Ryan gets caught by his sister while she is working Chad’s cock, and is forced into a proposition he can’t refuse. Brenda, ever the entrepreneur, makes an offer.
*Note* I don’t like how Brenda is a dirty blond with blue eyes, so I’m making her a shoulder length dark brunette with dark brown eyes. *End Note*
“We need to talk.” Is all Brenda had to say, and she was right. She didn’t seem mad at all, unlike when I first saw her when she pulled me from her closet, that’s good. “How long have you been spying on me? How long have you been hiding in my closet? What do you know? How long have you been wearing my panties? Do you like wearing my clothes too? Does anyone else know about this?”
Question after question came like a hail storm, and each one struck a pang of guilt deeper and deeper into shame. She must’ve noticed this, and gave me a hug and kiss on the forehead.
“I’m not mad, I’m just curious. I was pissed at first, but only by the surprise of you being there, and the fear of being discovered,” she explained.
I finally found my voice after I calmed down a little. “The first time I saw you was when you were with coach Ives when you were 15. I was basically hooked from there. I pieced together your little business arrangements, and would get into your closet and watch everything. I know who you see and how much you charge for your… services. The first time I tried on your panties was a couple years ago, and I loved the feeling so I kept taking and wearing them. I’ve never actually tried on your clothes, but I have been curious. Nobody else knows. This is my- our secret now I guess.”
Brenda gave a sigh of relief and her shoulders visibly lowered as she relaxed. “So you know everything, huh? Ok.” She gave a quick look away to her closet, and I could see gears running in her head. “Would you like to try on some of my clothes? We are about the same size.”
My curiosity piqued, as her words escaped her plump lips. I looked at her closet then nodded slowly.
“Great!” She said as a grin formed on her face. She first pulled out a pair of jeans and a t-shirt, “put these on,” she ordered. As I did, it was surreal having my sister watch as I pulled her jeans up. The hem slid right into my ass and shaped it quite well. My raging hard on however, didn’t allow me to zip it up all the way.
“Uh oh,” my sister said giggling. “We should probably take care of that,” she said pointing to my dick. “Hurry up and jerk off to get rid of it.”
I felt a little silly as I lowered the jeans and grabbed my dick and started clumsily jerking it. My sister watched like a cat on prey. Though awkward, the situation made me ready to cum in no time at all. “Do you have a towel? I’m about to cum.” Brenda gave a quick look around, and had none.
“Just cum in my mouth, it’s easy clean up.”
That put me over the edge as the first dollop of cum appeared at the tip of my dick. She quickly got on her knees, and put her mouth over the head of my dick as I stroked. “I’m cumming!” I grunted as spasm after spasm flew into my sister’s mouth. Easily one of the biggest loads I’ve shot in a long time. After I finished, I fell back onto her bed, her jeans around my ankles, and my dick, still hard but deflating on my stomach. I looked down at Brenda. She was still on her knees, contemplating the taste. She looks at me deadpan, opens her mouth to show she still had my cum in her mouth, and then swallows it with a loud gulp.
“Easily one of the better tasting loads I’ve swallowed,” she giggled as she stood up. “Ok, get dressed.”
My dick now soft, I tucked it in and zipped up the jeans and put the t-shirt on. She walked around me, inspecting everything. “It’s cute, but I’m just not sure. Take it off,” she ordered.
I obeyed. She then pulled out a red knee length dress. “Put this on.” As I did, it felt more natural, and fit like a glove. The soft stretchy material hugged my curves, and I looked at my back and could see a shapely ass with a very visible thong line.
“Much better,” she commented. “Now sit,” ordering me while pointing to the vanity in her room. She then produced her makeup bag and grabbed a few items. “I assume you’ve never worn makeup before?”
I shook my head.
“Well, there’s a first for everything.” She went about her business applying make up all over my face and directing my eyes and lips, and face for best application. The whole process took about a half hour. She then went to her closet and produced a platinum blond wig. I’ve seen her wear it before as some of her “Chads” like to see her in different models. She placed it on my head, and pulled this lock, and that. “Ok, go look at yourself.”
I got up and looked at myself in her full-sized mirror. I looked amazing! I almost looked like a real girl, less the boobs. Brenda came up behind me and put her arms around my shoulders and smiled at her work. I saw Brenda pull out her phone and start taking pictures of me.
