From Bro to Sissy Sub Pt. 02

From "Bro" to Sub Sissy Part 02

I had discovered my best friend dominating my wife and submitted to him myself. I solemnly pledged to trust and obey his commands, no matter what. The following morning, I awoke the with a hangover and pain all over from being tied up, fucked with dildo, and spanked. The first few seconds, I thought, it had been a bad dream; but, as I came to full consciousness, I recognized our guestroom, and I knew it was all real.

The alarm clock on the nightstand read 11:30. I usually wake up around 6 AM; even on the weekend, I wouldn't sleep much past daybreak. I got up with a jolt, wondering what Magnus--I mean Master Magnus... fuck--meant when he said we'd start to answer the question about becoming a "girlie" for him.

I sensed no one else in the house. Once out of the guestroom, I wandered from to room to room calling out, no answer. I knocked quietly when I came to the door of the master bedroom--perhaps they were still in bed, I thought. I heard nothing and opened the door slowly. Inside, the bed was neatly made and an envelope tucked between the pillows. The note inside read:

Dear Sissy Cuckold,

Master Magnus decided we should be apart for now. We are moving to his condo downtown, until his house is ready. I think this is for the best. I am so sorry we hurt you, but I have never been sexually satisfied, and the thought of you as a cuckold sissy, having to obey my new master, delights and arouses to me to no end.

Meanwhile, know Master Magnus will take good care of me, even if he has to abuse and punish me for our pleasure (ha ha ha). I cannot convey to you how much I've needed a real man to take me, or how satisfying it is for me to sexually please my Master. I will do anything for his pleasure; it feels so good, when he abuses me. The desire he has awakened in me too powerful to ignore.

Obey Master's instructions! Be a good sissy cuckold, so we can see each other soon.

Sincerely,

Flora

This didn't sound like her; I suspected it was dictated by Magnus. A business card with Magnus's scrawl on the back read: "Go here; talk to Roxanne; 2pm." It was past noon. I showered, got dressed, and drove downtown to "La Boutique"; a one-stop shop for "transition services" for transgender people. It included: a shoe and clothing store (with business and sexy attire), a full-service spa, a sex shop with toys and paraphernalia, and a counselling center, where I would meet Roxanne.

I spent time looking around the shops, until, Roxanne, a tall blonde buxom woman led me into a small but pleasant office with two comfy chairs. We made our introductions, and she got right into the matter.

"Our mutual friend Magnus has told me a bit about you. You've been friends a long time, but things have changed? Why don't you tell me, in your own words, why you're here today?"

"Well... umm..., Roxanne. Yes, something has drastically changed, and I need help figuring out how to proceed."

"Let me reassure you, first, that I am a licensed sex therapist, with a PhD in clinical psychology. I have known Magnus some years, and am aware of his sexual tendencies. But only you would be my client, and I value confidentiality and professional ethics. I will share nothing you say to me with anyone, including Magnus or... erm... your... uhm... wife?"

The awkward pauses signaled Magnus had told her some of the particulars of our situation. Until the previous night, I had no idea of Magnus's "sexual tendencies." He had managed to keep that from me. I gave Roxanne a substantially edited and less X-rated account of the events of the night before.

"Have you felt you were a woman trapped in a man's body? Or, just didn't fit into your body?"

"Well... frankly, no, not really. I have always identified as male. But sexually... I realized now; I had been neutered. Magnus said, when he had sex with my wife the first time, she might still have been a virgin. Does that make me a virgin... too? That means I had never penetrated her vagina deep enough to break her hymen! What does that make me?"

"Yeah, so... uhm... I wouldn't put too much stock in what Magnus said. That's not actually how it works, and it's highly unlikely, even if she'd never had sex; "breaking the hymen" is kind of an exaggeration. It's much more likely that Magnus's very large penis tore her mucus membrane, causing the bleeding."

She said this reassuringly, but it made me question how well, and in what capacity, she knew Magnus to be familiar with his penis size.

"But you raise an interesting question... regarding your feelings of inadequacy. Tell me about your sexual history." She went on.

"Not much to tell, really. Flora was my first and only, and we did "it"--or something, anyway--maybe a couple of dozen times in our first two years. I thought she hated sex, and I didn't really enjoy it much either. So, we stopped altogether about four years ago."

"Hmm, tell me about your masturbatory habits."

