Through The Shades

After years as a reader, finally dabbling in contributing. Sharing some stories from my past, present, and some plain old fantasies.

My wife Tessa (Tess) and I had a pretty innocuous introduction, one of those 'we met through friends of friends at work' things.

A dozen or so years ago, I was in my late thirties, a few years after a divorce, chugging through a typical life. I worked at one of the larger global consulting firms in a branch near the twin cities where I was born and raised. I worked in the Human Capital division and was doing well professionally, I was on a solid if not spectacular path and was steadily moving up.

The personal side was a bit of a struggle, the dating world had changed quite a bit since I'd last had to worry about it, as it was just about all done via online dating sites. I dabbled in it here and there, but never really could get the hang of it.

Writing and re-writing profiles to try and sound somehow interesting and yet not cocky, pouring over which pictures to post, and having to endlessly scan my inbox for replies and swipes just wasn't my thing. I did a bit of the bar scene with a few of my old friends, but outside of a few random hookups and one-night stands nothing much ever really came of that.

I had known 'of' Tess prior to meeting her, but only via being copied on random e-mails when projects we were working on would intersect. She worked for the same firm, but in a different division that was located about 25 miles from ours. I finally met her during a three-day all-hands meeting at our main office in Minneapolis. Stephanie was another coworker that I had been friends with since joining the company after my divorce, and she had been on a rather constant quest to cure me of my single status. She had talked to me several times about Tess, telling me she was attractive and single, sure that Tess and I would hit it off.

We finally met on the second day during a breakout session that Stephanie had made sure we had both signed up for. I wish I could say that sparks flew and the heavens sang, but it was a professional introduction and interaction. Tess was indeed very attractive, about 5'6, wavy brown hair just past her shoulders, and bright blue eyes. She had an athletic build, as she was a passionate runner and was seemingly constantly training for a marathon. She had smallish firm breasts, that I spent a lot of time trying to get a look at through her loosely buttoned blouse, very full lips (that I would later learn looked amazing wrapped around my cock), and an out of this world ass.

I don't know if it was genetics, or years of running, but her ass was stunning. Full, round, firm, the slacks she was wearing were doing all that they could to contain them. I was concerned (and a little bit hopeful) that they were going to split wide open. To this day it remains amazing. I've seen it thousands of times in my life at this point, and I will still stop what I'm doing to sneak a peek at her trying to stuff it past the waistband of a pair of jeans or into a pair of yoga pants, or crane my neck for a peek at a bit of cheek showing from under a small pair of shorts.

After our initial introduction, I did go out of my way to chat with Tess more often. She was part of the larger friend group of similarly aged professionals that Stephanie had constantly been nagging me to join for happy hours and whatnot. So, I started to occasionally show up, usually finding time to chat with her. She was sharp, witty, and incredibly intelligent. She also always cut an amazing figure in whatever she was wearing. The occasional chats became more frequent, which led to IM's and texts throughout the day, and the conversation gradually shifted to a much more personal nature than professional.

We started to hang out after work and on weekends, however it was always very platonic. Although I would have taken it farther, at that point Tess was very ensconced in the online dating world. Ten years younger than me, she was looking for "the one" to settle down and start a family with. A dude 10 years older, divorced, with a couple of kids in tow was not exactly the profile she was looking for.

And so, we remained friends for quite a while, going to Twins games, hanging at bars, taking a couple weekend trips to visit friends, but always platonically. I listened to her rage about a nearly constant litany of bad dates and short-lived relationships, and life went on. At some point, there were a couple of drunken hookups that we both laughed off after the fact, but we were in fact growing closer. Finally, one night after passing a bottle of whiskey around my backyard firepit for a few hours, we took the plunge, with her cautioning me that this was only going to be a "friends with benefits" situation for both of us.

I couldn't have cared less at that point, I finally had her underneath me in my bed, slipping inside her after all that time was incredible and we drunkenly fucked the first night away. After the damn broke, I was insatiable. I'd always had an incredibly strong sex drive, and it had been dormant for years, we spent that entire first weekend in a sweaty tangle.

I finally got to see that gorgeous ass bent over in front of me, my hands firmly gripping each hip as I thrust into her over and over, watching her ass bounce off my pelvis, feeling the round curve of it against me drove me over the edge time and time again. I'd been with my share of women in my day, but I had never been behind an ass that was anywhere near this league. She also had amazing stamina, never shying away from my almost constant need to be inside of her tight pussy or watching her gorgeous lips slide up and down my cock.

Weekends turned into months, and Tess and I took full advantage of our "arrangement". Shy at first, she slowly opened up to me about some fantasies. I introduced her to Pornhub, where she learned quite a bit about a lot of different things that she didn't know that turned her on.

One evening, we were lying in my bed, my head was on her shoulder, and I was half-awake as she lazily scrolled through various types of videos on my iPad. I was drowsily running a finger up and around the outside of her panties, slowly outlining her pussy. I suddenly noticed that she had stopped scrolling, and the volume of the iPad was suddenly alive with a woman's moans. I felt her breath quicken, and the panties I was slowly tracking around became noticeably more wet. I rolled my eyes toward the screen to see what she was looking at...

Onscreen, a pretty brunette sat astride a man on a couch, reverse cowgirl, facing the screen. She was arched backwards against him, rising and falling on his cock, occasionally grinding into him, rolling her hips back and forth slowly. On either side of her, two almost identical blonde women knelt, each attending to one breast. They were licking, sucking, tweaking and massaging her hard nipples. Kneeling between her legs, a third blonde was busy at work, running her tongue up from the exposed shaft of the man inside her to the top of her pussy, ending each long lick with a gentle suck on her clit.

I slowly slipped two fingers around the waistband of Tess's soaked panties and slid them into her, they glided in easily. Watching the onscreen action, I slowly matched the thrusting of the man on screen, sliding in and out of her, occasionally holding my fingers buried and curling them up against her front wall. The woman on screen was now gasping and writhing, as both blondes on the couch had latched on hard to one of her nipples and the third was sucking directly on her clit as the man increased his pace pounding up into her. Tess was matching her escalation breath for breath. The woman on screen came hard, every muscle tensing and rippling up her abdomen as she wailed with pleasure. Tess went off at the exact same moment, the iPad fell to the side, her head flew back, mouth open wide as her back arched up off the bed, her legs clutched closed hard as her orgasm took her, I felt like my fingers might break. Her orgasm went on and on, spasm after spasm, until with a weak moan she collapsed back onto the mattress, her legs finally opening enough for me to get my hands out.

"Well, looks like we found something that really hit close to home" I said, a little awed at how hard I had just seen her cum.

We discussed often and openly the things we wanted to do, and it seemed nothing was off the table. Sex in public, exhibitionism, sex in cars, light bondage, even multiple partners, threesomes and more-somes. She was becoming more and more adventurous and knew just how to tease me. Often when on a road trip if I was driving she'd slowly circle my cock through my pants until I was rock hard and leaking, take my throbbing dick out as if she was going to suck it, slowly run her finger up the underside until a bead of pre-cum was on her fingertip, and the slowly suck that fingertip into her mouth while looking me in the eye. She'd then smirk and zip me back up to suffer until we reached our destination.

I was a bit hesitant as we discussed arrangements involving sex with others, as I wasn't quite sure how'd she'd feel about how turned on I would get to see her getting fucked by someone else, man or woman (or both). She assured me nothing was off the table if we were both comfortable with it. We started to put together a list of our top 50 fantasies that we were bound and determined to make happen for each other. I couldn't believe it, but it seemed I had finally met my sexual soulmate.

