Bill & Annie Ch. 01: Friday Night

The girls probably could have gone on like this indefinitely, but Jack's shoulders finally gave out on him and he collapsed on the bed between Annie's knees. About this same time Freddy's cock slipped gently out of Annie's ass of its own accord, and he quietly shuffled back and stood to go into the bathroom to remove the spent condom and freshen himself. I bent down and licked Jack's cock once again to get his attention and we shared a grin. Annie finally let up on Diane's clit,and crawled up to kiss her lover and share the sweet nectar that now covered her entire face. Diane licked hungrily all over, stopping every so often to stick her tongue in Annie's mouth and share the treat.

Our wives then kissed Jack and I and moved over on one side of the bed. As the girls caught their breath and cuddled I pushed Jack over on his belly and straddled his butt. From here I rubbed his shoulders and neck to help keep any soreness from his sexual calisthenics at bay. I also took the opportunity to rub my cock up and down his ass crack. Jack moaned in pleasure.

Freddy came back out of the bathroom and said "mmm, is man pussy next on the menu?"

"Could be, amigo," I replied. "Annie and Diane love a little gay love show. Want to do a threesome with me and Jack?"

"Always up for a three way, in any combination, Mate!" Freddy replied enthusiastically. "Make way, ladies, the boys are going to play."

"You guys get started," said Annie, rising from the bed and pulling Diane along. "Diane and I are going to freshen up a bit, and then we'll come cheer you on. Come on honey, I need some help getting that plug back in. I want to work up to having Jack's cock in my ass before the weekend is out."

"Get the next size up out of the toy chest baby," I coached my bride. "You should be able to handle it now, and it will make your next fuck even better."

Annie compared the buttplug that had been in her rectum when I came in to the collection I kept in the locked chest in our closet, and picked out a new candidate. She also took her Hitachi out and set it on the side table in what we referred to as "the Bleachers." This was a small sitting area with two comfortable chairs that came in handy when one or more people were showing off for the others. Diane reached into their overnight bag and pulled out her own Hitachi. Jack and I had seen our women spend a solid hour bringing themselves and each other off over and over again with these two magic wands.

Annie and Diane padded arm and arm into the bath while I moved down Jack's back and began to knead his butt. Freddy came up behind me and began to play with my nipples, nuzzling my neck and ears.

"Freddy, that feels great," I said. "Very few of the Hispanic guys we play with around here go in for much in the making out arena. I'm glad to learn that you are comfortable enough with your machismo to let go a bit."

"Oh, our boy Freddy can get downright feminine," Jack chimed in. "I saw him in full drag at La Playa."

"It's true, I'm man enough to be a woman," Freddy said with a touch of pride. "And I hope you'll stick this nice cock of yours in my pussy tonight, Bill."

"Happy to oblige, my friend. Anything for the guy who opened the door to my wife's ass. I want to thank you for how gentle and sensitive you were with Annie just now." I turned my head and kissed Freddy full on the lips, slipping my tongue into his willing mouth. "Why don't you hand me that lube and let's get Jack and each other ready for some fun?"

Freddy handed me the jumbo bottle of water based lubricant. I put some on my hands and warmed it up, then used it like massage oil on Jack's butt, kneading firmly and spreading his cheeks with my thumbs. Jack raised his hips and gave me more access. I took another dollop and dripped it on Jack's rosebud, then brushed it around with my thumb tips.

Taking the bottle back from me, Freddy greased my hole while continuing to kiss and nibble my neck and ears. He slipped one and then two fingers into my very willing backside, and let his other hand return around my waist to find my cock, which I was brushing up and down the backs of Jack's calves.

I bent over and rimmed Jack a bit, the lube was passion fruit flavored and I knew he would be squeaky clean.

"Oh, yeah, baby," Jack hissed. "That's great. Get me ready for some cock. I want you both to pound my ass."

"I think we all want the same thing, lover," I replied. "But let's have a daisy chain going when the girls come back, and then we'll treat them to some "manwich" sex in rotation, okay?"

Of the four of us, Diane and I were the ones who came up with ideas for playtime. I could be kinkier than Diane, but she was more forceful in her directions. Between the two of us we never got any complaints from Jack or Annie, or any of our play partners at house parties.

