Chapter 3: Guilty Sex

YES! He wanted to fuck me! I had been just about to lose hope but now all was good again. I tried to hold back my excitement - and my relief. At that moment I would have gone to his room even if I wasn’t escorting. Normally this would be where I reminded him that I needed a “tip” to go anywhere with him but with Dan I knew I didn’t need to say anything. As classy as he was I was sure he understand the rules and I wasn’t going to spoil the moment by unnecessary negotiating.

“I would love to Dan,” I replied with a sexy smile on my face.

Dan had a look of relief come over him as if a sudden load had been lifted from his shoulders. I almost smiled since what did he think I was going to do, say no? Wasn’t the point of going out with an escort instead of hitting the bar scene so you knew you had a sure thing going? I kept my composure though and tried to look as seductive as I could for him. Then it struck me, maybe he had the same worries that I had and thought I might have been an undercover cop looking to book a john! I giggled to myself a bit at the thought of how maybe both of us had been worried about the other.

Dan stood up and helped me from my chair and led me out of the restaurant to the elevators. He had to put his key in a special slot to get to his floor which told me we weren’t going to just any old hotel room. On the way up we stood there silently, like two strangers almost, waiting for our floors. He didn’t even have his hand on me!

The elevator went to the top floor and from the spacing of the room doors I figured he must have booked a suite and sure enough, that’s what it turned out to be. It was bigger than my school apartment with a huge bedroom, large living area and small kitchen. There was even a big hot tub set in a room off from the bedroom! The room overlooked the shopping area which was not exactly the New York Skyline but it was still pretty. The living area had a big screen TV and an oversized plush couch which caught my eye immediately. I slipped off my heels and flopped down on the couch on my back with my dress gathered under me. I laid on my side on one elbow with my ankles crossed. The tall slit in my dress let him have a view of most of my topmost leg and of course I didn’t bother doing anything to rearrange it.

I was hoping Dan would sit by me but he took up residence in an armchair facing the couch. He crossed his legs, put his hands on the arms of the chair, and just looked at me as if he was uncertain what to do next.

“Wow, nice place you have here Dan,” I said in a cheerful voice, trying to put him at ease.

Dan smiled slightly, just the corners of his mouth raising. He looked like he wanted to say something so I just kept quiet and let him compose himself. In a soft voice he started telling me more intimate details about his wife than he had during dinner. They had been married now for over twenty years and while she had never really been wild in bed, it was satisfactory for him at first. However, over the years it became less and less until now it was something they did maybe a few times a year and even then it was just boring for him. She was a virgin when they married and was raised thinking sex was something a woman was expected to do for her husband but that was about it. It was missionary only, no oral ever.

They both had gained some weight over the years but while for him it just filled out his frame bit, she had almost doubled in size since their marriage. He said he still loved her but just wasn’t turned on when he saw the bulges of fat and her sagging breasts. He was always afraid to even look at other woman because she was so insanely jealous although on trips out of town he went to strip clubs and then back to his hotel to masturbate, dreaming of being with a girl like the ones he saw there. He had considered going to a whore in the past but concerns over disease was the biggest deterrent plus he wasn’t sure if he could pay for sex. Finally one of his friends in a similar situation had confided to him about how he had gone out with an escort from an agency and what a great time he had. Sure they were technically whores but it wasn’t like you were going to a brothel or picking up a streetwalker.

At this point my ears perked up a bit. Hmmmmmm, so he considered me a whore? I’ve always proudly worn the label of “slut” but “whore” seemed so degrading. I liked the phrase “escort” and it may be semantics but to me there’s quite a difference. I could still refuse to have sex with him tonight and there was nothing he could say since he only booked an evening with me, not sex. Sure I might be paid but the agency had paid me to have dinner with him so out contract had been fulfilled. If I decided to have sex with Dan tonight it would be because I wanted to whether he tipped me or not.

I wasn’t in this for the money, I wanted the experience and the thrill! I guess if he considered me a whore I would just have to live with it though although if I got the chance I was going to educate him on the subject better. I think Dan was ready to give me his full confessional but honestly I wasn’t here to be his analyst so I finally cut him off.

“So tell me then Dan, do I turn you on?” I murmured as I stretched out on the couch which let the dress fall off my legs.

“Oh my god yes Kelly, you look incredible in that dress!” he responded with a smile.

I looked at him and wrinkled my nose. “I don’t think my being a whore is what bothers you, is it? You’re worried about your wife and what she would think, aren’t you?”

He started in on how he had never cheated on her and always been faithful to her even if he did fantasize about being with other women when he was in bed with her. He started to say how he wasn’t sure if could go through with this but I was horny and just having dinner wasn’t my game plan for the evening!

“Dan, your wife deserves to be cheated on for not keeping herself desirable for you,” I started out, “You have needs that she should fulfill. She’s being unfaithful to you actually so don’t worry about her. Think about yourself, think about your needs, your desires, your dreams and fantasies. Let me satisfy them, let me be your dream girl for just one night.”

