My Night of Anal

My night started with pleasures of the oral kind. I met 3 girls for a late dinner at Osteria Morini Soho. The setting was a simple rectangular room with exposed brick and wooden tables. We devoured meats, cheese and roasted peppers as a prelude to pasta, the main event, washed down with several bottles of red.

The star dish was truffled ricotta ravioli with prosciutto and butter. It was impossible not to roll my eyes in pleasure every time I slipped a heavenly pocket of ravioli into my mouth (despite having to eat around the prosciutto for kosher reasons!). The creamy ribbons of rigatoni with wild mushrooms and fresh rosemary were a very close contender.

The girls rolled home, but I was full of spontaneous energy. I caught my friend by phone as she was boarding the subway home, and convinced her to backtrack and meet me for drinks. She took me to Mayahuel, an inconspicuous tequila bar near my East Village apartment. We sat at the mosaic-ed, candle lit bar, drank whatever the bartender recommended and caught up.

Cocktail on a bar stool black and white

Now 3am, we went separate ways. The intention was bed, until I passed my local fave, Goodnight Sonny, open til 4am. Feeling carefree and mischievous, in my short cream dress and no bra, I decided a nightcap was in order. Within 2 minutes at the bar, I was approached by a dark haired man, who struck up non-descript chit chat as I watched my lemon and vodka cocktail being poured into a coupe.

I wasn’t interested in him, but I noticed his friend at the end of the bar, chatting with an older man. The friend and I clocked eyes, and the old man was ditched. I’d be lying if I said I remembered the conversation: he was from Georgia, but grew up in New York and loved his job, which I think was something to do with data. He was dark haired, lean, medium height with large, almond shaped, deep brown eyes. His manner was gentle, but his smile spelled naughty.

Within 10 minutes we were outside, kissing, and I was hot for him. He invited me to his, but I suggested my place, which was empty that night. Tipsily, I overshared that I was finishing my period so it wasn’t the best time for sex. He said he didn’t care, and I was soon to find out why.

When we entered my bedroom, I unzipped my dress and it fell to the floor. I was wearing knickers and heels, which he demanded I keep on. He bent me over the bed, got down on his knees and before I could protest, pulled my underwear to the side, and began licking my asshole.

Dress being unzipped from behind

Now I’ve never been shy of an anal finger slip; it’s highly erogenous and can result in incredible orgasms. I’ve had anal sex a few times in my life, with varying success. This was the first time that someone had gone down on my ass. I thought I’d have a problem with it, but it felt fantastic, and this guy was so astonishingly adamant and turned on, who was I to deny him the pleasure? My inhibitions flew out the window.

The next few hours were a blur of kink and bliss. We even got my toy box out at one point. This man knew exactly what he wanted, and it was all ass. Lets just say that my vagina has never felt so neglected.

As I said goodbye at the door at 7am, in my white dressing gown and over-sized glasses, we started kissing heavily again, and before I knew it I was bent over the kitchen table for round…I’d lost count. When he left, I wondered if it had all been some crazy dream.

He’s texted me once since to invite me to a concert, but I told him I was picking up a new mattress and had dinner plans. His response: ‘We didn’t ruin yours last time, did we?’

For me it was a whirlwind, one off experience: impossible to recreate. Plus I’m not entirely sure I would recognize him again. One thing’s for sure though, you can never predict where a New York night is going to end up, or for that matter, what exactly is going to end up where.

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