Thursday, November 27, 2008

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.

Read the rest...

Thursday, November 13, 2008

Why is everyone so lonely?

I checked out Chinaski's pub (great name!) the other night, and had a decent time. It wasn't too crowded (shocker, bars are dead), but I made a few chatty friends. Guys, gals, one person who was a bit ambivalent in sex. All of them seemed lonely. Two of the guys said they were out looking for women. One woman said she was hoping to meet up with someone later, but he'd probably blow her off. The one girl who was very cute (Cuban, meow!) said she was recently dumped, and her ex went with a girl much less attractive than her. She said she was feeling in the dumps, and alone. And she was gorgeous, but down.

I used to think that recessions were horrible for one reason: couples who should break up can't because they can't afford to live by themselves. Maybe we need a site called "BreakUpRoomateFinder.com" or something. Looking to breakup? Find a person of the same sex as you who is also going through a breakup so you can move in together. Not a bad idea.

But, still, I see so much loneliness. I get it, on rare occasions, but it's usually solved by a nice dinner with a friend, or getting together for wine and movies with a cuddle buddy. I never use sex to try to fill any void from being lonely. Fucking is, pure and simple, about shutting the outside world out completely and sharing an intimate moment with someone who needs to do the same. But it's never about trying to fix a lonely night.

If you're lonely, do you seek companionship with a mate, or with friends, or with family? Sometimes, a good book in the bathtub is enough. The biggest damn problem with the Internet, the blogosphere, and the social networks is that we end up MORE disconnected with people.

Oh, and I didn't get the Cuban girl's number. Damn it. Soooo cute. But I don't take advantage of lonely women, as they're preoccupied in bed.

Read the rest...

Monday, November 10, 2008

Found $500 in the bank

I closed a bank account today because they kept hitting me with these ridiculous $8 fees each month for no purpose. Used the ATM a few days in a row to get rid of the $1980 balance, then went into the branch this morning to close it. She cashed me out $683, which was $533 more than I figured I had coming.

Ends up I had a savings account that was debiting $53 a month out of my checking account, and I didn't realize it. So now I have to go shopping this week and spend it before it ends up in a bank and out of my reach.

What should I buy?

Read the rest...

Sunday, November 9, 2008

Suck buddy worth her salt

My new almost-beer buddy contacted me yesterday. I had promised an ex-girlfriend (Theresa) a night of video games and vino at her new apartment, to meet her new roommate. But the beer buddy texted me twice, once to offer to hang out, and then a follow up to promise no physical desire.

She gave me head the first time we met, and it was fantastic, but I'm just not interested in a girl who only wants me for my sexiness. A friend, partner-in-crime, that's what I'm seeking.

So I call Theresa, modify our plans from a long night to an early dinner at her place. She's fine with it.

I cab to Theresa's, and when she answers the door I forgot how beautiful she was. I can't really remember why we broke up, but I think it was because I wanted more than she could give. I'm fairly certain that I did the breaking up, and that she fought it for a few weeks. Since then, a few years later, we've been decent friends. Her boyfriend is a complete loser: I see him all over town with various gross, trolly, mousey girls. Theresa has no clue, and I have no desire to share those details.

Her place is great, her roommate is perfect (student, in bed by 10pm, Iowa farm girl type). I decided to cook, so I looked in the fridge and the pantry and whipped up some chilliquilles. They had nachos, they had eggs, they had some odd dried fish, and all the rest. 30 minutes of prep, 10 minutes of cooking, and dinner was served. Damn fucking good, too.

And that meant I ran late. 8pm, and I promised the beer buddy (Liz) that I'd see her around 9. Of course I won't make it home for a shower, so I beg Theresa to use hers. She's fine with it, so I shower, using her terrible Aveda shampoo, and hit the road.

I get to the bar where I'm meeting Liz early, amazingly, and she's already there. She's dressed in sweats, which is perfect because I jerked off twice thinking about her nice body from the previous night.

She gives me a big hug, and her friendly smile is beaming just that: friendliness.

We chat. Her boyfriend was very inquisitive about me. I wonder if he noticed any of my spooge on her cheek or chin from the other night. Oops. She belayed his fears, and said that I'm a decent guy and probably gay. So be it.

She's already drinking a beer (Pabst, ugh!), so I order a double Ketel with lemon and drink slow to match her pace. We chatted about the week ahead: snow, cold, boredom, nothing good on TV or at the movies, no concerts worth attending, and about 90% of our friends too broke to go out. I didn't tell her that I have cash up to my ears and no one to spend it on, because she's not sugar baby material, and I'd rather feign being semi-poor. It works better.

After Liz's first beer, I order us both some whiskey and sodas. Those are gone in a half hour, at which point I'm a bit weak-headed from not eating enough (Theresa and her roommate ate most of the chilliquilles). I offer to go to Webster Wine Bar, and Liz jumps at the chance. They have great finger food.

We hop a cab and end up at Webster around 11pm. It's busy, but nothing like last year. Economic pain, I guess. I order my favorite bottle of wine (around $60) and Liz asks "How much is that?" I lie: $25.

