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KaitlynneSissy

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5.0 (23) United States

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I am not 'new' to this - in fact I bought many items under my 'guy' account.

Long before the internet was easily accessible and I even knew what 's**' was, I was sticking things in my a** and just looking at how nice it was. It felt so good, and Im not even sure what prompted me to do it since I had zero access to porn or anything remotely pornographic. Before I even knew what any of this was, I wanted to dress like a girl and 'be pretty' for men.

As I grew older, gained access to porn, and the internet became a thing, I loved the sight of a hard d*ck and a big strong man’s body just as much as the sight of a naked womans body. I found myself watching lots of DVD and internet porn, but was more into watching the guy than the girl. Watching a**l s** was more of a matter of me wanting to 'be' the girl than enjoying watching her get it; though I do very much enjoy the sight of a womans body.

It was confusing for a while and I stuck to women, but now, I have fully experienced the best of both worlds...and both worlds are equally amazing in different ways.

I can and do switch back and forth from a 'normal guy' to a sissy. I can take on either a dominant role with women, or be submissive - both roles pretty equally fun. I very much enjoy complete degradation with women - forced a** eating, sp*tting in my mouth, and watersports.

My results from BDSM test seem accurate - I recently took it again and took the long version.

== Results from bdsmtest.org: ==
97% Non-monogamist
94% Submissive
92% Experimentalist
91% Exhibitionist
91% Degradee
86% Rope bunny
85% Masochist
73% Voyeur
72% Slave
71% Primal (Prey)
51% Switch
16% Primal (Hunter)
15% Pet
14% Vanilla
14% Master/Mistress
12% Brat
11% Dominant
4% Rigger
3% Owner
3% Degrader
1% Sadist
0% Daddy/Mommy
0% Ageplayer
0% Brat tamer
0% Little

Last few things:

I am *not* into Findom. I like Femdom - two very different things. I like mean-ish, take charge women but *also* free spirited, fun and happy personalities. In fact IRL if I were a womans sub it would have to be that free spirited type. 🕊

I do like to be a repeat customer...but that is 'when I can' and do typically buy from good sellers with 'that scent' over and over and over again. I hang out a lot here and am not always looking to buy.

Pushy sellers and sellers that ask for money for 'nothing' are not for me. Im typically looking for physical items, and very certain things. Financial domination is absolutely not one of those things.

Not really into instant content, though on repeat buys, sometimes I DO want to see more while I smell and taste you 💋

I am a bit of whore if you cant tell by my photos and BDSM test results. I cant be owned here on ATW. Life is short and I want to experience as many scents and tastes as I can. The human body is such an amazing, gorgeous thing...in all shapes and sizes.

Men: please do not approach me to pitch your sale; most of you are extremely s**y but Im not into buying mens products. I have a Grindr account that is constantly ON FIRE and dont need to pay for it. I have a couple regulars that give me what I need so Im just not looking to buy from men - even if you fond me on MTW. Sorry guys 🤷‍♂️

I also dont typically engage with content or items from overseas or across national borders - US Sellers only. Its a freshness and payment thing; its easiest to just limit myself to US sellers...it has absolutely nothing to do with anything other than convenience and freshness. I even prefer US sellers that are geographically closer to me to shave days off of shipping times. Believe me, there are TONS of gorgeous women from every nation here. I typically even filter the feed by 'US only' just so Im not 'enticing' overseas sellers to message me for a sale - Im not here to browse photos with no intent to buy, or goon out or whatever. Thats just how it is...I want your taste to be as close as gushing out of your body and directly into my mouth as possible 💕

Love you all!

About KaitlynneSissy

52 Followers - 119 Following - 13 Badges

Gender: Male

Age: 40-50

Joined: 1 year ago

Profile Visits: 5000

What I'm looking for

Socks Feet Accessories Feet Experiences

Photos 52 images

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Latest Activity

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KaitlynneSissy

If you haven’t already, check out the #GetYourAssOut contest!

21h

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KaitlynneSissy

Added a new photo > #ThatsMyKink

Crossdressing/Sissy life!

