Friday Night

A new story series with some of the same characters out of my other stories...

I pulled into my driveway on Friday afternoon. It had been a tough week, and I was ready to relax and kick back for the weekend. I went down to the street and pulled the empty trash can back to its place on the side of the house, then went around to go inside through the mud room door. As I passed through the kitchen I noticed the mail, but decided to ignore it until Monday. A note from my wife was on the counter next to the mail.

"Kids farmed out for the weekend," it read. "A shaker of margaritas in the freezer. Come on up and join the fun."

This last phrase gave me an instant rise in my pants, and I noticed the low smooth jazz music coming from the house-wide speaker system for the first time. There was only one reason she ever put this Pandora station on. Sex.

We had an adventurous sex life ever since we met at a wild after hours party at the hotel we worked for after college in Austin. Outdoor sex at Hippy Hollow, light bondage, some role play, and even more. I took a chance one night and admitted I was bisexual, and wanted to share a cock with her. Far from being shocked or pissed, Annie was thrilled. This opened a whole new world of sex for us, and pegging was soon a regular part of our repertoire. She was a tomboy anyway, so taking on a masculine role felt natural for her.

We got more adventurous with a trip to a hotel swingers party. Then came gay bars on 5th Street and an ABS, where we shared our first cock through a gloryhole. These were titillating but we worried about STDs. Finally we found a bisexual swingers house party, and we were home. Annie tried pussy and liked it, and we built a small circle of friends who were safe, but wicked wild at our quarterly orgies. We got together in various combinations in between "official"events, which were usually held in one of the McMansions out on Lake Travis.

I slipped off my shoes and hung my suit in the hall closet, then tossed my shirt, socks and undies on the washer. Nude, I went to the kitchen and fixed myself a margarita, shaken, on the rocks, no ice with a big wedge of lime. Then I padded quietly up the stairs toward our master suite.

I heard the unmistakeable sounds of my wife being fucked as I approached the open door. My cock, already beginning to stir, began to inflate. It was not unknown but highly unusual for her to fuck a man without my presence. I suspected it was one of our friends from the house parties. I slowed my pace to enjoy the tease for a minute. What, and with who, did my saucy wench have in store for me this weekend?

As I turned the corner into our room, I was treated to a sexy tableau. I was surprised to see a man I didn't recognize kneeling on the bed. His back was to me, and his ass was pumping slowly but rhythmically back and forth. This was who my wife was giving it up for. Next to the bed stood our neighbors from across the street and four doors down, Jack and Diane. They were also nude, with Jack standing behind Diane, his hands on her magnificent tits, rubbing his cock on her ass

We had been fucking Jack and Diane for several months. We had an awkward moment when we entered a bedroom at a house party last year and saw Jack getting spit roasted by two men while Diane sat in a chair watching and masturbating. Our relationship instantly transformed from school carpool partners and waving as we put out the trash to regular lovers. It turned out that Jack and Diane were very experienced swingers, and they took us under their wings. Jack's was the first real cock that ever penetrated my ass, and Diane taught Annie how to make a girl squirt. Diane's eyes flickered from the scene she was watching over to me and she smiled, raising her finger to her lips to keep me quiet as I came in.

I moved over to rub up against both Diane and Jack, giving them each a tongue kiss. My wife Annie was on all fours on our king bed, her eyes closed with a look of concentration on her face. The man fucking her was about Jack's build, that is to say about five foot ten or so with only a small bulge at the middle, balding, with light mocha skin that suggested some Central or South American blood. From the distance he was pulling back before plunging back in with a loud smack, I would have estimated his cock to be about half a yard long. But when I moved to the side of the bed and saw them in profile, I could see that he was really just pulling what appeared to be a nicely sized eight inch condom-sheathed cock all the way out of her pussy by a couple of inches, and somehow they were staying in alignment so that his cock found its target opening again and again. What really surprised me was that he had his thumb in her ass as they fucked. Annie was an anal novice. That explained the concentration on Annie's face.

"And you would be Bill then?" the man asked me.

I was surprised to hear the hint of an English accent. Annie's eyes popped open.

"Hi Hon, meet Freddy," she said with a smile.

"Hi, Freddy, I said, reaching out to take his proffered hand. "How do you like my wife's pussy?"

"It's divine," Freddy replied, never missing his slow, regular beat of fucking Annie. "It's been a while since I had such a fine piece of ass."