High on the list for both of us (especially after her video discovery) was the idea of adding some more people to the bedroom. We both wanted to come as close as possible to recreating that scene where she was the center of attention and receiving multiple pleasure points at the same time.

We decided to start small. I had a birthday coming up and she came up with the idea of getting some videos of her with another person, as she knew that was probably 1 or 1A on my list of things that blew my mind.

We created an account for her on Adult Friend Finder, and she put up a pretty generic posting explaining that she was looking for a partner of either sex to join her in making some amateur videos to surprise her pervert boyfriend, with the intent of it potentially leading to a threesome. We laid out our hard and fast rules of engagement; couldn't be in a relationship and cheating on someone else, had to be in reasonably good shape, had to be sane (toughest one), had to be ok with being on video, had to understand that this was for fun and nothing more, and had to agree to meet beforehand for a feeling out drink. It wasn't going to happen overnight.

Her inbox was soon flooded with replies as expected, and she set about sorting through all the junk, random dick-pics with no content, and other people who obviously didn't read the posting. We weeded them down to a few individuals, a couple of gals and a guy, and she struck up some back and forth to get to know them.

One gal flaked out and stopped responding, so we were left with two. She shyly asked me what my preference would be. I would have been thrilled with either, but I also knew that while she found lesbian porn a turn-on, she'd never had an even remotely bi-sexual experience. I wasn't sure how into it she would be when the chips were down. I also was a bit worried that if it did progress to a three-way, that she may have some insecurities about what I should and shouldn't do with another woman. Lastly, I also really wanted to see her lips and ass in action with a guy, so we decided on Chad.

A happy hour meet was arranged, so they could chat, get to know each other, and make sure they were each comfortable. Tess dolled herself up, sheer white blouse under which you could still make out her nipples through her bra, and tight black pants. I gave her a quick kiss, "good luck, remember this is for both of us. If you aren't feeling it, ask for the check and thank him for his time, don't force it."

"Don't worry, I know this is technically your present, but this has to work for both of us," she replied.

She texted an hour or so later to say things were going great, Chad was attractive, polite and charming. He made her comfortable and that was most important. She arrived back home a few hours later and let me know they were planning to get together for another drink on Friday, and if things still clicked, would be going back to her apartment for a nightcap.

I couldn't wait for Friday to arrive. Each day dragged like an eternity, while I silently held my breath each night that she might change her mind. She didn't, and our evening sessions became hotter every night as it drew closer. She'd tease me relentlessly, whispering in my ear while we fucked, asking me if I thought Chad could fuck this well, always causing me to cum before I was ready.

Friday finally arrived. Tess wore a tight long-sleeved top that hugged her figure tightly, no bra, and a short black pencil type skirt. She seemed both nervous and excited, "Well here goes nothing," she said, pecking me on the lips and heading out the door.

"No, you are definitely something," I muttered to myself, watching her tight ass sashay down the drive to her car, black high heels forcing her calves into stark muscular relief with each step.

Time passed like molasses. I went for a run. I showered. I walked in circles around my house. I jerked off twice to ease my stress and leaking cock. My phone pinged with a message. "Drinks good, heading back to my place, chat soon."

Argh, my cock was instantly hard again, despite the fact that I had just taken care of it moments before. My mind was racing. I couldn't sit still. I tried to watch some TV but was 41 minutes into an episode of Sons of Anarchy before I realized I couldn't recall a single minute of what had happened.

Finally, at 10:30 or so, my phone pinged several times, a message "He's leaving soon, be on my way home, let's watch these when I get there" and then several video files downloaded back-to-back.

There was absolutely zero chance I was going to be able to wait even a second, much less the 15 minutes it was going to take her to get to my place from hers. I sat back on my bed and pressed play on the first video.

Chad must have been holding the phone, about chest level or so, as I saw the bottom half of his body laying perpendicular across her bed, with his knees hanging over the edge. Tess was between his legs, standing up, yet fully clothed. She was slowly sucking his cock, her head bobbing slowly up and down along it. The only sound I could hear was her breathing heavily through her nose as she attended to the task at hand, and Chad's appreciative moans. She was sucking slowly, almost tentatively, and occasionally glancing at the camera as if for affirmation. After about 30 seconds of this the video stopped.

My breathing heavy and cock straining I queued up the next video and pressed play. They were in the exact same position, however Tess's top was now off, her breasts swaying back and forth as she continued working his cock in and out of her mouth. She was much more into the moment at this point, eyes closed, fist pumping up and down his shaft in concert with her mouth. Wet, sucking sounds now accompanied her heavy breathing and his moans. An occasional moan from her around his cock as well. Occasionally she took it totally out and licked up and down the shaft, collecting her own dripping saliva back into her mouth. The camera shuddered a bit and I saw one of his hand reach down and start to knead and pinch one of Tess's nipples. Her moans around his cock intensified. Then that video stopped as well.

I quickly pressed play on the third and final video, this one thankfully looked to be close to two minutes long. Tess was now on her knees, wearing only a black thong and her high heels. Chad was standing above her, and she was sucking him aggressively. Beads of moisture, a mix of pre-cum and saliva, steadily formed and dripped from the bottom of his shaft onto the floor. She alternated between closing her eyes and staring directly through the camera into his eyes. Chad's moans were now almost constant as she rapidly pistoned her mouth up and down the full length of his hard dick. He suddenly gasped "Oh god, I'm going to cum," and I saw his hand replace hers on his dick. Tess rose from her knees, pressing her breasts together to give him a target as rope after rope of cum erupted from his dick and splattered them. I heard a few final mangled gasps and saw her smile up at him, and the video ended.

I sat in stunned silence. I had never in my life been so turned on by anything. I watched them all again, one by one. Then again, I slipped my hand under my waistband to adjust my dick and the minute I touched it I exploded, soaking my underwear right through to my jeans.

I was still in that state, watching the videos a fourth (or fifth) time when heard a small giggle and looked up to see Tess in the doorway. "Guess you didn't wait for me?" she asked with a nod to my ruined pants. "I assume that's your stamp of approval?"

I wordlessly grabbed her and laid her down under me, fumbling my way out of my wrecked pants, I slid my half hard dick into her, it wasn't half hard for long. I started to pump into her, at least confident that I'd be able to give her a decent fuck since I'd already cum three times since she left.

Tess put her arms around and drew me close. "His cock was really nice, I want to fuck him tomorrow if it's ok with you," she whispered. So much for my theory of giving her a good romp, her words in my ear as usual triggered me immediately. Being my fourth orgasm of the evening, and literally 15 minutes after my last one, I'm not even sure what was left but the pained throbs were unmistakable. She laughed, "I take it that is a yes?"

Chad and Tess did get together again the next night, sending me both video and audio files of their romp. One long video, in which he'd finally figured to lean the phone on the nightstand, had him standing next to the bed, Tess kneeling in front of him working his cock. Her hands were locked tight behind his thighs and his were knotted in her hair, as he fucked his cock in and out of her mouth. Again, the sight of the steady drips from the base of his cock drove me wild. I came immediately at that point.

A minute or two later, she disengaged from his cock and looked up at him while slowly stroking it, "Do you want to fuck a little?" she asked. He must have nodded as I saw her stand up and watched her red-thong ass walk over to her dresser where I knew from experience she kept her condoms. The video ended.

