Paulo's reaction was immediate and positive. “Outstanding, my dear, I never would have thought you could achieve a look this good so quickly. I mean I knew who would be here, but if I hadn't, well I might have been perplexed.” Paulo continued to stare at me as he moved toward me and his fingers touched my tissue-filled bra.
"Now I see why you begged me to fuck you in this outfit last night. How appropriate to have her wear things anointed with my semen. Despite what you think, my dear, you do have a talent for dominance.” Paulo turned to April and pulled her in for a passionate kiss.
"Of course they're nowhere near your talents as a slave and it's in watching those that our little Stacy will learn so much.” Paulo turned back to me and ran his fingers down my bare belly making me shiver at his touch. His touch felt electric to me and I didn't understand why.
"May I?” He asked as his fingers came to the waist band of my tights.
It was a crucial moment, but I realized I wanted him to touch me. “Yes, Sir."
He ran his fingers down into my crotch, lightly touching the soft powder blue fabric covering my trapped clitty.
"Chastised, I see. I approve and locking her improves her look. Unsightly erections can be so annoying, but we'll talk more about her sexual needs at supper. Right now I'm going to shower and change. It's your decision of course, but I suggest we have Stacy serve dinner. I think she'll enjoy the experience.” Paulo patted my chastity as he looked me over one more time just before he finally departed into the bedroom.
"As you wish, Master.” April responded and we made our way to the kitchen to get April's Parmesan chicken casserole and asparagus ready to be served. As I followed April, I wondered if Paulo's touch would always feel like it did to me.
"Your clitty is trying to get hard, isn't it, Stacy?” April asked me as soon as we entered the kitchen.
"Yes, My Lady, it has never stopped.” The pressure alone was quite uncomfortable and I was so glad April had decided not to put the sharp points of intrigue in my chastity.
"Well then, let's give you some relief. I have to free your wrists to serve so let's free your clitty. I'm sure Master will be amused at what pops up in your sexy tights.” As she was no wearing my key, April hurried to the bedroom and quickly returned with it.
However as she unlocked me she warned me, “Don't you dare touch your clitty. If you do, or if you climax you'll be severely punished."
I was more than a little concerned that I'd just spontaneously orgasm because of the situation and the soft sensuous nylon which would encase my hardened organ. “But, My Lady, what if . . . it just happens?"
"No exceptions, no reprieves, if you touch yourself or climax you'll be punished.” April stated with resolve.
Clearly my sex life was no longer mine. It had become a form of amusement for others, but only because I seemed to want it that way.
By the time Paulo entered the kitchen in black leather pants and a red silk shirt, I was erect with the head of my cock pushing up close to the waistband of my tights. When Paulo saw me, I discovered a whole new level of humiliation to be so exposed in his presence. He smiled and they seated themselves at their kitchen table and I began serving the food, but it became impossible for me to not be intimately aware of every sway and bob of my erection.
There was silence until I poured Paulo's wine and then he made an observation with my engorged clitty facing right at him. “I see Stacy likes the changes you've made in her lifestyle. I expected she would. Do you have a plan to take her further indulging her deeper desires?” He wasn't speaking to me he was speaking about me and I knew it.
"Yes, Master, I plan to allow her relief in planned certain situations designed for my amusement and at some point, I haven't decided when, I intend to open her up as you suggested.” April turned to me. “Stacy, would you show Master your backside."
I'm not sure why considering the situation, but the idea of showing my plugged ass was somehow shocking to me. My surprise caused me to delay and that displeased April. No doubt she wanted to show Paulo how dominant she was so she leaned towards me and slapped my flank with all her might. “I said, show your plug, bitch."
"Yes, My Lady.” The crisp slap jolted me to action and I put down the wine, turned, bent over, and pulled my tights down over my bottom thereby displaying the pink plug in my ass. Wave of raw humiliation rolled over me and my male side raged over how I had allowed this to happen. No real man would do this.