Poor girl is now mixing all 3 types of alcohol. Dangerous for some, but she takes it in stride. We're laughing now, mostly because we look completely out of place in a wine bar on a Saturday night. She's dressed in sweats, and I'm in really poor looking jeans and a t-shirt (which cost me over $400 together). Midnight rolls around and the place dies down a bit, gets packed, then dies down again. Up and down all night. Liz and I share a couple of plates of finger food, and it's amazing, as Webster always is.

Liz is starting to look VERY cute. I notice an almost-dimple, and her face is precious. Plus her lips keep reminding me of her little send-off gift for me just a few days earlier. Kari didn't want to see me tonight, so I figured I'd have a weekend of porn and wanking. When it comes to porn, I really prefer the amateur stuff over the pro stuff, smaller boobs versus big fake ones. Kari, though, prefers the opposite. We don't share a similar taste in porn.

Liz looks at her phone for the first time, and she has 3 texts from her boyfriend. Oh, oh. She excuses herself (good girl!) to text him from the bathroom. I tab out, so she doesn't see the total of the night ($115 with tip).

Liz returns with a pout: she has to go. Boyfriend isn't happy that she ignored him, but she told him that she left her phone in silent. I prefer a girl, even a friend, who ignores their cell phone when they're out with others. I turn my off. Fuck those who aren't with me when I'm out having fun with friends.

So we hop a cab and zip back to my place to grab my car. We're both sober. I wanted to pick up my car since I figured I'd zip out on the highway to just do a mini late night road trip. No point in wasting a decent night in the house, bored. Fresh tunes on the iPod, full tank of gas, and a new air freshener. Perfect. I tell Liz this, and she's jealous that she'll be at her place with her boyfriend.

I drop her off, right in front. No smooch or offer for head, but a lot of knee touches and she even touched my hair a few times. Whoa.

Wait for her to go in, then zip off. 10 minutes after I'm on the Kennedy, she texts me: "He left, had to get up early. Come back and grab me." No problem! A U-turn at Addison, 15 minutes back down the highway and road, and she's hopping back in my car.

She loves my iPod. A great mix of Tom Waits, Public Enemy and Morrissey on my current playlist. We're jamming, and she's definitely fun for a 27 year old, a few years younger than me. Close in generations, though.

We're about 50 miles out of Chicago when she screams "JERKY!" Ahh, a girl who eats meat. Thank god. Sorry, vegans, but you fucking bore me. I can't take you anywhere nice, and I can't cook for you without it tasting like salt. Why not just suck my cock and swallow my load if you want something salty? Ugh.

We pull off the road just past the Illinois/Wisconsin border, and grab jerky, Redbulls, smokes, and some other fun things. Liz grabs a pack of condoms (!!!) and gives me a snarky smile. I assume they're not for me, but I say nothing.

We get back in the car, and instead of getting back on the highway, she points to the left: a seemingly long, dark country road. Fine!

20 minutes of driving down the Wisconsin highway and we reach more of nothing. It's great. We have the heater cranked to maximum, the sunroof open, and wrappers of Slim Jims on the backseat.

We both notice a bright light mist ahead, and driving 70MPH brings us to a gorgeous old farmhouse that is brightly lit. It's in beautiful shape. She thumbs me to pull over, and I do, down a not-quite-a-road dirt path that surely doesn't lead to the house. Probably a tractor access road.

"I should turn around, I bet this goes nowhere," I mention.

"Just put it in park, let's stare at that house." Liz is very forceful, which is good for a beer buddy. Most chicks can't make up their mind anyway, but she can.

We're talking about the house when I notice Liz is pulling her sweatpants down. I do a double-take, surprised because she wasn't flirting or anything.

"Warm, are you?" I say as I look into her eyes. She blushes, but in a sexy way. Off come her panties, next as she holds her eyes on mine.

"Look, I like your dick, and you got it hard twice for me in record time. My boyfriend can't keep it up for even 10 minutes, if he lasts that long. Let's fuck, and then we can go back to being friends."

"I'm not looking for a fuck buddy," I tell her. She nods, and then rubs my cock through my jeans. As she's doing that, she's got her fingers on her pussy, and her soft moans drive me nuts. I roll over to kiss her, slyly pulling the seat lever to lower her flat. I also push the seat back to give me floor space.

"I'm going to go down on you," I tell her, but she shakes her head no. She reaches over her back to the gas station bag, opens the condoms (not Magnums, ugh) and tells me to get out of my pants and boxers. I do.

The poor girl spends about 5 minutes trying to unroll the Trojans on me. When I'm this horny, I'm thicker than usual, so I prefer the extra space of the larger condoms. To the guys who don't know: Magnum boxes are bigger only for shower. The actual condoms are barely 1mm thicker. They're more comfortable.

Finally, I finish putting it on. She grabs my hips with one hand, my cock with the other, and slides me in. Tight, but not too tight. I'm sick of girls who brag about how tight they are, but then cry after an hour of pounding because they can't handle it.

