tagTransgender & CrossdressersSissy Meets Master's Male Fiend

Sissy Meets Master's Male Fiend


This is part 5 of my Master turning me into a sissy and his woman.


Master Gene has now taught me that when I around him or his friends I will dress and act like a sissy girl thinking of being one for real. He now expects me to arrive at his house as Tiffany. No longer treated like a man I will only go by Tiffany and be his girl. I now spend every weekend at Master's house dressed femme doing whatever chores he gives me and being there for his pleasure of my mind and body. He has even given me space in his or I should say our bedroom for my female lingerie and clothes. I feel so special now and happy being his woman on weekends and hoping maybe one day to deserve full time as Master Gene's woman feeling like his wife and I have come to accept my new role. I want to live every day with the dream of making my man happy and proud of his woman Tiffany.

Master Gene has informed me this Friday a long time friend of his Frank is coming to town and he will be showing me off as his new woman and I must be on my best behavior to make him proud. I am so excited and feeling so girlish knowing my Master wants me to meet his male friend. I am thinking he is proud of me and wants to make his friend envious of him for having such a sexy lady.

Knowing I need to look extra special for Master to show off his woman I decide to go shopping and look for the perfect outfit, one I will look sexy in, but not trashy for this special night. I now belong to Master and will do anything that he ask of Tiffany, but I must admit it does feel so good knowing men think I look pretty. I decide on a very short low cut red dress with shoulder straps and red 6" stiletto heels to match. From Victoria Secrets I find a red with black lace trim matching bra and thong panty set with black garters, and black thigh hi sheer stockings.

During work Friday I find myself thinking only of tonight as the day drags on looking at the clock. Finally 5:00 pm and home to get ready. Such a special evening for me and I spend extra time shaving my body, painting my nails, make-up, and putting on my page boy cut auburn wig. I then put on the clothes I bought hoping to please Master Gene and make him happy, like a man should about his woman.

On my way to Master's house I receive a text from him saying he and Frank is stopping for a few drinks and to go inside as I now have my own key and to be ready to entertain them later in the evening as Tiffany.

This being the first time we have entertained together as a couple I want everything to be perfect and light some scented candles to provide atmosphere and wait.

Soon I hear the front door opening and get so excited, feeling all tingly inside, knowing Master, but tonight I have been instructed to just call him Gene, is home for me and getting to meet one of his male friends. I can tell Gene is pleased by his facial expression as I walk to him and give a big welcome home kiss and say I Love You. Frank is introduced to me and I can tell he is checking me out from head to toe as we move to the living room. Gene and I sit on the couch and Franks sits across from us in a chair. After chatting for a moment I go in the kitchen as instructed returning with drinks for us like a good woman does for her man and guest.

Gene leans over and whispers in my ear "You look beautiful tonight" and his warm breath sends shivers down my body.

"And I would like for you to tease Frank with some views of your panties to make him envious of the woman I have, but to be discreet when showing him" Gene also tells me.

"I whisper back, anything you desire of me, Tiffany will do for you, to show my love."

As we talk I slowly uncross my legs and open them a little towards Frank and I immediately see he is checking my panties and clitty out. I also notice a nice slight bulge forming in his pants thinking he must like what he sees.

I then feel Gene's warm manly hand on my leg as he says "I have a special surprise for you tonight Tiffany."

And continues "You will be pleasing me and Frank tonight and will do whatever he desires, but I will be here and to trust me in what might happen as I think you will enjoy having two cocks together."

I lean over and kiss Gene passionately on the lips as I tell him "I always trust you Gene and love you very much and will always be here for your desires and pleasure."

Gene looks at his friend Frank smiling and saying "Tiffany has agreed tonight to please your desires since you are our guest."

Frank looks at me and says "Great Tiffany I look forward to rest of this evening."

"First I would like for you to dance to the music on the radio for me and take your dress off slowly as I enjoy the rest of my drink while admiring your beautiful body," Frank continues.

I get up and start swaying my hips to the music moving my hands down my body and legs as I do and then up feeling my breasts as I lick my lips smiling at Frank and Gene. I then slid my dress off my shoulders to the floor and step out of it exposing my panties, bra, garters, and stocking with my 6" heels and notice both my man and Frank looking me over with delight.

Frank then tells me to unhook my garters from the stockings and remove my panties and then rehook the garters. After complying with his desire he says "turn around slowly where I can inspect your body, clitty, and pussy," which I do obeying him as Gene has instructed me.

