The shop I run here in this beach-side community is built on a marina at the very end of the island. The marina consists of a few small shops, a carry out, restaurant, and some apartments above the shops. Well, I have been eating lunch at the restaurant almost every day for the last 5 months so the entire staff knows me well by now, I don't need a menu, they know what I drink and etc. I always take a book with me so they are always asking what I am reading, and one waitress in particular is a prolific reader herself, so she and I struck up a quasi-friendship based on my regular appearances and the subject of books. This was very pleasing to me not only because I love books and talking about them, but also because she is a beauty! Average height about 5'4" 5'5" thin, approx. 105 110 pounds, dirty blonde, a face shape and lips that remind me of Cameron Diaz with that wide mouth and stunning smile, but her ass is EPIC. One of the best I have ever seen! Great curves, perfect shape, tight but not too small, just excellent. And since I am an ass-man, watching her walk away left my cock thick and hard on more than one occasion (okay almost every time!)

So after a few months of this "friendship", I'm in the restaurant after work for a drink, its the first time I have ever gone in for dinner much less a drink so the staff were surprised and happy to see me. I decided to sit in the bar to eat and needless to say I had a few free cocktails! Well, she is working the bar seating area that night and we chit chat (it was slow for some strange reason) over and hour or two as she works and I nibble and read. Finally she goes on break and swings into the chair across from me, leans forward and says, "So the word among the wait staff is you have a thing for my ass." YIKES! So I guess I wasn't as sly as I thought I was when I watched her walk away from my table all those weeks. So I’m caught, what can I do? (she IS married) but instead of shrugging it off, or playing dumb, I blush and say, "Yeah I do, its one of the best I have ever seen my entire life and I'm a man who likes asses so I’m always looking at women’s backsides." WHY did I say this, I have no idea - call me an idiot if you want, I felt like one as soon as it left my lips. But more surprising than my comment was her smiling reply saying she was flattered and thought it was a hot that men thought of her in that way. I pointed to her ring and said, "I bet your husband wouldn't be too happy." She replied that he was not a jealous man and was always noticing when she was being watched by other men and it made him feel lucky to be with her.

So she goes back to work, I go back to my drink and book. As I am leaving she drops my check with a note, "Dave (her husband) would like to invite you over for dinner tomorrow night" (I had previously told her I had no plans). Not thinking anything about it other than, I had found a new set of friends (and being new to the island that seemed like a nice thing) and on my way out I accepted.

Jump ahead to the next evening I swing by their house for dinner. Dave answers the door (he is a big man, like me slightly shorter around 6’2” but even more muscular and powerfully built, dark hair cut very short, goatee, deep blue eyes and a Hollywood smile) we meet exchange hellos and I am invited in to the delicious aroma of grilled scallops. Brooke (the waitress) bops into the room to say hi, brings me a beer and walks back to the kitchen and in typical pervert fashion I watch her walk away, her perfect ass swinging in a criminally short tattered, TIGHT, denim skirt. I must not have been too sly because Dave says, "So that's what Brooke means when she said you have a thing for her ass." HOLY SHIT! Despite what she said in the bar I expected a punch in the nose. Instead Dave goes on to say its okay he doesn't mind if I look, her ass is what attracted him to her in the first place. Dinner is great and after we move out to the deck for a view of sunset over the water and the two bottles of wine and few beers we had took their effect and our discussion drifted towards sexual topics. I sat across from them on the deck and Brooke was in Dave’s lap. I noticed he had a hand stroking the inside of her thigh and occasionally slipping up into the hem of her skirt. I pretended not to notice and watched the beautiful colors of the western sky. Meanwhile I am sitting there with a huge thick hard as steel cock thinking of where his hand was on her long thin smooth leg.

