The First Time

We took a quick trip upstate to visit a winery and booked an overnight at the Casino to blow off a little steam and spend some time together. We've been together over 20 years and like all busy professionals don't make enough time for one another; so a night away was just what we needed.

My wife (Sara) and I (Jeff) had a great day together, the winery was off the beaten path and a nice ride into the country. It's a pretty mild day for the end of July, but the weather was beautiful. Sara heard about this winery from a friend of hers and wanted to check it out, it's run by a group of women and they offer retreats there as well. She thought it might be a fun weekend trip to take with her sister and sister-in-law this fall.

Sara and I were sitting at the casino bar having a cocktail after a few humiliating rounds of blackjack. We had a decent amount of wine on the tour and shared a bottle at dinner as well, so we were a bit tipsy at this point. When we drink wine together we get pretty flirty, and I have a habit of gazing at Sara when I'm drunk.

After 20 years I still find Sara to be stunningly beautiful. Have you ever had your breath taken away when you see a beautiful woman? Well that's what Sara does to me, it's not like all the time or anything; but there are times I see her walk out of a store or into a room and my heart skips a beat when I see her; she really can be breathtaking.

Sara is 5' 7", and if she's wearing heels or boots, as she is tonight, she is closer to 5' 9". She's got almost waist length light brown hair, blue-green almond eyes, high cheekbones, her face is slender and she's got beautiful straight teeth. If you have ever seen the actress Olivia Wilde you would think they could be sisters. She works out almost daily and has an amazingly fit hourglass figure with long muscularly toned legs. Sara is mostly European, but she has an exotic look from her high cheekbones that makes you think she could be a little Asian. If you met her you wouldn't guess she was in her early 40s.

Tonight she's wearing a pair of jeans with her favorite pair of cowgirl boots and some kind of green sleeveless blouse that I can't really describe, and a tank top under it. The green blouse really makes her eyes pop, and they look more green than usual tonight. She's been hitting the weights and high intensity training for a quite a while and she's been rightfully proud to show off her toned arms. Needless to say, she is on point tonight.

Sara is in a flirty mood, and she's had some wine; so I am already looking forward to heading back to our room in a bit. She and I have some of the best sex when we've had a few drinks. We lose all of our inhibitions and often communicate our desires and fantasies much more honestly when we've had a few. We are both in a playful mood, so I know tonight will end well.

It was nearly 9:30 when a large group entered the bar area. Must have been at least a 75 or so, the comedy show at the casino just ended. I figure this is a good time for us to head out because the bar was getting busy, but we just got a fresh drink so it would be a bit before we left.

A younger guy steps up to the bar next to Sara to order a drink, he's standing there waving his money to try to get some attention. Sara, who's always outgoing and chatty with most people, asks the guy "How was the show?". He answered her and she giggled a little, but I can't hear his response over the influx of noise in the bar at the moment. I move closer so I can get into the conversation.

Sara and I start talking with "Curt", who turns out to be some sort of industrial mechanic that is in the area to fix machines at a manufacturing facility nearby. He came into town on Wednesday and was going to be here until the following Friday. Curt was a mechanical engineer, so he was a mix of blue collar humor and college educated wittiness.

Curt was about 5' 10" with dark features, he was from Phoenix so he might be a little native american or hispanic, but mostly European. He had short trimmed hair and beard, medium build, and his left arm was fully tattooed to his elbow. He had a pretty deep voice, and a nice set of white teeth with a good smile. You could tell he worked on his feet and used his hands often as he had pretty muscular forearms. He appeared to be in pretty good shape and was well groomed. He had on a pair of jeans, some clean boots, and a rolled sleeve flannel shirt or a "country shirt" that was crisp, with it tucked in and some Arizona appropriate belt buckle on. Curt was 33, had an eight year old daughter and had been divorced for just over a year.

Sara loves to laugh and is always attracted to humor, and Curt was pretty funny. A strong sense of sarcasm and quick wit. Him and I hit it off pretty quickly as well, he's smart, polite, and funny; we have a few things in common and get to clowning around. Curt and I are now up staging one another just trying to make Sara laugh; and it's working pretty well. I can tell in Sara's body language and the way she's smiling at Curt that she's attracted to him.

