Archive for the 'Sissy Lessons' Category

Page 29 of 32

A Sissy’s Appreciation

Published on in CBT Phone Sex, Control Phone Sex, Guys Sucking Cock, Humiliation Phone Sex, Phone Sex, Sissification Phone Sex, Sissy Lessons, Sissy Phone Sex, Spanking Phone Sex and Strap-On Play Phone Sex. 0 Comments Tags: , , .

My little sissy lisa wrote this for me…. just had to share:

Dear Raylin,
I love talking to you. You make the best in me come out. I love how you take over my body completely and do whatever or heart wishes. I wish we could talk for ever on the phone. When I hang the phone up from you it is like I am just waking up from a dream. I never knew a girl that could complete me the way you do. I love when you make me dress up in the really slutty girl’s clothes. But better than that I fell in love with the way you abuse my ass with your toys. The paddle is a good warm up, I have been enjoying that a lot. The one thing that makes me go into complete orgasm though is when you use the strap on, on me. It makes me feel powerless at the same time it hurts in the rear. Although it is hurting it makes me hard and makes me squeal like a little girl. Maybe in the future we can try some bigger ones and stretch my little hole to be really loose. I tried the ginger you told me too- “oh my god”. That was pain full. I also put one in and slept with it in through the night. I was unable to go number two today because when I tried it burned really badly.


Oh yeah I did something really bad last night. I cheated on my girlfriend I was telling you about. I am on the way back up to school. I am traveling with another female and we made out and one thing lead to another well you get the picture. I think I am going to need to be punished for this.


Another thing I have been contemplating on going to a gay bar to see if I can’t pick someone up while I am wearing girl clothing. What do you think about this? I figured if I could do this then I would know what it feels like to really get pounded in the ass or to suck someone off.

Love,

sissy lisa


Don’t worry my little pet… you will be punished.  I promise.  That dick is mine and no one touches it without my permission.


xoxo

Raylin

1.877.470.3647

So, I am a tease. That’s a good thing, right?

Published on in Barely Legal Phone Sex, Cuckold Phone Sex, Cuckolding Phone Sex, Dating Phone Sex, Fantasy Phone Sex, Financial Domination Phone Sex, Humiliation Phone Sex, Naughty Teasing Teens, Sissy Lessons, Sissy Phone Sex and Young Phone Sex Voice. 1 Comment
I had a date last night that involved a lovely, expensive meal and such good company that I didn’t get to bed until, well, very late :D   Oh and this guy is HOT, let me tell you: gorgeous, loaded, with a nice thick eight inch package to finish me off and that he did. I shouldn’t brag too much, all you little sissies and cuckolds reading might get jealous that I got to suck cock last night while you were just fantasize about it. Wait, what am I saying? Craving is good for you. It makes you desperate which makes you weak which makes you easy to fuck with, LOL. That’s why I love to be a tease.

I know how to use my assets against your weaknesses and that means I always come out on top–except when I want to be on the bottom, as was the case last night. Now that really is all that I’m going to say. If you want the details you are going to have to call me. I know it’s humiliating to hear about all the things I do with my lovers but that’s the point LOL. you need to get used to the idea of sitting at home alone, humping your hand, while I’m out getting what I really need from a real man, and if you are lucky, I will tell you about it when I remind you how unworthy and undeserving you are while I laugh at you and take your money, HAHA! Pick up the phone.

Closing the deal- a sissy slave story

Published on in 2 Girl Phone Sex, Anal Phone Sex, BDSM Phone Sex, Blowjobs, CBT Phone Sex, Cock Sucking Phone Sex, Control Phone Sex, Crossdressing Phone Sex, Domination Phone Sex, Face Sitting Phone Sex, FemDom Phone Sex, Forced Bisexuality Phone Sex, Guys Sucking Cock, Humiliation Phone Sex, Phone Sex, Sissification Phone Sex, Sissy Lessons, Sissy Phone Sex, Spanking Phone Sex and Strap-On Play Phone Sex. 1 Comment Tags: , , , .

The other night I had an amazing call with the very beautiful Tyler and my own little pet- Sissy Lisa.  My little sissy refers to me as Mistress Raylin and he, well she, is always at my beck and call.  I so love having her wear my panties while I punish her.  Anyways, getting off topic.  Little Sissy Lisa asked me if we could do a two girl call, I of course said, hell yes!  I chose Tyler because she and I have great chemistry.