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KaitlynneSissy

Added a new photo > #getyourassout

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KaitlynneSissy

Added a new photo > 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… 😂

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KaitlynneSissy

Added a new photo > Learning makeup…and anglefrauding 😂😘

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Added a new photo > Had a playdate with The Machine today 💕

Made me squirt HARD but I won’t put that in the feed 😂❤️

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KaitlynneSissy

Week 1 of Full Time Chastity:

If curious how day to day life went, I have almost daily posts in my profile feed.

Overall, such an amazing experience. Self imposed chastity is one thing; I’d cave in and vibrate it at times. (Especially teasing myself with panties, socks and other ATW items)

After one week of real world full time chastity, I haven’t caved once. She IS letting it out almost daily, so there’s that. But I think even without it, I’d be a good girl and leave it alone. To be fair, I’ve used other methods to ‘get there’ (✌️🍑) BUT that’s a completely different type of O.

I notice so much more about her. I listen better. I’m even nicer to random people in public - I was always a very polite person to anyone in service industry jobs but even more so now. Women especially - even encounters with grumpy ladies in the grocery store.

I notice and appreciate so many more subtleties of her body. Every little jiggle, wiggle and ripple. Every slight waft of her scent drives me mad. All I want to do is exist to make her life better…but also make powerful, mind blowing ❤️ to her.

And we do. I was already dirty; that’s why I’m here. But now? Wow. She’s still easing in to it in a way, but sometimes I want to beg for her 💦 or when she has to go I want to beg for her 🍋. I want to taste and savor everything about her from top to bottom. I discovered that I liked feet here but it’s so much more intense. I can’t wait for her to come home so maybe, just maybe, I can get a taste before we get into the pool or something.

I love the sensation of it being locked up. Unavailable to me for the most part. Belonging to her. I love feeling it slightly compressed and bundled up all snugly. I love seeing it and knowing I have to be good to get it out…and when I do, it’s for her - not me.

She’s been noticeably in a better mood according to her coworkers. She even said she noticed a difference in having the keys on her all day, or hidden away in the car.

I’m leaking just thinking about all of this. Full time chastity is a life changing, amazing experience for both of us. I highly suggest this for any couples open to it. You may already love her, but you will become completely devoted to her. She in turn will experience a much closer bond with you. Her life will improve, no matter how good it already is. Lock it up and give her the keys forever.

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KaitlynneSissy

Day 7 of Full Time Chastity: A Milestone!

We made it to day 7!

She has let me out 6 times in 7 days, with two of those times being in the same day. Shes a very needy lady and we are definitely doing this differently - and its been great. Shes in complete control of erections and orgasms, but she wants it almost daily...and sometimes multiple times a day.

We've found a 'switchy' balance - while she is very much enjoying ownership and control, when it comes off, she needs to switch and become the sub. That works for me - I have so much pent up energy that its honestly a perfect arrangement. She gets it harder than ever before, and I get to enjoy one of two sides of my own sexuality.

We've also done some exploring with new things...which fits the theme here. She was just introduced to chastity a week ago, after all! Shes smacked my bundle of bliss around a few times, making me whine and yelp in torturous pleasure. She'll also walk by or reach down and randomly slap it now and then. Yesssssss!

Shes also watched me reach under with two fingers and...rub my spot inside 🍑. She held me while I did it, and it didnt take long to make a huge mess - it never does. Following that, we discussed adding new accessories to our lives - which we will definitely be doing. I brought a couple of toys I had stashed away in, officially part of my top drawer now.

Thus far this has been an amazing decision to introduce to our lives. It was a risk, but she was very open minded and is now very much enjoying this whole new dynamic to our relationship. Our bond has only gotten stronger.

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KaitlynneSissy

Added a new photo > Waking up like this with a real life key holder next to me is pure heaven. I’m so happy 💕

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KaitlynneSissy

Day 6 of full time chastity!

I’m calling it full time chastity since it’s not ‘permanent’. That seems more accurate. She’s let it out and used it 5 times in 6 days, but it immediately gets locked up after. (Hygiene prior to relocking of course) Out for showers with the understanding that she will be checking on me and supervising.