He licked his lips and I knew he wanted me, it was just getting him to go over the edge and make the first move. I lifted my bare leg up and put my foot on my knee, letting my dress slide down until my entire leg was showing. I pulled it up higher to reveal my thong which was pulled tightly to my pussy making my pussy lips appear clearly outlined in the thin material. I started to rub myself through the thong, pressing on my clit and reaching down between my legs. I closed my eyes and rolled on my back. I lifted my inside leg up onto the top of the couch and pulled my thong to one side with one hand while I started to play with myself with the other.

I heard him take a deep breath when I inserted one finger inside of me and moaned softy as I felt the wetness inside. For the next fifteen minutes or so I masturbated on the couch as if I was home alone on my bed or in the family room with my parents. I kept my eyes shut and never even looked over to where Dan was sitting. I wondered what he would have thought though if he knew what I was dreaming about as I laid there with my hands between my legs? At least I kept my wits about me enough not to say, “Oh daddy!” when I came!

After my first orgasm I was now as hot and horny as ever! I wanted to cum again but not with my fingers this time. I opened my eyes and looked over at Dan. He was shifting in his chair but there was no mistaking the bulge in his dress pants! I got up off of the couch and pulled my dress up and over my head leaving me standing there barefooted wearing nothing but my thong. I cupped my breasts and lifted them up and squeezed them, feeling my hard nipples between my fingers.

I walked over to Dan and gently pushed his legs apart so I could kneel down on the floor in front of him. Without saying a word I slowly unbuckled his belt, unzipped his pants, and spread the flaps open. He was wearing boxers, thank goodness, and I was able to easily reach in through them to find his warm hard cock waiting for me. Dan’s hands were still on the arms of the chair and he wasn’t moving an inch yet as I ran the tips of my polished fingernails up and down his hard shaft.

Dan dick wasn’t very big, maybe six inches at most, but his cock head was larger than average in comparison to the rest of his dick. Even though he had obviously showered and used cologne, I smell his crotch odor as it slowly made its way from his open pants and I breathed in deeply to savor the musky aroma. I looked up at him and smiled. We were both still silent as statues as I kept my eyes locked on his while I lowered my head to his crotch where I took his sooth cock gently in my mouth.

I started to softly suck on the head while playing my tongue around it. It occurred to me then that my mouth was the first one to ever hold his cock as his wife wouldn’t suck him! I encircled the base of his cock between my thumb and forefinger, holding it upright so I could suck him easily. Mmmmmmm he tasted so good! My wet tongue run up and down his shaft, going from the very base where it met his crotch to the tip where the hole was. Then I licked my lips and ran them up and down his shaft, using my tongue to tickle him as I moved up and down.

Dan’s dick was nice and wet now so I started some serious sucking. I bobbed my head up and down on him, taking more of him in with each stroke and then burying my face in his thick pubic hair as I took all of him in my mouth. His cock was surrounded by one of the thickest bushes of curly stiff hair I had ever had the pleasure to bury my face in. My face was pressed against his crotch and I sucked his entire cock until he finally couldn’t take it anymore and had to say something to break out silence.

“Oh ... my ... god,” he groaned, saying it over and over again and then finally, “That is just soooooo incredible. God that feels soooooo good!”

I let him loose just long enough to ask, “So how does it feel to have your cock sucked for the first time?”

“Ohhhhhh, better than I dreamed,” he moaned, “Always wanted this ... always dreamed of it ... god please don’t stop ... that’s it - just like that!!!!”

I was working him with every trick in my considerable arsenal. My hands were on his thighs as my head weaved and bobbed around his dick, twisting around his cock and slurping my tongue against it. I reached under him and cradled his hairy balls in my hand and gently rolled them with my fingers as I sucked him. His hands finally left the damn chair and he ran his fingers through my hair, sending chills down my spine!

I took him all the way in my mouth and he groaned out load and pushed my head firmly down onto him as if trying to keep me from letting him out of my mouth. I needed some air though and pushed up against him just in time to keep from gagging but I went down on him again and gently gripped the base of his cock with my teeth, teasing him as I rotated my head around his dick. I had enough experience with cocks in my mouth to realize that he was about to cum but I didn’t want him to. Somehow I didn’t take Dan for the multiple orgasm type and I had more plans for him than just a blowjob!

I stopped sucking him and started to pull his pants down. He lifted himself up enough to let me get them off. He was a little overweight as he had admitted before but his ass was still pretty firm. It didn’t matter anyway as his cock still worked and that was all I really cared about. I pulled his pants and boxers down to his ankles but left the rest of his clothes on. I turned around and pulled my thong down to my ankles without bending my knees so he got a great view of my ass and pussy from the rear. Stepping out of the thong I reached between my legs for his cock. I sat down on his lap as I guided his cock to my soaking wet pussy. As small as he was he easily slid into me and I felt my bare bottom meet his hairy lap.

Speaking of small (and forgive me for the tangent), does size really matter? As far as I am concerned it is not nearly as important as guys seem to think. I like a fat cock to fuck me but a smaller one to suck so the average guy probably is best overall. Big cocks look great on porn films I guess but have you ever tried to swallow one? I like to feel more than the equivalent of a finger in me so a fat cock definitely feels better but in the end I can cum regardless of what size he is and I have found size has nothing to do with how much cum he gives me (the more the better!).