Anna's Playtime free porn video

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The following story is a work of fiction. It contains sexual themes and descriptions. It includes Transgender themes and depictions of Bondage, Domination and Submission. It is meant purely for entertainment and no endorsement or condemnation of the subjects is implied or intended. IF YOU ARE BOTHERED, REPULSED OR OTHERWISE OFFENDED BY THIS SUBJECT MATTER DO NOT READ THIS STORY. Anna's Playtime A short story By Bootlover I stood there, cuffed to the ceiling, naked, my body completely hairless and my cock standing out so hard it hurt. Meanwhile this absolute vision of blonde hair, smooth skin and black leather was so near to me and yet so unattainable. I think that one touch of her, any part of her, directly on my cock would had sent gallons (yeah, I said gallons and I meant gallons) of cum erupting from me. But, it was not meant to be. Anna walked slowly back and forth in front of me, not pacing, not really strutting but moving fluidly like a lioness moves. Muscles rippling, smooth skin showing the flex and relaxation of her thighs, her arms, her shoulders. And that big black dildo ominously protruding from her crotch, swaying and bobbing with each step. Even the way her corset seemed to ride from side to side on her rolling hips with each stride was arousing, animalistic and dangerous. And the sound, those spike boot heels clicking loudly on the concrete floor with each step. The click - click - click was almost mesmerizing. If I had lusted after her back in the office I was now truly enraptured with her. I had not noticed before, but as she walked Anna was spinning her crop around the index finger of her right hand by the loop attached to the handle. I noticed it as she stopped her walking right in front of me and turned to face me. Lie a propeller it was spinning around and around, making a faint wooove, wooove, wooove sound as it cut through the air. Without thinking I took visual inventory of this statuesque woman in front of me. Her six foot frame perched upon the 5" heels made her so tall, easily taller than me. The power in her body was evident at every point - thighs, backside, and arms but while she was clearly muscular, she was not "ripped". The flow of her body from the power of her thighs through her hips to her small, but not skinny, waist up to her large, luscious boobs was just fabulous. Topped by her beautiful face that had more of a model's glamour look than the fresh faced "girl next door", Anna was a truly amazing example of the female of the species. As my ocular inventory reached her face it was clear that she was intently watching me. "Have you had a good look, Lassie?" she asked. Her voice was quiet, controlled and dangerous. Clearly she was not thrilled to be appraised like some piece of art, or worse, some side of beef. I did not answer, I just averted my eyes from her stare by looking at her gleaming black boots. Unfortunately for me, my leather and my boot fetishes were fed by the sight of her right foot extended, heel on the floor and toe raised in the air as her leg jutted out to the side. Her left foot, toe flat on the floor, point right at me. Thoughts of how good those boots would feel, wrapped around me, under my tongue or over my shoulders filled my head and, if possible, increased the ache in my cock. Without ever stopping the twirling crop her left hand darted out and the gloved palm smacked the head of my cock. I was so stunned at the speed and accuracy of her action that I did not feel any pain for some time. Then the head of my prick began to feel warm and then almost hot. "The only hard cock I like around me is this one" Anna sneered as she caressed and stroked that false dick between her thighs. The sight of the supple leather glove fondling that dildo made me even more aroused and my cock never came close to losing it's tumescence. I could only imagine those long, leather encased fingers playing along my shaft and swollen knob. I saw her move this time, but not soon enough that I had time to react. The spinning crop moved forward and on one revolution, as it moved from the 6 o'clock position to 2 o'clock, caught my cock in the soft flesh beneath the head, where my circumcised flesh was pulled back from the rim. This hurt. I yelped in pain and my cock shriveled quite quickly. My enticer now seemed pleased with the reaction and pain she observed in me. Her sneer became more of a smile and I was growing more concerned that what I had hoped might be a rambunctious sexual escapade, had expected might be an interesting exploration of BDSM might now turn into a painful session of indulging Anna's whims. I was in no position to fight it, captive as I was and hanging (from both my wrists and my groin) in front of her. "I can see that a revelation has occurred to you, it's written all over your face." She laughed. "I do so enjoy that moment when one of my pets suddenly realizes that this isn't about him or her, this is about me." "Stand straight" she commanded, "eyes looking forward at that wall." Her heels began to click as she began to walk again. Only this time she wasn't walking back and forth, she began to circle around me. Doing as I was told, looking straight ahead, allowed Anna to disappear from my peripheral view as she moved behind me, and then, in a moment, or more appropriately, three heel clicks, she reappeared on my other side. The crop began to whir again as she twirled and walked and clicked. I tried so hard but my cock had a mind of it's own and began to swell again. Just the sound of those clicking heels made my mind go wild. As she walked in front of me Anna trailed her fingers across my chest, lightly teasing my nipples as they ghosted by. My nipples jumped