My First Time Was with an Older Women

My First Time Was with an Older Women


It was the early 1960's in small-town Connecticut. I had just turned 18 and would graduate high school in a few months. Having the grades to go to Yale if I wanted to, and the parents that could finance it, what was missing was self-confidence.

Part of it was my non- success with girls. The other was that I was 6 foot two and 165 pounds. Add to that skinny kid a pair of eyeglasses and the occasional zit, and you have got one big case of lack of ego.

Of course, I blamed my absence of experience with women on what I perceived to be my awkward, Poindexter looks (Poindexter was a science nerd, before the words nerd or geek were even around). Today I see young ladies hanging all over fellows that look now pretty much like I did then and acting like they cannot get enough of the guys, so I figure I was just born ahead of the times. Or cursed. Take your pick.

Anyway, President Kennedy had only been laid to rest about 6 months when I turned 18, so the country wasn't in any rollicking good mood. The Beatles had just started to raise everyone's standards of listening on this side of the Atlantic, so the forthcoming Youth Revolution I remember so well wasn't there to thrust me (yet) into a world of long hair on men, Free Love, and the any-excuse-to-get-high life that would soon rule many of my generation.

So, I made do with masturbating. It is not like I had a choice; my dick would get hard if I just got a glimpse down a well-filled blouse on the cafeteria line at school, for crying out loud, in those days.

Vital to this world of unfortunate self-help necessity was the finagling, by whatever means necessary, of men's magazines. Playboy (Penthouse and pubic hair were not out yet), Gent, Adam, Nugget, and other magazines, now long forgotten, passed around between us boys (especially my fellow losers) like prized possessions. I shoplifted them whenever I could get away with it, not that many stores had them right out on the racks next to Good Housekeeping. Being skinny was great for shoplifting, especially in the winter when I could wear a large coat. Not that I recommend any such thing.

Edward Brenner and I were especially palsy when it came to these magazines, swapping them on a regular basis. Often, we would get together to peruse them at Ed's older brother's house, a roomy old place on the opposite side of town, past all the auto repair shops. I would ride my bike there with a few magazines tucked inside my shirt and just down the front of my pants. Ed kept his stash at his brother's house, in the guest bedroom upstairs.

It is not like Ed, and I pleasured ourselves in front of each other as we looked at these mostly black and white shots of topless women and bare behinds. We were friends anyway, so it seemed like a natural extension to admit we could not get enough of looking at naked women, even the often-mediocre beauties like those featured in such disposable rags. We started out in our early teens looking at worn old copies out in the woods, borrowed from the bureaus of our respective dads, so this was not some new preoccupation for either of us.

I am sure we were both aware of what we used such pictures for when no one else was around, we just never spoke of it to each other, you see.

The reason for this whole reminiscence I have been putting you through is that Ed's brother's house was where I would have my first female sexual encounter, albeit a weird one.

Harland was Ed's brother, and he was about six foot and built like the construction foreman he was. A mean-looking face, I remember, but nice as you could get. I never saw him raise his hand or voice to anybody, and he seemed always happy to see the two of us (me and Ed) despite being almost eight years older than us. I had my first beers from his fridge and learned to hate my first cigarette from his offered pack of Chesterfields.

Thank you, Harland.

Since we were there a couple times a week, we took notice whenever Harland had a girlfriend. Sometimes Ed and I would speculate on whether Harland was "getting any" from any particular lady friend or other, or euphemisms to that effect. We figured he was. It was easier to identify with him that way. Life is more exciting imagining yourself a winner, even if you think you, are a loser.

His latest was Rosemary, Rose for short, and she was remarkable not only for being prettier than the others but also because she said hello to Edward and me, whereas her predecessors would have barely glanced in our general direction if we were on fire.

I do not know why, but she made me blush when she simply said hello. Even a needful geek like me could generally hold his own by 18 in a conversation with a woman, or fake it, but I just got hot in the face with her. One time she smiled in amusement when she saw that flush creep up my neck. I cursed myself for days.

We did not see her much at first but soon it was evident she moved in with Harland, which was a surprise. Women did not usually move into a guy's digs at that time without being married to him first, not even if the house was out past the auto yards.

She be in the living room watching Art Linkletter when the two of us would ride up on our bikes from school and nod hello on our way up to the guest bedroom, to check out this month's Swank, or whatever.

