Archive for the ‘roleplay phonesex’ Category

From Kendall to Kathy, A Phone Sex Caller’s Journey (Part 2)

At the first lull in the conversation, Helen offered Kendall a tour of the house. Passing her bedroom, Kendall couldn’t help but notice a smart, grey tweed suit, rose silk blouse, ivory slip and nude nylons neatly laid out upon the bed. Helen remarked, “Oh! Do pardon my mess! I’ve recently lost a few pounds and was planning to give those away to Goodwill.” A sly smile crossed her face when she asked, “Would you like to try them on? No one will ever know except you and me,” she said, with a little twinkle in her eye. Kendall blushed as he stammered, “Y-yes…b-but you p-promise not to say anything, right?” At this moment, he knew full well that his career now resided in the palm of Helen’s hand. “But of course,” Helen smiled as she motioned for him to follow her into her bedroom. Opening her dresser drawer, she removed a few other items: black lace panties, a matching bra, and a girdle. She directed Kendall to remove his clothing which he did modestly, feeling very self conscious to be nude in front of one of his co-workers—especially one with as much authority and poise as the genteel Helen.

Call me and get a preview of WHAT HAPPENS NEXT!

XOXO,

Mistress Isabelle

1-866-391-8568

www.sissyslutphonesex.com/isabelle.html

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Princess Plays Dress Up With The Phone Sex Sissy Boys

OMG! How long it’s been since we played dress up! Come on little sissy I got tons of clothes for us to play with. We walk into my room and I have all sorts of dresses on the bed, floor length, knee length, mini, nylons, panties, bras, and skirts too.

Your eyes light up as you try to take it all in, you see the wigs and makeup even the little dainty tiaras and heels. Oh how much fun this will be! Me and  you like two girlfriends playing dress up! I can show you what you missed all those years you living as a yucky masculine fuck!

Come play dress up with me now and see what you have been missing out on!

~ Princess Laylene ~

866*289*3963

My Palace

From Kendall to Kathy–A Phone Sex Caller’s Journey–Part 1

It was a day just like any other day at the office. Kendall, the IT boy was at his desk working on an assignment. A recent graduate, he’d been at his job for the last 6 months and he liked it. The ability and opportunity to solve the seemingly inexplicable problems of others on a regular basis made him feel like a superhero. Feeling the need to stretch his legs, Kendall ventured to the break room for his obligatory morning cup of joe. On the way there, he bumped into Helen, the executive assistant to the company owner as well as his right hand “gal”. Everyone knew that the power behind the throne at this mid-sized firm was Helen and that her approval of you was key to the company owner’s approval of you. Helen was an older woman in her mid 50’s. She was stout with graying hair, wore wire-rimmed glasses and was rather prim and proper. Even on weekends, which she also spent at the office, Helen was always properly attired in suit, nylons, heels and pearls, which Kendall secretly admired. She stood out in vivid contrast to the ubiquitous business casual attire seen nowadays, which even Kendall admittedly embraced. They exchanged their obligatory “good mornings” and Kendall made his move. A devotee of women, to the exclusion of male company, Kendall knew the quickest route to the heart of many a woman was flattery. “Helen, you look very nice this morning. In fact, it’s so nice to see somebody at this office who cares about her appearance. I know you must put a great deal of effort into looking so professional and put together. “Helen smiled her carefully applied smile and responded, “Oh, it’s not as much effort as you’d think, Kendall. All that’s required is organization. I can put myself together in under an hour, easily.” Amazed, Kendall blurted out his reply, “Really?” “Yes, REALLY,” retorted Helen who was well accustomed to the familiarity and informality of the much younger new hires. “In fact, I could put YOU together in under an hour, “she chuckled while surveying him head to toe in his golf shirt, Dockers, and well worn oxfords. “Well, I don’t know Helen, I admit I’m a pretty rough case,” Kendall chuckled back, secretly smarting at Helen’s resigned disapproval. “Oh, I could fix you up over lunch, Kendall. Would you like to go have lunch today? There are some issues concerning the Accounting department’s new software that Mr. Howard would like me to discuss with you.” Jumping at the chance, to curry favor with the all-powerful Helen, Kendall accepted her invitation, grabbed his coffee and headed back to his office to continue his day.

