A Sissy is Forged

This is my first go at writing. I've had a lot of fun writing this, I'm publishing this to see if other people enjoy it as I have. If it's a success, I'll continue the story. Hopefully, more chapters to come :)

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When I told my girlfriend, whom at that point I'd been with about two years, that I was interested in exploring my sexuality, she was more than accepting. When I asked her to use a strap-on on me, again she was all for it. And quite honestly, I thought a few times she should have been born with a cock based on how well she used the store bought version. Even when I told her I was wearing panties at dinner one night, she wasn't shocked. Instead, she asked if she could see the ones I picked out!

When I told her I was interested in crossdressing, things didn't go so smooth. I remember the conversation like it was yesterday and could easily recite it to you. All evening of it. But in the interest of keeping this story to a reasonable length, I'll spare you. She did, however, give me her blessing. With the stipulation that she didn't want to take part in my adventures with me.

Though pursuing this side of me was something I was very anxious to embark on, doing it solely on my own stung a little. But I agreed to keep it to myself. With my girlfriend working the night shift, I had plenty of opportunity to adventure without impeding on the agreement.

Over the next several months I fell in love again. I almost immediately realized, being a woman was what I was missing being a man! It was heaven in heels! I loved shopping new outfits, I had a flare for skimpy, sexy and slutty from the get go. Panties, bras and lingerie were my at home attire almost exclusively once my girlfriend left for work. Hair removal had a bit of a learning curve, along with painting my toenails. When it came to the makeup, I was a natural. Well kind of. I watched all sorts of tutorials, read articles on contouring and shading based on shape face and features. Highlighting the color of your eyes with different palettes, etc.

I enjoyed my girly time more so than I could have ever imagined. Every time I stepped in front of the mirror completely done up, I was in awe of who was standing in front of me. I was beautiful. At least to myself I was.

I got into quite the rhythm in the following months. I'd get home around 6, make dinner, shower and shave, then start into my femme transformation.

First, a pair of panties and a plug, I always took my time putting my panties on. I never knew how fast they'd be coming off so why not soak up some of the fun. Plus, I loved the view of my smooth legs and chastity being overtaken by whatever lacy set I'd picked out for the evening. Next was my bra and breast forms (32D). I was been blessed with a relatively petite frame (5'11" and 140lbs), especially given my genetic disposition. Luckily my girlfriend and I wore almost identical sizes so my selection was plentiful to be modest.

As I sat there in the bare essentials, I would always feel my anticipation grow. Exponentially at times. I'd tease myself by playing with my caged clit, admiring my breasts, their weight, their shape and the cuteness of the tiny amount of cloth covering them. Gosh, how I wished they were real! I loved the slight pressure applied by the bulbous glass plug spreading my cheeks and gaping my pussy. I'd sit there and grind against the pillow, which sat right in front of the makeup mirror so I could watch my hips rock and sway, to add to the sensation and really work myself up. I'd go almost to the point that I couldn't handle anymore and then I'd stop.

This moment always came with some regret. Largely because, FUCK ME! THAT FEELS SO DAMN GOOD! But additionally, now the tedious work of makeup began. Face, primer, light foundation, contour, highlight, blush, set. Eyes, primer, shadow, lashes (one of my favorite parts), liner and mascara. I always hated doing my eyebrows, that's how you know you need to improve on something in my opinion. Once those were up to snuff, next comes lipstick and a little plumper. I had a knack for just the right amount of makeup from the gate. This is generally a case where, less really is more ladies!!

Seriously.

I rarely wear jewelry beyond a necklace and some earrings. I love the dangly kind. They always just feel so girly!

Once I was satisfied with my fleshly appearance, it was time to get dressed. As I think I mentioned, I always had a flare for clothes on the sexy side. One of my favorites is black thigh high stockings with matching lace garter belt and a black body con sequin mini dress. The dress comes down to mid-thigh, just high enough to see a little skin between the bottom of it and the paisley-esque top of my stockings. After a few minor adjustments, it was time for my crown.

