“A Sissy is Forged” – KassiSmart7
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!!
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.
“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.
I’d never been called a faggot before. In the truthful sense anyhow.
“Oh? I’m glad you approve! I’ve been doing butt workouts to improve my shape and firmness for a few months now. I think they’re working!”
I had my shorts around my ankles now. I stepped out of them as more instructions came out.
“Now, what I’m about to show you, it’s him. John said it will help you feel, uh, I think he used the phrase, ‘cemented in your new role in our relationship.’ If you don’t mind, I’d like it if you watched this video on you own. Lay down and enjoy.”
“I guess. Ok.”
Without any more words, she stood up, kissed me with a peck, handed me her phone and walked down the hallway into the bedroom. I couldn’t see anything except that the camera roll had been opened, and a video was pulled up. Play. Wait, pause. Do you really want to see whatever this file holds? Yes! Kassi does! I do. I do.
I heard my girlfriends voice, then a whisper of what sounded like a man but nothing visual had populated the screen yet. Jet black, with only the hum of white noise momentarily, then he spoke.
“Hello Kassi. My name is Johnathon. If you’re listening to this, congratulations. You’ve taken a big step forward, more on that later though. I understand you have made a lot of changes in your life recently. You’ve made changes that were necessary for you to continue on the path best suited for you. I don’t know a lot about you, beyond what Brie has told me. Shown me even. You’re very skilled in the art of physical transformation. Not that you were much of a man to begin with. You take pride in the time you spend as a woman. It really does suit you. You even seem to know a thing or two about handling a man sized cock. The way you put on a show, how you brush your hair out of the way while you struggle to put more and more cock in your mouth to provide a better view, even the way your little shave clit flops helplessly between your legs as you impale yourself with, Bull? Is that it’s name? That’s cute.” He snickered as though someone had told a mediocre dirty joke.
He really knows a lot about me, I thought. My clit was uncaged this afternoon and I wished it wasn’t. His voice was deep, not too much so, but certainly more manly than my own. His words and how confidently he spoke them made my clit ache as it stirred inside my panties. More so, my pussy was tingling, and moistening, practically begging for him to have his way with it. With me. I hadn’t seen any part of him, as it was still purely audio, yet I still couldn’t help but let my mind wander.
He continued, “however, don’t let your special skill set go to your head just yet. You have a lot left to prove sissy boy. The fact you’re listening to this now, probably wearing some frilly panties, with a growing appetite for my grown man cock in your mouth, tells us something. Would you like to know what that something is, faggot?”
With that, there was video to the recording. Initially it was out of focus and whoever was operating the camera was moving it. When it came to a stand still, the image immediately came into focus.
“Yes, you sissy bitch, that’s your girlfriend down there on her knees. She looks like she’s rather enjoying sucking my fat cock, wouldn’t you say?”
He’s not wrong I thought! Her hand while it was tiny, looked even more so wrapped around the base of his long, girthy member. I gauged how big he was by how much of his cock disappeared before her gag reflex kicked in. I’d figured 8-9″ and fat! Double what my I had standing at full attention now. She was incredible at giving head! She took her time, she genuinely enjoyed it, her mouth was always warm, wet and eager to suck the life out of a man through his penis. I guess she was my ‘mentor’ in that sense. I wanted to make a man feel how she had made me feel so many times before.
Why am I so fucking aroused by this? I quizzed myself. That’s your girl, on her knees, working hard to milk another mans balls! I had no idea, and I didn’t care. My inhibitions fled when he said my name. I needed something occupying my pussy. My fingers would have to do. I quickly paused the video long enough to roll on my tummy and pull my panties aside and slid two fingers deep into my very adequately self-lubed pussy. Every plunge of my fingers matched the rhythm they had paced. I was knuckle deep and I couldn’t get enough! I watched intently for the next few minutes as his now saliva covered cock was gagged, spit on, taken to the back of my girlfriends skull. Willing my fingers deeper and deeper. Finally I figured if I adjusted my position to more on my knees and removed my undies I could go deeper, just then his voice came on again.
“Hey faggot! You ready for this?”
I guessed he was talking to me.
“Babe, I’m going to cum!” He grunted.
