From Bro to Sissy Sub Pt. 03From Bro to Sissy Sub Pt. 03


Part 3

Drew Makes a Choice

Author’s note: all characters represented in this story are fictional and at least 24 years of age. All sexual contact is consensual, among fully aware and willing adults.

The whole night I had heard my wi… I mean His slut… in the next room being ravaged by nearly two dozen men. I heard them not being very gentle with her; there was a lot of slapping and screams from her. I couldn’t believe I had been there, and all I did was blow strangers who were about to, or had just, fucked and ejaculated on my w…, I mean, Master Magnus’s slut.

Finally, back home, I was still disturbed. I got ready for bed, but couldn’t go to sleep. I turned and tossed in my big empty bed and couldn’t shut my mind off. I alternated between trusting Master’s main premise and noting inconsistencies in his story. He promised I would be watching just him with Flora; sent three different costumes, and picked the maid outfit; then the cock-and-bull story about friends coming suddenly from out of town, when clearly the event had to be planned.

He claimed not to be blackmailing me with Flora. But he withheld her from me to force my decision. What else could that be but blackmail? Yet, he was my best friend since forever, my “big brother”; he had battled to protect me countless times. I counted on him in every situation. I promised to trust and obey him, in front of Flora, and felt especially obligated by that promise. And, what about her? could I totally lose her, if I didn’t choose as he wanted?

Had she been there, I would have talked it through with her, until I knew what to do. I missed her terribly in so many ways.

The next morning, I got up groggy from the lack of sleep, my jaw aching from sucking all those cocks. I heard nothing more from Master Magnus the whole day. He had never returned my call for a talk the previous day and not okayed me contacting him, when he put me out after the bukkake gangbang with his whore.

I was losing my mind. I spent the next three days in a state of total distraction. I had finished the week as a woman, and had generally loved it. I had to go back to being male for a whole week, and was dreading it.

I was still hairless from the waxing and lasering, caged, and plugged, but I got dressed in men’s clothes, with white cotton briefs, which suddenly felt alien and rough to my smooth skin after the frilly silky panties I had been wearing. I was really not liking it; by Wednesday, I called Roxanne to meet for a counselling session. I asked if it was okay to dress like a woman for the visit.

“Of course, honey, it’s all about what’s most comfortable for you,” she said. We settled on four O’clock.

I had trouble not using my feminine voice. When I tried to speak in my old voice, it sounded harsh and weird to my ear. I did not use the fake tits, which, honestly, was the only part of my experience I did not like. They were really convincing visually, but for the wearer it was like a heavy rubber vest that caused tremendous sweating. As I took it off before leaving for the appointment, I cupped my flat chest and squeezed, wondering what it would be like to have real breasts. I pinched my nipples, which sent a twinge to my ever-aching caged clitty.

I called Jayden to see if he was working and wanted to have a drink after my appointment. I knew the dangers of this, probably not a good idea, but I needed companionship, and he was the only one, besides Roxanne, with whom I could speak openly about my situation. He was very happy to hear from me and delighted to meet for a drink, but he pressured me about the decision. I told him again that I had not really come to a decision, but that I couldn’t really go any further than friends having drinks until I had Master’s permission.

“Why…?” he scoffed and pleaded, “he wouldn’t even have to know. Doll, I wanna sex you up!” My emotional response to his interest made me think I should proceed transition. My little clitty pinged against its cage, and I had a warm feeling all over. The idea that this handsome 24-year-old virile man was so interested in a confused sub-cuck sissy bitch, made me feel pretty and desirable. I finished getting dressed and went to my appointment. I was so excited to be in panties again. Roxanne was as kind as she had been the first time.

“Hi Drew, tell me about your experience this past week.” She greeted me effusively.

“Well, Roxanne, I am positive I want to proceed with feminization and almost ready to commit to the gender-reassignment process.”

“Tell me a little about the feelings that prompt you toward that path.”

“Yes, I have felt so much happier in my everyday interactions with the world this past week. As a woman, I just feel a calmer spirit, which slows me down and makes me feel more confident. I love when men look at me and smile, or just check me out, and look away when as I catch them. As a man, I’ve never felt sexually desirable to anyone, Ankara Escort even to Flora.”

“Drew, have you ever heard about imposter syndrome?”

