This story involves a wife knowingly and freely cheating on her husband right in front of him. If you don’t appreciate cuckold stories, do not read this.
As with all my stories, this story is inspired primarily by Jet Lag, and similarities in theme or style are credited entirely to him.
About a week ago, my wife Annie and I were invited to a beach resort along with a bunch of her coworkers. She works in the marketing department at a large company which did very well in the past few years, and the employees were starting to get a lot of perks, one of which was the resort trip.
I was eager to go, although I was worried about meeting Annie’s coworkers. Her company had a very informal culture, and Annie would sometimes tell me about all the flirting and pinching that went on during the workday. I worked at a law firm, which was very uptight and professional, and flirting was considered inappropriate. Over the years, some of it had rubbed off on me, and I was becoming more straight-laced and formal. I wasn’t sure I would fit in with Annie’s group.
Annie herself is a knockout. She’s twenty-six, with very short, stylish blond hair and a beautiful face. She’s a little shorter than average, with slim legs leading up to a tight, curvy bottom. She would look like a pixie if she didn’t have magnificent C cup breasts, which look fantastic on her frame. They’re full and round, and they sit high on her chest. We met in college and hit it off pretty quickly, and married soon after we graduated. She wasn’t very experienced sexually, although I wasn’t her first.
The day of the trip, we drove out to the resort. On the way there, Annie mentioned that she bought a new bikini for the weekend.
“Trying to show off for everyone, huh?” I kidded her.
“Maybe,” she answered, with a smile.
“What’s that supposed to mean?” I asked. It wasn’t like Annie to really show herself off. I had a difficult time just getting to wear skimpy underwear.
“Nothing, nothing,” she laughed. “I’ve told you about all the flirting that goes on at the office. This is just another way to tease the guys.”
“What are some of the other ways you tease the guys?” I asked.
“It’s not just me, silly, all the girls do it,” she said. “Just flirting and stuff, you know. Talking dirty and a flash or two.”
“Wait, what?” I practically shouted. “A flash? You’ve flashed guys?”
“Oh, sweetie, it’s no big deal,” she replied. “It’s teasing. We just pull up our shirts sometimes. It’s just boobs.”
I was flabbergasted. My wife was showing off her tits to other guys? Other guys at work? That was unlike everything I knew about Annie. Just how friendly was she with these guys, anyway? I started to feel a bit of dread as we approached the resort.
We pulled up to the resort soon after. As we carried our luggage into the lobby, a group of people waved Annie over. They were some of her coworkers, and she introduced me. Among the guys there was Alan, Dave, Eddie, and Gary. Among the girls there was Ashley, Christine, Molly, and Nicole.
The group told Annie that everyone was meeting by the private pool to get in the water and have a few drinks before going to the beach. We agreed to meet them there as soon as we got in our swimsuits.
As we turned to leave, Alan reached over and pinched Annie’s tush. She squealed and pushed him away. I was about to jump in, but everyone started laughing, including Annie, so I figured it was some harmless flirting. I didn’t want to come off as prudish in the first five minutes, so I kept quiet.
We got to our room and started changing into our swimsuits. Annie went into the bathroom to change and came out wrapped in a towel. I wanted to see what she had on, but she cut me off before I could say anything with a “C’mon, let’s go!”
I grabbed a book and followed her around the hotel and onto the pool deck. The company must’ve rented out the entire pool, because there were company logos on the towels and welcome signs. There were about fifty people milling around the pool. Most of them were guys, and to my disappointment, many of them looked young and attractive. The girls were nothing to complain about, though. A lot of them were wearing skimpy bikinis and looked great.
I turned to ask Annie where her friends were, when I saw her open up her towel. I was stunned at what I saw: she was wearing an extremely revealing dark red bikini, that looked a size too small. The top was straining against her breasts, and it looked like the strings were ready to snap. The bottom was almost a thong, cut high to show off her legs. She looked absolutely gorgeous.
No wonder she wrapped herself in a towel in the room, I thought. She knew I’d be concerned about her wearing that. I was about to say something when I heard a voice from the pool shout, “Hey, look at Annie!”
This was followed by a chorus of wolf whistles and howls from guys all over the place. Annie giggled and struck a pose, showing off her tight stomach and great legs. She turned to me and said, “See? It’s just teasing!”