Next was an audio only file, they must have hit record and just tossed the phone on the bed next to them. I heard her ask what position he wanted, he mumbled something so wasn't sure, as all I could hear for a minute was the phone sliding back and forth on the sheets as they both got onto the bed. I then could clearly hear the sounds of them kissing each other, a low groan and intake of breath from Tess told me he had just pushed into her. I heard more kissing, and the slow sounds of their bodies meeting together. It quickly rose in tempo, and they must have broken their kiss as I clearly heard them both moaning. The slapping sound quickly reached a crescendo and I heard him groaning repeatedly. Although a tiny pang of disappointment hit me that he hadn't lasted longer, I couldn't blame him. After all I knew intimately what that woman could do with her mouth and what her pussy felt like. I'd also cum again listening and was a complete mess, so who was I to throw stones?

Tess had discussed with Chad the possibility of the three of us getting together next, and he was all for it. I couldn't wait, and neither could Tess. The idea of one of us going down on her while the other sucked and rubbed her tits was high on her bucket list. It wasn't quite three mouths, but it was a start, and she couldn't wait. Chad had to leave for a few weeks for a work trip so we planned it for the week before Christmas. However, it was not to be.

The next week, Tess missed her period. It wasn't anything to worry about she assured me. She was often irregular. However, after a few days she took a test just to be sure. And there wasn't any more doubt. Although it hadn't exactly been in our immediate plans to start a family together, we were both excited. We began planning for a more dedicated future together, and I got to enjoy her changing body more than ever as her hormonal fluctuations often had her ravenously horny. Our son was born happy and healthy. We moved to a larger home and started to settle into our new life, less than 5 months later she was late again.

Fast forward a bit and we were managing 3 kids under the age of 4, in addition to two stepchildren. Our lives were happy yet constantly busy, and as you can imagine sex had become an afterthought. As with countless other marriages, the passion and time for each other became increasingly infrequent, and when it did happen it was more out of routine than anything else.

I was still horny as a teenager and ready to go at the drop of a hat, but her sex drive had taken a severe hit. Back-to-back-to-back pregnancies, both of us at new companies and bigger jobs, managing a family of 7, it had all taken its toll. She always took on more than her share and gave everything she usually to meet everyone else's needs, she was incredibly selfless. By the time we got around to trying to think about sex, one of us usually fell asleep.

We did finally manage to make things official and get married. Tess always had loved Halloween, it was her favorite holiday. I put together an undoubtedly corny proposal involving our kids' costumes, and she said yes. We were married the following fall, and for the short weekend that we took to ourselves immediately after, it was almost like old times.

We spent 48 hours doing nothing but eat, drink, and fuck. The bed, the shower, the floor, over the hotel desk, it was incredible. Tess was as hot as ever; motherhood had done nothing but accentuate her figure. Her ass was somehow bigger and still perfect. Her nipples had always been incredibly sensitive and were even more so if that was possible. Laser hair removal had done away with any semblance of hair on her beautiful pussy except for a tiny tuft right at the top of her delicate lips. I'd always told her she had a 'porn star pussy'. It was perfectly shaped. Delicate, symmetrical, perfect lips meeting in a prominent V, that my trained eye could make out in swimsuits, underwear, and certain athleisure. It was also delicious. Going down on her was my favorite pastime, and she still came like an avalanche every time. I almost felt bad about the noise for our hotel neighbors. But when I mentioned that we were being loud and other people might be listening, it seemed to turn her on even more and fuel the fire. I began to think maybe we'd finally start getting back to our old form.

However real life quickly took back over, and we found ourselves right back in the same routine. I had hope though. Work and family commitments had kept us from honeymooning right after our wedding, so we were planning a trip for February of the following year. No better time to get the hell out of Minnesota.

We wanted to go somewhere warm, where we had nothing to do but relax, and we didn't want to travel for 2 straight days to get there. We decided on an adults only all-inclusive resort in Barbados. We needed the time away, deserved it, and spared no expense and treated ourselves. The resort was 5 stars, and Tess was thrilled to learn that it had butler service, a literal fleet of people to wait on us hand and foot.

We arrived at the resort and were met in the lobby by a concierge who took us to our villa, pointing out local landmarks and how to best find our way around the extensive resort grounds. Our accommodations were amazing. A garden walkway led to a keycard door, where we entered a private villa with a spacious outdoor seating area, our own private waterfall pool, and an outdoor dining area.

A sliding glass door led into a large bedroom with a seating area and enormous bathroom. Both the south wall with the sliding door and east wall of the room were floor to ceiling windows with beautiful bamboo shades that could be pulled up to enjoy the warm sun or lowered for privacy in the evenings. There were villas on either side of us that were separated by large privacy fences overgrown with vines.

After dropping us off, we were told to come back to the lobby once we were comfortable for a short walkthrough of resort services. We took quick showers to wash off the travel, changed into some cooler outfits and headed down. The concierge again met us and explained more of the features of the resort. Which restaurants were which, their hours and menus, showed us the pool, hot tub, and poolside bar. He described some of the activities for the week. We signed up for a morning catamaran sail, but other than that we just wanted to relax.

I already envisioned an entire week in one of the lounge chairs soaking up sun, sipping cocktails, and watching Tess's ass in one of the small bathing suits I'd convinced her to bring along. At the end of the walkthrough, we were also introduced to the butler service team, the head butler was named Derrick, and he met us with a warm smile and welcome.

Derrick explained that there were always at least 8 butlers on shift at all hours of the day or night, and they were responsible quite simply for anything and everything we asked. They would bring meals, drinks, sundries, help arrange reservations, help with luggage, arrange beach and pool cabanas, tours and transportation, room requests, dropping off random gifts and treats, you name it. They were all native to Barbados, and all seemed to be chiseled from the same block of Onyx. All of them were impeccably dressed in black linen pants, stylish sandals, and lightweight white shirts.

Their age was hard to place, but they all seemed to be on the younger side, and were all fit, well-spoken, and handsome. The resort quite obviously had a certain image they wanted to project with their staff and had hired accordingly. I caught Tess out of the corner of my eye checking several of them out, and it seemed Derrick was speaking more to her than me as well.

We thanked Derrick for the introduction, headed back to our villa, changed into our swimsuits and headed back to the pool, books in hand. Tess snagged us a couple loungers, and I headed over to the bar for a few strong Pina Coladas. The bartender was a tall middle-aged man who introduced himself as Leon. We chatted a bit and he explained he was born and raised on the island and had been working at the resort for many years. Tess joined me and introduced herself, and we had a few drinks and chatted a bit longer. Regardless of our urging, Leon (and all the butler staff) insisted on calling us formally "Mr. Steven" and "Ms. Tessa".

We spent the balance of the afternoon at the pool, lounging, sipping drinks, cooling off when we got too hot, reading and dozing off. Leon made strong drinks, and we spent time shooting the shit with him every hour or so when we returned for refreshers. The butlers seemed to be everywhere and also seemed to be mind readers. Showing up silently to take an almost empty cocktail and offer a glass of cool infused water, or a dry towel after the ones we had been using became sodden. They always introduced themselves, referred to us as Mr. Steven and Ms. Tessa, and refused all attempts at tips with a smile and a quick "no, no, we are always at your service".

"Mr. Steven, you and Ms. Tessa have a nice evening," Leon called out as he left the bar at the end of his shift. "Don't hesitate to call them boys for anything you need, don't let that pretty lady lift a finger!"

We smiled and waved and soon returned to our room. It was late afternoon, and we were both relaxed and had a nice buzz. I had been staring at my wife's ass in that small swimsuit long enough. I pushed her back onto the bed and was inside her instantly. She was soaking wet and ready, as I stroked in and out of her she reacted with a vigor I hadn't seen since our wedding weekend. Something had definitely gotten to her. Throwing caution to the wind I whispered in her ear "You know I saw you checking out those butlers every time they walked by you, you see something you liked?"

