“I’m in love with someone else.” Those words, uttered by my (now-ex) wife, started me on this journey. My name is Terry, and I’m going to tell you the story of how I got here today.

Heather claimed that telling me was for my benefit, but it was really because she felt guilty. She felt guilty that she hadn’t loved me for the entirety of our relationship and never thought to tell me. I had a slight suspicion that this was the case, but I couldn’t bring myself to believe it. She said that she never got physical with the guy she’s in love with, but it’s not like that mattered anymore. It was all a betrayal of trust.

She promptly gave me divorce papers that day and went about her merry way. Thanks to a pre-nup and no kids (she’s infertile, luckily), we got the divorce done pretty quickly. I started seeing pictures of her with another guy about a week after the papers were handed to me. She must have forgot that I have her on social media. I could have pushed for a dissolution of the pre-nup due to infidelity, but I just wanted everything with her to be over and done.

Once the divorce was finalized, I tried going on dates again. Some relationships fell flat pretty fast, while others just eventually didn’t work out. I often took a break from dating after the longer relationships, but got back to it after a month or two. After a few years of dealing with the same cycle, I just gave up. I told myself that I was probably meant to be alone, but if I wasn’t, then the right person for me will come into my life.

Following my declaration of loneliness, I had to get out my sexual frustrations from time to time. Like what most men would do in this situation, I went to porn. On the weekends, I spent a lot of time browsing porn sites. I didn’t jack off much, to be honest, but I liked to see what turned me on so that I could go back to the videos later. This may seem like a porn addiction to you, but I didn’t really see it that way.

One day while I was browsing around, I found something that I had never really explored before: transgender porn. I was initially a little skeptical, because that seemed out of my wheelhouse when it came to porn. But then I figured, why not try it once? So, I did just that.

I clicked on the video, and there on the screen was a beautiful woman in some sexy lingerie. At first, I thought that the video was mislabeled because that woman did not look transgender. Soon enough, though, the woman took off her underwear and her cock sprung to life. It almost made me jump out my seat! Who knew that a man could become such a pretty woman while keeping their penis intact? I gotta say, I was turned on instantly, and I began to masterbate. The woman in the video was fucking herself silly with a dildo, and she acted as though her penis wasn’t there. I was so horny that it didn’t take long for me to cum. I cleaned myself up, but kept watching the video until the woman also came, semen flying out of her penis like a rocket. God, that was hot.

For a few months after that fateful day, things were still pretty normal. Nothing had changed with my work or social life, and I was still just a normal dude. I did, however, begin to watch transgender porn more frequently, but that was really the only new thing for me.

One Saturday morning, after one of my porn-watching sessions, I was a little bored. At a certain point, I had wandered into the house’s spare bedroom. Heather had kept all of her stuff in this room because we didn’t have any space in the main bedroom. When she left me, she only packed a few clothes and not much else. Even after the divorce, she didn’t want to come back to get anything. So, most of her stuff has just been sitting in here collecting dust, and I never thought about getting rid of it.

Anyways, I was looking through the room’s dresser drawers when I caught my eye on one of Heather’s old lingerie sets. It had a pair of panties with a lace trim, a see-through babydoll, a garter belt, and pantyhose, all in black. I had seen her wear this set multiple times, and she looked sexy with all of it on. I was about to close the drawer when something in the back of my mind stopped me. I had also seen the women in the transgender porn wear a similar set, and it looked sexy on them, too. If it can look good on someone who used to be a man, would it look good on me, a current man?

“There’s no harm in trying it once,” I thought. “I can just take it off if I don’t like it. Plus, it’s not like Heather needs it anymore; she would have taken it if she did.” It didn’t take long for me to make my decision. I took the set out of the drawer and set it on the bed. I stripped down to my birthday suit and mentally prepared myself to get started.

I grabbed the panties and slowly slipped them up my legs, its satin feeling nice on my skin. After getting the panties over my groin, it seemed a little tight. In the transgender porn I’ve watched, the women had their penises tucked in between their legs. So, I tried that, and the panties fit much better. I then strapped the garter belt around my waist, letting it sit above the panties.

