From Straight To Slightly Bent h. 02byAkito01©
My decision to continue the affair is not a clear cut one. In the past, I never would have considered myself the sort of person who would cheat on their mate. On the other hand, I continued to play out the events of our first night together in my head, and all the things that I could still yet do to you... In the end, I knew I had to have you again. The fact I was cheating on someone of my own gender was troubling, but if it had been an ordinary woman who also gave themselves over to me as you have, I don't think I would have felt differently. This was about power, not gender -or at least, that's how I chose to see it at the time. Maybe it was simply the allure of cheap and easy sex, proof that frustrated man will fuck anything with an available hole.
We arrange another 'date'. I promise to make this coming evening at least as special as last time, and that even more might be required of you. I leave this last statement ambiguous, but I know almost exactly what I want to do.
I buy a new Cheongsam dress, the classic style of Chinese apparel that always looks very exotic and classy. It's with a strange sense of guilt that I realize that I've never spent this much on any particular item of clothing for my current girlfriend. Truth is, she would never fit into it anyway. There must be something ironic in the fact that of my two current lovers, the one with the more feminine physich is actually a man.
I also buy a couple of even less pragmatic accessories. I feel a bit like a criminal planning his latest crime. I don't think I've ever been so excited at the prospect of an evening's tryst, regardless of partner.
I arrive at your door, no earlier or later than the time agreed to. We both had to make sure we had the time to be alone, and that our alibis to our significant others were all in order beforehand. We may be foolish in the pursuit of our lusts, but we aren't stupid.
As soon an I am in your presence, I once again feel that cold, seething emotion that isn't quite anger, but which is definitely a bulwark against expressing any weakness or concern. Tonight, you are to be my tool, and I remind myself of this fact as I look at you. The last thing I want to do is lose my resolve at this critical moment. Despite the fact we have done this once before, there is still a large part of my conscious that is rebelling against this. In the realm of fantasy, I have played this evening over and over, but to look you in the eye and be in your presence, and knowing what it is we have come together for, it is more difficult than I let on. I sometimes wonder how it is for you. To give yourself over to someone else, to give them complete power, entails a great deal of trust I may not be worthy of given how short a time we have known each other.
"I think you know what I want," I say. "Now, get changed."
I hand you the large garment bag, containing the gift that I wish you to wear for me. This time I permit you to shower and prepare in private, allowing you that much dignity. Well, perhaps that is not the right way to put it. I think I worry that, seeing you as a man, I might lose my nerve. I will wait and see what the final transformation will bring.
I know, or at least suspect, that the whole cross-dressing thing isn't your typical style, but I simply cannot get beyond that, not yet. It's become too much part of the game, at least for me. It's part of the expression of control that I dictate your appearance when we are together. With the wig in place, and your make up applied, the momentary illusion of an exotic if flawed Asian seductress has been created. I know that it is a fiction, but one I am content to live with. I can only imagine how it is for you. Is it different to have the eyes of a straight man look at you in passion than your usual lovers? In the past, if I'd thought a man was looking at me that way, I'm sure my skin would have crawled. I must be a terrible hypocrite.
The dress is flattering on you. Colored a deep green with an ornate gold pattern, the skirt is slit high on the side to show off your legs, sheathed in the shiny tan hose. With proper heels, you legs would undoubtedly appear even more ladylike, but you don't own a pair, and I didn't bring any, so you remain in bare stockinged feet, which I find I rather like anyway. I get you to spin around to show yourself off to me, then to get you and I a drink.
Your eyes lowered, I only permit you to stand as I sit on the couch to sip the scotch you have provided. You really have used a fair amount of eye shadow this time, I note. It's a pleasing effect, and I remark on it, telling you what an attractive woman you make. I have you show yourself off to me, going so far as to make you stand on the coffee table and pose as per my instructions.
"You're a terrific little vixen," I smile, "Why don't you show me just how much of one you are. Work it. Show me how turned on you are."
You take the cue, seductively gliding one hand from your bra-stuffed bosom down the stretch of your abdomen towards your crotch. Your eyes close, and you raise the hem of your dress so that I can see the well defined outline of your cock through the pantyhose. You lick your lips in a slow circle as you brazenly rub and caress your own erection through the thin nylon.
Mouth going dry, I drain the last of my drink in a final gulp. I gather my bag and remove one of the special items I intend to use tonight; a pair of handcuffs.
"Get down from there," I order you.
Hardly giving you time to think, I force your arms behind your back and handcuff your wrists together. I tell you to be still, but also not to be afraid. I circle around you, noting your restive expression. No doubt you have no idea what will come next, and I must confess I am not so certain either. Looking at your hands trapped by the cold circlets of metal, I reflect that a little nail polish probably would have helped complete the illusion. Women's fingers are always a little more delicate and refined than mens. Still, I could pretend.
At first, I only prowl around you, trailing a hand over your body as I do so; over your chest, your arms, your back, your neck and your face. I come to stand before you, looking you brazenly in the eye as I slip my thumb between your lips and force open your mouth. I bend forward as if to kiss you, but instead I grab the back of your neck and pull, putting you terribly off balance.
