Scott's Dominant Fantasy (12 page)

From a high stool near the kitchen counter I ate trying hard to resist my desire to touch my clitty. Watching and listening to them, I couldn't help but wonder how diabolical these sessions would become. What sort of things would they do to me and how would I react? Would every session be as new and sexually exciting as this one? What surprised me was I was not afraid; I wanted to be here.

After dinner I was told to take my tights off and walk about with my erection bobbing. This did two things; first it exposed my clitty to the teasing, light touching, squeezing, and occasion licks by April which lasted throughout the evening. However it was the second effect which distressed me. I found it quite hard to imagine myself female with this as openly engorged male organ jutting out from my crotch. My own body was causing me great consternation and upset by thwarting my desire to feel female.

Most of the evening I was merely an observer as April and Paulo engaged in a prolonged session of deeply sensual anal sex. Paulo rode April's ass, his massive cock buried deep in her bowels while he grabbed her long raven hair and it might have seemed she could not be enjoying her situation. However it was soon clear to me she enjoyed it as much as he did and when April finally collapsed in exhaustion she looked over at me.

"That's how you want your Master to fuck you, Stacy. No let up, balls deep, and taking his pleasure. It's not important for him to be concerned with you because it's his pleasure that matters. Now, would you like to try it?” April's voice sounded like she was teasing me about taking Paulo's huge cock inside me, but I wasn't sure.

"Don't misunderstand, Stacy, she means do you want her strap-on tonight. I'm well aware that you're not ready for this.” Paulo's clarification brought relief from the stress of the moment, but then I had a new thought.

Looking at Paulo with his cock still jutting out like a sword, I could see how inferior my organ was to his, but I suddenly realized there was some bubbling desire there, just under the surface. As I kept by eyes riveted to his hard body and beautiful cock I thought things I never would have imagined weeks ago.

"Stacy, Stacy, hello, I expect an answer.” April was angry at my daze and when I looked at her she was frowning at me.

"Easy, dear, this is one of those moments I was referring to earlier. Stacy is having new thoughts, things she's never experienced before.” Paulo's sense of my psyche was amazing and I was grateful to him for the time.

"It's beautiful, My Lady and I think I understand why you want to give it pleasure, but I just don't think I'm ready tonight.” I sensed April would be disappointed in me and perhaps part of me was disappointed, Paulo understood.

"Don't press her, let these things come. Processing experiences and understanding the emotions they provoke is important for new subs. You do remember how reluctant you were to take me up your ass, don't you?” Paulo smiled and April suddenly got a rather sheepish look.

"Yes, Master, as always you're right. I think it's time to ice you down, Stacy, and put your clitty back in chastity. I'm going to keep you chaste for now because I have a delicious idea as to when and where your first orgasm should be. Come, Stacy, let's get some ice.” April got up off the sofa and led me to the kitchen and so ended my first live session.

As I drove home sitting on the plug and the sensation of having it pushed deeper in my ass was powerful. I'd been told I would wear it to work, like my chastity and I now began to understand how as it stretched my anal ring, making my ass more open to penetration, I would begin to enjoy the sensation and then crave it. Of course this was being done to alleviate pain when I was fucked, but that didn't cover up one simple glaring fact of my status. I was yielding up the primary mindset of my gender, falling from the ranks of those who fucked to those who were fucked. In the tribal mindset of those ultra-masculine, primitive mammoth hunters of thousands of years ago, I was no longer the hunter, I was the hunted.

[Back to Table of Contents]

"Shopping, Lady April, you mean right now?” I was surprised when April strutted into my office at lunchtime on a Wednesday afternoon and declared her intentions. I'd had another live session with her and Paulo this past Saturday and things had gone well, but there was something about this shopping expedition which alarmed me.

"Yes, right now, with some friends. I've researched company policy on your transition and I've decided to move forward so we're going to get some things for you. Finish up what you're doing and meet me at my jeep in fifteen minutes.” She turned to go apparently feeling there was no more to be said.

