Lillian’s Place – Christopher’s Story F/M

I could tell you just where Lillian’s Place is but it wouldn’t do you any good. I could tell you about the street and the little the alley that runs off of it; what the sign outside looks like; the steps you have to descend to gain entrance, but unless you needed to show up there, you wouldn’t find it. That’s how it works.

Of course, I didn’t know any of this the first time I found myself sitting across the bar from Lillian herself ordering a Jack and Coke. At least, I was trying to order a Jack and Coke. It had been a Jack and Coke type of day. Lillian didn’t seem to care.

“Jack and Coke, please.” I looked the proprietress up and down. I would have guessed her age to be somewhere just shy of fifty, but she could have just as easily been twenty-five. She looked Eurasian (later I would learn I was wrong – her father was Native Alaskan and her mother was Jewish) with dark wavy hair, deep red lips and a very large, full bosom.

“Have you ever noticed that San Francisco is a city of clocks? Really they’re everywhere – the ferry building, on that church up on California and Grant, all up and down Market Street. There’s one almost every block. We’re never far from the past in this city, Christopher.”

“How…how did you know my name?”

She laughed and pointed to the lapel of my suit. “Name tag. You must have forgotten to take it off. Some type of conference?”

“Yeah – Intellectual property law and the Internet. It’s thrilling stuff.” I ripped the tag off my suit jacket.

“I’m sure it is.” She replied. The funny thing was I believed her.

“Now what about that Jack and Coke?” I really wanted nothing more than my drink at that point.

She turned from the bar to reach the bottle of Jack, “By the way, if you want to see my tits, you have but to ask.”

“OK, let me see your tits,” I said to her back. Forward sometimes worked for me.

She laughed and turned to me, holding not a bottle of Tennessee’s finest, but a bottle of milk. “Perhaps later, Christopher.”

A woman slid on to the barstool next to me and giggled as Lillian poured the milk.

She glanced my way, smiled and turned to Lillian, “I’d like it to be public. Out here.” The woman gestured to the patrons of the bar.

Lillian answered, pushing the glass of milk towards me. “No. Not this time. Not for his first time. But don’t worry – they’ll know.” Lillian looked out at the people in the room. “They’ll hear.”

I was only half-listening to the women’s conversation as I fully took in the room and the odd assortment of characters at Lillian’s Place. Regulars, I later learned. In fact, we’re all sort of regulars here.

Now, I live in San Francisco, and (not to make generalizations, and apologies to those who live in the middle of the country) but San Francisco is not Kansas City. But looking at the people in Lillian’s Place I was a bit taken aback. It was the satyr over by the pool table that got me. They guy in the nun’s habit really wasn’t all that unusual. Nor were the doctor (later I learned named Melissa) and her male nurse (Devin). I could deal with the pixyish woman sans shirt with electrical tape on her nipples. The woman dressed like she stepped out of Mayberry RFD wasn’t all that strange either. But the satyr, the half man, half goat holding the pool cue, now that was weird. Even for the City by the Bay.

Lillian must have noticed my look. “That’s Joe.”

“Huh.”

“Goat-man, over there, playing pool – his name is Joe. He’s a satyr.”

“I know what a satyr is,” I said.

“Christopher, you’re not here to stare at Joe.” It was the young woman who had sat down next to me.

I turned to her and three things happened all at the same time. One: I realized she was young – very young, maybe 16 or 17, far too young to be in here. Two: she looked staggeringly familiar. Like déjà vu, did-I-fuck-you-drunk-in-college-and-can’t-remember familiar. But this would have been impossible given her apparent young age. And three: ok, I wear silk boxers made by Hugo Boss. It’s an indulgence of mine. I mention this not to impress anyone, but because as I turned to this impossibly young woman I felt the fabric of my underwear changing, becoming rougher, losing its silken feel. I felt it shrinking, constricting around my thighs as the rough fabric drew up against my ass.

“What the fuck?” I couldn’t help myself. The ‘what the fuck’ just came out.

“His cock is a monster.” Lillian said.

“Huh?”

“Joe’s. His member. His package. His ‘say hello to my little friend.’ This last one Lillian drew out in her best Pacino. Leee-telllll friend. “It’s huge. I’m sure it’s much bigger than yours.”

“No, not that. It’s my…never mind.”

“Your underwear.” The girl (I couldn’t call her a woman anymore) reached over and put her hand on mine.

I was down the rabbit hole. Or at least I thought I was. Little did I know I was merely standing at the entrance.

“My under…how…?”

“Explain it Connie.” Lillian said as she slid a Sierra Nevada to the girl.

“You’re name is Connie?” I looked deeper into the girl’s eyes. “But…”

Connie smiled. A warn, inviting and nurturing sort of smile. “You know me, don’t you?”

“But I….no….I….no, I don’t.”

“But nothing. You know me. Just as sure as you know you’re leaving here tonight with different underwear than you came in with.”

I tried to reach in under my slacks and pull the a bit of the underwear out to look at it. No luck. It sure did feel different. Very different.

She continued, “your rational, Stanford-educated brain just won’t let you admit it. But you and I do know each other. Quite well, in fact. Drink some milk.”

It wasn’t the Jack I so desperately needed, but I took a gulp and as the milk hit my tongue, the glass slipped from my hand and tumbled end over end through space and I saw Connie and I knew her and I knew it was possible, however improbable it seemed, and just as the glass was about to shatter on the floor, it stopped spinning, hovered in the air and then ever so gently settled to the ground as flying milk coalesced into the shape of the glass and filled it once again.

