My Hypnotist Girlfriend chapter 9 (Patreon)

My Hypnotist Girlfriend chapter 9




It was a few days before Lenore broached the subject of her hypnosis with me again. I'm guessing she was letting me recover from the time spent serving as her feminized maid.

Not that I didn't enjoy it, I just never thought it would be something I would ever end up doing. But of course, Lenore had a different plan. She had already admitted to me that during one of the trance states I was in, she had asked me about my sexual fantasies, fantasies I had kept hidden from her, and she apparently had a plan to help me experience some of them. Whether I liked it or not!


It was Friday afternoon when Lenore actually brought up the subject again. We had already been out and ran a few errands, so we had the afternoon to ourselves.

We were sitting on the couch in the living room, TV on for background noise, both scrolling through our phones … a very modern relationship.

“So, you should know that the strap-on I ordered was delivered yesterday.” Lenore said to me I was watching some sports highlights on my phone. I damn near choked on thin air when I heard what she said.

“Really? Well, have fun with that.” I said, trying to sound dismissive of the idea.

“Oh I will, babe. Don't worry about that.”

“You know what I mean.” I said, wondering how serious she was about actually using a strap-on with me. It had long been a fantasy that intrigued me, but I never really thought about bringing it up with a partner. I guess it always felt kind of weird for a guy to ask a girl to fuck his ass with something.

“Oh Shaun, I know you might not be a hundred percent sold on the idea of getting your ass fucked, but I know someone who is.” Lenore replied in a teasing voice.

“Oh yeah, who's that?”

“Charlotte.”


“And who the hell is Char-” I started to speak before I realized what she was talking about. Charlotte was the name Lenore had given me after she had dressed me in a frilly maids outfit and spent the evening tormenting me with hidden triggers and suggestions.

“You know exactly who Charlotte is, babe. And I think she may be a bit of a slut!” Lenore said in a suggestive tone.

“Look Lenore, whatever I told you when I was in trance was just fantasy that's all. It's not like I actually want to have a dildo shoved up my ass.” I said, adjusting my position on the sofa to hide my growing erection.

“Oh please, if this wasn't something you wanted, then you wouldn't be so turned on right now.”

“Who says I'm turned on?”

“Shaun, I can tell when you're trying to cover up your hard-on you know. I have to admit I was a little shocked when you finally told me about your most hidden fantasy. But seeing you all embarrassed and flustered in your pretty panties is kind of a turn on for me.” Lenore was smiling at me mischievously as she spoke, I really didn't expect her to be so into this, but she was definitely having her fun.

“Well I'm glad you're having fun at my expense.” I said, still unable to face up to my own humiliating desires while not under Lenore's influence.

“Don't act like you're not having fun too. Or is that what you need to do to preserve your masculinity? Do you need me to ‘make’ you do these things so you don't have to face up to your own kinky fetishes?” She had me there, I don't know if it was the hypnosis or if she could just read me so well, but she was pretty much spot on.

“I guess you're not totally wrong.” I admitted after a brief pause.

“That's what I thought. I don't know why you didn't tell me about all this before babe. We could've been having so much fun!” Lenore said, brightly.

“Now, one way or another, Charlotte is coming out to play tonight. We can do it the easy way … Orrrr, we can do it the fun way.” She said, with a wicked glint in her eyes.

“Ummm what's the difference?” I asked.

“The easy way is you go upstairs and get dressed like we all know you secretly want to. The fun way is I put you back into trance and ‘make’ you do it.” She said, putting emphasis on the word ‘make’, like we both knew I would enjoy it.

“Okay, then I guess I'll choose the fun way.” I said.

“I thought you might, but just so we're clear. You're telling me you want me to turn you into a hypnotised plaything for the evening?”

She was effectively asking for permission to spend the rest of the day humiliating me using her hypnosis, and I couldn't deny the idea turned me on!

So all I could say in reply was, “Yes.”

“Great! Then get ready to have some fun, Charlotte.”

With that said, Lenore set about putting me back into trance. It must not have taken her long to do it, maybe because she had already put me under so many times before, or maybe because she knew I was such a somewhat willing participant. Either way, before I knew it, I was floating in that weird space between asleep and awake, all I could hear was Lenore’s voice washing over me, somehow sounding like she was right up close to my ear and distant at the same time. I tried to focus on what she was saying but I could only really pick up on little snippets of her speech.

Before I knew it, I felt myself start to wake up and return to consciousness.

“3….4….5…. And wide awake again, feeling happy and refreshed.”

I blinked my eyes a couple of times as I returned to consciousness, still in the same spot on the sofa, except maybe a little more slouched. I took stock of my situation and was somewhat surprised to see that I was still dressed appropriately.

