Sexual Sissy Awakening

JASMINE: Have fun.

She texted me the address. I checked it on my phone and saw it was a fifteen-minute walk.

Still wearing my panties and pantyhose, I stowed the room key in my wallet, and went for a stroll.

For fifteen minutes I pondered what I was about to do.

Fifteen minutes also to admire the beauty of downtown Toronto.

Fifteen minutes to observe the diversity of people.

But then suddenly, I was there.

I paused.

This was it.

Showtime.

It was one thing to fantasize about this.

It was a very different thing to do it.

I considered turning around and leaving, but my need to obey Jasmine, my desire to explore this feminine side of myself, and the curiosity of an adult theatre where most of the action wasn't on the screen, had me opening a door, going up a flight of stairs, and then needing to make another decision.

To my surprise, there were two turnstiles. One for gay films and one for straight films.

I had no idea which to go through, and each had a slot to put money in.

After some thought, I chose the straight one, as it seemed a little... well... less... gay.

I put the coins into the slot and walked in. I wandered around and found doors for movies, and then a hallway. Curious, I walked past the two movies and walked down the hallway to see six small rooms with doors. Four were open, two closed. In one that was open, I saw a small television. Clearly these were rooms for jerking off, or perhaps having sex. I also noticed there was a hole in the wall between the room and the hallway.

I then walked back to the two movie rooms, took a deep breath, and walked into one.

A movie was playing on a large screen television, not an actual movie screen like I'd imagined. Two men were sitting on opposite sides of the room watching a girl on the screen sucking cock. I stood in the back and watched for a moment, before I walked out and checked out the second room. It had the same setup, a dozen chairs on each side, and this one had four men. Two pairs of men were each side by side on opposite sides, and as I got closer I saw a younger man was stroking an older man's dick on one side, while an older man leaned down to suck a younger man's dick on the other side. I glanced up at the screen to see a brunette getting spit-roasted.

I don't know why, but I took a seat right across from the older man currently sucking cock, and the other two men were directly behind me.

I attempted to watch the movie, the brunette was hot, but my eyes kept glancing over to the grey-haired man who was sucking dick. When the younger guy being sucked glanced my way, I hurriedly turned back to the film.

The door opened and closed, but I didn't look back, since I wasn't sure what the etiquette was... although staring at a blow job was probably rude.

I glanced over a few more times, my cock hardening, as I couldn't help but wonder what it would be like to suck a cock.

"First time here?" a voice from immediately behind me asked.

My eyes went wide while I nodded, "Yeah."

"Come sit with me," the voice said.

I turned around and found the two men who were behind me were gone, but a guy around my own age was sitting there wearing a suit. "Um, okay," I said, as I got up, glanced at the blow job again, and went to sit beside the new man.

"Hi, I'm Mike," he said, extending his hand.

"Bill," I said, shaking his hand, which seemed strange in such a location.

"You from here?" he asked.

"No, New Jersey," I said.

"Explains the accent," he said.

"Yeah, I just arrived here today."

"I see," he nodded. "Top or bottom?" he asked.

"Curious bottom," I answered.

"Have you sucked cock before?"

"No."

"Want to see mine?" he asked.

"Yeah," I said, really excited to see his dick.

"Pull yours out too," he said, as he fished his cock out.

"Okay," I nodded, as his cock was suddenly free and looked to be about seven inches, "but I'm wearing pantyhose."

"Oh, interesting," he said without judging. "Just pull your pants down, then."

"Okay," I said, doing as he instructed.

"Nice," he said, as he moved his hand to my hard cock and rubbed it over my panties and pantyhose. "Go ahead, you can stroke mine."

"Okay," I repeated in a daze. I had imagined sucking cock, oddly I hadn't imagined stroking one, or having mine stroked.

"Get me nice and hard," he said, as I wrapped my hand around the first dick ever that wasn't my own. It was awkward, sitting side by side as we were, but also exciting. It was so hard. A couple inches longer than mine, and also thicker.

"You have a nice dick," I said, as I slowly stroked it.

"Thanks," he said.

For a couple minutes I slowly stroked him to complete hardness, he slowly rubbed my cock through my pantyhose. Then after that time while I spent more time admiring his cock than watching the brunette getting double penetrated, he invited/ordered, as he took his hand off my cock and placed it on my head. "Go ahead Bill, bend down and suck my cock."

