First Time with a Stranger

My wife and I were staying at a resort in Cancun with a group of friends. We had been there for a few days and were having a great time. Our group was sitting in the lobby and had just finished watching a show with some local entertainment. Kathy had walked over to talk to the DJ, to ask the name of a song he had played. I was watching the crew break down the show when she walked up and put her hand on my shoulder. I stood up and the two of us started to walk across the lobby.

We were walking across the lobby when she turned to me and said, "Pretty sure I just got hit on." I was a little surprised, but this woman loves to flirt -- my first thought was that the DJ had said something to her. But she turned and looked back to where we had been sitting. There was a tall, thin younger man sitting on his own looking back at us. "Oh, yep. That's for sure what is happening," she told me as she turned back to me.

My imagination is instantly on fire. The picking up a stranger scenario has always thrilled me. Kathy and I have discussed it a few times, but she didn't seem to see it as something that would work out for her. But now, here we are in Mexico, 2000 miles from home. Maybe, just maybe...

We have played with others before, people we met online. But we always got to know them first -- chatting online, meeting them for drinks, and then discussing whether it was someone we actually wanted to explore further. This was someone she knew nothing about! I certainly wasn't going to push her about it, she knew it was a fantasy for me but he had to make that final decision. I smile at her and say "Whatever you want to do babe. If you want to go talk to him, go talk with him." She looked worried as she told me, "Yeah, but talking is going to lead to other things, and is that what we want?" I note that she didn't say "may" lead to other things, was that a slip on her part? I tell her, "Entirely up to you. I do not want to sway you in any direction. I'll support you in whatever you want."

She rewarded me with a big smile and "Okay. I want. I'm going to go see if he's still around." I let her know I would go meet our friends at the sports bar and tell them she was chatting with someone she met earlier in the day. I did tell her to text me what was happening. I got to the bar where our group was playing pool and told them she would be along in a bit. They accepted it without question, they knew she made friends easily and would show up eventually.

She would fill me in on the details later that night about the next parts. She walked back into the atrium and spotted him sitting alone at the lobby bar talking to the bartender. She stood off to the side without saying anything, waiting for him to realize she was there. She quietly checked him out; he was attractive, in his early 30s, well over 6 feet tall, with brown hair and a short beard. She can see a tattoo on his arm. He's wearing cargo shorts and a pink T-shirt. After a moment, he looks up and sees her and his eyes widen in surprise. "Why are you drinking alone?", she asked him. He jumped up and told her, "I don't want to be! Let me get you a chair." He grabbed a chair from a table and set it down next to his. Kathy sat down next to him and he asked what she was drinking. She tells him a tequila sunrise; no surprise here, as some have found before, tequila is a pathway to getting her naked.

They introduce themselves, his name is Brian and he's from North Carolina. She guesses he may be ex-military. Kathy tells him she is there with a group of friends and will be there another 3 days. He and his wife just arrived at the resort today for seven days. She fell asleep early and he was bored, he expected to be partying with her right now. He likes to stay busy. The mention of a wife is disheartening to her, we prefer to play with single guys and avoid drama and guilt. She tells him that she is there with her husband, knowing that he watched us leave together a little earlier. "Where is he? Is he watching me right now?", he asks, looking around. She tells him, "No, but he'd like to be."

He checks her out for the third or fourth time; head to toe, eyes lingering on her impressive cleavage. "I don't have anything to offer but this," he says, gesturing up and down his body, "it's big though, and you'll like it.". Another turn-on for Kathy, self-confidence makes her hot. She smiles and tells him, "Oh yeah? I like a confident man."

She tells me later that she is torn, she is sure that he would be a lot of fun. He didn't bat an eye when she mentioned me. But that wife is nagging at her. Kathy stands up and cups his face with her hands leans in and kisses him. Long and deep, tongues exploring each other. "Maybe you should go upstairs to your wife." she sighs and walks away. One look back and he's watching her leave, his face crestfallen.

Kathy walks into the bar where I'm hanging out with our friends. I can see that she is not happy and I break off from them. I meet her halfway and we find a quiet place to talk.

She fills me in on everything that has happened and I can tell that she is really regretting that it isn't going to work out. We had talked about things not counting when we are on vacation, we can break some of our rules as long as we are both OK with it. I say to her again, "No judgment babe. Do what you want to do. Why don't you go see if he's still around? Text me." She kisses me and I can taste him and tequila in her mouth. She looks at me, nods, and hurries out the door.