She looked at me and grinned "and? Those guys are hot as hell, I don't recall you ever having a problem with me having a wandering eye?"

Hearing her confirm that she had been checking them out and was so willing to flaunt it excited the hell out of me and I came deep inside her with a groan.

Rolling out from under me she gave a small laugh, "It seems like me checking them out didn't bother you too much anyway!" Tess rolled over and was soon dozing contentedly, after a long day of travel, sun, drinks, and sex. I left her to rest, grabbed my book and headed through the screen door to the hammock to read. I cracked a beer from the stocked fridge by the pool and sat down to relax.

I barely turned a page when a soft cry caught my attention. At first I thought it might have been some bird that I wasn't familiar with, but as it continued I realized I was listening to the cries and moans of a woman getting a good fuck. It was coming from the villa next to ours. I couldn't resist quietly making my way over to the privacy fence and looking for a spot I might be able to see through.

The fence and the vinery were really doing their job though and it was a struggle. I eventually found a small hole in the fence where I could just see a portion of the neighboring villas waterfall pool. A svelte busty blonde was bent over the whirlpool and was obviously getting fucked hard from behind. She was doing her best to not be too vocal but whoever was fucking her knew what they were doing and every third thrust or so a small moan or cry would slip out.

Now that I knew what I was listening to I could also pick out the discernable slapping sounds of their bodies meeting. I couldn't see who was doing the fucking, but I could see a pile of clothes in front of the blonde, a pile of black and white cloth. Could she be fucking one of the butlers? I could swear I had seen her down by the pool with a partner, where was he? My cock was straining at my swimsuit, and I quickly freed it and started to softly stroke it while I watched her body rock back and forth, large tits with dark nipples swinging beneath her. Her cries started to be more constant and rise in volume and frequency, and as she threw her head back it seemed like she was looking directly at me. I didn't think she could see me, but I still slowly backed away.

There was no way I was not going to take care of my condition however, my dick was hard as a rock. I slipped back into the sliding door and slid behind my sleeping wife; she woke up suddenly with a moan when I plunged into her still wet pussy and started frantically pumping into her. She pushed her ass back against me reflexively and reached behind my neck to pull me closer "what the hell got into you?" she whispered.

"Kept thinking about the way you were looking at those butlers" I whispered back, "these things were always on our list back in the day, you haven't had any strange dick since Chad. You think you'd really consider it if one was interested?"

Mentioning Chad triggered a loud moan, all the confirmation I needed and I again exploded deep inside her, thinking of her being the one bent over the whirlpool with a large black cock being hammered into her by one of the staff. We both drifted back to sleep, where my dreams were filled with my images of my wife's ass in her tiny black bikini.

We awoke later in the evening and after a quick rinse, put on some fresh clothes and wandered down to one of the onsite eateries, with all that happened that day we had neglected to make a reservation but once again the butlers saved the day. A tall dark gentleman in the standard ensemble glided up to us as we entered the main lobby, almost as if reading our minds "Good evening, my name is Ryan, can I help you with any dining questions this evening?"

"Thank you, Ryan, that would be great. We seemed to let the day get away from us today and forget to get something booked." I replied.

"At your service" he said, with a small bow and a wink in my wife's direction.

In no time we were seated at a small oceanfront steakhouse at a table for two, enjoying the open air and a good bottle of cabernet. Our conversation since waking had been rather banal; the fantastic weather, wondering how the kids were doing back home, how good the wine and our shrimp appetizer were. However, my thoughts were consumed with both what I'd seen earlier and my wife's seeming indication that she would be open to some extracurricular fun. It had been my experience though that with these things it was best to let her take the lead, as being too insistent about it would usually shut her down.

She was the one to finally initiate the topic, "It's been quite the eventful day, hasn't it?"

"It had indeed" I said, (if she only knew the half of it! I still had the blondes heavy swinging breasts in my head), I haven't seen you this turned on since our wedding weekend."

She reached across the table and took my hand, "what we were talking about earlier, about maybe checking a thing or two off our old list? I am interested, but only if the right opportunity presents itself and we are both ok with it. If it happens, it happens, I just don't want to feel like I'd be disappointing you if it doesn't."

"Honey, if the totality of this week is this weather, watching you in that bathing suit, meals like this, and sex with you, it will be the greatest week of my life. Anything else will be icing on the cake" I assured her.

That put her at ease. We continued to chit chat, had a great dessert, and were just wrapping up when yet another butler appeared at our table. I was beginning to think these guys were half ninja the way they suddenly showed up. "Good evening, Mr. Steven, Ms. Tessa, my name is Harry, if you will allow me I will have your turndown service completed prior to your return, and as a reminder, do not forget to complete your breakfast order and hang it on the door outside. We will collect them this evening and deliver your morning meal at the time of your choosing."

"Thank you, Harry," my wife said, "that sounds fantastic."

"At your service Ms. Tessa" he said and glided away. I wondered for the 100th time how these guys always seemed to know the name of every guest they were addressing.

We returned to our room, filled out a breakfast order of various fruits, yogurts, and juices for a 7:30 am delivery. We were taking an early morning catamaran trip, so there would be no sleeping in at least for one day. We hung the placard on the door, stripped out of our clothes and fell into bed. I was in the process of reaching for Tess for one last round when exhaustion apparently claimed us both.

We awoke the next day to a doorbell from the entrance to the villa, and a voice over the wall asking if we were ready for breakfast. I opened my eyes and looked at the clock, 7:30 on the dot. After hastily dressing and stepping out, Derrick appeared in the doorway pushing a breakfast cart. He greeted us warmly, "Good morning Mr. Steven, I hope you are enjoying your stay with us so far?"

"We are Derrick thank you, when you order for 7:30 I see it means 7:30 on the dot" I said.

"We pride ourselves on that Mr. Steven, not a minute early, not a minute late," Derrick replied.

While he was speaking to both of us, his eyes were looking past me at my wife, who had stepped out of the villa in the light linen robe that was provided. It was fairly apparent she had nothing underneath it, her nipples were tenting the fabric in the front. My eyes widened slightly, and I felt my cock jump. She had locked eyes with Derrick and responded, "we are very much enjoying it Derrick, your butler team is fantastic, and I'm looking forward to their future services".

Had she slightly emphasized the last word, or was that just my imagination? After a quick awkward silence, Derrick busied himself arranging our meal at the table and chairs outside the bedroom windows. "Is there anything else I can do for you folks before I take my leave?" he asked, eyes once again locked on Tess.

"This is great Derrick, thank you" she said. "We have to eat quickly and be on our way for the catamaran ride, but we should be back around lunch and might need your services then." She had for sure emphasized it that time, it wasn't my mind paying tricks on me. Derrick heard it as well, and nodded slightly, his eyes never leaving Tess's chest, where her nipples appeared to have become even harder and more prominent against the fabric of the robe. "At your service Ms. Tessa" he said with that slight bow they all gave, I did detect a slight catch in his breath, then he and the cart were gone.

"Good lord Tess, you almost gave that poor man a heart attack, and you didn't do me any favors either!" I said, indicating my cock straining against the bathing suit I had thrown on to answer the door. "Hurry up and eat, that boat is going to be the second thing I ride today".

We ate quickly, and fucked even faster, watching Tess flirt so brazenly with Derrick had me on a hair trigger, and as I bent her over the bed and started to fill her tight pussy she tossed me a look over her shoulder "Steve if you hadn't been here it would be that man's cock inside me right now."

Well, that did it. I lost any control I thought I had and came immediately, my hands holding her hips in a death grip as my cock spasmed over and over. Breathing heavily, I rolled over and she giggled and went to clean up and get dressed. Returning to my side a few minutes later she quipped "you better be drinking a lot of water hon, the amount of cum you are losing here is going to dehydrate you."

