Ask Matt anything.

[LitDarkness]

What embarrasses you the most?

Did you know you have pretty male underwear?

How does sucking your dildo feel?

Did you like your caged dick yesterday?

What arouses you the most?

What underwear are you wearing?

If you had to choose between a year's chasisty or a ruined orgasm everyday, what would you choose?

[Matt:]

Originally Posted by LitDarkness

What is the most severe punishment you have received and why did you receive it?

The worst punishment would be for the offence I mentioned in a previous answer when I accidentally came without permission

Was basically a day of punishment. I had to get up at 5am on a Saturday, spend 5 mins kneeling in a cold shower. Was only allowed bread and water to eat all day. No clothes, hot water, TV, music, radio, laptop or phone (other than to report to Sam or answer others calling/texting me (keeping to minimum))

I had to pee into a container and keep all pee for later...

Approx every hour I would be given a task to do, pegs on various parts of body, spanks, corner time, lines, exercises, hang things from my balls...

At end of day had to put a white t-shirt on, kneel in bath soak some socks in my pee, gag myself with them then pour the container of pee over my head and stay like that for 20 minutes before having a cold shower and going to bed...

Definitely was very good incentive not to make that mistake again....

[Matt:]

What embarrasses you the most?

That is very hard to say, lot's of things embarrasse me, it's difficult to rank them and can change depending on the situation and other things. Maybe pee related situations, such as if I'm made to wet myself. Or being forced to share embarrassing pictures with someone for the first time..

Did you know you have pretty male underwear?

Thanks, now if only I got to wear them more often...(the more colourful one's at the top of pic are quite a recent addition after being told my underwear was mostly black/grey lol)

How does sucking your dildo feel?

It feels very embarrassing and humiliating, but can make me horny too...

Did you like your caged dick yesterday?

Can't say I ever really enjoy having my cock caged, not being able to touch and it being so tight around my balls.. yesterday was not for a long time though, so was not that bad even if certain things did make me horny while wearing it.....

What arouses you the most?

Not easy to pick one thing, but ultimately I'd say being in a 69 position with Sam..that is just so amazing...or if on my own then just imagining 1 or more ladies taking advantage of me and having their way with me...

What underwear are you wearing?

White panties

If you had to choose between a year's chasisty or a ruined orgasm everyday, what would you choose?

They are both evil....but I would pick a ruined everyday, I could not cope with a year's chastity, not being able to touch or play, as well as the discomfort.

[LitDarkness]

Originally Posted by Matt:

The worst punishment would be for the offence I mentioned in a previous answer when I accidentally came without permission

Was basically a day of punishment. I had to get up at 5am on a Saturday, spend 5 mins kneeling in a cold shower. Was only allowed bread and water to eat all day. No clothes, hot water, TV, music, radio, laptop or phone (other than to report to Sam or answer others calling/texting me (keeping to minimum))

I had to pee into a container and keep all pee for later...

Approx every hour I would be given a task to do, pegs on various parts of body, spanks, corner time, lines, exercises, hang things from my balls...

At end of day had to put a white t-shirt on, kneel in bath soak some socks in my pee, gag myself with them then pour the container of pee over my head and stay like that for 20 minutes before having a cold shower and going to bed...

Definitely was very good incentive not to make that mistake again....

Yeah, it being for that offense doesn't surprise me.

Your underwear is mostly black and grey to be fair. Which one of the colorful ones do you like the most? (You can answer based on athestics if needed.)

How bad does the riding crop hurt?

What would be the max you could stand in the cage?

[Matt:]

Originally Posted by LitDarkness

Yeah, it being for that offense doesn't surprise me.

Your underwear is mostly black and grey to be fair. Which one of the colorful ones do you like the most? (You can answer based on athestics if needed.)

Haven't had chance to wear them all yet due to certain pm dares and rule's...but maybe the red/orange striped briefs. Think they look nice.

How bad does the riding crop hurt?

it comes quite sharp, especially if someone else is hitting me with it! If just getting hit by the lose leather bit at the end, it's not too bad, but often end up being hit with the solid rod part, that can be very painful... I have currently misplaced it though..find it surprising that I can lose something like that in a 2 bedroom apartment, wouldn't think there was many places it could be haha

What would be the max you could stand in the cage?

Probably only 1 day really due to the fact that it interferes with my sleep. If it wasn't for that, then I could go a few days maybe, possibly 2 weeks, although not sure about that.... I seem to find that unless I'm being directly teased or watching/reading something that turns me on, that I just don't seem to get horny when wearing cage.

[LitDarkness]

Maybe you subconsciously misplaced it? (And are apparently good at hiding stuff.)

You don't think if I knew you were wearing the chasisty cage, I wouldn't tease you, did you? (Don't worry, I have no plans to even attempt to make you wear that cage long-term or short term in all honesty.)

What is more comfortable, boxers, briefs, or panties, and why?

[Matt:]

Originally Posted by LitDarkness

Maybe you subconsciously misplaced it? (And are apparently good at hiding stuff.)

maybe haha

You don't think if I knew you were wearing the chasisty cage, I wouldn't tease you, did you? (Don't worry, I have no plans to even attempt to make you wear that cage long-term or short term in all honesty.)

well, I guess that would be likley..but glad you have no plans for it!

What is more comfortable, boxers, briefs, or panties, and why?

Well there is not much difference between my boxers and briefs (my boxers are boxer-briefs, so just a bit bigger) they are more comfortable than my panties, they just have a bit more room for movement (and possible growth...) Some of the panties are just a bit on the small side..and a few of them have a tendency to slip down as I move about. But they can feel nice

[LitDarkness]

I seen your new picture request album.

What is the scariest thing that could get put in there?

Did you enjoy fondling your fake breasts a bit ago?

Do you wish I didn't mention that?

[Matt:]

Originally Posted by LitDarkness

I seen your new picture request album.

What is the scariest thing that could get put in there?

I'd really rather not say.......

Did you enjoy fondling your fake breasts a bit ago?

Errr yes, kind of....

Do you wish I didn't mention that?

Yeah, it is rather embarrassing....

[LitDarkness]

You do realize this is Ask Me Anything, right? But, keep quiet, will just make it all the more fun.

Anyways, getting used to heels?

Enjoying sitting to pee?

[Matt:]

Originally Posted by LitDarkness

You do realize this is Ask Me Anything, right? But, keep quiet, will just make it all the more fun.

Anyways, getting used to heels?

Well I'm a bit better at walking in them, don't feel like I'm going to fall over every step now haha

Enjoying sitting to pee?

As I have to wear an overall at work, it is a bit annoying as have to basically take it off every time I pee, but otherwise it's okay.

[LitDarkness]

Better at walking in them is good.

What do you think about walking in them a little bit all week? (Excluding Sunday)?

Overalls and sitting to pee are a bad combination.

Is there a moment (non-kinky) that you would like to go back in time and change? If so, what?

[Matt:]

Originally Posted by LitDarkness

Better at walking in them is good.

What do you think about walking in them a little bit all week? (Excluding Sunday)?

I guess I could cope....

Overalls and sitting to pee are a bad combination.

Is there a moment (non-kinky) that you would like to go back in time and change? If so, what?

That's difficult, there are a few things! Hmm maybe pick a different college course, as the one I did was a total waste of time and was not useful, or learn to play an instrument.

[LitDarkness]

What was the college course you did?

[Matt:]

Originally Posted by LitDarkness

What was the college course you did?

It was an IT/computer course, but it was totally out of date even when it was taught. As an example, they were still using 5.5" floppy discs.....!