She looked up, directly into the lens and grinned an evil grin the Grinch would be proud of and spoke, “cum in my mouth baby! Please, cum down my throat!”
She never let me cum in her mouth! She certainly never swallowed it! She always said, I don’t like the taste! Screw it, I thought as my fingers took back occupation of my steaming and insatiable fuck hole.
“Yeah baby, right there! Fuck! Fuck! Oh fuuuucccckkkkkk! Unnnngggg!”
His manly groan, and the fact he just dumped a solid load into my girlfriends mouth had me on the edge of exploding myself. I’d never been so uninhibitedly aroused by anything in my life! Deeper! Harder! Faster!
Stop. Ouch. God! Leg cramp! Leg cramp!
Shit! I was almost there!
“Now,” he began to speak to me again, “I told you earlier, you still have a lot to prove. Remember? Good girls get rewards, Brie was a good girl today. And she’ll be further rewarded later with this big boy in her fine little ass. Do you want to be a good daddy’s girl..?” He paused for a moment, I did! I did in a bad, bad way!
“There’s a phone number in your phone. It’s under ‘Daddy’ I had Brie put it in there. It’s my phone number. Text me with your response. Then, you’ll get your first task.”
The screen went black and the ‘play’ button reappeared where his cock had just been.
Where the hell is my phone? I wondered, kicking myself a little. Ah, gym shorts! Yes. I rolled over, grabbed my phone and went straight into contacts, D.
💕Daddy💕 as it was in my contact list.
Cute. Ok, now what…text him? That seems uninspiring. These panties are kinda cute. And my butt does look pretty good in them…hmmmm.
I got up and pulled them up and over my now shrunken clit. Taking my time of course 😉 I opened my phone to the camera, video, and placed it on my favorite perch for recording Kassi and hit ‘record’.
“Daddy, please, you know I want to be your good girl,” I said seductively. The close up of my panty clad ass barely contained by the teensy-tiny scrap of lace fabric slowly swaying in front of the camera, putting on a little show. I reached around and slapped my nearly bare right cheek being sure to leave a red mark, “ooooooh, Daddy! Is this what naughty girls get?” I cooed. “I want to be whatever you want me to be, Daddy.” I blew him a kiss as I turned to hit ‘stop’ on the recording.
I played it back to make sure I fit the desired effect into the 30 second clip. I approved. We’ll see what he thinks.
A couple minutes passed and no response. Has he seen it? Did I try too hard? What is taking him so long?
I heard the doorbell just then. I’m in no shape to be answering the door, I thought. I was still in my panties! Only my panties! As I went to run to the bedroom my phone buzzed. I picked it up and read the message.
Message: It’s me. Answer the door princess.
My mind went blank and I couldn’t move. Just then, Brie emerged from our room.
“Well, are you going to answer the door?”
She had on an absolutely stunning black, lace top, pleated bottom babydoll. I was gawking, and she called me on it.
“I know, I look good. And guess what? As soon as you answer the door, you can have yours too sweetie,” she bribed as she dangled a matching ivory pink teddy in front of me.
Pink!! My favorite color!
I bit my lip and weighed the options. If I don’t let him in, she will. Then what? Am I ostracized? I couldn’t risk it. I decided the reward was worth the plunge. I tried my best to cover myself, but with all of the excitement I had to be showing my hand a little.
As I reached for the deadbolt I realized I still hadn’t seen any of him besides his legs and obviously, his impressive dick. I wonder what he looks like! I felt a little more at ease thinking about those possibilities.
I unlatched the deadbolt and stepped behind the opening door to shield my panty wearing ass from the world outside. I peaked around the corner of the red painted door and saw him. He was handsome! Like really handsome! At 6’3″ he had a few inches on me in height, elsewhere too. His build was gym going, but not buff. Somewhere in the 180-190 lb. range. His hair was short, brown but a light brown. He wore it combed to one side, clean shaven with a friendly Paul Walker-esque smile and gorgeous green eyes.
“Hello beautiful,” he greeted me before I could say anything. “Where is she?”
“Who?” I inquired.
“The woman I came here to see of course.”
I wasn’t sure if he was talking about Kassi or Brie, then she broke the momentary silence from the other room.
