Confession Ch. 02

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.

I led her to my TV room and invited her to sit down. I had at least a dozen candles providing the only light in the house. Enigma played in the background. Don't ask me why but Enigma and Mazzy Star became my music of choice for what is called the hobby by many, the addiction by me. I could tell she'd been drinking, but she wasn't drunk. She admitted that she'd been out with some girlfriends and was excited to meet me. I put her in her mid-20's. I guessed at the time she might have been a stripper in her late teens or early 20's. I definitely could tell she had experienced much more life than I had. She asked for a gin and tonic when I offered her a drink. I told her to make herself at home, and I went to get some liquor out of my cabinets.

She took off her heels and followed me to the kitchen. She asked how long I'd lived there and what I did for work. I spoke in generalities. I didn't want to give her too much private information. Sure, I wanted to bury my face in her bosom, but I didn't think that meant I needed to tell her my life story. Even with my guard up, we had a nice conversation.

She came a little bit closer to me and leaned in to give me a kiss. My body soaked in the warmth of her lips. They were so soft. I could feel her chest push against me and then her fingers rubbing up and down my arm. She pulled back just a bit and whispered that I was cute. I don't know if she meant it or not, but it had the intended effect. My nervousness subsided and I went with the flow.

I put my hands on the side of her cheeks and slowly kissed her. I extended my tongue only slightly, just far enough for her to feel it against her lips. She opened her mouth just a bit and pushed herself against me. For the first time in years, I actually felt a woman tight to me and wanting me. Her hand went behind my neck and pulled me tighter to her. I could feel her smiling as my cock sprang to life. She moaned just a bit and placed my left hand on her chest. Even through the fabric, I could feel that her breasts were real. She then took her hand and started to rub it up and down the front of my pants. My cock was so hard it hurt. The intensity of our kissing increased, and I started to wonder who wanted this more.

As we kissed she deftly unzipped my slacks and worked her hands inside my briefs. For some odd reason, I always find cock, ball and even pussy play so much sexier when clothed. There is just something naughty about a woman's hands finding their way to one's cock rather than just having it sitting their waiting for her. Maybe in my warped mind it makes me feel like she wants me more, because she's working hard to please me. Regardless, her hand found its way to my cock and down to my balls. She stopped kissing me and fell to her knees in the middle of my kitchen.

She looked at me as she pulled down first my slacks and then my briefs. She really was beautiful, and I'm not just saying that because she was getting ready to blow me. She stared at me and circled the head of my cock with her tongue. My cock twitched when she pursed her lips and slowly wrapped them around the head crown of my penis. I tilted my head back and relished in the sensation of my first oral stimulation in years.

I'm sure she could tell this was more than a quick fuck for me. I think she was enjoying the pleasure I was getting from her visit. There simply was a passion in her touch that belied that this was just a transaction. Looking back, this was just more rationalization by me.

When I looked down I could see her saliva on my cock. I could see her hard nipples protruding through the fabric of her dress. She pulled back and ran her hand up and down my shaft and gently sucked my balls. She leaned lower and gently flicked her tongue across my ass. I moaned and my cock got even harder.

I reached out and ran my hands through her hair and she in turn grabbed my ass. She pulled me deep into her throat, and I clenched my ass cheeks together. And just like that I came in her mouth. She hungrily accepted my seed as I convulsed. My body went limp and she withdrew her mouth from my cock. She looked up at me and smiled. She had swallowed all of my cum and wanted me to know that she had enjoyed it. She raised herself up and lightly dragged her lips across mine. I could smell my cum in her breath, but I didn't really care. I said thank you and gently kissed her lips.

I was hoping she'd spend the night, but deep down I knew that wasn't going to happen. It was something inherent to my addiction. As much as I wanted to think "dating" escorts would be a way for me to meet a significant other, that just wasn't part of the deal.

I walked her to her car, pushed her against the door and gave her one last deep kiss. She thanked me, told me to call her anytime and drove away.

Call her anytime, I thought to myself. That would happen very soon.