As I lay there after that mind-blowing orgasm deep in Connie’s ass, my mind was a jumble. This sexual fantasy land was, clearly, illegal. The city, selling raffle tickets for mutual sexual slaves? I mean … come on. And open sex in public? Questionable but certainly gratifying and, apparently, consensual and tolerated. Then there’s my still unfulfilled Partner For a Day obligation. I was stuck here until at least midnight.
I thought about weighing anchor first thing in the morning. My mind was flitting about. But who was this Chad that I kept hearing about? He held some sort of record. I saw him at the raffle when the young teenage boy won Chad for the week. Wondered how their day was going.
Suddenly, I became aware that Connie had dismounted me and now lay alongside, twirling my hair around her finger. “What ya thinkin’ bout, Sailor? Wondering what my requests are gonna be? Hoping it’s gonna be something you like doing, Sailor?” “Ah, yes, exactly what I was thinking about. I think we should rustle up some grub, refill our drinks and discuss it over dinner.”
We found ourselves in the same corner booth at the only bar in town, where Carla works. Carla brought us waters. “What’ll it be today, Partners?” I replied “Our usual Sea Breeze and single malt. Make mine a double, please. Oh, and we’re not Partners. Neither of us bought tickets.” “I don’t care if you bought a ticket or not, Sailor. I just want to be there when you beat Chad’s record.”
“What is this record?” I asked. Carla and Connie looked at each other and had girl talk without saying a word. They both turned toward me and said, in unison, “We’ll let you know when you’ve beaten it.” With that, we ordered our food and Connie ended with “And bring our drinks now, please, but keep an eye on us before you put in our order.” Carla gave Connie an understanding nod and disappeared.
Once Carla left, Connie wasted no time. She looked me in the eye and said, straight up, “Sailor, I have a request. I want you to suck my clit and lick my pussy, right here, right now.” “Here? Now? What? How?” “I’m gonna lay on the table, legs spread, and you’re gonna stand or kneel between my legs.” Holy cow! What had I gotten myself into?
She gave me a blank stare and abruptly stood up. Just then Carla returned with our drinks and she helped Connie clear enough of our booth table for the upcoming events. As Connie got herself situated on the table, her back against the wall so she could watch, I pounded my drink. Connie got her dainties removed and had her snatch at the edge of the table, poised and ready to go. With her drink in one hand and her other busy at her crotch, she said “She’s ready; are you?” I motioned to Carla to bring a refill and emptied my glass.
Her pussy was attractive, in a down home, rugged, fuck me every day, fuck me for hours straight, sort of way. I started by caressing and tickling the inside of her thighs. I used my fingers to massage around her vagina, gently teasing her outer lips apart. I worked on rubbing her pussy lips until I got them parted, exposing her clit. It had fattened up but wasn’t fully erect yet.
Then I bent over and ever so gently put my lips on her exposed clit, encircling it, running my tongue around it in a spiral motion. As I sucked it up to full attention, she began to moan and grind her hips. I licked her clit from base to tip and twiddled the tip with my tongue. Then I licked her lips, from ass to clit, both inner and outer lips. They were swelled up and tasted like her pussy juice, a mild taste, very pleasant.
I tried to tongue fuck her hole but the angle just wasn’t right. Instead, I got my mouth tied to her clit, nibbling on it, grasping it between my teeth as my fingers found her hole. I got them lubed with her pussy juice and used two, then three fingers to fuck her cunt. I kept up the assault on her clit and the finger fuck until she bucked her hips and let out a very satisfied moan.
As if on cue, Carla showed up with my drink and a fresh one for Connie. “Your food will be out shortly.” Connie excused herself for the ladies room as I collected myself and got comfortable in the booth. As I sipped on my drink, I surveyed the crowd. A bit over half full and not a soul seemed to have taken any notice of our antics. There was no one whispering, no furtive over-the-shoulder glances, no finger pointing. Either no one had seen or no one cared. This place was unreal.
Connie returned just as our food arrived. The burly guy brought it to our table. As he returned and went through the kitchen door, I could see Carla on her ass fucking table, getting her ass reamed by some guy. This town was too much. I only had one more of Connie’s requests and then I was free. Or I could keep it going until ….
Connie was very relaxed as we ate and drank. She sat quietly, obviously lost in thought. I asked her what she was thinking about. “I have one more open request, Sailor. I’m exploring what it’ll be.” “Well, I’m hoping it’s something that I can satisfy without having to try and find a surrogate.”
“Don’t worry about that so much. If it gets to that point, I can help with a surrogate. I have some pull around here. You see, my ‘equipment’ if you will, has a reputation. My pussy and ass are built tough, like a Sherman Tank. They can withstand hours of constant fucking. My previous Partners and those that I’ve been a surrogate for are all amazed at how I can easily let a guy just have his way with my cunt for hours on end. Same with my asshole. Kinda like Carla. So, if you can’t perform and need a surrogate, I’ve got your back.