Last night was a locked night. There was lots of teasing and play time but it stayed locked up. Once again: an amazing experience. Trying to desperately to get an erection but not able to…teased in allllll sorts of ways from touching to body contact to…stuff being put in my face. But no, it remains locked. At one point I wound up flipped the other way just snuggling her foot against my face.

Every wiggle, every jiggle, every breath of her is intensified. Every peek of a nipple, the slightest glimpse of cleavage through her nightie. The view of her kittie and peek of her little cheekies from the front. The scent of her body. All of the curves from subtle to the view of her back down to her butt sitting up. So divine. Just the scent of her foot gently wafting across my face. Just….wow.

Waking up this morning was the most intense morning yet. I’ve never had it struggle so hard to…get hard. The cage totally encases it. It just tries so hard in there, but can’t. The buildup of pressure is indescribable. I can only imagine what this is like for those let out a lot less; in a way I look forward to it when the novelty of this whole new dynamic wears off. I can tell I will be even more devoted with true denial, but even without it…I’m not playing a role or exaggerating here. This is very, very real. The level of submission and desire is already off the charts; I asked her to spit in my mouth last night. When she had to get up to go pee, I was so close to begging for it.

This is a truly amazing experience. I know at the end of these little bloggy posts I recommend it, and I’m going to again. Women, if you can lock you man up, do it. Men, give her that authority over your erections and orgasms. She is truly a goddess and should be worshipped as such. ❤️

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KaitlynneSissy

Day 5 of Chastity with a real world key holder!

I’ve been let out every day except one. We have had sex 5 times in 5 days - twice in the first day. This would be almost a months worth of sex in a bad month. She is very clearly enjoying this - and so am I.

Even one day waking up and not being able to have morning wood is fun. I get that denial - often long term - is usually a part of this. We seem to have a different dynamic. She’s in complete control of it and wants it daily. Few men would complain about that, and I’m not going to either. She’s in charge and she gets what she wants. She teases throughout the day by gently touching that tight bundle of bliss. She’s even smacked them around a little, which was a mind blowing experience. This is just eye opening…and mind opening.

I do wait in anticipation of our first 3 or 5 day stretch without release, but what we are doing now is just as fun.

An important detail of this is that she was just recently introduced to this lifestyle. I am not sissified 24/7. While that would be fun, that’s just not what she wants. She met me as a guy and then later learned about this ‘dual sexuality’ I have. She has never seen me dressed outside of photos.

No butt stuff has happened yet, though she said that is ok with doing it. We’ll ease in to that (no pun intended🤣) My current plan is to just use two fingers on myself, rub that sweet spot inside, and cum for her.

I can’t recommend this strongly enough to men and women out there. She is so much happier, and our already strong relationship is only getting stronger. While it may not be the standard for living in chastity, it shows that there are many ways in which this can work.

I love you all, and have a happy Saturday!

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KaitlynneSissy

Real World Keyholder: Days 3 & 4

Thus far, she has released me in order to please her 4 times in 4 days!!! On Day 3, I was not released - she just released me twice on the first day from her excitement.

She is definitely loving this, and so am I. Self imposed chastity was one thing...but looking down at it or just feeling it there knowing theres absolutely nothing I can do about it is just amazing.

For her, she is very much enjoying being in complete control of my erections and orgasms. She is VERY possessive of the keys and it doesnt even feel like shes just playing along - she is truly enjoying this. She WANTS to be in charge of it. And I want her to be. I want her to be in complete control of my erections, orgasms, and...all of it. Its hers now, not mine.

I pay so much more attention to her. For example, I barely touch my phone all evening now. I havent gamed at all. I am totally invested in what she wants to talk about. I am so much more attentive to her physical cues; a neck stretch and I reach over to rub it for her. As the other posts said, Im more attentive to her needs - getting her drink refills and whatever other things she needs without even being told/asked to. I serve her her dinner...I pick up the plates...I get her seat ready the way she likes her blanket on the leather furniture...I make the bed the way she likes it...I sleep closer to her; I used to like to roll over in the figure 4 position and fall asleep that way. Now I hold her...and the last couple of nights she has immediately fallen asleep - highly unusual for her.

