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Sissy - the unpurest form of love -

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.

Thread replies: 211
Thread images: 58

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I did it.
I spend a few weeks talking to a guy online and he finally talked me into meeting up.
I prepared for hours, made myself as pretty as possible before driving to his hotel. I had been out dressed like a girl before but that was only for dress-up parties, halloween and stuff like that.
My hearth was racing as I myself raced up to his room. He opened with a smile, which put me at ease right away. We started talking for a while, we smoked some weed on the porch where he slowly started fondling me. For some reason, the trust was there so I was able to let go of controlling the whole situation.
He took me lovingly at first but made me his slave for the rest of the night, just like he promised while chatting. Ended up cumming 4 times without touching my dick once. Probably the best night of my life.

And now he wants to do it again in a few days. But he asked me if he should invite a trusted friend.
I haven't said yes or no yet. I kinda want him too but I'm scared 2 dicks filling my holes will prove to be to challenging.

Post some inspirational webms/gifs and ask me anything I guess / give advice
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>>10970689
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>>10970694
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>>10970696
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>>10970700
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>>10970705
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>>10970711
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>>10970717
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>>10970727
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>>10970732
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I'm very close to suckin my first. I don't have any clothes or makeup, but nonetheless, I will serve and please very soon. I'm excited.
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>>10970739
The devil is in the details though. I wouldn't have been able to let go as much as I did without the clothes, lingerie and make up. And waxstrips. A lot of waxstrips.
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>>10970746
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>>10970755
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>>10970694
MAN I wish I knew who the first girl was :( Anyone know? Good karma will rain upon you for life
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>>10970786
https://biqle.ru/watch/-67482437_456239102
jhenifer dalbosco
http://www.trannytube.tv/movies/429708/shemale-vivian-merillo-and-andre-garcia-bang
Vivian Merillo
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>>10971037
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>>10971041
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>>10971049
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>>10971055
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>>10971063
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>>10971079
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>>10970689
If you already took the step once then doing it again shouldn't be an issue
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>>10970689
There a full length of this? Looks like it got cut off
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A couple wants me to come suck their dicks tonight pls give me enough brainwashing to go do it thx
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>>10970689
If you're looking for an honest answer, no. 2nd date is way too early for that shit, I'd try that shit closer to the 8th-9th date, and even then only if you really like and/or trust him.

tl;dr: no
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>thread is filled with trans bullshit again
Why the fuck is normal sissy porn so hard to find? The one where the bottom CLEARLY looks like a male, not trans/trap/shemale bullshit
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>>10972084
>normal
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>>10972096
yes? It's supposed to be guys fucking guys in women's clothes, not guys fucking chicks with dicks
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>>10972106
>guys in women's clothes
>chicks with dicks
there's a difference?
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Anyone ever try understall cruising?
Thinking about seeing if I can get anyone with it.
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>>10972124
Guys are attractive, that's the difference
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>>10972045
this, you need to wait before you allow him to bring someone. as much as it probably excites you to think about being in the center of a spit roast, getting your mouth and boi pussy filled, you need to wait months before doing that. you don't want to overdose on dick.
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>>10972084
I don't think you understand what sissy is. You're interested in regular gay porn, not sissy porn (which is a special subset of gay porn targeted at males who want to become females).
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>>10972263
I'm interested in gay porn where the bottom dresses in women's clothes and acts feminine, but still looks like a male. It's very common in yaoi, but for some reason almost non-existent when it comes to regular porn
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>>10972288
>bottom dresses in women's clothes and acts feminine, but still looks like a male

Crossdressing/trap gay porn then, again not really what sissy is.
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>>10972332
>sissy - a boy or man who enjoys little girls clothing
And again, all these tags are filled with the same shemale bullshit. Calling this >>10970694 gay is an offense to fags everywhere
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>>10970689
Good girl.
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>>10970694
>>10970696
>>10970700
>No audio
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>>10972363
>a boy or man who enjoys little girls clothing

No that's crossdressing. Look I'm not the one who made up the tags people use in porn, I'm just telling you what they are.
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>>10970689
Do it. The degradation and satisfaction of pleasing two men at once is like ten times the feeling of one.
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>>10972603
What if one of them is kinda ugly tho
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>>10972045
>>10972237
The trust is there. He took his time before meeting up and before jumping me, he seems smart and honest.
You are right about it being too early. We've made plans to get drinks together and talk about it first. It's just a dream of them and considering my first experience, I at least want to hear them out.

