Exposed Sissy: Sissytoes

A brand new sissy diary entry ~ Sissy Toes can be proud of her exposure since she is the first sissy exposed on my sissy website for the year of 2019.

I am SissyToes. I am a 30 year old closet, sissy crossdresser. I have been secretly crossdressing in women’s clothes and heels since I was 15. A good female friend of mine, whom I used to live with, introduced me to crossdressing when I was in my teens.

We were bored sitting around her house one day when she looked at me, with a big, mischievous smile and asked me if I would model some of her clothes for her.

I said yes and agreed to be her little model for a bit. I wore lots of her sexy clothes, including dresses, skirts, camisoles, nighties, leggings, swimsuits, panties and bras, and lots of feminine footwear (high heels, sandals, and girly flip flops).

She knew I enjoyed it A LOT! the proof was in her panties and there was no denying it!! I was more erect and turned on then I had ever been! I was leaking in her panties while I sashayed around for her, fully dressed like a girl!

My friend loved it and laughed so hard, which made me even harder and more aroused!

Ever since then I have secretly worn girls clothes. I have bought a decent amount of girl clothes and heels, but its more fun secretly raiding other women’s wardrobes and prancing around in their clothes and heels!

This is me secretly crossdressing and posing in the house of that same female friend that talked me into it all those years ago – here I was, years later…in her newer house(we no longer live together unfortunately).

She was away from her home, so I snuck into her clothes and secretly posed in her bathroom. I was very turned on, and felt extremely girly, and gay!! I have worn her clothes on more than one occasion, but never got caught. I kind of wish she had caught me and “forced” me to be her little sissy bitch boy!!!

Thanks for reading. Kisses to all, MUAH!!!

Xoxoxo ~ SissyToes

There is something exciting about playing with fire a bit. Being so close to being caught. I’d wonder if your friend would have the same reaction now as she did so many years ago. Tread carefully my dear.

Continue embracing your little sissy bitch boy self!

Diary Entry: Real Changes and a Sissy-gasm

There are real changes happening.

I noticed them Sunday night as I put my 5″ stilleto high heels on. I thought I would manage okay in high heels, but I couldn’t really walk, and I couldn’t control myself sexually either. That last one bears repeating.

I couldn’t control myself sexually in high heels.

Mistress Lillith had me purchase a chastity device and had been making references to sexual frustration and compliance in some of her messages, which sounds both fun and a little scary.

Prior to Sunday, I had been chaste since last Thursday. I had a pink ribbon tied around my clit.

It’s constant rubbing causing very mild irriation. I was wearing panties occasionally, and I dutifully listened to my mantras prior to bed–playing them on repeat with Mistress Lillith’s subspace hypno goodie as I fell asleep.

Sunday I had some alone time for the first time since … Thursday.

My shoes and cut-offs arrived on Saturday.

I put on the cut-offs with my tank top and thong underwear. WTH, size 31 is never tooooo big for me. I didn’t realize they would stretch so much. Okay that was a little disappointing.

How about the shoes?

Oh my gosh, perfect fit. The strap tied around my ankle, locking them in place. (The strap was surprisingly hard to lock and unlock!) I tried standing: my butt and chest instantly pushed out in opposite directions. Whoa, weird… and interesting. I took a few wobbly steps and realized I didn’t know how to walk in 5″ heels. “I’d better sit back down,” I thought.

Mistress Lillith’s twitter feed had showed some unusual NF activity for her on a Sunday, especially a holiday weekend. I thought there might be a chance of contacting her. I even tried reaching out to her on Skype, which I’ve never used before. No luck.

I purchased a tease and denial dice game video instead.

Stroking. Slow and fast. Alternating styles. It was clear there wouldn’t be a chance to orgasm at the end fo this video. On the last 5 of the dice rolls Mistress Lillith had me edge the number of times as on the die.

Pausing the video… stroking… staring at my shoes. Edge… Breathing… Again… Fuck, my shoes. A tiny pink ribbon bow sticking out from cut offs that were now riding up my ass. Edge. Again.

I was pulsating and twitching. An extra five dice rolls were granted, more stroking but ultimately denial. Staring at my shoes as I stroked… Oh no, I’m cumming. I tried to stand and to make it to the bathroom, but I COULD NOT WALK. ERUPTION. I collapsed in my chair. I completely lost control. Lost control of myself, of my feelings, of my arousal. I hardly recognized the view of my legs… a pink ribbon… a sticky mess… my shoes.

