Letter Between Friends Ch. 02: Jerry

A Guy Named Jerry

I'm sitting on a cushion now, sore from one hard night but I have to write you about it. You are going to love this one!

To start, this wasn't the night I had envisioned but it was so damn fun!

After I left my two sisters by the train station I was going to meet up with my friend Sue and maybe go to a girl bar. Susan texted 15 minutes before we were meeting up. She was too tired to go out. It was only 9PM! Moments like that make me feel so old. How quickly the carefree twenties go by, followed by the fleeting thirties and now the fast paced forties. Ugh.

Sue was once the main lady for all things lesbian. She threw the biggest, the best all night gay girl parties at the hippest venues in the city. And now she is in bed by 9:30. Hard to believe 20 years of friendship and parties have gone by. What a great ride it's been but I'm not done yet!

I usually don't mind going out on my own. I like having dinner at a nice restaurant, sitting at the bar minding my own business but still absorb the vibe and energy around me. Last night was different. I wanted company, conversation. I set out into the city with the thought of visiting a few places in my old stomping ground downtown.

The first place was under new ownership with a new name. The age range was at least half of mine. I'm sure I looked like someone's mom looking to give my kid a ride home. I did an awkward two step out the door hoping no one noticed the out of place 40something woman.

At the next stop the women looked about my age which was a relief but they also looked like they just got off the farm! What was up with that?! I really hate the old lesbian stereo type but in this instance it fit like a glove. I get embarrassed for my people. Needless to say, that place was a no as well.

The last place (I'm starting to feel like Goldilocks) was just the hotel bar where I was staying. I sat in the far corner, ordered a drink and enjoyed the bad theater playing out in front of me - men of all ages shamelessly trying to pick up girls. I can't even say they were women, they looked too young.

As I'm somewhat minding my own business this guy pulls out the high bar chair next to me and sits down shimming the chair closer to the bar. He smiles and nods "Hi" in my direction. I look over to my left thinking he is saying hello to someone next me, forgetting I am sitting in the last seat at the end of the bar.

We continue our silence. The bartender noticing my empty glass, asks if I would like another glass of chardonnay, at the same time my new silent friend next to me said "Put her drink on my tab." I guess that was the icebreaker.

We start to make observational comments about the men across the bar from us, picking up two women. Or maybe it was a 'business' transaction? The women were beautiful and perfectly dressed - in a whole other league than the two men buying them cocktails. I'm not saying it isn't possible for two equally pretty women to like two equally below average looking men. I just think it's highly unlikely.

My new barfriend is from Ireland. He is here for a wedding. He is nice, funny and average looking. Sandy blond hair, blue eyes, maybe 5' 9". After the 3 maybe 4 beers he had, he starts to tell me about his kids and his wife leaving him. We talked about 'his feelings' and how he wasn't emotionally there for her. Why- o- why do I attract the men that want to talk about their feelings??!

Anyway, the bar is empty now. The two below average men left with the above average women.

I said "I'm going to bed, nice to meet you," as I slide off my chair, feeling tipsy. I shouldn't have had that third glass of wine.

I walk a few steps and for some unknown reason, I think it's called impaired judgment, I turned and said "Would you like to join me?"

He quickly nodded "yes," like an obedient puppy.

I wanted some fresh air so I opened the door to the terrace. I went to the bathroom and when I came out he was smoking a cigarette outside. That's a no. "I hate that smell" I said with disdain. I'm sure my expression conveyed the odds of him getting laid were dwindling.

"I'm taking a shower," he announced in reply to my disapproving look. "I'll wash off the smell."

While he was showering, I took my clothes off in the bedroom. I wasn't in a rush, I took my shirt, jeans and underwear off like it were any other night. Only this night I was going to have sex with a man. Not something I normally do. I thought about that for a moment while I folded my clothes into a neat pile on the dresser. I then walked naked towards the sound of the running shower. I pulled the shower curtain back to join him. With a glint of surprise in his eyes he said "You are one sexy fucking angel." I stepped into the shower with a sly smile.