"Here?" I asked, as I looked around and saw the older guy was still sucking the younger one.

"Yes," he said, "here is the perfect place," as he guided me towards his cock.

A rush of adrenaline coursed through me as my mouth was summoned to his dick. I mindlessly opened up and took his fat cock inside.

"There you go," he groaned, as I wrapped my mouth around his dick.

I can't explain it, but just like so many first time cock sucker stories as well as many forums, as soon as I had his dick in my mouth I felt... at home. Alive. Excited. It felt like this was what I'd always been supposed to do. Suck dick.

I began to bob slowly, getting used to having a dick in my mouth, although bent sideways was awkward.

"Oh yeah, there you go," he groaned. "Nice and slow."

"Mmmmmmmm," I responded, wanting to let him know I acknowledged his words, but didn't want to stop sucking his cock.

"Such a natural," he said, as I continued slowly bobbing. After a couple minutes, he said, "Why don't you get down on your knees? It'll be a lot more comfortable than the position you're in now."

"Good idea," I said, quickly sliding down off the chair and onto my knees, allowing my side to stretch, which had begun to hurt while I was sucking the way I had been.

I moved between his legs and took his cock back in my mouth. This position felt so much more comfortable... and natural. Like this was the position I was meant to be in.

"Oh yeah, suck my dick," he groaned, as I resumed bobbing, going a little faster in this far more comfortable position.

This was even better. It felt so natural... so good... as if this were why I was born: to suck cock. I know it sounds ludicrous, but that's what I felt. I brought my hand to my pantyhose-covered cock and began rubbing as I bobbed.

"Oh yeah Bill, you're a natural cock sucker," he moaned, as I was taking over two-thirds of his cock into my mouth. Being called a cock sucker made my cock flinch... since it was a term that always turned me on when I read it, and especially when I listened to sexy female voices calling me one while I was watching those hypno-sissy videos.

I moaned on his cock in response, suddenly wondering what this cock was going to feel like in my mouth when he came. I wondered what it would feel like to have his cum shooting into my mouth. I wondered what it would taste like. Well... I was about to find out!

"That's it, take more and more of me," he groaned softly.

As odd as it sounds, I was in a self-contained, all-encompassing zone. All that mattered was his cock. I continued bobbing for a couple more minutes until he warned, or perhaps it's better to say announced, "Here it comes, cock sucker!"

I had to have that load! That cum! I bobbed faster, and a dozen bobs later I heard him grunt, and I felt his cum shoot into my mouth, slide down my throat, and warm my belly, even as my cock twitched and a rush of adrenaline coursed through me.

"Yeah," he groaned, as I swallowed every drop.

Once there was no more cum left, I wasn't sure what to do next, so I just kept slowly sucking him.

"That was great," he said, and I backed off.

"Thanks," I said, unsure of what else to say.

"You're a natural," he said, beaming down at me.

"Thanks," I said again.

"I need to go," he said.

"Oh yeah," I nodded, standing up extremely awkwardly, reminded my pants were around my ankles.

"Nice to meet you, Bill," he said, as he got up and headed out.

I stood there, realizing no one else remained in the small theatre.

I pulled my pants up and headed out. I thought about going to the other theatre, the one that wasn't 'straight', and I also considered visiting the gloryhole, but my head was spinning from what I'd already accomplished. So I headed out and strolled back to the hotel with the taste of another man's cum lingering in my mouth.

.....

Back at my hotel, I texted Jasmine a rather lengthy report.

ME: Mistress Jasmine. I went to the theatre. I ended up sucking my first cock. Swallowing my first load. Was called a cock sucker for the first time. I have never felt more alive than I did when I was on my knees with a cock in my mouth.

ME: It was exhilarating; it was completely intoxicating; it was life changing. Okay... enough hyperbole. Simply put: thank you. Eagerly waiting to know what to do next. Pet Cock Sucker Brittany

I got undressed, except for the pantyhose and slightly stained pink panties from my own pre-cum and sat in bed with my laptop open and clicking on one of my favourite hypno sissy scenes.

I was only a couple minutes into it when I received a text.

I grabbed it, and was disappointed to see it was only from Emma, which made me shake my head at my own pathetic-ness (I'm not sure that's a word, but it fits for this).

