At this point, it feels like a dream. Sometimes I still can’t believe that I used to be a straight man in a committed, monogamous relationship with my girlfriend of six years. And now I’m . . . well, I don’t want to ruin the suspense. My transformation story begins in 2009. So, that’s where I’ll begin.
My girlfriend Morgan and I met during our sophomore year in college. We were both in the theatre program and instantly hit it off when we were cast in a play where we had a few kissing scenes. We found ourselves continuing the action in either her or my dorm room after rehearsal had ended. Eventually, we made things official and started dating.
Morgan is a bigger girl, about 5’11” and 220 pounds. But her curves are in all the right places, and I love that. I, on the other hand, was a short and frail lad—5’6” and 120 pounds soaking yet. Our friends would sometimes poke fun at us as that classic BBW meets scrawny guy pairing. We didn’t care, we just loved each other and had great sex to boot.
Our sex life sort of reflected our statures. Morgan liked to be in control in the bedroom and I was more submissive. I loved that I had found a girl who knew what she wanted. She loved that I was great at giving her oral, and I loved performing it. There were more than a few occasions where, for two or three weeks, our sex life consisted of me going down on her with nothing in return. For me, getting her off was sometimes satisfying enough. And I could never get her to cum just from fucking anyway, so even after we fucked, my tongue would always find its way down south.
Morgan and I stayed together throughout college and, after graduation, moved into a tiny NYC apartment together where we both pursued careers in the theatre. I was an actor. She was a playwriter. We both struggled. I got bit parts here and there but nothing serious. And she found freelance work, writing for gossip rags, but was never able to close the deal on getting one of her plays produced.
When the 2008 financial crisis hit, we found ourselves unable to pay rent. That’s when Morgan first proposed the idea that changed our lives. We were sitting around our apartment brainstorming ways to come up with the cash to pay our landlord later that week. She closed her laptop and looked at me very seriously.
“Babe,” she started, “what if I did a little online cam stuff?”
I paused. I knew what she meant, but I had never considered something like that.
“What do you mean?” I asked.
“Y’know, like, setting up an account on one of those cam sites and fooling around for tips and stuff...”
I took a few seconds, trying to collect my thoughts. The thought of other guys on the internet watching my girlfriend get naked and masturbate was so off-putting. To be honest, I had clicked on a couple of those sites before. I had jerked off to girls just like her, so I knew what would be happening on the other end of that connection. But we really needed the money.
“You’re not, like, trying to hook up with other guys or anything?” I asked.
“No. No. Absolutely not, Babe! I love you. This is just to see if we can make enough money to pay rent without getting kicked out on the street next week. What happens then? You don’t have any family to fall back on, and my conservative asshole parents won’t let you move in with me if I have to go crawling back to them. If you can’t think of any other ideas, I think this might be our best shot.”
She was right. My parents died when I was young. Without Morgan, I’d be alone. After another short pause, I gave the answer that set the course for every life-changing event coming our way over the next few years.
“You’re right. I can’t think of anything. If you think this will work, I guess I support it.”
****
Morgan was right. She made enough money to pay rent that month. To keep us both comfortable, we worked out an agreement that I would always be in the chat so I could see what was going on. I must admit, my feelings about the whole situation began changing. I started to really get turned on by all the chats flooding in while she would slowly peel off her clothes one by one.
When she would pull down her bra and expose her fluffy, pink nipples, I’d read comments like, “I’d suck those titties, slut,” or, “let me put my dick between those jugs,” and I’d find myself getting really turned on. Maybe it was because I knew what it was like to actually be doing those things. Maybe it was because I always had a bit of voyeurism in my blood. I don’t really know, but I do know that all my initial hesitation faded after a few "shows". Not to mention, Morgan had a hard time actually “finishing” on cam, so she would usually fake orgasms and then ask me to finish her off once the cam was off.
Two months had gone by. Morgan was camming three or four days per week, but we were still barely making ends meet. We both were still unable to find work. No one was paying for freelance writing anymore, and I hadn’t been offered a part in months, not even in commercials. That’s when Morgan floated the second idea that would change our lives.