She walks across the lobby seeing if she can spot him. He is no longer at the lobby bar. She walks out the rear doors and stands on the patio overlooking the pools and the ocean. She can hear the waves and feel a steady breeze. The moon and stars are out and it feels like she can see forever. She looks to the right and there he is sitting on a lounger by the pool. He sees her and gets to his feet as she walks to him. He comes over, standing very close; "I was looking for you." She's looking up and him and he is at least 6'3'. He leans down and kisses her, she describes it to me later as intense and greedy. They both want more and there is no longer any doubt in her mind. They stand there in an embrace for several minutes, both of them running their hands up and down each other's bodies as they continue to kiss. It finally breaks and they walk back into the bar area, sit at a table, and she tells him to get them shots.

She and I text each other almost simultaneously.

Kathy -- He is pretty drunk.

Lee - If you find him, I think it would be better if I just watched. I'll be right there for touch if needed. Maybe should stick to just a blow job - unlikely he has condoms.

Kathy - Oh

Lee -- Up to you babe.

He sees her phone as he comes back with tequila. "Who are you texting?", he asks. "My husband. Telling him to meet us at the room.", she replies. He states strongly, "Watching only, no touching." She is disappointed, when we play, we like everyone participating equally. We both enjoy bi-play, but that isn't what this is about tonight. We have talked about this scenario, but neither of us thought it would really happen. She knows I will be OK with this.

Kathy -- Come to the room, Watching, no touching.

Lee -- You're not already there? Will I be able to touch you?

This was all new to us. I was hoping they weren't already in the room. And it was important to me that I could touch her occasionally to reassure her I was there and OK with what was going on. I excused myself from our friends and headed towards the room.

Kathy stands up and tells him to come on. "So where are we going?", he asks. She tells him, "To the gift shop, unless you have condoms on you." Again with the self-confidence, "Baby, I'm fixed we don't need any condoms!" I know she smiled to herself at that point. They head for the elevators.

Kathy -- In the lobby, headed up. You come to watch.

Lee -- Just oral, ok?

Kathy -- He's fixed.

Now I am confused and a little worried. We have played without condoms with one of our regular FWB, but only after our first few get-togethers. I panic a bit.

Lee -- Not sure I'm OK with this part. Will I be able to touch you?

Kathy -- OK, only oral then.

Damn, she must really want this!

Lee -- We can see. We just should have talked it out more.

It's obvious that she is ready to do him bareback, and I know that I'll be into it pretty quickly.

They reach the elevators and push the button. After what she says feels like an eternity, she gives up and pulls him up the stairs. He follows her and put his hand up her dress, caressing her ass as she climbs the stairs in front of him. They reach the top and he asks how old she is. "How old do I think I am?", she asks with a grin. He is quick with a reply, "25 or 28.". She tells him that she is 42. He wants to know how old I am. "What does that matter?" she asks and then repeats when he doesn't answer. "Is he 20 years older than you?", he asks. A damn good guess, she tells him I am. His next question is, "How big is he?". She stops in front of our door and asks again why that matters. He tells her, "I'm trying to figure out if I can take him if he tries to hit me!" She assures him that no one is hitting anyone and they aren't going through that door until he understands that.

I hear that last part of this conversation through the door. It worries me slightly, but I know Kathy is a good judge of character. I hear him ask if he can fist bump me when he goes in and she tells him that will be fine. He tells her, "I just want to make sure it's all ok.". Kathy opens the door and I am right there. I put my hand out and we shake hands and say hello. "So, no touching?", I ask, "Is it OK if I touch her while you two play?" He grins and says, "Of course man! She's your wife! I'm not going to get in the way of that!" I nod and Kathy pulls him over to the bed.

She wastes no time, pulling him in tight, pushing her chest against his, as her tongue gently brushes against his. Quickly, it turns into a deep, passionate kiss and I can tell that their tongues are in each other mouths and Brian's hands are moving quickly over her body. I watch as his hand roams under her dress over her thick ass. After about a minute, she pulls his shirt over his head and drops it on the floor. His physique is not skinny, but there isn't any fat on him. He has tattoos on both his chest and back. Her hand moves to the waistband of his shorts and unbuttons them. He is wearing boxer briefs under the shorts and in no time they are both on the floor. He is already hard and it is the biggest cock either of us has ever seen in person -- at least 8 inches. A thrill runs through my body as I watch her small hands circle that cock and jack it up and down. I am stunned at how small her hands appear as she grasps his long penis. I realize that I can see her wedding ring glinting up at me as Kathy strokes this stranger's cock. This just acts to increase the lust I am feeling for the scene in front of me.

