We’ve all got our kinks. I enjoy it when a woman straps on a large cock and fucks me in the ass. I’ve never thought it was normal, and I do feel ashamed of my needs from time to time. The shame hasn’t lessened my desire for this form of submission. I’ve always known I needed it. Ever since I first experienced it.
My first time was actually not my idea. My college girlfriend and I were experimenting with BDSM and she found she enjoyed the dominant role. After we graduated from college we ended up moving to different cities. We tried to make it work, but the distance was forcing us apart. She suggested to me that I submit to strap-on play so that she could demonstrate to me to whom I belonged. I agreed to try it. She scheduled a flight to come to visit me and I visited the sex toy store to buy the instrument of my eventual defilement.
The two-week period I had to wait for her visit was filled with fear and doubt. I was focused on two main questions: how much would it hurt, and would it make me gay. The night of my deflowering had the tell-tale passion, awkwardness, and pain that is associated with most women losing their virginity. She put me on all fours, tied my arms and legs to the bed frame, put on her cock, and moved behind me.
She took me slowly. She pressed the head of her phallus against the tight ring of my asshole and proceeded to ease it back and forth. She was courteous and sensitive to me and made sure to keep withdrawing the dildo to apply more lube. It didn’t take me long to find out that being anally-penetrated was an uncomfortable experience, but not altogether painful as she forced the length of her cock into me.
And then… nothing. She moved her hips back and forth and moved the dildo in and out of me, but there was no culminating moment of orgasm as there is for traditional male penetration. She had a lot of anger that she had hoped to exorcise by this act. She had hoped this violation would inflict upon me a bit of what she had herself gone through, and in that moment, I could sense that she was a bit disappointed. She could, of course, have channeled her anger into the act, and more violently taken me, but she couldn’t bring herself to do that. We had silently flirted with the idea of her using dildo play to degrade and denigrate me, but the act itself did not accomplish this.
We broke up not too long thereafter, but the experience stayed with me. I kept reflecting back on it over and over again. Perversely, I had wished for a more painful experience. One that could more successfully make me feel degraded and broken. In my fantasies, strap-on scenes became a complete role reversal where the woman would painfully fuck me until she came. I started to try to create just such an experience with the women I dated, but I never found someone who had the same desire to defile as she did.
My life as a submissive man was probably characterized by Shel Silverstein’s children’s book, “The Missing Piece Meets the Big O.” You wander through life just not feeling complete. You do the things you’re supposed to: earn a living, find a girlfriend, stay in shape. But you feel really empty inside. You keep wishing that the significant other would just take charge in the bedroom instead of demanding that you ravish her.
That’s the way we submissive men seem to go through life. Doing what we’re told, but paradoxically wishing we were told more to do by our special lady. This lack of fulfillment eventually leads to unhappiness. Life feels empty. You start to feel that you’ll never get what you really want except perhaps by seeking a professional. Of course, this state of “quiet desperation” is not unique to the submissive men in the world. In fact, it seems part of the human condition. Few people seem to achieve real happiness with their lives.
Fortunately, this has changed since Roulette came into my life. She has the same undercurrent of anger underneath our BDSM that I’ve found I strangely need. What’s more, she loves strap-on play. Absolutely thrives on it. We often argue over who loves strap-on play more. After a lifetime of being with women who simply did not get beyond the bizarreness of such a request, it’s a wonderful feeling to be with someone whose needs complement my own.
We’ve talked about my strange desire to be denigrated and broken down by the experience. She’s helping me come to understand where it comes from and why I want it like I do. But understanding where it comes from doesn’t change the fact that I want it as I do. I can tell that she wants it, too. Sometimes, when she’s talking dirty to me, she tells me she’s going to cane me until I’m sobbing and then fuck me silly. When the sex haze wears off, she denies that she’d ever want to engage in play that heavy, but I can tell she can. She’s taking me along a predetermined path towards the result she wants.
She started by suggesting larger dildos to me. We began with the basic 6″ dildo and slowly graduated to larger and larger. The one she recently settled on is the largest Vixen Creations makes, the 8 1/2 x 2″ Outlaw. She fucks me so hard with it sometimes it leaves me sore for days. She claims it’s just because the dildo is stimulating her so much, but I think she just likes causing pain.
A couple of nights ago, we had an experience that was the culmination of many of my fantasies. She ordered me over to the bed and chained my hands to the headboard. She then attached ankle cuffs and a spreader bar to my feet and linked them to the same chain. I was totally helpless and she wandered the room and began preparing herself to violate me. She enjoys the nervous anticipation I have in my bound state as I’m forced to watch her load the dildo in the harness and pull it on. (She’s fallen in love with the Spandex harness from Stormy Leather because it’s a one-piece and she doesn’t have to mess with all the buckles and straps like a traditional harness.) She says it also gives me a lot more control over the dildo.
Her favorite part is lubing me up. She has me right where she wants me. I’m bound up and helpless and she’s looking down at me as she’s stroking lube onto her shaft. She tells me how much I need the fucking that she’s about to give me and assures me that she’ll be gentle. I can see how much she loves the power of that moment reflected in her eyes. Often the anticipation has built up so much that real fear begins to overtake me. I start to shiver and my teeth chatter even though the room isn’t all that cold. Intellectually, I understand what’s about to happen to me, but, on a more primal level, I’m very afraid of it. It’s strange.
At those moments when I’m gripped by real fear, she comes and cradles my head in her hands. She nurtures the frightened little child on display in front of her and tells me everything’s going to be all right. She gets me to calm down. Then she moves back to right where she was and starts lubing up my ass. Sometimes, I beg her to stop. Sometimes, I don’t. Regardless of what I say, she continues her work at an even pace. Soon, she’s placing the head of her massive phallus against my ass and slowly starts pressing it in. This is where the power-play really begins.
The dildo feels so massive I feel like I’m being split apart. I beg her to stop, and she does. She doesn’t take it out, however. She just stops her assault momentarily to allow me to adjust to the massive intruder that’s forcing my ass open. She tells me that it’s going to be all right. If I persist in telling her to stop, she places a finger over my lips to quiet me. Then she proceeds to force the dildo even further into me. It’s a continual process like that: she pushes, it hurts, and she stops to comfort me before pushing it in even farther. It’s similar to deflowering a virgin, except that we do it all the time. I can tell she loves doing it, and that’s why she loves such large dildos. She loves the power that comes with the pain.
And then it’s in. I suddenly feel the sensation of sudden fullness as she forces the head of her monster cock deep into me. Having forced its way past my asshole, there’s nothing left to stop her from ramming the entire length of the dildo deep into my soft flesh. Then she starts to fuck me. She pretty quickly can find a rhythm, and her breathing gets deep fast. I’ve always wanted a woman to fuck me until she comes; two nights ago, I got my wish. Maybe, it was the power of what she was doing, or maybe The Outlaw really does rub her just the right way, but I could see herself building to an orgasm. She just kept fucking me faster and faster as her breathing deepened. Then she came. Witnessing it was the most erotic thing I have ever seen.
Afterward, we just lay in each other’s arms. She played with my hair and told me how proud of me she was. All I know is, it’s the most peaceful and fulfilling feeling I’ve ever had. Suddenly, everything seems right with the world.
Last Updated on 1 year by pseudonymous