discovering anal pleasure

I started discovering self anal pleasure a few month ago (fingering and enema) and i want to try sextoys but i felt a little lost after seeing the large amount of choice so here is my question:
Whit what type of toy should i start ? Plugs, beads, prostate massager, ...?

 

I LOVE my vibrating plug. It's large but I worked up to it. 7 inches deep with a bulb end and the tapered neck us about 1.5 wide. Comfy for long wear.
You just have to find what works for you. Graduated sets are a great way

 

I love my vibrating plug. It’s just really amazing feeling.

 

What's the biggest you can take comfortably and how big do you want to go?

 

Depends on the shape. But largest I have used is about 8 inches long and 2.25 wide at the bulb end.
I don't know how large I would go... Nothing that would damage anything for sure. Y'all know how much I love my anal, well EVERYTHING

 

My goal is to eventually have 2 guys DP my ass

 

Woo hoo. Good goal!

 

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Anal play is sooooo much fun! Try plugs, dildos, beads, etc! You never know what's gonna give you the best pleasure until you try it!

 

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Yikes!

 

Have you anal DP?

 

Start small and use lots of lube! You can work your way up just go slow. I have used lots of different toys, beads, plugs, dildos. It’s all fun and jacking off with a plug in or riding a big dildo leads to amazing orgasms and cumming!

 

I started anal exploration when I was young. Anal had always fascinated me.
I remember sneaking a couple of my dad's screwdrivers into the shower one day. It was a mixed emotion of pleasure and taboo.
Once I was old enough to be on my own for a weekend, my parents went away. The first morning started off with a very small screwdriver handle then I progressed to the largest ones he had. Deeper and harder was the goal. Then inserting a second, then a third. For hours those plastic and runner handles were being jammed up my colon.
As the day wore on and turned to night. I had the idea to go outside. Living on a farm there was no one for miles. Stripping off my clothes, the cool night air on my exposed cock, I was quick to jam 2 of the larger handles in my bowels. I walked around the yard and could feel them grinding and bumping against each other. My cock was dripping pre cum like mad.
Then I noticed a handle on one of our tractors.... It was "massive " in my mind. I quickly cleaned it off with soap and water to remove any dirt or grease. Pulling the screwdriver handles out of my now loose hole, I lowered myself onto the handle. The plastic knob and steel shaft were cold and rigid but also exhilarating. The large knob made its way deep into my young body and its outline was slightly visible in my lower body.
I think I sat on that handle for over an hour that night enjoying the sensations and stroking my cock.
Fast forward to today, I have a toy collection that ranges from going deep (18") to wide (3"+).

 

One of my deepest desires is to have someone do me in the ass. I once stuck a pill-shaped vibrator up there, and it didn't do anything for me. I wanr rhe real thing.

 

Once. Not entirely intentionally. But woo Hoo it felt so nice.

 

One in vagina, one in ass and the vagina guy slips out and goes anal by accident?

 

I can't stop thinking about doing anal with a girl. my only experiences have been trials and the girls haven't been that into it which doesn't work for me. Is it still something guys can ask for or random luck and hope the girl just grabs my head and slides it in?

 

I started with a smaller, thinner toy recommended by someone and that went OK. Tried a butt plug and that was not so much fun. It was just a stretch...which by itself was good but I wanted deeper. Ended up with a couple of Aneros toys which touched deep inside and still gave a good stretch.