I completely lost control. Wow that was an intense orgasm. Shades of my teenage self. There are real changes happening to me sexually.

Diary Entry: Sissy Shopping and Thoughts

During part of the training, there is shopping that happens. That seems like a ‘DUH’ kind of expectation – but, with a new sissy you, you need a new sissy wardrobe.

Here was the diary submission for that week


The shoes from Yandy didn’t ship with the rest of the items Mistress Lillith assigned me to buy.

They were to come separately but there wasn’t a tracking number. I contacted customer support with the order number and inquired. A customer service rep named Linda, who had a girl in lingerie for her profile picture, emailed me an apology:

“Robert, the tracking number for *your shoes* is…” Size 10. My shoes. A thong string bikini and leather and chains were the other part of the order.

Kind of humiliating.

A review on for the leather and chains outfit was from a guy: “My wife looks great in this.”

Uggghhh… Super humiliating.

I asked Mistress Lillith for a little more time on this week’s assignment. She agreed immediately. I wanted to tease her as a pushover but didn’t have the nerve. I guess I did here.

I wonder if she’ll really push me and my boundaries. This is already as far as I’ve gone. I think I could probably cum just thinking about intense pyschological domination… Being told

“No. Get it done bitch.”

Yep that would make me cum.

This was a crazy week at work. A really positive, memorable one. But still one that sucked up everything from me. I wasn’t sure I could juggle everything I had going on. By some fortuitous circumstance I found myself alone for an hour. I could hardly believe it. “Okay, now or who knows when.” I thought.

Need to shave. Foundation. Eye shadow. Damn I messed it up again. Pink blush. That looks better. Hot “cocksucker” red lip stick. Mascara. 20 mins in. Makeup takes forever.

Slave 4 u by Brittany Spears played in the background and her music video was on my TV. I fumbled as I tied a string bikini for the first time. It didn’t cover anything downstairs! I set my cell phone up to record and walked, posed.

Next outfit: the leather and chains one. Oh my gosh. I kneeled. I got on my hands and knees. Whoops my balls made it in the shot. Now the black dress.

Stress was washing away somehow.

45 mins in. Time is getting tight, need to clean up. Rushing. Double, triple checking things–yes, all put away. Unbelievably I finished, mostly. Still have my shoes and cutoffs that haven’t arrived yet.

My body hair is growing back slowly. I really like my nude skin better than being a wookie. Waxing is expensive and painful but who knows. I have a week or three to think more about it.

I missed my mantras twice this week. Just completely forgot. I’ve tried to make up the time here and there.

I had a sissy dream on Monday.

These are RARE for me. In it my hands and legs were bound in purple blocks. My headphones were on and I was being forced to listen my sissy slut mantras.

Work meetings have been different too. I’m admiring women’s makeup and how they do their hair. That’s NEW.

I’m tired and still having fun.

Now you know why women are sometimes exhausted. It’s a lot of work looking so perfect! 😉

Diary Entry: Sissy Waxing, Part 2

My male ego NEEDED that blush.

That was a lot of femininity to absorb and that shot in the arm toward the end helped me recover a little.

There’s of course another possibility–one that is deeply erotically humiliating–but I still suspect my gut instinct interpretation was correct.

My legs and chest feel different. Actually super weird is more apt.

It’s the strangest sensation but I swear I feel like my legs are wet all the time, like I’ve just gotten out of a pool. Does hair soak up moisture or something? Actually I think what’s happening is in the past when dry, the hairs protruded a bit and on contact with something they would trigger the nerve. Previously when getting out of water the hair would be weighed down by the weight of water and pressed flat against the skin, and wind or something else would trigger the nerve. Now without hair, any brush against the skin is triggering a sensation has historically been associated with wet hair and my mind is confusing the two. At least I think that’s the explanation but I’m not sure. I keep reaching down to brush water off my legs but they are dry and smooth. WHAT IS HAPPENING!?

The strangest, most surprising thing I still quite can’t get over though is my stomach. It’s like I don’t even recognize it. I look down but I’m still not quite convinced it’s my stomach and my belly button. I can hardly keep my hands off of it, feeling the smooth foreign skin over and over again.

For the first 18 hours a red bump appeared in place of every single hair that was ripped out.

Jessica assured me those would recede and they did.

I have smooth hairless skin from my neck down (okay, my arms still have some fine hair and i didn’t have my armpits waxed or my bikini line).

While my shoulders are a little broad, I don’t quite have the physique of a masculine male… Not many muscles anyway.

