Switch! She Dominated Me | 2016

This story is from several years ago, but I wanted to share it anyways

It had been three years since we last talked, so with nothing to lose, I messaged her on Facebook and hoped our conversation would end up taking a kinky turn. We used to work together but were never close. However, I knew she was special, as her strong personality clashed how society told women to act. Perhaps she also noticed my submissive qualities which conflicted with what society thinks a man should be. Whatever it was, there was a unspoken connection between us that we had never explored.

I always found her sexy. She had long brown hair that flowed down her back. Flawless skin. Her tight shirts accentuated her perky tits, while her short skirts struggled to cover her round ass. Her legs were smooth and toned, a product of her rigorous workouts. I had a huge crush on her but could never act on it. Her boyfriends were usually the alpha type. They were strong and masculine. They rode motorcycles. And even if she was into me, I wouldn't have cared, as I have no desire for having typical sex. In the back of my mind, I knew I'd be nothing more than a disappointment for her if she preferred dominant men. Consequently, I needed a dominant woman, someone to control me, but I knew dominant women are rare in a society that tells them to be submissive. Plus, I wasn't about to expose my kinky side to her for fear of my co-workers finding out about how perverse I was. By the time we stopped working together, I had never dared to find out if she was kinky or not.

Years later, I realized I had nothing to lose and lots to gain. Within a few generic messages (e.g. How have you been? Where do you work now? Zzzzz.), she asked me if everything was going well for me outside of work. In autopilot mode, I was going to say everything's good and move on. Instead, I took a chance and said I've been having self-esteem issues, knowing she would pry deeper.

"I worry about what kind of man I am. I feel so inadequate."

Within minutes, I admitted to her how I've always been the beta type and that I've always enjoyed feminine things. Without hesitation, she asked, "Can I dress you up like a woman?"

In shock, the conversation had gone exactly where I wanted it to. I've tried similar tactics before. Usually, I get a girl's number and we get to know one another. Knowing that I don't care about having sex with her, I'll bring up things that suggest I'm submissive. For example, I'll bring up crossdressing and see if they're interested. Nine times out of ten, the girl thinks it's strange and eventually loses interest in me, which I'm totally fine with. This time however, I put my submissive side out there and she was receptive.

With a sense of security established, she began telling me about her fantasies. Mainly, she was infatuated with having a penis. She owned multiple strap-ons, but none of her previous boyfriends were open to anal sex. It made sense, as they were the alpha type, close-minded, or too dominant to get fucked. Her biggest fantasy was to dress like a man and fuck a guy. I had never fantasized about women dressed as men, but I was open to the idea.

After exchanging messages for hours, we made plans to meet up the following day. She told me to shave everything and be ready, as she had lots of outfits to dress me up in. I found out she wasn't lying. She had me try on a plethora of outfits until I finally settled into a short, black mini dress complimented by a sky blue scarf. She even gave me multiple pairs of panties and a pair of pantyhose. When I looked in the mirror, I saw a beautiful woman.

She dressed in men's clothing consisting of black slacks with a dress shirt and tie. With both our transformations complete, we sat on her bed and talked for hours over a bottle of champagne. I noticed a big bulge in her pants and couldn't take my eyes off it. I knew she was wearing a strap on. I also knew that she was more powerful than me. She had been lifting weights for years and could kick my ass. I felt comfortable talking with her, but also knew I was vulnerable. Here I was in my little dress, with a person who was stronger than me, ready to fuck me at any moment.

By the time we finished the second bottle of champagne, our conversation had steered to "The Girl with the Dragon Tattoo." I mentioned the femdom scene which led to a discussion about sex toys. Not hiding her excitement, she fetched her toy box and began showing me her collection. When she pulled out her restraints, I couldn't contain myself: "I wanna wear these."

Immediately, I found myself on my stomach with my skinny little wrists handcuffed behind my back. Next, she tightened the restraints around my ankles and finished the job by strapping a ball gag in my mouth. I was in the position I feared, I was completely powerless. I couldn't yell. I couldn't wriggle free. She could literally do whatever she wanted with me.