I could tell she wanted something that night because she made my favorite meal and gave me one of the best blowjobs I’d ever gotten from her. As we lay in bed together afterward, she started stroking my arm.
“I have a sort of crazy idea, but I think it might solve all our money troubles.”
“Well, your last one worked, so let’s hear it,” I chucked.
“This one involves you, though, sweety.”
“What are you getting at?” I asked. I assumed she wanted me to start being involved in the show, having people watch her blow me, or getting fucked.
“I’m thinking we should get you on cam too.”
I knew it! I thought to myself. I laughed out loud before replying.
“Babe, no one in their right mind would want to see me on cam. Who would want to see a scrawny guy like me jerk off or whatever?”
Morgan paused for a moment. I could tell she was formulating her words in her mind. Then she came out with the proposal.
“Well, you’re right. I wasn't thinking you as you are now, but you as someone . . . different.”
“What do you mean?”
“Okay, so I was chatting with another cammer and she mentioned that she was jealous that we don’t make as much money as another . . . demographic.”
“You mean, like, skinny girls or something?”
She slapped my arm, “No, that’s not what I mean!”
“Sorry, sorry,” I chuckled, “I’m not sure what you’re getting at.”
“So, there’s this very specific type of camming that apparently has a big audience but not a lot of players in it. And the more I think about it, the more I think I’ve found a niche that’s really underexplored and could make us a ton of money. That is, if it works, and if you’re willing to do a little acting.”
She knew just how to push my buttons. She knew that I love acting. I wanted nothing more than to make a living acting. And I’d told her before that I was willing to play basically any role, that I thought I could make anyone believe I was someone else.
Morgan went on: “Have you ever heard of sissy porn?”
I was vaguely familiar with it, boys turning themselves into girls, that sort of thing.
“I guess, but what, you want me to do sissy porn? No way, Morgan. No way.”
“No, not like that, I had something else in mind, actually. So, here’s the idea. Apparently, there are men out there who love the idea of being able to dominate and feminize other guys. I’m thinking we play into that fantasy. I’ll set up a cam profile called ‘The Group Sissification Project.’ And I’ll play your mistress who is feminizing you, and then we can have viewers pay us to have you do all these little tasks and stuff. But, in reality, we’re both in control and you’re just playing a part—the role is to play a guy becoming a sissy, not actually doing it. What do you think?”
Morgan bit her lower lip and put her hand on my knee. I was dumbfounded. On one hand, I couldn’t believe what she was proposing. On the other, we needed the money. I was thinking things through when Morgan pressed the issue.
“You’ve always said you think you can handle any role. And there’s been male actors who’ve won actors for playing trans women recently, right? Wouldn’t this be a great acting experience, really let you build your chops?”
She had played her cards perfectly. After all, this would a challenging role that would test my acting skills. If we could get paid handsomely, why not?
“Okay, let’s do it,” I said, "but how do we start?"
***
Morgan set up the site and did a little online promotion. Her promotional materials said things like: Have you ever wanted to turn a submissive man into the sissy (s)he was supposed to be? Tune in at 8:00 PM this Tuesday to play a part in the first-ever group sissification project!
That morning, Morgan prepared a list of things I had to do. The first was to get rid of all the body hair below my eyebrows. I stepped into the shower, grabbed Morgan little pink razor, and got to work. I still remember that first time feeling my hairless body as I got out of the shower, that sense of vulnerability and sensitivity as my skin came alive in a way it never had before.
