Where Flirting Leads

My wife, Sheila, is an incurable flirt! She is a sexy brunette with a voluptuously curvy figure, and she gets a lot of male attention. I always found her behavior, flirting with other men, to be harmless fun, sexy and even arousing for me.

All of this took a new turn when we spent a week vacationing in Miami, Florida. We were staying in a beachfront hotel with a pool and a hot tub. Our first night there was a Friday, and we went to a club that had a band playing with people dancing. I like to dance, but I am noticeably bad. Sheila got me out there anyway. But, after a couple of songs, I wanted to take a break.

As we walked back to our table a guy I had noticed at the bar checking out my wife stepped up and asked if he could have the next dance with the lady. I just shrugged, and she said "Sure! That would be nice."

We are in our mid-40s and he looked like he might be a few years younger. He was in incredible shape, and clearly was a way better dancer than me. I'm sure Sheila enjoyed having him as a partner. I watched as they danced to some fast songs, and tried to talk to each other over the music. The music slowed down and he pulled her into his arms. Everything seemed pretty innocent, but as they spoke to each other, I noticed his hand on her back sort of caressing her. Sheila pulled her head back a little and said something to him that made them both chuckle. Then he said something and they both laughed out loud as the song ended.

Then she grabbed his hand and led him to our table.

"Dan this is my husband, Bill," she said. And then to me, she added "Guess what Babe, Dan is staying at the same hotel as we are. He's here for a conference that starts Monday."

"Great, maybe we will see you around," I said.

"Oh we're definitely going to see him around, Babe," Sheila said. "He's going to give me a massage tomorrow."

"Oh really!?"

"Yeah, Bill," Dan said. "I'm a trained masseur. I own a therapeutic massage business. The conference next week is our annual industry event."

"Honey, Dan was rubbing my back during that last slow dance and it really felt good. I told him if my husband touched me like that he might get lucky more often!"

"Your wife is a riot," Dan said. "I had to laugh at that one. But I couldn't let that pass, so I asked if I had a chance of getting lucky! But she never answered. She just grabbed my hand and brought me over here to meet you."

"Well, you never know," my wife said flirtatiously as she gave him a sexy look.

Dan said he would be right back and went to the bar to get his drink.

"Your new boyfriend is pretty hot!" I said.

"He sure is," she said. "He's definitely boyfriend material. That's for sure."

He joined us as he finished his drink, sitting next to my wife, across the table from me.

He told us he was from Milwaukee, has been divorced for a few years, and is really glad to have a chance to spend some time in sunny Florida.

We told him about ourselves, that we live in Atlanta. I'm and engineer, and my wife teaches high school.

Then as I kept drinking, they made their way back to the dance floor. And it was obvious they were having a good time together.

They came back to the table to take a break a few times, but spent most of the night dancing together. And my wife was glowing!

When they came back to the table the last time, Sheila could tell I was half in the bag, and just said "We have to go."

He was quite the gentleman, offering to help as I staggered toward the exit. He got us an Uber back to the hotel. He helped Sheila get me into our room and onto our bed. She took off my shoes and turned to thank him and see him to the door.

I heard them talk about the massage tomorrow, and she gave him her cell number. They were talking quietly, not quite whispering. I could hear him thank her dancing with him tonight.

He said, "I had a great time with you!"

"I had fun too," she said "You're a wonderful dancer!"

"It felt great having a beautiful woman in my arms tonight. I wish I could take you to my room."

"Stop that, you funny man," she said.

"I'm not kidding! You're gorgeous!"

"You're not so bad yourself," she said.

It was quiet for a moment, and then I heard the sound of a kiss. They were kissing! It seemed to go on for a minute or so.

I hear my wife quietly moan, "Mmmmmmm."

"I want more. I want you," he said. "Are you sure you can't come with me?"

"I better not. See you tomorrow."

I heard the door close. My wife came into the bedroom, took off her clothes and went into the bathroom to take a shower.

+++++++++++++

It was late, just after 10 o'clock when I woke up the next morning. I had a crushing headache. I hit the bathroom to pee and look for some aspirin. But we didn't have any. I came out of the bathroom, calling for Sheila, but got no answer. Next to the coffee maker, she had left a note saying she was at the pool sunbathing.