“So, how do you feel?” Lenore asked me.

“I feel fine, pretty good actually. I expected … something more I guess.” I replied.

“Ah well, I was just going to throw you in at the deep end and let the Charlotte persona takeover again, but then you’d miss out on the best parts. See, I know you have a teensy little thing for humiliation, so I wanted to make sure you get the full effect.” Lenore explained, leaving me a little nervous as to what the ‘full effect’ might be.

“What do you mean?” I asked.

“What I mean is, instead of putting you into trance and making all the changes while you were under, I thought I’d just focus on some triggers and post hypnotic suggestions this time. For example, how do you feel about me fucking you with a strap-on?”

“Well, I’m pretty nervous about it, but I trust you, and I’ve always wanted someone to fuck my ass!” My reply was much more honest than I had planned it to be. “Wait … that wasn’t what I meant to say. I was actually thinking that … I really can’t wait to know what it feels like to bent over and fucked like a girl.”

Lenore had burst out laughing at this latest statement, causing my face to flush red.

“Hahahaa. Figured it out yet, babe? The first thing I did was make it so that you couldn’t lie to me for the rest of the night.”

Shit she was right, the humiliating admission I had just made about getting fucked by her strap-on was all true, but of course I hadn’t planned on actually admitting to her. I guess on some level I still thought of the whole situation as taboo. Unfortunately, playing it off like I wasn’t interested didn’t seem to be an option today.

“There’s no way that was the truth. You did something to make me answer that way.” I said, still not wanting to admit outright what I really wanted.

“Really? Okay then how about a test. Tell me your name is Phil, or that the sea is purple and grass is blue. See if you can tell me any lie at all.” She replied in a challenging tone. I decided to do what she said and test out her truth command.

“My name is … Shaun. The sea is mostly blue and the grass is mostly green.” Dammit, I thought. There had to be some way for me to lie, how about … “I fucking love it when you tease and humiliate like this!” Oh fuck.

I immediately realised my mistake when I had tried to lie about how much I was enjoying this, because Lenore’s eyes lit up like a kid at Christmas.

“I thought as much. Now we should probably think about getting you ready to serve, Holly will be here soon.” Lenore said, matter-of-factly.

“Wait, WHAT? I don’t want Holly to think of me as some kind of sick weirdo in a maids outfit!” I said, incredulous at the thought of Lenore inviting one of her friends over to further my humiliation.

“Don’t worry, Shaun. She won’t think of you as some kind of weirdo, she’ll just assume it’s a kinky game and I’m pulling all the strings. But you know what’s interesting? See, you said ‘you don’t want Holly to think you’re a weirdo’, but you could have said, you don’t want Holly to see you in the maids outfit. Or anything along those lines really.”

Shit, she had a point. I didn’t actually think I wanted to be seen by my girlfriend's hot friends while I was dressed so humiliatingly, but just the thought of being exposed to her friend had caused my cock to surge to full mast in near record time. I didn’t want to risk accidentally exposing any more of my own kinky secrets, so I resolved myself to say as little as possible for the rest of the night.

“That’s what I thought.” Lenore said with an extremely satisfied smile on her face, clearly my silence was consent enough for her to go through with her plan. “Now, enough stalling, it’s time for some ‘Maid Service’.

Those last two words must have been some kind of trigger, because as soon as I heard them, I had a sudden desire to go upstairs and get changed. I stood up from the couch and headed up towards the bedroom, knowing exactly what it was I would be changing into, but unable to stop myself or even object in any way.

I walked straight into our bedroom and opened our shared wardrobe, hanging dead center, with all the adjacent clothes already pushed off to the side, was the maids outfit. My cock pulsed at the sight of it, betraying my thoughts to anyone who might see me wearing the ultra-feminine outfit.

Every second I stared at the outfit, the compulsion to wear it grew, until I was pulling it out of the wardrobe and laying it on the bed. Before long, I had all my own clothes off and was stepping into the open back of the black and white frilly dress. My movements were pretty much automatic as I zipped up the back of the dress and sat down to pull on the stockings.

A few minutes later, I was standing in front of the wardrobe mirror, staring at my feminized reflection. Once I was (somewhat) happy with my appearance, the compulsion that had caused me to don the outfit seemed to pass, but the thought of taking the outfit off never occurred to me. So instead, I headed back downstairs to where Lenore was waiting in the living room.

“Ah there she is!” Lenore said brightly as I entered. “Nice to see you again Charlotte.”

“Umm, Hi. So, what now?” I asked, refusing to argue against her use of the feminine name she had decided on.

