Becoming A Sissy Slut (Part 1) free porn video

It was a Friday evening in late January as I walked through the lounge in the back of a bar in downtown Spokane Washington. A friend from work named Mark had invited me to come to his wife’s 30th birthday party and even though I didn’t know her, it was a good excuse to get out of my apartment.

I had just moved to Spokane the previous fall, taking a job as an engineer for large road building company. At 21 years old and just out of college, I was pretty proud to start out with a $60,000 a year job. Previous to accepting the job I didn’t know a soul in Spokane, however I’d made a few casual friends through work.

“Hey Ryan, over here” I heard Marks voice though the music playing in the lounge.

“Oh hey man” I replied as I approached Mark and his wife.

“This is the birthday girl, Lacey” Mark stated as he introduced us.

“Nice to meet you Lacey” I said as I shook her hand.

“You too Ryan” she replied with a friendly smile. “I’m gonna go talk to my friends honey” Lacey said to Mark as she kissed him on the cheek and headed towards a group of girls across the room.

“Well are you glad to be done for the year?” Mark asked me.

“Yeah I guess, not like we have a choice” I replied with a chuckle.

“Yeah, now that we’ve already engineered this coming years projects on the computers, nothing for us to do until the snow melts. Cheaper for the company to lay us off until April. At least we get to collect unemployment and just hang out until then!” Mark said with a smile then taking a big swig out of his mixed drink.

“Can’t complain about that!” I said cheerfully. “I’m gonna go get a drink.”

“Alright man” Mark said to me as I made my way to the bar.

The bartender was busy making a platter of shots for a large group of girls at the other end of the bar so I sat down on the edge of a stool to wait for him to come take my order. While I was waiting a woman walked over and leaned up against the bar next to me, obviously waiting to get a drink as well. She was stunningly beautiful; medium toned skin and short jet black hair. Her tight black t shirt and well fitting blue jeans were quite flattering. I couldn’t help but notice her stature as she leaned there next to me, oblivious to the fact that I was there. She appeared to be at least the same height as me, which at 5’8 isn’t too rare, but her physique was even more impressive. She looked like a pure athlete. Her shoulders and upper were well defined through her tight black. Though not broad nor sculpted like a man’s, you could clearly tell she was very very fit.

“Looks like it’s gonna be a while” she said in my direction, as she sat on the stool next to me. I didn’t even know she was aware of my presence.

“Yeah the birthday girl is keeping the barkeep pretty busy” I replied while looking down the bar at the group of girls ordering more shots and taking selfies.

“I figured they would be” she said as she turned and looked at me. Her stone blue eyes were piercing and her dark maroon lipstick made her look like the villains wife in an action movie. Needless to say I was quite intimidated.

Though I had slept with a half dozen girls or so through college I was no Casanova. My sandy blonde hair, fair skin and freckles made me look like I was still 17, I got carded every time I bought a pack of cigarettes and bartenders were very weary of my ID. Being 5’8 and 140 lbs didn’t help with my confidence but I tried to make up for it with friendliness and an upbeat attitude.

“I’m Ryan by the way” I said with a meek smile.

“I’m Kassy” she said back, surprising me with a smile of her own. “Mind if I sit here while I wait?”

“Absolutely not!” I blurted out, immediately regretting it.

“Ha ha your cute!” She said while laughing out loud.

Eventually we ordered drinks and to my surprise she continued sitting next to me as we got lost in conversation and alcohol. She told me that she was 34 and divorced, she owned her own beauty salon in Spokane. She was good friends with Lacey and came to celebrate her birthday party. As it turns out she had played college softball at Washington State University, which explained her remarkably athletic build.

I told her my story, that I was from Seattle, took the job in Spokane but didn’t really know anyone in town outside of work and that we were about to be laid off for 2 months.

We ended up sitting at the bar together the rest of the night drinking who knows how much. When the bartender yelled last call I couldn’t believe that it was 2 o’clock already, I stood up to pay my tab and realized I was hammered drunk!

“We better get you a cab Ryan!” Kassy said while laughing hard.

“I guess so...” I slurred in a drunken haze.

Once our tabs were paid Kassy helped me into the backseat of a cab then climbed in next to me. She told the cab driver something that I could barely understand as I leaned up in the corner of the back seat and quickly passed out...

“Good morning!” I heard as I snapped awake.

‘Where am I?’ I thought to myself as I looked at my surroundings. I’m on a couch without a shirt on and a sheet is over me. This definitely isn’t my apartment, this is definitely a girls house.