I look feminine with my hairless skin. Dressed, I would look quite feminine. Dressed and from behind I would be indistinguishable from a female. I look like a sissy.

I’m acting and behaving girlier too: getting waxed, chatting about skin care with a pink haired girly girl, shopping for girly skin care products.

I’m acting like a sissy.

Something that’s kind of turning me on too is that the mantras feel different now. They feel … more effective and more real. Something about looking girly and doing girly things and having it repeated in my head is powerful.

I am a sissy.

It’s been a deep, erotic fantasy of mine for more than two decades to have hairless legs and a hairless chest. Always fantasized, never realized. That limit has just always been too far and out of reach. Until now.

My legs, chest and boobs look so much better too.

Thank you Mistress Lillith!

It’s amazing what can happen when all the sissy puzzle pieces fall into place.

Diary Entry: Sissy Waxing Part 1

I believe in Feminine Rituals. I am female, and I do engage in said feminine rituals on a regular basis. I believe that sissies must learn these rituals and complety them daily in order to live their sissy lives. How can you call yourself a sissy if you DON’T engage in these rituals?


Mistress Lillith’s rituals assignment is due in 1 week and I needed to get started early.

I searched through a few local salons–one that was super pink and girly and another that was more gender neutral–and settled on the gender neutral one. I called to book an appointment.

“Hi, I’d like to come in and have my legs and maybe areolas waxed.”

“We can do that. Are you looking for a brazilian? We can’t do brazilians for men, is that okay?” the receptionist asked. “That’s okay, I just need my full legs waxed.” “Okay, let me check with the beautician to see if she can fit you in today. Hold on.” “Okay, are you able to come in this afternoon?” “Yes, thank you.” And I booked the appointment. But…

2 hours later I received a call from the salon… “Hi Robert, I’m sorry, I’m new at this salon and I’m afraid the beautician isn’t comfortable waxing the entire leg. We do have another staff member that will wax your full leg but we would need to wait until tomorrow.” 🙁

… And the appointment fell through.

Needing a backup I called the super pink and girly and intimidating (but highest rated Yelp) salon in the area and booked an appointment. Everything was set.

Immediately after booking I received a call from the first salon’s manager. “Hi Robert, I’m sorry for the mix-up. We can get your full leg waxed today at a discount if you’d still like to come in.” Lol.

I think I might have inadvertently caused quite a stir.

This part of the story almost got deleted from the diary but made it in because–without passing judgement–I think the reaction caused by crossing gender boundaries is interesting.

The super pink and girly salon turned out to be super pink and girly. The entire area oozed femininity. Next door was a bridal shop. I entered the salon and approached the receptionist. There were a few women sitting in the fluffy pink and light green chairs and couches, staring at their glowing rectangles.

I was handed a new client form to fill out and given a bright pink glitter pen.

I was in foreign territory.

After finishing the form I handed it to the lady who would do my waxing: a young, cute bouncy, bubbly girl, who obviously cared about her makeup. Her dark green eye shadow extended out far from her eyes and then cut off sharpy at a 45 degree angle. Glitter shined from parts of her face. Her hair was HOT PINK and was pulled tight into a scrunchy that sat at the crown of her head, from there her hair flowed outward above her head like the stem above a carrot. This was Jessica. I was deep in foreign terriotry.

“Follow me,” she said. And we proceeded through the facility into the waxing room. “Take your clothes off. Leave your boxers or underwear or whatever you got on down there on. Lay down on this bench with your head on this end and I’ll be back in a few minutes.” I did as I was told. She entered after a few minutes and I meekly asked for a vanity towel and was obliged.

Something hot was being spread on my leg. “So why do you want to get your legs waxed?” the pink haired girl asked. Hmmm… How to answer this? … … My Mistress is feminizing me?

Probably not a great answer. I began to sputter something about my hair and being unsatisfied with it and suddenly in the middle of my sentence my lungs gasped for air and my speech was cut short as sharp pain shot up through me like a lightning bolt. “uuuuuuggghhh…” I ended my answer prematurely.” Jessica giggled.

HO-LLE SMOKES. Waxing hurts. A. LOT.

I had read reviews about it being bad but I was genuinely surprised how much it hurt. Jessica and I made chit-chat the entire time. She was young, not married, into music, gave me tips on skin care and exfoliation, had 3 male clients and blah blah blah. I was constantly having my speech cut short by sharp pains as hair was ripped out my skin.

My nerves were on fire. “Maybe I can’t handle BDSM pain,” the thought occurred to me.

