Digital Dominatrix 2.0 chapter 5 (Patreon)

Digital Dominatrix 2.0 chapter 5



I made my way to work feeling both more and less conscious of myself at the same time. Less conscious because my erections would be kept under control for the day by the cage, but more conscious because I now had to make sure I was wearing a bra as well as panties to work. This effectively meant that, although the clothes had an androgynous look to them, I was now wearing a one hundred percent female outfit to work.

I had on a light green, button-up office shirt with long sleeves, this colour seemed to do the best job of hiding the bra I was wearing. The shirt was tucked into the waistband of the plain black office pants that had become my go-to legwear for the office. If you looked past the higher than usual waist and the way they zipped closed, they were just a normal pair of trousers.

I must have been used to the feeling of the cage by now because, for some reason, it felt less restricting than usual, maybe it was because I had put it on willingly this time.

Or maybe it was because sissies belong in cages.

No! I had to stop myself from thinking like that, I didn’t really think like that. It was just because of all the videos and recordings Mistress had made me watch over the past week or so. I was just enjoying a fantasy that’s all, I wasn’t really a sissy.

I made my way into my office building, and after a cursory greeting to both my co-workers, Emma and Jake, I went straight to my desk to get started. I couldn’t let this whole ordeal affect my work, especially when the digital mistress kept deciding to spend my money on items to further my humiliation.

I worked away at my desk for a while, getting through a lot of the previous week's invoices and data dumps without any distractions. No teasing from Emma, who was clearly just as busy. No requests from Mistress for panty checks (not that she needed to now), it was starting to feel like a normal boring Monday.

Of course, that couldn’t really last long, not when I knew Emma was desperate to find out what I had been up to at the weekend. She got her chance a little before lunch. She must have found herself a little free time because she wheeled her office chair over to my workstation with a smile.

“Hey there sissy. Have a fun weekend?” She asked, thankfully, in a quiet enough voice that we wouldn’t be overheard.

“First of all, stop calling me that. And yeah, I guess it was … fun, I suppose.” I replied.

“Are you really still trying to deny it, Mike? Even after you practically begged me to spank you last week in your little maids outfit?” Emma replied, raising her volume a little higher towards the end of her sentence.

“Shhh! Would you stop? I didn’t ‘beg’ to be spanked, I was just … curious, that’s all.” This was mostly true, really.

“OK Mike, if you say so. But any time you get curious again, just let me know.” Emma answered with a not so subtle wink. “So, what did you get up to at the weekend? I’m assuming that you either went to the Bahamas for a day or you got a spray tan.”

“Oh, yeah. Well, it was Mistress ' idea, obviously. But I guess I don’t mind the color so much.” I replied, deciding not to tell her about the feminine tan lines I was sporting under my clothes.

“It's a nice color on you, you should keep it topped up. So did you get up to anything else?” Emma was insistent on finding out what else had happened, so I figured I would have to give her something.

“Well, I was made to toss out all my male underwear. So I guess I’m stuck wearing panties for the foreseeable!”

“Oh dear, well you look better in panties anyway Mike, so what pair did you go for today? Wanna give me a peek?” Emma said, reaching one of her hands towards my crotch as she did.

“Hey!” I yelled as my hand shot up to intercept hers.

I knew she wouldn’t actually be able to see anything, not while I was sitting in this position with my shirt tucked into the pants, but I still reacted a little instinctively. I went to grab Emma by the wrist to stop her from touching me, but in the process I actually swatted her hand downwards so that it made contact with the crotch of my trousers. Of course, given how little room there was in the crotch, there was no way Emma wouldn’t feel the bulk of the chastity cage I was once again wearing.

“Oohhh hello there. Has someone been a bad sissy? Got yourself locked back up?” She said in a teasing voice.

“No actually. I actually asked to put it back on this morning.” I told her, causing her to give me a rather quizzical look for a second before replying.

“Wait, so you ‘asked’ to have your cock locked away?” Emma asked.

“Yeah, I figured it would keep me from getting distracted while I worked. That, plus it will make it more difficult for you to torment me. There’s barely any room in these pants as it is without … you know.”

“Without your little cock standing up all the time you mean?” She said with a laugh. “But hey, I’m not one to judge, if you’d prefer to keep your little clitty locked up that’s fine with me.@

My clitty … Now Emma was calling it that, how does she even have that word in her vocabulary, and why did it turn me on more when she said it?

“It’s not that I ‘want’ to keep wearing it, it just helps me keep focused is all.” I said, but I wasn’t sure if that was true or not by this point. Honestly, I was starting to get used to the feeling of having my clit squashed up in its cage.