Caught off guard and confused, I stammered. “But . . . we both have work to do. It's awfully early in the day to leave.” The truth was the workload wasn't especially high, but I was frightened by the suddenness of April's decision to take my cross-dressing fetish full time and make me appear to the whole world as a female. I'd been warned it would happen, but it was a huge step and I worried if I had the courage to let the world see me in a skirt.

"Are you getting cold feet? You're the boss, Stacy. At least they think you are. No one will question you leaving and after all, you want to do this.” April paused and moved towards me making sure her body was facing me and thus not exposed to the glass front wall of my office. She unbuttoned her blouse to show me her magnificent breast in a sheer, aqua, push-up bra. “You want to wear pretty things like this, don't you? Let Stacy come out, set her free."

"Yes, I do, but it's just so fast . . . I'm not sure I can . . .” I was terrified of the prospect of transforming this quickly.

April pulled the thin chain which ran down into her pretty bra and there was my key. “We're going shopping, Stacy in fifteen minutes. If you don't want to come, if you've lost your courage, then we can go to the men's room right now and I'll release you from chastity. You decide.” April showed little emotion as she spoke making me think she really would end our kinky game.

I couldn't let that happen. “Okay I'll meet you at your jeep in fifteen minutes to go shopping."

"Good, eventually you'll be glad I pushed your sissy ass here, Stacy. You're going to have a fabulous time. I'm so excited about this.” As April strutted out of my office and my eyes followed her long legs encased in skin tight, white spandex leggings, I thought I hope so, but I was still very worried.

It was just my luck to run into Greg as I left the office for the parking garage. He was perhaps the one guy in this office I'd developed somewhat of a relationship with because we'd been hired together six years ago. Coming up from behind me he gave me a manly slap on the back before he spoke in a hushed voice. “Hey, man, what's up with you and April. I see you're back with her, you lucky dog. Are you leaving for a little afternoon delight? She's so hot, but then I love those Latina bitches. What's she like in the sack, a real tigress I bet?"

For the first time in my life it struck me how I hated these male conversations about women. Not only were they mostly innuendo and gossip, an activity men professed to dislike in women, but there was so little information or emotion expressed. No doubt Greg assumed I'd scored with April and he wanted carnal details, but I wondered what he'd think of me if he knew my ass was plugged and my penis was locked up and covered in panties. Part of me wanted to tell him what my relationship with April really was, but the other part was afraid to because of what he might think.

"Yes, I'm . . . with April again, Greg.” I accented the word with as I imagined how badly Greg's mind would be blown if he knew the truth.

"So what's she like in bed? Does she take it in her backdoor?” Greg asked and I thought
no, but I may soon

"Sorry, buddy, but you'll just have to keep fantasizing about how April is in bed because I don't kiss and tell.” Quickly I slipped into the elevator and was gone, but a strange feeling lingered in me. My conversation with Greg highlighted some of my fears about transitioning. If I wasn't going to think like a guy, then I'd have to think like a girl, but how did they think? I really didn't know what the differences were, but I supposed I was about to find out.

When I reached April's jeep it seemed like I'd stepped into some surreal feminine world, a place I'd never been before. Already sitting in the back seat of the jeep was Anita Valvano, a longtime employee in her late forties whom I'd never even thought about in a sexual way, and Laura Curtis, a young girl who we'd barely hired as a file clerk. I had interviewed Laura briefly so I knew she was nineteen and a local college student, but seeing both of them in April's jeep and knowing they probably knew about me changed my whole perspective on them.

As we departed the parking garage there was a sort of polite silence until April broke it. “Anita, Laura, I'd like you to meet Stacy. You know Stacy as Scott, our boss, but deep down inside she's really just one of us girls and soon she's going to look the role. Stacy's been roleplaying as my slave, but not as a male, as my feminized, sissy slave. That's really why we're going to the mall today, to help Stacy pick out a nice new wardrobe."

Of course April's comments were followed by girlish giggling from the back seat and my face must have been beet red with embarrassment. Having no idea what to say, I stayed silent, but Anita had no such qualms. Pushing her face forward from the back seat, she looked me over. “I guess this goes to show you never know what someone is on the inside. I was quite surprised when April told us you let her . . . ahh . . . lock up your privates. Can we see it, Stacy?"

