Does She Know

Note: This is story that involves wife-sharing.

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"Does she know?"

"No, does yours?"

"Nope."

This was how most conversations started. For the past few years I had been chatting with other married men online. Many of us had similar experiences. We stumbled onto the terms "Wife Share" and "Cuckolding" online and it wasn't long before these became our new fetishes.

I was regularly signing onto chat-rooms where men shared porn links, chatted and even swapped pictures of their wives. I enjoyed discussing scenarios with others where we pictured our wives seducing and fucking other men. We all seemed to enjoy going into detail about what our women would be wearing, where it would take place and what the other man would do to her...or her to him.

Usually, I'd end up chatting with a different person every time, having the same conversations over and over. Although it was the same conversation, it was always a huge turn on for us to admit our secret anonymously to one another. Every so often I'd reconnect with someone and we'd pick up where we left off, still it was never the same as the first confession. That was until one night when everything changed.

I can't remember where the conversation started. I can't remember who started it but we chatted for over an hour. We went into a detailed role-play that started with us going on a double date with our wives and ended in swinging. Since both of us seemed to be into very similar stuff, the conversation flowed naturally. We were very horny and did a great job of turning each other on.

When the conversation finally ended, with intense orgasm of course, we left agreeing to meet again soon. I wasn't sure if it would actually happen but about a week later I saw my new friend online.

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It wasn't long before we were trading links and talking about how turned on we were.

"I'm so horny, " I told him.

"Yea same here. My cock is really hard."

"Mm, nice."

"Would you jerk off with another guy in the same room?"

"Actually I have thought about it...the idea turns me on."

"Fuck. Same here. Imagine us jerking to these in real life?"

After reading that my heart started pounding. I had never really admitted it to anyone before, but I was actually a bit bi-curious. I was turned on by the idea of mutual masturbation. I was even turned on by the idea of sucking another guy's cock.

"How far would you go with a guy?" I asked.

"Depends on how horny I am, lol."

"Same here," I admitted. We didn't take it much further that night. We continued trading links until eventually we came. It would be another couple of weeks before we chatted again.

This time I had been sharing wife-share porn links. This got us into chatting about erotic stories we had read online. Will told me he loved stories where the wife dressed really slutty and went out into public. He loved imagining her being ogled. I admitted that what turned me on the most was the woman taking charge. I especially loved stories where she would fuck another guy with a bigger cock. In fact, in one of my favourite stories, the woman ties up her husband and forces him to watch her with another man. Additionally, I also enjoyed first-time swinging stories where couples got flirty and had sex in a sauna or a hot tub.

We were both very turned on by each other's stories and as we continued to meet online to chat, we would go through scenarios of our wives going out in sexy clothes and seducing men. We also chatted about swinging together.

Months passed by. Will and I continued to chat online every so often. He was no longer a some stranger form a pervy chat site. We were actually friends. So much so, that when a business trip took me to Miami where he lived, we decided to meet.

Will came to see me at a pub near the hotel. We had a few drinks and chatted about sports and movies mostly. I almost forgot that we had met online, it felt as if we had known each other for years. The following day, we planned to meet up again. Will showed up a bit early so he came up to my hotel room. While I was getting ready he turned to me and said, "Hey, remember there was a video you sent me with a hot brunette? I found another of her...did you want to see it?"

This was the first time we acknowledged our perverted conversations. I remembered the video he was talking about and responded with, "Sure why not?"

We sat next to each other on two chairs with my laptop on the desk. Will brought the video up. It was a sultry striptease. The woman definitely looked as if she was enjoying herself - something I loved to see. When the video was over, I decided to show Will my stash. I opened the hidden folder of pictures I had saved. They weren't many but they were the ones that I found really hot.

"Mmm," he moaned, taking it all in.

However, it got a bit awkward. We both felt silent. Will stood up and we left. We picked up some food and had a couple drinks at the same pub. This time it was a Friday night so there were more people. We were both enjoying the great view of women in sexy clothes. The alcohol seemed to take away our inhibitions and we finally started to talk about our wives. At the time, Will's wife Jennifer, was away visiting her parents. He admitted that he was really horny but was so busy the last couple days he didn't even have time to watch porn.

