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TS Boss "You better get up, Lari, or you're going to be late for work," My Mom said as she passed my bedroom. I looked at the clock, it read 7:00 a.m., my summer job came rushing back into my head, along with my memory of Carol the day before. I wondered if I was secretly harboring some of the desires portrayed by the dream. When I reached down I noticed that the front of my pink thong panties was wet. "Jesus," I thought, "you had a wet dream about playing with gorgeous shemales?" "My mind must have been conflicted after I sucked Carol's cock," I reasoned, "that's why I had the epic dream about becoming enslaved to Carol and her TS friends." I got out of bed and walked to the shower. As the warm water ran over my smooth body, I thought about what today would be like with Carol. I wondered if it would be awkward after things got physical at the end of my first day at work. My small cock grew hard as I remembered how she sucked my little cock and came in her mouth. I wondered if I could convince my tall, beautiful customer to let me fuck her as well. What an incredible thing it would be to get paid $8000 to paint a house and fuck the owner whenever I wanted. I made it my goal to make that happen. After I showered, I rushed downstairs to grab a quick breakfast before I made the short drive to Carol's. "How did your first day go Lari," Mommy asked, as she drank her morning coffee. "It went well," I answered, "She's a very nice lady, thanks for helping me set this up, Mommy." "Of course," Mommy replied, "it is a very convenient and lucrative summer job, isn't it." "How is Carol as a boss?" Mommy asked, "she's always very polite to me." "She's great, Mommy," I replied, "She's very professional but also very considerate; not overbearing." "Tell her hello for me, and have a great day," Mommy said as I headed out the door. "Will do mommy," I yelled back as I made my way to my truck. Soon, I arrived in front of Carol's house. I wondered if our morning would be awkward after giving each other oral the night before. "Good morning," I announced as I entered through the front door. "Back here Lari," I heard Carol say from the kitchen. When I entered the kitchen, I found Carol at the island drinking her coffee, sitting behind her laptop. From what I could see, it looked like she was wearing a bikini. I poured a cup of coffee and walked around the island; as I did, my bikini suspicion was confirmed. Carol caught my gaze and said, "I went for a swim this morning, it's going to be a hot one." "Yeah, highs in the mid-nineties with high humidity," I answered, "It'll be a little brutal painting out there today." "Well feel free to take anything from the fridge you need to keep cool," Carol offered, "Take a break in the air-conditioning if needed." "Thank you, Carol," I answered, "I might take you up on that." "I'm going to be in and out today," Carol mentioned, "I have some appointments in the morning, but I'll be back by 1 p.m. or so, and working from home for the balance of the day." "I'm hoping to make a lot of progress today," I said confidently, "I'm going to put my earbuds in and get in the zone." "Awesome," Carol laughed, "can we talk about what happened yesterday for a minute?" My face blushed. I was hoping we were just going to forget about it and move on. "I think we both needed something, and we let our needs over-ride our logic," I said, hoping to nip the conversation in the bud. "You're so right Lari," Carol agreed, "You're a very attractive young sissy boi, I shouldn't have let my desire invade our working relationship, I'm sorry." "You're gorgeous, Carol," I said, smiling and blushing, "I could have stopped it too, but I didn't." "You didn't tell anyone did you?" Carol asked, "I was so worried you might mention it to your mother, Betty." "Betty is none the wiser," I laughed, "and I didn't tell anyone else either. I don't want people to think I took advantage of you." "Don't be ridiculous," Carol said, "I was the spider who caught you in my web. I made the first move." "Actually, when you put it that way, I do feel like I might have been sexually harassed," I said, smiling at my bikini clad customer. "Oh really?" Carol said, "I bet you'd drop those shorts in two seconds if I asked you to. By the way, if you were harassed, then I was overpowered and taken against my will." "So now you're asking me to drop my shorts as a condition of employment?" I said, feigning disbelief, "you are so brazen, Carol." "A young sissy boi like you shouldn't play