How to go deep with anal toys

I have had 19 inches inside of me but I did have to work up to it.....it was 1.5 inch x 19 inches. Before this I had a 18 inch x 2.75 buried to the balls, again it took lots of time and a boat load of lube....I love the feeling of have my ass filled and I hope someday to have the real thing in my ass. I usually start with a 20cc syringe of lube injected into my ass then my 7 inch x 1 inch, Then my 9 inch x 1.5 inch, then my 12 inch x 2 inch. In between each cock shaped dildo I shoot 20cc of lube......by the time I get to the longer cock shaped dildos I am into this for about 2 hours......take your time and enjoy!!!!!
Would love to spend 2 hours doing what you do! What fun!
 
If you want to go deep perhaps a good enema or two beforehand then start slow with the softest most bendable flexible toy you can find. Go slow and enjoy the ride. Think of how your insides are shaped and the turns it takes. And yes. If you stretch your pussy to much think about some panty liners to soak up what may or will come out
 
it definitly is up to the individuals personal preference, for me I start with some tranny porn or gay crossdressing porn. that leads to my fem side coming out , drawing a bubble bath. the make-up then putting on some sexy lacy panties and bra, after getting all dolled up i go on-line and play on the cams so several guys can chat me up and i usally tease them enough to get their dicks hard. its indescrible what that does for my arousal. im so horny I start sucking and deep throating my smallest dildo a 7in. x1.5 thk. than View attachment 2215636after a few minutes my largest dildo comes out to play, a 12in.x2.75in. and that one gets the same tongue and throat treatment. ..by than my ass is ready and i take each one alternitly like i was with two guys,...and i usally end up with both deep in me at the same time.. a little pain at first but the desire to take both will replace that pain with sheer pleasure and a smile on my face. stay in practice and you will always be confident and ready when you meet that special guy or two.
I would love to be one of those guys!
 
I guess you can call me a bi male. I am not “attracted” to men per se, but I am very interested in dicks and also getting penetrated. I have had a few experiences but one issue has been that my rear end is tight. I have had some recent success in loosening myself up and have been experimenting with a few toys. My concern is how do you get a dildo beyond the rectum wall? I have some idea but have always experienced sharp pain as whatever is up there just hits a wall. Seems like it would be easier to get more than six inches up my butt, but I sure as hell don’t want to hurt myself in the process of trying. Any direction that can be provided is welcomed. Not something I want to talk to the doctor about!

Just call me a bit clueless!!
Take it slow and use lotts of lube, lube is the key :)
 
Would love to spend 2 hours doing what you do! What fun!
I love my playtime with my toys! When I get really worked up I have a cock shaped dildo in my ass, one in my mouth and my fleshlight is getting a workout from my cock....which at the end I get to lick and drink from my fleshlight while still having a cock shaped dildo in my ass! MMMMM!!!
 
Start small and increase size. Copious amounts of lube. If I have a date with a top with a large cock I will pre-stretch my hole before he comes over. I don’t over stretch though. I still want to be tight and able to grip his cock with my ass.
 
Finding a top knows how to stimulate my p-spot is not necessarily a given. I often coach the top to use his cock head about 3 inches in my ass. Once he does his job and I have orgasmed I want him to pound my hole.
I know when he hits my prostate. Good communications is key.
 
I have fished around with my finger really didn't feel anything in there lol so is it something you have to do yourself?
 
I have fished around with my finger really didn't feel anything in there lol so is it something you have to do yourself?
Through experimentation I have found a few minutes of his cock rubbing my prostate and as I feel my self coming I have him slowly pull out. Results in a mind numbing orgasm with a huge load of cum. This is me and may be different for others. It also works with a dildo.
 
I hit a hard stop at almost 9 inches where it becomes uncomfortable, would love to go further but haven't figured out how safely.
I do as well...I think it's a prostate issue where things get very uncomfortable, even painful, at about 9 inches in.
I actually enjoy the feeling or sensation I experience right around my hole and maybe a couple inches in but my hole and initial penetration feels better to me than having something deeper...😉
 
I do as well...I think it's a prostate issue where things get very uncomfortable, even painful, at about 9 inches in.
I actually enjoy the feeling or sensation I experience right around my hole and maybe a couple inches in but my hole and initial penetration feels better to me than having something deeper...😉
The pleasant sensation you experience at your hole and a few inches is from your prostate. It’s only a few inches inside your hole.
 
Well, interesting thread i started. I wish i could get a nice cock up my ass bareback. Not in the cards for obvious reasons
 
Finding a top knows how to stimulate my p-spot is not necessarily a given. I often coach the top to use his cock head about 3 inches in my ass. Once he does his job and I have orgasmed I want him to pound my hole.
Yummmmmm
 
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