Sasha : Sheridan's Sissy
Would you please tell us about yourself?
I'm a young, single guy from the UK, with a full-time job and a regular social life. And yet, despite normal appearances to my friends and family, I also enjoy crossdressing and being a devoted sissy slave to the divine Princess Sheridan. I have a few sissy names. Sasha is the identity I'm particularly focused on now, and it's a wonderful name Princess chose for me. But I also go by the name Glenda, which I chose a bit randomly really, as I simply liked it when I saw it. And Princess also uses the nickname Fucking Faggot when She's humiliating me.
Apart from that, I enjoy a lot of classic rock and pop music (ABBA, ELO, Lynyrd Skynyrd, Queen, The Who, etc), comedy (Monty Python, The Two Ronnies, The Big Bang Theory, Family Guy, etc) and action dramas (Doctor Who, 24, Chuck, Prison Break, etc). I could carry on for hours, they're just tiny examples of what I like. I'm not particularly into chick flicks, girly music or stuff like that, despite how I like to dress. I'm not religious, I consider myself an atheist, and i don't get heavily involved in politics, though I do exercise my right to vote of course. And I'm not particularly sporty either, though i do enjoy watching big events like the Olympics, and I enjoy playing pool and ten-pin bowling with my friends. I should get more exercise really. But I'm happy with my life as it stands right now, it's going well.
Do you believe you were born submissive?
Not really. I think it's been influenced by my life experiences more than anything. I was very shy as a kid, partly because I struggled at school somewhat and was a prime target for bullies in my earliest years. It was a huge knock to my confidence, and it took quite a while to come back from that. I'm fine now - still a bit shy, but otherwise it hasn't stopped me doing well in life, which is why I'm happy as things stand.
Nevertheless, I've always found it hard to take control of people and situations, partly because of that background. I struggle with my confidence in those scenarios. I'm generally more of a follower than a leader. And I'm happy with that, that's where I feel most comfortable. So I guess that's filtered into my kinky side, along with other factors I'll deal with in the next questions. Or maybe it's nothing to do with it - I'm no psychologist. But it seems logical to me.
How and When did you figure out that you are a submissive male?
The first big awakening of my submission was down to a girlfriend I had in my college years. She had a wonderfully playful and mischievous streak, and we got very hands-on with each other, to the point where I was lucky to receive a few handjobs from Her. It was on one of these occasions, in order to prevent her hands getting sticky, that She decided to pull her hand out of my underwear at the point of no return, leaving my cum to dribble out into my boxer shorts. What you would call a ruined orgasm, though we didn't know it was called that back then. Not only that, but we were staying in a boarding house with other people, and we were in the communal lounge area when doing this sometimes. So I had to rush to my room and change my clothes before anyone came in.
It was very amusing for Her, because it was very embarrassing for me. And yet I rather enjoyed it too. Getting a handjob and the risk of almost being caught were thrills in themselves, but there seemed to be more to it than that. I loved the way she was controlling me. I was turned on by it, though I couldn't explain why, and I wasn't really aware of BDSM terminology at the time. I was just enjoying it, and I allowed her to do it to me a few more times after that. I still felt embarrassed every time, but I never had a strong urge to stop her, even though I could have done very easily.
Some time back, Princess Sheridan did a re-enactment of this scenario for me in a custom video, pretending to be my ex-girlfriend. Her idea, it must be said, and it worked wonderfully. I've written all about it in my blog (good excuse as any to give it a plug, lol):
http://sheridanssissy.blogspot.co.uk/2015/01/history-repeating-part-1.html
http://sheridanssissy.blogspot.co.uk/2015/01/history-repeating-part-2.html
It was only when I realised that I was a sissy, though, that I truly understood that I was a submissive as well.
How and When did you figure out that you want to be a sissy?
In the relatively brief period where I was small enough to fit in my mother's clothes as a kid, I tried some of them on out of curiosity, and found I rather enjoyed it. Not sexually - i was too young for that - but it was simply fun. I wasn't able to do much, and it didn't last long, but it stuck with me. I liked women's clothing, there was something so beautiful and intriguing about it. It was so different to all the male clothes I wore. Whenever I looked at women on TV or in magazines, not only would I admire how beautiful they looked, but I also found myself wondering how I might look in those clothes. I never thought I would ever explore it further though, I figured I'd be too busy with other things in life as I got older.