I slapped her ass. "At least I'll die doing what I love". We dressed and headed to the docks to catch our boat.

The boat ride was delightful. I know my way around a boat; I don't think you are allowed to live in Minnesota if you don't know how to run a Lund or catch Walleye. However, I knew jack shit about sail powered vessels. Watching the deckhands work back and forth, tying and untying lines, raising and lowering sails, maneuvering to take advantage of wind I barely felt was cool. There were light refreshments and cocktails, and we were back at the dock before lunch. Tess and I decided on a quick power nap, and another afternoon at the pool.

We ended up in our familiar loungers by the pool, sipping drinks, reading, and relaxing, attended by the ever-present fleet of butlers. Tess seemed almost anxious and agitated, shifting her legs around, squeezing them together and letting them part. She was wearing a black suit and we were in and out of the water so I could not tell if it was wetter than it should be. Had the discussion about the possibilities with these men started to really get to her? Derrick strolled over, and with his eyes never leaving Tess's ass asked if we had enjoyed our breakfast and if we would be dining in our villa again in the morning. Tess rolled over, her hard nipples standing out under her suit, and assured him we would, without breaking his gaze. Derrick swallowed a lump in his throat, bowed 'at your serviced' us, and was on his way.

We spent a bit of time in the hot tub and met a lovely woman named Heather who was visiting the resort for the 5th year in a row. She was older, single, and said she made a point to get here out of the cold every year after she discovered it. "There are other great resorts in Barbados, but you cannot beat the eye-candy here can you Tess?" she said with a smile and a nod at butler who was walking by.

"No, they are definitely easy on the eyes" Tess agreed with a laugh.

We found the whirlpool a bit too hot, so we retreated to our loungers, Tess laid down and I headed over to the bar for a few drinks and a chat with Leon. I had a feeling he might be a reliable source of information if I could get him talking.

"Hey there Mr. Steven" Leon said, leaning back against his bar. Leon dressed similarly to the butlers, but not as formal. A wide brimmed hat cocked casually to the side on his head. I had not noticed previously but Leon was in great shape for his age, he sure put me to shame and I had worked hard to stave off the dreaded dad-bod. If he were 10-15 years younger, I imagine he'd be walking around in a butler outfit himself. "You and Ms. Tessa still enjoying yourself?"

"Sure are Mr. Leon" I said, giving it right back to him. "Hey listen, I had a bit of an awkward question, and if it's too weird, I'll just take 2 pina coladas with a float to go."

"Anything Mr. Steven" he said, starting to pull bottles off the shelf behind him.

"Have any of the butlers ever provided uh, additional 'services' to the ladies in the resort outside of their regularly scheduled duties?" I asked, putting that extra emphasis on the word like Tess had.

Leon stared at me for a long moment. "I think I get where you are coming from Mr. Steven, Ms. Tessa looks like quite a package, perhaps more than one man can handle at times?" he questioned with a raised eyebrow.

"Exactly" I said, "she is really a lot to keep up with, she seems to enjoy her conversations with Derrick, and I was wondering what might come of that. They had quite the chat at breakfast this morning, however he was a gentleman throughout."

"Well, that's not surprising Mr. Steven, first of all, I know Derrick as a consummate professional, as the head butler he gets plenty of attention around here from ladies that have had a few drinks in the heat. However, he's not likely to risk his job on something that may end up just being a quick flight of fancy, especially if you were standing right there."

I thought back to this morning, he had sure seemed locked into Tess, but still hesitant. I did remember him occasionally cutting his eyes at me as if unsure of the situation. I also recalled the scene I had stumbled upon in the villa next door. The blonde bent over the whirlpool, crying out as she was solidly fucked. No husband in sight. I started to come up with a plan, the windows of the room were tinted and you couldn't really see into the room unless you pressed your face into it. If I left some of the shades up and sat on the far side of the bed....

I was jolted out of my reverie by Leon's voice "So if you think this is something Ms. Tessa is really interested in, I'd make sure you weren't around, and she's going to have to make it pretty damn obvious what her intentions are. Like I said, they are all going to be cautious regarding starting any unwanted drama. Being unemployed and blackballed from these resorts as a butler is not a good place to be in, and Derrick is a really good kid." He placed the two drinks in front of me, finished them off with a splash of rum, and looked at me, seeming to be searching for confirmation.

"I am sure she's interested Leon, but I will absolutely make sure of it before she would attempt anything. I do not want any drama and would feel terrible if something happened to impact Derrick negatively. If it works out the way I think it will, he is going to have a positive experience"

He nodded and I took my leave with our drinks. Tess was sound asleep when I got back to the loungers, so I ended up having my drink and half of hers before joining her in dreamland.

We slept longer than expected near the pool, and when we awoke we made our way back for a quick shower and down for a casual dinner at one of the buffet style restaurants. The conversation again started fairly generic, while my mind was racing with possibilities. I wanted her to be the one to bring it up. Thinking back to the conversation with Leon, this had to be something she wanted as much if not more than me.

About halfway through, she suddenly grabbed my arm, "Steve, breakfast, that conversation with Derrick, at the time I was having fun and being flirty, but it's been on my mind all day, I really want to do this, that man is stunning. We are far from home, I don't have to worry about anything if it happens," she said, "I mean, assuming you are ok with it. It's been a long time since Chad, and a lot has changed in our lives since then."

"I'm more than ok with it, you know that. I've been all about this since we started dating and it's never been far from my mind. Now that we are here and it has seemed possible to do again, I've thought of almost nothing else. I've come up with an idea..."

I shared with her my plan, her being alone at breakfast tomorrow, wearing even less than she had this morning, me hidden behind the bed with a few of the shades open so I could see out yet could not be seen, etc. "You can tell him I've gone for a walk down to the point on the beach and won't be back for a few hours. I do think you are going to have to come on strong and let him know what you want without doubt, I think he'll be a bit hesitant if it's just you trying to flirt your way into him making a move on you."

Tess agreed, "I think I can do that, you thinking totally naked sprawled out for breakfast? I feel that is a bit too much, bikini bottoms?"

"I was more thinking topless with those rose-colored panties" I said. They are a little bigger than your swimsuit, but they are completely sheer and hug your pussy perfectly. I'm actually getting hard now thinking about it." I laughed a bit but I was indeed growing uncomfortable in the pants.

"Ok," she said, "that sounds good. I'll have to come up with something to say but that outfit should speak for me I think."

We finished dinner, swung through the lobby and grabbed a couple packages of condoms, some regular, some magnums (just in case). As much as I loved the idea of seeing her fuck bareback, I knew that would be a non-starter for her, and in the end for sure the safest bet. I really hoped I would see one or more of them get used. We filled out our breakfast order sheet, hung it on the villa door, and headed into the room.

We had barely gotten out of our clothing when Tess grabbed me, tossed me on the bed, and straddled my face, "lick me please, I need it badly." I gladly obliged, I never turned down an opportunity to spend time going down on Tess. I licked long and slow, up her center, pausing to press the flat of my tongue gently at the top, just like I knew she liked it. I ran my hands up her body to rub her hard nipples between my thumb and forefinger, pinching and tugging them. I could tell she was not going to last long. Soon she had both hands firmly grasping my hair as she ground herself against my tongue, she was moaning loudly, and it turned into a steady babble of the kind of talk I loved to hear.