Liz never complained. I know she came once, for sure, and I finished 3 times. Once in her mouth (mostly), once on her stomach (she never took her sweatshirt off but pulled it up for me), and once on her back and asshole. She even squealed when I shoved some spooge in her ass with my finger. Good girl.

We banged for a good 90 minutes, and she loved every minute of it. She may even have orgasmed a second time. The fact is, she loves to drink with me, and go on road trips, but she always likes my cock a lot. I got her to say the filthiest things ("Fuck my ass with that big cock," and "Bang my throat until I choke.") But I still don't want her as a fuck buddy. She's too much fun otherwise, and the fact that her boyfriend stays over once in awhile means she won't call me over for a booty call much.

If I'm going to have a friend-with-benefits, I'd rather her boyfriend live outside of her house. I don't like having a fuck buddy who is single, girls with boring boyfriends are better lays.

We ended up driving almost 200 miles out of Chicago, ending up in Sheboygan or so at 6am. We napped in the car, and woke up around noon. I just dropped her off, and she promised that next time we hang out, it will just be for beers.

And I gave her this link. Hope she reads it today.

Read the rest...

Thursday, November 6, 2008

manipulations, et. al

So Craiglist strikes again. In a drunken stupor, twenty minutes after dropping Kari off at home. We went to a bar, some rank dive.

Kari's got her monthly visitor this week. She teased me all night, promising a blowjob. By night's end, she'd forgotten. I was relieved, as her teeth kill me.

So when I spotted a '"friend's only" section post at CL that intrigued me, I responded. The post was 4 days old, looking for a guy or gal to just get beers with. Perfect.

I dropped an email, and received one back before midnight. Liz, 27, Uptown gal. She didn't ask for a pic or anything, not even a gay MySpace request. Just a request for my top ten bars. I responded.

5 minutes later, she responds: "Love them all. Best reply yet. Tomorrow at Five Star?"

Sure, I say. Kari's working late at the store she manages, til 10. Then needs to hit the sack to be up early. I tell her I'm making plans for tomorrow night. She's cool with it. I shoot off a response to Liz, 9pm confirm. Hear back her confirm. Then I crash.

Wednesday's a bore. Made enough cash wagering on Obama's win percentage that I'm free to ignore work till spring. Awesome for me.

8pm rolls around. I shower, toss on jeans and a T-shirt as it's not a date.

Grab a cab to Five Star. It's packed. Liz said she's be wearing a blue hoodie. Not there when I arrive. I magically snag two seats, order a Maker's and water, and watch the crowd.

This brunette wonder in a blue hoodie arrives 10 minutes later. She notices me and smiles. Cute. She's got a great body, dick sucking lips, and a cute haircut. Too bad she's just a beerpal.

She sits, and we talk immediately. I let her do most of it, since she's obviously more bored with life than I am.

Her: boyfriend of 15 months, live together 4 nights a week. Works for a local college. Most of her friends are marrying and running to the burbs. Happy overall but bored.

Our first round turns into 4. I'm definitely tipsy. I ask her if she's ready to leave, to which she says "as long as it's another bar!"

Cute.

We cab it to my car, and drive to some bar in Ukie Village. Little dive bar. 2 more rounds, lots of fun convo. She's touching my arms and knees A LOT, but I ignore it. Before i 'd believe it, it's last call.

"Do you need a ride?" I ask. She does. Her place is nearby.

I head toward Augusta when she tells me to take an alley shortcut. I do, and 2 blocks later she points to a garage for me to pull up next to. This isn't her street, I tell her.

She looks at me, puts the car in park, climbs her abs over my armrest and puts her fingers on my fly.

"Don't you have a serious boyfriend?" She does, but I turned her on and it's just head.

It takes her 5 minutes to get my button fly free, enough time to get me very hard. She digs my pants down, and slides her finger into my boxers. "Whoa," she says as my cock pops out. It's shorter than average but thicker than most hands can handle.

A few amazing licks and kissed and then her nose is down to my thigh. The girl's got talent.

15 minutes of the sloppiest, best head I've gotten in 3 years, and I'm getting close. I tell her to sloow down and get me a napkin from my glovebox.

She pops her adorable face up and says, "that's nice of you to warn me. You taste great, squirt your load down my throat. Fuck my face if you want."

I oblige. She's using all her spit to keep things noisy, so I unleash right into her mouth. I pulled on her hair to back her off, and on the final spurt ripped her back so my cock blasts a little on her cheek. She smiles. Beautiful.

She licks up what she missed, off her first and then me. That causes me to get hard again, not 30 seconds after my first load.

"Holy shit!" She exclaims. The girls familiar with lame, poor 24 year olds. I just sit, smiling, as she goes to town once more. 10 minutes later, she's swallowing every drop.

I offer to go down on her, but she admits to ragging. She does tell me as I drive her the last 4 blocks that she'll be done in2 days, and to bring condoms.

There goes a beer buddy. Thanks, Craiglist.

Read the rest...