Hitchsexing Diary: Katie and her Dad
New Teacher trains her first student in the back seat of her dad's car.
Actually, it didn’t take that long before I had my own in-the-flesh participatory sexual experience while hitchhiking. The recollection of the afternoon the prior summer in the back of that pickup was still fresh in my mind. And the look that young girl had as she jerked off the farmhand was forever emblazoned on my mind.
On this particular June day I was hitching a ride back from a neighbor kid’s graduation at Bowdoin College in Maine. I had ridden up with his parents and the plan was for me to take a bus back home the next day. It was late on a Saturday afternoon and I was only then hitting the road, which was a recipe for getting stuck someplace at night but I had no money for a motel room and all the dorms and frat houses on the campus were now closed for the summer. All I could do was hope for some luck. Best case was I would make it home around midnight. Worse case? I tried to never give that much thought. Actually the very best case would be to make it home sexually satisfied. I was ever the optimist.
I was just a kid, not yet nineteen. All I ever thought about was sex. I probably averaged 5-6 erections a day. Had I not been in college, with a roommate, I would be masturbating at least every night. I looked for sex constantly. Every girl I met I thought about bedding. So you can imagine my thoughts when about an hour after I got to the on ramp I saw a car approaching with Connecticut plates. I immediately assumed my oh-please-pick-me-up I-am a normal-guy going-in-your-direction look.
At the speed they passed me I doubted they would stop. But then I saw what looked like a girl in the back seat turn around and a second later lean forward. Brake lights came on and with a slight squeal of the breaks the car stopped. I grabbed my back-pack and took off a runnin’ toward the car. I always had this neurotic fear they’d change their mind and peel away were I to tarry.
Just as I was about to grab the door handle I caught a glimpse of a blonde girl in the back seat. Her head was down and she seemed to be engrossed in a book. There was a box and what looked like a case of some kind on the front seat. When he saw me hesitate before opening the door the driver, a middle-aged guy with charcoal hair, gestured with his left hand toward the left rear.
I scooted around back and with a click the door unlocked. I got in awkwardly. Almost diving into the girl’s lap. In the process I tried to make eye contact with her while I looked for a place to stow my bag, but she kept her head down acting very disinterested.
“Just hand it up to me,” the guy said, “I’ll put it on top of this other bag.”
I expressed the usual “oh-thank-yous” to which he responded: “We saw your sweatshirt so we figured it was safe to pick you up.”
“Uh…oh yeah, wow, that’s right my sweatshirt.” I laughed. It was more like a stoned giggle since I had shared a farewell joint with Billy before his parents took me to the highway as they turned off to spend a week at their cottage on a nearby lake. I had put my college sweatshirt on because the late afternoon sun was fleeting in typical June fashion and the temperature had dropped into the low sixties. I remember thinking that I needed to get it together quickly. The dad looked really square and conservative. And the daughter, well she was straight out of Chi Omega.
I could see that she had long legs. She was probably taller than me. Her flaxen hair was shoulder length I imagined, but she had it in a pony-tail so that was just a guess. She had on a pair of goofy granny glasses (true to the times) that didn’t match the rest of her outfit. She was wearing an oxford men’s cut yellow button-down collar shirt, dark blue skirt which I later determined was a jumper, matching yellow knee socks, and Bass Weejuns penny loafers. Her skins was flawless and there was no sign of any makeup, except maybe some lipstick applied earlier in the day. This girl was definitely out of my league, and obviously not of my lifestyle. She was either preppy or horsey; both fashion genres were common in the New England of the 1970s.
I had long blonde hair, and was pretty skinny. I stood only about 5 foot eight. I was hippie cute but still had lingering acne. Generally girls like her looked right past me. For the most part it was OK because I’d become used to that, and had low expectations when it came to chicks of her ilk. I certainly didn’t look threatening to anyone thinking of giving me a ride. In fact, even some of the women who stopped could have done me harm. I was pretty mellow and pretty passive and certainly looked the part.
“Katie here graduated from the university today.” The dad said as we accelerated to highway speed. “Show him your degree, honey.”
