My First DP – NOT!

By Kendra Holliday | February 24, 2013

A while ago I announced I was going to try DP for the first time.

We scheduled it for a laid back Saturday afternoon.

Our friend Homer helped us fulfill our fantasy. Homer is a total sweetheart, we both like him a lot – he’s the perfect choice for this intimate experiment.

That morning, I woke up hornier than usual. I got off twice, once with the vibe, and once with oral. Matthew was so attentive and supportive. I’m so grateful to be in a relationship where we can make our wildest fantasies come true!

We worked him up a few times as well – sucking him, jerking him off in the shower, taking him right to the edge of orgasm, and then backing off.

Mid-morning, I felt pretty nervous and had an upset stomach. I don’t know about you, but it’s not always easy to plan anal – it’s something I have to be in the right mood for, physically and mentally. I didn’t want to miss this golden opportunity, so I fasted to keep my system clear.

I ran to the drugstore to get an enema. I bought a bunch of stuff so that the enema would blend in with my purchases, but when I got to my car with my saline solution, body lotion, mineral water, and eyebrow brush, I realized I FORGOT to get the enema, so I had to go back inside and buy it solo.

Me = anal dork

The woman checking me out said, “Have a good one!”

God I hope so.

Back home, I holed myself up in the bathroom and gave myself an enema. Usually it only takes one round to get the job done, but today I did it three times just to be sure. Eek, Homer was going to show up any minute now!

I went with a relaxed, playful look for our encounter, wearing a little crocheted peasant cover that offered easy access:

Right before we got down!

Right before we got down!

I was sooo giddy! I kept jumping up and down and giggling:



OMG Homer arrived! He had a surprise for me – he grew A BEARD! I couldn’t believe it! I was going to be sandwiched between two, great big burly bearded men!!!

He also brought a bottle of FIGHTING COCK! LOVE IT! Seen here with my anal prep tools – Flexi Felix and Boy Butter!

DP ingredients :)

DP ingredients 🙂

Matthew put on Beethoven’s Third Symphony. He’s making each symphony in the series so special! I wonder which one he will play for the gang bang?

We hung out on the couch and chatted for a bit. I sat between them, of course! I put my hands on their thighs, stroked their beards. They caressed my hair, shoulders, and generally stimulated my erogenous zones. I was ready!

We moved to the bedroom and I lay back and let them do their thing. They sure know how to worship a woman!

First, they started out by lovingly kissing me and sucking on my breasts. I couldn’t believe my eyes looking down at their great, shaggy heads. It was surreal. They both filled up the room, and soon, they would be filling ME up! They pleasured my body seamlessly, it was like they were cloned, all of our energy was in tune. They’re both such great lovers! No weird vibes, only a positive force radiating in the room. I felt so incredibly relaxed and filled with happiness. It felt supreme. They both knew me so well.

Homer expertly ate my pussy as Matthew fucked my face. He was SO hard – he loves when I cum with his cock in my mouth!

Once I was even more turned on, Matthew lubed up the anal beads and inserted them inside me (the Boy Butter is great, by the way – very moisturizing with an innocuous smell). I was so turned on, I didn’t even feel it! They sucked on my tits and I used the vibe. When I came, he slowly pulled the beads out – ahhhhh!

I wanted cock!

There was plenty to go around. Even though I was with two straight men, there was no one in the room afraid of cock, which made things work so well. Cockphobia is an unfortunate affliction that causes great harm in our society and can impede hot sex if left untreated.

Both men tasted, smelled and felt fantastic. Homer has this thing where he jams his cock down my throat until tears run down my face. I love/hate it so much!

I loved cumming over and over again. They kept making me do it. They wouldn’t have it any other way. I was absolutely high on endorphins.

I was so turned on, open, relaxed. Homer was on his back, at the edge of the bed. I was seated on top of him, his cock all the way inside me. Somehow, he stayed hard and in place the entire time. Matthew kept trying to work his way in my ass, but they were both so large (Homer is 250 lbs and Matthew is 300) bellies and thighs kept getting in the way. I was ready, but the logistics were another matter. If they were smaller guys or we had figured out an alternate position sooner, it would have worked.

(During our attempts, the doorbell rang. It NEVER rings. Of course we ignored it, but when it rang again, Matthew finally stopped, pulled on some jeans and answered the door. It was a guy selling gutter cleanings.)

After a while, we gave up on the DP and they took turns fucking me. They were both so pent up! It was like they were two hungry cavemen watching me gorge on steak. And now I was the steak. The bulk of the time it was all about me, and then for the last 10 minutes, it was all about them, which I LOVE. I love when men use me to cum, and that’s just what happened. Homer fucked me with a purpose, then pulled out and came all over me. Then Matthew moved in and had his way with me. I felt so used and delicious! Then HE came on me, in scalding hot spurts all the way up to my chin. He was so worked up and came so hard it hurt his balls.


I rubbed the cum into myself and squirmed in delirious ecstasy.

They stood over me, panting and smiling. Right on the last note of the symphony, the two men arm bumped.


I love that it didn’t work out exactly as planned – that means we get to try AGAIN!

Next time we’ll try working off the corner of the bed so the men have more thigh room.

Here was me after it was all over:

They wore me OUT!

They wore me the fuck OUT!

After the DP, I sent Homer’s wife a message: “Thank you so much for lending us your man. He was fucking amazing. You should rent him out to couples for MFMs!”

All women should be so fortunate to be engulfed in loving, hot male energy!


Justin 2013-02-24 08:43:54

I wonder if a sex swing would help you guys out with the acrobatics involved? We’ve been loving ours (haven’t tried DP yet) …the amazing thing about it is that it obviously minimizes the gravity factor for all the usual positions and you spend a whole lot less energy fighting to hold up your bodies and readjusting, and more energy thrusting. But with the straps adjusted appropriately positioning a female vertically you’re freeing up a whole new dimension! Front and back door simultaneous entry I’m therorizing should just be a matter of lining things up right. 6 legs will still probably get in the way to some degree, but that’s going to be a lot easier to deal with.


Castiel 2013-02-24 10:07:02

Amazing, simply amazing. I can’t tell you how much I enjoy your stories… my gawd, I think I need to go and take a cold shower. One day I would love to watch, just watch. Would love to see your reaction while you were being fucked and MAn-Handeled. Listen to the sound and enjoying the smells of SXE in the room.

Next time, here is what I suggest. If the guy’s don’t mind that there legs touch each other, why not have you lye on top of one guy and his cock inside you, then the other guy upright doing you doggy style. Its how they always do it in Porn. But I’m guessing you’ll tried this…yea?


Homer 2013-02-24 11:51:48

Thank you both for allowing me to be a part of such an amazing experience. We’ll get it next time!!! 🙂


Jade 2013-02-24 19:33:49

I feel ya on the logistics of making it work. We’ve done it several times now (and even managed two cocks/one hole!) but it *does* take some effort and pre-planning, and we had our share of “logistics failure.”

Not that I mind, because the planning and do-overs are so much fun! 😉 And hell, as you said, now you just get to try again! (And again!) (heh)

PS – that last pic is adorable!


Matthew 2013-02-24 22:02:11

Great accounting of the afternoon! What a fantastic time it was! I look forward to the second attempt. …and even the third, fourth, fifth….
It’s great to have amazing friends to call upon for whatever we need. It’s equally as great that they can call upon us to help realize their fantasies as well!
Life is good! Much Love makes it truly amazing!


CrazyCockAcres 2013-02-28 08:40:10

So glad we learned about your blog, great article. Not everyday you can read about someone’s attempt at real life DP that failed, because in the movies of course it never fails. Keep up the great work!


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