The Reluctant Anal First-timer free porn video

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He had never forgotten her, but how could a man forget his best sex experience? He knew he was a dirty old man, and she was a horny young woman, but it all seemed so good to remember. He had enticed her to the hot tub room and gotten most everything he had desired without pushing her beyond her limits, but he wanted more. He always seemed to want more. He closed his eyes and remembered the experience… with a new ending.

After a long drive, he checked into the motel and hoped he wouldn’t be stood up. Is the manager wondering what he has in his toy bag? Will they see the young hottie come in and knock on his door? He tried to be as calm as possible and acted like nothing was unusual.

Finally, all of the bags were in the room, and he prepared the toys to be within easy reach. He was always in the mood for some bondage, and he made sure the straps were all untangled and latched to the bed corners. This wasn’t non-consensual, she wanted it…thankfully, but the thought of restricting her and keeping her in place and in position turned him on.

~~~

The toys are ready, he is ready, and then the worst part of the experience… the wait. Will she back out? Will she be late? He paces, and re-checks his toys. It’s all ready, he’s ready, he paces some more until…the knock-knock-knock. A quick peek through the peephole and its showtime.

“Hello,” he says it as if he’s calm, and he sees the nervous look on her face. He’s in charge now, and he likes it. Once inside the door, she hesitates and glances at him again as if to say “How do you want me?” or “What do you want me to do?” This all takes a fraction of a second, but he memorizes it all with his video-camera-like mind.

“Put your bag down and assume your position.” She acts like she’s not sure what position she is supposed to assume, so he continues to instruct her. “Step over here… turn around… hands behind your head… look up… mouth open… spread your legs.”

Standing behind her, he paws her like a teenager that is feeling tits for the first time. He steps close and smells her hair before pulling it into a ponytail, exposing her neck. He ruffles her top up her belly and back before tucking it into her bra exposing her bare skin.

This leaves the belt line of her yoga pants easily accessible, and he runs his fingers between her skin and the material and begins easing the pants down. He peels the material down to her knees, bringing her panties down with the pants and reaches between her legs from behind to cup and finger her slit. She’s wet, like always. It’s going to be a good day.

Her pants are still bundled around her knees, so he pushes them to her ankles before sitting back to admire the view. There’s something about an adult woman standing bottomless with pants around their ankles that he finds enticing. He likes the way she stands there…waiting. He likes the way her butt looks, and he paws at her round butt cheeks before saying, “Bend over.”

He had already positioned her in front of the bed stool, and she rests her forehead on her hands. He’s still pawing her flesh and opening her up a little to see between the cheeks. Her pussy peeks at him from the bottom curve of her ass. A sudden smack gets her attention, followed by two more on the same spot. He rubs her skin and watches it turn pink where he smacked her.

“Are you my bad girl?”

“Yes, sir.” She says it like she means it.

She says it like she’s really a bad girl and she knows she deserves it. Three smacks land on the opposite cheek, and he returns to rubbing the glowing bottom. He wants to dive in and enjoy her right now, but he’s waiting, savoring the moment, making her wonder what’s next.

Although he does have a thing for long-term spanking scenes, he doesn’t want to hurt her. He just wants to keep her wondering, to keep her guessing. A few swats will get the blood flowing to all the pink parts between her legs. He massages her legs and admires the smoothness. A woman’s legs can be so erotic, freshly shaved and with lotion applied, they are soft and smooth with a hint of a scent that reminds him of sex.

“Reach back and spread yourself for me.”

A “yes sir” is not necessary, she just does it, and she holds herself open for him to see everything, everything a man wants to see and a woman keeps hidden. This is a ritual position that he just can’t get enough of. He sits back and makes her stay that way. What better way to show her who is in charge? Her head begins to tire on the stool, and she wishes she could put an end to the embarrassing position, but he makes her wait. He even slides in closer to her to get a better look, before gently touching the precious sex holes. Both of them are going to get a workout today.

He tickles her clit a little and rubs between her lips searching for fluid. His wet finger polishes her button and she almost forgets about her aching neck, still supporting her body on the stool. His finger finds the opening, and he buries it all of the way to the knuckle before wiggling it and inspecting her pussy. A little searching uncovers her G-spot and the pressure makes her quiver as he uses his thumb now on her clit. But it ends as soon as it starts, and he makes her stand up to give her neck a break.