“It’s packed away in the trunk, dad.” She answered so dispassionately that I actually began to feel uncomfortable. In a way she intimidated me, this lowly freshman was wondering how I was going to be able to converse with a stunning graduated senior, so instead I just went back and forth with the dad. He asked me what I was studying, how I liked the school, what year I was in—the typical small-talk stuff.
“Are you going back to the campus?” He asked eventually. Since my school was in Boston, he may have thought I was going back there.
“Oh no, I’m going home. I live in Wethersfield,” I said thinking he was probably going at least that far into Connecticut.
“Great, we live in Greenwich. We’ll get you almost to your front door.” He said smiling at my in the rear view mirror
“Far out,” I exclaimed coining the vernacular of the day. “I can call my parents and they’ll come get me.”
Southward we rolled along Interstate 95 in Maine. Past the sweet smelling Burnham & Morrill baked beans plant in Portland and the stinking paper mill town of Westbrooke. We passed Ogunquit and Saco. The dad and I talked baseball, politics, and since we were New Englanders we got around to everyone’s favorite subject, the weather.
We crossed into New Hampshire and circumnavigated the traffic circles of Portsmouth. Still I was having no luck engaging the girl sharing the backseat. I had been able to learn her name: Katie. Only because I stuck out my hand and introduced myself. She gave me a displeased look. “Oh yeah, that’s right Katie. Your dad…” What an idiot I was. That felt even weirder because in the tribal culture of long-haired America names weren’t always exchanged. Introductions seemed horribly formal to people rebelling against formality and tradition. If you didn’t know a guy’s name you simply referred to him as man. The polite freak in those days substituted the word lady when addressing a female.
Next came Massachusetts state line and the dad asked a question that drew her blondeness’s head out of the book. “Is anybody else getting hungry? “ He asked.
Katie actually looked at me for a second. Our eyes locked and it was then that I fell.
There isn’t an adjective in the English language that could truly describe those eyes of hers. They were blue; blue sky blue. They were big, and they were locked on mine. Her eyebrows were sparse, perhaps even enhanced with a pencil. She later told me she heard the same music in her head when she saw my eyes. She had the kind of eyes that could lead a man both down a dark alley and to a place of flowers and soft breezes at the same time.
We sort of nodded in agreement that something to eat would be nice. “What were you thinking about, dad.” She said after a few seconds.
“How about the Hilltop?” He was referring to the New England institution that was also a Route 1 landmark The Hilltop Steakhouse in Saugus. Ooh I liked that idea. A steak would really hit the spot.
“Daddy, I can’t eat that much. Besides, I hate that place.”
I could see his visage change in the rear view mirror and he flashed disappointment but Katie was adamant. Frankly, I was kind of bummed myself. I could see him thinking about alternatives. He eventually asked, “How about some chowder and clams?”
This time she didn’t look at me. “That sounds better, daddy.” Down went her head again. And down went my confidence level as I began to feel more than a little foolish ever thinking that there was something in her eyes that could give me hope. Her father said the name of some place I’d never heard of. She said “OK.” I just shrugged my shoulders.
A few miles up the highway we exited and a mile or so down a back road we approached this place that if it weren’t for a fresh coat of paint and the 6 or 7 nice cars parked in front you’d drive by it. It bore an old mid-20 th century white plastic sign with the Coca-Cola logo on one end. It was the Chowder Something or-other. They also had a sandwich board in the parking lot that said “Clams and Cold Beer.”
When we got out of the car I was able to confirm the fact that Katie was tall. But it was more like she was statuesque. She had this hauteur that you’d see with women who had million dollar legs and other striking features, especially women who are taller than many men. She strode purposefully toward the screen door hanging slightly off hinge, obviously from being swung many times a day.
I was pretty sure at the time her purpose was to not give me any hints that she was interested.
I noticed at least three heads turn as we slid into a booth, them on one side me on the other. She was a sight. Other than that wonderful smell of deep frying clam batter and the sound of a corner jukebox playing away, what you noticed was a buzz in the place. Like people were excited to be there. But it wasn’t so loud that you couldn’t chat normally. And I was bound and determined I was going to engage Katie in conversation. Her degree was in English and she thought she might just start teaching right away.
