At WINGS, we always love a good talk about fisting. We sat down with three kinksters who told us all about their experiences, desires, fantasies, and more.
After hearing beginner Pup Derix, it’s now time to let two experts share a little word of wisdom. 32-year-old Boy4Sir (he/him), raised and ‘made’ in Poland, has been living in Berlin for six years. It has given him the chance to explore, learn, and experience much more than he could have anticipated. 30-something-year-old Pup Rew (they/them) started their kink journey in 2016 by exploring the pup and leather communities in Chicago, a city full of many vibrant kink events.
How did you get into fisting?
Pup Rew: “One evening, I had an incredible threesome with a friend, and we were dom topping this boy’s butt. After a few hours, I realized he was worked out enough and that my hand would be able to slide in fairly easy. So, I kissed him hard and slid in. When I felt the inside of a hole wrapped around my wrist I was hooked. I didn’t know yet fisting was an established kink, I just knew I loved making people feel amazing and giving them pleasure. And of course, I loved how it felt to have a body around my arm.”
What sets fisting apart from ‘regular’ fucking?
Pup Rew: “There is just so much more possible the moment you involve more body parts, instead of having the primary focus on ‘dick in hole’. There are times when fisting transcends what is possible with a dick. There is something about a hand that feels much more connected. Of course, there are also times that it’s not a transcendent experience, but it’s just being carnal animals together, and that can be a blast too.”
What was your best or worst fisting experience?
Boy4Sir: “My first fist experience was given to me by my good fuckbuddy from Portugal. He has nice little fists – perfect for a first time. The feeling was very good, I was overwhelmed. I wanted more but my ass was not ready at that time. The best experience is ‘weekend nights with friends’. It’s always a great feeling to get fisted and to fist others. In the meantime, chatting and getting to know others deeper is even better. My worst experience was when I did not listen to my body. I really wanted to meet a guy for a fisting session, but my stomach had a different opinion.”
Pup Rew: “I don’t know if I can single out one worst experience, but there have been many times where the chemistry is just not working.”
What are the best practices for a safe and sexy fisting session?
Boy4Sir: “For me, it’s very important to be clean. If I know something is not as it should be, I will never relax, and fisting wouldn’t give me any pleasure. I reduce my food portions, I take extra fibres, and after the enema I play with my toys – my favourite is an inflatable plug. The environment of the session should allow you to fully relax. It should be warm, not too bright, and with enough space for all players.”
Pup Rew: “Lube! Lots and lots of fisting lube! The last thing you want is micro-abrasions or tears that take you out of commission for a few days. Also, while stretching, avoid toys without bases. There have been too many people ending up in the hospital because a toy went up too far. Lastly, respect your body. Sometimes it can feel like fisting is being turned into some type of competition, but you don’t have to prove anything to anyone. Just have fun.”
What are things to look for in a fisting partner?
Boy4Sir: “I like to see if the partner cares. It doesn’t matter if it’s fisting, BDSM or a regular fucking session. If I get the feeling that he cares, that’s the base from which we can start. In the end, we are both giving each other pleasure, aren’t we?”
Pup Rew: “Short nails! Honestly, it’s often hard to tell virtually. You just have to try it out and see if they are a match. The energy someone gives is key for me. Some people are just naturally intuitive in ways that make them amazing from their first experience, so it’s difficult to use ‘experience’ as the primary measure. I also love to see videos of someone fisting to get an idea of their approach, to better determine if we are a good fit.”
What are some of the dos and don’ts?
Boy4Sir: “Taking a whole fist is a big step. What I would definitely recommend is to train your ass. Take your toys, lots of lube, and play. When you play solo, you really know when to push and when to stop. Push a bit more than last time, hold in that big plug two minutes longer, and so on. Before a session, have a good enema, reduce your meals – I take protein shakes or bars – and drink lots of water. During a session, try different positions, put a pillow under your ass, and make sure you feel safe and good. The fister can also help by doing small things, like warming up his hands.”
Pup Rew: “Start practicing with larger and larger body-safe toys. Topped Toys have helped me overcome some obstacles. They have a great guide for toy play in training for fists. Treat your hole like any other muscle when exercising. Warm it up, stretch slowly, and push your limits as it grows. Also, remember that a lot of the porn you see are only the most intense parts of a session. That shouldn’t be the goal or any measure of ‘success’. Let goals go and just have fun with your body as you learn what feels right for you. To relax more, connection and trust prior to playing make the difference. When you trust the top, it’s so much easier to lean into what is happening and open up and relax – instead of being nervous and tense because you are worried the next move might be too much to handle.”
“Fisting transcends what is possible with a dick”
Some people experience a block when getting fisted. I call it “the wall”. You can’t get past this one point, no matter how much you try. For me, it’s more of a mental block than a physical one. Any advice to break down that wall?
Boy4Sir: “Sometimes I have this block. It happens when I know that I haven’t been able to prepare myself for the fisting session. Or when I don’t feel the spark between me and my partner. Chemistry between players is essential. Sometimes it’s better to stop and not to continue at any cost. Something trivial from personal experience: if I feel cold, my butt will never relax. If the room is not very warm, wear socks and sneakers. It looks sexy and you are not concentrating on your cold feet, but on your precious asshole.”
Pup Rew: “It felt like I had hit a wall early in my fisting journey, where it was difficult to get past just having a hand inside me. The moment you stop focusing on breaking through the wall and just do whatever feels amazing, the wall might just vanish.”
Pup Derix, a beginning fistee, would like to know how to make more local connections and form a group of trusted individuals to have fun with? He tends to build up walls with folks he doesn’t trust yet.
Boy4Sir: “Building trust is key to safe and exciting fisting. Stepping into a group setting with people you don’t yet trust can be scary, and that makes it difficult to feel safe and sexy. I would recommend building your network one step at a time. Meet one fisting friend, through them you will meet another, and so on. Focus on the social aspect of the community. Build trust over drinks before play is in the mix. From there, the effect usually snowballs!”
Want to know more about these kinksters, go follow them:
Boy4Sir
Instagram @boy4Sir
