The last sane bloke in Chicago

She has a wonderful boyfriend (a true story)

Black Wednesday. My most hated night to go out, even more so than New Year's Eve. I was planning on staying in, making some pastrami from scratch, and watching a movie or reading a book. At 9pm, a good friend of mine who is a bartender at a trendy bar texts that she's bored, and the place is dead, so I should pop in for a few free glasses of whiskey, on the rocks.

I considered it, twice. I checked my email, my social networks, and my phone, and decided to just go. So many people were out, but none at this bar that I'd know. I could sit at the bar, sip my cocktail, and maybe talk to my old friend.

I put on some clothes, fast: great (GREAT!) shoes, an amazing tailored shirt, some jeans, and my new early winter coat. I looked surprisingly handsome and fresh, even though I skipped a shower today. It happens. Then I hopped in my car, and found myself at the lounge around 10pm. 30 people in a room that could hold 200. Not good for business.

I sit down at the bar and my friend already has my drink pouring. 3 ice cubes, 3 ounces of liquor. I like it done right. I sip, we chat. She's going through some bad times with her guy friend (2 years, now living together), and doesn't know how to get out. I always tell people who move in together to pay their rent, but to also put an additional half rent in savings each. That way, you know you can pay rent yourself, and you have money saved. If you can't do that, you're renting a place too big or too well located for your meager budget. Her tips have fallen 50% year-over-year, so she's hurting. Moving in with him was a financial move, and a bad one at that.

An hour passes and I listen, intently, to her talking. A friend walks in, let's call him Paulo. Spanish. Dark. Tall. Handsome. We hug and shake, I buy him a drink, he buys me a shot, and we talk here and there until his 6 buddies arrive. They're all gorgeous. Paulo's been dating Celine for 6 1/2 years, living together. He's not a player anymore. Celine is gorgeous, but I've only met her twice. They usually don't go out together here, even though they live 2 blocks from this lounge that I frequent at least twice a month.

Paulo leaves with his buddies just as Celine arrives. She doesn't want to go to Frat Boy Square (Rush and Division, ugh), so she stays behind. I didn't recognize her at all when she sat down next to me, she had changed her hair and her clothes looked nicer. She seemed to not recognize me either, and I continued to listen to my friend complain. Then it got to sex: my bartender friend's sex life sucks.

Eventually, Celine starts putting in her own story about wanting more in bed, but not sure her man will be the right one for it. I talk to her, look in her eyes deeply as I do with all people I speak with. An hour of hearing her complain surprises me: she's tall, slim, beautiful. I ask her her name and she says "Celine." I look perplexed, and she says "Wait, are you ChicagoSane?" Yes, I am. And you're Paulo's girlfriend. Oh shit.

I listen more, the one good social skill I have, and we talk for a total of 3 hours. 11pm to 2am. Her boyfriend never returns, but he texts around 2:30 that he's going to another bar, a late night. The bars in Chicago close at 2am or 4am, depending on their luck and licensing. So texting at 2:30am means he already went somewhere else. What a fuck. Her and I were sharing cigarettes outside, waiting for a cab for her. It never came. 25 minutes of waiting. I offer to drive her home, and then realizing she only lives 2 blocks away. Why wait for a cab, I ask. "I just wanted to talk more."

There it is.

So I ask her if she wants to go get food or another drink. "Sure, drinks sound great, but things are closing in an hour or so." There's a bar not far from my place on the edge of town that's open later than 4am, so I offer to drive her there. We go, passing the city limits in less than 10 minutes. The bar is dead, but quiet and dark. We talk more, or actually she talks more, and I listen. She holds my eyes strongly, full of confidence and friendliness and courage. I wish more women could lock eyes with me when we talk.

It's 5am and the bar is closing, so I offer to drive her home. I'm a little tipsy, but she's sober. "I think you shouldn't drive." As I get up, my keys fly out of my hand, forgotten, onto the floor. I agree. "Let me drive you home, you're close, right?" I told her it's just one street all the way, about a 10 minute drive.

We get in my car, and she drives me home. I ask her if she wants to come in and I'll buy her a cab. She agrees.

We sit on my couch and talk some more. She opens a bottle of wine (an expensive one, but she knew) and sits next to me instead of on the softer, large chair. We talk until 6am, at which point her hand is on my thigh, and my hand is on the small of her back. I'm not sure how it happened, but we were in my bed by the time I noticed the clock said 6:10am.

We kissed in my bed for over an hour straight. During that time, she removed her shirt, herself. Her jeans were at the foot of the bed, also her doing. Her hand unbuttoned my shirt and my pants, but I didn't remove them. I just wanted to kiss her and let her lead with her passion. When my hand accidentally brushed her pussy through her panties, she moaned. I didn't grab her tits or her ass, but kept my hands on her back, her shoulders, her arms and sometimes her knees and calves. She was beautiful, and graceful.

Finally, her hand went under her panty band, but I pulled it out. I could see her fingers were wet, and she was ready for more. Every time she tried to tickle her clit, I pulled her hand away and kissed her deeper. By now she was moaning and begging. I told her she needs to take my clothes off, and she did, while locking those amazing eyes with me. The remainder of her clothes were off now, and her small tits and slim waist had me extremely hard. Her beauty was a huge turn-on.

