Some Guys Have All the Luck

When we were naked - which did not take long - she dragged me backwards onto the sofa on top of her. She reached into a small cabinet beside it and to my surprise, produced a condom. "I leave a few around the place for emergencies. Don't worry, the one and only time. Just means we can get back for round two without a prolonged clean-up."

She lay across the sofa, one leg dangling onto the floor as I covered up, holding herself open for me. Neatly trimmed, the silky folds beneath the v-shaped bush looked wet and inviting. At her command, I went in hard, then she held me there for a moment, legs wrapped around my buttocks. She kissed me once more. "Tear me a new one, Steven O'Hara. Make me fucking scream."

I was now doubly glad of my evening with Aspen. Not only had it been an amazing experience, but I was much better placed to service the needs of this almost insatiable woman. That first rabbit fuck bordered on the brutal, the sofa creaking beneath us. After a few minutes of mindless shagging, I really did begin to wonder if it was indeed as durable as Taylor said. It was just pure, animalistic rutting, our only pauses allowing us to change position. We were almost telepathic as we switched. Taylor knelt up, her hands on the back of the sofa as I went in from behind, kneading her breasts at her insistence. She urged me to go harder, tug at her nipples, squeeze her buttocks. A cool breeze blew in from the open patio doors, but we were both coated in a patina of perspiration in a matter of minutes.

I somehow held back when she went on top, twerking down on me in a manner that Aspen would have been proud of. I tried to hold back any thoughts of the two women together as I would have lost it there and then. It was after fifteen minutes of utter bliss that we came together, her buttocks on the edge of the sofa, ankles up around my shoulders, hands gripping the soft leather cushions as if she were scared of flying away. She didn't scream, but the keening sounds she made as she approached orgasm spurred me on. As I emptied into my latex covering, she let out a guttural moan from the back of her throat, eyes and mouth wide open.

We collapsed in a panting heap, me still inside her, and held onto each other tightly for a long moment. Finally, she found her voice as my now flaccid cock slipped from her and flopped inelegantly and wetly onto her inner thigh. Her voice sounded a little hoarse and strained.

"Well, that was certainly what the doctor ordered, Mr O'Hara. Two weeks of celibacy smashed out of the ballpark." She squeezed the end of the condom gently. "Oh what a waste, but needs must. Mallory would probably upend it over herself, but I shall save myself for the real thing a little later." She reached up and kissed me. "There will be a later, won't there?"

I assured her there would be and after a beer for me and a glass of wine for her, she proved that she would indeed grace any professional production with her oral skills. Aspen's youthful exuberance was replaced by over two decades of experience. The beneficiary of said experience watched on in dumbstruck awe at the talent of the woman. One moment her lips and tongue were like the caress of a butterfly, the next I was balls-deep in her mouth, her hand pressing my fingers against my erection in her throat. She held me in there for longer than I had ever experienced and marvelled that she was barely out of breath when she withdrew, saliva coating my cock and splattering down onto the bed.

After ten minutes of exquisite torture, she stretched herself and indicated with a long forefinger that it was my turn to reciprocate. I could only hope I was able to match even a tenth of her skill level.

My ex had never been a devotee of oral sex - either giving or receiving. For me, it was a long overdue treat. I may have been out of practice but given the murmured stream of filth that provided a graphic commentary to my actions, I didn't do too badly. I felt quite a pride in that fact that she made Aspen sound like a maiden aunt and her musky taste was an amazing contrast to the fresh, sea-salty aroma of the wonderful PinkyBlue.

There was just something so arousing about the language she used in her cultured New England drawl. The contrast between her almost formal greeting in the Dockyard and her now gutter-language spurred me on.

Despite her urgings, my tongue and jaw were beginning to ache a little when at last she politely invited me to "get your fucking dick in there." We set up a slow burn as she kissed and licked her juices from my face and as previously, we seemed to change positions on a whim, totally attuned to one another. The difference this time was that it was slow and relaxed as our hands and mouths explored every inch of skin we could reach.

Laid-back modern jazz played in the background, a cool breeze blew in from the patio doors and we passed drinks between our mouths as we made love. It was utterly idyllic and while my time with Aspen was spectacular and unforgettable, I knew that somehow this moment would mean more to me as time passed.

