Sissy Side Job

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A days work leads to an afternoon of pleasure.
2.2k words
4.52
1.6k
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It was summer time, hot and humid. My Uncle had asked me to help him improve the curb appeal of a home he was trying to sell. Me, being a 19 year old, could always use the extra cash. So, I agreed.

I woke up that Saturday morning really feeling like a sissy in heat. So, even for this most masculine of landscaping activities, I could not resist dressing a little fem. I had shaved my legs just the day before so I decided I had the perfect short-shorts for the hot day of planting shrubs and flowers. I picked out a pair of lacy pink panties, pulled them over my smooth legs and adjusted the sides just perfectly over my girly hips. I noticed as put on the tiny little low rise shorts on that the top of panties were definitely going to be noticeable above the waist of the shorts. Oh well! I threw on a matching pink bralette, white t shirt and just a hint of eyeliner and headed off!

When I arrived at the landscape nursery where my Uncle has placed the order for the plants, the order was all ready and on a cart. There was a middle aged gentleman behind the counter that seemingly jumped at the chance to help me out to the car with the order. The first thing I noticed, as he placed his hands on the handle of the cart, were his very muscular, hairy forearms and I could only imagine the hairy trail leading from his stomach down into his waistband. My sissy mind for a split second could only imagine licking my way down his stomach as I unbuttoned those khaki shorts to find the prize! I snapped out of my daydream as the man said "after you" prompting me to show him to my car. As I walked across the parking lot I could feel the breeze on the small of my back and knew this man must be getting an eyeful of my pink lacy panties. The thought of his gaze was making me tremble all over.

When we arrived at my car and opened the trunk, I realized I was going to need to move some things around to make room for the plants. Among the things that needed moving was some high heels and a wig. Oh my, I'm sure this guy was getting the full sissy picture in technicolor by this time. But as I bent straight legged over the lip of that trunk, I felt the string of my panties and the tiny bit of material from my shorts press against my little pink boi pussy. I wished like everything that he would take his big hands and cup my ass. That he would push and grind against me, show me just how much a man he is and make me feel even more like the sissy gurl I am. But, alas, we were in a public parking lot and I'm sure he had a job to keep and heck, maybe he was not even into it. This was all in my imagination to this point anyway. When I had made the space in the trunk for the plants and turned back, I smiled at him he smiled back.

My gaze moved down ward and I saw a gigantic bulge in his shorts. My eyes retuned to his and he had an even bigger smile. I wanted so much to reach over and give his big cock a squeeze or better yet drop directly to my knees, get those shorts undone and get my mouth wrapped around his cock where this sissy belongs. But, I moved aside and let him get the plants loaded up. When he had the last plant loaded up he looked at me, smiled and said "I sure hope to see you around again soon"... I sighed, looked down to his still gigantic bulge. Then assured him that I had more "business" to "take care of" and would be back around soon. I gave him a wink, strutted girlishly to the passenger door of car, and of course took my time swinging my sexy legs into the car.

When I arrived at the vacant house with the for sale sign I noticed a shirtless man washing his truck in his driveway across the street and a couple houses down. Yes I do seem to notice shirtless men! Especially when I have tiny pink panties tickling my smooth pink hole. There is just something about wearing slutty panties that makes me want to have a cock in my mouth. I guess that is what being born a sissy is all about. I noticed the shirtless man looked my way for short time, but turned back to his truck washing seemingly uninterested. I began unloading the plants carting them one by one up to the beds where they were to be planted. With each trip back to the trunk of the car I would of course bend over, straight legged as can be, linger a few seconds with each trip. After a time, I now could tell I had this gentleman's full attention. He was still finishing up his truck wash but he sure kept looking my way.

Having all the plants placed symmetrically in the beds where the needed to be planted I proceeded with getting them planted. As the sun rose in the sky and the morning moved towards noon and it was beginning to heat up. My white shirt had become wet with sweat was turning sheer and sticking to my body. The lacy bralette and its straps were no longer a secret. Anyone near by could clearly see what I had on underneath my shirt.

As I was wrapping the plantings I saw my truck washing admirer walking down the sidewalk across the street. Damnit he had put a shirt on though, I didn't know if he was just playing it cool or truly disinterested but he walked on by. As I kept an eye on him I noticed he had walked to the end of the block and and was now walking back up the side walk on my side of the street. There I was on all fours, ass facing towards where he would approach. Of course taking my time as I planted the last plant and I heard his sexy manly voice. "Hey there," he was walking up the yard from the sidewalk as I turned, still on my knees. I returned his friendly greeting and smiled. He said "it's so hot out here today, would you like a glass of ice water or something," as he spoke the breeze blew in my direction I could smell that he must have just taken a shower after washing his truck and he smelled terrific. I love that soapy smell on man. Of course this breeze also felt cool on my now drenched shirt and reminded me that my lingerie was clearly visible. I told him that a glass of ice water sounded great and he suggested that walk down to his house and cool off in the air conditioning.

