Escapades: "Judy"

I was a waiter, in a restaurant when I met Judy. I was 21 years old and cocky. I was full of testosterone, more so than was good for my sensibility. I was foot loose and herpes free supporting eight inches in length and loved to be told my cock was big. I was a show off with my trophy girlfriends and really did not deserve any of them. I did not know what I had, but it really did not make a difference, I was 21 and not getting married any time soon.

It was a Saturday morning and the restaurant was slow. I just walked through the kitchen doors and there she was talking on the payphone in the hallway. She wore a chamber maid's uniform, not to tall but her legs were to die for. In my arrogant nature I strolled over to her and enticingly looked her up and down. Made a coy sucking motion with my mouth and told her, "Nice".

She had a very cute slender face with blond hair and blue eyes. Maybe five feet tall and carrying 100 pounds soaking wet. I strolled away into the kitchen and ignored her for the rest of the day. The players hand book says, "Never show too much interest and make them come for it".

Maybe a week had past and I was wondering downstairs in the employee cafeteria when I noticed she was eating in one of the booths. She looked up over the booth and caught my eye. She could not help but smile and I quickly looked and continued on to the food line. I took a hotdog and some fries because that is what they served everyday and confidently strolled over and sat down across from her.

I told her my name was Jim. She smiled and put her hand over her mouth in the middle of a bite and mumbled "My name is Judy; it's nice to meet you". I told her I could not help but notice her attractive legs a week earlier and I wanted to make sure they were ok. As she slightly choked on her hotdog she jokingly looked down and said they were still connected. I told her I came over to ask her permission to take those legs out for a walk. A brisk walk and she said it would probably be good for them. I told her if she would be as so kinds as to have them give me a number where they could be reached I would try to break away tonight and give them a call. She turned my hand over and wrote her number in my palm. I told her I would never wash it hand again and she stood up and left the cafeteria.

That night was great. I picked up my girlfriend Amy and took her out to eat. Yes, at this time you are all probably thinking what an ass I am but I could not help it. Amy was drop dead gorgeous. She had hair so blond it made you melt. She was model skinny and also her eyes were blue as the Caribbean Sea. I could not resist her and enjoyed my time with her tremendously but I needed more.

Amy went to school during the days; she was a sophomore at Keene State College and was always out of school to see me at four. We spent most days together. We were young and infatuated with each other and I could not keep my hands off of her. We would do something until 6:00 and end up in my bed until 8:30. She lived with her parents and they had strict rules to be home no later than nine. She was a daddy's girl and would never cross him although he was meek and as nice as any person I knew. A humble man he was and she respected him for it.

I can't say that I did not feel guilty a little in the fact that I was having gorging sex with her nightly. Although she was not thunder in the sack she did not need to be. She was so beautiful all I had to do was to see her and it was enough. There were times I pushed for her to initiate something but it never seemed to work. The good thing is that she let me do anything and everything. I could take naked pictures of her, anal sex was a trip and when it came to a blow job I just humped her face because she just was not the bomb. God was I arrogant!

The next day at work I happened to see Judy again. Judy was a little less shy this time and approached me on her own. She stated "These legs were looking for your call and felt a little let down last night". I could not tell Judy it was because I was tired from banging Amy until nine and having to drive her home. Yes, she was late for her dad.

Judy said she had to work until eight, but she would like to take that walk after nine. "Works for my schedule" I told her. Neither did she know it worked all too well. I asked Judy if she worked every day until 8:00 PM and she said yes, she had to get the rooms done on her list by six and clean and deliver the linens down to the laundry room. I don't need to say this made me real happy, but I did not know how difficult it would actually become.

That night I created a little tiff with Amy intentionally. I asked her for a little time off with a little devious plan on my mind. Young as we were we both never experienced the "it's not you it's me tactic" until now. Nor had we seen the "we were on a break so I did not do anything wrong by sleeping with her trick".

I did not have sex that night with her to make a point, but it hurt anyways, in my crotch. I dropped her off at 9PM and made a B-line to Judy. I picked her up by 9:45 because she lived a ways from Amy's house. The game began, could I be successful in dating two girls at once seriously. Some people had bragged about it but was it ever pulled off smoothly. Jealousy was a big ordeal. My strategy was real simple. I had to let each girl know about each other gradually, but fast enough so they could not say "You dirty rat bastard!"

That night I immediately told Judy that I was on the rocks with my preset girl friend. Pretty good huh? I told her we were not too serious although we had been going out for over two years. OUCH. I think Judy felt Amy as competition and told me she was fine with it. A sigh of relief swelled through my body, but the biggest feat to be had was about to come. Amy was a meek girl and not loud spoken as her father was. She would have to be handled in the, "We were on a break due to you and it was not my fault ordeal".

I drove around for a couple of hours with Judy in my truck. I had to get to know her and driving had a soothing sense and I had many things to break the monotony if there was one of those uncomfortable silences. It was not long before I convinced her that going to where I lived was a good choice.

