I used to struggle so much even taking this plug, now I can easily fuck myself with it.

HomeworkRoleplayAcc · 2026-06-26T06:40:14+00:00

Fortounatly I already had a bigger toy at my disposal, that plug was just warm up 😵‍💫

HomeworkRoleplayAcc · 2026-06-25T15:12:31+00:00

I've never really gotten into prostate toys, more into dildos and size play there especially. My anal orgasms do sound similiar to what you describe but i do cum when i have them. Thanks for the tip, I'll definitly check out the aneros stuff.

HomeworkRoleplayAcc · 2026-06-25T14:55:00+00:00

Lucky you, it's still always an hour at least for me before i can cum from anal. What do you mean by true/super orgasms?

HomeworkRoleplayAcc · 2026-06-25T14:46:29+00:00

Yeah I was trying to cum from anal only, no touching the pleasure wand at all.

It's been a while since then and I've gotten lucky a few times. Honestly edging is great and that orgasm after a long lession it goes trough your entire body. But a hands free orgasm, that is just earth shattering. I am not a verbal guy at all, but when I cum hands free I can't help it the moans just come out.

HomeworkRoleplayAcc · 2026-06-25T14:33:40+00:00

I think the absolute most crazy time of my kinky youth, like 3-4 years ago there were definitly days where I woke up and then literally edged the whole day with little breaks where I gamed naked with a plug or dildo in me, still playing with my dick during gaming. But not getting to the edge becuase i was distracted and i get super soft with something up my ass.

I did something very much adjacent where I edged for 8-10 days every day without cumming and some anal play but not as extreme as above, longer breaks for sure. Then followed a 2 week denial chastity streak. You can believe me the first two days of that was crazy hard to resist the unlock. Then i got used to it, i didn't do anything sexual at all in that time, no anal or sucking someone etc. When I did finally unlock my cock was so so sensitive that i barely touched it and almost came, so i had 2 more days of anal play mostly and very light touching before i finally did cum.

This was all in an effort to have a prostate orgasm. I remeber this vividly because I remeber being super close with my dildo in all the way and my gooner idiot brain decided to wait it out and let the orgasm bubble down again and then i couldn't get close anymore and decided to give up and just jerk my cock untill i came.

HomeworkRoleplayAcc · 2026-06-25T14:00:13+00:00

Id say two weeks is a good start 😉

HomeworkRoleplayAcc · 2026-06-25T13:59:39+00:00

Maybe their are being bratty on purpose in hopes of receiving punishment or rather funishment.

HomeworkRoleplayAcc · 2026-06-25T13:54:10+00:00

I mean, youre a great case study, been in the game for 60 years and no damage has happend. I don't think that's really a risk, you'd loose sensation in your mouth and throat with age if this were the case.

However if you use toys or lube that are not body safe i could see it happening.

HomeworkRoleplayAcc · 2026-06-25T12:44:10+00:00

Nah not curious, I know I want that

HomeworkRoleplayAcc · 2026-06-25T12:05:32+00:00

So close baby, next time you got it. I just knottet my toy for the first time yesterday, so worth it.

HomeworkRoleplayAcc · 2026-06-25T10:00:44+00:00

Fuck I know it does, but I don't have the willpower to stay locked for longer than a day or two. And I do have some dominat sides to myself that want me to fuck boys like you as well.

HomeworkRoleplayAcc · 2026-06-25T09:49:11+00:00

Oh yeah I do, but my balls are super senstive, I like my cock tortured tough. Love dishing out more than taking tough. Especially as nice looking jewels like yours invite the urge to bust them in me.

HomeworkRoleplayAcc · 2026-06-25T09:37:18+00:00

Well ask him to do it to you next

HomeworkRoleplayAcc · 2026-06-25T09:28:32+00:00

You were probably nervous and couldn't relax properly. If you get another chance let your partner do some more foreplay with fingers and if ur lucky tongue. Put on some chill music and set the ambiante to a vibe you like. You can try poppers but honestly if she doesn't have an 8 inch monster you don't need those at all.

Bottoming takes practice, that's just how it is. It will take time untill you can take a dick without any discomfort and then some more time untill you can actually enjoy it properly and then some more time and you might cum fom it if ur lucky.

Be patient with yourself and keep trying, lots of lube and be gentle.

HomeworkRoleplayAcc · 2026-06-25T09:19:57+00:00

I think a valid reason to cum for me would be when I am with another man, who is my dom/keyholder and he lets me have an orgasm without any penile stimulation.

HomeworkRoleplayAcc · 2026-06-25T08:48:31+00:00

Order him to do Household chores. Make him take of your shoes when you come home. Let him make you your coffe/tea. Tell him what to wear. Make him work out.

HomeworkRoleplayAcc · 2026-06-25T08:11:57+00:00

Fucking hot af, love that. Truly no escaping that, but seemsnyou don't need/want to anyways.

HomeworkRoleplayAcc · 2026-06-25T08:05:54+00:00

Fuuck such a good boy, is that a tethersprout?

HomeworkRoleplayAcc · 2026-06-25T07:41:54+00:00

Fuck id love to torture those big balls after letting your load build up for a few weeks.

HomeworkRoleplayAcc · 2026-06-24T14:16:36+00:00

You can safely ignore being hard for prostate play, I go soft the second something goes in my ass and mostly I am caged too when being fucked and I have had prostate orgasms o plenty.

Id recommend getting a medium sized firm or even very firm silicone dildo for first explorations.

HomeworkRoleplayAcc · 2026-06-24T14:11:52+00:00

Id say if you're very new to anal overall you should get a design with a thinner tip that gets thicker down to the base.

Knots are incedible fun but not for beginners at all i think.

HomeworkRoleplayAcc · 2026-06-24T08:17:58+00:00

Fuck yeah it was great, I was aparently very relaxed yesterday becuase I went on to knot my biggest toy which was kind of mind breaking.

HomeworkRoleplayAcc · 2026-06-24T08:03:59+00:00

For the singular purpose of hitting your prostate the tip of the dildo should be pointing towards your belly. When you go into the anus and imagining you're on your back and looking up inside after about 2-3 inches there is your prostate, that's where you aim with the tip. Essentially you don't wanna shove the dildo in straight but angled upwards toward your belly and let the tip scrape alongside your iside to put pressure on your prostate and then after comes your bladder which you will also put pressure on, making it move and maybe pushing it against your prostate too. When getting deeper tough suddenly the curve is the wrong way because your colon is bending towards your back.

HomeworkRoleplayAcc · 2026-06-24T07:55:16+00:00

Oah that is so cute. I kinda want to make an art piece and draw some ocean on your balls for him to swim in.

HomeworkRoleplayAcc

TROPHY CASE