“Now we make sure you’re ready for our guest. First, a test. Tell me your name.” Lenore said.

“It’s Charlotte.” I replied, pretty much knowing what was coming. I had of course tried to say ‘Shaun’ but just like last time, the name ‘Charlotte’ came unbidden.

“Oh good, I see that one’s working fine again. So if you’re Charlotte, then who am I?” Lenore asked with a knowing smile.

I focused all my efforts on saying the word ‘Lenore’, I really tried to make sure the word was right on the tip of my tongue, but as soon as I opened my mouth to speak, I knew I had lost. “Mistress.” I said, inwardly cursing the word that had come out of my mouth, while Lenore just giggled.

“Perfect! I made it so the triggers from earlier in the week would re-awaken as soon as you put on the maids outfit again. So that’s mine and your titles dealt with. Now tell me, who is coming over for the evening?” She asked me.

“It’s Miss Holly, right?” I replied, taking a second to realise what I had just said. “Dammit Mistress! Miss Holly is coming!” I said again, trying once more to get Holly’s name right.

“Yes she is.” Lenore replied, happily, just as the sound of the doorbell rang out through the house.

‘Ding Dong’

“Oh good, that will be ‘Miss Holly’ now.” Lenore said with a chuckle. “Why don’t you be a good maid and go and answer the door?”

“What?! Like this? No way am I risking any of the neighbors seeing me like this!” I said, defiantly.

“I thought you might say that. I was really hoping you would embrace this fantasy of yours, but I do like seeing a little defiance in you, babe. It makes it more fun for me to do things like this.” Lenore said with that devious look in her eyes again as she stepped quickly towards me.

All I saw was Lenore's hands shoot quickly up to my face and ‘Snap’ loudly…


…’Ding Dong’

My mind was brought out of some kind of stupor by the sound of the doorbell ringing once again.

“I think you’d better get that, babe. But first, what was your name again?” Lenore asked me.

“I’m sissy Charlotte! And it is my pleasure to serve you.” I replied automatically, before dropping into a deep curtsey, lifting the hem of my dress high as I did, almost flashing the pink panties I was wearing.

As soon as I was finished with the curtsey and my reply, my eyes shot wide and my face flushed red at the humiliating performance.

“Mmmm that was perfect. Now, are you going to get the door or do I need to make it worse for you?” Lenore said.

Fuck. She had me beat this time. I grumbled out some pseudo complaints but I left the living room all the same.

I briefly paused at the door, heart pounding as I prepared to expose myself to my girlfriend's girl-friend.

I slowly opened the door, hiding most of my body from view behind it as I did.

“Hey Shaun!” Holly said brightly as I cowered behind the door. She quickly let herself in, walking straight past me into the house, allowing me to slam the door quickly behind her.

“So Lenore tells me I should expect some kind of…” Holly’s voice trailed off as she turned around and finally took in what I was wearing.

“...Pfffft hahahaha oh my god, Shaun! What the hell is this? Hahaha.” Holly burst into laughter as she saw what I was wearing.

“Oh my god Lenny told me I should expect something a little ‘out there’, but this was not what I was expecting.” Holly continued laughing as I stood there, red in the face and with a hard-on doing its best to escape the confines of the tight panties.


“Ah I see you’ve met our maid for the evening.” Lenore’s voice came from the door to the living room.

“Yeah, I guess I have. But what is … what the hell is going on?” Holly asked Lenore.

“Like I said, I’m helping Shaun indulge in some of his fantasies. With a little … hypnotic help.”

“Wait, this is Shaun’s fantasy? Is he into humiliation? Like BDSM and stuff?” Holly said, her question was aimed at Lenore, but her gaze remained fixed in my direction.

“Turns out, yes, he is. Although he would never admit that to me himself. Thankfully, he doesn’t have any secrets anymore.” Lenore explained. “Oh and by the way, her name isn’t ‘Shaun’ for tonight.”

“Oh really? So what is it?” Holly asked.

Oh no.

“Why don’t you ask her?” Lenore said to Holly.

I felt my whole body tense up in anticipation at what I knew was coming.

“Ooookay. So what should I call you sweetie?” Holly said to me.

“I’m sissy Charlotte! And it is my pleasure to serve you.” I said, once again dipping into a deep curtsey, causing my face to redden at the humiliating gesture.

“Hahaha ‘sissy Charlotte!’ That is precious. Ohhh tonight is going to be fun.” Holly said, gleefully.
“Now why don’t we head into the living room so we can catch up and go over a few ground rules.” Lenore said, leading the way back into the living room.