And while the words might have been a bit crass and sexist, I had to agree with the sentiment.

At age forty-two Annie kept herself in great shape. She had perky 34c tits with no hint of stretch marks, despite having nursed two babies. Her hips were still narrow, and she had only the tiniest of tummy bulges that she worked on like a demon in the gym. She had ash blonde hair that lightened nicely in the summer, and she kept it cropped short to fit her active lifestyle. In addition to being a "fine piece of ass" she was a soccer coach, PTA secretary, and worked with me in my business part time. And she was more than a fine piece of ass. She was a great fuck, and I enjoyed sharing her within our small group of swingers.

"Bill, meet Frederico Escobar," Jack chimed in. "He's a friend of ours from El Salvador who is in town on business for a while. We met at La Playa last year and really clicked. Freddy's fully bi like us, and as you can see is a pretty sharp cocksman."

"Me Mum was English, and raised me in the Bahamas," Freddy affected a Cockney accent, still steadily fucking my pretty wife's cunt.

"Well Freddy I won't say 'welcome to our home' since Annie is obviously already doing the honors," I replied. I bent down and kissed my bride. "How does that thumb in your bum feel, baby?"

"Better and better. Diane and I had coffee this afternoon, and she convinced me to give it another try. She says DP is incredible, and I have to try it. I was already working on getting Jimmy farmed out for at least the night. Ashlyn's gone on that band trip. So once I dialed the right soccer mom we came up here to play. She showed me how to get good and cleaned out, and began working me up with some of your butt plugs. Oh, wow." Annie sucked in a breath and blew out slowly. "I think we just graduated to two fingers."

Note to self: Buy Diane a great bottle of wine and offer to be her slave. I've been trying to get Annie to try anal again for years.

Freddy wouldn't be deflowering Annie's ass. That honor went to me in some of our earliest explorations. But I hoped he would be gentle and go slow. I wanted my wife to give up her ass regularly, and a painful experience would be a setback. I kissed her deeply again, both to distract her and out of real desire. Then I stood back up and spoke to Freddy.

"Be careful with that ass, buddy. Make sure she enjoys the fun even more than you do. I want some of it myself, later." I looked down and saw that, while long, Freddy's cock was considerably thinner than mine or Jack's.

"Freddy's cock is perfect to get her stretched comfortably," Diane said. "That's why I had Jack call him when we set our plans for the evening. Now why don't you and I go take a shower together and get you ready for some fun too?" She extracted herself from her husband's grasp and came over to give me a seductive kiss. "I think Freddy and Jack can take care of Annie for a bit."

And that's just what we did. Jack climbed on the bed and offered his cock for Annie to suck as Diane led me into our ensuite. She had me do a quick rinse shower by myself ("to get the grime off") then helped me with my enema. Diane has a bit of an anal watersports fetish. Then we got in the shower together and had fifteen minutes of warm, soapy fun before toweling off and rejoining the others. I always particularly enjoy playing with Diane's piercings. Both nipples and her clit hood sport jewelry, and seem to be more sensitive as a result.

Annie was on her back when Diane and I reentered the bedroom, with Jack fucking her furiously. I noticed one of my medium buttplugs had replaced Freddy's fingers in her ass. Freddy was standing by the bed, rolling a fresh condom down his long, thin cock. Jack grunted and cried out as he suddenly came, spurting his cream deep into my wife's womb. We weren't worried about pregnancy or STDs when he barebacked her. Jack was v-safe, and we knew Jack and Diane were very selective about their lovers. Jack liked to cum early in a play date, so that he could last longer as the evening progressed. He stiffened and thrust deep into Annie one last time, his eyes tightly closed and a low growl escaping from his grimacing lips. Then his body relaxed, eyes opened, and the grimace transformed into a "kid in the candy store" grin. He bent down and kissed my partner thoroughly before sliding his still firm cock out of her sloppy vagina, and falling over onto the bed.

Diane and I hurried over and shared some creampie from Annie's cunt. This brought Annie off and she bucked and moaned in orgasm. Then Diane and I pulled back and shared a snowball tongue fight.

Jack stretched back on the bed with a satisfied look on his face as Annie caught her breath and rolled over to offer her ass to Freddy. Diane took charge of this evolution, adding lube and gently working the buttplug in and out of Annie's sphincter several times while stroking and cooing sweet nothings. Freddy climbed onto the bed behind Annie.