Putting on my wig has always been, and will always be my final piece. It's the icing on the cake. It has this "and now you're a woman" effect unlike any of the other "steps" combined. It's euphoric. Anyhow, I have a couple wigs to choose from. A wavy blonde with highlights, or a dark chocolatey brunette with bangs. I tend to go blonde more often than not. Blondes really do have more fun, trust me :)

At first, being en femme in itself was electrifying! I buzzed as my heels clicked wherever I went. I swooned at the girl in the mirror as she walked by. I adored every bit of my femininity, every second of it. After a week or so, I started taking pictures of the heavenly creature that I'd birthed. I strongly believe this was the beginning of Ms. Kassi's sexual prowess. I would run through different outfits, and poses. At first completely innocently. As my confidence grew, along came pictures of the more revealing variety. Instead of selfies in cute outfits and makeup I'd spent the evening applying, the photos evolved to POV shots of dildos and how much of them I could make disappear. I had plenty of them to choose from! My favorite I called "Bull." Bull is black, all of 9 inches that was wider at the tip than at the base and plenty girthy, with a huge pair of balls where the suction cup attached. I learned a lot when it came to patience with him. The first time I was able to get the head to pop past the point of no return was magical. I had him stuck to my bed frame and I was in doggy.

I had been warming up to him for a while, first with my plug, then a small pink similarly shaped dong, and plenty of lube. I pushed back on him and felt his tip press up against my incredibly moist pussy. I rested there for a second, almost as to indulge in the waning seconds prior to ecstasy. As I pushed back I could feel my body tense, I reminded myself to relax and reached between my legs to guide him to the promise lands. As the tip entered me, I dropped my hips and the next few seconds became a bit of a blur. It hurt in a way I hadn't felt before. A good way. My heart was racing, my arms were a little shaky, and I can't recall much as far as emotions felt, except that I wanted him deeper. NOW! I slowly pushed in a little, then back out. I was creating the cadence of how I wanted him to fuck me. I felt a slight euphoria come over me as I felt his enormous black balls press up against my thong that was cradling my throbbing clit and shaven sack. I hadn't removed the panties, I just pulled them off to the side (maybe for the cinematic effect). I looked over my shoulder to soak it in as I began to grind my hips, I could just see the base of the enormous synthetic cock spreading my ass cheeks. And it was beautiful. I could only dream of what the real thing felt like! But for now and in the coming weeks, I became a slave to the toy that owned my asshole.

I experimented with different positions, one of my favorites became being spit roasted, riding Bull and deep throating any of my other delicious dongs (flavored lube is great!). I grew hungry for him in indescribable ways. Insatiably at times. Our sessions grew longer and longer, very quickly. I learned to enjoy the time I spent with him inside me. Instead of enjoying the experience by jerking my cocklette to cum, I enjoyed working up a bit of a sweat, having him creep into my depths just to pull him almost to the point of popping out. I never came from anal stimulation alone, but I experienced almost a pride that I held the skill to work such a beast. If only a dildo could cum.

My girlfriend was timid but curious about my adventures after a few weeks. She said I was in a better mood more regularly, more energetic, she even said I was, and I quote, "more house-wifey" at one point. I couldn't deny it. I knew I was. And my Google search history was only there to support her argument. I loved the feelings I felt en femme. I had more zest, a different pep in my step. Or as I like to think of it, a different sway to my hips (hehe).

I started sharing my stories with her, and I can't say I think she was shocked by any of it. I told her I had been growing curious about what the experience of going out en femme would be like. I wanted to get more than just the bloggers attention. I wanted to have a girls night, maybe go out and dance and feel the freedom of being open to the world about who or what I was.

After much working myself up and self coaching, I told her I wanted to know what a real cock felt like, tasted like. More so, what it felt like to be a woman and please a man. We had a lengthy conversation about it, and we settled on if I could do it, she could too. I knew our sex life had suffered as a byproduct of my sudden need for all things girly, but it was something I knew I needed to explore. And I held the same feelings reservations when it came to her having a guy on the side. Initially, I was apprehensive, to say the least. All of those insecurities subsided when she suggested we find guys together.

"Are you serious?!" I inquired.

"Hun, I think it would be good for us," her response.

"How so?" I inquired again. I was excited, but slightly baffled by her initial reasoning.

After a short pause to gather her thoughts, and almost a look of growing apprehension, "I've been talking to someone else. I love you! I do.."