Sara has always been a flirter and I have known that since we met. Most of the time it doesn't bother me, and I know it's just her way of feeling sexy or desirable, and scratching the itch for some new attention. She is a beautiful woman inside and out, men (and some women) are easily attracted to her. She brightens up the room when she walks in, her outgoing, playful nature is really intoxicating. So it has never surprised me when others find her attractive, she is.

That said, from time to time I feel like a chump when she's too flirty or some guy is coming on too aggressive. I'm not a cuck, I'm a patient alpha; and there are a few times I've considered going full on silverback at certain types of what I would call "pursuers".

Tonight was not one of those nights, I wasn't feeling threatened at all. Curt was respectable to me, and flattering to Sara. He was a good conversationalist, in part I think because of his time alone on the road, and part because he was just easy to talk to. He was smart, good looking, and funny, and I could see Sara was attracted to him.

Sara doesn't really have a type, she finds many people attractive, men and women alike. For example, I'm a bigger guy, I've always struggled with my weight, but I've been a gym rat for 30 years. So I am a mixture of a middle aged dad body and a retired bodybuilder. I'm just over 6 foot tall, with a wide frame. People often ask if I used to play football, so that should give you an idea of my body type. I too have dark features, a little middle eastern and mediterranean mix. I think I'm handsome, I have gentle eyes, and have a nice salt and pepper thing going on that some people find attractive.

Other than the dark features, Curt and I don't really look anything alike. He's got a thinner face with a squarish chin under his beard, and well defined cheekbones. I'd say without the beard, he'd probably be more of a pretty boy; in fact he kind of resembles a young Ricky Martin. The beard makes him look more manly and older, and it fits him well.

After about 45 minutes, Curt excuses himself to use the restroom.

Sara looks at me and says "Maybe tonight is the night Honey."

At first I'm not sure what she means, I kind of blank stare and blink at her for a second as to ask, "What now?"

Sara turns to me and says "You know what we've talked about before?" and raises her eyebrows.

My heart steps up a beat. In my head I'm like "Shit, is she talking about a threesome?"

Sara and I, like most couples, have had fantasies in the bedroom. We talk pretty openly about what turns us on and from time to time we talk about threesomes or group sex, swapping, etc. It turns us both on, and makes for some kinky sex. A few times in the past we've done some light girl on girl and same room sex with friends of ours. One of the times she and I just kind of put on a show. But it's been a long time now since those days and since we started a family a lot of those types of things have cooled off.

I'm a little shocked at what she said to me; and she can see the surprise in my eyes.

Sara says "Nevermind honey, I'm just kidding."

I respond "No, no hang on babe, do you want to for real?"

She blurts "Yolo" obnoxiously and starts laughing.

"For real honey", I rolled my eyes at her but at the same time laughed a little.

I ask "Seriously do you really want to?"

Sara coyly says " Well yeah.. kind of."

I nod. "Well then let's make it happen."

My heart is racing now and thoughts are racing through my head. I'm scared and nervous at the same time. I can see the same type of look on Sara's face. I smile at her to reassure her, and I know she reads some apprehension from me as well.

Sara leans into me, kisses me and puts her hand on my forearm.

She stares searchingly into my eyes and says "I love you Jeff."

I stare back at her and say "I know you do babe, and I adore you."

Curt returns from the restroom and orders a new drink, We go on chatting a bit more and laughing, Sara and I refresh our drinks. It's getting close to 11 or so, I'm getting tired, I've pulled back on the booze a bit so I can keep my wits about me. Sara excuses herself for the restroom. I watch Curt check her out as she walks away in those sexy cowgirl boots, he does it respectfully, he takes a few glances but doesn't stare. He doesn't want to miss the view, but he's not trying to be disrespectful or a creep.

I lean towards him "Hate to see her go, love to see her leave, right?"

He looks at me like he's busted "Sorry man, I'm not trying..."

I interrupted, "No worries man, she's a beautiful woman, I don't blame you."

He grins shyly "You're not wrong Jeff, you have a beautiful wife."

Sara is gone for a bit in the restroom, Curt and I chat a bit about his Ex, his dating status, work. He hasn't dated anyone since his divorce was finalized over a year ago. He has his daughter on the weekends that he's home, and the rest of his time is consumed with work and travel. He's just been going through the motions.

I see Sara coming out of the bathroom across the casino floor.

I look at Curt and say "Want to have some fun with her tonight?" and I motion in Sara's direction.