to attention and my cock grew to full size as she passed behind me. With no warning the flat, leather tip of the crop smacked my right butt cheek sharply and then, a second later my left cheek was stung. I imagined her right hand swinging the crop in a descending blow to my ass and then hitting the left side in a backhand motion, no effort wasted. Despite the extraordinary image in my mind of this blonde in black leather wielding her weapon the pain was more than my cock could stand and it deflated rapidly. "OOOhhh, big strong man can't take two little hits from a weak little girl" she teased, the sarcasm dripping from her mouth. Anna was anything but a weak little girl, and even though I had not seen her hit me I knew the blows I had received were far from full strength. While passing in front of me again Anna stopped, turned away from me and bent at the waist, reaching to the floor and then smoothing the leather of her boots around her ankles. I had the view of a perfect ass, two firm, full, globes separated by the leather strap of the dildo harness and two swelling hips. I could not help myself. In spite of the lingering sting in my cheeks, Mr. one eyed, purple helmet was growing again. Anna straightened and the heel clicks began again. Her hand moved to my chest. The leather felt wonderful against my newly smoothed skin and she gently caressed me but didn't touch my nipples, making them ache for her. Then, in an instant she held my left nipple between her finger and thumb, pinched tightly and then slowly pulled it away from my body, twisting it as she did so. I felt as if she were ripping the nubbin from my body. I said nothing but the burning and pain grew in intensity. "Does it hurt Lassie?" she cooed. "Yes Anna" I croaked. "Let me try and take your mind off this nipple" she said and with that the crop struck my thigh. I knew this would raise a welt it hurt so much. And then my nipple was loosed from her grip. Again the metronomic click, click, click of her heels began as she circled me again. My nipple was on fire, my thigh hurt and my ass still smarted. Without warning another blow from the crop landed on my other thigh. I could only assume that my other nipple was due for assault very soon. But instead she walked away from me. As sad as I was to see her spectacular form glide away from me I welcomed the respite. Anna went to her closet and then quickly returned, in her hand she held an alligator clip. As I suspected my other nipple was in for it's share of attention. But I was wrong! Moving swiftly Anna attached the clip to my already tortured left nipple. The teeth bit into my raw and blood engorged nipple and made me cry out. "Poor baby" she soothed. And then I felt exquisite pleasure. Her glorious gloved hand was cradling and fondling my balls. It felt so good I forgot all the pain. Just as my member was beginning to respond to Anna's gentle manipulations she quickly closed her fist around my two balls and squeezed. She hissed in my ear "I've never actually squeezed so hard that I popped one or two of these. I wonder if I could?" I was dancing on my toes from the pain. Then they were free and the sensation was at once one of overwhelming relief combined with a nausea that I only experienced with the worst of hangovers. Again the clicking of her heels. Now she did not speak, only walked and lit into my ass with her crop whenever she wanted. There was no rhythm to the blows and I almost did not realize that she had stopped, both hitting me and walking. "Would you like some water?" I heard through the haze. I barely gasped a yes and weakly nodded my head. Her heels moved away and then back to me. I felt the cold water in a cup brought to my lips. As I began to sip I felt the warm leather covering her projecting breasts massaging my shoulder, arm and side. She felt warm, the smell of the leather was intoxicating and she began to tease my free nipple. With all of these sensations, and concentrating on drinking the water it was a moment before I felt one more thing. That dildo was prodding my groin! Whatever reverie I was about to enter was shattered by the reality of where I was and who I was with. As if reading my thoughts Anna's teasing of my nipple turned serious and she began the same pinching, twisting and tearing that had nearly ruined my left nipple for life. I was totally messed up by this woman. On the one hand her looks, the feel of her tits, the smell of her leather and the kind way she was offering me the water made me long for her. On the other hand the pain she inflicted and was inflicting, the ominous rubbing of her "cock" across my thigh and into my groin and the power and attitude she possessed made me fear her. "Well, I think we've had enough fun for one night, eh Lassie?" she said letting my nipple snap back into it's proper place and form. Never had any words sounded so good. "Why don't we get you dressed?" She unclipped my cuffs and let my arms fall to my side. "Over to the closet with you and get back into your pretty things." Even putting on the women's clothes would be a welcome relief from what I had just been through. "Stop" she barked. I froze. Now what am I in for? "I almost forgot" she said, walking toward me. Amazingly the sound of those heels still thrilled me. "This" she said as she released the clamp from my nipple. The pain was close to the worst of the night as the blood rushed back into my tortured flesh point. "Now into your things Lassie." I half walked, half stumbled over to the closet and began to pull the items off the shelf. Reaching first for the corset I heard Anna say "You won't need that tonight Lassie". I turned and looked at her, one leg across the other at the ankle as she leaned against the door frame, arms folded across that big chest.