However the bottom line was clear and despite my shame my clitty was so hard, so ready to explode. This experience was far more excited than any masturbatory session as a man had ever gotten me so I knew this was the way.
"Excellent, I hope you'll allow me to watch at least once, my dear. I'd love to critique your technique. You may stand up now, Stacy.” Paulo was looking right at me when I finally stood straight up and no doubt my face must have been red, but in my gut there was a smoldering desire which he addressed.
"Right now that plug is strange and uncomfortable to you, but you'll soon begin to desire it right where it is. When it's taken out you'll feel empty and deprived. Then when April starts fucking you, at first you'll be unsure if you like it, but gradually you'll begin to accept it and then enjoy being penetrated. It will begin to define you and you'll start acting like a little sissy tart begging for a good fucking. After that, well, who knows what might happen.” This was clearly another in a series of astute observations by Paulo yet as I listened and realized April intended to switch the sexual roles on me to become the penetrator rather than the one penetrated I could barely believe this was the life I wanted.
"April, what do you think Stacy wants more than anything right now?” Paulo seemed amused, but he was clearly treating this as an opportunity to teach both of us.
"That's easy, she wants to cum. Her clitty is probably harder than it's ever been before.” April's assessment was correct at least in my mind.
"Yes, but let's be more specific, shall we? What if we told her she would be stroked to climax, but gave her a choice of whose hand would be on her clitty to jerk it off? Whose do you think she'd choose?” Paulo was staring at my erection tenting my tights as he asked this.
"Well I suppose she'd want me to do it. She's a little unsure about being touched by you and she's more than used to her own hand, but isn't it my choice, Master, as to when she climaxes. I'm not sure I really want her to tonight. I'd like to build her desire.” April clearly seemed reluctant to end my chastity this soon.
Paulo was surprised by April's assertiveness, but he was also pleased. “Yes, absolutely, it is your decision and I'm glad you realize that. By all means keep her chaste if you desire, but in the meantime talk to her about how she feels and what she fantasizes about. This accomplishes two things; it allows her to vocalize her feelings and validate them with you which we know females need, but also by listening carefully to her you can get ideas, a sort of a road map of her submissive psyche, on how to best dominate her.” Paulo's capacity to not only do, but to explain and teach others amazed me.
"Really, I never would have guessed that. Does it truly work, Master.” April seemed all too impressed with her Master's acumen.
"It worked well with you, slave. You gave me all the ideas I needed.” He smiled and then turned his eyes to me. “It will work for Stacy too, believe me."
"So, Master, in reference to your question before, whose hand do you think Stacy wants on her clit?” April was already applying her lessons. She was probing her Master's mind.
"Oh it's not important what I think, what does Stacy think?” Paulo looked up at me in expectation of an answer.
This was confusing and suddenly I felt all warm and dizzy. I knew I couldn't say my own hand because they'd know I wasn't sincere, but each time I tried to decide between the two other choices I simply couldn't. “I'm not sure . . . it's hard to think. . ."
April looked angry at me as if she thought I was dodging the question, but Paulo observed. “Don't be angry with her, m
y dear. She probably can't think. See the confusion you've brought about is the result of the male mind trying to override its lifelong programming.” Paulo statement immediately raised April's eyebrows in curiosity.
"How do you mean?"
"Simple, the inner submissive, Stacy, knows the answer, but poor Scott is muddling things up with all he's been taught. He simply can't say it so every time he tries to think he runs into a roadblock of mental confusion. For the next few weeks there will be a battle between the two to see who really controls their desires. Apply gently pressure to her, but don't be too harsh if she has difficulty deciding as there really is a lot of inner turmoil going on. You see, the problem really is, poor Scott knows he's losing and men don't like to lose.” Paulo paused a moment before deciding. “Let's not confuse her too much now. Let's eat, before the food gets cold, there'll be plenty of time for games later.” With these words, Paulo ended the possibility of my sexual relief coming right now.
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.
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Chapter 7
"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 an
d 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?"
Scott's Dominant Fantasy Page 9
