A few years ago I was presented with a proposal that dropped my jaw. My friend group that had been together mostly since high school was fairly sexually open. I had played the role of "bull" for a few of my friends who wanted to experience the hotwife lifestyle, and in pretty much each case, everyone walked away happy and content. It wasn't a secret in our group, nor was it something we talked about often.
One couple in the group, Nora and Rob, were relatively new additions. Nora worked with my friend Kelly right out of college, so at this point I had known her and her husband for about 6 years. She's very outgoing, gregarious, and positive. Tons of fun to be around. Rob is great too, but a bit quieter. He's definitely content to hang around with friends and enjoy the vibe without being the center of attention.
Anyways, one evening most of us were at Kelly's house on a weekend evening when Rob pulled me aside.
"Nora and I have been thinking a lot about adding something new, and we think we might want to try sharing her with another man."
My jaw dropped. Not because I had never done something like that before for a couple. I have. And it's usually awesome. But Rob never struck me as someone who wanted to try something like this. I told him that they'd need to think deeply about it and if it's something they wanted, I'd be happy to help out.
A couple weeks passed and I mostly forgot about that conversation until Rob texted me asking if I wanted to come over and talk about it with them. Later that evening I was sitting in their living room. I had been to their home by myself a few times before, but never with this topic of conversation. Luckily, any potential awkwardness was immediately assuaged by Nora, who's always the life of a conversation.
"Rob and I have been talking about this for months. Roleplaying, fantasizing, even a couple times we went out with me showing more skin than usual and I think we're fully ok with it," she said, excitedly.
"That's good, but you know actually doing something is a whole different ballgame," I responded.
"I know," she replied. "And to be honest, our only hang up is that we think it's best if Rob isn't there for it."
This part caught me off guard. The next part blew me away.
"So we figured the only way to truly relax and let whatever happens happen is if its done far away. Like on vacation or something."
I've had men ask me to have sex with their wives before. I've never had someone ask me to take his wife on vacation and have sex with her there. I looked over at Rob. He was looking serious, but excited.
We talked it out a bit more and once I was sure they're both fully on board and ok with this happening, we started to plan something out. Nora and I are both teachers and summer break was coming up in a few weeks. They had a bunch of airline points saved up and decided it was worth it to cash some of them in to fly us to Jamaica to visit Hedo, a swinger resort.
Normally, I would have thought this was too much, too soon. But Nora is not the kind of woman to half-ass something, and I wasn't going to argue against it. And in any case, the chance to be alone with her in a sexually-charged atmosphere for days was more than I could give up.
Long story short, a few weeks later Nora and I found ourselves in hot, tropical Jamaica, walking into the lobby at Hedo. Everything that led up to this was a whirlwind, especially with how busy work was to close off the school year. Walking into that resort started to make it all real, however.
What made it even more real was when we were walking to our room after checking in, we passed by a woman, probably in her late 40s, wearing nothing but flip flops and a big smile. I didn't want to stare, but the novelty of the situation was almost too much for me. She clearly wasn't bothered by us looking, and as we passed by her, laughed a bit under her breath and said, "First time?"
In the room, we began to unpack and an awkward silence descended on us. Other than generalities, we hadn't exactly discussed *what* we would be doing. I was comfortable with everything, even if she didn't want to play at all, at least I got to take a few days off in a tropical haven for a change.
Nora went to the bathroom to shower and freshen up. I laid on the bed, having changed into swim shorts and a t shirt. Twenty minutes or so later she came out, in just a towel, wrapped around her chest.
"I think you might be overdressed for a swinger resort, Nora," I teased.
She blushed slightly and smiled at me before going to her bag to dig out a bikini set. She faced away from me and dropped her towel, gifting me my first view of her naked body, although she continued to face away from me as she got dressed. I wasn't going to push her, but I was happy to enjoy whatever she felt comfortable showing off.
After she got dressed in a bikini with a small wrap skirt around her waist, we went down to check out the resort. Hedo has a clothing optional side and a fully nude side. We opted to stay on the clothing optional side to start off. We walked the beach a bit and then settled down into a couple of lounge chairs, staring out at the ocean. Seeing so many diverse people in varying states of undress walk around was a totally unique sight. Nora and I barely talked much as we walked around in awe.
"Do you think you'll be brave enough to go nude at some point while we're here?" she asked.
"Maybe. I don't know yet. In my current state, I might poke an eye out though," I said jokingly.
Nora laughed. "Seeing all these naked women has had an effect on you, huh?"