I sat up to see Kassy standing at the arm rest of the couch near my feet wearing a skin tight white tank top with no bra. Through my hazey eyes I could barely see the outline of her nipples perfectly centered on her perky tits.

“There’s coffee in the kitchen” she said sweetly as she reached down for my hand to help me up.

“Oh um, thank you” I replied through my hungover stupor. I grabbed her hand as she easily pulled me to my feet with one arm. As I stood to my feet and the sheet fell to the floor it became obviously apparent that I was stark naked standing in this goddess’s living room.

“Oh my god!” I blurted out as I covered myself with both hands. Not only was I shocked to be in the nude, my package is not the most impressive. At a mere 5 inches long when rock hard, completely soft it’s quite embarrassing. In fact it almost perfectly resembled a tube of chapstick when flaccid.

“Whoops!” Kassy said jokingly with a smile.

I reached down to grab the sheet to cover myself up, as I grabbed the sheet to lift it Kassys foot came down on the fabric. “What do you need that for?” She asked mysteriously.

“Well...I don’t know where my clothes are” I replied meekly.

“I don’t think you need them” she stated as she looked me up and down.

“Wha...what?” I asked.

She took a step towards me and lifted my chin with her soft hands. In one fluid motion she leaned in a kissed me while pushing my hands aside with her other hand, completely revealing my dick.

I kissed her back passionately all the while in awe of what was happening in the first few minutes of me being awake. As we stood in the living room for a few moments making out I couldn’t help but notice that she smelled freshly showered and had her hair already done for the day. All at once she pulled her mouth away from mine and shoved me back down onto the couch hard enough that I landed on my butt before I could even get my hands down to balance me. It surprised me how easily she blew me off my feet and onto the couch.

I sat there in awe looking at her figure. She had on extra small maroon shorts that were barely lower than her crotch. Her smooth, tan, defined thighs looked like you could bounce a quarter off of them. Here I was sitting on her couch with the physique of a boy just starting puberty, nearly zero muscle mass, non existent body hair, and a pathetic 5” rock hard cock in plain view of this athletic goddess.

As I sat there in complete awe she looked down at me with a smirk. “I’m gonna have some fun with you Ryan” she said with a friendly tone. She leaned forward and placed her hands on my bare thighs then dropped down to her knees in between my legs.

‘No fucking way’ I thought to myself. I knew better than to say anything out loud and risk changing her mind.

With her piercing blue eyes fixed on mine she slowly lowered her head down to my crotch. With her right hand she firmly grabbed the base of my dick, then took the head into her mouth and began massaging the underside with her tongue. The feeling was incredible as I watched in amazement. Next she began working her mouth up and down the shaft until she was taking the whole thing into her mouth. I couldn’t help but notice that the head of my dick probably wasn’t even near her throat, but I didn’t care. I was too lost in the moment to be concerned with what she thought of my penis size. She obviously liked it enough to put it in her mouth!

While going up and down on my dick she took one of her hands and wrapped it around the upper part of my balls, near where the scrotum meets the base of my cock. She slowly tightened her grip then began tugging on my balls, just hard enough to where it slightly hurt, but not bad enough to make me say anything. After a few minutes of this I couldn’t take anymore.

“I...I’m...I’m gonna cum soon” I gasped between panting breaths.

After saying this she took her hand that wasn’t pulling on my testicles and slid it under my ass cheeks. With her thumb she very firmly pressed against my taint, between my balls and asshole, and began massaging in a circular motion.

“Holy fuuuuuck!” I exclaimed as I felt an orgasm come over me. It was incredible as I felt shot after shot of cum shoot into her velvety smooth mouth. She kept sucking until I was entirely done, then pulled her mouth off my deflating cock. I leaned my head back onto the back cushions of the couch as I felt her climb onto me, sitting down on my lap. She put both of her hands onto my cheeks then leaned in and open mouth kissed me deep. Immediately I could taste the warm salty liquid in my mouth as I realized she was spitting my own cum into my mouth! Though I wasn’t all for it, I was in such a state of euphoria that I didn’t put up a fight. How could I after what had just happened to me?! She stayed on my lap for another few minutes while we made out and swapped my cum back and forth between our mouths, then sat back and stood up to her feet.

“How was that?” She asked with a big smile while wiping off her chin

“Fuckin...fucking...incredible” I somehow got the words out.

“Good! I’d love to do it again sometime!” She said excitedly.

‘What the hell is going on?’ I thought. ‘Am I in the fuckin twighlight zone?’

