Any sissies willing to share stories where they were pushed too far? Uh, asking for a friend

Well done

>i have some more wine and get relaxed and drunk after a while
>starting to insert the big plug
>the tip feels quite good as i´m stretched out already
>i work my way down under the cheering commands of my dom daddy
>i can´t get any further than about 2/3 of the plug as it hurts too much
>he insists and gets really aggressive that he is going to doxx me and ruin my live
>i really try to push it in
>change positions where it´s on the floor (it had a suction cup) and i sit on it to have more force of my bodyweight
>after a short very intense pain my ass swollows the whole thing
>i reach down to losen the suction and after i look at my fingers i see it: blood
>i get in full panic mode as i think i hurt myself badly
>dom is laughing at me and tells me that my pussy is will ruined now and i will always remember him for it (he was right though lol)
>i try to remove the plug but it´s stuck
>as i haven´t eaten in 3 days i´m close to passing out from exhaustion and panic
>considering calling ambulance
>still full makeup/wig and so on
>try to remove it by myself
>getting in a hot bathtub and drinking more wine beforehand for muscle relaxation
>after about 2 hours i´m able to get it out
>inspecting my asshole the day after
>no bigger issues fortunately, only a little ruptured skin
>still a big shock for me
>cancel all contact with dom
>haven´t dressed or done anal for 2 years after that
>eventually came back as i´m still a sissy faggot
>started doing anal again aswell
>now i´m well experienced and stick to my boundaries

pic related, my pussy after a good dildo ride

Attached: 2.jpg (1920x1080, 1008.48K)

I'd love to see you bleeding

not gonna happen anymore mister

This is delicious. Absolutely exceptional. The best. We often see tranny threads filled with people who, for one reason or another, refuse their sexuality. I'm completely heterosexual but have been comfortable with- and am still comfortable with being topped by a beautiful shemale, Just last month I was topped by two African trannies in the back of my Robin Reliant. So steamy. So incredibly sexy (think of the sex scene during Titanic). I tell my wife and her son that my hours are taken up by work - that the long hours and pain in my lower back are from hours of being sat at s desk. I feel that what she doesn't know, won't hurt her. I'm currently in talks with a lad called Geoff from Bangkok who is saving up to undergo a transition - I have agreed to help so long as he moves over here or vice-versa once it's complete. The thought of excavating a petite cavern with a frail exterior excites me and I can't wait until I can share a bed with my new Bangkok wife.If you haven't tried it yet - I would absolutely recommend sex with a tranny, it's fun, fresh and fabulous. For clarity, i'm not gay, nor have I ever been - I have never sucked a man's penis (a woman's penis is different), although I do have gay friends.

This is just sad. I really wanna punch you it the face for being stupid and I wanna strangle that 50s guy for being a absolute degenerate

Shoot yourself

Attached: ezgif-7-e1a654b9fc35.gif (100x100, 553.51K)

reading this gives me braindamage lol

yeah i was indeed young and stupid. lesson learned i guess

>be 20
>meet bbc on grindr
>calls me degrading things: whore/slut etc
>treated like a true white girl
>decide to finally meet
>he asks me not to wear panties under my skirt
>meet at walmart parking lot an hour away from my house
>he's late
>finally gets there and i hop in his car
>drive to motel parking lot and he makes me suck his cock
>keeps reminding me how much bigger his is than my little white boy clitty
>he dominates me on the back seat until he thinks he saw a cop
>drive off and i'm shaking, laying back seat
>drive behind near by supermarket
>get facial
>i cum ALL over his car
>get dropped back off by my car
>whatever self esteem i had going in is absolutely gone
>still is
>drive 110 without, thru backroads without seat belt all the way home

Attached: 7D973952-4E78-432F-95AE-17F111B04B8D.jpg (748x672, 93.76K)

>whatever self esteem i had going in is absolutely gone
>still is
lol.

Did you return for 2nds?

no i ghosted him out of shame
still think about him tho

oh, you pussy. Do you fap to the memory? Have you had any dick since?