To my surprise once we started aboutcareer options she relaxed and seemed to lose the attitude. After quickly perusing the menu she doffed the granny glasses for the first time. I could feel my heart start to thump faster. How the Hell can I keep my composure? It was more than just the eyes. She was charming and captivating to the point I was probably being a little rude to the dad. My focus was on his daughter: 100%
The wind changed direction so fast. Before long it actually seemed like she was flirting with me. There was so much eyelash fluttering, stroking of the hair, and nervous giggling the guy working the counter had to have noticed it. She seemed incredibly interested in what I was saying, though I can no longer remember the specifics of the conversation. Once our drinks arrived the old man proceeded to sip on his beer and turn his attention the Red Sox game on the TV above the cash register. She’d play with the straw, twirling it around in her drink. She’d cock her head and rest on her elbow leaning forward as I talked.
Now I was beginning to wonder if maybe her father would not approve of the way things were going, and dump me off some place in the middle of what was a long lazy New England early summer evening at the time, but would eventually become a dark night somewhere outside of Boston. He seemed cool with it all.
Sometime between the chowder and the basket of clams she had taken her loafers off and I felt what seemed like a foot rubbing first up and then down my shin. A short time later I felt her rub the side of my leg, then hook around and go down to my heel. She must have seen my eyes grow bigger as I stopped talking for a bit.
Then the father turned away from the game on the screen and asked, “Is everybody’s food alright?”
“Oh yeah, dad. I love my soup.” She replied. His eyes moved to me.
“Yes sir, chowder was great and I love these clams. They’re perfect.”
He sort of nodded and went back to watching the game. And we went back to talking. Sure enough I felt the foot again, this time a little higher. By now my cock was up and bulging in my bell-bottoms. My heart was beating still faster. I wanted to take my own shoes of and return the favor but I was wearing Earth shoes with laces, which made them impossible to slip off.
Her father excused himself to see about getting s desert menu and once his back was turned a mischievous grin came across her face while she leaned back in the booth. She was stretching that right leg so that she could get her foot up into my crotch. I think I jumped as I felt her big toe dig into my scrotum. I can’t imagine my expression.
“Katie, what are you doing?” I whispered. “You’re getting me all turned on.”
“Am I?” She asked coyly.” You’re blushing and it’s really cute?” She looked away to see where her father was. “Haven’t you ever had a girl play footsy with you?”
“Yeah, but not a girl I just met…and not when her father is at the table.”
Thankfully, her dad got back so that my cock had a chance to de-inflate before I had to stand up. As we all headed toward the cash register. The mister says: “Oh no, young man, I’ve got this. Don’t worry about it.” I had the money for the meal but he was insistent. “I’ll catch you guys at the car, after I visit the boy’s room.” Katie and I went out the door and turned right to where their car was parked. She went in her side and I in mine.
My ass had barely hit the upholstery before she was on me. Her lips locked on to mine like a warm suction cup. This big amazing, extraordinary woman had this still awkward inexperienced teenaged boy pressed against the door. My head was in her hands and it was as if she was trying to crawl inside my skin. I smelled it. I smelled it immediately. It was the smell that every man loves and looks for. It is the odor of arousal that comes from deep inside a woman and is emitted on her breath when her genitals swell and moisten. It is musky and earthy and if a man isn’t erect before, he almost always is after that odor of love hits his nose. That odor is as primal as humankind itself.
I came alive. I pushed back and was amazed at how easily she caved and started to go down on to the seat. Just as I got my thigh between her legs, she jumped and said: “No, no, stop. I need you to keep an eye out for my father.” By then she was pushing down her skirt and her panties at the same time. “Unzip your fly, hurry.” I hesitated in disbelief, so she grabbed the button for my jeans and tore it open. In almost one motion she pulled them down to my knees. My cock boinked out into the air, pointing skyward and quivering.
“Do you see him?” she whispered with breathy urgency I had never ever heard from a woman.