I want to touch her more, love her more. Every little detail of her body is noticed now; a slight jiggle or wiggle here or there sends a flood of warmth through me. I notice her toes. I notice a tiny bit of saliva as she speaks, I notice her lips. I notice her breasts and nipples more; almost as if its in slow motion. Everything about her is absolutely gorgeous.

Her scent - just the air as she walks by - results in a deep breath and slow exhale. The smell of the top of her head. The scent of her feet after work...drives me absolutely NUTS. In fact, I was home yesterday and while she was gone, I picked up one of her dirty socks and smelled it several times as I went about my day. It filled my chest with this feeling thats hard to describe. Just like any slight whiff of her body...just WOW.

Waking up in the morning has also been extremely fun. The poor little guy doing his best to achieve morning wood...desperately trying to expand and escape. The sensation is intense - theres so much pressure feeling it try its best to harden, but being completely encompassed by the cage...just the tip desperately poking out of the hole. It doesnt hurt like a lot of guys say it does; it just feels GREAT.

She has let me out 3/4 nights so far. It does take a little 'warmup time' for everything to return to normal, but thats ok. Thats time to literally worship her feet. I love the scent; I love the taste of each toe as I gently suck it and make sure my tongue makes a full circle for complete coverage. (I even brushed and mouthwashed first; her feet deserve nothing but the cleanest, freshest mouth) I love the final steps of cleaning her feet with my mouth in licking the arch and heel...Im leaking a little just typing this up!

We move on to more; she is in to oral pleasure even more than she was before. So much more thigh crushing, hip thrusting, and gyrating/pivoting. More of her powerfully grabbing my head and holding it as tight as she can to her. And then the booty...crack and all. My god. It already really got me going, but wow. I appreciate her scent and more importantly taste so much more...up and down her sweaty crack. A sweet yet salty taste...Im going nuts in my cage just recalling this to type it up.

Her coworkers have noticed that she is much happier already. I myself can tell she is so much happier already.

Best of all: thus far I have not been doing any of this in a conscious attempt to appease her and get out of the cage. Im doing it because I want to; this energy is driving me to essentially LIVE for her. This is just...amazing.

Women: talk to your men about chastity. Even if they already treat you well as I did her, their care for you will turn into complete admiration, devotion, and possibly true worship.

Men: give her control. Have her lock you up. Let her take charge of your orgasms and erections. You will NOT regret it. Everything you love about her is enhanced, and you will notice so many new things to love about her. She is already the most beautiful woman in the world, but she turns into an actual, real life Goddess when youre living in chastity.

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KaitlynneSissy

Good Morning all you kinky people ❤

I should probably start blog posting this experience and will look into it, but for now its going in the feed.

Day 2 of Chastity with a real world keyholder:

During the first two days, we have had sex three times. (really just a day and a half) This is crazy LMAO. I guess we are doing a slightly different style of keyholding; I mean she's in charge, but she wants it 🍆. (Its actually a pretty impressive unit when released, so I cant blame her🤣) While I would much rather be completely denied and not use it, shes in charge of it and she gets what she wants. So three times it is LMAO.

But you know what? So far it doesnt seem to detract from the experience. I am so much more attentive and caring. I already did lots of little things for her; but now I do *all* of dishes and laundry - not just my fair portion. I cook a LOT but I never want her to have to cook again unless she wants to. I already made her coffee and pour it every morning. Its ready to drink as soon as she is ready to drink it. Shes already never once had to scrub a toilet or tub with me.

But now? I do even more. She doesnt have to take plates to the sink after dinner. She never has to refill her drink when shes ready for another. Everything she needs, I get - no matter how trivial or easy it would be for her to do herself. And I WANT to do it. I enjoy it. Im constantly 100% attentive to what she will want or need next. Im not even doing it to be released or 'earn something' because I WANT to be in the cage. Shes not doing it in a traditionally dommy way either; she doesnt degrade me or do anything 'mean' in any way.

