Judy, Jeff & Me Ch. 1

In the late eighties I was a regional manager for a restaurant chain. I was still living in Kansas City and spending a lot of time on the road. Although I still did a glory hole gig when the opportunity presented itself, other exciting sexual adventures were just around the corner.

In the late summer of 1988, my region was expanded to include Wisconsin and Michigan. Since I had never visited any of the company locations in those states, that became my first order of business. Jeff Pearson was the manager of one of our better grossing restaurants in the region. He and his wife Judy lived and worked in Madison. I had met Jeff once at a company get together but had never met Judy.

I arrived at the restaurant mid morning to observe the staff preparing for the lunch crowd. Jeff welcomed me and we worked together for several hours, going over his operation and books. He had s decent size office where we could work and talk. Several staff members had interrupted us but had always knocked before coming in.

Suddenly the door to the office opened and in walked about the feistiest little redhead I had ever seen. Jeff is normal height and weight but this little bundle of sex wasn’t an inch over 5 feet. She had on tight white shorts, the kind that are so tight that the crack in her pussy is clearly visible. She had on what I call a “poorboy” sweater….short sleeved, tight fitting with a banded bottom ending just above her navel.

Jeff said with only a wee bit of embarrassment in his voice, “Reg, this is my wife Judy.” Judy had a fantastic mouth that turned into a big smile showing full lips and lots of white teeth. All of which encased a red tongue that looked very talented. I stood up to meet her and shake her hand. Standing 6 foot 5 inches I towered over this little bundle of heat. My first impression, arrived at in under 5 seconds of our introduction, was, “There is NO fucking way he can handle this hot bitch!”

Judy was friendly and sexy in an intriguing way. After all I was her husband’s boss so she couldn’t exactly either ignore me or grab my cock. She came across perfect….self assured, sexy, spunky with a lot of energy, good looks and smarts to back her up. This broad could “walk the walk”! She was no bullshit. She also wasn’t wearing a bra. Lots of guys like big tits, but I have always been partial to smaller tits that don’t sag and which have nipples that get hard as hell when the woman is excited or just cold. Judy was perfect for her height…….slender legs, prominent nipples that were making bumps in her sweater, a tight cute ass and a face with blue eyes that made me want to shoot cum all over it. And topping off this hot babe was red hair that you knew was natural.

Jeff set back down at his desk and I set down in the guest chair. Judy set on the corner of Jeff’s desk, dainty feet not touching the floor. She was something. While I was trying to be courteous and respectful, I had a vision of her mounting me and trying to take my big cock up her tight, hot pussy. I had a hard on which she later told me she was very much aware of. Thankfully, Jeff was on the other side of the desk and couldn’t see the bulge in my pants. The disadvantage of wearing boxer shorts is that they don’t contain the meat when it wants to greet someone.

I looked over at Jeff expecting to see a look of embarrassment or maybe even anger. If he was the jealous type she sure was acting in a way to fire that jealousy. I thought of her walking past all the studs who tended bar and waited tables and the affect she must have on them. Jeff was no dummy. He knew exactly how she affected men. He either had learned to live with it or liked it.

After some chitchat Judy asked Jeff if we were working that night at the restaurant. He said we hadn’t discussed it but it was up to me. “Well”, Judy said, “if you aren’t going to work why don’t we invite Reg over to the house for a steak. He looks like a red blooded American boy who likes his meat rare.” Jeff smiled, looked at me and said, “Sounds good, Reg, what’s your pleasure?” Since I was going to be there for the weekend, it wasn’t necessary I watch the operation that night. “Great” I replied I will bring the wine.” “Then it’s settled”, said Reg, “I will pick you up at the hotel at seven. No need for you to drive to our place. It is a little hard to find.” Judy clapped her hands said, fantastic, slid off the desk and said she was going home to get ready for the evening. As she left the office it was impossible not to watch her cute tight ass. When I looked around at Jeff, he just smiled.