When we eventually got the internet at home, though, around the time I started university, I naturally started looking into porn. What guy doesn't? And like any guy who first discovers this treasure trove of online sexiness, I loved it. I didn't have any particular fetishes at the time, I just enjoyed regular sexy porn. So far so normal.
Somehow though - and bear with me, this is relevant - I stumbled upon the Wet And Messy (WAM) fetish. I hadn't realised it was a genre of sexy play, but I had always enjoyed gameshows where people were pied and gunged, so it was always appealed to me. And so I was fascinated by this new discovery and loved exploring it all. That was my primary focus for a good couple of years I'd say.
But within that I found a sub-genre of material - men being dressed as women, sometimes by forceful, dominant ladies. It didn't come up very often, but the more I stumbled upon it, the more aroused and intrigued I became by it. Terms like "forced feminization" and "sissies" were completely new to me, but when I Googled them, doors immediately started opening to lots of amazing places - sissy sites, picture galleries, clip stores, etc. It appealed to me hugely. I loved the idea of being forcibly dressed and humiliated by a Mistress, as well as just being a submissive to a Mistress in general, so i realised this was exactly the sort of thing i wanted.
As I delved into it, learnt all about it and got more excited by it, I eventually got up the nerve to buy a few feminine things of my own and sneak them home to try dressing up a little bit. That just confirmed everything. It was fun and it turned me on, I was very happy. And still am.
Of course, I continued to explore and picked up a few other fetishes along the way - Jerk Off & Cum Eating Instructions, Forced Bi, and Humiliation in general all became big favourites. And Princess Sheridan has got me into even more things, like Foot Worship, which I hadn't paid much attention to before. But sissy play has always been the big one to me, the central pole around which all my other fetishes revolve.
Goddess Lindsey Leigh once said “Sissies are the cheapest [lowest] slaves.” What do you think?
And a wonderful Mistress She is too. Prior to devoting myself to Princess Sheridan, Goddess Lindsey was one of the many dommes i had enjoyed clips from. So i have a lot of respect and admiration for Her and all dommes out there, as noted in a later question.
I see where She's coming from with the quote, but it is a very sweeping generalization. Not all sissies are slaves, and some sissy slaves are extremely clever and talented while others find it a real struggle. Some sissies find it really easy to be exceptionally good looking, while others have a hard time with it - and a few even enjoy looking as pathetic as possible on purpose. There's a whole spectrum of sissies out there, we're certainly not all alike.
In general terms, though, are sissies the lowest type of slave? It is true that, instead of acting like real men in any way, they try and be feminine and slutty instead, maybe even prostituting themselves to make money for their Dommes. So for a superior woman looking for a real man, a sissy is arguably as far from that as it's possible to get. But still - the lowest? What about toilet slaves? Stooping to the level of eating a Domme's waste to get your sexual kicks and some attention from Her would seem lower to me - and it is something I've happily fantasised about doing for Princess Sheridan, so I have nothing against those thoughts. But it would seem much less likely for a normal person to consider doing that, whereas crossdressing is actually quite common in comparison, and slightly more socially acceptable these days.
Do you believe there are levels in submission, so there will be alpha slaves that are higher than others?
There are certainly levels in relation to how experienced each slave is. New, keen, wannabe slaves are very different to long-term, veteran submissives. And some slaves do have a dominant side to them - those that are called switches, in other words. Mistresses may also have their own favourite slaves who they regard as being above the rest in their collection, but that's an individual decision for each domme.
Other than that, though, each slave is a unique individual, and a good Mistress will treat them as such, focusing on their particular fantasies and avoiding their limits. Every slave has different talents and abilities as well, which again a good Mistress will make best use of. Among Princess Sheridan's 'fucktards', for instance, Yuri is the whizz of graphics and body-writing, while Widdledick is awesome at building things and being musical, and I spend much of my time writing reviews of all Princess's clips and making things like captions and videos. And there's this guy into ballbusting who's rather good at doing interviews and reviews of clips by various Mistresses... can't think of his name now... ;)
Have you ever tried to be a top?
