Chapter 37:
Sundowners With Rachael
Once comfortably aboard, I studied Rachael. She was a stunning beauty. Clearly out of my league. Her jet black hair framing her crystal blue eyes made a striking appearance, one that turned heads in public. She had nice firm tits, standing up with no sagging. Her blouse was tight enough to reveal her nipples and low cut enough to give an inviting view of her ample cleavage. She had on tights that wrapped around well-proportioned thighs and encased her perfectly shaped ass. All-in-all, she was truly a beauty.
I showed her my purchases from the liquor department and asked if she’d like a drink. “Oh, please, yes. How about a vodka and cranberry?” “Coming right up.” I mixed her drink and poured myself a three-finger tumbler of scotch. We took our drinks and retired to the cockpit to enjoy them as we viewed the incredible sunset. Sundowner time, we boaters call it.
I was quite nervous sitting next to such a raving beauty, alone on my boat. I started gulping my drink, hoping that it would still my nerves. My mind was racing, wondering what was next. I was tacitly hoping for some action, yet the reality of the situation looked otherwise. We made some small talk. How beautiful the sunset was, how good the drinks tasted, our taste in music. Nothing sexual. Drat.
Soon the effects of the alcohol started kicking in and my glass was empty, as was hers. “Let me refresh your drink, Rachael.” “Yes, please” she responded, and gave me a sultry glance. “Do you need any help with that?” My response was uncharacteristic. “I don’t need help pouring more drinks, but you can help in other ways.” I said this looking straight into her beautiful eyes, trying not to appear desperate or pleading.
Before she could respond I grabbed her glass and made a quick exit down below. I half expected her to follow me, given the sultry glance she had flashed earlier and the implied innuendo I had just delivered. Instead, she remained seated in the cockpit. When I returned with our drinks, she turned to face me. “So, how can I help? You said that I could help in other ways. What do you need help with? Just name it and I’ll see what I can do.”
I was now on the spot. She had taken the bait so now I had to either reel it in or throw it back, catch-and-release style. I took a few healthy sips of my drink as I contemplated my response. Do I blurt out my desire to have sex with her? Should I punt and let it go, asking for help cleaning my boat? The scotch was starting to take it’s intended effect. My mind was reeling around, not certain of the “correct” response. I slugged down more drink as I considered my options. I decided that the best option was to be candid, giving her a straight up answer.
“Well, Rachael, I have to be honest with you. You are an extremely attractive woman with a killer body. I’ll admit that I’m somewhat surprised to find myself in this position with you – alone on my boat, drinks in hand. I realize that you’re way out of my league and never in my wildest dreams could I envision this. My fantasy is that I’d like nothing more than to suck your pussy, have my cock explore your holes, make you cum on my face. You name it, my mind has gone there. But, the reality of the situation is that I doubt you’d be interested in any of that. There. Now you have it. The honest truth.”
She took a long, hard swallow of her drink before she responded. The silence was killing me. My nerves were tingling and I slurped down the last of my drink. I feebly said “Before you respond, let me get another round. My nerves could certainly use it.” I scurried down below, returning with fresh drinks.
Once seated, she looked me dead on with those fantastic eyes. They seemed to pierce right through me. “I’ll be honest in return, Sailor. As I said before, your vibe is captivating. I don’t focus on outward appearance so much, everyone’s different, but you’re a handsome man. Ever since we met, I’ve been weighing the pro’s and con’s of hooking up with you. After hearing the gossip around town and getting to know you in person, I think the pro’s outnumber the con’s. In fact, I’d almost consider it an honor to sample your wares. So, there. Now you have it. The honest truth.”
I was dumbfounded. I never expected that response. So now the ball was back in my court. How to proceed? I’m not usually shy when a woman gives me the green light as she had just done. Yet, for some unknown reason, I felt frozen. The alcohol had made my brain freeze up, I was nervous as a cat considering her beauty, and I was having trouble deciding on how to proceed. I simply stared at her, swallowing hard, with a look of complete surprise on my face. Instinctively, I reached for my drink and chugged it, bottoms up. As I looked back at her, she was looking at me with an expectant look in her eyes. “Well, Sailor. Where do we start?”
“I’m sorry, Rachael. I’m just a bit taken aback with your response. I wasn’t expecting that and my brain short circuited.” “How about you stand up, drop your drawers and let me get you in the mood” she said matter-of-factly. With little hesitation, I obliged. My manhood was partly hard, about a quarter of the way there. She grabbed my hips and pulled me closer as she took him in her mouth, no hands.
She started working on his head, lips encircling it, tongue wiping around it. Her mouth and lips were soft and warm. She continued to concentrate on just his head, using her lips to pleasure it. Soon her tongue started sliding towards his underside as she put about two inches into her mouth. Her lips and tongue technique were marvelous and within moments she had him fully erect. She would continue to take more and more of him into her mouth, eventually getting him to the back of her throat, her deepthroat door. In response, I began gently fucking her mouth, taking care to keep it shallow.
