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The First Time

Does everyone remember their first time? I do, but not the way most people would imagine.
Does everyone remember their first time? I wonder about that, and I wonder just how many people actually remember their first time with any accuracy and without enhancement for nostalgia or for ego or pride.

I started early with my first girlfriend in high school, but nothing more than kissing, feeling each other up (or down, as the case may be) and some oral experimentation. I always went out with girls my own age, so I never had the benefit of the older, more experienced woman showing me the way. No Mrs. Robinson in my world.

My first time? If we’re talking about the Bill Clinton definition of sex, that came when I was sixteen. We were both sixteen, in fact. An afternoon in my bedroom after school, since my parents wouldn’t be home until much later. I remember we did enough to make sure the pieces of the puzzle fit together, but we were young enough and too ashamed to buy protection, so it was a quick in and out for just a minute or so, and then out for good, because we knew enough not to want any unexpected surprises nine months later.

Then another girlfriend. I was nineteen, and she was eighteen, and it was the same story as when I was sixteen. Both too afraid to go into the pharmacy and buy condoms, so once more, in and out and then we settled on our hands and mouths for further enjoyment.

Sure, I had dipped my pen in a few inkwells over the years, and I had my share of mutual masturbation, oral sex and the like, but the first time I had intercourse and went all the way to a climax? I remember it. I was 24 years old before I ever went all the way. Not for lack of opportunity, but out of fear and embarrassment. Maybe lack of confidence too.

24 years old and she was 35 years old. Yes, my very own Mrs. Robinson. We started as classmates in university (she was returning to school after having been married, two children and then divorced), and we were casual friends but no more. Then we met each other one day by chance in a grocery store. It was a very cold day in January, and we talked for a while as we walked through the store together. There was the proverbial unspoken dialogue going on between us, as for some reason there was an attraction that day which had never surfaced in two prior years of acquaintance. But for some reason, on that cold day, something clicked and there was more subtext going on than actual talking.

A pencil in a purse. A receipt from an ATM. A phone number written on the back of the receipt, with the mutual promise to get together one day. No mention of why. But that is where the subtext comes in.

That was a weekday. I called her on the Friday of that week, and she said I should come by on Saturday night around 8:00 p.m. (her kids were at their dad’s place for the weekend), and we could watch a movie on television. Bull Durham. I remember the movie’s name, but I confess I don’t remember much about the movie.

I came over, we watched, she made popcorn, we ate some of it, we talked and then somewhere during the movie, we ended up sitting closer together. Quite close. Me sitting on the floor with my back against the sofa, she sitting in front of me, leaning her back into my chest. My arms around her waist. Quite close.

And somewhere during the movie, we ended up kissing each other. And my hands ended up on her breasts, feeling the softness through a heavy wool sweater. Her apartment was on the cold side, so the sweater did not seem out of place at all.

We watched the movie until the end, still staying quite close to each other, and at the end she turned off the television and asked if I wanted to spend the night. Just like that. I had nothing with me, no change of clothes, no toothbrush, no pajamas – this wasn’t the kind of sleepover I had ever had before. I said yes, and we retired to her bedroom.

As naturally and as casually as can be imagined, we both undressed. We had never been naked with each other before, but there was no shyness or apprehension. She was definitely older than me, and her body showed the extra years as well as the effects of having two children. Her belly was round, and sagged a bit with some stretch marks. Her breasts, although full, also sagged a bit, and her prominent and long nipples pointed more downward than up. Her ass also was soft and full and not as firm as that of a woman a decade younger with no children to her credit, but it was still very sexy and alluring.

If truth be told, I am not sure about what I saw when we were naked together for that first time. But I do remember one thing.

I was in awe at just how beautiful she was.

We climbed into bed with each other, and she motioned for me to lay down on the bed on my back. She then leaned over me and began to take my hard cock into her mouth. The word hard does not even begin to describe my cock at that time. I was aroused, excited, nervous, scared, stunned – so many feelings reeling around inside of me at once, but I was just so damn excited by the situation that my cock stood at attention from start to finish that night. And that is how it started out, fully erect and being taken into her mouth.

I don’t remember anything about that blowjob. Was it good, satisfying, the best I ever had? My brain wasn’t registering any of that. I remember she did it, and I remember coming in her mouth and her swallowing it all. Then I remember us switching positions, and I lay down on my stomach with my head between her thighs, and I remember going down on her. This was the mid-1980’s so a shaved pussy was a rarity, and she was sporting a full bush of blonde hair. I remember nothing about eating her that night, except that she responded favorably and reached a climax.

Then came my first time. I assumed she was on the pill, because an older, more experienced woman, who had been pregnant twice before, obviously knew about contraception, and she didn’t bring out any condoms or ask me if I had any. I assumed, but of course, rule number one is never assume anything.