EMMA: Settled into the hotel yet? How was your flight?

I decided to phone her, and we chatted for a few minutes while I watched a hypno sissy video on mute that focused on sucking cock. God, there were just so many different sizes, shapes and colours of cock. Pussy was pussy... it all looked almost identical to me; but cock... no two were alike.

And not just their size (although the length can vary so much), or girth (thin cocks, fat cocks), or shape (straight, curved up, curved down, even curved sideways) or colour (black, white, and a variety of other shades), but also the way cum explodes out of a cock (like a rocket, in streams, or even just weakly oozing out).

Just as we were finishing up, I got a text. I assumed it was from Jasmine. I resisted looking at it until I hung up with my wife after we both said 'I love you'.

I checked the text. Yes! It was from Jasmine.

JASMINE: Two choices for tomorrow. One... more cock sucking (a minimum of three); two... a visit to a salon to femme you up. Of course, you can choose number two first, and then do number one, or I suppose you could get your fill of cock first and then get feminized. I need to know if you wish to include option two, since I have tentatively booked you at a spa I used to go to.

I didn't even hesitate, even though I likely should have, but the hypno sissy videos I had been watching only enhanced my subconscious decision to choose option two.

ME: Mistress Jasmine although I definitely want to suck more cock, the idea of being feminized is too big a temptation to resist. Please tell me when and where.

JASMINE: 5 o' clock. I'll send the address in the morning. Be sure to be wearing pantyhose throughout all your meetings. Good night, sissy.

ME: Thank you, Mistress. I will obey. Have a good night.

JASMINE: PS: No touching your clitty. If you're going to be my submissive pet, you must learn self-discipline.

ME: Of course not, Mistress.

I resisted watched more sissy videos, since they would only get me excited. So instead I watched sports highlights and went to bed... excited and curious about tomorrow.

.....

Surprisingly, the next day flew by quickly... and I ended up at a salon just a couple blocks from the scene of last night's sordid affair. (Well, I guess a proper sordid affair would include passionate kissing and embracing instead of just a blowjob, but you know what I mean.)

Being in an unfamiliar city, an unfamiliar country, made this appointment a lot less stressful. I walked in and said simply, "I have a five o'clock appointment." Presumably they sissified guys all the time, since the receptionist didn't even raise an eyebrow.

She took my information, then led me down the hallway to a room. She said, "Get completely naked and climb under the blanket."

"Yes, ma'am," I replied, even though she was substantially younger than I.

I got undressed, and lay on the massage table. I waited a few minutes before, to my surprise, a man walked in. He asked, "So you want the full monty?"

"Yes please," I nodded, Jasmine having explained what was about to happen to me.

"All right," he said, as he pulled the thin blanket off of me. "First, I'll wax you."

"Okay," I said.

"Lucky for you, you're not too hairy, but this will still hurt," he warned, as he went to a table.

"I understand," I said, having seen 40-Year-Old Virgin... although other than my legs, I didn't have a lot of hair on my chest or anywhere else.

He returned and applied warm wax to my back, ass, and to my surprise, some oozing way down between my ass cheeks, and my legs.

After waiting a few minutes, he said, as he put stuff on my back, "On three."

"Okay," I said.

Then for the next five minutes I suffered some serious pain. It made me wonder why women did this. It also made me wonder what childbirth could possibly be like. Women... they have it a lot tougher than we men, if I can still call myself one.

He even did between my ass cheeks, which I discovered was a pretty sensitive area... as was the back of my legs... which were still burning five minutes after they were waxed and yanked.

"Roll over," he ordered.

It was then I realized I was only halfway done... and he hadn't even done my scrotal area... which was rather hairy.

He waxed me again.

He waited a couple of minutes.

He did my chest, which thankfully didn't hurt much since I didn't have much hair... but the area around my nipples, an area where I was always sensitive, hurt like hell.

He did my legs and then finally my groin area. He said, now holding a razor, "Don't move."

'Okay," I repeated, praying I didn't twitch or get an itch.

He took fifteen minutes, before he had made me as bald as the day I was born. I looked down and was surprised how a shaved groin made my cock look substantially larger.

He then went to the counter, grabbed some lotion and rubbed it all over my chest, balls and legs. "Flip back over," he ordered.

I obeyed, and he lotioned up my back, ass and legs. He then said, "Grab a robe and follow me."

