Sissys First Time

By the time my wife, S, and I had been married for fifteen years, there was not much that we didn't know about each other. If you're going to make it that long, you're going to have to learn to be honest with each other. This is what had led to me recently, cautiously, come out to her as being bi, turning at once tepid physical relationship into one of ongoing smoldering, passionate experimentation. She was amazingly supportive. She bought out first strap-on, found us male-strip clubs, and even encouraged me to let my hands wander and linger while slipping dollar bills into the dancer's g-strings. But before tonight I had not been able to completely indulge this fantasy. But tonight was going to be different. An off-hand drunken joke in a bar, last night, led to an "are you serious? I'm serious if you're serious" exchange and soon she was picking out my perfect first-time stud. Now, tonight, she and a man half my age are drinking wine and flirting in my kitchen. She knew I wanted to be with a man and even arranged this experience for me, but she didn't yet know everything.

She never said a word, but the woman at the lingerie shop knew the bra and panties, thigh-highs and garters I spent all afternoon shopping for were not for a wife or girlfriend. My stomach was in knots the whole time, but the excitement of this woman knowing they were all for me was delicious. It was exhilarating, us sharing a secret I've been too embarrassed to speak aloud...that I was going to break all the most sacred taboos. Not only was I going to be on my knees sucking cock, begging a man to splash his hot cum across my face, shoot it into my eager mouth and fill my ass with it, I was going to do it all as a cross-dressing, lingerie-wearing sissy.

Back at home, S continues to entertain the young man while I finish dressing. The panties I picked out today will be just big enough to cover me when not aroused...now, as I slip them on over my stockings, the lace riding up my ass and the satin clinging against my tight skin, they leave nothing to the imagination. My cock, raging with anticipation, juts from the top of the waist band. It's head swollen, red and pulsing. I smile wide. This is just the look I was going for.

Once dressed, I take a few minutes to appreciate the complete image in the full length mirror. This outfit isn't going to fool anyone; I'm clearly a man in drag. Still, the outfit itself looks great. The stockings shape and tone my legs. The sweet bow in the front brings a certain level of femininity and innocence to them, and a sense that they are not in-line with the sultrier image I want to present. It's a detail that I wanted just for that conflict. S' high heels extend my legs in a long line, further defining the curve of my calves. My new tanga panties shaping and hugging my round ass. The rear seam rising higher inside me, titillating tonight's ultimate prize. The panties are slipped-on over the top of my garter straps, to be easily slipped off later. In the front, I manage to slip the tip of my sex back inside the slim fabric. Tightly outlined in the pink satin, it's no longer exposed, but certainly not hidden. Far from timid or embarrassed, I feel confident, emboldened and powerful...sexy. There is a strength in owning your nakedness, in being exposed and unashamed. I love my silhouette cannot wait to show it off.

I close my eyes to remember this moment just the way it was, the scent of the perfume, the sound of the music, the touch of the fabric. My stomach flutters as I imagine all the sins awaiting me...my mouth watering as his veiny long shaft first pops out from crisp jeans, my slippery soft wet lips opening wide to envelope the shiny tight skin of his mushroom head, for the first time ever, my tongue lapping at the smooth glans, toying his slit, the taste of salty pre-cum and musky scent filling my mouth...pulling him towards me, I take in his full length. Or later, laying back, legs spread, panties down around one ankle, hand leading his hard cock to my eager hole, arching my back and raising my ass to meet him, gasping from the shock when the big swollen bell first touches my virgin hole, begging him to push forward, moaning and grinding like a bitch in heat as he first enters me, and whimpering in pleasure as he begins slowly fucking me...giving in to be a man's bimbo slut, loosing all control and inhibition as he repeatedly drives his stiff cock in and out of my fuck-hole until, finally, he begins trembling inside and I feel his hot cum flooding inside me. Body flushed, I come back to reality with a shudder...I shocked myself I'm such a cross-dressing dick-slut. I can only imagine my wife's reaction. With a deep breath, I reach out and open the door.

The two of them go silent as I enter the room with a confident air and exaggerated hip and shoulders sashay...eyeing my man over the rim of the wine glass, playing coquette and finishing my wife's wine in a gulp. Setting it down loudly, they're both taken aback at the sudden noise. Wasting no time, and still without a word spoken, I step forward and forcefully kiss the young man, biting his lower lip, reaching down to feel for the bulge I pray would be there. Relief and bliss, it is, but before I can reach my fingers inside his pants and feel his tip, S grabs me around my naked waste and swings me round. When I finally look her in the eye, I see her face filled with desire. She takes my face with both hands and kisses me deep and passionately. Then lowering lowering them around my ass, she simultaneously pulls me to her and raises her thigh between my legs...grinding against my swollen cock. Her hot, wet, mouth finds my ear, tongue teases me before she whispers, just for me, "You look fucking fierce! This is going to be fucking amazing. You're going to love it!"

S takes a step back and with a wink, sternly announces "well aren't you a pretty fucking fag? So frilly and girly, all painted up like a cheap whore. Sure I've always wondered if you were gay, but this? I had no idea! Here all these years I thought I was the woman...turns out you were the real cock sucker in this marriage. I'll bet you can't wait to get this guy's big dick in it in your mouth. Well don't you worry, slut, you're going to get that, and so much more." With a flirty smile, she turns to my stud and asks "so what do you think, are you ready to fuck my husband in his dirty slut-hole? You can tell he's ready; look at his panties. They're already wet from his dripping dick-slit. Just remember, I want to see your thick hot spunk on his pretty painted lips before tonight is over."