Thirty. Nine. Days. 🥵 I only set out to do Denial December, but now that I've come (definitely not cum) this far, it feels like I should just keep going 🙈 How much longer should I go? Or how should I be allowed to cum?2yr ⋅ helpmedrip ⋅ r/chastity
I've been getting laser treatment for my body hair so I can be smooth all the time. 🔫☀️ Would you let me wrap my legs around to you? Would you prefer them around your waist or your face? 🤭4yr ⋅ helpmedrip ⋅ r/Sissies
Locked up and going nowhere. At least my cage is pretty, don't you think? ☺️3yr ⋅ helpmedrip ⋅ r/chastity
13 days since I last came and my mind is shrouded in a pink cloud of arousal and desperation to be good in the hope I get to keep trying to sissygasm.3yr ⋅ helpmedrip ⋅ r/Sissies
I never used to like pink as much as all the sissy content out there suggested I should because I think hot pink is just too garish for me. But then I found baby pink and I think I'm in love 😍💖 Do you think it suits me?3yr ⋅ helpmedrip ⋅ r/Sissies
Wishing I had curvier hips and a tighter tummy, but still liking my body as it is 😊 I'm supposed to be getting work done oops! 🙊4yr ⋅ helpmedrip ⋅ r/SissyChastity
I've just finished making dinner and our guests are at the door. How much longer are you keeping me like this?4mo ⋅ helpmedrip ⋅ r/SissyChastity
You can't tell in the photo, but I gave myself a creampie for this shot. Better luck capturing it next time, perhaps?5yr ⋅ helpmedrip ⋅ r/SissyChastity
29 S 4 Tops, online • Looking for someone to tell me a thoughtful story about what they'd do to seduce me to this point and beyond • I like petplay, sissy maid training, chastity, bondage, and mind games • I share photos if your way with words makes me want to • Kik helpmedrip3yr ⋅ helpmedrip ⋅ r/sissypersonals
I'm really enjoying my Cherry Keeper. The headlock feature is great, though I still need to smooth the inside. Has anyone found a effective and easy method to do so?4yr ⋅ helpmedrip ⋅ r/chastity
You can just tell your girlfriend, She followed me home, and she's such a good girl! 🙎♀️💁♂️🐕🎀5yr ⋅ helpmedrip ⋅ r/FemBoys
I mean, you've come this far. So what if I have a tiny bit more than other girls? 😉4yr ⋅ helpmedrip ⋅ r/traps
Locked and needy 🥺 Do you have any suggestions to help me get some relief?4d ⋅ helpmedrip ⋅ r/chastity
28 S 4 Tops, online | I'm really stoned rn and would love to chat or role play right now. I like stories of chastity, feminization, and I want to explore humiliation 🥺🙏🙇♀️🌺 | Kik helpmedrip4yr ⋅ helpmedrip ⋅ r/sissypersonals
Daddy has taught me to maintain this position anytime he enters the room 🙇♀️5yr ⋅ helpmedrip ⋅ r/Sissies
What are you hoping Santa brings you for Christmas? I'm wishing for some sexy Christmas clothes so this caption can be more relevant 🙃4yr ⋅ helpmedrip ⋅ r/Sissies
New lingerie set and I couldn't be happier! What do you think? I had to use a garter from another set. Could you tell?3yr ⋅ helpmedrip ⋅ r/FemBoys
What do you like most about chastity play? What mentally excites you about it? (Question open to all of you, no matter how you identify)4yr ⋅ helpmedrip ⋅ r/chastity
8 days without cumming. In this time, I've been made to edge ten times. And no relief in site unless I can learn to sissygasm. Do you have any advice to help me find some relief? 🥺3yr ⋅ helpmedrip ⋅ r/SissyChastity
You know, I actually don't get to take that many mirror selfies. What do you think?4yr ⋅ helpmedrip ⋅ r/Sissies
I finally got around to sanding down the inside of my CherryKeeper, so now, hopefully, I won't need to take it off 😳3yr ⋅ helpmedrip ⋅ r/SissyChastity
Numb and unable to get hard, even when out of its clitty cage. Extra small with no feeling at all. What would you do with it?4yr ⋅ helpmedrip ⋅ r/Sissies
I got asked by a lovely Domme to copy a hentai image that she thought was cute. How did I do? 🍥🎠4yr ⋅ helpmedrip ⋅ r/chastity
Your girl made it through all 31 days of Denial December ☺️ How should we celebrate?2yr ⋅ helpmedrip ⋅ r/chastity
I finally got around to decorating my cage!, ⚪⚪⚪🎀⚪⚪⚪ What do you think about my handiwork?3yr ⋅ helpmedrip ⋅ r/Sissies
I'm still searching for the perfect plug. Any recommendations or requests? ♟5yr ⋅ helpmedrip ⋅ r/SissyChastity
Eating clitty isn't that different to eating pussy. Go on, have a taste! I bet you're a natural!3yr ⋅ helpmedrip ⋅ r/traps
I'm working towards losing some weight. Does anyone want to take me for a walk? ✨ 🐕🚶♂️💨5yr ⋅ helpmedrip ⋅ r/Sissies
Standing ready for morning inspection. What daily tasks would you require of me?4yr ⋅ helpmedrip ⋅ r/SissyChastity
Two weeks since I last came 😳 I keep fantasizing about having someone to give me obedience training to be a perfect sissy maid and have my clitty constantly leak from underneath my skirt.3yr ⋅ helpmedrip ⋅ r/Sissies
Belly ring got me feeling cute 😊 What piercings/body mods do you like sissies to have?4yr ⋅ helpmedrip ⋅ r/Sissies
36 days of denial. I'm frustrated, but taking refuge in being pretty. Please don't share any sexy thoughts in the comments, they'll just make me more desperate 🥺2yr ⋅ helpmedrip ⋅ r/traps
Should I go smooth and hairless? Has anyone got any good explanations to tell people why IRL?5yr ⋅ helpmedrip ⋅ r/SissyChastity
I think I want an even tighter and more shapely corset. Does anyone have any good recommendations?4yr ⋅ helpmedrip ⋅ r/traps