Reading some of this stuff isn't exactly making me want to even contemplate meeting a guy anymore. Why do any of this?

the only way i could cum with my last gf was thinking about his cock pounding me

his cock permanently warped your sexuality. nice. Well, it's only a matter of time before you repeat your experience.

i dunno if it qualifies, but this guy facefucked me really hard before. it was a blow and go, i was crossdressing and he just wanted a quickie. he stopped by and i was sucking him for like 10 minutes until he starts to thrust in my mouth a bit. starts thrusting faster and deeper and kept doing it. started to hurt and i was gagging really hard, surprised i didnt vomit. he kept it up another 15 seconds then came on my face

Me and my best friend fuck every now and then. Once in highschook it started hurting too much and I told him to let off so I can recuperate. Instead he pinned me down and forced my legs further apart and fucked me harder for another 20 mins. It hurt but it was super super hot tbh. I wish we knew about silicone lube at the time though

You can start getting with guys in real life you getting old now you're going to waste your whole life.

or kill myself

your mom was gone for a week and you didnt suck his cock?

i was a camwhore for a really abusive dom but he was really nice, but he said stuff like 'im gonna keep you forever 'fucking bitch!!!!!' il fuck you with all my strength' il fuck u til you cant even walk for a week' you say that because are pussy' just stuff like that, it was a little scary at first but it was the hottest thing of my life. being treated so special and degraded too. it fucked my head up. then he left me. but i started to write a book about it where a guy meets a sissy and in three weeks first beats her up fucks her lots second week ties her up keeps her caged and gets harder, then third week just goes all out and fucks her completley. it sounds rough but besides the sex hes like most gentle man. i guess i got used to the abuse. it was pretty fun tho

Super hot

its just roleplay its kinda rough but safe, like safewords, theres no actual abuse but i still had no say. just going from one minute brushing my hair and kissing to chasing me down and fucking me seemed pretty hot

dude, relax. If you're a sissy fag, then be sissy a fag. The best part is no one needs to now that you secretly get fucked like bitch.

i mean thats not the sole reason but it certainly doesn't help

No greentext because mobile and it's a pain, but I guess I got raped. Story:

Never been attracted to guys in a relationship kind of way, but started crossdressing pretty early around 12 or 13. Was already regularly looking at porn but never had any sissy thoughts. One day I was home alone and decided to raid my mom's panty drawer. Got turned on and decided to try them on. Then a bra. Horny so started looking at porn. For the first time, pictured myself as the girl in the porn while I was jerking it. Got super turned on. This became a thing everytime I was home alone. Eventually started anal play. Just small things... fingers, a candle, etc. Super small conservative town so no chance to do anything about it without being called a faggot.

Fast forward: 21, live in middle of nowhere, and nearest city is about an hour away so I drive there every once in a while to go out and usually crash in a hotel. By this point, I had been fucked by a few guys I met on craigslist and had my own average sized dick dildo. I was used to taking average dick. Decided I wanted to be a real sissy bitch for somebody. Go to said city, get drunk, get hotel, and post an ad on craigslist to be tied down and fucked. Get a response from a black dude that looked pretty hung in his pictures and decided to try it. Holy shit the pictures didnt do it justice. He pulled out his cock and it was uncomfortably large in my mouth even soft. As he got hard, I could barely get my lips around it and he was easily 10 inches. He said something along the lines of "if you cant suck it, guess it's time to get fucked."

Cont...

> your sexuality is permanently warped
> nice
This is why people call faggots degenerates

im willing to accept that. but im not happy abt it

your sexuality should make you want to live life, not want to kys. Just accept and embrace yourself. It's not like repressing it is a viable choice.

I was nervous as I'd never taken anything close to that big, but I was so turned on by this massive cock that I figured it might hurt at first but I would get used to it. He slipped my panties off and I got out the rope I had brought with me. He tied me spread out in an X. I told him to go slow because he was so big. I felt him lube up my hole and slip a finger in. Then he positioned himself and pushed the head against the opening. I was sure I was ready. I was wrong. There was no easing it in. He kind of pressed it in until I was starting to open up. I could feel myself stretching and was getting ready to tell him to go slow because it was already starting to hurt... and then he slammed it all the way in. His pelvis smacked my asscheeks hard enough to make an audible slap. It felt like somebody stabbed my in asshole with a knife and punched me in the stomach all at once. That's one of the few times in my adult life I've actually cried out in pain. He just smashed my face into the mattress and put all his weight into holding it as deep as it would go. Once I got over the initial pain of my hole literalling being torn open and the pain inside to somewhat regain my composure, he let go of the back of my head and I raised my head to catch my breath. I told him to pull out because it was way too big and hurt really bad. He told me to beg. To say please sir. And I did. I was truthfully and wholeheartedly begging this man to take his cock out of my ass because I was in pain. I cant begin to to explain the relief I felt as he started pulling it out... until he shoved my face back in the mattress and slammed it in again. The pain wasnt quite as bad that time but it really felt like getting punched in the stomach. I had never had anything that deep in me, let alone something that thick. He said "this is what you told me you wanted so I'm going to give it to you." And then he started thrusting.

