You're A Cuckold And That's Okay

You want her to be happy.  You love her so much you would do anything for her, and she loves you.  Being a cuckold isn't for everybody.  Some get the wrong idea it's about her hating her sissy, and that's just not the case.  Not for all of them anyway.

The sissy may feel inadequate.  Maybe sissy can please her just fine, but sissy feels it's not enough.  She wants her to really get off for all the happiness she gives her sissy.  I mean, she has dressed sissy up nice and pretty.  Maybe she's even taken sissy out all dressed up.  This is because she lovers her sissy, and being pretty makes sissy happy.

Maybe she went even further and used a strap on with her sissy.  Sissy just loved it.  Being locked in chastity, sissy experienced a different kind of orgasm, much more intense when Mistress used her strap on.  Sissy loved it so much that Mistress does it for her when it's needed.  Sissy has become an oral devotee.

So much so that sissy seemed to get a kick out of it when Mistress suggested making sissy please a guy.  Then, Mistress was there to make it happen.  A nicely endowed guy, and her sissy's lips wrapped around his manhood.  Mistress encouraged sissy to make him cum, and when he cums, sissy swallows it for Mistress.  Mistress is so proud.

So, here sissy sits with a man in the bedroom.  Mistress is doing what sissy recently did, pleasing him orally.  But it won't be her mouth he cums in.   Not this time.  Sissy is exited, because he is pretty well endowed.  Sissy feels lucky to get to see Mistress being pleased in this way.  She can tell Mistress loves every moment of it too.  Then, he cums inside her womanhood just as she has an orgasm too.

Sissy can only watch in chastity, leaking but unable to finish herself off yet.  Mistress calls to sissy as her lover leaves, and sissy knows what is required.  She must clean Mistress up, and she does so with glee.  She loves every drop as she tastes Mistress and her lover, mingled together.  Sissy thanks her for the treat.

Mistress is proud of sissy and allows her to cum.  Mistress knows sissy is way to exited to last, so she makes sissy stroke it in front of her.  Mistress allows her the honor of cumming on her pussy, and once she does, she orders sissy to clean it all up. 

Mistress is proud of her sissy as she tells her, "We will be doing this again."

Sissy can't wait.  She wonders when she will get to have sex with Mistress again, but she is happy that Mistress is going to be pleased by somebody else.  At least she'll get to be there.  Who knows, maybe Mistress will make her suck her lover next time.  She's excited about the idea, but she can't do anything locked in chastity once again.  She considers herself a lucky cucky.

Mistress Brings Her New Sissy Assistant Into A Session

Mistress Clara was a vision to Tiffany in her black shape wear dress with her long black hair tied back in a bun.  Clara wore glasses that gave her more of an air of authority, not that she needed it. She was already somebody who commanded respect.

Clara had a heart of gold, but when she lay down the law to a sub or a sissy, she was all business.  She looked over her sissy Tiffany's eye makeup.  "You look very pretty."

Tiffany smiled and blushed. "Thank you Mistress."

Clara gave her a stern look.  "Now, are you sure you're ready for this?  Once he gets here, I expect you to do as you are told without question, or else.  Are we clear?"

The sissy nodded.  She was nervous about how things might change between she and the woman she had become very close to.  "Yes Mistress."

Mistress smiled reassuringly.  "I know what you're thinking, but you know how I feel about you.  So, don't worry about anything you see or are asked to do here.  In fact, if things go well, we will be doing a lot more of this together.  And, you'd like that, wouldn't you?"

Tiffany couldn't help but be nervous.  She had thought about this a lot, but now it was about to become real.  "Yes Mistress."

She smiled devilishly.  "Of course you would, my pet.  Now, I need you to pull down your panties."

Sissy was wearing a pink satin chemise and matching panties and lace bra over her budding breasts.  She wore knee high white stockings and three inch pink heels.  She dropped her panties without protest.

