Sandy leaned back in her chair and sighed. The day had been a long one–non-stop depositions in the morning, and an afternoon filled with planning tomorrow’s strategy. Papers and laptop computers were spread out on the table of the bar that overlooked the all-ages pool, and the outdoor air and sun were just warm enough to make the business suit she was wearing uncomfortable.
The work was always tiring, but two unique factors made today’s work even more of a challenge. First, the corporate travel agent had booked Sandy and the associate working with her on the case into a decidedly non-corporate hotel, and second, the associate working with her on the case was Sonny.
As for the hotel, Sandy knew it well. She had come there for fun many times–so many times, in fact, that she had lingered near the cab outside until Sonny had finished checking in, because she knew she’d be greeted by name and offered an upgrade to a suite. While the hotel looked like a traditional property on the surface, it was well-known in certain circles–circles that Sandy ran in outside of work–for having an “adults only” area that was decidedly…adult.
Sandy had been coming here for years, and was shocked when the corporate travel agent booked it–other options must have been limited in the post-COVID travel surge–and, in fact, used to sneak into the hotel’s adults only pool area without a room in the hotel when she was a starving law student at a law school nearby. Even when she would get caught without a room key, she found that there were other ways to make yourself…welcome…at the party.
Sonny, on the other hand, she did not know well at all. He was young. And cocky. And prone to jokes and stories that others couldn’t get away with but that he could, because his father was the Managing Partner and founder of the firm. Sonny wasn’t even his real name–it was the nickname his father gave him so that people wouldn’t confuse the two of them in internal communications.
Sonny had guaranteed job security, and he acted like it. Many was the time he had walked up a flight of stairs in the office behind Sandy and said “Man, I could walk behind you all day.” Or they would come out of a long day in court and he would say, “Damn! You were on fire in there! That’s the sexiest shit I’ve ever seen! I got hard just watching you.” Sandy found it easy to ignore–she’d spent her entire career around guys with big mouths and small dicks–but the urge to teach him a lesson was sometimes hard to resist.
“Too bad we weren’t here last week,” Sonny said, “it was National Bikini Day and it would have been fun to see your hot bod in a bikini out there.” He pointed in the direction of the pool. “Guess we’ll have to book another trip down here next year.” He laughed a smug laugh, and something inside of Sandy snapped. “Gather up those papers and laptops and come with me” she said, and rose from the table. She walked across the pool area and turned a corner, Sonny running to catch up.
As they rounded the corner, they approached a privacy-fenced area with a gate labeled “Adults Only: Nudity and Adult Acts Allowed.” Sandy swiped her hotel key in the lock on the gate and stepped inside. She looked at Sonny and said, “I would have thought that someone who knew about National Bikini Day would know that today is National Nude Day.”
Sandy slipped her suit jacket off her shoulders and tossed it on a nearby lounge chair, then peeled her silk blouse over her head before deftly unbuttoning her skirt and letting it fall around her ankles. Because she never wore a bra or panties under her work clothes, she was completely naked except for her high heels, which she very intentionally kept on.
Sonny’s eyes grew wide and his mouth fell open. Sandy was stunning–perfect stomach and breasts, and the high heels made her long legs and terrific ass look even better. “You need to do a better job with your calendar, Sonny” she said, “and you need to get those clothes off if you’re going to join me and the rest of the grown ups in here.” She walked slowly over to the chaise lounge where she had thrown her jacket and laid back, high-heeled feet crossed at the ankles.
Sonny clumsily undressed and Sandy watched, curious to see what he looked like. He was clearly trim and fit under his work clothes, but she was unprepared for how toned he was naked, and the usual cliches about “big mouth, small cock” definitely did not apply. “Come sit down on the other chair next to me, Sonny, and let’s finish talking about this case.”
He didn’t respond, and in fact wasn’t even looking at her. He was staring at the hot tub, where a man and two women were enjoying National Nude Day to the fullest. The man was leaned back while the two women gave his cock their not-quite-full attention, alternating kissing one another with running their tongues up and down his length.
Another couple on a nearby lounge chair watched them, her sitting on his lap and riding him slowly, in time to the rhythm of the music that played on the overhead speakers around the pool. “How quickly I became uninteresting to you, Sonny.” Sandy said. “You’re never going to be much of a lawyer if you don’t learn to focus on the case at hand.”
She paused and admired his body again, fixated on his impressive cock growing hard in response to the action taking place in and around the hot tub. “Would you like to go over to the hot tub, Sonny? I’ll bet those women would be happy to have you join the party.” She stood, grabbed his hand and led him to the hot tub.