And that's when it happened, Brooke says to me, "Shawn, we have something we have been talking about for years and now that we know you would like to ask you about it." They went on to explain that they had not got into the swinger lifestyle yet but it is their number one fantasy. They wanted to know if I would be interested in helping them explore it! Well you can imagine my reply! I said sure I'd be very interested and like to play what ever role they had in mind. Dave said they wanted to start slow to see how they felt, because it could be weird at first. I agreed of course, I mean these are two beautiful, very sexy people, and the thought of swinging with a married couple has always been a fantasy I never thought would come true. Now I’m no slouch in the sexual department, I’m relatively attractive, tall 6’5”, muscular football player build, decent package, 8” when hard and thick enough to get compliments from nearly every partner I’ve had. I have had more than my share of sex, with multiple partners, older partners, younger partners, all races, even a few bisexual experiences, but never a married couple together! She then asked if I'd like to watch them make out. I nodded and they started. Their mouths opened and tongues flashed out in a hot open kiss, her arms went around his neck and that hand of his that had driven me so crazy already went up into her skirt. I could tell he had moved whatever kind of panties she had on aside and was flicking and rubbing her clit. She sighed into his mouth and I could see her hard little nipples poking thru her tank-top. You have no idea how bad I wanted to rub my hard thick cock thru my shorts but chose not to as I didn’t want to make them feel uncomfortable. This went on for about 15 or 20 minutes, their mouths locked in a hot wet kiss, his hand between her smooth thighs, fingertips spreading her pussy lips no doubt coating his hands in her wetness. Her hips grinding down on his crotch rubbing his hard cock under that perfectly shaped ass.

They finally stopped and asked what I thought. I told them it was very hot watching them, I was very turned on. They both said it wasn't too weird to make out in front of someone else, in fact they liked the idea I was turned on watching. We all agreed we should get together again soon, and I went home stroking my hard cock all the way. I don't need to tell you what I did as soon as I walked in the door!

So the next day at lunch I am sitting in Brooke's section of the restaurant, she was nice as usual and did not mention one word or even hint at the events from the previous night. Of course watching her work it was all I could think about. So as I sat there (with a rock hard, uncomfortably thick cock) I was puzzled at her silence, but assumed she felt too weird about it after she got to think it over and maybe the 'lifestyle' she and Dave were interested in wasn't for her, or not with me, or whatever. So as I pondered all of this, plus how I was ever going to get back into work without the entire marina noticing the tent in my shorts, she drops off my bill and in the credit card folder is an envelope with my name on it. So I pay, try to ask her a question but she was busy so I leave, race to my office in the back of the shop and tear open my envelope.

So the next day at lunch I am sitting in Brooke's section of the restaurant, she was nice as usual and did not mention one word or even hint at the events from the previous night. Of course watching her work it was all I could think about. So as I sat there (with a rock hard, uncomfortably thick cock) I was puzzled at her silence, but assumed she felt too weird about it after she got to think it over and maybe the 'lifestyle' she and Dave were interested in wasn't for her, or not with me, or whatever. So as I pondered all of this, plus how I was ever going to get back into work without the entire marina noticing the tent in my shorts, she drops off my bill and in the credit card folder is an envelope with my name on it. So I pay, try to ask her a question but she was busy so I leave, race to my office in the back of the shop and tear open my envelope.

Inside I find a note from Brooke and Dave, explaining that they had the hottest sex ever after I left and would be interested in having me over again the next night, if I was still interested. Also inside was an interesting cock ring (rubber figure 8 with a loop for the base of the cock and one for the balls) with a note attached, "put this on before you come over." I was so turned on I quickly reached over locked the door, pulled out my throbbing thick cock stretched the ring around it, closed my eyes, imagined my favorite fantasy (an ex-girlfriend getting gang banged) and jerked off HARD - mmm what a great orgasm, I came tons!

So needless to say, I was defiantly interested in going back over to their house. The next day D R A G G E D by. Me spending most of it in a semi-hard state! I could not wait to get over there, I had no idea what they had in store for me!

So, about 7pm I showered, made sure my cock and balls were shaved close and smooth, slipped the cock ring over my semi-hard but thick cock and cum heavy full balls. It felt good and tight but squeezed in such an erotic way that I instantly got hard. Pulling my shorts over (I didn't bother with boxers because I knew I'd never get them over my stiffening shaft comfortably) I zipped them carefully and threw on a shirt. Gently stroking my now rock hard throbbing prick all the way to their house, I kept thinking how hot our conversation the previous visit had been, as we all discussed sex over dinner and drinks. Hot erotic it was to watch them make out for me, knowing they fucked like wild animals after I left, knowing how hard I had jerked off and how much I had cum in a spine shaking orgasm when I got home. I could not wait to see what this night had in store for me.

