One of the perks for reaching a certain sales level at my wife's company was a free trip to the Bahamas. Sell a little more, and your husband is free, otherwise you have to "buy him in" for, like $2000.
Everyone in my wife's circle either sold enough to take their husbands, or bought them in. Except for Gloria. She came by herself, and the rumor was that her husband could have come, but didn't want to, which really pissed her off, leading to the latest in a string of big fights. Between that and the free drinks, she was being pretty flirty with me.
Now, you'd think that might bother my wife, but she encouraged me to flirt right back. For one thing, she adores Gloria, but can't stand her husband. The other thing is, my wife would prefer to get my attention off of her. It seems like our vacations are about the only time I get any sex, and I had been warning her that I expected a lot of it this week. She promised me I'd get some, but she didn't seem too happy about it.
So we're laying in the sun by the pool, and I'm enjoying the scantily clad women from behind the relative safety of my sunglasses.
"So have a good time without him! That'll show him," my wife is telling Gloria. "Stan'll show you how a man is supposed to treat a lady."
"Really..." Gloria slid her sunglasses down her nose and leered at me. "Would you like to show me a good time, Stan?"
"I'll do my best, Ma'am," I said, tipping my imaginary hat.
"Hey, no Ma'am or Mrs., okay? It's Miss Gloria... No, wait... this trip I'm 'Mistress Gloria'." The girls dissolved into laughter, and I nervously joined in.
Every so often we'd slip into the pool to cool off. One time the girls started horsing around with me, splashing, then ganging up on me, trying to dunk me. I enjoyed touching Gloria, nothing inappropriate, just horsing around. I touched my wife, however, a bit more intimately, and she was returning the favor. After a while, suddenly I realized that I wasn't so sure it was always my wife grabbing me down there.
"C'mon," said Gloria, "Let's go get something to drink!"
"I think Stan wants to swim for a while. Let's dry off first."
"Stan, I thought you were gonna show me a good time?"
"Gloria," my wife lowered her voice, "You got him all worked up. He needs to... cool down."
"Uhhh... Oh! Did I do that?" she looked at me. I turned all red. "I guess I did!" Then in a louder voice, she said, "Stan, don't be 'long'! I think you've had too much sun! You're all red!"
And the girls had some more laughs at my expense. I paddled around as they dried off. They were huddled together talking in low voices when I finally was able to get out of the pool. I was still half erect, but at least it wasn't sticking straight out. I noticed both girls' eyes were glued to my crotch as I approached.
"You guys ready?" I said as I toweled myself off.
"I'm gonna work on my tan," my wife said. "You two go, you both need to get out of the sun. And Stan," she lowered her sunglasses and looked me in the eye. "Make sure you show her a good time. I mean a really good time!" and she winked at me!
"Sue, you're the best friend a girl could have," Gloria said, pecking her on the cheek. As I leaned down and kissed my wife, she gave my cock a squeeze and whispered in my ear, "A reaaallly good time!"
I wrapped my towel around me so my excitement wouldn't show so much, and Gloria took my arm. We headed for one of the many bars not far from the pool area.
"Two Bahama Mamas," I ordered as we flashed our bracelets that got us free drinks.
"Oooh, these are big," Gloria said as the bartender handed us the frosty cups.
"They certainly are," I said, looking at her boobs. "The cups are almost overflowing!"
"Your Bahama Mamas look quite tasty, no?" the bartender said to me, nodding first at Gloria and then towards the pool where my wife was sunning herself. Then he looked at me and grinned broadly.
We walked a while, then sat down at a table in the shade with our drinks.
"Am I making you uncomfortable?" Gloria asked.
"As long as my wife approves, I'm fine," I smiled.
"She's such a doll. You're okay?"
"Yeah, sure. What do want to do?"
"Step one is almost done," she said, raising her cup. "Dinner is next, then dancing. And then, if you play your cards right..." she giggled and pulled me along by the hand.
She dragged me to my room. "Let's see your dancing clothes!" She pawed through my things till she found something appropriate. "Here, try this on. I won't look!" she said, turning away. But I knew she could see my reflection in the TV screen. And I think she knew that I knew. I took my time taking off my swimsuit, drying off and putting on clean briefs. I was pretty confident she'd like what she saw.
"Okay, I got my undies on, I'm decent." She turned around.
"Ooh, I'd say 'decent' is an understatement. That bulge you're packing there is downright indecent!" I smiled and started to pull on the pants she had selected. "Wait! Before you do that..." she threw her arms around me and kissed me, pressing her bikini-clad body into my underwear-clad one. You know, my wife isn't into kissing much anymore. I'd forgotten how much I love it. No tongue, but I still loved it.