Kathy pushes him down on the bed, pulling her dress over her head in the same motion, She climbs onto the bed and straddles him. Brian pulls her down and kisses her passionately while running his hands through her long black hair. I can see her moving slightly up and down on his cock. I step around behind them and look down at her luscious ass, while she is moving her pussy slowly on his huge dick. She raises up a bit and his hands are on her bra. He knows what he is doing and suddenly her large tits tumble out. Instantly his large hands are on her breasts and pulling them down to his mouth. He sucks on her nipples, alternating between the two. I hear her moan as she responds to the feel of his mouth. Brian's tongue flicks over her nipple and then I sense he is using his teeth on it as she gasps in pain and delight. He switches to her other tit and repeats the process.

I am standing at the foot of the bed, totally turned on, yet feeling like some kind of pervert watching this man enjoy my wife's body. At the same time, my cock is as hard as a rock. As if she senses my feelings, she looks over at me and checks to make sure I am OK with all that is happening. I give her a small nod and she shoots back a quick smile.

I can feel their need to take this to the next level. She moves down his body and I shiver as she licks the head of his cock. Kathy leans down to lick his balls and then slowly moves her mouth up his shaft, her tongue covering every inch of his cock. I can see the desire in her eyes, but I doubt that she can take all of this monster. She places both hands around his shaft, opens her mouth, and sucks the head of Brian's cock, eliciting a groan. Oh man, this is even hotter than I expected. I grab my phone and start snapping pictures so I can remember all the details later. Kathy opens her mouth wide, straining to take as much of him as she can. She keeps trying to take more of him, but a couple of inches were still visible outside her lips. She settles for bobbing her head up and down on his long cock. Several times he reaches up and tries pushing her head down further, but that is one of her pet peeves and she keeps pushing his hands away. The sounds of her slurping on Brian's dick fill the room. Finally, she let the big head pop out of her mouth looked up at him, and grins as she kisses it one more time.

Brian climbs off the bed, rolls her over on her back, and almost tears her panties off. He grins as he looks down on her naked body and I can see his cock twitch in anticipation. Then, just as quickly, he flips her over onto all fours. He is a strong man and moves her body around with ease. He kneels over her and I watch his cock slide between her ass cheeks and he begins kissing the back of her neck. He slowly works his way down to her ass, kissing all around it. His hands move to the sides of her tits as he buries his face into the crack of her ass. Kathy has only recently discovered the joys of analingus and a moan escapes as his tongue penetrates her asshole. He takes his time and has his face in her ass for several minutes. At one point I look down and she has her eyes closed and a small smile on her face. He moves back up to kiss her back and neck again, draping himself on her. I move behind them and his hardness is rubbing against her clit and she is moving against it in response. She is so turned on, I can barely understand the words coming from her mouth. But it's "Yes, yes, yes" and then "More, more!"

Next comes a move that is so quick I'm not sure how he does it. Suddenly he is lying on his back and Kathy is in a reverse cowgirl position on his face. He has literally thrown her up into this position to eat her pussy. Her knees are on either side of his head as his tongue works her clit. Her weight is completely on him and I have no doubt that his tongue is also finding its way well into her cunt. She reaches behind her and grabs the headboard of the bed for support. She is gasping with pleasure and I can literally hear the orgasm starting to build in her. Kathy opens her eyes and I follow them down his body to his huge cock twitching as it stands straight up, hard and waiting. She lets her body fall forward on top of him and takes the length of him back into her mouth. He eagerly adjusts and buries his face in her pussy and works his tongue in circles around her clit. She writhes on top of him and screams escape her mouth still wrapped around his dick. He grabs a boob in each hand and once again throws her up into a sitting position. His talented tongue resumes its assault, switching from sucking on her clit and poking deep into her pussy. His hands are on her tits and he is squeezing and twisting her nipples. She does not enjoy pain as part of sex except with her nipples. She loves being taken right to the edge of tolerance when they are bitten or twisted. She once again grabs the headboard for dear life as she makes louder and louder noises. Suddenly she opens her eyes to see me watching. Our gaze is locked on each other, I'm sure she can see the look of desire in mine as I can see it in hers. The first orgasm flows through her in a wave and she screams it out. As I watch, visible shock waves continue to ripple through her. I can hear her giggle, a sure sign of a fantastic orgasm.