"Oh Baby, you're going to love this," Diane purred to Annie. "Freddy really knows what he is doing, and you're nice and stretched and ready for him. Why don't you eat me out while he slides into you?"

With that Diane removed the buttplug and scooted around to Annie's face. She spread her legs and propped herself up on her elbows to watch the festivities. Annie dove down into Diane's center, savoring the pussy she knew best.

I came over and took Freddy's cock in my hand, smiling at him as I did so. This was my first male to male contact of the evening, beside my kiss with Jack, and it whetted my appetite for more. I guided him forward, slathering on more lube as we went. I rubbed his cock up and down and around Annie's asshole several times, then focused him on her sphincter. I used my index finger to lightly penetrate that orifice, then removed my hand and gave Freddy a nod.

Freddy took over and kept a gentle but firm pressure on Annie's ring. He stroked her back lightly, and moved his hips in a circle to vary the angle of attack. Annie moaned in a bit of pain as his cock head popped past her resistance, but Freddy wisely held still for several moments to allow her to adjust to the invasion, all the while stroking her back and telling her how good she felt to him. Reassured that my wife was in good hands, I moved away and left the trio to their ménage.

Jack was laying on his side, idly stroking his cock and watching Annie eat Diane's pussy, something the girls did often during the day while our kids were at school. I looked at his cock and literally licked my lips. It was about the same length as mine at seven inches, give or take based upon how worked up he was, but he had a larger girth. I've never been able to deep throat that wide a cock, though I have tried many times.

One of the things that makes Jack and Diane stand out is the fact that they are both utterly hairless and smooth below the neck thanks to many hours of laser hair treatments. Jack recently took the smooth look even further and shaved his head. Something about that look just really gets my juices flowing, and my cock twitched as I climbed on the bed. Jack turned his smile to me and rolled onto his back, offering up his rod. I didn't hesitate as I went to my knees, grasped his cock at the base, and licked the underside of his shaft and head like a lollipop, the musky flavor of my wife still evident on his dick.

Annie was clearly beginning to enjoy herself by the sounds she was making. With her lips wrapped around Diane's clit she couldn't vocalize her pleasure, but I was encouraged by the tone of the moans and groans I was hearing. I glanced to the side and noticed that Freddy had begun a slow, shallow fuck, and was dribbling still more lube onto his shaft.

Diane was also enjoying herself, she expressed this through a steady stream of dirty talk.

"That's it, baby, suck on my clit," Diane coached. "Just like that. Oooh I love it when you tickle my piercing with your tongue. Is that cock starting to feel better in your pretty little butt? Are you enjoying Freddy's cock in your ass?"

"Mm hmm," Annie affirmed, continuing her ministrations to Diane's vagina. She wiggled her hips to assure Freddy that she was enjoying the experience. Freddy responded by increasing the depth of his penetration.

"Fuck her good, Freddy," Diane said. "She's a hot little slut, and is going to be real popular as a 'three-hole girl' at our house parties. Show her just how good getting your butt fucked can be."

Jack decided to contribute to the cause, and he made me pull off his cock. He twisted around flat on his back, and scooted his torso under Annie's. Raising himself on his shoulder blades, he began to eat her out while Freddy fucked her. I returned to Jack's cock, this time licking the top instead of the bottom, swirling my tongue around the head at the top of each stroke. In this position I could look to my right and see Annie eating Diane. She must have felt my glance, because she opened her eyes and looked over at me. We could see the love in each other's eyes and exchanged a smile as we shared one of our favorite pastimes, same-sex oral.

This enjoyment went on for several more minutes until Annie lifted her lips from Diane's cunt and said "oh fuck!" in pleasure, not in pain.

I released my vacuum lock on Jack's cock and looked over to see what was going on. Freddy had finally bottomed out in my wife's bottom. He was beginning to fuck her ass in earnest, and I guessed that Jack's oral talents were contributing positively to the cause. Annie began to whimper as Diane reached over and pulled her face back into her crotch.

"Uh, uh, you slut," Diane sad in a stern voice. "You're getting me close, and you're going to get me off! You know how to do it. Make we squirt my cum all over your sweet face."

