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I am a sissy who's hooked up with men on a few occasions. AMA.

This is a red board which means that it's strictly for adults (Not Safe For Work content only). If you see any illegal content, please report it.
The stories and information posted here are artistic works of fiction and falsehood.
Only a fool would take anything posted here as fact.

Thread replies: 212
Thread images: 89

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I am a sissy who's hooked up with men on a few occasions. AMA.
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>>716089571
Biggest cock you've taken
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>>716089893
More
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>>716089571
FUCK YOU FUCKNG FAGGOT
>>
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>>716089951
Eight inches my first time ever. It was an experience!
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>>716089571
Are you on hormones? If not why? Do you wear a chastity when they fuck you in the ass?
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>>716090057
Oh I bet your tight sissy ass got stretched so much
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>>716089571
kik?
mines sirpunchblock
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>>716090080
I'm not on hormones b/c I'm not sure if it's something I want to do fulltime or not. I have a chastity cage but haven't been fucked in it.
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>>716089571
Do you still fantasize about women or is strictly men now?
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>>716090292
I still fantasize about women, but mostly fantasize about men.
>>
how feminine is your penis?
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>>716090436
It's very small when flaccid but grows to about 5.5 when erect. It's thick but not super thick when erect.
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>>716090345
more of this i love chastity
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>>716089571
How big is your cock? Also any pics of you?
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>>716089571
Do you enjoy being a dirty slut?
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>>716090411
Will you ever go back to women?
And I agree with the anon above, post pics.
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>>716090554
do you ever wish it was smaller? i sometimes find myself having a weird kind of reverse cock-envy.
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>>716090749
I'm of a mixed mindset over it. Some times I love it, other times I hate it.
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>>716090752
Maybe. I still really like women too.
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>>716090904
Have you ever been tag teamed?
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>>716090411
I'd love to watch someone do this in front of me
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>>716090757
Sometimes I do, sometimes I don't depending on how hard the sissy feelings are hitting me.
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>>716090981
Not yet, but I'd love to be.
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>>716091127
show your amrpits
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>>716091127
How many men at once would you like to do
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>>716091227
I would like to be tag teamed and I would also like to experience getting gang banged.
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>>716090591
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>>716091127
show feet OP ;)
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>>716089571
Would you let an indian guy with a small cock fuck you?
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>>716090411
Thats hot af.
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>>716091233
My god.
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>>716091526
If he was good looking, yes.
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>>716091643
cute
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>>716089571 (OP)
Where can I meet sissies in Germany? Which website can you recommend?
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>>716091822
>Indian
>Good looking
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>>716091822
What made you start wanting cock? Was it /b/?
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>>716091906
I would just use craigslist, that's what I've used in the past.
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>>716092070
I've always wanted cock though I was in complete denial about it for a long time.
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>>716090517
Source?
>>
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>>716089571
What are your preferences regarding body and pubic hair on men?
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>>716090411
more like this
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>>716092417
I prefer shaved, but I'm also ok with trimmed and in certain but rare cases natural.
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>>716089571
What's the biggest dick you've ever taken and what color was it?
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>>716092512
Have you ever thought of topping another man? Do you want to?
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>>716092687
Probably the eight inches I took when I lost my virginity. Guy was white.
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>>716092728
I don't want to top a manly man, but I'd top a young attractive (18-30 yo) boy, another sissy, or a trans girl.
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>>716089571


what is the difference between trap and sissy?
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>>716093120
The definition if a trap is someone who can pass as a girl
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>>716093037
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>>716093120
A trap is a feminine guy who can trick others into thinking he's a girl. A sissy is a guy who likes crossdressing and usually erotic humiliation, BDSM, being used like a piece of fuckmeat, etc.
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>>716093209
>>716093341


So, basically the same fuckin thing?

A trap can be a sissy or a sissy can be a trap?
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>>716093481
All sissies aspire to be traps, but few are. Not all traps are sissies.
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>>716093481
All traps are sissies but not all sissies are traps
A gross fat guy in a shitty skirt can be classified as a sissy but not a trap because he doesn't look like a girl
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>>716093481
A trap is a sissy that can actually trick someone into thinking he is a girl.
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>>716092917
>>716093315
wew
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>>716093602
Not all traps are sissies. Some traps could just like dressing up and not be into sex or any of the BDSM stuff.
>>
favorite size/shape dick?
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>>716089571
>>716089571
>>716089571

I've been waiting for a sissy ama omg


How long have you been doing this?? Did you start cus of /b/?

Do you have a daddy who buys you stuff? If not how much money have u spent on clothes?