Curt's eyes widen, and he swallows hard "Umm, what do mean exactly?"

"You know.. We could show her a good time" I say and bounce my eyebrows up and down.

"Are you fucking with me Jeff?" he stammers a bit.

I look at him and smile, "Nope."

Sara is just about back to us and Curt is trying to find his composure. The question caught him off guard and his cheeks are now a little flushed. Sara sees that Curt is a little shaken, and asks "You guys doing alright?"

"Yeah we're fine, right Curt?" I smile.

A big grin comes over face as he looks at Sara and he says "Oh hell yes!"

Curt's definitely got a little more swagger in him now, I can see he's trying to peacock a bit for Sara, and I can see she's into it. This goes on a bit more and we are laughing and having a good time.

Curt's phone rings, He says "This is my daughter, I need to say goodnight to her." and he moves out of the bar area to take the call. Sara's eyes kind of linger on him as he exits.

I look at Sara "Well babe, you still wanna do this right? He's down."

She looks at me nervously "Really?" she asks.

I say "Yeah, when you went to the bathroom I tested the waters, he's in."

Sara's eyes widened "I dunno." she muttered

The idea of crossing from fantasy into reality has her second guessing it.

She stutters a bit and then looks me dead in the eyes. "I.. I.. are you really ok with it Jeff?"

Sara's trying to get a read on me to make sure I'm not just trying to please her.

"I Love you honey, if it's what you want it's not my place to deny you." I respond.

"But do you want this?" she asks.

I smile at her and say what she already knows. "I love watching you get off honey, I am ok with this as long as you are."

She leans into me on the bar stool and puts her hand on my cock.

She whispers in my ear "You better wake this guy up then."

My heart starts racing, I know now, that is really going to happen, I've got goosebumps or nerves. I'm excited, I'm scared, but hell I'm excited.

Curt comes back from his phone call, I tell him that we were ready to turn in for the night. Curt looks confused and a little sad like he has missed the opportunity.

He says "Oh, sure, ok, well it was nice meeting you two.."

I open my mouth to speak, but Sara beats me to it and says "I thought you were coming with us Curt?"

The color returns to Curt's face and he smiles, "Yes please!" he says.

Curt says he needs to run up to his room first, Sara and I give him our room number and we head to our room.

We get back to the room and Sara and I start making out as soon as we get in the room. She is really worked up at this idea. She's kissing me very passionately and using lots of tongue; something she only does when she's extremely horny. I unbutton her pants and slip my hand down the front of her panties. Her clit is swollen already and her pussy is soaked. I let out a soft grunt, she feels so fucking good in my hands.

I spin her around standing in the doorway, and run my left hand up her shirt and squeeze her breasts while I start kissing her neck, she's breathing hard already. I'm teasing her pussy with my right hand and rubbing her swollen clit between my fingers. She makes a soft moan when I run my fingers up her slit.

My cock is so hard, I unbutton my pants and she pulls it out with her hand behind her back.

"Whoa" Sara whispers, "Somebody is ready."

"You said to wake it up babe, surprise!!" I laugh.

Her hands feel so good on me, and the way she's responding to me kissing her neck and teasing her. Fuck it's so hot listening to her.

I break away from Sara, she is so close to cumming I can tell. I tell her we should probably take a shower. She doesn't want to stop and keeps tugging on me.

"Hold up baby." I pull her hand off of me. It's hard to stop when she's this excited.

We get in the shower together, the suite we have is really nice; it's got what we would call a "sex" shower. It's got a rainfall head, a big bench and barn doors on the shower. We could probably get 5 people in here if we wanted to.

It's hard for me to keep my hands off of her as well. I keep teasing her pussy, she's soaking wet in there already; and she's stroking my cock as we wash. We get out of the shower, and she puts on the hotel robe, and I wrap on a towel. I'm still pitching a tent, she laughs at me trying to conceal it under a little hotel towel.

It's been about 25 minutes now and we are starting to think maybe Curt bailed on the idea, got cold feet, or just chickened out. Sara sits down on the edge of the bed next to me looking a little disappointed when there is a knock at the door.

I get up to answer the door, It's Curt as expected. He's got a change of clothes neatly folded in his hands, and he's wearing the same hotel robe Sara has on, and some flip-flops.

He smiles "I took a quick shower, I see you guys did too."