This is an amazing experience and we're only starting on day 3. I cant even fathom how great this will be after she has a spell where she doesnt want it; 3, 5, 7 days of not letting it out. And shes nice, not mean - so if youre into humiliation and degradation, we arent doing any of that. Not yet at least LOL.

I highly suggest this to all men. Put her in control of your erections and orgasms. Life is truly happier when she's in charge. I have not even been slightly annoyed or remotely unhappy in any way since I gave her the keys. She has been much happier too; just having the keys gives her these little bursts of happiness; she'll get them out of her pocket and jingle them once in a while with a big smile. Her whole demeanor has changed; like even when she talks about nonsense at work its...different. Shes still decompressing but shes not like 'mad' about it still; shes just venting it out - which is extremely healthy.

I highly suggest this to all men that are even slightly open to the idea. It doesnt have to be a mean, humiliating, or hardcore dom/sub experience if thats not your relationship dynamic. Its completely possible to do this with a loving, caring, 'traditional' relationship if both of you are open to the kinkier side of things. It has done nothing but vastly improve our 'normal' relationship.

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KaitlynneSissy

Added a new photo > First full day of chastity with a real world key holder. It’s amazing. Keeping yourself locked is fun on its own, but having zero access to it unless someone else says it’s ok is just absolutely amazing. She’s a very sexually active woman so these first few days I expect it to be let out, but I’m super excited for the first 3, 5, 7 day stretch with no release. I also got to see my regular BBC today and it’s been weeks. As always, it’s some serious porn quality sex…moaning, crying, primal guttural noises while he used me as a girl. This is been a spectacular week so far 💕

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KaitlynneSissy

Yesterday, I reached a HUGE milestone in life.

I actually have a real life keyholder. If you follow me, you'll know that I am extremely bisexual and love sex with both men and women. I have a regular woman along with the two regular guys. Well, last night, I finally got the courage to introduce her to chastity.

She loved it!!!

After discussion and explaining the benefits of keeping me in chastity, I immediately went and put it on. As she came back in and I exited the bedroom, we met in the living room...and I handed her the keys.

The rest of the evening was amazing. She constantly had this smirk when she wasnt outright smiling or grinning. She was constantly looking at the little lump in my comfy grey pants with a smile. She'd jingle the keys now and then with a smile.

There was already an immediate change in my demeanor. I was more attentive and affectionate. I already treat her very well and almost tend to her every need, but it was clearly amplified last night. All it took was handing the keys over and I had already changed. We havent even reached the true 'control' part yet! In fact it was quite the opposite...she wanted to take it off TWICE and have sex!

We still have some learning to do; after all it wont typically just 'spring to life' after being caged for hours or days. Timing to 'warm up' while I eat her booty and kitty kitty will be important, but to improvise on the fly, I just worshipped her feet while getting things going. And OH. MY. GOD. You have not lived until youve sucked a womans stinky work toes and licked her sweaty work feet clean. I knew I liked feet from this site having learned it here, but WOOOOOW. Actually doing it in person, for real was a truly amazing experience.

We (she) also needs to learn that she doesnt *ask* me if I want it off. She decides when it comes off and when it doesnt. I am not in charge here and my needs arent supposed to matter. That said, I am very much blessed in that she is a VERY sexually active woman and wants the 🍆 pretty much all of the time.

Im so excited to start/continue this journey. Everything about her already smelled and tasted so much better - something I didnt think was even possible. Every little touch, and even look was much more...intimate and 'special'. I can only imagine what this will be like a day, three days, 7 days into it. This is already a truly amazing, mind blowing experience...and its just begun.

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KaitlynneSissy

This is an EXCELLENT blog post and window into what some Sissies deal with/go through.

https://www.allthingsworn.com/blog/finding-power-in-your-sexual-identity

Im also going to repost the comment I made, since it somehow posted as one giant paragraph instead of separate thoughts in their own paragraphs.

I LOVE this!!! I was actually thinking about doing a very similar blog post, and yours came up.

