Sherry got fucked by the Shemale hairdresser Shemale Sex Stories
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What She Wanted free porn video
Chapter - 1
So here I am, following my dick around again. Such power HE wields, haha. After I met her, purely a chance occurrence, I seemed to end up at her house. I did not know who she was, or how she acted, but I am a guy, so, like that really matters, haha. But, I digress...
Lots of fantasies passed through my mind during the drive over, lots. I pulled up to her place and composed myself. Since I was winging this, I was running on the normal assumption "You can't fuck up a plan you don't have." So, not really sure what was going to happen, I walking up to her door and knocked.
After a few seconds, she opened the door wide and peered out. I smiled and said hello as she showed me quickly inside. I turned around and watched her close the door. When her back was to me, I stepped forward and stood, pinning her between the door and myself.
I leaned into her and whispered into her ear, "Are you wet?"
"Oh God! Yes I am."
"Are you nervous?"
"Y... Yes."
She was trembling, from fear or excitement? Hopefully both. I rubbed her shoulders and asked her to get me a drink. Giving her something to do would calm her down. She was nice looking, very cute. She was in her 30's, short, about up to my shoulders. She had thin legs that looked nice. She had on sweat pants and a cotton shirt. Her tits did not seem to be huge, but beggars cannot be choosers.
All in all, I would say I got quite lucky, considering all the different kind of people out there. We sat on the couch making small talk about her apartment and all. To break the ice, I asked her to rub my shoulders. Sitting in front of her on the floor, she rubbed my neck. She seemed much more relaxed not having me look at her while we talked. She said that she had a boyfriend that was really blah, boring, and just wanted to get his rocks off and go to sleep. He was out of town and she stayed late at work, nothing else to do.
I asked her if she had panties on and she stopped rubbing my neck and said, "Yes". That seemed to catch her off her guard. Still sitting in front of her, I changed the tone of my voice to be a little more demanding and said, "Rub your pussy with your fingers and let me taste you."
She hesitated a second, and mumbled "Oh god" and then I felt her start squirming around. A second later her fingers, dripping wet, slid around in front of my face. I took her hand and sucked her fingers into my mouth. She squeezed me in-between her legs and stood up. "I can't wait any longer, lets go into the bedroom."
"No," looking into her eyes. "Take your shirt off, Now"
She looked away, sighed, and I said, "I can leave!"
"No, no. Please stay."
"What do you want?" I asked.
She did not say anything, just standing there... I sat down on the couch. "Take your shirt off."
She lifted it over her head and stood looking at me. "The bra also!"
As she removed it, out popped some nice tits. They were full, no sag, and had big long nipples. I let her stand there a few seconds, just watching her, and then reached out and touched her chest. She closed her eyes and moaned as I closed my hand and pulled her nipple out. She started to sit and I loudly said, "No, keep standing!"
She stood straight up and opened her eyes. I made sure she watched as I leaned close and moved my mouth towards her tit. Slowly opening my mouth, I slid it over her nipple and sucked in. I rubbed my tongue back and forth over her nipple and pulled my mouth away, grabbing with my teeth and gently biting. "Oh, ohhh" she said grabbing my head.
"Are you going to be good? Going to do everything I say? Or am I going to leave? I hate to think you were lying when you wished for someone else to be in control."
"No, Yes, No... I will do what you say. I don't want you to leave. I am so hot."
"You understand, there are consequences if you do not follow instructions. Consequences that are both good and bad, painful and pleasurable."
"Yes, I understand. I will, but please don't hurt me!"
"That should not concern you. I am only here for your pleasure. You expressed an interest in being submissive, letting go. We are going to explore that. If I go too far, your safe word is "jelly beans". If you can't take it any more, don't want to continue, just say the safe word, and we will stop."
"Ok, I understand."
"You liked that story about the woman being a sex slave I will use you sexually, both mentally and physically, and you will have many, many orgasms, so remember, you only get to use the safe word once, only once, so use it wisely. If you say stop, it all stops. Remember, you are capable of much more than you know."
I sat back down and pulled her directly in front of me. "Take your pants off!" She hesitated and I repeated myself. "I will not repeat myself again!"