Now Jack moved up so that he was lying across the head of the bed against the pillows. He rolled to his side and lifted his knee to make his cock available for sucking. I jumped up to the toy chest and came out with three medium sized dildos, handing one each to my playmates. Then I climbed onto the bed and laid my head on Jack's thigh, taking Jack's cock directly into my mouth.

Freddy had been applying some lube to his own ass while Jack and I shifted about. He then mounted the bed with his head toward the foot, and raised his leg to give Jack access to his rock-hard dick. Freddy completed our chain by literally swallowing my cock to the root. I didn't care where Jack and Diane found this guy, he was a keeper!

We began to suck each other and play with assholes as we did. Fingers went in and found prostates. Tongues swirled on cock heads. And balls were slurped and tugged upon.

I felt the dildo in Freddy's hand probe my anus, and raised my knee higher to allow him free rein. Freddy seemed to realize that I had a well-trained sphincter, because he slipped the silicone phallus smoothly and steadily in. The invasion felt wonderful, and I moaned around Jack's cock.

Jack apparently did the same to Freddy, because Freddy began to moan and hum around my dick. The vibrations felt great, and he kept them up as he raked his teeth lightly across the bottom of my cock head. This inspired me to put a vacuum lock onto Jack's cock and begin to insert my dildo, which was hot pink, past his ring. Jack always amazed me with his ability to relax his sphincter and then contract it, practically sucking a cock into his bowels. I emulated Freddy and began to give Jack a hummer while fucking his ass with my little friend.

We worked on each other for several minutes this way. I loved the feel of Jack's cock head against my tongue. The spongy texture, and the way it expanded when I sucked hard, really pushed my buttons. Within a couple of minutes the salty sweet taste of precum was added to the mix. I could tell that I was hitting Jack's prostate perfectly with the dildo.

My own cock was in a velvet heaven. Freddy really knew his way around a cock, spending a lot of time tickling the underside of my clock head and my pee hole with his tongue. Sometimes flattening his tongue out and licking the entire length of my shaft, and often giving me five or six quick vacuum strokes. All the while plumping and twisting the dildo in and out of my ass, and humming.

Jack must have been giving Freddy at least as good as he was getting from me, because Freddy was becoming more and more enthusiastic as we played. Jack is a consummate cocksucker, and I was sure he was enjoying Freddy's long, thin pole. I wanted to get that organ in my own mouth soon, and try out the dick that had brought my wife such pleasure in my ass for myself. We were concentrating and humming (in harmony!) so loudly that I didn't hear the girls come back in.

"Ooh watching guys suck cock is so hot!" Annie exclaimed. "I just love watching my husband with a hard dick in his mouth." She walked over and lovingly stroked my cheek.

"Too true," agreed Diane. "The only thing that would make this a better picture would be if their asses were all nice and red." She slapped Freddy's butt, hard, causing him to increase the pace on my rod.

Diane was in a dominant mood. I glanced over and saw that she had attached weights to the barbell piercings through her nipples. I raised my head momentarily to confirm my suspicion. She had a weight hanging from her clit hood piercing as well. I wondered what she had done to Annie.

The girls went over to "the bleachers" and plugged their Hitachi Wands in. They angled the chairs so that they had good views both of the bed and each other. I heard the two vibrators begin to hum.

"Alright you cocksuckers, it's time to see some fucking," commanded Diane. "Show us how real men do it!"

Truth be told I was ready. As much as I love sucking cock and the taste of cum, I was really obsessed with feeling Freddy's cock in my ass. It would give Annie and me another shared experience to talk about. I loved being able to discuss our lovers with her.

I directed the guys, and it may have been selfish but I put myself as the meet of the "manwich" first. I grabbed the bedspread and put it on the floor in front of the bleachers. I wanted the girls to have a bird's eye view of the proceedings. As we shifted about, I saw that Diane had put clamps on Annie's nipples. The two women were sprawled in the chairs, with their knees thrown over the arms and their vulvas spread lewdly open. The wands were humming on their lowest settings.

Jack went to all fours on the floor, and I started lubing him thoroughly. Freddy did the same to me. Being familiar with Jack's anal talents, I quickly had four fingers stretching his sphincter. Freddy was more conservative with my ass, but his thinner cock wouldn't need my ass as relaxed.

I got up behind Jack and slipped into him. This tunnel was very familiar with my cock, and I loved the way he could flex his muscles to milk my organ. I was bareback thanks to our relationship and trust, but Freddy was considerately putting on a condom without being asked.