Oh my god.
Now I realized April had told them everything about me and a fresh wave of shame and embarrassment rolled over me. Inside my chastity, my clitty was stirring, hardening no doubt because of my humiliation as it always seemed to do now. My masculine side screamed at me.
What the hell, you aren't really going to show it, are you?
My brain was in such conflict I was unable to respond to the question or even move.

Leave it to April to reach over and feel my crotch, pushing against my chastity. “Oh come now, Stacy, don't be shy. It's only us girls here. You know you want to show your clitty.” April's tone was coy and sexy, designed to lure me deeper into self-humiliation.

There was a fresh giggle from directly behind me. “Oh my god, what did you call it?” It was of course Laura reacting with shock to April's reference to my penis as a clit.

"A clitty, Laura, sissy slaves don't have cocks because they're not men.” April advised Laura.

More giggling and then Anita pleaded. “Please, Stacy, let us see."

All sorts of thoughts were cascading through my mind, but I tried to focus on this moment because I knew I had to move forward, it was the only way. Taking a deep breath I reached down and undid my belt. As if comforted by my ability to move, I unzipped my fly and pulled down my pants just enough for the eager female eyes to see today's choice of pink panties.

"Oh, very cute, Stacy, but we want to see under them.” Anita pointed out.

It was at this moment I felt a release of sorts as I understood I no longer had to hide my hidden desires from these two women. They would now join April and Paulo as the only members of my new world; the world which knew I desired to be female. Soon they might be joined by the whole office and then perhaps the whole fucking world, but for now, by virtue of what they knew they were my closest friends.

From the back came Laura's squealing, high pitched voice. “Jeez, he's wearing pink panties, it's fucking unbelievable."

April reacted immediately to correct Laura. “She's wearing pink panties, Laura. Always use the female pronoun when referring to Stacy. We will respect her desires to be a gurlie especially when she is obedient and shows us what's underneath her pretty panties. Right, Stacy?” April cleared her throat as she looked at me and I understood she wanted me to get on with exposing myself.

Slowly I pulled my panties down revealing my chastised manhood and as I looked down at the penile flesh pressing against the hard plastic, it seemed like I was looking at someone else's penis not mine. I felt separated from my manhood.

"Oh, gosh, this is amazing. I wish they had these things when I was twenty. Things would have been much different in my marriage if I could have controlled Barry like this. Imagine if I'd been able to lock his little pecker up so he couldn't run around fucking anything in a skirt. It would have been great and would have kept him locked up until he begged me for relief. That would teach him.” The sad story of Anita's marriage to the handsome but womanizing Barry had been told many times at the office. Three years ago, her sixteen year old marriage had ended when her husband ran off with a much younger woman. When I'd heard it before I'd always thought it was sad, but now I saw it from a more female perspective and I could understand why Anita would lock Barry up.

Now Laura chimed in. “Where do you order these and how did you get hi . . . I mean her in it? I'm not sure my guy is fucking around, but with this I could be. It sure gives a girl the upper hand.” Laura giggled softly, but I had a hard time imagining any guy cheating on her because she was a knockout with short blonde hair with streaks of black running through it. I'd assumed it was some sort of Goth thing when I first saw it, but with her dynamite body most guys wouldn't have cared if her hair was green.

"I can send you the link to the website where I purchased it.” April reached over to my chastity and tapped the plastic with her finger.

"Stacy, why don't you tell the girls how it feels to be locked-up? I'm sure they'll be interested.” April teased.

At first I hesitated, but then, perhaps because I wanted to tell, my resistance crumbled away. “Well, I thought I'd go crazy at first when the desire was first building beyond the point where I would have masturbated, but you do learn to deal with it. I never believed I could get this horny and my first instinct was to try not to think about it, but that's almost impossible. What eventually happens if your desire to cum, your arousal, and your need become like a drug and you stay high on that instead of the pleasure of climax. I'm probably not making any sense because it's hard to explain, but I feel like wanting is almost like having now.” The truth was I felt supremely frustrated by my inability to communicate to them how I felt.