24 9 / 2012
Anonymous said: BEANIE BABIES
this is a really thoughtful question. I’ll have to get back to you.
24 9 / 2012
Anonymous said: I feel like I need a couple new tricks in bed. I heard spitting on his dick is hot. Should I try that?
yeah but your lips will get chapped so make sure you have burts bees for the morning after.
29 3 / 2011
Anonymous said: do you think it's possible for a guy to be afraid of my boobs?
i think there are very few instances when men are afraid of boobs. one of these instances is when a man is at risk for asphyxiation (i love to spell that word) via boobs. another is if the man is a very timid gay man. lots of gay men are not physically turned on by boobs, but can appreciate them for the silly sacks of flab that they are. a third scenario is if the boobs belong to someone old and gross or perhaps a relative. even an old and gross relative. If none of these is the case, then rest assured he isn’t frightened of your bosom—just a pussy.
28 3 / 2011
Anonymous said: What is the meaning of life and why are we here?
"Dear Loser, [Chris]~~~~!!!!!
I thought you liked me you said it yourself I hate you .People only say you asked me out because you needed a date for the dance and that after the dance you would dump me well guess what bastert I dumped you cause you were thnking that I cheated on you i didn’t so like that you guys are and so marty that you are you called me a slut.I hung up on you cause you tol me it on the phone because I guess werent man enough to tell me it in my face!I hate you and also guess what my mother hates you to that she the one who put me to do this ,you come to breakfast every morning and I aint stupid you try to sit next to me and my lil bro who only 7YRs old hates you to and dont even know what you did and it always blocking your chair.haha!I went out with another boy after you and after we were over you an idiot dared you even tried to ask me out again I didnt break up with him for you OK! I hate you ive always hated you spreading to everyone that i cheated on you when you just got jealouse that i used to talk to your friends to your so jealouse you automatically think I like them well guess maybe i do maybe i dont gotta problem you aint my boyfriend anymore I dont have to tell you who i like or who iam with and why got it i dont like you anymore the other day you told me that I have to who I like or who Iam thinking of going out with its none of your buisness got that to you loser!I hate you and I know you but i dont like you i dont care what your stupid freinds say you make me touch your hands for stupid reasons u accidentally say you hugged me i will never like you again I HATE YOU I HATE YOU MORE THAN ANYTHING IN THIS DAMN WORLDDDDDDDDDD id rather date a spider or rat den u ur soooo ugly and fat !!!!!!!!!!And then saying that i loooooooved you pleasssse!!!!!!!!!!!Your such n ass wipe n bastert!! I HATE YOOOOOOOOOO
Well bi you piece of shit i have more things to do right now then remember YOU”
28 3 / 2011
Anonymous said: I've been watching clips of tranny/trap movies (like Bailey Jay doing other she-males), and am a little confused. I'm a little turned on, but don't know how to tell my girlfriend without her freaking out. Should I even tell her at all?
Dear Tranny Chaser,
Everyone is a PHREAK. you probably dont need to tell your girlfriend unless you are really drunk. She will probably be weirded out. and tell her friends. so unless you want this to be public knowledge, keep this to yourself. Occasionally I ask boys i am kissing what their fantasy-weird-shit is because what if it was something i’d be into? then we could get hella freaky/phreaky. just keep watching your special films under your covers in bed. unless you have a hella progressive honey.
p.s. call me.
09 2 / 2011
Anonymous said: Dear Madeline,
I think I spend too much money on alcohol. Do you have any tips on how to spend less money on alcohol without having to stop drinking it?
Here are some tips on how to stop spending so much.
- wear a low cut shirt.
- drink a glass of pop or something between your alcoholic drinks. sometimes i just want to have something else to sip on and so i get another drink when really i could have been drinking juice and have been just as happy. I usually dont realizes this til i’m wasted and have been chugging whiskey sours down for 3 hours.
- come up with some game that you rig to make sure you are making people buy you a drink. This past weekend I made a fortune teller where 5 out of 8 fortunes were ‘you will buy me a drink.’
- DRINK AT HOME. quit going to the bar you slut, and down your PBR in the privacy of your own home.
- start hanging out with people who are mormons or jehovahs witnesses because usually they do some fun stuff that is not boozing. just make sure they aren’t trying to convert you—unless you’re into eternal salvation and stuff.
09 2 / 2011
Anonymous said: wanna go on a date?
obviously i would like nothing better than do go on a date. Is it with you? Let me know if you are hot and/or loaded because I am in the market for a sugar daddy.
29 1 / 2011
michaelstandish said: I'm too broke to keep dating the way I am, how do I get the guys to pay for every date? Except not lose any of the sort of leverage that exists in a gay relationship when you pay for stuff?
Put out. Obvy. Next question. Kidding (kinda). As a girl who has only been paid for like 3 times in her life*, I can give you good advice. If a dinner date has gone well, have a plan by the time the check arrives. Slyly suggest that you go dutch this time, but that you’ll pick up the tab on the next date. Make this next date something cheap. You can’t hide that you’re broke from this guy for too long if you want it to get serious. Tell him your date is a surprise and then lead him someplace like White Castle and apologize that you’re broke but youre still trying to Tim Gunn it (MAKE IT WORK for all you non-‘mos). Then get this fucking White Castles to go. Take it somewhere cute. You could take it to the Chicago Cultural Center and then walk around the building because there is really awesome stuff in there and even when the stuff is shitty you can lol at it and gauge this guys sense of humor and therefore the size of his throbbing cock.
Then you just hope that his triflin’ ass isnt broke and that he takes your sorry br0ke ass (jk you real sexxi) on some expensive date to see Blue Man Group or something. (WILL SOMEONE TAKE ME TO SEE BLUE MAN GROUP?)
or just put an ad on craigslist that you’re a fyne chicken searching for a sugar daddy who gives bomb beejays.
*When Sam was my kinda boyfriend I think he paid for me to see Tropic Thunder. When this weirdo from OkCups took me on a date, he showed up wearing vintage military clothing and paid for my dinner and bowling. I didn’t call him back. When Ian was my boyfriend, he paid for my dinner one time but he is gay now so i think that might render it invalid.
29 1 / 2011
Anonymous said: My penis is 'too big'.
Thanks for consulting me. Penis size is a big struggle for many of us. I know I struggle with it. I have a few follow up questions for you! Too big for what? For vaginal or anal intercourse? For your underpants? For insertion into a gatorade bottle?
If its too large for a gatorade bottle, consider insertion into a Pom Wonderful Tea bottle. They have very large mouths and are almost more like a cup than a bottle.
If it is too large for your underpants, why not go commando? It’s becoming more and more socially acceptable to do so.
If its too large for intercourse, I’d recommend some vaginal dilation kits that can be found by googling ‘vaginal dilation’. Or just fuck him/her until their butt/vaj loosens up. Fun tip: use tears and blood for additional lubrication!
Thanks for writing,