>>10972603
I'm afraid I won't be able to keep up and disappoint them. It's all happening so fast.

>>10972435
Thanks!
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>desperately want to fuck a sissy
>don't know how to even meet one
What do
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Can i get a pic of you all dressed up?
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any of you guys know good sissy workout routines? wanna look more gurly
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http://imgur.com/4c9SeEW

Should I do it /gif/?
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>>10972777
I'd gladly let you fuck my sissy ass daddy.
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>>10973526
Where are you from sissy?
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>>10972704
If it's happening too fast for you, then the best option is to take things slow. Take some time for the two of you to get to know each other better, and for you to properly prepare yourself for when it happens. And then, when you think you're ready, tell him you can take both him and his friend at once.
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Is there a big pack with videos/gifs on Mega? Could someone please link it?
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>>10970689
omg you have to do it!! If you enjoy being a sissy slut then you'll love being spit roasted! Easily the most exciting thing I've done sexually. I would just practice with some dildos if you can :)
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>>10972363
>Calling this >>10970694 gay is an offense to fags everywhere
it's men fucking other men that look like women. if that's not gay, then i don't know what is. look, i enjoy this shit, but i'm not deluded enough to call it anything other than what it is.
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>>10972629
for me that would be instant boner kill, but a lot of people into this stuff would get off even more on one of them being ugly.
but look at it in a birds of a feather kind of way. the other guy will most likely be in a similar league as the one you hooked up with.
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>>10972777
grindr and fetlife have worked best for me. be selective, don't just jump into anything. craigslist seemed a little too scumbag for my tastes, that site is for selling old furniture, not hook ups.
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>>10974229
What about in the UK? Aside from grindr
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>>10974248
can't help you there, anon. i'm not from the UK.
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>>10974276
Using craigs right now... got someone coming to fuck me, ah well...
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>>10974248
try squirt doot org
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>>10972009
So... watch some porn that's of the same type for what you'd be doing with them. Do a bit of jacking off to it and get in the mood. When you're hard and high on porn, set your meeting with them and commit to it. Get your mind right; you already want to do it, you just need to jump in that pool and start swimming in cum.
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>>10973399
Nice. Get you some.
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>>10974292
okay then, well good luck
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>>10972629
sauce
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>>10970689
https://xhamster.com/videos/joi-cum-7679728
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>>10971079
Yup. This feels awesome.
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>>10970689
>>10970696
>>10970705
>>10970727
I literally found the sauce for this last night and was too much f a dumb bimbo to save it fuck
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I just want to taste some other guy's cum, I've sucked cock a few times but never actually tasted cum, at least, someone else's.
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>>10974592
deepslutpuppy 8. you can download it pretty much everywhere
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>>10973148
This
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I'm not trans, just bisexual, but honestly my life's been so depressing lately that if a rich dude just showed up and wanted to feminize me (hormones, tits and all that shite), and in exchange I'd have to leave it all behind and be his bitch.
Actually. Now that come to think of it, it would be a relief not to worry about anything but taking cock. Sounds even kinda hot. Well, just had to get it off my chest, I'm sure many can relate.
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>>10974248
Go on Recon, it's a gay BDSM website/app, I'm sure you'll find plenty of doms to dress you up and punish that ass for days unending.
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>>10970739
I sucked my first when I was quite drunk at NYE.

Turned out the two guys were gay together (didn't notice)... Ended up spending the night while sucking their cocks!

The 'initiator' had a thick but shorter cock while the other one had a huge (20cm) hard dick. I sucked them so good and at one time the dude with the huge cock started assfucking the one while I tried deepthroating him.
Finally they came, both. Over my body. On my face. Cum everywhere!

