My Hotel Room

I was traveling for work and had just returned to my hotel room after a long, tedious day of client meetings and conference calls. As a thirty-year old mid-level executive, I had gotten used to the stress of frequent travel and the tedious routine of living in and out of suitcases and hotels. With such a hectic schedule of work and travel, I had grown accustomed to going many days without any real alone time to unwind and relax.

I looked at the clock and realized I had almost two hours until my client dinner. I walked to the closet and began undressing by carefully hanging my jacket and slacks. I continued to remove all of clothes until I was left naked except for my underwear. Clad only in my silk, low-rise bikini briefs, I continued preparing for the next morning of meetings by laying out a fresh shirt, socks and underwear.

Having accomplished the majority of my morning tasks already, I decided to relax by performing some light stretches and yoga exercises. After about twenty minutes of activity, I was profoundly more relaxed and I had a thin sheen of sweat across my entire body. As I walked into the bathroom to examine myself in the full length mirror, I realized that I had not engaged in any sexual activity in almost two weeks.

Feeling relaxed and horny, I moved to the desk where I had my laptop and work materials. I sat myself in the large cushioned desk chair to log in to my computer and access the attached wireless card. I began scrolling through my bookmarked pages until I found my favorite website containing erotic stories.

Although there was a wide variety of themes and fetishes available to me, I always found myself searching for scenarios involving sexy older, experienced woman who would seduce and initiate adolescent boys into the world of intimacy and erotic sexual encounters. Although I did not act submissive in the other aspects of my life, I would always become sexually aroused at the thought of an older woman seeing me naked, controlling me and teaching me the proper ways to please and perform sexually with an attractive, experienced woman.

As an adolescent boy, I would frequently find myself naked in my room fantasizing about my babysitter or the attractive mother of my friend catching me fully naked as I masturbated. My favorite fantasy involved my mom's friend, Cyndi . Cyndi was a physician's wife and stay-at-home mom so she had a lot of free time to spend at yoga, shopping and socializing with my mother. She was about five foot six inches tall and had a petite body with nice small breasts. My mom and Cyndi would often sit around our house for hours talking and sipping wine while wearing their sexy yoga outfits.

As I sat in my hotel room, I fantasized that I had just turned eighteen and my mom let my stay home alone while she visited her friend in New York City. In my fantasy, my mom had asked Cyndi to stop by the house after yoga to check on me and to make sure that I was not causing any trouble. I would strip off my clothes and underwear so that I would be lying naked on my bed, with a pair of my mom's nylon panties in my hand. I would immediately start masturbating as I inhaled my mother's womanly scent and as I rubbed the sensitive head of my erect penis against my mom's silken underwear.

I would be so focused on my mom's panties and my own arousal that I wouldn't hear Cyndi coming into the house and up the stairs. Suddenly, the door would open and there would be Cyndi staring wide-eyed and open mouthed at the sight of my exposed genitals partially covered by my mom's purple satin bikini panties. I would immediately attempt to cover myself while Cyndi's shock began to turn to amusement and arousal at the sight of my young toned body and hard cock. Feeling completely exposed and immobilized by shame, I would frantically attempt to cover my erection with my hands and hide my mom's panties while my face exploded in bright red embarrassment.

After a moment to regain her composure, Cyndi would slowly walk towards me with a smile on her face while gently telling me that I was "a naughty little boy for playing with my penis" and "what if your mom found out that you like sniffing her dirty panties?" Her comments drove me to a level of arousal that I had never experienced as began to fully explore the shame and embarrassment of being completely exposed to my mom's best friend. Knowing the dramatic affect her words were having on me, Cyndi gave me sultry smile and slowly started walking towards me.

As she reached the side of my bed she would quickly grab my hands and pull them away to expose my hard penis standing straight up from my smooth belly. I don't have much body hair and I could tell that Cyndi was concentrating on visually exploring my adolescent body and genitalia. Even without being touched, the excitement of being caught naked while masturbating caused my erection to bounce and to start leaking a thin stream of precum. I could feel my arousal and the sexual tension building as my head swooned and my stomach turned with the excitement of standing naked before such an attractive, mature woman.

As I continued reliving my boyhood fantasies in my hotel room, I started to slowly rub and squeeze the tip of my penis and my shaft through the soft silk material of my briefs. I would imagine that I was back in my boyhood bedroom using my mom's silk panties to masturbate as Cyndi directed me to lie on the bed and to resume stroking my hard cock. I imagined Cyndi slowly climbing up onto my bed so that she could get a better view of my young cock and tight ass. Once comfortable, she would look at me and say "don't stop. Show me what a naughty little boy you are. Keep playing with your hard penis and show me how you make yourself cum."