I arrived knocked and was greeted by Dave. Wearing only a pair of board shorts and holding two beers he invited me in. Brooke met us on the sofa wearing yet another dangerously short skirt and a halter top, showing off her sexy smooth long legs and full breasts. I looked closely of course to see her hard little nipples showing and noticed her looking at my crotch. She smiled when she realized I was rock hard causing a considerable bulge in my shorts. As Dave told me how hot they thought the last time had been and that tonight they wanted to take a step further. I listed but was rapt by Brooke who was doing her best Sharon Stone impression across the room from me, spreading her legs slightly to let me get a glimpse up her skirt to a perfectly shaved, moist pair of bright pink cunt lips. She jumped into the conversation interrupting Dave as he searched for the words to tell me what it was they wanted tonight. Brooke said, "Shawn, we want you to watch us fuck each other. I want you to continue sitting in that chair, pull out that hard prick of yours and stroke it as we fuck for you.

I immediately reached for my zipper and as I was opening my fly I watched as Brooke bent over right in front of me. She pulled her skirt up over that perfect ass of hers and bent down putting her hands on her ankles. Looking thru her legs she smiled and said, 'Take a close look, we all have this to thank for tonight.' And she shook her ass slowly from side to side. She then reached up between her legs slid her hand along the soft smooth skin of her inner-thigh to her clearly wet pussy lips where she spread them with her fingers. The flood of pussy juice surprised me as it covered her fingers and ran down her thigh. But I loved it, so erotic, so forbidden, sitting here inches from the wife of a man standing just across the room, watching her pussy gush forth because she is so aroused by the situation. I finally got my rock-hard, throbbing, swollen cock out of my pants. The cock ring biting into the base of my shaft and squeezing my heavy full balls causing my cock head to swell to such a size I was surprised at it. My head had never been so big, so wide so sensitive. I tentatively stroked at it and let out a groan that I could not hold back.

'Oh yeah,' I heard her say to Dave, 'Look at that prick – god damn...' She stood up, turned to me pulling her halter top off over her head exposing her firm full (c-cup I’d guess) tits with hard nipples sticking out as big as pencil erasers. She pulled them out about an inch pinching them hard as Dave walked up behind her and unzipped her skirt and pulled it down over her shapely hips. She stood before me naked and my cock jumped in my hand. I wanted to grab her and fuck her hard and deep. It was all I could do to stay seated, so I concentrated on stroking my cock which responded to every touch with an amazing rush of ecstasy to my brain. Meanwhile Dave was pulling Brooke over to the sofa directly across from me and down into his lap. It was only then that I realized he too was naked and I got my first look at his hard cock...