“Hey!”
“Wow, Riley! You look great!” as she slipped a hundred dollar bill in my top. “You earned that!” she said with a wink.
“Riley?”
“Yeah, silly. You can’t look hot as fuck, without having a girl’s name.”
“I guess not,” I responded looking back at her mirror to admire her work. I looked back at Brenda, and she was on her phone texting with someone.
She then asked me, “What did you think about sucking dick for the first time, Riley?”
“It wasn’t bad, kinda liked it, a little awkward, but you know…” She gave a little chuckle and nodded.
“Would you be game to do it again? You can earn some extra money…”
My sister was trying to pimp me out!
“No,” I said shaking my head, the long blond locks sashaying around my shoulders.
“Oh, c’mon, Riley! We can charge two-hundred a pop, a hundred each for a pair of cousins,” she said ‘cousins’ using air quotes, “making out then sucking their dick together. Easy peazy, I can even do most of the work.”
I sigh, and thought about it, then remembered her threats if I didn’t comply. “Fine,” I reluctantly agreed, but secretly, I was thrilled. Money? My sister’s position? This could be interesting.
“Yay!” she squeaked, and busily got on her phone and shot off a quick text. Her phone buzzed almost immediately. “Ok, I have another Chad coming over. Two-hundred dollars for about an hour’s worth of work in one day, ain’t too bad, eh?” she said giving me a little wink and elbow nudge.
“Yeah I guess not.” I smiled to myself
About twenty minutes later, Chad arrived.
“Ok, he’s here, Riley. You know what to do?”
“Yeah, keep my mouth shut, except when we make out and he’s sticking his dick in my mouth, if I do make any noise try to sound as feminine as possible.”
“Perfect, ok here we go.” With that Brenda opened the door, and a tall well built blond man stood at our door with a dumb look on his face. Brenda hugged him and gave him a peck on the cheek.
“Hey there, it’s been a while.”
“It most certainly has,” Chad said in a low voice. “So, where’s this banging cousin of yours?”
“Right over here,” Brenda said, as she swanned her arms open presenting me in my feminine glory.
Chad gave a long whistle. “Wow, this is going to be great. Real incest. I can even kinda see the resemblance.”
“Money upfront,” Brenda said holding out her hand while closing the door.
“Of course,” Chad replied pulling two bills out of his front pocket.
Satisfied, Brenda took the reins, “alright, to my room, everybody.” Chad led the way, and Brenda fell back to whisper to me. “How are you feeling? What do you think? Pretty hot, right?”
I shrugged, not really sure how to feel. We got into Brenda’s room and Chad plopped down on her bed ready for the show.
“You ready?” Brenda asked Chad, smiling at him as she took me by the waist and brought me in.
“Oh yeah,” he responded with enthusiasm.
“Just like before, but this time grab my ass and feel me up, Brenda instructed. I nodded. Brenda came in and we interlocked in a passionate kiss. My hands caressed her body. Her shapely ass fit perfectly in my hands as I groped her. I let out a quiet moan as our tongues danced. She let out a gasp when my hands separated her ass cheeks. My hand snuck its way up the front of her shirt and went searching for her breasts. I pinched a nipple when I found areola. She hissed a sharp breath of air in, and her kissing became heavier. She grabbed my ass and ground my panty clad cock into her pussy, and began dry humping me.
Chad was already naked, stroking his hard cock. It was bigger than the guy from earlier, and his balls hung low, his legs spread. Brenda looked at Chad, and I was lost in the make out session. She was first to detach, and got on her knees in front of Chad and eagerly took his cock in her mouth. Expertly, she worked it from tip to base. I followed suit and got on my knees in front of her, watching intently. She stopped.
“Riley here isn’t taking her clothes off, and you’re not allowed to touch her, except her ass, understood?” Chad nodded as she took his cock back in her mouth. “You’re on ball duty for now, Riley.”
I got underneath her. Her mouth full of cock so close to my face, it was wild having gone from a distance to RIGHT there! His balls were bouncing gently as she sucked him. I reached out a gently rubbed them. They were soft, and shaven. I nestled my head in and stretched out my tongue and licked one. Chad gave out a low moan, and so I did it again. Each time gaining more confidence until I was sucking and licking them with gusto.