I lived with an older man Ray. Ray was an alcoholic but had good intentions. He fell asleep on the sofa every night in a drunken stupor, but I did not mind, he never bothered a soul. When I brought Judy home he had already passed out. I showed Judy the house and ended with my bedroom.

I had bought a beautiful waterbed that was gigantic. I did so for obvious reasons and it was always the talk piece. We sat down on the beer bumper (The cushion on the side of the waterbed frame. I called it this because when you were drunk it always saved you from hitting the hard wood surrounds when you fell). Judy said, "It is always a problem when a man's biggest item was his bed". We laughed and I pushed her playfully onto the mattress where she fell all too easily.

I did not kiss her or approach her sexually yet. I wanted to build a little anxiety first. I asked her frivolous questions for about fifteen minutes or so until she kissed me. I backed off with a smile and said, "Jeese, you are aggressive!" She smiled coyly and said, "Oh yeah, you seem so innocent!" and forced another kiss on me again. I met aggression with aggression and just pulled her pants off and underwear. Surprisingly enough she was satisfied with this. She had a nice shaven pussy. A landing strip was too much for a description. How about that it looked just like an eye brow, a small manicured one. It looked so neat and clean I was tickled pink.

As we kissed she fumbled with my pants and I helped her indirectly. When my pants were free of my body she grabbed my cock and began to stroke it as I straddled her. Her entire little body was between my legs when she slid from my mouth down to my cock. She pushed me over confidently and began to suck my cock intensely. Not necessarily in speed but in confidence. She rolled her head in circles and seemed to be one with it. She never made an abrasion and always mouthed with style. She never overly played with the head as so many women thought was good, no, she mouthed it! She did not need her hand. I was writhing in sensation. I could not keep my hips still. I could not be as so arrogant to not respond to make her work harder. It was the best blow job I had ever had! Then, for the first time ever, in total shock I was, she swallowed it to the base. Not with apprehension, she just swallowed it. It felt so amazing the warmth of her mouth and the saliva on my balls.

Holy shit, she had me shuttering. I pulled her ass around to my face as she worked and began to eat her pussy. I thought I knew my shit in those days and lapped and licked and licked and lapped, aggressively until I exploded. When I came it was so deep in her throat I am not sure she even knew it happened as she continued. The sensation was so intense and I needed a second. I knew my stamina would hold true to continue but I needed one minute.

I motioned to pull free and rolled her over for a re-positioning. I did it smoothly as to not interrupt the flow of the moment. I quickly slid in between her legs and raised them slightly and pushed my cock in. I could feel her tighten up due to my size and I probably should have worked it a little slower but what did I know. Her pussy was so tight I had not quite felt anything like this before. As I slid in and out it felt as if her insides turned inside out and came out of her as I went. She slowly adjusted to my cock and she began to have orgasms.

Judy I now refer to as an "easy cummer". She seemed to cum every three to four minutes. Her body would shudder and would rock one out. Boy did that do wonders for my ego. In defense of me though, I would swing my hips and hit the spots like a porn star.

The sex continued, as the rhythm rolled like thunder. I would position her body in ways that I could hit her g-spot. I knew I was on track when she would shudder. I would roll my hips low and my cock would ride up and almost hit her stomach. It was quite a sensation for the both of us. I would go in circles and made sure it passed by it every time.

I then flipper her onto her side with one leg between mine and one on my shoulder and began my beat. Slowly I slid in slowly knowing I could hurt her easily in this position. Again I circled to hit her spot and grabbed her hand. I forced her to play with her own clit a little. At first she showed a little reluctance due to her age but she soon taunted it like I was not there.

I licked my finger and easily slid it into her ass. She tightened a little but allowed me do it. I did not insert it too far, just enough to tough the right areas to electrify her. Then she began to orgasm hard. Her juices flowed like a fountain. My cock slid so easily in and out, in and out. I had a large mirror on the front of my head board that I loved to use creatively and made sure my positions accented it. I could see my cock sliding in and out of her pussy, my finger in her ass and although I could not see her fiddling with her clit I could see her arm slightly moving. I felt like the conductor of a large orchestra and my crescendo would be as good as any.

The pressure built in my lower back. I resisted it as long as I could. As it grew to my chest and my face I knew I had to release. I pushed deep in her and began to cum. Thrust after thrust I deposited it deep inside of her looking from mirror to her pussy then the mirror to her face. I loved to watch. She was cumming also, but it was my turn this time.

As I finished I continued for a minute or so longer and glanced at the clock. It was two AM and I have been screwing for over an hour and a half. I had to bring her home, I had to work at 6:00 AM. What a hard day I would have the next day. I kissed her and told her we had to leave, but I promised this would continue. She made me promise that we would do it again tomorrow night and I drove her home.

One final note: I received a speeding ticket for driving 90 in a 30 with a notice to appear trying to get at least two hours of sleep, but it was well worth it.