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Published at 6:16pm
Published on 9/5/08
Video
To you, double penetration (affectionately known as DP) may seem like a porno circus trick. But the idea of getting filled up and stretched out has always appealed to me, and since group sex has moved from fantasy to common practice for me, I’m hungry for a new challenge.
Before starting, I talked to a longtime friend and dirty-adventure coconspirator with some personal experience. Jefferson, something of a New York playboy who records his exploits on his blog, One Life, Take Two, was the perfect go-to dude to help out with the mechanics. “My advice on position,” he advised, “is to regard one cock as the anchor, with its possessor reclining under the woman, with the second cock entering her from the rear.”
Worrying about keeping one flesh-and-blood dick happy and excited seemed tricky enough, so I arranged to borrow Jefferson’s girlfriend, Madeline (who also has a sex blog, MadelineintheMirror), and combine her with my boyfriend, Bobby D. And so on a sunny Sunday afternoon, while other East Village denizens were still waiting for tables at 7A, I was getting my nether orifices filled up by my boyfriend and a strap-on.
We started with a good old-fashioned threesome—a two-girl blow job, one girl on cock and the other riding my boyfriend’s face—before we got more advanced. I encouraged them to tongue-fuck my “naughty hole” (as Bobby D affectionately calls the anus), and after I had a sheet-soaking orgasm, we decided that Bobby D should enter me anally, on the principle that my vagina would be more stretchable once I was half full (an optimist’s DP!).
Though we were prepared to do the standard anchor position with Madeline on her back on the bottom, me in the middle and Bobby D fucking my ass from behind, we somehow worked ourselves into a weird position (Madeline joked: “Right foot green!”). With me on my side, they went at me piston style, resulting in three heavy orgasms for me, a squirting one for Madeline and an anal cream pie (a.k.a. come in my anus) from Bobby D.
Afterward, I lay in my sticky, postcoital trance for a while and then realized that I was totally famished. Over a sushi dinner, Bobby D and I reminisced while Madeline, having returned to Jefferson, sent me naughty text messages. We may have a date next month.
Jamie says:
When choosing a third party, you have a major decision to make: Should they be a friend, a stranger or someone in between (e.g., your local Starbucks barista)? I’d recommend the in-between person. Friend: too dangerous relationshipwise. Complete stranger: too dangerous in other ways. In-between person: They know you know where they work, so they’ll be on their best behavior. Of course, if things get awkward, you will have to find a new coffee place.
TeamGBUK
Tue, Sep 02, at 04:08am
We are 2 guys in the UK and have been 'specialising' in this for about 18months now, our advice is look for 2 totally clean, but dirrrrrrty strangers, such as ourselves, and let the party begin. A study has shown, that over 94% of women fantasise ( I am English, we spell correctly with out the Zeeeeeeeeee's) about having 2 men, but only 6% of those ever get to try. I think the problem is finding to guys to actually perform in front of one and other. Any advice email ivorbiggun69@hotmail.co.uk
llk
Wed, Aug 20, at 04:04pm
Just because you can, does not mean you should or it makes it right.
American Girl
Mon, Aug 11, at 12:55pm
glad you picked a girl as partner number two. this seems normal. 2 guys would have been gross.
ralph
Thu, Jul 03, at 04:18pm
wow i would love to have a threesome with two women!!!!!!!!
mymember
Sat, Jun 07, at 08:17am
anything goes, always do what you please. no law broken here.
Parson
Wed, May 28, at 09:15pm
I used to live in Manhattan during the late 80s-early 90s.
M
Fri, May 02, at 09:21pm
I'm there...
PTintheplacetobe
Thu, Apr 17, at 05:50pm
i work at starbucks..... serisously, i do.
DoubleShocker
Mon, Apr 07, at 12:53pm
Are you serious? You leave the crummy comments up on this page, and the glorious review I give you based on YOUR well written content is ripped away for what reason? Maybe because I run an ADULT website. Oooooh! Well, that IS the content here, right? Maybe it's because I listed the site as being at doubleshocker d0t c0m or something in the nature. If people want to see examples FOR FREE what you are talking about, have them visit the site. Again, like I said last time, VERY WELL WRITTEN. KUDOS!
DoubleShocker
Fri, Apr 04, at 04:19pm
As a huge fan of double penetration, I was very impressed with your recollection. Some stores online even sell DP harness kits, although it doesn't seem like it would be much fun without two partners going at you. Kudos on your well written and educational article. Stop by sometime and check out all the DP goodness we have on our site, doubleshocker.com - you might even get some ideas for your first double anal or double vaginal experience. I would love to hear about it!
Grrrl
Fri, Mar 28, at 01:47pm
No condom?
alana
Fri, Mar 28, at 01:48am
all i am looking for is sex...
alana
Thu, Mar 27, at 11:52pm
and i am soo horny so for all the hot guys that are looking at this rub ur penis and if you have a hotmail address or even if you have msn add me on that...
my email address is......
alana_loves_soccer@hotmail.com or you could add this one
anala_iz_cool@hotmail.com
alana
Thu, Mar 27, at 11:47pm
ello
JK
Sat, Mar 15, at 12:07pm
'guy kinda backed out' - kinda?? LOL, what does that mean?
ted
Sat, Mar 15, at 06:57am
thought you'd enjoy this
Mike
Sun, Mar 09, at 12:54pm
Wow, this helped out so much... I've been urging my girl to find someone to have a threesome with. We tried it but the guy kinda backed out last minute.
ww
Wed, Jan 16, at 07:25am
chjec i out
Marla Jo
Sun, Oct 07, 07, at 7:43pm
i think that's the day i had lunch with your 'anchor'. -- yes, yes, it is. i told her she smelled good, and she affectionately informed me it was the scent of sex. - nice!
