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Sissy

KaitlynneSissy

Online

5.0 (25) United States

Message Sissy

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 for pure domination (generally in person 'for real') but *also* free spirited, fun and happy personalities. If I were a womans sub IRL, 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.

Im typically looking for physical items, and very certain things. As above, financial domination is absolutely not one of those things. Im 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 found me on MTW. Sorry guys 🤷‍♂️

I also dont typically engage with content or items from overseas or across national borders - I generally buy from 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. 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

62 Followers - 153 Following - 13 Badges

Gender: Male

Age: 40-50

Joined: 1 year ago

Profile Visits: 6119

What I'm looking for

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Latest Activity

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KaitlynneSissy

Added a new photo > 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’

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KaitlynneSissy

Added a new photo > 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 💕

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KaitlynneSissy

Added a new photo > Image from playtime the other day 💕

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KaitlynneSissy

Added a new photo > 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.

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KaitlynneSissy

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

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KaitlynneSissy

Added a new photo > Good morning ATW! ☀️

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KaitlynneSissy

Added a new photo > Sissy Saturday!

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

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KaitlynneSissy

Added a new photo > A good sissy wears her cage at all times 💕

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KaitlynneSissy

Added a new photo > 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 💋

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KaitlynneSissy

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

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KaitlynneSissy

Added a new photo > It feels like less is more with makeup...subtle highlights seem to work best.

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KaitlynneSissy

Added a new photo > 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 ❤

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KaitlynneSissy

Ive been posting regular updates about my experience with what we call 'full time chastity'. Its not 'permanent' as it gets let out when she wants it. At this point we are on day 4 with no release except to shower - and Ive been a very good girl about not doing ANYTHING with it at all not even the tiniest tease.

Ive mostly posted about what it does for you emotionally and mentally. Youre more attentive to her needs, listen better when she speaks, and care more about what she needs to talk about. A level of natural obedience comes with it.

But theres more to it!

For better or for worse, you notice *every* woman you pass. I was never a rude person in public, but Im *even nicer* now if I interact with someone - especially women. Even women far beyond my age limits as far as sexuality goes. (and to be fair I have no hard upper age limit; its all about shape/size/health) I notice every curve...every jiggle...every cute little wisp of hair. Ive always appreciated women of all shapes and sizes and ages but this is so much more...intense. Im not like leering at every woman I pass to be very clear - I see 'all of her' in an instant. Its difficult to describe but its not necessarily sexual. Its not like Im walking around gazing at every woman I pass with dirty thoughts racing through my head. For lack of a better way to describe it, I see and 'submit to' every woman I encounter - but completely non-sexually.

Physically, I LOVE waking up in the morning, my body doing its damndest to have an erection, and it being stifled. The feeling of intense pressure and sensitivity...its another one of the indescribable pleasures of being caged like this. Just reaching down and gently holding everything is pure heaven - almost like the beginning stages of orgasm but not quite that.

The sensation of having the cage on. Wow. Again, I struggle to find words. Its almost like being about 85% edged...but 24/7. All day. Everywhere you go. Everything you do. Theres this 'energy' down there thats *almost* frustrating...but definitely not. Its pure pleasure. Its such a weird combination of desperately wanting to f*** something and not wanting this blissful sensation and energy to go away (having climaxed). The slightest tap from her as she walks by me is almost orgasmic in itself. It sends a wave of energy through my lower abdomen, pelvic floor and thighs. All it takes is one little light backhanded smack to make me feels this intense, deep, submitting love for her while that energy radiates outward from the cage. I literally want to do almost anything just to see her happy.

The words to properly describe this feeling and mentality are very difficult to find...I highly suggest every man experience this for himself. I am highly considering making a mold of my erect penis to make a strap on out of and using that to please her when she wants it. After all, she does love the size and shape of my unit, which to be fair IS impressive when unleashed. But I prefer it to be locked.

Those brief moments when Im not in the cage? Things like showers and the recent doctor appointment? I cant wait to get back in it. I feel like something is missing. It doesnt feel right to be out. Its not just mental; its almost like Ive become physically attached to wearing it too. I even LOVE to look down and see all of my stuff bundled up nice and tight, in a cute little nugget of blissful energy.

Im even more sensitive everywhere else. I already had erogenous zones more like a womans with *some* overlap into mens erogenous zones...but its SO much more intense when caged long term. T shirt rubs me? Instant hard nipples (which then intensify the whole thing). Her touch on my inner thighs, across my tummy, below the waistline, down my sides...pulling my hair at the back of my neck...holy wow. And then a light graze of the cage as she touches my perineum and cheekies...gently running a finger across my hole if Im lucky enough. Even just touching the skin beside the cage without actually touching my genitals...I cant even begin to try and describe the tingles and waves of energy that flow out from her fingertips (or even my own). This part Im already somewhat familiar with, from sleeping with men that touched and held me and treated me like a woman....but WOOOOOOOW its even better now.

I never thought this would be THAT good.

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KaitlynneSissy

One Month of Chastity

There is no feeling in this world like not having any control over your erections and orgasms. Waking up in the morning, desperately trying to have an erection, filling the cage with explosive pressure.

Being hyper aware of every jiggle of hers, every soft curve.

The scent of her feet; the taste of her toes driving you absolutely mad. Finding a pair of her socks or undies is like a gift from the heavens...yet a blissful, torturous tease.

You cant do anything about it unless she permits you to. Its not yours any more. Its hers.

Last night, she slapped it all around, squeezing me between smacks. The blanket was absolutely covered in leakage where I lay. I almost orgasmed just from the smacking.

Then, she made me eat her. After violently squeezing my head between her thighs as she orgasmed on my face, she sent me to bed. I tried to eat some more, intensely focused on her extremely hard and engorged clit, not just at the tippy top but feeling its hardness wrap down around her...but she'd spasm away and slam her legs shut while pivoting her hips inward. All I wanted to do was feel it on my lips, feel it's stiffness with my tongue again...but she'd gotten what she needed.

Maybe tomorrow...

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KaitlynneSissy

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

1mo

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KaitlynneSissy

Added a new photo > #ThatsMyKink

Crossdressing/Sissy life!

1mo

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KaitlynneSissy

Added a new photo > #getyourassout

1mo

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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… 😂