I nodded and kept my mouth shut. I wish she had said something about how revealing the swimsuit was, but that wasn’t anything to really get mad about. It was still a bikini. Besides, if some guys wanted to ogle my wife, what was the harm in that? I could even see myself being proud of it.
I laid back in the lawn chair and opened my book while Annie walked over to her friends. I had planned to spend some reading, but I found my gaze wandering back to Annie. Every time I looked at her she was flirting with a guy. Eventually I stopped reading altogether and just watched her while pretending to read.
The company had an open bar on the deck, which I visited a couple of times to get a beer. There was a lot of drinking going on, though – apparently this was a real party crowd. I saw Annie go there several times for margaritas, and there’s no telling how many times other people got drinks for her. But she was definitely getting more drunk as the day progressed. It didn’t help that guys were goading her, and the rest of the girls, to drink. At one point, Dave even challenged Annie to a chugging contest with their mixed drinks. Dave won easily, since Annie was already somewhat tipsy.
I eventually went back to my reading, until Annie came up to me. She had just been in the pool and was soaking wet. With her bikini clinging to her every curve, she looked even hotter. “Hi, hon,” she said, somewhat slurred. “You relaxing?”
“Yeah,” I said. “You having fun?”
“Oh, yes,” she giggled. “I’m a little drunk.”
That was obvious, but I didn’t push it. Annie dried herself with her towel and went back to her friends.
I went back to my reading, until I suddenly heard a scream. I looked up quickly, in time to see Molly covering up her naked breasts. One of the guys had pulled off her top and was running around with it. Molly chased him around the pool, arms covering her chest, until he stopped and grabbed her and pushed her into the pool with him.
I heard another scream, and a girl I didn’t know was now topless, too. Instead of covering up, this one just let the guy run off, and went back to chatting with her friends.
I looked over at Annie. She was in the shallow end of the pool chatting with some of the guys, and I looked over just in time to see Alan swim up behind her and yank the strings on her neck. The top was stretched so tight that it practically sprung off her, and suddenly my wife’s tits bounced into view. She squealed and spun around, slapping at Alan. He raised her top over her head, and she laughed and started jumping for it. Her breasts bounced firmly with each jump, showing off her soft pink nipples, while all the guys around her cheered.
Dave waded over behind her and, grabbing her by the waist, lifted her high enough to reach her top. She snatched it from Alan’s hands and whipped it at him, tipsily laughing. She started putting her top back on, but not before Alan reached over and squeezed her naked left breast. She squealed again and slapped his hand away.
The girls didn’t let the top snatching go unanswered, and started pantsing the guys. A few minutes after Dave helped out Annie, Molly sneaked up behind him at the bar and yanked his trunks down. A huge cock fell out, and all the girls gasped, including Annie. Dave laughed and started chasing Molly around the pool, wagging his huge dick like a stick at her, as she ran screaming and laughing.
After a few more minutes, Annie got out of the pool and walked over to me. Before she could say anything, I demanded to know was what happening over there.
“Oh, sweetie, nothing. The guys were just having some fun, that’s all,” she replied.
“I don’t think seeing you topless and feeling you up is just fun!” I said back.
“Sweetie, don’t be such a prude. Besides, I put my top right back on, didn’t I? Look, they pulled a bunch of tops off, and half the girls didn’t even put them back on.”
She had me there. Several girls were walking around topless now, and occasionally one of the guys would squeeze a tit here and there.
“Besides,” she cooed, suddenly lowering her voice, “doesn’t it turn you on to see the guys ogling at me? Seeing my boobs and feeling me up a bit?”
I got quiet, because it sort of did. I had a hard-on after watching those guys play around with my wife. But I was also incredibly jealous.
“It’s just some harmless fun,” she said again. “Think about how naughty your wife is, letting all these guys see her boobs and fondle them.”
I nodded a bit, and she smiled widely and walked away. I felt like I should have said something, but the moment was gone. Besides, if guys were doing it to all the girls, there was no reason why I should be upset.