It was hard to stay focused on what was happening and not daydream about why I was here getting waxed. Fortunately I managed to stay soft and OH MY GOSH am I thankful for that. Finally after two hours it was over.

As I was paying the receptionist and getting ready to leave Jessica came to the front desk and reminded me: “Don’t shave it when it starts to grow back. Let it grow for 4 to 6 weeks and then come back and see us. It won’t hurt as bad next time. Use an exfoliater tomorrow and moisturize afterward.” For the first time since arriving I looked her in the eye and thanked her. Something curious happened next.

Jessica turned bright red as she smiled, looked at the ground suddenly, mumbled a thank you, and then hurried out of the room.

Jessica blushed hard! I wonder… (to be continued)

This part of the training always cracks me up. Obviously I don’t expect ALL of my sissy trainees to get waxed, there are work around and other rituals. But the ones that DO go out and get a wax, are always in for quite a sissy adventure.


Diary Entry: Sissy Bottoms Should Never try to Top

During week 2 of Mistress Lillith’s training she had something come up IRL that rightly required her attention. They were a difficult 7 days for me. I was new to her training and felt like I needed a lot of instruction, boundaries, a lot of structure. I remember watching several videos of female subs being flogged by dommes and other tops (most subs are females, it now occurs to me). Strangely, it had a deeply soothing and reassuring effect on me. I vividly remember watching some of these videos and reading about d/s relationships and thinking “I just need to wait patiently for my Mistress.” But this was all being created in my own mind and I actually have little experience with this type of relationship and so doubt crept in.

How should I be behaving?

In week 4, after completing a particularly arousing assignment, I lost my composure. I was pining hard for Mistress Lillith. She is more experienced than I am and has a better understanding of our relationship and what is objectively happening.

I am less experienced and it’s easier for me to confuse our relationship and get carried away by some of the most powerful feelings a person can experience.

I had expectations and made demands of Mistress Lillith.

I think my reaction was a typical pyschological one. But it was not acceptable for a sissy bottom. And I have goals to be a better sissy bottom.

“You are the submissive. I am the Mistress. You came to ME with a need. Follow my lead. Period.”

Yes Mistress. It’s what I needed to hear.

“You belong to me.” “I’m okay releasing you should you feel the need.”

Ownership. Consent. Thank you Mistress.

OMG Mistress Lillith sent me a personal video too (what an amazing domme!!!).

“I am your Mistress. You fucking belong to me. You want to be my bitch? You want more of me? I hope you’re ready.” “You serve me. Not the other way around.”

Yes Mistress.

Sometimes when a newer sissy is going through sissy school and training with me, they will have new and intense feelings that will overpower them. Think of renewed hormones, thing of that teenage angst. It is very similar to that.

Yes, it is important to understand that Dommes, Mistresses, your Sissy trainers, they are people too- there are lives that we have and live outside of our sessions – be it online or in person.

While the feelings can be very intense, and you can have a very strong connection with your Mistress – and right then and there she may be your whole world – understand there is more to the picture. I don’t always share with my subs and sissies the ongoings of my personal life – in this instance I was taking care of an elderly family member that had been hurt. Why do I share this? Simply to say – don’t act as though you are the center of the world or the one and only thing that she is focused on. You could actually damage your relationship with your Mistress by making demands and assumptions.

Here, this sissy was learning. Im slow to anger and adore this sissy – she just needed some redirection.

I am the Mistress, I am the Sissy Trainer, it is I who will be obeyed and I who make the demands. NOT the other way around. 

Exposed Sissy: Lisa

Sissy Diary Submission from Sissy Lisa – aka MARK

My sissy journey started at a young age, when I raided my Mums panty drawer. The obsession started and I fell in love with the feeling of soft feminine items.

All these years later and now I wear panties 24/7 and wouldn’t have it any other way.

I love slipping in to a nice dress and matching them with tights and sexy heels.

We girls deserve to feel great and look amazing.

I regularly go for long walks at night dressed in sexy outfits, always with tights. It’s my dream to be able to go out on these walks during the day.

I love exposure and humiliation but always come back to my Twitter account and delete it, this allows me to be exposed and I can’t do anything about it.

That is such a wonderful feeling and one I crave so much. After years of dressing I decided I needed to get out and meet guys, I wanted cock so bad and I’ve had my fair share. So far I’ve met 14 guys and enjoyed a mouthful everytime.

I want a boyfriend one day who I can snuggle up to and suck off at will.