games like this with an older, more experienced, businesswoman," Carol warned with a sly grin, "I might call your bluff. In fact, I'll throw in an extra $500 if you drop your shorts and paint my house nude." "Just today, or every day?" I asked for clarification, my cock starting to harden from the game that was being played. "Why every day, of course," Carol replied, "I'm not paying an extra six percent for one day of fun." "Make it $800," I said, smiling from ear to ear, "and I get the option to trade the $800 for something I want from you." "I'm buying you for $800 faggot," Carol argued, "if you want to buy something from me, the price is much higher." "We'll see about that," I replied confidently, "so we're agreeing on $800 then?" "Yes," Carol agreed, "but you must leave your clothes in your car when you arrive each morning, there will be no safety net for you. I also have the right to touch you anytime I want." "I guess I can agree to that," I acquiesced, "but I do feel a little cheap selling myself like this." "You'd do it for free, smart ass," Carol said, looking at the growing small lump in my shorts, "Now drop those things so you can get to work." I placed my thumbs under my waistband and lowered my shorts and panties in a single move. As I did, my hard little cock sprung out. I stepped out of my shorts, then picked them up and handed them to Carol. "Looks like my painter is ready for action," Carol said, looking at my small hard cock. She got off her stool and approached me, looking at my cock the entire time. She reached out and caressed the tiny end of my rigid member. As she did, I felt a million shock waves shoot through my thin body. "It's going to be hard for you to concentrate on your work with this little thing sticking up like that isn't it," Carol said softly, looking up from my cock to my eyes, "We should probably take care of that, shouldn't we." I stood and watched as she wrapped her fingers around my cock and then lowered herself to her knees. She looked up at me as she slowly stroked my cock that was now just inches from her face. "Would you mind if your boss sucked your clitty for you?" Carol whispered, smiling a seductive smile, "after all, I paid for you so I kind of own you now." I just nodded my head, trying hard not to fuck up what had become a dream-come-true situation. This was going to be an epic summer job. Carol took me in her mouth and started to suck on just the small head. Her experienced tongue was focused on the most sensitive part, right underneath my glans. I felt like I was going to explode in thirty seconds. Carol pulled off, sensing my reaction. "I bet a young sissy like you masturbates every day to keep these balls empty, doesn't he?" Carol said, taking me back in her mouth while she waited for an answer. She kept my cock in her mouth as her hands moved back to remove her bikini top. My customer was now topless, sucking my clitty in her kitchen before I went to work for the day. "God Carol, I'm very close," I sighed, "You've got me turned on to the limit." Carol worked my shaft further into her mouth and then 3" deep into her mouth. She held her nose against my tummy as she sucked my clitty. I hadn't been sucked like that in a long while. It was driving me even closer to blowing my load. I was doing everything in my power to keep from exploding too quickly. Carol pulled off and then licked me again and again. She knew I was close, and she was driving me crazy with her oral skill. "Momma's hungry baby," Carol groaned, "Feed momma your college boi cum." I loved her dirty talk; it was so dirty to call herself Momma. This woman was really getting into my head. Carol's hands reached around and grabbed my smooth, hairless cheeks. Then, she pulled me in, balls deep, over and over. I literally felt like I was being manhandled by my beautiful customer. I couldn't hold back any longer. "Oh God, Carol!" I growled, "I'm cumming, oh God yes!" My knees buckled as I fired rope after rope of thick semen into Carol's throat. My legs were shaking as I tried to stand while Carol sucked my soul out through my clitty. "Mmm hmmm," Carol moaned as I filled her with my cum. She held my butt cheeks to keep my clitty buried in her throat until she sensed my orgasm was past. Then she sucked on the tip to draw out any cum that was left in my shaft. Carol let my small clitty fall from her mouth and sat back on her knees to look up at me. "There. That must feel much better," Carol said smiling, "Now my painter can focus on his work." "Holy shit, Carol," I said, "That was