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My First Time

"We all go through it (except perhaps Catholic Priests), that first time, we struggle, we fumble, we blush, and hope for a happy ending."

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I was anxious. My heart raced as I opened one of the double doors to enter. My eyes blinked and squinted, adjusting to the dim light, as my mind strained to remember the instructions given me over the phone.

I looked to the left down the hallway, two red lights solidly lit above each of the first two doors and another one blinking above the third. No. That wasn't the way; it was to the right. I remembered and turned as I felt each heartbeat thumping in my chest.

The hallway appeared endless as each step took me deeper, possibly trapping me if I needed to escape. Finally, the sign I was looking for was The Fitting Room. The letters fading and peeling. The brass doorknob is polished and loose from possibly thousands of hands that had turned it before me.

Hesitantly, I turned the doorknob and pushed the door open. My eyes were flooded with the bright lights as I slowly walked in. The door closed with a heavy bang jolting my stance and that's when I saw her.

Like a goddess in the light, but she was no angel. I felt my blood rushing to my cock. It grew with each step she took towards me. Her strut gave me palpitations. Her cowboy hat matched the long brown hair that flowed from under it. Her smile was broad with dimples on either side. Her large bosoms stretched the buttons of her plaid shirt tucked neatly into her low-rise jeans held up by a belt with a large buckle featuring a pistol on each side of the silhouette of a seated sexy woman. The tight jeans molded to her figure, revealing a gap between her thighs.

"Hi, you must be Tom?" she said as her gaze traversed down my body, pausing at the bulge of my crotch. "Is it your first time? It's alright to be excited," she continued speaking before her gaze went to my face again.

"Is it that obvious?" I asked, blushing in embarrassment.

"Come on," she said, clasping my hand in hers, leading me across the room through a slatted double-swinging green door. A single wood chair sat in the middle of the room that she led me to. "Sit," she commanded.

I did as she asked, my face in line with her bust, causing me to forget how to breathe. Her left leg pushed between mine, forcing them open, and then stood between my legs, looking down at me.

She giggled as she openly stared at my obvious excitement, then looking directly into my eyes, she said, "Let's get you measured to ensure we get a good fit."

My cock jerked in the confines of my jeans, momentarily catching her attention again. She bent slightly towards me, positioning her breasts an inch from my face as she reached into her back pocket and extracted a flexible measure.

I sucked in a long breath as she placed the end of the measure against my head. I inhaled sharply as she ran her fingers along the measure and then held it in the air.

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She let out a little giggle and said, "Kind of small... six and seven-eighths. It's okay, we'll find one that fits you," and smirked.

My face turned red at her reaction. No one had referred to it as small before. My mind and ego were frayed but quickly dispersed when she turned around to walk away. The sway of her derriere with the swing of her hips was mesmerizing.

I let out my breath that I didn't realize I was holding as the swinging doors closed with her exit. I quickly reached down and squeezed myself, trying to get some relief to my hardened state.

Time seemed to stand still as I waited. I looked around the tiny room. Mirrors were everywhere. They adorned each side of the double-swinging doors from the floor to the ceiling. Each side wall was also covered in mirrors, as was the ceiling.

I heard faint footsteps making my heart start to race again. They grew louder and louder until she came through the doors again. Her smile was broad as she paused her step. Another button was unbuttoned, exposing the lace at the top of her red bra. Her hands were both behind her back as if presenting her luscious mounds of pleasure to me.

The dimples of her smile and the twinkle in her grey eyes were driving me crazy. My cock was throbbing in anticipation. It was obvious she was deliberately antagonizing me, taking slow, small steps towards me.

When she finally stood in front of me, her gaze went down to my crotch. Her tongue grazed her lips. I naturally spread my legs apart for her as I expected her to return to her previous stance.

She giggled and brought one hand from behind her back, using just one of her fingers to coax my legs back together before straddling my legs and sitting on my thighs. I swore I could feel her heat against the bulge in my jeans as her gaze again came back to my face.

It was torture like I've never experienced before. Her breasts were just inches from my face and, now with that red lace, taunting and teasing me. Her nipples were pronounced and begging to be grasped between my lips.

I blinked my eyes rapidly before tearing my graze from her breasts. Slowly I raised my eyes to her smile and those teasing dimples and then to those twinkling grey eyes.

Finally, she pulled her remaining hand from behind her back and placed the cowboy hat on my head. Her other hand joined to ensure it sat properly.

"Perfect," she said in a husky voice as she trailed a finger down my front and stopped at my crotch. She stood, then grabbed my hand to stand with her.

I looked in the mirror and said, "Thank you. It's my first time for a cowboy hat!"

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Written by PA_Mike
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