I would love everyone to share my exposure and love have sissy chats with others.

I used to think this was just a phase and I would go back to women but I guess being a pathetic sissy means I’m totally gay now.

Thank you Mistress Lillith for allowing me to submit my exposure

When you mentioned that you would ‘go back to women’ I snort laughed out loud. No one is going to accept you as some ‘macho stud of a man’ – there is no going back my dear. 

Once a Sissy, Always a Sissy

Diary Entry: A Stern Chat and Redirection Pt. 2

Something’s is different with me. The past couple of days my go to search term alone at night is “sissy sex slave” or “submissive sex slave”. But this is new. Despite years (or decades?) of a sissy fetish somehow I’ve managed not to follow this route so much.

The chains, and whips, and bondage. The humiliation. This next paragraph invovles EXTREME humiliation so the reader is asked to just skip ahead if neccessary *^-^*

Thursday night I came across a video called “Slave Training”. It appeared to be taking place in a cellar, or a dungeon. It didn’t quite seem like an amateur video, but it definitely wasn’t a professional shoot either. Perhaps the recording equipment was slightly higher quality or more accurately the players in the scene clearly did this type of thing as a lifestyle. A woman was naked on her knees on the concrete floor. Next to her holding her leash was a dominatrix, her shoulders covered in leather and thin chains drapped around her body in loops. She was orchestrating the entire scene. She was in control. Mutlipe cocks extended out from behind a black curtain hanging from the ceiling on one side of the cellar. One after another the dominatrix forced the slave girl’s mouth on to the cocks, pushing her head down on them and slapping her a little. One after another after another the slave girl was dragged down the line, choking on each man hidden behind the curtain. Few words were spoken. Next the slave was moved to the middle of the room, and then suddenly, the curtain was ripped down by the men standing behind it. 7 or so of them stood there stroking themselves, staring at her. The slave girl gasped and stood to her feet, only to realize her role again and get back on her knees. What happened next has stayed with me. The domina got on all fours in the middle of the cellar in a submissive position. Another top came up behind her and placed a bulb of a whiteish enema type liquid in her ass, filling her with it. The dominatrix tugged on her slave’s leash, bring the slaves face inches from her ass, close enough to smell her. And then, she expelled the liquid in bursts all over the slaves face. One after another after another…. White-ish liquid expelled from her ass, soaking the slaves face and hair. The slave was shaken. She was visibly shaken. This wasn’t acting (or it was professional level acting). This was hardcore kinky shit among, I think, players in the lifestyle who video tapped themselves breaking in a sex slave and then posted it on the internet, maybe making some money along the way.

Speaking as a submissive, I’m like 100% certain that I would NEVER be able to look that dominatrix in the eye, or make chit-chat, or do anything but SUBMIT and OBEY if she had orchestrated a scene like that with me in it. She would have completely and utterly broken me. That was some hardcore power exchange and humiliation.

How is this diary entry reflecting Part 2 of Thursday night’s chat? That’s a good question and I’m not sure it is honestly. So maybe my writing got away from me a bit.

Mistress Lillith and I made a connection on Thursday night. I gained a better feel for her as a top and a person, and I saw a side of her I was hoping to for a while. I’ve been savoring it and replaying it over and over again in my mind. In all seriousness, I feel like I’m taking a first few steps into a lifestyle of becoming a sissy sex slave.

Let’s say I complete Mistress Lillith’s training two or so months from now. Do I ever come back from it and suddenly not be a submissive sissy? I don’t think that’s a realistic outcome. There’s also this itch to submit as a bottom. This training is altering and refining my sexual identity. And I’m excited.

Once you are a submissive, you will always be a submissive. You don’t really come back from it. Let’s say that someone does the inevitable sissy purge…you are still a submissive. PRETENDING to NOT be a submissive or pretending to NOT be a sissy, doesn’t make you any less of one. All it means is that you are living in a state of denial.

Complete the training and you have a firm grasp and foundation of what is expected from a sissy and how to be a sissy – afterwards, we get to have the real fun and explore beyond the basics of sissyfication.

Sissy Diary Entry: A Stern Chat and Redirection Pt. 1

Something happened….

Mistress Lillith was on NF earlier than usual, mostly because of my asking I suspect but it’s hard to say. I sat around at the chat window hoping, pining she would join the chat.

Mistress Lillith is typing a message…

The purple text read. Excitement coarsed through me. I had questions I wanted to ask her, some I had fantasized about all day. As nonsensical as it may sound I specifically wanted to try and playfully draw out her dominant side. I thought I had some good questions.