Lenore and Holly took a seat opposite each other, Lenore on the couch and Holly in the chair opposite her. I had no idea where to put myself so I just kind of hovered there awkwardly. Thankfully, Lenore had something for me to do.

“Before we get started, I think the maid should serve us a couple of drinks.” Lenore said.

“Oooh good idea. I'll take a vodka and coke if you have it?” Holly said, before Lenore added her own drink order.

“And I'll have a glass of wine.”

Was there really any point trying to refuse at this point? I figured not so I just grunted my approval and headed into the kitchen to fetch the drinks.

I busied myself making the drinks as Lenore and Holly talked in the other room. It sounded like Lenore was giving Holly a few ground rules about what she could and couldn't do during the night, but I couldn't quite hear everything they said.

I walked back into the living room with the drinks and placed them both down on the coffee table that sat in between the two. I still wasn't quite sure what to do with myself afterwards but thankfully I didn't have to think about that.

“Thank you Charlotte. Now why don't you take your place here at your Mistress’ side.” Lenore said, pointing to the spot next to the arm of the couch near where she was sitting.

“Good girl.” Lenore said, the two words causing a pleasurable sensation to run through me. I chanced a look over at Holly, to see her watching my servitude with a gleeful expression.

“Now Charlotte. I have just explained to Miss Holly a few ground rules for tonight's little game. I have also explained to her that, in order to make sure we don’t do anything you don’t enjoy, I have removed your ability to tell a lie for the evening.” Lenore explained. “Now, having said that, tell me sissy, do you find Holly attractive?”

Oh shit, I couldn’t answer that question without potentially getting myself in trouble, so I opted to keep my mouth shut. The truth was, Holly was very attractive. She was the same age as Lenore, but had larger breasts than she did, and an ass to die for. Whenever Holly came by the house or we went out together, I would have to stop myself from checking out her rear. Which was difficult because she always seemed to wear tight leggings and yoga pants that seemed to purposely accentuate the shape of her butt.

I found myself looking over to Holly who was eagerly awaiting my response. Tonight, she was wearing a pair of tight, gray workout pants. I had already taken more than a subtle glance at her ass as soon as she entered the house.

“Well Charlotte. Your Mistress asked you a question. Do you think I’m hot?” Holly said, leaning back a little to give me a better view of her form. Her breasts squeezed into a tight, long sleeved top with a zipper that ran down from her neck. Currently it was zipped all the way up, hiding any cleavage but squeezing her boobs together under the top.

“Silence will not be accepted as an answer, sissy. Answer the question.” ‘Snap’.

Lenore punctuated her order with a snap of her fingers that seemed to reverberate through my head. I found my honest answer leaving my lips before I had a chance to think about it.

“Yes Miss Holly. I think you’re very hot.” My face reddened once again after I had answered.

“Ohhh ‘Miss Holly’ I like that.” Holly said with a smile.

I looked over at Lenore to see if she was angry with my answer, but she seemed more amused than anything. At least she did until she saw me looking at her, prompting her face to switch into an expression of mock surprise.

“Oh my! Is my boyfriend lusting after one of my friends?” Lenore asked, placing a hand over her mouth in a facsimile of shock.

“N-no Mistress. I’m not lusting after Miss Holly I swear. I just … she’s just … I only meant that …” I struggled to think of something to say that would make this situation better but Lenore was just giggling at my desperate, stammering response.

“Relax, babe. I think Holly’s pretty hot too.” Lenore said, putting me at ease. “But what do you like most about her? What do you think is her most attractive feature?”

“I think MIss Holly has an amazing ass.” I replied, once again unable to lie to either of them.

“Oh you do, do you?” It was Holly that replied first this time. “So tell me Shau-I mean Charlotte, do you stare at my ass when I come over?”

“Y-yes. I do.” I really tried to stop the answer leaving my lips, but clearly Lenore’s hypnosis wouldn’t be overcome that easily.

“Charlotte!” Lenore said, “How dare you ogle my friend that. I think you should apologise to Miss Holly for checking her out like that.”

“R-right. I’m Sorry Miss Holly.” I said, staring at the floor as the two women continued to embarrass me.

“That’s okay Charlotte. I guess it’s okay to stare at my ass from time to time.” Holly said.

“But I’ll bet he wants to do more than stare. Isn’t that right, sissy?” Lenore said. I tried to focus all my efforts on not answering that question as thoughts of Holly’s perfect ass filled my head.

“Y-yes.” I lost my fight and answered once again, prompting Holly to get back in on the fun.

“Oh really? And what is it you could possibly want to do to my ass, Charlotte?” She said, smirking.

