My Unusual First Time Ch. 01


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’ve got one big case of lacka 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 can’t 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’s 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 weren’t 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 ’em 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.

Myself and Edward Brenner were especially palsy when it came to these magazines, swapping them on a regular basis. Often we’d 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’d ride my bike there with a few magazines tucked inside my shirt and just down the front of my pants. Ed actually kept his stash at his brother’s house, in the guest bedroom upstairs.

It’s 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 couldn’t 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’m 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’ve 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’re 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 actually said hello to Edward and me, whereas her predecessors would have barely glanced in our general direction if we were on fire.

I don’t 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 didn’t see her much at first but soon it was evident she’d moved in with Harland, which was a surprise. Women didn’t usually move into a guy’s digs at that time without being married to Gaziantep Mutlu Son Escort him first, not even if the house was out past the auto yards. She’d 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 very 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’d 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’re 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 airbrusher falling asleep on the assembly line from boredom. Oh, yeah, and those wonderfully illustrated medical textbooks….I forgot to mention those. Next paragraph!

It didn’t 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” wouldn’t 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’d 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’d 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 wasn’t 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 didn’t 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 don’t 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’d 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 couldn’t read the expression on her face, but thought maybe it was concern crossed with amusement. She didn’t 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 wasn’t 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 awhile to subside, even under a circumstance such as this.

“Yeah” Ed nodded. “Sorry if we were loud.” Oh, good one, Ed.

“I just wondered if you two would like a little supper, was all. I was getting hungry and was going to reheat some chicken.” Now her eyes rested for a moment on the magazine nearest her, directly below her gaze as she stood by the bed, just a moment to verify what was expected, before returning to mine. Yes, they were dirty magazines.

“I’m sorry to interrupt. I knocked twice, you see” she added in an even voice.

“It’s okay” both of us chimed. Rose didn’t say anything for a few seconds, just kept looking at me. I could smell the liquor, but she didn’t seem drunk. In fact, she looked rather pretty and friendly, like usual.

“Uh, I’m gonna be getting home for dinner, but thanks anyway, Rose” piped-in Ed, practically jumping to his feet. He looked at me to see what I was planning, but I couldn’t budge. Then he looked at all the magazines, made for a moment like he would help to put them away, and then thought better of it and began to sidle his way around the bed.

“Okay, Eddie” observed Rose, looking full at him now but seeming not to be taking any great pains to avoid talking about what we all knew to be on the bed. “See you later this week.” Ed nodded, squeezed by her, and was gone. I remember wondering if we’d ever again get together to check out the latest skin mag. Maybe not.

I don’t know why I felt calm about this, after the initial adrenaline rush. Something in Rose’s manner as she surprisingly settled her behind onto the lower corner of the bed and idly leafed through a copy of Playboy, I suppose. I noticed how quiet the room, the whole house, was. I tried to think of something to say. Maybe I needn’t try?

“I hope you aren’t ashamed,” she said. This struck me strongly, because she was right: I wasn’t ashamed. But, wasn’t I supposed to be? “These were all over the house when I was a kid. Did I tell you we had eight people in the place, including my older brothers and a couple of unmarried uncles?”

“Um, no. We haven’t talked about your family” I replied politely, watching the curls of hair that draped over her shoulder move as she continued to leaf through the pages. At least it’s Playboy, I remember thinking, meaning I was glad it wasn’t one of the less-classy ones in our collection. “Where are you from?”

“Wilkes-Barre, Pennsylvania” she sighed. “Heard of it? Not far from Scranton. Like I said, lot of people in a little house. You learn to tolerate and understand a lot in a small house with a large family.” Her voice was almost a whisper, like she was remembering some incident or other from her past. I liked the sound of it.

“What’s the story with you and Ed here, wasting time on these?” It wasn’t an accusatory tone she used, but her question still cut at me. Her hand moved to a Gent issue and drew it to her side on the bed. The cover model was spilling over her hands as she cupped her breasts and hid the nipples from view.

“Old habit, I guess.” I surprised myself as the truth of what I just said came through. It really was a sort of bad habit, more than anything else. I suppose I’d thought of it like this: I’d quit looking at these cheap magazines as soon as I had a girlfriend and didn’t need to masturbate. Now, suddenly, that thinking just seemed foolish.

Rose turned her head to smile at me. “I guess we all have those. Bad habits, I mean.”

“Ed and I have sort of traded these for a long time, ever since…..” I trailed off, trying to think how far back it was. “Well, you know…”

“Yes” she agreed. “I know.” Had she just stolen a glance downward at my pants, or was I imagining things? If she had, could she tell anything? I wasn’t as hard now as before, but I figured there was something showing, still.

