Chicago Bottom Boy

A young smooth bottom in Chicago. Your soon to be favorite internet sissy. Love to be submissive for guys and girls who know what they want. Message me at [email protected] for anything! Kik EvanSilvy33 Love to chat and trade pictures!

[sissy-slut-captions]

[chicagobottomboy33]

Dream

[coupleuk2018-deactivated2018080]

Yep we do

[dirtytrucker6969-deactivated202]

Dirtylorrydriver

[gobriggsy]

I do ….. jonjon080

[inge1964]

Inge1964

[inge1964]

Sorry, inge line

[squeezemyballsplease]

Squeezemyballsplease

[gew35]

gew47

[chicagobottomboy33]

EvanSilvy33

[badgirlkimmy]

[bottomgurl]

This is funny! Who could call themselves a sissy if they’ve never had their ass fucked? Really?

[alexxlacee]

heard that!

[jeanettethebimbosissy]

Betore I began my sissification, I’ve tried to be ass-fucked just from curiosity and found that was great and happy thing!

[allen226]

Got used by 4 guys as a cum dump one evening

[subbipantyboy]

I do enjoy riding a bull to his completion

[purplegfdgirl]

Men get pegged, Good boys get super pegged

Reblog this if you’re a good boy who needs to be super pegged

[ts2m]

Inbox your number

[honeyfeelingfree-deactivated201]

Yes❤️❤️

[cdneeds8daddy-deactivated201811]

I do

[myers2010]

Yes i do

[intrepidsoul924]

Yes!

[flatbedder77-deactivated2019080]

Absolutely

[robertapacd-deactivated20190217]

Yes I do and I’m one too 👙💅💄👠💋

[marcanderson01]

Yes I do

[kellieskirt2-deactivated2019021]

Yes

[oldermanlooking]

Beautiful

[inazumablr-deactivated20221107]

Yes i love crosdresser

[mommyloveshergurls]

Of course.

[chicagobottomboy33]

I do because I am one!

[sissyfairyschoolslut89]

Trans dates http://bit.ly/2X92vBR

[wannabecucknsissy]

Yesss please <3

[chicagobottomboy33]

Oh yes

[afterdark116]

[chicagobottomboy33]

Pleasseeee

[varietyofsexuality]

[wetmamacitas]

[lazywitchgardener]

Always!!

[malehierarchy]

This.

[sunsetjames-deactivated20190916]

Please do

[northwestnewjersey]

Absolutely

[chicagobottomboy33]

Please do!

[princessselya]

[juicylucykitty]

All the CHICAGO people that’ll actually meet

Gone head and reblog this post

[chastitypitt-deactivated2020120]

[brooklynnsissyworld]

oh yes baby

[chantal-sissy]

Definitely

[silverfoxneedsplaymates]

I have!

[iminherpanties]

Almost daily

[goodoldhairy716]

All the time

[cuckoldsissyfaggotslavemichelle]

That’s not hard to do💝❤💅👡💋🎁🔒💘💗💄💓🔑🍒💃🖤😍👠🍭🎉💖👙👅

[girdleluv]

👅👄👅👄👅❤

[petslaveneedsmistress]

Haven’t we all? Hehe

[thedepravedmanor-deactivated201]

[whitesissyrapetoy]

Mmmmmmmmm😍

[kinkysissy4u]

Ohh….so like looking into the mirror

[lacesatinstilettos]

A new poll addition… Please respond and of course, REBLOG!!!❤❤

[sexyfairy69]

B and C of course

[futuristicmuffinalienshark]

B and C please

[kinkysissy4u]

Poll#7. .. B

[chicagobottomboy33]

A B and C

[sissyhotwetpanties]

[texasbimaleslut]

Yes Please

[kinkysissy4u]

BBC train

[sissyslutandiloveit]

Absolutely 😘

[priscillapressitin]

Please please xxx

[subbttmbitch]

Yes

[sissycumgreedywhore]

Yes pls

[trannysissycrossdresser]

Yes