“Take everything off.”

She strips the clothes off and returns to her first position, standing with hands behind her head. He’s still behind her, and he cups her breasts and rolls her nipples a little too roughly. He pinches and rolls the nubs until she makes a little squeal and flinches her arms. He pulls her arms back even further than they were before and resumes the nipple abuse.

“These will get much more than that today.”

She doesn’t know what he means, but it makes her worry a little and keeps her heart beating fast. He likes messing with her mind. He likes to keep her guessing. The breast and nipple abuse continue as he manhandles the soft orbs with squeezes and pinches.

“Spread your legs wide and bend over again… just like before… only spread yourself wide and don’t move.”

She assumes the position and he gathers a toy for her. The enema tube and his favorite lube. He loads the tube with water and begins to lube her butt hole quite well. His finger can’t help but penetrate and prepare her for things to come. He continues to lube and finger her tight brown hole until he slips the tube inside of her and begins to empty the water into her ass.

It feels strange and she whimpers a little. He intentionally drains it slowly into her. He wants to increase the embarrassment of being bent over, holding her ass cheeks open, slowly getting filled with water as if he’s a doctor or a nurse. When the water is gone, he slides the tube out and says, “Hold that and don’t move.”

She’s concerned now about this predicament, but she obeys, and when she really gets concerned about the pressure, he says “Go empty that out and come back for another.”

Another?… she thinks this to herself, but just says, “Yes sir.”

She runs off to the bathroom with a slight giggle and a glance at him. She sits and tries not to make much noise as she releases the water. She can hear the bath water running, and when she returns, she sees he indeed does have another full enema tube waiting for her. He’s playing with the bubbles building in the tub, and she returns to the stool, bending over into the full-spread position.

He smiles when she can’t see him, and applies a large blob of lube to her hole. Never missing a chance to insert a finger, he works her asshole over with more lube and two fingers this time. Another precious whimper escapes her mouth and he eases up on her a little before draining the second enema inside of her. “Go empty that out and get back in here.”

“Yes, sir.” She does as she is instructed. She sits on the toilet and releases the water again, hoping that the cleansing is over.

She returns to the tub to find him already inside the tub soaking. “Get in,” he says to her, and she eases a leg over the side of the tub. “Not like that… reverse… with your ass to me.” He watches her ease herself into the steaming tub of bubbles, ass first. She is on all fours and he plays with her from behind. He soaks her back and legs, and ass of course. He massages her with the soapy bubbles and she rises up on her knees while he soaps her belly and breasts.

The slippery flesh excites them both, until he gently pushes her back to all fours. She’s slippery all over, but he uses more lube on her rear hole and works his fingers deep inside of her. One, two, then three fingers going inside and opening her sphincter. The warm water and the enemas have her relaxed and ready, but he continues to play with her over and over.

“Tonight’s the night,” He says.

She’s not sure exactly what he means, but she assumes… anal. Yes, the anal that she denied him on each previous visit. She tightens at the thought, and his fingers push back on her ass muscle.

“You need to relax,” He says as he continues to play with her.

She tries to relax and mentally prepare herself. Yes, she said she wanted it, but each time, she denied him the pleasure. As soon as she said, “stop,” he did, but she just wasn’t sure… even now.

“Let’s get dried off,” He says to her as she looks back a little concerned. He just nods his head like… yes… it’s time. She gets out of the tub and begins to dry herself. Then he gets out and she dries him without him asking. After a while, he realizes she stalling for time.

“Get on the bed, at the foot, on all fours.”

She moves into position, and he begins to buckle her in. The ankle straps are locked and she’s spread wide. He pulls her hands between her legs and fastens her wrists into the straps, jerking them toward the end of the bed, he locks her down and says, “Slide up… pull your legs up… farther... farther… good.”

Her legs are wide and pulled toward the head of the bed, her hands are locked between her legs and pulled tight, forcing her head down on the mattress, and she’s trying to look back at him… questioning her decision to submit. He fetches one more toy and returns to the bed to say, “Once this goes on, there’s no turning back… are you ready?”