"We should go back to the hotel and continue what we started," I heard myself say. This actually seemed to be what Will was waiting to hear. Before long we were back at the hotel sitting next to each other watching porn together. We had always talked online about how hot it would be to have a jerk off buddy in real life, now here we were. We started talking about our wives, mostly going over the same scenarios we had discussed previously. However, this time there was something about discussing it in person that added to the excitement.

"I'm so horny," I admitted.

"Me too," he responded. I adjusted the way I was sitting because of the bulge in my pants. I glanced over and saw he was clearly hard as well. Then his hand reached for his cock and I could see him rubbing it through his pants. "What the hell?" I thought, then I stood up, unbuttoned my pants and pulled my zipper down to take my cock out.

"Thank God," he said before doing the same. I looked to see what Will had been hiding in his pants. I was surprised by what I saw. He said his cock was 7 inches when we had chatted online but he didn't mention how thick it was. Will had one of those beer-can cocks. Although it was only an inch longer than mine, it was probably twice as thick. Seeing his hard cock made me so much hornier.

We spent the rest of the night there jerking off to porn. When we both finally came, Will simply got up, fixed his pants and left.

The following day I was leaving. We got together for a quick lunch. We didn't discuss what happened the previous night but it was clear we had both enjoyed each other's company. We talked about how strange it was that we had become so close but our girls had no idea. As we talked about it more, we decided on a plan. I'd book a short vacation with my Angela to Miami and we'd orchestrate a situation where four of us would meet. We'd act like we didn't know each other but then set things up in such a way the four of us would hit it off.

I was really enthusiastic about this idea and when I went home I told Angela about how nice the beach looked and suggested that we should go back together. She was into it. I told Will.

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It felt like our trip couldn't come fast enough. I was perpetually horny thinking about the possibilities. Deep down I knew nothing would likely happen the first time we all met but that couldn't stop me from fantasising.

Finally, we were at the hotel. The view was great, it was right on the beach. Will and I had a plan in place about he would meet us. Angela and I would go for a walk on the beach and from there we'd find Will and Jenny.

Angela and I didn't plan to go in the water just yet so she didn't bother to put her bikini on - unfortunately. Nevertheless, she looked great in her yoga pants and tank-top. The weather was perfect, we strolled up and down the beach. I suggested renting a beach chair under a big umbrella, Angela was up for it. Then as I reached for my wallet I "realised" I had forgotten it. In came Will.

"Hey! Jack, right?" Our back story was that we had met when I was here on business previously. Will then insisted on paying for the chairs and umbrella and hung out with us for a while. He was very polite and charming with Angela which I appreciated. She seemed comfortable with him. That said, where the hell was Jenny?

When Angela excused herself to use the washroom, I saw Will staring at her ass. "Mmm, you weren't exaggerating. She's so hot. That's such a perfect ass!"

"I'm glad that went well," I said with some relief. "Is Jenny coming?"

"So here's the thing, Jenny's mom is sick. It's nothing serious but last night she had to go her parent's to help out. She should be back in two days but I was thinking you and I could lay some groundwork for now."

"Fuck. Oh ok. Well let's make the most of it. It's still a great get away for Angela and I. We haven't done a trip in quite a while."

Soon enough Angela was back and we all got talking, Will told us as a local he knew the best spots and recommended some restaurants. I insisted that the next day he'd have to come back for me to buy him a few drinks to return the favour for the chair and umbrella. That night Angela and I went to a restaurant nearby that Will suggested. We had a romantic dinner and went back to the hotel for some more fun. While having sex that night I looked at her body thinking about how Will had gotten an eyeful earlier. This thought turned me on so much. It turned me on further to imagine him at home jerking off to the image. After we came, I went down on Angela and made her cum a second time.

