Dear Mandy

by Patricia Violet

  

Note: The following is a letter to my dear friend Amanda after a night I spent with her boyfriend Jake.  Jake recently confessed to Amanda that he enjoyed when she dominated the sexual aspect of their relationship.  He encouraged her to experiment in light bondage and role reversal.  Now, Mandy is a sweetheart and tried her best to be accommodating, but confided in me that she felt somewhat uncomfortable trying to be a dominatrix, even if she did enjoy the control that she now exerted in the bedroom.  So, she arranged with me, as a special treat for Jake, to have him spend one night at my house, since I am a trained and working domme.  After an interview with Jake where I probed him with questions about his fetishes and fantasies, I gave him a date and time to arrive at my house for his domination.  I also warned him that I would provide Mandy with a full report on the night's events.  That report is what follows.

 

Dear Mandy, 

You did a good job stalling Jake's departure from your apartment as I instructed, and he arrived ten minutes tardy for the appointment we scheduled.  When he knocked on my front door, I yelled to him that he was late and would be accordingly punished.  I then commanded him to strip down to his bare ass for me before I would allow him entrance into my domicile.  He did as told, with a little hesitation, and I opened the door for him.  His face was red, and he was obviously embarrassed.  He walked in with his head lowered in shame, unable to meet my eyes. He was carrying his clothes and the bag I had you pack for him in front of him to hide his intimate parts.  Without saying a word, I took these from him and placed both hands on his shoulders, pushing him down to his kneel before me right there in the foyer.  He did not resist at all and assumed the submissive role right then and there.  As he knelt before me naked and with his head bowed, I was fully clothed in a short, black cocktail dress with stockings and black pumps, a stunning ensemble for an evening of domination.  Putting a man on his knees, and being fully clothed while he is in front of you naked, are two very easy ways to make him feel vulnerable and submissive to you.  And in Jake's case, as I could tell from his erection, that those feelings began to arouse him, so I pushed forward with the domination.

"You are to do as I say and as I please," I commanded.  "This is your role tonight while you are here.  If you are a good little boy, you will be rewarded and your dear Mistress Mandy will receive a good report from me." I paused and looked down at him with malice.  "You may begin by showing me the proper respect a Mistress deserves from her slaves.  Kiss my feet!"

"Mistress?" he questioned, so I gave him a light backhand across the face.

"Do as I say and kiss my feet!  While you are here tonight you will only speak when directly prompted to do so.  You will address me as Mistress Tricia and refer to your girlfriend as Mistress Mandy.  Do you understand?"

 

"Yes Mistress Tricia," he replied feebly.  And with that he bent down and softly kissed each of my stockinged feet once in their open-toed heels.  Jake's dick was already stiffened to full height at this point, and I continued my plans.

"What did you come here expecting?  A free night pass to cheat on your girlfriend?" I asked sternly.  He seemed to quiver a bit, but then whimpered out a response.

"No, Mistress Tricia."  His head was still lowered, so again I lifted one of my feet up to his face.

"Worship this with your tongue while I explain to you what is going to happen tonight."  His tongue obediently flicked out of his mouth and he began licking my foot.  I must tell you darling that he really does have quite a talent for foot worship.  You'd be crazy not to make him your slave.  "Tonight," I told him, "is not for you, as you may be mistaken, but it is in actuality for your girlfriend.  Because you are not enough of a man to properly take care of your Mistress, and you made her feel unnatural in her natural role in your relationship, she feels as if she must send you off to another woman.  To make you pay for this, tonight, I will punish you.  Unfortunately, one night with me will not be able to transform you into a real man.  In fact, quite the opposite.  I plan to make a sniveling little girl out of you.  Because to me, that is exactly what you are."  I was worried I was pushing a bit far too early here, but Jake's tongue seemed to begin licking my foot more furiously after the last remark.  It was obvious I had hit the mark and Jake's sexual humiliation and excitement only grew.  I saw his hand begin to drift from his side to his thigh and continue to move up his body.

"Oh, don't even think about it!"  I moved my foot away from his face and used it to kick away his roaming right hand.  I then turned and walked into the parlor to have a seat on the couch.  Jake knelt still in the doorway, naked and confused as to what was to come next.  I patted my lap, "Why don't you come and sit on Mistress' lap and we'll start your lesson," I said as I smiled at him now.  He still couldn't look at me in my eyes, but didn't hesitate to come and join me as his enormous erection stuck out and flopped awkwardly as he walked across the room.