Again my throbbing, rock hard dick jumped in my hand as I caught a glimpse of the thickest cock I have ever seen. Shorter than my own by an inch or so, his cock was twice the girth at the shaft of mine and despite my head being more swollen and plump than ever before, the head of his cock was so huge I audibly gasped. So much wider than his thick shaft, all swollen up and dark purple from the biting cock ring he too was wearing, his head was honestly the size of a small peach. Instead of being put off by the bulbous nature of the thing, I found myself so turned on imagining how wide he must stretch the tight lips of a pussy when he first enters a woman.
It did not take me long to find out just how he stretches a cunt, as Brooke turned to face him, her sweet ass towards me, climbing onto the sofa one foot on either side of his thighs. She slowly squatted down towards his raging impossibly thick cock, her feet flat on the sofa, and her arms around his neck, she threw her head back and sighed and whimpered when her soaking wet lips and clit rubbed into his fat cock tip. He grasped the base of his shaft with one hand and I could see that despite him being a big man his fingers and thumb did not even touch as he wrapped them around it. Holding his horse-thick cock steady with one hand he reached up and grabbed the top of her shoulder with the other. She cried out to me, “Tell him to fuck me Shawn, tell him you want to see him fuck me.” Glancing at his head I could see her wetness dripping down his shaft and coating his cock in a glistening glaze of desire and eroticism.
“Fuck her Dave, fuck your wife for me, I want to see her ride your incredibly thick cock.” With that he pushed down on her shoulder hard, shoving every inch of his monster up into his tiny wife. I swear I heard an audible ‘pop’ as his several inches wide head punched thru those wet lips. She screamed as if she was in pain, and it shook me back to reality for a second. Was this really happening? Was I really stroking my own, hard as steel cock in the living room of this couples home as I watched the thickest, most animal like cock I’d ever seen tear this sexy little thing in two? It was really happening, and right in front of me, and the pleasure of my hands stroking my own bulging, throbbing cock reminded me of it with each pump. I could see the pre cum already oozing out of my swollen and ultra sensitive head; down my shaft; over my fingers and I knew I didn’t have long before I would be cumming in thick torrents all over, but I had to keep watching, keep jerking, keep this erotic moment lasting.
“Oh god, oh god, oh god, oh god damn, oh god damn, oh god…” One of the things I have found interesting over the years among the people I have had sex with is the different things they say, or the sounds they make when they are fucking. ‘Oh god damn, oh god…” was what Brooke kept repeating over and over and over as her husbands T H I C K cock stretched her wide open. From where I was sitting I had the perfect angle between her legs as she rode him facing away from me. His cock looked so damn good, covered in her slick wetness as it slid in and out of her bright pink lips. She rode the entire length of his shaft stopping at the base of his head which I could see as it bulged wide her cunt wanting to pop out but being so damn wide it was stuck inside.
The urge to get up slip in behind her and shove my cock up her tight little asshole, double penetrating her, was so strong I had to push the thought from my mind. The last thing I wanted was to screw this arrangement up! So I concentrated on not cumming all over their living room, which was growing increasingly difficult as my cock was swelling by the second, bigger and bigger, harder and harder and so sensitive each stoke made me moan in pleasure. My pre-cum had by now coated my cock’s pulsating, swollen purple head, and was running down my fingers to my full, shaved smooth balls still in my shorts.
“I want to watch him, watching us.” I heard her whisper to Dave. She got off of him with a huge moan and whimper as he popped out of her, that comically huge head looking so fucking hot. She turned, bent at the waist and put her elbows on the ottoman directly in front of me. “Take off your clothes.” She instructed and as I struggled out of them she noticed my heavy huge balls swing free from my shorts. “Those are so big,” she said, “play with them for me as you jerk your hard prick.” I reached down felt the smooth, stickiness of my pre-cum covered balls and pulled on them as I jerked with my left hand. “Oh yeah, I like the looks of that,” she said.
Smiling as I locked my eyes with hers I said sternly, “Fuck her Dave. Take your sexy little wife from behind while I watch.” She reached a hand up under her and starting pulling and rubbing at her hard little pink clit as Dave positioned his monster between her waiting pussy lips. He reached around and grabbed her hanging titties by those sexy long hard nipples and pulled them hard. I could see her visibly brace as her face tightened in anticipation of his horse thick cock stretching her little slit open. I could not wait to see the look on her face when he plunged it in and at that moment her eyes bugged out, the air went out of her lungs in a long moan that turned into a gasp and Dave grunted like the animal he was as he buried his cock deep into her.
After only 4 or 5 pumps she was cumming, screaming as she never took her gaze from either my hands stroking my swollen cock and heavy balls or my eyes, as I kept them locked on hers and the expression of surprise and utter delight on her face. I couldn’t hold out any longer and within seconds of her screaming at her orgasm, I too lost control and came so hard my body shook. I let out a series of moans with each thick, hot creamy white spurt of cum that landed on my thighs, stomach, chest and even my chin! “Oh yeah,” Dave said as he saw my load splatter and he came next grunting deep guttural noises as he filled his wife’s pussy.
He pushed her forward, sliding his quickly sagging thick cock out of her and slumped back onto the sofa. She fell forward onto the ottoman still gasping still pinching and rubbing her clit, still cumming, still moaning and whimpering, as I continued to stroke my still rock hard dick (the ring biting so hard I couldn’t go slack after my hard orgasm). She finished, collapsed to the floor and we all looked back and forth at one another.
Panting, excited, spent and in dis-belief of the situation & how hard we came, we all began to laugh. Don’t ask me why but it was then I knew that this would be a long and adventurous relationship. I stood up grabbing a towel offered by Dave and wiped myself off; Brooke looked at Dave and then me saying. “Let’s keep taking these steps sexually, I’m loving this progression.” Both Dave and I nodded and we all laughed again.