"Oh god... Steve... I am going to fuck him so hard, I want to fuck him so bad, I want to cum for him while you watch me, I want this so bad, it's been too long," her last word vanished into a long deep moan that came from the center of her being as she convulsed on my face. I locked my hands around her hips, licking and sucking for all I was worth. I knew from experience it was going to be hard to hold on, she became extremely sensitive after she came that hard, and no matter how I wanted to keep going it was always too much for her.

True to form, she wrenched herself off me and threw herself to the side, breathing heavily, her hands held up in front of her to ward me off, her legs tightly closed to any more oral attention. I was used to this, I knew I could either wait 20 minutes for her to calm down to keep licking her, or I could slide into her, as she could usually handle that right away. I uncrossed her legs and positioned myself to thrust into her, "no!" she mumbled, and she dove down and swallowed my raging cock in her mouth, sucking down to the base in one motion and aggressively bobbing up and down while she rubbed my balls.

"No?" I questioned, looking down at her. She peeked up at me, taking my cock out of her mouth she gave me an impish grin, "I want to keep this 'porno pussy" perfect for Derrick tomorrow morning," she said, "we can't have you sullying it." She returned her attention to my cock. I liked a rough blowjob, she expertly alternated running it roughly between her cheek and teeth to the point where it was almost painful, then swapping into her soft throat. In no time I began to throb into her mouth. A quick rinse (she rarely swallowed) and bedtime routine, and she was curled up next to me again.

Tess slept soundly beside me, I was sleepless. Rolling back and forth, constantly hard, agonizing for the dawn to arrive. I finally drifted off at some point into a heavy slumber.

I awoke to the sound of the shower turning off with a squeak, my eyes shot open, my eyes searching for the clock, 8:30. We had ordered our breakfast to arrive at 10:30, more of a brunch. Rubbing the sleep out of my eyes, I immediately worried if perhaps Tess had changed her mind with the reality of the moment so near. Those doubts were put to rest as she stepped out of the shower, gave me a kiss on the lips and did a quick twirl. I could see that the small soft tuft of hair that remained just over the lips of her pussy was gone, completely silky smooth. That was usually a sure tell that something sexual was on the horizon.

She spent the next hour or so getting ready, she left her hair in damp ringlets, applied some light fresh makeup, and spent some time painting her toes and fingernails a bright, festive red. Wandering to the drawer, she picked out the underwear I had described the night before and slipped into them. True to my memory, they clung to her ass and hips, and absolutely hugged her gorgeous pussy in the front, low slung and ending in a dainty point between her thighs. She looked at me and struck a pose, "Well? Think this will do the trick?"

"If it doesn't, we'll need to have his head(s) examined" I said back.

It was 10:20, close to showtime. We stepped out of the villa around to the windowed side where the breakfast chair and nook were against the window. There was a small stack of beach towels neatly rolled up nearby, and we slid the packages of condoms underneath them within easy reach. She sat down in the chair facing the villa door and took a deep breath. She leaned back, thought more of it, then softly slung one leg up on the arm of the chair, leaving her spread wantonly wide...

"Is this too much?" she asked, "I know you said I should make it obvious, but don't want to look ridiculous."

"No, that is perfect, I think there are just a couple more finishing touches," leaning over I kissed her lightly, one hand slowly twisting and pulling her already hard nipples into even more pronounced points, while my other hand softly massaged her pussy through the outside of the panties. In no time at all there was a very noticeable wet spot in the front. "Now that, is perfect" I said, breaking our kiss with a smile.

We were interrupted by the abrupt chime of the villa doorbell! "Shit" I thought, looking at my watch, 10:22! What the hell happened to not a minute early or late Derrick? I stood up as silently as I could, made a shushing motion to Tess, and started towards the door to the room. I had barely taken a few steps when Tess called out, either out of nervousness or need "come in!"

Holy hell! I thought, I leapt through the sliding door at the front of the room, blindly reaching behind me to pull the screen closed as quietly as possible, it hit the doorframe with a soft thud. Fuck! I had grabbed the wrong handle and closed the glass door entirely! Further complicating matters was that the bamboo blinds were all still down from last night. Thankfully I was lazy and it was already dark when I had dropped them so they weren't all the way to the floor. Basically, what I had to work with was roughly 2 feet of window give or take a few inches on each blind. Son. Of. A. Bitch.

I crouched near the bed, I certainly did not have to worry about being spotted, but I also wasn't going to be able to see or hear very much. Hopefully, those windows were on the thin side and would let some sound through. I could see the floor of the villa outside, the legs of the chair my wife was sprawled in, and one foot, freshly painted toes pointed towards the villa door.

I heard the villa door open, and the cart start to rumble through, a deep voice started what sounded like a salutation and dropped off suddenly as the cart rolled to a stop. My wife replied. Something. I could not quite make it out with the damn door closed, but I heard the lilt in her voice as whatever she said rose in the form of a question or invitation? I saw my wife's second foot join the first on the floor, as she stood and took a few small steps forward. I heard her voice again, low and conspiratorial sounding, I assumed she was explaining my absence and what she had in mind.

More silence. A pair of black sandals with dark linen pants appeared, taking slow steps until they were directly facing my wife's. More muddled conversation drifted through the glass, a man's voice, and her response. The sandaled feet shuffled a bit as Derrick shifted his weight side to side, as if pondering. More silence. God what the hell was happening! Stupid blinds!

Suddenly I saw my wife rise slowly up to her tip toes, I could see the muscles flex in the bottom of her calves, and the two of them both subtly shifted their weight forward. They were kissing. Derrick was a good bit taller so she had needed to rise up. I imagined her arms encircling his neck as their tongues danced.

The sun chose that moment to slide from behind the hazy clouds, and cast their shadow on the blinds, confirming what I thought. One solid mass of shadow, two people obviously pressed together so tightly not a crack of light shown through, joined all the way to their separated legs. This continued for several minutes, Tess rising and falling from her toes, their feet shuffling ever so slightly as they explored each other.

The sun disappeared behind the clouds again. Tess's feet stepped back as they broke their embrace, and her feet turned around momentarily as she stepped back. A rolled beach towel was tossed to the concrete ground in front of the sandaled feet. My breath caught.

Slowly my wife's feet stepped back as her knees came into view, kneeling on the rolled towel before him. A moment later the black linen pants were pooled around Derrick's ankles, followed by a pair of black boxer-briefs. I heard a small exclamation but again couldn't discern what she said. Her hands briefly appeared holding the pants for him as he stepped out of them and kicked them backwards out of my view.

I heard a long, low, deep throated groan, it ended with something sounding like "Ms. Tessa". I could only see from her knees to about a quarter of the way up her thigh, but could see the slight flexing forward and back, swaying back and forth, her mouth around the cock she was undoubtedly sucking on.

I was beside myself. My cock was rock hard, straining against the underwear I'd worn to bed the night before, the front of which were already soaked. I freed myself of them, careful to avoid contact as I was sure the slightest touch would have me blowing my load everywhere.

Outside, the motions continued, slightly faster as she shifted back and forth. The agonizing silence punctuated by an occasional low groan. I also thought I could hear sloppy wet noises, like a cock working in and out of a mouth, but I was sure I was imagining that.

The sun emerged from the clouds again, the shadow showing in stark relief the image of my wife on her knees, her shadowy arms gripping somewhere about his waist or thigh, her head moving back and forth along what appeared to be an enormous cock. It looked unnaturally huge, but I realized that shadows distorted images.

Now that I could combine the vision with what I was hearing, the wet noises I had heard were definitely coordinated with his thrusts forward into Tess's mouth. Fuck I wanted to see her gorgeous lips sliding along that dick so bad, for the 10th time I cursed the shades, the timing, the fact that she had called him in before I had a minute to prepare. The sun chose that moment to further my frustration by again sliding behind the clouds. This was going great...

