Tales From the Tail — You Want Me to Stick My Toe Where?!

Dr. Evan Goldstein
Bespoke Surgical
Published in
6 min readJul 14, 2020

Client’s Tale.

Must. Get. Laid.

I know I’m not the only one having these thoughts. I’ve been isolating for months. Zero physical contract. Zero dick in my ass. AND, I live alone, so I’m talking to the fucking walls at this point. I haven’t given up my *apps* because sexting is a great physically distant activity. And even though I have yet to initiate any meet-up, because of my duty to be social responsible, Scruff has been bopping lately.

Then I thought to myself: how long can this actually go on?

Last week, I got a notification from Scruff and this one really piqued my interest. His profile not only discussed his fetishes and demands, but also that he was recently seen by his anal surgeon, where he received a full STD panel, along with an active Covid-19 test. He even sent me a picture of his negative results (along with, of course, the requisite 🍑 and 🍆 shots). I was so happy and relieved that someone had taken the initiative to analyze every risk — not just the standard STD and HIV precautions — all the while looking for partners with the same morals and ethics.

We chatted for quite some time and eventually, when I knew it was leading to something, I told him I would make an appointment to get tested as well — STD, HIV, and Covid-19. We agreed that as soon as my negative results returned, it was game on. We both understood that there are many factors to safely hooking up during the pandemic, but if we placed ourselves in social circles where everyone adhered to frequent testing and abided by the CDC guidelines in between testing, then we would be putting ourselves in a position that would mitigate risk while still allowing us to live our lives.

The time came and we decided to finally meet up. I thought we had both checked off all the boxes, when he sent over some additional (and significant) demands. First, I could only refer to him as “son”. Second, he wanted me to wear a surgical mask, while he would be in full leather protection from head to toe. Third, I could only fuck him and he had to be in complete control. Fourth, talking would only be allowed if he initiated it. Lastly, and most importantly, if I were to break any of the rules, I would be asked to leave immediately. No pressure, right? 😳

Sadly, it didn’t go as planned… at all. I was terrible at following the rules. So much so that on numerous occasions he had to break character to ask me what my problem was. 😬 Fortunately, he was kind enough to give me more than a few attempts at obedience and, finally, we got into a good rhythm. I guess it’s just like bottoming — you can’t dive right in without warming up a bit! At one point, he told me to lie in a chair, near his bed. While facing away from me, he then sat down on my cock. Not long after, he began riding up and down and then he told me to slap him super hard on the ass. He loved it. With each slap, I got harder and it seemed he did, too.

Then, he jumped off to catch his breath, before telling me, in a rather mean tone, that the final act he would like to request is for me to stick my big toe up his ass. Caught off guard, I asked him to repeat himself, so that I could make sure I heard him correctly. To be honest, I’m 65 and although I’ve heard (and done) a lot, I have yet to encounter a demand like this one. I did hear him correctly and then I thought to myself, why the hell not? He was already slick as whistle from fucking, so my toe slid right in. I thought slapping his ass did it for him, but this was on a hole new level. He was experiencing total euphoria.

He was riding me — I mean my right big toe — like a stallion… and then it suddenly stopped. I didn’t know what had happened. I honestly just started to hear snoring. I couldn’t believe it. Did this guy just fall asleep in the middle of sex?! Here I was with my big toe in his ass and he down right passed out! I tried to wake him up, but he was sound asleep. Of course, I checked and he was breathing. He was just asleep. Maybe he was a narcoleptic?

Then I thought to myself, what am I doing here? This is fucking ridiculous. So I took my toe out of his ass, got dressed, and walked the fuck out. I mean, what would YOU have done?

I’m a gentleman, so I did have the decency to text him the next day to make sure he was alive and well. Thankfully, he was, but no explanation was ever given.

So how will I recount this tale to future guys? “I once fucked a guy so good he passed out…”

My Discussion.

The big toe!? Never in a million years would I have thought of using this appendage as a fuckable object, but I guess we all learn something new every day. All that matters is that it’s safe and it gets you off, right? No judgement.

However, I have strong feelings about using fingers for anal play, so you can imagine the same rules apply to toes.

  1. Make sure the nails are trimmed and manicured. You don’t want to cause any tears (called anal fissures).
  2. Especially during warmer months, please make sure you don’t have any any fungal infections (like athlete’s foot), as this may transfer to the ass.
  3. Use lots of lube and don’t wiggle your toe(s) too much. Stick with in-and-out thrusting, just like you would with your 🍆.

OK, OK. Enough on the toes. Just remember: different devices, same precautions.

Now, let’s get into risk reduction. I think we can all truly appreciate what these two went through to try and help reduce risk by getting active Covid-19 tests before hooking up. The leather community, in particular, has been way ahead of the rest of us (for years) with its potential inclusion of masks. Putting aside the quirks of the encounter (read: someone’s sleeping habits 😝) the preparatory precautions were on point and we should applaud their effort.

Risk-assessment with STD screening is paramount to minimizing any potential exposure. And now, we at Bespoke Surgical have added active Covid-19 swabbing so that it’s synonymous with any other sexually transmitted risk. It’s a new dawn for fucking safely and we hope you’re part of the solution and not a part of the continued problem. Because we need everyone’s help in order to make a meaningful impact.

We know people are slowly venturing out of isolation. Some are staying vigilant and others are letting their guard down. We’ve seen it clearly on social media and while out and about. Some have resorted to publicly shaming those who stray, but we want to help arm everyone with the right resources and testing to make informed decisions. The key always has been and always will be to provide a platform for people to understand all the potential ramifications of their actions, with the hope that mitigation, if not complete eradication, will ensue.

For those who can physically come into my office, I hope that once they leave, they not only act responsibly, but also pass along the information I’ve shared with everyone they come in contact with. We need to accept responsibility for ourselves, understanding that these actions will impact the community at large. It has for years before Covid-19 and will continue in the future.

So I urge you to take the lead and demand social responsibility for our interactions both in and out of the bedroom. It’s for the betterment of all of us. There is a scientific rationale behind sexual encounters and our mission is to help spread that knowledge. And don’t forget — we are always here for you if you have questions or need guidance.

Don’t forget to stay in touch on Instagram: me, Bespoke Surgical, and Future Method.

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