But I assumed that night, and as she lay down beneath me, still panting from her climax, I slid my way up her body and entered her. I don’t remember if I did it slowly or quickly, I just remember entering her and finding her pussy completely wet inside, and it stayed wet all the while we fucked in the missionary position. Then she pushed me off of her, and rolled me onto my back, and she mounted me and rode me, facing me. Then after a while she got off of me and knelt on the bed, and I entered her doggy style.

I came three times inside of her, and no lie and no exaggeration, my cock did not go down for a moment. It scared me a bit, and I was afraid something was wrong, and I pictured going to the hospital complaining of an erection that wouldn’t subside.

She came several times too. I don’t remember when, from what position, whether it was at the same time as me. None of that made its way into my memory.

All I knew was that we had fucked and somehow it became one-thirty in the morning and we were still awake and fucking and sucking and licking and stroking. And I was still hard.

At some point we both fell asleep with the lights on, lying naked with each other on top of her sheets, uncovered. And then at some point in the morning, we awoke (yes, I was still hard), and she asked me if I wanted to take a bath (no shower was suggested – just a bath). I said I would, and she drew a bath for me, and handed me a towel. Twenty-four hours before, I was in the comfort of my own apartment, alone, anticipating what kind of evening I would have later, and now, twenty-four hours later, I had made love to this woman several times and was sitting naked in a tub full of bath water as she sat down on her toilet and pissed in front of me, and then got up and brushed her teeth, still naked, only a few feet away from me.

I watched her ass from behind, and marveled at how two people who had just connected for the first time could be so casual and natural with each other. She turned around as I washed myself in the bath, watching me, and I felt no shyness in front of her. I saw her prominent pussy lips as she stood in front of me, and my thoughts were turned to how my cock had been between those lips and in her pussy just a few hours before, and yet I was unsure how she would react if I were to simply reach out now and touch her.

I stood up in the tub and grabbed the towel and began to dry myself off as she watched me. After I stepped out of the tub, she stepped into it, into the same water I had just been sitting in, and she took her bath. It was my turn to stand and watch her as she soaped herself, washing her breasts, and I was mesmerized by the way they simply squished under her touch, almost like Jello, and how her nipples became more erect as she washed herself. I stood speechless as she took a washcloth and washed between the folds of her labia, and then as she stood up and washed her sensuous ass with the same cloth, and then sat down again.

I watched as she stood up and grabbed a towel and began to dry herself off, and then as she stepped out onto the bath mat beside the tub, next to me, and despite our naked bodies being so close, she never touched me and did not invite me to touch her. There was nothing overtly sexual about our nudity together, and this was an education for me, as the whole night had been.

We walked together back to her bedroom and then proceeded to get dressed, and she suggested we go out for breakfast down the street to a small café she knew.

That’s exactly what we did, walking side by side in the cold, but not holding hands or showing any outward signs to the rest of the world, giving no indication that just hours before, we had been lovers.

Breakfast ended, and I couldn’t tell you now what it was that I ate. I simply remember walking her back to her apartment afterwards, and we simply kissed briefly and said our goodbyes, each knowing we had things to do for the rest of the day.

Casual. Natural.

My first time. I remember it, and yet so many of the details remain vague, or perhaps they didn’t really matter. We got together several times more over the next few months until our semester ended, and we took one road trip together spending three nights in a hotel before she took a flight overseas to visit some family.

We saw each other one more time after that, and then I returned to my home town to start my career, and she carried on with her life, with her two children. We kept in touch for the first year, but then life as always gets in the way of good intentions, and by that time I had dated another woman for several months, and then after that I met my wife.

It has been over twenty years since I last spoke to her, and almost a quarter century since my first time. Do I remember it? Yes, I do. Was it important? Only in the sense of the importance between the two of us at the time, as with any relationship, and only in the sense of me learning some very important lessons. Not about sex, but about how we see ourselves and each other.

Some people say that sex changes things. That once you go down that road with anyone, whether a friend or a stranger, you can’t ever go back. I don’t know if I agree.

The only thing that changed for me after my first time? Sex was no longer this mystery, and I learned that you and your partner still have to wake up, still have to bathe and get dressed, go about your daily business and be individuals in a bigger world. Nobody looks at you the morning after, as you walk down the street, and can tell what you’ve been up to inside those four walls of the bedroom.

Sex isn’t so much about your body as it is about what is in your head. A bath or shower can wash away the traces of intimacy, at least for the outside world, but for yourself, sex is all about how you see yourself and that other person.

My first time? When I picture her now, I don’t see her naked in front of me, but I see her in her heavy wool sweater or walking down the aisles of a grocery store. I don’t see her breasts swaying as I thrust into her from behind, but I see her walking down the street going to breakfast.

And those memories are the most enduring and remind me of why I found her so sexy and attractive in the first place. Even if I can’t remember all the details of my first time, I remember what is important.

Maybe that’s the best lesson I learned from my first time and the one which I remember each time I am with someone.

Maybe that’s why each time for me is still like the first time, and I never lose my sense of awe at just how beautiful every woman can be.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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