Great, now that damn word was sneaking into my vocabulary. I don’t have a clit…I have a cock!

“Mhmm. You keep telling yourself that, Mike.” She said, still with a smug smirk on her face. Even with the cage stopping the full erection, she could clearly see the flushed cheeks and uncomfortable squirming in my seat, indicating just how turned on I was.

“Whatever Emma. Don’t you have work to do?” I said, more petulantly than I had planned.

“Mike, I don’t think I like your tone. Do I need to put you over my knee for another spanking?” Emma said, whispering harshly into my ear.

“Hm!” The smell of her perfume, her proximity to me as she leaned in, and the content of her words, sent a visible shudder of need through me, causing some kind of horny squeak to escape my lips.

“Ha, it sounds like you’d enjoy that. Why don’t you bring that maids outfit over to my place again tonight and you can make it up to me for being snippy just now?”

“Emma I … I don’t think-” I didn’t want to give in to her so easily again, but I wasn’t really convinced I wanted to say no either.

“I think you need to stop thinking so much, and just start enjoying it. We both know you’d love to come over tonight, so you can either do so willingly, or I can send a message to the Mistress app. I’ll bet she would like my idea.” Emma said, before I could even think of a way out.

“Fine. But I don’t have the uh, the outfit with me. So I'll have to take a train or bus to your place later.” I said, feeling another pulse of arousal at the thought of serving as Emma’s maid once again.


“Great! I’ll see you tonight.” Emma said, brightly. “Well, we’d better get back to work, see you later, sissy.” She added the last word a little too loudly as she wheeled away from my desk.

Well, it looked like I was going back to being a maid for the evening again.


The rest of the work day passed in typical boring fashion before I headed home to get ready for an evening with Emma, or Miss Emma as I assumed it would be for tonight.


I briefly forgot about the new locking system on my apartment door when I got home, I automatically reached into my jacket pocket looking for a key as I felt my phone vibrate with a message.

“Sissy, you must present evidence that you are still wearing a bra and panties before I let you into your apartment.”

Shit, I quickly looked up and down the hall to make sure no one was in sight before I started undoing the buttons on my shirt to expose the bra to the doorbell camera. With my shirt hanging open, I unzipped my pants and pulled them just low enough so the panties could be seen and step back a few steps to make sure the underwear was in frame of the camera.

I held the pose for an uncomfortably long amount of time, feeling very exposed standing in the hallway flashing my bra and panties to seemingly no one.

Thankfully, I heard the click and whirring of the lock disengaging, granting me access to my apartment. “Hello Mistress.” I greeted my AI domme as soon as I was safely inside.

“Hello sissy. I hope you had a good day at work.” The AI voice replied, just as unemotional as ever.

“Yeah, fine. I have to go over to Emma's house again tonight. She, uh, she wants me to be a maid for her again.” I explained, not expecting any objection to this.

“That is excellent news sissy. I’m sure you will have lots of fun with Miss Emma.” Just as I expected. I quickly grabbed a bite to eat and packed the maids outfit into a bag before making myself ready to leave.

“Make sure you head straight to Miss Emma’s house, sissy. I will be keeping track of your journey via GPS. You will be punished if you attempt to go anywhere else. This was unexpected. I wasn’t planning on going anywhere else anyway, but the thought that Mistress could control where I go and stop me from going anywhere without her permission was worrying.

I decided to put that to the back of my mind as I made my way via bus to Emma’s street. The nerves started to kick in a little again as I made the short walk from the bus stop to Emma’s. It's one thing to sit at home and fantasize about this sort of thing, it’s a whole other thing to actually dress yourself in a maid's outfit to serve a strong woman like Emma.

I knocked on Emma's front door and waited, after a minute or so I heard her unlock the door to let me in.


She was a sight to behold, Emma had clearly dressed for this occasion. She was wearing a tight black leather skirt that reached to mid thigh, this skirt combined with the tall heels she had on her feet gave her a powerful, severe look. Her top half was covered with a white button up shirt, not entirely unlike what she would have worn to the office, except that she had a tight black corset like band wrapped around her waist, which served to accentuate her womanly curves even more than usual. The outfit pulled in her waist and pushed up her boobs, giving her a great hourglass shape.

“Ah, there you are. It’s about time, it’s not nice for a maid to keep the Mistress of the house waiting, you know.” Emma said, standing aside to let me into her home. I had to stop myself from staring at the older woman as my cock started to wake up in its cage.

