Moment of Truth

The conversation was stiff, and a bit awkward. But we were talking. And so far she hadn't shown any kind of repulsion to the fact that I was wearing a dress, with her panties and bra underneath. We talked loosely like that for several minutes while she drank her coffee. We both knew it was about to get deep. It was just a matter of finding the courage.

Finally, after a bit of silence she took a deep breath and jumped in. "Tim, I don't really know where to start. This is all just so...not what I expected." She was obviously choosing her words, and so I just sat quietly. I had already made my confession, so it was her turn to talk. "It's a little easier to think about now than it was the other night, since I've had a few days to process it. I'm still not sure what to think about everything. But at the same time I have to admit, I think I've known something was going on for a while. I just never could put my finger on it."

Her statement caught me a bit off guard, but she was smart so of course she would have sensed something. From there things just poured out. As she talked I could hear bits of hurt and disappointment in her voice. But it was clear almost from the beginning that she wasn't mad, and that she was trying to accept it, which made me relax even more.

She asked some interesting questions, like did I want to become a woman, or take hormones or get implants. She asked me outright if I was gay, or even bisexual. I answered as honestly and completely as I could. No I didn't think I wanted to be a woman or take hormones. And no I wasn't gay, but wasn't sure about bisexual.

We talked for almost two hours, but it was good to get everything out in the air. And by the time the conversation started to wind down I felt fairly good with how things were going. In a nutshell she had said that this wasn't what she expected when we got married, but that she loved me and was willing to at least see how things would work out. I told her that I couldn't expect anything more.

She was quiet for a long moment. I wasn't sure what was going through her mind but I could tell there was something else she wanted to say. "I've been doing some research online," she stated. It came as a bit of a surprise but I took it to be a positive thing. "I've been reading some articles and things about other couples in relationships like this. About how wives cope with husbands that...are feminine. I was surprised at how common it actually is, at least to some degree. You're much more...into it...than most. But the articles were helpful. And based on what I read I'm willing to try. Things will obviously change for us. But we can talk about that later. Right now, I think we need to try and...reconnect."

The last statement was almost a question. But rather than answer, she stood up and slowly walked back to the bedroom. She paused at the door and gave me a look that told me she expected me to follow her. So I got up and followed her into the bedroom. She was standing at the foot of the bed, and as I entered she said plainly, "take your dress off and lay down on your back."

The way she said it was more like a command than a suggestion. But I was curious to find out where she was going so I did as she said. Letting my dress fall to my feet I got onto the bed, still wearing my panties and bra. She came over to the side of the bed and said in the same tone, "keep your hands to your sides. I don't want you to touch me. At least not yet." Again, I did as was instructed.

I lay still and watched her as she looked me over. She knelt on the bed beside me and ran her hands over my body. "I see you shaved. You did a very nice job." Her hands felt wonderful as she touched my smooth skin. I started to respond but was cut off before I could speak. "Don't talk. Just be quiet."

Feeling her hands on my body was very arousing, and in no time my cock started to harden until it was straining against the panties I wore. She ran her fingers lightly over my erection, making me squirm in anticipation. Then after a few minutes of heavenly torture I watched as she reached under her dress and pulled off her panties. She repeated her instruction to keep my hands at my sides and not to touch her, then climbed onto the bed and straddled me.

Hiking her dress up to her waist she rubbed her pussy against my throbbing organ. I could feel the heat and the wetness of her arousal. I was pleased that she was clearly enjoying herself so far. I felt her hand on my cock again. She gave it a squeeze before pulling it out from its panty home. Then with little prelude she pressed it to her opening and settled herself down, taking my cock deep inside her pussy.

I wanted to touch her, to caress her legs and cup her breasts. But I kept my hands to my sides as instructed. She moved on top of me for several wonderful minutes. And the whole time I could tell she was focused on herself entirely. I was just a tool for the moment. I could sense that she was getting closer to a climax. But the excitement of the moment and the feel of her pussy on my cock was more than I could take and I came hard, deep inside her.

I could tell immediately that she wasn't happy. "Dammit, Tammy, I wasn't there yet. You aren't supposed to cum before me. Now you'll just have to finish me off another way." And before I could respond she moved herself off of me, letting my shrinking cock fall out of her, and positioned herself above my face. "You said you like tasting your own cum. So since you didn't let me finish, you'll have to clean me out."

She lowered her pussy onto my face so that I had no choice but to do as she said. She rubbed herself on my mouth and nose while I licked her pussy as fast as I could. I could indeed taste my own cum as it dribbled out of her pussy, mixed with her own juices.

"Oh yeah, girlfriend. You like the taste of your own cum? You like eating pussy like a slut?" Her taunts were unexpected and a bit unnerving, yet a bit arousing at the same time. But there was no way I could respond. "You like the name Tammy? Because that's going to be your name from now on. You're now my girlfriend Tammy". She ground her slit on my face for several minutes until she was moaning and grunting through her own orgasm.

Finally, as her orgasm passed, she got off of my face and sat down on the bed beside me. "Well, that really wasn't so bad. I think this might actually work out after all. But there are clearly going to be some new ground rules around here." I was still too stunned at what had just taken place to respond so I just listened obediently.

