Ask Emma Pool

Ask Emma: We had a vacation cuckolding experience and I don’t know how I feel about it.

Hi Emma,
Thank you so much for your articles, I can relate to so much of what you write. My name is Tanya (not my real name) I am 46, 5’9 and unfortunately curvier than I want to be. My husband Brett (not his real name) says it is my best trait but he has always been excited for bigger girls. We have 4 grown kids and we have a great sex life but we are looking to expand after 20 years of marriage. We have some mild kinks (panty fetish for example) but this last year has been pretty vanilla. I have only been with him for our whole marriage and actually my whole life. I never really knew about his fantasies until about 2 years ago. I feel like I barely know the man now but he is so loving, caring and respectful to me. I would do anything for him. That is why I am writing asking for advice.

I am no stick in the mud but I like to dance, sing, and have some wine but never really get drunk that much because of the kids. We have done the extra partner “cuckold” thing once on a trip but even at my age I am learning. I’ll get to that later though. I think i even have shocked him about my fantasies. I have held them in secret for so long. Guilt too. I felt guilty for having them. Like I was a terrible person for having these kinky, pretty bawdy thoughts. Brett didn’t even know how to process them. Still doesn’t, so I can’t really talk about it with him and roll with his kinks and fantasies for the most part. My friends can’t even understand this, the hardest part is I have nobody to talk to about this side of me. I have been so vanilla until this last year. My kinks might even offend you. Lol.

So here is the story of the first time we tried his cuckold fantasy. We got a fancy resort condo in a tropical place and it was beautiful. Anyway to get right to it there was a pool party at the resort. We started drinking a lot. And you can guess after the music started that I was dancing pretty well with anyone that came close. Brett tries to dance but he is not that coordinated. Getting to the point, a few younger guys (for me) 25ish were wanting to get real close with dancing and getting hands on. I have to admit that I felt sexy that these young guys wanted to dance with a woman almost twice their age.

Brett was just looking at me smiling and I was a little at first upset he wasn’t stopping them but I think he saw how much I enjoyed having the undivided attention of these men. I was buzzed so I decided to let them feel parts, my behind, breasts, cupping my butt a lot. It was thrilling to have the attention but at same time, I don’t know I was mad at Brett for not stopping it and taking me. I looked into Brett’s eyes and then I kissed one of the two men pretty deep while he groped my butt. I opened my eyes and looked into Brett’s. I’ll be honest, it was extremely hot and I saw a fire in my husband’s eyes. Shortly after our dance we left but Brett insisted that I ask for the phone number of my new “friend”. He said that his name was Rafael, he was Hispanic with darker skin and very charming. Kept saying things to me in mixed Spanish and English which I found to be hot even though I had no idea what he was saying part of the time.

We went to dinner, ate and went to a drag show which was fun and danced some more. We danced closer this time and when he was dancing with me I felt him push himself against me and he was huge. Brett is just under three inches erect and this was easily twice that I couldn’t tell for sure but probably more I just couldn’t tell yet. We eventually invited them back to our resort and I was feeling a good buzz but not too drunk so we went out to the pool with them and pool and they were taking edibles with alcohol. There was music playing so I started dancing by the poolside with Rafael and he asked for my underwear. I told him to ask Brett and my husband couldn’t have been more excited to get them off on me to the point he almost knocked me in the pool! Clumsy.

We eventually went back to our room to hang out and we three are in our hotel sitting on the bed with Rafael on my left and Brett on my right. Rafael starts touching me and i was so worried for some reason for Brett’s approval. He was just looking at us with a blank stare. Finally, I was shaking to the point of fear, anxiety, pure horniness, lol that I didn’t know in what order. I didn’t know what to do next so I waited for Rafael to make the next move, he touched my breast and next thing you know we were lying on the bed kissing. Rafael led my hand down to the front of his pants and OMG it was even bigger than when I felt him grind on the dance floor. I was part afraid and fascinated but extremely turned on.

Brett was sitting beside us, just watching and he was so excited. I asked Brett for protection and he had one of course but for what reason I don’t know. He must have picked it up earlier in the night because we haven’t used them for 15 years but whatever. I took the condom and asked Brett if he was sure about this, he nodded his head and barely let out a quiet yep. Turns out the condom Brett had didn’t fit, Rafael was too big in the head of it so we couldn’t get it over. So Brett goes back to the pool to ask people like a college kid losing his virginity and turns out Rafael’s friend had some. The pool was close so Brett wasn’t gone long but I stroked Rafael and explored his penis while my husband was away. Rafael was everything my husband wasn’t and that turned me on in a big way. Rafael slipped his fingers into me and there was no mistaking how aroused I was. I pulled some lube from my suitcase to stroke his cock with. I was embarrassed to even try a BJ because I didn’t think I could get my mouth around due to Rafael’s girth so I just used my hands. Brett came back in the room holding two condoms that he got from Rafael’s friend. It struck me as he was standing in the door that my husband went out to get condoms so another man could have sex with his wife in front of him. Insane.

We did alot of doggie style because he didn’t fit at first and I was so worried about his thickness I was all tightened with anxiety but I remember clearly that he kept saying respira which I think was Spanish for breathe. It was painful at first but his calming eventually helped me relax and took most of him but I felt so full and so different. To be honest it was overwhelming and so sexy all at once. I felt helpless in the arms of this man but so powerful looking at my husband who could do nothing but watching as another man took me. His eyes wide and mouth open, he was just amazed at what was happening in front of him.

