How this straight guy became a sissy bottom

I grew up straight for most of my life. It wasn’t until I turned 40 that I started to experiment with gay fantasies. I was surprised to find that imagining that I was having sex with another guy resulted in my most intense masturbation orgasms. As my mind got over the fears I had about these new sexual desires, I realized that I had always been turned on most when I saw a hard cock. And while my sex life started with a guy so many years before, it was a bad start.

I had recently turned 40 when I began to examine my gay fantasies. I remembered my one and only gay encounter. I was only 18 and still a virgin when a 24 year old guy got me drunk and tried to have his way with me. I was curious and too drunk to protest, but I also couldn’t maintain an erection. He kept frantically sucking my cock and alternately jerking me off, but to no avail.

He finally gave up on me and decided he would just get off himself. He stood up and grabbed my hand placing his penis across my palm. He then wrapped my fingers around the girth of his manhood. I’ll never forget holding his cock that night because he was as hard as a man can get. I could even feel his pulse race as I gently stroked his smooth foreskin that seemed to barely contain the granite-like shaft underneath. I watched him react to my touch and felt the power I had over him. I started to jerk him off with my left hand. The problem was that I was right handed and too drunk to be coordinated. I quickly tired and reluctantly let go of my prize.

My magic moment was over much too soon because I was too drunk to enjoy it all. But he was not to be denied. I was slumped down in a chair and he positioned himself over me with his legs straddling my hips. He started rubbing his erect cock against my stomach and then leaned forward until his phallus was sandwiched between his pelvis and my stomach. He began pumping his hips as his precum greased the skin around his cock. Soon he was desperately fucking my stomach and cried out with a huge groan as his cum forced its way between us. My torso was covered with enough of his spunk that I looked like a glazed donut. I found I was more excited than grossed out. I had just stirred this man’s most primal desires until he got off any way he could. Still, I was too drunk to do anything else except fall asleep. I left the moment I awoke and we never saw each other again.

Years later, I realized that holding his erect cock and knowing I was the one making it hard was the best part of that night. That had been the most turned on I’d ever experienced despite not being able to cum. I realized that I was much more interested in getting him off than in cumming myself. I was too young to understand what being submissive meant, but I should have known then that my sexual desires were not typical for most guys. Later, I would realize that I was more effeminate than most women, but that part of me remained hidden for many years afterward.

Conditions in my life steered me away from other gay men. I found that women wanted to fuck me and that an orgasm in a pussy felt pretty damn good. However, I found that when I was with a woman, I made sure that I was well-serviced and satisfied. Not that I didn’t make them cum as well, but that was not my top priority. I came to see sex with a woman as I did masturbation. It felt great. I did it as often as I could and I didn’t mistreat the hand, pussy or mouth that got me off.

And so I remained heterosexual, in practice, for 22 years after my first gay experience. I began to view my first time as an anomaly. It was just a one-time experience that tended to prove that I wasn’t gay because I didn’t achieve orgasm.

If it hadn’t been for internet porn, my latent gay desires would have remained hidden for the rest of my life. When I turned 40, I decided to re-examine myself to make sure I was getting all I should out of life. I finally admitted how much I liked seeing a hard cock on my computer screen. I began to browse every gay website I could find and took note of what turned me on the most. It came down to seeing hard cocks and watching guys cum.

At first I compromised with my fear of being gay by preferring trannies. I fooled myself into thinking my sexual history could be explained if what turned me on the most was a good looking female with a hard-on. I enjoyed watching guys have sex with trannies but it took a while to admit that I identified more with the tranny than I did with the guy fucking her.

Eventually, I admitted that I wanted to be the one who made the guy’s cock hard. I would imagine dressing as a woman and sucking straight guys off without them knowing my true gender. My sexual fantasies kept expanding until I couldn’t deny it anymore. What I really wanted was to be fucked. I wanted to feel a man thrust his raging hard-on inside of me and fuck me silly. I wanted my second gay lover to know just how effeminate I am and that he would want me all the more because of it. I was a bottom and my desire to fulfill the female role meant I was also a sissy. Luckily, I was naturally cute in an androgynous way and largely hairless even at 40 years old.

I decided my first step would be to get all my body hair waxed off. I made an appointment at a beauty spa in the next town. The woman who did their hot wax hair removal was nice and kept telling me how good I looked when she was finished. I was embarrassed that my cock stayed erect through the entire process. She asked me if I wanted to get a second opinion on what else I should have them do to complete my new look. I was embarrassed but hesitantly nodded my consent.

