Gettin' Down in Chi-Town

Post(s) tagged with "chicago"

Yes, my darlings, you can "like" me now. ⇢
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Confidacation and CommunidanceDear Lucy, I’ve been with my boyfriend for just about a year now and I lost my virginity to him ages ago. Recently, he told me I wasn’t great in bed. I thought everything (sexually) was great. Major confidence drainer; I’ve felt awful since he told me. My only saving grace is that he’s the only guy I’ve had sex with so it’s partially his fault too ;P How do I recover from hearing this? :( I’ve had awful confidence issues all my life, improved dramatically, now I’m back to where I started. :(Pardon moi? He said WHAT?!It is way not cool to tell someone they aren’t great in bed, and then just leave it at that. Did he offer anything else? Specifics? Things he wanted that you could try together? If not, then you are left with no way to move forward, and that is his bad. You can’t “recover” from an insensitive comment like this. You can only discuss it fully, and come up with a plan together on how to make your sexy-time improve. And, are you sure you’re entirely satisfied? Maybe you can also bring up some things that would make you happier in bed, as well.As for your self-confidence, it is a total dick move for this dude to bring you down like that. It is his responsibility as your partner to make you feel good about yourself. If he is not complimentary and confidence-boosting in any part of your relationship, then it is time to end the relationship. Start seeing someone who will make you feel GOOD, emotionally and physically, and who understands that communication is the only way for a healthy relationship to develop.Everyone has the power to be good in bed. It takes practice, and most importantly, COMMUNICATION.xoxo,Lucy

Confidacation and Communidance

Dear Lucy, I’ve been with my boyfriend for just about a year now and I lost my virginity to him ages ago. Recently, he told me I wasn’t great in bed. I thought everything (sexually) was great. Major confidence drainer; I’ve felt awful since he told me. My only saving grace is that he’s the only guy I’ve had sex with so it’s partially his fault too ;P How do I recover from hearing this? :( I’ve had awful confidence issues all my life, improved dramatically, now I’m back to where I started. :(

Pardon moi? He said WHAT?!

It is way not cool to tell someone they aren’t great in bed, and then just leave it at that. Did he offer anything else? Specifics? Things he wanted that you could try together? If not, then you are left with no way to move forward, and that is his bad. You can’t “recover” from an insensitive comment like this. You can only discuss it fully, and come up with a plan together on how to make your sexy-time improve. And, are you sure you’re entirely satisfied? Maybe you can also bring up some things that would make you happier in bed, as well.

As for your self-confidence, it is a total dick move for this dude to bring you down like that. It is his responsibility as your partner to make you feel good about yourself. If he is not complimentary and confidence-boosting in any part of your relationship, then it is time to end the relationship. Start seeing someone who will make you feel GOOD, emotionally and physically, and who understands that communication is the only way for a healthy relationship to develop.

Everyone has the power to be good in bed. It takes practice, and most importantly, COMMUNICATION.

xoxo,
Lucy

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Until You’re Mine, I Draw the Line
Dear Lucy,
I’ve been on 2 dates with a guy I could end up dating long-term. On our 2nd date I conveniently forgot my apartment key; ending up staying the night at his place. We made out, he fingered and caressed me, and I gave him a couple of hand jobs. I feel comfortable with the casualness of the night, but I denied him when he asked for a blow job (price of admission is eating me out!). I want to experiment more with him (I’m a virgin). How do I tell him I’m drawing the line until we’re more official?
Based on what you’ve written, I am a bit confused about where you want to actually “draw the line” with the guy you’re seeing.
You’re already involved in sexual acts with this dude, and it sounds like it’s going well so far. You gave each other manual stimulation, and you said you felt comfortable.
Then you denied a blow job, supposedly because you wanted to balance it out with receiving oral, as well. That’s totally reasonable, but is this something you explained to him? Did he know you wanted it, and he denied it? Or did you not bring it up fully and honestly?
Also, when you say you “conveniently forgot your apartment key,” was this intentional and you wanted to stay the night at his place, or did he convince you to went you weren’t to keen on it? These are important aspects of your blossoming relationship that you need to consider seriously before moving forward. Essentially, are you going to take control of your own wants and needs, or let yourself be swayed when you’re not really feeling it?
It’s great that you want to experiment, and if you’re comfortable with your new man-friend, then you should totally go for it. When it comes down to it, my main piece of advice on how to tell him you’re drawing the is to tell him you’re drawing the line.
It’s your responsibility to explain to him what you want out of your relationship, romantically and sexually. And then you need to listen, and have a conversation and what he wants. If you find that you are on the same page about being safe and honest, and you are both genuinely interested in making each other happy, then you will be in a good place to move forward. It’s not fair, however, to lead him on, making him think that you want something that you will later deny or revoke.
Maybe it sounds contrived, but it never fails to be true: the key to any relationship in life is communication. Use it well.
xoxo, Lucy

