Tag Archives: first time for everything

First Time For Everything: Deflowering A 30-Year-Old Virgin

Virginity Regrets
Regretting the way you lost your v-card. Read More »
5 Sex Moves
sex photo
Five sex moves women love in bed but can be too afraid to ask for. Read More »
Failure To Squirt
Should you feel bad if you can't squirt? Read More »

I’d never slept with a virgin. On our second date, Jim and I escaped from a hot and overcrowded bar and sat on a bench outside. Fueled by a few pints of Guinness and the urge to confess, Jim admitted to being a 30-year-old virgin. He’d never even had a girlfriend. After a long moment of silence, I asked him, trying to sound as non-intimidating as possible, why that was.

Jim didn’t have a concrete reason. He rattled off details about his life. He was Catholic, but didn’t go to church and definitely wasn’t saving himself. He went to an all-boys high school. He lived at home during college and grad school, though he owned an apartment now. He really didn’t know why. The desire was there; the opportunity just hadn’t presented itself. Keep reading »

First Time For Everything: Sinning With The Pastor’s Son

Dungeons Date
A writer is sure she will find love at Dungeons & Dragons. Read More »
Sugar Baby
A writer talks about her experience as a sugar baby. Read More »
True Love Waits
A writers shares her experience dating a "true love waits" Christian. Read More »

Ryan* and I started dating during my junior year of high school, when I was going through my Christian good-girl phase. I dutifully attended church lock-ins, Bible camps, and crushed on worship band boys. Ryan, who played guitar in a Christian band (sigh) and just so happened to be the son of my 6’5″ Pentecostal Pastor, was the one I chose. In addition to being a couple, we were best friends who were in choir and church drama team together. Ryan was absolutely hilarious, super tall like his dad, and best of all, my mom LOVED him. He really knew how to get old broads to swoon.

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First Time For Everything: Dating A Couple

Poly Dealbreaker
Is polyamory a dating dealbreaker? Read More »
Not For Everyone
Polyamory is not for everyone. Read More »

I met Greg* through a dating website and we talked online and  then on the phone for about a week. I was very hesitant because I had never tried online dating before, and also because of one more very glaring fact: Greg was in a four-year relationship with Jen*.

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First Time For Everything: Phone Sex

As I laid on the couch, having a very regular, very non-inspiring evening alone watching baseball, I got an onslaught of sexts from the woman I was dating. After a series of lewd and kind of hilarious d**k pics, she replied with what looked like a Vogue magazine worthy, very tasteful, classy black and white digital nude. I got harder than Chinese algebra. I went from zero to phone sex in a matter of seconds. I dialed my woman. It was the next logical step. Keep reading »

First Time For Everything: Hitting The Big O

In the spirit of Columbus, Magellan and Lewis and Clark, I spent my teenage years as a fearless explorer of uncharted carnal terrain, reporting back to my tight-knit group of girlfriends with play-by-plays and handy tips from my randy sexual exploits. I was the first in my high school crew of gals to do pretty much everything: kiss a boy, get felt up, get naked, get fingered (in a movie theater), receive oral sex, give oral sex, and finally, have sex (on the floor of my high school boyfriend’s parents’ basement). A new world of experiences was opening up, and I took on my role as trailblazer with fervor, drive and anthropological scrutiny. That first night on the basement floor, I remember thinking to myself, Wow, the cavemen did this! Keep reading »

First Time For Everything: Fisting

In my early 20s I was still new to relationships and sex with women. I hadn’t yet completely identified as a lesbian and the idea of sleeping with a woman totally freaked me out. I was terrified of oral sex and to me, that was the only way to do it with women. When I finally broke through my fear and got together with my first girlfriend, the sex was amazing but pretty vanilla — no dildos, no spanking, no bondage. Keep reading »

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