When we woke up at NYday I sucked them both again on their couch and swallowed their loads again :).

Never seen either of them anywhere afterwards.

Have more stories, if interested.
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>>10975654
Literally one of my fantasies.
I'm interested, more!
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Low self esteem: the fetish.
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>>10975678
>>10975684
Filename tho, top kek
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>>10975665
Another time I want to share is way more to the point...

I was really hot for a cock. Just wanted so suck one off and prove I could take it all down my throat. Luckily a guy from grindr sent me a picture of a really nice 18cm strong man-dick. He offered to pick me up, as I stayed with friends, and drive to his home!
We didn't really talk much as I been feeling his bulge, whereafter I took is from his jeans and started sucking it on the road like a little slut.

Arriving at his apartment left no doubts; I would suck his cock until it would explode, and hopefully twice!
I let him trust in my throat, licked his balls, polished his beautiful knob and forced it straight down my throat as I promised myself (and him ;))!

Eventually he came 3 or 4 streams that landed in my mouth, on my face, my chest... :) Of course I continued sucking him until I had swallowed all of his tasty stuff..
Unfortunately he didn't cum twice, but he told me I did better than anyone he'd ever let him swallow his cock and sperm!
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>>10975699
you have no idea
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>>10975805
I'm jealous, wish I could be brave enough to do something like that.
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>>10975852
It's stepping over that one boundary which makes it worthwhile ;)
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>>10975039
I honestly understand and completely agree with you, I wouldn't mind being trans but don't really want to go through all the work of coming out as trans and doing hormones, makeup, shaving all the time, shit like that. If OP sees this you mind telling us how you feel about the small things like I just mentioned above?
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>>10970776
Man always wanted head from someone with a tongue piercing.
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>>10976025
Well, to be honest, hormones and the whole medical shebang is just time consuming, and the hormones change the hair on the body anyways so shaving will get much easier as your hairy body becomes curvy, smoother and sexier. Once you changed enough you don't even need to tell people it's the same you. Heck, just move to a different city or whatever.
My problems aren't with plain old coming out, I really couldn't care less about what people think, although I would miss my friends and the possibility of finding actual love and respect and all that. Tho it doesn't seem like I'm gonna get it. Besides, I got big feet, it would never work.
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>>10976025
OP here, not sure I'd go for it. The doubt is there though. And it's within my realm of possibilities.
The shaving (more like waxing) is easy enough. Makeup just requires practice and a friendly hand to help you out (my older sister taught me). I've got natural long hair that I just brush differently for girly mode.
Hormones, that's another story. They have a lot of drawbacks that kinda leave me worried. And I'm still into girls too.
I'm actively considering it in any case but I can't really say yes or no. Leaning towards yes though.
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>>10976875
Unless you're already a feminine twink the chances that hormones will do anything other than turn you into a depressing freak is slim.
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>>10976893
>Unless you're already a feminine twink
I kinda am. When I dress up, I fool nearly everyone. Even neighbours, some completely oblivious and others did a double take on a dress up party. When I go out around strangers, nobody seems to question anything. All I do is dress up nicely, walk and talk differently.

I'm still young now and I realize I won't be able to pull this off for much longer. Hormones could help me if I want to carry on in that route. There's surgery too.
I'm already seeing a therapist about my whole sexual identity. I'll figure it out sooner or later, for now I'm just enjoying the possibilities I currently have.
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>>10975805
Thats impressive. All the girls I've had give me blowjobs have never been able to deepthroat my 19cm cock
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>>10974180
truth
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Does anyone know the address of the site that permits to create infinite compilations of images and gifs, and select them by category?
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>>10972009
sauce on webm? she's incredible
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>tfw innocent_gal's videos are still gone
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>have account on app
>small town hoping to be discrete
>sucked a few cocks nothing more
>random guy messages me with my real name
>what do i do
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>>10979498
let him blackmail you into sucking his dick daily
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>>10970732
who the fuck is that at the 0:03-0:04 mark? HOLY FUCK
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>>10979515
looks like it might turn out that way
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>>10975039
Poor uni fag here.
I've been thinking about an offer I got not too long ago. A guy I've known for a while offered to start a live in master/slave relationship. It would mean moving in with him, being trained by him, and being obedient to him.
He said it could just be until I'm finished with school, but he also mentioned that something more 'long term' was possible if it goes well.