After a few more minutes of recovery time I found my clothes and got dressed. We exchanged numbers, gave each other a hug and I made my way to the door. “Hey, I’m serious, I’d love to do it again so don’t be afraid to call me” Kassy said in a serious tone as I opened the door to leave.

“Ok I won’t be!” I said as I left.

Once I got home I immediately crashed on my bed, even after the mornings events I still had a massive hangover.

I awoke in the afternoon feeling much better, and since I had an apartment all to myself I ended up jacking off twice while thinking about the blowjob I’d received that morning. To try to relive that morning as realistically as possible, right before I came I would firmly press in between my balls and anus, it was incredible how much more intense it made my orgasm. And just to further relive things I would gather my cum off my stomach and suck it off my fingers. ‘It’s just my own cum, not like it’s someone else’s and it’s not like anyone knows about it’ I thought to myself trying to justify my lewd behavior.

I waited 3 days before I texted Kassy, I didn’t want her to think I was too eager.

“Kassy? This is Ryan”

“Oh my god what took you so long! I thought you’d never get ahold of me!”

“Haha sorry I’ve been busy”

“Oh no you haven’t, I know your laid off lol. So what’s up?”

“Oh not much, seeing if maybe you wanted to hang out again”

“Of course! When were you thinking?”

“Whenever your free I guess”

“How bout you come over tonight around 7?”

“Perfect! See you then”

“Can’t wait! Xoxo”

I was so excited thinking about the night to come I must’ve walked 3 miles inside my apartment while watching the clock. At 430 I got into the shower to make sure I was fresh for Kassy. I made sure to shave my crotch completely smooth, while I had the razor out I figured I might as well shave between my balls and ass in anticipation that she would press there again. While doing that I noticed that it looked kinda silly to have a line there of smoothly shaved skin and then an area with hair. Not that I was overly hairy at all but I figured it wouldn’t hurt at all the get rid of the little hair I did have in my butt crack.

I arrived at Kassys door at 545 as eager as could be, to my surprise she met me at the door.

“What took you so long! Come on inside!” She said excitedly.

She looked incredible. Her jet black hair was combed forward, almost like a classic man’s haircut but a little longer on the top and sides. She was wearing a very tight white polo shirt with the top 3 buttons undone which showed just enough cleavage. Her tight khaki slacks hugged every curve of her muscular ass and thighs.

‘Why is this amazingly beautiful woman so into me?’ I couldn’t help but wonder.

“Soooo, I’ve gotta ask you a question” she said to me as I came in the door. “Have you ever had a rub and a tug?”

“Umm like a happy ending massage? No I have not”

“Well sweetie, would you like one?”

“Of course!” I nearly shouted.

“Great! In the bathroom there is a towel for you to wear, I’ll be in the bedroom across the hall when your ready”

‘How the hell did I get so lucky? What is it this woman enjoys about me so much??’

I went into the bathroom and tried as hard as I could to take my time getting undressed. I looked at myself naked in the mirror, my shaved groin matched my chest, stomach and arms which were naturally hairless minus a few whisps of blonde peach fuzz. ‘I’m not sure what she likes about me but I’m not gonna give her time to change her mind’ I thought to myself. I wrapped the towel around my waist and walked from the bathroom across the hall to the bedroom.

She had the room set up just like a massage parlor, the blankets were off the bed and a white sheet was stretched tight across a twin sized bed, the lights were turned down dim, candles burned on the night stand and soft music was playing from a small boom box.

“Go ahead and lay dow sweetie” Kassy said in a low soft voice.

I approached the twin size bed and lifted my left leg to climb onto it, and when I did my towel came undone and fell to the floor, completely exposing my backside with one leg on the floor and my other knee up on the bed.

“That’s okay” Kassy said in a calm and collected voice.

I laid face down onto the bed, a soft pillow beneath my face and she laid the towel over me just above my butt cheeks.

“Just try to relax now sweetie” she said so softly it was almost a whisper.

I felt a soothing warm liquid pouring onto my back followed by her strong hands beginning to massage. She worked her way up and down my back, down my arms and hands then back to my back. Next she started onto my feet and worked her way up my calves and to the back of my thighs. When she reached the towel she calmly asked “would it be ok if I removed this?”

I was in such a state of relaxation from the last half hour of massage that I was thinking I was in an actual massage parlor.

“Mhmm that’s fine” I quietly said back to her.

She slowly removed the towel as I felt the air on my exposed ass and balls. She began working on the back of my thighs up to my ass cheeks, taking her time and using her strong hands to rub deep into the muscle. I felt her hands slowly and gradually massage their way to the top of my freshly shaved ass crack. With her thumbs she began rubbing the inner most part of my butt cheeks, taking her time and working her way all the way down to my inner thighs along my groin. In my state of relaxation, and without even realizing I had done so, I spread my legs apart and let out a barely audible moan.