Her mouth was on my cock in seconds, without my prompting. She was good, too, only gagging a few times as she took my length into her throat. I'm not long by any means, but I'm thicker than most, so someone without a gag reflex is a nice addition. She kept looking at me, noticing my smile. Her free hand grabbed my right hand and placed it on the back of her neck, offering me to pull her mouth onto me at the speed I needed. I told her I wasn't going to last, and she just looked at me as I came in her mouth and down her throat. She swallowed it all, only letting the first pulse slip out of the side of her mouth.

"You taste amazing." It's my diet, but I didn't say that. She was still rubbing my cock head lightly, and he returned to full attention just 30 seconds after I unleashed my load in her. "Wow, ready for more?"

I turned her over on her stomach with a fast move of my strong arms. She yelped, but let me run my hands from her head to her feet, focusing on all the areas her boyfriend doesn't. She was writhing when I noticed it was closing in on 8am. I spread her legs, still with her stomach flat on my bed, and I kissed my way up her legs and thighs. When I looked at her pussy, finally, I noticed she hadn't shaved in quite a while. Poor girl had no reason to.

I turned her over, and tasted her for the first time, my hands and mouth still having avoided her nipples and tits and pussy and clit. I teased, as I needed to, as she needed me to, until she pulled my long hair hard and told me to eat her. I did. I didn't have to even touch her clit as her pelvis shoved into my face. My thin beard was glistening in moments. Her clit was beautiful, just small enough to be a game to find, but large enough to be very sensitive. Not 5 minutes of my tongue and lips on it and she was there, thrusting her hips as I licked harder, and then softer and softer as she came down. She fell back, exhausted, but I kept my tongue softly on her clit, not moving.

After 5 minutes of her breathes and heaves slowing down, I lightly licked again. "No, I can't a second time" she told me. I still licked, even lighter than just 15 seconds earlier. Her lips parted again, by themselves, and her moans started up only 60 seconds into my second attempt. "Oh, oh wow," were her words. "Oh wow, what are you doing?" she asked. I actually was doing nothing, my tongue was barely on her clit, my breath was warm but not heavy. I had to do nothing as I noticed her clit was now fully out of its sheath. Sensitive, I know. I just let her hips gyrate into my tongue, which I pulled off so I wouldn't hurt her.

60 seconds. She came a second time. She screamed, probably waking the neighbors. Her hands were on her thighs as she lunged into me, soaking the sheets beneath her that I had just dry-cleaned Monday.

During the final moment of her second orgasm, I jumped my body up to hers and held her close, her face in my neck and hair. She held me back, shaking and moaning "Thank you, thank you" even though I didn't do as much as I had wanted.


We laid there, me on my back now, her cheek on my chest hair, for about 15 minutes. 8:20 or so this morning, just 3.5 hours from when I'm writing this.

Her hand was playing with my still hard cock, running her finger tips lightly under my the head, just like I like it. "Do you have condoms?" she asked. Of course I do. I pointed to the nightstand next to the bed. She went and got one. "Bring a few," I said, as she threw the sexiest smile at me.

The condom was on (her doing), she was laying back, her fingers rubbing her open pussy lips. I didn't wait, I turned her ass to the edge of the bed, dangling her feet over, stepped back, and then stepped forward and rammed right into her. "Oh, God." Tell me to fuck you. "Yes, fuck me." Tell me louder to fuck your pussy. "Oh, God, fuck my pussy, please." And I did.

I fucked her for 45 minutes and came. I had my hands in her hair, my elbows pinning her shoulders, my mouth on her mouth and her chin and her neck and ears throughout. I pulled out, pulled her by her ankles and waist to the floor with her head against the bed, yanked off the Trojan, tied it off, and put my cock in her mouth. I was hard again in less than 3 minutes. Another Trojan, and made her stand up and lean over the edge of the bed. She came in less than 10 minutes in this position, as did I, at the same time. I pulled the condom off, and let her taste my come a bit more.

I asked her if she wanted more, and she said "I've never orgasmed three times with a guy before." I told her that was terrible, but it always depends on the chemistry and the build up. She just nodded. I pulled at her hair a little and brought her to my mouth. We kissed, my come on her lips, hers on mine. I removed her hand from my semi-hardening cock, and we just held each other.

At 11am, Paulo texted her, he was heading home. She smiled, kissed me again, and said "I needed that. So badly." I told her I loved sharing, and I understand that it won't happen again. "I could only wish, but you know where I am." I did. I understood.

She put her clothes on as I called her a cab. It was here in 5 minutes. I ran out, paid the cabbie, and gave her a hug, not a kiss. She smiled, and as she pulled away, she mouthed "Thank you." I just smiled, turned, and walked back into my front door.

Condoms and wrappers are now in the trash. The sheets are pulled from the bed and replaced, ready to be dry cleaned Monday. My cigarette is dangling from my lips, my pants are back on the couch, and I'm wishing she didn't leave today. I would have loved to have just held her, let her laugh, cry, talk, suck, swallow, fuck, and just be a woman for a day. She was a woman for a night, though, but that's never enough. Even if it's temporary, she deserves to be recognized for all she is, not just her body or her mind or her face or her body or her smarts or emotions. Just everything. I gave her this address and know she'll read it and clean it from her history right after.

Thank you, Celine. And you're welcome.

Posted by ChicagoSane at 11:25 AM