Tag Archives: first time for everything

True Story: My Crazy Craigslist Casual Encounter

Your To-Do List
What's On Your To Do List?
What's on it? Read More »
My First Time...
...being polyamorous. Read More »
Guide: Airport Hookups
Ami's practical guide to picking up dudes at the airport. Read More »
True Story: My Crazy Craigslist Casual Encounter

The results are in — after asking you guys to share with us the thing you’d most like to check off your to-do list, we’ve got a winner! Turns out sex with a near stranger is something that we’re all kinda into — check out this piece on using Craigslist for more than just finding an apartment, and be sure to see “The To Do List” starring Aubrey Plaza, in theaters today!

When I was 23, I moved to Seattle from New York City, for no particular reason except that I felt compelled to. When I got there, I was coming down from a pretty irreverent sex life in the Big Apple. I’d just had my first foursome and I was at what you could call a sexual peak. So basically, I was horny all the time.

I moved into a condominium which was like living on Pluto or some planet where I was the only inhabitant. My new condo had an elevator, a gym downstairs, two bathrooms, and a dishwasher. I’d never lived in a nice place before –  especially one with a dishwasher — and I truly didn’t know what to do with myself. Keep reading »

First Time For Everything: Attending A Sex Toy Party

First Time: Cock Ring
The first time using a vibrating cock ring. Read More »
First Time: Orgy
orgy
What happened at Jessica's first orgy. Read More »

I’d been invited to three adult novelty parties via Facebook. The first two I skipped, but decided the third time was a charm. You see, I’m a scientist, a doctor, with the capacity to deduce conclusive results from my experiments, even failed ones. After my divorce I concluded that a successful relationship requires me to think of what I can give to a partner both emotionally and sexually, rather than focusing solely on what he could give to me.

That’s what sent me to a relationship seminar about sexuality and spirituality. It’s also what solidified the decision to say yes to this party. I am in a new relationship, considering spending the rest of my life with a man and his two children. I figured, subscribing to my friend’s philosophy: “You must try everything once or you’ll die stupid.” Besides, alcohol, food and sex talk with a bunch of strangers didn’t sound like a bad way to spend an afternoon. Keep reading »

First Time For Everything: Using A Vibrating C**k Ring

First Time: Orgy
orgy
What happened at Jessica's first orgy. Read More »
Peeing Or Squirting?
7 ways to know if you're a female ejaculator. Read More »
First Time: Anal Beads
A writer tells us about her first encounters with anal beads. Read More »

The other weekend I was at brunch with some friends and the topic of our conversation was cock rings. Not your average brunch convo, but a lively one nonetheless.

“If you haven’t already, you girls have to get a vibrating cock ring. It changed everything.”

I know, this sounds like one of those cheesy tampon commercials. I’m paraphrasing from memory, but this was a near-exact approximation of what she said. Next, she went on about her amazing orgasm thanks to said vibrating cock ring. She is also a squirter. So she’s one of those orgasmic overachievers. Bitch.

By the end of brunch the other girls wanted to rush to the CVS down the block to buy them. I spent most of brunch trying to stifle an eye roll. Not because I’m single and have no one to fuck and have never squirted in my life (although that might be part of it), but because I find vibrating cock rings to be highly overrated and the time I used one was farcical at best. Keep reading »

First Time For Everything: Hooking Up With A Woman

I'm A Bisexual
Carrie is an out and proud bisexual. Read More »
Reasons Women Experiment
Six reasons women experiment with other women. Read More »
Definitions Of Sex
How lesbian sex changed Rachel's definition of straight sex. Read More »

Simply put, I have been boy crazy since elementary school.

Men have always been the ones I kissed, fellated, fucked, Skype-sexed, you name it. All of my sexual experiences and struggles coming to terms with my sexual kinks have involved cisgendered men.

But until recently, there was a side of myself that lay dormant so long it would probably more appropriate to call it “stagnant.” It was a side of myself that I didn’t act upon out of fear of what would happen: the one that had sexual and romantic feelings for women. Keep reading »

First Time For Everything: Two Blowjobs In One Day

First Time: Spanking Party
spanking photo
This is what happens at a spanking party. Read More »
First Time: Anal Beads
A writer tells us about her first encounters with anal beads. Read More »
First Time: Fisting
A woman talks about her first fisting experience. Read More »

Once upon a time in 2005, there was a young lady in her mid-20′s who lived in a faraway land known as New York City. This young lady was single and, as a result, was in constant pursuit of a man to be her boyfriend. She searched far and wide throughout the land for a proper companion. Eventually, many years later, she would find one to call her own, but in 2005 she was rifling through as many men as were available, ready, and willing. In the summer of 2005 she was balancing two different gentlemen, and it was in said balancing act that our fair maiden accomplished the near-impossible – the arguably slutty, the inarguably promiscuous – and put two penises into her mouth in one day.

