Becoming Cara's Sissy_(1) by jonialabaster

A literotic sexstories: Becoming Cara's Sissy_(1) by jonialabaster ,
Cara, my first love, and I dated in junior high. We broke up after her dad caught her and I in a compromising position. Years later, she’s married and we reconnect.
Cara and I met in junior high at a school dance. We had met via MySpace, and we met at the dance and fast became an item. She was a very cute, punk rocker girl and right up my alley. Before we made anything official though, her friend, who was very slutty, cornered me and basically forced me into a relationship with her. Being young it was fine, as I didn’t know any better. She also sucked my dick every day, which I had no objections to. I had never had any kind of sex up until then, so I was all for it. Those two weeks though, I couldn’t get Cara out of my mind, and I eventually had to end it with my little cock sucker.Cara and I got along famously, and had a lot of fun and adventures that were both romantic, and exciting. She accepted and loved me for who and what I am, and was more than happy to please me, and receive my loving. In the course of our relationship I revealed to her that I had a huge thong fetish, and she quickly stocked up on a few pairs beginning to wear them on a nearly daily basis. She was smoking hot, with the cutest face, easily a foot shorter than me, a fit body from playing volleyball, with hips to die for. Her long thick wavy brown hair accented with green bangs, gave her the alt look I craved.

My fetish for thongs escalated and I eventually started wearing them from time to time, and she thought it was funny, and kind of sexy. I even started wearing some of her clothes. There was one time, I asked her about putting on one of her dresses. She normally wore jeans and a t-shirt, and so she humored me. She immediately stopped laughing saying the dress looked before on me than it did her. We both shared a laugh and I took it off.

Blossoming in me from the early stages of our relationship and throughout was a need for blowjobs. When I talked to Cara about this, much to my excitement, she was happy to oblige. She didn’t have any experience in this realm, so she asked me to coach her in what to do and how I liked it. I later learned that her older brother when she was a child would actually make her suck his dick, but that’s for another time.

She became, to date, the best cock sucker I have ever experienced. No one compares to her. Oh sure, I’ve had other girlfriend that can do certain little tricks, but the amount of love and devotion she put into her head game is unparalleled. The first time she gave me head, was magical, we were in my bedroom and I was sitting on the bed with her on her knees before me. I was coaching her, telling her to use her hand here, and watch the teeth, although a little scraping was good. When I was about to cum, I forgot to tell her. I thought she could feel me engorge and get extra hard, and we also hadn’t discussed swallowing. So when I came, it caught her by surprise, she suddenly pulled off with a sputter and it began to shoot thick ropes in the air, some landing in her bangs and face, but mostly on her hand and my lap. I laughed and apologized and she was kind of pissed, but she eventually laughed it off too. We then discussed a signal system and her swallowing. From then on, I would tap her head and say “I’m cumming,” she would redouble her efforts and swallow it all. She’d then take a swig of Listerine and rinse her mouth out as she didn’t want cum breath. Swallowing every time, as I loved the sound of it going down her throat, she easily ingested at least a gallon’s worth of my cum at one tablespoon a pop. She loved me a lot.

Sadly, my blowjob beauty and I separated one fateful day when we had bicycled over to her house, and her dad wasn’t home. I remember it clear as day she said, “Drop ‘em.”

“What do you mean?” I looked her dumbfounded.

Exasperated, “Your pants, I’m going to suck you dick!”

Not needing to tell me twice, I quickly took my pants off and sat down in the chair she had sitting in the middle of her room. She then slid right into her customary position on her knees and began giving me the most memorable blowjob I had ever had. She was really working it, up and down her head bobbed, giving twists with her mouth and hand. My hand resting on top of her head feeling the rhythm as she took my cock in and out of her mouth with the loving efficiency she had honed over the two years we were together. I heard a door open and close in the distant room, but it didn’t register. I was close to cumming.

Suddenly the door burst open and her dad began asking Cara about something, then his eyes befell his beautiful daughter on her knees in front of me, as she was on her way down.

“Oh hell no!” He exclaimed.

She quickly got up and I tried stuffing my hard cock back in my pants, but the trouble is the sudden excitement was enough to make me cum and I began spurt white ropes up the front of my shirt, scared to death.