“I’m in here baby!”
“May I come in?” He asked.
“Of course! Cum, cum anywhere you like.” I smiled. I was still incredibly aroused, I never got to cum myself, and seeing him here now, unsure of his intention, made my libido kick into overdrive.
“Thank you. I will,” he sternly walked past me and then turned in slight disbelief. “Nice panties by the way. Dear, won’t you go give our little girl her outfit for tonight?”
Brie was his right now. He hadn’t been in the house for two seconds and she was already at his beckon call.
She strutted past him and up to me, still next to the front door and handed me the teddy. “I hope…we hope you like it!” As she leaned in to give me a smooch on the cheek.
“We have something else for you too. But first, come. Put that on and sit with us. We have a lot to talk about,” her voice sounded distant, friendly. Not girlfriend-ly.
I was quickly realizing what he meant when he said I had a lot left to prove. They were a thing, I was simply a play thing to be enjoyed. I didn’t so much mind I guess. But I was already certain him and I would need some, uh, him and I time. My mind turned towards the teddy in my hand as I embarked on my journey toward the laughter in the other room. I held it to my chest, no boobs yet. Dang. I shrugged it off and pulled the garment over my head. As it fell into place I felt at home. The pink lace chest was form fitting, but not tight and very, very soft. It even had little daisies embroidered into it. The waist, where it tapered inward sat perfectly on my hips and the pleat flowed gracefully just below the bottom of my butt cheeks. I twirled mid stride as if I were a ballerina and came to rest, now in the same room as Daddy and his queen.
She looked really comfortable on his lap. They both smiled as they saw me twirl, and I’m sure they caught a nice view of my shapely buttocks. I didn’t care. I felt a freeness come over me the moment it fell onto my shoulders and draped over my hairless body. I was at home.
“Hi,” I giggled. “Nice to meet you, should I go pour us some drinks? Dinner maybe?”
“That would be nice,” Brie responded. “He drinks whiskey, you know what I’ll have.”
I wasted little time taking on my first duty, I hope he notices I pondered as I sashayed into the kitchen. I wasn’t gone but a minute when Brie poked her head in.
“Are you okay?” She questioned.
“I couldn’t be better!” I matched her whispering tone enthusiastically. I wasn’t entirely sure why yet though.
“When you serve him, he likes to be masculinized. Flirt, make sure he knows you’re into him. I saw you playing while you were watching that video, you’re DEFINITELY into him. Take your panties off. You won’t be needing those tonight. I’ll be the one making you guys dinner. He wants to get to know you better. Go. The glasses are going to start sweating!”
I did exactly as she said. I pulled my panties down and tucked them between my elbow and ribs as I carried our drinks into the living area. As I came into the room, he immediately greeted me with his generous smile. He hadn’t moved from left of the two the arm chairs facing the kitchen. Luckily, there was a wall impeding his view so he had no idea my ass was bare underneath my new favorite teddy. I handed him his glass, and as I turned to take my seat to the right of him I dropped my now vacant panties.
“Oops!” I said playfully as I positioned my smooth, supple ass to be right in plain sight as I bent over to pick up my dirty laundry.
“That’s ok. What took you so long beautiful?” He asked with a jester like tone.
“Oh, you know, girl talk. I’ll be right back, I’m going to go toss these in the hamper.” I knew his eyes were following me, and I loved it.
I returned and took my chair next to his. I’d learned proper form in one of my many ‘study’ sessions. As my derrière planted itself into the cushion, I crossed my right leg over my left, letting it dangle a bit and adjusted my slip accordingly.
“You’re quite exquisite, you know that?” He palmed my smooth moisturized thigh momentarily and continued. “I’m sure you know by now, you won’t be my first girly boy. You present yourself different than the others though. Elegant, to a degree. I appreciate your effort. Genuinely.”
He motioned to the left side of his chest, he was genuine. I blushed again, lightly, but I didn’t have anything to say, so I filled in with a thank you.
“Elegance is rare. Not to be cliche, but a real woman in the streets that’s also a freak in the sheets is even more of an endangered species. Your girlfriend possesses similar qualities. I’m sure at one point you were well aware of that.”
