Babysitter Loses Control

"Wait so what's your plan this week? I don't understand why you are gone a full 5 days if Lydia's only going for the weekend."

I was talking to my fiance, Amy, about an upcoming trip she was going along on as a babysitter. Lydia is the 4 year old who she looks after as a nanny 3 days a week. She is the only child of Joe, a successful lawyer who is probably around 30 and his wife, Avery. Coincidentally, my name is Avery also- guess it's one if those names that works regardless of gender. Most people who know me well call me Ace, however.

"Joe and Lydia are going to the beach just for the weekend with the Smiths. Lydia is going to leave with the Smiths to go to their cabin in the mountains for a couple days. A couple of Joe's college friends are coming in to stay with him at his condo for a couple days just to relax and play golf."

"Right, so since you are there to care for Lydia, why aren't you leaving when she does? And why isn't Avery going to the beach with her husband and daughter?"

"I'm staying because Anna's going to be in town Sunday and we are going try to hang out. And because it's a free room at the beach for a couple of nights. I've been so stressed from wedding planning, and I need to work on my tan. It won't bother Joe, he and his buddies will be out golfing and drinking the whole time. Don't worry- I have a whole separate condo room that is right next to theirs."

"I'm just not sure I'm comfortable with you shacking up with a bunch of 30 year old dudes for several days. And you still haven't explained why Avery's not going."

Amy sighed and gave me a strange look. "If I tell you something," she said, "you have to promise not to tell anyone."

I wasn't sure where this was going, but I nodded for her to continue.

"Joe hired a PI because he was suspicious Avery's cheating on him. It turns out she definitely is- the PI started following her and pretty much immediately caught them red handed. I've seen the photos and they are... not good. Joe and Avery are separating. That's why the Smith's are taking Lydia for a couple days, to give Joe a couple days to unwind- he seems pretty torn up."

The more I heard about my beautiful blonde fiance's upcoming trip, the less I liked it. But bothering me even more were these photos she mentioned. "So wait- Joe showed you sexually suggestive pictures of his wife?"

"Well yeah, if I send them to you, you can't show anyone."

"Joe SENT you these photos?!" I asked. "I hardly think thats appropriate."

My phone buzzed. It was a text from Amy that contained three photos. I opened them and gasped. They weren't suggestive, they were pornographic. Avery and her new lover were nude on a boat, and the pictures appeared to be taken from some distance with a powerful lens. In the first, they were standing side by side, their backs to the camera looking toward the water. I felt my cock stir a bit in spite of myself. Avery was a skinny petite 25 year old and her bare ass looked amazing. In the second, she was on her knees, with a rather impressively sized dick in her hands, as she smiled up at the guy. This picture was in profile and offered a side view of her perky tits. The final one was Avery riding the guy as he lay on his back. They were having sex, no question. Avery was squarely facing the camera, a look of ecstasy and concentration on her face.

I was horrified. "Amy, Joe should not be sending you pictures like this. It's inappropriate- you're his babysitter."

"Ace, I'm 22 years old. I'm not a child. And give Joe a break. He's hurting right now. Besides," she said taking a step closer with a devilish grin, "don't act like you didn't like those pictures of Avery. You sure examined them thoroughly. I bet you're hard right now." She grabbed my dick through my shorts.

"That's what I thought," she said grinning and starting to rub gently. "Not as hard as that guy in the pic though, that thing was huge. At least Avery got her money's worth," she joked.

I refrained from reacting negatively to this comment because things were looking pretty favorable for me to get some action here. After all, Amy was leaving tomorrow for five days- I'd better get it while I can. Moments later, she was peeling her shirt and bra off, the last remnants of her clothes, as she straddled me and climbed onto my cock. Amy's about 5'5" with medium length blonde hair. Her tits are at least C's- maybe D's now as she's probably gained 5-6 lbs in the past few months. Not that I minded at all, she still looks fantastic naked- it's just enough to make everything bounce ever so slightly as she wiggles on my cock. Even with the few extra pounds she still has a slender, tight little heart shaped ass that is maybe her best feature.

In only a couple minutes I'd cum on the floor (Amy never let me cum inside her or onto her). She all but kicked me out of her place after that, claiming she needed to shower and pack and get a good night's sleep before her trip.