Miss Clara reached into her bag, pulling out a paddle that made Tiffany gasp.  She laughed.  "No, you aren't being punished...  Yet.  You won't have to be if you do as told.  Oh, here it is, and this too."

She pulled out a stainless steep bird cage chastity device.  "You will be in chastity for me.  I'd prefer you in chastity all the time, but you will be at all times when we were working."

Mistress put the chastity device on her sissy, who was starting to get aroused.  Tiffany blushed.  "I"m sorry Mistress."

Clara laughed.  "Of course you are, but it can't be helped.  You won't have to worry about it when you get it removed, but in the meantime, this is how we deal with that nasty little thing of yours."

As she put it in place, Tiffany smiled.  "Thank you Mistress."

Mistress grinned.  "I'm not done yet.  Bend over."

Tiffany nervously complied as she felt warm liquid being applied to her sissy hole, followed by the intrusion of a plug.  It hurt a little and she let out a moan as it was inserted.  She felt something dangling.

Clara laughed.  "Think of it as your tail."  She squeezed the end of it a little and the plug inflated inside of Tiffany.  "Much better.  It's inflatable.  Just what my sissies and subs need.  Now, get on your knees."

Tiffany complied as Clara produced a collar with three link rings on it and put it on her.  Had Tiffany been able to read the tag she would have read Clara's Sissy Slut.  She showed her the leash.  "This will be for later.  Now, I need you to sit down in that chair."

Tiffany was hesitant at first, and Clara snapped at her.  "We don't have time for this.  He'll be here in a minute.  Am I gonna have to spank you already?"

Tiffany sat down.  Clara produced four sets of cuffs, cuffing each of Tiffany's wrists and ankles to the chair.  "Miss Clara, I don't know if I like this.  You know how I feel about things like this."

Clara smiled at her with a hint of anger in her eyes.  "Yes, I know how you feel, and you have to trust that I'm not gonna hurt you.  Can you do that for me?"

"Yes Mistress."

"Good.  Now I know you have an aversion to ball gags, so I would hope you keep you mouth shut and do what you are told so I don't have to gag you anyway."

Tiffany looked down.  "I'm sorry Mistress."

A knock came at the door.  "You will be if you don't behave.  I may need to spank you later."

Miss Clara opened the door to reveal two men on the other side.  Tiffany was suddenly very nervous.  Two guys?  Just what did Clara have planned for tonight?  What she didn't know was these two guys were two of Clara's best clients and had a very kinky side.  The night could get very interesting.  Clara was giving her a trial by fire.  Could she handle it?

Mistress Clara smiled at her two subs.  "On time as usual.  That makes me very happy."

"Anything to please you Goddess, " said one of them as they entered the room.

Clara looked back at Tiffany, who had the most adorably frightened look on her face.  She winked at her sissy.  "We shall see."

A Newly Captured Sissy

James lay tied to the bed in a most precarious position.  He was blindfolded.  His skin felt funny, caused by the fact that he had undergone a full body wax and was now wearing satin feminine clothes.  He was groggy as he had just woken up.

What the hell happened last night?  He remembered meeting a woman at a bar, a Miss Jasmine.  He was amused because somebody introduced her as Miss Jasmine and not just Jasmine.  He had no idea what that really meant at the time, but it should have been obvious.

In his mind, he was meeting a tall, attractive brunette woman who was dressed in black.  She came off as rather bossy and opinionated, but he liked that.  Plus, she was buying him the drinks, which made it all the more better.  Too late did he realize what was going on.  He had been drugged.

He felt a paddle strike his posterior, which was sticking up in the air.  A lady's voice laughed.  "Are we awake now Jessica?"

"My name is not Jessica, it's James, " He replied in defiance.  Only to feel the paddle stroke him again.  "Ow.  Stop it!"

She swung the paddle hard three more times.  "Don't you dare tell me what to do, Missy!  Is that clear?"

He was starting to get angry and had thoughts of what he would do to her once he was free from the restraints.  He figured he'd better humor her until then.  "Yes."