Absorbed in his work, Kendall was shocked into reality by a knock at the door. It was noon and Helen was reminding him of their lunch meeting for today. Kendall quickly tied up his loose ends, grabbed his windbreaker and escorted Helen out the front door and to her car which she insisted upon driving.” Pulling out of the parking lot, Kendall asked Helen where she’d like to go have their lunch meeting. “Well, Kendall, normally I eat lunch at home. I’m really not a fan of the restaurants here in town. In fact, I have some pot roast, potatoes, carrots and rolls left over from yesterday. Would you prefer a home cooked meal, Kendall?” Kendall couldn’t help but jump at the chance. The last home cooked meal he enjoyed was over the Christmas holiday some months ago. Before he knew it, Helen was pulling into the parking lot of her well-tended condominium. They went inside and it was exactly as Kendall expected it, pin straight and tastefully decorated. Within minutes, Helen set in front of Kendall a mouth watering plate of sliced pot roast, covered in brown gravy surrounded by new potatoes and baby carrots followed by a roll surrounding a pat of rapidly melting butter. Like a ravenous wolf, Kendall devoured his lunch and, when finished, began discussing the accounting department’s various software issues with Helen. Issues quickly resolved, the conversation quickly turned to other things…such as their earlier exchange in the break room. As long as he could remember, Kendall harbored a  secret desire to be a woman—a secret he never dared to reveal for obvious reasons. Ever since childhood, he held a fascination for all the trappings of femininity….the pantyhose…the constrictive undergarments…the lipstick, rouge, and perfume…etc. It all stood out to him in soft-focus contrast to the rough and aesthetically unpleasing world of men. Helen, always being a keen observer, picked up on this immediately upon meeting Kendall at his first interview six months ago.

To be continued…

XOXO,

Miss Isabelle

1-866-391-8568

www.sissyslutphonesex.com/isabelle.html

www.sinfullysexyphonesex.com/isabelle.html

Phone Sex Sister’s Feminist Revenge: Part 6

Part 6:

Once the strap-on feminists knew their “girls” were close to cumming, they started to get really nasty, shoving their strap-on cocks deep inside, and yelling: “take it like a good sissy bitch! Take it like a lil girl! Cum like the sissy-girl whores you truly are!” With that the teen boys began to cum, squirt after squirt, their big clitties emptying weeks of pent-up frustration all over the bed!

The foursome collapsed in a pile of sweat and cum, laughing and panting from their hardcore sissy fuck session. The teen brother turned to his older sister, trying to catch his breath, looked her in the eye and asked: “When can we do that again sis?”

THE END

If you like what you’ve read so far, you can read the whole story on my Sissy Slut Phone Sex story page, it’s called “Phone Sex Sister’s Feminist Revenge Transforms Teen Boys into Pretty Strap-on Loving Sissies.” A lil naughty something for all my sweet sissy panty fuck sluts! Enjoy!

Fetish Mistress Ava

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Pool & Panty Party Phone Sex

Brittany (my best friend) and I decided we wanted to have a pool party, so we went and booked the YMCA pool for the day and invited a few friends and Brittany’s cousin, Mike. Daddy said he would chaperon  the party for us. We were so excited, so we went swimming in our little bikini‘s with our friends and then I noticed Daddy looked lonely…

I invited him to come in but he said he didn’t have anything to swim in…Not a problem, Brittany and I took him back to the women’s locker room, and gave him a cute pair of boy short panties (blue with yellow polka dots) and a matching training bra. Daddy looked so cute, then we all went back out into the pool area to swim. We weren’t swimming all that long when Brittany’s cousin, Mike arrived. Now, daddy and Mike have a history together. *giggles*

Everytime we have a “dress up” party with daddy we invite Mike, so it took all daddy had to hold back from reaching over into Mike’s trunks and pulling out his big little boy cock! Daddy has an addiction to Mike’s cock, it’s such a big cock for such a young man. *giggles* Finally, Brittany gave daddy permission to take Mike’s cock out and suck it. Daddy’s face lit up as he did so. *giggles*

Then Mike, turned daddy around and began to fuck him in his tight little pussy, Mike loves making my Daddy his little bitch! Daddy begged to be his bitch, begged for his cock and his baby juice and sure enough Mike gave it to him. Daddy was so excited that I decided he needed a pair of plastic panties to cum in himself. *giggles*

I handed the plastic panties to daddy and told him to fill them up as Brittany finger fucked his cum filled sissy pussy and Mike face fucked him some more. Daddy looked like a true little whore as he played with his clitty. It was such a great pool party I can’t wait to have another one soon!