“Hmm, hm…”

“It’s where one is in a situation, where you feel like you are just pretending.”

“Yes, yes! I think that’s it, but in reverse, right? I’ve been pretending to fit the role arbitrarily assigned at birth. But, so much in denial I never once questioned it.”

“How have you felt this week going back to projecting a male identity?”

“Uhm… that’s exactly it; I’ve felt like an imposter. When I left here last time, I felt a little like that in women’s clothes, but once I adjusted, I wasn’t afraid. Now, I feel that way in men’s clothes. I feel like someone is going to find me out, discover I’m not a real man. I think I probably felt that way all along, but tuned it out, which is why I never had much of a sex-drive.”

“Okay, Drew. I think it’s clear we should at least proceed on this path. We should plan on seeing each other once a week for a while. I will refer you to a colleague of mine, Dr. Harris, who will help on the medical side of the equation, if you choose that route. What we do here is about the emotional, psychological and social aspects of transition, but I can’t provide prescriptions, or—thinking down the line—surgical intervention.

“Just be assured we can go a long way before anything is irreversible, if you take it slow. How about your other… erm… situation?”

“Oh, I wish I was as clear on that as I am about the gender transition. It’s tangentially related, but it’s a really important tangent. I feel like I had been desexualized, maybe asexual, all of my life. And now, because of Magnus’s intervention, I feel all horned up all the time… and everywhere I go, if I wanted to, men signal their sexual interest in me.

“I walked into a coffeeshop the other day—I was wearing these realistic fake boobs and a low-cut blouse—and at least eight guys were smiling and staring at me. I could have easily taken one of those men home and let him have me. As a guy, there were zero women willing to be taken home by me. And now, my clitty… sorry, my penis gets hard in a light breeze.

“Anyway, my problem: I know just like I know I want to be woman, that I am submissive. The thought of Magnus and his magic penis drives me crazy; I am ready to be dominated by him as a woman. So, it should be easy, right? But no! Master… I mean… Magnus…”

“Hrrmmhm, hrmhrm, sorry,” she snickered, then apologized.

“No, no, I get it; it’s ludicrous, but there you have it. He wants something from me I can’t give him. He wants me to do this, for him… I really want to do this for me! Though it seems just semantic, there’s an attitudinal difference. If I tell him I am doing it for him, then I am lying, and if I tell him I can’t do it for him, I wouldn’t have fully submitted to him.”

“Have you talked to him?”

“That’s the other problem; he has been keeping me at arm’s length, I think, to give urgency to the decision, but for a misguided reason; I think he believes I may have second thoughts about feminization, but I don’t. He’s also keeping my Flora from me, though frankly, she’s likely in on it; she is so totally submissive to him now.”

“Well, Drew. One thing I can do is act as an intermediary. As I said, our sessions are totally confidential, but if you want me to talk to Magnus on your behalf and give me permission to share some of our discussions, perhaps I can facilitate a resolution. I’ve known Magnus a long time, and can reason with him.”

I wondered exactly what their relationship was about, but was happy to give her permission and let her do what she could to resolve the situation. Our session over, we said our goodbyes, and I went off to meet Jayden at the bar. The same friendly, butch bartender was there she gave me a big wink, and I was able to give my order aloud in my woman’s voice.

Jayden came in about ten minutes later, and we moved to a booth near the restrooms, as the after-work rush was starting, though the bar never got that crowded. He kissed me hello, again in that delicate, but firm sensual way. I nudged him back gently, though I would have loved to just melt into that kiss. We sipped our drinks slowly as we were in constant conversation. He pausing mostly to make moon eyes at me and tell me how sexy he thought I was.

I had to pee desperately, and walked into one of the ungendered single user bathrooms behind the bar. Peeing with the cage on is an adventure, especially at first, but I was getting pretty good at it, though sometimes, if I wasn’t careful enough, I could end up pissing all over my clothes. Since I mostly wore short skirts, I would pull them from the hem toward my chest, before I squatted hovering above the toilet with the lid up.

I was in this precarious posture, when I heard footsteps and realized I hadn’t locked the door. I was somewhere mid-hover with Ankara Masaj Escort one hand holding up my skirt and the other a wad of toilet paper ready to clean up my clitty cage, and inner thighs, which invariably got wet. When I saw Jayden’s handsome face peer through the swinging stall door.