Her dad got right in my face, a short stout Irishman, “If I ever catch you in this house again, I’m going to kick your ass!”

I mutter a meek “yessir” as I scurried off and tail between my legs. Cara followed me out telling me I didn’t need to go, but I feared for my life, and fled. Cara and I broke up shortly afterwards, never being able to face her dad ever again.

Years past and I had other girlfriends and sexual experiences and she was a distant “fish that I let go.” Until one day I was working in retail and her and her brother both came into the store. Scared shitless, but needing to provide customer service, I greeted them. They treated me like we were old pals!

“Hey, Ryan, it’s soo good to see how! How have you been?”

I was stricken with surprise. I knew he hadn’t forgotten what he saw, so how could this be?! We made small talk and caught up some and when I got home I contacted Cara via Facebook.

“What was that all about?! Your dad and brother came in and treated me like nothing had happened.” I asked her.

“Yeah,” she said, “out of all my boyfriends, you were my dad’s favorite.”

“What!? How so?”

Well it turns out that Cara had had a string of abusive boyfriends, both physically and emotionally. And Even though I had his little girl’s mouth on my dick, I treated her with love and care. But above all that, she told me, I wasn’t afraid of her dad. I wasn’t afraid to engage him and make conversation. Apparently, all her other boyfriends were only in it for the cock sucking, and too nervous to talk with him. And he respected that. So now I make it a point to engage parents when I can.

We stayed in touch a little bit from there on out, and had a yearly check in and catch up. She moved to a different state, got married, had a baby, and proceeded to get much higher level education. She was always intelligent, too smart even. I feel blessed that she even graced herself with me, never mind loved me once upon a time. She loves me still, but it’s something non-romantic.

Some more years past, and I was living my life getting my own education, when my family suffered a devastating blow, my mom died. Cara always loved my mom, and she showed up to the memorial we had. It turns out she was moving to the town I lived in and wouldn’t be too far away, and suggested that we should have dinner parties.

Absolutely, I agreed and the summer was filled with weekly dinner parties, games and laughter—me getting to know her husband and child. It’s difficult not to flirt with her. She’s so easy to get along with, especially given our history. So we would flirt with one another, playful and tame stuff, just making sexual references and such. She was expressing her frustration with some clients one day, and I joked about her getting out a riding crop and get these bitches in line. She laughed and agreed.

Throughout our chats, I started recounting different sexual adventures I had had. Confessing that I had accepted myself to be a cross dresser, that though I don’t cross dress all the time, only in the bedroom, I do always wear thong panties, I even pulled the strap up of the g-string I was wearing at the time to accentuate my point. She giggled and kind of cooed me. I also told her that I enjoy being dominated by women. I even disclosed that I was bi, and that one super hot night, I had met up with a couple on Craigslist, and I sucked “Mistress’s” husband’s (“Master’s”) dick while she watched. It took some goading, but eventually we met up with me going over to Master and Mistress’s house. I was to wear lacy black panties, undress, put on a cute little jersey mini skirt, a lycra cami, and give him a lap dance until Mistress told me to get on my knees and please Master until he cummed on my face. “I still fantasize about that night, but I wish Mistress would’ve pegged me, or let Master fuck me.” I laughed. Cara didn’t say much seeming nonchalant and pleasant as she always is.

The school year was progressing and her work picked up and the dinner parties continued, several months had gone by and we all became very close, making chit chat, and board games, and dinner parties. One such dinner party, Cara invited me over, and when I came in with my customary drinks, I noticed right away that their daughter wasn’t there.

“Where’s the child?” I asked, referring to her as if she were a queen.

“She’s with my dad for the weekend, so we can have uninhibited…fun.” She replied.

The subtle pause went right past me, so I carried on and we had a pleasant dinner and a round of Cards Against Humanity, without needing to stifle our language or content. She had won, and we all shared a good laugh. We stood up and proceeded to the TV room where her husband, John, put on the basketball game and began to watch it. Cara sauntered over to me, and kind of got quiet and put her head down a little and smiled. I smiled too watching her, always having a soft spot for her and we walked over to near where John sat. She put her arms around my neck and gave me a quick little hug not letting go fully and said quietly, “I had a really great time tonight, but you know what would really make this night amazing?” She looked at me with her cute smile, and sparkling eyes.

