Best Friends

by maryjane

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Cheating, Oral Sex, Anal Sex, .

Desc: Sex Story: He's Dick and I'm Jane, but this is not a story for children. He was my best friend, now he's my lover.

He's Dick, I'm Jane, but this story is not for children.

The sweet taste of his cum lingered on my tongue. I reached between my legs and felt the last of his little swimming sperm dying inside my cunt. Even before my brain began to reconstruct the night, I knew that I had given my best friend at least two orgasms.

With the blackout shades open just a drop, the morning sun had finally reached the point where its bright rays had caught me squarely in the eyes. I stretched my arm out to the other side of the king-size bed, expecting to touch Dick's warm body, but he was gone. My body sat bolt upright, the sheet falling off my naked breasts. My nipples were instantly hard, remembering the frantic sucking of his lips as he had tried for the ancient adult male Holy Grail, the quest for milk from a barren teat.

My fingers massaged between my legs, attempting to rub away the soreness in my cunt. I had known when I first saw that gorgeous, immense cock that he would dilate my vaginal walls as neither man nor boy had ever done, yet I hadn't expected him to ravish me like an animal. An animal, yes, but such a wonderful, beautiful and gentle animal, one who had in an instant made me forget every other cock I'd ever known.

Which I guess is normal when friendship finally turns to lust and then, in the millisecond of that first carnal insertion, turns to romantic love.

I removed my fingers from inside me and brought them to my mouth, to taste again the sweetness of his grunting discharge.

The bathroom door was open, the light off. Definitely he wasn't there. My ears strained to hear any noise from the other part of the suite. Nothing. Maybe, probably, he had gone downstairs for coffee. Maybe, hopefully, he would bring me back a cup. Regular, black, two sugars, as he well knew.

Or maybe he was belly up to the rail of a Craps table, hoping to get as lucky at the table as he had gotten lucky last night in bed. But of course last night hadn't been a question of getting lucky. We had known, wordlessly, for what had seemed like weeks that this trip to Las Vegas had not been to gamble but merely as an excuse to be alone, to consummate our lust, to fuck and suck and to make love.

The suite was one of those run-of-the-mill accommodations for regular guests who gave the tables good action. Just a living room and a bedroom, keyed-elevator upper floor, two baths, decent view. In no way did it approach those penthouse monsters reserved for those (mostly) foreigners who bet the equivalent of the average person's annual salary on a single card or roll of the dice. Those were the suites that came with champagne, flowers and clean whores. Or with pretty young boys (over 18, of course) for those so inclined.

No, my Dick (Richard, really) was always comped for room, meals and shows, but he didn't get a free flight from Big-D-little-a-double-ell-a-s or a free limo from the airport. Nor did he get his personal Casino Host to cater to his every whim and lust. That was my job, and it would always be my pleasure to please him in every way humanly possible.

I leaned back against the headboard. As I reached for a cigarette, I felt wetness under my ass cheeks. Ah yes, it reminded me that I must have made him cum at least three times, not twice. He'd been surprised when I'd offered him my back door, but I'd been fucked anally often enough that I could survive it. I closed my eyes to relive the night, the kissing, the fondling, the sucking and fucking. I knew that when he came upstairs, with or without coffee, he'd be naked when he came into the bedroom, his cock pointing the way. And that we'd be repeating the 'I love you' chorus in the same romantic way that we had first exchanged the previous day and evening.

But more of that stuff later.

Although I had known him for a long time, he became my best friend when I started high school. Oh, of course I had the usual collection of female BFFs who came and went, but he stayed on. And as we now know, he has stayed forever.

He became my best friend when he asked for advice about a first date. Like should he wear a tie, where was a restaurant that she might like. And circuitously, very very circuitously, and almost with a whisper, what he should do or say in order to get into her pants. I didn't know who he was talking about, other than that I knew he didn't mean me. Still, I was flattered, what with me still being a virgin and instantly fell into serious like with him.

When I saw him the following day, he was obviously in a depressed mood. He didn't go into the gory details about how far he had gotten, but definitely he had not hit a 'home run'. Second base or third base, depending on your definitions, but that was it. Yet him trusting me with that information, though still not her name, left me feeling very warm.

No, I do not mean sexually warm, I mean just plain platonic best-friendship, a friendship that was to continue for a number of years – high school, college, grad school and beyond. And up until just before the present time, all talk about sex was about sex with other people, not with each other.

A few words about us. He's tall and slim, but without the abs of an athlete. He's adequate at swimming, tennis and badminton, but not good enough for any team. He does occasionally play some touch football, but like an old man. The best that he can see without specs is 20/100, but even without them, he thinks that I'm beautiful. He looks like a nerd, but it balances out by him being brilliant. His cock, as I've recently learned, is like his body, long and slim. But it fills me like none other.