As he settled on my lap, I mockingly reacted as if I were surprised by him.  "Oh no, that won't do," I scolded.  "By the end of the night you may be my little girl, but right now you're just a baby.  So crawl off Mistress's lap, crawl back to you were kneeling, and then, when I tell you to come, you crawl back over here, okay?"  He hesitated for just a moment, so I cupped his chin between my thumb and forefinger and nodded his head up and down as I answered for him.  "'Yes, Mistress Tricia.'  Now go!"   The poor baby did as I had laid it out until he was settled back on my lap.  "Why don't you suck on your thumb like the little baby you are?" I meant it to simply ridicule him, but wouldn't you believe your boyfriend followed that order as well!  I couldn't help letting out a devious laugh at that.  "Good girl," I giggled at him.  Again, his body (mainly his penis) reacted to being told he was a girl.

Even though he vehemently denied it when I asked him if he had a fetish for women's clothing, you were right in your suspicions.  I wouldn't be surprised if he has tried on your clothes while you weren't home, since the two of you are so similar in size.  Maybe he'd like to dress as a girl full-time?  He certainly seemed to enjoy my teasing at the Halloween party when he came in your old high school cheerleading uniform, as much as he tried to hide it.  Perhaps you could have him wear it to bed for you?  Like I said, you really don't know what kind of potential you got with this sissy.

Anyway, back to the nights events.  I held Jake on my lap.  "What time were you supposed to arrive tonight?"

"Ten o'clock, Mistress Tricia."

"And what time did you get here?"

"Ten after."

"Care to explain yourself before your Mistress corrects your ways?"

"It was Man-Mistress Mandy.  She made me do the dishes before-" I put a hand over his mouth to stop him.

"Now Jake, don't you think you could have better planned it out and had them done for Mistress Mandy ahead of time?"

"But Mistress Mandy, uhh, required my presence elsewhere..."  Ha!  I should have known you'd use your best skills, your skills of seduction to accomplish the task I gave you.  Bravo Mandy!

"Even so," I explained, "It is not up to your Mistress to make sure you fulfill all of your responsibilities, it's yours.  So, as punishment you will do all the cleaning for Mistress Mandy, ok?

"Yes, Mistress Tricia...." he whined to me.  See, I solved one of your problems for you before you even got a start on him.

"That's not it though, darling.  Also, I will have to punish you right now."  I picked up a large wooden hairbrush from the end table.  As soon as Jake saw it his eyes lit up with fear and excitement.  "Now lie down on your stomach across my knees and take your spanking like a good little girl."  As he was doing as I told, I felt his hard prick pulsate against my leg.  Soon he was in the proper position.  "I would just like to preface this by letting you know that this is for YOUR good, so you should show the proper gratitude when one of your Mistresses corrects you."  He picked up on my cue like the good little submissive he is.

"Thank you Mistress Tricia!"  I could tell our little pet was really going to enjoy this part.  I put the back of the brush down so it was right against his lips.  "Kiss!"  He did as commanded with closed eyes and then lowered his head down.  I raised the brush and delivered ten stinging blows across his backside.  One for each minute, I pointed out to our poor girl.  As I administered his punishment, I began to feel Jake's cock rub into my thigh on the soft, velvety material of my dress.  I pretended not to notice, but actually began moving my thigh to maximize the friction with each stroke.   As my arm came down, I let the tops of my breasts graze his bare back ever so slightly.  I know how to work these sissies, and hopefully you'll learn, too, Mandy.  When I brought down the final blow, I felt his cock erupt into my leg.

"Oh my!"  I stood up in mock surprise, and let Jake tumble off my lap and into a pathetic, sticky heap on the floor.

"Sorry Mistress Tricia."

"Damn right you are.  Can't wear this anymore."  I lifted the dress over my head as I scolded him.  "I can't imagine how Mistress Mandy will feel about this when you tell her."  He looked afraid at this comment, but became even more overwhelmed once my dress was all the way off.  I was wearing a black, leather corset that lifted my D cup breasts up to make them appear even bigger than they already are.  I also had on a pair of silk black panties with, as I mentioned before, matching garter belt, stockings and heels.  I have to say, your boyfriend licked his lips appreciatively.

"Slave, stop drooling." I snapped my finger and snapped Jake out of his trance.  I threw the stained dress at him.  "Go put this in the hamper in the bathroom upstairs and clean your tiny prick off.  Also, I want you to take the bag Mistress Mandy packed for you and put on whatever you find in there."  While Jake was doing as I commanded, I went and got some toys from my room.  When he came out of the bathroom, I was very pleased.  You picked a nice set of lingerie for your boyfriend to wear during his domination at my hands.  He stumbled out of the door awkwardly in his three-inch heeled, pastel pink, strappy sandals.  The sandals that matched his satiny thong with the lace on the front panel and spaghetti strap babydoll with the lace bodice.  MmmMmm.....a delicious choice my dear Mandy.  Jake obviously agreed because I could tell his prick was once again rock hard inside of its lace and silk encasement.

