True Dating Confessions: Double Booked

Planet Out presents a brand new feature where readers Spill Their Gay Guts!! Everyone's got at least one juicy, sexy, hilarious, crazy, unbelievable, embarrassing, or steamy story to share. Check out this anonymous True Dating Confession, then submit your own today.

Have you ever been confronted by multiple people you were dating at once?
"No, but ended up having two dates for the same night. One, I was desperately in love with, who informed me he didn't feel the same way and was moving away for work.

The second date was with a wonderful guy that was my 'friend with benefits'.

We went out to a club where we met a guy that was to become my beau for next thee years."

True Dating Confessions: 3Some Repeat

Planet Out presents a brand new feature where readers Spill Their Gay Guts!! Everyone's got at least one juicy, sexy, hilarious, crazy, unbelievable, embarrassing, or steamy story to share. Check out this anonymous True Dating Confession, then submit your own today.

Have any threesomes, fetishes, or new experiences you've attempted ever gone awry?

"During my first threesome, the guy that joined me and my then partner, realized that he and I had actually had sex together (years before). We both got the giggles and that ended the sex... but lots drinks and laughs afterward."

True Dating Confessions: Hookup Sites

Planet Out presents a brand new feature where readers Spill Their Gay Guts!! Everyone's got at least one juicy, sexy, hilarious, crazy, unbelievable, embarrassing, or steamy story to share. Check out this anonymous True Dating Confession, then submit your own today.

Ever secretly surfed a hookup site for a date? What were your results?

"I ended up meeting a guy that I'd seen for you years on the commuter train and didn't know he was gay.

It was a short but sweet involvement, we are still friends though and happily involved with other people."

True Dating Confessions: Very Adult Charades

Planet Out presents a brand new feature where readers Spill Their Gay Guts!! Everyone's got at least one juicy, sexy, hilarious, crazy, unbelievable, embarrassing, or steamy story to share. Check out this anonymous True Dating Confession, then submit your own today.

What's the weirdest activity you've ever tried on a date?
"I had a date with a guy and we met up with some of my performing friends.

We ended up playing an evening of naked charades...

and that's all I'm going to say about that one for now."

True Dating Confessions: Diamonds Are a Guy's Best Friend

Planet Out presents a brand new feature where readers Spill Their Gay Guts!! Everyone's got at least one juicy, sexy, hilarious, crazy, unbelievable, embarrassing, or steamy story to share. Check out this anonymous True Dating Confession, then submit your own today.

What has been the most romantic moment of your life?
"The most romantic moment in my life was during a Valentines Day getaway with my boyfriend of 3 years, in the picturesque seaport town of Mystic Connecticut (pizza, et all.) We were together in the Jacuzzi tub of our charming B&B overlooking the village. The candles were lit, the champagne was poured, and from out of the bubbles came a diamond ring that he put on my commitment finger. My first and only diamond ring given to me by a boyfriend...

True Dating Confessions: She Couldn't Say No to Her

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What's the strangest place you ever did the deed and how/why there?
"I stayed over my gf's house, and she lives with the rest of her family. Everyone slept on the floor that day. her, myself, her sisters and cousins. For some odd reason she got the urge to get on with it, while people were lying asleep all around us!

Of course I can never say no to her. I'm still worried till this day that maybe one of them wasn't really sleeping and witnessed some of it."

True Dating Confessions: His Initial I.M. Encounter

Planet Out presents a brand new feature where readers Spill Their Gay Guts!! Everyone's got at least one juicy, sexy, hilarious, crazy, unbelievable, embarrassing, or steamy story to share. Check out this anonymous True Dating Confession, then submit your own today.

Ever secretly surfed a hookup site for a date? What were your results?

"When I first got online, I did not know men would lie about their ages online to get laid or to even get a date. Ok so I was naive back then, but weren't we all when we first started out? Well this guy IMed me on AOL so I checked out his profile. Under birthday it said '72 so I figured he was just a few years younger than me.  

I know you know where this is going already but I will continue any ways! 

True Dating Confessions: Coming Out About Barry

Planet Out presents a brand new feature where readers Spill Their Gay Guts!! Everyone's got at least one juicy, sexy, hilarious, crazy, unbelievable, embarrassing, or steamy story to share. Check out this anonymous True Dating Confession, then submit your own today.

What was your coming-out affair like?
"It was a continuous process, first to my best friend (straight), who just hugged me ant told me it was good to know and were we still going to be playing racket ball together? I then told my Dad after he asked (during my 18th year) who I was bringing home for Thanksgiving dinner. I told him I was bringing my friend... Barry.

True Dating Confessions: Love Among the Trees

Planet Out presents a brand new feature where readers Spill Their Gay Guts!! Everyone's got at least one juicy, sexy, hilarious, crazy, unbelievable, embarrassing, or steamy story to share. Check out this anonymous True Dating Confession, then submit your own today

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What's the strangest place you ever did the deed and how/why there?

"In a tree in the middle of a park at night...we had been out walking earlier in the day and decided we would come back that night and just have at it!"

True Dating Confessions: His Romantic Rendezvous

Planet Out presents a brand new feature where readers Spill Their Gay Guts!! Everyone's got at least one juicy, sexy, hilarious, crazy, unbelievable, embarrassing, or steamy story to share. Check out this anonymous True Dating Confession, then submit your own today.

"I was new to New York in 1974. At 24, I should have been sowing wild oats (okay, I was). But, I was looking for Mr. Right not Mr. Right Now. So, I was dating two or three guys at the time and one of them wanted to go out dancing. We went to the Galaxy 21 on 23rd Street between 7th and 8th Avenue (south side of the street near the Chelsea Hotel).

It was 4 floors (plus the basement) of debauchery…YEAH!!! The entrance floor had the bar and dancing. The second floor had another bar, bathrooms, and a lounge. The third floor had sex movies (gay & straight). The fourth floor had live entertainment (that night was Gloria Gaynor). I’ll leave the basement for you to decipher....