“No, not yet.” What is happening here? Is this girl is about to rape me?
“Let me know when he comes.” By this point it was dark enough so no one could see into their car, including her father. She jumped on to my lap with a velvet thigh on either side of my torso. I felt her grab my cock and again with one move not only was I inside her but my turgid rod was buried to the hilt.
To say she was wet would be an understatement. Katie was soaked and hot. And the entire length of my shaft –every nerve—was bathing in her lust. I hadn’t been with many women but I knew that this woman was horny. Then she started bouncing. Her feet were on the seat and she used them to push; up and down, up and down. Her body became a piston. Her wide, sensuous, and shapely woman-hips were rising and falling maybe a foot with each stroke. She was like a wild horse the first time she’s saddled, snorting, gasping in big breaths of air and then exhaling as many as two or three times a second.
Thinking back I’m glad I was given the job of being the lookout because I wouldn’t have been able to last a minute against that assault otherwise. “Don’t come; please don’t come honey, please.” I think I was coherent enough to say OK, I can’t remember for sure. I just couldn’t believe what was happening and that her father still hadn’t come out the door. Twice I had to fight back the tingle. Again she yelled: “Don’t come, baby”
Then she went off. OOOOOOOOHHHHHHH My Gawwwd. She actually shouted and I was tempted to cup her mouth to stifle the noise, but right then she fell forward off my cock and onto the seat moaning while at the same time pulling up her pants and skirt. She kept breathing hard and later whispered: “ Oh baby, Oh that was so hot, so-o-o good.” Then she bolted back upright and again locked onto my lips for a few seconds.
“Did you like it too?” She asked pulling away and staring deep into my eyes.
“Oh, Katie baby, of course I did. It was amazing.” I eked out the words trying to catch my breath as well as doing everything I could to push the sperm load back down into my balls.
“Good, pulls your pants back up.”
I told her I couldn’t believe her father hadn’t come back yet. She replied by saying. “Are you kidding, my dad always spends at least ten minutes in the bathroom, especially after a big meal.” Then she snuggled in my arms and lifted her lips up to my ear. “We’ll probably have to stop one more time. Hang on; I’ll take care of you then.” Just hearing her say that brought my cock back to the erect state. She cupped my swollen member in her palm and then squeezed it while saying: “OK, hon?”
Thanks Katie….” I paused for second a little nervous about having this kind of conversation: “I almost came twice.”
No sooner had she uttered “I wish you could have,” than her father appeared coming out of the dark and walking briskly toward the car. We checked each other’s appearance just as he reached the driver’s door.
“Sorry, I took so long guys.” We exchanged glances and slight smiles.
“No problem, we just continued our discussion about grad schools.”
She had slid back over to her side of the back seat leaving me sitting there so close but so far away from a dream that only a moment before had come true; and held the promise of coming back around in short order. There in the dark, I sat staring out the window at the passing night trying to make sense of it all. I repositioned myself so I could lean my head on the seat and just gaze at her profile 18 inches to my right. She was real. I convinced myself of that. I could reach out and touch flesh that had been hot for me fifteen minutes earlier. This perfect creature with the incredible eyes, silky hair long legs and round curvaceous hips had taken me inside her. Me, a perfect stranger. Me, a man between my legs but between the ears still very much a boy. She had called me baby and honey. She had whispered my name. She had held my sexuality in her hand. The only thing better would have been for her to tell me she loved me.
But a girl like Katie would have never done that. She wouldn’t fall in love with someone like me. This was a woman over 21 now. She now held a college degree. She had talked about grad school at NYU. She had closed her eyes and she was a sleeping beauty if ever a sleeping beauty there was. No wonder she was tired that girl had done a lot of living in the three minutes of so we were in flagrante.
Now we were on the Mass Turnpike and awakened myself to see us on an exit ramp with a toll booth dead ahead. As the car was bathed in all those lights Katie opened her eyes, as well. The first thing she did was look over in my direction as if to make sure I was still there. Then she squeezed my hand.
“We have to pull for a second I need to pee.” He said in a very matter-of-fact way.