A feeble, “yes,” escapes her lips before she has time to think, and the gag goes on. The same gag that he used the first time they met. The full-face strap gag with no escape. OMG… it’s in my mouth now… and there is no safe word… there is no stopping this…and I’ve never been able to handle it with him before.”  

She felt like she was on a roller coaster. The moment it leaves the station, you want to stop, you want to return, but there’s no stopping it now. It’s going to happen. She feels the straps tighten and she makes a few noises just to test the gag, but it only turns him on more. The gag is tight now, and she tries to turn her head left and right, but she can’t find a comfortable place. He’s touching her gently, patting her ass, the ass that he now owns. He begins to mess with her mind.

“Oh, my… what have you done?”

“There’s no turning back now.”

She whimpers a little. He’s scaring her. Her heart is beating faster and faster. He just continues to prolong the moment, pawing her and stroking her. He keeps saying things that make her want to be released, but he just continues to play with her thoughts. As if her legs weren’t wide enough, he pulls her knees wider and straps them open. She’s completely open now, ready for anal… or at least in position for anal. Mentally, she’s not sure. Why did she say yes? How did all of this happen? She feels the lube going on again. She’s already felt it many times today, but it’s all different now. She tightens.

“Yes… that’s it… tighten up for me.”

He plays with her hole over and over and gets into position behind her. He’s not stretching her this time, and she feels the need to tighten. She’s not ready. After all of this foreplay and cleansing, she’s still not ready… mentally. OMG… he wants me tight… he intentionally trapped me into this with a gag and no escape, because he wants me tight for him!”

“No more teasing and saying no…” She wanted anal, but she was always too afraid to allow it. She said she needed to be tied down to get past the fear. She knew that once the gag was in, she was committed.

He begins to probe and push on her hole. She tries to resist, then tries to relax, but he still doesn’t penetrate her. The lube helps his cock slip in a little and then he pulls back, only to push deeper. She tightens and relaxes and tightens again, until she has a moment’s relaxation, he pushes, but this time he continues in...all the way. A groan and a muffled cry fill the room, and this is where she would normally say…”STOP!” But there’s no stopping, and he’s pulling back just for his own pleasure now, stroking and pumping her asshole while she continues to tighten and try to relax and fight through it.

He leans into her and plunges deep, all the way… opening her and burying himself into her. They are connected, and she’s battling the pain and the thoughts of relaxing with the involuntary tightening. Moans and whimpers are filling the room, he spreads her wide and plunges in and out. It’s all about him now, the orgasm building. The whimpers and moans only help to turn him on before he climaxes and blows a huge load. Deep inside, the jerking pumps squirt deep inside of her freshly rinsed colon, which she continues to squeeze and push open for him.

She’s milking him involuntarily now, and he remains inside of her, not wanting the moment to end. Until he eases out and rolls onto the bed beside her. She’s breathing hard.

She wanted it, but the only way to get past the fear was for him to strap her down. She had agreed to a night of rough sex, and it was all she could take. She remains ass-high and strapped down until he gathers himself and releases her. He then rolls her over and gives her the best oral she ever had, and they fall asleep in each other’s arms.

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It’s time to go to the land of chocolate fountains and golden showers. That’s right. Scat, piss, shit, and every fluid in between. Ever fuck a chick in her ass and freak out when you see that little bit of shit on your dick? Then I’m sorry to say that scat isn’t for you buddy. Were you the only one of your friends that saw two girls one cup and didn’t get grossed out? If so, it’s time to celebrate it! Don’t get pissed off, get pissed on! Scat porn has the craziest, kinkiest chicks and dudes...

Scat Porn Sites
1 year ago
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Motherless Fappening

I’m not saying anything controversial when I say men love seeing women naked. It’s a fact of life as fundamental as gravity. It’s a force of nature that cannot be stopped by beast, man, or God. It’s an eternal truth and a divine mandate. As sure as the sun will rise, men will attempt to view as many women naked as they possibly can. Any man not doing so is either a sad or a gay one.This means that any woman a man sees regularly is mentally stripped down during every interaction. If any women...