She pulled her sweats down and the crotch was soaking wet. She stepped out of them and stood there, looking down. Her nipples were hard as rocks and her inner thighs were glistening. I slapped the insides of her legs and said "Spread em'". Her pussy was shaved smooth except for a little patch above her clit. It was big and wet and swollen and... juicy.
I made my middle finger hard and hooked it as I reached out and cupped her pussy. My finger slid right inside her and my hand went at least an inch into wet pussy lips. "Now this is a pussy!" I said. I rubbed my hand all around and got my finger in tight. It felt soft and velvety inside.
She was kind of squatting down on my hand with her knees bowlegged. She had to hold onto my shoulders to stand up. She took a deep breath and held it and had not let it go yet. I pulled my hand tight against her cunt and wiggled my finger. It was curled right behind her vulva, right where the G spot is. She let out an "Auuggghhhmmm" and started to cum.
As I wiggle my finger inside I rubbed my thumb against her clit and she just froze up and I felt her pussy just flood with moisture and then she started to hump my hand like crazy. Her legs were shaking and about to give out so I smacked her on the ass hard and loud and said, "Stand up."
She jumped and strengthened her legs and rubbed her ass where I hit it. She was right on the edge of another orgasm when I pulled my hand away. She opened her eyes and looked confused. "Not yet, not yet. Your first orgasm is free, the rest you have to earn."
"Turn around... Around! Good, Bend over... lean... Good girl." SMACK, smack. "OUCH", she said, but she stood her ground, she did not move. I started spreading swats across her backside. Light, then hard, different all the time. She was bent over, with her hands on her knees, pushing her ass back towards me. "You like that huh?" "Yes, yes it feels good." I stopped and pushed my hand between her legs and rubbed her clit.
She was dripping wet, so I got my hand completely wet, rubbing her cunt and fingering her, until just before she came, and then I pulled away and started spanking her ass with my wet hand. It must have stung like crazy. She moaned, yelped and gritted her teeth, but she wanted more. I slapped her thighs, her ass, and worked my way to her pussy. I started light and got progressively harder. Slapping my fingers right over her clit. She started to shake and quivver and she came like mad. She squirted a stream of cum out of her pussy all over the floor. I rubbed it for a second and then started spanking it again. She came again, or was still cumming and squirted two more times. It was incredible.
She fell to her knees, unable to hold herself up. I leaned over and started kissing her ass and legs. She was red and hot as I ran my tongue over her ass.
"I bet you did not know you could squirt, did you. I did not even have to try very hard."
"I had no idea! I have heard of it, but... ohhh... everything is all tingly. That orgasm was the best thing in the world."
"Well, you ain't seen nothing yet. You wanted to become someone's sex slave. Here's your chance. "Turn over, sit, sit-up."
"OK, this is where you can turn back. You only get one. Is this a taste of what you want? I will train you to act properly around me, to follow instructions perfectly. You will be punished for not doing them correctly. But... the payoff... you just got a taste of." I stopped and looked at her, stared into her eyes. She was still breathing hard from her previous orgasm. She looked down, unsure.
"Do you submit to everything I am, everything I do, everything I say? For my pleasure and yours! Go think about it. Go sit on the edge of the bed. Just sit there; don't touch your pussy, your tits, nothing. Just feel what you want. If you want this come back and ask me to train you."
She just sat there. Looking down. I waited and she looked up and said the magic words. "This is hard. I am not sure what to do, but I love this feeling and I want to know more. Please train me, use me, and make me cum like that again. Make me feel like a... a slut." I stood up and took off my clothes. She just stayed kneeling in front of the couch. I sat on the edge of the couch and pushed her knees apart. Sitting in front of her naked, my dick as hard as diamonds, I reached out and rubbed her pussy and got my fingers wet. I slid them across her mouth, leaving a wet, slimy trail.
"This is where it starts. There is no turning back. Now... rub your nipples. Move your hands and rub your tits and twist and pull your nipples."