As they approached, one of the women looked up and said “Sandy! I didn’t know you were coming in for National Nude Day!” The woman shifted her focus to Sonny. “Well, aren’t you a lucky boy. The rest of us hate to see Sandy come to the hot tub, because she’s gorgeous as hell and even better at fucking. You’re in for a good time.” Sandy laughed and said, “He’s a co-worker, Anne, and the boss’ son, and I don’t fuck co-workers. So why don’t you show him a good time and I’ll take your place with your husband.”
Anne pushed away, looked at Sonny and said “Sit down here on the edge of the hot tub and let me see if I can help you out with that pesky hard-on, honey.” Sandy watched Anne begin to ease Sonny’s large cock into her mouth, then turned her attention to Anne’s husband Dave, who was one of Sandy’s favorite men to play with when at the resort.
As Sandy joined the other woman in sucking Dave’s cock, she heard Anne and Sonny leave the hot tub and head for the cabana nearby. She glanced up and saw Anne lowering herself down on Sonny’s full length and girth. As he entered Anne, she groaned so loudly that Sandy could hear it over the sound of the bubbling hot tub, and a surge of heat and wetness swelled between Sandy’s legs. Sandy shifted her hips so that the water jets in the hot tub hit her clit, and she nearly came on the spot from the rush of water. She had to admit, for a guy with an entitled, sexist attitude and a big mouth, Sonny seemed to know what he was doing in bed…but she reminded herself that fucking the boss’ son was a terrible idea.
Sandy looked up at Anne’s husband and over at the woman she was sharing his cock with–whose name she had not caught yet, but whom she had already kissed deeply–and said “Come on you two, let’s go join the party in the cabana.”
The trio rose from the hot tub and scampered over to the cabana. Anne looked at Sandy and said “you may want to break that no-coworkers rule, because this guy’s cock is an absolute masterpiece.” Sandy said “I’ll start with Dave and my new friend here, and we’ll see where the afternoon takes us.” Sandy laid back on the other bed in the cabana, and Sandy’s new friend lowered herself onto Sandy’s face.
As Sandy began savoring her new friend’s taste and wetness, Dave slipped inside of her and began fucking her slowly but deeply. The three of them formed a triangle shape as Dave and the new friend leaned in and kissed one another while each enjoying opposite ends of Sandy’s body.
Sandy was losing herself in the experience of being fully naked on National Nude Day, in the moans and sighs of the people around her, and in giving and receiving pleasure in the warm sunshine and fresh air, when suddenly she remembered that just a few feet away, her boss’ son was fucking someone she had introduced to him. In the adults’ only area of a resort. While on a work trip. “Jesus, what the hell have I done?” she thought, but was surprised to discover that her first instinct wasn’t to stop, it was to…go even further.
As this thought passed through her mind, Anne came loudly and said “I need a break, Sonny! I know you haven’t cum yet, but your cock is too much for me to take for very long.” She looked at Sandy, “I’m telling you, you don’t know what you’re missing here.” Sandy looked at Sonny and said, “If you ever tell anyone about this, I’ll sue you and your whole family for everything you own.”
She moved over to Sonny’s bed and got on her hands and knees, pressing her face and chest into the mattress and raising her hips into the air–she knew she couldn’t look him in the eye in the office elevator ever again if she looked him in the eyes now. “Now, fuck me absolutely senseless before I change my mind.”
Sonny’s cock slipped inside of her, filling her the way that few men were thick enough to do. She moaned and then gasped as he went deeper, and then even deeper still, before pulling back slowly and plunging in again. Anne was right–his cock was magnificent and his skill with using it was even better. He increased his speed, and then reached around her waist, and between her legs, where his fingers found her clit and began rubbing it in time with his thrusts.
The cumulative effect of all of the fucking and sucking here and in the hot tub meant that neither lasted long–Sandy came furiously, her muscles clenching around him, and moments later he pulled out as an enormous arc of cum sprayed across her ass and back. Sandy knew it was probably the worst decision of her professional life, but it was also the best National Nude Day she had ever experienced, and she decided to face the regrets and consequences later.
She rolled onto her side and looked Sonny in the eye for the first time since she had dropped her clothing in a pile near the entrance to the pool. “Get yourself dressed and meet me back in the bar. We’ve still got prep work to do for tomorrow’s depositions, and after that I’ve got…other work for you to do in my suite.”