Tales from the Tail — Double (Penetration) Trouble

Client’s Tale

OK, OK, so I am not a porn star. And, although I work out regularly at an undisclosed gym (they may offer Kiehl's products), I never thought I would be a part of one of those steam room scenes. Don’t get me wrong — I am not passing judgement and don’t think there’s anything wrong with it, it just wasn’t part of my regular post-workout routine…until that day. I am a muscular bottom, on PrEP, and can get some nice-sized cocks in my ass, that’s for sure. I am not a huge fister, but have had my fair share of periodic fun.

On this particular day, I found myself heading into the steam room, all toweled up, and the second I walked in, a younger guy gave me eye contact that everyone immediately felt — it was that intense. I didn’t pay any mind until he moved closer to me and I saw his cock. It was beyond beautiful — as was he — from what I could see among the mist of the steam passing by. Hard as a rock, and now with the steam on full blast, he got behind me, licking me with abandon. All lubed up with his spit, he entered me from behind and before I knew it, out of the corner came another guy in front of me. At first I was hesitant, but I’m sure a couple of you can relate, sometimes you just have to roll with it. It felt so good and the scene was so hot that even now I am getting hard just recounting the tale. The way the steam room steps were located was actually perfect for the two of them. I was lifted and with one in the front and the other in the back was able to take them both. Yes, you read that correctly — double penetration. The guys were so into it, as was I, and believe me, we all came so fucking quick. They both exploded in me, filling me up to the brim and I must say, it was fucking hot. I came so hard it went all over his face. Never have I had such an experience like this.

I sure had my fun, but, unfortunately, as the saying goes, it’s all fun and games until someone gets hurt. Luckily, the encounter ended without any pain or bleeding. However, fast forward to the next day when I found myself taking what I thought was just an ordinary BM — soft and easy, but clearly some predisposed irritation (I did recently have two cocks in my ass at the same time) — and then boom 💥 — it happened: the pain and bleeding. After a few days of treating my symptoms with Preparation H and some over the counter stool softeners, as well as taking baths, I saw minimal improvement. So I decided it was time to see Dr. Goldstein, my go-to anal surgeon at Bespoke Surgical. He found that I had developed a few anal fissures, but was able to cauterize the front and back tears and we continued standard, over-the-counter meds to help them heal. Par for the course, he also swabbed for STDs and it turned out I had contracted gonorrhea. While being on PrEP sure has its benefits, it definitely doesn’t cover everything.

After discussing treatment, we spoke of some modifications to assist when taking two cocks at once, making sure I am fully prepared for next time. I don’t know when it’s gonna happen again, but if the two guys from the steam room are reading this tale, I hope to see you again. 😉

My Discussion

If you Google “double penetration”, one of the results is a fucking hot shower scene from Sean Cody. Not so much different than the tale above, to be honest. There is lots to talk about with this tale; however, I am not going to touch on the use of public spaces for sexual experiences. I will leave it up to you to determine your stance as it pertains to its ethics. Let’s just focus on the two-fer of cocks in your ass.

Clearly, just taking one cock can be quite challenging, let alone two. It’s definitely for the more seasoned bottom and can take significant practice to perfect. One of the big things to think about is positioning. There are many ways, but upright (cowboy) or on your back seem to be the most popular (and easiest to maneuver). Either way, it’s somewhat of a sandwiched approach — literally. Now, if you follow my work, you know by now that spit is a poor choice for lube, but I also understand that sometimes it’s all there is. Make lemons out of lemonade, right? Yes and no. The best option is to begin by attempting to have all the necessary paraphernalia ready, as well as plenty of patience.

Let’s look at the anatomy of double penetration. One big toy or one huge cock at a time is a lot for your ass to handle, but it’s only one friction point that affects the skin and underlying muscle. Now, adding a second toy or cock, as well as the asynchronous thrusting, can clearly cause a tremendous amount of shearing force that can lead to tearing and/or localized issues. Yes, I know sometimes you have to take one for the team, but if it’s going to be part of your repertoire, then you must practice. Analyze the diameters required and with one partner, you can slowly introduce a dildo at the same time as his cock. Check out what entry works and what doesn’t. Slowly manipulate the skin to learn to accommodate fully. The key here is to create enough controlled friction on your own terms to toughen the skin lines. The weakest spot of anyone’s asshole is towards the front or the back. And that’s where the largest pressure points are located during a double pounding. It definitely takes time to perfect the motion and, again, you’re being put in more of a submissive position any time you are in the middle. Armed with this new knowledge, make sure you have partners that you trust and set up a safe space for exploration.

But if I’m being truly honest, I have to say, it stresses me out just thinking about DPing. It truly is a set up for failure with all the uncontrollable and unforeseen circumstances that come along with it. I 100% see the positives and why people love it so much, but I cannot stress enough the importance of knowing one’s limitations. We have an in house physical therapist, who specializes in pelvic floor therapy to assist you in learning how to fully accommodate one or multiple cocks. I can make sure there are no functional limitations and, if so, correct them. Also, if one is just missing full acceptance of double penetration, then, again, Botox in the muscle or skin line can allow for complete success.

There are so many things we can do to set us all up for success, both receiving and giving. I’m not going to lie — the steam room scene even had me hard. Am I alone in thinking this? But we all can analyze this play-by-play to attempt to manage risks and maximize pleasure. I’m glad he was on PrEP. I’m not so glad he didn’t use proper lube. I applaud him for being on top for his first DP — probably the best position to start off in. But did the second guy attempt to get consent before sticking his cock in? The bottom was quite seasoned to handle such force, but, in the end, even he wound up torn and with an STD. Yes, PrEP + condoms 100% of the time is ideal — we all should know this by now. But we also have to be realistic and understand that risk analysis is key. By talking about these issues and circumstances allows all of us to learn and figure out preventative approaches for the betterment of all bottoms — especially our own.

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