First the makeup assignment. That was a mess on my end. Next, I asked her about being a better sub. I was saving my favorite question for next but waited for her reply.

Honesty, integrity, and follow-through… Sissification is one of my specialties… But if I don’t connect with the sub or sissy it isn’t going to work.

Oh no, what could this mean? Maybe she was monologuing?

For example I was going to send you a little message [to correct something you said]

And as she typed and typed for about 4 mins in chat, it suddenly occurred to me I had done something wrong and I said as much in chat.

I don’t like anyone using a forum to speak well of me and insult others . I feel what my subs do in public or say about me does reflect me and im one that expects you to respect all others.

Oh shit. I was not expecting this.

Some want to put others down, some don’t care… I kind of do…. Just as I have to sift through some bad seeds to the rare gems (such as you my dear sissy)…


Subs have the same task and… we hope we find each other… Never think that a put down of others is a compliment to me.

The seemingly innocuous feedback read: “Her knowledge of the submissive psyche, and experience with a variety of kinks and fetishes is a huge step up from a lot of the amateur dommes.” I had even specifically purchased one of her teaser clips just so I could leave that specific feedback to share publicly. Really, really unlucky.

I was a little stunned into silence. I felt a pang of shame at my behavior. There was some truth in her criticism. She had a philosophy on the topic I had not considered before, something she must have dealt with for years. Something deep. Something, I suspect only now as I type these words, around the challenges of the sex industry. I had accidentally hit a nerve.

Another feeling began to well up inside of me as I sat at the keyboard in silence. A feeling I’m not sure Mistress Lillith will like to read but it was there true enough… I felt turned on.

I’m like 99% sure her feedback wasn’t intended to turn me on. It read and felt like genuine disappointment. But it did.

She flashed her dominant side. It wasn’t soft and gentle and playful. It was direct and critical and strict. And sexy.

The idea of Mistress Lillith calling me her sub and the emphasis on changing my behavior publicly because I was a reflection of her and her training… It made me hot. What else can I say? It made me hot.

I wanted to send Mistress Lillith a tribute for her time but I worried about the implication of tributing now. Would she think I was using money to apologize for the mistake she clearly cared about?

I sat in silence and also wondered about asking my favored 3rd question I had planned all day: “What would you do if I disobeyed you?” How would this question be interpreted now?!? The timing was all wrong!

Even the simplist missteps no matter how well meaning, will be addressed by me. Part of Sissy School is to learn how to act and behave in all aspects. That is part of my submissive training all in all. I know my darling sissy meant well, there is not a bone in my body believes that she meant it as an insult or backhanded compliment. She was genuine. However, there is still an aspect that needed redirecting.

I will always redirect. How a sissy that belongs to me or a submissive belongs to me acts in public forums is an almost direct reflection on me. SO, I expect you to walk with poise when my name is attatched. In any way, shape or form.

Of course, she was in a fiesty mood this day so any kind of redirection was going to be a bit of a turn on – she had clearly been yearning for something a little more strict. LOL

Exposed: Sissy Penny

I am a 35 years old closet sissy with an athletic body trying always to look as sexy as possible.

My goal is to look feminine and not just a man in lingerie.

I adore women and the main reason I crossdress is trying to look like the girlfriend i would love to have. I love skin tight clothes and i adore high heels.

I want to find a girlfriend that will love me the way i am.

I always fantasized about being in chastity by my girlfriend and where that could lead me. I do not like men and do not wish to serve one also.

I consider my self a man with fetishes one of which is crossdressing. It is not a mandatory fetish but one that can spice things up a bit. I don’t know why I made this submission, I guess I needed to confess my feelings.

One of my fantasies is to be dressed as a maid in ballet boots, on a locking corset and in an arm binder with a locking gag as well locked in chastity and forced to serve my girlfriend and her friends in a kinky party.

The need to be trained in becoming a better serving sissy is something that exists in my mind for quite some time now and hopefully in the near future this will be a reality.

I hope you all loved this diary submission and hopefully this will persuade many more to do the same.

With Love Sissy Penny. <3

Thank you for sharing! It’s important for everyone to understand that not all sissies/crossdressers/panty lovers/ etc are made alike. There is no such thing as a one size fits all box.

Many of us fetish lovers and seekers just do it because we like it, we want it and we are going to engage and enjoy.

I hope you make that connection you seek that goes above and beyond. Best of luck, Doll!