Mickie and Laurie Pt. 09

The next morning, I woke up and immediately remembered my new extensions. I felt the back of my head to confirm that the braid was there. I jumped out of bed and scooted to the bathroom to take care of my urinary needs. After flushing, I looked at myself in the mirror. With the make-up washed off, my face had lost some of its feminine appeal, but I still thought I looked OK. I reached back and undid the elastic on the end of my braid, then carefully unwound it. As my new hair spread out, I once again marveled at how it looked and felt. And Candy had been right--the braid left some wave to the hair, making it extra cute.

I studied the rest of myself in the mirror. My skin was soft and pale, except at my pinkish-brown nipples. The breasts underneath were pretty flat, but there was noticeable tissue there, which I could clearly feel when I poked it with my finger. My waist had continued to slim, and last time I had measure it was at 27 inches. I had hopes of getting it to 26 soon. Moving further down, I admired my smooth, flat belly, and the neatly trimmed patch of dirty blonde pubic hair above my caged clit. My hips were slender but rounded, and my butt and thighs were legitimately hot. If I were a regular guy, I would want to do me, or "tap dat," as Jamal had said.

I put my hair up and took a quick shower without shampooing, then started trying to figure out what to wear. My experience the day before with the outfit Mickie selected for me, and the make-up (and the hair!) made me wish I could go to work as a woman. But there just seemed to be serious barriers to doing that. I wasn't worried about the overall climate of acceptance among my coworkers, but some of the people I reported to seemed quite straightlaced, and my immediate supervisor in particular struck me as someone who could have a problem with a transgender employee, and that's what I would be. I had to admit to myself that I had undergone a major transition, and was now having to work fairly hard to disguise it.

Reluctantly, I wound my long hair on top of my head and covered it with my new wig. It looked weird to me, and I had to fiddle with it for a while to make sure it was fitted properly and secure. Once I had it the way I wanted it, I gave it a quick comb to make sure it didn't look to disheveled, and went into the bedroom to select an outfit. My narrow waist and rounded hips had been creating problems for me when it came to wardrobe. I settled on a loose, long-sleeve button-up shirt (to better hide my incipient boobs), and some roomy khakis to accommodate my butt. I used suspenders to hold up the pants, since their waist was way too large, then put on a cable pullover to cover up the braces. It was makeshift, and not very stylish, but it would be deemed acceptable at work.

I came out into the living area and found Mickie in the kitchen finishing up her breakfast. Evidently she had been up for a while. She raised one eyebrow at my appearance, but said nothing. She had made it clear for weeks that I needed to present my authentic self to the world. Maybe she was right, but I just wasn't ready to pull the trigger on that. The idea of putting oneself out there, open to ridicule or even violence was utterly intimidating to me. And there would be no going back, once I did it.

Mickie offered me a cup of coffee, which I thankfully accepted. I was not interested in any breakfast--I still needed to slim down a bit, especially if I wanted another inch off my waist. She asked how my hair was, and if I was still happy with the extensions, and I bored her for 5 minutes with all my enthusiastic opinions on what we had done the day before. She told me that she felt a real sense of accomplishment for thinking of and arranging the extensions, and that she though Jamal would be very happy about them. That comment caused me a little shiver of fear and anticipation: Jamal! When would he be back, and what would be in store for me.

It was shaping up to be a normal week, or as normal as my weeks could be in this new regime of continuing gender transition, constant efforts to disguise it, and dealing with my new hair. I tried shampooing on Tuesday, and Mickie gave me pointers on which products to use. Then there were the periodic romps with Mickie and a strap-on. On those occasions, when I was able to "let my hair down," I became obsessed with seeing what I looked like when she was fucking me. On Monday night Mickie moved a big mirror to floor level and put it against the wall near our traditional sex spot, and now I could look at myself being penetrated by my beautiful wife. And what sight it was: a thin, flat-chested woman with nice, shoulder-length blonde hair on her hands and knees getting railed from behind. If not for the metallic cage the peeked out of my crotch, it would have been easy to conclude that this was a pair of lesbians going at it.