unbelievable, I need to sit down for a minute." Carol picked her swimsuit top off the floor and sat next to me at the island. "I think it's going to be fun having you around this summer Lari," Carol said, smiling, "You're going to go a good job for me, aren't you sissy boi?" "Right now, I'm the most motivated employee you'll ever have," I said, "Good, let's catch up at the end of the day," Carol said, "I'm going to go take a shower and get to work." I watched Carol leave the kitchen, then I grabbed a bottle of water from the fridge and headed outside, nude, to the scaffold to get to work. Working Hard Until Lunch I headed back out to the scaffolding, put in my earbuds, and got to work. The morning flew by in a flash. I made great progress and was ready to take my lunch break. It was mid-day and the temperature had to be close to one-hundred degrees. Sweat was pouring off my nude thin body. So, I decided to head inside for lunch. On my way back to the kitchen, I stopped for a dip in the pool to cool off. It felt great to have the cool water washing over my bare skin. I swam around for a minute or two before I stepped out of the pool and grabbed one of the towels in the basket Carol kept nearby. I dried myself off as I headed for the patio doors that led to the kitchen. I slid the door open and headed inside. The cool air of the air conditioning caused a slight chill to race across my damp skin. I dropped the towel on the kitchen island chair and walked over to the fridge to get my lunch. I grabbed a can of RC out of the fridge and opened the freezer to fill my glass with ice. There on the fridge door I saw a bottle of vodka and tequila both chilling for convenience. "Hmm, don't mind if I do," I said to myself, and took a long swig off the tequila bottle. I grabbed some ice and sat down at the island. As I enjoyed my lunch in the air conditioning, I congratulated myself on landing the Cadillac of summer jobs. I was getting paid a fortune to paint a hot TS woman's house, and she was paying me extra to do it nude. To top it all off, I was now getting regular sexual favors from my as well. I started wondering if I would get another blowjob during our end of the day meeting. Or better yet, maybe I could convince Carol to let me fuck her. As I daydreamed about my hot , my clitty started to grow underneath the countertop. It took every bit of willpower I had to keep from spanking my monkey right there in Carol's kitchen. After lunch, I decided to take another swig of tequila before heading out to the scaffold. There's something fantastic about the taste of cold tequila on a hot summer day. With a mild buzz, I went back to work working on the east side of Carol's big, beautiful house. The nice thing about painting is that it's not very mentally taxing. I spent the rest of the afternoon fantasizing about convincing Carol to do more than just blow me. I was hell bent on figuring out a way to convince her to let me fuck her boi pussy I wondered if Carol even thought about sex that way. She was a very capable businesswoman who had a team of almost a dozen professionals working for her. Maybe she didn't get fucked, maybe she was the top in every relationship. I kept wondering how to find out, so I could formulate my strategy. Soon, it was 3:30 p.m. and I heard Carol's car in the driveway at the front of the house. I figured I'd work another 30 minutes and then meet Carol by the pool for our end of the day meeting. I had planned to make certain I was rock hard at that meeting so she would feel the need to help me find a release. It had been almost 4 hours since lunch and I was dripping with sweat after working in the hot sun all afternoon. A little before four, I climbed down from the scaffold and prepared to head to the pool to cool off before our meeting. I jacked myself to a raging hard on before walking to the pool and jumping in to cool off. Carol was sitting next to the pool wearing red bikini bottoms, a big floppy hat, sunglasses, and nothing else. She was sipping a cocktail and reading her emails from the iPad in her lap. As I approached Carol, I couldn't help but secretly admire her pert tits before she realized I was there. She looked fantastic wearing only a tiny thong and that floppy hat. I had no problem maintaining my small erection. "Mind if I take a quick dip before our meeting, Boss?" I asked, looking over at Carol. Carol looked up from her iPad and quickly glanced at my cantilevered clitty. "Have you even been working today? That thing looks exactly the way it did this morning," Carol