“What?” I asked quietly

“If you sucked my husband’s dick,” she said innocently.

The walls kind of closed in around me, and all I could say was, “What!?”

“I said,” her tongue suddenly becoming spiked as she grabbed a fistful of my hair, tilting my head back and forcing me down to my knees, “suck my husband’s cock!”

I looked at her face, no longer innocent, but stony and devilish. She had a feral look in her eyes, that told me I had no option but to comply. I looked at her husband, and he had a similar wicked grin, as he stood up. He was taller than me by about a half a foot, and he was very fit. He was wearing jersey shorts and no shirt which is his customary attire for summer days. His cock bulging out the front of his basketball shorts.

Cara shook my head by my hair as if to pull me from my trance, “Well!? I’m waiting! Pull his cock out for him and get to it!”

I timidly, slowly reached my hands to his waistband, hooked my fingers under his shorts and boxers, and began to reveal what looked like the longest cock I had ever seen. Half mast, and he was easily 7 inches long, he stood there naked before me while I’m on my knees. Cara’s hand was firmly in place, watching me intently. I reached forward and took his heavy cock in my hand and began to lean forward to take his thick, veiny, mushroom head in my mouth.

Cara cooed, “There’s a good slut. Put that cock in your mouth and work it.” She guided my head to his, and when my mouth made contact, I could taste the salty musky flavor of him. Cara mashed my head into his pelvis, filling my mouth all the way up with his limp cock. “Get him hard, you cock sucking slut! Love it as much as I do!” That’s a tall order because I know how well she gives head, and she’s had 15 years more of practice. I began sucking harder and with more enthusiasm as John began to harden to his full 9 inch length.

“That’s it, sissy! Suck his cock!” She said letting go of my hair and standing back as my head bobbed back and forth on John’s cock. Cara pulled out her phone and began videotaping me working her husband’s cock.

She put the phone away and thought for a moment. “Sissy doesn’t apply here, something’s missing. Get up!” She demanded.

Catching my breath, I looked up at her. “When I give you an order, you respond, ‘yes, Mistress!’ Do I make myself clear?” She instructed venomously.

“Yeah,” I responded.

WHACK! She slapped me hard across the face, “What was that?!”

I recoiled, “Yes, Mistress!” I exclaimed meekly.

“That’s better, John is also Master, is that clear?”

“Yes, Mistress.”

“Good, whore. Now get up!”

“Yes, Mistress,” I said as I slowly got up to my feet.

“Now, drop ‘em!”

I was suddenly taken back to her bedroom, those years ago when she gave me the same command. I guess she always was a femdom, but I never noticed or realized, and that’s what I found attractive about her. I undid the buckle of my belt, the button and zipper of my jeans, and stepped out of them.

“The shirt, too, off with it!” Cara barked.

“Yes, Mistress!” I responded as I quickly took off my shirt, now I’m standing before her and her husband in only my leopard print Victoria’s Secret v-string.

“See, I told you he was a sissy!” Cara chuckled to John.

“You were right,” he conceded with a haughty chuckle.

Cara went into their bedroom and rummaged in her closet for a moment, and came back holding the same dress I wore for her those years ago! “Put this on!” She demanded. “You looked so good in it those years ago, better than I did,” she admitted. “But then again, I always one to wear the pants, wasn’t I, you cock sucking sissy!”

“Yes, Mistress” I obediently said as I slipped the dress on over my head and donned it. It was shorter now that I’ve grown taller, barely covering my ass, but it still fit! I couldn’t believe it. “I can’t believe you kept it.” I whispered under my breath.

“Of course I did, slut! I was waiting for the day that you would come crawling back to me, and I was with a real man, who knew how to fuck, unlike you!” She chided me. “Now, get back to sucking!” She casually got out her phone and began recording again.

“Yes, Mistress.” I got back down on my knees again, Master’s cock still rock solid. I grabbed it and guided it back into my mouth, gingerly bobbing my head back and forth.

