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Memoirs of a Secret Sissy, Part I

"In which I explore the origins of my sissy desires"

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Author's Notes

"This is all true, but names have been changed and some dialogue has been embellished."

My name is Michael and I'm a sissy slut. I also have a girlie name, which I'll tell you about another time. I wasn't always this way, but strangely I never even questioned my sexuality until sometime after high school. I still remember the exact moment it happened. I was watching a video that a friend had lent me, one I'd watched dozens of times already but usually just for five to ten minute spurts.

In one of my favorite scenes, a blonde woman with a very nice tan and sporting an orange bikini is kneeling in front of a tall blonde man, whose hair is almost down to his waist. She playfully bites his huge shaft while squeezing his tight ass and then slowly deepthroats his cock. Watching this play out for perhaps the tenth time now, something suddenly clicked. I'd fantasized about having this woman many times but now I started wondering what it would be like to be this woman. What would it be like to actually be in her sexy skin and feel that big dick in my mouth? She seemed to be enjoying herself so much. From that moment on I considered myself bi-curious. But "curious" was never really the right description, because I just plain wanted dick.

In college I only dated women, but this "curiosity" was always there in the back of my mind, and it was a big part of my masturbation fantasies. Looking back on that time now, I don't know why I didn't try harder to explore these fantasies in real life. I suppose I just didn't know how I could. Until my final year, I was too young for gay bars, craigslist was only just coming into existence, and I had no connection to any gay scenes or communities on campus. Fear and social pressures definitely played a part as well, and it seemed like something that should remain just a fantasy.

But as luck would have it I was presented with an opportunity to explore my bi side late one night during my senior year when I found myself in the dorm room of a male acquaintance named Ben, along with his girlfriend, Crystal. All of us had had a lot to drink, but she was generally uninhibited to begin with. She wasn't all that different, physically, from the woman in the porn scene that had sparked my bi-curiosity. And Ben had long hair like the guy, although it was dark. Anyway, at one point, completely unexpectedly and in mid-conversation, she made it clear that she wanted both of us to fuck her when she started kissing him while feeling me up through my jeans. To my surprise, Ben's hand appeared right alongside hers, also trying to grab my now-growing cock.

"I want you guys to take turns on me," she whispered. Then she walked toward the bed and took two condoms out of a jar on the desk. They both stripped quickly and I followed their lead. That's when I first noticed that Ben was the proud owner of the biggest dick that I had ever seen in real life. He must have had at least eight inches of meat and a huge pair of saggy balls that I immediately wanted to put my mouth all over.

Crystal sat on the edge of the bed, spread her legs, and started playing with her pussy. The bed was low enough to the floor that Ben could kneel down and slide his cock right into her. I watched while I started to stroke myself. She moaned but kept her eyes fixed on mine while I played with my cock and listened to the sound of Ben's balls slapping against her ass as he fucked her. After a minute or two she gave another instruction: "Fuck my face while he puts his dick in me."

She lied down with her legs hanging over the edge of the mattress. Ben crawled up and knelt above her face, tapping his cock on her lips. "Open that mouth as wide as you can and say ah," he told her. She complied and was rewarded with a beautiful, glistening cock slowly penetrating her face. "Good girl," Ben added. For the second time in my sexual life, I felt something click. It was something I knew I could never undo, nor would I ever want to. I repeated the words to myself: "good girl." From that point on it became one of my most powerful triggers. I was obsessed with the notion of being a good girl and pleasing men. I wanted to do a good job: to suck well, and fuck well. In an instant, I was changed forever.

I wanted to suck his cock so badly, but he was using it at the moment and Crystal wanted to take two at once, which I was more than happy to help with. I knelt down in front of her and felt her grab my dick with two hands, easily guiding it into her now-extremely-wet pussy. I started to pump her gently while I watched him fuck her mouth from behind. I could see his ass moving up and down, his balls nearly reaching her chin as she tried to deepthroat him. I instinctively reached out to take his balls in my left hand while placing my right hand on his ass, gently encouraging him to keep going. "Oh, that's so hot..." he said, half moaning.

We continued like that for what seemed like many minutes. I was grateful that my level of drunkenness prevented me from cumming too soon while still allowing me to stay hard. Finally, Ben lifted himself up, turned around, and stuck his cock, which was just completely dripping with spit and precum, right in my face. Crystal slid herself off of mine and went to sit in a chair to watch us while she played with herself.

"Kiss it," he said. I kissed the head while moaning softly.

"Lick it." I complied, licking the shaft and head until it was slick and no longer messy.

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"Suck my balls." I looked at him while licking my lips and then immediately took one of his balls in my mouth, sucking eagerly, while stroking his big cock. I moved to the other one and then took them both together, although I couldn't completely fit them in there.

"Now gag on that dick." I had imagined myself to be a talented deepthroater, not realizing that it required some training. The best I could do was get about half of the length into my mouth before it touched the back of my throat and I gagged. But I liked gagging on it. It made me feel dirty, and it was what he wanted. I repeated it over and over, feeling like I could cum at any second just from sucking cock.

"You like being a little slut?" he asked me. I kept his cock in my mouth and made an "mmm-hmm" sound, to indicate that I sure did. He put a hand on the back of my head and made me go a little deeper. At one point he touched the back of my throat without causing me to gag, but I was still a long way from deepthroating.

"Good girl!" he exclaimed. Oh my god, I thought, I was so hooked on this feeling. After a few more minutes he said: "I want to cum on both your faces." He got down off the bed and Crystal came over and knelt down next to me.

"Tongues out. Beg for it..." he instructed. Crystal and I both opened our mouths and let our tongues hang out.

"Yeah, feed us that fucking cum," she said. "Give it to us," we both said at the same time, smiling and giggling at each other when we realized what had just happened. It all felt so right, and so fucking good.

Ben started to breathe faster and deeper and then whispered "yes yes yes." I couldn't wait to taste his cum. He aimed it at Crystal's face first and hit her tongue and then her cheek in two quick bursts before quickly pointing it at me and shooting part of his load right into my mouth and some on my nose. I felt like I was ready to burst and started stroking myself again, getting ready to cum. I was in heaven.

"Can we do squeegee?" asked Crystal.

I looked at her curiously and then Ben said, "Sure, baby."

He took his cock head and started carefully wiping the cum off her face and into her mouth. She licked it off the tip, kissed it, and then proceeded to pass out on the bed. Ben tapped his cock on my lips a few times and then repeated the process, pushing the cum from my nose down into my mouth using only his cock. I finished myself off and came all over the floor at the same moment. It tasted like nothing I had ever tasted before. It was strange but I loved it because it made me feel so slutty. I swallowed it almost immediately and then regretted not savoring it longer.

My cock was still pulsating and dripping cum onto the floor.

"Do you understand what just happened?" he asked me.

"I'm not sure, but I loved every second of it," I replied.

"You'll always remember this moment," he explained, "because you just became a cumslut for life." I smiled at him. I felt so happy. He continued to tap his cock on my lips and cheeks. "That's right, you'll be a cum whore forever. You love cum. And you love that you love it."

I shivered with excitement. I knew he was right.

To be continued...

 

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Written by brooklyndan
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