u/sissy_girl_nj

With my sister in college I use her room as my feminine space when I am dressing up. On one occasion about two years ago my parents were away visiting my sister at her college so I had the house to myself all weekend. I took the opportunity to be fully femme all weekend and play with my pussy as much as possible. Eventually my dildo just wasn't enough and I hopped on Grindr and invited a guy over who I had been flirting with for a while. When he arrived he was tall, well built and cute. I answered the door fully enfemme and was immediately on my knees and sucking him. Eventually we took things to my sister's bedroom and he fucked me. It was a lot of fun and I didn't think anything much about it after he left. A few days later he sent me a message and asked if I knew a girl named the same name as my sister. Eventually I confessed she was my sister and I was horrified that this guy knew my sister in real life. Turns out one of his friends had dated my sister and the guy I had over always thought she was hot.

I should probably describe my sister, she is very pretty, has strawberry blonde hair and has very large breasts. She also has a history of primarily only dating black men, which partly explains my own taste in men. We talked about her over Grindr and it got very hot and sexual about how he has always wanted to fuck my sister. This led me to order a strawberry blonde wig and tease him with photos of me dressed in her clothes and her old cheerleading uniform. A couple of weeks later I had the house to myself again and invited him over. He insisted on calling me by my sister's name and made me put together a slideshow of photos of my sister that he could look at as I blew him and he fucked me. At first I was a little weirded out by it but eventually I got fully immersed in the fantasy and got so turned on imagining myself as my sister and taking BBC like I know she has so many times.

This continued with him for a few months and eventually photos of my sister became a regular part of my sissy gooning routine along with sissy hypno and BBC porn. I've also done this with a few other guys since and it always makes it so much hotter for me. I've also done the same with my mom from time to time, as she is also very attractive and has huge tits like my sister. It is now at the point where I have hundreds of photos of my sister and my mom that I regularly use to pleasure myself and for black men to view as I please them.

So I've been with my gf for a while now and posted before about trying to have sex with her before but I wasn't able to due to not getting hard. About a month ago I was considering breaking up with her due to this but took advice from some of you and quit all sissy hypno, porn, dildo play and jerking off. Last weekend was my senior prom and I knew we would have another opportunity to try having sex again and a knew she wanted it. Prom was great, she looked beautiful and then we went to party at my friend's parents beach house. I took it easy on the alcohol because I wanted to be able to perform. I also took a little blue pill I borrowed from my dad's medicine cabinet. I took my gf to our room and we started kissing and getting undressed. Some mild foreplay and I definitely noticed I was harder than I ever have been with her. Eventually I was able to enter her and it felt like heaven. Sex was okay, I kept slipping out but we eventually found a rhythm. I was nowhere close to cumming but sex felt good. Then we switched positions to doggie style. Grabbing her hips from behind brought back memories of all the times I've been fucked by black men in this sane position which naturally got me thinking of BBC. The combination of imagining my gf getting fucked by a big black cock and thinking of my own experiences with BBC pushed me over the edge and I came.

The orgasm was okay, better than jerking off but not as good as when I sissygasm with my dildo and not even close to when I have sissygasmed while getting fucked by a real BBC. Has anyone else found this to be true? Am I just conditioned now to be a sissy?

I've fingered a few girls and have gone down on my current girlfriend. I've also had a few failed attempts at fucking my current girlfriend but couldn't get hard enough to penetrate her. I hear my friends talking about how good it feels and I have to pretend I know the feeling. From fingering it doesn't feel much different than when I finger myself. If it ever happens does it feel so good I will reconsider being a sissy? I've also had sissygasms from getting fucked, which is always amazing, how much different is it to cum in a pussy?