A little bit, here and there. I've tried it on sissy sites in the past, creating a dominant persona anonymously (so the friends I already had there didn't know it was me), and seeing how it went. I didn't do badly and I enjoyed experimenting, but I did still struggle with it. So I never got into it in a big way. It's down to the confidence issues I was talking about earlier, and the fact that I'm always inclined to be nice to people. So I'm always scared of saying the wrong thing - either being too mean to them, or not being as dominant as they were hoping for.
And I've never been overly confident in my creative side - I tend to think the 'creative' things I do are too basic or obvious, or just not as clever or exciting as the things I see other people doing. Princess has helped me deal with that to a large extent, and I have produced some things for Her that i'm proud of. But my self-doubt still gets me sometimes.
All that said, I am working on developing my 'switch' side at the moment, with Princess Sheridan's expert help. I probably shouldn't say too much right now, but it's all part of a wider plan for me to try and make more money for Her. I did a test photoshoot for Her with me in some dominant poses just before Christmas, and we were pleased with what came out of it. So who knows? It'll be interesting to see where that leads. I'm looking forward to playing around with it, to see how I get on.
When was your last time you had normal sex?
Never, I'm still a virgin, and I'm happy admitting that. The closest I ever got was the girlfriend I told you about earlier, so I can at least say I've touched that part of a girl before, even if it was very briefly. I've been single since then - partly out of shyness, but mainly because my family and I have had plans which really need to be sorted out before I can properly look at settling down with someone. Fate has made that more than a little bit difficult, it must be said, and if I'd known it would take this long at the start, I would have done things differently maybe. But, still, things are finally heading in the right direction at present, hopefully...
What’s your favourite fetishes and what are your limits?
Forced fem, forced bi, jerk off & cum eating instruction, humiliation and body worship are what I would consider my top 5, if you hadn't guessed already. Having my appearance, masculinity, sexuality and orgasms controlled, and having to debase myself to make women happy, are all things I enjoy. And in terms of a woman's appearance, I'm a sucker for tight-fitting clothing, sexy leather outfits and schoolgirl uniforms, to name three things that particularly appeal to me.
Financial Domination is also a core part of my servitude to Princess Sheridan, as you'd expect, though I don't think of it as a 'fetish' as such. To my mind, I'm simply showing Princess the gratitude and appreciation She deserves by spoiling Her, as She's worth every dollar and more. But I do get a thrill out of it as well, of course, knowing that it's making Her happy. That said, however, it is also very important to say that I'm very careful about how much I spend on Her. I pay Her a lot, but only what I can safely afford at any given time, a rule that all paypigs should follow. It's very easy to get too carried away if you're not careful, so always monitor your spending carefully to be safe.
As for limits, I don't like heavy pain play. I don't mind fantasizing about Princess punching my balls or beating me up, that's still fun, but I would never really want it to happen. So when I'm commanded by Princess to slap my face or balls (in a clip or during a chat), I don't do it particularly hard, just enough to sting a little. I also wouldn't want to have any body modifications like tattoos or piercings, I've never fancied those. They look great on Princess, but not on me. And smoking's my big turn off - I'll never do it, and I don't like it when a Mistress does it either. It kills the mood above anything else for me.
I managed to create a fetish checklist page in my blog some time back, which will give you even more of a sense as to what I'm into:
http://sheridanssissy.blogspot.co.uk/p/fetishes.html
Have you ever been with a professional Dominatrix in person? How was your first experience?
No, but I really want to. It's a long-standing dream of mine. Even if, for some reason, it turns out I don't like it, I want to try it at least once. I'd rather do that instead of getting to a 'what if' stage later in my life, wondering what might have been.
There are a couple of friendly people online I've met through Princess Sheridan, who I'm hoping I might get to meet and become good friends with in person one day. And in turn I'm hoping that might eventually lead to a bit of fun playtime, with me in a submissive role. So there is potential there. But I would also love to visit a dedicated professional dominatrix, who has playrooms or a dungeon and all the stuff that goes with it. It would be a completely different and much more intense experience to serving a Mistress online, I know that.
Don't get me wrong, I'll always be devoted to Princess Sheridan, and I would only do things like that with her blessing. But it is definitely a 'bucket list' thing for me, I have no doubt about that. Where I live now, it's simply not possible to do it, but in the coming year or so, I'm hopeful opportunities might start to open up a bit.