What was your first time taking cock like? How did u meet him?
>>
>>716093753
That doesn't make them any less sissy.
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>>716092804
did it hurt? o.o
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>>716093481

mostly.

a sissy might now be able to pass.
a trap might not be into the "sissy personality"
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>>716093834
Big, black, and circumcised :).
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>>716093602
Wrong, traps are crossdressers who are passable or sometimes transvestites. Sissies take the femininity to the extreme which makes them different.

Don't spread misinformation please :/
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>>716089571
Do you have any race preference of a guy?
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>>716094014
>Sissies take the femininity to the extreme
No, that's incorrect. I see tons of videos of ugly old men with shitty makeup jobs and the titles are always like "SISSY BOY GIVES ME A BJ AND I CUM ALL OVER HIS CLITTY"
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>>716093563
>>716093602

Are the guys who fuck traps or sissys considered gay by you?
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>>716093860
I've been into crossdressing since I was a pre-teen and sissy stuff since I was 18ish.

I don't have a daddy who buys me stuff, but I'd love to have that sort of arrangement.

My first time taking cock I was in the Navy in A-school and had rented a car for the weekend. I was late and by myself stuck in traffic so I was cruising craigslist while I waited. One guy said he wanted to meet up with a sissy so I (very very nervously) agreed to meet up.

I went to his apartment and he was an older guy round 40-45, tall, not super good looking but not ugly either. He invited me in and told me to get undressed. I did and he pulled out some panties for me to slip into. He said "get on your hands and knees" and I did and he pulled the panties to the side and started eating my ass. It was heaven. We got on his bed and he had me sit on his face and I started sucking his cock which was very big and very hard. After a while he asked if he could fuck me. I nervously agreed and it took him forever to get it in and it hurt really really bad. He fucked me missionary for a while and as soon as it started feeling good I felt his cock twitch and him cum (he was wearing a condom). He collapsed on top of me and slowly slid himself out of me. I showered, chatted a bit, and then was on my way.
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>>716094076
No, I like all races.
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>>716094226
Nope, I'm sorry but you're still wrong. Sissies dress up in frilly pink stuff as the kind of calling card

They also dress in women's cloths but you don't call them a sissy until they put on a babydoll or frilly stuff :p

They also train to like worship cocks and deny themselves pleasure, cus they're just fuckdolls :3

if they just look like dudes in drag they're crossdressers
>>
>>716093602
sauce on this qt
>>
>>716094365
Sexuality is a spectum, and labels are labels. I wouldn't consider them 100% straight, but most guys who fuck sissies aren't 100% gay either.
>>
>>716094526
omg you took the plunge and did craigslist?? I'm really scared of getting like craiglist raped cus I weigh about 110 lbs +-... I also thought about gloryholes with condoms just to kinda test cock I dunno..

there's this guy who said he wants to drive down and buy me an outfit to fuck me in but I'm so nervous of dressing up in front of people for the first time ugh. plus what if he's gonna like straight rape me?
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>>716094804
Traps have been studied and found to be more appealing to straight males than gay guys did you know that??
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>>716095144
how come you can cum free hands?
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>>716095061
There's a certain amount of risk that goes with using CL or grindr or whatever, so you have to ask yourself is the risk worth the reward? Just put yourself in the sissy mindset and I think the question will answer itself.
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>>716095201
"Straight" guys. When you're balls deep in another guys ass, no matter what he's dressed up as, I still call a little gay.
>>
>>716091127
Mmmm, source?
>>
>>716095306
I already know :x I'm gonna suck his cock at least I can't wait any more I need it now

How do I find out when gloryholes are active?? All the adult shops are always empty right around me ):
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>>716095416
There's a obvious gray area thought, the study wouldn't have shown those results if it wasn't true :3

masculine culture and stuff will keep it from being admitted though and ever being accepted
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>>716095658
I've never used a gloryhole, only ever done hotel hookups.
>>
If any crossdressers or sissies want to add my kik: joed2244
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>>716095888
Don't feel bad about liking traps. It doesn't make you "gay". Sexuality lies on a spectrum.
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>>716096062


They áre so fuckin uglys.
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>>716091822
Hooray.
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>>716096062
hah, I'm a sissy myself and it's bi as fuck. (: I wanna get my ass filled of coure it is

just easing the pain for the guys thinkin about tryin one of us...
>>
>>716095971
I'm gonna try both, one cock isn't enough >:3

condoms at the gloryholes tho
>>
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>>716096337
And damn proud of it.
>>
>>716089571

Questions for all traps

Why are most of you always alone and without friends?