Next I felt a liberal amount of the warm oil being poured along my inner ass cheeks, running it’s way down my balls and onto the sheet below me. I felt all 4 of her fingers on my lower back and her thumb on my tailbone, she slowly ran her thumb all the way down until it was touching my balls, then ran her thumb back up to my tailbone. She went back and forth this way gradually increasing the pressure. Very slowly on one pass she stopped her thumb on my asshole and began massaging in small circles, with her other hand I could feel her lightly caressing my cock and balls. I hadn’t realized until now that I was completely erect! The pressure on my virgin hole was ever so slightly increasing and I could feel the tip of her thumb begin to protrude into me.

I had never considered putting anything into my ass myself or letting anyone else for that matter. But in this situation I was so relaxed, so turned on from this tanned goddess wanting to give me pleasure that I never once thought about stopping her.

Her thumb kept working it’s way inside of me until I could feel her knuckle reach my entrance, all the while her other hand was lightly grazing my dick, keeping me at full attention.

“Would you like me to keep going?” She softly whispered into my ear

“Mmm. Yes please” I replied.

“I want you to ask for it sweetie. Ask for more inside of you”

Without thinking and without realizing that the words came out of my mouth I heard myself say in a moaning voice “Please Kassy, please put more inside of me”

As soon as the words escaped my lips I felt her thumb continue inside of me, past the knuckle, until her entire thumb was buried in my ass. I couldn’t believe how good it felt. The minor stretching sensation, the first ever time feeling of having something inside of me combined with the light tickling on my penis almost sent me over the edge.

I let out a soft moan as she began working her thumb in and out of me, slowly at first then picking up to a medium pace.

“Would you like more sweetie?” She asked once again

“Oh yes, yes I would!” I nearly shouted

“All you have to do is ask for it...”

“Please give me more in my ass Kassy!”

“Mmm ok” she replied.

Gradually she removed her thumb from me, I almost felt empty without it as she had been working it in and out of me for the previous 10 minutes. I heard her open a drawer and looked over to see her putting on a latex medical glove. ‘I wonder why she has those in here?’

“I’m gonna need a little better access sweetie, would you mind propping yourself up onto your knees” she said firmly while adjusting the rubber glove.

Instinctively I did as she asked, putting my knees underneath me, my head still down on the pillow. As she approached me I felt so vulnerable with my legs spread and ass in the air, it almost felt like it wasn’t real life, I never imagined myself in this position, but the blood was pumping so hard to my penis that my sex drive was calling the shots, not me.

She applied another healthy amount of oil to my ass and then also covered my cock and balls with plenty of oil. Slowly she began inserting a gloved finger into my ass, it slid in much easier than her thumb and within 30 seconds she had her whole finger in working it in and out. Every so often she would give my raging hard cock a few strokes to keep me attentive, but not letting me get close to cumming. Soon I began wanting more inside me, my mouth once again worked before my brain could comprehend what I was saying.

“Please give me more inside my ass!” I exclaimed.

“Mhmm yes sweetie” Kassy said with excitement in her voice.

She removed her index finger and I could feel the tip of 2 fingers begin pressing against my entrance. She was slowly starting to work her way inside when I felt myself pushing back against her fingers to get them inside of me quicker. The familiar stretching feeling returned but was quickly replaced my tremendous amounts of anal pleasure. She held her fingers all the way insides me then asked “What would you like?”

“Please please finger fuck my ass! Please give it to me!”

“Good boy!” She replied with glee then began working her fingers in and out of my ass faster and faster. Before long she was finger fucking me with full force and I was loving every stroke of it, my ass wide open in the air and my face buried in a pillow.

“Are you ready to cum you little ass whore?” She asked in a loud voice over my moans

“Yes please! Please make me cum Kassy!”

With her left hand she began pumping my cock, essentially milking me, all the while feverishly finger fucking my ass.

“Oh god! Oh fuck!” I shouted as I felt my orgasm nearing.

Upon hearing that Kassy forcefully pushed a 3rd finger into my hungry ass and kept pumping away. I was not expecting it and the stretching was painful but I was experiencing so much pleasure I took it in stride. She milked my cock until it felt like a gallon of cum spewed out of me.