Jerry didn't waste time. I was up against the shower wall, my hands against the tile, my ass pressing against his growing cock.

He slid his hands up my side and around, cupping my breasts. The shower head above streaming water down my back, lubricating his cock as it rubbed between my ass checks.

I took his hand from my breast, guiding it down between my legs. I wanted to feel his fingers in my smooth shaven pussy. He let out a low moan as his fingers glided over my clit, his cock pressing harder against me.

I've never been fucked in the ass but I was so turned on I wanted to try it. With warm water running over me, his fingers playing with my pussy, I spread my legs a bit more and leaned into the wall. He accepted the invitation.

"I am going to fuck you so hard," he said as he teased my ass checks with his cock.

I responded by moving my ass back and forth against him. I held onto the shower handle, bracing myself for the hard fucking he promised.

He moved his fingered between my ass, finding the holy hole he slowly inserted his finger. I sucked in my breath with this new sensation. My god, I was so fucking turned on, I started to rub my pussy as his finger went deeper.

He pulled his finger out and replaced it with the tip of his cock. He pushed the head in a little and then out, in and out, teasing me again. With the next tease of his tip of his cock, I pushed against his body making his rock hard shaft go deeper in me. He let out a primal groan as he thrust his full length into my ass. I screamed out with the mix of pleasure and pain.

I managed to say "Yes," as he drove into me again and again. He took over fingering my clit while his cock was buried in my ass. I help onto the shower handle feeling an explosive orgasm rising in me.

"Fuck yes," he said as he drove deep again.

I could feel him release inside, pumping his cum into my ass. I cried out, my cum dripping off his fingers. He held my hips as he pushed in deep one last time shooting his last drops before pulling out.

We giggled with exhaustion as we stumbled out of the shower and onto the bed.

We were still wet from the shower but we didn't care. Jerry didn't waste any time spreading my legs. My pussy was slippery from my explosive orgasm in the shower. He sat back on his feet while he had my legs spread wide, finger fucking me. I moaned, wanting more.

I sat up and pulled his head down between my legs. I loved the feeling of his hot breath and tongue in me. He was exceptional at eating pussy, he should be a lesbian. I pushed his head into me, holding onto his hair as I fucked his face. Jerry lapped up everything I gave as I shuddered and came.

Needless to say, this left him with a massive erection once. I was about to get fucked hard again.

He sat up, face wet with my cum. "You are one sexy bitch."

I responded by sliding my fingers over my clit while putting my leg over his shoulder.

Jerry pulled my hips in closer as his cock found my pussy. He didn't need his hand to guide himself in, he held onto my waist as he entered me slowly. He sucked in his breath with the feeling of my tight warm pussy enveloping his thick cock. I think it was a good thing I came so much before, I needed the lubrication to manage taking in his girth.

As gay as I am, I do love the occasional hard cock. There is something erotic and primal about a cock driving hard into me, swallowing it to its base that makes me throb with excitement. Don't get me wrong, I love pussy and would never abandon a good muff dive for cock.

I didn't think it would be possible to have another orgasm but I could feel that sensation rising again. Jerry wasn't pumping in and out. He stayed deep in me, rolling his hips as his entire cock did a little dance inside of me. Dear lord, he was good! I rubbed my clit as we could feel each other reaching another climax. He held my waist, pushing as deep as he go. He arched his back and let out a guttural cry as he let go, releasing his creamy juice inside me. This sent me into a huge orgasm as I rubbed my clit. I know my pussy was gripping his cock tight, feeling him cum more.

He collapsed next to me his chest heaving from that stellar performance. I put my fingers between my legs, feeling his deposit ooze out of me.

Jerry asked for my phone number, I said no. That didn't stop him from starting to lick and suck my tits again and sliding his hand up and down my soaking wet but sore pussy.

I kicked him out the door a short time later. As he was walking out he said "I want to get to know you better."

"You just did," I replied with a devilish laugh.