“All I mean, Danny” she said, using my name for the first time that day, “is that you should be out going after what you want, instead of looking. You’re not an ogre, you know. Aren’t there any girls who’ll go out with you?” She turned on the bed so she could face me more comfortably. It was weird, having this sudden heart-to-heart with an older woman who absently held a magazine in her hand that I’d used many times as an aid to masturbation. I could practically tell you the phony names of every nude model in that issue, I’d used it so much.

Now I blushed. Again, Rose hadn’t used any sarcastic tone of voice or even seemed impatient with me. That was the good part. The bad was that she had my number. Nothing worse in life, I’ve learned, for the ego, there’s nothing more unnerving than someone who sees through the bullshit and has your number. If I said anything false now, Rose would be able to tell.

“I haven’t really made the effort.” There, it was out. “Too scared I guess.” Part of me was suddenly aware that I was having a real conversation with this woman, for the first time since we’d met. Another part of me was also aware that she was getting more attractive as we talked. It was as though by trying to help me Rose was exuding some sort of warmth. I understood in an instinctive way why Harland had wanted her to move in, and I remember thinking that he’d better hurry up and marry her because this was a woman you could talk to.

Rose smiled and reached out to touch my face. I didn’t flinch. Her eyes were bemused and the grey-green combination seemed to burn at me with hidden mirth. Or so I imagined. Her hand felt cool against my face. “Trust me, we all look just like that” she grinned, waving at the magazines around us. “Or some variation of that. Nothing you should be scared of, Danny.”

She pulled back and put her hands in her lap, studying me. “If you’re anything like my Uncle Rob, you’re probably at yourself all day over these.” Again she gestured around us. Before I could protest what she’d said or even feel the embarrassment that was rushing forward because of it, she continued.

“He had a collection that rivaled anyone’s, at least anyone I knew. I’d go by his room and hear him in there, sometimes three times a day. I knew what he was doing. He was loud.” Rose giggled and I liked the sound so much I didn’t even feel that huge rush of embarrassment I’d expected. My face was still red, but getting cooler. Hell, here I was in a bedroom with a woman amusingly referring directly to a guy jerking off, and I hadn’t been struck dead or anything else. I was liking her more and more by the minute.

“It seemed a shame, actually” she continued, after her giggling was under control. “Several girls in the town asked me about him all the time, you know, with that very interested attitude. Rob could have had his pick. Eventually he figured things out and ended up with a great wife. We poke fun about his obsession at family holidays, but he’s okay about things now.”

She eyed me as if to see if any of this was getting through. Of course it was, but my defenses were up automatically, still. I really didn’t feel like admitting to anyone that I was wasting my time doing something that felt so good, even if I knew she was right. I instinctively stalled.

“But it’s not like I’m hurting anyone. And, well, I can’t help it. I just get the urge. I don’t know if you can understand.”

“Because I’m a woman?”

“No, no, I don’t mean anything like that. I mean because I can’t get up the nerve to try to get anywhere with a girl. I just think it would turn out bad.”

“I see.” Rose studied me again. Her expression was perplexed and seemed a tad frustrated. I saw that she was at a line and she didn’t know whether to cross it. Little could I know what she was considering. What happened next was never even in my fantasies, that’s how far out in left field it seemed.

“I’ll help you if you let me.” With that Rose calmly began gathering up the magazines and putting them in a neat pile on the dresser, letting me chew on her offer. Of course I couldn’t know what help meant, in her plan. I first thought she would try to set me up with someone, then I thought maybe she’d try to talk to me to build up my confidence, or something.

The idea of a set-up date terrified me more than one I might try to arrange for myself, so I immediately rejected that thought. Talking might help, but wasn’t Harland going to be home in a little while?

“How?” was my carefully thought-out reply. No sense assuming anything, my biology teacher always told the class.

“Well, first we’d work on the sex thing and then I’ll help you know what to do to get women to like you, I guess. It’s clear you need some building up, you know?”

All I heard was “the sex thing”, naturally. Did she mean…?

“That is, if you’ll keep quiet about it. I have a good thing with Harland, we may be in love, so if you’re not as mature as I think we can stop right now.”

Confused, I got up to walk around the room. I turned to look at her as though for the first time. What had I gotten into here? Suddenly I was threatening my best friend’s brother’s happiness, or something? And what was “work on the sex thing” about.

“You want a drink, come downstairs and I’ll get you a beer” was Rose’s way of dealing with my confusion. She walked out and stepped lightly down the stairs. She seemed happy. Before I got up the nerve to follow I took the time to put away the magazines in the closet, up in the ceiling pocket that was there, just like an eave. I wondered if I’d ever retrieve them from that hiding spot again.

She was in the living room pouring a Schlitz from the can into a tall glass for me by the time I got there. The TV was off. She set the glass on a coaster by the chair opposite hers and then turned to sit. She raised her Southern Comfort and ginger and we saluted each other.

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