"Okay," I said, the lotion soothing my body and cooling the earlier burn.

I followed him out of the room, down the hallway, and into a room where three women were getting their nails done. "Go to station five," he said.

"Okay," I said, although I felt self-conscious because I was about to get my nails done while three women wondered about me.

I sheepishly went to a seat between two older women, and sat down. The guy left, and a minute later an older Asian woman knelt before me and guided my feet into warm water.

I won't bore you with the details of the next thirty minutes, but I received a pedicure and manicure. My fingernails and toenails were then painted ruby red. Once done, I was led back to another room with a wardrobe and a person I instantly could tell was a cross-dresser in his-her early twenties, I would guess, was waiting for me.

"Hi, ready to be made beautiful?"

"I am," I said, instantly feeling comfortable around this person.

"Well, let's have some fun then," they said (I think that's an acceptable pronoun). "I'm Janet, by the way."

"I can't wait," I said, excited to look half as good as Janet did, noticing his Adam's Apple, confirming my assumptions.

She took my hand, I decided if she was called Janet, I should accept her as a girl in this adventure, and she led me to some outfits

Again, I won't bore you, but in thirty minutes, I had acquired some extra-large silicone tits (which were so exciting), a long blonde wig that looked so real, sexy lace black panties, three-inch heels (I know, but I didn't want to break my inexperienced ankles), a black garter-belt and stockings, all topped off with a sexy red gown.

"Okay," she said. "Now let's get your face done."

Twenty minutes later I'd been painted with mascara, red lipstick, blush, eye shadow and more.

"Ready to see yourself?" she asked, there being no mirrors in this room... trust me, I'd looked.

She pulled out a phone and said, "I need to send a picture to Jasmine."

"You know Jasmine?" I asked.

"She's the one who helped me discover my true self," she said.

"No way," I said.

"Yeah, that's' why it's so much fun for me to help you," she said, taking my hand again, just us girls together. "Come with me."

I wobbled a bit, even these modest heels were a little awkward to walk in, as I followed her.

Then I caught my first sight of her... I mean me.

"Wow!" I said, looking at myself in the mirror... but not recognizing myself.

"Yeah, you look hot," she said.

"You think so?" I asked, thinking I did look quite pretty....

"Yeah, I definitely think so," she nodded. "Want to go to a club and show off your new self?"

"With you?" I asked, feeling an odd connection with her.

"Sure," she said. "Plus, if you're feeling ambitious, it's amateur night."

"Amateur night?" I asked.

"Yes, we're going to a drag queen club," Janet said, "And I bet you'd be very popular onstage."

"Oh my," I said, my cock flinching, although I also felt instant anxiety.

"You don't have to," she said. "But you will be encouraged."

"Let's just go and check it out, and then see how I feel," I said, before I could change my mind.

"Sure," she said, taking my hand and leading me out. I paid for the two and a half hour makeover, I won't tell you how much, and when Emma saw the credit card I'd have some explaining to do, but at the moment, that was the last thing on my mind.

Tonight I wasn't Bill, but I didn't know what name I should use instead. As we walked outside onto the busy streets of Toronto, I asked, "Would you please name me?"

"Pardon?" Janet asked, still holding my hand, I realized... and oddly, I liked it.

"I need a stage name," I said.

"Oh, yes," she said, stopping and looking me over. "Hmmmmmmmmmmm."

"I know, there's no simple feminine version of Bill," I said. "Except for Billina of course, but she wasn't a person, but a hen in Ozma of Oz, the third Oz book. And I don't want to be named for a talking chicken."

"No, that wouldn't work," she agreed.

"And I don't feel like Brittany tonight, even though that's the name I've been using."

"Agreed, you're not a Brittany," she said. "No, you're someone else entirely."

I took that as a compliment, as I asked, "So who am I?"

"Give me a minute to think," she said, really putting some thought into my new feminine persona.

"Okay," I said, as we resumed walking hand in hand.

About a minute later, as we stopped at a Don't Walk light, she said, "In honour of Jasmine, as well as for myself, your girlfriend du jour, I think your new name is...."

She paused for dramatic effect, which was killing me, "You... are... definitely... a... Janelle."

"Janelle," I said, savouring the name as it rolled off my tongue.

"Yes, it's perfect," Janet said.