Confession Ch. 01

I was enjoying, if that's what one can call it, another ritualistic Saturday morning. My coffee cup was filled with Starbucks, a donut rested on a napkin on my kitchen table, Sportscenter played in the background and I was thumbing through the local alternative paper much too early for a late 20's, healthy and virile male that should have be sleeping soundly after another late night of fun rather than taking on the persona of a man more than twice his age.

My life at that time had become very boring. Too much focus on my career had left me in life limbo. I was too old to really enjoy the bar scene, and I wasn't making enough money nor did I have the aura around me to make it work at the nicer clubs and restaurants in the area. The few friends I had were beginning to settle down, so their weekends were committed either to kids or future wives. I hadn't had a serious relationship in years and my dating life was pretty much a constant stream of speed dates. As sad as it was, the weekends had become nothing more than time I had to kill before I could get back to the office and focus on building my career.

I flipped through the pages of the paper. The schedule of local concerts, check. Dan Savage's advice column, check. Naive letters to the editor, check. I read through all of those column inches to help me rationalize my true intentions; I had picked up that newspaper to read through those last couple pages that promised lots of adult fun. As of that time; however, I had yet to act upon any of that promise.

Don't get me wrong, I did not lack for an amazing sexual imagination. Even my weekdays were filled with multiple masturbation sessions prompted by rabid reading of various erotic literature sites. The internet was still new at that time, and I routinely started my day with a quick review of new postings on my favorite sites; Richard's Realm, Ann Douglas's homepage and Nifty Archive. For a boy that didn't start to masturbate until he was 21 and didn't lose his virginity for another two years, lots of masturbation had given me an advanced degree in understanding my body.

Oddly enough for that same 28 year old "boy," erotic literature turned me on much more than naked pictures. Even as a youth, Penthouse letters elicited a more acute erection than the pictures within the magazine. The advent of the internet allowed me to revel in my desire for erotic stimulation pretty much whenever and wherever I wanted. A picture or a porn dvd just couldn't match my imagination, and an explosion in masturbation soon followed.

Solo fun only can get one so far, though. It had been years since I'd been intimate with anyone, and I was craving touch. My right hand was a poor substitute for the soft skin of a woman's hands or lips. This was the day I decided to act upon my need.

One of the ads promised an erotic body rub. I liked the sounds of that. There were others that offered sex, but I wasn't quite ready to pull the escort trigger. That would have to wait. No, an erotic body rub was just what I needed. I collected my thoughts, took a deep breath, paced back-and-forth in my kitchen as I stared at the phone and finally worked up the courage to the call the number in the ad. It went straight to voice mail; damn! If the advertiser knew how nervous I was, if she knew how much courage it took me to make that call, she'd punish herself for putting me through such agony. I left a message and went back to my coffee and donut.

A few hours later, the phone rang.

"Is Justin there," a female voice said very matter-of-factly. Shit, I hope it wasn't a bill collector or telemarketer.

"This is."

"This is Sarah, you left a message for me a few hours ago." My mouth went dry. My stomach turned over. I actually felt like I was going to get sick. The moment of truth was upon me.

"Hello. Yes, I...I...I saw your ad in the paper. I'm sorry. I've never done this before."

"Would you like a body rub?"

"I would."

"How is your schedule this afternoon?" This was my first time, but it clearly wasn't for her.

"I'm free all day."

She asked me a few questions. My age? What I looked like? What I did for fun? We talked for maybe 2 or three minutes and then she asked, "How's 3:00 PM work for you?"

"Not a problem."

She gave me the address of the hotel where she was taking appointments and told me to knock on the door at 3:00, no earlier,no later.

I hung up the phone and looked at the clock, 1:15. I had some time to kill before I left. It was then that I started to have second thoughts. What if she were a cop? What if she had a pimp? What if she had a gun? The questions running through my head had my heart beating at an accelerated rate. It's not as if I could call one of my friends and tell them if they never heard from my again it's because I was killed by a pimp. Still, for my boring life, there was an undeniable thrill I simply had to realize.

I made the trip to her hotel. It was off the highway at the outskirts of a smaller suburb, ironically enough, not too far from my house. The hotel really was a motel. Doors opened to the outside rather than a hallway. I'd driven by that particular motel a thousand times to and from work; I never drove by it the same way again.

I entered the parking lot and drove around the entire hotel once. I was much more nervous about a sting than a pimp. A pimp only would take my money; the police would ruin my career...my life. There only were a couple cars in the parking lot, and I saw no signs of a police presence. I parked, swallowed hard and walked to her room.

My stomach was in knots as I lightly tapped on the door. My hands were sweating, my heart was racing. I hadn't felt that way since my college sports days. Adrenaline was racing through my body. If there were a pimp on the other side of the door, he would have had a helluva time controlling me.

