Chapter 15:
Clubbing With Sandy and Ashley
The Uber ride home from Sandy’s seemed to take forever. The dinghy ride to the boat was worse. I was barely aboard and down below before my pants were off and I was stroking my cock. I was so horny it didn’t take but a minute before my creamy white cum came squirting out of my dick. Satisfied for now I climbed into bed and soon drifted off with pleasant thoughts of eating Sandy’s pussy and tomorrow’s possibilities echoing in my head.
Woke up and fixed coffee and some breakfast. Read some internet news just to see if the world was still falling apart. It was but my mind was really wondering if Sandy would follow through. I busied myself with some minor “fix it” projects on the boat. Before I knew it, it was 3 o’clock. Hadn’t heard from Sandy. Should I call? Would that be too pushy? If I don’t call, will she think I’m not interested? I was torn. I popped a beer and retired to the cockpit to contemplate my next move.
About 3:30 she called. “Hey sailor. Got a proposition for you. How ’bout we meet at the bar and mutually *********** our partner for tonight. Sound feasible?” I had hoped to just show up at her place to find Sandy and some slut getting it on and sort of join in. This new plan involved, well, work. “Gee, I guess so. Not sure how the dynamics are gonna work.” “Not to worry sailor. Leave all that to me. Just show up at the bar on Main by 7. Got it? Oh, and wear something nice, a collared shirt maybe. Maybe even some cologne. Not that you need it, but the girls go for that stuff.” “This is getting complicated Sandy.” “Oh, fuck off dick head. You asked for this. You could have just fucked my ass last night and been done with it. But NOOO. You wanted to see two girls getting it on and maybe fuck two assholes. You play, you pay. Suck it up sailor and just meet me at the bar.” “OK boss lady.”
I walked in the crowded bar and surveyed the crowd. About 2/3 women, some on the dance floor dancing with each other, some with guys. Didn’t see Sandy right off so I made my way to the far end of the bar and ordered a draft. Kept scanning the crowd for Sandy. The music stopped and the dance floor cleared. Suddenly a woman was aiming right toward me. “Hey sailor. Glad you could make it.” Holy fuck. It was Sandy yet it wasn’t. She was all made up, bright lipstick, heavy mascara, eyeliner, thick rouge. And she had on a very tight, very revealing top showing her midriff and lots of cleavage. Her nipples were on full display. Her skirt was a micro-mini, skintight. She had her hair teased up or something, couldn’t really tell. “Whoa! You certainly look different!” “Different bait catches different fish.”
“Here’s the plan, Sailor. When songs play, I’m gonna go dance with a girl. Whoever I’m dancing with will definitely go home with me for sex. Different girl each dance until there’s one you like. When I’m dancing with the one you want, come start dancing with us. After the song we can get drinks and talk. Got it?” Before I could answer the music started and she flitted away, grabbing some hussy to dance with. Wow. This was weird, not what I expected at all.
I sat and sipped my beer wondering what I had gotten myself into. As the third song started, Sandy escorted a young girl to the dance floor but worked her way right past me, sitting at the bar. She shot daggers at me, hesitated with her partner briefly right in front of me and slid onto the dance floor. Her partner was young and attractive, at least with all her makeup on, and would do in a pinch. Not my first choice but not my last one either. Throughout the song Sandy kept her eyes riveted on me. Her dance partner noticed, looked over her shoulder at me and said something to Sandy. I could see Sandy laugh and then the music stopped. They made a beeline to me. Uh-oh. The jig is up I thought.
The girl was cute, about 22 or 23. Dressed about like Sandy. Definitely fuckable but not the type usually attracted to older guys like me. “This is Ashley. She thinks you’re cute and that we’re married.” I roared with laughter and nearly fell off my barstool. “Hi Ashley.” “You’re cute. I love your long blonde hair. Looks cool on an older guy” Ashley said. Not knowing how to proceed, I looked at Sandy with pleading eyes. She took over. “Hey Ashley – sailor and I were just gonna go back to my place for some drinks and some adult fun. How ’bout you join in? You look like you’re up for some adult action tonight, huh? How ’bout it?” Ashley squealed with delight, jumping up and down. “Oh, absolutely! I’d love to!”
At Sandy’s, Ashley wanted a Rum and Coke. Sandy made a strong one and produced her usual bourbon pour for us. The girls sat on the couch; I was in an easy chair across. Sandy had on her tight micro-mini with no undies and made sure to keep her legs spread, pointed right at me. What a view! I remembered a dumb college drinking game aimed at getting the girls wasted. Girls had to drink whenever they said certain words. Ashley wasn’t the sharpest pencil in the box and Sandy and I easily had Ashley taking drink after drink. Before long she was on her third drink, Sandy making them extra strong.
Being the impatient sort and having had to stare at Sandy’s clean-shaven cunt for a half hour, I suddenly got up, walked over to Sandy, leaned over, and planted a big kiss on her mouth, grabbing her boob as I did so. “Hey! What about me?” protested Ashley. I pulled away and Sandy immediately started making out with Ashley. They kissed for a couple of minutes, then came up for air. I had a full blown hard on, quite visible through my pants. Ashley noticed, giggled, and reached out to touch it. “Want to give it a kiss, Ashley?” “Oh, I’d love to!” “Well, you’ll have to follow me then.”
