Sissy Cuckolded by Girlfriend Ch. 01


My name is Josh and I’m a 19 year old white guy with a beautiful girlfriend. Her name is Angel and she is the best thing that has ever happened to me. I love her with a passion and intensity that is hard to describe, she is everything a man could ever ask for and more.

She is caring, sexy, understanding, kind, intelligent, and totally a bad bitch. We have been together for going on two years now and with few exceptions our relationship has been a successful one. We went through a couple of rough patches, but not for the reasons you might expect.

See, I have a couple of secrets. I am a crossdresser, I’ve been dressing in women’s clothing since before I was age 8 and I have a full feminine side. My interest in crossdressing developed over the years until it was almost like a separate person who lived in my body. Her name is Sara and she is my total opposite in countless ways. I am totally addicted to sissy porn hypnos and have been for a long time; I like being a slut, getting fucked by dominant men, sucking dicks, and being a fucking bimbo girl. I have tried to stop but I can’t, I always come back to it.

I have come to become comfortable with this side of me, but whenever I am in a relationship its easy to understand the concern I have about revealing this side of me. Not all women can accept their boyfriend sometimes gets dressed up like a whore, meets up with strangers on Craigslist and gets fucked like a bitch. It has cost me some previous relationships.

Not only do I like to get cock in my ass, but I am in love with big black cocks! I find myself watching interracial sissy porn and getting rock hard jerking off to it, wishing it was me on the screen taking those huge dicks. It wasn’t long into my relationship with Angel that I slowly revealed my feminine side to her. She was less than enthusiastic about this girl who lived inside of me, but she allowed me to continue indulging my sissy side from Ümraniye Fetiş Escort time to time. I could tell that she was confused by my sissy side and disgusted with it in a way. She only put up with my antics because I give her a decent life and a nice house to live in, and because she is madly in love with me.

Not only am I a sissy slut but to make matters worse… I have a pathetically tiny cock, only about 4 inches long at most but fairly thick; it is most certainly not a cock that could satisfy an amazing woman like Angel and I know it. As we dated and she found more about my sissy addiction another fetish started to appeal to me. During my long sessions watching hypno I found out about cuckolding and small penis humiliation. I discovered it aroused me a lot to fantasize about other men with bigger cocks then me plowing my gorgeous girl. Men who were worthy of her. Men who didn’t have sissy thoughts and men who didn’t bend over and get fucked while dressed like a slut. As time went on my cuckold fantasies became more intense and I found myself incorporating elements of femdom and SPH in them. I was ashamed at myself, but I couldn’t stop thinking about all of these nasty things that rushed into my mind whenever I got aroused.

These growing urges were made into a burning desire to submit to my lust and to be a sissy cuckold bitch with a limp dick. One day I was going through Angel’s messages with a friend way beyond when we had started dating. I was just bored and was being nosy. It was then that I saw these pictures of her with another guy; a guy with a huge cock, at least 8 inches and thick. There were pictures of her sucking him off, getting fucked by this monster, and pictures of her worshipping his cock. It turned me on so much I masturbated to these pictures several times and sent them to myself before I went to confront her about them, pretending to be upset. I wasn’t though Ümraniye Gecelik Escort for several reasons; the date on the messages was long before we met and I was excited at seeing her with another man. I had been jerking off to fantasies of her with someone else for weeks, now I actually had dirty pictures of her with someone else. I was beyond overjoyed. Anyways, shortly after finding the pictures I brought it up to her.

“Angel, we need to talk about something I said…” a scowl on my face, “…I found some pictures on your phone of you with another man. Who is it?”

She was a little embarrassed when I showed her the pictures and she explained everything to me. “Josh, what the fuck? Why were you in Elaine and I’s messages so far back? Those conversations were kinda private, I never expected anyone to read them other than Elaine.

The guy I was with was this jerk I fucked like twice. We didn’t date and I didn’t have feelings for him.”

I just nodded and dropped the subject for the moment, not wanting to rush what I was planning. Later that night we went to have sex. After we had stripped and she got my pathetic cock hard, I went down on her and got her nice and wet for sex. After she climaxed I prepared to stick my small prick in her warm, juicy, pretty pussy. Outside of her entrance, I hesitated before entering her…

“Angel, sexy babe, I want you to talk dirty to me while I fuck you.” I had never asked her to do that before, so she started by complimenting me and telling me I was sexy.

I stopped her. “No babe, not like that. I want you to tell me a dirty and nasty story. I want you to indulge a fantasy I have. While I fuck you I want you to talk about you cheating on me. I want you to tell me how much better than me he was, how his dick was bigger then mine, and I want to cum to the thought of that.”

She looked shocked, but she indulged my fantasy, awkwardly Ümraniye Genç Escort at first but then with increasing skill and arousal… As I fucked her hearing about this imaginary other man I was painfully aroused. It didn’t take long at all for me to cum inside her, begging her to make the fantasy reality and to please cheat on me. She managed to cum as well, hard, and not because of me… She had never came that hard for me. She was cumming to the fantasy and I knew it. When we finished she asked me about what had happened during sex early…

With no shame at all I told her everything, my cuckold fantasies, how I wanted to be humiliated for my small dick and for being a sissy. She listened to me intently before asking me if this was just a fantasy I had or what.

“Babe, its not just a fantasy.” I said, “I want you to cheat on me. I want you to find pleasure that I can’t give you by fucking better men. I need this. I need you to start humiliating me about my dick that I know is too small for you and about my disgusting sissy fetish. Please…”

She said, “I don’t know. I’ll have to think about all of this babe… I love you and I have never really thought about cheating on you, but if you are giving me permission and are begging me to do so… Maybe…”

It was at this point that I had gone too far, I felt like I had crossed a boundary I couldn’t return from. Right after we had finished talking I felt ashamed and concerned. I got second thoughts, but I knew what I wanted and I continued to pressure her to cuckold me for weeks… It annoyed her she said, but eventually she agreed to start talking to some guys online. I was so glad, I knew what was going to happen sooner rather then later.

I was starting down a path that would change me and my relationship… Forever… I was being a pathetic bitch boy, begging and pleading for my woman to cheat on me and she was letting me degrade myself and convince her to cheat. I’d never been so aroused in my life, I caught myself masturbating several times a day to cuckold porn and to thoughts of my girl cuckolding me, I couldn’t stop. Every day that went by the lust grew and I eagerly awaited for my girlfriend to warm up to this fantasy of mine…

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