A bit later I returned to my hotel, returned some calls and got ready for the evening with Jeff and Judy. I took a long shower to get all the road dust off me and to use the light spray from the hand held shower head to tingle my balls while I slowly stroked my hard cock with a soap covered hand. As I slowly masturbated, my mind was full of Judy. I envisioned each wonderful part of this newfound treasure. At the office I had briefly thought of her naked and in heat trying to take my hard cock up her tight cunt. I was reminded of another small woman I had fucked that after trying several times and being unable to get my cock in had climbed off and gotten some oil out of her purse. While she looked me in the eye and anointed my cock, she smiled and said to my unanswered question, “I thought I might need this!” That was one of the finest compliments I was ever paid.

I came close to shooting my hot cum while in the shower, but didn’t want my lustful vision to be dulled even the slightest. I rinsed off, dried, shaved and put a light covering of my favorite aftershave over my body. I always put some on my cock and balls when going out. Women appreciate a clean smelling man.

Jeff picked me up and we stopped at a wine store and I bought a very nice California Merlot to go with the steaks. When we arrived at their house, I was glad Jeff had picked me up. I would have had a hell of time finding it. It was secluded and overlooked a small lake that begged to be fished for bass.

Judy met us at the door, with her radiant smile and outstretched arms. “Welcome to our home, Reg. You are welcome here”, she said as she reached up to give me a light kiss on the cheek. Even though I definitely wanted to fuck this woman, I still admired her skill as a hostess and wife. Jeff had a real asset in this one. I was introduced to Katie, their five year old daughter who was a miniature version of her mother. Poor Jeff. He was definitely outnumbered!

Jeff fixed me a wonderfully dry vodka martini while Judy put a mild chill on the wine and finished her preparations. Jeff and I walked around the backyard, out to a deck area overlooking the lake where he had his bar-b-que set up and ready for action. Show me a guy in the restaurant business who doesn’t like good food and booze and I will show you a guy who should get out of the fucking business. A round table on the deck was set for three.

Judy came down to the deck with refills for the martinis and the steaks seasoned to perfection. While she and Jeff busied themselves getting the steaks on I could take Judy in without being obvious. She had changed the shorts and sweater for a cute, colorful sundress. It was short and kind of lose fitting. I was happy to see her smallish tits moving unencumbered under the light material. Although the dress covered her front it was held in back by a single button. Her back was visible and I had a vision of her spine running down to a set of dimples just above her ass. The hard on was returning! I knew that if either looked it would be visible. At the last minute, when dressing, I had decided to forget the underwear. My cock had no alternative but to make a tent out of my pants if it was hard. Soft, it simply lay against my left thigh, its outline visible to anyone interested.

Dinner was excellent. Good food, wine and booze and excellent company. I helped Jeff clear the table while Judy checked on Katie to make sure she was sound asleep. As Jeff and I finished the wine, Judy put some dancing music on the boombox CD player. “OK”, Judy said, “which one of you is going to dance with me”? Jeff looked at me and said, “Go ahead Reg, I am not much of a dancer”. I said OK and walked to Judy and her outstretched arms. The music was a little harder than soft rock so it didn’t call for close dancing. Our height difference would have made that difficult. However, watching that sleek, cat like body move made me hard again. I tried to keep my back to Jeff, who just watched and smiled. Every once in a while Judy would spin backward into my arms and bump into my hard dick. She didn’t indicate she noticed, but she didn’t stop doing it either.

About eleven I thanked them for a wonderful evening, but it had been a long day and I should be getting back to the hotel. Jeff turned to Judy and said, “Judy can you take Reg back to the hotel? I have had more than enough martinis and wine and probably shouldn’t be driving.” “OK by me”, she replied, “As long as Reg doesn’t have anything against women drivers!”

“Whatever works for you two is fine with me”, I replied.

Jeff and I arranged to meet at the restaurant mid-morning to continue our work. I thanked him and followed Judy to their car. She pulled out of the drive and proceeded back to town. She didn’t say a word and neither did I. About two miles from their house she pulled into a secluded side road and drove a few hundred yards back into the woods. She turned the car around facing the way we had come and turned off the engine. I reached over and lightly touched her knee. I wanted to let her know it was her show. I was not going to instigate anything, but wasn’t going to put up much of a fight either.

