A New World Opens Up

I was 25 when my parents were killed in an automotive accident leaving me with a sizeable inheritance and after settling the estate and having no family to speak of after my divorce, i decided to quit my job and travel the states. I found myself in Chicago on a beautiful Sept. day and needed a haircut, it had been 3 or 4 months since my last one decided to see a cubs game instead. After the game i wanted to enjoy the evening and started walking back towards downtown figuring to grab an uber when i tired out. As evening fell i slipped into a local bar and opened a tab, the Saturday crowd slowly streaming in.

Sitting at the bar i began reading my phone and steadily drinking. I must have lost track of time because someone tapped my shoulder and asked if the stool next to me was taken, I turned to find a beautiful brunette with flowing chestnut brown hair and legs to kill for. Her green eyes looking at me with a perfect smile, she was wearing a summer dress that gave her the girl next door look.

I nodded to her and said she was welcome to sit if I could buy her a drink to which she agreed. I introduced myself as Jim and she told me her name was Lisa. The conversation flowed easily as we shared a few drinks when Lisa looked at me and asked if I was gay. After seeing the puzzled look and my face she laughed and explained that we were in a gay bar, I paused to look around and seen we were indeed in a gay bar and turned to ask her why she was here.

Lisa read my mind, as i looked into her green eyes she explained she was a transexual. I was looking at this beautiful woman who I was sexually attracted to trying to comprehend if that was even possible when she took my hand and placed it on her leg just above her knee, while looking into my eyes she gently pushed my hand below the hemline of her dress. Her skin was warm to the touch and soft beneath my hand as it slid up her smooth silky skin, my head was spinning from the alcohol and my desire for her. I've always considered myself straight and here I was confused on what to do. Lisa continued to push my hand up her leg as I felt my cock growing hard, as my hand reached the cool fabric of her panties I felt the bulge that lied within.

Instead of pulling back my hand I cupped her cock and balls, leaned in to kiss her. Our lips met, tongues intertwined and I felt the electricity I haven't felt in a long time. My mind was swimming in the cloud of alcohol and it felt absoulety natural to want to feel her cock in my mouth and to taste her. The passion of the kiss only increased my desire for her as she pulled away and asked if I would like to go to her place.

I readily agreed and reached for my wallet as she reached for her phone to arrange for an uber ride, after I paid the bar tab we went to the curb to wait for our ride. I was excited as much as

nervous not really knowing what to expect but that quickly melted away as Lisa pulled me to her and ran her hand up my leg grabbing my cock and whispering in my ear that tonight would change my life.

The uber driver pulled up to the curb and we piled in, Lisa leaned over to say that she coudn't wait to feed me her cock as she made sure my cock was still hard. It was a short ride to an upper class neighborhood where her condo apartment was located and we raced inside getting no more than a few feet from the door locked in a passionate kiss.

Lisa started to show her dominant side as she pushed me to a wall and ordered me to remove my clothes, I quickly shed my clothing as she slipped of her dress letting it slide to a heap at her feet. I removed her bra freeing a set of tits any women would love to have with rose colored nipples which begged for my attention.

It wasn't long before she pushed me to my knees and grabbed my hair pulling me into her crotch, I grabbed onto her legs and slid down her thighs and worked my way back up with my tongue lightly grazing her legs until I arrived back at her white pantied encased cock, I traced the outline of her cock through the thin material until she ordered to remove her panties

I slipped them of her hips exposing a thick seven inch cock and balls with skin as silky as her legs and let them drop to the floor. Lisa cock was sticking straight out to my face, a fleshy pink with a purplish mushroom head, I hesitated for a second before she grabbed a fistful of hair and told me I was her little cocksucking bitch before shoving her cock into my mouth

As the head of her cock touched my lips I felt the velvety smoothness and opened my mouth to accept my gift, as I closed my lips around her hard shaft my tongue swirled around the mushroomed head. Lisa let out a moan and forced her cock deeper into my mouth telling me what a good little slut I was going to be. All I wanted to do was please her and started to bob my head up and down on her shaft. She picked up the rythym and began to fuck my mouth thrusting in and out of my mouth. I slipped a finger up her ass and she began groaning, telling me not to stop and what good cocksucking slut I was. I felt her spincter tighten up around my finger as she started pumping her cum in my mouth telling me not to waste a drop, The cum shot out of her cock like a fountain spraying the back of my throat as I tried to swallow the salty seed

After making sure I swallowed her load I licked her cock clean and waited for her to give my cock some relief

I stood up slowly while Lisa was inspecting me, I am about 5'9 to 5'10 around 145 pounds, she commented on how shapely my legs and ass were. Then she told me that she could work with that and that she guessed right about me, I was ordered to follow her to a spare room that had what appeared to be bondage equipment

When I hesitated she grabbed my cock and told me I was to be her little slut and if I wanted to cum I had better listen, my cock gave me away bobbing at attention, I was under her spell and she knew it. Lisa cuffed my wrist and attached to a pulley system raising them up, then attached a spreader bar to my legs, satisfied I wasn't going anywhere

She stepped behind me and I felt a vibration running up my calf as she explained she liked her slaves smooth shaved, with a small set of clippers she removed all the hair on my body. I was leaking so much precum as she buzzed my cock and balls then spreading my asschecks running the clippers up my ass. I never wanted relief so bad in my life and I was willing to do anything for it. After the clippers she shaved me clean leaving no trace of body hair

When she was done she grabbed my balls and squezzed until my knees began to buckle asking me how I liked my new look, laughing that my dripping cock gives it away. She then told me I was to address her as mistress. Mistress said that she knew right away I would be a good cocksucking sissy but was suprised how easily I was turned into a slut

Releasing me from bondage mistress ordered me to get her cock ready to fuck my virgin pussy, once again I was on my knees sucking my mistresses cock. Once hard she ordered me on all fours as she reached for a tube of ky jelly telling me she can't wait to break in my pussy. mistress lathered her cock and then began working a finger into my ass telling me how tight my pussy is. As she sawed one then two and three fingers in my boy pussy I began moaning how good it felt and begged her not to stop. Mistress laughed and told me not to worry because she was going to fuck my brains out.

As she lined the head of her cock at my pussy I attempted to look back and she pushed my head down as she pressed her cock past my spincter. I thought she was going to split me in two as she worked in cock into me balls deep, I began to beg her to fuck me, that I would be her slut but please don't stop. Mistress started slow then began thrusting her cock taking my virginity, I never felt such pleasure in my life

As she pounded my ass she told me that I would be turned into a full time sissy and promised I would be her sissy because I needed her hard cock fucking my boy pussy, Mistress said she was going to cum and reached around grabbing my cock and with a few strokes I began cumming while my spincter muscles began to spasm grabbing her cock as she filled my ass with her cum. I came so hard I blacked out for a few seconds recovering as mistresses cock slipped from my ass

I was put to bed and told to rest up for the adventure begins tomorrow.

To be continued