The Vacation - first time being cuckolded

As months passed I began to get over the fact that my wife had been unfaithful. It seemed understandable on a certain level - if she had these needs and desires and I wasn't able to fulfill them, why should she be denied, as long as we still had a great relationship and were otherwise happy.

I planned a vacation in the Caribbean, just Lisa and I, so we could have some time to ourselves without the kids. We arrived on a Friday and spent most of the next few days relaxing and enjoying ourselves. On the last evening we planned a sunset dinner cruise and then were going to go out for drinks.

It was a great night, the people on the sailboat were friendly and dinner was great. Lisa had several glasses of wine and I noticed she had been chatting with the boat captain every time she had a chance. He was about 28 years old, and seemed to be enjoying talking with her. As the boat sailed back into port, Lisa whispers in my ear that before we leave she needs to talk about something...She invited him to meet us at the bar for drinks..."Do you mind?".

At this point it dawned on me what was happening. I asked her why she had invited him and she looked me in the eye's and said "He wants me". I could feel my blood pressure rise, a knot in my stomach as she kissed me and said "I'll be back in a few minutes" then walked over to talk with him again.

As we left the boat, Lisa told him we'll be waiting at the bar for him. He looked at me and said he'll be there in 20 minutes... a smirk ran across his face, as if to say you poor bastard, your wife is flirting with me - it was really the first time I felt like I was being cuckolded as I now know it.

We sat at the bar and waited. Lisa told me she was in the mood for some excitement, would I mind if she had some "fun". I asked what she meant by fun and she "You'll see".

He arrived and was very cordial to me while paying very close attention to Lisa. I could see her brushing up against his leg under the bar as they drank and laughed. At this point Lisa was very tipsy and I could tell she was getting too friendly with him. His Buddy's were there as well, they could all see what was going on as he and my wife flirted at the bar as I watched sports on the TV's there.

This went on for about 2 hours, it was getting late, around 11 PM and I needed to find the restrooms. I told Lisa I'd be back in a few minutes and went to seek relief. There was a line so it took about 10 minutes before I returned to find the bar stools where they were seated empty.
I searched the bar to no avail. I went outside, searched the parking lot, still no Lisa -I started to get very worried.

When i returned they were back at the bar. He excused himself to go to the restrooms and I asked Lisa where she had been...She said they were in the photo booth, she pulled out a strip of pictures of the two of them kissing and groping each other. One photo his hand under her blouse. Another pic, his hand between her thighs. She leaned over and said "It's all set, we're leaving when he gets back".

She now you can watch it, that's what you really wanted...I was very nervous at this point, could not believe she was actually doing this. He returned from the restroom a few minutes later, she said he was going to give us a ride to the hotel and we got it the car for the short drive. She told me to sit in the back, up front I could see his hand reach over and fall between my wife's legs, I heard her moan softly as her breath quickened.

When we arrived at the hotel, as I got out of the car, Lisa leaned over and kissed him and said "You're coming up for a drink". He looked over at me, all i could do is nod and he was out of the car in a flash.

At the room, Lisa and her friend went out on the balcony, she told me to please get them drinks - which she clearly didn't need. When I brought the drinks to them his hand was up her dress, Lisa's legs were slightly spread and I could see her rocking as he fingered her.

Weirdest moment was probably when he had to take his hand from under the dress to hold the drink I poured for him. I'll never forget seeing my wife's wetness on his fingers as he sipped that drink.

Lisa took his hand, kissed me and said "We're going to have some fun, you ok with that?" Without waiting for an answer she led him back to the room, closed the balcony door behind her and laid on the bed.

From the window I saw everything. They laid on the bed and clothes were quickly removed. Lisa's legs spread quickly for him as he kissed her and fingered her pussy. As he licked her pussy i could hear her moan and see her buck her hips. He kissed her deeply and then I saw my wife reach between his legs and stroke his cock. He was big, very big and hard as a rock and I could tell she was so aroused.

She spread her legs, he mounted her and with a single stroke was balls deep in my wife. I could not believe my eyes and what was happening. This was supposed to be a last romantic night for us after a wonderfull vacation and here I am outside on the balcony and there's a man 15 years younger fucking my wife and there's nothing I can do to stop it.

This goes on for well over 2 hours. Eventually I need to use the bathroom badly and at a lull in the action I gently knock on the window. They look over and giggle then she gets up to open the door. She kisses me deeply, she asks if I like watching, I can taste all sorts of things on her breath, I know what has been happening.

She climbs back on the bed and starts riding him. The guy is stroking the hell out of her and I can hear her have orgasm after orgasm, a sound I rarely hear when we make love. I take a seat in the corner of the room and watch. He flips her over and starts fucking her from behind, after a few minutes I hear him groan, straighten and roar as he unloads. I could not see where he had cum, i was hoping he had pulled out but fearing he had not.

He backed away and now I could clearly see He had cum inside her. He turned to me and said "man, your wife is good, she drained me!".

They laid together for some time as I awkwardly tried to deal with what just happened. Soon he got up, dressed and left, again thanking me and saying something like "she's a good lay, you're a lucky guy"...

After he left, I laid down next to Lisa. She asked me it I liked seeing that, another man fucking her...I told her I would rather be the one doing it but if this is what she needs I'd rather be around making sure she was safe than her being on her own with someone who might be crazy and do her harm. She agreed, and added that it was a turn on knowing I was watching them. She said she was sorry she lost control a bit but this was what she wanted and needed and appreciated that I understand.

She told me she wanted me to fuck her, something she rarely asked me to do, it was always my initiating sex. As I entered her, I could tell things were different inside her. The walls of her pussy were not tight against my thrusts. Her pussy felt like it was filled with lube, which we sometimes used to get her started. She asked me if it felt any different...I mumbled a weak 'Yes', and she said "it's because his cum is in there hunny, now fuck me". I came almost immediately, start to finish less that 4 minutes.

Although I didn't know it at the the time... on this night, at this place, I was cuckolded for the very first time.