Travel Diary: Double It Up

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Gay Raw Double Penetration

Washington, D.C., will always be my kind of town. Having lived there for more than a decade of my life, I still miss it terribly. So when I get a chance to return — even for an overnight trip — I leap at the chance. Back in the summer was such a chance and I wasn’t quite in the funk, having not yet met the bi Birmingham boy.

At the time, this youthful, smooth 22-year-old blond guy from the University of Maryland had been begging me to breed him, asking for me to set up a session with other “top friends.” Generally, I’m not quite trustworthy of such unless I’ve fucked them first and find them worthy of such an effort. He caught me in a giving mood, I guess, and he’d pursued me for a couple of months, so having set a time about an hour away, I went to seeing if I could get a few other tops and versatiles to join in the fun.

Since I’m familiar with D.C., I chose a good location, on the edge of Dupont, Adams Morgan and not too far from Logan Circle. With less than an hour from the blond’s arrival, I’d given out my lodging location to five or six men, not expecting them all to show.

The first candidate turned out to be a less-than-enthusiastic tweaker, grinding his teeth and nervously pacing the room. When the second guy showed — a non-traditionally hot-as-shit top — tweaker bailed. Good for us. The top, in his mid-30s, gave the classic look of a slightly beefy legislative assistant on Capitol Hill. Probably once in a fraternity in his day at college, his brown wavy hair still pressed down from the motorcycle helmet he’d worn over riding some high-powered bike over. He didn’t look like a biker. Yet, even my pussy got a little wet and I figured he could fuck me if blondie didn’t show.

He was easy to chat with anyway and didn’t put on any pressure. Soon there was a knock at the door.

In walks a six-foot, 40-something baldy with a fucking-rocking body. We’d find out later he was a bike messenger, which would explain how he had the perfection of no fat. Two minutes in the door, after I explained the U of M boy was a few minutes overdue, baldy had us all stripping down anyway.

Dynamics of a three-way can always be questionable, but baldy had it down pat. He’d just look at one of us and say something like, “Are you going to make me suck your big cock?”

So you made him suck your cock. Not that it was difficult. He turned out to be rather willing. Bouncing back and forth between the two of us, we soon began tag teaming him. My buddy started off, as he had a respectable six-inches, tapered at the top to open him up with a nice curve. Mine proved thicker and harder to manage.My Cock The poppers, of course, helped open him up and we all were enjoying ourselves. Soon we forget about blondie (who never bothered to show up).

Soon the bald guy started one of his submissive taunts: “You both aren’t going to fuck me at the same time, are you?”

Former frat guy and I looked at each other. We cracked a smile.

Within moments, I’d maneuvered myself to flat on my back and the bald bicyclist sat on my cock and leaned forward, beginning to kiss me. Within a moment, I felt the poking and prodding of the cock, finding the right place to enter the tight hole.

Kissing stopped. And the grunting began. Then it turned into just pain as he really put on the pressure. But I have to give it to the bottom. He never pulled away as he left himself there and waited for his sphincter to give way.

Finally, it did as the tapered head of my bud’s cock came in and pressed against my shaft. After a moment, the other top began pushing in and inching his way inside deeper. And the bottom grunted more. Soon the painful noises dissipated and the fucking began in earnest. The kissing started again and I was in heaven.

In a tight ass, raw, another hard cock, rubbing against mine. The sensation just seemed too much. Of course, the bottom was tight and I kept slipping out. We’d adjust, shoving me back in going back to it. But the intensity, I slipped out at the right moment at my top buddy unloaded into baldy’s ass. I hated missing it, but there’s nothing better than sloppy seconds.

So I repositioned, this time behind him. Egged on by Mr. Motorcycle, I began to breed his ass, feeling the cum inside and fucking in earnest, I left a huge load inside him, pushing my new bud’s load deeper.

Since I remained hard, baldy then rode me until he pumped a nice load across my chest.

And who the fuck needed a 22-year-old blond boy, who despite all be begging for months, never showed the fuck up? Instead, I had something much hotter.

Travel Diary: Double It Up, 5.0 out of 5 based on 2 ratings

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4 Comments on "Travel Diary: Double It Up"

  1. bigredfoxman says:

    Very hot

    Makes me want to be dp now

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  2. Thirty3 Naked Laydies says:

    Great story. Talk about making the best of a situation. We’ve always fantasized about messenger boys. In DC, they tend to hang out at the Asylum in Adams Morgan.

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  3. Michael says:

    I lived in DC for over 10 years too. And the first time I was double penetrated was at a *very* hot orgy in an apartment just off Logan Circle. Thanks for the great story and for helping to bring back some great memories!

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  4. Mike says:

    Great story. The fuck party endings are often hotter after some last minute line-up changes. I too love the willing bottom that can orchestrate the action like your bald dude did. Sounds like a hot DP raw session I had in NYC last year. Nothing better than two dudes rubbing their shafts together in a hot wet pussy.

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