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A Sissy's Second Sexual Encounter With An Older Man.

anal stacielana69 2018-06-11

A sexy black, tall, skinny, naked daddy came from around the couch and sat next to me. It turned me on so I moaned very loud to let him know that I wanted more in my ass than just his finger.  I lubed up his cock and my ass and then climbed up onto him as he sat on the couch. Once he slammed his BBC in my little hole, I realized that I was officially a bottom slut and loved a mans cock in me. He pulled out for a second to lube up more but before he could slide back into my ass, I told him I was done and needed to leave.

Sissy in the Woods

anal emmadeevine 2018-04-24

I was eager and kept jerking and sucking tasting a different cock every minute another two loads were shot in this time one down my throat and one down my back which I could feeling rolling down me in the cooling night air. The pace increased as I got fucked on both ends, I was already moaning for joy as Pete reached in and started pulling at my cock literally miking me in the middle of this field. I could see the finish line as Pete put his dripping wet cock in my seed filled mouth and the b*****rs proceeded to give me the last fuck of the night.

Saturday strapon date night for my sissy.

anal nicksphilly 2018-03-24

Every Saturday night I bend hubby over,lube up his ass/pussy,insert a butt plug,and start out with his punishment. Then as I have hubby on the bed,bent over,I slowly pull the plug out,as I tell him "It's Saturday Night",I make him know what is coming,My strapon up his ass. I let him beg me for his training,"Please Mistress,please fuck my ass",I lube up the thick cock,put the head on his asshole,and thrust it in real fast,He moans like a sissy,but isn't that what a strapon session is all about? After a good 30 minutes,I tire of training his ass,the rubber is filled up,his cock is drained,I have milked my slut.I grab the condom off his clit,and put it on his mouth,as I have him lick it all out,"Swallow",I command,"Swallow all that jism.

Crossdresser's First Anal Orgasm

anal ksha 2018-03-17

This is the story of the first time this young man would discover the joys of prostate pleasure. Zack had experimented over the past year with various toys and methods to reach this mythical prostate orgasm everyone was talking so much about. He wondered to himself why he didn't go out in public dressed like this and find a real man, instead of using a fake silicone dildo. He teased his nipples till he couldn't stand it anymore, he was so horny at this point he just wanted the dildo in his ass. He felt the pleasure getting stronger and stronger as the dildo rubbed his prostate more and more. As he rode out another prostate orgasm, he felt the pleasure slowly fading from his body.

my transformation

anal elisatv 2018-03-17

Mistress and I live rather far apart, and I am not able to serve Her in person very often (She has slaves from all over the world who come to serve and worship Her), but She says that She gets almost as much pleasure from just whoring me out from afar as from me serving Her in person, and She definitely seems to get great pleasure from listening on the phone while some total stranger rams his big, hot manly cock repeatedly down my throat, choking and gagging me with his strong, throbbing dick, or roughly rams it up my tender ass, making me moan and whine to the rhythm of his insistent fucking, then dumps his hot, sticky load all over my pathetic, worthless sissy face and in my lowly, humble cumsucking whore’s mouth, and leaves me to wallow in a messy mixture of my own tears of shame, humiliation, and embarrassment and his salty, gooey sexual effluent, as he waltzes off on his merry way.

Following BBC home after the Gloryhole

anal Lozo44 2018-03-04

I was told to go greet Aaron's guests, so with my knees wobbling I slinked off to open the door.Opening it I was delighted to see four handsome guys holding bottles of good liquor and beer, hollering out it's party time!The all felt me up as the door closed making me even more dripping wet than before.Clothes went flying,beers were popped open, shot glasses were filled then emptied, loud music turned on and sissy was told to kneel on the floor with is fuck hole perched up for cocks to use.A big bottle of lube was set on the counter and it was on!

A flower for my Mistress

anal waraxe13 2018-03-03

'You dirty little slut!' She exclaimed, pulling my hand away from my cunt, 'How dare you disobey Mistress. 'Oh yes Sissy,' She said, grasping my hips tightly, 'I am going to ruin that little cunny of yours.' 'What a good little cunt you are sissy,' She said, as she grabbed my cunt with both hands and pulled it open, 'Shall we see if you can rosebud?' 'You will like this sissy,' She said, as she had me sniff some more poppers, 'The baking soda is going to react with your little sluthole and then I'm going to fist it till your rosebud appears.' She lubed up her gloves and then squeezed a generous amount of toothpaste onto her glove, rubbing it all over her fist.

