tagTranssexuals & CrossdressersSissy Meets Master's Lady Friend

Sissy Meets Master's Lady Friend

bysissysubTiffany©

This is part four in my continuing story of meeting a Master and changing me into his sissy.

The next morning after Friday night of Master Gene abusing my body for his sexual favors and turning me into his sissy girl Tiffany I was awakened by a text message from him informing me to check my emails for further instruction. I immediately checked to see what Master was wanting from or for me.

Master said he was impressed with my cock sucking skills, but I needed to practice on my gag reflex and to buy a realistic natural feel dildo about the size of his cock and to practice on it. He also directed me to a website for women that had articles and videos on how to suck cocks and please your man.

I was told that even though I was a good sissy faggot for him and did all he required of me and my body I needed to become more feminine to please him further and before he could show me off to his friends and possibly whore me out to them. And not only my mannerisms to be more femme but my looks also.

Master's lady friend Anna that he had mentioned to me in earlier conversations would be contacting me by Skype to assist in this transformation of becoming a proper girl for his desires. She would be teaching me female traits on how to walk in heels, make-up, clothes, shoes, lingerie, and talking plus acting more like a girl. This would all be done over the computer as I was not allowed to meet her without his permission and him being present.

Soon after, Anna contacted me and I began my sessions with her. She had several websites for me to go study on what she was teaching me which I did as I have now accepted my role of becoming more of a sissy to please Master. In fact I was enjoying my training with Anna and excited to become more of a woman and beginning to wish I was one for real.

I have learned proper techniques on applying my make-up and what shades of lipstick and nail colors go with my facial and body color. Anna picked out an Auburn wig cut into a bob style that she had me purchase along with some lingerie, outfits, heels, and perfume. She said no more manly cologne for Tiffany.

The most embarrassing thing Anna had me do was go to an eyebrow place in the mall for thinning out my eyebrows and making my eyelashes more feminine. Very humiliating for me to ask the lady to do, but I managed to and it really made my face look more like a woman. I have gotten used to purchasing women's clothing so that was no big deal.

Anna would have me dress in full drag and walk while on Skype for her to give me tips on how to walk more feminine, placing one foot then the other in front of it in a straight line and try to change my voice to sound more like a girl. Finally she said the transformation of me to a sissy girl was complete and she would let Master Gene know.

Master has kept in contact as Anna had been informing him on the progress she was making on turning me into a girl of his liking and letting me know he was pleased. This current email after Anna let him know my transformation was complete informed me he wanted to give Anna a reward for her hard work.

Anna liked sissy girls and has requested what Master called a lesbian experience with me made up in one of the outfits she had me purchase. I also had finally earned the right to visit his home and would meet Anna and him this Friday night at 8:00 p.m. for this to happen and to arrive already dressed and looking like his new girl.

The first thought going through my head was not being behind closed doors as a sissy, but leaving the house dressed as a woman. Would I be able to do it?

Luckily my car stays parked in the garage with my motorcycle and I should be able to leave being at night without the neighbors seeing me.

Friday night finally came and I have taken a considerable amount of time to put on my make-up, wig, painting my lips and nails, and dressing in my new clothes Anna picked out to look perfect for Master Gene and herself hoping they will like their final product in person.

I am wearing white lace thong panties with garter and thigh-hi white sheer stockings, pink bra, and a pink halter top with a very short white skirt and 4" pink heels. Looking in the floor length mirror I admit to myself I make a pretty good looking woman and hopefully the type of sissy bitch that will please Master and Anna. Lastly my new perfume to smell like a proper girl for them.

I have butterflies in my stomach as I walk into the garage to get in the car never being outside dressed femme. After getting into the car I realize I cannot drive in the heels and remove them placing next to me in the seat. As the garage door opens and I back the car out I am relieved to not see any of my neighbors as I drive away.

What seemed like forever as at every stop light I was wondering if people in the other cars knew I was a man in drag I arrived at Master's house.

I put on my heels, straightened my skirt and blouse and walked to the front door ringing the door bell. Master opened the door eyeing me up and down "Damn girl you look hot. Get that sweet ass in here now."