As my most intimate sexual fantasies played out in my mind, I continued to gently massage my genitals while picturing Cyndi's sultry eyes and pert breasts. I imagined how she used to look in her yoga pants and fantasized about seeing the contour of her mature pussy outlined through the tight spandex material of her pants. I became fully erect almost instantly, creating a prominent seven inch bulge in my underwear. As I became increasingly aroused and fully engorged, my shaft began leaking pre cum leaving a large sticky area on the crotch of my underwear.

Not wanting to create a further mess in my underwear, I slowly pulled the waistband of my briefs away from my body exposing my fully erect penis and heavy testicles. I slowly slid my briefs down my buttocks so that my underwear was tight across my thighs and the waistband was just below my hard penis and balls. I gently massaged and stretched the skin of my scrotum and pulled on my testicles as I felt their weight. I began to imagine how I would feel when I eventually ejaculated and released the weeks of pent up frustration.

Imagining that I was in my bedroom as a teenager with Cyndi standing in my room, I started to slowly slide my hand up and down my stiff cock. I imagined Cyndi lying next to me on bed as she gently whispered words of encouragement to me. She would repeatedly say to me "what a nice penis you have" and beg me not to stop until I had shown her how I could make my young, hard cock shoot big loads of cum.

I continued living my fantasies while stroking my cock until I was just shy of cumming. Once I reached a point where I was only a stroke or two away from orgasm, I would firmly grip my shaft and balls to avoid a full-blown explosion. As I would slowly recede from the brink of orgasm, I would gently manipulate my penis and testicles so that a large amount of milky white cum would slowly stream from the tip of my cock onto my pubic hair. Then I would gently rub my juices all over my cock and balls while waiting for my level of arousal to subside before resuming my activities. I repeated the process four or five more times until I felt a dull ache in my balls and the air was thick with the scent of my sweat and my arousal.

When I couldn't stand the feelings of my denied orgasms any longer, I reclined in my chair and placed my feet on the desk. From this position, I was seated almost horizontally with my legs spread wide apart exposing my genitals and tight anus to anyone who could see in my hotel room windows. My room was dark and quiet and the only audible noises were my heavy breathing and the sticky smacking sounds of my hand as I stroked my cum-covered cock. I increased the speed and length of my strokes while imagining the sultry voice of my mom's friend encouraging me to masturbate myself for her while she rubbed her swollen clitoris through the outside of her yoga pants. She would keep repeating "that's a good boy" as she slowly rubbed a finger along her crotch while staring intently into my eyes as she watched me masturbate.

With those thoughts running through my head I increased the pace of my stroking until I finally reached the point of no return. My right hand was a blur as I frantically pumped my shaft up and down while my left hand squeezed my taut scrotum and heavy testicles. Leaning back in the chair, I aimed the tip of my penis towards my chest preparing for my rapidly approaching orgasm. Unable to control myself any longer, I let out series of loud moans and softly cried out "Oh Cyndi" as four or five large spurts of hot cum shot all over my chest and neck. I continued stroking myself as my orgasm continued to ripple through me and as I continued to pump my remaining cum all over my chest. As my orgasm subsided, I stared intently at the thick pools of my semen all over my neck, chest and hands.

As my breathing calmed and I slowly recovered from my powerful release, I closed my eyes and imagined what Cyndi would say to me as I lied there naked and content while enjoying the feel and pungent aroma of my warm cum all over my body.

Perfectly satisfied and relaxed, I would imagine how Cyndi would push her fingers through my sparse pubic hair and across my chest so that she could touch and taste the copious amount of semen that had collected there. She would stare intently into my eyes as she licked her fingers to experience the erotic flavor and texture of my young cum. After consuming most of my warm semem, she would gently grab my hand and lead me to the bathroom where she would close the drain and begin filling the tub with warm water and bath salts.

Now that a few minutes had passed since my orgasm, my penis hung limp and diminutively from my belly. Cyndi's eyes were glued to my groin as she took in the sight of me standing there completely naked with my shriveled member and tight scrotum hanging innocently between my legs. Cyndi seemed to enjoy my embarrassment as she openly enjoyed her visual examination of my nearly hairless body and my small boyish-looking cock.

Cyndi would start to breathe heavier as her soft hands reached out to me and she tenderly lifted my soft, cum covered penis and balls. My face went bright right as I again experienced the embarrassment and arousal of standing naked before my mom's best friend while her hands slowly manipulated the shaft of my penis and palmed my hairless scrotum. Sympathetic to the intense feelings running through my body, Cyndi softly cooed "It's okay honey. There is no reason to be embarrassed. Your Aunty Cyndi is here to take care of you." With that she slowly pulled me into the warm, soapy water of the tub.

To be Continued.