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Outdoor playtime

True story.We were out on a date in Columbus Ohio, had a few drinks and dinner, I was thinking about fucking Lee all night long, I must have slid my hand up her dress at dinner at least 10 times. It was warm and clear that night (unusual for Columbus) so I suggested we drive over to a local park/lake for a walk over the dam and she agreed. We were both feeling good, the wine and drinks were having the desired affect on her libido . . . we were both feeling very horny. It was really very dark...

2 years ago
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Hotel Playtime

Got a call last night from Jim who wanted a cocksucking and a taste of my pussy that I could not resist.He was rather nice looking and clean cut. A 38 y/o white guy with a 7 1/2" rather fat cut cock. He got us a room at the Hilton and I was excited by this. He was serious I thought, rather than the usual Motel 8 type. I always pay half and that was okay. It was nice of him. Wore a new short black dress, slutty lingerie and strutted a little for him. Then I slowly licked and nursed on his cock...

3 years ago
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Bringing a new girl for playtime

Carrie, Huda & Carlin Masturbation, Voyeurism, Bondage, The last session with Carrie ended with her sleeping for twelve hours without covers, we would check on her and she was dreaming so deeply there would be quivers and jerks. She finally got up and came for some food and sat in a daze while she chewed, we asked her if she had plans today and then she perked up remembering she was meeting someone in two hours. The wife helped her get ready and we drove her to her house to meet her...

1 year ago
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Naughty Playtime

I moved slowly around the room, lighting candles. There were twelve, placed all around the room. They were white and thick. Several of them were WoodWick candles and gave off a slight flickering sound, reminiscent of a crackling fire place. The lights were dim, and the shades drawn. Darkness had set several hours ago. I sat down on the leather couch to wait. I inhaled the aroma of the room. It smelled of sandalwood, vanilla, and leather.I could hear the sounds of my wife in the bedroom changing...

2 years ago
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Workers Playtime

Maybe sometimes life isn’t fair, and you can feel like you’re emptying a swimming pool with a spoon. However for every grey day there has to be a dazzling sunny one, this is a sunny day story.Sitting outside a pavement café one warm morning in July, just watching the world drift past me, sipping coffee and enjoying the leisurely pace of the day, nothing particularly on my mind, nothing pressing to attend to.“Hey Dan, how’s tricks?” a voice comes out of the blue and breaks my daze, it’s a face...

