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Mammeries are Made of Moments Like These – or – Alice Falls Down the Rabbit Hole

Typically I love those moments in life when I feel like Alice falling down the rabbit hole. Normally that “What the hell is this?” sensation makes me sheepishly smile inside my heart because I know that whatever comes next it will not be anything I expect or have encountered before.

Walking through a really well put together haunted house at an amusement park can give you this feeling. And it is fun.

Discovering that the man you just picked up at the local cruising place and followed back to his place has boobs - is not fun. In fact it can put you off sex for several weeks.

So how does something like this happen? It usually happens when you leap before you look.

I was at a local cruising park. It was a nice day, late afternoon and I had been sitting in my car doing my usual looking-but-not-looking-for-sex thing. My usual M.O. at a cruising park is just that – to park. If something happens, it happens, if not – then you go home. I don’t chase after people or sidle up to them and start conversations. If someone wants me, or if something is meant to happen, it will happen.

So I’m there for about twenty minutes when I notice this black car. The snow and ice has been melting on and off for the past week and most cars in the area are splotched with a combination of grime and road salt, but not this car. It is sparkling clean. It gleams. I watch as this car checks out another car in a remote parking lot very few cruisers bother with because it is close to one of the main buildings. Sometimes they have events there that make sitting in your car uncomfortable and your presence all too noticeable. A good cruiser keeps it on the down low and wants to avoid detection by others with the sole exception of other cruisers like themselves.

Another ten minutes go by and I am bored, so I decide to mosey down to another parking lot to see if anyone is there. On my way I see the black car exiting the park and heading across the road to a place cruisers go to be alone with their tricks. It is not a weekday, so the area, which is industrial by nature, is pretty vacant. I watch the vehicle head down the road toward the railroad tracks and think to myself “I should follow that car”. Why not? I have nothing else to do. Plus I am really curious about who is behind the wheel of such a fine vehicle.

As I arrive at the little parking area next to the railroad tracks I see the black car. It’s parked itself next to a semi trailer. There is room for me to park next to it, but it’s a little too close for my comfort and also, I don’t want to seem like a stalker or risk being rebuffed for being to obvious. So I pull in the opposite side of the parking lot and watch the black car in my side mirror. After about three minutes the vehicle backs up to where my car is, his vehicle is now about twelve feet away from mine. He rolls down his window and I do the same.

He’s very tan, very bald and has an almond shaped face. Not bad looking at all. He also appears to be much younger than me. From my disadvantaged view, he appears to be wearing a teal ski sweater.

Now, when I cruise, I typically don’t wear my glasses. This has caused me on occasion to misjudge the age of a given individual and/or the individual’s general state of attractiveness. Everybody looks younger if you blur your eyes just a little bit. For this reason I have begun to make a point of wearing my glasses even when cruising. I cannot state for certain that I was wearing my glasses at this time… but for the sake of my ego and pride… let’s just say I wasn’t wearing my glasses.

We do the usual small talk.



“How are you?”

“Good. How are you today?”


(Obligatory period of silence punctuated with strained smiles)

“You want to go to my place?”

“Where y’ at?”


“Cool. Okay.”

So I follow him.

The drive there.

The drive there – as in, to a trick’s house – is always fraught with anxiety and anticipation. The anticipation is generally acceptable. The anticipation is all about what is about to happen. It is an unknown, but you assume it will end with you having an orgasm, preferably one landing in the place of your choosing.

The anxiety stems from a multitude of ‘what if’ scenarios that float in and out of your peripheral psyche. What if he’s too young for me? What if he thinks I’m too old? What if he doesn’t find me attractive? What if his place is a filthy mess? What if he’s taking me back to a place where his buddies are waiting to beat up a fag? What if he drugs, tortures and kills me?

What if? Sure sounds like a fun time to me. Oh – and oh-so worth it!

We arrive at his place, which is one of those god-awful condo courts, where the garages are lined up on the perimeter like some protective castle wall sheltering the living quarters secreted within. I park and immediately reach for my ‘supplies’ – which, like any good whore, I have tucked away in a hidden, zippered pocket in my brief case. When I look up, the object of my soon-to-be affection has exited his vehicle and slipped sight unseen down a narrow passageway to the courtyard inside. This annoys me a little, but I shrug it off. I grab what I think I will need (which is nothing) and follow.

The passageway opens up onto a sunken yard which is surrounded by stacks of identical living quarters. I quickly thank my stars that I have never had the desire to live in such anonymous, tasteless digs and scan the stairways and entryways for signs of life. Where’s Waldo? Just then, a screen door at the top of a staircase swings open as a jean clad leg disappears within. Got it. Here we go.

I get inside. The place is kind of a dump, exhibiting absolutely no personality whatsoever. It envelopes me in an overpowering wave of indifference and lack of effort. It is dark because it’s almost dusk and the room is lit only by what natural light remains. I remove my shoes, even though I sense that the carpet is no stranger to dirt. Without a word, the man heads up the stairs. I follow. There are DVDs and clothing strewn everywhere. There is a cat. I can’t see the cat, but I sense it there. Finally I enter a bedroom featuring lots of abdominal exercise machines, lots of clothing on the floor and a large bed.