"Almost nil, I've masturbated in the shower on very rare occasions, for a few minutes and dribbled out a bit of fluid from my teeny, usually semi-soft, penis. I was just never really that interested in sex; that is, before last night. When other guys were trying to get laid or beating off to porn, I was happy coding or playing video games. I believed I was asexual."

"And... last night?"

"Last night my libido was on hyperdrive; I couldn't have gotten harder or more aroused. I never really looked at another man's penis. I got occasional glances here and there, sure, but none made an impression on me."

"Are you attracted to women?"

"Yes, I think so, but I realized last night, it's not really sexual. Like... erm... well my wife... Flora... she's gorgeous. Men check her out all the time. She has a beautiful face, a stunning body, but since we've been together, I've seen her nude just a few times; I never once tried to sneak a peek. I've never felt the kind of desire for her I did for Magnus's penis last night."

"Hmmm. So, are you aroused at the thought of having sex with a man?"

"Well... before last night, I would have said absolutely not, but I guess so..., or at least one man, anyway. It's not like I've had much exposure or experience,"

"When you imagine that, what role do you assign yourself?"

"Yeah, that part is suddenly crystal clear; I Googled it: I'm a submissive bottom."

"All right, in that passive position, are you male of female?"

"Again, yesterday, I would have known, today... I'm not so sure..."

"Okay. I have quick test, nothing conclusive, or anything... just to see what directions to explore. You're familiar with the Rorschach test?"

"Yeah... yeah, the... uhm... inkblots, right?"

"Yes. Well... this is like that, but more targeted. I'll flash some sexual images. For each, there are two questions: does it arouse you? and who do you most identify? Don't overthink; just your first thoughts, don't stop to consider what it means. Here's a practice one."

She nudged an e-tablet into my hand; an image of two burly hairy guys appeared, one on his back, legs spread wide; the other had his cock half-way up his hairy ass. I checked my mind; it didn't do much for me. I tapped, no. And, she asked if I was ready to continue. She tapped the screen and next image appeared. It was a woman on her knees, her hands bound, with a big man, not unlike Magnus, fucking her mouth, most of his big penis showing.

I was instantly aroused and tapped, yes. It was easy to pick with whom identified. It went on like that: different configurations, two women, two men, transwomen, transmen, trios, orgies, all conceivable combinations. I identified with the girl, especially in bondage. Images of manly looking gay men together, or women were not arousing, unless the bottom was androgenous. Roxanne confirmed what I surmised.

"As I said, Andrew, this is not conclusive or exhaustive, but for you, it does point in a very specific direction. Based on this conversation and these results, here's what we are going to do, if you agree, of course. We're going to do a little experiment: we'll give you a full spa treatment and makeover: massage, facial, full body depilation, and new hairstyle. We'll help you pick out some everyday women's clothes and lingerie. Don't worry about cost; Magnus will cover it.

"Just to be clear, it doesn't mean you are definitely transgender or that we should proceed any further. I'll make an appointment for you to see me in a week and we'll continue our conversation. In the meantime, try out what it feels like to be a woman. You can start just at home, but I would encourage you to go out in the world and see how comfortable you are in this new persona."

She asked if I had questions; I shook my head.

"Liz, are you ready for... uhm... Andrew." She said into the intercom on her desk phone.

"Drew... is fine," she made a note of it and guided me to the door.

"Sorry... Drew. Yes, full treatment, thanks. Okay, Drew. Liz will take you the rest of the way... Pleasure to meet you. Whatever you decide, you are really brave to go through it."

She hugged me; Liz was already coming for me, as I got out the door. She led me downstairs to a very nice spa. I started in the steam room, then a massage, done by a handsome young man, who I could see from the bulge in his chinos was well-endowed. Something I never would have notice before last night. Then a facial, waxing, and mani-pedi.

They cut my longish hair into a woman's hairstyle, then makeup. Liz helped me pick out some everyday outfits for life as a girl and some sexy lingerie. When I saw myself in the full-length mirror, I was stunned by how much I looked like a real woman.

Looking at myself, my first thought was a fantasy of myself on my knees, tied up, sucking Master's big cock. I posed sexily for the mirror, while Liz, my sprite-like guide encouraged with pretend catcalls. I was so excited; I insisted on leaving La Boutique as a girl.