Frank then rises, comes to me and slaps my ass hard a couple of times, my ass stinging as he does, and says "Go to the bedroom and lay on the bed and I will be right in," which I do moving my ass in my heels for him and Gene to enjoy.

As I lay in bed it seems like an eternity as the excitement in me builds wondering what next will be required of me, but I know that my man will not let any harm come to me or make me do anything I am not conformable with.

Finally I hear the door open and see Gene entering without Frank, my heart skipping a beat hoping I have not disappointed him and Frank. Gene sits on the bed looking into my eyes saying "I am so happy with you tonight and how beautiful you look," easing my thoughts.

Then continues "Frank will be right in, as he had to get something from his vehicle."

Gene holds my hand and tells me "You have been the perfect hostess and followed my desires perfectly, but tonight is not over yet, but just beginning."

"Frank has loved what he has seen in you Tiffany and I have agreed as his friend and host to let him continue with you tonight for any desire he has and you will obey him like you do me."

"But remember I will be here also to make sure you are at ease with Frank and would never let anything happen to you."

"I know and trust you Master with all the love I have for you and the love you have for me," as I kiss Gene on his lips.

Master Gene explains to me that Frank is into BDSM and he will be coming in the bedroom with some toys and equipment, but assures me that I will be okay as he is staying in the bedroom also to watch and might even participate some.

Frank enters the bedroom carrying a gym bag eyeing me on the bed saying "I am looking forward to rest of tonight as you are a beautiful sissy woman and truly excite me. Tiffany you are to obey me completely and do you understand this command?"

"Yes I do, Frank" I answer back looking up to him smiling.

"Great choice Tiffany, and remember you are here for my pleasure and amusement, not yours, and you will be severely punished if not obeying one of my commands" Frank tells me.

"Now spread your legs and arms wide apart for me" which I immediately do.

I see Frank reaching into the bag and he pulls out wrist and ankle restraints and confines my arms and legs spread eagle to the bedposts. I watch as his eyes inspect my body laying here and he smiles and says "Good girl, you have been obedient and I am going to have fun with you tonight."

Laying there on the bed I then watch Frank remove his clothes exposing a nice huge cock as he climbs on the bed sitting across my stomach. He reaches down and starts rubbing my tits through my bra, my body moving as he does, and then removes it freeing my tiny titties for him to see. He pinches my nipples between his fingers making them hard as he smiles at me saying "Nice little sissy titties."

He then rises from the bed and pulls nipple clamps from his bag and places one on each of my nipples, the coldness from the metal making my nipples harder. As he tightens them I start to feel the pain but do not want to admit it to Frank, but the more he tightens them I start to squirm and tell him they are starting to hurt a little. Frank laughs as he tightens them a little more and then stops, looking at me, and says "I will not apply more pain than I think you can handle," but I can feel the sensation from the clamps on my nipples hurting.

Frank again moves back to his bag removing a blindfold and places it over my eyes and I cannot see anything, but feeling the pain from the nipples clamps. I am now confined to the bed blindfolded with just my stockings, garter, and heels on with clamps to my nipples, hurting some, wondering what is next but excited at the same time.

The next thing I feel is a hand to my pussy lubing it up. I can tell it's not Master Gene's and assume its Franks as I feel a finger enter my pussy slowly and then two as they start to finger fuck my pussy. The fingers in my pussy feel so good I start to buck against them heightening the pain on my nipples. All of a sudden the fingers move from my pussy and I hear Frank say "I am about to insert a dildo in that sissy bitch pussy and it will stay there until I am ready to remove it."

I feel the dildo spreading my pussy lips wide as Frank slowly inserts it all the way into my pussy hurting a little as he does as it seems to be very big in size. Now moving the dildo in and out of my pussy slowly fucking me with it as there is movement on the bed and I feel balls up against my chin and a cock laying across my face. Gene has not said anything but I can tell they are my Master's since I have sucked them plenty of times and know them and his aroma well. I reach my tongue out licking around and underneath them enjoying smelling his scent as I do, but now Master Gene pulls back and inserts his cock between my painted lips and I hear his manly voice tell for me to suck and lick his cock like a good slut should.