The Fappening
3 years ago
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First Anal With My Irish Exchange Student

I woke up as usual on a Saturday morning and expected to see my boring 45 year old wife lying next to me. Instead, I looked over and realized how lucky I was. I glanced over and there was my beautiful naked Irish exchange student twenty year old Kathleen next to me with her long red hair covering the pillow and gently brushing up against her bare breasts. Then it all came back to me. Last night I was lying flat on my bed, Kathleen straddled me as she furiously rode my cock. Out of the morning...

2 years ago
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A WellLived Life Book 9 AnalaChapter 46 Summer of 84 Part I

July, 1984, Stockholm, Sweden Sitting at the gate at Arlanda airport, I thought back over the final six days of my trip to Sweden. They had been filled with sightseeing, talking, and dinners, both in the apartment and out, with Karin’s parents. And of course, making love. I did, finally, on the last evening, take a trip, alone, to see Birgit. I put flowers on her grave and knelt there, imploring her for answers to the difficult questions that were swirling around my head. She, like the...

3 years ago
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Sexual Encounters of a Young man 21 First Anal with Rukhsana

Maanvi and Rupali started to give him food every alternate month as he got stomach upset due to outside food for long and on one fine morning when she went there to give him morning Coffee on seeing his erect 9 Inch cock while he was asleep and she was lured into sucking it and then while bathing she fell in bathroom and Montu Kumar treated and helped her and then fucked her. They were facing problems to find a safe and secluded place for regular fucking afterwards so one day he fucked her...

3 years ago
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Absinthe Dreams

‘To me it’s not really a green. When I think green, I think of grass. That’s more like lemonade color.’ Erica’s nose was far too close to the glasses for my taste. Pouring the nearly clear absinthe over the rough-cut, cane-sugar cubes I favor, I tapped my spoon for a second to get her to back up. I wished I had my full setup here like I have at home, my Absinthe fountains water drippers are missed when I began to try and slowly pour water over the sugar cube. ‘Don’t you light it on fire?’ she...

3 years ago
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A WellLived Life Book 8 StephieChapter 60 Anala Part I

August, 1983, Chicago, Illinois Friday went by quickly at school, and we were starting to get into the routine again. I talked to Julia and Stephie at lunch about dinner that evening, and Julia said that she’d take care of it. I had all the ingredients and a recipe, so she was totally comfortable. I hadn’t quite figured out the logistics with cooking dinner for Anala, though I had put up a note saying I needed the ‘Indian’ room that evening. In the end, I figured that Anala and I could do a...

4 years ago
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Surprising FirstTimers

Friday night had arrived and as usual, I was at the sex club early to assume duties as a greeter for any first-time visitors. Quickly, I changed into black latex shorts and a pair of black boots ready for the night to begin. After setting up the equipment in the dungeon I returned to the bar waiting for the guests to arrive.Slowly the room began to fill with the usual mix of friendly faces. By now I was well known to the clientele and almost everyone greeted me with a hug, handshake or kiss. As...

BDSM
1 year ago
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Motherless Arab

Have you ever heard about a wonderful site called “Motherless”? I have a feeling that was a dumb question, of course, you fucking have. Well, I am here to talk about Motherless, but I shall also pay special attention to their Arab category. If you think Arabian sluts are hot, well you are in for a tasty treat, believe me.First, I should probably warn you that the name of this place comes from the fact that their content might be a bit too hardcore or questionable for some of you. Back in the...

Arab Porn Sites
1 year ago
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Motherless Facials

Fuck yeah, life’s a bitch! So here I am, awake at 3:45 AM, after dreaming I was fucking this freaking hot MILF neighbor with heavy boobs, a flat tummy, a nice bubble butt, and sexy long legs. It was all hot and steamy, up until when she was sucking me off and just as I was about to obliterate her cute face with hot cum canon, my dream cut right off and I woke up with a tent on my pajamas.That dream ain’t coming back, but damn it! I sure gotta cum, so I boot up my laptop and type “cum facial” in...