As I got in my car, I was feeling fabulous. I had never had a massage, or any of the other things they did to me. I was eager to get home without incident, but it was past four, and my stomach growling; I had only had a cup of tea in Roxanne's office. I thought I'd slip into a fast-food place (maybe drive-thru) and eat in the car, so as not to draw attention. Then, I caught a glimpse of my girlie face in the rearview. I decided to go to the bar in the same stripmall as La Boutique.

I got out of the car and sashayed my skinny little ass, in my short mod dress with leggings and Doc Martens. I sat at the bar and looked around nervously, expecting someone to jump out of nowhere and shout I was not really a girl, but no one noticed or cared. The bartender, a hot woman effecting the look of a butch biker chick, shot me a quirky smile, as she handed me a menu and asked if I wanted something to drink.

I ordered a gin and tonic and a burger, and settled in to nurse the drink, while I waited for the burger. I furtively scoped out the scene, thinking maybe there were other "girls" like me. I was demurely observing everyone, when the young man who had given me the massage, walked in the bar, spotted me, did a funny double-take, and came over.

"Oooh, mmm, honey, you look just scrumptious! Yum, yuum!"

I turned beet red at the compliment and whispered my embarrassed thanks. I was afraid to speak out loud with my boy's voice. I had whispered my order to bartender. Because of this concern, I let him do most of the talking. His name was Jayden, a young, tall, black man, with sharp angular features; he was so sexy, muscular, but more gawky than burly.

An observation, I had never made about a man before, but it was like a switch had been flipped in my brain and now I was evaluating every man I saw. As I thought about this, I realized I hadn't really done the same with women. I would look at beautiful women as art unapproachable aesthetic objects, like the Mona Lisa. They might inspire awe, but no arousal.

I gestured to a booth in a corner behind the bar, where we could be more private, and maybe I could talk more freely. Without no real options, I told him about my situation and my recent discoveries. He was really sweet and genuinely interested. I was aroused by just his presence as with Magnus the previous night.

We ordered another round, and shared my burger and fries. He was so easy with me that my concerns relaxed. It was so weird to be out in public as a girl, with a hot man chatting me up. We exchanged numbers, he said "Sugar, call me if you ever want to hang... um umm!" As we parted, he leaned in and kissed me, not just a peck, but a passionate kiss. I let him for a moment, enjoying it, but turned away soon. It felt wonderful, but I couldn't possibly...

I got home totally dazed, my brain doing loop di loops all the way home. Scenes from the night before flashed through my mind, but with Jayden's handsome face and what I imagined his big penis to be like. I found myself fantasizing about him replacing Magnus in the previous night's events. At home, I couldn't settle on anything; at about 9 pm, I got a call from Master Magnus.

"Hey, little sis, how'd it go at La Boutique?"

"Really well! I had a spa treatment, new clothes and..." I went on and on until he stopped me.

"Shut the fuck up, faggot! Are you dressed like girl, right now?"

"Yes, Sir. I am." He had me take sexy pictures and send them to him.

I was wearing sexy lingerie, a pink see-thru baby doll with the matching frilly panties. I couldn't get over the feeling of the panties on my bare mound, against my tiny penis, and my freshly depilated ass, so much nicer than tighty-whities. I posed as women do for these pictures, took a few, including with my panties tugged down and my clitty dangling, and sent the best three.

"Damn, little sis! you look fucking hot. That last one reminds me; I am sending you a package tomorrow, call me when you get it. Are you ready to answer my question, yet?"

"I'm still not sure..."

"Well, sweetie, take your time, but you'll need to decide, before you see my whore again; not trying to pressure you, little sissy, but you need to choose, and she needs to know your choice."

"I understand, Sir. Couldn't I at least talk to her?"

"Aww, no, sissy. I'm sorry; you can't... just now, her mouth is full at the moment, ha ha ha!"

He must have moved the phone down because I could hear the gurgling sounds of her mouth being stuffed by his big fat cock... "Gwgh, glub, glub... gurg," she gurgled.

"Anyway, text me when you get the package tomorrow." He hung up.

Next morning, I woke up much less dazed and confused. I prepping for the work week ahead, when the courier brought the package. Eager to open it, knife in hand, I recalled he said text when the package arrived. I texted; in the three hours before his callback, I picked up and put down the knife ten times. I was dying of curiosity, but couldn't disobey his command. Maybe it was my Catholic upbringing or some submissive impulse in my personality, but having promised absolute obedience to him, I didn't feel I could deviate. I felt duty bound to obey.