Next was the pantyhose. I rolled each leg up and brought them up my legs one at a time. It was surprisingly a better feeling than the panties. With the pantyhose completely up my legs, I secured them in with the garter belt. Last but not least, I took the babydoll, slid it over my head, and let it fall into place. I’m actually surprised all of this fit me.

Looking in the mirror, I was shocked. Below my neck, it was hard to tell that I was a man. I guess this isn’t noticeable with my other clothes, but with the lingerie, you could tell that I definitely had a feminine body. I was skinny, had an hourglass figure, and a firm butt. I was practically like the women in the videos I watched. I could feel myself get horny at my own image, but my penis couldn’t get hard due to it being tucked away.

I wore the lingerie for the rest of the day that day. I did laundry, I cooked, and I cleaned all while wearing the sexy lingerie. Even when I was just watching TV, I sat on the couch with my pantyhosed feet kicked up on the coffee table, getting giddy every time the panties rubbed against my butt. I loved every minute of it. I even wore it to bed that night.

Unsurprisingly, I decided to do it again that next Saturday. Before I got dressed into everything, I decided to use the bathroom attached to the spare bedroom. As I was sitting on the toilet, I looked around the bathroom. Heather had rarely ever used the bathroom attached to our bedroom (kind of a red flag, looking back). So, her toiletries, makeup, and other miscellaneous things were in this bathroom. I eventually found the stuff she used to take a bath, like her soap, shampoo, and fragrances; there was also some shaving equipment, which she had used often. That got me thinking about the porn again. The women in the videos often had their bodies completely shaven, especially around their groins. It was in that moment that I decided to follow suit, and hair grows back anyway, right?

I drew up a warm bath, and put some bubbles and oils into the water. I slipped into the bathtub and turned on some relaxing music. I let myself enjoy the bath for a few minutes before I got to work. I took Heather’s shaving gel and spread it across my entire body. I then used her razor to shave every bit of hair on me, which luckily wasn’t hard, since I’m so used to shaving my face. I touched my hairless skin, and it felt amazingly soft. Feeling satisfied with my handiwork, I washed myself up with the girly soaps, and it all smelt really nice.

I got out of the tub and dried myself off. I decided to use some of Heather’s lotion on my body, as I didn’t want to get any razor burn in uncomfortable places. The lotion made my skin even softer than before, which I didn’t think was possible. I saw one of Heather’s old robes hanging up and decided to put it on, as I still wasn’t completely dry yet. I decided to make myself a little snack while wearing the robe. With every movement that it took to get to the kitchen, I could feel the robe brush up against my hairless skin, and I loved it.

After I knew that I was dry, I went back to the bedroom to change into my lingerie. I decided on a red set this time, which had the same pieces of clothing as the previous set. I got dressed into everything, taking note of euphoric feeling that came with the clothing on my soft, hairless skin. It was even better than the last time I wore the lingerie. Like last week, I did some things around the house while in the lingerie. Once I finished, though, I discovered that I had gotten really horny. I decided to have a little fap session, but my first time in the lingerie.

I went to my computer and pulled up more transgender porn for my viewing pleasure. The video I had up was a woman dressed very slutty and had her large penis in focus as she stroked it. I copied her as I whipped my dick out and also started stroking. I watched the woman stroke like there was no tomorrow as my dick slowly got hard. Towards the end of the video, I saw her penis spasm, and she repositioned herself. For a split second, I wondered what she was doing, but then she came, and the cum splattered all over her face. She slowly licked everything off of her, which practically sent me over the edge.

Before I came, I decided to do what she did and changed my position. In no time, I exploded like never before, and it all ended up on my face. I took a little lick of my cum; it was salty, but surprisingly not bad. Unfortunately, post-nut clarity hit, and I cleaned myself up in the bathroom. I decided to hit the hay early, still in my lingerie. I fell into bed, thinking about how wonderful things have become lately. I fell asleep smiling about the good times I’d had.