Tyler and I were business partners, co-owners of a women’s clothing line.  We were embarking on a multimillion dollar deal that was going to put the company on the map.  The business men we were meeting with needed just a bit more persuasion, we knew Lisa would be the perfect thing! 

We stripped lil Lisa buck naked and put her in a very sexy red backless dress- no panties.  Lisa served the men drinks and snacks while we finished our presentation.  When we were done, it was time for the main show.  I had Lisa get on her back and Tyler got her strap-on out.  While Tyler fucked Lisa’s tight lil asshole, I had three of the business men unzip their pants and free their cocks.  The first began to fuck Lisa’s mouth, choking her with it.  The other two cocks were grasped in Lisa’s hands.  I raked my long fingernails over Lisa’s chest while she got the men off, one by one.  Tyler and I decided to make Lisa’s mouth our lil cum dumpster, so each man came deep down her throat. 

I decided Tyler looked like she could use a lil pleasure so I had her sit on top of Lisa’s face.  Tyler fucked our lil sissy’s face, dripping her pussy’s juice all over.  In the mean time, I continued to fuck Lisa’s ass raw with my strap on while I smacked her ass, inner thighs, etc. viciously with my belt.  I could hear Lisa screaming up into Tyler’s pussy at the pain.   When Tyler had had enough, we switched out my strap on for one of the men’s thick cocks.  He was ramming it into Lisa’s poor ass.  I made Lisa clean the strap on I was wearing as I attached some binder clips from our presentation to her nipples.  I loved smacking her in the face with the strapon as I smacked the binder clips with my hands, causing lots of pain!  I threw a few to Tyler who clipped them on Lisa’s ball sack.  Oh the moans, whimpers and screams were unbelievable!!! 

I cannot wait to play with my lil Sissy Lisa again.  Maybe Tyler will join us for twice the fun.  Maybe you can be my little sissy too! 

My Rules

Published on in BDSM Phone Sex, Bondage Phone Sex, Cock Tease Phone Sex, Control Phone Sex, Cuckold Phone Sex, Cuckolding Phone Sex, Domination Phone Sex, Family Fun Phone Sex, Fantasy Phone Sex, FemDom Phone Sex, Financial Domination Phone Sex, Goddess Worshipping Phone Sex, Humiliation Phone Sex, Panty Worship, Pantyhose Fantasy, Sissification Phone Sex, Sissy Lessons, Sissy Phone Sex, Stocking Fetish, Submissive Phone Sex and Torture Phone Sex. 0 Comments Tags: , , , .

1. The Female always makes THE RULES.

 

2. THE RULES are subject to change without notice.

 

3. No Male can possibly know all THE RULES.

 

4. If the Female suspects the Male knows all THE RULES, she must immediately change some of THE RULES.

 

5. The Female is never wrong.

 

6. If it appears the Female is wrong, it is because of a flagrant

Misunderstanding caused by something the Male did or said wrong.

 

7. If Rule #6 applies, the Male must apologize immediately for causing the misunderstanding.

 

8. The Female can change her mind at any time.

 

9. The Male must never change his mind without the express written consent of The Female.

 

10. The Female has every right to be angry or upset at any time.

 

11. The Male must remain calm at all times, unless the Female wants him to be angry or upset.

 

12. The Female must, under no circumstances, let the Male know whether she wants him to be angry or upset.

 

13. The Male is expected to read the mind of the Female at all times.

 

14. at all times, what is important is what the Female meant, not what she said.

 

15. If the Male doesn’t abide by THE RULES, it is because he can’t take the heat, lacks backbone, and is a wimp.

 

16. If the Female has PMS, all THE RULES are null and void and the Male must cater to her every whim.

 

17. If the Male, at any time, believes he is right, he must refer to Rule #5.

Loser Alert!!!

Published on in ABDL Phone Sex, Anal Phone Sex, Ass Licking Phone Sex, CBT Phone Sex, Cock Tease Phone Sex, Control Phone Sex, Cuckold Phone Sex, Diaper Babies Phone Sex, Face Sitting Phone Sex, Fantasy Phone Sex, FemDom Phone Sex, Humiliation Phone Sex, Milking Phone Sex, Mind Control Phone Sex, Scat Phone Sex, Sissy Lessons, Sissy Phone Sex, Small Penis Humiliation, Spanking Phone Sex, Stocking Fetish, Strap-On Play Phone Sex, Submissive Phone Sex, Tease & Denial Phone Sex and Toilet Training Phone Sex. 0 Comments

You know that caught your attention! I bet for some of you it even made your cock jump!  Sometimes I sit back and wonder how many pencil dick pathedic loser’s we actually have on this site!

