What was it like the first time you tried anal pleasure?

[Rue Rue]

I finally tried fingering myself and it is so awesome! It just slips in now. Does anyone want to share their first time doing it? It is so easy now that I've done it a few times. And yes. I have short nails and wash my hands. 

[barnburner]

My first time I was reluctant to put a finger up in there, but I found something I wouldnt mind tossing if I used it there, I went with a sharpie marker, maybe around half an inch in diameter, I wrapped it inside of a plastic grocery bag, slathered some lotion on it and went to town, I did enjoy it, I got spooked about the possibility of the sharpie exploding like pens do so I ordered my first plug of similar diameter. I then tried a vibrating half inch anal bead thingy that an amazon seller was selling for just under $10usd which may have been a price error as soon after it was up to nearly $50usd. I have worked up to 1 inch diameter plugs, I am now looking into training aids to try and get past an inch because I have a 1.25in vibrating plug that I cant get into me fully yet.

 

Along this time I have eventually used a finger in there every now and then and now have no issue covering up my toys that will get poo on them.

 

Sliding a finger or plug in and out repeatedly is also fun.

[Snugglebear_69]

Toys and fingers and things are ok but absolutely nothing compares to the first time my Daddy entered me anally and especially the first time He reached completion. Toys and fingers just don't compare.

[tommyneedsdiapers90]

i had a daddy plug me as punishment and that was my first experience. he used lots of toys on me to make me squirm and be obedient. he never went inside me tho, id always go in him. someday ill have a daddy take whats his

[Rue Rue]

21 hours ago, barnburner said:

My first time I was reluctant to put a finger up in there, but I found something I wouldnt mind tossing if I used it there, I went with a sharpie marker, maybe around half an inch in diameter, I wrapped it inside of a plastic grocery bag, slathered some lotion on it and went to town, I did enjoy it, I got spooked about the possibility of the sharpie exploding like pens do so I ordered my first plug of similar diameter. I then tried a vibrating half inch anal bead thingy that an amazon seller was selling for just under $10usd which may have been a price error as soon after it was up to nearly $50usd. I have worked up to 1 inch diameter plugs, I am now looking into training aids to try and get past an inch because I have a 1.25in vibrating plug that I cant get into me fully yet.

 

Along this time I have eventually used a finger in there every now and then and now have no issue covering up my toys that will get poo on them.

 

Sliding a finger or plug in and out repeatedly is also fun.

Oh my gosh! A sharpie was what I used my first time too! I was dared by one of my exes. 😆

[LittleRen77]

I think my first time was with the handle side of a small screwdriver (like, not the screwing end!!!).  It was all I could find that seemed the right size and shape.  It had a soft rounded end, and I wrapped it in plastic wrap to keep it clean (and me... it was a tool after all!), and rubbed on a bit of olive oil.  And I was careful not to go too far!  I recall it feeling very nice!  I've graduated to real toys since then, of course!

[foreverdl]

I think my first time was just fingers. I then went to banana it was hard to find a small but sturdy one. It smashed, so since I was doing enemas I used the excuse I needed stuff to hold my poop in and that way my wife would not think things. Well yrs later I really just tell her I need my butt toys. I have all sizes and a good assortment , I wish I could get the real thing but scared of hurting my marriage, and then the STD's But I do have to tend to my self for sex, my wife due to health issues hasn't been able to do it for over 10 yrs. So she is a lot more understanding with my toys.

[barnburner]

I have finally graduated from a 1 inch plug to a 1.25 inch plug!

 

My behind needs time to adjust I guess.

[Snugglebear_69]

It's a muscle like any other. I remember when I first started and a finger was too much and now my Daddy, with patience, can go a full fist.

A lot of people think anal play makes things looser when in reality it actually improves muscle strength and control.

[PullUpDiaperLover]

The first time I really do not remember, but the first time with a vibrator in while having sex I nearly passed out. Its an incredible feeling having that done to your prostate while having intercourse or someone servicing you.

[Goodniteswearer89]

Like others have said my first time was also with my fingers I would then move on to using tampons and I would even try to use my moms dildo that I found when I was a teen I would eventually once I got my own place buy a small vibrator and now I have a few plugs some that vibrate and some that don’t. The first time I did it I liked it but just didn’t like how I would have poop on my fingers or anything that went up there. It took me a while to realize that I need to give myself an enema before I do anything back there.