Molly and I had been dating for over a year, and for half of that time my cock had been locked in a male chastity cage. It seems that since she insisted that I wear the chastity device, the prolonged periods of orgasm denial grew longer and longer. She loved teasing and edging me until I could barely control myself, and she always seemed to know exactly when to stop. She would usually leave me begging for release as drops of pre-cum would drip out of my cock, though other times she knew how to extend her edging just a bit longer, just enough to elicit a ruined orgasm. I’d feel the semen exit my body, but would once again fail to experience a satisfying orgasm, leaving me feeling just a frustrated as before. When this happened, she would remove my chastity cage and hold it up to my mouth for me to clean it off with my tongue.
I hated the taste of my cum, but I loved the humiliation of it, and Molly did too. It turned her on tremendously to see me humiliated in any way she could think of. I think that’s why she enjoyed keeping me locked in the stainless steel chastity cage for so long. It seems that it had been months since I last experienced a true orgasm, and the only time I would ever cum was through the ruined orgasms she’s administer. On the other hand, she experienced no shortage of orgasms, and her appetite was insatiable. I was giving her oral nearly every day, and it still didn’t seem to satisfy her. I would even use a strap-on over my chastity cage to give her the sense of having a cock inside of her, yet she still craved more.
“I love how your tongue satisfies my pussy and I love how much you make me cum, but I need more” she said one day. She continued “I need to get fucked hard and I need more men. We’re going out tonight. I’ve laid out an outfit for you to wear. Put it on and follow me.”
I obeyed and went to the bedroom to see what she laid out for me. When I arrived in the bedroom, there was a miniskirt, a turtleneck sweater, bra, thong panties, tights, and knee high leather boots waiting for me. Molly walked in and saw my confused face, but only chuckled. She simply point to the outfit and ordered me to put everything on.
Rather than leaving me to my own devices, she sat down to watch, so I undressed. I started with the thong panties. As I pulled them on and felt the thong rise up between my butt cheeks, I found I quite enjoyed the feeling of the women’s panties. The soft silky feeling was arousing, and the thong supported my chastity cage better than I had expected. I looked at Molly and saw her giggling, which aroused me instantly. I wanted to continue. I put on the bra, followed by the tights, and eventually the entire outfit. Molly came over and began applying makeup. I was surprised at how long the process took, but enjoyed the feeling of humiliation and arousal as I could feel my cock struggle to become erect within my chastity cage.
Molly then attached a wig to my head, and I knelt down to put on the boots. When I looked in the mirror, I was surprised at how feminine and sexy I looked. Molly liked it too, and she snapped to photos on her phone. I posed for her a bit as she snapped a few more photos, giggling the whole time. I was thoroughly embarrassed and humiliated. Molly knew that, and she was clearly enjoying it. “Let’s go” she said.
As we left the apartment, I grew nervous. What if someone recognizes me? What if I can’t pull it off and people notice I’m not actually a woman? Molly saw how nervous I was and she just chuckled. This made me more nervous, but even more turned on.
After a brief taxi ride, we approached the club. It was a typical dance club in downtown which catered to a diverse crowd. I followed her in, and we landed on the dance floor. She began dancing and I followed.
As we began dancing, I started to loosen up a bit. I was enjoying feeling sexy and began moving my body in a more feminine manner. Molly loved this. As she saw me start to loosen up, she began to move a little further away from me. I grew nervous, but was also having fun.
I then saw something which caught me by surprise, but in a quite unexpected way. Molly was dancing with two other guys in an extremely suggestive manner. I was overcome with jealousy, but was even more overcome with arousal. My chastity cage struggled to keep my aroused cock in place as I watched Molly gyrate, rubbing her ass against each stranger’s cock, and allowing them to fondle her. She was having the time of her life. Our eyes met and we smiled at one another.
I never expected to enjoy seeing her enjoying herself with other men as much as I did. For the next few hours, we all danced on the floor as I constantly stole glances at Molly as she rubbed her body against the two strangers, they took turns making out with her, and they fondled her breasts and her ass.
Part of me wanted to go over there to stop it, but I couldn’t help watching and enjoying the show. I was also painfully aware that I was completely feminized at the moment, leaving me feeling completely powerless and emasculated. Molly knew this, and I’m sure this was part of her plan. Feeling so powerless and emasculated was thoroughly humiliating, yet intoxicatingly arousing. I leaned into the experience and enjoyed the show. I continued dancing.
