insertion techniques painful?

[dubpistol]

hi
have any of you guys ever tried jacking off but with a dildo up your ass?
i have had this before with my GF but i was trying it out solo yesterday
while jacking off to some domme TS pics and fuck me it really hurt
i could hardly get it up there, anyone know how to relax more or what lube to
use, im always freaked that when i finally do get to make love to a TS and
they want to penetrate me I wont be able to recieve or elsse it will hurt like
hell. its the same when my GF does it to me.
whats a boy to do?

[Loki]

That's a good question. I wonder if I should try some things solo before my first time with a t-girl. Or should I just wait and hope I find a t-girl that will be gentle with my tight virgin ass the first time?

[Bionca]

The sphincter needs to be coaxed to relax since it's job is to keep stuff in until the right time. If you can slip a dilio in the bottom without any prep time, there are probably going to be some issues later.

First realize that dildos and real life cock are not the same. the real thing has more give than a dildo, so it's actually tougher to insert a dildo. One thing to do is to massage the pucker with your fingers first while masturbating. the combination of arousal and stimulation of the prostate and sphincter will loosen you up. A little finger-fucking will go a long way - trust me. For goodness sakes, also remember to remove hang-nails or sharp nail edges!!!

With a partner, rimming is an option. There are some health and cleanliness issues around this (see my posts on enemas), so you or your partner may not want to do this. Goodness knows I keep mine sparkling clean and don't get that kinda booty lovin' (grumbles).

[Nielsholgerson]

Start slow and go deeper every time, this way it doesn't realy hurt.

[Htowner]

Originally Posted by Bionca

Goodness knows I keep mine sparkling clean and don't get that kinda booty lovin' (grumbles).

You come to Houston and I will personally see that you get that kinda booty lovin'!!!

[sesame]

Originally Posted by Bionca the sweet

Goodness knows I keep mine sparkling clean and don't get that kinda booty lovin' (grumbles).

Now, now, dont you lose heart.

[twistedone]

I served an online Domme at one time. We went to a web site together, and she selected both a (lifelike) dildo, and a penis shaped buttplug for me to order. Which I did.

The size of the dildo wasn't supposed to be that big, just average size. When it arrived to my horror, and my Domme's amusement, it seemed that whoever measured the thing was illiterate and didn't know how to measure. It was huge.

Under the instruction of the Domme, she tasked me to begin using it. I was like "You want me to do what with that?" After awhile, I found I rather enjoyed it. I wasn't allowed to masturbate while it was inserted.

The very simple things she instructed me to do, turned out to be the key in me enjoying it.

1. Clean yourself. A cleansing enema, followed by a couple of rinse cycles.

2. Lube. Use a water based lube. Use a lot of it, use copious amounts of it.

3. Start with the buttplug first, Lube it and DON'T force it. Relax, soon it will find itself inside you. Keep it in awhile. Sit down, walk around, etc. She had me walk to a grocery store 4 blocks away and do my grocery shopping with it inside of me.

4. After removing the buttplug, lube the dildo up with lots of lube just like you did with the buttplug. DON'T Force it!!! By then, you should be used to having something inside of you, and it should slide in. DON'T force it all the way, let it naturally go in as far as it wants to go, DON'T force it to go any further.

5. Sanitation - keep it clean. Make sure you clean it very well after each use. Very important.

The dildo the Domme had me order has a suction cup base. I recommend it. She had me stick it to the wall and get on my hands and knees and back into it. As well as stick it to the floor and sit on it. She also had me lay on my side and pump it in and out with my hand. I would do this a twice a week as she instructed.

To my astonishment, I found I rather enjoy it. Its not unpleasurable to me.
And I'd love to experience the sensation of a Shemale Domme cock inside of me.

Incidently, the Domme had me order a black lifelike dildo, with head, veins, and balls. Think she had something in mind for me?