He must know we hadn’t had sex in a couple of weeks, I thought.
“She is really something special,” I was drawn to this man, but my mind wasn’t populating responses, I just wanted to listen. Perhaps he doesn’t want my opinions? I continued to ponder in between brief phrases.
“When dinner is over, and I’ve had my fill of this shit whiskey, I’m going to fuck her. In your house. In front of you. Do you know why I’m going to fuck her?”
He paused. Shit. Am I supposed to have an answer?
“Because that’s what men do! They fuck! We make…erm, excuse me. I make babies, I kill so my babies eat, I work hard so my babies thrive!” He paused again, this time to take a swig of his whiskey.
“Do you know where faggots like you fit into that chain?” His inflection on the phrase ‘faggot like you’ again made me stir beneath my slip.
“No, where do sissy faggots like me fit in?” I prodded, completely unsure what was coming next.
“You are the mistress.” He spoke without hesitation. “You were put here to suck my man cock, to fuck when and how I choose, to be my cum dump, and luckily for us both, you can’t make babies. The mistress has fringe benefits as well. She gets to shop, she gets to pamper, she even gets gifts. Anniversaries, I liked how you sucked my cock clean last night type of gifts.”
I had nothing. Where is the pen? Where do I sign? Mistress Kassi. That has a nice ring to it! I think he could read my facial expression, I was eager.
Just then, I thought, “why do you keep calling me beautiful? I’m not wearing any make up, my boy…everything…is on full display, I’m barely concealing my little friend underneath this gorgeous teddy. Thank you, by the way! I love it. But still, why?”
He leaned back in his chair, I could see he didn’t have an answer for me immediately. Slick talker didn’t…
“Because it’s not solely your appearance that attracted me, or brought me here tonight. Actually, your decision is the reason I’m here. You see, you’re not in female form, yet here we are. I bet if I pulled my cock out right now, you’d be on your knees within milliseconds trying to milk a load from my sack. You were once a pleasure of a guy at one point, I’m sure, but now you want to be a woman. That’s why I call you beautiful. It radiates from you. The skin care regiment, the constant shaving, plucking, and waxing. The time you account for out of your daily routine to apply your makeup. The hours and hours I’m sure you spent perfecting your walk, the way your butt jiggles but is firmly planted in place, how cute and happy you looked twirling around earlier. May I see another twirl?”
I hadn’t taken my eyes off him in what seemed like forever. His words resonated within me, they were all true. He knew all that after only spending 30 minutes in the same room as me! I couldn’t wait for him to make a move.
He’d made me into his bitch in less time than it takes to get through TSA on a regular day! I wonder how else we could be waiting for dinner to be ready.
“Of course I’ll spin for you, Daddy.” I had one thing on my mind, get him hard.
I uncrossed my legs, and stood up. My knees were a little unstable, probably from sitting cross legged so long. I patted out my teddy and flatten it in the front. I gave him a twirl and then some. My panty less crotch fully exposed, my ass bouncing and twirling for only my Daddy to see. I twirled and twirled and twirled some more! When I began to get dizzy, I decided it was time to take a seat. This time, in his lap.
I grabbed his now empty glass from his hand, and set it on the end table. He looked up at me, smiled and he knew exactly what I wanted. He opened his arms and it was like rolling out the welcome mat. I planted my pussy right where his belt met his khaki colored shorts. Right where the base of his cock should be. There was definitely a bulge! He grabbed my hips and rocked me forward as to reposition me. His hands felt great right there. Now I was two feet on the ground, ass buried in his lap, not giving a fuck about any of it. He started rocking his hips, and using his strong hands to create a mimic with my hips. I was grinding myself slowly but more and more firm with every revolution of our hips. I started to feel him stiffening as I came to the 4 o’clock part of our clockwise motion. I couldn’t help but push harder against the few millimeters of fabric separating him from me. If only that fabric weren’t there!
Well, he didn’t say I couldn’t suck his dick I thought to myself. Only he was going to fuck Brie tonight. As I watched.
“Hold on, I need to go get something from the kitchen,” I told him as I stood up, separating myself from him for the first time.