Suprisingly, she reached right up and started playing with her tits. She seemed to like grabbing her nipples and pulling them out and letting her boobs fall back. When she was not paying attention, I reached out and grabbed hold of her tit and twisted it tight. They were just the right size to fit like a soft Nerf football. I pulled her towards me by her tit and said "Suck my dick, slut!" She moaned and leaned forward and swallowed the whole thing. Now, a six or six and a half inch piece of sturdy meat is what I carry around. Not like some stories where size is not an object, haha. I let her tit go and grabbed the back of her head and started fucking her face. She tried to use her hands, but I made her stop.
"Rub your nipples and just fuck me with your mouth. If you can make yourself cum, by twisting your nipples, you first punishment will be free, and that one is always the worst."
She moaned from somewhere in her throat and grabbed both boobs. Her fingers were twisting her nipples and she was bobbing her head up and down my shaft. Her pelvis started to curl and move like she was fucking someone. She was pulling her nipples harder and her breathing was getting faster.
"Go on, make yourself cum. I am not helping this time. You either do it by yourself, or take your first punishment. Come on! Any decent slut can make herself cum. If you can't even do that, your pretty worthless."
I waited and watched. She was right on the edge. "Twist those nipples, Yeah! Cum for me. Squirt on the floor, just like before. Do it, squirt for me, or I will spank your ass until you cry."
Right then she froze up and then shoved her hand to her pussy and rubbed her clit. She came like a flood. It looked like a dam had broken. Twice she froze up and then came, squirting when she moved her hand. After about 2 minutes, she stopped jumping and just sat their, head hung, breathing heavy.
"I leaned down to her ear and said "And just think how hard you will come when I help!" I raked my fingernails down her back as I walked past her and it looked like she had another orgasm. She was having little mini-tremors.
I walked around and had a look at her place. It was nice, 2 bedroom, little kitchen. I turned around and she was standing right behind me. "I did not tell you that you could get up?"
"I have to pee."
"Well then, let's pee." And I turned into the bathroom. I sat her down on the toilet and stood there waiting. She just sat there and said, "I can't with you here."
"Get over it then, because you will. Go on just pee. I am only standing here."
"I can't."
"Do it, you had to pee, so pee."
"Please leave, I have to really go."
"No, not a chance. Pee, or don't, up to you."
"I won't with yo...
"WON'T, won't do what? What you promised to do, anything I said. I said you could pee, and you won't?"
I yanked her up and turned her around. Grabbing her hair by the back of my neck, I bent her over so her face was over the toilet. I smacked her ass and held her in place with my legs.
"You promised, SMACK, to be a slave, smack, smack, and now you want out, smack, smack. I should just fucking leave, this isn't worth it."
I stood up and turned and she grabbed me and said "No, no. I will."
"I will what?"
"I will try to pee for you."
"Try, you better pee, right here, standing right there. PEE, NOW, right where you are standing."
She closed her eyes and pee started running down her legs. She must have been holding it for a while. It was making a big puddle on the floor. I reached down and rubbed her pussy while she was going.
"What a little slut you are, standing here, with a stranger rubbing your pussy, peeing all over yourself. All done? Feel better? Let's go."
"Wait, I need to wipe."
"No, you are such a nasty slut, that should be a rather nice smell for you to carry around. Now, SMACK, get going. To the bed, get on your knee's with your ass in the air."
I walked into the bedroom and opened the blinds. She was not comfortable with this, afraid someone would see inside, but I just ignored her. She had a nice sturdy wood futon style bed. I swatted her upturned ass a few times and rubbed her wet pussy. I pulled her upright and stood her at the end of the bed.
I got into my bag of goodies that I had brought and soon had several pieces of rope. It was a short bed, so her ass was way above the top. I tied her ankles to the bottom corners and her wrists at an angle down to the top of the corners. I reached into the bag and pulled out a handful of clothespins. She was not looking too happy about this and started asking a bunch of questions. I took one pin, made her open her mouth and stick out her tongue.
"Do not flinch." I clipped her tongue for a few seconds and then removed the pin. This obviously hurt a great deal. "Hold this in your mouth and DO NOT drop it. If you talk again, or drop this clothespin, I will clip it to your tongue and leave it there."