Clara Bow's Academy For Would-Be Ladies Part

anal midsummerman 2018-02-14

“I’ll use the ‘bunny run’ next time; it’s a bit of a walk to the far end of the wall but if it’s good enough for the girls on their illicit tours…” The sissy he’d given the vodka to smiled softly and looked up at Bruce with puppy-dog eyes as she led him into the lean-to building opposite the potting shed, Bruce stumbling into the back of her as she paused to open the door; he sniffed at her sweetly scented soft hair and his cock grew as he squeezed it against the firm little bottom. He closed his eyes and thought of the sweet ginger new girl, and in no more than fifteen or twenty stokes, his cock exploded in the hot tight little anus, emptying his balls with a long and pleasurable grunt and groan.

Time Spent with a Sissy

anal 2018-01-15

Your ass will be fucked ONLY when it is beaten, sore and hot to the touch. I my allow you some comfort of licking you tears off of my cock. You begin to sob and weep, yet your ass gets wet and your little clit gets hard. Once your ass is penetrated for the first time, you orgasm and drop you little load down your leg. I look into your eyes that are tearing up while you violate your ass with the hair brush. You start to sob a bit and I know are ready. I pull out of your fuck hole and mix my cum with your tears. You are such a little sissy beauty, make up smeared with tears, sweat and cum.

Whos the Boss

anal mrdexs 2018-01-15

Admit it your no real man, Tish said I looked at all three in the room my wife, her bull and my employee and opened my dick sucking lips and said I'm a sissy, Oh I Just love being Daddy sissy bitch and love taking his big cock in my sissy pussy doggy style is my favorite position, are you satisfied Tish, I asked, now everyone knows? than to my surprise all three smiled and said its about time!, Nate pushed me over my desk, pulled my pants down and shoved his big cock up my ass, I could hear Tish and Jill laughing and cheering as Nate fucked my sissy ass.

First time stallion continued – A Black stallion

anal dirtyjenna 2018-01-06

The fucking of my life is what he’s now subjecting me to, though a huge regret that I let him inside me as his length is pushing too deep for comfort or pleasure mostly pain with each big hit of those balls onto my ass, my hand inconspicuously trying to hold my boyclit out of his view and the sound of my voice a fast repetition of “arh-arh-arh-fuck-FUCK” it’s not even fake like those porn stars give out, mine is of a real outcry of taking too much and I’m worried I’m being loud again and the T.V isn’t disguising anything this time either its off and even that is rocking now with the f***e of the desk moving and getting weaker as if it’s legs and fixings seem to also be crying out or giving way to this power house of a man, and sure enough there it goes the T.V falls onto the floor and I give into him completely knowing he isn’t going to stop until he’s done.


anal tvsllutmichelle 2018-01-02

I filled my large, long shoulder strap "whore's bag", a flashy, fringed, gold number with my makeup bag, a tube of my favorite lube, Albolene cream, two packs of long white Virginia Slim 120 Menthols, a half pint of cheap and raw 100 proof Old Crow whisky, several viles of sparkly blow, a heated, beautiful natural looking nine inch thick dido with balls and my light blue open toed 6" stiletto heeled springolators. Both of our cocks were raging hard and ready to blow so Kristl slowed down, slowly running her tongue up and down my pulsing throbbing shaft, licking and kissing my smooth balls looking up into my eyes with her smoldering, sultry heavily made up long-lashed eyes.

Devina in trouble

anal Devinatv 2017-12-14

"I think it does David, same Mac, same stains and look at the profile. the Mac. I looked in the mirror, god I looked like a slut and that got me David Jones, I am a sissy faggot whore who loves to suck real mens cocks As he continued to fuck my sissy hole Master David started to speak. "Now Devina, you have made such a good little sissy whore, and the web Master David opened his laptop and showed me a web site called Devina arms pulling in my Mac to f***e his hard cock deeper into my sissy hole. Master David, "we only cleaned that Mac yesterday you filthy tart," he "Take that Mac off, it will need cleaning again," shouted Master David.

Continued Sissy Date

anal MatureBrownMan 2017-12-06

I had fantasied about a man taking and owning my ass for what seemed like such a long time, but having James behind me with this swing cock, licking my puckering star had my little clitty leaking. “Wiggle your ass” “Tell me how much you like it” “Wink it” a few times his tongue went from inside my hot little cunt to the base of my smooth sissy balls. The sound of the tube being cracked opened, how cool the lube felt oozing down my crack as James drizzled it over my ass, the contrasting warmth of his strong hand separating my cheeks and my thoughts of me, giving my virginity to a man I met less than 12 hours ago on a gay porn website.