Throwing you forward over the arm of the couch, I roughly move your legs further apart, making it impossible for you to get up. I press myself against your upturned ass, my hands gliding up the backs of your thighs, feeling the texture of the nylon. I quickly strip off my shirt, continuing to press my pelvis against your skirt covered bottom. My erection must be obvious to both of us by now. Undoing my belt, I pull down my trousers and underpants, leaving them as a bundle at my feet. With your face against the cushions, you look awkwardly back at me as I pull up more of your dress, slipping my erection underneath in order to rub my cock against your pantyhose sheathed buttocks. From your restive movements, your own cock must be engorged as well, as you squirm against the rounded arm of the couch to stimulate yourself.
I order you to remain as you are as I remove myself, finally taking off my shoes with the rest of my clothes. Reaching inside the bundle to my pocket, I take out one of the last items I had prepared -a tri-pack of lubricated condoms.
I pull you up from the couch and move you over to the wall. I make you lean against it, face first, your shoulders taking most of the weight. I run my hands all over you, from your neck to your knees, placing kisses as I go. I murmur in your ear about how hot you are making me, and how good I am going to make you feel. My hands slide audaciously underneath the hem of your dress until I am feeling your prick underneath the hose. I press against your length with my palm, feeling you tremble with the erotic pressure. I then release you, and proceed to pull down the waistband of your nylons to just below your buttocks.
I open one of the condom packs and roll the slippery plastic sheath down over the two most prominent fingers of my right hand. Since one of my favorite things to do with any woman I am with is to tease and stroke her from the inside, I intend to do the same to you. Making sure your legs are well apart, I press my rubber covered fingers against the opening of your anus. After a brief moment of resistance, my two appressed digits penetrate within you.
I feel the soft, tender tissues of your rectum. It's much tighter than any vagina, but with something of the same soft feeling. It occurs to me that while I always had to be careful while probing my girlfriend not to touch her sensitive cervix, here there were no such worries. In fact, I knew from what I'd read, that the prostate could be reached and stimulated this way. Looking over at your tense and hardening erection, I wonder if it weren't possible to bring you to orgasm this way. Not being a doctor, I'm not entirely certain what I should be feeling for, but I begin to gently probe around.
Perhaps this would be better with bare fingers, but that's not something I would have been comfortable with. Even so, I think I have found that golden spot, especially from the way your erection practically jumps as I rub it. I'm sure I must be smiling at this point, and I lock into a steady rhythm.
Your cock is rock hard and quivering. Drops of pre-cum drool slide from the slit and coat your glans. The feeling must be ecstatic; I can tell from your face. You are on your toes now, straining for release. Continuing to finger fuck you, my digits curling to access that elusive prostate, I watch with unblinking eyes for the moment of crisis. I can feel a sudden tightening from within, and you let out an uncontrollable grunt as your untouched penis ejaculates in thick long spurts.
You collapse slowly onto your knees, just as the splashes of semen begin to trickle down the wall as well. Whether it is drama, or you are genuinely wiped out by the intensity of the experience, I don't know, but seeing you prostrate on the floor as the result of your orgasm is incredibly arousing.
I turn you on your side, and kneeling down beside you, direct my prick to your lips. Painted red, your lipstick leaves a slight smear on my glans as it brushes against you before you open your mouth and take my erection. My eyes close, and my hands grasp the back of your shoulders as you start to suck me. I let my mind drift in an abstract haze as you work your tongue against me, only capable of using your mouth to arouse and stimulate me with your hands still bound awkwardly behind your back. In complete control, I thrust my hips in a short motion, fucking your mouth as I become more and more excited.
"No, wait, I want to do it," I pant, making the spur of the moment decision, "I want to do it inside you. I want to fuck you."
In a panicked rush, I open another package and swiftly roll the slick condom down over my tense quivering erection.
I move you back towards the couch. Laying you flat, your legs dangling off the edge, I press myself on top of you, wrapping an arm around your torso. With one hand around my cock, I guide the tip against your slack anus, applying steady pressure. Soon your muscles relax, and my glans are practically sucked up inside you. I continue to gently insert the remainder of my penis, amazed at the feeling. I have never had, or even been interested in anal sex before. It's definitely different that good ol' vaginal sex, much tighter.
I begin to pump inside you in short, sharp digs. From your labored breathing, I have no idea if what I'm doing is hurting or pleasing you, but it doesn't really matter. What matters is how I feel, and it feels damn good. I am not going to last very long at all like this. There is so much pressure all over my cock, so much warmth. I grit my teeth, looking down at your sexy, shiny legs and my own rough naked pelvis jutting against yours. I grasp your hips tightly, feeling the inevitable crest of pleasure rise within my tightening balls.
I come hard, my seed filling the deeply buried teat of the latex condom. Bracing my arms on either side of your shoulders, I loom over you as I ride the waves of my orgasm, and remain like that until those feelings fade away and my softened erection slides out of your behind.
"You're a great little fuck, bitch," I rasp, still giddy from the experience.
I only release you from the cuffs after extracting the promise that we shall meet yet again for another evening's fun. Again, my mind is brimming with all the yet to be realized possibilities, though at the same time, I wonder if I'm falling headlong into some potentially dangerous territory. Is this the road to greater self awareness, or self destruction?