I went out onto the balcony to look for her at the pool, and there she was, face down on a lounger in her tiny white, high cut bikini. And there was Dan kneeling at her side rubbing her down with sunscreen. This guy is persistent! As he finished covering the exposed cheeks of her very sexy ass, he bent down and kissed her butt.

Her head lurched around and it sounded like she said "Dan, you naughty boy!" But then they both just laughed. And then as she turned and sat up he leaned down, put his hand under her face and kissed her on the lips.

I found my swim suit and got down to the pool to find my wife rubbing sunscreen into Dan's very muscular back.

"Hi Honey," she said. "Dan rubbed me down with sunscreen, so now I'm returning the favor. I hope you feel okay. You had way too much to drink last night."

"I know sorry about that."

Dan offered to buy us drinks at the outside bar. I passed, but Sheila asked for a margarita.

A few minutes later he was back with a margarita in a huge plastic souvenir cup with two straws and found my wife in the pool.

"The souvenir cup is so big, I thought we would just share," he said as he got into the pool.

"Ha, sounds good to me," my wife said. "That is a monster-sized cup!"

I told them I was going to the drug store or the hotel convenience store to get some aspirin.

I came back about 15 minutes later to find them on the other side of the pool, heads bowed together as they furiously sucked up the last dregs of the margarita through their straws. They came up for air and laughed.

"I think I got more than you did," my wife said.

"We both got plenty, but you're a tough competitor," Dan said. "So how about that massage?'

"That sounds great! But I want to hit the hot tub first. Come on," she said. "Bill, Dan and I are going to get into the hot tub. Why don't you grab our stuff and join us."

I came around the corner of the building to the hot tub as Dan was climbing in and just in time to hear her say, "Wow! Looks like you have a lot going on down there."

"You are hilarious," he said. "I've never had any complaints in that department. Hey Bill. Just in time, I think your wife is sexually harassing me."

"Ha! As if," Sheila shrieked.

"She is a flirtatious girl," I said. "But that's one of the things I love about her!"

He and I sat on either side of Sheila in the hot tub. He was sitting just as close to her as I was. Right in front of me, I noticed her stretch her right leg out and over to his left leg and hold it there. The two of them looked at each other and smiled.

Fuck, I was getting hard.

He put his left arm around her and caressed her shoulder. Moments later her right hand moved to his leg and she began caressing his thigh. He leaned into her, and they kissed.

I cleared my throat, and she turned to me. "Are you okay, Baby? Are you getting jealous or aroused, or both?"

She reached down and grabbed my dick. "Aha, just as I thought hard! Very hard. Very nice. I like that! What about you, Dan?"

With that, she moved her right hand from his thigh to his hard cock.

"Oh my! Very, very hard. And very big!"

"Jesus, you are so fucking sexy," Dan said, "How about that massage now?"

As she kept fondling both of our cocks, she looked at him and deadpanned, "I think you're just trying to get me naked, Dan."

"I can't deny that I'd like that. I would love that, actually! But I am only talking about a professional massage, unless... Unless you want something more," he said with a wicked smile.

"Okay then," my wife said with a laugh. "I guess we'll just have to see about that."

She took her hands off of our cocks and, more seriously, Sheila said, "I think I should shower first. Are you going to come to our room, or should I go to yours?"

"Why don't you come to mine, since I have all the oils there. I'm in 308, just a few doors down from your room," he said. "And you can just wear the hotel robe if you want. I'll put modesty towels over you for the massage, so you won't need any clothes."

"Okay then. That sounds provocative. Give me about 45 minutes and I'll be there."

"And Bill," he said to me, "you're welcome to come and watch the massage. I might show you a few moves to help you get lucky more often."

They both laughed at that. I just nodded and smiled. "Maybe, I will ... just to keep an eye on things!"

Back in our room, I said "Baby, that guy is definitely hitting on you. And you are clearly leading him to believe he might get lucky with you!"

"I know," she says. "Does that turn you on?"

"Fuck, you know it does. It makes me jealous, but watching the two of you flirt and touch each other and even kiss right in front of me makes me hard! I can't explain it. It's just what happens."

"I think he's big down there," she says.

"I noticed. I think you might be right."

"You like that don't you? That's part of your kink isn't it? You get excited thinking about me with a guy who has a bigger dick!"

"I don't know. Maybe. I do think about that. It just seems so erotic!"

"Let's be honest about this," she says. "I think you want to see his dick as much as I do!"