I pumped in and out of Jack's ass a few times, then draped myself over his back and reached around to fondle his cock. He would need both arms to steady the three of us as we fucked, and I wanted him to enjoy more than just my cock. Freddy dropped to his knees behind me, and set the bottle of lube next to us on the floor. Because he was a few inches taller than me, and slightly taller than Jack, his cock aligned well with my ass.

I held still as Freddy entered me. The beauty of a long cock is the feeling you get as it seems to just keep going in forever. Freddy obviously appreciated this fact, because he moved very slowly and smoothly. I shuddered a bit as his cock head rubbed my prostate. I was bottomed out in Jack, and soon Freddy was bottomed out in me. I nodded my head, and he began to fuck me.

The secret to making any threesome sandwich work in any sexual combination is communication and rhythm. I let Freddy set a pace and get into a groove before I began to add to our common motion. Freddy's swinging experience showed once again as he set a regular and steady pace.

"Oh Freddy that feels fantastic," I said with real enthusiasm.

"Let's...fuck...Jack's...ass...together," Freddy responded, communicating the pace of fucking verbally.

"With a cock like that I'll follow you anywhere, buddy," I said. "You set the pace, and I'll pass it along."

Jack was focused on two things: flexing his sphincter around my dick and my wife's pussy. It was splayed open at his eye level about a foot and a half in front and a bit to the right of his face. I noticed that she had my favorite copper-colored silicon bullet in as her butt plug, and her pussy was dripping copious amounts of lubrication, both natural and man made. As Jack stared at her vagina, it flowered open for a moment as she came. This caused his dick to flare in my hand, and his sphincter to pulse again around my shaft. I thrust extra hard into his anus on my next in stroke.

We settled in to a great rhythm for several minutes, and my cock was responding predictably to the feeling of a warm, tight ass wrapped around it, and a warm, firm, pulsing cock sliding smoothly in and out of my own butt. Add in the visual stimulus of two beautiful, wanton women masturbating just a couple of feet away, giving off wonderful scents and pheromones, and the aural stimulus of everyone's moans and groans, and my balls were tightening quickly. Freddy's cock really just felt delightful, and he was picking up the pace as his own need built. I flexed my own sphincter around his shaft, and transferred the quickened pace to Jack's ass.

I grabbed some lube, squirted a bit on my hand and worked harder on Jack's cock with my fist. I added some twist to my motion and ran my thumb back and forth across the head. Jack growled. And Diane moaned.

"Oh yeah, Baby," she said to Jack. ""Doesn't that hand on your cock feel good? I bet that cock in your ass is pulsing and ready to shoot. And God but wouldn't you love to get at Annie's pretty little pussy right now? Look how red it is. How swollen. Look at the juice dribbling down to her asshole. How close are you, Honey? Are you ready to cum all over Bill's hand? Go ahead. Do it. Cum on his hand. He'll catch it for you and smear it all over your face. Cum on, be a dirty boy and eat your own cum out of Bill's hand."

"Yeah, boys, get nasty for us," Annie added. "Honey, doesn't Freddy's cock feel unbelievable in your ass? That's the same cock that was fucking me just a while ago. It felt so good sliding in and out. Tickle Bill's nipples, Freddy. That will get him off. And then make my husband clean you cock off after you cum in his ass!" Freddy complied, and his fingers on my nipples had the intended result.

This woman certainly knew her husband's buttons. No sooner had I cupped my fingers around Jack's cock head than his body tensed, he cried out, and began to shoot jet after jet of hot sticky liquid all over my hand. I rode Freddy's next thrust and slammed my cock into Jack's bowels, and he shot yet again into my palm. I immediately reached up and rubbed my wet palm and fingers all over Jack's face, and be damned if he didn't cum again!

All this time Jack's ass was pulsing and clenching around my cock. What with the nasty feelings that smearing his own cum on a man's face gave me, having him stick out his tongue and greedily lap his own nectar from my fingers, gave me the extra kick to send me over the top. I yelled "fuck me hard, Freddy!" And started to cum.

Since this was my first of the night, and I had been on sensory overload for a while, I shot a massive load deep into Jack's rectum. Freddy was slap-fucking my ass for all he was worth, and began shooting his own load. My cock was throbbing inside Jack's ass. It was on fire, and my own ass was feeling the beautiful spasms of a cock in the midst of orgasm inside it. The shared intensity with these two men was mind blowing. Muscles were rippling and testosterone was pervading the room as we bucked and fucked each other.