“Sorry er, Miss Emma.” I said nervously.

“You will be if you don’t hurry up and get changed.” She replied in a stern voice.

“Er, right. So I’ll go to the guest bedroom again?”

“Yes you will. And be quick about it. I’ve already been kept waiting too long.” Emma replied as I scurried quickly towards her stairs to get changed.


I quickly stripped off all my office clothes and got myself ready for my duties, whatever they might be. Before too long, I was back in the ultra-sexy maid outfit with white panties and bra underneath, white to match the stockings that were encasing my still smooth legs. Just how long did the effects of that cream last anyway?


“There she is.” Emma said as I made my way back downstairs and into the living room. “I have been looking forward to having a sissy maid serve me again. But first, I think we need to complete your outfit.”

I wondered what she meant as I looked down at myself, pretty sure that I was dressed the same as I was the last time I was here.

“What do you mean?” I asked, a little uncertain.

“I’ll show you what I mean.” Emma said, reaching down to retrieve a box from the floor at the side of the couch she was sitting on.

“Is that a shoe box?” I asked as I saw what she was holding.

“It is indeed. Quite an expensive one at that. But my sissy deserves the best doesn’t she?” I didn’t know if I was supposed to answer that question, so I just stayed quiet. I wasn’t sure how I felt about being referred to in the feminine, but my locked up cock seemed to like it.

Emma laid the box down in front of her and lifted the lid, revealing a pair of shiny black high-heeled shoes with a pointed toe. They had a strap that looked like it would wrap around the ankle and buckle in place to keep the shoes on my feet. The sight of the heels made me nervous, up until now I had always just stayed barefoot while dressed en femme.

“Well, don’t just stand there sissy. Try them on. I’m pretty sure I got them in the right size.”

I didn’t know what to say to the heels, so I just bent down to retrieve them from the box, feeling the petticoats of my skirt lift up as I did. I took the shoes out of the box and took a seat next to Emma on the sofa to pull them on. Emma slid down onto her knees in front of me to help me get them in place.

The shoes felt tight on my feet as Emma reached around my ankle to buckle the straps in place. Once she had both of them tightly strapped on, she reached once more to the side of the sofa to grab something I couldn’t see.

“Just need to add the finishing touches.” She said, bending low over my outstretched feet so that I couldn’t see what she was doing. I felt her fiddling around with the buckles of the ankle straps, after a few seconds, I heard a small ‘click’ from each of my feet. Emma leaned back onto her knees to reveal what she had been fiddling with.

Padlocks! Two small padlocks had been threaded through the buckles on the shoes, effectively locking my feet into the heels.

“There! Now my sissy can’t take her shoes off without my help.” She said, standing back to her full height. In my seated position, with Emma standing tall above me and me dressed like a demure sissy maid, I felt very intimated.

“Stand up, sissy. Slowly. You’re going to need to adjust to the heels a little before you get to work.”

I did as Emma said, rising slowly from the couch on my new heels. I wobbled a little unsteadily as I brought myself back to a standing position.

“Well, how do they feel?” Emma asked me.

“Um, tight. And tall, I’m not used to wearing heels.” I said, still nervous about taking a step in them.

“Just remember, heel toe, heel toe. I’m sure you’ll pick it up in no time- What’s this?” Emma changed her tone mid-sentence as she reached her hand up to my shoulder, pulling the frilly, puffed shoulder section of the maids outfit down to expose my bra strap.

“This bra is filthy!” She said, indignantly as she studied the shoulder strap of the bra. “Wait, did you get a spray tan while wearing this?” She asked.

I didn’t have a chance to answer before she slid the strap of the bra to the side, exposing the obvious tan lines I had. Emma stared at my shoulder for a beat before bursting into laughter.

“Hahahaha, Oh dear that is too precious!” She said through her laughter, her previously stern tone being replaced by mirth. “Mike, you have tan lines! Ahahaha.”

“It wasn’t my fault! Mistress made me-”

“Of course she did, dear. Oh wow she’s even more creative than I thought. But still, you have completely ruined this bra. And after I was kind enough to give it to you. We’ll have to find you another one. Come with me.”

Damn, I didn’t think some staining on a bra would matter that much, not like I was intending for anyone to see it.

Thankfully, Emma took my hand to help me walk as she led me towards the stairs. I had to really concentrate as I walked in the locked heels.

“Careful on the stairs, dear. I’ve got you.” She said as I navigated the stairs, one step at a time.

When we made it to the landing atop the stairs, Emma led me over to a door that led to her bedroom.

