Chapter 30: Connie Shows Me How It Works
We settled in the back corner booth of the bar, the throngs of people now gone. The place was a third full, not too busy. Shortly, Carla came to wait on us. “Oh, I see you’ve met Connie. What are you two having today?” “Hey, Carla. Yes, I met Connie after the raffle this morning. She’s been trying to explain how it all works. I get the basics but some of the nuances escape me.” “No worries, Sailor. You’ll catch on in no time. From my experience, I’d say that you have a decent chance of replacing Chet.” She gave a quick wink to Connie and took our order.
As we waited for our order to come, I saw an older woman, probably in her mid-70’s, in an adjacent booth, lean over and start giving head to the barely legal teenage boy sitting with her. No one else in the bar showed any interest. Even though I had witnessed Carla doing the same thing, it still shocked and amazed me.
“So, Connie. Is this the bar where everyone comes to have their dick’s sucked? Why aren’t you sucking mine?” “I will if that’s your partnering request. Typically, partnering requests go back-and-forth. You just gave me a much needed, satisfying pussy fuck. So now it’s your turn. Do you want a quickie blowjob here and now? Or would you rather wait a bit to satisfy a different need or desire?” Just then our food arrived, saving me from having to make an instant decision.
As I enjoyed my fish sandwich, I thought about my sexual appetite and what I craved from Connie. She certainly had a splendid pussy. No doubt there. She had treated me to a memorable, sloppy, wide open fuckfest that had drained my cum. What did I want next?
“I’m having a hard time deciding, Connie. Our mid-day session was wildly successful. Can you work that same magic with your mouth?” “That’s not my strong suit, Sailor. I’m better with my pussy and asshole. I can always call in a surrogate if you want mouth servicing for your dick.”
“Uhm, maybe another time for that. I think I’d like to have you doggy style, so I can fuck your pussy and your ass, switching from one hole to the other. Does that sound better?” “Sure does, Sailor. I’d love that. Just remember, though, that having my pussy counts as one partnering request. Then switching to my ass counts as a second request. So afterwards, I’ll get to have you do me twice! It’s still early afternoon and we have until midnight. Let’s stop at Timmy’s for more drinks to take home.” I stood up and reached out my hand. “OK, Connie. You’re on. Come with me.”
I led her down the block to Timmy’s, the only package liquor store in town. It was a small store, tightly packed with every way to escape reality imaginable. Connie wanted vodka and cranberry; I chose a single malt. As Timmy rang us up, Connie introduced us.
“Sailor, this is Timmy. Not only does he supply us with our poison of choice, he is also a surrogate for guy’s who can’t get it up. Somehow, Timmy can always get it up, and fast, too. Timmy, this is Sailor.” “Nice to meet you, Sailor.” “Likewise.” As I grabbed our bag and turned toward the door, I saw Connie and Timmy making a clandestine exchange.
Back at Connie’s place, we made drinks together in her one butt kitchen. As we moved about assembling our drinks, our bodies kept touching. A subtle hip bump, a glance on the shoulder, the front-to-back full body squeeze between the counter and the island. It’s as if our bodies were magnets, poles aligned just right.
We took our drinks to her outside back patio. She had an appropriate array of tables and chairs, a small fire pit at the outside corner and a corrugated roof. It was open on the sides and you could see the neighbors back yards. There was no real privacy. At the moment, there was no one else outside. We settled in on some chaise lounges, a small table between us. As I settled onto my recliner, I noticed that it was much wider than a normal chaise, half again wider. Whoa! Two can fit on here! Sweet!
“Hey, Connie! Come join me. There’s plenty of room.” She joined me and we both chugged at our drinks as we snuggled in. Like oversexed teenagers, we were instantly kissing, groping, rubbing, writhing maniacs. It felt like we had just discovered how wonderful sex is and had fallen prey to it. Our bodies were meshed together, our legs intertwined, our hands caressing each other. We were basically having sex with our clothes on.
It washed over us simultaneously that we had to shed our clothes. We rolled apart and sat up, grabbing our drinks en route. As we were fumbling with buttons and draining our drinks, I asked “That make out foreplay was terrific. But since neither of us requested it, how is that scored?” “Usually, make outs, lap dances, strip teases and the like, are considered tips. I’ve had a guy who, after fulfilling my request, always ‘says goodbye’ to my tits with a quick nipple suck, one on each boob. I’ve been known, after a guy fucks me silly, to bend down and suck his cock head, briefly tonguing his soft spot. I’ll consider our make out session a mutual tip.
