Q:
I have a fantasy about my girlfriend that plagues me. I am a thirty-three year old lesbian living with my girlfriend nine years my junior. Like me, she has always been aware of her sexuality. But unlike me she has slept with a man. He was actually the last person she slept with before we got together.
They both worked at the same spot bartending and the hours were gruesome. At four in the morning after doing shots and drinking on the job she would usually go sleep at his place because it was two blocks away versus her commute home which was over an hour. They would continue the party at his, and inevitably wound up sleeping together. This went on for nine months. She practically lived with him. It all ended when he confessed he was in love with her. She told him it wouldn’t ever work because she couldn’t love him the same way he loved her.
I knew her and went to the bar where she worked with him for months before she and I got together. We were friends. We always had chemistry. When we finally got together, the sex was explosive. I’ve never experienced anything that comes close. A few months in we bought a strap-on and I began fucking her with it. When I do she cums harder and more intensely than any other way we have sex. It turns me on so much I usually orgasm from watching and feeling her orgasm.
The thing is, now I can’t stop thinking about seeing a man fucking her. I have never in my life been attracted to a man and I don’t have any desire to have sex with one. But I can’t help but fantasize about a man fucking her from behind while she’s going down on me, feeling her face fuck me with each one of his hard thrusts. I wonder what she would taste like with a man’s juices inside and outside of her. I fantasize about eating a man’s cum off of her. I think about walking in on her and catching her fucking a man behind my back. These thoughts make me cum harder and more intensely than anything I’ve ever experienced. They are my main thoughts when I masturbate and always when we’re fucking. The thing is, I’m not sure if I want to try this in real life. Part of me is scared she might like being with a man so much she will leave me even though we have a great relationship and we’re madly in love. I’ve only shared this with my best guy friend who laughed and told me I was a cuckold. He said I should tell my girlfriend, but I am afraid she will feel degraded or actually want to try this, and I don’t know if I’m ready or if I could handle that. I definitely don’t want to ruin our relationship. Is there a science behind cuckolding? Do you think I’m a cuckold? Should I tell my girlfriend about my fantasies? Do you think we should try them? Could something be wrong with me? I am tormented holding all of this inside.
A:
I am so sorry to hear of your torment. You’ll be relieved to know nothing is wrong with you. Everyone who has a healthy imagination has fantasies—even the non-sexual kind. So please show yourself some compassion and try to stop being so hard on yourself.
As far as cuckolding goes in the traditional cis-male sense, there are indeed quite a few theories behind it. The cuckold is so turned on and titillated from seeing his wife getting railed by a stud, or “super stud” (typically with a much bigger cock), that the cuckold’s feelings of jealousy dissolve. Some theories suggest there is a sperm-competition drive: seeing his hot wife being pleasured by the stud with a bigger longer-lasting cock makes the cuckold’s balls more productive, thereby granting the cuckold a stronger orgasm. Another theory is that the cuckold has a subconscious desire to submit to a bigger cock, and therefore in his mind, the way to do that is to give his hot wife to the stud with the bigger cock. And then there’s the whole delving into matriarchal societies in relation to cuckolding but I’m not going to go into all of that here.
Because Darling, I actually don’t think you’re a cuckold. I think what’s really happening here, from your email and all the background information you’ve given me, is that you’ve fetishized your girlfriend’s past. You’ve sexually processed what she went through, but you haven’t processed it emotionally. Maybe that’s because it’s difficult for you to fully understand why she would ever sleep with a man if she’s a lesbian. And I bet that scares you a little. That’s also why it turns you on. In the field of fantasy research, it is commonly known that what scares us a little (or disgusts us) is often the precipice of what turns us on the most.
I’ll tell you about something I went through when I was much much younger, in my early 20s. I was dating an older guy who was a big shot hedge funder. We had great sex, though it usually involved a lot of alcohol and cocaine. One day he was really high and looking through folders on his computer searching for old pictures to share with me. He mistakenly opened one called TR-Investments, which from the name, I assumed involved his work. WRONG! It was his stash of trans porn—an entire folder devoted to nothing but movie clips of trans folx with big dicks and big tits he had downloaded from the internet. And instantly, I became insecure. I was threatened. I wondered if he was closeted. I wondered if he needed something sexually I could never give him.
Add time, more alcohol, and more cocaine, and the next thing I know, I’m watching the same damn porn left and right—with him and on my own. It turned me on like mad.
We broke up. I still loved this porn category. I even gleefully hooked-up with and then dated a wonderful and stunningly gorgeous trans person, who was fully functional and had great tits. I lived out the fantasy—a big cock inside me and big tits in my face— but it wasn’t as exciting as I had built up the fantasy in my mind to be. I too was processing my internal fears and insecurities sexually rather than emotionally, which manifested itself into a fantasy. And when I tried that fantasy in real life, it wasn’t all I’d dreamed it would be. It’s no longer a common fantasy for me anymore, nor is it a go-to thought or fav porn category, but every now and again, I do find it hot. It just doesn’t do it for me now the same way it did for me back then. And that’s totally okay and normal because our sexual fantasies change and go through phases based on what we’re experiencing at any given moment in our lives.
I believe fantasies are much healthier if they go through phases and you explore them, because when you evolve, so do they. Being stuck on the same fantasy your entire life just seems woefully boring anyway.
So should you tell your girlfriend? Absolutely. Keeping your fantasies locked in and all to yourself is not fully sharing who you are with your partner. It’s a recipe for torment, because while you’re having sex, your mind is playing a movie of something else to get you off, and you’re not being fully present in the moment, fully enjoying your lover. That’s not fair to either of you!
How and when you tell her is the important part. For example, I wouldn’t blurt out, “I want to see a big cock pumping you from behind,” during sex. But what you can tell her, perhaps over dinner or whilst snuggling together on the couch, is that feeling her cum when you’re using the strap-on makes you more turned on and excited than anything you’ve ever experienced. And so you wonder if she ever misses being with a man. See where the conversation goes from there. If she says no, I suppose that’s good for you, and if she says yes, I suppose that’s good for your fantasy. Either way, having this conversation is going to be a catalyst for your relationship to grow—erotically, emotionally, and intimately.
The place all sexually liberated couples should strive for is a place where you can openly and honestly share your fantasies, and even talk them out during sex. Does it mean you’ll try it in real life? Not necessarily. And if you do, it might not turn out to be as exciting in real life as you’ve built it up to be in your mind.
Mr. Malsauce and I talk out our fantasies during sex. But it takes two truly secure people in a secure relationship to do this. Being open and honest is a constant test of how strong you are together. And you know what? Sometimes I tell him things or show him porn clips he is so not into and he just tenderly shakes his head and chuckles. And that’s okay. No two people are the same. No two people like all the same food or all the same music, and therefore, no two people are going to be 100% into the same fantasies 100% of the time. It amazes me how many people profess their unconditional love and acceptance for one another, but then their actions don’t align. Just be sure to use laughter and acceptance as building blocks, axe judgment and mockery out of your repertoire.
It’s helpful if you have a close group of friends to confide in as well. The more fearlessly authentic you can be with others, the more you finely tune yourself, and the more you let go of shame and accept yourself. Self-tuning is a constant process. You don’t tune a guitar once and expect it to stay that way forever. Working to keep it in tune while you play is key to making beautiful music; working to keep yourself constantly in tune is the key to making sexual evolution beautiful and satisfying.
So tune away, my dear beautiful being. Practice having more real conversations with your guy best friend—he sounds good for you. Laugh, especially at yourself. And talk to your girlfriend already! Stop holding this stuff inside that’s tormenting you. If you don’t accept your authentic self, who will?
Love Always,
Mal