Master Mike - Part 4

Sissy Jersey Meets Master’s Lady Friend

Read Part 3 First? -> Read Here

It was now Saturday morning. Just last night Master Mike abused my body for his sexual favors and turned me into his sissy slave Jersey. I was awakened by a text message from him informing me to check my emails for further instructions. I immediately got up and went to my computer to check my email to see what Master was wanting from or for me.

Jersey, I am impressed with your cock sucking skills, but you need to practice on your gag reflex. You will need to buy a realistic and natural feeling dildo about the size of my cock. You will need to practice sucking on it for one hour every day from now on. I attached a link at the bottom of this email that has more cock sucking training articles and videos.

My friend Anna will be contacting you to assist in your transformation of becoming a proper sissy for for my needs. She will be teaching you female traits on how to walk in heels, make-up, clothes, shoes, lingerie, and talking. This will be done over skype and you don’t need to meet her unless I am present.

Be good and listen to her.

Master Mike

Soon after, Anna contacted me and I began my sessions with her. Over the next week, she would spend hours on Skype with me. She had several websites for me to go study 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 for 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 Jersey.

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’s. I have gotten used to purchasing women’s clothing so that was no big deal.

Anna made me dress in full drag and walk while on Skype while she gave me tips on how to walk more femininely, 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 slave was complete and she would let Master Mike know.

Master kept in contact with Anna and she had been informing him of the progress she was making on turning me into a sissy 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.

Sissy Jersey, Anna likes how much of a sissy you’ve become and has requested a lesbian experience with you. You will be dressed in one of the outfits that you recently purchased and be ready for her. You have earned the right to come to my house, and there you will meet Anna as well. Come to my house this Friday at 8pm. You will arrive already dressed as a sissy. I will send you my address in a later email.

Master Mike

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 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, and wig, paint my lips and nails, and dress in my new clothes Anna picked out to look perfect for Master Mike and herself.

I am wearing white lace thong panties with a garter and thigh-high white sheer stockings, a hot pink bra, and a hot pink halter top with a very short hot pink skirt and 4″ pink heels. Looking in the floor-length mirror, I admit to myself that I make a pretty good-looking sissy 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 text Master at 7pm and inform him I am ready, I quickly get a response back with just his address. It’s about 30 minutes away.

The butterflies in my stomach are intense as I walk into the garage to get in the car never being outside dressed, sissy. After getting into the car I realize I cannot drive in heels. I removed the heels and placed them 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.

I seemed to be hitting every stop light and I was wondering if people in the other cars knew I was a man in drag. After what seemed like forever, I finally arrived at Master’s house just a few minutes before 8pm.

I got out of the car, put on my heels, straightened my very short skirt, and started walking to the front door. I rang the doorbell. Master opened the door eyeing me up and down “Damn bitch you look hot. Get that sweet ass in here now.”

Upon entering I hear “Hi Jersey, glad to finally meet you in person and see my work” as I turn to face Anna.

“Come over here and give me a hug and kiss.”

I walk towards her knowing Master Mike 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/sissy cunt 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 gently massage 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 and 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.

“Both of you, take your clothes off, but Jersey 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 sissy cunt cheeks.

His hands massaged my sissy pussy cheeks for the moment, but then undone my garters and slid them down my legs along with my panties and off my body. I now only have on my thigh-high fishnet stockings and my heels exposing my sissy pussy.

Before I can react I feel Master’s hand slapping against my sissy pussy cheeks softly at first, but harder with each slap, and I cannot see but know my cheeks have to beat red. My cheeks sting from the slaps and I cannot explain it, but I am stimulated by 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 Mike’s hand on my sissy pussy rubbing it, spreading me open, and then a lubricated finger pressing against my sissy pussy and slowly sliding in. My sissy pussy tightens at first but then loosens up as more of the finger moves into my sissy pussy until it is all the way in. Feeling Master’s inserted finger now moving and rotating around in my sissy pussy, then a second, and it feels so good I start moving fucking his fingers.

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

“Not yet Jersey, I’m only getting your sissy pussy ready for Anna.”

I looked up at 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 pussy mouth with it. Anna then tells me to get on all fours, doggie style, as she is going to fuck my sissy 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 sissy cunt cheeks, not once, but several times, my sissy pussy cheeks stinging even more now. Then feeling her spreading me open and entering my sissy pussy with her strap-on.

Damn it feels so good as Anna eases her fake cock into my sissy pussy slowly, then pulls out and slowly enters 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 sissy pussy fucking feels so great.

As I hear myself screaming “Please Anna, fuck my pussy, please don’t stop” begging her.

“I love fucking tight sissy pussy” I hear Anna say as she moves faster and faster in my sissy pussy and hearing her breathing heavily and moaning more.

Her thrusts shoved me into the bed when I hear her scream “I’m cumming” and felt her weight falling on my back as she shoves her dildo deep into my pussy. 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 pussy mouth and sissy pussy Jersey.

Present yourself for your Master’s cock.”