I tried to concentrate on my book, and eventually I put on my sunglasses and fell asleep. When I woke up, things had gotten a bit rowdy at the pool. Many of the girls were topless now, including Christine, who walked by me. She was taller than Annie, but her breasts were much smaller, more perky and teardrop-shaped. They were fully exposed, and her top was hanging from her neck, probably after some guy had just untied the strings.
I was drowsy but awake, and with my sunglasses over my eyes it looked like I was still asleep. I scanned the pool looking for Annie, and saw quite a bit of debauchery going on. Some of the guys and girls were openly making out in the pool.
I finally located Annie, who was on the edge of the pool with her feet in the water. Alan was with her, in the pool, his arms resting on her legs. They were talking, with their faces only each apart. Annie had a very coy look at her face, while Alan looked like he was pleading for something. Every now and then Annie would burst into giddy laughter. She sounded like she was still drunk.
After a couple of minutes, Annie lifted her arm and grasped one of the shoulder straps on her bikini top, and slowly pulled it off her shoulder. Alan said something which caused he to laugh again. Alan then grabbed her hand and pulled it underneath the water between his legs. Holy shit, I thought. Did he just make my wife grab his cock?
Annie squealed in surprise for a second, then laughed. She kept her hand down there, though, and her arm started moving around. Alan said something and she laughed again, then took her hand from the water and pulled down the other bikini strap. She glanced over at me, and I froze. I must have convinced her that I was still asleep, because she turned back to Alan.
Her top was now barely hanging on, held up only by her full breasts. Alan was openly staring at them, talking excitedly. I don’t know what he was saying, but it must have been the perfect mix of humor and seduction, because she seemed to be doing everything he wanted. After another few seconds, Annie reached her hand back down into the water. This time, I could see her gasp. Whatever she had felt down there, she must’ve been impressed. Alan laughed and whispered something that made her laugh even harder.
Annie lifted her hand back out of the water and squeezed her forearms together. Her cleavage shifted just enough for the top to fall a few inches, completely exposing her tits to Alan’s gaze. Her puffy nipples were hard and stood out tantalizingly from her round, gorgeous breasts.
I was hard as a rock. I couldn’t believe my wife was exposing herself to a guy like that, and I couldn’t believe I was turned on from watching it. What the hell was wrong with me?
Alan ogled Annie’s tits for a while, then leaned forward and whispered something into her ear. She giggled and reached back down into the water again. They were quiet for a minute while her arm moved up and down in the water. It was obvious she was stroking his dick. After a few seconds, she looked over at me hesitantly. I was sure that if she saw me move, she would stop whatever she was doing, but I didn’t. As jealous as I was, I wanted to see where this was going to go.
After making sure I was still asleep, Annie slid off the edge and into the pool. Standing face-to-face with Alan, her top now clinging to her stomach, she reached both hands into the water, and the two started squirmed around a little bit. I couldn’t tell what was happening until Alan’s swim trunks suddenly rose up from the water right next to him. She had taken them off!
They both laughed, then Annie put her hand back under the water. Alan started breathing heavily and stared intently at her beautiful breasts. Annie giggled at his ogling and a couple of times she lightly bounced up and down to give him a show.
Eventually Annie moved her arm up and down faster and faster, all the while watching Alan stare at her tits. Suddenly he closed his eyes and bit down on his lip. Annie looked down and stared hypnotically at the water as he started bucking. After a few seconds, he stopped and opened his eyes again. Then he whispered something that made her squeal in mock indignation and push him away. He laughed and grabbed his swim trunks while she put her top back on.
I wasn’t sure what was more surprising: watching my wife jerk off another guy right in front of me, or the fact that no one else really noticed. Looking around, I saw a lot of horse-playing, and I guess the two of them were quiet enough that no one noticed. I sure noticed, though. Surely I wasn’t just being prudish now, was I? My mind said yes, but my hard-on said no.
After another half-hour, Christine stood up, still topless, and announced that everyone was going to the beach. Since parking was tough, the company had provided several vans to haul everyone there, rather than people taking separate cars.
I pretended to wake up as Annie walked over to me. She was still tipsy, if not drunk, and I decided to see if she would confess anything. “Anything happen while I was asleep?”
“Not really, sweetie,” she said.
“Any more top-snatching?” I pressed.
“Why?” she asked teasingly. “Would you want to hear about it?”