A few weeks passed by, with me having done my new routine each weekend, and I enjoyed every moment of it. This Saturday, I had just finished taking my bath and was wearing a pink robe. I was about to get dressed when a random thought entered my mind. I pictured one of the women in the porn videos, and thought about how sexy her makeup was. Curiosity got the best of me, and I went to look through Heather’s own collection of makeup. She had lipstick, mascara, and nail polish, all of which I have seen on the woman I was picturing. If makeup could look good on someone born a man, could it also look good on me? I figured, “why the hell not?” And so, I got to work.

I looked up videos on how to apply makeup. I started with the mascara, which was probably the easiest. I used the wand to plump my eyelashes, which I could now see each time I blinked. I then moved on to the lipstick. I chose a red color I had never seen Heather wear, but did like it on the woman in the porn videos. After watching the makeup tutorial, I carefully traced my lips with the lipstick. I messed up in a couple places, but was able to fix it. Finally, I went to the nail polish. I decided to match my lips by using a red nail color. To get some practice, I painted my toenails first. One by one, I brushed the polish on my toes, and soon enough, I had bright, shiny toenails. Since I had gotten the hang of it, I painted my fingernails, too, and realized that it was harder to paint with my non-dominant hand. I waiting for my nails to dry before I moved back into the bedroom.

I looked through the lingerie and found that I had worn every one of the sets in the drawer. I decided to look further in the bedroom’s closet. Heather had left an array of tops, skirts, and dresses hanging up in the closet. I figured that I might as well try something new and chose a black skirt with a frilly pink top. I grabbed a matching red bra and panty set from the drawers, and put the entire outfit on. I also found a pair of open-toed sandals that I felt went well with the outfit.

Seeing my reflection in the mirror, there were practically no masculine features left. I looked almost exactly like a girl, head-to-toe. The hairless skin, feminine body, makeup and nails done, and the girly outfit, all contributing to making me completely look like I was born a woman. This was such an amazing feeling.

As expected, the image of myself was making me horny again, and so, I went back to transgender porn. I put on a random video and watched intently. I was about to untuck my penis when I noticed what was happening in the video. The woman did not take her penis out, but rather rubbed herself through her panties. Seeing this, I tried it out myself, and it was a whole new feeling. The rubbing of the material against my penis was like nothing I had ever experienced before. It was such a sensual feeling. Before I could even finish the video, I reached orgasm, and cum flooded my panties. I used my fingers to scoop out as much cum as I could, brought it up to my mouth, and licked it, as I had grown fond of the taste. I then changed out of the panties and went to do some chores like normal.

Now, over the coming weeks, I had decided to try dressing like a woman full-time. My job was completely remote, and I never had to be on camera, so this was an easy decision for me. This allowed me to try new outfits and styles to see how I felt in them. I kept practicing doing my makeup, mixing and matching the colors that I use. I also polished my fingernails and toenails, changing out the color every week, and I let my nails grow longer to make them look more feminine. There was rarely a moment that I looked or acted like a man anymore (outside of when I have to run errands in public).

There was a point where I decided to make a few impulse purchases online. The porn I’ve been watching often has toys involved, like butt plugs, dildos, and chastity cages. I had yet to try out any of these things, so I bought one of each for the sake of experimenting. They all arrived just in time for the weekend, and I was pretty excited. I was mostly interested in the chastity cage, as I was tired of having to tuck my penis all the time.

Through my endless searching, I had learned of a site that helps out solo chastity cage users. Following the instructions of the site, I stuck my penis in my personal cage. Making sure that the cage fit comfortably, I locked myself up with the key that came with it. I stuck the key in a lockbox, randomized the code, then, using the site, I took a picture of the code without looking so I couldn’t cheat. The site then chose the amount of time that I would stay in chastity before I was given the code: 10 days. I was nervous and thrilled at the same time.

Now that I was locked up, I decided to wear my new butt plug. A lot of people online said that it was best to warm up your asshole before going to bigger things (such as the dildo). Since I had never done ass play before, I definitely needed a butt plug to do this. I took my new butt plug, lubed it up, and slid it into my asshole, which elicited a little moan from me.