She sucked the pin into her mouth and held it firm. She watched wide-eyed as I slowly grabbed each tit and placed pins around the nipple. I got ten on each boob, in a neat circle. She was breathing hard and steady, but was not going to drop that pin in her mouth.
I shook her tits, making the pins rattle together. She moaned and leaned into her ropes, struggling to get out. I went into the bathroom and got one of her hairbrushes. She did not see me when I came back, and jumped when I swatted her ass. I just kept hitting her, slow and hard, fast and light. She was really breathing hard as I stopped and bent down to my bag.
"Give me a number between one and five." She mumbled four as I pulled out one of those leather slappers.
"The shape of this paddle will do just nicely. Please count for me..."
I swung upwards, and hit the bottom of her tits. She jumped and made the clothespins wiggle. Her tits were great for this. She never said anything, just leaning with her eyes closed.
"COUNT! That earns you four more swats."
"Oonnne," she mumbled.
"Nope, start again."
I swung and hit the top of her boob. "MMMMmhh Oonnee"
SWAT
"Ttooo" SWAT
"Ttrreee" SWAT
"Aaugg ffourrrr"
I reached over and removed a few pins. It left little red teeth marks. I swatted again, right where the pins had been. She flinched, groaning, and then "Fiiive"
Swat
"Mmm Siisss"
I removed a few more from the other tit. She almost dropped the pin in her mouth. She was clenching it with her teeth. SWAT
This time was a clear "Aauugghh Sseven" SMACK "Eight, nnooo mooooree"
I took my time removing the rest of the pins. I grabbed both of her tits and roughly mashed them and rubbed the teeth marks. I still had not touched her nipples and when I leaned over and sucked one in my mouth, she started to cum. She was pulled tight against the rope and trying to get away from my mouth.
I moved to the other tit and when I sucked her nipple and she gasp, the pin dropped from her mouth. I stopped and smacked her nipple with the paddle. "I told you that you would not like it if you dropped the pin."
I slapped each nipple, one after the other, not too hard, but she started coming like a rabbit. She held her head back and pushed her tits out and clenched up and shook each time I hit them.
Once I quit, and she stopped cumming, I untied her and she slumped back onto the bed. I stood over her and jacked off and when she looked up at me, I came all over her face. She lay there licking my sperm off her fingers and either fell asleep or passed out.
I picked up all my stuff and left a note. "Next time..."
Chapter - 2I was unsure how to next approach her. We had met online one evening and then met at her house 2 hours later. Not the safest thing in the world, but certainly adventurous. She emailed me continuously during the days following our encounter. At first she was mad that I had just left, but after re-affirming the fact that she was not in control, the tone with her letters changed.
There were a few really fun days where I had her following orders and doing sexual things. They were really nothing, but having to finger her pussy at work in her shortest skirt and bra-less top was unheard of. She of course did these things I dreamed up. She would do anything.
On the following Friday, during her lunch hour, I sent her a list of instructions. She was to go into the bathroom and remove her panties. During lunch, I had her sit at her desk, skirt pulled up, and spank her pussy. To prove she did this, I asked her to use her PC microphone and record the sounds and email me the file.
"If I get no file, I will not see you again. If I like the sound file enough to get my dick hard, then I would be at your house promptly at 6PM."
Sure enough, 30 minutes later, I was listening to her spank her pussy and moan. She was talking and saying she wanted me there to fuck her. She could not understand why she did these things, "Why, how do you make me do this? Please, tonight, use me, make me scream with pleasure."
I listened to her ramble for a few more minutes and closed the file. I typed out a return email and told her what I expected.
1) Do nothing for the rest of the afternoon. Just sit at your desk! No bathroom, no snack-break, NOTHING! Just think about how you will please me tonight!
2) Go straight home from work and I will be waiting. Lock your car and go inside your apartment. Leave the front door open and immediately remove all your clothes and leave them in a pile by the door.
3) Crawl, on your hands and knees, to the bedroom. Get in the middle of the bed with your head face down, your ass pushed up in the air. If these orders are not followed exactly, I will not even enter your house.
This should prove to be a fun time! I was actually salivating at the nasty, wicked thoughts running through my head. My head, well, brain, was in overdrive, but certainly not in control, haha.