"Hey, sissy cuck. Did you open the box?" He began, jocularly, when he finally called back.

"No, Sir!"

"Ha ha ha! You're such a good sub faggot! Little sis, are you my pathetic sub sissy-bitch!"

"Yes, Sir."

"Ooof. Fuck! Little Drew, your fucking slut wife is killing me, sis. I tell you; I just can't stop fucking this whore. My dick is sore from fucking the bitch, and she's still begging for more. I got her tied up in the bedroom waiting to get fucked again. What a nasty fucking whore she is! Damn! Does it make your sissy clitty tingle when I talk about the whore that way, cucky?"

"Uhm... yes, Sir." I felt really guilty and humiliated having him describe my wife this way, but his crudeness about her did make my clitty swell against its restraints.

"Open the fucking box, sissy bitch!"

Inside the box were: a tiny metal cock-cage (I had learned what it was at La Boutique); two butt-plugs, one medium, one XL, with remotes; an enema kit, and fake silicone boobs.

"Put the cock cage on, then put the keys in an envelope addressed to me, and post it in the mailbox on Poplar Street. Text me when it's done."

To get the cage on, I struggled with a problem I had never encountered--couldn't keep my peenie limp. I finally had to fold it and jam it in as hard as possible while closing the latch, and clicking the miniature padlock shut. It was hurting already, and I had a brief moment of resistance, but I knew Master was right. This was a way to exert total control over me; I welcomed it as a way to cede him my body, which was suddenly my driving concern.

This feeling was an impulse at first; a subconscious logic I had no immediate access to, but followed intuitively. The very erection that made my penis ache was achieved through his commands. Were I putting on the cage before last Friday night, it would have fit comfortably because I had never achieved the kind of arousals I was now brandishing.

"Start with the medium butt-plug. Wear it all day every day, except to clean it and do your business. And Drew, you've been such a good little sissy bitch. I'm letting you watch me fuck the slut wife, Friday night. Do you want to see me cuckold you again; show you what filthy whore she is, sissy faggot?"

"Yes, Master. I would love that. Will you allow me to suck your cock, Sir?"

"We'll see, cucky. Remember, you are not to cum, unless I give you specific permission. Pop that butt-plug in your ass, before mailing the keys." He hung up.

I did as he said; I cleaned myself up inside and placed the butt-plug in my ass. It was a little fatter than Flora's dildo, but much shorter. It felt good filling me up; fucked myself with it. But my clitty twinged and hurt, so I pushed the plug to and drove to the mailbox on Poplar.

Wearing a kimono over my baby doll, I dashed out of the car to post envelope, and ran back in the car, the plug moving delightfully in my ass. I was hyperventilating, when I got back home and giddy like a frat boy pulling off a cool prank. I texted Master, had a drink, and went to bed in my sexy new baby doll and set the plug on very low vibration.

Roxanne told me I should try as much as possible to live as girl for the week. Nothing was irreversible, and I should try to "feel" the experience as much I could, to gauge, which was more comfortable. The week after, I would reverse the experiment. The proposal had a logical structure to it, I was totally behind. But I was still nervous in public as a girl; at the bar, I was still riding the spa high. But now, I felt unsure, and feared getting caught.

Roxanne had made me an appointment with a voice coach. It was critical because my voice was my biggest tell. The voice coach, an actor and voiceover legend, worked out of his apartment. His office was set up like a recording studio, with foam eggcrate on the walls for soundproofing and two industrial looking mics on stands and assorted electronic equipment. I was pretty sure he already knew my story, and, in confessional mode, I blurted out the basic plot of my drama.

"Well, Ms... uhm..."

"Drew will be fine, Mr. Johnson."

"Well, Drew... what I do is performative. Usually, I train actors for specific roles, requiring either a range, accent, or emotion that is best drawn with the voice. I adapted my techniques for use in the transgender community, and it works rather well. Today, when you leave here, you will be able to "perform" a woman's voice convincingly. However, it will not be transformative. Have you ever done any singing, my dear?"

I had sung in church choir and his technique was entirely amenable to me. We sang songs together (hymns of all things) and he modulated the pitch, so I had to keep reaching higher, beyond my natural range. Then he had me speak some complicated sentences in my voice but trying to sound like a woman, without sounding like comic imitation. Then, he had me sing the sentences, and try again to say them in a woman's voice.