Jamie & Bush

There was a notorious gay bar in my college town.

I liked to go there once in a while because it was such a wild and uninhibited place. I had no personal interest in gay sex, but enjoyed the outrageous scene. You could smoke a joint while dancing, do lines at your table, and quite a few people would be walking around and dancing half naked. I have never seen more dirty-dancing than in that place, as some people were practically having actual sex on the huge dance floor.

While most of the patrons were gay or lesbian, probably 20% or 25% were straight like me, but just liked a place you could cut completely loose. That was fine for straights as long as they had a date. Going in there alone was a formula for getting constantly hit on, to the degree that you could not really have a good time.

So if you were straight, you basically had to go with a date.

Well, there were a couple of friends of mine, Jamie and Bush, that I'd met in a class. Jamie was a girl, and Bush was a guy. They were ultra-intellectual and liked to party, too, but did not have a "crowd" they hung with.

I really liked both of them and enjoyed their company, but could not figure out the nature of their relationship. They seemed to be boyfriend-girlfriend in every way except a very significant aspect--the sexual part. Not once did I ever see them kiss or make eyes at one another or do anything remotely sexual. They went on dates and out to the movies and concerts, and he was always a perfect Southern gentleman opening doors for her and giving presents and driving and paying for everything, but there was not one sign of anything physical.

Yet, they were not prudes. They laughed at my sexual jokes and would comment quite openly about other's sexual behavior, including my own. But there was not one iota of sexuality regarding their own lives. They made no secret that they went home together after dates, but what that actually meant, I had no idea.

I badly wanted to just come out and ask them, "So, do y'all fuck?" but never did, as it really wasn't any of my business. I figured they were just very private about that sort of thing when it came to their relationship and would make it my business if they chose too, and let it go at that.

Well, anyway, Bush, who was from a very wealthy family that resided in the college town, had me over at his parent's mansion to join him and Jamie for dinner one evening. He said he would soon be rendezvousing with his parents, who were already in the Alps, for a ski vacation, and asked if I would mind entertaining Jamie while he was out of the country.

I, of course, agreed without hesitation, and after the live-in butler served chocolate truffles for desert, we retired to the paneled library to smoke cigars, real Cubans, no less. Bush gave me a couple hundred dollars cash with which to entertain Jamie before I left.

The weekend after he left, Jamie came over to my apartment and we drank a few beers and got high for a while, enjoying each other's company as usual. If ever a man and woman were just friends, it was Jamie and I. I had absolutely no sexual interest in her whatsoever.

She was not BAD looking; in fact, she was slender and kind of attractive, but you really had to look hard for it. Even so, there was simply nothing at all sexy about her looks or behavior. She always wore stovepipe-leg jeans, a button-down collar shirt, docksider shoes, no make-up or nail polish, and big, thick glasses.

I mentioned the gay bar and asked her if she'd like to go, and she simply said, "Sure, why not." Not only had it been a long time since I had gone there with my previous girlfriend, but going with Jamie would surely tease out any latent sexuality she might have at such an over-the-top place. So we walked there together.

We got there quite late, and things were really cooking. Gay guys prancing around in pants with the seat cut out, lesbians making out in the next booth, a few straight frat-boy types groping their perfect sorority-girl dates on the dance floor. Everyone was totally wasted, and so we set about catching up by ordering expensive, exotic drinks with Bush's cash and unabashedly smoking a big joint at our booth.

The place had a killer sound system and a well-known local DJ playing terrific tunes, so, sufficiently sauced and smoked, we got up and danced our booties off with the rest of the out-of-control crowd.

We were having a great time, and before long, the flamers in the adjacent booth broke out the Bolivian marching powder, which they generously shared with us. We snorted, we smoked, we drank, we danced, we talked. Repeat. Repeat. We were both having a very large time.

With all the dancing we were doing, we were necessarily touching one another a lot, and I felt through the back of that blue oxford cloth shirt that Jamie was not wearing a bra. That seemed out of character, and, for the first time, I felt a slight twinge of sexual attraction for her.

She was a surprisingly good dancer, and, loose from the medley of psychoactives, at the end of one song I dipped her, just as a silly thing to do. Suddenly, her lips looked so kissable, so I just laid a big one on her. She not only kissed back, but her tongue plunged into my mouth like an expert, and the next thing I know, we are making out and groping each other all over the dance floor throughout the next song!

Back at our booth, we continued. I unbuttoned her shirt to the waist as she eagerly helped and jutted out her extra-firm B-cup breasts with tiny, dark nipples that I twiddled to points. My other hand pawed at her crotch through her jeans, and it was remarkable how poochy it felt down there. She must have really big pussy lips, a fetish of mine, I thought. She wasted no time in returning the favor, massaging my cock with vigor through my jeans.

Unbelievable! This was Jamie, of all people. Jamie! JAMIE!