She drops once again and takes him fully in her mouth and moves up and down, up and down, up and down. His hands run the length of her, fingers wrapping in her hair, running over her skin. Her mouth pops off of his cock and she swings around to straddle him. This is it, I'm going to get to watch her slowly take his big, bare cock inside her for the first time. I can't tear my eyes away as the head penetrates her pussy lips, It spreads her open and I can see her labia wrapped tightly around his cock. I have my doubts that Kathy can take the full length of his member. To my surprise, she drops all the way and sinks down on him. For a moment all I can see are his balls right up against her ass. She must have been extremely wet to take the full 8 inches in one motion. Kathy moves back and forth, Brian works his hips up and down and they find a rhythm. At first, she is doing most of the work, bouncing up and down on his cock. I step around from behind them and I can see that her eyes are closed and she is biting her lip in concentration, trying to focus on the cock deep in her pussy.

Then muscled arms grab her ass cheeks and he is moving her up and down quickly.

Her pussy is obviously well lubricated by her arousal. His cock comes almost all the way out when he lifts her and then disappears as he forces her down on it making her fleshy ass jiggle beautifully. He slams the length of that meaty dick deep into Kathy's cunt, hitting her in places I have never touched. She tells me later that the head of his dick is bumping into her cervix with every motion, causing her to cry out once again. She describes it as, "Right on the beautiful cusp of hurts so good. There is nothing but this." She picks up their pace and her moans are louder than the squeaking of the bed or the slapping of his balls. His hands are moving her up and down, then he suddenly slaps her hard on the ass and she cries out in surprise. Every time she rises above him, I can see her pussy being stretched and pulled out by this man's cock, before she plunges down on him again and again.

Kathy's mouth falls open as she gasps for air. She is moaning with each thrust as her body tenses, her hands grasping the sheets on either side of his body. At this point, I am not sure that she was aware that I was even in the room, all her concentration on slamming down on that huge cock. Her breathing gets heavier and I can tell she was closing in on cumming again, He was clearly hitting all her pleasure points. I had never seen Kathy go this hard for so long. There was something about the force that this stranger was showing with his dick working like a piston into her pussy. His hards alternating between twisting her nipples and grabbing her ass. It hit suddenly, her moans began to intensify, and then she cried out "Oh God!" as he continued to plunge in and out of her. She collapsed onto the bed next to him and they both lay there panting. I walked over and grasped her hand to let her know that I was there for her. I smiled down at her to reassure her all was OK, and she looked up at me with a small grin on her sweat-covered face.

Kathy and Brian lay there next to each other on the bed, trying to recover from the exertion. His cock was only semi-erect but still impressive. He hadn't cum yet but had helped Kathy get there multiple times. I was hoping it wasn't over, but knew that she had enjoyed it thoroughly. I had never seen another man's cum running out of her pussy, but it was a fantasy I had shared with Kathy before. As they catch their breath, she rolls over to take his cock in her mouth again. She looks up at me, leans forward, and starts licking his balls. She licks and mouths her way up his long shaft, teasing him with that incredible tongue. Brian's hands roam through her black hair, holding her head. She lets his dick glide along her tongue before closing her lips around it. Her head starts to bob up and down enthusiastically. I could see his cock hardening again as she administers her perfect oral skills. She pulls off of him and starts jacking it hard with her hands. This gives me a great view of his now erect cock as she stares, transfixed by his member. Brian's hands are on her breasts, twisting her nipples and making her moan. After about two minutes of this, he reaches up and pushes her head back down on his cock. Her head starts bobbing up and down on his cock again -- this was even better than I imagined it would be. Brian began to moan as Kathy expertly blew him. Her lips wrapped around his member, her tongue swirling over it as she sucked, her hand gripping the base, jerking him as her mouth worked its magic. Brian's hands works their way to her pussy and I could see two fingers sliding in and out. The sight of my ever-sexy wife on her knees on our hotel bed sucking on this stranger's dick burns itself into my brain. She looks so sexy taking him into her mouth as his cock disappears deep into her throat time and time again. I will never forget the slurping sounds of her cock sucking as Brian begins to moan louder, actively thrusting his hips upwards to fuck my wife's mouth.