Home > anal, it hurts so good, memories, sex, travelog > road trippin’ with my two favorite allies

road trippin’ with my two favorite allies

I spent the weekend on a road trip with SR and various friends he picked up/dropped off along the way, ending in New Jersey at, of all things, a car show. It’s called Waterfest and apparently a prime event to geek over VWs and Audis at. Saw some pretty slick cars, heard plenty of things I couldn’t decipher, and probably got 3 shades darker from being in the sun (not to mention the reflection off all those cars and motors). I walked around a bit with my tongue plastered to the roof of my mouth, refusing to pay the $3 for the tiny drinks they had at vendors all around the event.

Later we met up with some of the guys from Waterfest and SR got to drive a friend’s modded Audi on the highway to see how fast it could go. And sitting in the back, feeling the vibrations of the car and the exhilaration from the speed coursing through my body, I got a glimpse at what it really means to drive a car. Mmmmmm. Hot hot hot.

But perhaps not as hot as the teasing that occurred the night before the show, when SR, one of his guy friends, and I crashed at a cheap motel for the night. In a tiny one-bed room. So the friend slept on the floor by the bathroom, and SR and I shared the bed. And as soon as SR got under the covers, his boxers came off and he pulled my hand over to feel his erection. And I was thinking, I don’t want to be that couple that has sex in the same room as a friend and makes things awkward for him. I mean, he was already sleeping on the floor!

But it felt good to grip his hard-on in my fist, and after awhile we started spooning and I could feel how hot his crotch was. It was getting me horny, and him rubbing me from behind just made it harder to refuse. So I pulled my shorts off as quietly as I could and pulled his cock to me, and he slid in easily. God. It was so difficult to stay quiet and not gasp/fuck him back/moan, which just turned me on even more. And I’m sure the bed was shaking in a very obvious way. It was amazingly hot, despite the fact that we were on our sides and couldn’t fuck hard or fast. He wrapped his arms around me in a body hug that also pushed me deeper onto his cock, and I was slowly being driven crazy from the slow buildup, silence, and underlying intensity of the moment.

SR pulled out and I tried to let out my breath quietly, until I felt a finger pressing against my ass.

Oh. He wants it there.

It wasn’t completely unexpected; SR has made it obvious in past romps in bed that he wants to fuck my ass. And that night, after getting teased for what seemed like forever, I was feeling more than a little malleable and compliant. I let him open me up with his finger, which felt amazing, and then guided his cock to my anus, already puckering in defense. He slid inside surprisingly easily, and I couldn’t help gasping then. I always get more vocal during anal sex, and I knew that I could not do this with his friend 20 feet away.

Not to mention it has been a pretty long while since I was last fucked in the ass, and after the initial entrance, every movement he made burned with pain. I grabbed his hips to stop him from moving, turned my head so my lips were near his ear, and whispered at him to slow down. He whispered back, wanting to know if it was okay, so I nodded but repeated my request to slow down, it’s been awhile. I guess he sensed something was wrong and just pulled out completely. Only to try penetrating me in the pussy again. I grabbed hold of him and asked what he thought he was doing. He told me he wanted to fuck me, and, exasperated, I told him there was no way he could now that he had been in my ass.

Oh, right. Good call.

Dear lord. That made me wonder for the rest of our trip whether or not he’d had anal sex before. But it seems like mere common sense that that kind of shit cannot be done except in pornos catering to those kinds of fetishes. I suppose, though, that ass-to-mouth is so commonplace now that the concept is just desensitized? I have no idea, but the thought icks me out. Not my kink, thanks.

But I felt bad cockblocking him, so when I heard him start to jerk himself off, I moved down the bed and hovered my mouth by his cock, telling him that I wanted his cum in my mouth. That helped him ejaculate pretty quickly, even though for the most part my mouth wasn’t really touching him.

Fast forward to Sunday morning, when we finally find ourselves back in Boston, and more importantly alone. We park his car at my place, and he goes straight to the shower while I relax for a bit in my room. He comes into my room as I am catching up on my RSS feeds, pulls me across the bed, and pulls all of my clothes off. I’m not as wet anymore after showering, sleeping, and then driving for 2 hours, but slowly he works his way inside me again, standing behind me while I strain on my toes to take him all the way. Our height difference makes some positions a little difficult. But we both love doggie style, so we make it work.

After lots of sex in several positions, we’re back with him fucking me from behind, a finger in my ass. I know what’s coming, and sure enough, he pulls out and I feel pressure against my ass. It’s harder this time, I’m tired and tight and still recovering from the last session. But slowly, I back my way against his cock and feel him penetrate.

God. I don’t know how to describe the feeling of being anally penetrated like that. After the initial painful stretch, I become lost in the deepness of the sensations. Ever since I began exploring my body sexually, anal penetration has drawn my curiosity and intrigue. And it just feels so damn good! He didn’t fuck me too hard, but it felt amazing and it was making my pussy flood. It is like I have an alter-ego with anal sex, too. I am so much more vocal, and talk so much dirtier, than with vaginal sex. I begged for him to fuck me harder, and to cum deep in my ass, and he just couldn’t last. He fell forward spasming from his orgasm, pushing me flat against the bed, his cock still embedded in my ass.

While we both caught our breath, I started playing with myself. SR left to clean up in the bathroom, and came back into the room just as I was starting to come myself. He traced fingers down my back as I was shuddering, before turning to lie on his back as I started breathing normally again.

I do believe anal sex makes me come the easiest. Probably something to do with the massive amounts of fluid that I leak during it.

Recalling all these details of this morning is making me achy again. So I’ll leave off here while I attend to my needs.


  1. No comments yet.
  1. No trackbacks yet.

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: