A Male Chastity Story
I first met Lori through mutual friends as we clicked instantly. We exchanged phone numbers at the party and agreed to meet for drinks later that week. While having drinks, the mutual attraction and flirting was so intense that we wound up back at her place for a passionate evening.
Lori was assertive and confident in bed, which as a submissive male, I loved. She loved that I was willingly submissive and went out of my way to please her. We continued our relationship, dating as couples typically do. We began to explore a bit more in the bedroom, playing around with some light BDSM. We also began to open up to one another. I learned that Lori was bisexual and even had a girlfriend back in college. She told me that she typically gravitated toward men and assured me that she didn’t feel the need to pursue women any more. I also opened up to her about my private cross-dressing, which seemed to intrigue her. We agreed to explore that a bit more at some point.
One evening, I decided to surprise her by wearing a pair of my Daniel Alexander DA780 men’s thong underwear. When we got back to her place and began undressing, she was truly surprised, and from her reaction, she loved seeing me in a thong. Our lovemaking was extra passionate that evening. When we awoke in the morning, Lori asked if I’d be interested in wearing one of her thongs. I immediately agreed. I put on a lacy red thong panty and immediately got an erection, which Lori saw. She then handed me a matching bra, but this time she ordered me to put it on. I immediately followed her instruction.
As I walked around her apartment, her eyes followed me around, checking out my body, and I could even hear the sound of her giggles. She was clearly loving this. She then invited me over to the bed. When I arrived, her legs were spread as if to invite me to go down on her. When I began licking, she was extremely wet. She was clearly more turned on than I ever saw her, and she came more quickly than she ever had since we’d been together.
Instead of reaching over to satisfy me in order to reciprocate, she laid down in the bed and went to sleep, but first ordered me not to touch myself. This was a first — Lori always reciprocated. I was turned on beyond belief, but I didn’t want to disobey her. I held her in my arms and fell asleep next to her with my erection popping through her panties.
When she awoke, she announced that we would be going shopping. Lori then brought me to some of her favorite stores for women’s clothing. She held up various items of clothing and lingerie, asking what I thought about them. The sizes didn’t seem to correspond to her size, but I didn’t ask any questions. After an afternoon spent shopping, we went back to her apartment.
Lori then spread out all of the purchases on the bed and asked which were my favorites. I picked a matching black thong and bra set, a black leather miniskirt, and a pink turtleneck sweater. She then told me that I should get dressed while she awaited in the other room, motioning toward the clothes I mentioned. I slipped on the sexy lingerie, the miniskirt, and the sweater. She ordered me to come to the living room so she could see. When I arrived, I could tell she was pleased. She then went into her closet and pulled out a brunette wig, some black tights, and a pair of knee high leather boots in my size. She had clearly planned for this.
I was again ordered to sit in front of her. She applied makeup to my face and painted my fingernails. Eventually, she announced that she was finished and that I should go take a look in the mirror. I was quite amazed — I really loved how I looked. Very sexy, demure, and feminine. Apparently Lori thought so as well. She seemed quite aroused, and couldn’t keep her hands off of me.
At that point, Lori told me that her feelings for women had been growing stronger, and that she needed to continue to have relations with women. She revealed that she was growing less and less fond of penetrative sex and of touching male genitalia. Lori told me that while outwardly we could continue being a traditional heterosexual couple, I’d need to be her “girlfriend” privately while we were together in her apartment. She asked if this was okay. As I loved cross-dressing, and I loved Lori even more, I readily agreed even though I wasn’t sure how this would play out.
Then, Lori informed me that there was one more thing I had to try on. She went into her closet and pulled out a metal chastity cage. She informed me that I’d need to wear it from now on. She knew that I was aroused from the cross-dressing and she couldn’t take a chance that I’d touch myself and not be aroused enough to please her. She said it didn’t matter as she wouldn’t be playing with my cock anymore anyway. I would now remain permanently locked in male chastity.
We spent some time finding the right size cock ring for the chastity cage, applying lube, and figuring out how to get it on. After about 20–30 minutes, we had it figured out and it was locked onto my body, with my cock squeezed inside the miniscule tube. Lori took the key and locked it away. I quickly realized that an erection would be impossible given that there was barely enough room in the chastity cage for my cock when not erect.