I think Rafael kept talking to Brett and saying something but I couldn’t make it out. I didn’t care really I was pretty dizzy from orgasm after orgasm and music was blasting. Brett went in the kitchen area of the room to apparently masturbate. Then after a while he came back and laid next to us while we continued for what felt like hours off and on. Turns out it was only about an hour but over the course of that time Rafael and even Brett kept asking me if I was alright which I thought was sweet but I was near passed out because I never knew sex could take you to another place, another level even. When he left I was not even sure I knew because I was face down and I may have even passed out for a few minutes. I can’t even count the number of orgasms I had, after the first three or four it became a complete blur. I swear one of them lasted a full minute, I just kept cumming and telling him to not stop. Afterward the whole scene was pretty disgusting. Used condoms on the bed and it looks like we used half the bottle of lube. I guess I must have tore too because there was some blood on sheets. Sorry if that is too much information.

Get this, Rafael has sent a picture of his penis to be every few months since. No words, nothing. Just a damn dick pic. Guess he was young and stupid don’t know if you have been with a bigger man but I had not. Nothing like him. I was so sore for days, it pretty much cancelled the rest of our weekend. Every time my mind would wander to the soreness it reminded me of the sex and I got turned on all over again.

Brett was so excited for details even though he was right there for most of it and he wanted to know every detail and how I felt about it. He was so hung up on how much bigger the guy was that after a while I didn’t want to talk about it because he was so focused. He kept repeating the same questions like I was somehow not giving enough information or giving the wrong information.

I am not ashamed per se but embarrassed if this is what a normal couple should act like. It was amazing sex. So amazing doing things Brett can’t do that I felt guilt too. It took 4 months before Brett let it go but I think about it almost every time I masturbate. I even think about it when I am with Brett sometimes and now I think I am ready to expand. I know what I want, a man who is assertive, dominant and even arrogant. I want a “bigger” man. I do not want anything like Brett. I do not want anything to resemble what we have. This isn’t the man that I’d ever be in a relationship with. My husband is more sensitive and we have a beautiful connection. That is our marriage. Our bond. I want something he can’t give me. Wild passionate sex with a man who isn’t anything like my normal type. “Forbidden”. It is such a turn on to have sex that is not allowed, a secret that I share only with my husband.

Brett and I have tried to duplicate the positions, we tried to role play we even tried a “sleeve” but Brett kept slipping out. I felt so sexy and I felt so in charge of the situation. I also want to incorporate some humiliation into it because I know how much it turns Brett on. For example he loves when I “force him” to wear my undies and the humiliation aspect. I can tell he thrives on the humiliation. His eyes light up when I tell him that he can’t have me. I think that may even add to making me feel the power of being dominant and in charge.

Now my question for you is this. How do you get over the guilt of doing this? I was raised in a family that went to church every Sunday and this goes against everything that definition of marriage should be. But part of what I love about exploring sexuality with my husband is the fact that it is wrong, the taboo turns me on. Am I a terrible person, an unfit parent? I don’t know but I get these tinges of guilt but I don’t feel like I’ve done anything wrong. I just know that it lights me up inside and I would never do it without my husband present. That is something I know was important to me and to the experience. I want to see his eyes and I want to see that he is getting as much from it as I am. I thrive on the fact that it is wrong but I struggle with the guilt. I am sorry this is so long but I just want to be able to get past the guilt because that is what prevents me from doing something like this again. How do you get over the guilt and how do I stop him from pestering me and laser focusing about it afterwards?

Hi Tanya! Welcome to the site. I completely empathize with some of the things you said and my first reaction is that this fantasy may have been less about you and more about your husband. That is entirely fine but we should be clear about it. It sounds like during the course of the fantasy you may have found some elements that you enjoyed as it played out. Believe it or not this is quite common; as women we are often burdened with guilt around our sexuality. I think that is stupid but there is a reality about shedding the heavy burden of guilt. We can’t feel sexy if we feel guilty. Sexual guilt holds us back from sexual openness and free sexual expression because we hide behind the guilt.

Let’s switch gears to your husband for a moment. His lack of communication is concerning and it seems like some of this scenario may have been coordinated behind your back through communication with Rafael and his friends. Before you consider anything like this again, I think you need to have a series of conversations about your feelings and desires. Tell him exactly what you enjoyed with Rafael and tell him what you didn’t like. If you liked when Brett went into the other room while you were with Rafael, let him know. If being left alone with another man made you feel uncomfortable (as it would with me) make sure you let him know that as well.

It sounds like both you and Brett enjoyed this experience in different ways. Through communication, you can figure out which parts of this experience should be repeated and which parts should not be permitted to occur again in the future. From what you said, it sounds like his presence, seeing his eyes and feeling his love even while you are with another man is comforting to you and helps you feel like you have his approval. It also sounds like teasing and humiliation are important to you as well. Through discussion with Brett, see if you can figure out the balance of his presence and intentional humiliating dirty talk from you. Now remember that there are several types of humiliation, one is denial and the other is inadequacy. Denial is based around your sexual needs being a limited resource and an example would be “How does it feel to know another man can have me but you can’t?”. Inadequacy would be centered around his inability to please you “He is so much bigger, yours doesn’t feel this good.” Both are centered around making him feel uncomfortable and will undoubtedly create a hormonal boost for him as he hears you say it amid the scenario that is unfolding in front of him. When you chat with him, make sure that he is able to handle humiliation, if you see the slightest bit of anger you should consider keeping humiliation a fantasy even if he seems to like the idea of it.

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You need to pinpoint the things about an experience like this which work for both of you. If anything works for only one of you, never compromise with a situation because it will create resentment. Do things that you both love and enjoy to ensure that you both have a wonderful time together. This is about bringing you both closer together and not pulling you apart. In the meantime, enjoy your unsolicited monthly Rafael dick pics. 🤣

I hope that helped, let me know in the comments if you have any other questions or if I left anything out.

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This question was submitted by SmallDCouple via Twitter.

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