Taylor came as I took her from behind, lying across that wonderful leather sofa, her fingers gently strumming her clit as I teased her nipples. She went rigid in my embrace, mouth wide open, screaming silently into the New England night before informing me that my next ejaculation would not be wasted like the first.

Before Aspen, it had been fifteen years since I had seen a woman smile up at me, her face covered in my cum. Now it had happened twice in a few days and the sight of long strands of it dripping down from her chin onto her breasts will live with me until they put me under.

She purred, playing and toying with it, then smiled sweetly. "Steve, my phone is on the nightstand. My hands are rather cummy. Please immortalise this moment for me, then send it to Mallory and Aspen. They are the first two ladies on my contact list."

I obliged, then was dispatched to the bathroom to bring back a damp towel for her. "Just a quick wipe down, then another beer for you and a Chenin pour moi. Oh, and don't think you are done, Mister O'Hara. The night is yet young."

By the time we were done, there wasn't much left of the night and there wasn't much left of me.

Smuggler's Cove was proving to be an exhilarating but exhausting place.

Five

Our early-morning lovemaking was the perfect start to a perfect spring morning. Afterwards, Taylor stirred in my arms, glanced at the clock and let out a low groan. "Oh shoot, I gotta head into the office for a while. Got no other plans after that. Howzabout you meet me for coffee on the harbor at eleven-thirty, then we do a nice coastal walk to work up an appetite?"

I stroked her left breast. "Already got me an appetite. Why don't we just stay here all day?"

Taylor wriggled from my grasp. "You may have a one-tracked mind, Mr. O'Hara, but as well as sex, I also require fine food from time to time. I thought we may lunch together."

"Sounds good. Food in the Dockyard is just great."

"So it is, but I have unhappy memories of that place. I called in last evening and some no-good chancer took advantage of me. Wouldn't leave me alone. Know the type?"

I laughed. "Yeah, we low lives just lay in wait for the Desperate Housewives to float by and hope we get lucky."

Taylor dug me in the ribs as she got up. "Buy me a seafood platter at the Salty Dog and you may just get lucky again. Now get yourself next door and shower off the filth that Desperate Housewife left on you while I go get rid of the mess that no-good chancer left on me. See you at eleven-thirty. Don't be late or I may have to resort to the Dockyard again."

I was on time and it was wonderful to be sitting on the dock, shooting the breeze with a lovely lady over coffee. It felt like my first date in twenty years. The walk afterwards was now over familiar territory for me, but all the better for Taylor's company and she pointed out the local landmarks and gave me a little of the history of the place.

Our late lunch was wonderful, sharing the amazing seafood platter at the Salty Dog over a couple of bottles of Chenin Blanc. My old life seemed a million miles away. When I glanced at Taylor checking her phone for the fifth or sixth time, she pulled a face.

"Sorry, just a big deal going down at the moment. Need to keep checking things are all hunky dory."

We walked back to the condos along the river in the early evening sunshine. I had come to the Cove to find some kind of peace but instead had stumbled into a very pleasant den of iniquity. Aspen had been one thing and the darkly beautiful Mallory was another, but something about Taylor Whiteley resonated with me. I already knew that when the time came to return to Boston, it was going to be difficult.

We walked in silence, as though allowing each other to process our thoughts. As we cleared the town, Taylor slid her hand into mine. The smile that passed between us said that this was a lot more than a vacation fuck. She pulled me into a secluded grove of trees that bordered the river. It was all we could do not to just go for it there and then. Somehow, we held ourselves in check and continued on our walk after a brief rearrangement of clothing.

Back at the condo, she checked her messages one last time and we were good to go. Five minutes later, a beautiful lady straddled my face, holding herself open as I licked at her delectable wet folds.

As with the previous night, I was really getting into my work as she ground down on me, my eyes closed, hands kneading her buttocks. Then a hand encircled my erection and I opened my eyes, expecting to see her leaning back, hands outstretched behind her. It took a moment to process the fact that both her hands were on my shoulders. Either Taylor Whiteley had suddenly grown a third hand or something else was at play. Then soft lips encircled my glans and I moaned into Taylor's slippery wet pussy.

