Hit the Road Jack
Publish Date: Feb 19, 2008
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I was an ugly duckling as a young woman: tall, clumsy, nearsighted, and shy. My personality matched my appearance. I was an accountant, and I dressed and looked Ms. Dowdy.
At age 33, my sex experiences had been as uninspiring as my person. A one-year affair at college, (he dumped me) and a marriage that lasted ten years (he dumped me), and two wonderful out-of-character one-night stands, which should have tipped me off to the delights of variety. (I've learned that lesson -- more than 100 men have spilled their seed in me since then. Wine is not the only thing that improves with age.)
I was still looking for the perfect relationship when I ran into Jack. He was a decent fellow, a few years older than me, and had never been married. Like most unmarried men approaching middle age, Jack was old-maidish in his methodical habits and too attentive to his mother but, hey, I had modest expectations. I had been divorced for more than a year and had gone months without sex -- except one memorable sweaty night in Thailand. See "Beach House Bingo."
Jack and I followed the script for conventional romances. On our third date, I invited him to my apartment "for a drink." He didn't set off any sparks in bed that night, but we became a couple and I was happy to have a man and the security of a relationship.
We went out a couple of nights a week. I stayed over at his place once, but in the morning he was in a hurry to see his mother, it being Sunday -- and he always, always spent Sunday with his mother.
We were one-trick ponies -- missionary sex after a brief warm-up. He just climbed on and hunched himself to climax and I usually climaxed about the same time. And that was it. It began to get just slightly weird when we had been going out for three or four weeks. I was lying on my back, my legs spread and waiting for him to mount up and ride, when he asked, "Would you masturbate me?"
I said, "Sure." I was nothing if not compliant in those days. I made a feint at his penis with my mouth, but he didn't respond. A hand job was what Jack wanted. I gave it to him. I enjoy masturbating men -- and I hadn't done very much of it during my unadventurous sex life. So, jacking off a man was new to me. We had enough light in the room for me to watch cum spurting out and pooling up on his chest. I stuck my finger in the pool and tasted it. I got the impression, however, that Jack didn't like me tasting his cum. Maybe his mother wouldn't have approved.
Jack got up quickly and said he had to go home and I was left lying there on the bed wishing that at least he had finger-fucked me. Well, sex isn't always satisfying, I told myself, and, in fact, the next time we went out he missionaried me adequately. But then next time he asked again for a hand job (you get the idea why I am calling him Jack, don't you?) and after that we rarely fucked. Our dates sometimes began and usually ended with a handjob for him and nothing for me.
I consoled myself that Jack was presentable, had a good job, and didn't molest children. Most of all, it pampered my tiny ego to have a boyfriend, inadequate as he was in the care and feeling departments. Things went on this way for six months until I got a job with the State Department and was told to report to Washington in a month. Suddenly, I had a bright shining alternative to Jack and my built up resentment against his sexual selfishness came to the fore. I was looking forward to saying sayonara. I didn't plan, however, to do it in the spectacular way that it happened.
On our next date Jack wanted to be jacked off before we went out. I acceded to his wishes, as usual. He just pulled his shirt and pants off and laid down on my bed and I stroked him to completion. I didn't even take my clothes off -- and he didn't care. Then, we went to a restaurant to eat. The dining room was full, but we saw several friends at a large table in the bar and sat with them and drank margueritas and ate nachos.
"Sly" showed up. I had gone to high school with him. He was tall and handsome and slick and a notorious lady's man. Sly had never paid the slightest bit of attention to me. Until then. "Becky," he said, kissing me on the cheek. "You're looking good." That was an exaggeration, but I had been working on my appearance, and I'm a sucker for a compliment. Sly pulled up a chair and joined us, sitting by my side. Jack was on the other side of the table, talking about football with another guy.
To make a long story short, I ordered another marguerita and drank too much too fast. Then, I was sick. Sly helped me out of my chair, saying to Jack, "Stay where you are, Jack ol' boy. I'll take care of this." Jack looked at me with a puzzled expression, but he didn't offer to help. Football was more interesting than my gastric distress.
Sly half-carried me to the parking lot and I vomited all over the boxwood bushes. He helped me into the front seat of his car and wiped vomit off my dress with a paper towel. I was alert enough to notice that my dress was hiked up way over my knees, and my legs were splayed. I didn't care. He sniffed my breath and clothes and recoiled. "I'd better take you home. You're a mess." he said, "and so am I." I muttered my address, and went to sleep.
Sly hauled me up to my apartment and found the key in my purse and opened the door. I staggered into the bedroom. The bed was still stripped down to the sheets where, two hours before, I had jacked off Jack. I toppled over onto the bed; I was waking up and feeling better. I could still smell Jack on the sheets.
"You want to take a shower?" Sly asked.
"Yes," I said. And I sat up and began taking off my clothes. Sly helped me unzip my dress, and pulled it over my head. Sitting there in my panties and bra I had a twinge of romantic feeling. I put my arms around him and started laughing hysterically. Or maybe I was sobbing as I contemplated the bed where Jack had been, thin penis upright and quivering, as my hand stroked him. "Jack and the Beanstalk!" I shouted. "Hit the Road, Jack!"
"Shhh," Sly said. "You'll bother the neighbors." Quickly, he slipped my bra off and I sat there dumbly surprised, my breasts hanging free. I didn't protest when he pulled my panties off and led me to the shower, turned on the hot water, and pushed me inside. "Jack be nimble, Jack be quick" I shouted. "Jack me off with a hockey stick." I continued my loud recitations until, suddenly, Sly was in the shower with me, naked, and he put his hand over my mouth. He handed me a bottle of mouthwash. "You need it," he said. I took a swig, swirled it around, spit it out, and then he kissed me, his soapy finger finding its way to my clitoris.
I was as hungry for sex as a bear is for honey. I was still noisy. "Fuck me gently, fuck me slowly," I sang. "Take it easy, don't you know, that I have never been fucked like this before." I was so, so out of character. Sly and I dried each other off, headed for the bed, and reclined together.
That was when Jack stuck his head through the door. He had a key to my apartment and had come looking for me. It must have been a sight. I was lying on my back, my hand on Sly's penis, his body half covering mine, his finger inside me and his mouth on my breast while I tunelessly sang "Fuck me gently, fuck me slowly." It was a mortifying moment -- but Jack turned soundlessly and left. For just a moment I froze in the bed. Sly paused, but he didn't look over his shoulder at the retreating Jack. He looked at me, and I smiled, and we continued. Jack was history.
Sly was into Tantric sex or something that gave him enormous staying power, and I hit all four opening notes of Beethoven's Fifth with booming orgasms. I should have called Jack the next day to apologize, but in the sober light of day I couldn't -- and I was leaving town anyway. I never had another encounter with Sly. I hear that he got married, got religion, and became a perfect family man. I hope his wife appreciates him the way I did.
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