Facial Cumshot Porn Sites
4 years ago
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A WellLived Life Book 9 AnalaChapter 13 The Waiting is the Hardest Part

January-February, 1984, Chicago, Illinois I mailed the letter from the Lisle Post Office on Tuesday during my lunch break. I had no idea what Karin’s response would be, or how that would affect her visit. All I could do now was wait. I was also waiting for Friday, and dreading talking to Anala about the situation with Joyce. I was waiting, nervously, for my lunch date with Becky. And I was waiting for a call from Connie. All of those things weighed heavily on my mind at work and in class...

3 years ago
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My first anal orgasm

This is a story about how my body felt during the first time I had an anal orgasm. I had always wondered about the enjoyment of anal play. I also enjoyed my asshole being touched and licked, but when it came to the penetration part, the enjoyment was gone. I thought I was missing something. Anal penetration never ‘hurt’ but was somewhat uncomfortable. So because of that, anal was a special thing that was rarely done. The feeling of anal sex was neutral to me. It didn’t feel good, but it didn’t...

2 years ago
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Club Orb First Timers

This is my third transformation story but my first straight up transgender romp. I'm a fairly new author and I'm striving to improve. Hopefully the story will be enjoyable and thank you for reading. Club Orb: First Timers "C'mon! Please come to the club, I know it's not your thing but I swear you'll have a lot of fun. My personal guarantee -- we will both get laid." Danny attempted to bribe his extremely undersexed buddy Jack. "That's... not really something you can...

3 years ago
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My Suhagrat And First Anal Fuck

MY SUHAGRAAT AND FIRST ANAL FUCK Hello ISS readers, my name is Nisha Lapoor and I am from Punjab. My age is 25. I am a beautiful slim girl having very sexy features. I am post graduate and doing Govt service. My marriage took place recently on 2nd Nov 2009. I have read many stories of this web site but after my marriage when I got real sex experience then I came to know that many stories appeared on this site are work of fiction and not real as their writers claim. I am writing below the true...

2 years ago
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First Anal Together 25 years ago

At first she was shy and just lost her virginity in college. I was the older married man. She was dating her boyfriend who popped her cherry. I was "technically" separated and was about to go through my second divorce. She was the 24 year old - "girl next door". I knew I loved her from the first day we met. I never imagined that she would be interested in this 30 year old - two time loser. At first we dated casually and visited parks and museums. We went to dinner and a movie. Dirty Dancing....

3 years ago
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Thea

Und draußen schallte wieder Punkmusik aus dem Ghettoblaster – von der Eisenbahnunterführung bis zu seinem Haus! Punks und Skater hingen da ab. Das war diese Art von Jugendlichen, die ihren Eltern das Leben schwer macht , die von Arbeit nichts hielten, sich an keine Regeln hielten, ständig auf Party machten. Die soffen viel zu viel und kotzten dann in irgendeine Ecke. Denen bedeutete doch nichts und niemand etwas. Wahrscheinlich nahmen sie auch Drogen und trieben weiß-Gott-was mit...

BDSM
2 years ago
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My first anal

Preamble: This is the story of the first time I did anal. I wrote it on vacation at my parent's house, got a little carried away reliving the experience in my mind, and got very excited ... so sorry it is so long. I got so excited that I actually soaked through my panties my sweat pants. I have posted a pic of me after writing this story, wetness and all, and a pic of the guy from the story (well, at least his cock, which took alot to talk him into letting me take it). My First Anal:I was...

2 years ago
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Manali Ko Naye Dost Se Chudwaya 8211 Part I

Manali bohut cute ladki hai,sab uspe fida the.Wo bohut slim aur sexy bhi hai,par wo bohut conservative thi.usne mere sath bhi kabhi sex,yeha tak kiss bhi nahin kiya.Mai usse bohut pyar karta tha,mai bhi bohut conservative tha.mai kabhi usko kisi or ke sath sex karwane ki baat kabhi sapno mein bhi soch nehin sak ta tha.yeh tak usse sex karne ki khayal kabhi mere demag mein aaya nehin.Humare bech kabhi sex ko leke baat tak bhi nahin hoti thi.Par ekdin jab mai cricket practice se ghar wapas aa...