I've been honestly considering it since it would help me cost cut (since he said he would be paying for living expenses) and something about the idea seems really satisfying to me.
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>>10975678
Who on earth is this?
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Where's Captain Islam when you need him
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>>10979879
fapping to this shit too. those fuckers are so undercover gay it's unreal
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i sucked a dick today and it's was awfull. Worst idea i ever had
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Anyone got the gif where a chick is sucking dick at a gloryhole I think with a blackmail caption?, would be much appreciated
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Heteroflex top here.
You guys are doing God's work feminizing more people. So grateful there's more to choose from / play with, hooking up with my fantasies as visuals has never been easier compared to say like 5 years ago.

and pic related
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>>10970689
and you've got an opportunity to take two dicks? Where have you been all my life? Would pay ya to hang with my and my mates.
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>>10980301

Then you did it wrong.
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>>10976106
Pretty amazing desu
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>>10979811
>tfw you will never be nice dom couple's live in sissy maid
>tfw older dom couples don;t look for sissy subs like they look for young girl subs
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>>10980301
I thought that too a couple years ago but I still throat a cock once a year because porn keeps fooling me into thinking "THIS time it'll be good".
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>>10981264
I-I'll be your fleshlight anon
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>>10975039
>>10979693
>mfw get messages like that all the time
they don't even seem real because the kind of stuff these guys write it seems like borderline unrealistic fantasy stuff, it's actually funny.
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I see all these posts saying become a sissy... but like how does one actually become a sissy, tits and all?
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>>10981571
Anytime. Hope you're good at keeping eye contact ;)
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>>10981900
most wear fake ones.
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>>10972777
just go on /soc/ literally that easy
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>>10973605
Sauce?
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>>10971055
sauce?
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>>10982984
Harder than you think
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I've been interested in becoming a sissy for about a year, is it worth it?
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>>10983595
You should be interested in becoming a dead sissy
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>>10981797
I can't vouch for others, but I'm well acquainted with the guy who made the offer. He also took the time to outline some of what I'd be doing. Honestly a big chunk of it amounts to pretty much being a live in house keeper. Handling chores, cleaning, cooking, running errands, stuff like that. It's not exactly glamorous or particularly titillating stuff.
>>
sissy discord
https://discordapp.com/channels/229599873077346314/229599873077346314
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>>10970689
>mfw im a 6 ft tall hairy wog who has no chance of being a passable trap
feels bad
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>>10970689
>sissy, the unpurest form of faggotry