I expected another woman to join us but it was a man instead. He was well-built and handsome, but he hardly looked like he was into guys. I was almost ready to run out of the place, but his expression changed my mind. I could see his desire for me growing as he surveyed my hairless body and raging boner. He suggested that they do a complete female makeover on me so I sat down at the vanity as they went to work. A wig and 20 minutes of make-up application quickly turned me into a very passable woman.

They added some transsexual lingerie and a little black dress so I could experience the entire transformation. I had to admit that I even thought I was sexy. I stood and kept turning around to see all sides of me in the mirror. I hadn’t noticed that it was only me and the other guy in the room. The lady had disappeared knowing what was about to happen next.

The guy, whose name was Carlos, did exactly the right thing to get things started. He disrobed quickly exposing his impressive erection all the while telling me how sexy I am. He then lay down on the waxing table with his 7” uncut cock standing straight up in the air. I had a preference for uncut cocks because my only gay experience had been with an uncut guy all those years ago. I walked slowly toward him moving my hips like a stripper doing a table dance. I used my hands to perform hairflips with the long-haired wig and I put on a wicked smile. I started telling him about the blow job he was about to get and how hard I was going to make him cum.

The lust in his eyes was undeniable. I bent over him and teased the head of his cock by running my tongue between the uncut foreskin and the sensitive head of his penis. His gasps turned me on all the more and I started taking more of his delicious manhood into my mouth. He moaned softly as I started to bob my head up and down on his penis. I cupped his balls with my left hand as I stroked his shaft in synch with my mouth moving up and down the length of him. I wanted to taste this man’s seed. I wanted him to let go of everything he had inside me. I completely embraced my newfound femininity.

Suddenly Carlos jumped up from where he was. He moved around behind me and pushed on my shoulders until I was leaning over the waxing table. He wasted no time in hiking up my dress from behind and ripping away the lacey panties that covered my ass. I was surprised at this turn of events but I realized that Carlos was about to fuck me. I almost fainted because wanting something and getting it are often two very different things.

Carlos spit into his hand and rubbed his saliva into my anus. I was still deciding if this was a good thing or not when I felt the heat from his approaching cock as he spread my butt cheeks apart. I had watched this sort of scene many times on the internet, but this time it was me getting fucked. I was alternately full of dread and anticipation as the head of his uncut cock pushed gently against my anus. My transformation into a sissy bottom was about to become complete.

The next moment I couldn’t believe the pain that shot through me. Carlos had managed to get the head of his cock inside of me and then he forced himself inside me the rest of the way with one forceful thrust. I was seeing stars and let out a high pitched yelp like a girl. Carlos began gyrating his hips as he fucked me with everything he had. I managed to settle into a rhythm with him as he rode my ass and kept gasping loudly about what a sexy bitch I was.

The pain was still intense, but I started to appreciate everything else I was experiencing. I felt completely feminine as his cock battled with my sphincter for control. I could feel his energy driving into me. I could feel the friction lessen as his sticky semen coated me from the inside and made his powerful thrusts more bearable. I enjoyed knowing that he found me so desirable that his rough entry was forgiven. It was as if I could feel all his fears, anxiety and frustrations melting away as his balls slapped against my exposed and newly hairless crotch. I could tell that I was born for this. Servicing men gave my life new purpose and I relished this man’s cock impaling me, teaching me how to please him more.

I was surprised at how feminine I felt. How sexy that feeling was and how we both looked in the vanity mirror as Carlos continued to fuck me. The way the black dress hung down from my hips concealed the raging hard-on I had and I looked like a hot chick taking one up the ass. The wig and tranny make-up made the rest of me looked like a woman taking proper care of her man.

Carlos’ thrusts suddenly became more focused and intense and I could tell he was ready to cum. He managed to gasp, “Are you ready for it you sexy bitch? I’m going to cum inside you as I’ve never cum before. I’m going to fill you with my seed. You are going to remember this moment for the rest of your life and all the other guys you fuck will be compared to me. Get ready mamacita, here it comes!”

And with that, Carlos rammed his thighs against my butt cheeks with a ferocity I hadn’t known was possible. I desperately wanted to feel the spurts from his cock inside of me. As his primal groans filled the room, I did feel his seamen, saliva and sperm escaping my anus as the mixture drew sticky lines dripping down my newly waxed legs. I could feel my own climax flood over me as I had never experienced before. I kept feeling waves of pleasure crashing through my body as Carlos’ hands moved from my hips to caressing my back signaling that his orgasm was finally subsiding. Then he stopped moving and I sadly felt his softening cock slipping away from me.

At first, I felt the pride of a great accomplishment. With a seductive smile on my face I was already planning what this sexy bitch was going to do next.