The Sissy Ultimatum

I'd only been dating Chloe for a few weeks when I discovered her fine and very expensive collection of lingerie. Chloe was from Paris, an attractive graduate student who had recently moved to San Francisco to pursue her studies in linguistics. We met on the University of San Francisco campus, and we hit it off almost immediately. Our first date was at the Exploratorium, where we both impressed each other with our knowledge and love for science. I was a fan of foreign languages too, and I used the opportunity to work on my French. Neither of us will ever forget the first time I stammered out je t'aime to her, late at night on Market Street after dinner at Zuni Cafe, her being half-moved by my gesture, half-laughing at my pronunciation. We moved in together shortly after, into a one-bedroom apartment in the Lower Haight, and things were moving along pretty well.

It was late at night when she was out with friends that I stumbled upon her lingerie drawer, and realized that the French stereotype applied a lot to Chloe! No woman I'd ever been with had such an extensive collection. There were sexy babydolls, panties in every style, elegant hosiery, sheer stockings, bras.. It was paradise.

Of course, seeing her in her underwear was a really nice perk of our relationship. But the lingerie collection was of interest to me for another reason entirely. For as long as I could remember, I had had a deep attraction and desire to wear women's clothes and underwear. Over time, it had blown up into an addiction. I had a small collection of bras and panties myself, although not as large as Chloe's, and I kept it well hidden.

I couldn't resist the temptation. I started trying on her underwear whenever she was out and I had some privacy. It didn't happen too often at first, but as time went on I would start making excuses to go home early without her, so that I could have some underwear time. I was very careful, of course, and always left every item I tried on exactly where I left it. She would never find out...

--

It was Wednesday night. We'd just come back from a movie downtown. Chloe was reading a book on the couch, and I was busy folding our laundry on the dining table. Folding her laundry was always a thrill and a frustration at the same time. A thrill to handle her delicates so closely, a frustration because I couldn't do anything more than touch with her around. I stole a few glances at Chloe as I folded her panties, trying to see what she was wearing under her tank top and shorts. A flash of orange, around her ample breasts, surely that was the orange bra from Agent Provocateur I had tried on just last week!

Almost on cue, Chloe took a deep breath, as though preparing herself for something unpleasant, and closed her copy of L'Insoutenable légèreté de l'être with a snap. Her piercing green eyes met mine directly.

"Honey", she said in a steelier voice than normal, "we need to talk."

I dropped the blouse I was folding, looking at her with a certain nervousness. Surely she couldn't know? "What's going on?", I asked, trying to keep my voice calm.

Chloe held my gaze for a second, and cleared her throat, as though searching for the right words. "We need to discuss your taste in underwear," she said firmly, her eyes dropping to the table of now-folded clothes in front of me.

"What are you talking about?", I asked.

She threw back her head and laughed. "Are you really going to make me say it?", she demanded. "You know what I'm talking about! You've been stealing and trying my lingerie for weeks, probably since the day we moved in together!"

Chloe has lost most of her French accent since moving to the US, but notes of it return to her voice when she is angry or passionate. I find that an intense turn-on, despite the direness of the current situation.

"How did you - ", I started, and then stopped, realizing how silly the question was. Of course she knew. There were probably bits of pubic hair in everything I had tried on, maybe even precum stains. A lot of them were probably stretched out by my wearing them. It wouldn't have taken an intelligent woman like Chloe long to put two and two together.

Chloe sighed. She checked her watch, and then beckoned to me to come sit on the couch next to her. I obeyed. She put her hand on my knee, rubbing it all the while looking at me with an expression of sympathy.

"I was really mad at first, you know. I was wondering what kind of sicko I had moved in with. You seemed so masculine, on all our dates. But here you were, trying on my panties? My bras? Rubbing yourself all over them, by the looks of it. It was awful. I thought I'd found the right man, the perfect man, but here it was, the illusion all ruined. I was ready to break up with you, then and there."

I could hear the anguish in her voice and see it in her beautiful face, and I felt more guilty than ever more. I understood the tightness in her voice talking to me the past few weeks. She must have been really upset. And who could blame her?

"But then I decided not to make a hasty decision. I decided to look this up online. And what I found there was really interesting, mon cheri. Turns out, you're not weird at all. In fact, all things considered, you're actually pretty normal. You are what people call a sissy. Yes, a sissy. A sissy is a heterosexual man who likes to wear women's clothing. And you know, the more I read into it, the more it all made sense. In addition to being into women's clothing, sissies are also generally submissive individuals. They crave a woman's authority. I had never really thought about it before, but it makes sense. It makes particular sense for you. Now that I thought about it, you'd always been happy to cede authority to me. You let me pick the movie tonight. You rubbed my feet in the theatre. Even right now, you were being a good boy and folding my clothes while I lounged around with a book."

