XXX A Helpful Handyman
A mistress leaves a list of chores for her sissy, but does not mention the handyman coming over.
Posted on
Add A New Story
I have been a VERY good sissy for my mistress. I do not cum unless commanded, pose unless ordered, and I do all of my chores happily, promptly, and sexily. I thought that this all changed for a moment, but she, my mistress, even had this planned.
While my mistress is at work, I am to be a good little sissy and take care of the house: clean the floors, take care of the laundry, and make sure that the house is pristine when she returns. Today, however, things were different. A man, a very strong, rugged, and handsome man, arrived with orders to replace the gutters around our house. I was not so much shocked by his arrival as my mistress takes care of the tougher things that are not suitable for a sissy, as much as I was dumbfounded by his hotness!
"I'm here to replace the gutters and collect the first installment for the job. I can accept cash, checks, or even other things." His wry smile made me cum a little in my Super Girl panties. I wish that he knew I was a sissy, was ok with that, and my mistress allowed it!
"Thank you for coming over," I said with a hint of seduction, knowing that my mistress would not mind me flirting too much 
As he began to work, the day got warmer and warmer. I got more and more aroused, and he looked hotter and hotter! I was amazed at the effectiveness of the hormones that I had been taking. My mistress truly is a miracle worker! He worked solidly until noon. At which point he got his lunch out of his truck and sat on sawhorse to eat his sandwich. I watched secretly through the window, wishing that I could gobble him up like he did that sandwich!
I could not take it any longer! I wanted, no I NEEDED him, NOW! I went to my room, got my sexiest lingerie, tightest shirt, and skimpiest top. If I could not fuck him, then maybe he would barter a nice BJ for a discount. I mixed up a nice cocktail and took it out to him on a tray, strutting, sauntering, and posing like a good sissy.
"What do you have there?" He said with lust dripping out of his mouth and into my ears. I nearly came right then!
"Thought you might like a little refreshment, and then some dessert," I said as lustily as I could muster. He reached out and fondled every so expertly one of my erect nipples, then the other. I moaned, groaned, and then fell into his open arms.
I found myself on the floor, kneeling between his muscular, flexing legs. I slowly stroked his crotch . I felt the movement underneath his jeans that was all to familiar: a MASSIVE ERECTION. I could not restrain myself! I opened his fly and was blessed with the most perfect cock that I had ever seen!
I stroked, licked, and sucked it wantonly! I relished in each moan from him as his legs quivered, shook, and flexed eagerly. I stopped and lead him to the couch, where I continued. He was so eager by then that it did not take long for him to cum. I drank every drop of his essence lustily! He sighed and started petting my head, treating me like the good little pet that I was.
I was not! If he would not fuck me, then I would suck him some more. I quickly got to work stroking, licking, and sucking. Soon he was hard again. This time he stopped me from putting that gorgeous cock into my mouth. "I know what you are. Why do you think your mistress sent me? Now, I want to fuck you!" With that he pushed me on all fours, ripped off my skirt and lingerie, proceeded to insert that huge, throbbing cock into me!
He pushed and pushed, stretching my tight little man pussy to fit that enormous cock. I groaned in pain, in pleasure, and then he came.

More to cum!

I felt his cum fly into my man pussy, it felt warm, smooth, and heavenly! I cried out in pleasure, gyrating on his cock until it relaxed. He withdrew from me, asked for the bathroom, and I returned to my room to get my clothes back together and straighten up the mess that we made in the livingroom. When he emerged from the bathroom, we kissed, me sliding my tongue all through his mouth. I could still taste the sweat from his efforts and wanted more! He then went back outside and this time finished the work without his shirt. I just sat by the window and relished the activities. I knew that when my mistress, Miss Missy, returned home I would be in big trouble. She could always tell when I've been naughty, and I learned quickly that it was better to fess up and face the punishment right away than to try and fool her, awakening a more devious punishment.