Straight Sex
2 years ago
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Andreas Playtime

When they left the party they couldn’t stop looking or thinking about each other and the excitement kept building in the two of them. They arrived at her building and Andrea invited John up for a drink. She gave him a brief tour of her place, and then offered him a glass of wine while they were in the kitchen.He kept looking at her lips wondering how soft they were, she could feel him looking at her lips and the excitement was building within her. He wrapped his arms around her waist and pulled...

Straight Sex
4 years ago
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Playtime

I want to snuggle with you and give you a backrub.Give me any shit and I will spank your ass...Oh, you want to play, huh? You will soon see how big my hands are... :)Now that your butt is stinging and red... if you want me to kiss where it hurts, you have to play with yourself first... lick your finger and gently rub yourself, giving me an erotic show! :)I sit back and watch- I lean back so you can see what effect you have on me..Soon your finger is glistening with your juice- you slowly stick...

1 year ago
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TWINNIES PLAYTIME

I came home and found my twin sister propped up on the couch reading a book. She didn’t even acknowledge my entrance into the living room; she was too engrossed in the book she was reading.I started to say hello when my eyes beheld a sight that gave me an instant hard-on. Her undies had ridden up into her pussy and provided a glorious sight for an eighteen-year-old boy— a camel toe! I just stood there gawking and feeling my hard-on throb. It was something that I had never seen before. But my...

3 years ago
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Playtime

Far into the heart of corporate gonglomorate Globotech, the CEO Mrs. Keegel sets foot in the office of two lead toy makers to talk about the direction of the next line of Heartland Playsystems products. During the meeting, one of the toy developers shows off his prototype for the Commando Elite, a boys' toy like no other. They move, talk, and above all, can learn with the help of the technology that Globotech gives its employees access to. He activates it during the meeting and Chip Hazard...

3 years ago
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To Love Honour And Fingers CrossedChapter 9 Private Playtime

Kenneth held Paula Chapman's hand as he looked around the room they were standing in. It was one of the exclusive private rooms of a club that Marc belonged to and was only available to full members who occupied a certain position on the business and social scale, which Marc did. To the left as they walked in was a table big enough to serve eight and the accompanying eight leather upholstered, high backed, chairs. At the back left was a regulation sized double bed while on the other side...

3 years ago
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Adriannas gift

Her long, blonde tousled locks tumble further down body as she sips another mouthful of the chilled Bailey’s Irish Cream. The ice cubes clink against the side of the glass as the velvety liquid begins trickling down her throat. Her white mini-dress clings flawlessly to her slender frame, and stops just below her petite buttocks. The matching white, spiked, platform shoes draw attention to her smooth, bare legs and her elegant clutch bag completes the stunning look. Adrianna is picture perfect....

3 years ago
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Subriannas first dungeon experience

She parked in the parking lot across the street like Master had told her to. She watched a couple get out of a car next to her pull two bags out of their car and walk to the dungeon. She felt her nervousness settle in as she checked her face in the mirror and saw heavily lined eyes, mascara, and retro red lipstick on her lips. Master had wanted her to look slutty tonight. Her instructions were simple, wear something sexy with no bra or panties under, red lips, slutty eyes, stripper shoes. She...

3 years ago
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Johannas Abenteuer

Johanna ist gerade einmal 18 Jahre alt. Jungfrau (bis jetzt). 1,72m groß. Blond blauäugig, hat große Brüste, und einen geilen, knackigen Po. Curvy, nicht dick. Die Haare sind schulterlang.

BDSM
2 years ago
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leannas week of fun

Leanna had decided to go visit her best friend in Boston for a weeks vacation. She sat at her computer looking at flights and her schedule as she was a big time writer and had hit a wall in what to write. So she gave her bestie a call and said she need to get away from Georgia for a few days and asked if she could stay with her and her roomie for a week. Her bestie, Rosa said yes both her and Chris would love to have her stay. they decided the best time to visit was at the start of July when...