I was looking at the babysitter I had when I was twelve.

“Hello Christopher. It’s nice to see you again.”

“Connie?” I looked at the unblemished skin, the long, straight Marcia Brady hair and the perfect, nubile almost-a-woman breasts. “It’s you isn’t…but how…”

“Stop looking down there, Christopher. Eyes up here.” A finger – pink fingernail – tapped next to a blue eye. “Lillian may not have a problem with that sort of thing, but I do. You should have learned that.” She paused, “A long time ago.”

Lillian walked by on her way to the other end of the bar. “Tick-tock, tick-tock,” she sang to herself.

Connie leaned in to me, “Let me ask you this, Christopher. And I really want you to think about it before you answer, but are the man you wanted to be?”

In my mind I saw my Pacific Heights flat. I saw the stewardess I brought to that flat last Thursday. I saw my well-stocked, temperature-controlled, vibration-free wine cellar – mainly big meaty reds. I saw my ex-wife and our home – her home – in Portland.

“You’re….sixteen…seventeen?” I asked. I don’t –“

She laughed. “No, I’m forty-four.” She gestured in the general direction of the door to the bar. “Out there, I’m a mom in Fairfield. Married, two kids in high school, minivan – the works. In here, I’m the me that you need me to be. Believe me, it’s kind of a nice break from being the middle-aged me.”

“How is it possible?”

She gestured out to the bar. Joe the satyr lined up a shot on the pool table. “This is just a special place. Now answer my question. Have you become the man that you wanted to become?”

Lillian was walking past again. “Make sure he tells you about the stewardess,” she said to Connie. “Her name was Carla, Christopher.” She raised her voice from the end of the bar. “In case you forgot.”

I thought about the stewardess’s shaved pussy. “No.”

Connie spoke softly. “’No,’ what Christopher?”

“No, I’m not the man I wanted to be.”

“OK then, finish your milk. We’re going to go work on that.” She glanced at Lillian who was at the other end of the bar, telling a joke to the doctor in surgical scrubs. “I think she’s right – this time will be private. Just you and I and my hairbrush.”

I drank the milk. When I was done, she took me by the hand and led me to a door next to the bar that I hadn’t noticed before. The room inside was comfortable: over-stuffed furniture, a fireplace that emitted a soft glow, there was an old-fashioned radio and a big bed. Connie sat on the bed and looked me up and down. I did the same to her.

Connie blushed. “Damn it, Christopher – I don’t even need Lillian to tell me what you’re thinking! Good God! I shoulda done this long ago.”

“But you’re in your forties, but you also look like you’re…I always had a crush…and you know I can’t help –“

She interrupted my impromptu and ineffective defense, “Over here now mister! I didn’t do this twenty-five years ago and look where it’s gotten us. NOW!”

It was then that I became fully aware of the hairbrush on the bedside table and fully understood my fate. She wasn’t forty-four. She was sixteen. Her name is Connie. I shuffled over, eyes downcast, hands at my side, a rock forming in my stomach.

She unbuckled my belt. Unbuttoned by dress slacks. Unzipped me. Pulled the boyish tighty-whitey underwear to my knees. I wondered briefly where the silk Hugo Boss boxers went and if I’d ever see that pair again.

My one-time babysitter didn’t say a thing, merely pointed to her lap with the hairbrush. I complied.

I felt the wind, air displaced by the brush, a split second before

SPLAAAAAT

And before I could register an “Oh JE-sus” another

SPLAAAATTT

Holy-fuck-my-god-that-hurt! This was not a little boy’s spanking.

SPLAAAATTT
SPLAAAATTT
SPLAAAATTT

“No more Connie! It hurts!!”

SPLAAAATTT

“It’s supposed to hurt.”

SPLAAAATTT….It…. SPLAAAATTT….is…SPLAAAATTT… SPLAAAATTT….supposed…. SPLAAAATTT…to…. SPLAAAATTT SPLAAAATTT SPLAAAATTT…..hurt! Christopher…. SPLAAAATTT SPLAAAATTT SPLAAAATTT SPLAAAATTT SPLAAAATTT SPLAAAATTT SPLAAAATTT SPLAAAATTT SPLAAAATTT SPLAAAATTT SPLAAAATTT!!!!

“Get up!”

SPLAAAATTT “I said, GET UP!!”

I half-fell half-staggered off her lap and to my feet.

“You are not the man you want to be today because I did not take care of certain things, traits I saw in you as a young boy.”

She was breathing heavily from her exertions and continued. “For lack of attention, I accept responsibility, and there are certain consequences that I will face one of these nights because of what I didn’t do when I watched you.

She waved the long-handled oak hairbrush at me. “HOWEVER, tonight is your night. Tonight we start to remake you into the man you should be. Get back over my lap.”

As though with no will of my own, I got back down over her lap.

“Tonight, you begin to learn to respect women.”

SPLAAAATTT

Later. Much, much later, when my babysitter from 1978 was done with me and my ass was a five-alarm-fire-red and we reentered the bar, all eyes in Lillian’s Place were upon me.

I knew that they all knew what had happened to me. Joe, the satyr, began to clap. Slowly at first, and then others joined in. A dam broke and soon I was surrounded by people hugging me, patting me on the back, welcoming me to Lillian’s Place as I made my way back to the bar.

When I got there, there was a Jack and Coke waiting for me.

End