Curt comes in, I shut the door behind him and throw the latch. He looks at Sara and shyly says "Hey"

It was one of those funny innocent moments, like when you're a kid and it's the first time someone lets you see their boobs. Like you're excited, but you're nervous, and you're feeling vulnerable. Curt was clearly a gentleman, and it showed in his general demeanor.

Sara was sitting on the bed still, looking nervous now as well.. I'm nervous, too. We're all nervous. I'm in this towel with a hardon strapped down against my leg. I laugh and draw attention to it and nervously say "Well, at least one of us came prepared!"

We all let out a nervous chuckle, I think that helped break the tension a little.

Sara nervously says "Come over here you two." and she lays back with her feet off the edge of the bed and opens up her robe ever so slightly. Her right leg is completely exposed all the way to her hips. You can see just a little bit of her pubic hair showing and some of her right breast.

It's mid-summer so she's got full on tanlines, you can see her bikini line just above her bit of pubic hair that is showing, and the tanline wraps her hip. I love her look this time of year, and her confidence and sensuality match her outward appearance.

Curt pauses a second taking it in. Sara has an amazing body for a woman her age. She's got curves in all the right places, she's got wide hips and a narrow waist; she's built like the old pin-up models from the 50s. She oozes sexuality and femininity when she's feeling confident. Tonight was one of those nights.

Curt and I approach the bed. Sara looks up at Curt and opens her robe a bit more. Her pussy is now in full view, she has a beautiful pussy and lips that are like a butterfly. Her clit is swollen from teasing her in the shower. I can see Curt is starting to swell up under his robe.

Sara looks up at Curt, and sensually says "Well, what do you think?"

Curt stammers a bit "Holy shit you're sexy!"

Sara says "Not bad for someone my age right?"

Curt echoes "Not bad for someone my age." and throws a big smile.

Sara beams at this. As she's gotten older she worries that she's losing her appeal, no amount of reassurance from me means much. I'm the default, and her biggest fan, so I get that. Here is a guy 10 years her junior that is currently drooling over her; it is validation she craves in this moment.

Sara pulls her robe open all the way so Curt can take it all in. He's now got a very visible hard-on under his robe.

Sara spreads open her hips and asks "Do you want to taste it?" and runs her hand across her pussy with a smile.

Curt nods and lets out a whispery "oh yeah!" and immediately drops to his knees. I'm a bit in shock to be honest, it's all so real now. Sara glances at me nervously as if she wants my approval, I smile and raise my eyebrows in surprise.

Curt goes to work, he starts by lightly teasing her. Her clit is so swollen, but it's like he's intentionally skipping it. He licks her up and down her lips, then a big wide tongue up her slit. She's dripping in excitement, he rubs his nose a little across her clit and his fanned out tongue. Sara moans.. he's driving her nuts. Every time he grazes her clit she lets out a soft 'mmmm' sound.

Her robe is open all the way now and she's looking down at Curt and he's making good eye contact with her. She's squeezing her breasts as he teases her, she's so turned on and fixated on watching him eat her pussy.

I'm dumbfounded still.. Standing in this towel with a raging hardon, super turned on by what I'm witnessing. My left hand Is just squeezing my cock through the towel. Watching her excitement has me so fucking hard.

Sara looks at me and says "Jeff, were you just gonna stand there all night?"

I laugh. "Sorry baby, taking it all in."

She looks at me "Want me to take it all in honey?" she winks at me.

Fuck I love it when she's dirty and assertive. I drop my towel, my dick is ridiculously hard. I climb on to the bed, and pull my cock up next to her head. I grab a few pillows to prop up her back and neck. Sara wraps her mouth around my cock. Fuck does that feel good.

Now, I'm not the biggest man, but I've got a little above average cock.. When it's at its hardest it's almost 7 inches, and it's about 6 inches around. I've always said it's handsome, and well, it does the job most of the time.

Sara continues to suck my cock, and she's into it. When she's really horny she tries to take all of my dick. I'm not sure if she's channeling her inner porn star, or if it's a personal challenge. But it sure feels amazing. I can tell how turned on she is by how hard she sucks it.

My dick is in her mouth, but she's watching Curt eat her pussy. Curt has her edging so bad it's driving her nuts, every once in a while he'll hit her clit and she'll suck my cock in harder and moan a little. He really has her worked up by denying her orgasm