I felt intense shame and arousal at the same time. Shame, at the way my girlfriend was talking to me, and the way she was calling me a sissy in such a matter-of-fact tone. But arousal too. I hadn't been this hard in a while.

I looked up to see her staring at the bulge in my pants with a slight smile. "Yes," she said, "you're definitely a sissy." And I thought my cock would explode.

"Now, there are two things we can do", she said, reaching for a shopping bag next to her and drawing out two packages. "Either way, of course, you need to stop trying on my lingerie. It is mine, not yours. One way this relationship can go, is that you can stop wearing my panties and we go back to being a normal couple. I still love you. And I think you love me enough understand why we need to make this choice."

She held out the first of the two packages to me. It was a pair of blue Andrew Christian designer boxer briefs, a very nice pair indeed. "This is the blue pill," she said. "It's an invitation to go back to the way things were before. We will pretend this conversation never happened. You will replace all the underwear that you damaged. You will gain one additional pair of boxer briefs. Frankly, your entire wardrobe could use an upgrade, I've been meaning to tell you for weeks," she said with a smile.

I relaxed slightly. She seemed sincere. Whatever happened, it seemed like she was ready to forgive me for it.

"Or", she said, with a sudden change of tone, "you could swallow the red pill."

She held out the second package, and I took it, trembling. It was a pair of bright red crotchless panties from Agent Provocateur, with a scalloped front and a bow detail, and ruffles in the back. As I turned the package around, my cock starting growing hard again. Panties had that effect on me.

"Should you choose this option," she said quietly, "you will become my sissy. What that means exactly for our relationship, I can't tell you. I'm still getting my head around everything myself. But it will certainly involve you being feminized, permanently at home, and partially when you're out. You will become my submissive. You will learn to address me as your Superior, and take care of all the chores around the house. Most importantly, you will accept that as a sissy you lose sole right to my pussy, and you will accept my right to take on extramarital lovers. Yes", she said, smiling slightly at the horrified look on my face. "If I'm going to have a sissy boyfriend, I am going to need some real men to fulfill my other needs."

We sat there in silence for a bit.

"I don't expect you to come to a decision immediately, of course. Let's both take two days to think over this. I want to know your decision by Friday night. I will be working late that night, you will return early. I want you to be naked, except for one of these two items. Either the blue boxer briefs, or the red panties. When I walk in, I will know what you have chosen."

"If you choose the boxer briefs, wow, you'd probably look really good in those! I would probably grab you and have you take me then and there. I would fuck you so good baby. I would even let you do me in the ass. I know you've been wanting to do that for a while." She was slightly breathless as she said all this.

"Of course, if you choose the panties, forget about that. Or any kind of sex with me really. You will have waived your right to fuck me, or any other woman. You will have to start getting used to a life of service, submission and humiliation. This would be an easy choice for most men, you see. I wouldn't even have to have this conversation. But for you, well..." she trailed off.

"I think it's best if we spend this time apart. I don't want to influence you, you know. I have made arrangements to stay at Marie's place for a couple of nights. But I will see you Friday." She stood up as she spoke these words, grabbing a bag she had presumably packed earlier. She called an Uber on her phone. "3 minutes.. 2.. he's outside, baby. Whoops, I forgot to change", she checked herself in the mirror distractedly - she was still in her tank top and short shorts, "well, it can't be helped now. I guess the driver will get a nice view won't he?" She winked. "See you in two days!" And she walked out of the door.

I sat there dumbstruck on the couch for several minutes. What had just happened? What was going to happen? And how was I going to be able to make this choice?

What would you choose, dear reader?

It was not an easy choice to make. I wanted to be normal, have a normal relationship with Chloe. Every time, I thought about that, the blue pill tempted me. We would be back to a normal relationship. I would take care of her, have sex with her, go out with her. Best to leave things less complicated.

But the red pill... every time I thought of it, a chill went up my spine, and I grew aroused, so aroused. Those words she had spoken... the way she had called me sissy. She had spoken to my soul, to my deepest, darkest desires.

--

On Friday night, at 8:45 pm, everything was ready. I was back on the same couch on which we had had our conversation. I was naked, except for the bright red panties I was wearing, which left most of my hairy butt exposed. I could see the outline of my hard cock in the front.

At exactly 9 pm, I heard the sound of footsteps in the corridor, then a key in the lock. The door opened, and Chloe walked in.