I laughed teasingly at him.  "I thought we didn't like crossdressing sweetie, hmmm?  How's it feel to be wearing your girlfriend's clothes again?  I could tell since last Halloween party that you were more than just playing at being a woman.  You should just admit to yourself now that you're a little sissy."  He just looked at me.  "I said, ADMIT IT!"

"I-I'm....I'm a little sissy...."

"Yes, a little sissy who'd like to be a real girl.  Hmm?  Do you wish you were a little girl?"

"Yes..." he was whimpering at me now.  Putty in my hands.

"Yes what, sissy!?"

"Yes I wish I was a little girl!"  He almost yelled it.  Like I said before, Jake is the type of submissive I could picture pantied, petticoated, and plugged everyday, ready to wait hand and foot on his Mistress.  You'd do good to look into it.

"Good," I replied, "because that's exactly what I'm gonna make you!  Sissy's gonna need a girl's name, though.  Anything in mind?"  He shook his head.  "How bout Jessica?  That's a nice name for a quiet, docile, little girl; don't you think so, Jessica?"

"Yes Mistress Tricia."

"So sissy, what is your name if anyone asks?"

"Jessica."

"And what are you Jessica?"

"A sissy..."

"And what is Mistress Tricia gonna turn you into?"

".....a little girl....?"

"Good.  Very, very good."

I walked over and gave "Jessica" (I hope you liked the name I picked out for your sissy boyfriend, hehe) a smack on her sore thong-clad bottom.  She let out a girlish squeal, which amused me.  "Now we must teach you to walk like a lady, so you're not stumbling around in those heels.  Practice.  Here in front of me."  Jessica began to wobble in front of me with difficulty.  "Take smaller steps, one foot in front of the other," I commanded.  I watched her until she developed a level of competence on her new pumps.  "Good girl Jesse!" I encouraged her.  "That's right mince for me like the little girl you are.  Shake that cute ass of yours," I said as I clapped for her.  "Give me a turn.  Aha!  Now, do a spin for your Mistress.  Wow, you're a very quick-learning sissy."  Jessica smiled at me and even blushed at my compliments.  I really suspect Jake is really much more Jessica on the inside than she ever was Jake.

"You're feet are probably sore from the walking.  Here."  I handed her a pair of thigh-high stockings that I had brought down for her.  "Put those on sweetie.  They'll protect your delicate feet from blisters.  Oh wait, before you put them on," I said as if a great idea had suddenly struck me.  "Let's paint your nails!"  I handed her the bottle.  "A nice soft pink to match your pretty lingerie. It'll be good practice for you....'cause you're doing mine next.  And trust me, you don't wanna make a mistake then, hahaha."

Under my instruction, Jessica delicately applied a coating of the shiny pink polish to her feminine feet.  She was a natural at it.  I suspect this isn't Jessica's first time painting toenails, either.  No doubt she's probably done it for you before, and more than likely tried it on her own toes once you were gone.  When she was finished, I showed her how to roll her stockings into an "o" shape and properly put them on her legs while keeping the seams straight.  Once that was finished, I removed my own heels and stockings and had Jessica apply a coating of glittering gunmetal-colored polish to my toes.  Once she was finished, she sat at my feet and blew on my feet until the paint was dry.  "What a pretty job!" I exclaimed.  "Pretty enough to kiss don't you think," I hinted.  Jessica worshiped my feet with her tongue again for a few minutes.  When I was pleased with her job, I ordered her to stop.  I got up from my position on the couch and led her by the hand upstairs to my bedroom. 

"It's time for the finishing touch of your transformation from Jake to Jessica."  She carefully walked into the room, swaying nervously on her heels.  I led Jessica by the hand over to my vanity and sat her down on the bench.  She looked warily around at all my special toys in the room.  "Look straight in to the mirror, sissy!"  She did as told and stared intently at her effeminate reflection in the mirror.  I carefully applied some cosmetics to Jessica's face. I started with some foundation and added mascara, eye shadow, and blush; I ordered her to pout her lips as I did up them in a soft pink gloss with glitter.  All traces of your boyfriend had vanished as the sissy inside revealed itself.  She sat there quietly and patiently with her legs pushed together as I worked.  

For the final touch, I walked over to my closet and pulled a platinum blonde wig off the shelf.  It had spiral ringlets that barely reached the shoulders.  I pinned it to Jessica's head and had her turn her head so she could feel the silky texture of her new ringlets drag against her shoulders as she moved.