“Damn! You look fine even when you piss. Can you help me with this?”

Before I could finish wiping or figure out how to stop him, he was through the door, holding his massive cock out of his pants at me. I instinctively opened my mouth to the biggest cock I had sucked so far. Jayden’s cock was huge, and shaped like a corkscrew. He sank it down my throat, and I fell back from my hovering position directly onto the unlidded toilet.

I tasted his sweet sweet precum and smelled that intoxicating musky masculine scent that drove me crazy. I was in a swoon as he began to pick up speed. For a moment, I tried to hold him back, but he was pushing my face into his crotch. I wanted him so bad; desperate to suck his cock; though I knew I probably shouldn’t. Looking up at him, his face was ecstatic. I was so happy to bring him pleasure. I nodded my head and let him know with my eyes that it was okay to go ahead and fuck my face and cum down my throat.

As he built up speed, I could feel the pressure of his spiral cock as it spun into my mouth and down my throat. My asshole squeezed down on my plug at the thought of what it would feel like in there. He was throat-fucking with the intention of coming in my mouth. I waited anxiously to taste his cum, the first man I would make come in my mouth after the disappointment of Mr. Johnson coming on my face. And all the guys I had blown at the bukkake party under strict instruction not to come for me.

I didn’t have to wait long; he pushed deep down my throat. I was so glad to have had all that practice as he spurted wads of cum down my throat finishing off on my tongue to let me taste his delicious salty spunk. I lapped up at his cock while wiping and licking up the last of his cum, making his big head slimy with it, then cleaning it off with my tongue. I held myself up with his hips and pulled him into me. He let me play with it for a while; I held it down my throat and suckled on it until it was too sensitive for him.

He pulled out and walked out of the stall; I heard him washing up in the sink. I got up, wiped my bottom, and readjusted my skirt and panties. When I walked out, Jayden was standing smiling like the cat that ate the canary—though maybe I was the cat in this scenario.

“Jayden, honey. You can’t do that. You know my situation! Fuck! You have such a nice cock, I loved sucking it. You’re the first man to come in my mouth! You know that? And, you taste so good!” I licked my lips still tasting his cum. “Shit! I’m in so much trouble. Fuuuck, Jay! I have to go!”

“C’mon, baby!” He reached out and kissed me hard, and I let him and returned the kiss. I was already in so much trouble. While kissing him the taste of his cock and cum was even more present for some reason; I loved that we were both tasting it. But I worked my way free of him and practically ran out the door, and out the bar toward my car.

I ran right into Pam, whom I’d met at The Boutique, while we both got facials. She was like me (someone who realized their gender dysmorphia later in life), but much further along in her transition. She was scheduled for the big surgery within a month. She had discovered soon after marrying a woman that she just couldn’t play the role of a man. She told me it was hell, and she felt so miserable and guilty about failing her ex-wife.

Pam could see I was distressed and walked me to my car asking what the matter was. I tried repeatedly to put her off, saying it was nothing, but she wouldn’t buy it. I let her in my car with me, and we sat there and talked. I finally told her what had just happened, and she began to get the wrong idea about Jayden.

“No, no. I don’t mind what he did. If I was free, I would have led him into that bathroom and blown him on knees.”

Pam was taken aback, I could tell. Her transition was much less a sexual. She had said she decided to be celibate through her process, so as not to conflate gender identity with sex and overcomplicate things. Probably sound advice for me too, but with my libido raging, it seemed impossible. She felt she was lesbian, but she did not have the personality of someone who blows or gets blown in a public restroom, under any circumstances.

I told Pam the rest of my story, the details of which I could see shocked and maybe repelled her. But she was a real trooper letting me relate what to her must have sounded like horrors. She was older and more conservative in her social and political beliefs, but she cut the whole issue down to basic principles.

“Drew, honey, a promise is a promise, if you said you’re going to do something, you must carry it through, or explain why you can’t Ankara Olgun Escort to the person you promised. Jayden should still not have done that, even if you would have agreed; you felt you couldn’t because you ‘belong’ to this other man. Jeez!”

“You’re right, Pam. I know. But I’m sure it was my fault; I’m sure I was sending him all kinds of messages because I couldn’t help it; I can’t say I didn’t subconsciously leave that door open; he did just what I wanted, but knew I wasn’t supposed to. I am really attracted to him. But I shouldn’t even be meeting with a man for drinks.”