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Angela and I spent the following day relaxing and enjoying our time together. It wasn't until the evening that Will showed up. I suggested we go to the bar near the hotel pool. We picked up our conversation from the day before. Will got a chance to talk about Jenny. We all agreed that the four of us had to double date. Of course Will shot me a cheeky glance when Angela showed enthusiasm about the idea.

As it was off-peak season, the pool area was fairly quiet. I suggested going in for a swim. Angela went up to change into her bikini, Will and I were already in shorts. With both of us alone, I told Will what I was thinking about while having sex with Angela. He admitted he came really hard the previous night to the thought of a foursome.

When Angela got back, Will couldn't help but stare. He blushed when she smiled at him. Her bikini was black and white. The top did an excellent job of putting her 36C breasts on display. Her shoulder-length brown hair blew in the wind as she came closer, it looked like a slow-motion scene in a movie. I looked into her pretty, brown eyes and thought about how happy I was that she was mine.

We all swam around in the pool for a while. Little by little the already quiet area cleared out even more save for us three. With the wind it got a bit cooler so we decided to go into the hot-tub. It was Will's idea. He did a great job of acting as if it wasn't a scenario him and I had chatted about multiple times.

Of course, in real life it turned out to just be three of us having a regular conversation. Nothing sexual happened. Still I took some mental pictures to enhance the jerk off sessions I would have later. She looked so sexy, all wet in the tub. Her nipples were hard under the top. I could tell she was getting horny as she rubbed up against me. She didn't seem to mind Will being there though. Maybe that was a good sign? Still, the idea of her with someone else in real life terrified me as much as it turned me on.

Soon enough Angela excused herself. She was getting tired. As she headed off Will had no shame in enjoying the view of her ass. It looked great in that tight bikini bottom, like a perfect handful.

"How hard are you?" he asked. My heart started to beat rapidly.

"Very," I admitted.

"Mmm, fuck. I'm gonna go home and jerk off so hard!" we both laughed but we knew it was true. Will towelled off at the pool and headed back home, I went up to find Angela in the shower. We started in there, ended up in the bed, then on the floor then the bed again. It felt like a second honeymoon. ---- The following day was Angela's spa time. I slept in late while she went to indulge in the full package - massages, mud soaks etc. I mostly lazed around the room but then I had the idea to pick out an outfit for Angela. We had in mind to go dancing and I wanted to dress her up nice and sexy.

I took out a sexy black dress with a very thin material. It reached about six inches under her ass. The straps were the thinnest they could be without falling off. The chest area was thick enough and shaped so that she didn't look trashy without a bra. Next, I got her some black matching stockings complete with a garter belt. For underwear I put her black satin thong. The truth was this was my go-to outfit for her. I loved seeing her in it. Nothing turned me on more than garters and stockings.

The heels completed everything. I loved how she looked in her makeup. Because Angela doesn't always wear makeup when she does there's something extra sultry about it. I love how she looks with the smoky eyes and dark red lipstick.

When she got dressed up that night, she did not disappoint. She seemed in a really good mood after her day at the spa. We couldn't keep our hands off each other while dancing. In the end we only stayed out for about an hour, we needed to get back to the hotel.

We got back into the room and started making out like a pair of teenagers. I groped at her ass and could feel the outline of her thong underneath her dress. One of her hands grabbed my hair and pulled at the back of my head while the other moved to caressing my chest. She sucked at my lips harder and bit gently then pushed me onto the bed. I moved backward to make room for her to climb onto me. She reached into her bag and pulled out a pair of handcuffs. She held them up with a smirk. I put my hands up to the bed-head anticipating her next move. She cuffed my wrists so my hands were above my head attached to the bed-head.

Angela then kissed me, put a finger to my lip and slowly traced it down my neck all the way until the bulge in my pants. She patted it then turned around and walked away toward the bathroom. I assumed she was going to change into lingerie. She didn't need to. I loved the way that black dress looked on her.

Just then there was a knock at the door. "Shit, who could that be?" I thought. I was hoping it would be someone Angela could get rid of quickly. The door opened. I heard a low murmur.

When they came in front of the bed I wasn't fully surprised, but it still felt like a dream. My heart started to beat faster, my breath quickened. My stomach was filled with butterflies. I didn't know what to say so I just stared stupidly.

