Evolution of a Whore Pt. 01

I'm married and straight but have always been somewhat curious. About a year and a half ago, I was introduced to cross-dressing and sissy porn and quickly became hooked. The fantasy turned into a driving desire, however, it remained only in my imagination. I ventured into chat rooms but never found the courage to expand beyond that, and soon realized it would always remain a hidden fantasy.

I travel extensively for a living and cross-country travel takes its toll on a body. To help mitigate the wear and tear on my body, I enrolled with a national chain of massage therapy spas. I always chose a female masseuse as a natural comfort zone. The inconvenience of locating, finding, and making an appointment soon became tedious and I began requesting onsite visits to my hotels. While I stay at safe, and most upscale hotels, most women, and rightly so, are reluctant to perform onsite massages at hotels. I made the change to male masseuses for legitimate therapeutic massages.

I have a vivid imagination and my fantasies pushed me to take small risks to make travel more exciting. I always wore underwear beneath the towel during any massage. I decided to try and wear a pair of women's panties during one massage and the thrill was so exhilarating, I chose to do it each time. The risk of being caught helped fulfill some of my desires.

On my last massage, I decided to wear a lace thong under my towel, and could barely hide my erection as I laid on the table. During the back massage, the masseuse brushed the towel with his elbow and it slipped slightly. I froze in fear and waited for the repercussion, but none came, and I relaxed slightly.

The masseuse returned to the front of the table and began rubbing my neck and shoulders when I felt something brush the back of my head as I lay face down on the table. I soon realized it was his cock through his shorts rubbing the back of my head, and the farther he reached down my back, the more I could feel his bulge.

Suddenly, the towel slipped to the floor and my exposed ass with a lace ladies' thong was exposed. Before I could react, his strong hands grabbed my ass cheeks and roughly groped them. I felt his now rock-hard cock against my forehead and my head started to spin.

I felt his hands lift my shoulder and place a pillow under my face so I was no longer in the cushion hole. I glanced forward and faced with a large, thick 8" cock directly in front of me. Before I could react, his hand was on the back of my head and the tip of his cock was on my lips.

"You and I both know this is what you want."

He pushed his cock past my lips and into my mouth. I instinctively began to suck his cock like my wife sucked mine. He placed my hands on his rock-hard ass and pushed his large cock deeper into my mouth. As I clenched his ass cheeks in my hand, I could see in the mirror behind him and watched as he slowly moved his ass and hips in and out, watching in awe as he slowly fucked my mouth. He pushed his cock to the back of my throat.

"You're a good little cock sucking whore!" he quipped. "Take it all, like the slut you are!"

I was stunned to realize I had another man's cock in my mouth and now his balls were against my chin and the cock was halfway down my throat. My cock was stiff and I was more excited than I have ever been in my life. He began to stroke faster and faster and starting to moan. I panicked, realizing he was about to cum in my mouth and down my throat, but surprisingly he stopped and pulled out.

"You will still swallow my seed bitch, but first I'm going to pop that cherry hole of yours."

So much was happening so quickly, my head was swimming, but both lust and fear. He picked me up off the table and dropped me on the bed. I was frozen like a deer in the headlights as he straddled my legs. I watched everything in the mirror and it was akin to an out-of-body experience. He poured oil onto my ass and massaged it into my cheeks and the crack of my ass as he moved the thong out of the way.

I felt his thumb rub my asshole, and as he poured more oil, he slid his thumb into my ass. I was shocked, surprised, and excited. He worked his thumb in and out of my ass, adding more oil all the time. When he took his thumb out, I felt empty, but he began to slide his cock up and down my ass crack.

He stopped and I could feel the head of his cock against my hole. He slowly began to push and it hurt, his cock was thick, far thicker, and longer than mine. The pain grew more intense the further he pushed, but I could only gasp and moan. I couldn't believe that first I sucked a cock and now was going to be fucked in the ass. He kept sliding slowly until I felt his balls again mine, and realized he was deep in my ass.

He leaned down and said, "Your manhood will be gone forever, and you will want only cock from now on, slut."

He began to slowly move back and forth, then began to fuck me in earnest. I watched in the mirror as a stranger fucked me, and the vision matching the feeling of being fucked was beyond intense. I felt a puddle of precum pool between my stomach and the bed. His pace quickened and I felt an itch deep in my ass that I couldn't explain It felt like the moment just before you cum, but I never did, and it seemed to last for an eternity.

"Yes, yes, oh, fuck me, fuck me harder!" I was shocked to realize those words came from my lips.

I realized I was moving in rhythm and moving my hips back to meet his thrusts. I could feel his cock swelling larger, and I was on the edge of orgasm when he stopped and pulled out.

"If you going to dress like a slut, then I'll fuck you like one."

He ripped the thong off and turned me on my back. He put his forearms in the crux of my knees and spread my legs wide, pushed my ass up by leaning forward, and slid his cock back into me. He thrust to the hilt and I could feel his balls on my ass as he went deeper than before, and my eyes rolled back in ecstasy. He began to fuck me fast and hard, with the bed moving under the stress. My cock was only half erect, but each thrust forced a stream of cum onto my belly. He grabbed my hand and made me move my cock and balls out of the way. He then grabbed me by the hair and tilted my head down to watch.

"That's a real man's cock fucking your slutty little panty wear ass. Watch it, watch it take any manhood you ever had. Tell me you want it, bitch, or I'll stop right now!"

"Please, please don't stop! I'll do anything you ask, please." I begged.

The sight of that large cock pounding my ass was almost more than I could bear. I watched and knew this was far better than any of my fantasies.

He lifted my hips higher and fucked me harder and faster. He grabbed my cock and stroked it, pointing it directly at my face. I knew I would cum soon and I felt his cock swell even larger. He was hitting a spot that was driving me into a frenzy.

As I was feeling my orgasm approaching, I felt him shoot his hot cum deep inside me, and at that moment I came in a gush, more than I have ever cum before. Six or seven large spurts, covering my face, eyes, and in my mouth. He gave one final groan and collapsed on top of me and pulled his shrinking cock from my sore ass. He rolled me over on my stomach, I couldn't move, I was physically spent. I could taste my cum and felt his cum dripping from my ass onto my balls.

I could barely keep my eyes open and I was drifting off to exhausted sleep, but before I passed out, I heard him on the phone.

"You won't believe this sissy slut I just broke. You guys need to get over here and bring Mike, we're going to give this one the full treatment."