Anna slept for about an hour, exhausted from her explosive orgasm. I, on the other hand, was wide awake, thinking about my new found arrangement. It was a lot to take in; I still wasn't sure exactly how far Anna wanted to take this. I expected she would break by the end of the week and let me have some relief of my own.
Anna showered quickly to freshen up, and then dressed for the evening. Well, dressed is a relative term. The only thing she wore was an ankle length green flower-print sarong around her waist, which left her breasts hanging freely in the open.
"Ready?" She asked. "Or do you need more time to get ready?"
"Very funny." I tugged playfully at her sarong and she slapped my hand away.
"Hey," Anna said, taking my hands in hers and facing me. "I need to tell you something before we go..."
"OK..."
"Lisa and I were talking this afternoon while you were napping at the beach and, well... I don't know how to bring this up. It's not a big deal, really."
"What is it?" I asked nervously.
"Well, remember when Chad said he had worn a chastity device before?"
"I remember."
Anna continued, "I thought that was weird, so I asked Lisa about it. I guess she and Chad are into some kinky stuff themselves."
"Like what?" I asked, not knowing where this was going.
"Well, pretty much what we've been playing with. Female domination, chastity, control."
What were the odds of that? I thought. "And what did you tell her?" I asked Anna.
"Just that we've started exploring it recently. I said we were just starting out, and that this trip was the first time we have really tried anything. She was very nice about it. She even offered me some pointers since we're new."
"I don't know how I feel about you sharing our sex life with them." I said, surprised.
"Lisa and I used to share everything in college! We don't have any secrets. It will be fine, trust me." She hugged me close and gave me her sexy eyes. "Besides, I want to make sure I'm doing this right. She really sounds like she knows what she's doing. Now, let's go. We're going to be late!"
The sun was low in the warm afternoon sky as we returned to the boardwalk to meet Lisa and Chad for dinner. We found our destination, a little seafood restaurant, and discovered our friends were already seated at a table.
"How was your afternoon?" Anna asked Lisa as she gave her a quick hug before sitting down.
"Relaxing. We ended up soaking in the hot tub in our room and doing some shopping on the boardwalk."
"That sounds nice! I wish our room had a hot tub!" Anna commented.
Chad was quick to offer, "You guys are welcome to come over and use it sometime."
"Yes!" Lisa agreed. "We'd love the company! There are only so many things to do by ourselves, especially after the boardwalk closes down at night." She squeezed Chad's arm and grinned. We all knew what she was referring to.
The rest of the meal was casual and uneventful. The food was good and the drinks were even better. Everyone was having a few; after all, it was an all-inclusive resort and it was just a short walk to our rooms later. Anna and Lisa hit it off like the old friends that they were, and Chad and I made small talk. I discovered he was a personal trainer (go figure) and that's how he and Lisa had met. She taught a yoga class at the gym he worked at. I could have guessed Lisa was into yoga...she was fit and toned everywhere, with that perfect tight "yoga butt".
The night was still young when we finished eating, so Lisa suggested we go to a bar down the boardwalk where they have live music and dancing. We made our way out of the restaurant and down the dimly lit boardwalk. The bar had a tropical theme with open walls facing the beach, strings of lights hanging from the thatched roof ceiling. Chad and I left the ladies at a table and went to get some drinks.
"How do you like it here so far, Tim?" Chad asked as we waited. "Is it what you expected?"
"I didn't know what to expect to be honest. Anna is having a great time, and I'm glad she ran into Lisa. I'm still adjusting really." I glanced down at the cage on my crotch.
Chad laughed. "Yeah, I know what you mean. The first time we came here, being in chastity took some getting used to. That's for sure. It really opened Lisa and me up to some new things though." He turned and leaned back with his elbows on the bar, watching the crowd in the room. The way he was standing had the effect of pushing his hips forward, causing his large red chastity device to protrude from his waist obscenely.
A couple of gorgeous young ladies walked by at just that moment. Their heads turned as they passed, keeping their gaze on Chad as long as possible before giggling and turning away. He didn't even seem to notice.
"What kinds of new things?" I asked, trying to keep talking.
"Oh, the same kinds of things Anna tells us you are trying out... female-led relationship, chastity, that sort of thing. Well, I don't do the humiliation thing, that's for sure." He chuckled at that. My face grew red...I couldn't believe Anna had told him about that!
"No?" I asked, not sure what to say.
"Nah, not really my style. It just didn't fit for us, no pun intended." He pointed to his cock and laughed. He glanced over at my vastly smaller package and his tone dropped. "Sorry, man. Wasn't thinking."
Sorry?!, I thought. Who did he think he was?
"Anyway," he continued. "We got bored with the chastity thing, so we started experimenting with some...other things. And other people." He said slyly. Before he could explain, the drinks came and we returned to our table. Not a moment too soon, I thought.
Anna and Lisa were whispering as we approached, but they quickly stopped when they saw us.
"It's about time!" Lisa joked. "We were about to find some other guys to dance with!" She grabbed Chad's hand before he had a chance to sit down and dragged him onto the dance floor.
"Why do you look so down?" Anna asked, concerned.
"What? I'm not." I wasn't about to tell her what Chad had said.