I sat in the corner of her apartment parking lot, watching as she drove up. She looked around but could not see me. She hurried up the stairs but I could not see inside due to the angle of the door. I waited a second and then proceeded to her place. The door was indeed open with a pile of clothes. It was kinda messy inside, but she did not know I was coming.
I closed the door and silently walked to her bedroom. I could not hear anything, so I slowly peered inside. Sure enough! She was face down and ass high. What a sight she was.
"Close your eyes and do not open them until you are given permission!"
She jumped at the loudness of the quiet room. I went into the kitchen and lit a couple of candles that I had brought so they would have time to melt. I wet back into the bedroom and opened the blinds and the big glass sliding door. I stood behind her and enjoyed the view of her upturned ass. I could see her pussy lips pushing out all wet and glistening.
"Did you touch your pussy after I instructed you to do nothing else?"
"No."
I could tell she was scared as hell, but she was so horny.
"What about in the car?"
"No."
"You did not use the bathroom, or drink anything?"
"No."
"So, nothing but your thoughts and wet pussy have been between your legs all day?
"Yes."
I leaned over and put my nose right up to her pussy. I took a big, loud, deep breath, and smelled her excitement. "Umm. Now that is what fresh pussy smells like!" I made it sound as nasty and rude as I could.
I still had not touched her so I stuck my tongue out and quickly licked from her pussy up to her ass and said "Now that is what a good pussy tastes like!" She shivered when I did this and moaned loudly.
"What did you ask me today on your recording?"
"Umm, I don't. to."
"You asked to be treated like a slut."
I waited. "Well?"
"Please treat me like a slut, Sir. Use me over and over. Anything you want I will do. Whatever I can."
"Shut up Slut! If you want to talk, I can leave, otherwise, keep your mouth shut unless I ask you a specific question. Understand?"
"Y Yes, Master."
I could tell she was unsure, just feel the tension in the air. Loudly, so she could hear, I slowly removed my belt, shoes, and clothes. I let her wait for each piece. I stood on her bed behind her, pointing my dick right at her pussy. I just leaned forward and sunk it in to the hilt. It was tight and slick and there was no resistance.
"OOHHHH GOD. OhhHHhhhh. Auug."
I left my dick pushed all the way in and rose up and down moving inside her pussy. I pulled it all the way out, slowly, relishing the squeezing muscles. It felt so great. I slammed it back in and pulled it out slow, dripping. I stood and moved to sit in front of her head and lifted her face up by the hair. She started to say something and I shoved it in her mouth.
"Suck your cunt juice off my cock, slut."
She struggled and finally got into a good up and down motion. I leaned up and grabbed her nipples, which were swollen and hard. I pulled roughly on them and she moaned my dick. The harder I twisted and pulled, the more she groaned. I pushed her mouth off me and rolled off the bed. I paused to look and watched her squirm and fidget.
"Get up. Get up and come stand over here."
She got up, unsure of herself while blindfolded.
"Walk over to the balcony, come here. Sit in this chair."
"People will see!" she squeaked.
SMACK I slapped her ass hard. "I said no words unless spoken to. Did you not understand that?"
"Yes, sorry Master, never again."
"Come here and SIT!"
She walked to the rail, and found the chair and sat in it. I had it facing the outside and no one could actually see, unless they were just standing there watching, which was ok too, I guess.
"Spread your legs! Raise your arms, clasp your hands behind your neck.
Good, good girl. I like a slut who follows orders."
I ran my hands over her legs and chest, stopping to play with each of her tits. Lifting and holding each. Sucking on each nipple. Biting them and making her squirm. "Just gotta get these little guys nice and hard."
"Now. DO NOT move. Do not flinch, and since your neighbors are able to watch, I would not cum too loudly, unless you want them to hear enough to come and see what is going on."
I roughly slid two fingers up her pussy and jerked them around until she was nice and hot. I flicked her nipples with my fingertips until she almost cried out. I grabbed her elbows and told her to keep them up.
"Point that chest out like a proud slut. Aren't you proud of these tits? Proud of this big, wet cunt?"
"WELL!"
"Yes, yes I am proud."