1 year ago
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Nannas Texas cowboy pizza boy

Note : This story is completely fictional!Terry Priest was divorced. His wife caught him banging his 18 year old cute" gushed Nanna."He thinks he is in love with me" said Doreen."He's in love with your pussy" teased Nanna."Boys are like that" laughed Doreen."Where is you mom?" ask Nanna."Out getting laid somewhere" said the girl."Does she know you fuck boys?" ask Nanna."She encourages it, she got me birth control pills" bragged the girl.Doreen went to the answering machine and pushed a button....

Incest
2 years ago
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Anna My Patient My Lover

Anna -  My Patient and My Love - UpdatedA Completed and Restructured Submissive Love Storyby Lewis Chappelle(Author’s Note: This story was originally written in seven chapters. Due to confusion in the publishing process, I have decided to reorganize the story as one continuous work.)She signed the new patient information form stating her name was Anna Bree; her health insurance card indicated the same. She said her reason for seeing my assistance was that, ?She wasn’t sleeping at night, she...

3 years ago
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Anna Comes to visit the Cousins

As she sat exposed and aroused in her bed, she wondered who could have been doing this to her. Each night she'd tried to stay awake, but simply could not resist sleeping, she was kicking herself for not waking up during the experience as well! She fantasized about Tony's thick neck and shoulders, about Andrew's bodybuilder physique, or maybe Michael's lanky runner's body - maybe his height gave his cock the reach to make the back of her throat as sore as it was, maybe it was Lewis,...

1 year ago
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Anna

Anna looked again at her reflection in the mirror. Nature had been good to her. she stood five eight, with long blonde hair that flashed a ginger shade in some sunlight. Herm waist was a trim 26 inches, with hips that gently swelled to measure 34 inches. But it was higher up that nature had been really good to her. her breasts, the dark hard nipples topping her 38 D breasts. Lowering her gaze she smiled at her shaven crotch. Her parents had never noticed she shaved, but, they never saw her...

2 years ago
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Anna Saves the Compant Ch2

When Anna opened the door to leave the bathroom, she noticed Mr Davies had left. In a slight panic she looked around the room and found he had left her a note.Dear AnnaI know tonight seemed cruel of me but I couldn't resist. You are the most beautiful woman I have ever laid eyes on. I just simply couldn't turn down the offer once I had seen you. I have signed the contract and will keep to our agreement.Yours sincerely Alan Davies."Turn down the offer?" she said out loud to herself.Anna sat...

1 year ago
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Anna and my Swiss holiday experience

Anna and I have been best friends since university and like all best friends we have had our ups and downs mainly fuelled by far too much drink, my insecurities over Anna's stunning looks and her ability to attract far more attention from guys than I ever could, but despite this we have remained truly loyal to each other and as my best friend I really value that in our friendship. Anna and I are very similar looking and we are a simular size as well, (which has always been fab for swapping...

1 year ago
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Annas Neighborly Pool Seduction

I was staring at her now, watching as she peeled down her shorts, slowly exposing her gorgeous ass. Her naughty bits were concealed by a conservative bikini. Her shirt was already in the pile of clothes at her side, and her big tits were being held snugly by her elastic top. I was lounging at her side in my patio chair, sipping on a margarita by our pool.My wife, Anna, is a beautiful specimen of a woman. She has dark flowing hair, grayish-green eyes, and a soft feminine face. Her body is curvy,...

1 year ago
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Anna Saves the Company Ch1

Anna thought she had the perfect life, at 27 years of age she was young, beautiful and intelligent. Married to her husband of 2 yrs, they both had good jobs and made each other very happy. They weren't rich by any means but they both had good salaries and were particularly careful with their money. This however was about to be put in jeopardy, as the world braced itself for a recession. Anna was one of six office staff working for a small clothing firm. The company had taken off extremely fast...

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