“Switch!” Brenda playfully called out, and stopped sucking giving me room to take her place. I grabbed the base and leaned in to take it in my mouth. God it was stretching my mouth. I bobbed up and down, minding the teeth.
“A little teeth isn’t bad,” Chad said. I relaxed my jaw a little and my teeth gently scraped his skin. He moaned and Brenda got to work on his balls. Like before, I had my mouth and hand connected as my shoulders bobbed up and down on Chad’s member.
Brenda giggled, “Hey Chad, I’ll cut you a deal. Usually I charge fifty for this but, for an extra thirty, I’ll go lower.”
“I’ll give you another twenty after that if I can cum on your faces and you lick it off each other.” Brenda thought about it.
“Deal.”
True to her word, she went lower. She couldn’t quite get the right angle as is, “Riley stop sucking for a second.” I stopped. Brenda grabbed his legs and pushed them up and his asshole was exposed. She started gently flicking her tongue over it then worked her way into tongue fucking his asshole.
“Riley, suck his balls and stroke him.” I did as directed.
Chad was moaning like crazy, and he announced he was going to cum soon. We picked up our enthusiasm, and I took him back in my mouth. I could taste his warm precum.
“I’m going to cum, get your faces together.” We knelt down, our faces together.
“Say aaaahhhh,” Brenda directed and we opened our mouths and awaited our prize; a copious globular of white splattered across our faces and into our mouths. Five, six, seven ropes of thick oozing cum flung from his cock. We were completely covered by the time he was spent. Brenda smiled at him, as she took the first lick of his cum from my face then I hers. Back and forth we went until we were completely clean.
“Oh my god! That was amazing!” Chad declared and gave a loud WOOT!
“I’m glad you liked it,” Brenda replied coyly. “”fifty more, please.” She said holding out her hand.
Chad fished out another couple twenties and two fives. He even pulled out a ten as a tip. He stood up put on his pants. “Easily the best two-sixty dollars I’ve ever spent, thank you!”
“No, thank you. It was a pleasure doing business.”
Chad laughed. “Yeah, I’d be happy to do this again sometime.”
We’ll see,” Brenda said with a smile, as she put on her robe and escorted Chad to the door, locking him out. Brenda came back in her room. I was still on my knees, her dress covered in cum—a distant look on my face.
“What’s wrong?” Brenda asked with concern, “Are you alright?”
“Yeah, it’s all just so surreal, I’m processing it all.”
“Yeah, it’s a little strange sucking dick with my brother.” She laughed. “What did you think, are you game to do that some more? Maybe even do some by yourself?”
“Yeah, sure, I guess. I’ll need your help with everything until I get the hang of it, but it’s definitely easy-ish money,” I said rubbing my slightly sore jaw.
Brenda laughed, “yeah, you get used to the girth after a while. Oh here’s your cut,” she handed me my half. Two-hundred thirty dollars made in an hour. That’s half a week’s worth of pay for me at my full time job.
“You can charge the same as me. Just let me handle all the business end of things.” She went over to put her money away, and paused. She slowly turned to me, “Have you ever done anal?” I completely forgot she offers that service and I went a little pale.
“I almost did with Tiffany, but she said it hurt too much.”
“Hmm, that’s where some good money is, and since you don’t have a pussy, that’s can’t even be asked for. Are you ok with that?”
“I don’t know, I’ve never experienced it before…”
A pregnant pause hung in the air.
“I have an idea,” announced Brenda as she got into her drawer and rummaged around for something. “Ah ha! There you are.” She said excitedly.
My curiosity was alive and well and I tried to peak over her shoulder but then she spun around and presented a smallish five in purple dong, about an inch or so in diameter attached to a bunch of straps.
“What’s that?” I had never seen one before, though I knew what a dildo was, but never with straps.
“This, my dear Riley, is called a strap on. I don’t usually offer this service as most men don’t want it, but once I had a Chad who wanted it, so I got one. It’s called pegging, and basically it’s where the guy becomes the girl and gets fucked!” She had stars in her deep brown eyes, and I could see the wheels turning.