"Of what?"
"Of... proud of my tits and cunt." She said with despair in her voice.
I stopped touching her and let her sit while I got a drink. I grabbed the candles when I returned and held them over her chest. I let one drop hit her and she flinched. Drop two hit the top of her tit and she finally felt the heat.
"Ooaauughhhhh... that's hot. aauuuu."
I ignored her and kept up a steady drop of wax. I blew on them when it was too big, and soon she was moaning and pushing her chest out. I got her right to the edge and then started dripping down her thighs.
"Quiet now, remember the neighbors, UNLESS... you want them to hear."
"No, no, god, ohhh, can I talk. please"
"Yes, what do you want slut?"
"Oh god, what is this. What are you doing. It burns but feels so good. It is hard to hold my arms up."
"Well, DO IT! Keep them up. I am dripping hot wax on your chest and legs. (She moaned) I have several candles to go so let everyone know how much you like it." I chuckled.
I took her by the back of the neck and told her to drop her arms to the chair arms. "Don't move them, grab on." I took the second candle and dripped much more wax onto her areola and nipples. She almost screamed until I moved to the other nipple and she gritted her teeth and held it in. I got both nipples completely covered with wax and put the last few drops right above her clit.
"Look, look how wet you are, just dripping out of your cunt. What a slut you were all along. Here. Do not wipe this off. I want you to smell how much your nasty cunt likes this!"
I wiped my fingers through her pussy and rubbed it on her mouth and under her nose. I jiggled her tits and slapped her pussy a few times and just sat and watched her for about five minutes. She was not sure If I was standing there or not.
I leaned down and startled her as I spoke directly into her ear.
"Open your eyes and watch your pussy. Do not look anywhere else."
I took a red magic marker from my bag and wrote "SLUT" across the top of her pussy. She had a tear in her eye as I leaned over and kissed her roughly.
"You wanted nasty, well you certainly look nasty. Your face is all red and flush, your pussy is dripping onto the floor, your tits are covered in wax. Do you want more my little sex slave?"
"oh my, my. oh, yes... please. more, please anything. I really want to cum, please fuck me until I cum. please... more."
She was just babbling so I started to pick the wax off her chest. I would take
a small piece and pull it off in strips, slowly. She moaned and squirmed and
gasp when the cold air hit her bare nipple. It was the most fun to remove,
being one big blob of wax. I just lifted it up, higher and higher, until her nipple pulled out of it. It must have been painful, but she shuddered and I watched her pussy contracting like there was something in it. I reached down and slide my middle finger inside as far as it would go.
"Ooouch" she said. My bladder is full, that hurts."
"OK then, lets relieve ourselves."
I stood next to her and started to piss on her. She gasp and tried to get up when she realized what was happening.
"SIT the FUCK DOWN!"
She slumped into the chair and I continued to pee. "Any slut worth her weight love piss. Loves to drink it, smell it. Nasty, wet fun." She obviously did not have the same opinion, but it was fun treating her this way!
"Now it is your turn. You have full bladder, I would suggest not holding it too much longer. You seemed to like peeing on the floor from our last time together, and you do not have much of a choice anyway. Now, start pissing or I will lock the door and leave you out here on the balcony."
I sat down and just watched. She did not like this, but I could se her trying to relax, or strain, or something. Suddenly, a few drops then a flood. She had been holding it all afternoon and it flowed for several minutes. It ran down the concrete and watered the plants down below. When she was finished, I did not dry her, left her wet with my piss all over her, and had her get back on the bed with her ass in the air.
"Since you have not opened your eyes, and have been a good girl, I won't punish you for getting out of the chair. I have something else in mind instead."
I opened my bag and put on some latex surgical gloves. I opened a bottle of sex lube oil and poured it down her ass cheeks. I spread it around with my hands and then slid a finger in her hole. She yelped and moaned and tried to pull away. I said "Stop, stay still and relax." I let her relax and then started sliding my finger in and out of her ass. Stretching it out, using two fingers and then three. I had to rub her clit to get three fingers in her ass, but after a few minutes, they were sliding in nice and easy.
Eisley
- 07.05.2022
- 5
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