Being pegged

[BabyJessica]

My wife pegged me for the first time last week. She pulled my diaper down and went to town. It was amazing - it felt so yummy and good, and also made me feel so girly and humiliated (in the best way). 
 

I wasn’t able to make stickies from this, though I did rubbing my diaper after. Any advice for how to have a real sissygasm? Or good positions to try? I was on my tummy, knees under me, cunny up for my wife to probe. It worked but I imagine there are many other fun positions, too. 
 

I’d also be interested in hearing other ways you’ve enhanced the pegging experience. Definite newbie here, but both my wife and I expressed interest in continuing to explore with it. She loved the feelings of the harness rubbing against her womanly spots. 

[foreverdl]

On 4/25/2026 at 12:28 PM, BabyJessica said:

My wife pegged me for the first time last week. She pulled my diaper down and went to town. It was amazing - it felt so yummy and good, and also made me feel so girly and humiliated (in the best way). 
 

I wasn’t able to make stickies from this, though I did rubbing my diaper after. Any advice for how to have a real sissygasm? Or good positions to try? I was on my tummy, knees under me, cunny up for my wife to probe. It worked but I imagine there are many other fun positions, too. 
 

I’d also be interested in hearing other ways you’ve enhanced the pegging experience. Definite newbie here, but both my wife and I expressed interest in continuing to explore with it. She loved the feelings of the harness rubbing against her womanly spots. 

I say you are soo lucky, I have explained the pegging to my wife and that I would love to try it, and she's like grossed out.. She knows I use my butt plugs and toys, I haven't told her I use dildos in both ends...

[cuteandfun99]

My wife and I have been pegging for a long time and I love it.  You can experiment with positions (onyour back, on your knees, spooning).

Sissygams without other stimulation are harder but possible. I find I need to have a multi-day build up woth plenty of edging and once that happens I can often have a sissy gasm.  Sometimes its easier to sit on top so you can control the feel to get it to happen.

[JP403]

It is my dream to one day experience being pegged and have a women be so gentle when doing it

[Sissy baby Jess]

Regardless of whether you are being pegged or not, in my exeperience, having a sissygasm, needs you to be in the right head space. You need to totally let go of any sense of 'adulthood and manhood'. If you're a sissy baby, you need to accept, you have no control - and your partner will dictate when you are allowed sexual pleasure. They may starve you of that for days, weeks, or months - that's their call and should be respected. Ideally, they will 'tease' and gently humiliate you on a regular basis with 'baby talk' and 'diaper checks' and making you feel little. Once you are in that 'head space' I'm condfident you'll be able to achieve a sissygasm when being pegged.

Would love to know if this works for you.

[Meeseeks88]

I have only been pegged a handful of times but I've found that being gagged with a pacifier helps me. I guess it adds to the overall humiliation.

[DiaperLover84]

I get pegged or toys used on me weekly.  Wife has gotten new toys and larger ones to to fill me up.  Largest dildo slides in with no issues now, and slowly working to possibly fisting.  Whenever I am pegged a condom is used to collect all my cummies and then occasionally she will feed me my delicious nectar.

[wetste]

Whenever my wife pegs me i just want it out. I find it so uncomfortable. Is this just a case of building up the time? We only use a small dildo too. 

I really want her to go to town on me but the reality is its too uncomfortable 

[Snugglebear_69]

4 hours ago, wetste said:

Whenever my wife pegs me i just want it out. I find it so uncomfortable. Is this just a case of building up the time? We only use a small dildo too. 

I really want her to go to town on me but the reality is its too uncomfortable 

Not everyone enjoys anal sex. For some folks the idea is more enjoyable than the action.

[jesse78]

Plenty of lube and starting slowly and gently until you've relaxed is the key to wonderful anal sex.

[backdoorlarry]

98% of the "She caught me by surprise" stories are fake. Posters should make the disclaimer when they do. You need to get cleaned out first or the mess will end up being intolerable. Don't get me wrong, they're just "Stories", not reality.

[foreverdl]

I have done butt play with not cleaning out and really pumped myself with it, and it feels sooo good, to think it is someone else doing it... Its a little mess to wash off the toy and butt, but not as bad as I thought it would be.. I think if someone used the real thing they would definitely need a good condom to keep themselves cleaner. I generally do butt play after my nightly enema but sometimes spur of the moment is very nice..