Until You’re Mine, I Draw the Line

Dear Lucy,

I’ve been on 2 dates with a guy I could end up dating long-term. On our 2nd date I conveniently forgot my apartment key; ending up staying the night at his place. We made out, he fingered and caressed me, and I gave him a couple of hand jobs. I feel comfortable with the casualness of the night, but I denied him when he asked for a blow job (price of admission is eating me out!). I want to experiment more with him (I’m a virgin). How do I tell him I’m drawing the line until we’re more official?

Based on what you’ve written, I am a bit confused about where you want to actually “draw the line” with the guy you’re seeing.

You’re already involved in sexual acts with this dude, and it sounds like it’s going well so far. You gave each other manual stimulation, and you said you felt comfortable.

Then you denied a blow job, supposedly because you wanted to balance it out with receiving oral, as well. That’s totally reasonable, but is this something you explained to him? Did he know you wanted it, and he denied it? Or did you not bring it up fully and honestly?

Also, when you say you “conveniently forgot your apartment key,” was this intentional and you wanted to stay the night at his place, or did he convince you to went you weren’t to keen on it? These are important aspects of your blossoming relationship that you need to consider seriously before moving forward. Essentially, are you going to take control of your own wants and needs, or let yourself be swayed when you’re not really feeling it?

It’s great that you want to experiment, and if you’re comfortable with your new man-friend, then you should totally go for it. When it comes down to it, my main piece of advice on how to tell him you’re drawing the is to tell him you’re drawing the line.

It’s your responsibility to explain to him what you want out of your relationship, romantically and sexually. And then you need to listen, and have a conversation and what he wants. If you find that you are on the same page about being safe and honest, and you are both genuinely interested in making each other happy, then you will be in a good place to move forward. It’s not fair, however, to lead him on, making him think that you want something that you will later deny or revoke.

Maybe it sounds contrived, but it never fails to be true: the key to any relationship in life is communication. Use it well.

xoxo, Lucy

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“Out with the cold, in with the woo!”
-E. Marshall
(Spring may be slowly seeping in, here in Chicago…
Can’t WAIT!! xoxo, Lucy)

“Out with the cold, in with the woo!”

-E. Marshall

(Spring may be slowly seeping in, here in Chicago…

Can’t WAIT!! xoxo, Lucy)

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Sex Advice Relay: Spring Edition 2011Happy St. Paddy’s Day! Things are always crazy on this night here in Chicago. It’s like Chicago’s Mardi Gras, for real. I’ve seen multiple trolleys driving about the city, packed with drunk Chads and Trixies, bagpipers on the roof. Rigoddamndiculous. So, no, I am not out partying. I am here, cozy at home, writing to you, my darlin’ wee lads and lassies.I know it’s been an agonizing 10 days without a post, but I’ve been really swamped. Yeah what else is new? Well, something IS new, that’s a pretty big deal, but you’ll have to wait til my next post to hear about it. In the intervening time, here’s a bunch o’ questions to fill that empty space in your sex-advice hungry heart.
 