“However, I want you, not some surrogate, to fulfill my request. So, I’m gonna choose it wisely. Tell me, Sailor. How are you holding up? And is there anything that you’re particularly good at? Inquiring minds want to know.” “Well, Connie, I’m holding up OK. I still have some wood available but it probably wouldn’t last as long as you say your pussy can. And I’m sort of drained of cum, so if a massive load shot on your face is your request, we may need a surrogate for that.” “Duly noted.”
We sauntered back to her place after dinner, making a brief stop at Timmy’s for more supplies. Once back at Connie’s, she poured us some drinks and settled in on the couch. “Come join me, Sailor. Want to watch some TV?” “You’re welcome to turn it on. After all, it is your house. But I must admit that I don’t watch much TV.” “That’s OK. Maybe it will provide some background as I decide what’s next.”
We sipped our drinks as some talking head delivered the reality of all the bad things happening everywhere. At the first commercial break, she turned to me and said, in a soft, almost whispered voice, “I think I’d like you to service my tits with some pussy fingering thrown in for good measure.” “That’s totally doable, Connie. But won’t that be either just a tip or will that count as two?” “You can count it however you want, Sailor. Just keep in mind that it’s almost 11 p.m., so we only have an hour left.” “Got it. Let me work on your boobs and get your pussy all wet. We can call it even after that. Deal?” “It’s a deal.”
She proceeded to take her top off, remove her bra and pull her pants down. I started with some tentative, gentle kisses on her mouth, cupping her boob in my hand. I then dipped down to begin giving her tits a mouth job.
I planted my lips on her nipple and started sucking, like a baby nursing, as I fondled her other boob. My lips and tongue were working on her nipple and areola as my other hand started caressing her other nipple. “Ooohhh … that feels good. Don’t be afraid, Sailor. My tits are like my pussy and ass – they like it rough. Pinch and twist, nibble and bite. I’ll let you know if it’s too hard.”
I stepped up the action and moved my free hand to her crotch. I ran my fingers up and down her slit; it was moist and inviting. As I switched from one boob to the other, I slid my finger into her hole and started sliding it in and out. “Oh, yes! Harder now, harder. They love to be abused. Don’t hold back, Sailor.”
I stepped it up another notch, sucking, pinching, biting, twisting her nipples as I kept up my finger fuck in her now wet pussy. I had two fingers up her cunt and I used my thumb to stimulate her clit. She was moaning and groaning now, obviously enjoying this. I gave her clit a hard squeeze between my fingers as I bit down on her nipple.
“Oh, fuck, Sailor! You’ve got me! That’s it! I’m gonna cum, I’m gonna cum!” With that, her body jerked and shuddered as she let out a loud gasp and moan, her pussy flooding with that wonderful pussy juice. I quickly got on my knees between her legs, hoisted her hips up and started licking her sweet cum juice from her pussy lips. At the end, I gave her clit a tender kiss and suck, just for good measure.
“That was great, Sailor. Just what I needed.” We worked on our drinks, finishing them in unison. As we both set our glasses down, she said “Well, Sailor man. It’s almost midnight. Our Partner For a Day contract has been fulfilled. You have performed admirably and once word gets out, you’ll be a very popular catch at the weekly raffle.”
“That’s nice to hear. We’ll just have to wait and see, won’t we?” “I guess so” she said with a hint of suspicion or disappointment in her voice. At that, I stood up to leave, to return to my floating home, and sort things out. “Before you go, I’d like to give you a small tip, just to thank you for taking such good care of me today and lifting me out of the doldrums I was in earlier.”
She reached over and unbuckled my belt. She fumbled with the button but soon had both my pants and my boxers on the floor. She leaned over and took the head of my dick between her lips. He was soft but immediately started to stiffen up as her warm lips enveloped my cock head.
She twirled her tongue around my dick, making sure to find my sensitive spot on the underside. “I thought you didn’t give head, Connie. Or was that just a ruse to avoid letting me fuck your mouth?” She stopped for a moment to respond “It’s not that I don’t give head. It’s just not my strong suit. I can’t do deepthroat. I gag and puke.”
Hmmm…. So, I grabbed her head and started fucking her mouth. Shallow, gently at first. She seemed to tolerate it well so I ramped it up a bit, sliding my now erect cock deeper into her mouth. My pace quickened and soon I was full on mouth fucking her. She had reached around and grabbed my butt cheeks, pulling me in. I got my dick in as far as the deepthroat door at the back of her mouth. My hard dick was knocking on that door, sliding in and out faster and faster, harder and harder.
But she just wouldn’t relax and let me all the way in. I tried the soothing dirty talk, advising her to relax, open up, called her nasty names, ran through my whole repertoire. Nothing seemed to work although she patiently let me fuck her mouth with abandon.
She just sat there on the edge of the couch, her mouth firmly attached to my cock as it slid in and out of her mouth. It was warm and wet and my cock was feeling it. Then the drool started. As it dripped from her mouth and dribbled on her tits, I watched my rod stroking her mouth. Before long, this had it’s intended effect and I held her head tight as I squirted my cum in her mouth. I gave out a loud sigh of relief but just kept my dick in her mouth until it got soft.