She swung the paddle hard at his rear end again.  "Yes what?"

That one hurt, and he thought he heard metal clang against the paddle.  Only too soon did he realize that he did, and he was not happy about what that was.  What had he gotten himself into?  "Yes ma'am."

She laughed.  "Good girl.  Now I'm sure you are wondering what you are doing here..."

"The thought had crossed my mind, " he interrupted before feeling the paddle strike him again.

"Do not interrupt me again, " she swung the paddle once more.

"I'm sorry Miss Jasmine."

She swung the paddle one more time.  "You will be if you keep this up.  Now, the reason you are here is because you are a part of my stable of sissies, and you will serve me as I see fit..."

"Now wait a minute.  I never agreed to any of this.  I'm not into all of that..."

She swatted him again.  "You will be by the time I'm through Jessica.  Trust me.  And, you will find the experience of being one of my special girls pleasurable if you do as told."  She swung the paddle again three times.  "If not, I have ways of making you accept it."

James had heard about these type of women, but he never desired to be in this lifestyle.  He realized the signs were all there at the bar last night, but he was thinking with the wrong head.  Now, he was in trouble.  He had better keep his mouth shut and wait for an opening to escape.

Jasmine smiled as she stood over her conquest.  This one was feisty and had an attitude.  She'd broken bigger men than him.  He would soon be one of her girls and be happy to serve her.  Of this she was certain.  The question was, would it be accomplished the easy way or the hard way.  She hoped for the latter as she swung the paddle once more.

Overcoming Fear Is A Big Step For Some Sissy Subs

Some sissies simply know they were born to serve a strong Mistress.  Some aren't there yet.  They may have thought about it, but what they are thinking first and foremost is they need help.  They need help with make up, picking out nice outfits and help bringing their feminine feelings to the outside.

When a sissy cant find her, there are a couple options.  You can either give up because you have no help, or you start doing what you can.  This is a topic we address elsewhere, because many sissies do just that.  It's not easy, but it can be done.

However, you have to consider that Mistress has a kinky side too, and she needs to have it indulged.  Look at it this way.  She helps you pick out things for your wardrobe.  She helps you learn make up.  She coaches you on how to walk (in heels) and how to talk.  You learn presentation from her.

That's all fine, but ask yourself a question.  What are you doing for her?  So many sissies think a woman should just help them out of the goodness of her heart, but when something is asked of them, they get nervous or just run away.

What if she asks you to submit to her?  Can you do it?  I know the worries start to come up.  You worry about giving up control to her.  You like her, maybe even love her.  If you submit, you worry that she will think of you as nothing and things will change,  This is amplified by things she will say to you when you submit.

You need to talk with her before you go into anything  An open discussion is important.  What are you willing to try?  What is she looking to do?  You reach a clear understanding of what will happen, but also an understanding that she will push you past those limits.

Why would she do that?  Part of the act of submission is to test yourself.  What are you willing to do to please Her?  If it's outside your comfort zone just a little bit, can you test yourself?  You may get something out of it and it's almost a given that she will.  And she deserves that too.

Trust is a big issue here.  You, as a sissy, are about to enter into a power exchange with a beautiful dominant woman.  It can be intimidating and a lot of things will enter your mind.  Since we're talking lifestyle Mistress here, she has suggested taking the relationship into this area after helping you bring your inner girlie to the forefront

Did she do a good job with you in helping you explore your feminine side?  Are you happy exploring this with her?  Then, you need to consider letting go and trusting her. She wants to do this for both of you.  It's about making both of you happy, and she wouldn't have suggested it if she didn't think you'd like it.  Talk about it and then commit.

Once you do, don't spend time undermining her while you are engaged in a scene.  Talk about those things later.  Let the scene play out and give it a chance.  If she's testing you, she has a reason that should become apparent as it plays out.  You have to be able to surrender to the moment.