What is the need to always look for attention on the internet?
>>
have you ever been fucked without a condom?
>>
>>716095201
Yeah... because gay guys like manly men because they're gay. Don't need a study for that. Fucking dudes is always gay. Always. It's not so hard to get a woman to fuck you, ya know.
>>
if you're really looking for sissies in germany craigslist is bullshit. try travesta dot de but beware of being a onesided person. profiles without pics and without any texts don't get much attention.

trust me, i'm in this for about 10 years now. sissy from berlin, but right now on my shitty old ipad so can't and won't post pics.
>>
>>716096481
They can't get pussy so they resign themselves to gay sex. Kinda like prison.
>>
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>>716096521
Never, though it's a fantasy of mine that I'd love to try if I ever had a long term partner. Just the thought of it though... sploosh.
>>
>>716096062
looks like that was a fun party
>>
>>716096618


Im a r9k citizen

Get a woman is very difficult
>>
>>716096618
That's like saying guys are only attracted to women due to femininity, what about brohoes and southern chicks and I shouldn't have to explain this to you, faggot
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>>716096741
I've had sex with lots of women. I like steak and pizza. Why only eat pizza when there's steak available to you as well?
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Did any of your sissys here ever topped men?
Tell us about it.
>>
>>716096788


why?
You're not going to get pregnant anyway.
>>
>>716089940
Who is her? I loves her!
>>
>>716096838
I'm not an overwhelmingly attractive guy plus I browse this shitheap, but I've had 3 women agree to fuck my sorry ass and if I can do it you can do it. Stop all this prison shit and get out there -- the only way to meet people is to go outside. Maybe .003% of people I've met have had sex with me, so work on those numbers.
>>
do you ever eat your own cum/ when sucking a dick do you swallow?
>>
>>716095888
im fucking this shemale tomorrow
>>
>>716096966


Not all people are bi-sexuals, my friend.
>>
>>716096741
Not true at all, I got tons of pussy before I started doing this and I could get tons more if it's what I chose to be doing. Still randomly cum to chicks even when I'm in sissy mode

This feels different and is addicting and is its own thing. Bisexuality faggot, bam. You're missin out.
>>
>>716096966
Being bisexual is fine, but if you're straight and fucking men I think there's something wrong with you
>>
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>>716097058
STDs, duh. I love being a sissy but I'd have to be an idiot not to recognize the risks that go with unprotected sex.
>>
>>716097149


Hookers dont count.
>>
>>716097197
Tons of pussy huh
>>
>>716097149
>>
>>716097149
fill his boipucci all up anon >:3
>>
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Far more people are bisexual or have bisexual tendencies than would care to admit to it.
>>
>>716097336
Up to you if you believe me, I don't have anything to prove to /b/.. I'm anonymous
>>
>>716097267


You can get crabs with condom anyway.
Or aids if touch cum.
You stupid.
>>
>>716097307
shes not a hooker im surprised as you when she said it

we met up yesterday for lunc, she manages a lingerie store and has been in a relationship for 12 years

you dont need to believe but im gonna green text about it tomorrow
>>
>>716097340
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>>716097519
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>>716094526
What was your MOS in the Navy?
>>
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>>716097450
Crabs can be cured, AIDS you're only gonna get (unless you're very unlucky) by having unprotected anal sex.
>>
>>716097701
That one's a secret :)
>>
OP, you have images or kik?
>>
>>716089571
Are there respectable-looking guys who would fug a 25-year-old sissy who looks young for his age? How old is it even possible to be a sissy?

Would they care that I can't do a girly voice?
>>
>>716097782
Aw but why? :(
>>
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>>716097887
Lots and lots of fucking people my friend.
>>
>>716097782
You were a SEAL huh? lol.
>>
>>716097454


>A relationship of 12 years.
with who?


Is she cheating on you?
>>
what does it feel to be fucked?
>>
>>716089571
Therapy or GTFO.
>>
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>>716098118
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>>716097887
depends what you look like I guess

I'm 25 but have the body of a 15 year old and have a femme face so I can kinda get away with it :p over a dozen new messages on kik cus I posted in two threads today
>>
>>716097995
That's an old ass TV.

Not talking about you :p
>>
>>716097729

It is not like this.

The cum transmits the AIDS,
A facial and pum you have AIDS.
>>
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>>716098118
Really, really intense. Unlike anything else. Dildo's are not the same as the real thing.
>>
>>716095306

Source on that one?
>>
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>>716098410
http://lifehacker.com/how-to-give-and-receive-a-facial-the-safe-way-1536437947
>>
>>716098117
no with her current bf
>>
File: emily-travesti-25.jpg (80KB, 634x1069px) Image search: [Google]
emily-travesti-25.jpg
80KB, 634x1069px
>>
>>716089571


Why are most of you so well shaved?