"Since it's clear that you're mind is made up, this is the way things are going to be around her from now on." There was no question, based on her tone, that this was an ultimatum that I would have to follow if we were to stay married. "Since you seem to get your pleasure from dressing like a girl, you can experience the girl's side of sex too. That means that I get off first. You can hold your own orgasm until I've had my first. And you won't touch me while we're fucking until and unless I say you can."

She went on with her list of demands and changes. "From now on, since you obviously prefer it, you'll wear only panties, and you'll always wear a bra or cami. No matter what you're doing you'll have a bra or cami on, unless I say. And you'll wear whatever I tell you to. I'll pick out your clothes for you from now on, at least until I think you really know what you're doing, or you get your own clothes. You can keep some of your man clothes for special occasions. I'm not ready for my parents to know that my husband is a girly girl yet. And you'll need some clothes for work, at least for now. But otherwise you'll wear only women's clothing."

"You'll also be Tammy from now on, unless we have guest around who I don't want knowing your true nature." She had a few other rules, but it was clear that the bottom line was that she was in charge. I wasn't prepared for anything that extreme. But I wasn't ready to protest either. I was still too stunned by her aggressiveness. And beside all that, I was going to be able to wear panties all the time.

Finally she looked at me as she put her own panties back on and said, "Get up and get dressed. We're going out to do some shopping." I kept my mouth shut as I pulled my dress back on, thinking, 'oh shit, what have I gotten myself into.' Never before had I worn women's clothing in public, except of course for panties which were hidden under my clothes. But it was obviously all or nothing at this point. So far everything that had happened, and all of Vivien's demands, I could actually live with. But I wasn't so sure about going shopping dressed as a girl. I guess I was about to find out exactly what it is that I've asked for.

Vivien dragged me into the bathroom and gave me a quick and basic facial, insisting that I pay close attention to what she was doing so that I could learn to do it on my own. I had never worn make-up before. But I liked the attention. It was far and away more feminine that I had ever been. She then did some kind of magic with my hair. My hair was a bit shaggy, but still relatively short. So there wasn't much to work with. She did some minor trimming, and a lot of fluffing. But after a few minutes she was done. I got a brief look at myself before she dragged me out to the car. She had done an amazing job for what little she had to work with.

It was only a short drive to the mall, but the whole time I couldn't help shake the fear that someone would immediately know I was a guy in drag, or that someone might actually recognize me. Fortunately Vivien did some pretty amazing work. I checked myself in the mirror several times before we actually got to the mall. I had to admit that, if you didn't know I was a guy, you'd have to get pretty close to figure it out for sure. Still, the walk through the parking lot was torture. I was sure everyone around was watching me. But when we finally reached the door I realized that most people are minding their own business and probably haven't even noticed me at all.

I was able to relax a bit after that. Which is a good thing, because from the second we walked through the door I realized I was about to live another part of a dream that I figured would never come true. Up until that point, most of the clothes I had worn were purchased online, or under false pretenses at a smaller department store. But now I would be shopping for real, in person. I could browse the racks and try things on. It was such a wonderful prospect that I completely gave in to the experience and let Viv lead me where she wanted.

Over the next five hours we tore through three department stores and a few smaller shops, and tried on just about everything we could think of. Seeing an item online is one thing, but being able to touch it and try it on before buying it was amazing. Together we tried on everything from dresses and skirts, to bras and negligees, to even swimwear. It was a wonderful experience. And admittedly one I would never have had if Vivien hadn't caught me wearing her panties. I wasn't prepared when Viv dragged me into a salon and had my ears pierced. But I was glad, afterward, that she did.

After shopping we stopped and had dinner at a mid-level chain restaurant. The whole afternoon had been wonderful, like two girls hanging out at the mall together. That mood and conversation continued through dinner. And as she has always been able to do, she put me totally at ease. By the time we got home I was exhausted. But I had some great new clothes. And I was excited about the way things were turning out with Vivien. It was looking as if our relationship, and our marriage, would survive, and I would be able to continue living my feminine dream.

We got our new things either put away or put into the laundry. Then we spent another hour taking most of my old clothes out and packing them in boxes. It was an odd feeling to consider that I would be wearing mostly women's clothes for the foreseeable future. But t was also one that gave me butterflies.

Finally it was time for bed, and I went about getting ready as I always did. Except now I was putting on a babydoll nightie instead of a pair of shorts, and Viv was watching. I was looking forward to making love to my wife, albeit on her terms. And as she approached the bed my loins started to tingle. She was wearing a sexy robe that covered what I knew was a very revealing babydoll.

As she got to the edge of the bed I actually reached out for her before she gently scolded me. "I told you earlier, you won't touch me until and unless I tell you to. Now come here and sit on the edge of the bed." I still wasn't sure I was ready to be bossed around like this, but I was already turned on so I obeyed. And her tone has calmed quite a bit from before.

"Now, are you ready to be my obedient girlfriend? 'Cause I'm about to rock your world." She then opened her robe and let it fall to the floor, revealing the lovely babydoll I knew was underneath. But it wasn't the babydoll that held my attention. It was the 8 inch strap-on cock she was wearing.