I walked into the kitchen where Brie was, her eyes met mine as I entered the room but quickly drifted just down to where my little cocklette was creating a tenting effect in my evenings attire.
“Looks like someone is enjoying themselves!” She laughed. “Dinner is going to be ready in about 20 minutes. I’m…”
“I want him,” I interrupted. “I want him now.”
“Oh?” She paused briefly. “Do you think he knows how you feel?”
I didn’t think there was any doubt, but I bashfully turned my gaze toward the floor and replied, “I think so. I just gave him, I sorta gave him a lap dance. I just wanted to see if I could get him hard, it worked! Now…but…”
“But, what hun?” She interrupted my stammer in a motherly voice.
“I don’t know. I don’t know how to make the next move.” I cowered.
“Awe, my little girl has a little crush! Isn’t that adorable! Here,” she turned to where her purse was still propped up on the kitchen, “I told you we got you something else, didn’t I?”
“Oh, yeah!” I perked.
“We were going to wait until after dinner to give it to you, but I can see you’re already pretty excited. So, here,” she turned back toward me, extending a little black and pink striped gift bag.
“What is it?” My voice cracked from a little over excitement. And I’d never ‘practiced’ my girly voice for such an extended period of time.
I looked into the bag and pulled away the tissue paper. I gasped when I laid eyes on the contents.
“You didn’t!!” I exclaimed.
Brie smiled, “no. He did, baby.”
I’d been telling her for weeks that I wanted to get into more frequent and permanent chastity. Anal orgasms had always eluded me, due to the flexibility, and easy removal of my silicone chastity cage.
“Is this the CB6000?” I chirped.
“Yes dear, we special ordered a pink one just for you.” She smiled again, “we hope you like it. First though, you need to call off your little friend that’s, um, poking through?” She kind of giggled and gestured towards my rock hard 5″ penis pitching a tent south of the border.
How did I ever please her with this thing? It’s not big, it’s not even average! How do I get it to go down while I’m so excited though?
“Babe, I don’t know how to get it soft,” I whispered. “I normally have some fun with Bull, or you. Neither of those seem like options at the moment.”
“Um, do you want my help?” As she leaned in to whisper.
I nodded enthusiastically.
“We have a guest, so you’ll have to be quiet!”
I nodded even more enthusiastically.
“There’s cucumbers, we can sneak into the garage…”
“Hello, am I interrupting something ladies?”
His presence startled us both and I dropped the present at my feet. He looked down, as it clinked on the tile floor. Breaking the surprised silence with a grin, “you dropped something. Shouldn’t you be picking it up?”
“Oh, of course! I’m sorry, you just..”
“No need to apologize. I came in unannounced, I should know better than to interrupt women talking,” he returned.
Brie laughed, then caught herself. “We were just discussing his, uh, her little problem here.” She pointed to my tiny erection.
“We can cage that later. Right now, you,” he turned his gaze to Brie, “come speak with me in the other room.”
He sounded stern. That was the first time I’d heard that tone from him.
“I guess that leaves you to finish up dinner,” she gave me directions of what needed finishing up, and just before she breached the doorway to the living area she added “cucumbers are in the grocery bag next to my purse” with her adorable smile.
I tossed the salad, pulled the chicken out of the oven and was finishing up dishing of the last of the potatoes au gratin when I heard a loud WHACK! from the other room.
What the hell was that?! I thought. I poked my head through the door, my eyes nearly popped out of their sockets when I saw them. Daddy had moved over to the couch, and Brie was draped over his lap from the right (I was onlooking from the left). Her skirt was pulled up, and from what I could tell, and her panties were nonexistent.
The slap I heard must’ve been a spanking! Ooooh, I wonder what for? The thought was obviously too much to handle as just then my knees caved slightly.
Her head moved ever so slightly up and down, up and down. Was she? As quickly as that thought filled my head, it was confirmed, she flipped her strawberry blonde hair up and out of the way. She was sucking his dick! Perhaps she flipped her hair for him to get a better view, perhaps they knew I was watching. I don’t think either of them cared, quite honestly, neither did I. I looked on completely mesmerized for what felt like an eternity! His face said it all, completely relaxed, completely at home. His right hand now stationary between her spread legs, by the way her hips were thrusting upward into it, he had to have buried his fingers inside her.
