid inch into her willing depths.

Alyssa is one of those girls who reaches climax quickly, which is one reason why she loves to fuck as much as she does, but even I was surprised this time when her body froze for an endless moment as warm fluid washed over my cock and trickled down both of our thighs. She shivered violently and expelled a desperate breath before a long and warbling moan of pleasure followed, and her back arched and her ass pushed back as her body went rigid.

This was the instant I bottomed out, my waist nestling up against the pillows of her rump, and we paused then, her immobilized by pleasure, me savoring the sensation as the fierce muscles of her pussy clutched at my cock.

I did not give her time to recover; I knew Alyssa and what she wanted, and what she could take, well enough to know she wanted me to blow right through her orgasm and keep on fucking her, which I did with enthusiasm.

I began to move, my wet cock sliding past her wet folds again and again, in and out, in and out as I set the tone and tenor of our session together. Beads of sweat broke out over my skin as I worked, varying my speed, varying my angles as I penetrated her. Soon her body began to respond and the sexual rhythm was developed; she rocked forward as I withdrew, drawing my cock further and further out until only the tip remained within, a position held for the briefest moment before I plunged back in, burying myself completely, filling her, fucking her, only to withdraw once more to begin the process anew.

I looked down happily as I fucked her, watching my gleaming cock as it disappeared into and reappeared from within her pink folds, her tight little anus winking up at me from its place just above; it was a luscious hole, that one, and my opportunities with it were always relished. I wondered fleetingly if tonight would be one of those nights.

Our pace quickened and her back arched, and I reached down and around with one of my hands to clutch one of her tits, pinching and squeezing and toying, enjoying all the delights her body had to offer. Her skin glistened with a light sheen of sweat.

The sound of my stomach slapping against the flesh of her bottom as we came together combined with her moaning and gasping to form a simple symphony of sex as we fucked, our rhythm long now established, its cadence set. Our bodies moved together as one, grunting, groaning, whimpering, my hips thrusting, hers bucking back, straining and jiggling as my cock pierced her, invading her depths.

And then the end came as I let myself go and orgasm ripped through me, and I spurted what seemed to be the whole contents of my balls into her womb, filling it completely with my hot sticky fuck syrup.

Alyssa screamed as another climax conquered her, too, her head snapping back, face to the ceiling as her body quaked, utterly overwhelmed as waves of pleasure crashed over her like surf upon the sand. Her limbs were a mess of inexorable trembles.

My drained cock was still pulsing inside her as I sagged forward, no longer capable of supporting myself in the aftermath of my own exemplary orgasm, and the heat between our bodies as my weight came down upon her could have practically created steam.

And then she stirred, shifting under me, and I heard the slightest hint of a laugh slip from her lips, and I knew without seeing that Alyssa was smiling happily.

"Oh my god," she said, one of her favorite sex refrains.

I grinned. "Well, maybe we don't need to quite go that far," I said.

As usual, she turned it around. "Maybe we do," she responded playfully.

I laughed, and she laughed, and while laughing I gently pulled my softening cock from her pussy, and her laugh instantly morphed into a breathless gasp. A whimper followed, and following that a gush of fluid from her now unplugged hole that trickled down her leg, and she gasped again.

It did not take long, thankfully, for the two of us to recover; we both knew from the outset that this would not be a one-pop evening. My apologies to Elton John, but Friday nights were made for fucking. It was a fierce first round, however, and Alyssa knows how much I enjoy having women in the shower, so in little time I found myself being dragged down the hallway to the bathroom, where the girl proceeded to blow me almost to completion before spitting my cock out, mounting me, and bouncing frantically on my cock in a stand-up position.

She was a hellcat, no two ways about it.

The lag time between rounds two and three was longer, thankfully, and after cleaning up and drying each other off, which is always a pleasant experience, we took to her bed, lounging naked as we basked in the afterglow. Alyssa was draped across my body, her head upon my chest, and my left hand was gentle stroking the supple flesh of her bottom, squeezing here and there, dragging my nails down into the small of her back, pushing my fingers into the dimples, and just enjoying the smooth feel and texture of her body without, for once, any real sexual implications.

"How well do you know Doug and Sadie?" I asked suddenly, surprising even myself at the question.

Alyssa did not move, but replied, "I don't know Doug all that well, to be honest, but I've known Sadie for a long time, since college. Before she got married, we hung out all the time. I've known her longer than I've known you, actually."

I felt like I should have known that. "I forgot about that," I said sheepishly.

"Clearly," she said with a touch of amusement. "Why?"

"Doug has just been acting a little weird lately," I said, deflecting, "and I wondered if Sadie might have said something about it."

She was silent a long moment, then lifted her head and turned it to face me. "You know, at dinner the other night Sadie asked me something a little strange when we were in the bathroom. I didn't think about it much at the time, but after you said something, I thought about it more and remembered. She asked if we'd ever taken part in a threesome together, you and me."

"Really?"

"Yea, I thought it was a little weird, too," Alyssa admitted, "but then she told me a friend of hers was thinking about doing it and wanted some advice, and Sadie said she'd never had one before, which was kind of surprising."

"Why?"

Alyssa giggled. "Sadie's certainly not a prude," she said, "and let's just leave it at that."

I thought for a moment, then smacked Alyssa harshly on the rump. She squealed and wiggled, but my firm grip held her in place. "Alyssa," I said ominously, "spill it."

She settled and pushed her butt back into my hand. "We've fooled around a few times," she revealed with another giggle, "and she eats pussy really well. I kind of figured she'd have had a bunch of threesomes by now, since she's also into girls."

Well, that was not what I expected to hear, but it did grant a layer of insight I might not otherwise have gotten. Sexual person, indeed, Sadie Stillman.

The wiggling bottom beneath my hand did not stop wiggling, and when I heard the quickening of Alyssa's breath, I knew it was game time, once again. I took a deep breath, and said, "This time, Alyssa, I'm taking your ass."