From one Slave to another, what is your advice for the newbies to be better slaves?
1. Be respectful. Be polite and acknowledge that the domme is superior. If you're rude, impatient, bossy or demanding, it really won't go down well. And for goodness sake, don't send them dick pics they haven't asked for. There isn't a single domme who wants that, believe me.
2. Communicate clearly. The domme/slave relationship requires a lot of work on your part too, and dommes are not magical mind readers. You need to help them understand what your fetishes and limits are, so they can build on them to give you the best experience possible. Never just say you'll do anything, as it makes their job so much more difficult. They need your guidance to know what's going on inside that dirty mind of yours, so they can fuck with your head in the best possible way.
3. Show your gratitude. If you're enjoying yourself with them, make sure you regularly express your gratitude and admiration for them, so they feel appreciated. Words are obviously very important here, as they need your feedback. But the most important thing of all is your money. You absolutely must make sure you pay them for their time and effort, and a decent amount to. It's their job, after all, for which they need and deserve the income. So if you're not prepared to spoil them and you try to avoid paying, they won't be interested in you.
I'm sure there are other points, but those are the 3 that immediately spring to mind. It all comes down to the basic point of showing respect really, which you'd think is common sense, but there are so many wannabe slaves out there who fail to consider these basic things, or who assume they can get something for nothing.
When you purchase a clip that has tasks or orders, do you care to follow every step or you jerk off to the hot lady?
I prefer to do them if possible, but it depends on the tasks really. Things like JOI, CEI, line/body writing are easy. But some tasks have to be altered or avoided for whatever reason - e.g. if I don't have the items needed, or if they'll impact on my limits or privacy. Sometimes it can be hard to predict what you'll need as well - if the clip's description doesn't give you a sense of what's required, it can be frustrating to buy it only to discover you can't do it. But then you don't want clip descriptions that give everything away either, so it is a hard balance to get right sometimes. And it is still fun to jerk off to task clips without doing them, but it does defeats the point a bit.
Princess Sheridan always writes good descriptions for Her clips though, and I always try to complete Her tasks as best I can. Where possible I send Her proof and/or write a detailed blog post about it as well. But sometimes I have had to adapt them - e.g. only lightly slapping myself for CBT tasks, using washable instead of permanent marker for body writing, etc. There was also a challenge involving a toothbrush, toothpaste and a condom, for which I deliberately avoided the most painful element. Princess would much prefer it if I'd done it, of course, but we discussed it and She understood my reasoning. And it gave Her more reason to humiliate me for being a wimp, which is fine by me, I love that stuff.
Of course, there are also one or two of Her clips where the task involved isn't meant to be taken seriously anyway - e.g. being forced to eat your own waste or play with scissors while jerking, which have been custom requests. Things like that are deliberately meant for jerk off purposes really. But the vast majority of tasks Princess dishes out are achievable and safe, from simple JOI to more elaborate offerings.
When you are on a clip store, what’s the first thing catches your attention; preview picture, fetish category or description?
The title and preview picture stand out the most first, and I'll have a quick glance at the categories as well. If I'm still tempted after all those things, then I'll delve into the description. It's a combination of the description and preview image that ultimately swings a purchase decision for me. A good animated preview GIF can be particularly powerful I find, as they can be very arousing in themselves.
Of course, now that I serve Princess Sheridan, I simply buy every clip She makes, because She's wonderful and I'm her slave. So there's no decision making involved in that sense. Granted, there are one or two themes that don't appeal to me so much, which is inevitable given the amount of material She produces and the variety of custom requests She receives. But 99% of Her clips are a big turn on for me. Even clips involving tasks I wouldn't want to do are still exciting to watch, because I can easily enjoy the fantasy and keep it separate from reality.
You are a devoted sissy to Princess Sheridan. Would you please tell us how that began?
Having enjoyed hundreds of videos from clipstores over many years, I had been wanting a custom clip of my own for ages. But it took me a long time to pluck up the courage to get one, and to decide on which domme to spend my hard-earned money on.
When I did eventually pick someone, it wasn't Princess Sheridan. I won't say who it was, but they were wonderfully friendly and the custom I got was truly amazing. So I did give serious consideration to becoming a slave of theirs. And had I done so, it would have been great fun I'm sure. But I couldn't shake off a nagging feeling that maybe they weren't quite right for me. And when looking at the times they tended to be online, it became apparent the time difference between us would make it very difficult to have any live chat sessions.
