u/femboy_vickyy

A little context (we're both over 18 at the time)
This is my second confession, first confession is with the same bully so I recommend you read it first so you can have some background knowledge

Let’s get started, about 2 years ago or so I lost my anal virginity to my bully, I’ve had cock in my mouth and have been fingered by Redditors online during CarPlay but I have never actually had a dick inside my ass pussy, so I was determined.

After getting a throat pie by my bully who I am addicted to, I begged for him to fuck me, he always said he was busy and that I was too worthless for him but I would do anything he told me to, I would contort my body just for his amusement and send him nude pics of me in flexible positions.

Eventually he agreed to fuck me on my college campus, a different stall from when we met last time but still during school hours. At this point I was a more experienced being a sissy but I still had my anal virginity and at the time I didn’t have a dildo so I couldn’t really stretch it or train myself so I knew it was going to be painful but I wanted it no matter what. Eventually the day came for my bully to fuck me, the plan was for me to get into the stall get ready and wait for him to arrive, so I arrived about 20 mins before our meet time so I could prep myself as best as possible, I put on my lingerie I had kept in my backpack secretly, I put on my makeup to be extra fem for him, and then I texted “I’m ready” before while he was waiting in his car outside my heart was beating out my chest, I could feel my ass pussy pulsating already I had been wearing a butt plug all morning because of how scared I was. He texted back “I’ll be there in 2 mins” I began to question this I couldn’t believe I was going to let the guy who bully’s me and makes fun of me actually fuck me, was I going crazy? Is this a mistake?? That’s when he asked if I wanted him to use condom or not, out of being so horny I said he can fuck me raw, but then I immediately regretted saying that and asked him to use a condom, he said “too late you already agreed” those words made me feel sick yet excited, I quickly spit in my hand and tried to lube my ass pussy as much as possible before he came but as I did I heard the restroom door open, he was here, he put his hand over the stall door which was the sign to let me know it was him, I did as he told me to, I unlocked the door and immediately presented him my ass bent over the sink and facing the mirror looking at my self ( the stall had its own sink and mirror) I heard him lock the door and then felt those masculine hands grab my waist, I look up in the reflection and see him those eyes full of hate and hornyness he was my abuser and I was begging him to fuck me, then I felt it, his hard yet soft tip press against my ass pussy, I was twitching so much, I said “please go slow” he told me to “shut the fuck up” then he put his hand in my hair and held my head up and told me to watch him claim me in the mirror, I covered my mouth and stared at his eyes while he slide his thick cock into my ass pussy hole, I could feel every inch, his warm wet cock beating like his heart, I helped him by spreading my ass and I could tell he was smiling, with no hesitation he started fucking me while I watched him in the mirror my clitty dripping precum and mouth covered, I was in sissy bliss I couldn’t believe how amazing it felt, he was actually inside me using me for his pleasure and I didn’t mean anything to him, he pulled out and told me to get on the floor, I did and went into doggy, he started fucking me even harder, I was in absolute shock.

He then told me to get on my back as he was going to fuck me in missionary, I pulled my legs back as much as I could almost putting my feet behind my head but that’s when he said he was done, he left me there laying on the ground like a stupid slut waiting to get fucked hard, my ass pussy gaped and super pink/red. I felt so so so humiliated, my face had never felt so hot I couldn’t believe what just happened, I didn’t know if I should be more ashamed I let a man fuck my ass pussy or that he didn’t give me his cum. I’m still thinking about that day ever since

A while later I asked him if it was good he said I was alright

I have a lot more stories to tell let me know if you wanna hear ;)

A little context first (we’re both 18 at the time)
I’m a sissy sometimes activity posting sometimes not
I’m closeted so no one in real life knows I’m a sissy slut

Okay so a couple years ago when I was still new to being a sissy online and talking to strangers on Reddit I would post mainly ass pics while wearing women’s clothing since I was shy that’s mostly all I would ever post nothing too crazy, well this one guy would comment about the stretch marks on my ass saying how they were ugly and that I was fake since I wouldn’t post any pics of me meeting up with guys.

So I commented back saying “mhu me and I’ll show you I’m real” I did the standard writing what he wanted on a flash card and put it on my ass to show him proof. After a couple months of talking I was addicted, I had never met a man as degrading as him and even to this day I just can’t get enough of him talking to him makes me feel like such a girl I always call him daddy. But anyways he would eventually make me do things like taking fully nude pics, make me buy a dildo and butt plug and post my whole body, after a while he wouldn’t even have to ask for me to do things I would do them to get his attention and approval, one time when I went to church with my family I wore my anal plug and a thong underneath my normal clothes and went to the restroom set up my phone and took videos of myself fingering and tasting my ass pussy.

So yeah after maybe less than a year he said he finally wanted to meet saying I was girly enough as he had feminized me and trained me, at this point he already has my phone number and has countless embarrassing pictures and videos of me being a femboy sissy slut, so we agreed and made a plan to meet at my college during school hours.

The day was here we were finally meeting before I left my house I put on my lingerie under my normal clothes since again I’m closeted, I packed my makeup and went to school. When he finally texted me saying he was on campus i went to a restroom to get ready, i put on my makeup quickly while my heart was beating uncontrollably and my useless clitty leaking precum in my panties, I had never been so excited to meet up with a guy before, one thing I didn’t mention was I had sucked a couple dicks before but i only spoke to them for s couple days before meeting and never spoke again, this was the first time i had spoken with a guy for a year or so and i was addicted to his bullying, so as a show of extra gratitude i folded a $20 bill and stuck it between my ass to give to him. He started texting me to “hurry up bitch” so as my legs were shaking I put on a mask and slowly started to make my way over to the restroom he was waiting in.

As i got near I couldn’t believe this was it I was finally going to meet my bully, I walk into the restroom I could feel my heart shaking my chest no one else was in the restroom besides the paid of black shoes underneath the big stall where he said he was, i texted “I’m here daddy” i saw the stall door creek open slightly and a hand poked out gesturing to come forward, i wasn’t knowing what to expect I just knew he was white but he never sent me any dick pics, i walk in with my fave down afraid to make eye contact and without any words being exchanged he locks the door and lowers his sweat pants showing his already hard cock and puts it right on my lips I instinctually open my mouth and start sucking his dick I get enough courage to finally look up and him and give him eye contact while while I do my best to satisfy him, he is wearing a hoodie and a mask so all I can see is his eyes starting right at me with pure masculinity, he would shove his cock deep into my throat making me produce embarrassing sounds, he would pull me in so my nose would be buried in his big bush, he pulled out and I saw his throbbing cock covered in my spit I turned around and presented my pussy to him smooth and tight so I spread my ass and he took the $20 and told me to turn around when he grabbed my hair and shoved his cock in this dick all way to the back of my throat again balls deep, then that’s when I felt it, no warning no pulling out, the pulsating thick cock had cummed down my throat I could feel his warm thick cum shooting out and oozing into my mouth any masculinity left in me was gone for sure now, he made me his bitch, I felt so humiliated and loved it, he held it for a while then pulled out when he was done, he slapped my face then walked out without saying a word.

I laid there on the floor humiliated, cum filled and emasculated by my bully, I think of that day all the time. A little while later I texted him if I did a good job, he just replied with “you did okay” that made me feel so embarrassed and worthless I loved it, and so that’s how I paid my bully to cum in my mouth

I have a lot more stories I can tell about my encounters and I have one when he actually fucked me and took my virginity away, I can write about that one too in another post if you guys wanna here