“Now you just wait here and I’ll see if we can find you a nice ‘clean’ bra that goes with your outfit.”

I leaned against the doorframe as Emma headed over to her own wardrobe and began fishing through a drawer at the bottom, giving me a good view of her ass as she bent over to search. As I was staring intently at her ass, Emma quickly spun around to face me, catching me starting as she did.

“Mike, were you just staring at my ass?” She said with a coy smile, knowing the answer already.

“S-sorry.” Was all I could think to say.

“My my, you are a horny little pervert aren’t you?” She said, walking over to me holding up a replacement bra. It was white like the one I had apparently ruined, but a lot flashier, with scalloped lace edges around the cups, giving it a more alluring look.

“Let’s get this on you.” She said, reaching up to grab hold of both of the shoulders of the maid’s outfit and quickly yanking downwards, pulling the outfit down to expose my upper chest.

I didn’t object as she reached around to undo the clasp at the back of the bra. As soon as the old bra was removed, Emma once again let out a laugh as she took in the full effect of the tan lines.

“Hahahah well, she really did a number on you, Mike.”

I held out my arms to let Emma slide the bra down to sit loosely on my chest. She slowly walked around to my back to fasten up the clasp. I noticed that the cups of the bra sat loosely and dishevelled without Emma's large breasts to fill them. This was something Emma noticed too as she came back around front to examine the fit.

“Hmm. This just won’t do. I wasn’t planning on this just yet but I think I’ll have to show you your next gift a little early.” Emma said.

“Next gift?”

Emma answered by heading back to the wardrobe, opening up the double doors this time and lifting up another box. She placed the box on her bed and removed something from it, as she turned around I saw what it was she was holding. Two large, realistic looking silicone tits.

She carried the fake boobs over to where I was stood, I watched them jiggle heavily in her hand as she brought them over.

“I was saving these for later but seeing as you've gone and ruined the bra I gave you, I'll have to use them now. But don't worry, I won't glue them into place just yet.” Emma said as she placed the fake boobs in the bra cups.

She fiddled around with them, making sure they sat naturally in the cups, adjusting the shoulder straps a little to get them in the right position.

Did she say something about gluing them on?

When she was happy with the position of the boobs, she helped me pull the maids dress back up into place on my shoulders, hiding the false tits from view. But the front of the dress was now stretched tightly across the new bra and boobs, making it obvious that I had tits hidden underneath.

I felt even more off balance now thanks to the heels and boobs combo.

“Perfect. What do you think, sissy? Are they big enough?” Emma asked with a smile.

The only answer I could imagine appeasing her at this point was, “They're good Miss Emma.”

“Oh goody! I knew you'd love them. Now let's get you back downstairs and you can pour me a glass of wine. I think I've earned it.”

Emma helped me back down the stairs, working extra hard to keep me from falling forward with the weight of the boobs that were sat in the bra.

“I'll take a glass of red in the living room when you're ready, maid. Do be careful in the heels.” Emma said as soon as we were back downstairs, walking into the living room with a dismissive wave.

I watched her ass for a second as she walked away, before heading slowly into the kitchen to pour the wine. I found the bottle she must have wanted on the kitchen counter, with a glass next to it, at least she was making it easy for me.

Oh so slowly, I made my way into the living room with the glass of wine, taking extra care not to spill a drop as I wobbled in the heels.

“You know you're really going to have to work on becoming more graceful in those heels, sissy. I can't have you stumbling around all ungainly and sluggish.” Emma said in a mocking tone as I placed the glass down on the table next to her.

“Sorry Em-err, Miss Emma. I'm trying my best.” I said, truthfully.

“I'm sure you are sweetie. But I think you need to get some practice in ASAP. Why don't you start by walking around the living where I can see you. I'll direct you from here while I drink my wine.” Emma said with a smile.

“Sure, I'll give it a try.” I made my way to the outer edge of the living room, preparing to start a few laps while concentrating hard on where to place my feet.

“Now remember, Mike. Make sure you have a firm footing on the heel, then let the rest of your foot follow to the floor. You can start off nice and slow.”


I did as Emma said, walking slowly around the living room. I managed a couple of laps, feeling like I was starting to get a little more sure-footed, when Emma spoke up.

“You're looking a little better, sissy. Try to pick up the pace a little, and focus more on what your hips are doing as you walk. You've spent enough time staring at my ass to know what I mean I'm sure.”

My cheeks flushed a little at that comment, but I couldn't argue, she had a point.