Now she did lean back and settled down onto my chest, grinning down at me. "All that shit about a big deal going down? Only thing going down on you now is my good friend Ms Mallory Felder! Just needed to check she was home and raring to go. The former was the issue -- the latter is a given. So, Mr Steven O'Hara, I proudly present..."

As she peeled off me, Mallory's eyes burned into mine, her mouth working wonders on me. She sucked hard on the tip of my cock and let saliva drip down the shaft. Then with a loud 'plop', she broke our intimate connection and rubbed my erection across her cheek, leaving a wet trail. She regarded me as if she had just walked into the Dockyard for our aborted meeting.

"Evening Steve. Apologies for being late. Some shit got in the way. Pleased to say that shit ain't in the way anymore. Let me make it up to you."

The way Mallory made it up to me would probably have cost one of her clients a small fortune. Add in the charms of Taylor Whiteley and had I been paying, I would have needed a second mortgage.

At first, Taylor sat back to enjoy the show. "Oh, I do love watching VW go at a handsome guy! She feels good going down on me, Steve -- can't imagine what that sweet mouth feels like on you."

I didn't have to imagine. It felt incredible. It felt even better when Taylor joined her after five minutes of bliss that had me racking dollar signs up in my head. I suppose I had dreamed of having two women together occasionally, but never believed it would happen. Now it was happening, I had to pinch myself at the sight of the lovely blonde and the sultry dark-haired woman working on me together with practised ease. I just lay back and took it all in, not wanting to miss a second of the action and determined to make it last as long as possible. This may be my only chance at a threesome and I wasn't going to let it pass me by.

For all my good intentions, I almost lost it when the two women worked their way up my shaft, tongues flickering before they met in a long, wet kiss with the head of my erection between their lips. It was one of the moments of my life to see two pairs of eyes burning into mine as they broke away and Mallory knelt on the bed. Taylor guided me into her now slippery, wet snatch and lay back so Mal could go down on her.

It was only the start of a long, torrid and wonderful night when things I didn't even know were on my bucket list were ticked off. At first, I was surprised that Taylor was the main orchestrator but given that she was tasked with producing and directing a lot of the Cottage Industry's output, it made sense. When she and I went down on Mal together, the inimitable Ms Felder let go with a stream of gutter filth that any Vegas Whore would have been proud of. Licking her wet folds and sharing kisses with Taylor was another unforgettable moment in a night full of them. By the time I entered Taylor again, our faces were wet and sticky and Mal had her work cut out doing a little clean-up job.

Taylor came, moaning fit to bust as I hammered into her, Mal licking and sucking at her clit, ramming my fingers into her wetness. Taylor's face was buried deep in a pillow, blonde hair all over the place, her racking sobs muffled by the bedding, hands gripping the bed rail until her knuckles whitened.

Grinning from ear to ear, she took a moment to regain her breath, then set us up for the big finish. I was again taking Mal from behind, gripping her hips as I thrust towards the now inevitable climax. Taylor was positioned below, licking at Mal's clit and my erection. It was too much for me after the last amazing twenty minutes or so and I let go inside Mal as she now gripped the sheets, twisting them in her hands as she came with me. It took me a moment to realise that for the last few nights I had been watching this woman on the internet. Now I had just come inside her as she squeezed down on me, urging me to fuck her harder.

It got even better when I slid out of her and watched in sheer ecstasy as my cum began to dribble out of her sopping pussy into Taylor's open mouth. Then she squeezed down with a grunt and it began to pour out over Taylor's face. She fingered herself as she sucked at her friend until her mouth was full, then flipped her over and cheeks bulging, moved in for the big finale.

Mallory's hand flapped about on the dresser and picked up her phone. She handed it to me. "Just a few souvenirs for our private collection please!"

It seemed to be a reoccurring theme with the ladies of Smugglers Cove. I had never been into selfies, but was rapidly coming around to the idea.

I held the phone up and Mal's mouth was open in readiness as Taylor slowly began to let it dribble out between parted lips. I managed to immortalise the moment the long strand dropped onto her chin and hung down towards her breasts. Then I took a shot of the cum kiss and the stuff oozing out between parted lips and dripping down onto the bed. I took a lot of images and they would all have graced any porn shoot I had ever seen.