So I decided to try someone else, as I could afford it, and it would be fun to compare styles. So I looked at the other options I'd been considering, and that's when I turned my attention to Princess Sheridan. I'd been tempted by Her before, because She's incredibly sexy, Her custom pricing is very reasonable, and She'll edit out your name for store versions at no extra charge. I loved Her website too, including all of Her wonderful pictures, plus a page of fun task ideas that seemed perfect for a beginner like me to try out.
I'd been too shy about going to Her originally, because I'd been a little worried Her style might be a bit too harsh for me. But now I'd experienced relatively light humiliation in my first clip, I felt more tempted to try a more bratty approach this time. So I got up my nerve again and emailed Her - and to my amazement She got back to me just a few minutes later, kindly accepting my request.
Suffice to say, I adored the custom when She delivered it! She didn't just push my buttons, She hammered them home firmly. So I took it to the next stage and started going through the tasks on Her website, sending Her the required tributes and evidence of their completion. That led to Her following me on Twitter (which I was also new to at the time) and we got chatting from there. The rest is history, and I've never regretted it since. :)
How long did it take her to enslave you?
Only a couple of weeks. I first emailed Her on May 8th 2014, She delivered the custom on the 16th, and I created my slave certificate on the 22nd. She hooked me in very quickly. I still thought about it carefully before making it official with the certificate, of course, but I knew She was right for me, everything just fell into place. And I had nothing to lose by trying it, other than some money and dignity. I would only have regretted not trying it later.
Did she turn you into a sissy? Did you ask for it?
I was already a sissy. I already had panties, lipstick and a dildo handy to begin with. So I asked Princess to train me to be a proper sissy slut. It's safe to say She's been rather good at that, as you'll hopefully see from my blog (http://sheridanssissy.blogspot.co.uk). Over the past year, She's taken it a stage further and turned me into a 'rubber doll' - in the sense that I now own a rubber hood with pigtails. Apart from being fun to wear and keeping my real face private, it also gives me a sexier appearance. And we're hoping that will help me make some money for Princess when I try making videos She can sell. That's our big goal at the moment - one that still needs work and is limited in some ways given my living arrangements, but we've been making very good progress. It's been very exciting to see it coming together, bit by bit.
How do you feel about other dommes?
I love them and have a lot of respect for them. There are some who appeal to me more than others, naturally, and Princess Sheridan is the only domme I spend money on now of course. But I have great admiration for every single domme out there. Being a successful Mistress (or Master) takes an incredible amount of dedication, time, effort and creative energy. It's not as easy as they make it look, and there are lots of idiots they have to deal with along the way. So they deserve all the praise they get, I could never do what they do.
If you want to tell a new submissive boy about Princess Sheridan, what would you say?
That She's incredibly beautiful, creative and fun. She'll degrade you, test your limits, fuck with your head and drain your wallet - and it will all be done in the most wonderful way possible. You may well be scared and humiliated - but you'll also be safe and happy, I can assure you. She knows how to get the balance right so it's fun for Her and for you. So don't be shy. Just be respectful towards Her, spoil Her and obey Her, and you'll have such a rewarding experience. I appreciate I'm biased in saying all that, but it is all true!
Is being a sissy something you will continue in your life? Or do you think about having a girlfriend in the future?
Being a sissy is something I do purely for fun. I'm fortunate that I don't feel any conflicts about my gender or my sexuality, and I have no desire to become a full-time sissy or girl. I'll never have any hormones or surgery or anything like that - they may be mentioned in custom clips occasionally, but extremes like that are purely fantasy. I just dress up and act like a sissy slut in my spare time because I enjoy it.
So yes, I do hope to get a girlfriend one day, and I'm confident I will do so. I'm still a man and I do get on well with the opposite sex. And, sure, I would probably stop my sissy play if things got serious with a girl, unless I somehow discovered She approved of such things. My sissy side will always be part of me and is something I'd have to deal with, I realise that. But sharing my life with a beautiful, loving woman is far more important to me in the grand scheme of things. I'd be envious of her in her wedding dress when we get married though! :)
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