Next was the wardrobe. When I stepped out of the shower, I saw that Morgan had laid out a pair of matching black lacy bikini-cut panties and push-up bra, a jean skirt, a black off-the-shoulder long sleeve top, and a pair of three-inch black pumps. Next to the clothes was my laptop with a sticky note on it, which read: “Watch this video. It will help complete the look before we go live. Xoxo”
I opened the laptop and she had a video queued up called Tucking for Crossdressers. I watched it, learning how to push my testicles into the inguinal canal and pull my cock back and keep everything in place with the panties. From my research, I knew that this was something sissies did, but I guess I didn't think I would be doing it just yet. Nevertheless, I followed the instructions. I slid the panties up to hold everything together. It was a little uncomfortable at first, but I was surprised at how quickly the feeling became . . . natural. I dressed myself in the rest of the outfit and walked out to meet Morgan at the laptop. When she saw me, her mouth went agape.
“Oh my God, you look, like, really quite hot!” she laughed. I felt my face flush. She reached her hand out and squeezed my butt cheek. She left it there for a second, gave it a little jiggle and a pretty hard smack. I felt my cock get tight in my panties, but they were on so tight that the feeling quickly transformed into a tingling sensation in my torso. That's a new feeling, I thought to myself.
“This is so going to work," Morgan exclaimed, "Holy shit. I had no idea how convincing your little body would be!”
I didn’t know whether to be offended or relieved. Either way, I sat down next to her. It was 7:30 PM, a half-hour until show time. Morgan instructed me to get into character. I really dug into the idea that I was already submissive in my relationship with Morgan. I channeled that submissive energy into the idea of femininity. I did some meditation exercises where I imagined feminine energy slowly tingling through my veins.
“So, how is this first night going to work?” I asked.
“Well, this is fucking crazy, we already have over 500 people in the chat and the video isn’t even live yet! I think we’re going to make a boatload. So, I think tonight we just start out with a little introduction. I’m going to tell them the story we came up with, and then tonight I’ll put makeup on you for the first time. Then, we’ll open up the chats and the bids we talked about. Sound good?”
“Yeah, I guess I’m as ready as I’ll ever be.”
When the video went live, comments immediately started rolling in. It appeared that Morgan was right about the demand to turn boys into girls. My mind was racing trying to stay in character, trying to fight back whatever urges I had to shut this down, and contemplating the words I was reading.
The chats consisted mainly of things like:
Can’t wait to sissify this little slut
Look at her there all nervous, get ready baby
Can’t wait until she’s a real slut
Morgan began speaking to our fans:
“Welcome, boys and girls, to the group sissification project. My name is Mistress Morgan, and I’m going to be your guide as we turn my boyfriend, Sam, here into my girlfriend Samantha. This started a few weeks ago when Samantha told me her secret desire to become a sissy. And I came up with the idea to do this together with you, our loving, lusting community.
“So, here’s how this is going to work. Tonight, we’ll kiss this little plain-faced boy goodbye. You see we’ve already got her into a nice little girly outfit. And now I’m going to put makeup on her for the first time. Tonight, we're all going to get our first glimpse of Samantha. Then, we’ll open the task bar where you can superchat and have our girl here partake in some sissy tasks. You’ll notice that the tasks tonight are pretty tame. But, don’t worry, chat, if you stick with us on this journey, I promise they’ll get better as we go.”
With that, Morgan turned to me. She looked deep into my eyes as if our souls could connect through the look alone, letting me know that we were in this together and that she was here for me. “Are you ready, Samantha?”
“Yes, I think so,” I replied in best feminine voice.
Morgan spun me sideways and started applying my makeup. I could see chats pouring in out of the corner of my eye, but I couldn’t make out what they were saying. But every so often, Morgan would catch one and snicker or laugh. She replied out loud to a few.
“You’re a naughty one aren’t you, Banger,” she replied to one chat, “In due time, we’ll see.”
After about thirty minutes of brushes, pencils, lipstick, and gloss, she affixed the long blond wig she had finished styling earlier that day. It had a pink streak in it because we had discussed how Samantha's personality would a bit on the emo side. (I had sort of a thing for emo girls, and Morgan thought it would be fun to play into that.) Morgan squeezed my thighs. That was our signal that she was communicating to me as me and not me as Samantha.
“Are you ready to see yourself?” she asked hesitantly.
“Absolutely.”