After a few minutes of this, she pulled her head back and looked up at me. With her gaze glued to my face, she started long, slow strokes all the way to her deepthroat door, then back to the tip again. She kept looking at me and worked her magic on my cock. I’ll admit that her crystal clear, blue eyes framed by her jet-black hair with my dick sliding in and out of her mouth was erotic. It sent shivers throughout my body. I was falling prey to what she had described before. Men didn’t last long when watching her give them a blowjob. I was no exception.
I felt the tingling in my privates as my orgasm welled up, racing it’s way down my shaft, coming hard like a freight train. There was no stopping it. I put my hand on the back of her head and pushed my throbbing cock all the way in as I let out “Oh, Christ! You’ve got me! I’m cumming, I’m cumming!” I held my dick against her deepthroat door and shot my wad. I could tell it was a big load and it took several spasms for my nuts to empty themselves in her mouth.
As I pulled him out of her mouth, she kept her face pointed up at me. She opened her mouth and let me see my jism on her tongue. She mimicked so many of the porn queens by sluicing my cum load around her mouth, on her tongue, on her lips, finally allowing some to dribble down her chin. I took my dick in hand and washed her face with it. I smeared it around, slapping her pretty face with my cock. Finally, she took a big swallow, licked her lips and said “Did that help get you in the mood?”
She had set the bar; I now had a challenge. Once we were nude, we embraced, held each other tightly and started making out. Not only was Rachael a looker, she was an expert kisser. Her lips were full and wet. She had complete control over her tongue, and she was a wet kisser. I was glued to her mouth, no thought even of bending down to suck on her ample breasts. Time for that later. I had one hand on her ass, the other holding her head against mine. After what seemed like an eternity, we broke, panted a moment, and turned our heads to the opposite side. We went at it again, kissing passionately, our bodies grinding against each other.
When we finally parted, I stepped back to survey just how I was going to continue making out – only now with her pussy lips. I suggested that she lay on her back on one of the cockpit benches. I gave her some cushions, one for under her butt. I got on my all fours between her legs, wrapped my arms under her legs, and scooted her down into optimal position. I had her entire inner thighs and fuckbox laid out in front of me like a smorgasbord.
It started with light, gentle kisses, from her knee down to her crotch. I spent my time covering every inch of her buttery inner thighs with kisses, nibbles, tongue flicks, hot breath. I started licking and kissing all around her slit. Still closed, I lapped at her outer lips and nibbled on them. Knock, knock, I thought. My tongue, starting at the top, began parting her outer lips. I’d run my tongue from the top down to her hole, back up the other side. By now she started moaning and sucking in her breath.
At the top, my tongue found the ridge leading to her clit, still hidden by her inner lips. I stroked my tongue up and down on it, eventually getting her inner lips parted, revealing a fully erect clit. Her pussy was dripping wet. I could smell it and her juices were saturating my beard. My tongue circled round and round her clit, sizing it up. It was normal size, maybe a bit thicker than most. But it would do nicely. I gave it a quick bite as I pulled my head away.
I lifted her hips a bit and directed my mouth to her vagina. She rocked her hips up even more, exposing both holes in all their magnificence. My tongue found her cunt hole and I sucked up her pussy juice. I tongue fucked her hole best I could, alternating between her pussy and her asshole. I’d circle it with my tongue, then push it into her asshole hard. She was moaning louder now and her hips were twitching around. She called out “That feels so fucking good, Sailor. Soooo good. Your tongue in my asshole is delightful. Haven’t had that feeling in a while. It makes me twitch. Ohhh how nice. Now more on my clit. I want you to ravish my clit.” As she said this, she put her hand on the back of my head as if to guide me to the right location.
I refocused my attention on her clit. My lips started with sucking it in and out, like jacking off her clit with my mouth. I used my lips, my tongue and my teeth to cajole it into an orgasm. It got twiddled and squeezed, it got sucked, it got pushed and pulled every which way. I’d use the tip of my tongue to flicker on it, hoping my fluttering tongue would carry her to ecstasy.
As I continued my assault on her clit, she was nearly crying out as her hips started bucking. Between gasps of air sucked in, she nearly squealed “Oh, Yes! That’s it! Oh, YES!! I’m right there – right there!!” Suddenly her hips thrust upwards and she screamed out “OH FUCK OH SHIT OH FUCK!!” as one long word. Her pelvis slumped back on the cushion and her whole body shivered. I gave her a moment, then very gently rubbed my lips and tongue on her clit. I gave it a very slow, very gentle massage. She was nearly purring when I sat back up.
“They were right, Sailor. All the rumors are true. You certainly know what you’re doing down there.” “Well, I enjoy doing it. I enjoy it a lot. And, at my age, I’ve had a good long time to practice.” “Sailor, not to break the mood, but do you have any Cointreau? I’m feeling like an orange liqueur, as a nightcap.” “Your every wish is my command, my angel.”
Shortly I reappeared with two shots of Cointreau. She cuddled up to me and I put my arm around her shoulders. As we sipped our liqueur sitting in the cockpit under the moon and stars, she casually said “I’m kind of tired and this drink is making me even more drowsy. Would you mind if I spent the night here on your boat?”