“Reg”, she said, “please take your cock out. I have wanted it in my mouth all night!” There was a little moonlight so I could see the serious expression on her face. “Can we kiss first?” I said light heartedly. “NO! Later! I want your cock in my mouth. I will take your tongue later.” God, she was the most aggressive female I had ever met.

I unbuckled and unzipped my pants while she raised the tilt steering wheel. Her eyes were wide and reflected the moonlight. Her gaze never left my hands as they followed her instructions.

“Pull them down” she commanded. “Yes, I knew you don’t have underwear on. Neither do I!”

As I raised my ass and lowered my pants my hard cock stood up proud and firm. “Now stroke it for me”, she commanded. I noticed her left hand slide under her sundress. I did as she instructed as I watched her face as she watched me jacking my cock.

Suddenly, with a groan she literally fell into my lap as she grabbed my cock with her free hand and inserted the wet head of my dick into her hot mouth. It was now my turn to moan! She was hungry for my cock, maybe any cock. Who the fuck cared? She literally devoured me. She lifted her head and looking into my eyes said, “Please don’t cum yet. I am going to cum with my fingers, but please wait. OK?” It was more a plea than a command. I nodded as her head dropped back down to continue her efforts. I could hear her moan around my cock as she was wracked with an intense orgasm. I almost lost it then. I wanted to shoot off in her mouth so bad. I had wanted to shoot in her and on her for hours! Fortunately, she stopped sucking and jacking my cock as she experienced her orgasm. Otherwise I would have broken my first promise to her.

She kissed the head of my cock before she raised up to look me in the eyes. “Please kiss me now”, she whispered as her lips parted and her eyes slowly closed. She was so beautiful this girl/woman. I took her head in my hands and lowered my mouth to hers. I felt an unusual tenderness. Particularly considering how badly I wanted to plunge my cock into her soft body. Maybe it was because I liked her. Who knows?

After exploring each other’s mouths she got up on her knees on the car seat, lifted her sundress and straddled my lap. Never taking her eyes from mine, she reached down took my cock in her small hand and lowered herself slowly but surely onto my eight inch monument. Any concern I had earlier about her not being able to take me disappeared as with deep concentration she pushed herself down, down, down, until my balls were tight against her ass.

“Reg” she whispered, “we don’t have all night, so please do as I ask. OK?” It was a plea from a hot woman who knew exactly what she wanted and how she wanted it. In other circumstances I might have gotten pissed, but I knew I would be rewarded by granting her request.

“Sure baby. Use me anyway you want. I want to please you.”

“Oh God, Reg, you are so deep in my cunt. I have never had a man so deep. It feels so good. God it’s good! Reach behind me and undo the button and pull my top down” she moaned.

I did so and as the light fabric fell away my cock spasm as her young girl tits with long hard nipples came into view. They were at least half an inch long and the size and hardness of pencil erasures. I cupped her tits in my hands and squeezed as she started to rock back and forth on my cock.

“I want to grind my clit against your pelvic bone, Reg. I won’t raise and lower myself on your cock now. I want it all the way in all the time as my clit is stimulated. While I do that, I want you to suck and bite my nipples and then give me your tongue and fuck my mouth.”

True to her word she started to move back and forth while pushing down against me. I took her soft ass cheeks in my hands and helped her movements without raising her on my cock. With her hands gripping my shoulders she leaned back raising her fantastic tits to my mouth. I filled my mouth with first one and then the other as I whipped her nipples with my tongue.

“Suck them, bite them. Hurt them, please make me cum on your cock”, she cried as she rocked back and forth faster and faster. In a voice that demanded she said, “OK, I am close. Give me your tongue and fuck my mouth. Use your fingers to twist my nipples, HARD! Hurt them!”

As her ass picked up speed in her back and forth frenzy, her mouth found mine and I filled it with my long, hot, wet tongue. I took a nipple between the thumb and index finger of each hand and pulled and twisted as hard as I dared.