Slowly she removed her fingers from my ass, leaving me feeling empty and exposed. I rolled onto my side so I could face Kassy, she was smiling as she removed the latex glove. “Looks like you made quite a mess!” She said with a smile as she pointed to the giant puddle of cum on the sheets. “We probably shouldn’t let it go to waste...” she said looking right at me with those steel blue eyes.

“Ryan, I want you to lick it up then kiss me” She said in a serious tone.

After just cumming so hard I wasn’t really thinking about more kinky fun, but I wanted to please Kassy after all she had just done for me.

Slowly I leaned forward towards the pool of hot sticky cum.

“No-“ she said quickly “On your hands and knees when you do it”

“Yes Kassy” I replied obediently.

I got up onto my hands and knees and slowly began lapping up my own cum. The taste was familiar and I was beginning to associate my own orgasms with the flavor of hot cum. I licked up all that I could get off the sheets then looked up at Kassy, she smiled then leaned in and kissed me. It was a long, deep passionate kiss, both of our tongues in a slow wrestling match with salty cum in between.

“Well, what did you think?” She asked cheerfully

“That was fucking incredible, I’ve never had anything done like that to me” I said back to her as I got off the bed and stood up

“I’m glad I could do that for you! I can do a lot more for you Ryan if you want me to! I think you will really enjoy it” she said in a chipper voice as she gathered up the towels and sheets. She made her way into the bathroom and I heard her load up and start the washing machine.

“I’m gonna change into some more comfortable clothes” I heard her shout from the bathroom, I heard her footsteps head down the hall to what I assumed was the master bedroom.

“Ok sounds good” I called back out to her, not sure what to think of her comment about doing more for me.

I made my way back into the bathroom to get dressed again. I looked behind the door where I had left my clothes but they weren’t there. I checked in the dirty clothes hamper in the corner, went back and checked in the bedroom where we had just been but they were nowhere to be found.

‘Damn, she must’ve put them in the washing machine’ I thought. I walked down the hallway to a closed door that had light coming from underneath it.

I lightly tapped on the door “Umm Kassy?”

“Yes sweetie?” She said as she opened the door.

She had changed into a pair of black yoga pants that were so tight they looked like they were painted on and a sports bra with a diamond shape cut out of the front so it showed plenty of cleavage. This was the first time I had gotten a look at her body without so much clothing, she looked like she could be an Olympic athelete; she had a fuckin 6 pack! Her thigh muscles were well defined through the thin spandex. And here I was stark naked with both hands over my genitals standing in her hallway.

“I think you might have accidentally put my clothes in the washing machine” I said sheepishly

“Oh no! I’m so sorry! Come on into my bedroom, I’m sure we can find you something”

“Oh that’s ok I guess, I can just wrap a towel around myself” I replied as she invited me in

“Oh don’t be silly Ryan! Surely we can find something for you in here”

‘She’s right, she probably has a robe or some old sweat pants or something I can wear’ I thought.

Her bedroom was fairly simple, a few framed pictures on the wall, a queen size bed, 2 large dressers and a night stand. “Come on over sweetie, let’s see what we can find for you” She said as she opened up a drawer.

I walked over to where she was going through the top drawer. I could clearly see it was her panty drawer. “Hmm I think my hips are a little wider than yours so I’ll see if I have something a little tighter in here” she said to herself while rummaging through the drawer. “These should work” she said to herself while holding onto a small garment then going back to rummaging through the drawers. “And these” she said as she pulled out another piece of clothing.

“Here you go” she said as she handed me the clothes.

I looked down at what she had placed into my left hand, my right hand still covering my crotch.

“Ryan, you don’t have to cover yourself silly! Nothing I haven’t seen before” she said with a smile then turned back to her dresser “now we need a top” she muttered to herself as she pulled open another drawer and began searching.

I set the clothing she had given me into the bed. ‘No way am I wearing this’ I thought. The first was the skimpiest g string I had ever seen. The strings were barely thicker than dental floss and the front piece of fabric was smaller than the tags on my t shirt. The second was a very very short pair of shorts, when I turned them over they had the word SLUT printed across the ass.

“Kassy, you don’t expect me to wear these do you?” I asked

“Umm why wouldn’t you? It’s not like anyone is going to see you besides me and you can’t just walk around naked”

“Well yeah but...are the panties really necessary?”

“Well you have to wear underwear sweetie!” She said with a smile. “And besides, no offense but we both know that your not too big in the pants for them”

“I guess” I said feeling slightly humiliated.