There I was cowering in my ivory pink lace teddy, body completely hairless, rock hard and more than a little jealous of my girlfriends current position. I was starving, and not for the food that had just been prepared. I had to do something.
I didn’t think another thought before I walked out of the kitchen and into the room they were in. My knees were unstable, my stomach was in knots but I walked in with a mission.
“Dinner is ready, you two!” I announced.
Brie stopped briefly, and Daddy lifted his head from his relaxed state. Neither of them seemed even slightly out of comfort by my presence.
“I’m already having desert baby,” Brie sultrily offered.
“I can see! It looks…delicious!” I shot back as I continued towards them.
She had already wrapped her lips back around his swollen tip by the time I opened my mouth to respond.
Daddy laid his head back and casually spoke, “you should try some! Babe,” he tapped on Brie’s head, “ride me.”
“Mmmm, you sure baby? Mmmmm your cock feels so good in my mouth though.” Brie countered between mouthfuls of his beautiful cock.
“I want to cum home,” he persuaded, as he pulled her hips towards him.
That’s all it took! She kissed the tip of his cock one final time as she repositioned. She unbuttoned her blouse and tossed it in my direction falling just short of my feet, followed quickly by her white bra and skirt. As she threw her leg over him I realized exactly how big he was. She couldn’t have both knees on the couch without letting him enter her first. She grabbed his shaft just below the tip and guided him into her glistening wet pussy. As he entered her she gasped quick short breaths and groaned incoherently. It was a familiar groan from our own adventures, but of a different tone. More carnal. More animalistic. He was sliding in so easily, and she was soaking up every second of it. I couldn’t take my eyes off the two of them. I was salivating, I had been reduced to a puppy at their feet, begging for scraps, I had been morphed and molded into their bitch in an afternoon.
I took a seat in the arm chair I’d gotten out of minutes earlier and watched in silence. Their rhythm had a beautiful melody to it, she had him engulfed in his entirety and she was spinning her hips as a hula dancer would. There was a sloppy wetness to their gyrating, the sound effects were intoxicating and filled the room. As he pushed farther in, she pushed harder down. I was familiar with the body language and the hardly discernible “oh fucks,” and “oooh baby’s” from my time spent with Bull. I wanted him inside me.
“Baby,” I softly broke the sex in the air, “do I get any desert?”
They kept at it almost as though nothing had come out of my mouth. I didn’t want to interrupt twice, so I turned again to silence and wishing it was me instead of her being impaled ever so agonizingly slowly. Just then Brie broke their series of fucks and shits and other colorful vocabulary describing how amazing they felt to one another with, “I think she’s ready baby.”
“Good. I’m almost there,” Daddy grunted.
“Mmmm, I’ve already gotten there,” Brie said as her voice peaked and came back down. She turned to me, without disturbing their cadence and asked me a question I will never forget.
“Do you want his cum?”
It was both startling and welcomed. I was a nomad that stumbled onto an oasis in the middle of the desert, a smoldering fire that was offered a relentless downpour, a bitch in heat and service had finally been offered.
“YES!” I proclaimed, “yes please!”
I was on my knees between his feet within seconds, her pussy leaving her slippery glaze behind as she began to speed up the pogo-stick action she was performing on his cock. It was literally happening inches away from my face! I had an idea to help speed things along, and no inhibition left to dispute it. I reached up and cupped his hairless balls with my fingers and as he let out a familiar groan, he was close. I lowered my face in about an inch of the two, the scent was incredible, and opened my mouth to welcome his balls into my mouth for the first time. Brie adjusted her depth to work the tip and allow me space and his nugget slipped right in. It was quite the mouthful, and that was only one! I batted it around with my tongue trying to cover every millimeter of his salty sack and sucked with a variety of gentle then firm. The river of juices cascading south into my mouth was heavenly!