I'm decent looking, but not the beauty that he calls me. That adjective must be triggered by his friendship and love. My face should better be called perky, what with the red hair and tits which evoke the same word. I'm five foot two and a teensy bit overweight, on intermittent diets. Since I graduated from college, men whom I've dated have taken to referring to my hips as made for carrying babies. I quickly took that to mean fuckable, which appellation I appreciate. I have a good bit of experience in proving my fuckability.

Have I mentioned that he's my best friend? Or how much I wish that we had become lovers so many years ago?

He hadn't been a virgin that first day he asked me for dating advice. I knew that; it was obvious. And every once in a while, since our 'seduction' began, I've wondered if that very first plea for advice might have been simply an attempt at an ice-breaker to get me softened up for a discussion of sex. Well, I didn't take it that way then, even though many of our talks did cover the subject.

He did tell me whenever he scored, and did exhibit a bit of pride in doing so, yet always as someone who had to talk about it and didn't want to share it with any male friends of his. I reciprocated. I remember telling him the following morning after having surrendered my cherry. He smiled and gave me a chaste kiss on the cheek. After I had more experience, I gave him some pointers on how to eat a pussy, not that he was a novice, and he gave me instructions on the sexiest method of sucking cock.

But we spoke of much more than sex. Our talks covered money, politics, sports, art, even love, the whole gamut of human interaction.

He's a doctor now, a surgeon. It's the old familiar story. His first wife worked her ass off to put him through med school. Then, as his practice began to prosper, he dumped her for some bit of fluff who had gone to Nursing School for the sole purpose of stealing some woman's doctor husband. I know her. She's a good looking piece of arm candy, but I think she's a cunt. Too bad that he was thinking with his cock instead of his brain. He knows better now.

As for me, I'm a lawyer now. I'm on the Partnership Track at one of the major law firms in Dallas. That means that I work like a slave. It feels like 25 hours a day, 8 days a week. I exaggerate of course, but not as much as I'd like. In fact, I'm on call 24/7 and I know, everyone in the field knows, that a large part of my future at the firm will be based on how many billable hours I can generate. I like litigation for large clients because then it's easier to pad the time sheets with 'legal research' or 'drafting' hours.

I've been able to make it a habit of fucking the clients' house counsel so that they don't question my hours on the firm's bills to them. Hey, don't judge me. My wonderful lover does the same thing with coding bills to Medicare and the insurance companies, but he has a staff trained how to do it. He doesn't have to get his own hands dirty.

That's another element of our closeness. He knows what I do with my time sheets and also that I fuck for some clients. And also that I fuck around with any man who tempts me, married or not. I know what he does with his billing and which nurses and patients whom he's balling. Oh yes, he does cheat on that second wife. Not surprising, since after a year of marriage, he started referring to her as 'Queen Bitch'. As you can see, neither of us judges the other.

I've never married. No husband should have to put up with the hours that I honestly put in at the office, nor with my constant search for the perfect cock. Now I think I've found it, but my Richard knows me well enough to accept the fact that I'm liable to keep looking.

He and I speak almost every day, almost like an old married couple. 'How was your day? What are you doing now? Etc. We don't do any of that 'What are you wearing?' shit. Not yet anyway. All this is thanks to the invention of the cell phone, so nothing goes through receptionists or inter-coms. Of course, with both of us having hectic work schedules, sometimes it's difficult to get each other on the phone, but we manage.

His office is right next door to the hospital building in which his group has staff privileges. My office is barely two miles a day. Whenever we can, we meet for lunch, one of us walking if the weather is nice. We try to meet for dinner once a week, but it's always in a well-lit well-populated restaurant. We never considered one of those candle-lit places, because our relationship was simply friendship.

In retrospect – hey, I'm a pretty sharp attorney – I should have known that someday this relationship was likely to go beyond what it had been. Occasionally I even had a fleeting thought about that, but I'd dismissed it immediately. Occasionally too I'd notice his eyes on my chest, but I thought of that as a mere male glance at almost any female.

Then one evening we got to our favorite place and found that it had been sold and closed for renovations by the new owner. All we saw in the neighborhood was an Italian place, one of those restaurants with dim lights and candles stuck into Chianti bottles. That was the night when I didn't dismiss those fleeting thoughts so quickly. There was a lot of silent staring into each other's eyes and I felt the shivers as my mind conjured up the possible paths ahead of me (us).

In the ensuing weeks, I noticed more and more those gentle things, his eyes looking at my rear as we passed a mirror, his arm around my waist as we waited for a table, his longer intervals of silent contemplation. I could see 'it' coming someday and wondered how I would react to an overt approach. As for me, I could feel a gradual increase in my pussy juice whenever I spoke to him or looked at him. I tried to suppress it, but how do you suppress lust?

