I’m a 40 year old bisexual Femme Dom, but I wasn’t always so open minded about my sexual interests. I came from a very rural, homophobic sort of background. Homoeroticism, bisexuality, or reverse role playing were strictly taboo for me.
Perhaps one of the reasons why anal sex and strap on penetration has held such a fascination for me is because it because of that fact that it is so taboo. It remains a forbidden fruit, so to speak. It also makes me feel very powerful and in charge which is something which I didn’t feel growing up, coming from a very misogynist sort of background where women were treated like wives/servants or women/whores. It is nice to be able to turn the tables and treat men as servants and sluts.
My first exploration of kinky fantasies came in my mid-twenties. I was very shy then, and the easiest way to explore fantasies for me was on the phone. I started out very submissive. Something in my nature sought to repeat the way I had been treated in order to learn a lesson. So I sought out dominant men and daddy figures until something in me snapped.
At some point I figured that I had enough. I thought to myself that there was no reason why I should be serving their needs, and that they had better serve mine. That is when I began discovering my power and enjoying domination.
At first I just talked with men who were into oral servitude. I got off on telling them how I was going to put a collar on them and lock them between my legs to service me. I enjoyed the thought of using them as a sex toy and as an object only to fulfill my needs.
Then I started getting into denial and teasing. I enjoyed telling them how I would tie them up, tease their cock and maybe never let them cum. Perhaps I would just leave them to jack off by themselves, or maybe I wouldn’t satisfy them at all, but get off and hang up on them.
I enjoyed using men for my orgasm. IF I did reciprocate — I enjoyed doing it for them in a very humiliating way, like making them masturbate with their pants around their ankles, or telling them that they had to go out in public and find a quiet spot and jack off in the car for me while I listened. I liked making them feel like a pervert or a nasty slut.
I also fantasized about telling couples what to do in those first few months of my BDSM exploration. I enjoyed playing teacher and telling them exactly how to have sex. I gave the man very explicit instructions on how to perform. I began to explore my fantasies about women as well.
It was in my late twenties that I started talking to cross dressers on the telephone. It was an extreme turnon to fantasize about penetrating them with dildos or making them shave for me. I liked hearing their voices get high as they became excited and I liked hearing them moan like a girl if I talked about penetrating them with my finger or with a dildo.
I enjoyed imagining that I had a small penis that was an extension of my clit and that I could penetrate them with it. I enjoyed the thought of them becoming feminine just for me and me having the best of both worlds. It was the reverse role playing on the phone, and the level to which it excited me that finally gave me the motivation to go and meet with someone. Feminization fulfilled my needs on many levels.
I very carefully screened the person that I selected at that time. I wanted a virgin. I wanted someone who became so out of control at the thought of being feminine that I knew that I would have complete and utter control over them.
I listened for those tell tale signs in men’s voices when I talked to them on the phone. I waited until I had someone that I knew was so enthralled by the idea of being dominated and fucked that I knew that I had him by the balls. I could hear his voice become dry and cracked and I could hear the tremble in his voice when he talked about the fantasy. I knew I held ultimate power over him and that he would not switch on me because he wanted so much to submit.
When I found a beginner that I felt was thoroughly controlled by his desire, I invited him to come and meet me. He was in reality — not a very effeminate man. He was a 45 year old football coach and a very large furry guy. He had a mustache. He desperately wanted to be relieved from all the testosterone and macho behavior that he had to deal with on a day to day basis. He wanted to give up all of his control.
We met at the local no tell motel. I lived in a small town, so I shudder to think what the locals thought of me. I had told him ahead of time what I expected of him. He would bring an anal vibrator with him that had beginner attachments.
I would bring panties, a skirt, a bra, a blouse, lipstick etc. And I would dress him. I would spank him for being such a naughty slut and having such naughty fantasies about being penetrated. I would let him watch me masturbate, and there would be absolutely no exchange of body fluids. And then, I would take his cherry.