At first I thought Diane was being a bit selfish. After all, this set piece was about Annie's pleasure, and reintroducing her to anal in a positive way. I wasn't even really trying to bring Jack off, he'd just cum a few minutes prior, but to encourage his enthusiasm in eating my wife's cunt. But then I realized what was really going on. Diane was focusing Annie on pussy. Since women don't have prostates, they don't derive physical pleasure from anal sex in the same way as men. Diane was engaging Annie's biggest sex organ, her mind, to allow the anal experience to become simply a part of the overall event. This was confirmed for me when I looked up and saw that Diane was making eye contact with Freddy. When Annie slipped two fingers into Diane's vagina to find her g-spot, Diane nodded at Freddy. This was the signal to go ahead and pound my wife's sweet, delicate ass for his own pleasure

I redoubled my efforts on Jack's cock, and was pleasantly rewarded with some precum. Diane continued to orchestrate the affair like a symphony conductor, even as she was succumbing to Annie's oral and digital talents. Diane nudged her husband with her knee to get his attention.

"Make her cum now, Stud!" Diane commanded. "This bitch is sending me over the moon, and I want her right there with me. Do something good and I'll make it worth your while!"

Jack was well trained in obeying his wife's sexual demands, and had reaped many rewards through the years by doing so. He now fluttered his tongue furiously on my wife's clit (I learned this during the pillow talk debrief we always shared before drifting off to sleep) and he grabbed her nipples and rolled them between thumb and forefinger. This had the desired effect, and Annie moved quickly toward orgasm. This caused her sphincter to relax just a bit, and Freddy felt all resistance to his cock melt away.

Freddy held Annie's hips firmly and picked up his pace. He put a rotation in his hips, almost like a salsa dancer. His balls began to contract as he plunged his cock deep into my lover's bowels. He thought as he pumped that this truly was a fine piece of Yankee ass. He was so fortunate to have met Jack and Diane, who were proving to be incredibly well plugged in to the swinger network, and knew where to go to find like minded people like me and Annie.

Annie matched the flutter of Jack's tongue on her clit with her own tongue on Diane's. She had easily found her friend's g-spot from long experience, and she knew just how to push the right buttons. Even as she tried to concentrate on giving Diane pleasure, she began to wail from the multiple sensory sensations that were at play. The cock in her ass suddenly felt wonderful, and she couldn't believe what a different experience this was from earlier tries. Jack was a skilled oral lover, and was well experienced with reading and capitalizing on her reactions. He was playing a key role in her impending orgasm, particularly as he became more aggressive with her nipples. And then there were the tastes, smells, and textures of the beautiful hairless pussy in her mouth.

That pussy was red and swollen, and the woman it belonged to began to squirm her hips and cry out. Suddenly Annie's face was drenched with the sweet wetness of Diane's squirting. Diane didn't gush, but there was enough fluid to force Annie to lick her lips and swallow before returning her tongue to Diane's clit. Diane cried out and came again.

"Shit that is so fucking good!" Diane yelled. "Keep going baby, let's ride this together."

Freddy felt Annie's ass contract, then begin to pulse as Annie came. Her whole body stiffened and shook several times, and she was moaning loudly into Diane's pussy. Freddy's balls boiled and he erupted in orgasm, pounding his hips hard into Annie's. This forced Annie's clit past Jack's lips and down over his chin. The sudden new sensation of beard stubble sent Annie immediately into another cum. Jack took the opportunity to dip his tongue deep into Annie's vagina, and was rewarded this time with a scream and a mouthful of girl juice.

Diane reacted in sympathy with Annie's orgasm, slipping into a series of short, intense cums that wracked her body. She was almost chanting "fuck, fuck, fuck" with a constant underlying moan as she rode the waves of multiple orgasms.

Freddy's cum subsided, but he was a considerate lover and did not simply rip his cock out of what would surely be a sensitized ass. Instead, he let his cock slowly soften inside Annie, keeping his hips pressed against her butt and praising her.

"Oh, that was truly divine as I said, my dear. You have a wonderful ass. It drew the cum right out of me. And so shapely and tight! Your husband is a very lucky man," Freddy said.

Speaking of Annie's husband, I stopped sucking Jack's cock and raised my head to watch the ongoing show of two women cumming together. I kept my fist wrapped around Jack's organ and slowly jerked my friend as I marveled at the sight. Annie and Diane seemed to be getting into a common rhythm of orgasmic bliss. Their bodies were spasming and they were moaning in unison. Sweat glistened lightly on Annie's back and Diane's breasts as the evening sun poured into the bedroom during what photographers call "the golden hour."