Two months later, in a casual conversation about vacations, he mentioned that he had made a reservation for three days in Las Vegas. My mouth reacted without consulting my brain.

"Would you like some company?"

As soon as the words were out of my mouth, I realized the enormity of what I had said. His mouth fell open; my face turned white and then quickly beet red. He inhaled, but he never seemed to exhale.

"You know that Queen Bitch never goes to Las Vegas with me?"

"I didn't think so," I said. May as well continue this line of conversation and see where it leads, I thought.

The silence was deafening. His eyes burned through me, trying to ask me if I knew the meaning of what I had said. This, even though he knew that I knew.

"That would be nice," he said. That was the last thing we said about that for the entire meal, yet it was the only thing on each of our minds. He walked me home. At my door, he kissed me. All of his prior kisses had been on my cheek. This one was on my lips. He made no attempt to come in to my apartment, sought no invitation, acted as if he would have refused if I had invited him inside.

I masturbated myself to sleep. After my third orgasm, it finally worked.

He was a regular commuter from DFW to LAS, making the 2 hour 55 minute trip at the end of every month. Of course, the in-the-air time is less than that, but the runway delays at the busy busy busy DFW airport often made the trip take much longer.

I was awake and dressed long before he and the car service arrived to pick me up. On a day when I usually would have been wearing one of my severe going-to-court outfits, it was a special pleasure to don a simple blouse and skirt. Not wanting to look like a whore, I wore a bra for modesty. But knowing that only one man would see it, my bottom was covered, if you could call it that, with one of my three g-strings that I kept on hand for when I expected that area to be visited by cock or fingers – or tongue. Oh yes, especially tongue.

When he came to my apartment door to help me down with my suitcases – yes, plural, even for three days – we had our first passionate kiss. By passionate, I mean French kissing, tongues dueling. When we broke the clinch and he pulled back, I could see that he was blushing. I too looked red, I could tell, yet in my mind it was simply a glow.

In the car, we sat on opposite sides of the back seat. As far as the driver was concerned, we could have been co-workers on a business trip. But drivers are not stupid, and if asked his opinion, his guess probably would have been that we were a cheating couple off to Sin City to do some lusty fucking.

We arrived at the airport early enough to do some lolling around in the frequent flyer lounge, away from the majority of passengers waiting at the gate. Though it wasn't yet noontime, I let myself be treated to some Jack Black, neat. I felt that glow again. Heck, one more drink and I would have jumped his bones right there in front of everyone. And so it was that when the flight was called, we walked to the gate arm in arm. No one would have mistaken us for co-workers.

Since we were seated in first class – doctors can afford it – we were offered, and took, another drink as we waited for the plane to fill up and the doors to be closed. Once we were airborne, he asked a flight attendant for a blanket and spread over both our laps. We each had an arm on the wide seat separator, fingers entwined. I closed my eyes and leaned my head back resting it against the window.

Soon I felt his hand leave mine and move to my leg. In a second, it was under my skirt, gently squeezing the inside of my warm left thigh. My eyes remained closed but my smile let him know that all was well. He began to knead gently; my breathing sped up to keep pace with his fingers. Suddenly he stopped. My eyes popped open. He was smiling at me.

"The flight attendant was walking past us. I didn't think that you'd want her to see the motions under the blanket."

I returned his smile as he resumed the kneading. But that didn't last long, for his fingers quickly moved up, onto my g-string. The palm of his hand began to rub. My pussy began to gush, the string was soon soaking. He pulled his hand out from under the blanket and brought it to his nose. He smiled his approval of my womanly aroma, not that I would have had any doubt about it had I even given it a thought. Looking around and seeing no peering eyes, I gave his fingers a short suck, savoring the taste of my own loins.

Back under the blanket, he wasted no time in snaking his digits under the string, smack onto my pussy. I've shaved down there for years and that morning had given the area a last minute work over. Smooth as a baby's ass is the general description. He had two fingers inside me and his thumb was flicking my clit. Though I'd gotten myself off the previous evening, as I did most every evening when I was alone, it had been a full week since I'd enjoyed the silky touch of hard cock.

His fingers were well trained. My brain idly marveled at the skill with which he played me, bringing me closer and ever closer to that wonderful moment when nothing in the world exists but my screaming orgasm. Holy shit! Suddenly I grabbed his hand and held it tightly, immobile.

"What's the matter?" he asked.

"You bastard," I said, albeit with a smile. "You almost made me forget that I scream when I cum. We would have had the entire section staring at us for the rest of the flight." With that I gave the bulge in his slacks a quick squeeze and curled up against the window, laughing.