I have a very similar situation. Im an older sissy, and have been doing this for a long time. It started at about 14 years old...and this was long, LONG before the internet was widely available. I had never been exposed to pornography, much less anything related to 'this'. I just felt like I wanted to be pretty and cute and soft and 'vulnerable'. I wanted men to like me and my body. I didnt even know 'why' - IE I didnt really know what sex was back then. I started putting things in my butt very early, and actually stated quite large - I used the rounded end of a pair of plastic toy nunchucks and it just felt good.

Through the rest of my teen years I repressed it, and never did espouse any of the stereotypical traits of a gay guy. I liked women too and did all the normal boy stuff. But I also wanted to be that feminine girly girl I locked up. Not physically - I dont actually want to *be* a girl. I want to be me. In my 20s I opened up to myself a little bit and started crossdressing in private. Still only dated women outside of a couple of experimental encounters with guys.

As I got a little older, I opened up to my own self more and more. I started dressing as a woman more often. Dressing as a girl felt good. It felt better and more normal, more comfortable than dressing like a guy. It just felt so right; so normal and natural. Finally, I started meeting guys as a sissy. And WOW. This...this was me! I found myself. It felt so...freeing to take a girls role and fulfill it. And its not just the physical act of sex with men; its the entire experience. So much of it is emotional and mental. it just felt like I was finally being 'ME'.

So I started dressing up in normal womens clothing that you could wear out in public; any day I worked remote, I was dressed as a woman. I had never felt so natural, normal and comfortable in my life until then. Looking back, thats what that 'feeling' was that I never quite could put my finger on. I always felt some sort of 'being on the outside' type of feeling. Not exactly uncomfortable, but something else...just 'not quite right'...not 'whole'. Again....Im finally 'being me'.

Chastity was the final piece of the puzzle. I thought I felt right finally after freeing myself by fully dressing in womens clothing, but once the cage went on...it was another level of 'right'. It felt so good to bundle everything up into this little nugget of bliss, and leave it there. The physical sensation is amazing in itself, but the mental aspect is also a huge part of it. This actually makes me feel like I should...I dont want it (my junk) removed - like I said I dont want to *be* a girl, I just want to be *me*. Maybe if I were 19 again, Id go on HRT and go all in, full time 'in public' sissy...but thats where id draw the line. I dont want surgery or any other body altering procedures to physically change who I am. When I cant wear it (life is complicated lol) I absolutely CANNOT WAIT to get the cage back on. I am very very good at not touching it for pleasure when not caged, but it doesnt feel the same until its all slightly compressed and locked up nice and tight. I cant say enough about how 'right' and normal it feels. Plus, when locked, I have this sort of 'energy' that runs from my chest all the way up by my neck down to my sissy bits, then down through my thighs almost to my knees. Its very difficult to describe; its such a 'happy' energy and feeling. Im noticeably happier like this. Its almost a night and day difference in my whole demeanor, mentality and general everyday emotional state. Not that Im an emotional person; just that Im not in this depressed, unmotivated state of mind. Im much more energetic, caring and thoughtful of others, productive and just...happy

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KaitlynneSissy

Added a new photo > Not the greatest quality; its a still image taken from a deepthroating BJ video I made for the Top Sissy Contest. Giving a good BJ definitely isnt easy, so if your lady gives you top tier head, you better appreciate it! Its a LOT of work and a fine art to master.

1mo

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KaitlynneSissy

Added a new photo > It would be selfish of me to keep this juicy booty all to myself 🌸

1mo

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Added a new photo > Oops…gotta wash the sheets now 💕

1mo

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KaitlynneSissy

Added a new photo > After sex photo 💕 He wasn’t going to come today…then I sent him photos of me all done up. He dropped what he was doing and came to fuck ❤️ And it was amazing…hoooooow is anal sex so, sooooo good? It’s madness…he made me orgasm over and over again. Is this what women experience when they find that guy that they refuse to let go of even when he’s a terrible man? 😂🤣😂 Words can’t even describe the feeling of this…just…amazing.

1mo

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