Holli and an Evening Sail

Holli met me at the end of the dock… and my heart skipped a beat at she slid into view. She was dressed for an evening on board my boat – simple deck sandals, a lovely pale blue top and a pair of very comfortable khaki shorts swung easily on her curves, hinting at what she had to share beneath. 5’9” with blond hair, long legs and a fit athletic body, Holli had entered my world through a magical afternoon we shared on the Vancouver waterfront. This evening was a result of my invitation as we had cuddled and recovered, and just the thought of what we had shared earlier was enough to make me tingle at her first touch. As far as my boat - my family likes to call it a yacht when they mention their vagabond daughter, but at 38’, Huntress was simply a great sailboat for a solo sailor with no home address but the next marina.

I kissed her hello and led her down the dock to Huntress’ slip, very aware of her eyes on me the entire way. As a sailor, I don’t spend much time worrying about my hair and makeup, but days at sea tend to keep one in d shape and toned – and at 5’3” with my auburn hair pulled back in a ponytail, I was able to show off the curves that an active lifestyle gave me. As I pulled the spring-lines to bring Huntress to the dock so we could step aboard, I felt her hand slip around my waist and felt her fingers trace designs over my abdomen, leaving my exposed arms and legs rippled with goose-bumps and my breathing a bit ragged. She purred in my ear in appreciation of my reaction and said simply “I can’t wait to get to know you even better, Kat”.

Once we were aboard, I went below and pulled out some wine and cheese (a staple of my in any port) and came topside to visit and flirt with this wondrous woman. Holly had made herself comfortable and was letting her eyes wander over the rigging and helm station of my home, soaking in the details of a very important part of my world. I slid next to her and felt a tremor ripple through me as our legs touched. Before pouring our wine, I simply leaned and gave her a long soft kiss, letting our lips brush lightly against each other, bringing my tongue to explore hers and drinking in this amazing feeling. We sat nearly on top of each other as we shared experiences, discovering we had both been raised stateside and attended college not too far apart, her in Boston and me in Providence. The bottle of wine slowly emptied as we talked, and our hands touched, sliding up and down each others arms and across the warmth of our legs, kisses punctuating the pleasure we felt in those caresses. The wind had freshened as the sun dropped out of sight, and Holli asked if we could take a sail out toward the island. I eagerly complied and pressed her into service as first mate, casting off all lines and motoring out of the marina before hoisting sail and silently cruising the sound, the lights of the city slipping away as we reached toward Vancouver Island. Once offshore, she smiled and slipped off her top and shorts, revealing a very small black bikini that promised a wonderful evening afloat. Smiling, she wondered aloud if the scenery wouldn’t distract the captain as her hands, played over her breasts and down her stomach, thumbs playing over the patch of cloth covering that memory of her pussy against my lips earlier in the day.

My answer was a small smile and flipping two switches that locked in the course and connected my sat-nav to the helm. As I left the station and headed toward my lover, I revealed my own surprise, stripping off my tank top and shorts to reveal my body… naked and so ready for our next adventure….

Holli’s smile was like a beacon in the dark. “We’ve got about an hour before she rounds the point, baby” I purred “come join me and let’s enjoy the silence” I reached up and drew Holli to me, almost crying out in pleasure as her skin came into contact with mine. My nipples, taut and erect, became pinpoints of electricity, sending shivers coursing through my body as I felt her against me. Our tongues met in a passionate kiss as I quickly ripped her bikini away and ran my fingers across her back and ass. Her thumbs drew circles around my nipples and outward, cupping my breasts, gently squeezing as she did. I kissed my way down her neck to suckle each nipple and hear her softly moan her approval. Leaning her back on the settee, I let my mouth explore the geography of her breasts and tummy, kissing, licking and biting my way down to her clit, where I softly blew air over it and watch her shiver before letting my tongue tickle ever so gently….

My hand slipped between her legs and two fingers stroked the lengthy of her slit, slipping easily in the wet warmth, teasing her from her ass to her clit as my mouth covered her mound and my tongue teased her toward release. She responded by wrapping her legs over my back and holding me against her, her moans getting louder as I kept up my assault on her clit and pussy with my mouth and hand. As she tensed and I heard the pitch of her moans increase, just as she was about to cum, my little finger slid back and entered her ass… wiggling as she let our a moan than echoed over the sound and leg legs tightened around my. The warmth of her juices flooded my mouth and I gratefully lapped my lover clean as she came down from her orgasm. I kissed my way back up to her lips and shared our lovemaking with her. She pulled me close and began caressing my hair, kissing me and purring as we sailed into the night, then her hands began to retrace their earlier travels over my nipples, causing me to lean against her and nibble her neck in delight.

Apparently I had accidentally discovered one her erogenous zones with those nibbles, as she moaned, stiffened and suddenly flipped me under her, a look of pure lust on her face as her hand suddenly found my drenched pussy and two fingers slipped inside as she locked eyes with mine. The feeling was intense and unique as I watched her watch me react to what was a truly wonder hand-fuck. Her fingers alternately caressed my clit, teased my ass and slid deep inside my aching pussy as she brought me to climax. I reached up as I headed over the edge and brought her into a passionate kiss as I trapped her hand inside me, cumming over and over as I experienced her again.