Yet it was with a touch of nostalgia. I remembered all those years when we were far removed from sexual thoughts about each other, when that wonderful condition known as friendship, that Platonic hugs and squeezes were the only touches that we needed from each other. And now I was high in the sky, literally and figuratively, on a trip with him designed to allow me to give him my body, in all the ways that a woman can offer herself to a man, to do for him whatever and however he might wish – or fantasize. He would bring me, I was sure, to the heights of passion for which I lusted. To be sure, I'd hit those heights on many occasions with other men, those screaming orgasms of release, but never had I felt the lustful love as I did at that moment.

Carry-ons rolling behind us, we skipped the delay of the taxi line to grab a limousine for the short ride to our hotel on the Strip. We snuggled in the rear seat, kissing passionately. My hand was on his bulge, his on my breasts. From time to time I glimpsed at the driver and saw his eyes fixed on the rear view mirror. Enjoy it, I told him silently. Think of us when you're jerking off tonight, I telegraphed to him. Why, I asked myself, was it necessary for me to have such a nasty thought to someone who hadn't deserved it? Because, I told myself, he's driving too fucking slowly and I couldn't wait to have my lover's cock inside me. Silently I apologized and wished him a fabulous sex night. When we left the cab, I blew him a kiss, and he blushed.

The check-in seemed to take forever. We were able to use the 'Invited Guest' windows, but even so, seeing three or four couples ahead of us made me want to scream. And when it was our turn, I felt the clerk's eyes on my face as she made the mental calculations about my status; was I wife, significant other, hidden-from-the-world mistress or simple whore? Knowing what I know, I felt that my blush would have put me correctly into the mistress category. For none of the others would feel the necessity to blush. And since when do attorneys ever blush?

Key cards in hand, he rejected the offer of a bellman and we rolled our luggage to the elevator bank. I could see him glancing over his shoulder at the casino, jumping with activity, the crowds yelling with joy or moaning with disappointment. Then he glanced back at me. The choice was obvious. The tables would never be pissed off at him, would never curse him for leaving them horny and unsatisfied, had infinite patience, far beyond that of a live female.

We had the next car to ourselves. On what felt like the slowest elevator on earth, I kept moving up and down on the balls of my feet. To a casual observer, it would have looked as if I had to pee, but he knew better. He knew how much I craved his lustful touch, with hand or tongue, with that cock that I had never seen except in a covered silhouette and rarely even then. We raced down the long hallway to our room, laughing at the very idea of our childish game. And then we were there, he fumbling with the key card while I did my pee-pee dance.

We hadn't spoken since checking in. Once in the suite, it would have been easy, even for the inept Inspector Clouseau, hapless tracker of the Pink Panther. Our shoes were left within steps of the door, his socks three feet farther on. My blouse was over an easy chair, his shirt next to it, with an arm lewdly resting across the breast area. My skirt had flown onto the coffee table, while his slacks were bunched just inside the bedroom door. His shorts were at the foot of the king sized bed while my g-string had somehow managed to hook over a bedpost.

Truth be told, it looks more erotic on film than it does in a narrative.

I ran to the window to close the shades, a habitual but useless task since no one could possibly see us from outside. He pulled down the cover on the bed. When I turned around toward him, he just stood there, staring at my nakedness. His eyes devoured me, roaming over me, over my mouth, my engorged nipples, my dewy pussy, like a vulture circling overhead. But no, not a vulture, for his face told me that he had no desire to tear me apart. Rather, he was like a restaurant critic, ready to sample each tasty morsel before smiling and offering his compliments to the chef.

His hand reached out toward me, pulling my eyes temporarily away from the masterful cylindrical tube of love flesh jutting out from between his legs. He was inviting me to join him, not in a wild orgy of copulation but instead in a calm celebration of love.

We held hands across the bed and slid in together from opposite sides. We covered ourselves as protection from the chilly temperature set by Housekeeping. We turned inward and kissed, deeply, warming our hands on each other's backs. We needed no foreplay – he was hard and I was wet – and yet the kiss lingered for several minutes. Our tongues studied the insides of mouths, places that they'd never before been. Not with each other anyway.

When I could stand it no longer, my hand snaked between our bodies. I took his proud manhood in hand, my fingers savoring the silky skin and that little droplet of creamy liquid that for some biological reason is seen to signal a man's readiness for coition. As if any man is ever not ready. His mouth left mine and travelled slowly down, nibbling baby kisses at my neck, my throat. His lips reached one of my nipples as his hand caressed the other. He sucked each in turn, a baby seeking its fill. My pussy drooled. I stroked his head and wondered if this would be the arousal that I would feel when I first breast-fed my own child.

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Story tagged with:
Ma/Fa / Cheating / Oral Sex / Anal Sex /