Freddy's cock pulsed again and again in my anus. I regretted the need for a condom. I would have loved the feeling of his seed filling my butt. I was an experienced swinger now, and I knew better than to take chances. But by God I was going to fulfill Annie's direction and clean Freddy's cock of cum after he took off his sheath.

Jack pushed back into me so that I bottomed out once again in his rectum. Then he clenched his sphincter tightly and slowly slid forward, pulling the las of my cum from my cock. This was one of his favorite moves, and it certainly was a favorite of mine as well. My cock twitched a final time right before it slipped out of his ass. The feeling was intensely pleasurable. Jack held himself low, crawled out from under me, and dove straight into my wife's pussy. Annie sang out in delight.

"Oh yeah, Jackie, stick your tongue way up my cunt. Oh I'm going to cum!" Annie cried out, bucking her hips but keeping the vibrator firmly pressed to her clit.

Freddy pulled out of my ass, patted my butt cheek, and emulated Jack by diving into Diane's pussy. She also cried out in orgasm. I pulled the spent condom off of Freddy's cock, rolled onto my back, and engulfed his cum-covered member in my mouth. The slight latex taste did not distract from my savoring the sticky goo.

We stayed in this configuration for a bit, Jack and Freddy helping Annie and Diane to another couple of quick cums. Annie was the first to quit. She turned off her vibrator and gently removed the clamps from her nipples, while clinching her thighs together to force Jack's tongue away from her vulva. Similarly, Diane pushed Freddy away and removed the weight from her clit hood piercing, but leaving the weights on her nipples. I vacuumed Freddy's cock of the last of his cum, and rolled out from beneath him.

"Let's take a break and have drinks and munchies," Annie suggested. "Diane and I set up some hors d'ouvres trays in the fridge, and we can grill up some chicken wings. Honey, go get cleaned up and light the fire?"

"Great idea. I'm starving," I agreed. I took a sip from my now watery margarita.

Freddy and I went in and shared a quick shower to freshen up. He was a great kisser and this game of slap and tickle was an interesting contrast to the shower I shared with Diane earlier. Diane and Annie went to the guest bathroom downstairs for a quick rinse, then into the kitchen to lay out the goodies. Jack used the bidet in our ensuite to rinse, and then went down to the patio to lend me a hand with the grill.

We spent about an hour nibbling and socializing. Diane and Jack filled us in on their recent initiation to The Club, an exclusive swingers getaway out in the Texas Hill Country. Freddy regaled us with tales, no names of course, from his numerous visits to various Caribbean resorts. Annie held up our end with a detailed description of an adventure we had when she accompanied me to a recent convention in Orlando.

As the sun went down we drifted out to the pool. We had remained comfortably nude, so skinny dipping came naturally. Playful splashing turned to caresses and kissing, and we were soon engaged in more sex. Freddy and Jack DP'd Annie on a chaise lounge while Diane gave me a blowjob on the side of the pool. The girls gave us a great sixty-nine show on the large inflatable bed we kept in the pool box. And Freddy fucked Jack, though by this time neither man had another cum in them.

Jack and Diane had to go to relieve the babysitter, but Freddy agreed to stay on a bit longer. We went back to the den, where Freddy fucked Annie one last time while I had my cock buried in his ass. After a bit more cuddling, he thanked us for our hospitality and great sex, then left after a three way kiss.

When I came out of the bathroom after preparing for bed, Annie was sitting up on the bed with her laptop and smartphone.

"Hey, Diane texted while you were brushing your teeth," she said. "They are dropping Tommy off at her mother's place to spend Saturday afternoon and night with Grandma." Diane's Mother lived across town in an independent living facility for the elderly. "What would you say to cooking up some ribs and let's host an impromptu pool party tomorrow afternoon? Jack will make mojitos and Diane will whip up her cole slaw. She and I will put the word out, and whoever can make it on short notice will be who we play with. She's pretty sure Freddy can make it back too. I was just signing on to be ready to send some emails."

"Sounds like you guys have it all planned out. You already know that I'm in. Make sure and let Sally Garvin know, I'm pretty sure Frank is still in Europe on that job and their daughter is taking summer classes up in San Marcos. She and Freddy should get on famously, with her love of long cocks."