Exhausted, we collapsed against each other in tangle of arms and legs, laughing as we tickled our fingertips across each other’s faces between kisses. The beeping of my auto-pilot reminded me of our course change and I reached beneath the helm and tossed my lover a t-shirt from my stash kept there so we could start heading to harbor without raising too many eyebrows. As Holli was a good half foot taller than me, even my oversized shirt hung tantalizing close to the curve of her ass. The sight of her preparing to tack made me tremble as her cheek would slip in and out! She looked at me and wondered aloud if there was a cove nearby where we might anchor for the evening. I checked the navigation system and found a likely spot about 15 minutes distant by sail, closer if we motored.

We hove-to in a secluded cove on the leeward of the island and made Huntress fast. I turned on the audio system and let the sounds of Sinatra and Connick wash over us. We fished another bottle out of the cooler below and sprawled out on the settee in each other’s arms, letting our hands explore the contours of the other’s body, hearing the contended sighs of lovers as we talked about nothing. Our reverie was broken by the arrival of a smaller powerboat in the cove. A voice called out and asked if they could share the anchorage. Although loathe to give up our privacy, courtesy prevented me from waving them off.

Another voice called out, thanking us and inviting us for cocktails. I felt Holli stiffen slightly, then laugh as she looked up at me. “Kat”, she purred, “I hear two men”, her hand stroked over my pussy and told me what she had in mind. I called out and invited the captain to raft up for the evening. As they approached, we stood in our short t-shirts and smiled as lines were passed across. Holli made a point of reaching out to tie off the boats just far enough to confirm their suspicions that we were only wearing those shirts. The two men looked confused, and hopeful as we tied up and introduced ourselves. Keith and Brian were on a cruise to Seattle, bringing down a friend’s boat for the summer. Both appeared to be in their late 20s and were pleasantly surprised to find a boat, hoping to share dinner and drinks with fellow sailors. We shared the remainder of our second bottle with them as Holli slid closer to Brian and me to Keith. The boys were enjoying the attention and the wine ran out as we flirted and made contact “accidentally” with our newfound friends. Holli excused herself to get another bottle below deck, then called out for me to help her. I went below and we hatched our plan for the evening….

Coming back on deck we returned to our seats and cuddled a bit closer to each man. Their crotches gave away their feelings about our activities and both of us began to furtively caress the bulges, stealing kisses and snuggling in next to our targets. I made eye contact with Holli and we stood in unison, looking the boys in the eye as we both stripped off our shirts and kneeled, naked in front of them, unzipping their flies and taking those lovely cocks in hand. I said simply “Gentlemen, it’s your lucky day, but you have to agree to one thing” As their cocks were pulsing in our hands, I knew this negotiation wouldn’t take long. Keith and Brian readily agreed without hearing the condition. As I kissed the head of his lovely 7 inch member I looked into Keith’s eyes and simply said: “you have to fuck both of us” and proceeded to swallow him down to his balls, letting my tongue swirl over the length of his shaft. I knew Holli had made the same demand as I heard them both groan in delight.

Holli and I sucked the boys and brought them close once or twice, only to switch men and begin the process all over g again. Brian’s cock was a bit bigger than Keith’s, and tasting Holli on it made it even more fun to go down on. As we stood up the second time, we gave them another choice- whose mouth did they want to cum in? Keith immediately chose Holli, and Brian looked dejected. Holli took his cock in one hand and Keith’s in the other and smiled, letting them know it was fine with her if both unloaded in her mouth. For my part, I simply took advantage of the situation by having the mouth of the man not being serviced firmly planted on my pussy while Holli brought the other to a shattering orgasm.

Once the preliminaries were out of the way, we knew which man each of us wanted first and proceeded to get them ready for round two. I walked over to Brian and sat on his lap, firmly putting that lovely thick member between my ass cheeks and slowly riding him until he responded. Holli went to Keith and put his cock between her breasts, smiling as she tit-fucked him back to life. Once hard, the boys had no problem as I turned on Brian’s lap and guided him in and Holli laid back and Keith slipped in from above. The boat rocked at anchor in synch with our fucking. After a few minutes I slowed and looked at Brian and smiled as I stood. “Remember, you promised” I said as I reached over and tapped Keith’s shoulder. Holli stood next to me as we held onto those big cocks, all slippery from inside o us and led them to the front of the cockpit. We let go and turned, spreading our legs as we leaned against the cabin and invited the boys back in. Keith’s cock slid in and I recognized immediately one thing – he knew how to fuck soooooo much better than his slightly-more well endowed friend! His strokes were deep and even and his hands went to work on my nipples and clit immediately, send waves of pleasure through me as I pushed back against him. I looked over at Holli and saw her enjoying Brian as well. Reaching out, I touched her hand and brought it to my lips and was rewarded with a smile and a kiss as we continued to enjoy these perfect guests. The kiss must have set the boys off, because the speed and depth of Keith’s thrusts mounted steadily, along with the occasional withdrawal and slipping along the crack of my ass… almost like a request. I decided to honor his request the next time he slid out and pushed against him as his head slid over my ass. He froze, and I worked his slippery cock slowly into my ass, feeling the head pop in and then most of his shaft. I smiled back at him as he looked down in almost disbelief and let him know I wanted him to cum in my ass. Holli smiled over and kissed me again, whispering how hot she thought that was. Keith didn’t last much longer, firing off a huge load that I felt fill me up. Brian followed suit, although he pulled out of Holli and unloaded all over my lover’s beautiful back. I grabbed his cock and cleaned it, then lapped up his load from her back, explaining I hadn’t had a chance to get any earlier. Holli reached behind me and slipped her finger in my ass and pulled it out licking it clean as she smiled at Keith.

Smiling at the boys, we curled up in each other’s arm sand bid them goodnight, promising to have breakfast in the morning as they jumped aboard the boat for the night….