I started towards the bedroom, Ashley followed, and Sandy refilled our drinks before joining us. By the time Sandy joined us, Ashley and I were naked, me sitting on the bed Ashley on her knees between my legs sucking my cock. Sandy got undressed quickly and seeing that I was enjoying this blowjob, handed me my drink. Ashley wasn’t very talented, but her warm wet mouth felt good on my throbbing cock. Sandy wanted in on some action, so she took my drink from me and pushed me, so I was laying on my back. Ashley was still trying her best at my cock as Sandy climbed up and straddled me so that she was sitting on my face. Wonderful I thought. I started licking her smooth cunt, the delicious juices magically appearing again. I was only thinking about getting Sandy to squirt on my face when Ashley stopped. “Hey! What about me?” So, we rearranged ourselves so that Sandy could sit on Ashley’s face.
I stood aside for a minute sucking down my bourbon and watched Sandy rub her twat in Ashley’s face. After a few minutes of this Ashley said she wanted her cunt licked. She scooted up on the bed a bit, rocked her hips back with her legs up high and Sandy knelt between Ashley’s legs, sucking, and licking Ashley’s pussy. Seeing my opportunity with Sandy on her knees bent over, her butt raised up, I grabbed some lube and started preparing Sandy’s asshole for my hard dick. I started with my fingers, then stood on the bed behind her and found her tight puckered anus. I pushed my cock in hard and Sandy made a loud grunt but never stopped licking Ashley’s cunt. I started fucking Sandy’s tight asshole finally getting my cock balls deep inside her. I thrust my cock hard into her butt and started slamming my cock rough and hard into her butt hole. Over and over, I pounded her ass, like a madman. Her ass had started out tight and stayed tight. She later told me that she did special exercises, like Kegels, to keep her asshole tight. She said it just felt better to her when her asshole never loosened up and there was a cock slamming it.
Ashley was moaning with pleasure as Sandy worked her magic on her pussy. Ashley soon realized what I was doing to Sandy’s ass. “Hey! I want some of that too” she cried out. So, we regrouped again. We all got off the bed and reached for our drinks. Ashley said “I want your cock in my ass too. My girlfriend only pegs my ass and it’s just not the same. Sailor man, you’ll fuck my ass, won’t you?” As I was standing there sipping my drink I replied “Sure honey. But first you have to come and get on your knees.” She knelt in front of me and I grabbed her head. With no finesse or mercy, I just put my cock in her mouth and started fucking her face hard. Just like I had been fucking Sandy’s ass moments before, I shoved it in deep, over and over. Ashley was having some difficulty, choking and gagging, spit and drool running down her chin. I pulled it out, rubbed the drool around with my cock and rammed it back in. I fucked her mouth like a pussy for a good 5 minutes. When I stopped Ashley gasped for air and coughed, gobs of spit dripping from her mouth.
“Will you fuck my ass now sailor man?” “Well, we’ll get to that, but what about poor Sandy. Nobody’s paying any attention to her. Why don’t you see if you can make Sandy squirt? Let’s see how good you are Ashley.” Sandy was already laying on the bed. She had been watching me pound Ashley’s throat as she rubbed herself. “Aww. Poor Sandy. Let’s see about eating your shaved pussy. I love your shaved pussy. It’s so smooth.” Ashley got to it and shoved her face into Sandy’s crotch. Soon she was finger fucking her too. I sat and watched, excited by watching two girls pleasure one another.
Shortly Ashley turned around so that she was 69 to Sandy but beside her. Ashley kept mouth fucking Sandy’s cunt and Sandy grabbed her dildo and started fucking Ashley’s ass with it, alternating between her asshole and her cunt. Desperate to cum in one of the 6 holes I had at my disposal, I climbed on the bed and positioned myself behind Ashley’s ass. Her hole was gaping from the dildo Sandy had been using. I guided my still hard cock into Ashley’s asshole and started pumping. I’d go in and out slowly, then I’d switch to her cunt. I’d pump her cunt slowly, then switch back to her ass. I’d alternate between her two holes going faster and deeper with each switch. I couldn’t decide which one of Ashley’s holes I liked better. They were both sweet to fuck and each had their pluses and minuses. Finally, I decided that I wanted to drop my load in her ass. I started pounding her asshole without mercy, just ramming it in all the way.
Nobody had talked dirty during our orgy, so I started with Ashley. “That’s it slut. Eat that whore’s pussy. Lick it, suck it. Just let me pound my cock deep in your ass. Just be my little ass slut now. I want to shoot my cum deep in your skanky hole you slut. Give me that nice dirty hole bitch. Let me fuck it good, all I want. I’m gonna pound your dirty, skanky asshole till I cum deep inside. I love slamming my hard cock deep in your tight little butt hole. Squeeze that asshole tight around my hard shaft while I shoot my cum load deep in your ass.” Just then Sandy reached up and grabbed my balls as I was pounding Ashley’s ass. Her touch sent me, and I exploded inside Ashley, each thrust ending in a big squirt.
Having shot my load deep in Ashley’ asshole, I sat in the chair, sipping my drink and enjoyed watching the two girls pleasure each other. They put on quite a show ending with squeals of ecstasy and some serious squirting. It was awesome to watch these girls go to town on each other’s privates. The show now over and all three of us sexually sated, I ordered up an Uber for the ride home. “That was phenomenal, ladies. I thank you from the bottom of my groin. We’ll have to do it again sometime.”