I absolutely loved it.

She began gliding her hands up and down my nylon covered legs. I felt so weak not knowing what she was going to do to me. I began moaning uncontrollably as my anticipation increased. A multitude of thoughts ran through my mind, "How far will she go? Is she just playing around? She's not going to fuck me, is she?" I felt the cool air against my ass as she lifted my dress around my waist. Out of the corner of my eye, I saw her pull out a metal beaded whip. She raised her arm straight up and hit me harder than I've ever been hit in my life. I've been in fist fights, but I've never been hit full force like that. Pathetically, I whimpered, "Oww." So she did it again.

After spanking my ass red, she got on top of me and pressed her crotch against my ass. I could feel that big bulge and could no longer contain my excitement. When I turned to take a look at the action, she grabbed a leather paddle and nailed me with it. I quickly learned to behave. If I tried to rub my ass against her, she made me pay with a stiff spanking. Her point was this: you will not receive any pleasure from this. I am fucking you and I don't give a shit if you enjoy it.

She pulled my pantyhose and panties down around my thighs and began grinding against me. The anticipation was killing me. I wanted her to fuck me. I wanted her to get off while ignoring my pathetic little dick. I was wanted her to use and degrade me until she got off - I didn't care if I got off. With my face pressed down against her mattress, I managed to sneak of peak of her grabbing lubricant from her toy box.

She slow inserted the tip of her cock inside me. I knew it was big and I'm glad I didn't get to see it, as I knew I'd be intimidated by it's size. Luckily, I was buzzed from the champagne and subsequently, very relaxed. As she spread me open, she pulled my scarf tightly. I fought for breath as she slowly slid herself deeper into me. The way she fucked was so natural. As she built up speed, I felt like an object, there for her pleasure. I couldn't see her and I couldn't touch her. When she pressed herself deep into me, she grabbed my hair and slammed my face against the mattress. I had never been so thoroughly dominated and my muffled moans were making it clear how much I enjoyed it.

Trapped in restraints, my ass was red. My vision was becoming blurred from the choking and the hair pulling. I was getting fucked by a large cock. I was moaning in ecstasy. Amazingly, she also began moaning in ecstasy.

Despite all the pain and pleasure, I had some clear thoughts. While she moaned, I was happy that she was getting off, since her pleasure was my only goal. Also, I found it ironic. In all the time I had spent in the past trying to please women, I had never seen or heard a woman so turned on. I've read countless books and articles about how to pleasure women. I've tried different positions and have put in loads of effort. Yet the most sexual gratification I had ever given a woman came while I was handcuffed in a dress, being fucked by a strap-on. Days later, she messaged me and told me she had never been so turned on in her life.

Her moans became uncontrollably loud. Again, I've never heard a woman moan so loud (at least not from my efforts as a dom). As she got lost in the moment, I began sneaking peaks of her. She was screaming with her head tilted back as she rubbed her crotch against my ass. Hoping I could get away with it, I rubbed my ass against her increasing the pressure on her pelvis. She got off multiple times until her most intense orgasm caused her to collapse against my thighs. I could feel her pussy pulsating against my legs. It took her quite a while to regain her composure.

When she pulled my panties back up, she let me out of the restraints and passed out on the bed. The gender swap was completed. She had gotten off, ignored my needs, and was now passed out on the bed.

Days later, she told me she had never had such a rush of power. Never had she so dominated someone so thoroughly. I was surprised, as she always came off as dominant, and with me, she was perfect. She told me how much she liked my moans and that she had never been so turned on in her life, claiming she "would kill for that kind of power again." I think the vast majority of women, even if they have a dominant side, need to be dominated, or cannot rely solely on a submissive man. Yet, I also think they would be surprised how much they enjoy dominating if they're able to tune out society's messages that women are supposed to be submissive. Ultimately, the experience left me fulfilled, knowing that she could get off so easily while fucking me with a strap on.