Will gave me a wink then for the rest of the night he directed all his attention toward my wife. It didn't take long for them to start groping at each other. Seeing his hand on her ass, I imagined he felt the outline of her thong the same way I just did. Then his hand moved down to her thigh, he could feel the straps of her garters now. Meanwhile, I could see her nipples hardening through her dress.

Angela didn't waste any more time. She started unbuttoning his shirt. Caressing his body, paying particular attention to his abs. He stared at her hungrily. She unbuckled his belt, pulled his zipper down and yanked his pants off. His hard cock was free.

I didn't know what Will did to organise this. I had no idea what lead up to this moment. The only possible time they could have spoken was the morning before when I slept in and she had gone to the spa. But whatever he told her, she played the character well. It was exactly what turned me on. That said, at this point it was clear she had not seen his cock before. When it popped out of his pants, her eyes opened wide and so did her mouth.

Seeing this big, throbbing cock right in front of my wife's face drove me crazy. My own cock was bursting in my pants. I writhed on the bed looking at what was before me. Angela held his monster in her hand for few seconds. She was visibly nervous, not sure what to do next. Then, she shot a glance at me and saw the look on my face and my shallow breathing. I knew she could see how horny I was.

She closed her eyes and put her lips on it. He was so big that he couldn't easily fit in her mouth. She was just sucking on the tip really. Jerking the cock off with one hand she reached the other around and gripped his ass cheek.

Will's loud breathing turned into moans. His hands reached into Angela's hair and held her head while she serviced him. She was getting into it. It wasn't just a role-play anymore. As he slowly thrust back forth, forcing her mouth to take in more and more, I heard her gagged voice, "Mmmmhmmm."This took everything to another level. I was so horny watching this. It was hotter than I could ever imagine. At this point her nipples were threatening to cut through her dress.

Angela then changed gears. She stopped jacking him off and started massaging his balls and licking his shaft. After doing this for a bit she looked up at him expectantly. Will walked to the side of the bed and sat down next to me. I saw the huge cock glistening with the mixture of pre-cum and my wife's saliva. Angela, who had stood up, made eye contact only with Will and slowly pushed her straps off each shoulder, then rolled her tight dress off her body.

I lay there admiring her body. Her perfect face, with the red lipstick and dark eyes, hard nipples on those firm breasts. I loved the way her legs looked in stockings. She turned around and faced away from us, giving me the view of her ass that I badly wanted to see. As slowly as she could, she bent over and slipped the thong off. I could see how wet she was. Her crotch was glistening.

Will got up and let Angela lay down on her back with her legs open. Her head was facing the opposite direction to mine. She placed one of her feet on my chest and opened wide for him. Will came back next to me and kneeled down in front of my wife's hungry pussy. She just stared at his cock. Will held his cock with his right hand and pressed the tip against her glistening pussy-lips. He rubbed it up and down, slowly. Her eyes closed and the pace of her breathing quickened again. As he squeezed the tip in, Will let out a moan. She did too, except hers sounded more like she was in pain. Her eyes tightened. The way they were angled, I could see everything. I wasn't sure how to feel. It didn't feel real, it felt like a dream. I had secretly known Will for so long and our friendship was so perverse that in a weird way, it felt normal to be in this situation. Yet, with Angela there as turned on as I was, I was still freaked out and nervous. I resolved to just enjoy the ride and forget about everything else.

Their pace gradually quickened, I could hear his balls hitting against her. I could smell their sex. Will leaned forward a bit and grabbed onto Angela's breast. Seeing them bounce around must have taunted him so much. As he squeezed them she let out a louder moan. He pinched her nipples as he continued to slam her pussy.

Angela's entire body seized up. She was having the most intense orgasm that I had ever seen. Will took the hint and slowed down his pace just slightly but thrusted harder. When she collapsed on the bed, he drew his cock out and let her catch her breath. I had never seen her like that but when I glanced back at Will's still-hard cock, it was obvious why she had this reaction.