Archive for the ‘cross dressing’ Category

Sissies Wanna Wear My Phone Sex Stockings

I have a special sissy boy that loves to call me.  I know she’s a bit shy but she does love me and I know just which buttons to press to make her cream her pretty little panties.  She called me today for some lovin, all dressed up in her pretty little panties and hot little dress.  Complete with some sweet smelling lip gloss and her hair all done up nice and pretty for Me, her Mistress.

However, no outfit is quite complete without some sexy black lacey stockings.  So, while I layed on the bed showing my sissy my pretty black lacey thong that I was currently wearing, she was going through my drawer looking for my sexy little stockings.  She found 2 pairs of them and while I told her to put them on in front of me, I was running my fingers through the sexy lace of the pair I was holding.  Once she had them on, I passed her mine and lifted one of my silky sexy legs in the air.  “Put it on me darling” slide it over my leg, touch my perfect sexy legs as you slide those little stockings over my legs.  There…..I know how much you love it when we match.

She came up on the bed with me then, got on her back beside me.  I got up and knelt between her legs as she spread them for me, watching a wet spot form on her panties.  She moaned as she looked up at me as I flicked her little bitty clitty, already rock hard in anticipation.  I lifted those long legs over her head, tying them to the head board before I slipped on my 9″ strap on, squirting some KY on it and jerking it off over her panties as she whimpered and begged me to take her.

And I did, fucking her all night, making her cum over and over in her panties as I thrust inside her tight little sissy pussy over and over until we both passed out.

Do you wanna wear my sexy black stockings?

Maria

877-422-6457

My Bedroom

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

www.tlcphonesex.com/isabelle.html

Sissy Phone Sex Dress Up

I played a game with one of my sissies this week.  I had a very long day at work.  I was in meetings all day long off site and just wanted to get home and relax.  I was in a business suit consisting of a black skirt with stockings, garter belt and heels.  And of course panties.  Not to mention the blouse and suit jacket of course.  When I walked in my sissy love was there waiting for me.  I told him to be naked when I walked in and he was.  Such a good boy.  His assignment of the day was to remove my clothing one piece at a time and put it on himself.  I told him he didn’t have to put the blouse or the jacket on but i wanted everything else on him.

I sat in the chair while he removed my heels.  I stretched my legs as he unrolled my stockings and stood in front of me sliding them on and up over his legs and thighs.  I stood up as he took my skirt off.  I handed him my garter belt and turned around as I wiggled out of my panties.  When I turned back he was rock hard and gently squeezing his cock as I drapped my damp panties over it.  He moaned as he stroked a little.  After he finally had everything on he dropped to his knees and worshipped his Mistress properly but helping me relax.  I had such a stressful day, he offered me the relief I needed, wearing my sexy things and stroking as he brought me to orgasm

My sissy, my lover……mine…….

Love Maria

87-422-6457

My Place

This Weeks Phone Sex Winners

The weekly winners are:  YAY!! Sissy’s can win also.

3′SCOMPANY won the free 15 min call with a girl of

choice.

ZMAN won 10 free min call with a girl of his choice.

Must be done by 09-13-10

This is how you join in on the fun:

**Want to win free phonesex? We offer it every week, simply stop by the chat at http://www.tlcphonesex.com/chatroom.html to find out how to enter for your chance to win free phone sex this Sunday!

Daddy’s Girl Susan

866-239-2972

www.teenteasephonesex.com

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

Phone sex sissy time

My girlie boy is coming to visit for the weekend.I’m getting everything ready so we can have a great fun weekend.
I have the Lingerie the panties, bras, stockings,garter belt and heels.
I have different sizes of strap on is ready to fuck that tight sissy pussy.
I have nipple clamps, and clothes pins, string,q-tips, hot sauce and a safety pin.
I even have several colors of markers to decorate the sissy’s body and mark him as my
girlie one.So tell me  sissy as you read my list do you see anything missing we may need for a weekend of total naughtiness?
Riley
1-888-858-5127
http://www.sissyslutphonesex.com/riley.html
http://www.tlcphonesex.com/riley.html

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

Our Winner’s For The Phone Sex Drawing Is……..

Our Winner’s are for the weekly contest is…

BIGSTIFFY  won the 15 minute call

BI-SISSY-HUSBAND   won the  10 free min call.

Calls have to be done by 09/06/10

Want to join in on the fun? This is all you have to do.

Who doesn’t like FREE Phone Sex? Enter our voting contest to win a 15 minute phone sex call! To enter, click below our chat room, open it, Let it load, close it, then open it again. Put in the vote code and click submit. Bring us back the vote code and position of our site, and we will enter you for the contest. You can enter Every 3 hours. Drawing is Every MONDAY ! Also the person who votes the most for us gets a 10 min free call.

Mercedes

866-954-7325

http://secretwhispersphonesex.com/

Phone Sex Sissy Slut.

Crawl over to me now sissy slut, I want you to worship my pussy cause you wish you had a pussy like mine. Even better I can make you my sissy and fuck you like you had a pussy. Invite all my friends over so they can use you and gangbang you as a sissy slut you are. Sissy slut call me so I can make you my sissy slut.

Mercedes

866-954-7325

www.secretwhispersphonesex.com

Phone Sex Sissy Bitches doing what they do Best

Missy is one of my little sissy bitches.  I love her when she gets all dressed up for me.  When she puts on that nice red lipstick I know she is ready to suck cock for me.  She loves marking a cock with her red lipstick.  And I love watching her with him, coaching her.  Telling her what a good little sissy bitch she is and what a good little cock sucker she is.  I had a little surprise for her too.  I slid on my strap on and got behind her.  Whispered in her ear what I had planned and then spread her open gently, slowly sliding my hard cock up inside her.  Both of us fucking her at the same time while I reached underneath to rub her hard little clitty and spank her tight little ass.

Missy is a good little sissy bitch and she does everything to please me.  Everything I ask she does and it makes me very happy. 

Do you wanna be like Missy?  Do you think you can please me the way Missy does?   Call and we’ll find out.

Miss Maria

877-422-6457

Pleasure Me Here