Dear Lucy, 
I’m nineteen and I have just started kissing boys (and girls) but I have only had drunken hook-ups. For some reason I haven’t been turned on by any of them. Do you think I need a stronger emotional connection or just a sober one?
You probably need both. It’s real easy to get things started when you’re drinking- your inhibitions are lowered, you can act braver without as much worry, you can always pass off an embarrassing moment as a drunken mishap, or you can even pretend you don’t remember things that went down. If you have just started kissing people, you may not even know what being turned on is like! I would say to step back a bit. Work on getting to know people before making out, and go on some normal, sober dates. Then, once you’ve established that you have some sort of emotional connection with a person, you can move forward into kissy land. There, with a sober connection established, you just may find the horniness you’re searching for.
 hi i have a questioni wanna lose my virginity w/o a condom, at least for the initial entry. i just feel that it would be best that way. of course, i would put one on afterwards. im just wondering is this safe? if he doesnt masturbate for a week beforehand, would it be okay for that first moment to use no condom? thanks in advance I understand the first part of your question; it may feel more natural to have sex without a condom the first time. Condoms can be uncomfortable and hard to get used to. But, they are super necessary for safe sex. So, I would say that it would be a really really good idea to use one, even the first time. This depends a little on your situation, however. Who is the “he” that you’re planning to have sex with? If you are both virgins, then it would behoove you both to get tested for STDs before going very far sexually. You should also look into other forms of birth control besides condoms. If, AND ONLY IF, you both have a clean bill of health, and you are using a reliable birth control (like the pill, ring, or IUD), then you could consider sex without a condom.As for the second half of your question, I have yet to figure out what you mean about your dude’s masturbation schedule. The amount your sexual partner masturbates has absolutely no bearing on the possibility of you getting pregnant or STDs from unprotected sex. Even if he does not masturbate for a week, you should still follow my advice above (getting tested and birth control, stat!). In fact, I think that NOT masturbating could actually cause more risk for you! Ejaculating clears your dude’s pipes of bacteria, which keeps his dick cleaner and less likely to transfer things to you. Also, he may be so pent up from the anticipation of having sex and not relieving himself, that he may be more likely to prematurely ejaculate. What I mean is, if all that sexual tension is building up inside him, then it is possible that he could splooge right at the first moment he enters you. And that is the opposite of what you want.I know this is vague, but how can I get dates? I’m a somewhat attractive, 18 year old college student with no love life. I know it’s because I’m shy and not at all forward. How can I push myself to be a little more out there without it being forced or awkward?You’re in college! This is the absolute perfect time for you to get out there. You’re 18, so I assume a freshman. Not sure what college you’re at, but some things are universal in universities: the social scene is poppin’ off. Check out the functions that your school sponsors: clubs, art classes, dances, mixers, study groups, sports, trips, the list goes on. Never will you have an experience like the beginning of college again, where there is a whole organizational structure just to say “Here! Have some friends!” Don’t necessarily go into a new group experience expecting to meet your romantic match right off the bat. Rather, think about just building friendships with new people who are into the same sorts of things as you. Start hanging with like-minded folks, and relationships will develop. Eventually, you may find a spark with a new friend, or get introduced to friends-of-friends that you hit it off with as well. It’ll be a little awkward at first, but take baby steps, and don’t pressure yourself too hard. Just take advantage of the opportunities that surround you whenever you can.

So there’s this guy at my school and he stares. He knows I stare too and I stare cause I’ve got a crush on him, and I don’t talk to him at all, but why does he stare and don’t do anything? Could it be that he has staring problems?
Uh, why do YOU stare and don’t do anything? If you’re staring at this crush-worthy dude, and he’s staring back, chances are he’s into you, too. Or maybe he just keeps catching you staring at him, and he thinks that YOU have a staring problem! Get up and talk to the guy, for cryin’ out loud.
xoxo, Lucy

Sex Advice Relay: Spring Edition 2011

Happy St. Paddy’s Day! Things are always crazy on this night here in Chicago. It’s like Chicago’s Mardi Gras, for real. I’ve seen multiple trolleys driving about the city, packed with drunk Chads and Trixies, bagpipers on the roof. Rigoddamndiculous. So, no, I am not out partying. I am here, cozy at home, writing to you, my darlin’ wee lads and lassies.

I know it’s been an agonizing 10 days without a post, but I’ve been really swamped. Yeah what else is new? Well, something IS new, that’s a pretty big deal, but you’ll have to wait til my next post to hear about it. In the intervening time, here’s a bunch o’ questions to fill that empty space in your sex-advice hungry heart.