‘If she wasn’t so hot there’s no way I would do this’ I thought as I slowly pulled the g string up between my legs. Once I got it into place I immediately got butterflies in my stomach. ‘Oh my god this feels so wrong but so exciting! I can’t let her know that I don’t hate it.’ The way the soft fabric felt against my skin but still showed so much made me feel dirty, honestly, like a slut. It was only fitting that I put on the shorts. Kassy was right that I need underwear, without them I would have been hanging out of the bottom of the shorts.

“And these should just about do it” Kassy stated as she handed me 2 more garments.

I looked down to see a training bra and a spaghetti strap tank top with glitter on it.

“A bra? Really??” I asked with concern in my voice.

“Just try them on, for me...” she said looking straight into me with those cold blue eyes.

I sighed and pulled the training bra on over my head and down around my chest. It fit surprisingly well. I unfolded the tank top only to find that the glitter spelled out FUCK ME across the front. ‘Who cares’ I thought ‘I’ve came this far and nobody is going to see me anyways’

“Perfect!” Kassy exclaimed with glee “let me step back and get a better look at you!” She said as she walked to the center of the room and looked me up and down. I stood there humiliated as she checked me out from head to toe.

“My my my...Ryan can I try something with you? And if you don’t like it we never have to do it again? It will be our little secret I promise”

“Umm What is it?” I asked her back, unsure of what she was getting at

“You just have to trust me, if you don’t like it I’ll never ask you again” she said, almost sounding eager.

‘I’ve greatly enjoyed everything she’s done to me so far, and she’s soooo fuckin hot’ I thought.

“Ok, I’ll try whatever you want...”

“Oh yay! I bet you’ll love it!!!” She shouted gleefully “Ok take off all your clothes then meet me in the bathroom”

I obediently removed my top and shorts then followed her into the master bathroom where she was filling the bathtub with hot water. “Climb in Ryan and just relax. The only rule is no asking questions and no complaining, but you can quit whenever you want”

“Ok, that’s fine” I replied meekly as I sat down in the warm water.

Once the tub was full she began rubbing my legs down with some sort of lotion, all the way from my groin to my toes. It didn’t take long for my cock to get rock hard again as I tried to cover it with my hands.

“That’s okay Ryan, she said softly, “nothing to be embarrassed of” as she continued rubbing my entire legs.

She reached into the cabinet and pulled out a ladies razor. ‘What the hell...well maybe she just really doesn’t like body hair’ I tried telling myself.

Slowly but surely she began shaving my legs, feet and ass cheeks. Next she worked up my stomach, chest arms and shoulders; though there wasn’t much to shave off.

“Ok, you can dry off the have a seat on the toilet lid” she said.

I stood up while the water drained out and grabbed a towel, I couldn’t help but admire how much sexier my legs felt and looked now that they were shaved smooth. Before they had just enough hair on them to where they looked kind of dirty, but now they glistened in the light and were completely smooth to the touch. I dried off and sat down on the toilet lid wondering what she was planning next.

“Chin up” She said to me as she grabbed a make up brush and leaned towards me

‘Oh no way!’ I thought ‘Why the hell would she wanna do this?!’ But I didn’t complain, I figured whatever she wanted to do would be worth it for the sexual reward in the end.

For the next 45 minutes I sat in the chair facing her while she applied make up to my face and eyes, finishing it off with some bright red lipstick.

“Don’t look in the mirror yet!” She said with cheer as she ran into the bedroom, she came back into the bathroom with a long brown wig and began fitting it to my head and brushing it out. “Ok your outfit is laying on the bed. Go put it on and then you can come look in the mirror”

I walked out into the bedroom to find a white spandex mini skirt on the bed and a pair of 4 inch red high heels. I took a deep breath and thought ‘just think about the sex...this will all be worth it...’

I carefully pulled the miniskirt down over my head, being careful not to mess up my wig or make up. I pulled it down over my arms and torso, it was so short I had to pull and stretch it to get it below my crotch and the bottom of my ass cheeks. I couldn’t help but feel kind of sexy, even though I couldn’t see myself I could feel the spandex hugging my hips and the air coming up between my legs to my exposed ass and balls. I sat on the edge of the bed and slipped my feet into the high heels and strapped them over the top of my feet, I sat up and admired them. They did look pretty sexy up against my freshly shaved legs...

I stood up and very carefully made my way back to the bathroom on shakey legs.

“Oh my god Ryan, you look so fucking hot!!” Kassy almost yelled.

I stepped in front of the mirror to get a look at myself and almost couldn’t believe my eyes. I looked like a completely passable teenage girl! Kassy had applied my makeup on thick, the wig was flowing like real hair and went well with my natural skin tone and the miniskirt fit me so tight it almost made me look like I had curves. And standing next to Kassys muscular, toned body I looked quite frail and feminine.