“You are right there, sweetie. But, you know, … we’re all human; we make mistakes; as long as you own up it… that’s the best we can do. Honey, I gotta go! Here’s my card call me if you want to talk, or anything.”

Her card read, “Pamela W. Winslow, Mediator.”

Talking to Pam clarified some things for me. I got home, showered and was priming myself to call Master Magnus and tell him everything, when I got a text from him with a video file. “Watch this, sissy cuck bitch!” was all it said. I clicked on the file and saw it was about an hour long. So, I turned on the tv and linked my phone to it. The file was called “brutalslutwifebukkake,” I had an idea of what I was about to see, and steeled myself for it.

Having been there, I knew the video must be heavily edited because it lasted more than three hours the other night. I was quite rattled by the prospect of what I was about to watch. So, I got up and fixed myself a tall whisky. I sat cross-legged on the couch with my finger hovering on the play button on my phone and gulped my Scotch.

The video opened with a shot of the closed door to the room with the sign “Slutwife Cum Whore!” with an arrow pointing in. The door opened and the camera scanned the room, which was empty, except for a large ornate armoire, opened to reveal whips, chains, a whole panoply of BDSM toys and tools. In the center of the room, stood a padded leather-bound platform about two-by-three-foot central platform with ledges for legs and arms a foot long each with attached restraints.

Flora was strapped to it on her belly, in kind of all-fours position, her arms strapped behind her, bent at the elbows, forearms tied together. I could see marks and bruises both old and new all over her once pure alabaster skin. The shot switched to a mounted camera and focused in on her beautiful face. She looked tired but radiant. She was looking up and smiling a broad blissed out smile, like the believers on the cover of a Watchtower magazine.

Then Master Magnus’s head came into the shot. He kissed her tenderly and sweetly. She opened her mouth and let him explore it. He held her cheek in his massive hand like a gentle giant as she leaned into the kiss and closed her eyes and purred. Suddenly, he jerked her head back by the hair, pulled her away from the tender kiss and slapped her face with a clap. Her smile faded, when her face came again into focus, and tears sprang quickly from her eyes.

“Oooph, ooow, Sir. Please…”

“Please, what? My whore!”

“Please can you just use me alone tonight, Master. I love what you do to me so much, Sir. But… must we have to have that faggot loser watch us, Sir? I prefer it when we’re alone and you can do as you please. Why can’t that cuck faggot leave us alone, so you can concentrate on me.”

“Aww, tch tch, my little cumslut whore. I have enjoyed using and abusing. You are a truly a marvelous whore. But tonight’s lesson is not about your cuckold sissy husband, after all. It’s about access, and what access I can grant, when I want.”

“Hm… wha…”

“I’ll explain, but let’s talk about our good friend, the loser faggot cuck. I explained to you: our thing is not romantic. There is no time when we are going to live as married… talk about our day, raise a family, etc. That’s not who you are to me. I brought you here, away from the cuck, to train you for my purposes. When I’m not around, you’ll want companionship. The little sissy faggot loves you, even if she’s not really a man.

“I don’t care, Sir. I really resent her pretending to be a man. To be near thirty and find out, after six years of marriage, you’re still a virgin because your husband’s micropenis was too small!”

“It isn’t his fault, whore!” He looked away in contemplation as he pondered.

“You know something? …it might even be mine…”

“What about the lesson, Sir?”

“Oh yes, ahem… tonight, my slut, you are going to learn a valuable lesson and—knowing what a cumwhore you are—I know you’ll enjoy it. Remember when you submitted to me, I said I would share you with others?”

“Yes…, Sir, but I thought it would just be us and the cuckold, tonight? I don’t think I’m ready, Master.”

“Oh, you’re ready when I say you are ready, whore! That was the plan, but a friend of mine, actually you might remember him, Lou Mason—now, he goes by… L. Maxxxon. He makes a particular kind of porno to sell on his website. This morning, he called to see if I could suggest a star for his latest. The slut he had lined up backed out last minute, lucky for you.”

“Huh, you are making a porno of me, Master?” She seemed frightened, but intrigued.

“Yes! But don’t worry, your face will be digitally disguised in post-production.”

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