The door slowly opened. She stood behind it and whispered that I should come in. All of the blinds had been drawn. A dozen or so tea lights provided the only light for the room. She closed the door, locked it and turned to face me.

I put her in early 30's. She had sandy blond hair down to the middle of her back, wore little make up and just the slightest bit of perfume. Her smallish chest was covered with a bikini top, her bottom a wrap around skirt. I gave her a 7 in looks. She had the look of trailer court queen. She wasn't as refined as the women in my fantasies, but I wouldn't have been worried about being seen with her in public. I simply stared at her; I didn't know what to do.

"Do you have something for me?" she asked.

"Pardon me?"

"Do you have my donation?"

"Oh, yes, sorry. Where should I put it?

"Just put it on the TV and then take off your clothes."

I was so nervous I was shaking. I actually think she was laughing to herself, just a bit. Similar to my girlfriend that took my virginity, I think she also relished in the knowledge that she was going to be my first, albeit a much different first. I took off my shirt, my shoes and my pants. I was still in very good shape from my college sports days, and her eyes lit up when she saw the definition in my chest and the thickness of my legs. I left on my boxer briefs, because my cock had shriveled up to the size of an acorn. I didn't want to embarrass myself too much. She told me to lie face down on the towel on the bed and relax. Easier said than done.

I could feel the heat of her body as she knelt beside me. She poured some oil on my back and slid her hand across my shoulder blades. It had been so long; her touch was amazing. She dragged the tips of her fingers across my back and down my arms. My nervousness soon turned into goosebumps. She finally could see the tension leave my body.

She settled in between my legs and ran her hands down my hamstrings and over my calves. She lightly rubbed my feet; a first for me. Her fingers slid between my toes, and I began to feel a tingling in my cock. I was still shriveled, but there finally was life in my shorts.

Her hands climbed up my thighs, she leaned over my back and whispered in my ear that she wanted to help me take off my briefs. I shook me head and raised my hips just a bit. Her fingers worked their way inside the waist band, and she slowly pulled them down my legs. I now lay on my chest, legs spread, covered in oil waiting for her touch.

It was then that I experienced another first. She poured oil on my lower back and traced its flow down through the crack of my ass. Her hands cupped my ass and massaged my buttocks. I'd had plenty of massages in my life but never had received anything like that. I couldn't believe the strength in her hands nor how good her hands felt. Blood was now racing into my cock.

She pushed my legs further apart and ran her hands up and down the crack of my ass. Worries that I was gay because I enjoyed that stimulation ran through my head. I quickly started to understand why gay men enjoyed someone toying with their ass. Her fingers probed my opening, and I moaned. I'm sure she was smiling to herself as I let her have her way with me.

Her fingers continued to circle around my rosebud and my cock began to stiffen. She penetrated me with one finger and drug her fingernails across my balls with the other. My cock now was so hard it hurt. I was aching for more of her touch. I raised up on my hands and knees and her hand snaked between my legs and found my shaft. She sighed when she wrapped her hand around my stiffness.

Here I was in a highway motel, on my hands and knees, my chest on the bed, my ass in the air and a strange woman with a finger in my ass and a hand wrapped around my cock. I'd fantasized about a lot of things, but this position was never one of them. It didn't really matter, though. It felt too good to complain.

I tilted my head and looked down as she stroked my cock. Her hands looked so small wrapped around my engorged cock. My head was purple it was so full of blood; it almost looked angry. She started to finger fuck my ass as she quickened the stroking of my cock. And as fast as I started to buck my hips, my cum exploded on the towel she had laid down for me.

I collapsed on the same towel on which I had just had one of my greatest orgasms. She may have been talking to me, but I can't recall. There was a euphoria I was feeling as she lightly tracked her fingers down my back. She leaned forward, kissed my cheek and asked me if I'd had a good time.

"Holy Shit," was all I could mutter.

"You have a nice ass," she told me. "I liked exploring it." I think I could hear a smile on her face as she said that.

"I've never experience that. That may have been the most explosive orgasm I've ever had."

"I'm glad you enjoyed it. You're welcome to call me anytime," she whispered to me.

I laid there for a few more minutes collecting my thoughts before I slowly got dressed. I would have loved to have known what she was thinking when she watched me dress. Did she know she'd just put me on a path I'd never known existed? Did she know how much joy she had just given me? Did she think I was a shitty male paying for her sexual services?

I contemplated these and many other things as I drove home. I alternated between hating myself for searching out her services and loving the touch I had been so desperately missing. I had felt sick in my stomach, yet the only thing I knew would help me deal with it was another orgasm.