When we walked into his house into the kitchen, he started making the glass of ice water and handed it to me. We made some small talk when he asked "hey why don't you let me put that drenched t shirt in the laundry and we can go in the living room." When I hesitated at his idea of me taking my shirt off he said " don't worry, I know what you have on under there. I like it." So without hesitation I took off the shirt and handed it to him, he stuck it in the dryer and then directed me to the living room and said he was gonna grab a couple beers. When he entered the living room he sat on the couch directly across from the chair I had chosen to sit in. His legs had the perfect amount of dark hair and the way he sat, so manly with his legs spread apart in comparison to my girly posture with my shaved legs, panties under my daisy duke shorts and little pink lingerie top on. He cracked his beer and said "why don't you sit over here on the couch next to me where you can see the TV better."

In that moment I knew where I was supposed to be and it wasn't on the couch next to him to watch TV, on my knees between his legs was exactly where this sissy was supposed to be and that's exactly where I went. There I was on my knees rubbing his legs. As I looked up He said "well that works too," and chuckled at how instinctively I moved into sissy cock sucker position. My body was shuddering with excitement at what was about to happen. I slid my hands under his T-shirt and felt his fuzzy, manly stomach. This part of a man has always turned this sissy into a horny puddle of "just take me." As he lifted his shirt over his head to take it off, I started undoing the button on his shorts. Struggling a little because I couldn't focus as I kept gazing back at his hairy chest and stomach. The sight was making my mouth water and I could feel my little boi pussy starting to pulse. As I pulled his shorts down I could see his dick was starting to get hard.

Through his boxers I gave it a playful nibble and a kiss before pulling his boxers down, his hardening cock flopping out into my face. I love the way a man's dick moves and flops as I get it out of their underwear, I always have. After we got his shorts and underwear all the down his legs and all the way off, I could get in there between his spread legs where I belonged, I took his cock in my hand and raised it up where I could get underneath. I was licking him from his balls up the shaft and each time working my tongue around the beautiful purple head. I was rubbing my left hand on his thigh as my right hand held onto his cock. As I kept up working on his cock with my tongue, he quickly became hard as a rock. I do so enjoy the process of making a man hard, I always have such sissy giddiness, feel so girly and proud with what I have done! I could feel his manly hair on my cheek as I slid my face up his body to pry his hard cock up from his hairy stomach with my tongue. I really love to work it into my mouth hands free.

My mouth was watering so much and his cock felt so good in my mouth, as he said "I can tell you really love to suck cock don't you sissy." I made a humming sound to the affirmative as I kept working on his cock. I could feel his cock head swelling and the ridge on the head was flaring, he was really close to cumming so I slowed things down and Just held it in my mouth squeezing and releasing. He seemed to appreciate me making sure he didn't cum so fast as he stroked my neck and shoulder, moaning and saying "this feels so good, you are a natural born cocksucker aren't you." I again made a humming noise to the affirmative, to which he laughingly responded for me to not make that noise again or he would cum right that second. I tried my hardest not to giggle. I knew he wasn't going to last much longer, I could taste the pre cum. I just kept my mouth around his cock and slowly, concentrating on my breathing though my nose. worked him all the way down into my throat.

My face was buried against his hairy body, I loved the clean soapy, yet still manly testosterone filled smell. I felt his hands on the back of my head as he slowly started moving his hips up and down, fucking my mouth. His pace increase and knew he was close. He didn't even bother to ask if it was ok with cumming in me. I think he already knew what this sissy cocksuckers answer would be. He tensed up, pulled my head tight against him and said "holy!...arg!...ugh!" Then he shot two thick spurts down my throat, released my head and I backed off a little, still keeping my mouth around his softening cock as it kept oozing out more cum. When I finally looked up, smiling, proud of my sissy self, he said "wow! what a cocksucker!, you are really good at that." I stood up adjusting my panties and bra straps and buttoning my shorts back up, I had unbuttoned them during the blow job hoping he would be reaching down and working to take them off.

As I was planning to get my shirt from the dryer and get ready to go, he asked if I would like to take a shower and he could wash my clothes before I go. I definitely agreed!

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Christy_the_CDChristy_the_CD20 days ago

Great story! I hope we get a part two ;)

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