I shave but my hair grows very fast and thick, I am a man not a sissy.
>>
What sites should i check to start my sissyfication?
>>
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>>716098908
xtube.com has some really good amateur sissy videos. r/sissies is also a nice site.
>>
>>716098538


>Lifehack

Lel, enjoy your aids
>>
>>716098411
even different than riding a dildo fast?? I wonder what it's like for my ass to be tightly wrapped around a cock >:3
>>
>>716098908
Only cum to sissy hypno and have a dildo in your mouth every time you cum from now on! It fucking works......
>>
File: 1467109795137.jpg (747KB, 1879x800px) Image search: [Google]
1467109795137.jpg
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>>716099145
One time when I was getting fucked I literally could not help but screaming like a pornstar. I wasn't doing it just for show, it was just so intense that I couldn't help it.
>>
>>716097197
These idiots don't understand how good and addicting gay sex can be.

I dated a very attractive model for a year and 2 months. Sex was a daily thing and we both had quite a few kinks and fetishes. When we broke up, I started getting curious about traps. It started with just jacking it to trap porn but my desire to be with one kept growing. Eventually I hooked up with one and ever since I can't go back. The sex is too good, better than any straight sex I ever had.

Although I still find the female body sexy and hot, sex with a trap is still superior.
>>
>>716099383
I want it so fucking bad I hate you );
>>
>>716090554
Would you ever let a guy cum inside of you?
>>
>>716099383


Why traps are so sluts?
>>
>>716089571
>>716090345
>>716090517

does it feel better if you take something in the ass with a chastity device?
>>
>>716099756
we're sissies we're here to serve cocks .....
>>
File: 1423309317831.gif (953KB, 500x282px)
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>>
File: 7chan.org 141738450075.jpg (340KB, 1440x960px) Image search: [Google]
7chan.org 141738450075.jpg
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>>716099703
Only if it were a semi long term monogamous thing.
>>
File: 1422095259277.gif (991KB, 384x288px) Image search: [Google]
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>>
>>716097132
This
>>
File: 1400076233541.gif (830KB, 416x386px) Image search: [Google]
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>>
>>716099985
I wouldn't say it feels better, but there's something super kinky and hot about chastity that makes it hotter. I've never been properly fucked in chastity though, just played around with it.
>>
File: 000001.jpg (209KB, 1920x1080px)
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>>716099756

you have to be really slutty to dress up and pose for people on the internet.

if they were only kinda into it, they would never post
>>
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>>716100659
I do eat my own cum from time to time when I'm feeling extra kinky. I will usually swallow.
>>
>>716100992


And others's cum?
>>
>>716095306
>>716095658
Dude CL and Grindr are easy ways to get STD's.
use condoms with extra (tons and tons of) lube
>>
File: 1479842738130.jpg (493KB, 1280x1707px)
1479842738130.jpg
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>>716101401
I swallow :).
>>
File: Chanel Santini 01.webm (2MB, 1280x720px) Image search: [Google]
Chanel Santini 01.webm
2MB, 1280x720px
>>
what is it called when someone posts someone androgynous in a trap thread who has a vagina? An untrap? A trap-trap?
>>
File: 1406587655097.webm (2MB, 960x544px) Image search: [Google]
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>>716101883

Reverse trap.
>>
File: 1481261345323.png (499KB, 597x1075px) Image search: [Google]
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Goddamn I want to fuck a hot sissy/trap so bad
>>
Do you think there is any point me trying to be a sissy for people to meet up with people in england if Im on the chubby side? I havent had much luck so far.
>>
>>716097059
>her
>>
>>716089571
can we see more of you?
>>
>>716091056
moar!
>>
>>716104243
I wants more of her!
>>
>>716097701
>MOS
why
>>
>>716089571
roll
>>
>>716100862
Moar?
>>
>>716095306
Sauce?
>>
>>
next week ill suck my first cock, any tips?
>>
>>716098410
>Virus
>Surviving on skin for more than 1second
Do you even biology?
>>
>>716107613
>being this autistic
>>
>>716091233
Is that you OP?
>>
do you enjoy men? Do you want more?
>>
how did you become a sissy and are you passable?
>>
>>716089797
is that a sausage?
>>
>>716107877
>being this autistic
>>
>>716089571
I'd laugh if he slipped on those skates and jammed the dildo inside his ass.
>>
>>716093201
Sauce?
>>
>>716089571
What are you? Fucking gay?
Thread posts: 212
Thread images: 89


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