Funnily enough, after working me over on Wednesday night, Mickie suggested that we could go dancing at a lesbian club. She thought that would be a great, nonthreatening way to show myself to the outside world, since the people there were absolutely accepting of all kinds of nontraditional sexual personae. I was intrigued and excited by this idea. It would be a blast to go out socially with Mickie, something we had not done in ages, and I had used to like dancing. However, did I know how to dance like a girl? I asked Mickie and she promised to show me a few moves. I was so fired up about this date that I had a terrible time falling asleep. What would I wear? How obvious would I be as a crossdresser or trans woman or whatever I defined myself as? We settled on that Friday night.

On Thursday, I came home from work to find Mickie dressed to the nines. She had on a sleeveless red minidress, short enough that I caught a glimpse of her matching red panties underneath, and no bra. She had bracelets on both wrists and her hair was in an elaborate updo. I wondered whether I had gotten the date wrong on our outing, but she told me that she was going to be getting together with Jamal that evening. I felt a double pang of disappointment: no outing with Mickie, and no Jamal.

We went through the usual preparations, but then Mickie pulled another surprise. Instead of my usual dildo, she brought out her big black one. My eyes widened with trepidation and excitement.

She noticed, and said, "Let's see how you like this big one," as she began to cover it with lube. "It's almost as big as Jamal," she continued. "Now when you hear him fucking me, you can pretend it's you."

An involuntary shiver passed through me. It would be a lie to say that I had not thought about Jamal taking me from behind and stretching my ass to its limit, or maybe beyond. But I remained conflicted about the idea because it was unknown territory, and I would not be able to exert any control once things were underway. On the other hand, most of Mickie's training had really been about giving up on the concept of having any control anyway.

Mickie used a heavily lubed finger to coat my anus, then did something else new. As usual, she had placed a towel on the bed where I would be lying. However, instead of having me on my hands and knees to slide in the dildo, she held it by its base, pointing straight up. She ordered me to position myself with my ass over the dildo, holding myself up with my feet and one hand. Using the other hand, I spread apart my butt cheeks and slowly lowered myself until I felt the slippery end of the dildo touching my asshole. Another shiver passed through me as I imagined the girth of what I was about to take.

I let gravity help a little bit and lowered myself. The tip began to spread apart my anus. I let myself drop some more, and now there was some resistance, as I felt pressure where the head widened. It was not painful yet, but I knew that would be coming. I was both dreading and craving that pain, and I did not wait very long before letting myself down some more. Now the dildo was pushing hard against my tightness, and I was definitely experiencing discomfort. I thought of what I would have to bear if I was ever penetrated by Jamal, and decided to stop being a baby. I began to actively push down, and as the pain ratcheted up a couple of involuntary whimpers escaped my mouth. Mickie was giving me encouragement, and reassuring me that I would be able to fit it if I tried.

Suddenly the head pushed all the way in, and I cried out in surprise. I stopped pushing, knowing that I needed to take this slow. Then I began carefully letting myself drop, until I hung up again on the wide spot of the shaft below the head. This was the last challenge. I knew that I was more than 90% of the way there, but I worried this last bit might split me in two. I slid myself back up and inch or so, and then pushed down. As I encountered the widest point, my movement slowed but did not stop. My brain was being inundated with sharp pain signals, but I let the movement continue and then it was in! I had about 4 inches inside me. Mickie clapped her hands and congratulated me, and I felt an absurd sense of accomplishment. I realized that I was sweating profusely from my forehead and scalp.

With a little more work, we got the dildo all the way in, so that I could lie flat on the bed. I had never felt so filled, and I wondered it this big object had pushed beyond my rectum into my colon, or was merely stretching my rectum to accommodate itself. Whatever it was, that was what would have to happen if Jamal ever fucked me.

As usual, Mickie cuffed me to the headboard and left my phone by my ear, then left to meet Jamal. She was more chatty than usual during the drive to his house, and checked with me a couple of times to be sure that I was OK with the big dildo up my ass. I reassured her that I was fine, and told her to enjoy herself.

Mickie's session with Jamal started out as normal, with relatively little conversation. I could hear the sound of her sucking his cock, and the memory of having done so myself the week before caused a wave of arousal to wash over me. Involuntarily, my anus and rectum stiffened around the big dildo, prompting a little moan of surprise from my mouth. She brought him to an orgasm, and I could hear her hungrily gulping his load. I felt a pang of jealousy.

After taking a break, they went back at it, and as I heard his grunts and her moans of pleasure, I became increasingly frustrated. I wanted to be there, at least to watch and perhaps to take an active role. I started trying to make the dildo slide in and out by squeezing on it and lifting my butt off the bed by arching my back, and it worked. As I raised myself several inches, I could feel the slippery shaft push out of my anus until the base once again rested on the bed. Then I lowered myself and felt it slide back in. I realized that this was a major discovery--I would be able to fuck myself while locked to the bed.

