Memoirs: Hard Fails

For readers who doubt that the stories in my "Memoirs" actually happened, I include these tales of youthful ineptitude. They're about sex, and I hope you find them interesting, but they're not likely to drive you into a masturbatory frenzy.

Sometimes I fucked up because nothing had prepared me for what was going on, and sometimes I fucked up because even though I could see that the situation was weird I was trying to be cool.

In each of these stories I lost the chance for a memorable--maybe life-changing--experience because I missed the message or read the room wrong. In almost every case I was too proud to say, "I don't understand. What's going on, here?"

Alan and Lana

This was one of those deals where I knew something was going on but I wasn't sure what. I tried to be cool in a strange situation, and I ended up wondering for the rest of my life what I might have missed.

Soon after I left college, I headed for the San Francisco Bay Area, which was Age-of-Aquarius headquarters. I cared about sex, drugs, and rock 'n' roll far more than I cared about what I was going to do for a living.

I moved into a house with a rotating cast of other long-haired guys about my age. There were quite a few girls coming and going. It was the height of the sexual revolution in a university town, and potential partners were everywhere.

I secretly admired Alan. He was in some ways the "leader" in the household, although nobody would have said so. For one thing, he was calm. He didn't talk just to air his own thoughts, as I have a tendency to do, and he never displayed any insecurities, or sorrow, or anger. Looking back, I'm sure he had plenty of those things, but he kept them to himself. To me he seemed to have achieved a sort of Zen approach to the world.

Alan's default expression was of sly amusement. He had a lean, handsome face that always featured a two- or three-day beard, which was an exception in those days. Most people either shaved or grew a beard. He wore heavy, round, wire-rim glasses.

Although most people would have pegged him as a "hippie," he was careful about his clothes and appearance. His long hair was always clean, and whacked off in a devil-may-care style that somehow never varied.

He didn't walk, he rambled along. He was lean, with wide shoulders and a flat belly, like a swimmer. And for some reason he didn't bother with underwear.

After considering the question more than once over the years, I know I'm not gay, but it's obvious to me now that I was physically attracted to Alan. I can still see his face in front of me. If I were forced for some reason to have sex with one of the men I've known, it would be Alan, as he was then.

His girlfriend was a striking young woman from a Mexican family that had been in the area since before California was a state. Lana had long black hair and was slightly hairy everywhere else, too, with silky "sideburns" and downy suntanned arms and legs. I doubt that she wore makeup of any kind--she and her girlfriends were no-nonsense feminists--but her face was naturally beautiful and strong, and so were her eyes. She looked right at you.

But she didn't say much. In fact, I can't remember a single word Lana ever said. Obviously she talked, but she didn't make casual conversation, at least not to me. As a compulsive talker, I found that a bit intimidating. The only thing I knew about her life outside our house was that she and her girlfriends were always getting naked, in the sun or out of it.

Which brings me to a day when the only people in the house were Alan and Lana--and me. As I walked past the closed door to Alan's bedroom, he called out, "Tommy, come in here a minute." I stuck my head in, and he said, "You want to do some coke?"

He knew it was very unlikely that I would say no.

As I walked in, I noticed first that he was wearing a pair of jeans and nothing else, and then noticed Lana, propped up on the bed pillows, wearing absolutely nothing at all, not even a smile. I had never seen her luxuriant black bush before. I said hello and told her she looked even better than usual, and sat down on the bed--the only space in the room.

I turned away from her to face Alan. I was trying to be all cool and worldly. And in fact this wasn't the first time I had walked into a drug-related situation to find someone's girlfriend naked. It didn't mean she was available.

As I made small talk with Alan, who was chopping up a couple of small lines of cocaine, I wondered why he was doing this. We were friends, but he owed me nothing, and although he had more money than I did, he wasn't that well off.

He presented me with a rolled-up twenty and a hand mirror. With a cocaine grin, he said, "Is there any other... surface... around here that you would like to snort it off of?