How could this be any better, I wondered. Just then all knew got tossed out the window. I felt his weight shift away from me, I released his balls and looked up. Brie’s leg was swinging over my head and she was darting to get out of the way fast enough. I was still in my dutiful position and looking up at the most gorgeous rock hard glistening cock I’d ever seen. I didn’t get to enjoy the view for long. Before I even had a chance to gasp at it in all of its glory I was autonomously ascending it. ‘I knew my purpose, I wanted nothing in the world more than to fulfill my purpose,’ filled my brain as I now looked down on his mighty tool. I closed my eyes, and opened my mouth and guided it into my cum receptacle of a mouth. It was warm and slippery and it found the back of my throat in no time. I gagged slightly, and backed off knowing there was no need for showing off.
My lips slid up dragging my tongue along the huge canal beneath it until I reached the tip. I flicked my tongue underneath the head and swirled it around the purple head as I made a full loop, I stopped to pay special attention to the area just below the slit my treat would shortly be bursting out of. I glided, and caressed, and sucked his swollen head until I felt him place his hand on the back of my head, I knew what was coming. I slid my hand off his shaft and down to his balls and grasped them snuggly, his entire length seized and released as my mouth began to fill with his nectar. The first spurt hit me square in the tonsils, I gagged and coughed as a little escaped my mouth. I regained my composure quickly as he kept shooting, and shooting. The salty, clover-y sauce was thick and warm as it filled me to the brim. As soon as he completed emptying himself inside of me, I released his balls and slid my mouth over the tip, releasing it. I looked down, and then up at the two of them, still with a mouth full of seed. They peered at me with questioning looks, I grinned and lightly smiled and gulped every drop of it down.
“That’s a good sissy,” said Daddy.
Brie leaned over him and kissed him as passionately as she’d ever kissed me. I grinned again and went back to admiring his half erect monster.
“Oh, there’s more,” escaped me softly as I laid eyes on the spunk that had initially escaped me. I ducked my head to the right, below the doubled over shaft as I grasped it with my left hand and lifted it back to its upright position. I stuck my tongue out and starting at the lowest point of his sack, I licked every inch, and then some, all the way back up to the peak. I took his tip back into my warm goo coated mouth one last time, just to be thorough. He shivered tremendously, releasing his hold from the back of Brie’s neck.
“There’s plenty more,” Daddy managed between heavy breaths.
“Mmmm,” I responded. I think that was good enough. After all, his cock was still being milked by my mouth.
Brie and Daddy laughed as they soaked in the moment, I released him to laugh with them. I looked up at the two of them smiling down on me with Chester cat grins, I knew I had done well. I felt a pride wash over me as I began to blush again.
The next few hours were wonderful! We ate dinner, had a few more drinks. At one point Brie and Johnathon told me they’d been fucking basically every day since they were introduced. I was eating her pussy on a relatively regular basis still! How many times did she meet up with him and come home to me to lick her freshly fucked pussy? The thought turned me on! I thought his cum tasted slightly familiar, hehe.
That was the point where the night turned. It turned into a confession, of sorts. Daddy told us about his first sissy, and how she would fuck him like she was trying to get pregnant every chance she got. Literally, wake up, bang. Shower, bang. Car, suck his dick, and on arrival, bang. Etc. Brie gasped and made a darting devilish look towards me. I had big shoes to fill. It would be my pleasure to try my mightiest!
Brie came up next, hers was light hearted and quite cute. She explained how from the first time she saw my panty drawer, she knew that was just the beginning. She knew I’d look pretty in makeup, that I’d gravitate more towards women’s clothes than my birthed genders, she could tell when she used the strap on I would graduate eventually to the real thing. And most of all, she just wanted to share it with me. She stopped at one moment and looked at Daddy, then at me, she just wanted to share it with us.
My turn. I didn’t have that much ‘experience.’ I didn’t have a lot of wicked stories to tell, or hidden feelings I had been saving up. The only thing I was curious about was when I was going to have him again. So I asked. My question was met with something I wasn’t sure I could handle.
Daddy calmly leaned in and in a low, passionate tone, “When you’re ready to give yourself to me. Fully. I don’t half-ass anything, you’ll be 100%, or you’ll be none at all. I expect the best, and reward nothing less than that.” I saw Brie nodding as though the two of them had already had this talk. “When Brie tells me you’re ready, we can discuss this matter further.”