if you're gonna be gay, at least be a man who likes to fuck men. not a fucking "sissy" who has to pretend he's a woman to cope with liking dick.
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>>10979546
What do you mean?
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>>10974248
Fabguys is good, try that
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>>10974248
where abouts are you in uk?
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>>10974180
I'm sorry, but someone who looks exactly like a woman, has a female body, female face, female voice, has TITS is not man, no matter what you think. I don't care if they have a dick. For me, they are repulsing, just as they are repulsing for everyone who likes men
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>>10983886
if you like dick, you like men. that's all there is to it, man. when the fuck are you closet fags going to realize this??
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>>10983948
I am a fag you dumb fuck, girls with dicks are repulsing
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>>10983738
6'3 reporting in
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Does anybody have that link to the sissy servers where you can chat with sissies and there's sissy porn playing in the background? I really need it
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>>10974276
sauce on this?
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>>10970689
You are gay.
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>>10972107
What's the original called?
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>>10983886
>>10983961
Nope, I'm gay and I like girls with dicks. You don't speak for everyone, retard.
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>>10974327
<3
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>>10981242
Souce?
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>>10984367
Closet straight boi detected
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Just do it you only live once. Post here when finished
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>>10984533
That is a sentence I never thought I would read.
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I wish you guys would stop posting this futa hentai already
>>
Do any of you find it odd you have to "hypnotize" yourself to get turned on by your fetish? Serious replies only, please.
>>
Anyone have the webm with Seven Nation Army playing as the music? Really good webm desu
>>
There's always a lot of trolling and counter trolling and hurt feelings about who is and isn't gay in these threads so I'm going to try and explain the attraction to these threads in a comprehensive way that provides a solid answer to why people find this material hot. I'm not trying to comment on the relative value of any side, I just wish to enjoy these threads without having to read an essentially philosophical argument when I just want a good fap.
To start off, you need to make a distinction between people who are OPENLY gay/bisexual/pansexual/whatever the new phrase is and people who view this while maintaining a claim to straightness.
There are two possible explanations for being "straight" and liking this stuff: 1. The viewer is sexually subordinate and aroused by their own degradation. Being aroused by that which is the new boundary of your previous limits necessarily brings a person into the realms of taboo. Through a subordinate prism the complete abandonment of manhood in favour of hedonistic indulgence becomes the ultimate yet still societally acceptable thrill. It is as far from social norms of male sexuality as possible, while still remaining within the socially accepted framework (ie, men being fucked by other men ((by this I mean the VIEWER imagining being fucked)) and also remaining EMOTIONALLY and PHYSICALLY fulfilling. (CONTINUED IN NEXT POST)
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>>10970694
who is the girl at the end strutting towards camera?
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>>10979811
sauce or name
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>>10984367

you enjoy it because you're a bigoted moron that chooses to believe they aren't women
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>>10986693
The second (2ND) explanation similarly relies on the viewer being an individual that is aroused by the thought of breaking their own sexual boundaries and submitting/giving in to their own desire, however in the 2ND (SECOND) example the viewer does not explicitly know this, which makes it in many ways problematic.
The continual attempt to break the next sexual barrier (it is worth noting that this effect occurs over a number of years) eventually leads the viewer down a pornographic cul de sac in which the viewer reaches a level of distance from normal sexual desire. The form of this end-game depends on environmental factors and personal preferences, however it seems fair to say (without getting into a debate on free agency) that the fetishised material (in this case the VISUAL stimulus of beautiful women, penises, scenery/scenarios OVERTLY related to PORN (note, PORN not sex)) are the result of a combination of basic human sense gratification and the effect that achieving that gratification has on one's psychological outlook when combined with the images and underlying messages contained (whether consciously or not) within any erotic medium.
Suffice to say, there is a chance that attraction to this material is potentially the endgame to one particular route of perversion, similar to how a good RPG will have a different ending depending on the path followed.

I'm going to try and post OC booty pics tomorrow. stay tuned.
>>
>>10970689
I have a guy working on me I think. I'm not very good at dressing or anything but I've been talking to him a lot online and he's really stuck through my indecision. He wants me to call him and leave him a message as sort of a first step.
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>>10986722
oh that's just Steve. he's a little eccentric, but we still like him.
>>
>>10976940
I feel your pain. 23cm and only one girl that could ever deep throat me.
>>
>>10979746
Alexa Castano
>>
>>10970689
Wtf
>>
>>10983709
Doesnt work
>>
>>10982965
SAUCE PLZ
MOAR LIKE THIS
>>
>>10982984
>>10983523
Much harder than you think
>>
>>10984525
Tali Dova
>>
https://discord.gg/HPknz
Discord for sissies and all sossy realated things.
>>
https://discord.gg/3PUkVPx
>>
I need a daddy
>>
>>10992495
Kik or discord? I need a new dedicated princess
>>
Is banging a sissy the ultra power move

Banging a woman is cool
Banging a woman in the ass is cooler
Having a boy submit their ass to you is a whole different level
And then having a boy who will take pills to turn himself into a girl and then submit his ass is insane levels of power

Probably why BBC on white sissy is so popular, it also involves the highest race, whites, submitting themselves to the lowest race
>>
>>10976940
I can :). But it's really just pushing it through and knowing you won't vomit. . Sounds weird or easy, but practice (and not having a gag reflex) helps.
>>
>>10981242