“No, no, no, that’s all wrong. Daddy, show him how it’s done!” she reprimanded me, but spoke sweetly to him.

“Yes, mama.” He grabbed the sides and back of my head with both hands and proceeded to fuck my mouth. “Keep it open, slut” Master said forcefully. I obliged and opened my mouth as wide it would go, and he began fucking my throat with his full 9 inches. GLARG GLARG my mouth went, spit beginning to form around my mouth and drip a little down the dress Cara gave me.

“That’s more like it. Do you like that, sissy? Do you like Master using your mouth like a cum depository like you did me?”

“Y-esth, Misth-res” I was cut off when Master stuck his cock all the way down my throat and held it there filling my esophagus. Cara came right up to my face and lick Master’s balls. “Yummy, isn’t it?” she cooed at me then nibbled my ear. “Keep him happy until I get back.”

I couldn’t speak with a cock balls deep in my mouth, John pulled out and pushed back, I couldn’t breathe, but he fucked my mouth uninhibitedly. A few moments late Cara came back and I couldn’t see her. John unceremoniously tore his cock from my mouth and spun me around, and I was face to face with Cara’s asshole spread wide open with her black thong pushed to the side. “Lick it!” She commanded. John was recording now.

I spread her ass cheeks apart and tongue fucked her puckered hole. It tasted so good! “Ah yeah!” Cara moaned, I thought she loved it but then, pfft! She jumped back and started clapping and laughing. She had just farted in my mouth. I swooned from the sudden gas, and she grabbed me by the face, “how was that, slut!?” She growled at me. She then spun back around and shoved my face into her asshole again, “Lick!”

“Yes, Mistress!” I stuck my tongue out wary of more gas, but stayed true to my duties, as she pressed her shapely ass around my mouth. Her ring spread as my tongue inserted deep into her and she moaned and giggled. John stepped around in front of her and she took his cock in her mouth and started giving him the same pleasure I had received so many years ago. She suddenly moved, and directed my mouth onto John’s cock. “Yes, suck it, taste that cock!” She leered and sneered at me, pushing my head hard into his pelvis.

She stepped around behind me, and gave my ass several hard spankings WHACK! WHACK! WHACK! I moaned into her husband’s cock, and she laughed, “Good slut!” She mocked. “Now, let’s see what this ass can do!” Cara flipped up my dress hem, pulled aside my thong and began licking my ass! I was in heaven with this fit beast of a man, and his raging cock in my throat. And my released angel licking my ass, it doesn’t get better, or so I thought.

That is until I felt her stop licking and felt her pressing up against my rim. “Lube” I heard her murmur, and rush into her room and return shortly after. Her husband had taken his cock from my mouth and was rubbing it all over my face, smearing my saliva all over, and mushing his balls every which way. Cara burst back in and I could hear a slicking sound, “That’s better!” she exclaimed and before I knew what happened, my ass was stretched and I felt hands on my hips pulling me back. John got right in my face with the camera on the phone and snapped a picture. He looked at it, and said, “Ooooh, yeah! That’s a keeper,” he pointed the display towards Cara. “Yeah, it is, she agreed.” She held the camera and recorded, and began thrusting her hips and her strap on back and forth inside of me, filling me up and emptying me out, leaving a void feeling. My grunts became primal as she punched my prostate with her dong.

“You like that, my little sissy, buttslut!?” her thrusts became more intense, and my hole was afire. I couldn’t keep my breath as her fucked me hard. I felt her rhythm change and she began to pant. Her strokes became deliberate and pointed. I could feel her tensing, mounting, then she grunted and held very still as her orgasm came over her.

Master grabbed my face and began fucking it again. “Mama just cummed in you, slut, thank her for her cum!” he demanded. John pulled his dick out so I could follow his orders, “thank you, Mistress.”

WHACK!! An Even sharper pain than before came in my ass as well as outside as she thrust in hard and spanked me. “For what, slut!?”

“Thank you, for cumming in me, Mistress!”