The ‘practice’ continued in this manner for a while longer, me walking around and around the living room with the occasional comment from Emma. I was starting to get a lot more confident in the heels, but my calf muscles were definitely starting to feel it. I was saved from my laps of the living room by Emma’s phone ringing.

“Oh! It’s the big boss from the upper floor. I’d better take this. Sissy, get down here in front of me and rub my feet.” Emma said as she looked at the caller ID on her phone.

“Hello Tony! Odd for you to be calling me so late, I assume there’s been some disaster.” I listened in on Emma’s side of the conversation as I knelt down by her feet.

“Umm, Miss Emma. Should I take off your shoes?” I asked in as quiet a voice as I could.

“Hang on a sec Tony…” Emma covered the speaker of her phone with her hand to speak to me, “Yes. Obviously you should take them off, now keep quiet.”

“Sorry Tony, what is it?”

I unzipped a long zipper down the side of her boots and carefully pulled them off her feet, revealing a pair charcoal coloured stockings stretched across her feet. From my position on my knees in front of her, I had a great view of her legs, all the way up to her skirt.

“Oh has he? That’s a shame, I’m sure we’ll manage.” Emma kept talking into the phone as I gently rubbed one of her feet through the stockings. I lifted the foot I was massaging up a little higher, shuffling a little to get into a better position, Emma responded by moving her other foot into my lap. I was now holding onto one of her feet while the other rested right next to my crotch, over the top of the frilly maid skirt.

“Well I can give Mike a call and give him the heads up but I’m sure he won’t mind … No no, I have his number, I’ll speak to him straight away.” My ears pricked up at the sound of my name being mentioned.

“Okay sure. What is it exactly we should be prioritizing?” I drifted back out of the conversation as Emma kept talking, focusing instead on the feet of the dominant woman sitting in front of me.

Eventually pulled her foot out of my hands, and quickly replaced it with the other one. In the process of doing so, she planted her other foot dead center of my crotch. There was no way this was accidental, her stocking covered foot was resting right on top of my trapped cage. My arousal was sent into overdrive as Emma slowly began moving her foot in lazy circles around my trapped cock. I chanced a look upwards at Emma’s face, but she was deeply engrossed in her conversation, paying me no attention.

I swear it wasn’t on purpose, but my eyes were drawn to the space where her thighs disappeared into her skirt. Was it just the shadow between her legs, or was she wearing black panties?

“...Bye. Ahem!” My eyes snapped back to Emma's face as she loudly cleared her throat. I was too caught up in my ogling to notice her conversation coming to an end. “See something you like up there, sissy?”

“...Um, sorry Miss Emma.”

“Not to worry, if you behave yourself I might just give you a better look.” Emma said, suggestively, causing another throb from my trapped cock.

“That was Tony on the phone, Jake has called out of work for the rest of this week. Some kind of emergency at home, so it looks like me and you are going to be alone in the office for a few days. I assured Tony that you and I could pick up the slack while Jake is off. I’m assuming you don’t have a problem with that?” Emma explained.

“No. I’m sure we can manage.” I said, not sure what it would be like working with Emma without Jake forcing her to be discreet.

“That’s what I thought. Now, why don’t you go and refill my glass.” She said, holding the now empty wine glass out for me to take.

I was a lot steadier in the heels this time and quickly returned to the living room with the wine. When I placed it down next to her, I noticed Emma typing away on her phone.

After a minute or so of me standing awkwardly, Emma finally placed her phone down and spoke to me.

“Good news, sissy. I was just messaging your Mistress. I explained to her that since we are both starting work early tomorrow because of Jake’s absence, that it makes sense for you to stay here tonight. Won’t that be fun? A little sissy sleepover!” Emma said with a look of glee.

So I was spending the night at Emma’s place, what would that entail? I wondered.

—

I spent the rest of the evening serving as Miss Emma’s maid, I got a little more practice in the heels as I did. I ended up fetching her another glass of wine as well as tidying around and making a show of dusting random parts of the house. The whole evening was a fetish dream come true. I could feel Emma’s gaze on my ass every time I bent over to dust something or pick something up.

By late evening, my calves were aching so bad I was desperate to take off the heels, which would have been easier if they weren’t locked around my ankles.

“Well sissy, I think it might be time to head upstairs and retire for the evening.”

“Yes Miss Emma.” I was actually thankful to be heading upstairs, surely I would be able to take off the heels soon.

I followed Miss Emma upstairs, fully expecting to be sleeping in the guest room, so what she said next surprised me.