I started raising and lowering myself while flexing my ass, and as the pleasurable sensations grew I started making little moans of excitement. At first Jamal and Mickie were too busy with their own activity to notice, but eventually their sounds died down, and I realized they were listening to me. My devious wife had put her phone on speaker! I felt embarrassed, but there was no way I could stop now. I could feel a climax slowly building, and I wanted it so badly.

I heard Jamal speak. "That bitch is really getting into it," he said.

"Yeah, she's got a big dildo in her ass, and I'll be she's imagining getting fucked right now," Mickie replied.

I was starting to gasp from a combination of exertion and rising sexual excitement. I knew that they could hear me, and I was mortified, but I no longer felt it was an option to stop myself from climbing up the mountain. I didn't know for sure what was waiting for me at the top, but my body seemed to have bypassed conscious volition in the "knowledge" that it was something I wanted/needed.

"Bitch, you practice up," said Jamal. "I'm gonna fuck you so deep the cum's gonna pour out of your mouth." Mickie gave a tinkling laugh. Jamal's dirty talk only served to elevate my arousal further, and now I was beginning to make louder cries of excitement. I was raising myself higher and plunging down harder, and breathing heavily between my whimpers and moans. Sweat was pouring down my face onto the bed.

Suddenly I felt the surge of pleasure that I knew would now be unstoppable, and pushed my ass into the bed to make sure the dildo was as deep as it could go. My ass was clenched tightly around it, and I was shuddering uncontrollably. I felt wetness as semen began to leak out of my caged clit onto my balls, taint, and thighs, and as if from a distance I heard several loud, guttural cries that I realized I must be making. The whole thing seemed to last for a long time--minutes perhaps, though later I realized it must have been more like 20 or 30 seconds that were stretched as my climax caused time to dilate. As the sensations ebbed and my cries were replaced by gasps, I could hear Jamal and Mickie applauding me over the phone.

"You are such a good little slut, Laurie," said Mickie.

"I can't wait to slide my cock up that ass," said Jamal.

I lay there basking in the afterglow, and enjoying their commentary. Eventually they resumed their own activities, and both of them got off very loudly. I wondered if listening to me had helped raise their excitement levels. I hoped so.

An hour or two later, Mickie came home and walked into the bedroom. We looked at each other. I was in a thoroughly submissive situation: my hands secured behind my head cuffed to the headboard, still wet with sweat, massive dildo in my ass, and my crotch area covered in my slowly drying cum. She told me she had a treat for me. She climbed on the bed and straddled my torso and scooted up so that her pussy was over my mouth, then lowered herself down without saying anything. I knew my duty, and started tonguing her. Mickie was wet with her own juices, but Jamal's cum was mixed in and I hungrily plunged my tongue deep into her snatch to clean it thoroughly, while also giving her clitoris ample attention. She was moaning with pleasure, and eventually had an orgasm. As she climaxed, her contracting pelvic muscles squeezed out more of the liquid inside her into my eager mouth, and I happily swallowed it.

When she was finished with her orgasm, Mickie unlocked me, and told me that the dildo would not be coming out until I cleaned up my mess. I dutifully licked up the puddles of semen on the towel, then used my fingers to scoop up what was on me. It was cold and the texture seemed more runny than the jelly-like consistency of fresh sperm--certainly less enjoyable than normal, but a sissy's duty was clear, and anyway I craved the oxytocin.

After this, she unlocked my chastity device so that I could clean my crotch and my cage, then put it back on and locked it up. Finally, she gave me permission to remove the big dildo. It was an effort to remove it because much of the lube was gone, but Mickie did not let me apply any new lube. I managed to get it most of the way out, and then as my asshole clamped around the narrow spot below the head, I had to give it a hard yank. As the head popped out, I gave a cry of surprise. Once the dildo was out, she made me clean it thoroughly, saying that anything that had been in my ass had to be totally pristine before she would let it go in her pussy. I understood, and was very diligent in scrubbing its length with hot soapy water. Finally I handed it to her, and she put it away. I took a quick shower to wash away the sweat, then we went to sleep with Mickie spooning me. In my exhaustion I slept straight through the night.