Sissie

       The Contract 

           Pt 1 Flag

My name is Sissie it used to be Matt, but that name doesn’t fit. I just put up a sissy pride flag in my window. Mine has pink and white stripes with a modified phallus symbol that looks like a heart with a limp arrow jutting out of it.

        I use it to advertise that I love putting on lingerie and getting fucked like a woman. I was always unable to entertain my fetish beyond playing dress up at home and masturbating to sissy porn when I was alone. Although my family already knew I put on women’s clothes, and makeup entertaining with your family around ain’t easy. 

         That all changed When I was 22. After I started going to community college and got a job that I could support myself wirh at a marijuana dispensary that was very friendly to LGBTQ people like me. 

      Which is how I met Helen and who owned a hardware store across the street from my job. 

     We met after I picked up a cute but rundown 3 speed girls bike at a garage sale for $20 one day I got it in my mind to refurbish the bike. So went in to the hardware one day after work buy some tools and spray paint and other odds and ends. Feeling extra fem that day I definitely wasn’t hard to miss the way I was wiggling my cute ass. Dressed in tight capris to show off my new pink and white stripe socks and cute rainbow t-shirt and a pink bandanna I used to tie my hair tied back 

       Though some might think it, I’m not inept with tools and I knew what I needed. But I did want to talk about my idea for the bike.                       So when when the tall blond lady asked “Do you been help?” I accepted.  And ended up talking her ear off after she stepped in to offer help like a Chatty Cathy doll. OMG she was an Amazon and built to please.  And with her somewhat growling girl voice she sort of reminded me of Wendy O Williams of the Plasmatics .

      I find it easy to be friends with women but sexually it doesn’t work unless I use a dildo or eat pussy. Still I thought to myself Helen was hot and I’d definitely share a man with her. Talking to her was fun she knew all sorts of stuff about tools and the look I was going for. I ended up buying about $150 worth of  bike parts, tools, hardware  and promised to bring the bike back to show her my results.                                      

     Not long after making my purchase I rushed home. I could barely contain my self and needed my dildo to help me relieve the empty feeling in my ass. Helen was so hot I imagined her as a mistress telling me to do all sorts of naughty things to myself. I lay on my bed that day fucking my ass with a dildo till I came.

        I didn’t know if Helen was into sissy’s. What I did know was I wanted her to fix my lil red wagon. And I really didn’t have to wait long to get an answer 

      It seemed like I was running into her in the neighborhood near my work quite a lot. Either alone or with her husband Don. Who was total dad. A grey haired silver fox in his 40’with an athletic body I had the hots for him immediately. We soon formed a friendship . Quite a few time I ended up at Helen’s for BBQ’s and going out shopping and talking about my kinks. One night I both me and Helen got invited out to a bachelorette party by Helen my coworker Ann who was getting married . 

       Wow what a wild party. If you think a boys night out is nuts go out with a bunch of ladies on a bachelorette party. Stripper dancing about and swinging their dicks g-strings full of cash and drunken debauchery. Toward the height of the party Ann encouraged by her brides maids began sucking a stripper who’s claim to fame was being able to hold his nut back. I was so hot from watching Im glad my dress was able to hide my unladylike erection especially when he came all over Ann’s face. Helen saw the lust in my eyes and knew I was having issues. Whispering in my ears she said “Let’s fix you little problem in the ladies room hon.” 

         After going into the womens room Helen locked the door then said “Bend over the sink dear.”

       “Won’t your husband get mad?” I asked worried I’d cause strife.

        “Shush and do as your told sissy.” Helen commanded in a firm but gentle tone.

         Felling the strong urge to be commanded I did as I was told. As I straddled the saint Helen quickly fished a vibrator and lube which she applied generously. Then after pull my panties down and pulling my cock and balls back she commanded in that same firm but gentle manner “Okay now close your legs hon.” 

        Then unceremoniously she pushed the vibrator into my ass and set it on its highest setting.  It didn’t take much after that.  Helen knew what to say and do to make a sissy cum. She tormented me with that simple vibrator telling me if she let me cum I would have to pay the price and agree to read the terms of her contract.  Helen was fucking my ass with the vibrator so good I really didn’t care she was demanding I read her contract and whimpered “Yessss..Okayeee…please let me cum. Then with that she took me over the edge. 

       OMG I was a mess giggling Helen wetted down a bunch of paper towels with soap and warm water and cleaned  me up after throwing the mess  in the trash she produced a tampon inserted it in me and said “Whew…I must have knocked a little turd loose hon. I can’t have you shitting your panties.

          After the evening was over while sharing an Uber back Helen brought up the contract. Not caring who heard Helen asked “So did you have a good time sissy?” “Uh-hu.” I replied. Smiling and rubbing my leg she said. “Good and by the way I haven’t forgotten the contract you agreed to read. Be at my place at Noon tomorrow dressed in business attire. “