Here you go, the tumblr was deleted unfortunately.
>>
I wish there was a guy in Michigan who could make my gf dream come true of watching me blow and get butt fucked by a big dick man
>>
File: disney loves sissies.gif (2MB, 496x278px) Image search: [Google]
disney loves sissies.gif
2MB, 496x278px
>>
File: epileptic cock worship.gif (1MB, 540x338px) Image search: [Google]
epileptic cock worship.gif
1MB, 540x338px
>>
>>
serious question:

how does one find this stuff without the references to the viewer being male, without pics of shemales in them, and without (or at least fewer) black people)? I feel like this would be better if they focused on the slutty behavoir and feminization and didn't keep hitting you with the fact that you're a guy
>>
>>10978561
It's Brooklyn Chase but my link to the video no longer got DMCAed.
>>
>>10974205
>Birds of a feather cock together
>>
>>10979575
let us know the outcome anon
>>
>>10993704
moar
>>
>>10993340
Nailed it.
>>
what is the source? before the uploaded altered it.
>>
>>10986285
Always found that shit annoying and distracting desu
>>
>>10984142
What's your point?
>>
>>10986285
You mean the droning voice hypnosis?

I find that shit annoying as fuck. If anything it has the opposite effect on me because I find it so annoying.

Subliminal text with good rhythmic music on the otherhand.

Its also less about the 'hypnosis' as it is about an additional fetish layer.

You don't have to be tied up to get fucked. But some people like to be tied up too. Its the same principle.
>>
>>10972231
>>10972124
>>10972106
What a faggot
>>
>>10970689
>>10970696
>>10970705
>>10970727
>>10971037
Does anyone have the version without captions, I had it some time ago but i lost it...
>>
>>10972140
You're probably more likely to get arrested than dick that way. Just download grindr
>>
>>10970689
im gonna do it tonight, im so excited. Gonna have a guy come over and im gonna suck him and hopefully get fucked
>>
>>10971099
Sauce on full vid?
>>
>>10983886
>female body
>has a penis

That's a man baby.
>>
>>10997999
:thinking:
>>
File: gobble gobble.gif (896KB, 400x400px) Image search: [Google]
gobble gobble.gif
896KB, 400x400px
>>
File: angry narrator.webm (2MB, 850x480px) Image search: [Google]
angry narrator.webm
2MB, 850x480px
>>
File: ride my bike.webm (3MB, 640x480px) Image search: [Google]
ride my bike.webm
3MB, 640x480px
>>
>>10970689
>Weed
So you're a degenerate?
>>
File: 1500845559293.webm (3MB, 480x360px) Image search: [Google]
1500845559293.webm
3MB, 480x360px
and not a single greentext story in the entire thread once more
let me remind you that there is literally zero value in the gifs posted on these types of threads
and that the only value lies in the erotic tales told by anons cross the web.
for some reason there's been a quite severe decrease in greentexts being posted and this makes me a pretty sad panda.
its pretty obvious that the jew lost and people stopped pretending like they were a cumdumpster for men
>>
>>10993599
What part of Michigan?
>>
>>
How you guys feel after sucking dick? How is your relationship with girls? Im curious too, sometimes i crossdress when im alone at home but i dont know about sucking dick. I like girls much more, their smell etc lots of different thing but sometimes i just wanna crossdress and met with a guy.

So any of you regret after sucking dick? Im sort of scared to lose my interest on girls after doing this sissy shit.
>>
>>11000975
the gay part
>>
>>11001441
I crossdress at home too (never done so in public) and I've sucked dick. I actually like giving head more than straight sex, but despite that I'm still more into girls.
>>
>>11001441
My sissy bitch had the same concern. (I was his first) But, similar to what someone else said, we both still check out girls but the reality of fucking the sissy and her taking it is the better alternative
>>
>rapid slideshow of some porn stars with a few shemales mixed in
>derogatory and emasculating text commands
>2010 era club music in the bg
wow I'm cumming
>>
>>11000627
So you're a sad panda because people stopped...? If so then clearly you are (spoilers) 'the jew'.
Thread posts: 211
Thread images: 58


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