“FUCK ME”, she cried, “FUCK ME! Don’t cum yet, in just a minute. I will tell you! OH SHIT! OH SHIT, FUCK, CUNT! Oh sweet Jesus I am cumming! I was so fascinated by her excitement I was able to hold back. Watching her cum without any pretense, qualms, or embarrassment whatever was the sexiest thing I had ever seen. I raised my ass so she could get more cock and twisted her nipples harder. She kept on cumming crying out every fuck word I had ever heard as her orgasm took control of her sweet body. I was being used as never before and loving it and wanting it too never end.

As quickly as her orgasm began, it ended. She collapsed against me as I put my arms around her and held her close. I could feel her heart pounding in her chest and felt her shutter as small orgasms continued to jolt her body.

She slowly looked up at me. A look of concern crossed her face. “Oh baby, I am so selfish. God that was good. Thank you! I have fantasized about that all day, but it was many times better than even my fantasy. What do you want? What can I do? I will do anything. Suck you off? Fuck you hard? I will get out of the car so I can bend over and you can shove that monster up my ass if you want. Anything, Reg, absolutely anything”. I could see she meant it.

“What I want”, I said, “is to have you stay where you are and ride my cock hard. I want to lean back and have you fuck me and take all of my hot cum up your pussy. I want you leak my cum for hours!” With that I lowered myself down a little further in the seat so I could lean my head back against the headrest.

She smiled and slowly unbuttoned my shirt. As she raised slowly on my cock her hot tongue toyed with my nipples. I had never had my nipples stimulated during sex. It never occurred to me that it would be good. Just as she reached the point where the head of my cock was about to come out of her cunt she slammed herself back down. The pain in my nipples accentuated the pleasure in my cock as she twisted them. I looked at her and saw a smile that was almost demonic. It said, “Reg, you are going to learn a few new things from me!”

She would raise her ass slowly and then slam down. Each time she would twist one or both of my nipples. She picked up her pace until the pain and pleasure blended into the most erotic sensations I had ever felt.

“Talk to me Reg. I want to hear you as you cum. Say everything you are thinking. Don’t hold back.” As if to set the tone, she growled, “Now fuck me you son-of-a-bitch”!

Her tone and her words had an immediate effect. “Call me a son-of-a bitch! You hot cunt fuck bitch! Fuck me slut! Take my cum up your hot pussy! Serve me, you will always remember this fuck!”

We were truly two animals in the middle of a man/woman fuck of primal proportions. We were no longer pleasing each other; we were satisfying the ancient urge to be sexually satisfied in all its glory.

As I told her what I wanted to do and what a hot fucking bitch she was we looked into each other’s eyes and I exploded! She didn’t miss a stroke. Her ass was moving so fast she was a blur in the moonlight. My hands had left her ass and pinched her nipples hard as she pinched mine.

“FUCK ME, FUCK ME, FUCK ME Pleeeeeaaaase! I am cumming again!” she cried as wave after wave of spasms shook me to my soul and hot cum exploded into her tight hole. I kept on shooting as she cried, “I can feel your cum hit the back of my cunt!”

After a man cums, his cock becomes very sensitive particularly around the head. Mine was no exception. I grabbed her hips to hold her in place, as I couldn’t take any more stimulation. And then it happened, something that had never happened to me before. Judy laughed out loud. A fantastic laugh, a laugh of pure joy. I was dumbstruck. What was she laughing at? Me? Was I amusing? I started to be offended. She sensed my rising anger and took my head in her hands and said, “I’m sorry. I am not laughing at you! I always laugh if a man and I cum together. I am so fucking happy I can’t control it. It is a compliment, Reg. Please don’t be angry. You pleased me. We pleased each other. I laugh at that happiness.”

The look on her face as she explained was exquisite. Although she had just given me the best fuck of my life, her facial expression was that of a young girl seeking understanding and maybe forgiveness. I knew she spoke the truth. There was only one possible response. As my cock slowly shrank from supreme satisfaction, I let out a laugh that was as hearty as any I could remember. She was right. We had shared a joy that is as ancient as man and woman.