~ Luscious Laylene ~

866*289*3963

My Pool Party

From Sissy Butler to Sissy Maid Phone Sex

     Recently, I’ve been finding myself in need of a maid, a pretty little sissy maid who’ll sweetly attend to my every whim.   She’ll serve me dinner, wash my delicates, entertain my special guests…whatever I command, she will gladly do.  After many unsatisfactory interviews for the position, I had a wonderful idea!  I shall make my butler William also be my maid, “Willimena”!  Genius!!  As many of you know from last week, William is a bonafide sissy through and through and I knew he’d admirably fulfill his duties as both William and Willimena.  I knew William to be a quick study and was confident he’d master his new skills with ease; however, as I was holding a dinner party that evening, I knew time was of the essence in training William in his newly acquired duties. 

      I took the maid’s uniform out of my special closet and laid it on the bed.  “William!! Stop whatever you’re doing this instant and report to my bed chamber immediately!”  Within minutes, William was at my door.  “Yes, Mrs. Lace”, he said, softly, eyes downcast.  “William, after much consideration, I have decided to cease my search for a new sissy maid.  Instead I have decided to transfer those duties to you which you’ll perform in addition to your own.  Consider it a promotion of sorts, if you like.”  I saw a faint hint of a smile color his face as his downward gaze shifted to the maid ensemble lying across my bed.  “W-why, thank you, ma’am,” he stammered and blushed.  I smiled, knowing he was pleased.  You will start your new duties this evening for the dinner party.  He looked up with an alarmed expression on his face, “B-b-but…M-mistress….in front of all…all those people?”  “Oh, yes, William.  I am quite confident you’ll perform your duties admirably this evening.  In fact, you have no choice, as you well know.  Don’t you think the maid’s uniform is lovely, William?”  “Y-yes, ma’am.  It’s very beautiful.  Very well, as you command, Mrs. Lace,” William sighed.  “Very good, William!  Now, try on the maid’s uniform so I may see if it fits.”

      William removed his butler uniform and began trying on the maid’s uniform.  First, he began with the maid’s undergarments.  Trembling, he stepped into the black lace panties and pulled them up so they fit him snugly, followed by a lacey, black garter belt.  He then sat down on the bed and, one leg at a time, slid the black silk stockings up his freshly shaven legs, securing each with the garter belt.  Standing up, he picked up the padded black lace bra and put it on like I showed him.  Finally, he slid the very short, black satin maid’s dress over his head and presented himself to me for zipping.  Once zipped, I presented the white lace apron and cap to him which he wore and helped him step into his black, patent leather, high heeled pumps.  “Oh, WILLIMENA!  I dare say you look lovely!  My guests will be so impressed!” I gushed.  William, now Willimena, blushed modestly.  The doorbell rang.  I looked at the clock, it was 7:00!  My dinner party guests were beginning to arrive!  “Willimena!  Apply some powder and lipstick and get to your post, immediately!! “   I commanded.  As expected, William/Willimena performed her duties admirably for one so new to the position.  At the door, she greeted each guest with a deep curtsey.  When serving drinks to seated guests, she bent over at the waist and stuck out her rump allowing all guests a clear view of her black lace panties and garter belt.  And if a guest made a drunken pass, running an inquisitive hand up Willimena’s silk stockinged leg, Willimena was always gracious and never huffy.   As I expected, William made a perfect Willimena. 

If you’re a good little sissy and call me, I’ll gladly share with you what happened to William/Willimena NEXT!

Isabelle

1-866-391-8568

www.sissyslutphonesex.com/Isabelle.html

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Phone Sex Sister’s Feminist Revenge: Part 2

Part 2:

The boys looked shocked and embarrassed, but what could they do? They were at the mercy of this hardcore feminist, a girl who could and would tell their parents what she saw, and thus held the rest of their foreseeable lives in her hands, and certainly the freedom of their hard and horny cocks! So, both boys dropped their pants completely, and replaced them with the pink cotton panties they were handed.