The dildo fucking my pussy starts moving faster, deeper, and harder as Master is now fucking my mouth with his huge cock. This fucking of me goes on for what seems forever when suddenly I feel Master shove his cock deep into my mouth, his balls against my chin and erupts wave after wave of his warm cum down my throat as Frank shoves the dildo deep into me at the same time. I hear Master Gene telling me to swallow every drop of cum as he leaves his cock deep inside my mouth and after a minute sliding his cock out to the edge of my lips for me to clean with my tongue.

Master Gene moves off the bed and I feel someone on it again thinking it must be Frank but not knowing since I cannot see anything. I feel the nipple clamps tighten again hurting more as they are tightened and now another cock against my mouth lips sliding between them and starting to pump in and out. I wrap my lips tight around the shaft as each thrust bangs his balls against my chin. The mouth fucking goes on for a few minutes then I feel his cock start to quiver and spurt his cum running into my mouth and down my throat swallowing like a good woman should. Frank slides his cock from my mouth and starts to rub it across my lips telling me to clean it like a good bitch and I lick it with my tongue not wasting a drop of cum.

I now hear Franks voice telling me to not be startled as he is going to put a collar around my neck, but not to tight to restrict my throat muscles as he is not done with them yet. There will also be a leash attached to the collar for him to lead me around with. He continues to tell me he is going to untie me from the bed, remove the blindfold, and I must not move until he leads me off with the collar and leash or to remove the dildo. The dildo must remain in my pussy as I am lead around the room.

I now feel a tug on the collar and hear Frank saying "Move off the bed and get on the floor on all fours like the sissy bitch dog you are."

Now on the floor as instructed Frank pulls harder on the leash and says "Follow me bitch like my dog would" which I do around the room when he suddenly stops, and tugs on the leash pulling me to Gene's ass.

Frank tells me "Smell Gene's ass and lick it good like a bitch dog" as he laughs.

I do as told smelling and licking Gene's ass feeling so humiliated on all fours collared with a leash and a dildo in my ass pussy. But now hearing Gene start moaning and enjoying I forget about myself and start tongue fucking his ass while hearing Frank "Damn Gene your sissy girl is a good bitch, always doing as told."

Gene then moves, turning around, and shoves his hard cock again in my mouth looking down at me and saying "Suck it real good like my sexy woman knows how."

At the same time I feel a stinging sensation on ass checks as Frank starts whipping my ass with a cat-o-nine tails hearing him laughing again and telling Gene how good his sissy bitch looks sucking cock. Frank lands a few more whacks on my ass each hurting more as he does the pain hard to take now as he says with a sternness in his voice "Suck your man's cock like a whore slut should bitch."

Suddenly I feel Franks hands on my ass pulling the dildo from me and saying "I am going to fuck this pussy and you're going to like it."

His hands spread my pussy lips wide and he enters me fast and immediately starts pumping his cock in and out of my pussy, his balls banging against my ass cheeks.

I wrap my lips tighter around Gene's hard shaft feeling his heavy balls banging against my chin as Frank pounds my pussy. Within minutes I hear Frank in a loud voice saying he is going to cum and feel him shove his hard cock deep inside me twitching and shooting wave after wave of cum filling my pussy. And almost simultaneously Gene shoves his hard cock deep between my painted lips as he spasms cum filling my mouth as I swallow down my throat. All three of us moaning and breathing hard as they remain in my openings enjoying the moment.

Feeling Frank slide his cock out of my pussy, some of his cum running down my cheeks and then Gene pulling from my mouth as both move standing together before me as Gene says "lick us both clean Tiffany."

And I do cleaning both their cocks licking and sucking them clean not wanting to waste a drop of cum tasting my pussy on Frank's cock mixed with his cum as I do.

When I am done I hear Frank telling Gene "your woman was a good fuck and I really enjoyed fucking her sissy cunt and damn it was so tight."

Then looking down at me and smiling Frank says "I have enjoyed my time with you Tiffany and such a good host, but I must now leave as I have an early appointment tomorrow and need some rest. But I look forward to the next time I am in town."

Smiling back I tell Frank "and so do I Sir."

Frank removes his collar and leash from my neck and packs up to leave as I move and lay on the bed exhausted from tonight. As I lay there I hear Frank and Gene saying goodnight and Master returning to our bedroom and back alone with me again as his woman.

Master looks at me saying "I am so proud of you tonight Tiffany in how beautiful you looked and how well you accepted Frank and his wishes. You were my perfect girl tonight."

Crawling into bed wrapping his manly arms around me I am so happy belonging to Master as we fall asleep together and I dream of what the future might hold for us.

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