That was it for me, the lack of clarity sent my brain into a tailspin. What was he expecting from me? And at 100%, could I give it to him and make us both happy? What was the reward? Even more importantly, what was the punishment? My clitty still ached from all of the days excitement, and the thought of spankings from Daddy’s hands began to make it swell again. I stood from my seat at the table, my satin and lace teddy fell and brushed my legs softly, reminding me that I was wearing it, and began cleaning up. Daddy’s and Brie’s glasses were empty, I better make myself useful I thought. Keeping myself busy would surely ease my discomfort. I refilled their drinks, then took their plates and silverware. I excused myself and went on to wash the dishes and tidy the kitchen while they shared some alone time. I caught Daddy admiring his view of my shapely backside a couple times, but nothing more than an exchanged smile or two came of it. When the dishes were done, I realized it had gotten late. Daddy appeared to be getting ready to go, I could tell he was saying goodbye by the way he and my girlfriends lips and tongues intertwined near the front door. I groaned at the thought of going to bed, but tomorrow was coming sooner than I was ready for it. They broke their unification as I sauntered into the room, I didn’t say anything as I passed through. I just waved as nonchalantly as I could muster and said, “see you next time Daddy!”
“Goodnight beautiful,” he responded. I think I picked up on a little wink in there too.
I grabbed my new chastity device as I breezed by the coffee table and continued on my way to my room. I hopped in the shower, and turned on some music. Tonight’s theme: Ke$ha, love her! I heard the front door close as I was getting the water just right, and Brie entered the bedroom shortly after. She came into the bathroom, she had taken her clothes off, all of them. She leaned up against the pedestal sink and looked at me differently. Almost bitterly.
“He gave me instructions,” she spoke softly but with a slight sternness. “You can have me tonight, or you can have this.” She pulled out our strap-on harness from behind her back, but the cock in it wasn’t one I’d seen before.
With a playfulness in my voice I responded, “you know what I want, and it’s neither of those.”
“Where did that toy come from?” I continued.
“Johnath…Daddy bought it for me a while back. He is very big, much bigger than anything I’d had before. Anal came up some time ago, I was reluctant due to his size so he bought this and a plug to help prepare me. I never used the dildo, but don’t tell him. You know I don’t like those things.”
“So have you..” I started.
“Yes, it hurt like Hell too! Once I got used to him, I…I…” she reminisced.
“What? You what?” I inquired.
“I’ve never cum so hard in my life. I’m a bit of a masochist though, you know?”
I frowned and looked down on my shriveled little cock and thought, ‘damn, how were you ever lucky enough to lock this beautiful woman down?’
My silence must’ve prompted her to speak again, the sternness returning in her voice. “You can call me Daddy tonight,” she flashed her devilish grin again.
I opened the shower door, my answer was clear. I, for the second time today, had accepted my new role. I fancied pleasing him, I needed to have him, there was no way around it now. I imagined I was back in the living room, bare ass under my negligee.
I felt Brie’s leg brush mine as she stepped in behind me, her voice whispered, “ready Kassi?”
I again let my actions speak as I bent over, hands bracing myself on the wall, letting the water run down my back and poked my little bubble butt into her playfully.
Laughing ever so gently, my strap-on wearing girlfriend responded, “I guess so!”
With that she placed the tip of her synthetic cock in the crease just above my boi pussy, and briefly left it there. It wasn’t until then that I realized how big it was. It occupied more than its share of real estate! I tingled as I slid slightly forward, positioning my hips farther down and ass, begging to be fucked, farther in the air. It dropped right into place, the head was at my door and knocking, who was I to not let it in? I shimmied my torso so approach was at the correct angle and eased my way back. I savored the pressure as it gently pushed against my love button, as the tip began to open me up I felt her start to push from the other end, FUCK ME. My entire body quivered as the tip plopped in beyond the elastic like band just inside my honeypot. HEAVEN. The shaft was just like I remembered him, thick at the tip, tapering thinner towards the base. I felt it meet some resistance a couple inches in, Brie did too. She began to pump, softly out, firmly back in, hoping to get a little deeper with each of the latter. Successfully. I had nothing to compare my current state to, it felt absolutely incredible! My pussy was stretching, this cock didn’t appear to be any wider than Bull, but he felt completely different.