The guy I just followed up the stairs is bent over next to the bed removing his shoes. And that is when I see them. And by them, I mean his boobs.

The sweater he is wearing is one of those three-quarter cardigans women wear with the little knit belt. The jeans he is wearing are not man pants, but tight fitting women’s jeans. I learn later that women’s jeans have a very small zipper in the front – too small for man parts to spring forth from. The whole landscape is rather off putting and shapes his man parts like a giant camel toe. But I digress.

Back to the boobs.

I suddenly get that feeling – yep, Alice has just gone down the rabbit hole.

Now… what should Alice do?

I almost always go with the flow. There have been times when I have put on the brakes; extreme instances when I absolutely know I will derive no pleasure whatsoever if events continue to unfold in the direction indicated. In those instances, I pull up sails and exit – sometimes making polite excuses (I just remembered I have to… ) or (It’s me, not you), and sometimes being very blunt and to the point (Are you fucking kidding me? Dude? Come on! What the hell?).

In this case, sensing neither danger nor total repulsion, I decide to go with the flow.

This is not my first time ‘round the rodeo. And when it comes to the particulars of the female form, I know my way around and have experienced their pleasures. So I’m game, provided there is a penis tucked somewhere within those lady jeans.

Thankfully, there is.

But back to the boobs. Because that is what it all comes back to… those boobs.

They’re fake. Nicely weighted and secured in a snug, properly fitted bra. I try to play under them, but I can’t find his actual nipples, so whenever I go for the chest, I just give those bean bags a firm, manly squeeze.

I strip. She takes off her ugly sweater, lycra top, and, with my help, snakes out of her skin tight, tapered jeans. She takes my dick into her mouth while perched on the edge of the bed and I try to imagine myself getting hard. Well, fortunately for us both, I do. As I begin to respond to her mouthing my reluctant organ I struggle to come up with a game plan.

I push her back onto the bed and get into a 69 position. That’s when I discover that she’s wearing panty hose. And panties. I’m a bit flummoxed. After making pretty sure that there is a dick tucked beneath her leopard print panties, I disengage my dick from her mouth and strip off the panty hose. The panties I leave on. I just want to marvel at her ingenuity and determination for a bit. The camel toe effect achieved is quite convincing, especially in light of the size of the member being tucked. But I learn about all that a bit later.

I leave the panties on. She’s busy giving me head and my dick seems happy enough. I’m so distracted and perplexed by how I got where I am that I’m hardly paying attention to her technique, except to say that it is fairly amateurish and seemingly lacks variety and dexterity. She seems to be concentrating her efforts on only the first three inches of my dick, which leaves a good four and half not only teeth mark free (yes, she’s teething me), but also lip stick free.

Oh, did I forget to mention she’s wearing make-up? Well she is. Fairly subtle, but definitely there. She’s also so tan (baked is more accurate – and not in a good-420 way) that it makes her look much older than she probably is. The skin stretched across her stomach resembles that of a rotisseried chicken. Fortunately for her, I’m not bothered, because I like baked chicken and always eat the skin.

So after licking around her pantied crotch and asshole, I decide to find out just what it is I am going to get to play with. So the guy turns out to be reasonably hung and we get down to some serious 69ing, during which I decide 1/ there will be no kissing, 2/ there will be no anal intercourse, and 3/ that I am not up to titty-fucking her. Yes, I considered it. I thought I might go all macho on her ass, call her misogynistic names and come on her face, or at least give her a nice pearl necklace.

But in doing so, I would disrupt other possibilities and I really wanted to see what she had to bring to the table.

Let’s put it this way. If I had waited for her to serve up something, I would have left very hungry.

She seemed pretty content to just lay there on her back. So, after a point (probably when my poor dick could no longer stand the scraping of her teeth), I rolled her up on shoulders to eat out and spank her ass. She seemed to enjoy this – or at least she moaned a bit, which I took as a sign of pleasure. Then I laid her back down and finger fucked her ass really aggressively until she came. I got three fingers up there, but it was the lone thumb that brought her home. After she came, I shot my load on her dick, got up and asked to wash my hands. She pointed to the bathroom.

The inside of her bathroom looked as if the Pussycat Dolls had just rushed to the stage. There was make-up and hair-things and lady-doo-knobs everywhere. If anything it made me feel totally seedy, like entering a room two minutes after an orgy had shut down. I washed my hands, she handed me a towel. We dressed. She put on a men’s cranberry colored dress shirt, her still aroused member creating a sizeable tent beneath its buttoned front. She followed me silently down the dark staircase to the living room. I put on my shoes. Then I leaned in, gently taking her face in both my hands and left her the briefest, sweetest of kisses.

“You’re beautiful,” I said. And exited stage right.

Did I mean it? Yeah, of course I did.

See, I believe people are who they need to be. That need creates all sorts of variations due to the fact that people frequently are not what they want to be. As Melissa Manchester once wrote: “we need gardens to grow in, and there must always be room enough, for all of us.”

Yes, Alice, it takes all kinds to fill a rabbit hole.

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