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KaitlynneSis... US

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Sissy Life 💕


Good girls stay plugged. (This is the monster plug I posted this morning) Yes, I followed instructions like a good girl and left it in for 4 hours. It was quite literally a torturous bliss. Then, after I could finally take it out, I got a toy out and had some playtime. For the first time ever, I squirted lemonade ALL OVER THE PLACE while I came. I’d say that was 16.99 plus shipping well spent.


Rolled on a plug and chastity task on FapRoulette…which if you don’t know will give you 3-5 tasks depending on which game you play. I have to leave this HUGE plug in for four hours 😳 I could have picked any plug I supposed, but this is the one I had in mind when I was looking at the required times to leave in before I rolled. Gotta be honest and fair! (Pic from play time last night before bed)


Keyholder knows me as a guy. I show her this and she says ‘but it doesn’t even look like you’ I’m like ‘That’s the point’


Haven’t posted a pic of my greatest asset in a while….I love how the feeling of having it completely ruined lasts for hours after 💕


Image from playtime the other day 💕


Last week, I streamed me getting it from my BF for the first time. He didnt want the lights on, so it was mostly just sound…note how someone commented about how loud I am 💕 I’ve been wanting to record it in full light…this is legit porn quality sex. Friday was a GREAT day. I met my morning blow and go and made him cum in less than three minutes, getting a massive mouthful of love from him. He greeted me by grabbing me around the waist and kissing me, which was amazing - I used to not really be in to kissing men but it makes me feel so pretty and soft when he does that…so I’m into it now. Then my weekly BBC came and absolutely dominated me…it was rough and hard. Made me squirt all over the place several times and in one spot where he had me doggy, there was so much it soaked through a thick blanket down to the sheets. THEN my keyholder came over and we had drinks all evening. I wound up dildoing myself in front of her, then fingering myself to three HARD and impressive squirts under her supervision. After that I got sent to bed, still caged. The next morning she got it out so she could enjoy it too. It was a most amazing weekend! I feel so SO lucky to have a sex life like this as an older sissy.


Feel so lucky to wake up like this every morning with a real world keyholder 💕


Good morning ATW! ☀️


Sissy Saturday! Ok to be fair this was from yesterday’s fun but still. Good morning!


A good sissy wears her cage at all times 💕


I had some more fun with all the clothes I rarely get to wear...these were to tease my BF with since he couldnt make it today. He likes it when I wear black on black the most...and I had this new skirt to try on 💋


Not one of my favorites from this morning's "photo shoot" BUT I wanna share these gorgeous natural blue eyes with you 💋


It feels like less is more with makeup...subtle highlights seem to work best.


Its been a while since I got properly dressed and did some makeup, so today I decided to do it. I forgot how 'right' it feels ❤


#ThatsMyKink Crossdressing/Sissy life!


Got some b cup boobie inserts…it’s exactly what I needed! Looks like it was the perfect size to build the ‘curves’ a sissy should have. If only I were 20 years younger… 😂


Learning makeup…and anglefrauding 😂😘


Had a playdate with The Machine today 💕 Made me squirt HARD but I won’t put that in the feed 😂❤️


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