Cont...

Reminds me of the first time I successfully inserted a large plug.. I got some footage of that actually

i mean i just dont care abt anything anymore. that coupled with being trans deep down and knowing that ill NEVER be a woman im kinda just like fuck it who cares. appreciate the positivity tho. i feel like thats rare on here

lotta fag black dudes damn

That happened to me too and now I’ve been with like 15 black men

Attached: DB05CF3A-D2C1-4218-B712-A4949B2D0752.jpg (750x1028, 187.24K)

Attached: 72CEBE98-AD06-45E7-BF8C-66B632B03EF1.jpg (750x1334, 115.81K)

He started slow at first. Pulling it almost all the way out then slamming it back down to be met with me crying out each time. Every time it felt like my guts were being torn apart. He put all his weight into it and leaned on me. I thought he came and it was over. Wrong again. He started the pulling almost out and slamming it back again but gaining speed until he was straight up porn fucking me. I eventually stopped crying out every time he bottomed out, partly because I didnt even have time to get a breath between thrusts and partly because I was near blacked out from the pain. After what I'm assuming was a couple minutes of him just pounding my hole and me grunting every time he bottomed out, I felt him pull out. My temporary relief disappeared when I heard him pop the cap on the lube again. He told me to beg him more. And I did. "Please sir. It hurts so bad. I cant take anymore." Then he crammed it back in and the tearing sensation happened all over again. The temporary relief was enough for me to snap back to reality so I cried out again when he stuffed me full. Then he pulled it all the way out again and repeated it. Over and over until I near blacked out again and the cries of pain turned into grunts again. At this point I was just focused on breathing and what felt like trying to stay alive. He went back to pounding me until he finally came in my ass. It was the first time I ever actually felt the cum. Maybe it was because my guts were so sensitive and tender at this point or maybe he shot a huge load. No idea. But I've never been more relieved in my life. He pulled out, slapped my ass really hard, and said "you ain't the first white bitch that begged me to stop. Think you want a real nigga dick til you get one." Then got dressed and left. Left me tied up and all. After a long struggle, I managed to free a hand and untie myself.

Cont...

>ill NEVER be a woman im kinda just like fuck it who cares
well you can be a women when you have sex. You clearly need a bf to help deal with your issues.

I've since got into much more extreme anal training. It didn't start for quite some time after that, but now I'm fairly certain I could take him with ease. I often wish I could find him again and repeat the whole scenario, this time hopefully without the pain since I'm a little more prepared. I can only imagine the pleasure would be mind blowing. Unfortunately I've yet to find anybody with such a truly magnificent dick. He was a once in a lifetime and that once happened before I was ready for it.

That being said, I would never want to relive that actual experience. I'm pretty sure at this point it would take somebody fisting me elbow deep to repeat the experience, probably with a double fist to duplicate the asshole tearing, but it truly was excruciating.

fuckinnng hot

Thank you Sir

Attached: 34B60CA0-5585-4C11-B833-98436FE60FBD.jpg (1080x1920, 396.94K)

who the fuck dates trans women??? i thought that was like rare

Would love to do to you what that bitch up there said happened to her.

i didnt think guys actually dated trannies

whats up jew faggots i see you are on your fag shit early today

Did you feel any actual pleasure when he fucked you? How long did it take your asshole to recover?

youre a sexy little thing how old are you? are you on estrogen?

27 and I’m not
Why does being a Jew fag make the sissy urges so much stronger??

Attached: FCA00C4B-4BCD-48ED-B99B-B4BD4C6C6A6A.jpg (588x1024, 89.02K)

love this

No pleasure whatsoever other than the excitement while I was sucking him and the anticipation of getting as he was starting to press it into my hole. Once he crammed it in, it was true pain. From the hole all the way to wherever the tip of his dick reached. I really felt like somebody had used my stomach as a punching bag. It was sore for a couple days and my asshole hurt for probably 3 days but was tender for longer. Took me probably a week before I could even slip a finger it.

we're not jewish fags. We're ordinary gentile fags who have our sexualities warped into ever deeper faggotry with every new exposure to porn and decadence.

it's actually pretty nice

I just ordered my first pairs of panties, my first step towards becoming a sissy slut :3 i'm so happy.