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Written by: SailorVibe Category: Fantasy Tag(s): Male / Female, Older Male / Female Chapter 29: Connie Breaks Tradition Connie led me down the block, turned the corner and walked to the end of the street. She turned in at a small concrete block ranch house, typical in this part of the south. Once inside I placed the now half empty bottle of rum on the counter and asked her for some glasses. I got some ice and poured two drinks, still straight rum. We settled in on her couch, drinks in hand, to an awkward silence. As if on cue, we each took a sip at the same moment. That kind of broke the ice and we looked at each other and giggled. I was high as a kite and feeling sort of awkward. The rum was helping loosen my inhibitions, so I simply reached over and cupped her breast in one hand, through her sweatshirt. Her breasts were firm but not fake and of good size. She still had on a bra so I couldn’t find a nipple. Instead, I leaned towards her and lightly kissed her lips, lingered a moment, then kissed her full on. She responded and parted her lips so that our tongues could explore each other. As we were making out, my hand slipped under her sweatshirt and took control of her breast. After a few minutes of kissing, we broke and, in unison again, reached for our drinks. “So, help me with this ‘partners for a day’ arrangement. If we were partnered now, all I’d have to do is tell you to, say, suck my dick and you’d have to do it? Is that how it works?” “Well, yes. But when I tell you to suck on my boobs, we’ve got an issue. Who goes first? Or, say, you tell me to suck your dick but I tell you I want my ass fucked … well, obviously your dick can’t be in my mouth and my ass at the same time. Further, if we start with your cock in my mouth and I get you to cum, then you’re not gonna be able to fuck my ass with a soft dick.” “Hmmm. I see. So, if that happens, I’ve shot my wad down your throat and you demand ass fucking, am I allowed to use fingers to fuck you? Is that kosher?” “It is, but only if both agree beforehand. And there’s more. In that type of situation where you’ve cum and can’t get it up to satisfy your partner’s request, you’re allowed to call in a surrogate.” “Wait, wait. You mean that I can fuck your mouth and cum down your throat and then call in, say, Randy to satisfy your ass fucking desires?” “That’s exactly right, Sailor. And I’d love for that to happen. His big dick is very popular around here.” “Does it work both ways then? Say I want my partner to deepthroat me, but she can’t deepthroat without gagging or puking. Can she call in a surrogate to satisfy me?” “You catch on quick, Sailor man. I think you’re getting the hang of our weekly raffle. You see, the partnering works in the vast majority of cases. But not every person can deepthroat. And not everyone can tolerate ass fucking. Remember, it’s not always boy-girl. Rarely girl-girl, although that does happen, usually by some pre-arrangement. More commonly it’s guy-guy, because there are more males than females here. So those that can handle certain sexual acts stand in as surrogates for those who can’t or won’t.” We both took long swigs of our rum. She set her glass down and asked me to refill it. “Bring my drink to the bedroom, please. My pussy is twitching it’s so horny. And just so you know, partnering for a day is not a real thing. For partnering, you must buy a raffle ticket first. Traditionally, you get partnered for a week at a time. Since you’re new to town, and someone has to show you the ropes, I’ll go first. I want you to fuck my cunt till next Tuesday, Sailor. I want to see how good you are for the next raffle.” As she disappeared down the hallway, I poured the last of the rum into our glasses. I found her in the master bedroom already fully nude, lying on her back with her legs spread. She was slowly caressing her clit, getting herself in the mood. I put her drink on the bedside table and swallowed half of mine. As I intently watched her slowly circling her clit, buried in a mound of pubic hair, I shed my clothes. I climbed onto the bed next to her on my belly and started kissing her. She responded and we kissed passionately for quite a while. As we were kissing, I reached my hand down to her crotch and found it all oozing wet. I started by running my finger up and down her outer lips, soon parting them to find a sopping wet pussy. I pushed one finger into her pussy hole, then two. I stroked in and out a few times, then slipped my fingers up to her clit. It was fully erect and a tad oversized. Bigger than most, a good sign. We continued kissing as I began working on her clit. You could tell that she was eager as her hips were twitching, starting to buck and her breathing between kisses was short and quick. We broke our lip lock and I climbed between her legs. She instinctively reached down and grabbed my dick to guide it in place as she raised her legs and rocked her hips up. Her pussy was well lubed and my cock easily slid into her swollen cunt. “Oh, yes, yessss. Oooh that feels good. I’ve needed a good hard dick for days now. Keep it in there, keep going, it feels wonderful. Pump it in and out, let me feel your cock fill my cunt.” I was stroking it in and out slowly, going from tip to balls. Her pussy was a swamp and inside it was so swollen it felt like I was fucking with my dick wrapped in a mitten. “Wow your pussy is nice. Your cunt is sloppy wet, it’s warm and it’s swollen up like a whore's first trick. I love fucking wet pussy, driving my cock deep in your sloppy hole. Let me just fuck your whore pussy slowly for a while. It feels so fucking good!” “Oh yeah. Keep fucking me slowly like that, don’t stop, don’t stop. Fill my whole pussy with your hard cock. Fill me up with your cock, then dump your load of hot jism deep in there. Just fuck me, fuck me.” The feelings on my dick were incredible. Her sloppy wet hole, all swelled up and clutching my dick felt amazing. I started to quicken my pace, thrusting rather than just sliding my cock into her sweet pussy. As I went faster and harder, I could feel her twat starting to loosen up. “That’s it. That’s it, baby. Loosen up that tight little whore pussy. Give me your best sloppy slut cunt. Let me have your slut cunt to pound. I love pounding nasty, skanky slut cunts.” My pace had quickened and I was thrusting harder and harder with each full-bore stroke. I reached my arms under her legs to raise them. I got her legs folded nearly in half, up by her shoulders. This gave me wide open, direct access to her fuckbox, so I started slamming my rod deep and hard into her sloppy hole. By now her hole had loosened up, no longer so swollen but a wide-open cunt ready to take on whatever wanted to fuck her. I started to pound her pussy hard, ramming my dick deep into her wet cunt. I was pounding her hard and fast when, suddenly, she gave a low, guttural moan and I could feel her warm juices flooding her groin. I kept fucking her pussy, now at a slower pace. I was still hitting bottom with each stroke but I wanted this to last. “Yeah, come on baby. Let me fuck your skanky little slut cunt. Give it to me, let me pound you all I want. I love ramming my cock deep in you. I want to shoot my load way deep in your luscious cunt. Just lay there and let me pound you till I cum.” As I said this, she let out another deep, guttural groan, had the shivers and dissolved into a giant “AAAHHHhhh…” as she flooded her fuckbox with her second orgasm. Her wide-open pussy was a skanky, sloppy mess. The thought of her flooding her sex juices on my dick did it for me. My orgasm came on quickly and I thrust my cock deep into her drenched pussy, held it there inside her, and enjoyed my climax. Another hard thrust … another squirt of my cum far down in her hole. A third thrust ended in yet more cum filling her up. When I finally extricated my cock from her, I watched as my thick cum juice drained from her slit, big globs of it streaming down to her asshole. As we lay next to each other, we both drained our glasses of rum. “That was just what I needed, Sailor. Thank you, thank you.” It dawned on me that the rum was gone. “Connie, the rum's all gone. And I’m not done with my afternoon buzz yet. Any suggestions?” She thought for a moment, then rolled on her side facing me. As she started twirling my hair around her fingers, she said “How about this, Captain. What’s say we mosey down to the restaurant, grab a drink and a bite to eat and discuss what your partnering request is. 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