"No, wait! You're taking this idea too far. It is the fantasy of you and another man that somehow gets me excited. But, I...I don't want another man to take you from me. I don't want to lose you! And I don't know if I could handle it if you actually did something like that!"

I'm getting hard as we talk about this. I have to admit to myself, I would like to see his dick. I am not gay, but I am curious.

"First of all," she says, "you will never lose me. But the fantasy gets me excited. It just sounds like an erotic adventure we could both enjoy. And let's face it, Dan is a pretty sexy guy!"

"Just be careful," I tell her.

Minutes later I go into the bathroom to get some more aspirin, and I find her taking a bath instead of a shower. And she is carefully trimming the landing strip above her sexy pussy.

"Wow! You are getting it ready for him, aren't you?"

"Come on, Baby," she says. "I just don't want to look like an amazon woman, in case he catches a glimpse," she says.

After putting on some makeup and doing her hair, we are knocking on his door. And just as he instructed, she is only wearing the white hotel robe.

He opens the door, and surprises us, wearing only a pair of red, body-hugging boxer briefs. I can't help but glance at his crotch, and he looks sizable.

Sheila also takes a fast look, and raising her eyebrows, says "Well, at least you're not overdressed!"

"Ha!" He says, "I didn't bring my usual scrubs for doing a massage, and I don't want to get the oils on my clothes, so I thought this would work. I hope you don't mind."

"No, I don't mind at all," she says. "But, it is kind of distracting," she adds with a smirk and another look at his big bulge. Turning to me, she says "You don't mind, do you, Honey?"

"No, I guess not."

"I wouldn't think so," she says with a big smile.

He tells us he will go in the bathroom while she gets settled face-down on the queen-sized bed. And he tells me to put one of the large towels he hands me on her "bottom," as he puts it, and to let him know when he should come out.

I'm seated in a chair by a desk in his room as he starts in on my wife's shoulders and back, rubbing oil onto his hands and working her muscles. He has soft, sensual music playing in the background, and my wife is clearly enjoying what he's doing.

"Mmmmmmm, this feels so luxurious, so good," she says.

"I can feel some tension in your shoulders and back," he says. "Just relax and let me work that tension out of your muscles."

He spends quite a bit of time on her back, eventually moving to her lower back, just to the edge of the towel covering her curvy ass.

Sheila's face is turned toward me, with her eyes closed and a look of utter enjoyment.

Now he is massaging her feet and legs, starting with her toes.

"Mmmm, I love how that feels," my wife says. "No one's ever done that to me before,"

He takes his time on her calves and thighs, massaging the muscles slowly. But, soon he is working her upper thighs next to her butt, his fingers occasionally moving down between her legs. I notice my wife spreading her legs slightly to give him better access.

"Some people like me to massage their glutes," he says. The gluteus maximus is the largest muscle in the body. Do you want me to do that, or not?"

"Oh, God! Really?," she says. "Oh Jeez! Well okay, I guess, if that's what other people do."

"Bill," he says, "would you pull that towel off for me?"

I walk over to the bed a little embarrassed because I am hard. Then I notice, he is too, his cock trying to break out of those briefs. I pull away the towel, and hear a sharp intake of breath from him.

"My God," he says to her, "You are absolutely exquisite!"

My wife chuckles, turns her head back toward him and says "Be careful Mr. Masseur, you said this would be completely professional."

He starts in on her butt, saying "You're the boss. I will be as professional as you want!"

His hands all over her ass, massaging her luscious cheeks, and spreading them apart. It is very erotic! Very sexy! Watching him touch my wife like this has my dick so fucking hard. At one point, he drizzles some oil into the cleft between her cheeks and several times runs his finger up the crack of her ass from the edge of her pussy up to the top of her butt. His finger almost certainly grazing that tight rosebud of hers each time.

"Oh my God!" She says. "That is so sexy. You sure know how to turn a girl on!"

I can feel the sexual tension between them building higher and higher.

"Okay," he finally says. "Time for you to turn over. I'll go back into the bathroom while you get situated. Some women like me to massage their breasts. But if you don't want that, just have your husband use two of these towels to cover your private areas."

"What should I do, Baby?" She asks as she turns over. "Should I let him massage my boobs?" And then, before I could answer, she says "Oh my God! You have a fucking erection! This turns you on, doesn't it?"

"I have to admit, it is pretty fucking sexy! How about you, are you aroused?"