I could also notice other patrons stealing glances at me. Some women would notice that I was slightly more masculine than the other “girls” and would giggle when they noticed. I loved the humiliation, and when I saw them giggle, I smiled back at them, which would make them giggle even more.
I felt a hand on my ass. I turned around and saw a shirtless man with a chiseled chest smiling at me. I had never been touched by a man in this way before, and I was surprised by how much I enjoyed it. I began to move my ass as his hand ran over it. Soon we were grinding against one another. I let him rub his cock against my ass as he held my hips tight. I could feel his erection through my miniskirt, and I wanted to satisfy him. We moved away from the center of the dance floor and off to an unexposed area. I continued to gyrate my hips in front of him and reach my hand behind me, running it over the outside of his trousers, tracing the outline of his cock. I looked at Molly again and we locked eyes briefly. I could one of her partners grinding his cock against her ass as she returned to making out with the other while she fondled his cock through his trousers.
My new friend then unzipped his pants, and I took his cue. I reached my hand down his pants and grabbed his erect cock, beginning to stroke it. It was harder than my cock had ever been in the last six months. I found myself longing to be able to achieve such an erection, but was equally glad to have the restriction of the chastity cage locked on my cock by Molly. Somehow, I loved the inability to cum, and I loved how she kept me constantly aroused.
I could feel my new friend moving his hips as he grew more and more aroused, and I stroked harder. Within about a minute, I could feel his cum shoot all over my hand and all over the inside of his pants. I kept stroking until he pushed my hand out of the way. Without a word, he slapped me on the ass and walked away, disappearing into the club. I was left alone completely aroused, hornier than ever, completely humiliated, yet still loved every second. When I looked at Molly she was looking at me from across the club with a huge smile on her face. She walked over.
Molly had a glow on her face as she approached, and she appeared hotter and sexier than ever after seeing her with those other guys. Again, my cock struggled within my chastity cage. Without saying a word, Molly reach under my miniskirt and gripped my cage with one hand firmly, then with the other hand, she reach behind me and tugged at the top of my thong, pulling it hard against my asshole. It hurt, yet I loved how self conscious it made me feel, and I loved feeling dominated by her. Molly whispered in my ear “Let’s get out of here”.
We left the club and headed home. When we arrive home, Molly ordered me to undress down to my bra and thong panties.
“It was so nice to fool around with some real men for a change. Feeling their hard cocks rubbing against me and their hands all over me got me hornier than I’ve been in a long time.”
She remove her clothes and lay on the bed with her legs spread. “Come over here. You know what you need to do”.
I approached her and immediately began licking her wet pussy. I could smell her perspiration from dancing in the club, and it was intoxicating. As soon as my lips touched her pussy, I could sense how aroused she already was. I licked with a passion I hadn’t felt in quite some time. I truly wanted to please her, and as horny as I was, I wanted to continue feeling my cock locked in the cage, unable to grow erect, and with her in control of my sexual frustration. Molly didn’t disappoint.
She came quite quickly, and I could feel her muscles tighten as she screamed in ecstasy through the height of her orgasm. This was enough to push me closer as well, and I could feel some pre-cum exit the tip of my cock inside of my chastity cage.
After she came, I began kissing her all over her body as she loved me to do while she recovered from her climax. She then turned over onto her stomach, face down on the bed. She had an absolutely luscious ass, and the angle at which it was protruding into the air ever so slightly was irresistible. I worked my way down her back and began kissing her butt cheeks. She moaned slightly.
I continued kissing her ass cheeks, and began licking between them gently. I loved the taste and smell of her ass, and I began growing more aroused as I ran my tongue over her asshole. She moaned again slightly. I began to lick her asshole, and pushed my tongue as hard as I could against it. I could taste her perspiration and could feel my cock push again at the front of my chastity cage once more. As I began rimming her more excitedly, I could feel her grow limp, and I realized that she had fallen asleep.
As excited as I was, it felt selfish to lean into my arousal from rimming her without her fully present to enjoy it, so I kissed her ass all over until I had made contact with every part its surface with my lips. I then climbed next to her, held her in my arms, and tried to fall asleep as I replayed the evening’s events in my mind. My locked cock constantly reminded me of my sexual frustration, but fatigue eventually set in and overtook my body with sleep. I fell asleep beside Molly in a state of bliss I hadn’t known in quite some time.