The cocksucking continued for a long time, low moans and the steady thirsty sound of him plunging his dick past her lips into her mouth. Pre-cum was puddled on the tile floor in front of me as my dick throbbed agonizingly. A moment later the motion stopped, and I heard my wife's voice again. Once again I couldn't make out what she said but it ended with a questioning sound. I heard a low reply from Derrick.

Tess's knees disappeared as she rose to her feet again and again took a step or two away from her lover. A moment later a second beach towel was rolled out onto the ground, and another atop that one. Seconds after that, my wife's panties pooled around her ankles as she delicately stepped out of them. They looked absolutely soaked.

Her feet again turned away, and again I saw her knees as she knelt on the towels, joined by her hands a moment later. She knelt on all fours, offering her beautiful ass to Derrick's gaze.

'For the love of god,' I thought, my view was restricted to again part of her thighs, calves, and arms from the elbow down. Her nipples briefly appeared below the shade as she adjusted herself, then disappeared from view. His knees appeared next, as he slowly knelt between her legs, slowly nudging her legs farther apart. An empty condom wrapper fell to the ground at his side (Magnum, not surprisingly) and his legs fidgeted as he rolled it on. Another nudge of his knees pushing her a bit more out to the side, and I saw him suddenly flex forward.

"Oooooohmmmyyyyyygodddddd", there was no mistaking the words my wife used as that massive cock entered her, "fuckfuckfuckfuckohmygod." Then sudden silence again for a moment and their legs were still. I imagined he was holding steady, letting her adjust a bit to his size. Then began slow, almost indetectable movement in his legs, as he eased his cock slowly in and out of her, each rock forward drew a long, loud, moan that was quickly rising in volume.

Almost simultaneously, another sudden burst of sunlight displayed exactly what was happening as the figure behind my wife drove into her again and again with long determined strokes. Tess's face suddenly dropped into view as she fell to her forearms, her eyes closed, her mouth frozen open as every muscle I could see stiffened. She bit into a ruffle of the towel to muffle her cries, which were still carrying clear as day to my ears. "Cumming, cumming, cumming, fuck I am cumming!"

Tess rarely came from intercourse, and when she did it was almost always as she was riding me or missionary, where she could concentrate on rubbing her clit against me to finish herself. I can't remember ever having made her cum while fucking her from behind, and with my obsession with her ass, I'd say 90% of the times we have fucked it's been from behind.

It was too much for me, my ragingly hard cock exploded spontaneously in front of me, jets of cum arcing into the air and splattering across the tile, again, and again. I gasped, biting my lip to keep from crying out and giving myself away.

My wife was still face down in the towels, her body shuddering with each gasping breath. A large dark hand rubbed downwards across her ribs to roughly tweak and pull at her swollen nipples. A moment later it disappeared, into shadow again. I heard his voice, assertive sounding as Tess rose to her hands again. The shadowy arm reached forward towards the outline of her hair, as his feet suddenly lurched from a kneeling position to a flat footed crouch above her. He must have still been fully buried in her, as his weight shifted forward with the move I heard a long drawn out moan as his cock pushed even deeper into her.

The sun thankfully broke through once again. His feet firmly planted, I saw his calves twitching as he started to forcefully pound into her, one hand on her shoulder for balance, and to hold her up high off the towel. The outline of him crouching over her displayed his cock sliding in and out of her at a much higher angle, almost vertical versus horizontal. I knew his dick was sawing in and out of the full length of her, rubbing past her g-spot with every demanding thrust deep inside.

The sun faded again and I was left with just my view of feet, thighs, and my imagination. My cock was stiff as a board; it had never even softened from my enormous orgasm moments before. I listened to the resounding slaps of his thighs against Tess's huge ass, I was going nuts. I knew exactly what he was looking at, her ass rippling with each thrust, her back arched, I didn't doubt his other hand was firmly gripping onto her opposite hip.

The pounding went on and on, Tess's cries again grew louder and louder, without the benefit of the towel they were ringing clearly in my ears. I briefly worried about our neighbors, but then thought "fuck it, let them think I'm that kind of awesome." Suddenly Tess's constant moans stopped, I knew her breath was completely caught in her throat pre-explosion. Her thighs clenched, the slapping sound reached a furious crescendo and I knew he was on the verge of fucking a second orgasm out of her. Moments later a long, low, "ooooooooooooughhhhhhhhh" howled through the villa as she violently climaxed again. One hand knotted in the towels, the other slapping the ground, her back was convulsing, arching up and down. She was undoubtedly only held up by his strong grip on her shoulders, her breasts swung in and out of my view with each bend of her back.

I was afraid I was going to reflexively cum again, my dick was so hard it physically hurt. A raw feeling, the pressure in my balls felt like I'd been kicked, a slow ache spreading through my pelvis. I can't imagine how it would have felt without my prior release.

Outside, Tess's elbows drooped, thighs unclenched, it seemed the only thing holding her up was the long cock impaling her. He slowly edged backward out of her and my wife collapsed face down on the towel. For the first time I was able to see my wife's entire supine body, entirely beaded with perspiration, she faced away from the window, chest and back heaving with heavy, ragged, breaths.

The large black hand dipped into view again, palm down outside of her shoulders on either side, a lean torso lowered itself towards my wife, and for the first time I laid eyes on the cock that had been driving into her. Suffice to say it was enormous. I'm not good with judging sizes, I know that I am decidedly average and have never had an issue with that. I know most guys are average, some guys are cursed, some guys are blessed. Derrick was blessed, maybe twice. My best estimate is that he was more than twice my length and girth. The magnum condom came to an end a good few inches from the base of his cock, and it seemed to be doing the lords work to not burst into pieces stretched around a head like a small plum. Almost hairless, with closely trimmed hair around his stomach and balls, flecked here and there with grey.

Leaning on his left arm, his right hand took his cock and began rubbing the massive tip up and down between Tess's ass cheeks, seeking the sopping entrance to her pussy. Finding it, he resumed his push up position and lowered his cock into her again. I watched it slowly disappear into her, inch by dark inch, marveling at how she was taking it all, my wife's stamina was obviously paying off for her here.

The sun was out again, but I no longer needed it, as I finally had a full view of the action. I could finally see perfectly as he plowed into her over and over, her ass shaking with the force of his thrusts as he almost bounced back each time from the impact with her substantial ass. My wife's head turned to face the window, she couldn't see me through the tint, but I could see her. Her mouth was half open, her eyes lidded and slightly rolled back as he pushed his massive cock into places inside her that had never been touched before. I glanced at the clock, 11:15?!?! Had they possibly been at it that long? No wonder she looked exhausted, she had been taking that dick for near an hour.

The pounding continued for several more minutes, my wife's breathing was quickening again. Derrick's groans were becoming more frequent and his pace was now almost frenetic. He was pounding into her so fast her ass was a constant ripple of moving flesh. Amazingly, she started pushing her ass back to meet his thrusts, fucking him as hard as he was fucking her as his growls turned into one long steady moan.

I suddenly heard his voice again, assertive as his knees flexed and he got to his feet. Tess's eyes snapped into focus and she quickly spun back to her knees in front of him, her ass resting on her calves. The spent condom dropped next to his feet, and Tess's ass rose out of view. Repeated low guttural grunts rang out as Derrick finally unloaded. I heard the sloppy wet noises again, louder this time, then my wife's sudden exclamation. Wads of cum mixed with saliva spattered on her thighs and the ground. It was pretty apparent she had tried to take his load but it had just proved too much. The groaning slowed, and eventually stopped, as Tess again sat back on her calves and Derrick's feet shuffled backwards a step or two.