Harsh maybe but oh so true HaHa … You know you sit back and crave to call some of you dirty dick lickers even try to talk yourself out of it. But you can’t because your weak and you know some of us ladies including myself cause rock your world!

Little dick losers, pantie whore’s, diaper babies, & little pussy princess’s im calling you all out to play with one of the cockiest ones out here!

Come test the waters … It will be well worth it!

Submissive entertains his audience…

Published on in Domination Phone Sex, Enema Phone Sex, Fantasy Phone Sex, Forced Bisexuality Phone Sex, Forced Intoxication, Harley's Blogs, Phone Sex, Sensual Domination Phone Sex, Sensual Seduction Phone Sex, Sissy Lessons, Sissy Phone Sex and Submissive Phone Sex. 0 Comments

Occassionally there is that special call or caller that I just can’t get out of my mind.  Don’t get me wrong, all of my callers are special to me, but sometimes there is just that call that is above the top, overwhelming and memorable.

One of my favorite callers was so much fun to play with yesterday that I have had to rub my pussy numerous times since then thinking about it.  He is my CBT slut and is very near and dear to me because eventhough I am new to cock N ball torture he is patient with me and seems to enjoy my creativity.

He likes being my bitchboy, enjoying fantasies together of me selling him, pimping him out, using him for my entertainment and pleasure.  Yesterday was no different.  First of all I like for him to take a nice liesurely enema to get ready for the call.  Then he ties up his cock and balls and goes shopping for the grocery list I give him for playtime.  Today was a little different because he was also told to get intoxicated before calling as well.  In a matter of minutes he had guzzled enough that his typing skills were incoherant.  The fantasy was a bit quirky but very enjoyable.  I was the Ringmistress of a huge Circus and he was the star of the show.  Hundreds of people in the stands cheering him on as he performed for us, laughing at him and calling him names.  The tricks he performed for our entertainment were numerous, everything from having the baby elephant mount him and fuck his tight shithole to giving sweaty fat clowns blow jobs while we all watched.

While I humiliate him at the circus he is obediently doing any and everything I tell him to do over there.  His screams of pain and moans of pleasure are proof that he is indeed very submissive.  My pussy squirted good listening to him bone his own ass with his huge dildo.  Of course we brought a little of the Circus in to his playtime to include his cock being slathered and jacked off with some frozen icecream and him shoving popscicles up his asshole for me.

I truly do love our calls and hope to have many more climaxes while listening to you do everything from spanking your balls for me to shoving hotdogs up your ass for me.  You being truly submissive is not only a turnon, but deeply appreciated.

“sissy” sluts AKA my little sister

Published on in Crossdressing Phone Sex, No Taboo Phone Sex, Phone Sex Lexi, Sissification Phone Sex, Sissy Lessons and Sissy Phone Sex. 0 Comments

Don’t trust a whoe…you know the song right? Well my little sister heather fits the bill perfectly. She can hardly wait for me to leave town. Before very long, shes into my shit, stealing my clothes and strutting her slutty ass all over the fucking place, dripping in cum and getting stains all over everything!!! This time, when I left for my vacation to Hedonism, I told her explicitly she was not allowed anywhere near my room, or any of my belongings. When I get home, the lock on my door has been picked, and the steamer trunk with all of my club outfits and costumes from when I was dancing~~has the lock busted clean off!!! She, of course is no where to be found, so I bust into her room, infuriated! I started grabbing  everything I could get my hands on….then I stopped.

Silly little bitch left her computer on.

>:D !!!

I began my investigation, and what do you suppose I found?? Heather was a busy bitch while sissy was gone!!! I do hope she doesnt mind that I “borrowed” some pictures of her playtime in  Big Sis’s clothes, to show the world what a stupid shitty cock-sucking whore she is!!

My….they grow up SO fast!!!!

for more pics, go to www.phonesexlexi.com

 

Sucking Cock For Yours Truly

Published on in BDSM Phone Sex, CBT Phone Sex, Cuckold Phone Sex, Cuckolding Phone Sex, Cum Eating Phone Sex, Domination Phone Sex, FemDom Phone Sex, Financial Domination Phone Sex, Freaky Phone Sex, Hardcore Phone Sex, Humiliation Phone Sex, Latex/Leather Fetish, Mind Control Phone Sex, No Taboo Phone Sex, Sissification Phone Sex, Sissy Lessons, Sissy Phone Sex, Stocking Fetish and Tease & Denial Phone Sex. 0 Comments

I just laughed my ass off at a little cuckold bitch boy that called. He was so shy and quite, a true closet sissy-fag. Sounds to me like the girlfriend he had that introduced him into the lifestyle was really nice to him, kinder than I ever would be! He’d been domesticated, made to do chores for her and assist in preparing her for her dates with real men, but not really involved in her sexual adventures.