 

Dear Lucy,

I’m nineteen and I have just started kissing boys (and girls) but I have only had drunken hook-ups. For some reason I haven’t been turned on by any of them. Do you think I need a stronger emotional connection or just a sober one?

You probably need both. It’s real easy to get things started when you’re drinking- your inhibitions are lowered, you can act braver without as much worry, you can always pass off an embarrassing moment as a drunken mishap, or you can even pretend you don’t remember things that went down. If you have just started kissing people, you may not even know what being turned on is like! I would say to step back a bit. Work on getting to know people before making out, and go on some normal, sober dates. Then, once you’ve established that you have some sort of emotional connection with a person, you can move forward into kissy land. There, with a sober connection established, you just may find the horniness you’re searching for.

 
hi i have a question
i wanna lose my virginity w/o a condom, at least for the initial entry. i just feel that it would be best that way. of course, i would put one on afterwards. im just wondering is this safe? if he doesnt masturbate for a week beforehand, would it be okay for that first moment to use no condom? thanks in advance
 
I understand the first part of your question; it may feel more natural to have sex without a condom the first time. Condoms can be uncomfortable and hard to get used to. But, they are super necessary for safe sex. So, I would say that it would be a really really good idea to use one, even the first time. This depends a little on your situation, however. Who is the “he” that you’re planning to have sex with? If you are both virgins, then it would behoove you both to get tested for STDs before going very far sexually. You should also look into other forms of birth control besides condoms. If, AND ONLY IF, you both have a clean bill of health, and you are using a reliable birth control (like the pill, ring, or IUD), then you could consider sex without a condom.

As for the second half of your question, I have yet to figure out what you mean about your dude’s masturbation schedule. The amount your sexual partner masturbates has absolutely no bearing on the possibility of you getting pregnant or STDs from unprotected sex. Even if he does not masturbate for a week, you should still follow my advice above (getting tested and birth control, stat!). In fact, I think that NOT masturbating could actually cause more risk for you! Ejaculating clears your dude’s pipes of bacteria, which keeps his dick cleaner and less likely to transfer things to you. Also, he may be so pent up from the anticipation of having sex and not relieving himself, that he may be more likely to prematurely ejaculate. What I mean is, if all that sexual tension is building up inside him, then it is possible that he could splooge right at the first moment he enters you. And that is the opposite of what you want.

I know this is vague, but how can I get dates? I’m a somewhat attractive, 18 year old college student with no love life. I know it’s because I’m shy and not at all forward. How can I push myself to be a little more out there without it being forced or awkward?

You’re in college! This is the absolute perfect time for you to get out there. You’re 18, so I assume a freshman. Not sure what college you’re at, but some things are universal in universities: the social scene is poppin’ off. Check out the functions that your school sponsors: clubs, art classes, dances, mixers, study groups, sports, trips, the list goes on. Never will you have an experience like the beginning of college again, where there is a whole organizational structure just to say “Here! Have some friends!” Don’t necessarily go into a new group experience expecting to meet your romantic match right off the bat. Rather, think about just building friendships with new people who are into the same sorts of things as you. Start hanging with like-minded folks, and relationships will develop. Eventually, you may find a spark with a new friend, or get introduced to friends-of-friends that you hit it off with as well. It’ll be a little awkward at first, but take baby steps, and don’t pressure yourself too hard. Just take advantage of the opportunities that surround you whenever you can.

So there’s this guy at my school and he stares. He knows I stare too and I stare cause I’ve got a crush on him, and I don’t talk to him at all, but why does he stare and don’t do anything? Could it be that he has staring problems?

Uh, why do YOU stare and don’t do anything? If you’re staring at this crush-worthy dude, and he’s staring back, chances are he’s into you, too. Or maybe he just keeps catching you staring at him, and he thinks that YOU have a staring problem! Get up and talk to the guy, for cryin’ out loud.


xoxo, Lucy

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A Hard Sell: Chicago for Cynthia 2011

This is a blog about sex, yes, but it is also about the place I call home, the city dearest to my heart: Chicago, IL. Chi-town is a city of politics. And I am pleased to say that now I can write an article about sex in Chicago politics that is not involving some politician’s stupid infidelity scandal.