“That’s better,” she said, as she gave a few more gentle thrusts in and out, “your turn,” she offered John, as she pulled out of me and began to take off her harness. She came around front of me and I saw it was only 6 inches and about an inch in girth. Fear came over me, as I realized what was about to happen.

“No, please don’t!” I pleaded.

“What was that, sissy? No? NO!?” She bellowed at me, and slapped me hard across the face, “don’t you EVER tell me ‘no’ EVER again! Do I make myself clear?” She went into her bedroom and came back with a riding crop and started whipping me. “You-WHACK-follow-WHACK-orders-WHACK-when-WHACK-GIVEN! WHACK!”

I howl and wept, and through my tears I whimpered, “Ye-yes, Mis-stress”

“Good girl, now suck his cock and get it nice and wet, I used up all the lube.” She casually leaned back on the armrest of a chair, and I took his hard cock in my crying mouth, and began sucking it getting it wet and slick. When John was satisfied, he pulled back from my face and mounted behind me, aimed his heavy hard cock at my tight little hole and pressed in. It was painful, it stretched me beyond my means, and I felt like I was splitting in two. But then the head popped in, I howled. Cara laughed. I felt him slid another inch, and another and another, until I felt his balls pressed against mine.

“How does that feel, slut? Full?” Cara laughed and got close in on my face with her beautiful wicked smile. “I take that cock in the ass all the time, you’ll get used to it, oh and I didn’t even use my big toy.” Cara stood up and began to casually run her pussy over my nose and face forcing me to smell of and taste her pussy juices. “My real toy is much bigger than daddy here. And he can take it, like a man, but you’ll be taking it like a slut. I’m gentle with him, tender and loving, but you… only a fuck toy, meant for our pleasure.” She laughed as she gave my face a light slap. I felt John pull out slightly until it felt like his full length was out, and then he slammed back inside me. I howled again. John picked up speed and rhythm gradually, pulling me into him by the hips and pushing himself into me. I did eventually adjust and the pain subsided into an intense pleasure. My eyes rolled around in my head and my moans were guttural. I could feel my dick dripping precum as his thrusts became more rampant.

“I’m gonna cum, mama.” Cara’s husband declared.

“Oh good, hold on!” Cara excitedly hurried off. Coming back but not into view, “Ok, just let me know when you’re ready!”

“Ok, I’m ready!” He haphazardly ripped himself from my asshole, and stepped around to my front, and started jerking his cock, I felt something press against my rim again, and it caught on fire in a blaze of pain feeling it stretch. I screamed in ecstasy, and I felt fingers pull my mouth open, as what seemed like a quarter cup of cum dumped into my mouth, drizzling over the side, and down my chin. One rope landed in my eye blinding me. “Don’t you dare swallow yet, you fucking sissy cumslut!” I heard from behind me. As quickly as the pain in my ass appeared it was gone, and I was left with that empty feeling, Cara came around in front of me, and I could see her new turquoise dong was HUGE! “Open wiiiiiide and say ‘ah’.” Cara giggled her commanded. I did and she recorded. “Ok, you may swallow.”

I gargled Master’s cum and swallowed it all, heaving a great sigh once my mouth was clear, I slumped over exhausted. Master walked off and drew a shower and stepped in. Cara came over to me and settled back on her haunches and took my face in her hands and raised my eyes to meet hers.

“Thank you. That was a lot of fun.” She smiled brightly and sweetly and gave me a soft kiss on the cheek. My heart was confused and happy. She grabbed me by the hand and no longer had her huge strap on harnessed on. She was in a black thong, and nothing more. She set me seating on the sofa, and got into her customary position on her knees between my legs. She popped my cock in her mouth, grabbed my phone and took a blowjob selfie, and in practiced motion began to bob her head up and down. Lovingly she sucked, and she knew the symptoms of a cumming now, and didn’t need my warning as I erupted in her mouth. She opened her mouth wide and videotaped her swallowing my cum, giving a little kiss at the end. “Your cum, is still my favorite flavor,” she said genuinely, “I hope we can do this again sometime.” She kissed me on the lips, my cum on her breath. “You can keep that dress, it looks better on you anyways.”

I left that night, bedraggled and abused, but I looked forward to more. I need Mistress and Master.