Figuring that I was done for now, I got dressed up again. The chastity cage was very helpful in giving me a flat front. Sitting was easier with it on, too, as I was practically sitting on my penis before. There was also no telling that I had a butt plug in, even though I constantly felt it inside of me, especially when sitting. I only felt the need to take it out whenever I had to use the bathroom.

For the next week, I got hornier and hornier due to the chastity cage. But I ignored my male urges as best as I could. I sometimes teased my butt plug to try and get off, but it just made me even more horny. I waited to use the dildo for the weekend again, as I needed time to prep my asshole and wanted a whole day to do stuff with the dildo. But when Saturday hit, I was completely eager to use my dildo. This dildo was bigger than my penis had ever been, and it made my caged penis look pathetic. I can’t believe I was going to put this thing inside of me.

I pulled up some porn of a trans woman riding her dildo. I lubed up my own dildo and slowly slid it inside me. I gasped as the dildo stretched my insides like they were nothing. I rode the dildo like the woman in the video and fucked myself silly. It took almost 10 minutes of riding that dildo before I reached orgasm, and even then, almost no cum came out of me. It felt so good, but I was still completely horny. I continued to ride the dildo for close to an hour, getting 3 more orgasms within that time. The final one was what did it for me, and cum came out of me like a fire hose. God, that was amazing.

For months after that, I continued this way of life. I stayed locked 24/7, made myself look/dress like a woman almost 24/7, and only masterbated using anal toys. I bought a bunch more stuff online, competing with everything Heather had left behind so long ago. I was actually happy more often than I ever had before, and it was all due to this.

After much deliberation, I decided to do what I was holding back on this entire time: I wanted to have sex with a trans woman. This past year made me realize that, not only do I want to be like these these trans women, I want to be with them, too. I figured that it’s no more “gay” than what I was already doing, and so, I found a trans woman online, and she’s going to meet me at my house today.

I prepared myself by getting into the sexiest lingerie that I owned. I made sure that I was shaven all over, and used lotion to make sure I was extra smooth. I put on tons of makeup, and painted both my fingernails and toenails in a deep red color. I curled my now-long hair into a cute, wavy hairstyle, and put in some hair spray to keep it in place. I finished things off with a touch of perfume.

Not long after I finish up, there is a knock on the door. I lay myself on the bed and yell, “Come in!” in the best feminine voice I could muster. The door opens, and in walks the most beautiful woman I had ever seen. She wore a red strapless dress that showed off her devine legs. She had high-heeled stilettos that made her tower over me. Her wavy blonde hair flowed past her shoulders and lightly touched her breasts. Her cherry red lipstick and matching nails stood out the moment she entered the room. She did not look transgender at all.

“Hey there, sexy,” she said in a light, feminine voice. “You ready to get it on?”

All I could do was nod. She kicked off her shoes and zipped off her dress. As the dress dropped to the floor, it revealed her lucious breasts and big cock, right there in front of me. I drooled upon seeing her naked, wanting to touch every little part of her body. She slowly began crawling on the bed towards, and we started to make out. Our lipstick-stained lips touching each other was a new sensation for me, and I was loving it.

I took my hands and fondled her breasts, teasing her nipples with my red fingernails. She clearly liked that, as she made out with me even harder. We played tongue hockey for a little while, both of us become hornier by the minute. She guided my hands down to her cock and had me give her a handjob. She stopped me once she was hard enough.

With her cock hard, she shoved me down onto the bed and began taking off my lingerie. Upon taking off my panties, she saw my caged penis and smiled. To prepare for the night’s big event, she lubed her cock up and propped my legs up on her shoulders. She slid her dick into my asshole and I let out a big moan. The veiny nature of her cock was another foreign sensation that I couldn’t get enough of. She thrust herself inside of me as I kept moaning.

As she was deep inside of me, I had 6 consecutive orgasms, a new record for me. Then, I could feel her cock pulse, and knew that she was about to cum. In one final thrust, her cum sprayed all inside of me. I could feel the pool of cum sitting in my ass. She pulled out, and the cum began leaking onto the bed, mixing with my own cum. She took the mix of cum and fed it to me, with me being super eager to gobble it up.

We laid on the bed together in bliss, cuddling with each other. I guess I am officially a sissy now.