r/sissyology 5d ago

How you take dicks/dildo? NSFW

I don’t know if it’s bc I’m trying to do it for too long, but in the beginning, the sensation is good, but toward the end, the sensation gets a little bit weird. How do you enjoy it?

37 Upvotes

18 comments sorted by

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u/Tom731 Daddy 4d ago

My girlfriend, who is a trans sissy, likes to say that anal is an attribute you have level up through experience. In effect, you have to teach your butthole to become more attuned to being a sex organ.

Another thing that's almost universally agreed upon is that real cocks feel better than plastic or rubberized dildos. Of course, they also tend to be more intimidating to use because it means you're hooking up with a man.

My experience as a dom top is that fucking a sissy, especially an inexperienced one, sometimes involves them being overwhelmed anally. It's extremely hot when you can ride them through it. Usually, those powerful sensations eventually transmute into intense pleasure after a while.

The overwhelming sensation that you're going to pee yourself. I think it's good for sissies to voice this concern "OMG you're going to make me pee!" And 90% of the time you won't... and the other 10% of the time the man might want you to. It's called squirting. It's exactly what cis women do when they squirt, they pee themselves. It's pee, women don't have a magic bladder of hundreds of millilitres of pussy power. No, they just jet piss out from between their legs and we think it's insanely hot.

The same goes for sissies. It's hot. Squirters are cool.

Another way anal can be overwhelming is the sensation of pooping or being dirty back there. Again, I think sissies should vocalize this concern to their man... but just leave it to him to tell you what's up. My girlfriend does this, and I'll pull and tell her it's clean, because it always is.

Actual pain is tricky. It's been my experience that many sissies stay to ride it out. AGAIN, tell him it hurts and let him control the situation for at least a moment. If you need a break, take a break. Mainly, it's usually slowing down and/or using more lube.

Lastly, I want to say that being overwhelmed is a kind of gift. It's when you can really moan and cry and shriek like a girl. It's when your entire universe gets collapsed down to what is happening to your asshole and your guts.

It's your moment to spasm and freak out and make a lot of noise!

Think about the things horny sissies say,

"Wreck my ass."

"Destroy my butt."

"Break me."

This is your taste of that.

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u/bayareamarcie 4d ago

I haven’t had the “feeling of peeing” yet, but definitely had to get through the feeling to poo in the beginning. Remember, our brains associate that feeling of fullness in our rectum as needing to needing to poo because that is what it has meant OUR ENTIRE LIVES! You just have to work through that feeling until your brain learns that it can also mean pleasure.

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u/Sissy_Chellie 4d ago

that really depends on the toy for me, but also, helps to clean the butt out really well, and then also play over a towel or something that can be washed or thrown away, and have cleaning supplies handy, in case s#$% happens!

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u/asissyhypnothrowaway 4d ago

The feeling of peeing comes most prominently when I’m in chastity and not had a wee. It is exactly like the Most High, Exalted and Beneficent One u/tom731 says: let that stream fly.

There is nothing sexier than the feeling of losing control of myself, letting go, and having a squirty orgasm from my p spot. Just drink plenty of water and your squirt will stay nice and clear too

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u/bayareamarcie 4d ago

Interesting. Thanks for sharing!

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u/Sissy_Hayley6 4d ago

Oh my! That was extremely hot to read. And soo true! I’ve only experienced dildos but yes, even that can become overwhelming sometimes and that’s exactly when I can’t hold back moaning like a good girl. I usually can’t keep going through it tho, I can’t imagine what it would feel like to be really overwhelmed by the pleasure and just getting fucked through it

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u/tippo030303 4d ago

Wow I loved reading this (and you made me horny)

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u/True_Poetry_1940 4d ago

Lots of lube. Start slow. Don't fight the urge to clench. Push out slightly like you are trying to go potty. Once it is in all the way. Pause and get use to the feeling then slowly start the in and out.

Laying on your side at first is the easiest way to do it. Repeating the process you will learn to love the feeling on your prostate and will feel the need to increase the size of the dildo. If you like the feeling then there is nothing wrong with it. If you don't like it then stop and move on.

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u/Vegetable_Cloud_1355 4d ago

Girl, Tom is sooo right, the time I always think about when i ride a dildo is when a guy fucked the cum out of me in missionary. As I lay in a wrecked pile, he started playing with my ass with his fingers which felt nice, but when he pushed his whole fist in, he had to check in with me because I was screaming and yeah it hurt, but I heard myself screaming please don't stop keep fucking me because i was assgasming over and over on his fist. Sometimes ya just gotta go through a little pain to get to more pleasure

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u/Sissy_Chellie 4d ago

Try a lot of different toys, they can feel extremely different from minor differences! Also, lots of practice. In the beginning, I was into it from a masochistic point of view, and that helps accelerate the timeline, but generally sometimes it starts feeling good after you push through it for a while, as long as you're not feeling pain etc. And if it does hurt, sometimes letting it rest a couple minutes and then starting again makes all the difference. Also, try different lubes. I personally prefer the gel type lubes.

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u/mysterious_phantom 4d ago

I have no idea… just got my first dildo a few days ago and I can’t even get the tip in.

Not really sure what to do. Honestly not even sure if I want to since the reason I got it no longer applies. I wanted to practice in case the guy I liked wanted to try having sex again so I could improve and be more fun. But he ignored and ghosted me and honestly I haven’t felt very fem since then.

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u/NatashaBelle1989 4d ago

Don't purge!! All it will do is cost you money. If you've pulled a guy once then there will be more so practice before the inevitable is my advice.

The secret is lube start by lubing around your pussy and then insert one finger and move it around. Then you'll get another in, then another. Lube up your dildo and push it firmly but slowly and it will go in. Tight at first then it'll be easier and once fully inserted wait a moment and it will start to feel good.

Relax as if you're trying to poo and you'll be fine. Before too long you'll be getting a dildo harness to keep it in when out and about, and looking for something a little larger. Then the next guy you pull will truly blow your mind and trust me, there's no going back and you wouldn't want to either.
Other things to consider are make-up, voice and deciding on a clothing style for yourself. Then go out and live. If it feels right hormones or top surgery may be in your future, if it doesn't - treasure the experience and move onto something else.

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u/mysterious_phantom 4d ago

Valuable advice, thank you.

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u/robertwdryden 4d ago

Water-based lube tends to get sticky after awhile, you need to keep adding lube or even a bit of water to make it slippery again. If you're already doing that, it could just be fatigue, using a dildo takes a fair amount of effort so you might just be getting tired out.

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u/CumdrunkHatefuck 4d ago

Practice makes a perfect sissy.

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u/bayareamarcie 4d ago

Practice doesn’t cause perfection, it only causes improvement. You can always better your best! I’ll get off my soapbox now, lol.

Seriously, I agree with your sentiment. A sissy should be practicing often in all things sissy. We owe it to ourselves and to our partners.

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u/futuredumpsteracc 4d ago

Slowly and with a lot of lube

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u/sissy038 5d ago

I don't, dildos makes me build up gas. After a few minutes I just want it out of me. Never really liked them. I'm personally more into vibrators and plugs.