"Okay, we can go now." we pulled apart, and my indecent bulge was now obscene. "Well, maybe we should wait a little bit. Do you need me to help fit that in your pants?"
"I think I can handle it."
I thought it might get chilly later in the evening, so I carried a thin sweater. Besides, it gave me something to hide my erection with as I followed Gloria to her room. Watching her bikini strain to contain her bottom as she walked in front of me wasn't helping matters. I think she took the stairs instead of the elevator just to tease me. She hiked up her bikini, then started up the stairs ahead of me. Generous handfuls of ass peeked out, wobbling back and forth as she really worked those hips, her ass at eye level as I followed close behind her.
In her room, she looked for something to wear as I turned on some lights. I opened the brochure on the desk, and read off to her the dining choices within walking distance. She asked my opinion on various outfits, and a pile of possibilities grew on the bed. I called a restaurant and made reservations.
"Okay, turn around and I'll try this one." She studiously avoided looking in my direction so I could watch her reflection in the TV screen. Mmmm, nice. Her boobs weren't as big as my wife's, but they were fifteen years younger. You know, it was hot and sweaty outside, then we came inside where the air conditioning was cranked, so when Gloria took off her top, I guess it was inevitable that those nipples would perk right up. I like to think that my presence had something to do with it, especially since she knew full well I could see her reflection. And I knew that she knew. And she knew that I knew that she knew. And I knew that she knew that I knew that she knew. She took off her bottoms, and took her time drying off, completely naked.
"Can I turn around now? You got your undies on?"
"Actually, I wasn't planning on wearing any underwear!"
"You know, at this rate, I'm gonna have to keep my sweater in my lap all night!"
"Okay, how's this?"
Gloria looked really cute in a light summer dress. I love the braless look, and the cut of the dress and the thinness of the fabric really flattered her modest bosom. The dress wasn't super short, but the thought of no panties made it seem scandalous to me.
"Oh, that's perfect! You look great! Really cute!"
"Uh, 'cute' isn't exactly what I was going for. Besides, a girl has to try everything on before deciding!"
So she tried on several other outfits. Some were very elegant, perfect for dining, but not too good for dancing. Others were super sexy, which I think she just wanted to tease me with.
"Um, if you go dancing in that, they're gonna fall out!"
"I bet you'd like that, wouldn't you!" she pressed against me and we kissed again, much longer this time.
"Uh, what time was the reservation?" Her voice sounded a little husky.
"Oh, we've got less than fifteen minutes. We'd better get going."
"Damn!"
She changed one more time, back into the first one she tried on, and we headed out for dinner, hand in hand. When we got far enough away from the hotel that we weren't going to see anyone she knew, I slipped my arm around her, and she rested her head on my shoulder as we slowly walked and talked.
"You know, you're getting more attractive all the time," I said, looking down into her eyes.
"What, am I getting tan?"
"No, it's just that... we're getting to know each other and... You know, a lot of women are attractive until they open their mouths, know what I mean? But the better I know you, the better you look to me. I mean, I always thought you were cute, but man..."
"What?"
"Now I think you're pretty... pretty hot!"
"Stop it, or you'll get my panties all wet... Oh, that's right, I'm not wearing any!"
We arrived at the restaurant, and twenty dollars American later, we were seated at a relatively private table. You know, I always have a hard time enjoying myself at a fancy restaurant. But somehow that isn't a problem when the company's paying. We had drinks, we had appetizers, we had salad, we had a marvelous entree, and then we had dessert. We left a lot of each on our plates, or they would have had to wheel us out. Did I mention the drinks? We were both pretty loosened up by the time we walked out into the cooling evening.
We carried our sandals as we walked on the beach.
"You know what you were saying about when a girl opens her mouth and then she's not so attractive anymore?"
"Oh... yeah," I said trying to follow her tipsy train of thought.
"Well, it's true for guys, too. My husband is a prime example."
"Hey, I thought we weren't going to talk about him?"
"Yeah, you're right... Sorry. Let's talk about you instead. You are getting more attractive all the time."
"That's because you're getting drunker all the time."
"No, let's see if it works... Open your mouth!"
I did, in an exaggerated fashion, and Gloria attacked me, plunging her tongue into my mouth. We dropped our sandals as she pushed me against the rock retaining wall we were walking alongside. I was kind of shocked, but I was determined to just enjoy wherever this went. Our tongues alternated giving and receiving. Of its own accord, my hand wandered up to her breast.
"Ah, ah, ah! Dancing first," she teased, grabbing my hand and pulling me away from the wall.