Once again I tried to resist the urge to answer, and once again, I failed.

“I-I want to kiss your ass Miss Holly.” I said, furthering my own humiliation.

Holly and Lenore both broke out into giggles at my humiliatingly submissive response. This damn truth-telling suggestion was effectively forcing me to humiliate myself with my own submissive desires.

I looked back and forth between Holly and Lenore as they both shared a look with each other, before Lenore nodded her head slightly at Holly, as though giving her permission for something.

“You want to kiss my ass huh? Well I suppose I could allow you that much, you did fetch us drinks after all.” Holly said, standing up from her seat.

I watched as Holly turned around and placed one hand on the arm of the chair she had been sitting in, bending over slightly as she did to give me a great view of her ass. Her other hand reached behind her to grab the waistband of her tight pants and pull them upwards, causing the material to pull tightly between her round ass cheeks. She wiggled her hips from side to side as she pulled the pants upwards, causing her cheeks to jiggle slightly. The whole display was insanely erotic to my already horny mind. But was she actually serious about me kissing her ass?

“Well Charlotte,” It was Lenore who spoke, “would you really like to Kiss Holly’s ass?” She asked me again.

“Yes Mistress.” I replied.

“I thought so. Well, what are you waiting for? Go ahead.” She said, I couldn’t believe she was actually telling me to do this!

I carefully stepped around the coffee table to place myself behind Holly, before I could do anything else, Lenore spoke again.

“On your knees Charlotte.”

I dropped down to my knees, placing myself at eye level with Holly’s gorgeous ass. It looked a little bigger from this vantage point, and a lot better. I don’t know if it was Lenore’s order or if it was my own perverted desire that drove me, but without further ado, I found myself leaning in to kiss Holly’s ass.

I slowly leaned into one of her cheeks and planted a soft kiss on her ass, feeling my arousal surge to new heights as the flesh of her ass gave way slightly beneath the tightly stretched material.

“Mmmm that’s a good girl.” Holly said, sending another tingle of arousal through me. Was that the ‘good girl’ trigger working or was it just me?

I held the kiss on her left ass cheek for a few seconds before pulling back, my cock pulsing desperately in the panties.

“But the other cheek might get jealous.” Holly said, giving her ass a little shake in my face.

I needed no further instruction this time, moving over to the right ass cheek, this time I was less gentle with my kiss, putting more pressure on the soft flesh as I kissed, really forcing my face to sink into the meat of her ass cheek.

“Oh you might have to keep your eye on this one Lenny. I think he’s getting a little carried away.” Holly said, straightening up and pulling her ass away from my still puckered lips.

“I think you might be right.” Lenore replied. “Tell us Charlotte, are you hard in your panties right now?”

“Yes! I am incredibly turned on right now.” I said through gritted teeth, with or without the hypnosis, it would be impossible to hide how turned on I was at that moment.

“Well if you keep being a ‘good girl’ for us, then you’ll get a special reward later.” She said as Holly took her seat. The trigger word sending another pulse through my cock.


Holly and Lenore carried on talking with each other for a while after the ass kissing incident, leaving me back in my subservient position at Lenore’s side. Eventually Holly began asking questions about hypnosis.

“I never thought you could have so much fun with hypnosis! And it seems Shaun is really enjoying himself. Even if he can’t admit it willingly.” Holly said, eyeing me up as she did.

“Yeah, it turns out my boyfriend has a submissive side a mile long, and might just be a bit of a hypno-fetishist.” Lenore replied. “Isn’t that right, babe?”

“Y-yeah I … I really enjoy being made to submit like this.” I replied, once again having no choice but to answer honestly.

“So tell me, Charlotte. What do you like so much about it all?” Holly asked me.

“I don’t quite know. I guess I like the feeling of giving up control to Mistress. The thought of Mistress having the power to make me act in certain ways is an incredible turn on. I guess it feels very freeing having Mistress take some control of my actions.” I replied.

“Wow. I guess that does sound kind of hot.” Holly replied, genuine curiosity sneaking into her voice.

“Well … Would you like to give it a try?” Lenore asked, the question was directed at Holly, causing my eyes to widen in shock. Surely she wouldn’t …

“Ya know what … Fuck it.” Holly said, downing the rest of her drink in one gulp. “Why the hell not? Just don’t make me do anything too crazy.” She added

“Oh don’t worry, you’re in good hands with me.” Lenore replied with a mischievous smile creeping onto her face. “You just lean back and make yourself comfortable, I’ll do the rest.”

What the hell would happen next? What would Lenore do with two hypnotised playthings for the evening?

I guess I was going to find out.


End chapter 9