It suddenly came to me, “wait! You aren’t suggesting, what I think you’re suggesting, are you?”
“mmhmmm, what do you say? Wanna give it a try?”
I thought about it, and asked, “isn’t it going to hurt? It really hurt Tiffany said.”
“It might be a little uncomfortable at first, but you get used to it, and it feels super good! I’ll go slow, I promise.” I could see the pleading in her eyes. She really wanted this.
I sighed, “ok.” Brenda squealed in glee and began getting the contraption on around her legs and waist. It’s a quick hundred dollars at Brenda’s menu, so let’s see what happens. After she got her self situated, she pointed to the bed.
“Lay down on your side.” Brenda instructed. I laid down and she straddled my leg that was on the bed.
“I normally charge fifty bucks for this, but as a perk for working together…” She then lowered her head to my ass, pulled my thong aside and spread my cheeks. At first her tongue startled me.
“What are you doing?”
“Shh… trust me.”
I silenced myself and felt her tongue probe my asshole. It was strange at first. I was afraid I was going to fart. It felt like a wet warm worm crawling around down there, but then it took on a pleasurable tone, and I couldn’t hold back the moan that involuntarily escaped my lips.
She smiled, “see, I told you, you’d like it.” She went back to rimming me and got it very wet. She gave one last lick, and spit on my asshole. “You ready?”
I timidly nodded.
“Ok.” And with that, she pressed the tip of her dong up against my hole. It wouldn’t go in.
“Relax. Imagine you’re pressing out a fart or something, while I press in.” I was a little confused. I was afraid I would fart or worse, shit. I did though press out, and to my relief no fart or shit happened. The head of her dong however, made progress, and I could feel it stretch me. I groaned.
“Oh hush, I haven’t even gone in yet.” My sister spit on the dong and rubbed it around. Slowly, as promised, it made its way inch by inch in me. I felt my sister’s hips on my ass cheeks signaling her being in me to the hilt. “There, all the way in. How does it feel?”
“Full. Like I gotta take a shit.” She laughed and looked down at my stretched asshole with her dick in it.
“Yeah, it felt that way for me for the first few months too, but then it goes away and is replaced by pleasure after a while.” She began to pull slowly out, and back in before the dong left me. I was grunting and groaning. It was uncomfortable, but oddly satisfying. I became accustomed to the pressure, and she found a rhythm that worked.
“Ok, I’m going to start going faster, are you ready?” I nodded. “Good.” Brenda picked up her pace and began gently fucking me. My prostate was on fire and I started to grunt guttural tones from my throat, with every thrust. Brenda’s face was flush and she was lost in ecstasy as her humping became more and more intentional and wild. My sister spanked my ass eliciting a muffled moan.
“Oh you like that, do you?” she spanked me again. “You liked being fucked like a buttslut whore?” her spanking came regularly every other thrust.
“Yes!” I shouted through my quaking body. I could feel an orgasm boiling inside me. “I- I- think- I- think I’m- going- to -cum…” I sputtered out
With that my sister grabbed me by the hips and started fucking my ass with abandon. I was biting the pillow, and a wave washed over me as the most unique orgasm came over me. It was unlike sex or jerking off. I hadn’t even touched my dick, but I made a large pool on Brenda’s bed, and was rubbing it in as my body rocked back and forth with her thrusts.
Behind me, Brenda saw what happened, “Oh fuck that’s so hot! I never knew it could do that!” Her face and body clenched as her own orgasm took over her. She spasmed. “Oh….FUCK!” She shouted through gritted teeth as her cum trickled down her leg. Her thrusts became liberal as she followed her momentum through her orgasm. She slowed down like a ticking clock, and collapsed on top of me.
She rolled over behind me, dong still in my ass. She wrapped her arms around me and held me close. Kissed the nape of my neck and rested her cheek on my shoulder. She lifted her head and got next to my ear. “What do you think, partner? Want to make a buttload of money with me?” She said as she thrust the dong in me a good couple of times on the word ‘buttload’.
“Yeah, partner.”
We lay there spent for a few hours before getting cleaned up before dad got home.
Thank you all for reading. Once again, any and all feedback (not just positive or negative ratings) is appreciated. I want to give you all the best stories possible. I know I enjoyed this one. Until next time.