"Not exactly. More so the not-naked woman sitting next to me," I responded. I knew I was turning up the cheese, but she didn't mind. She turned a deep shade of red and fell silent for a bit.
A little while later I motioned to a couple about 50 feet down the beach from us. They were both totally naked, laying on lounge chairs. What was notable was that the woman was very obviously stroking the man's dick as he gently massaged her boobs. Outward sexual activity during the day is officially frowned upon at Hedo, but we soon found that this was loosely enforced.
We couldn't take our eyes off what was happening for a couple minutes, until a woman, wearing only a bikini bottom, came out of the water and started walking towards us. She looked to be in her 40s, and had a really fit body and a bright smile to match. I smiled and said hello and she asked if she can pull up a chair and sit with us.
"First time here, huh?" she asked, clearly noticing how amazed we were by the scene in front of us.
"Yeah, that obvious?" I replied with a chuckle.
"Only a little. You get used to it. My husband and I have been here almost yearly for years now."
"Where is your husband?" Nora asked.
The woman laughed. "He's the gentleman over there you've been watching," she said proudly.
Watching the look of realization dawn on Nora's face was quite a sight to see. "Wow. And this doesn't bother you at all?" she asked.
"Of course not. I find it really sexy. We met her and her husband last night. Great couple. Lots of fun," she said suggestively. "So how long have you two been together?"
I was about to explain our situation. Friends on a potential hotwife vacation. Perfectly reasonable and easy to explain, right? Before I could, Nora butted in. "About 5 years now!"
I slowly turned away from our new friend and looked Nora in the eye. This woman kept surprising me. But I figured we were going with that as our story.
"So I assume you've never shared partners with others before?" the woman asked.
"Not really," Nora replied. She paused. "But we're excited to try something new of course!"
The woman laughed. "That's the spirit!"
"I was telling my husband to drop his shorts but he's worried about being hard in front of everyone," Nora added.
My head was spinning. She was really enjoying this, partly because she could tell I was in shock at her roleplaying.
"Oh no one would notice or care, I'm sure," the woman responded.
"See babe? Just go for it!" Nora teased. I could tell now she was reveling in this.
Not one to back down from a challenge, I lifted my hips and pulled my shorts down. First time I was ever nude on a beach. Mark that off my bucket list. I glanced over at Nora. Her eyes were glued to my dick. I was pretty hard at this point and there was no way to hide it.
"See? You definitely shouldn't be hiding that," the woman said teasingly. "And by the looks of it, you need to take care of that anyways," she added, clearly meaning Nora.
Nora smiled. "I like to share. You're more than welcome to help out if hubby is ok with it!"
I couldn't believe my ears. I could only nod gently as Nora's devious smile indicated how much she was enjoying all this.
Without wasting any time, the woman (who's name I still didn't know!) reached out and wrapped a hand around my dick. She began to stroke me slowly but purposefully. She clearly knew what she was doing. I suppose multiple trips to this resort would indicate she's not a novice at touching men's dicks. Nora was gleefully watching, having shifted herself in her seat so she was on her side, facing towards me and our new friend.
She began to offer some verbal encouragement. "Do you like that, babe? First time I ever share you with another woman."
I almost laughed at how ludicrous that statement was, but I was too enthralled by the sensations to focus on her teasing. She reached for my hand and rested it on her thigh. I squeezed her thigh a bit, feeling her soft, smooth skin for the first time. I turned to her and we locked eyes. She was clearly enjoying this, maybe almost as much as me.
Our new friend picked up the pace. She was a master at this. I began to tense up. "I'm close," was all I was able to whisper.
Absolutely shocking me, Nora quickly shifted her body to lean over my torso. Before I could do anything, she wrapped her lips around my head while the woman kept stroking me. I was shocked. I had no idea what to do and couldn't hold back any longer. I erupted, hard.
My body tensed up as I shot spurt after spurt of cum into Nora's mouth. The woman continued to stroke me, although slowing a bit and letting me focus on Nora's lips on me. It took me a minute to catch my breath. Nora leaned back into her chair. She smiled at me. No cum on her lips. She swallowed it all.
The woman let go of my quickly softening dick. She leaned over and gave me a quick peck on the underside of my head. "I'm glad I was able to be your first experience. I hope you two have a good time while you're here," she said with a smile.
A minute later, she got up and left back to her room. I turned to Nora. I didn't know what to say.
She had a fulfilled and mischievous look on her face. "I forgot to mention. I'm a bit of a cumslut," she said with a laugh.
This was going to be a wonderful few days.