It is all about surrendering to her desires and letting her be your guide.  And what might that include?  She's probably going to do things to humiliate you a little, maybe some actions, maybe calling you certain names.  Many times, she will require a commitment from you, and that means you may be in chastity.

That idea will scare a lot of sissies.  They don't like the idea of having their most personal body part locked behind a device that somebody else holds the key to.  But, that's the beauty of submission here.  You are showing your commitment, even your love for her by letting her tell you when you can use it for pleasure.  It is a big deal.

She may requite you to wear the panties she picks out for you. She is very interested in introducing toys to the bedroom.  This may mean a plug, and it may also mean a strap on, or even both.  Her own personal requirements might involved lots of oral when she wants it.  For some Domme/sub relationships, this covers most of it.

However, it can go up a notch or many depending on what you want.  Restraints may be introduced next. She may like tying down her sissy to keep her in place.  Like chastity, this requires your submission, and it means trusting her not to hurt you.  She'll be saying things to you that may make you unsure, but that's the point.  Will she really go there with you? You'll be wondering.

You may have carelessly let it slip that you would like to orally please a guy.  Don't think for a minute she forgot that.  Now that you are her sissy sub, she may make it a reality for you.  Are you scared?  Good.  She likes that.  But you will do this for her, because it will make her happy.

How far are you willing to go, because this has so many more levels?  Can you sit and watch when she brings another man into the bedroom to please her?  Will you perform oral on him before he does it?  Will you clean her up orally afterwards?  She may bring in more than one guy and both of you may be in action that night under her supervision.  Can you handle that?

I probably just made you more nervous, but I can't speak for your Mistress.  Generally, you agree on where you want to go, and that is respected with some boundaries being tested as she sees fit.  However, she did so much for you, I think it might be fair for her to ask if you will be her sissy sub.  It may be the best decision you'll ever make.

Getting Started With Cross Dressing

When you think about it, it can be very overwhelming to take these feelings we have within ourselves, these fantasies, and make them reality. I mean, how do you even begin? Some may have a sister to "steal" panties or other clothes from, hoping not to get caught. Some may have wives or girl friends. Others maybe took their mother's clothes when they could get away with it.

They may be doing this hoping not to get caught. Some actually fantasize about getting caught and "forced" to dress completely with her supervision. I've heard that one a lot. She forced me, hehe. Sure, okay. Whatever makes it easier on you honey, just be happy.

Still others have a girlfriend or just a friend who has helped them pick out clothes, learn makeup and maybe even venture out the door on the town. Doesn't have to be a club. It could be shopping, a walk in the park or whatever. Those are the lucky ones.

For some "girls in waiting", they sit on the sidelines and wonder what it's like, never quite able to take that first step. Let's face it, society is messed up. We all have to deal with the "shame" put on us for expressing ourselves this way. It doesn't matter if you are CD or a t-girl, everybody faces it. How you deal with it and overcome it is all that matters.

Let me tell you this though. There is absolutely NOTHING to be ashamed of here and it is NOT a contest. You may see the beautiful t-girl in the video and say, "I'll never look as gorgeous as her."

You can't get caught up in that or the label of being "passable" or pretty enough. It's about how it makes you feel inside. It's about being yourself. Whether you aim to be 24/7 or just whenever you can, you can do it if you want to. Don't be afraid, even though I know you feel the fear. We all do.

So I am quite sure there are some "girls in waiting" reading this post.  You're probably a little shy, even though you took the time to read this. It's okay though. You are among friends here. Maybe you are in a similar situation as I was, and you don't really have anybody where you are to help you. You don't know where to start.

I can tell you a little of where I started. I spent more years than I care to remember wondering what it would be like if I were born a woman. I used to fantasize about being force feminized and forced to be with a man. It exited me more than anything else, but I would also feel the shame. This was long before I knew anything about the trans community or cross dressing or anything.

I'd tell myself that I shouldn't be feeling this way and I shouldn't think such thoughts. There was something wrong with me, I thought. Through it all, the feelings and those thoughts always came back.