"There!" I proclaimed, admiring my work.  The make-up was a bit overdone, like a hooker's, but then again, I like my sissies to feel like little sluts.  "Look at the little girl you have become."  Jessica just stared at the reflection of the timid-looking, but pretty young girl that was reflected back at her.  I smiled knowingly and reached my hand down between her legs.  Our little lady had a rock-hard, unladylike bulge in the lacy front of her pink thong panties.  "Hehehe," I laughed.  This seemed to bring her out of her trance.  "I see you like the new you," I whispered seductively.

I led her by the hand to my bed.  I sat down on the edge and pushed your feminized boyfriend to her kneels in front of me.  "Now, my little girl, worship your Mistress' womanhood with your sissy tongue."

"What, Mistress Tricia...?"

"I said, I want you to lick my wet pussy with your little, girly, sissified tongue!"

"But what about Mistress Mandy?" your little Jessica asked with worry.

"Right now you are serving me!  Now I want you, I am commanding you, to eat me out!"  With that, I grabbed Jessica by the curls of her wig and pushed her face into the moistness of my black panties.  I had her pull them down my legs with the waistband in her teeth.  Then, once again, I forced her quivering sissy face into my pussy.  This time there was nothing between my sissy's mouth and the wet folds of my pussy.  With her head clamped between my thighs, her warm tongue began probing the moistened core of my womanhood.  I rocked and bucked against her mouth, pushing her face forcefully as far into me as I could until her sissy tongue worked me to orgasm.  That's right, your boyfriend ate me out!  "Good girl," I encouraged her as I relaxed and lay down on the bed with your sissy boyfriend's head still firmly between my thighs.  I relaxed for a few minutes.  "Alright sissy.  Now it's your turn."

I lifted the little girl onto her feet and threw her onto her stomach over the footboard.  I produced a pair of handcuffs and while holding her down with my elbows, cuffed each wrist to a bedpost.  "Wait, what are you gonna do!?"  Suddenly he was no longer Jessica, but the pathetic Jake had returned.

"You fucked me with that talented tongue of yours, and now its time for me to fuck you."

"But how, with me like.....I mean..."

"Oh shut up, slave.  You know exactly what's coming.  Now it's time to really make a little girl out of you.  Hahaha."

"Tricia, no.  Stop!  Please, I don't think I'm read—" I cut him off by picking up my wet black panties off the floor and stuffing them into his mouth.

 

"Don't you even think of spitting those out, slut!" I yelled.  "I am in charge of you, and don't you forget it.  You're Jessica now, not Jake, and, haha, your ass is mine, literally."  I smacked him hard across his ass.  "You never address me as anything but Mistress Tricia, remember that!  Do you understand!?"  He nodded desperately and grunted as sweat, tears and make-up dripped down his face.  Your boyfriend was my pathetic sissy slave and completely at my mercy.  "Well, we will have to make sure you never disobey me again, missy!"  I laughed with delight as I yanked your pink thong panties down around his knees.  I put on a latex glove and rubbed lube into his asshole.  Then I put on my eight-inch strap-on dildo and slid it into Jake's ass.  "I'm fucking you, you sissy slut!  How does that feel?  How does it feel to have a woman's dick up your ass, sissy-girl?"  He cried out in pain and tightened his buttocks, but soon began to loosen and shake his hips to meet my thrusts.  I reached around and took his throbbing cock in my latex-gloved hand ("Oooh, Mistress...").  As I pounded thrust after thrust into your boyfriend's ass with my strap-on, I stroked faster and faster.  Soon he came in the palm my latex-gloved hand.  That's right, I made a faggot out of your sissified boyfriend.  I removed my dirty panties from Jake's mouth and wiped my hand clean with them before putting them back into Jake's mouth, or rather Jessica's.  She was all girlishness for good now.

I put a six-inch plug into her ass before taking my panties out of her mouth again.  "Here wear these, bitch."  She obediently put on the sticky, wet panties and smoothed them out over her ass.  "Now," I said, "it is bed time."  I opened up the door to a large dog cage with a blanket in it at the side of my bed.  "In there."  She obediently crawled inside and curled up. She looked so dazed and teary-eyed.  It was adorable.  Her make-up was a mess.  I had wrecked this sissy.  "What do you say, sissy?"

"Thank you Mistress Tricia." she whimpered from her cell.

"Good Girl."

We then went to sleep.

Before sending Jessica back to you that morning, I had her cook and serve me breakfast in her lingerie.  Then, I had her clean my house. Finally, I sent her back to you, Mandy, with a plug in her ass and my dirty panties still on.  I fucked your boyfriend and gave him the ultimate feminine experience.  If he hasn't had his fill, please send him back for more playtime.  You better take advantage of what a valuable little sissy slave you have in Jake/Jessica or I may take him off you for good.

Love,
Patricia

  

  

  

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