Their clean-up went on for a long time and they clearly loved sharing. Long before they had finished, I was hard again and had the pleasure of taking Taylor from behind as they licked the last vestiges of my first load from each other. It was a long time before I came in Mallory's mouth as Taylor stroked me, a long finger deep in my anus. I was then treated to a show beyond compare as the two women made out next to me on the bed until they were both sated and breathless.

Much later, we sat out on Taylor's bedroom balcony in the moonlight, Mallory and I necking beer from the bottle, Taylor sipping Chenin Blanc from a glass. She had called us vulgar and uncouth until Mallory reminded her of some of the things she had done in the previous two hours. There were only two loungers out there. I was on one and Taylor lay across her friend with her head on her breasts.

I was just thinking how lucky I was when it was almost as if Mallory read my mind. "Steve, I'd say that since you arrived in town, certain ladies of the Cove have looked after you royally."

"They have indeed. I seem to have crash-landed in the middle of a porn movie."

"Just what you needed, I guess."

"I didn't think I did, but it certainly has had its benefits."

She raised an eyebrow before pointing at me. "No such thing as a free lunch, Steve."

Oh shit, what was coming next? I had no idea, so decided to deadpan it. "Mallory, from what I hear, there is no way I could afford your rates."

Taylor chipped in. "She's expensive but there are rumors that she does fuck in her spare time -- albeit occasionally." She grimaced as Mallory squeezed a nipple hard. "Hey, quit that Felder. Now please, before I throw you out, tell the nice man over there what we have planned for him. Just a way of showing his appreciation for all we have done to help him over his traumatic d.i.v.o.r.c.e."

Mallory stroked Taylor's left breast tenderly. "Is that better, Whiter-than? Ok Steve, you already know that me and my gals are in the adult entertainment industry. We make movies of us getting it on together and with nice guys who we trust. Reason I was down in Coldwater Bay till this morning was to take delivery of some recording equipment to begin the set-up of our new studio. The shit that got in my way was the late delivery of said equipment. Meant that the stuff we were meant to do to test-drive it got put on hold. Bottom line is, we are now behind on our content and our clientele are discerning people with fine taste. They get a little cranky if they are denied their regular dose of our debauchery. Can you see where I am going with this?"

I took a deep breath. "I am beginning to build a picture - I think."

Mallory looked at Taylor. "I'd say he passed his audition. You?"

Taylor nodded sagely. "With flying colors, VW. And flying other things of course."

Oh shit, I was right. "Erm, look ladies -- I'm really grateful for what has happened here, but I think that might be a bridge too far. I love the thought of it -- who wouldn't -- but I can't risk being recognised if anyone who knows me sees it."

Taylor sipped her wine. "You've seen Mal and her friends in action. When it's Scott or one of the other Pro guys with them, they are credited and recognisable. We also have a circle of gentlemen who appear completely incognito and get their kicks knowing they have been immortalised on the internet doing naughty things to naughty ladies. Think of what I told you last night. I'm in a few of them and no-one will ever be the wiser but us. Don't worry, Steve -- your face will never appear and your own mother or ex-wife won't recognise you when we've finished with you. We're experts, ain't we Mal?"

"Sure are, Taylor. Just need you to make sure Steve's pubic area as smooth and shiny as his handsome head and cover that telltale birthmark on his hip with theatrical make-up. After that, no-one will ever know that the gentleman squirming under my expert care and attention is Mr Steven O'Hara of Boston, Mass."

The proposition sounded extremely exciting, but also more than a little scary. But of course, it wasn't just Aspen no-one could say no to. "Ok ladies, I'll throw myself on your tender mercies. But not sure I can be of much use after the last few hours."

Taylor extricated herself from Mallory's embrace. "Don't worry, your big moment is scheduled for tomorrow afternoon. We need to relocate next door to Mal's place. She has a small studio set up there. It will take me a while with the razor tomorrow morning, but fret not, I got a steady hand."

I supposed I had some sort of payback coming and I was already 'out there' in a very small way on Aspen's highlight reel. "Ok, I'm yours to do with as you please. Just go gentle on me. So do I get an inkling of the scenario you have planned?"

Mallory shrugged. "Oh, just a long, slow-burn BJ with a messy ending. May involve leather or latex. Who knows what I'll feel like by then?"