She was growing aroused again and began kissing me passionately. I was growing aroused as well, but couldn’t get an erection due to the chastity cage. We then made our way to the bed and began undressing one another. She was fondling me lightly, though more as a woman might fondle another woman. She also began instructing me on how to arouse and please her. I eventually made my way down between her legs and began to lick again. She came more quickly and more intensely than ever. That evening, we ordered out for dinner and sat at home watching a movie. When it came time for bed, she pulled out a thong bodysuit for me to wear, telling me that she wanted me to wear something sexy to bed. I was still incredibly aroused, but as I was wearing my new chastity cage, all I could do was submit.
Our life together continue for some time like this. I would go to her apartment at the start of the weekend, change into whatever feminine outfit she chose for me, and I’d live the weekend as a woman. She even gave me the female name of Jennifer, which is how I came to be known by her. She even would sometimes call me Jennifer outside of the weekend. Of course, my chastity cage would always stay on. Lori continued to have mind-blowing orgasms, though after about nearly a full month, I had yet to orgasm. I was torn. I wanted to climax and to feel my load shoot out of my erect cock, but I found I loved the frustration of being unable to even get an erection, and I especially loved being at her mercy, having no idea when, if, or how I’d ever orgasm again.
One evening, Lori invited some of her girlfriends over for dinner. I was still dressed as Jennifer, but she instructed me not to change back. I was nervous as heck, but I didn’t want to disappoint her. However, when her friends arrived, while they were surprised to see me as Jennifer, they loved it. I served them all drinks, let them take photos of me, and I was very happy to strut around for them to admire. This particular group of girlfriends were Lori’s bisexual and lesbian friends from college, so they were enjoying welcoming another “woman” into their fold. They also could sense that I was a bit uncomfortable and nervous, which they enjoyed tremendously.
At the end of the evening, I began cleaning up. They all had left except for Lori’s friend Allison, who I remember had briefly dated Lori back in college. As Lori and Allison continued talking in the living room, I stayed in the kitchen to do the dishes.
When I went out to the living room to check on them, they were passionately kissing and fondling each other. They immediately stopped and looked up at me when they heard me arrive. Lori then told me that Allison would be spending the night and that I would be sleeping on the sofa. I was instructed to go change into my silk night gown and thong and once I came out to the living room, her and Allison would go to the bedroom.
Honestly, I was so under Lori’s spell at this point that I was completely okay with this. I’d feel a bit lonely, but I was very happy for Lori that she’d be satisfied and would have fun. I was even quite aroused thinking about her and Allison together and I wished I could watch. I could hear them through the door, and I was growing more and more aroused listening to their giggles, their moans, and eventually their screams of passion as each of them had the opportunity to climax. I had never heard Lori have such an intense orgasm as when she was with Allison. I was jealous, yet quite happy for her. As I realized that I was now her cuckold, I grew even more aroused, and felt by body covered with a warmth I hadn’t experienced before.
In the morning, Allison left, kissing Lori on her way out. Lori then invited me into the bedroom. As we lay down next to one another, I could smell Allison’s scent on the pillow. I could tell that Lori was satisfied in a way I could never satisfy her, and rather than feeling jealous, I was intensely happy that she could experience this satisfaction.
“Jennifer, you know I love you very much. I love your companionship and I love having you as both as boyfriend and as a girlfriend. However, last night taught me that I can only be truly satisfied physically by another woman.”
“You will remain locked in a chastity cage 24/7 and will be let out only for cleanings. We won’t be having intercourse any more either. You are still my boyfriend and girlfriend, but our sexual relations will be limited to female on female sex. I will no longer acknowledge your penis and it will remain locked in my chastity cage. When I want true satisfaction, I’ll call upon Allison. However, in the interim, I will call upon you to offer whatever satisfaction you can. From now on, you will be my cuckold, and you will please me whenever I desire.”
“While I won’t be touching your genitals any more, from time to time I’ll allow you to orgasm by using a vibrating dildo and I’ll even be willing to peg you from time to time, but I won’t do anything I wouldn’t do with another woman.”
“Whenever we’re together privately, and sometimes in public, you must be willing to live as Jennifer. We will go shopping for more female clothing for you. And even when you’re not living as Jennifer, you will wear thong panties over your chastity cage.”
“Otherwise, we will interact as a traditional heterosexual couple and nobody will be any wiser. Only my girlfriends will know our secret.”
“I will call you Jennifer, as will my friends. I will enjoy the pleasures of other females whenever I please, and you will please me whenever I desire. You will experience sexual satisfaction from anal penetration via vibrators or pegging, but I will no longer be touching your genitals. If you’re in agreement with this, tell me that you love me and lick my wet pussy”.
I replied “Lori, I love you”, and I began to kiss her naked body, working my way down to between her legs.
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