What we were doing was not at all out of the norm for this club. This kind of stuff was going on all over the place, mostly guy-guy and girl-girl stuff, but we weren't the only heterosexuals in there on the brink of full-blown sex. So no one was staring, and there was no reason at all to be the least bit inhibited.

I had to piss like a muthah, and we were ready to leave anyway, so I stopped in the men's room on the way out. Standing next to me at the urinal was a transvestite, who said, "I just love your date; he's to die for! Prettiest tranny I've ever seen!"

He? The dude thought Jamie was a guy? A transsexual guy? Woe, could Jamie be a guy, after all? Oh, don't tell me. No!

I met her in the hall outside as the tune from the Rocky Horror Picture Show started up, "His name was Leo G. Carroll, Had him over a barrel..." How ironic.

She did have a certain, though very faint, masculine aspect to her face, and she had such firm boobs (implants?), and there was that thickness in her crotch (penis?). And what about that whole business of her and Bush's never saying or doing anything sexual in front of others? He was, come to think of it, not exactly the most macho guy, even slightly effeminate at times. What was his sexual orientation, or gender, for that matter? Oh my God, this was all too weird!

I was having one of those everything-you-know-is-wrong moments, a chilling feeling like when I learned at age 15 that my father had been married before. I could practically feel my brain neurons franticly attempting to rewire in order to deal with this new paradigm.

Yet those connections would not plug in until I knew for sure if Jamie was a tranny. Realizing the only certain way to know was to get her naked, on the one hand, that thought made me a nervous wreck, but on the other hand, I just HAD to find out. So, for the 20-minute walk back to my place, I continued to anxiously grope and kiss her/him/it, carrying on like teenagers the whole way.

When we finally got there, she immediately ran into the bathroom while I stripped in my bedroom and waited for her. What on Earth was I about to discover? What if Jamie was a chick with a dick? Even if she was all-girl, she was Bush's girlfriend, and I didn't fuck my friend's girlfriends. What the hell had I gotten myself into this time?

Then she appeared nude in the semi-darkness of my bedroom doorway. Wow, she was beautiful and so sexy. How could I have never seen this aspect of her until that evening? My eyes instinctively went to her crotch, and there was the thickest, darkest bush of pubic hair. If there were a penis there, I couldn't see it—yet.

I took her by the hand, removed her glasses, led her to my bed, lay her down, and began kissing her as my right hand went directly between her legs. Parting the hair, I felt something dangling down there! Oh my God!!!

It was her pussy lips. Whew!!! They were the biggest lips I've ever seen, in person or in pictures, almost three inches long, and extremely thick and puffy. Glorious, huge pussy lips! Jamie was a girl!!! The Hallelujah Chorus blared inside my head.

I wasted no time in diving in face first as I twiddled her nipples up to sharp points. Oh my God!!! She also had the biggest clit I've ever seen anywhere, too, a little bigger than my thumb, and I have very large hands. With just a few lick-sucks, it grew even larger and hard as a, well, dick.

The whole way home I had been wrestling with what I might do if she turned out to be a tranny. Would I suck her dick? If I did, considering she was a genetically XX female, it would not be, technically, gay sex, right? I'm no homophobe, but simply find girls the sexually attractive gender, yet, just exactly what was a girl, anyway? What if she wanted to fuck me in the ass? How different would that really be from a girlfriend fingering my butt? I realized I was trying to "heterosexualize" whatever behavior I might have engaged in, in the course of having sex with her had she been a tranny.

And now, though she was thankfully clearly a woman, I was sucking her clitoris, the morphological female equivalent to the penis. Because I seriously thought that she might be a transsexual, coupled with the fact that she had a huge clit I was now sucking, for the first time in my life, I was forced to consider that gay or straight sex was not so categorically separate, after all. Suddenly, my black-and-white world was painted in infinite shades of gray. Weird.

"I love the way that feels, but do you really like doing that?" she asked. "Of course I do, Jamie, it's better than great." "Why?" she inquired, curiously. "Well, doesn't every heterosexual male?" I answered, pulling her gigantic pussy lips between my teeth and lips.

"No. Bush doesn't. He's a great guy, but he has no interest in sex at all. He's not gay, but he just does not do sex of any kind--intercourse, oral, nothing. He's asexual, has no desire for sex whatsoever. We love each other dearly, plan to get married after we graduate, and since neither of us want children, that's not a problem. I do like sex, though, so I masturbate--a lot."

"Do you think he would have a problem with our doing what we're doing?" I asked. "No. Not really. He knows I have needs he cannot fulfill, but I'm definitely not going to tell him. I mean, I love him and would not think of hurting his feelings by making him feel inadequate." Well, so THAT was the deal with Jamie and Bush.