Sure, dad, Katie said as he went turned into the gas station. He headed off for the convenience store and the men’s room.
In an instant Katie was at my fly and my cock was rising. As she grasped it, it was still inflating. Her mouth was almost as warm as her pussy was, but the difference was her tongue. It was circumnavigating my penis like a calves tongue on an extended finger. OOOOOHHHHHs and the sound of quick breaths emanated from my throat and a soft moan of delight came from hers. She must have sensed I was close to popping since she pulled off my cock and looked up. “Go ahead and come in my mouth, OK?”
I’m not sure I had ever heard a woman say anything so drop-dead erotic as that. Her head then started really bobbing and the tongue continued doing its amazing work. Again I got the tingle at the base of my spine but this time I let it happen. She heard me take in two or three quick breaths and I know she felt my cock swell and its temperature rise. Soon my balls exploded and a load of hot cum poured into her. I felt her swallow a couple of times in order to handle the volume of thick tangy goo that filled her hungry mouth. Then she emitted a soft ummmm as she exhaled and relaxed her head in my lap.
Again, she managed to gather herself and climb back to a sitting position. Still there was no sign of poppa coming our way. “I’m so glad you got have an orgasm too. Besides I love having that taste in my mouth.” As she said that I turned her face toward me and kissed her deeply. Her tongue went into my mouth and I could taste my own saltiness. “Now you’re gonna taste it, too.” She was half giggling as she said it. I was so spent and so blissed out I was absolutely unable to speak. I started to close my eyes as we embraced when the glow was shattered.
“Here he comes. Is your fly zipped? “She reached into her bag and pulled out a compact with a light and mirror and checked face for any signs of semen on her lips or face.
“OK here comes the final leg of the trip kids.” He said as he inserted the key and turned it.
No words were said during the half hour it took to get to Wethersfield—at least between her and me. She did ask her dad if they could take me right to my house and he said yes. AS we were negotiating the streets of town I felt her push up the sleeve of my sweatshirt and write something on my arm that felt moist and clammy.
When we got to my home I profusely thanked her father, grabbed my bag and bailed out of the car. Tears were in my eyes but I didn’t want either of them to see them. As they pulled away I waved but it was too dark to see if anyone returned the wave.
My parents were in bed so I dropped my bag and ran up the stairs to my room. Once I had turned on the light I rolled up my sleeve carefully.
That number stays with me today, decades hence. I called three or four times and we spoke warmly the night she finally called me back, but the vibe coming from her was that there would be no us in the future. I was however successful it getting some answers out of her.
She complained of having made that trip with her father over a dozen times over the course of her years at college in Maine. It had become a crashing bore. She had hoped that one time she could hook up with a guy to make the ride more interesting. It had been her idea to pick me up that day and despite her coyness she fully intended to have some fun with me. She apologized for being a bitch at first.
She confided that she was basically shy and introverted; having always been taller than most guys she rarely got asked out. So she poured herself into her work and became very studious. She admitted being impressed with my intellect and liking me as a person, which made the trip “all the more fun.” She said her expressions of pleasure were real and that it was an “incredibly hot experience.” I in turn shared some of my feelings with her, but never summoned up the courage to admit how inexperienced I was at the time. Nor did I want to admit how much the whole scene had gotten under my skin.
I did however express my disappointment at never having seen her body; her breasts her vagina, her ass. Tearing up I remember saying, “Katie, technically I have carnal knowledge of you, but the truth is I have absolutely no knowledge.” I know I probably sounded like I was pleading with her for one roll.
She laughed. She paused, and then in a serious voice said: “There are some things better left unknown and unseen.”
She invited me to visit her in the city once she started grad school, but I never did. I didn’t have the round trip train fare and hitchhiking around New York was something I had already done and wasn’t eager to do again. Beside I had three more years of college to complete. I know now there was something about the fact that she had that event all planned out bothered me. Once I got older and had learned about sex, fantasies, and the genders it all became clear and remains to this day one of the sweetest experiences I have ever had.
Katie, if you’re out there. Thanks for turning this boy into a man.