"How long?!" I interjected.

"It's only been a few weeks!"

I was completely caught off guard. I had no idea, and for a person that has the attention for details that I do, it was quite shocking.

"Babe, I love you. I've seen how happy you've been since you discovered Kassi. You glow; you beam when you are her. I haven't been here when you've been dressed, but I see her in you. Your walk has turned into a cute little strut, your closet is packed with dresses, skirts and lingerie. I even stumbled on the new black toy you've been hiding from me. And the amount of sticky panties I've been finding in the wash, wow. I started to feel like you weren't getting something you needed from me, I just needed a person to talk to about it. I told Amber from work about it after weeks of keeping it bottled up and she talked me into going out with her and some friends. That night she introduced me to him, and we've been talking since. He's a friend more than anything, but I can tell he wants more," and with a big gulp that could've been mistaken for a baseball being digested "I kinda do too."

She was filling the silence with complete reason. I was hurt initially. Then it started making sense. Our rhythm had shifted, even more than I anticipated, when I awoke the girl inside me. Our sex life went from several times a week down to maybe once a week. I was spending more of my resources (time, money, effort) on my girly endeavors, and enjoying them profusely, and less time being the man she had grown accustomed to. We talked all the time, but the tone had changed. It was almost a chore more than it was fun or inviting. We were drifting.

"Well...what do, what do you want then?" I began to stammer.

"I want you!" Her eyes were pinned on mine as she shifted to squarely face me, "I want to share this with you. I know I said I didn't, but I do. If it's something you really want of course."

"I do, but..." I hated being interrupted. This time I didn't mind.

"No buts baby! I'm yours and you're mine! I want to meet her. I want to know why you're so passionate about all things her. I'd like to know why I'm washing so many panties I've never seen before! We both know you aren't having a girl over when I'm at work."

We both laughed and my guard began to come down.

"Ok, but.." Interrupted again...grr!

"I said no buts, remember?" She reminded me.

"Um, I was just going to ask, what about your, uh, side guy?" I probed.

She snapped back, "what about him?"

"Well, how does this dynamic unfold?"

"We share him," she again pinned her eyes to mine.

I was startled by the suggestion. Once it settled I was even more so. My mind began to race again.

In the most delicate tone I asked "so he knows about me?"

"Yes," she spoke in a calm, collected manner. "I told you, I needed someone to talk to about all of this."

"Oh, I thought..."

"He actually wants to meet you too!" She impeded.

"Wait, why? How does he know he wants to meet me? I'm a little confused why the guy you're fucking...wait, have you guys had sex??" I probed and met her eyes with my own.

When I saw her head drop, I knew.

A few months earlier I would have been livid. But here I was, relatively calm, sitting next to my beautiful and loving girlfriend talking about her fucking another guy. Us fucking another guy! Together! I can't explain it, I can only tell you I was aroused.

"We can get back to that in a minute," I tried to match her calm, collected demeanor from moments ago, "right now I want to know how he knows he wants to meet me."

"You're not mad?" She looked up at me, with a look of shock occupying her otherwise carefree face.

"I can't be. I wish you would've been honest with me about your feelings though. I haven't been the same, we haven't been the same."

I paused, and she acknowledged.

"So, he wants to meet me?" I poked playfully.

"No. He wants to fuck you!"

I was floored and she could tell. So, she continued.

"About a week ago I came home from work early, before you woke up and took your phone. I was curious, and I figured you'd have some pictures of yourself dressed on there. I wasn't disappointed." A sly smile came across her face, "you're fucking beautiful baby!"

I'm not sure what blushing feels like from a physical standpoint, but the room temperature immediately increased 10 degrees.

"Thank you," I cracked with a bashful smile.

"I mean it!" She insisted. "I didn't know what to expect I guess. Then I saw the pictures and I understood why you were so engrossed by her. She's beyond pretty, her taste in wardrobe is sexy and fun, and I saw your videos with the toys too. Hun, you need some real dick! It'll make you forget about even your favorite fake cock!"

"Well I guess there's only one way to find out," I quipped with another sly smile.

"There's something else," she said with a little hesitation.

"Jesus, what else could there be?" I responded.