A strange thing happened once their cocks touched that soft feminine fabric. Contrary to what they thought would happen, their dicks began to grow even bigger, and drool even more. The sister soon noticed this and commented: “So, you both like being forced to wear pink panties?” The boys shook their heads, but their cocks continued to grow like Pinocchio’s nose. “Well, it’s a good thing you like wearing panties, because I’m going to teach you just how difficult it is to be a real girl! I don’t want to ever find you looking at those disgusting pornography books again! Those magazines manipulate, and capitalize on the beauty of women, and lead young men like yourselves to objectify and degrade women before you even get to know any!”

But, the panties were only the first step…

To be continued…

If you like what you’ve read so far, you can read the whole story on my Sissy Slut story page, it’s called “Phone Sex Sister’s Feminist Revenge Transforms Teen Boys into Pretty Strap-on Loving Sissies.” A lil naughty something for all my sweet sissy panty sluts! Enjoy!

Fetish Mistress Ava

1-866-433-7524

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The panties were only the first step,

shopping for lingerie phonesex

I would love to go buy some new lingerie and pantyhose! You know what a girl really needs at these times? A cute girl friend to go shopping with! Will you dress up with me and come help me pick out some sexy lingerie? We can help each other try on some new panties, and sexy teddy’s. When no one’s looking, we can take some pictures of each other in all the naughty things we try on. Maybe we can even take some pictures together. They will be so hot. I can’t wait to show them to all the hot boys I know.

Would you like to come shopping with me?

Angie

1-866-538-2420

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Sissy Fucking at a Party Phone Sex Role Play

I had a hot phone sex call with a sissy boi. He has long blonde hair, which looked so pretty once we had done it up. We put some make up on him and a pretty short skirt, a slutty top and fishnets. I took my sissy to a party with me where I knew lots of horny boys. I made my sissy slut slip his panties off from under his skirt in front of everyone. It turned the boys on a lot to see his panties sliding off. I had fucked one of the  guys before, and I knew he had a really big cock. I made my sissy cum over and suck his cock for me. He got him really hard until my friend wanted to fuck me. One of the other guys wanted to fuck my sissy. I told him to fuck my sissy in the ass, and my friend started to fuck me.

It was a really hot call. Would you like to have some hot role play fun with me?

Angie

1-866-538-2420

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Phone Sex Sister’s Feminist Revenge: Part 1

Part 1:

So, this guy calls me and tells me all about how one day when he was a young teenager, he and his friend were looking at a Playboy magazine in his bedroom, and of course, being horny teen guys, they both popped huge hard-ons. He was embarrassed, certainly, but also excited, and really fucking horny. So, he turns to his friend and proposes that they masturbate together, and cum all over the hot naked Goddess in the centerfold. His friend agreed, so they pulled out their dicks and started stroking hand over fist. They were just about to pop when the bedroom door swings open and this guy’s older sister is standing square in the doorway. She took one look at their stunned and guilty faces, and their drooling dicks, before she grabbed the dirty magazine out of their hot hands.

“If you guys only knew what it was like to be a woman,” the sister began, “you would never look at this objectifying, exploitative trash!” You see, she was a college co-ed, and an active feminist who took her women’s studies classes very seriously. She grasped both boys hard by their ears, marched them into her bedroom (cocks still hanging out of their pants, and flailing mercilessly), and sat them down on her bed. Then, she reached into her top drawer, pulled out two pair of pink cotton panties, and looked at the boys. “Take your pants off and put these on right now,” she said with a twinkle of revenge in her eye…

To be continued…

If you like what you’ve read so far, you can read the whole story on my Sissy Slut story page, it’s called “Phone Sex Sister’s Feminist Revenge Transforms Teen Boys into Pretty Strap-on Loving Sissies.” A lil naughty something for all my sweet sissy panty sluts! Enjoy!

Fetish Mistress Ava

1-866-433-7524

http://www.sissyslutphonesex.com/ava.html

http://www.tlcphonesex.com/ava.html