I settled into my lounge chair and played back the massage in my head. I could still feel the warmth of the oil dripping down my sides, the softness of her her touch on my arms and legs and the look of her tiny hands wrapped around my cock. I could see myself on all fours bucking my hips as she coaxed an orgasm out of me.
Almost involuntarily, my hands started to rub up and down the front of my jeans. As my cock strained against my briefs and pants, I quickly unzipped my jeans, stood up, let everything on my legs fall to the floor and settled back into my lounge chair. I reached over to my side table and grabbed the bottle of ever present lube. My goodness I've spent a lot of money on Astroglide. I poured the lube onto the tip of my cock and watched it flow down to my balls. I dragged my fingers up and down the shaft and lightly rubbed my scrotum with my finger tips. I let my hand drop down just a bit and gently rubbed my taint and circled the opening to my ass. I couldn't believe just an hour ago I let a complete stranger finger fuck my then virgin ass on a motel room bed.
As I settled more deeply into my chair, I began to stroke my cock. I circled the head with my finger tips and then stroked myself some more. I spread my legs to allow myself easier access to my balls. Years of daily masturbation had taught me exactly what areas of my cock were most sensitive, how best to drag out my orgasm and how to quickly cum. Right then, I needed to cum, so I stroked myself with a fervor that I would later find turned on many women. I came all over my shirt and some even shot over my shoulder to the chair. I had cum twice in about 90 minutes. I felt guilty and excited all at the same time.
As the week went on I couldn't get the feeling of the massage out of my head, and I decided I needed more. So, again, I flipped through the back pages of the alternative paper looking for someone that could give me a fix. The actual ad left much to the imagination, but it promised more than a body rub. I knew I was dancing with fire, but I also knew I hadn't experienced actual penetration in more than 5 years and the need for more touch was an ache I needed to address. Everything related to my body rub transpired so easily, I decided I could manage the risk. I called the number in the ad.
The voice on the other end was soft, sultry and, perhaps, a bit husky. I could tell she was younger than the masseuse and not quite as experienced. I told her I'd seen her ad and was curious about her schedule. She relayed that nights were best for her and that she only could do outcalls. To be honest, at that time, I had no idea what that meant, but I said no problem. She said great and asked me for my address.
"What? I thought to myself. She wanted my address?" Shit, I didn't know what to do. I was ready for more, but at my house? Really? In a timespan I still cannot fathom, I weighed the pros and cons of having her come to my house, thought about how I'd explain her visit if my neighbors asked any questions and contemplated how I'd respond if she showed up at my door unannounced some evening. I rationalized everything knowing that a gnawing ache needed to be addressed. I nervously sighed, provided her directions to my house and agreed that a 10:00 PM date would work great.
Getting through the day was painful. For a diversion, I cleaned my house like a mad man. I went out and bought candles. I changed the sheets on my bed. Sure, I was going to pay for her sexual services, but I wanted her to enjoy her time with me. In some strange way, I wanted this to be a date for me that finally included a climax to a great evening. Hell, I even worried if my outfit would be acceptable.
As 10:00 PM approached, I waited for her in my front room. I paced back and forth looking out my window. I only can equate my anticipation at that time to waiting for the kick-off of a football game. My body was raging with excitement and anxiety. I didn't know it then, but I was laying the foundations of a ritual I would relive almost weekly for years.
My neighborhood was very quiet and dark, so I knew it was her when I saw headlights in the distance. I stared out the window and waited for her. I stayed far enough back to prevent her from seeing me watching her; I didn't want her to think I was some sort of stalker. I was transfixed on her car door and then a number of thoughts ran through my head that even now I still ponder. Was she worried about my looks? Was she worried about her safety? Was she questioning why she chose this profession? Was she worried about the criminal nature of the transaction?
The door to her grey Celica opened and my heart raced even faster. I can remember this moment like it was yesterday. She was beautiful. She was tall, taller than me for sure, blonde, busty and wearing a fuck-me dress. It came to about the middle of her thighs. She had curves. I don't know why, but I expected all escorts to be rail thin with big, fake boobs. I'm sure deep down I figured they all were drug addicts, and I was just paying for their addictions. This woman changed my perception forever. This woman was healthy, and she was hot.
I let her ring the doorbell and then made my way to the foyer. I left the porch light off to limit the vision of any peering eyes and asked her to come in. I was so freaking nervous I was talking at warp speed. Oddly, at that very minute I started to realize why I couldn't hook up when I went out. I was a bumbling mess.