1 year ago
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Motherless Fetish

Motherless is the mother of all porn sites. Motherless has no conscience or moral guide. Motherless will show you the stuff that all other porn sites are afraid to put up. Motherless will do this for free. This is seriously one of the nastiest and raunchiest sites out there and Motherless/Fetish is perhaps one of the dirtiest places on the web that are well within reach. Sure you can scan the dark web and find something even more naughty or puzzlingly gross, but why do that when you’ve got...

Fetish Porn Sites
1 year ago
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A WellLived Life Book 9 AnalaChapter 32 A WellLived Life Part III

April, 1984, Chicago Illinois “Who goes first?” I asked. “I believe I should,” Anala said. “I have the more important issue, really.” “I agree. Becky is not as nearly important as Stephanie. Go ahead.” “I wondered, for several months, what you were hiding from me. I had all manner of speculation as to what it could be. A criminal past. Some terrible thing you might have done to a girl. Some other dark part of your past. Never would I have guessed it was a sexual relationship with your...

2 years ago
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A WellLived Life Book 9 AnalaChapter 53 Changing Dynamics Part III

August, 1984, Chicago, Illinois Anala had pushed me hard to decide what I wanted from Penny. The thing was, no matter what I wanted, the fact that she was only fifteen presented what appeared to be insurmountable problems. In theory she could marry at sixteen with parental permission, but how did a twenty-one year old man approach the parents of a fifteen-year old and ask to marry her without potentially disastrous results? And even if I overcame that problem, was Penny really in a position...

2 years ago
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Absinthe 2 The Absinthe of Malice

Absinthe 2: The Absinthe of Malice By Morpheus The flight from Seattle to Boston had been extremely long and uncomfortable, even with the two hour delay in Chicago where I got to stretch my legs and change flights. My book had given me something to do during the countless hours in the air, though admittedly, Collin had been my largest savior from boredom. The two of us had ended up talking for over half the flight, and by the time we finally landed, I was even starting to consider...

1 year ago
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My Anal Life

BeginningsI suppose I've always been a bit obsessive compulsive, even from an early age. From as far back as I remember when I developed an interest in something it consumed me. These interests included gymnastics, playing the piano, and various other activities. I would go through periods when I would spend hours each day practicing piano or gymnastics. I also had a very intense interest in my bum from a very early age. I always loved the shape of my ass and how it felt (gymnastics helped a...

1 year ago
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PornPics Anal

I know videos play a huge part in your fap sessions, but I have also been here long enough to know that sometimes you just want to chill and look at hot images. It could be the nostalgia of older days or something else altogether, but it doesn’t really matter. The thing is, you will need a good source of porn pictures sometimes.PornPics has been a reliable source of sexy porn images for years now, but their anal galleries are particularly delightful. In their anal section, you will find a wide...

Anal Porn Sites
4 years ago
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First anal fuck after Suhagrat

Hello ISS readers, this is Saroj Sharma again from Rajasthan. I got so many inspiring, good comments on my previous real story “My suhagrat”, that I am submitting this real story of my first Anal (Ass) Fucking. For new readers of ISS, who did not read my previous story I want to tell them that I am recently married Post Graduate girl of 25 doing Govt service. My height is 5ft 6inches and vital statistics as 36-26-36. I have sexy features and always wear sex provoking dresses in home. My husband...

2 years ago
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How I Found My Anal Whoreslut On XHAMSTER

This story is 100% true and happened Sunday night. As you read the story you will learn of SWW's (stands for her screen name) desire to fulfill her destiny by becoming a true anal whoreslut. You will read how I accepted the responsibility of being her master and to help her fulfill her destiny. We are one and the same in terms of our passion for all things anal. She wanted me to write this story and to announce to everyone her favorite part in our chat where I said: "Hey fellas, just so...

2 years ago
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Erica Ranch Wife pt 4 her first anal

Introduction: After some hesitation , Erica finally tries anal Erica was pretty adventurous during our playtime. She had made suggestions about anal sex and offered none of the upturned-nose type behavior some people have with it. She had taken a rather vigorous anal fingering and had no problem with analingus when I performed it on her. In fact, she had motioned my head towards her butt,when I ate her out on several occasions. She was concerned about cleanliness and seemed pretty aware of...

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