If I’m really disgusted by a little dicked cuck, I’ll make sure to keep it busy with chores, but I’m much more amused and satisfied by them when I’m humiliating them in a more close up and personal way. I like to make sure you realize exactly why it is that I’d never use you for sex, and show you how real men experience me. There are so many different ways I take pleasure in being with a real man, so many ways that you could NEVER satisfy me, I like to make sure you’re familiar with all of them.

I’m just not happy unless you’re totally broken and humiliated into serving me in whatever way I see fit. Just don’t prove to be selfish about any contact I do allow you to have with the real man in the room, because I also enjoy correcting and punishing you little cock sluts. Call me if you think you can handle it.

 

 

Consider Me an expert in the following areas: Cuckoldress, forced-bi, feminization, Femme Domme, FemDom, tease and denial, orgasm denial, chastity, face slapping, sadistic role play, strap-on training, forced cocksucking, public humiliation, BDSM, bondage, small penis humiliation, forced intoxication, money slavery, financial domination, fetish phone sex, size queen, SPH, tiny dick humiliation, humiliatrix, creampie, sissy training, panty boys, foot fetish, pantyhose fetish, clothed female nude males, service slaves, submissive men, cuckold husbands, sissy humiliation, shopping slaves.

It’s all about the tease

Published on in Cuckolding Phone Sex, Dating Phone Sex, Humiliation Phone Sex, Sissification Phone Sex, Sissy Lessons, Sissy Phone Sex and Tease & Denial Phone Sex. 0 Comments

What a week and it’s only Tuesday! I had a date last night that involved a lovely, expensive meal and such good company that I didn’t get to bed until, well, very late :D   Oh and this guy is HOT, let me tell you: gorgeous, loaded, with a nice thick eight inch package to finish me off and that he did. I shouldn’t brag too much, all you little sissies and cuckolds reading might get jealous that I got to suck cock last night while you were just fantasize about it. Wait, what am I saying? Craving is good for you. It makes you desperate which makes you weak which makes you easy to fuck with, LOL. That’s why I love to be a tease.

I know how to use my assets against your weaknesses and that means I always come out on top–except when I want to be on the bottom, as was the case last night. Now that really is all that I’m going to say. If you want the details you are going to have to call me. I know it’s humiliating to hear about all the things I do with my lovers but that’s the point LOL. you need to get used to the idea of sitting at home alone, humping your hand, while I’m out getting what I really need from a real man, and if you are lucky, I will tell you about it when I remind you how unworthy and undeserving you are while I laugh at you and take your money, HAHA! Pick up the phone.

dress you up and take you shopping

Published on in Cheap Phone Sex, Domination Phone Sex, Fantasy Phone Sex, Freaky Phone Sex, Naughty Confessions, No Taboo Phone Sex, Phone Sex, Sissy Lessons and Sissy Phone Sex. 0 Comments Tags: , , , , .

Your a sissy boy in the closet..Not anymore. Put this on!!! See you like the white panties and the nice stocking and the heels..dont you?  Put on the short skirt and the nice shirt. We are going to the store to try on some clothes. You will allow me in the dressing room as you put them on and model them for me. I see they have some nice panties on sale you will try them on also. Some you will wear and others you will use a panty fuck.  Oh look the clerk knows to bring more. Look at that she is good she brought you in a red teddy. Maybe she would like to see you in that. Put it on. I now bend you over and start to rub your ass in the dressing room. You starting to moan. YOU SLUT. you like this. I hear a KNOCK KNOCK on your dressing room door. can i come in to help with anything. You shake your head no. I say sure you can. The buttons seem stuck can you help with them. You are bent over and you ass is sticking out and the crouch is open I am about to lick your ass. mmmmm and she walks in. She said i see you do need help. She sits down and pulls her skirt up and panties down..and has you eat till she cums. I begin to eat your ass. My tongue in and out like a small cock.  licking ever inch and you cum so hard in your hand and you are ask to eat it all.

what a submissive.