For some reason, a lot of cokeheads thought snorting coke off each other's private parts was sexy. I glanced at Lana, smiling to show that I got the joke.

She said nothing and her face gave me nothing. Damn. So I said nothing to her and snorted the lines from the mirror.

I was thinking that snorting coke off someone's body would not be an efficient way to deal with expensive powder anyway. She seemed unenthusiastic, and that meant it was unlikely that she would allow me to lick off the coke that remained on her skin, because that was what I would want to do.

I made some lame conversation with Alan, but like Lana he was giving me nothing to work with. I thanked him for the coke and left. I'm sure I said goodbye to Lana, too, but I don't remember her response. It was certainly not, "Oh Tom, stay and play with us."

To this day, when I think about that moment, I'm right back in that room again, feeling like an idiot. The whole thing was absurd, but I wasn't secure enough to say so.

I'm pretty sure that Alan--incidentally a psych major--was probably not just being generous. Cocaine was expensive. He might have been playing a game, betting Lana that I would pretend to be cool in that situation. Or he (and she) might have done it simply to see what I would do.

The worst possibility is, maybe they themselves were too shy to come right out with it.

In all the fantasies I constructed later, I said, "Thanks for the coke, Alan. I appreciate it. Now what can I do for you?"

Or I could have said, "Alan, Lana... You have to admit this is a strange scene even for us. Would you like me to stay and play with you guys?"

But I didn't. In my defense, it was an age of casual nudity, and it wasn't the first time Alan had offered me a free snort. It's possible that I was reading the room wrong, and Lana might have said, "God damn it, Alan! I told you not to pull this shit. I'm not doing a three-way!"

But who knows? The girl was gorgeous, and absolutely naked. Was I a fool?

Country Hippies

The Alan and Lana three-way that never happened reminds me of a night in Oregon, where I was visiting some friends who took the hippie "back to the land" ethic seriously. They lived on a farm, although there was little farming going on. This was a true commune, in the sense that everyone living there contributed to the general welfare. At its core was a group marriage, where the man of the house--we'll call him Archie--had two "wives." We'll call them Betty and Veronica. Only Veronica was legally married to Archie, but they all truly operated as a threesome. Even in bed, although the two women usually took turns sleeping with Archie.

People like me came and went, and "free love" prevailed: You could sleep with anyone, as long as they agreed.

I had been there only a day when Betty made it clear that she would be happy to play with me, and so we did. It was memorable. She was about five years older than I was. I thought I knew it all, but she showed me some things. (Both Betty and Veronica were registered nurses.)

The next day, another couple showed up--old friends--and that night the newcomers slept with Archie. I once again was in bed with Betty when Veronica came in. She knelt on my side of the bed and took my hands in hers, and started gently talking to me. I couldn't figure out what she was saying. It sounded sort of poetic, in a stoner sort of way. When she stopped talking, I still didn't know what to say, but god forbid I should just admit I was confused, so I just squeezed her hand.

The silence became long. Finally, Veronica said some sort of "good night" and left.

Betty turned to me and said, "Have you ever been with two women at once?"

I was aghast. "Is that what she was talking about?" I said.

"Yes," Betty said.

This was terrible! Not only had I probably hurt Veronica's feelings, but I had blown a chance to make love to two willing women at the same time.

"I didn't know that's what she was saying," I said. "I'd better go after her."

"I think you should just let it go for tonight," Betty said. "You can arrange to be with her some other time." Eventually, I did end up making love with Veronica. It was nice, but it was plain vanilla.

Through all the decades, I've agonized over the cheerful, eager threesome with two loving nurses that I missed. It was my only shot at it.

(You young men should know that a menage a trois is something you have to bring up with a girl very carefully, even if you notice that your sweetie is overly drawn to her clinging BFF, or even to a cocktail waitress. No matter what she really thinks, the response is almost certain to be something like, "So I'm not enough for you?")

Carolyn and Maggie

And speaking of menages a trois, I just remembered another shot at a quickie three-way, and for all I knew a longer affair, but I didn't fail, exactly. It was a slightly older and wiser me who killed it before we could even explore the possibilities.