“You know what, sissy? I think I might need to keep an eye on you while we sleep. Make sure you don’t get up to no good?”

“Umm, what do you mean?”

“What I mean is, I think I’ll have to keep you close to me tonight. You’ll sleep in my bed with me.” Emma stated, less of an invitation and more of an order. All I could do was stare at her in confusion, not quite believing what I was hearing.

“Oh don’t give me that look, Mike. Usually I wouldn’t dream of inviting such a horny young man into my bed. But I think I’ll be safe with you won’t I? What with your little cock safely locked away.” Emma said with a satisfied smirk. “I’ll let you get ready for bed in the guest room. I left you something to wear for bed that I think will suit you. I’ll be waiting for you in my room when you’re done.”

“Yes Miss Emma … Umm, do you think I could take off the heels now? My feet are killing me.”

“Oh right! I almost forgot about those, you’ve been doing so well in them I barely noticed you still had them on.” Emma said as she pulled a small key from somewhere inside her shirt and bent low to unlock the small padlocks. “There you go, you can leave them in the guest room. Chop, chop.”

I removed the heels and the outfit in the guest room as instructed, breathing a sigh of relief as I did. I took a moment to sit down on the edge of the bed and massage my own legs. I could see why Emma liked it so much. When I was stripped down to just my panties and the cage, I took a look at what Emma had left for me to sleep in.

Pretty much exactly what I was expecting. A cream coloured silky nightdress type thing that looked like it would reach to just above my knees. There was a matching pair of small, silky shorts to go with it.

I swapped out my panties for the shorts and grabbed the nightdress. It poured over my upper half like liquid, the silk feeling incredible on my smooth skin. My cock was desperate to get out of its cage by now, but I knew there was no chance of that after what Emma had said.

I walked nervously into Emma’s room, to find her already lying in bed waiting for me. By the looks of her shoulders, she was wearing almost the exact same thing as me, but hers was a deep blue colour, and was of course held in a much more appealing fashion by her own large breasts.

“Well, are you going to get into bed?” Emma said after she had left me staring at her long enough.

“O-of course. Thanks.” I said as I moved over to the other side of the bed and slid underneath the covers. Emma slid in closer to me under the covers, one of her hands sliding up and down the smooth silk of my torso.

“So, sissy. Tell me honestly, are you enjoying yourself?” Emma asked me as her hand moved down to the bare skin of my thigh.

“Yes Miss.” I answered, there was no point in lying at this point. Besides, I felt like she could see right through me.

“I thought so. And don’t you think you should do something to thank me for helping you to enjoy yourself so much?”

“O-of course, what do you want me to do?” I asked, willing to do anything she asked at this point.

“Well, sissy. I was thinking that since I’ve indulged your sexual appetite all evening, that you should do the same for me now.” Emma said, her hand leaving a trail of goosebumps everywhere it touched, I was sure I would be leaking in the cage by now.

“And just so you know, I decided not to wear the shorts of my own sleepwear.” She added with a throaty rumble in her voice. I knew exactly what she wanted, and I didn’t think twice about giving it to her.

I slid down the bed beneath the covers and between Emma’s legs. I couldn’t see very clearly under the covers, but my lips quickly found their way to the right spot against Emma’s pussy. My own arousal had taken control of me by this point, I was desperate for any sort of sexual experience that I lapped and sucked at her sex like a man possessed.

I could hear Emma’s moans growing more frantic as I eagerly licked her pussy, desperate to get her off. Desperate to make her cum with tongue. Her moans grew more frantic as she neared orgasm, my cock pressing painfully against the cage inside the silk shorts, deep down knowing there would be no relief for it tonight.

“Ohhhh, yes. Such a good sissy!” Emma cried out loud as her thighs tensed around my head, locking me in place as she came hard onto my waiting mouth.

“Mmm that was wonderful, sissy. It has been so long since I’ve been with someone so … attentive.” I was cuddled up to Emma after she had had her orgasm, one of her arms wrapped possessively around my shoulders with my head resting against her breast.

“Any time … Miss Emma.” I said, earning a small chuckle.


“I can’t wait for work tomorrow. I have the perfect outfit in mind for you.”

“Outfit? I have a work outfit with me.” I said, a little surprised at her statement.

“Ah but that’s a little too conservative for what I have in mind. Don’t forget sissy, Jake isn’t going to be in the office tomorrow. It will just be me and you, no need to hide who you really are. Just think of the fun we could have.”

Oh shit … Emma was clearly going to be having fun with me tomorrow.


End chapter 5