My journey to wanna be sissy cumslut 28[MM]

I had always been curious about having sex with another man in my younger years, to be honest. I was straight and mostly thought about women, but I occasionally had fantasies about what it would be like to try gay sex. One day, it happened with my friend Brian.

I have to preface all this by saying that I’ve always been very effeminate in appearance. I have long brown hair that’s very soft to the touch, big green eyes, and full lips. I was mistaken for a girl many, many times in my youth.

I don’t fully recall how it came up. We’d been smoking a joint together and Brian was complaining about how long it’d been since he’d hooked up with a girl. Somehow, we started talking about whether either of us would be open to experimenting sexually with another man. I could feel myself blush a little as we talked about it, perhaps giving myself away. He suggested that maybe we could give each other blowjobs, so long as we kept it our secret. I was hesitant, but curiosity overtook me and I agreed. We both stripped naked and proceeded to give each other head.

While I was hesitant as I went down on him, I quickly found myself really turned on by having his dick in my mouth. I was awkward and gagged several times, but I tried to suck him off the way I knew I liked it and he coached me through what he wanted me to do. When he began to cum, I didn’t know how to react and just swallowed all of it. “God, that was good,” he exclaimed and I was felt good to have gotten him off, but was determined to do better if I ever got the chance again.

I sucked his cock a few times after that and I have to admit, I was often the instigator of it. Once, he was over at my place and I showed him some porn. As he was looking at it, I reached down and touched his crotch, asking, “Do you like that? Is it turning you on?” He said that it did, so I asked if he needed help getting off. “Yes,” he replied, and I was on my knees before him, helping him to take his shorts down so I could suck his cock for him until he blew a huge load into my throat.

Other times, he took charge, like one night when we’d gone out to see a movie. As we were leaving, he asked if I would give him head in the car, as he’d been super horny. I was a little worried about getting caught, doing it in public. “Don’t worry,” he told me. “If anyone were to see us, they’d think you’re a girl. Hell, I pretend you’re a girl when you blow me.” Now I found myself really turned on. We got into the car, Brian driving, and I had him unzip his pants and take out his cock. I leaned down from the passenger seat and began to suck his cock. “Just make sure you stay down there for the whole ride,” he told me and I did as I was told, bobbing up and down on his big cock until we got back to his apartment.

As he parked the car, I lifted up off his cock and he told me, “Hey, I want to fuck you. I haven’t fucked anyone in a long time.” My heart was racing at his words, as I’d never done that before. I’d been curious ever since one time in high school, when I’d been showering and accidentally slipped a soapy finger up my own ass and surprised myself with the sensation. I was so turned on by having given a public blowjob, though, that I agreed to try it.

We hurried into his apartment and, luckily, his roommate was out of town for the weekend. We went into his bedroom and he told me to strip naked and get on the bed on all fours, my ass up for him. I did as I was told and waited as he undressed, put on a condom, and began to lube up. He got on his knees behind me and took me by the hips, pushing his cock into my asshole. As he entered my virgin ass, the pain became excruciating, even though he was probably only halfway in. “Stop!” I yelled at him. “It hurts to much.” He begged me to let him keep going, saying it felt so good being inside me, but it just hurt too much and I kept asking him to pull out. Finally he did, taking the condom off so I could finish sucking his cock.

Maybe I should have left it at that, but I was too curious about actually taking the fucking through to completion. I was determined to let him fuck me. It happened a few weeks later. My roommate was out of town and Brian came over to hang out. Remembering what he said about imagining I was a girl when we played, I made sure to be a bit more fem looking that usual. After we smoked a joint and got nice and high, I reached over and put my hand on his crotch, asking if he’d been horny lately. I could feel his cock getting hard as I rubbed it through his shorts and he said he was. I got down on my knees in front of him and took it out to play with, licking it and kissing it, before I took it in my mouth as he took the back of my head in his hands and pushed it down my throat. When I had him nice and hard and wet, I looked up at him and asked, “Did you still want to fuck me?”

“Oh, hell, yes,” he replied and we quickly went to my bedroom. This time I stripped and he instructed me to lay on my back. I did as he told me as he put on a condom and lubed up. He took my legs in his hands and put them over his shoulders. I could feel his cock pressing against my asshole and then he was entering me, filling me up, stretching me out with the width of his cock. It hurt momentarily, then to my surprise, I was overcome with pleasure as he pushed deeper and deeper into my ass. Before I knew it, he was fully inside me. “God, you feel so good he groaned,” as he began to fuck me, in and out so deep.

I closed my eyes, overwhelmed by how good this felt. As he picked up a rhythm, I couldn’t control myself and heard my own words coming out from somewhere, begging him to fuck me, keep fucking me, telling him how good his cock felt. He was spanking my ass, fucking me harder and harder, telling what a good slut I was and I just kept begging for that dick. I was out of control, but it felt so good.

He came deep in me finally and went to the bathroom to wash up. My own cock was so hard, that when I touched it, I came myself. We never did anything again after that and I don’t know if it was that I freaked him out by begging to be fucked. But it made me explore a different side of me, buying makeup some times to see how pretty of a little slut I could make myself, dressing up in panties and dresses.

I developed a fantasy about finding some straight guy in a sexually frustrated marriage, with whom I could have an arrangement to dress up super sexy and slutty and meet him at motel rooms, where he could use me as his little cum slut, making me get down on my knees and suck his cock, putting me up on the bed to pull my panties down and fuck me hard and deep. And always remind me that he was just using me for sex, his dirty little secret cum slut.

Source: reddit.com/r/gonewildstories/comments/9s97kk/my_journey_to_wanna_be_sissy_cumslut_28mm