I was in a five-year relationship with a woman named Samantha, who appears elsewhere in these memoirs ("The Dark Portal"). As I've noted before, we were living in Berkeley. At that time (and probably still), it was one of the world capitals of getting naked with people you're not actually fucking.

Samantha's best friend of many years was a woman named Maggie. They were not much alike, physically or mentally, but they were tight. I sometimes wonder if Maggie wasn't secretly attracted to Samantha the same way I was. We did live as a household of three, which is exactly what menage a trois means, but what we were was a couple and a friend. The friendship between the two women was strong enough that I could sunbathe or go to the sauna with Maggie even when Samantha couldn't make it.

Maggie and I were very much aware of our mutual attraction, but except for some rather personal massages we never acted on it. She was a true friend to Samantha, and for my part I was trying to make my first real adult relationship work out.

Enter another of Maggie's friends. Carolyn was a working sociologist, with a doctorate and a husband and an overt horny streak. Standing on the toilet tank in their bathroom was a framed photograph of her groomed pubic triangle.

On one occasion when Carolyn was visiting our house, someone suggested a trip to one of our local saunas. Samantha had a sick headache and that was the last thing she wanted to do, but she insisted that I go with "the girls" if I wanted to. I'll give her points: she knew very well that I wanted to. If she had any doubts about my ability to resist Carolyn, I imagine she figured Maggie's presence would prevent any hankie-pankie.

And that's what happened. We were all giving each other two-on-one massages and I was very happy. And I think they were very happy, too, and drawn to each other a bit. They were asking each other about whether they found women's bodies attractive, and about their gay friends. Carolyn's pussy turned out to look just like the photograph. When it was my turn to lie on my back and be manipulated on the bench, I realized right in the middle of it that my cock was so hard it actually hurt a little. A little embarrassing.

Without opening my eyes I apologized for the erection, saying that the little bastard had a mind of his own. (Not true, and I knew it and they knew it.)

"Oh, look," Carolyn said. "He does have an erection." After a beat she said, "What shall we do with it?"

So many possible answers. But Maggie had said nothing, and I was thinking of her long loyalty to Samantha. She might have been up for some mild sex-play, but we had never even broached the subject. And now here was another friend, another possible big-mouth, examining my willy. So many possible ways to go wrong.

"You don't have to do anything with it," I said. "I just wanted to say it's no big deal."

And that is literally the last thing I remember saying or doing that day. I had killed the deal. From the point of view of a possible three-way, it was a fail, but from the point of view of me being an adult, it was a fairly good moment.

I was interested to learn later that Maggie never said anything at all about that day to Samantha, who had Carolyn figured out pretty well and harbored suspicion for a long time that we had made some whoopie at the sauna. It was me who told Samantha I had been tempted but stayed true.

Fail?

Arlene

I have written elsewhere in these Memoires about Arlene ("Grand Prix"). We were camp counselors in neighboring camps. In spite of her absolute refusal to have standard intercourse, she was a wonderful sex partner, because she was a willing and talented fellatrix. But I also have to include her here among my fails, because I failed to hear her when she offered me a couple of other roads to travel.

Arlene had promised someone that she would never allow a penis inside her treasure cave until it was officially allowed under the laws of man and god.

She might have made the promise to a boyfriend, although when I look back at her enthusiastic embrace of cunnilingus, fellatio, and other things (see below for epic fail) I doubt that she was saving herself for some other lover.

I lean more to the idea that she had promised her parents or grandfather (it was a wealthy family and she was a treasure in herself) not to let some random adventurer--like me--into the cave. That might explain why she adhered so firmly to the letter of the agreement while enthusiastically violating the spirit of it as often as she could.

Anyway, I remembered (years later) that when we had first discussed her promise not to give up her maidenhead she had actually mentioned the possibility of me taking her anal virginity instead.