As I drove home, I kicked myself for not pushing back harder on Amy about going in this trip. She was going to the beach for five days with a 30 year old guy who was for all intents and purposes newly single. And she was going as a babysitter but staying well past the time any children would be there, replacing the family environment with a couple extra single guys. On top of that, Anna would be in the mix. Anna is Amy's college friend who's much sluttier than Amy ever was and tends to be a bad influence on Amy. I've stated in front of both of them that Amy makes terrible decisions when she's with Anna. Needless to say, Anna and I don't like each other much.

I trust Amy of course, she has a flirty care free side that is part of why I love her, however it makes me nervous when she's away. In retrospect, she's clearly used sex tonight to manipulate me and steer the conversation away from my reservations about her going on this trip. I resolved to keep close tabs on her the next five days.

Day 1- Friday

They left early Friday morning on the 4 hour trip to the beach. I was busy at work and momentarily forgot my worry about Amy. I took a break in the early afternoon to eat the lunch I'd brought and checked my phone. Amy had sent a text a few minutes ago. It was a photo. I opened it and saw it a picture of Amy in a blue bikini. It wasn't tiny but it was one if her more low cut ones and showed plenty of cleavage. She was crouching down next to the pool, holding a pool toy and apparently interacting with a child who wasn't in the frame. The way she was leaning forward showed even more of her large boobs. "Hey baby, we made it safely. At the pool playing with the little ones, I love being a babysitter!"

I was glad she was having fun with the kids but I groaned internally as I thought about her prancing around in that little bikini in front if Joe and probably plently of other grown men at the pool. Worse, another adult (probably Joe) must have taken the picture, fully aware of how much of her body was revealed in it.

I didn't get an update for a while after that so I called her when I got off work. No answer. After a miserable few hours of me trying to entertain myself with TV and video games, she finally FaceTimed around 8pm. "Sorry babe, my phone died. My charger isn't working so I had to borrow Joe's. We just got Lydia to bed, she was exhausted after a long day at the pool." I noticed she was still in the same bikini top.

"Amy did you wear your bikini all evening?" I asked.

"Well yeah, we were so busy after the pool getting the kids fed and in bed, I didn't have time to change. I put on pants though, see?" She scanned the phone down her body to reveal she had indeed put on some very tight black yoga pants over her bikini bottoms. Still, I silently lamented how much of her tits and bare midriff had been on display all evening.

"Don't you think you should cover up a little more?" I asked.

"Ace, I'm at the beach. Relax a little- no one's looking at me here. It's a family resort."

I knew for a fact that every dad at that pool had enjoyed the sight of Amy all afternoon but I kept my mouth shut.

We talked a few more minutes and I was relieved that she made her way back to her own room as we did. Finally we said our goodbyes. I went to sleep thinking that maybe I'd worried needlessly.

Day 2- Saturday

I woke up around 7:30 the next morning and decided to facetime Amy. I figured the kids would have her awake already. Surprisingly though, she looked sleepy eyed and I could tell right away that I'd awoken her. I also immediately noticed that she wasn't in her room where she'd been last night when we hung up. She appeared to be on a couch. She was wearing a pink nightie that I recognized- it was among her most revealing sleepwear items. It barely covered her ass and had a tendency to ride up and reveal her butt and pussy. I usually loved that thing but not in this context.

"Amy where did you sleep?" I asked.

"Fell asleep on the couch," she muttered sleepily. "I was almost asleep and then realized I still had Joe's charger. I went to take it back and planned on coming right back, but we ended up talking on the couch for 3 hours til almost midnight. Joe said I just fell asleep face down on the pillow as we were talking. Don't worry Ace, he was a gentleman. He just put a blanket on me and went to bed."

I sighed. There was no doubt in my mind that the nightie had come up to reveal her ass if she fell asleep face down. I'd admired her butt many nights as she slept in that position. There was only one question to answer.

"Amy are you wearing panties?"

"Well... um... no. You know I don't sleep in panties, and like I said, I never intended to stay over here more than a minute."

"Amy, I know that nightie you're in. There's a 100% chance your ass was showing in that thing. Hell, you were probably showing a lot more than that while you guys sat there talking for hours. No wonder he wanted to talk." I was getting worked up.