"What the fu..." I started to say.

But I was interrupted immediately. "No talking. You wanted to be more feminine. So now you can get your first taste. Suck my cock, bitch." Even if I wanted to respond, I didn't have the chance. She grabbed my head and pressed her rubber cock against my mouth. I had no choice but to open up and take it in. "That's it, girlfriend. Suck that cock like you know you want it." She held my head in her hands while she slowly pumped the strap-on in and out of my mouth.

After a while I took over the motion on my own and she let go of my head. And I quickly learned that the strap-on was two sided. There was obviously another end that was inside Vivien's pussy. When I realized that, by sucking the cock, I was actually causing it to fuck her pussy, I gave it my all. I sucked her cock like she had sucked mine before. No, I sucked it like the whores I had seen in porn videos. I sucked like the slut I had no idea I was. I sucked it until she was gasping for air as an orgasm rolled through her body.

She pulled the cock out of my mouth as her orgasm passed and she caught her breath. I started to get up, but she obviously wasn't done. "Hold on girlfriend. We're just getting started. It's time for you to give it up. Turn around and get on your hands and knees."

I immediately knew what was coming. And while I had pleasured myself with a dildo in the past, I had never had anyone fuck me with one. I was both excited about it, and dreading it. So I did as instructed and got on my hands and knees. I felt her hands rubbing my ass through my panties before she pulled them down to my knees. Then I felt the head of the dildo pressing into my rosebud. It was bigger than anything I had ever used on myself, and I was relieved when I felt her pour some lube into my crack. She massaged it around with the head of the cock and then started to press into me.

I was grateful that she went slowly. Otherwise she would have torn me apart. She would press in a bit before pulling out again. Centimeter by centimeter she pushed the massive cock into my ass, talking dirty to me the whole time. "Oh, yeah. My girlfriend is going to love getting her pussy fucked. You want this so badly, don't you? Tell me how you want it, bitch."

By that point I just wanted her to get it inside me so my asshole could adjust to it. So I answered her. "Yes, Vivien. Fuck my pussy. I want your cock inside me." It felt strange to speak the words. But as I said them I knew I actually meant them. It was just like my fantasies in college. I was about to be taken, and there was little I could do to stop it. And when she finally pressed the cock past my opening and into my bowels I couldn't help adding, "oh, god, yes.!"

Vivien quickly worked into a rhythm as she pounded my ass from behind. I felt like a dirty whore, but was loving every minute of it. And the feeling of the cock rubbing against my prostate, without me having to do it myself, was fantastic. I had never actually brought myself to an orgasm through anal penetration before, and it was starting to feel as if this might be the first time. But Viv beat me to it. She started grunting and moaning, and I knew she was having a second orgasm.

She continued to pump my ass as her climax washed over her. The she suddenly pulled out. My ass felt empty and all I could think about was having her cock back inside me. And I didn't have to wait for long. "Turn over. We're not done yet." Was all she said, though the words came out breathy. So I did as I was told. I kicked my panties off and rolled over on my back. I raised my knees to my chest and then spread them to the side. I was rewarded for my obedience as Vivien pressed her cock back inside me.

She fucked me again for another several minutes. But the change in position was all I needed. The longer she went meant more rubbing on my prostate. And then, for the first time, I was ejaculating from anal sex. My cock wasn't even hard. It had gone soft as she worked my ass. But I was still having an orgasm, and shot after shot of cum flew from my dick onto my belly and chest. It was the most intense orgasm I had ever experienced. And it kept going while she kept pumping. She gave several more thrusts until she was cumming again herself.

It was almost surreal. It was the orgasm that every man dreams about, lasting nearly 30 seconds until Vivien stopped fucking my ass and the dildo came out. Never has an orgasm lasted that long. And never have I cum so much. I had read about anal orgasms before, but never experienced one. I can now say that they are everything they are reported to be.

When her orgasm had finally passed, Vivien picked up my panties from the floor and used them to wipe the cum from my belly. Then she handed them to me and said, "Clean those off and then put them back on. No sense in getting another pair dirty tonight." I did as she instructed, licking and sucking every drop of my cum from my panties before pulling them back on.

By the time I was done, Vivien had taken off the strap-on and put on her own panties. Then she crawled into bed beside me. Apparently she had gotten her fill from the three orgasms she had just experienced because she was suddenly all loving and gentle. Pulling me to her she kissed me passionately, like we used to kiss before and right after we got married. Then she pulled my head to her breast and held me like a child. As we drifted off to sleep I heard her saying, "I think things are going to work out just fine."

We continued to experiment over the next week. Vivien was still in charge, telling me what to do in bed, but she was no longer demanding. And I was enjoying my new role as her sex toy. And each time I came I ended up eating my own cum, either directly from her pussy, or from whatever was used to clean it up. My 'pussy' was sore for a few days, but by the weekend I was able to fully enjoy being used like a slut.

At this point we're both figuring things out as we go. But the future looks bright. And I get to wear panties whenever I want.