Looking back, I can't understand why I didn't seize on that. It's possible that our limited time together in real beds, coupled with my botched earlier attempts at anal intercourse with other girls (if you haven't tried it, it's actually a difficult procedure), pushed the idea to a back burner. After all, she was taking me in her mouth on a regular basis and both of us were happy. I can see why I never followed up, but I do regret it.

Fail.

The other kinky activity that Arlene offered me one night, I didn't want to do.

Every girl I had ever been with had reinforced the idea that "gentle" was the only way to go, which was fine with me because I considered sex as good as anything could get, and I didn't want to be an asshole.

On our last night together for the summer and probably forever, she suggested that we do something special. She said, and this is fairly accurate, "You could bite my breasts, and slap them around."

And I replied automatically, "No, I don't want to hurt you."

What a fucking idiot. Why didn't I ask her if she would like that? Later in life I began to understand that some people enjoy a measure of pain, just as some people actually enjoy being degraded or misused. Here was a girl who was eagerly sucking off a near-stranger (me), and now was offering her body for abuse. It would have been at the very least an interesting night.

If I ever get my hands on a time machine, my first stop will be back at that camp, to have a little talk with that young man.

Again, Fail.

Andrea -- Perfect Storm of Fail

Speaking of time machines, the ability to talk with my younger self would have come in even more handy in saving my relationship with one of the most amazing, sexually free women I ever stumbled across.

I was at a house party on a spring night during my third year of college. I was wearing the coolest clothes I could find, and my hair--longer all the time--was clean and shiny. I looked as good as I was ever going to.

The collision of keg culture with marijuana was well under way, and things were loud. In the kitchen (as usual) we probably had more than a dozen people all talking at once and laughing at everything. My eye was drawn to a tall trim woman with a beautiful face and a honey-colored pony-tail. She was wearing a white T-shirt.

She was talking to a couple of other women when she suddenly grabbed the bottom of her shirt and pulled it down tight while she thrust her chest forward, intentionally showing off her breasts. She was clearly not wearing a bra. She was making some point to her friends, and they laughed. I quickly looked away. It was very important that I not be seen as a creep.

The women on campus were young and bright. They knew where babies came from and they didn't want one. If you were under 21 in those days, to get the Pill you still had to have your parents' permission, which meant girls were not likely to wave their tits around in front of people they didn't know.

But this girl had, and the memory of that moment is still in front of me as clearly as it was then.

I stayed in that kitchen until I finally found myself next to her, and we began to talk. Her name was Andrea. She said she had seen me before, at my student job on campus, and I told her truthfully that I had not seen her, because if I had I would have remembered. She was flattered, she said, but it was already clear that she knew she was special.

We had a couple of friends in common, and we also went through the usual argle-bargle about what courses we were taking and where we were from. I don't remember if we arranged our first date that night--the "date" being her coming over to my place--but I do remember one thing she said. We were talking very openly about whether the two of us would enjoy getting together--which was unusual in itself--when Andrea looked up at me and said, "I like smells."

I had no response to that. I spent a great deal of time trying not to smell, and a ripe crotch was not what I was looking for. What I managed to say was, "Oh you do?" And she and her friend laughed.

She gave me another chance to figure her out when we finally had our "date," and the conversation somehow went to toe-sucking. Instead of just going with the flow for the sake of scholarship, I somehow ended up standing with her in the bathtub while I washed her feet. This in itself was a total failure to grasp the concept, although I remember that my main concerns about smells or ugly feet had to do with my body, not hers.

I did end up sucking her toes, along with the rest of her, but our lovemaking was nothing really out of the ordinary.

We then had a couple of encounters that didn't go so well. The only time I went over to her apartment I found her suffering from a terrible cold. I tried to play nurse, but it was clear she wanted me to go away.

I also made the bad move of inviting her to visit the pizza joint where I worked as an assistant cook a couple of nights a week. The plan was to smuggle her a free meal, but she showed up with her bestie, and the two of them, even in their jeans and T-shirts, were the most attractive women the staff had seen for a long time. They even attracted my manager's attention. I ended up paying for the food.