“Now, while I’m super charged, what fantasy of yours can I fulfill?” “My desire is to have you refill our drinks, then come and straddle me, reverse cowboy, and have you use both your pussy and your asshole to fuck me.” “You know that counts as two.” “Precisely. You said we had until midnight, right?” “That’s right. After midnight, neither of us can ask the other to fulfill any desires and expect the other to comply.” “OK. So, if at the witching hour I still owe you a request, I can fulfill that with a surrogate?” “Yup. But you might have a hard time finding an available one. See, you didn’t buy a raffle ticket; neither did I. Surrogates only play with “outsiders” – those who didn’t buy a raffle ticket – if they feel like it.”
She brought out a tray which she placed on the other chaise lounge. It held our drinks and a coke snorting setup. Thanks, Timmy! As we claimed our drinks, she raised her glass in toast: “Cheers! To Partnering For A Day!!” We each took a perfunctory sip, paused, then glugged down a big gulp. She busied herself cutting lines, neatly arranging them for use. When satisfied, she took the rolled up $100 bill and snorted one line up each nostril. As she was sniffing and snorting, I followed suit. We washed it all down with the last of our drinks. My turn to play maid.
When I returned with fresh drinks, Connie had just shot another $100 up her nose. As I settled back in on the chaise, we clinked glasses and sipped politely. She spoke first.
“So let me get this straight. You on your back watching, me straddling you backwards, you watch me fuck you with both holes. Right?” “Right.” “Can I make just one suggestion, Sailor?” “Sure. What is it?” “I’d like you to fuck my pussy first, get it wet, then use my pussy juices to lube my ass. No KY. But before you enter my ass, rub some coke on the puckered hole. A fair amount. Maybe even some on my clit or pussy if there’s enough. It has a profound effect and your dick will thank you. Try it. You’ll like it!” “You’re on!” as we clicked glasses again. I took a big slug of single malt and used the $100 bill once more before getting in position on the extra wide chaise lounge.
She mounted me positioning her equipment right above my junk. This chaise was wide enough for me in the middle and Connie’s knees on either side. She reached between her legs and used her fingers to spread her lips. Despite our earlier sex with clothes on session, her pussy was dry. I spit on my fingers and spread it around the head of my dick. She used some quick up and down thrusts and soon my cock was firmly inside.
Knowing that her pussy swelled up at first, she used that to her advantage. She would raise up, then slam down hard and fast for 3 or 4 strokes. Then she would tease my head by using some quick in and out strokes on the top inch or two of my cock. Then back to full length slamming. From my vantage point, watching this was a major turn on.
I was high on coke, drunk, and, watching my dick disappear up this heavenly hole, took me to the edge. She kept this up for God knows how long. When she could feel that she was wet enough she said “I want to feel your cock stretch my ass now. Lube it up with my pussy juice and cake it with coke.”
I wiped some pussy juice and some spit on her tiny hole. I worked my finger in and out, then got some white powder to dab on her asshole. More pussy juice, more coke, rubbed randomly on her cunt. She reached around to guide my rod where it belonged. She was in charge; I could only lie there.
She got the head popped in with no trouble. Then started raising and lowering her hips while my dick was in her ass. I watched as she worked her hips, thrusting in various patterns, fucking my dick with her asshole. She was a temptress, making her asshole dance around with my dick tagging along. She had the right mix of going balls deep and taking short strokes at the tip, clenching her asshole tightly around my glans.
Her hip movement slowed to a crawl as she shifted her position slightly. With my dick still firmly up her ass, she slowly stroked it in and out a couple of times. The next time she reached the tip she kind of twitched and my cock suddenly found itself in her pussy. A dozen strokes in her pussy and, wham! There’s that twitch again and now I’m in her ass! I was closely watching my dick going in and out of her holes, but I could never quite see how she mastered that.
She knew what she was doing and she was good at it. She’d use her cunt, then twitch it into her ass, back and forth, over and over. She got this going in a rhythm faster and faster, never missing a hole. Her cunt opened and got dripping wet. Her tight ass got stretched and opened wide up. She was working hard rocking her hips up and down, switching holes, going fast, starting to pound my groin by slamming her holes down on my stiff cock. “Holy fuck Sailor! That coke on my holes made them numb but itchy. Can’t get enough of your dick.”
As I watched and felt her take 5 strokes in her pussy, then 5 in her ass, I felt my cum welling up. “Shit, Connie! You’ve got me, you’ve got me. I’m gonna cum and I want to shoot it in your ass.” She twitched it into her asshole as I reached up and grabbed her hips. At the bottom of a down stroke, I held her hips down with my cock fully up her ass. My wad came in 5 spasms, delivered fully up her ass. When I came, I let out a long, quiet “YYEESSSsssss” and held her hips tight against me.