When I met with him I was a little scared. But I could see that he was scared also. That gave me back my feeling of control. In spite of the fact that he was a big, burly, muscular guy, I still felt like I was calling all the shots.
I made him undress in front of me. I told him in no uncertain terms that he was going to be my sex toy and my bitch. I made him stroke himself to get himself hard. I dressed him, put makeup on him, and then I tied him. I didn’t have rope, so I improvised.
I had heard about saran wrap rope, so I twisted up some saran wrap, and I tied his hands behind his back and tied him to the desk in the motel. He was facing the bed. He had on pink panties and a bra. I put pink lipstick on his lips under his mustache. He was very turned on.
I laid down on the bed and spread my legs and started rubbing my clit in front of him and telling him nasty things like “I know you want me, but you can’t have me sissy.” Or “You look pretty in those panties.” I like the way your clit bulges in front.”
I shoved my fingers in my pussy right in front of him but he could not reach me to touch me. I enjoyed the feeling of denying and teasing him immensely. I enjoyed knowing that I could flaunt myself in front of him but that he could not have me.
Then I untied him and told him to kneel and lean over the bed for me. I spanked him for being so naughty and getting hard in his panties. I told him that he was a naughty whore and that I was going to fuck him good and take his virgin ass.
I lubricated the small latex attachment to the anal vibrator which was about the size of a finger. I pulled apart his cheeks and rubbed him with my latex glove clad finger. Then I slipped it inside. I turned on the vibrator and he started to moan. As I watched the small latex finger disappearing inside him, I thought to myself, “So this is how it feels to have a penis”. I know that I can never experience the real thing, but the feeling of his ass clamping down on my finger was very exciting nonetheless, because I imagined I could feel it on my clit.
I enjoyed the feeling of power as I slid the slim attachment in and out of him. I enjoyed as his moans got higher and more sissy like. I slapped him again even though his ass was a nice rosy pink already. I said to him “Take it slut! Take my dick.” If I had a dick I would have used it.
He started begging me — Please Mistress — I want more. I knew he was already really tight so I knew taking the whole vibrator was going to hurt him. So I took it really slow. I pulled off the latex attachment and I slid the fat tip of the vibrator inside him. It was so tight and I could feel the tightness because of how hard it was to move the vibrator inside of him.
I told him that I wanted him to stand up and spread his legs. He did as I asked. I turned him sideways so I could see his ass and his penis at the same time. I watched his penis bob up and down in response to my slowly twisting and pushing that lubricated vibrator in his ass.
“Oh Mistress, he said, I want it ALL”.
I said, “Okay slut, I’m going to give it to you.”
I pushed more firmly and watched the vibrator slide in, first one inch, then 2 inches, then three. I knew that it really right for him. I made him turn around and face me while I held the vibrator inside of him.
“Rub your clit for me, slut, I told him.” He was almost already there. “CUM ON MY TITS YOU LITTLE WHORE!” I told him, as I rubbed my hard nipples.
He obeyed immediately, and I could almost imagine what it might have felt like to have that cherry ass clamp down on my dick as he came. I’m sure that he must have felt that he was going to break the vibrator in half with the force of his cumming. Mm. He squirted volumes of cum all over my breasts and my nipples. I made him lick it off.
I enjoyed deflowering him and it was an extremely powerful experience for me. It made me feel powerful and in control. It was a one time thing for he and I. I always wondered if he ever met any other mistresses and if his fetish for being anally penetrated grew from there. I’m certain that he was probably sore for a few days afterwards, considering the fact that he took a full sized vibe in his cherry ass. I guess that I liked knowing that he was a little sore and thinking that it was adequate justice for all the times that I had been taken forcefully without my consent.
My fetish for anal penetration certainly grew from there. It was not long after that I began considering the possibility of obtaining a strap on harness. Vanilla sex would never appeal to me again.