Amy's eyes narrowed. "Sure Ace, it couldn't just be because I'm an interesting person or because he's lonely without Avery. Had to be because he just wanted to see my pussy. For your information I was very aware of it and very careful not to reveal anything."

"You couldn't gave been aware when you were asleep!" I exclaimed.

"Well if he saw anything, which I doubt, he immediately covered me with a blanket. I don't understand why you're so untrusting, babe."

"Whatever, forget it," I said. Arguing wasn't doing any good. "What are you guys up to today?"

"Eating breakfast, and then going to head to the beach. I'll call you later," she said, and hung up. She was clearly irritated with me.

I didn't expect to hear anything until that evening, but my phone rang again about 4 hours later. A facetime call from Amy.

When I answered, she was breathless and looked flushed and a little panicked.

"Babe," she said, barely above a whisper. "I'm in a situation and I don't know what to do. The girls got tired on the beach so Joe and the Smiths asked me to bring them back up to the condo and feed them lunch and then put them down for a nap. As I was carrying Lydia to her bed, she spilled milk all over me. I put her down and then walked next door to my condo room to put my clothes in the wash. I realized I had some stuff of Lydia's to wash too so I walked back over to grab it, but i realized I didn't bring my keycard with me. So I'm locked out of both condos."

I was confused. "So why not go get a key from the front desk, or from Joe? I don't understand what the issue is."

"Well, um... since their door's like 5 feet from mine, I didn't bother putting my clothes back on after I threw them in the wash. I was planning to just sneak into the other condo and be back in 5 seconds." She panned down her body to reveal that she was indeed completely naked. Holy shit.

"Ace, some college kids just got off the elevator and saw me. I think one if them took a picture before they left! What do I do?"

My heart was pounding. "Is there nothing you can cover up with?"

"There's only some kids toys- wait. Hang on I'm putting the phone down."

For a couple minutes I saw only blackness as she's apparently set the camera face down. Finally she picked it up.

"Ok the kids have this sand sifter toy that has handles on each end. I took the plastic handle off a toy bucket and threaded it through the handles on the sifter. It's at least covering my front, see?" She held the phone where I could see. It looked ridiculous. In any other situation I would have laughed. The toy was about 8 inches in diameter and would have done a decent job covering her front except for the fact it was a sifter that was full of holes. Still, at least it somewhat obscured the view of her pussy. The bucket strap went around behind her above her ass and hung on top of her ass cheeks to hold the sifter in place. Obviously it offered no coverage of her butt, and she was still completely topless.

"Oh shit, babe, someones coming." I suddenly got a very zoomed in view of her ass and then the screen went black again and I realized she was using the phone to try to cover up her butt as she retreated from whoever was coming.

"Amy?" I heard a male voice say. "What are you doing out here? Hey- uhhh... whoa why don't you have any clothes on?" It was Joe.

The call dropped- either she hung up or it got disconnected somehow. For several agonizing minutes I waited. My fiance was naked with another guy and I had no way of knowing what was happening.

Finally, she called back a few minutes later. She was giggling which surprised me. "What are you laughing at?" I asked.

"Well I was explaining what happened to Joe and I was so embarrassed and almost crying and midway through my explanation he just busted out laughing and then I realized how ridiculous the situation was and started laughing uncontrollably too. He let me in immediately but we were both laughing so hard that I fell on the floor. Babe I could hardly breathe. Anyway he got me a towel and went to the front desk to get me another key card."

"I can't believe you find this funny," I said.

"Oh, lighten up. He was nice about it and it's not like he was sitting there leering at me, he was laughing too hard anyway. Besides, I covered my boobs with one hand and my butt with another. He couldn't have seen much."

"Yeah," I said sarcastically, "I'm sure you did a great job covering yourself while you were literally rolling on the floor laughing."

"Babe, you need to relax. It was an accident and it's over and its funny now."

"I'm sorry I don't find my fiance horsing around naked with other dudes funny." I hung up in anger.

I didn't call her back the rest of the day. I expected her to call and apologize but I didn't want to be the one to cave. I slept poorly as I was worried about the way the week was developing. And tomorrow the kids were leaving and the environment would turn from a family vacation to a guy's trip. A guy's trip my fiance happened to be on.

