Cuckolded by Girlfriend
She is caring, sexy, understanding, kind, intelligent, and a bad bitch. We have been together for 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 what you might expect.
See, I have a couple of secrets. I am a crossdresser. Since I was age eight, I’ve been dressing in women’s clothing, and I have an entire feminine side. My interest in cross-dressing 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’m 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 become comfortable with this side of me, but it’s easy to understand my concern about revealing this side of me whenever I am in a relationship. 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.
I like to get cock in my ass, but I love big black cocks! I find myself watching interracial sissy porn and getting rock-hard jerking off to it, wishing it was me taking those big cocks on the screen. 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 time to time. I could tell that she was somehow confused by my sissy side and disgusted with it. She only put up with my antics because I give her a decent life and a lovely house to live in and because she is madly in love with me.
I am a sissy slut, but to make matters worse, I have a pathetically tiny dick, only about four 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 out more about my sissy addiction, another fetish started to appeal to me. I learned about cuckolding and small penis humiliation during my long sessions watching Hypno. I discovered it aroused a lot to fantasize about other men with bigger cocks than me plowing my gorgeous girl. Men who were worthy of her. Men who didn’t have sissy thoughts 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 of myself, but I couldn’t stop thinking about 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 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 eight inches long and very thick. There were pictures of her sucking him off, getting fucked by this monster, and photographs of her worshipping his cock.
It turned me on so much that I masturbated to these pictures several times and sent them to myself before I confronted her about them, pretending to be upset. I wasn’t, though, for several reasons. The message’s date was long before we met, and I was excited to see her with another man. I had been jerking off to fantasies of her with someone else for weeks. Now, I had dirty pictures of her with someone else. I was beyond thrilled. Shortly after finding the images, I brought them up to her.
“Angel, we need to talk about something,” I said with a scowl. “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’s and my messages so far back? Those conversations were 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 dick hard, I went down on her and brought 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.
“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 in 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 he was, how his cock was bigger than mine, and I want to cum at that thought.”
She looked shocked, but she indulged in my fantasy awkwardly 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 for me to cum inside her, begging her to make the fantasy reality and please cheat on me. She managed to cum as well, hard, and not because of me. She had never come 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 intently before asking me if this was just a fantasy I had.
“Babe, it’s 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 tiny dick. I know it’s too small for you. I want you to humiliate me 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 permitting me and are begging me to do so, then 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 than 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 I 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.
*This story has been edited to fix spelling, punctuation, & basic grammar, but the narrative and plot have remained the same. Remember, even with limited editing. It doesn’t mean any possible major flaws in this story were fixed.