She was usually in Capri-type slacks and one of Harland's shirts, like Laura Petrie from The Dick Van Dyke Show. Rose was about thirty, or so seemed it to me, with shoulder-length chestnut hair done casually in a sort of flip. She had a pretty, white, and pink complexion with more than a hint of Irish ancestry. Her eyebrows were incredibly soft looking, I remember, over those grey-green eyes.

Since in those days at least half of my brain concentrated on undressing women mentally and trying to guess what they would look like, I speculated that she had medium breasts with large brown nipples (I figured that for all brunettes, and was often wrong), a reasonably trim waist, and medium hips with probably a roundish ass.

If you are wondering why I didn't daydream about her vagina, the answer's simple: men's mags, the type we could get, weren't showing any. Any way possible NOT to show the pubic area was used in the photographers' set-ups. Now it seems silly, but back then such a concept (to actually show the area of a woman's body that men's libidos are most interested in, to oblige the very target audience the magazine is aimed at) would have seemed "too dirty."

Regularly obtainable pornography was a myth where I lived, so that was out. Even if you managed to flush out an old nudist magazine (and who would want to, with their average-looking people and their airbrushed private parts?) you never saw anything but maybe the hint of an opening between a woman's legs, probably just by accident due to an airbrushed falling asleep on the assembly line from boredom. Oh, yeah, and those wonderfully illustrated medical textbooks I forgot to mention those. Next paragraph!

It did not occur to me at first that Rose might wonder what two young guys were doing using a third guy's house after school or on a Saturday, squirreled away no matter the weather. Any excuse that we were "studying" would not cut it for too long. She probably wondered if we were homosexual.

With Harland often away supervising a steady succession of construction sites Connecticut was still booming in our area those days because of its proximity to New York City, we observed that Rose would sometimes have a bottle of Southern Comfort on the lamp stand next to her chair, keeping her company as she watched TV.

Sometimes we would sit with her and talk (in my case, just nodding a lot) and have a beer while she mixed the sweet-smelling liquor with ginger ale in an iced glass.

She was an interesting talker, giving us tips on movies we should get out and see or TV shows she liked or books she recently read, but mostly inviting Ed and I to talk about school and what we planned after graduation. We did our best for a while and then went upstairs, as usual. Like I say, this was a couple times a week, so she must have wondered.

One Saturday afternoon I remember Ed and I were loudly admiring a Natalie Wood look-alike model well, he thought she looked like Natalie, but I was not so sure. This model was spread all over a modern apartment set, languidly eyeing the camera with a sultry expression as she almost revealed her privates from behind on all-fours on the couch, or almost showed what was above her inner thigh in the kitchen, stretching to reach something in the cabinet, too bad about that strategically placed bowl on the glass counter.

I recall we were debating whether that just-got-laid look on the model's face meant she had slept with the photographer. I liked to have such fantasies, so it was probably me taking the position that the model and the (no-doubt, studly) photog had done exactly that, and graphically describing the positions the two had used. We did not hear the knock at the door, or that Rose had opened it.

One thing you always dreaded in adolescence was an adult catching you doing something forbidden. I do not mean like grabbing a smoke out by the back door of the gym. Something you would be REALLY ashamed of. Like, for instance, lounging on a bed with about a dozen or so men's magazines open. Or maybe, loudly using a phrase like "screwing like a mink" when describing the action in such a magazine to your friend. I figured we were dead.

Nobody said anything for a while. Ed looked sick. After all, this was his brother's girl. Ed stood more of a chance of being disowned from his family than did I for this sin. Me, I would probably just be grounded for six or seven years. Yes, a high school senior could still be grounded by his or her parents, back then. True fact.

Rose was looking steadily at me as she crossed the room and avoiding looking down, for now, at the variously displayed women. I could not read the expression on her face but thought maybe it was concern crossed with amusement. She did not look at Ed.

"Geez, we didn't hear you knock" came from my lips, lamely. Like that was an excuse.

Funny, for the first time in her presence my face was not hot, and my dick was still
hard. Like I said, it would get that way back then from the merest suggestion of sex, so, having been quite aroused for at least an hour before Rose came in it might take a while, to subside, even under a circumstance such as this.


to be continued