“Well what do you think?” She asked with intrigue

“I don’t know what to say...I think I look really good...is this what you wanted me to try?” I asked unsure of myself

“This is the first part Ryan, I want you to stay here while I go put my outfit on, I’ll call you when I’m ready” she said as she walked out of the bathroom and closed the door behind her.

I stood in the bathroom nervously, trying to balance in my high heels, wondering to myself what she would be wearing and what she had in mind...

After less than a minute I heard her call out through the door “Ok I’m ready”

‘That was quick, maybe she’s naked!’ I thought to myself as I excitedly swung the door open.

To my shock Kassy was standing in the middle of the bedroom wearing her same yoga pants and sports bra, the only difference was that she had a massive strap on dildo around her waist!

‘Maybe this has gone to far’ I thought as I stared at her rubber cock in awe.

“Come here Ryan, don’t be nervous” she said calmly.

On shakey legs I walked across the room to her.

“This is what I want from you tonight Ryan, I want you to be my sissy. I’m asking you to just try it for me, if you don’t enjoy it I will never bring it up again”

I stood there nearly in shock, biting my lip and wondering what I should do. My mouth worked faster than my brain.

“Ok Kassy, I’ll try it”. The words sounded like somebody else said them.

“Thank you Ryan” she said in a soothing voice. “For the rest of the night I want you to refer to me as mistress and I want you to do exactly as I tell you”

“Yes mistress” I said with a submissive feeling in the pit of my stomach.

As soon as the words escaped my lips she leaned in and kissed me deeply, massaging my tongue with hers, firmly rubbing her hands over my ass cheeks.

Suddenly she pulled her mouth apart from mine. “On your knees sissy” she said in a stern voice.

Obediently I got down on my knees in front of mistress Kassy, the rubber strap on dildo was mere inches from my face. It was much bigger than mine, my guess was at least 7 inches, quite thick, and very realistic. It had a clearly defined head, veins, and balls attached to the bottom.

“I want you to suck my cock Ryan, I want you to give me the best blowjob you possibly can”

“Yes ma’am” I replied as I focused on the rubber dick in front of me. I slowly opened my mouth and took the tip in. All at once I felt a rush of endorphins hit me, it felt like I was high on some sort of drug. I swirled my tongue around the head the way Kassy had done to me just a few days before. Sooner than later I began bobbing my head up and down on this massive cock, applying as much saliva as I could, being careful not to scrape my teeth on the shaft. I took my right hand and began stroking the lower portion of the shaft that I could not get to with my lips.

I could hear mistress very softly speaking down to me. “That’s it Ryan, suck cock for me. Be a sissy faggot for me Ryan. Open your mouth for cock Ryan...focus on pleasing cock...”

This dirty talk only made me feel higher, I could feel my own erection pressing with all its might against the front of my mini dress. In the midst of my cock sucking, mistress pulled out of my mouth abruptly.

“Ask for it sissy, beg for cock in your mouth” mistress Kassy ordered me.

“Please mistress feed me cock! Please allow me to suck on your hard dick!”

With that she put both of her muscular hands on the back of my head and pushed her veiny prick into my mouth.

“Hands down” she ordered me and she began slowly but deeply pumping in and out of my mouth, gradually working it into my throat. Within a few strokes she was shoving the tip down my throat, holding it there for a few seconds, then stroking out. After a few pumps of this I began to gag hard but she held my head firmly in place on her cock. I spit up a mouthful of mucus and saliva all over mistress’s magnificent dick, it ran down the balls and my chin in long strings.

Satisfied, she pulled out of my mouth then said “that’s a good girl, you must be willing to do whatever it takes to please cock”

‘Did she just call me a girl?’ And what did she mean Please cock? It’s a rubber dick, how can I pleasure it?’

No time to think, all I had on my mind at this point was how to please mistress.

“Lay down on the bed now sissy” mistress ordered me, I stood to my feet and took a few steps back, laying myself onto the bed on my back. “Sissy, this is the only time you will ever be fucked like a real girl, and that’s only because it is your first time. After this you will only be fucked like a sissy slut. That is because you are not a real girl, you are a sissy who’s purpose is to please cock. Do you understand me?”

“Yes ma’am I do” after the powerful orgasm mistress had given me earlier with only her fingers, all I had on my mind was another one.

Mistress climbed on top of me and began kissing me softly, nibbling on my neck, her rubber dick pressing into my stomach. With one hand she slowly reach down and lifted my my skirt up, I raised my hips allowing her to lift it up above my hips, revealing my freshly shaved genitals and ass. Slowly she reached her hand down, past my rock hard 5 inches, and began working her fingers around my ass. Instinctively I spread my legs for her.