Around four o'clock Miss Missy came home, saw the gutters, and then took me to the room for our end of the day rituals: spanking, hormones, and more teaching me how to lick her pussy. I always loved the last part! Despite my growing femininity, I have always had a deep love and envy of vaginas. I wanted one so badly, even as a young child that I would sneak into my mother's room and pretend to model her panties and bras. She caught me, feminized me at home, and when I grew older, introduced me to Pamela, Miss Missy's mom who, upon leaving a very abusive relationship, had become a talented dominatrix. Miss Missy and I became best friends. Apparently that was the plan. But enough reverie, I have to finish the story and then get back to doing the dishes
Miss Missy did not spank me this time. She had me sit at the edge of the bed and looked straight into my nervous face.
"Did my pretty Jasmine enjoy the gutter man?" she said with a demurely venemous voice. I knew I was trouble.
"Yes, Mistress Melissa. I gave him a nice time." I called her Mistress Melissa when I knew she was about to be angry.
She laughed, "You do not need to worry, sweetie! That was a gift for you. Today was the five year anniversary of your subjugation to me. I thought that you would like it. Did you?"
I was shocked. She knew about this? But then again, the worker man had mentioned this before as well. I tried to say thank you, but choked out a mere whimper.
"That's OK, Darling. I know you had fun. I had a purpose in it as well. I know you sucked him good, then let him plow you just as good. Now, how will you thank me for that wonderful gift?" she said, leering at me hungrily. I knew this would hurt, but I also wanted it.
She pushed me back on the bed, ripped off her clothes, then mine, and proceeded to....
More to cum
sit squarely on my face. I knew then what I needed to do: Lick, suck, bathe with my tongue every aspect of her cave of wonders. She came in no time and turned to examine my little sissy clit. It was rock hard. Without even saying anything, she turned around, grabbed it, and proceeded to stroke me to a climax. She then made sure to catch every bit of my little dribble and turned back to me.
"Open wide, Jasmine!" she said with a wry smile, and slapped the cum into my waiting mouth. "That was good, my little pet! Now let's get ready for the evening. We have a party scheduled and you're the main event!" she said ever so seductively malicious. I really am not sure if I like being the main attraction at one of her sex parties, but it is better than refusing and facing the consequences. Maybe there'll be others with me this time.
That evening I was prepped for the show. Mistress Melissa always takes the preparation VERY seriously. First, I am to scrub from head to toe with a rough exfoliant that removes any traces of unsissyish hair. Second, she takes a sweet lavender-rose ointment and thoroughly rubs it into my body. Third is my attire. She makes sure that it is UNcomfortable and fits the theme of the party. This one is a tight, leopard print bodysuit, open crotch and ass, of course. Leopard print thing-high stockings, a matching garter belt, and knee-high boots finish the legs of the ensemble.
Now it is time for the 'toys'. First is a toy with which I am very familiar and can enjoy: a well lubricated butt plug that she inserts slowly, smoothly. Second, a gag that is specially made for a sissy such as me. It allows others to fuck my mouth without bumping my teeth. Many of her friends' sissies LOVE this on me. So, I am to be the subject again. I smile as she straps the gag onto my neck, hoping that she will see what a good sissy I am being. I lay myself down and prepare for the chastity belt. She surprises me and let me know that I am going to be expected to cum at this party! Hrmm...maybe I will get to fuck someone else this time as well. She's so creative!
More to cum!
Last Post
4 posts
These lovely people support all the features in Sissy Kiss to contribute to our community! So it would help so much if you could check them out, and say your from Sissy Kiss. Some even give discounts, or free gifts by mentioning it!
Add your message here..
the story seems a little rushed, but nevertheless, it does have some potential.
I hope to see it continued in the fairly near future.
lots of love
from lilgirl stephy :)
There will be more, sweetie. I was rather in a rush and needed to get it out of my head before I forgot it. I appreciate the comments! Remember that sometimes impromptu is best:).
Never stop hoping
Not much preparation, but it continues. 
Never stop hoping
What kind of post would you like to make?
To post certain kinds of posts, like images, audios, or videos you need to be signed in first.