Jamie said she really did not know much about having sex with another person, but had been playing with herself since puberty, using not only her fingers but various phallic fruits, vegetables and household implements, always dutifully returning them when finished.

Between ejaculations, Jamie matter-of-factly relayed this incident from her teenage years:

"I was always trying something new as a pseudo-penis—dildos were impossible for a minor to get then—like a banana, zucchini squash, big kosher pickle, large carrot, screwdriver handle, candles, Tabasco sauce bottle, a small flashlight, to name a few. Those were fun for the novelty effect, but I always came back to Mom's trustee pestle, which sat in the mortar over the sink in the kitchen window sill."

"Yeah, I know what you're talking about, mortar and pestle, the heavy, deep-sided bowl with the smooth tool that kind of looks like a bell clapper. They used them in the old days to grind up drugs at the pharmacy," I clarified.

"Right, but, actually, it was known then as an 'apothecary,'" the brainy Jamie corrected "In fact, that off-white ceramic mortar and pestle had been handed down from my great-great grandfather, who used it in his store to mix up confections. A mortar and pestle can also be used to grind up herbs and spices, which is what Mom had it for. In fact, Mom is a gourmet cook, and used it frequently. That's what created the, shall I say, 'conflict of interest.'"

"All right, Homer, where in this epic does the pestle make it into your pussy?" I kidded, already feeling a twitch of life in my cock just at the thought.

She continued, "OK. OK. Well, I would nab the pestle from the kitchen window when I got home from school, then go in the bathroom and soak it in hot water while I got out of my school uniform. Then I'd slide it up in me. Oooh, it felt so good! So warm and smooth and slick with my vaginal fluid. I'd work it in and out and in and out, taking myself to the very edge of climax but intentionally not going over...Hmmm, looks likes something's 'come up' here!"

"Yes," I acknowledged, "Swirling my personal pestle in the mortar of stories like this tends to have that effect. Please go on to see the full effect"

She went on, "Then I'd pull on a pair of tight jeans, without panties, of course, and go about my chores--doing laundry, raking leaves, changing the beds, dusting, whatever. When I moved, the large end would roll around deep inside me but the tapered end allowed room to move around the lower part of my vagina, and the knob on the very end would press against my clitoris. I learned how to position my crotch so that the thick denim seam would push against the knob, which, in turn, rubbed against my 'knob' to make myself orgasm anytime I wanted as I merrily went about my tasks!"

"So where's the conflict of interest?" I wondered.

"When Mom needed to use it," Jamie rejoined. "Then I'd have to create some distraction, and quickly pull it out and put it back in the mortar on the window sill. I had some VERY close calls, but it was always so exciting. Even more exciting was the fact that I never, ever washed it off before replacing it. Call it teenage rebellion, but I got a real kick out of that, especially when the rest of the family would remark at the dinner table how good the sauce was, knowing that there was an ingredient in there only I knew about!"

Now I was as hard as that ceramic pestle.

"But you know what? I like yours even better, she said, grasping my tool with both hands, with a look of near adoration in her eyes." "I mean, actually doing it with a real, live person feels incredibly fantastic. I want you to teach me everything you know about sex, starting right now."

Jamie proved to be as good a student in bed as she was in college, a 4.0.

We stayed up past daybreak, and I showed her everything I knew, and she caught on very quickly, asking appropriate questions like the right amount of hand pressure, mouth suction, fucking pace, and so on. I showed her everything from how to swirl her hair around my cock to the finer points of the flying fuck.

She even swallowed my cum with ease the very first time she ever tried, making highly academic and accurate comments afterward: "Viscous, somewhat salty, quite vegetative in flavor, and a bit cloying going down the throat. Not bad. Show me some other stuff."

Jamie was not THE BEST sex I ever had, but I'd put her in the top quarter, remarkable, considering her complete lack of experience. She did not come right out and say so, but it was quite apparent that she was a virgin. Of course, many years of masturbatory experience with a wide variety of fruits, vegetables, and various household implements—including The Pestle—counts for something.

That day was the only time we ever had sex, as I just was not comfortable screwing her behind Bush's back. When he returned, things were just as they always had been with the three of us, and she never mentioned it again to me or gave even the slightest indication to anyone that we had spent many hours of sheer sexual pleasure together that one morning.

It was easy to select a Christmas gift for her (and Bush, har-har) though: a nice ceramic mortar and pestle very similar to her family "heirloom" I found in a mail order catalogue. Considering Bush's asexuality, it was the least I could do.

Naturally, I never again perceived her as the sexless intellectual I once had, and frequently masturbated to the image of her that morning so willingly learning all about sex. The memory of that mammoth clit and those humongous pussy lips are as fresh today as they were the day I enjoyed them. Moreover, the experience and subsequent resolution of doubts about whether she was male or female or transsexual shattered my formerly concrete categorization of gender identification.