“Maybe,” I replied, although the way she was taking the conversation, I came off sounding more enthusiastic than I did.
“Well, no top grabbing, but Alan wanted another look at my boobs, and he kept asking, so I thought that since he already saw them, I might as well give him another peek.”
“Oh,” I said.
“So I pulled down my top for a bit, and let him have a look, but that was all. Is that okay, sweetie? Do you mind me showing off for you and letting the guys have a peek at my boobs?” she cooed.
“I guess so…” I stammered. Maybe I was just imagining her jerking off Alan.
We gathered our towels and followed the group over to the parking lot to take the vans. We got into one with a bunch of people I didn’t know, and drove over to the beach. The ride was extremely bumpy, but I barely noticed, as I was focused on trying to remember what I saw with Annie and Alan.
When we got to the beach, we saw that the company had set up a volleyball net for the staff, and Christine and Nichole got a game started. I laid back and watched, trying to collect my head and get the lump out of my chest, while Annie joined in. The game was actually entertaining to watch, partly because the players were pretty good, and partly because the girls looked great jumping up and down in their skimpy swimsuits. The trash talking got worse and worse as the game went on, too.
After forty-five minutes, Annie got ready to serve. “Get ready, guys, this one’s not gonna be coming back!” she shouted.
“You want to bet your top on it?” Eddie shouted back.
Some of the guys whooped, while others gave a low “ooooh.” Annie paused for a minute, with a sexy look on her face, then shouted back, “If you can’t return it, you’ve gotta lose those trunks!”
“Not much of a chance of that happening!” Eddie replied.
Annie responded by throwing the ball up and delivering a powerful serve. I’m not sure how many of her co-workers knew it, but she used to play volleyball in college. The ball did exactly what she wanted it to do, slamming right in between the two weakest players.
The girls cheered and the guys slapped their heads and moaned. Eddie whistled and pointed to Annie, then grabbed his waistband and slid his trunks down. His dick wasn’t as long as Dave’s, but it was much thicker. It was definitely big enough to draw some whistles from the girls. Annie stared at him with a horny smile on her face. She never looked at my dick like that before.
Annie prepared for the next serve, and shouted to a guy I didn’t know, “Hey, Don! You want to make the same bet?”
Don looked over at Eddie, then over at Annie’s tits, and said, “Absolutely!”
Annie delivered another powerful serve, but this time one of the guys made a lucky guess where it was going. He dove and got a hand on it, throwing it up high enough for Dave to return it. As soon as the ball went back over the net, the guys burst into cheers, then started chanting, “Take it off! Take if off!”
Annie put her face in her hands, giggling, then reached back and untied her top. She held it against her chest for a second, then threw it to the side. Her gorgeous breasts and puffy nipples popped back on display. The guys started clapping and whooping, while Annie blushed and laughed.
Annie played the rest of the game topless, giving everyone a show. Every time she would run or jump to return the ball, her tits bounced obscenely. All the guys sported huge hard-ons watching her, especially Eddie.
The game soon ended with Annie’s team victorious. Annie walked back over to get her top, but didn’t put it on. She strolled over to Eddie, who had just picked up his trunks. I could tell she was arching her back, pushing out her tits. They started talking about something, although Annie was mostly staring at his huge cock and he was staring at her chest.
Eddie said something, then pushed his dick toward her. She giggled and shook her head, but didn’t stop looking. Eddie stayed still, though, and after a few seconds Annie reached over and grasped her hand around his cock. She held it for a second, then lightly bounced it and laughed.
Eddie laughed, too, then reached over and pulled on the front of Annie’s bikini bottom. He leaned over and stared down at her pussy, while Annie squealed with embarrassment but did nothing to stop him.
Suddenly Eddie yanked her bottoms all the way down to her ankles. Annie screamed, which caused everyone to turn and see her fully exposed pussy. She had a neatly trimmed light blond bush that barely hid her pussy lips. Her beautiful body was entirely naked now, and her embarrassed look made her even more beautiful.
Annie quickly pulled her bottoms up while the guys cheered, but didn’t put her top back on.
The sun was beginning to set, so Christine announced that everyone was returning to the resort, and that the group would meet again at the hot tub at ten o’clock.