Upon entering I hear "Hi Tiffany, glad to finally meet you in person and see my work" as I turn facing Anna.

"Come over here and give me a hug and kiss."

I walk towards her knowing Master Gene is watching my ass and hips move as I walk in my heels, pleasing him, and making me more excited. Our arms wrap around each other as our lips meet for the first time. Our tongues start to swirl around each other as her hands move down my back, stopping to gently squeeze my ass/pussy cheeks. Our breathing is getting heavy as both of us are getting more aroused.

"Don't stop now girls I'm enjoying the show" I hear Master say.

"I'm sure Anna would love her tits sucked on."

I slid my mouth down to Anna's neck slightly blowing and kissing as I remove her top and bra exposing her beautiful breasts, only wishing my tits were as nice and big as hers.

I now move gently massaging her big tits as I move my tongue to her breasts. Kissing and licking lightly brushing my tongue across her nipples and then the same to her other breast, as my hand gently squeezes one breast then the other. I move my thumb and finger to her nipple rolling it between them and sucking deep into my mouth. Flicking my tongue across her nipple as I continue to suck and then the same to the other breast, and hearing Anna start to moan in delight.

"Take your clothes off, but Tiffany leave on your panties, garter, stockings, and heels" Master tells us.

I then lean forward moving my small tits to Anna as she hungrily sucks my nipples into her mouth and I am oblivious to all around me. For the moment that is until I feel Master's firm hands on my pussy cheeks.

His hands massaging my pussy cheeks for the moment, but then undoing my garters and sliding them down my legs along with my panties and off my body. I now only have on my thigh hi fishnet stockings and my heels exposing my ass pussy.

Before I can react I feel Master's hand slapping against my pussy cheeks softly at first, but harder with each slap, and I cannot see but know my cheeks have to be beat red. My cheeks sting from the slaps and I cannot explain it, but I am stimulated from the slaps, begging for more like a sissy bitch as he slaps harder, stinging, but not hurting me.

It seems like a minute or two and then I feel Master Gene's hand on my pussy rubbing it, spreading me open, and then a lubricated finger pressing against my pussy and slowly sliding in. My pussy tighten's at first, but then loosens up as more of the finger moves into my pussy until it is all the way in. Feeling Master's inserted finger now moving and rotating around in my pussy, then a second, and it feels so good I start moving fucking his fingers.

Screaming "Please Fuck my Pussy Master, please fuck me" as I slid my pussy faster and harder on his fingers, moaning loudly, and breathing harder. Anna moves off my tits smiling watching me and Master.

"Not yet Tiffany as I am only getting your pussy ready for Anna."

What I think looking up to Anna and to my surprise she is now wearing a harness with a huge strap-on.

"Suck it like a real cock where I can enjoy watching my sissy bitch" Master says.

I do as Master desires, sucking her strap-on as she fucks my mouth with it. Anna then tells me to get on all fours, doggie style, as she is going to fuck my pussy real good with her strap-on cock. I do as told seeing Anna lubing up her strap-on as I wait on all fours like a dog in heat, then feeling her hand slap against my pussy cheeks, not once, but several times, my pussy cheeks stinging even more now. Then feeling her spreading me open and entering my pussy with her strap-on.

Damn it feels so good as Anna eases her fake cock into my pussy slowly, then pulling out and slowly entering again. But now she shoves her cock in deep and hard, holding my hips, pulling me deep into her thrusts. I am bucking back against her deep thrusts as my pussy fucking feels so great.

As I hear myself screaming "Please Anna, fuck my cunt, please don't stop" begging her.

"I love fucking tight sissy ass" I hear Anna say as she moves faster and faster in my sissy cunt and hearing her breathing heavily and moaning more.

Her thrusts shoving me into the bed when I her her scream "I'm cumming" and feeling her weight falling on my back as she shoves her dildo deep into my cunt. Precum leaking from my tiny clitty so hard myself but knowing I cannot cum without Master's permission. Exhausted we both collapse on the bed breathing hard but relaxing for the moment.

And then I hear Master saying "Now my turn to fuck that cunt Tiffany. Present yourself for your Master's cock."

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by Anonymous07/14/18

Meh

The fuck is this shit?

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