"When I saw the pictures and videos on your phone, I felt something. I didn't know what it was at the time but I knew I had to see more. I sent a few of the videos and pictures to my phone and deleted them from the conversation so you wouldn't find out. You want to know how John knows he wants to meet you?"

In a bit of shock, I just nodded.

"He's seen everything I have."

Again, I just sat there quietly as to propel her to continue. But internally I was all over the place. I thought Kassi was a complete secret. Nobody knew of her except the two of us. My phone was hacked and I was none the wiser. His name was John?! Wtf kind of parent names there kid something so generic?

She took a deep breath and continued. "John, the guy I've been seeing..."

"Fucking!" I interrupted.

With a scowl, she revised her phrasing "fine, John, the guy I've been FUCKING, knew about you before I saw anything. He'd made comments about how he wondered what you looked like, dressed like, even the color of your hair. Maybe he pushed me a little to find out for myself? Anyhow, I couldn't explain my feelings to him when I told him what I'd seen so he asked me to show him instead. I hesitated, but then I thought what the hell. He saw everything I saw. We watched that video of you crawling on the floor to that big, black toy, swallowing every inch of it with your cute little ass. Your moans made him hard, and me a little wet. We watched it like 5 times right then. I rode him like you were riding your toy. And holy shit! It was incredible! You ride that thing like a pro! He told me after we both came that he'd had a couple of girly boys back when he was in college and he wouldn't hesitate at the chance to fuck one again."

"That's kinda hot." I didn't even think before the words escaped my mouth. "He fucked you while thinking about me?"

"We were both thinking about you! I came so hard from I thought I might pass out!"

"Oh," I blurted.

I couldn't even form a full sentence. Perhaps my thoughts were short because all the blood was flowing to my now fully erect member. The imagery of my petite girlfriend being fucked to the point of nearly passing out, by a guy that wants to fuck me too! Oh. My. Fucking. God.

"Oh? That's it?" She spoke with surprised inflection.

"Uh, a million things are running through my head, sorry."

"Obviously, some are good! I see your little friend poking through your shorts." She shot back.

"Yes," very good I thought.

"So, what?"

"What's he look like?! Is he cute?! How big is his...you know?" I asked fiendishly as I flashed a bashful smile. "Do you think he can keep up with the two of us? When do we meet?!"

"Oh baby! We're gonna have some fun together?!?" She exclaimed as if she couldn't believe I was onboard.

I gathered myself slightly, smiled, and as if I still wasn't sure, I replied "if you think he can keep up with me."

It was the cutest smile I saw come across her face right then. Her eyes lit up, she kissed me, and she hopped on my lap only to say, "you have no idea!"

With that she hopped up and ran to grab her phone that was in the kitchen adjacent to where we'd been sitting. On her way back, she looked at me and I at her. Right then and there I realized things just got serious.

"What do you want to see first?" She asked on her saunter back to where I was still sitting.

"Huh? See what?" Slightly perplexed, I responded.

"We made something for you hun!"

"Oh. Surprise me then!"

"Ok!" She chirped. "First, I want you to be naked."

"Ummmm, why?" I responded.

"I want to see your body's reaction to what I'm about to show you. No clothing. Now please!"

I had no idea what to expect. I was swimming in my own thoughts. What could possibly be coming? Why do I have to be naked for it?

"I'm scared," I admitted.

"No need babe," she was calm. Reassuringly so.

I looked at her fiddling with her phone and decided what the hell. It's just the two of us. I stood up and peeled my t-shirt, then as I pulled the elastic on my shorts I realized I had made a mistake. When I woke up, I was naked. Too exhausted the night before (with Bull) to bother with petty things such as clothes. When I got up, I felt the need for something lacy and soft so instead of boxers under my gym shorts, I had white opaque VS bikini style panties on.

"Uh, I'm wearing panties. I just thought..."

"Perfect!" She responded. "Leave those on."

As my panties came into view I spun around to give her a view of my ass, and also to adjust myself without her knowing. I think she approved, as I felt her hand grab a handful of cheek and squeeze.

"Mmmmm," I moaned in my best impersonation of what I thought a girl might sound like.

"You really have a nice ass doll. I'm surprised you've never gone fag before." She laughed as the f word escaped her lips.