She spun me around toward the laptop and I saw myself as Samantha for the first time. I was shocked! We looked like two girls sitting next to each other. She looked like a young Adele, and I looked a lot, astonishingly, like Maisie Williams. The chat lit up. New messages were coming in faster than I could read them.
This is going to be fun. She’s already got a great start.
Look at how sexy this bitch is!
She’s already got dick-sucking lips.
Can’t wait to see what’s under that skirt, girl.
I was mesmerized, staring at my own reflection. I turned my head from side to side, admiring Morgan’s work. How did she do this? Morgan started talking to chat while holding my hand underneath the desk.
“Okay, we’re opening it up, boys and girls. Who is going to start buying these tasks?”
Almost immediately, the first task was purchased. Someone actually paid $10 just to have me stand up and spin around. I did so and added a feminine little heel kick before sitting back down. Morgan laughed at that. Almost immediately after I sat back down, another person paid $20 just to have me “pick something up off the floor”. I couldn’t believe it. We made $30 in less than a minute. Morgan was right again. This was going to work! Morgan tossed a pencil on the ground and I bent over with my ass facing the laptop.
"Hold it there for a second," Morgan said. I held my bent-over position. Then I felt her hand on my ass again, slowly stroking it. Then her fingers inched lower and I could feel the hem of my skit starting to rise. I started to panic. Was she going to show my ass off already?!
"Just teasing chat," she said to my relief. "There's time enough in the future to see that. We're going to end today's session. But be sure to tune in at the same time in two days for Day 2 of transforming Sam into Samantha."
Morgan closed the laptop and looked at me with a lust in her eyes I had seldom seen before.
"Come here and straddle me, Samantha," she commanded.
I was a little confused at first. My Samantha character was supposed to be confined to the web show. That's what we had discussed. But the look in her eye was turning me on. What would be the harm in remaining in character a little longer? I gave my best sexy strut over to her and straddled her lap. It was a strange feeling, being the straddler instead of the straddled.
Morgan grabbed my face and pulled it into hers, shoving her tongue in my mouth and kissing me harder than she ever had before. I put my arms on her shoulders and without really thinking about it started grinding my hips in her lap. Her hands reached down, lifted up my skirt, and placed each hand on one of my pantied ass cheeks. She pulled them apart slightly and squeezed with an aggressive grip.
I felt vulnerable but sexy and horny in a way I never had before. One of Morgan's hands then found its way under my blouse and under the cup of my bra. Her fingers pinched and rolled my nipple, sending electric sparks shooting all around my body, distracting me just enough, I suppose, because before I knew it, I felt a finger on her other hand push into my ass. I reflexively, but unexpectedly, moaned in Samantha's voice. I kept my hips grinding as her finger worked in and out of me.
"Get on your back in the bed," Morgan instructed.
I did so, and she was immediately on top of me, kissing my hairless body up and down. My mind was racing with a million indistinguishable thoughts and feelings. Her mouth found my tucked-back member and I felt myself enveloped in wetness. Morgan licked and sucked, sending pulsing tingles bursting from my loins through my arms and legs. I was tensing, ready to cum. She sensed it and, before I did, penetrated me again. But this time it must have been more than a single digit because it felt bigger than before.
"Oh, fuck, Morgan. Oh, my fucking god!"
I let out a high-pitched scream and moaned as my orgasm filled her mouth. I heard her swallow and then come up, kissing me. She'd never kissed me after a blowjob before. I could taste my spunk on her lips and tongue. As we lay in the bed next to each other panting, I couldn't help but feel that something had just changed between us. Some new aspect of our relationship had just been released. And, for reasons unexplainable to me at the time, I couldn't help but feel giddy.
Morgan turned and looked at me.
"I think I'm going to like having Samantha around a bit more than I anticipated," she said with a grin.
We started planning out what the next few shows would look like with an unexpected energy. That night, I fell asleep with her spooning me instead of the other way around. Little did we know where this journey was heading.
Stay tuned for Part 2.