When my sister passed away almost seven years ago, I recall going through her old clothes in the shed and finding some panties and bras and putting on her panties. It was a total turn on to me. It's the first time I shaved down there. I used a toy on myself, not for the first time. But, the shame kicked in. I didn't purge. I kept the clothes until I was ready. As I said, the feelings never go away if this is truly who you are.

You hear a lot about purging. Maybe you have first hand experience. I know of people who had dresses, skirts, lingerie, shoes, everything. The shame becomes too much, and they throw everything out. For most of them, though, that is followed by regret. They wish they could have that stash of clothes that cost hundreds and even thousands of dollars to build up.

I've spent a couple thousand myself in just a two year span, which is quite a bit for me. What's funny is I don't think I spent that much on men's clothes in at least 15 years before that. Not even close. I simply didn't care how I looked.

Now, here I am with a nice wardrobe of nearly two dozen dresses, over 20 nighties, over 50 pairs of panties, over 2 dozen bras, plus jeans, tops, shoes, makeup.

If you know your size, you can start by shopping online for what you want. There are also sites that convert men's sizes to women's sizes. Me, I just dove right in and started shopping for clothes at the store. A lady I know was going to take me shopping, but she kept putting it off. I had two choices, either keep thinking about it or go shopping.

So, off to the store I went. At that time, I was wearing my sister's old shorts and top and panties and bra. I went to Rite Aid and bought a pack of Hanes panties, a skirt and some white tights. Also some lipstick. From that moment on, I've always worn one shade of lipstick or another and bras and panties, every day.

I know first hand how nerve wracking it can be to shop, but how fun as well. In line at Rite Aid, a couple of guys laughed at me, but I didn't care. Fact is, I get called fag all the time, and I still don't care. I don't have to live my life to make people like that happy.

The second time I shopped at a woman's store. I walked up to the register and informed the lady I would be shopping for myself and asked if that was okay. She didn't have a problem with that. If you're really worried about something like that, that's the safe way to go. If they have a problem, move on, but most of the time they won't if you're serious about what you're doing.

Also, dressing rooms. If you are there dressed, in most cases it's okay to use a woman's dressing room. If you're nervous about it, you can always wait until nobody's around and then try things on or ask a sales lady. If in doubt, use the men's dressing room. As for purchasing your stuff and worrying about what they will say to you at the register, don't worry. They are there to sell. If they are rude, they can lose their jobs. Just pay for your stuff and go.

As I have been painting my nails since I started dressing, I get looks all the time. Some are shocked, some are very friendly. I've been complimented on my nails or the color of something I bought. For the most part, it's been pleasant, and I enjoy shopping when I can afford it. Usually, it's for the sales. I'd like to be a Macy's and Nordstrom girl, but I'm Sears and Penney's and that's okay. It's not a contest.

I never did a bra fitting. I did trial and error. Currently I'm taking an herbal hormone regimen. The results on my body have been slow, but noticeable. It takes a while, but I have time. Anyway, my advise on bras is if you are going to do a fitting, call ahead and let them know you are coming if you are looking for a more pleasant experience, and be honest. That's not to say you can't show up and do it, but some ladies may not be as understanding.

What I like about shopping in person versus online is you can look up close at what is there and try on things you like. I always try on different outfits. It's part of the experience and I want to make sure I have the right size.

If you aren't going dressed, but you want to shop, that's still possible to do. I found that starting out it's best to give women the right of way. If they are looking in an area you want to look, yield to them and come back to it when they are gone. Don't hover there. Less of a chance of attitude from somebody thinking you are infringing on their territory.

If a sales lady comes over to help you, don't be afraid to ask for help. It is their job to help, after all. Just be respectful and be serious about it. You are a paying customer, so if you are being serious, they are there to take your money. If they say something after you leave, who cares? Does it really matter? You never know, though, you may meet somebody that can help you with your look and help you take your first steps out the door dressed.