“Mmm feels like your sissy hole is still nice and relaxed, do you think you are ready for me?” Mistress whispered into my ear.

“Yes ma’am, please put your dick inside of me” I lightly said back to her, in my most feminine voice.

Mistress reached into the nightstand drawer, grabbed a bottle of lubricant and poured plenty of it onto the rubber dildo firmly attached to her waist. It was a beautiful sight, a powerful yet beautiful woman slowly stroking a hard rubber dick, about to push it into a virgin sissy ass. She grabbed a pillow and motioned for me to raise my hips, I obliged and she put the pillow under my lower back which raised my ass off of the bed, giving her better access.

She held the base of her lubed up dick and placed the tip of the head at the entrance of my sissy hole. She looked me in the eyes, I gave her a slight nod, signaling to proceed. Ever so gently she began pushing into me, I relaxed as much as I could, feeling my outer ring being stretched further than it ever had been before. She paused for a few moments then continued. The pressure was constant and I was beginning to wonder if I would be able to take it in, then at once I felt a pop, a sharp pain and a feeling of fullness like I’d never experienced. Mistress Kasey paused, obviously seeing my face contorted in discomfort. After maybe 30 seconds the pain subsided and a wave of pleasure took over; I gave mistress another nod of approval and she gradually buried the entire thing into my ass.

The feeling was almost indescribable, I’d never had a cock in my ass, I had just lost my anal virginity to a beautiful, muscular goddess, once I felt that it was all the way in a sea of emotion ran over me. I looked into mistress’s eyes; I loved her, i wanted to marry her, I wanted to serve her, I would do absolutely anything on earth to please her in exchange for her introducing this to me. I wrapped my legs around her waist, hooking my ankles together behind her back, and wrapped my arms around her shoulders, pulling her into me as she slowly began to fuck me

“Thank you mistress, thank you so much mistress” I softly spoke aloud.

Gradually mistress Kassy started fucking my ass with more force. She certainly was not pounding me but I could feel her hips starting to slam into me from the missionary position. Every time she would thrust into me I began lifting my legs slightly, allowing her to get as deep of penetration as possible. With every thrust I could feel the veiny shaft running along my tight entrance, the head sliding along my insides, pushing its way in with every stroke.

Mistress Kassy began whispering into my ear while she fucked her sissy. “That’s right Ryan, get fucked like a good girl. Take the cock, love it, do anything for it, become a cock worshiping sissy slut for me...”

“Yes mistress I will, I will do anything you ask of me, I am your sissy slut to do with as you please”

“Good girl Ryan, I want you to to cum for me now Ryan”

“Yes mistress I will cum for you”

I unwrapped my legs from mistress as she hooked her muscular arms under my ass cheeks. Without removing her cock from my ass she stood up while lifting my lower half until only the back of my head, back of my neck and top of my shoulders were touching the bed, with my lower half up above me. Mistress was standing in a crouched position, holding my legs upright while still fucking me with her cock at a downward angle.

“Cum for me Ryan, I want you to cum into your own mouth.”

I had been rock hard for the last 30 minutes and I was ready to cum. Mistress rocked my knees downward toward my face, bringing the tip of my tiny dick just a few inches from my face. While still plunging her dick into my sissy hole, mistress reached down and slowly began tugging on my cock, aiming it directly at my mouth. I felt myself getting close and opened my mouth wide. Mistress held her cock balls deep inside of me as I let loose rope after rope of hot cum into my own mouth. My orgasm felt like an electric chair as she kept stroking my cock, more and more sticky salty cum covered my tongue and i relished in the taste. Inevitably, I ran out of delicious cum.

Mistress laid me back down onto my back and slowly withdrew her rubber dick from my sissy ass. I immediately felt empty, I could feel my hole gaping, yearning to be filled again. She slowly crawled up towards my head and placed the head of her amazing cock near my mouth. “Suck it Ryan, clean the cock that turned you into a sissy slut”

“Yes ma’am!” I nearly shouted as I opened my mouth and eagerly began sucking the dick that had just fucked my ass so wonderfully.

“Good girl Ryan, good girl” mistress said as she gently stroked the cheek of my face. Mistress laid down on her side behind me, wrapping her strong arms around me snugly. “We need to have a conversation in the morning Ryan, till then sleep well” she whispered.

“Yes ma’am” I replied in a low tone and drifted off to sleep...

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