"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."