Day 3- Sunday

I caved and called Amy the next morning. She didn't answer and it took a couple hours to call me back.

"Sorry," she said. "I've been getting the girls packed for their mountain vacay. They just left with the Smiths."

"Gotcha. Where's Joe?" I asked, trying to sound as uninterested as possible.

"He went to get a workout in before his friends get here this afternoon," she answered.

"Cool, what are you doing the rest of the day?" I asked.

"Anna's coming by, we are gonna go shopping and maybe to the beach and then go out later tonight."

We talked for about 5 more minutes, during which Amy semi-apologized for yesterday's events, but still didn't really understand why I was mad in the first place. She called it "harmless".

We hung up and I tried to keep myself busy. Two hours later, I got a text from her. "Trying on bathing suits with Anna." A picture came through moments later and I did a double take. It was her and Anna, topless and covering their tits with their arms. In the mirror I could see their asses in matching bikini bottoms that were very nearly G strings. Anna may be a bitch but she was an attractive one with light brown hair and a perfect rack. It was a very sexy picture. Then I noticed something else. There were feet just visible in the mirror, with men's shoes on them. It had to be a tall person taking the photo, because it was taken at a slightly downward angle, even in relation to Anna, who was pretty talk for a girl. The feet and ankles in the mirror appeared just between the girl's knees and the rest of his reflection was blocked by their nearly bare asses and naked backs.

"Amy, who took that picture?" I texted.

"Oh, her boyfriend Seth came with us."

"What the fuck, you're just trying in bathing suits in front of him?"

"No silly he just barged in, but we heard him coming and covered up, and now we put our tops back on. He didn't see anything. I told him if he was gonna come in he had to give you the same view he got of us, so we took the picture just for you. But now he's being a tool and trying on Speedos." This one came with a shrug emoji.

What the hell? I angrily tapped my phone to make a call to Amy. She answered on the first ring.

"Hey babe," she said. "Ok this might be another situation where you have to be here to get how funny it is, but... um... Seth won't fit in this speedo."

"What? Amy why is he trying on swimsuits in the same room as you?"

"I don't know, Anna and him have some dumb bet that he wouldn't wear a speedo to the beach and he just came back here with one and tried to put it on."

I heard some crosstalk and Anna giggling in the background and I thought a make voice said "well help me out." I heard Amy gasp and more laughter from Anna.

"Amy, what the fuck us going on? You said I get to see everything the other guy sees, so clue me in."

"Ok fine, hang on."

She FaceTimed. She was red in the face and obviously had been laughing. "Ok babe don't shoot the messenger but you said you wanted to see. Just remember I am here against my will." Her occasional giggle told me she was not there against her will.

She flipped the phone around and there was Anna standing next to Seth. Anna was in a yellow bikini and Seth was naked except for a comically small speedo, with an enormous boner hanging out of it. Anna had the boner in her hand and was slowly stroking it while rolling her eyes at Seth who was cracking jokes about the predicament.

Amy narrated, "I guess Seth got his big thing a little excited when he took the picture and the speedo he was trying on wouldn't accommodate it. He said he needs Anna to get rid of it."

"Amy get the fuck out of there. Why are you watching this?" Anna was stroking faster now.

"Well the shop owner just knocked and said people are waiting on the dressing room and we need to hurry up. If I open the door, whoever's waiting will see whats going on. I'm stuck." She was whispering.

I heard a knock and a loud voice. "Ok if you guys aren't out in 2 minutes, I'm calling the cops."

"Fuck, Anna take your top off, I need a little visual to finish," Seth said.

Anna obeyed, removed her top and began playing with her tits. Even as dumbstruck and pissed as I was, I had to take a moment to appreciate how nice they were.

Amy put the camera back on herself and whispered that she had to put the phone down and change back into her clothes.

Wait- was she about to strip naked in there to change? I got my answer quickly as she pit the phone down camera up. She untied the back of her bikini top and let it fall. As her tits bounced into view she quickly hooked her thumbs in the bottoms and slid them down. I couldn't believe what I was seeing. She leaned over to pick her panties, and stood back up to turn them right-side-out. Just then I heard a loud grunt. Amy froze for a second that seemed to take forever as I waited for her to cover herself.