You are probably aware that our mayor of the past bajillion years, Daley the Jr., is resigning. This man has in charge of running our city- be it loyally, lovingly, loudly, or shadily- for most of my memory. And now he’s stepping down, and just about everybody else is stepping up to replace him.

Including, I have learned recently, a certain woman name Cynthia P. Caster.  Famous in some circles, and certainly admired by me, this is Ms. Caster’s first foray into politics. Caster is best known “for her work as an artist and iconic status as a rock n’ roll groupie.” A native Chicagoan, Caster’s interests in art and rock ‘n’ roll in the late 60’s led her to her life’s work: making plaster casts of rock stars’ cocks and, more recently, boobs.

Caster (the middle initial stands for “Plaster,” of course) is now changing her ways, and calls herself a “recovering groupie.” She’s passionate about our fair city, and seems to be creating a real campaign. Her campaign site (http://www.chicagoforcynthia.com) looks professional and patriotic, a far cry from her other official website, with menu buttons shaped like squirting penises (http://www.cynthiaplastercaster.com/index.html) . No, Caster is serious now. She’s running on a platform that she’s “hard on crime.” Really.

I’m not sure if I’ll vote for Cynthia, although it would be great to have a woman in office running this City of Big Shoulders. But if she’s really going for it, I’m certainly interested to see how she does. I’ll totally attend a rally. You see, I’m quite in love with Jimi Hendrix. In the heights of teenage angst, I used to lie on the floor staring up at my best friend’s spinning disco ball, wishing I’d been born earlier so I could’ve met Jimi. I swore that, had I the chance, I would have followed him around the world until I finally got to fuck the legend. And, while Caster claims she didn’t sleep with him, she definitely has a trophy to prove that at least she touched his hard dick. It looks pretty magnificent.

So, while I vote tomorrow for other important key figures in American politics, I’ll really be thinking about our next upcoming election. Caster says she cares about the people of Chicago, and I believe her. Maybe she could be the change Chicago needs. I’ll keep looking into Cynthia’s political progress.

In her own words, “So, townspeople! The skies are ablaze with Plasterness! Ooooh! Aaaah!”

 

Vote tomorrow!

Xoxo, Lucy

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[Flash 9 is required to listen to audio.]

“Over it Over Again”

-She & Him

Just saw She & Him play for free in Millenium Park. Feeling serious Chicago love right now. It was truly a lovely evening- pleasant temperature, everyone in good spirits with their picnics and summer dresses, fucking great music.

And that goddamn adorable Zooey Deschanel. Does anyone not have a crush on her?

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“Sex is like snow, you never know how many inches you’re going to get or how long it will last.”
-Anonymous
(In honor of the blizzard going on in Chicago right now…)

“Sex is like snow, you never know how many inches you’re going to get or how long it will last.”

-Anonymous

(In honor of the blizzard going on in Chicago right now…)

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Thanks for posting me, Dealbreaker. ⇢

dealbreaker:

GUESTBREAKER: You Don’t Have Sheets On Your Bed

No, I am not going to have sex with you on a bare mattress because I am not a crack whore and this is not a shack with busted-out windows. You are an adult and this is actually a semi-decent apartment.

Where were you raised? I’m sure you had sheets on your bed as a child. Yet, somehow you lost the need for them along the way. Perhaps you started doing your own laundry in college, and decided it was too much work to wash your sheets and then return them to your mattress. Perhaps they were stolen from the laundry mat, or you made them into togas for parties and they never made it back home. In any case, where are they now?

I’ll tell you where they aren’t: covering your extra-long twin mattress, which is stained with bong water, and what I’m praying is barbeque sauce. It would appear that your mother didn’t raise you right, and I’m sure she would not appreciate knowing that that is the message you’re sending out to your lady visitors.

What’s that? You have something for the bed? Oh… oh no. That is a nylon sleeping bag from your boy scout days, and that is a damp bath towel. Those are not sheets, and they are really not a suitable substitute. Go to Target and buy some sheets. They’re like $20.

A Guest Dealbreaker written by Lucy.

Source: dealbreaker

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Life. Love. Lust.

I'm Lucy. I live in Chicago and I like to talk about sex. Give me a topic: I'm happy to answer any questions about love, sex, and relationships. Email me at LucyRockwell@gmail.com


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