Silence for a moment, then my wife's voice, his answer, and their mixed laughter. She slowly rose to her feet again, bringing the towels with her. They stood together again, her rising and falling from her tip-toes as I imagined they wound down and said their goodbyes. Derrick's feet disappeared from view, and moments later I heard the rolling wheels of the cart, and the opening and closing of the villa door.

I stood and waited, motionless, my dick throbbing painfully in front of me. The door slid open and Tess stepped in, turned and clicked on the soft overhead light. She had a crooked smile on her face and seemed in a bit of a daze. Her body was still covered in a sheen of sweat. A massive rope of cum was in her hair, and her chin and chest shone brightly where more had been hastily toweled off. Her knees, elbows and forearms were reddened from the time on the concrete, even through the towels. Her pussy was red and swollen, slightly more agape than usual, and the inside of her thighs were slick with wetness.

"Well," she said weakly, how was that for you?"

I grabbed her and tossed her back onto the bed, she turned as she fell across it. "Tell me everything" I said as I pushed my pained cock into her. Her pussy was like a velvet vice. I guess one might expect after the cock it had just hosted that it might feel more open, but to the contrary it was swollen tighter than I had felt it before.

"Steve, he fucked me so deep," she said, "he was so fucking huge.." She barely had the words out when my orgasm took me. I came from somewhere in my soul, it felt like every time I'd cum in the last ten years rolled into one. My cock throbbed and pulsed against her swollen walls, feeling like it was going to split in two. It had all been just too much for me. I felt lightheaded, and I collapsed on the bed, completely blacked out from the force of my orgasm.

I awoke sometime later, largely in the same position I had collapsed in. Tess was next to me, freshly showered, tapping away on her phone on some crossword puzzle type game. I immediately pulled her back under me, she scooted in with a soft laugh, "easy, I'm a little delicate down there." I took my time and slowly eased into her, parting her gently before seating myself inside of her fully. I slowly began to rock gently back and forth, looking down at her.

"Now," I said, somewhat convinced that I would last more than 3 pumps, "Tell me everything, tell me everything that happened and everything that you felt while Derrick fucked you." I lowered my head to her shoulder to better hear her replies. I heard her little tinkle of laughter. She pushed me back up by the shoulders to look me in the eyes. "Honey, that was the bartender. That was Leon fucking me."

My eyes widened in surprise. My mind said "That crafty motherfucker!" while my mouth said "Were you ok with that?"

"Did it seem like I was ok?" she said breathlessly, "I know you saw that cock, I have never been fucked that hard before. I have never felt so full, almost to the point of it being too much, but also being perfect at the same time. I was stuffed, stretched, and he was touching places inside me I've never felt before. I cum hard with you, you know I do, but the orgasms that man ripped out of me were like nothing I've ever felt. It was like he was taking a piece of me each time. I really wanted to swallow him at the end, I knew that would drive you crazy since that is something I rarely do for you, but it was just so much and so fast, I couldn't handle it."

Hearing her talk like that sent me over the edge again. I always loved listening to her talk during sex, it always made me lose control. I was certain she knew that and used it to her advantage at home. Even if we had just started having sex, a couple of quick loud moans or a whisper about another man and I would be finished immediately. It really wasn't fair. This was no exception. I arched, and came again, giving her whatever I had left in me. Completely spent, I curled up next to her and we both slept soundly for the rest of the afternoon and into the early morning.

Tess shook me gently awake, she was wearing a sports bra and her running shorts, hair in a ponytail. "Wake up sleepyhead" she giggled. I blearily rolled over, my eyes locked immediately onto her hard nipples pushing through her bra and my morning wood poking against the sheets as I reached for her. She backed away laughing "no, no, no, not this morning. I need a bit of a rest. I'm going to go stretch these muscles with a nice long run on the beach and listen to my podcast. I'll meet you back here later this afternoon."

I flopped back into bed and dozed off for another few hours. I woke up and took a quick shower and headed to the pool to have a word with Leon.

Leon saw me coming and had started working on a Pina Colada before I even got there. "Leon you sneaky S. O. B., I can't believe you came up with that plan so quickly."

Leon laughed, "I wish I could take credit for being that quick, but you aren't the first person to ask me about that scenario, it comes up quite often. Like I said though, the butler jobs are highly coveted and hard to get, and you age out of them quickly, speaking from experience. The resort has an extremely strict no fraternization policy for the butlers, I've seen them fired for even looking sideways at a man's wife before. Bartenders on the other hand, have no such worries." he smirked.

I was a bit dumbfounded, I recounted for Leon the scene I had come upon in the villa next to us, the blonde getting pounded by her whirlpool, with the butler outfit in front of it. "Was that you?" I asked.

Leon laughed, "No, it wasn't me, but I know who you are talking about and wish it had been. I don't know what you saw Mr. Steven, but it likely wasn't one of the boys either. Like I said, they are damn strict here, and besides, the half of the butlers here that aren't gay get all the action they can handle outside of the resort. They aren't hurting for female companionship."

"Huh," I muttered, maybe it had just been coincidence and the woman's husband had just been wearing something similar? Or maybe it had even been her clothes? I chuckled to myself thinking that my misunderstanding could have been the catalyst to the events of the past several days.

Leon continued, "It was easy enough to sneak over and see the time on your brunch card and then catch Derrick on his way. I asked him to fill in for me for a bit and let me take your meal. I'm pretty sure he knew what I was up to, he sure looked a bit jealous but didn't say anything."

"I'd been thinking of that plan for years but was never bold enough to try it. Watching Ms. Tessa's ass bounce around this resort these last few days made it a now or never situation. If it got me fired, it would have been worth it. And I must tell you now, it was worth it. That wife of yours is a lot to handle, I gave her all I could and I have the feeling she still was up for more if I needed it. Just when I thought I had her fucked into submission she took me over the edge working that ass back at me. She definitely has a different side to her. It was all I could do to last as long as I did on that ass."

"I know" I said, "looked like you were struggling there at the end, and that was quite the load you blew."

It was his turn to look surprised, "you were there? Not on the beach?"

"Nope, I was there the whole time" I confirmed, " I didn't' quite get the view I was hoping for, but it worked out ok."

Leon stared thoughtfully for a moment, "Well Mr. Steven, I'm off at 6 these next few nights, I'd be happy to stop by and give you whatever view you'd be interested in if Ms. Tessa would be up for some more?"

Leon did spend another few evenings with us, and we also got to meet our villa neighbors. Our last night on the resort, Tess and I kept for just ourselves, but Leon did stop by again the morning of our departure for one more special breakfast. Those are stories for another time.

Flying home, our first-class seats reclined, Tess snuggled into my shoulder in the darkened cabin under our blankets. "Good thing we didn't get patted down by TSA on the way out" she whispered, "he left me wet enough to drown a fish, poor agent would have been mortified." We laughed and she snuggled in again, dozing lightly.

My mind spun, I couldn't believe the dreams that had come true that week. I had to wonder though, were we back to our wild ways? Or was this likely another flash in the pan that would quickly fade once we got back and were consumed again by the day to day grind?

I suddenly felt her fingers lightly teasing around my cock outside my shorts, rubbing softly, barely touching. In no time I was hard and leaking. Just as I was thinking we were going to try and join the mile-high club, she slowly slipped her hand up the leg of my shorts. I felt her finger rub up the shaft of my cock from base to tip, collecting a thick bead of pre-cum. Lifting her head off my shoulder briefly, she looked into my eyes, sucked her finger clean, winked, and laid her head back down.

Things were looking good.