"Actually," she says as she reaches between her legs, "I feel pretty wet down there. When he was doing my butt, his fingers touched my pussy a couple of times."

"Well, we're not the only ones," I tell her, "his dick is trying to explode out of his underwear! And his dick looks really big"

"Oh my God! That excites you doesn't it? What are we doing? Where is this going?" She says.

I lean down and whisper to her, "Honey, this is going as far as you want it to go. You are in total control. It's up to you."

"Baby, I really, really want him? I'm sorry. But he is just so sexy. Do you hate me?"

"No, just be careful!"

"Okay," she says. "I think I'll only need one towel!"

I place one towel over her vagina and start to go back to the chair when she says "wait. Baby, I ... I...God dammit ... I want this. I need this. Take that other towel. I want him to see me. I want him to take me!"

"Oh fuck! Should I leave?" I asked.

"No. You've always said you wanted to watch, This is your chance!"

She looked at Dan nervously when he came back into the room. "I guess I may as well get the full body treatment," she said with a big smile.

"Mmmmm," He says. "You look absolutely delicious. I am going to give you my absolutely best full body treatment!"

He glanced at me as I rubbed my cock through my shorts. I looked away, then back at him as he took off his briefs. His big cock bounced up like a clown popping out of a jack-in-the-box.

"Oh my God!," my wife said "You're so big. Honey," she said to me, "Look at him. His dick looks so powerful!"

He bent down and kissed my wife. She put her hands on his head and responded passionately, opening her mouth as he pushed in his tongue and laid down on top of her.

"Mmmmmm," she moaned.

"You are so luscious, so sexy," he said "I knew I would get lucky!"

His hands were all over her breasts, fondling them, rolling her erect nipples between his fingers then kissing them, nibbling them.

Sheila's head rolled back, her eyes closed as she moaned, "Oh God, mmmm, yes. I want you!"

He was sucking one of her nipples.

"Oh," Sheila said. "Not so hard."

He kissed her nipple then moved to the side of her breast and sucked hard.

"Oh, oh my God! Are you marking me?" she said

"Mmmm. I want you to remember me," he said.

He kissed his way lower on her body making love to every part of her on the way to her pussy. When he got to her slit, he inhaled deeply, savoring her scent. Then he kissed her lips, licked them, pushed his tongue into her. He licked up and down her slit, then went for her clitoris, kissing it, nibbling it and sucking it hard.

"Oh fuck!" My wife said "That's it right there. Oh fuck yes."

She moaned as he continued his passionate assault on her pussy and clitoris.

He put a finger inside her and rubbed her "G" spot as he kept sucking and nibbling on her clit.

She seemed on the verge of orgasm when she said "God dammit! You are so good. But, stop! I need you in me. I want you to fuck me now! Please!"

He raised up, moved up on her as he lined up his cock with her pussy. She reached down and guided him in.

"Oh, oh, stop! Go slow you are so big! You're stretching me," she whimpered. "But not too fast."

Soon he was halfway in, stroking slowly in and out just the first part of his cock. She was moaning.

"Oh God! You are so fucking good."

She looked down at his cock stroking in and out of her.

"Dan, your cock is so amazing. I'm falling in love with it."

Soon he was all the way in, stroking in and out, and she was moaning with pleasure.

She reached for his head and pulled him down into a passionate open-mouthed kiss.

"Mmmmmm. Mmmmmm," she couldn't seem to stop moaning.

When they stopped kissing, he bent to her neck and kissed her there several times, then sucked really hard on the side of her neck, planting another love bite.

"Jesus," she said, "you're going to have me all marked up. Dan, Sweetheart, I want to get on top. I want to ride you."

He pulled out. His dick almost looked like it was swaggering. Such an amazing love tool. They changed around so she was on top. She slid down onto him.

"Oh fuck," she said. "Sex has never felt this good. Your dick is a work of art!"

She slid up and down on him as he licked her nipples and played with her ass, pulling her cheeks apart, feeling for her anus.

This is her favorite position and soon, she exploded. "Ooooooh, aahhh oh yes, yes, fuck yes. Sooo damn fucking good. Oh God Dammit! Thank you, thank you."

She bent down kissing him with an open mouth. The two of them making love with their mouths as he seemed to be getting close.

He turned her over without separating from her and started hammering her. Thwap, thwap, thwap, his big balls slamming into my wife's ass as his cock stiffened even more and started shooting his sperm into her.