I exposed my sissy side to my gf earlier this year and also my fantasies about being cucked. We were both a bit hesitant about also because she's Bi but leaning towards liking girls more.
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In the past she's said she doesn't like anything too big going inside of her because it's painful but I wasn't sure if she just said that to not hurt my feelings. I've started collecting some decently large toys for myself but have used a couple on her before.
There was one night after she had pegged me that I asked if I could use my BBC dildo on her. Its about 10 inches long and 2.5 inches wide. My cock looks absolutely tiny compared to this thing which was also the point of me getting it. She agreed and I got lots of lube to start working it in. It was a super tight fit but we somehow managed to get it all in at that point. She said it was a bit too intense so we stopped and grabbed a smaller dildo for me to make her cum.
Fast forward to a couple days ago where I asked her to use it again. Since our last time, I also admitted that I enjoyed being humiliated, especially SPH, and she had incorporated it in a few times where she pegged me and I loved it. Apparently she had been practicing with the bigger toys to get more used to them.
I was already wearing one of my chastity cages and I was ordered to put on my flat cage before we started. I grabbed the bbc dildo again and the lube but she stopped me before I started to lube up her hole. She laid on her back and grabbed me by the hair, forcing my face into her pussy.
"Lick my tight pussy baby. Get me ready so I can get stretched by a real cock."
I started licking with all my heart as I felt her get wetter than I've ever seen her before.
"Stick that huge cock in me you stupid sissy."
I started straining against my cage like crazy as I started sliding it in. The entire thing slid in like butter. I could hear her moans and whimpers as I slid the entire toy inside her. She was making noises that I've never heard before. I still couldn't believe how incredibly easily it went in. I continued sliding it in and out of her and she instructed me.
"It's stretching me so good baby. Keep fucking me with that big fat cock. Your pathetic little dick could never make me feel this good."
I was getting so turned on and I picked up the pace a little bit. After just a couple of minutes, her legs started shaking and I could tell she was getting close to cumming.
"It's so deep baby. Keep giving me those deep, long strokes and fill my pussy up with that big dick. You'd never be able to make me feel this way could you?"
I shook my head no and she smirked at me. A few seconds later, she starts convulsing like shes possessed and has the biggest orgasm of her life.
She took a couple seconds after cumming to catch her breath and unlocked my cage. She took my throbbing dick out of it's metal prison and ordered me to fuck her. I slid in to her like it was nothing and I started pumping away. She was still so wet but no where nearly as tight.
I'm desperately fucking her but then when I looked at her face, it was just a blank expression. She just looked bored and told me to hurry up.
"I can barely feel your tiny dick. Hurry up and finish so I can cum again. You better not cum in me though."
I felt an orgasm building as I blew my load on her stomach.
"Now put your cage back on and lick it up cuck. I wanna cum again."
I obeyed and licked up all the cum and cleaned her up. I was struggling to put my cage back on and she was growing impatient. She grabbed the dildo herself and slid it back in. She started moaning again and I could see the pleasure in her face.
"This feels so much better than your little shrimp dick. I can actually feel something again."
My cock got hard again and I couldn't manage to get the cage back on.
"Hurry up and lock your pathetic little dick up. Does seeing your girlfriends tight pussy getting stretched turn you on that much?"
I nodded my head and she kicked me out of the room.
"Go outside and close the door until you can put that tiny little thing back in its cage."
I was a bit shocked so I made my way out of the bedroom and tried my very best to get my cage back on. All while her moans were getting louder and louder. The moans didn't help at all and I had to resort to icing my dick to get it back down and into the cage. Even after putting it on, it was throbbing so much, it was painful. I knocked on the door and asked if I could come in. All I heard were her continued moans. I knocked again and still didn't get an answer so I opened the door to see her furiously fucking herself. I don't think she even noticed me coming back in. She just had her 3rd consecutive orgasm and was completely unresponsive.
She just laid there, shaking like a newborn dear. My dick was in so much pain from straining against my cage. After a couple minutes, she recovered and we talked about it.
I told her how much I loved it but she seemed a but anxious to tell me something.
She admitted that she really couldn't feel me when I was fucking her and it wasn't just for show. I felt a bit of shame but also became incredibly aroused again. She also said that this dildo is now her favorite and we discussed getting some new toys.
While my gf still isn't comfortable with committing to real cucking, she said she may be open to doing it with another girl and a strapon. Fingers crossed!!
It's been the only thing on my mind lately lol
Ps Sorry for the poor writing, I'm not very good at this kind of stuff.

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