Two different penises, that is. Just so we’re clear. Keep reading »

First Time For Everything: A Spanking Party

Getting Spanked
spanking photo
There is a first time for everything! Read More »
Want To Try Spanking?
Doin' It With Dr. V explains how to spank and be spanked! Read More »

“Call me in one hour and tell me your boyfriend dumped you,” I told my girl friend as we stood outside the movie theater where we had just seen “Magic Mike.” “If the party’s weird and I want to leave, I’ll say ‘Oh my God, are you okay? I’ll come meet you!’ Got it?”

“Sure thing,” my friend promised.

“I’m texting you the address I’m going to right now,” I told her, tapping on my iPhone. “Just in case these people turn out to be rapist-murderers.”

“I’m sure they’ll be fine,” she soothed me. We hugged goodbye and parted at a street corner. “Have fun!” is what she called as I walked away.

Have fun at your spanking party is what she meant. Keep reading »

First Time For Everything: A Condom Got Lost Inside My Vagina

Angry Vagina
This writer had a falling out with her vagina. Read More »

I always laughed when, in middle school, my friends worried about getting tampons stuck inside of them. I was the first to brush off any fear that anything could actually get stuck inside your vagina. I mean, how could you not know if something is up in there? However, I have been converted – a vagina can be a cavernous hiding spot for all sorts of paraphernalia. Somehow, unbeknownst to me, I once got a condom lost inside my vagina for days. Yes, days. Keep reading »

First Time For Everything: Anal Beads

Peeing Or Squirting?
7 ways to know if you're a female ejaculator. Read More »

Years ago, in my early 20s, I dated a guy named Mike. Now Mike, by all accounts, was heterosexual. Perhaps you’re thinking, Um, hello? Duh. Of course he was. He was dating you, and you’re a woman. But as any lady in her 20s living in New York can tell you, this doesn’t always guarantee straightness. No. It does not. However, Mike seemed thoroughly, authentically hetero. And as evidence of that fact – and just to get down to the nitty-gritty of it – I offer you the following: He had a healthy sexual appetite and, more to the point, he really enjoyed the performance of The Oral Sex. And more to the point, he was unfailingly, ahem, aroused after having done so to moi et moi’s lady-bits.

So this one night, Straight Mike and I were enjoying a couple of post-coital drinks and chitting and chatting, and I – in a pathetic if nonetheless truthful attempt to make him think me more worldly than I was/am – mentioned having made out with a girl in college. I said, “Well, there was this month in college when I kept making out with my friend Barbara.”

I expected him to tell me how edgy, original, and adventurous this was, but instead, he went, “Oh, yeah. Well, I mean, I guess I never think that stuff’s that big a deal. I mean, well, I sucked this guy’s dick, like … last year I guess it was?” Keep reading »

First Time For Everything: Dancing At Coyote Ugly

My First Time...
...being polyamorous. Read More »
My First Time...
...being a dominatrix. Read More »
My First Time...
...posing nude. Read More »

Here’s a thing I can promise: If you invite me to your wedding, your other guests will comment on the quality of my dancing. It’s inevitable. I’ve never been to a wedding where the thank you note for whatever I picked off the registry didn’t do exactly that. Anything from, “My Uncle Morty loved your dancing!” to “You really got the party started!” My dancing skillz come down to one word: Commitment. I hear a song that moves me, and I commit. I give 100 percent. The way my best friend once described it: “It’s like, one second you’re in your chair eating a slice of cake or whatever, then the next second you’re shimmying so hard I’m, like, ‘OMG: I’m worried her head’s gonna fall off.’ You go from zero to 60 like that. Keep reading »

First Time For Everything: A Televised First Kiss

Dating Basics
5 ways to get back to dating basics. Read More »
How NOT To Kiss
The worst smooches ever. Read More »
First Moves
One guy talks about making the first move. Read More »

The other night I went on a date. I was following my own advice about getting back to dating basics, and thought it would be a good idea to invite my date to a live taping of a game show that I was offered tickets to. Perfect. A date where we could just have some good, clean fun. Three minutes in the door and the woman checking us in, who I should mention had a raging herpes outbreak on her lip, asked: “Are you a couple?”  Keep reading »

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