commented with a smirk. "I can't help it, Ma'am," I answered, "I guess I'm a closeted exhibitionist, I'm hard all the time since we agreed I'd work nude." "Well maybe the cold pool water will help deflate your little cock," Carol laughed, "I'm not sure we can have a serious discussion with that tiny thing distracting us both." I dove into the pool and swam down toward the bottom, enjoying the brisk pool water against my sunburned skin. By the time I surfaced, I had significantly cooled off but I was still sporting an undeniable hard on. As I climbed out of the pool, Carol watched and commented, "I know what you're doing, you know." "What are you talking about?" I asked, as I dried myself off with the same towel I had used earlier in the day. "You think that I'm going to help you get rid of that hard-on, don't you?" Carol speculated. "Actually, that would be great," I said, going for the presumptive close, "Should I relax in the chair again or do you want to bend over and let me take you from behind." "Oh, so we've graduated from cock-sucking to anal, have we?" Carol laughed, "If you knew me well Lari, you would know that I'm more fuck-er than fuck-ee." "That should probably be in the employee handbook, Boss," I said, smiling, "seems like a pretty important piece of information for our working relationship." "I think we can work this out less formally," Carol proposed, "we'll just adapt as we go. For now, why don't you just jack off while sucking my B boobs so we can discuss your progress today without distraction." This was a step in the right direction. Carol was proposing sex for a second time today and it was only day two on the job. I figured if I stayed patient, I could get what I wanted in the long run. "I'd like that," I said, kneeling next to Carol's chair and reaching out to caress her left breast. "You have nice hands sissy boi," Carol said as I softly caressed her, then pinched her nipple softly and pulled gently. I could feel her quietly watching my eyes devour every inch of her B cup breasts while I readied my mouth to suck on her nipples. My hand was now on my throbbing clitty as I lowered my head to take her left nipple into my mouth. I sucked on her nipple and bit down gently. As I did, I heard Carol sigh. I sucked on her nipple again and let my tongue flicker across the very tip of her nipple hoping to excite the nerve endings there. Carol's right hand slid down her stomach to her bikini bottoms. As I jacked my own clitty, I watched Carol pull her shaved cock out of her bikini bottoms and stroke it gently. Carol's cock started to grow as she stroked it. Soon it was just as hard as mine and extending past her navel. She had such a big cock for a hot TS gurl. Carols left hand was cradling my head as I nursed on her perfect breast. After a minute, I felt her hand start to push my head down. "You're making me so hot Lari" Carol whispered as her hand directed me down toward her huge cock, "Please keep sucking." I wasn't prepared for this turn of events. I had been hoping for a blow job from Carol and now she was expecting one from me. She lifted her cock off her stomach and pushed my head down until she was feeding me her cock with her right hand. I opened my mouth and let her in without protest. "That's it sissy boi, suck Momma's cock," She whispered. I was on my knees jacking myself off with my face in my new boss's crotch. I felt her hands on my shoulder rolling me off my knees and onto my back. I took the signal and waited for her to mount me into a 69 position on the pool deck with her on top. I felt Carol's mouth engulf my raging hard clitty as I took her huge cock back into my mouth. Now on my back, I looked up to see Carol's balls hanging down onto my nose. Behind that I could see the perfect orbs of her bubble butt. I felt Carol working my clitty into her mouth as she started fucking my mouth at the same time. I was so turned on, after working nude all day, I knew I wasn't going to last long. I was lost in the lewdness of our public sexual display. The backyard was silent except for the sounds of each of us sucking the others cock and the rippling sound of the fountains in the pool. I was getting very close and started to moan. Carol could sense I was close and started to take short strokes, focusing on just the sensitive head of my clitty. Then, after a few short strokes, she'd take me balls deep. She repeated that pattern a few more times. |
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mmmm lucky lari
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