Sissy Bachelorette Party

anal waraxe13 2017-12-02

Off!' He whipped off his jockstrap and my eyes must have gone wide at the size of his veiny black cock, as he said, 'You like that baby?' As he slapped it off my cheeks. Let me get a shot of that.' Said Cheryl, as she alternated close-ups of my hole being fingered and me being fed Jon's seed. 'That feel good sissy?' Said Cheryl, 'Tell Mistress how much you love your present.' Jake had enough of me controlling the pace and pinned my legs against my chest and started fucking me hard, his big black cock causing me to yelp each time it filled me.

The Making of a Sissy - Part Twelve

anal midsummerman 2017-11-20

I can’t wait to see you dressed as a French maid; despite our little joke with Aunt Jane, I think you’d look so sweet.” Ellen showed Bella her room, all done out neatly in pink with a huge double bed. The two stood caressing for a good three minutes, just with the pure wonderment of being alone together at last; Adam holding the beautiful sissy’s sweet bottom tightly, Bella’s little cock rubbing sweetly against her lover’s; their bellies tight against each other in a loving and sensual embrace.

Becoming a Sissy Part 10

anal snoozer2000 2017-11-19

Daddy then removed his cock and looked at Sarah "okay first of all cleanup my cock and balls and then eat my cum from sissys ass" this had been Mandy's idea and that he thought it was magnificent. Tom nodded approvingly "okay lie on the floor" she immediately got on the floor and Mandy led Sissy over to squat his pussy above Sarah's face. Daddy decided to exert some control "okay mistress and sissy come over here and clean up the cum slut" Sissy immediately went over to his wife and started sucking and cleaning the cum from her face. When they had finished Sarah walked up to Tom and said "please daddy, let me be part of your group I want to be your whore cum slut and will worship your manhood in whatever way you wish"

Master fucks Sissy Eve

anal camtvslut72 2017-11-01

I straddle you backwards with my stocking leg over you, my cute lil ass up over your face as you start to paddle my ass, all the time verbally abuse me for being a such a pathetic cock slut, Daddy's sissy whore and your secret sissy fuck-toy. I'm in sissy heaven and I'm trying so hard not to come but my ass-pussy is SO tight against Daddy's cock. Just as you deep dick fuck me and pull and push your large manly cock a few more times, gaping my ass futher. You whip your still hard cock out my newly gaped ass and you slap my face with your against my now ruined makeup as you make me suck it clean of your daddy's juice.

Thunder in Hell - A Dirty Western

anal rebelmanXXX 2017-10-19

“Sheriff,” June finally spoke up from the other side of the bed, “That man made us do perverted things!” Taggert turned to see June standing naked with her hands on her hips and Sissy cringing on the floor with a blanket pulled up to her eyes. “I was going to have June get her friend ready by licking her ass,” Lou said to Taggert. “That’s enough,” said Taggert, “Get under her and lick her pussy while I fuck her.” June moved onto her back and slid under Sissy while Taggert lined up his cock with her now lubricated hole.

Street Walking Sissy Boy!

anal nancyvasquez 2017-10-15

We kiss for a minute and I can feel my dick getting hard. If it's slow in the arcade, he takes me up to the road in back of the complex, where a lot of men park, looking for sex. This time he didn't kiss me, just gave me a hard stare - which I seen before - usually just before I got my ass beat. I got down on the floorboard between his hairy legs and began sucking his cock, first running my tongue around the head, then filling my mouth with saliva and engulfing his erect cock into my mouth. He pushed my head down between his hairy legs and I began blowing him again, sucking his cock and nuts.

An offer I couldn't refuse.... part 1

anal guru6969 2017-10-14

I bent over and took one of her beautiful nipples in my mouth and sucked it, then gently biting down on it made June yelp and her hand flew between my legs where she latched onto my still very hard cock. June broke off from sucking me and lay back on the couch, spreading her legs she placed a hand on her pussy and slipped two fingers between her swollen lips and played with herself, removing her fingers she held up her hand and said, '' Look sissy boy, that's how a real man makes a woman feel, unlike you, you only make me feel disgusted looking at your mini cock''. I gulped looking at June's beautiful sexy body her breasts huge hard nipples that soft hair covered pussy.

A Trip to the Bathroom

anal klammer 2017-10-11

I see your pretty face smothered in way too much brightly colored makeup, loads of cheap jewelry just dripping from your ears, fingers, wrists, neck and ankles as you lovingly wrap your lips around me and suck on my big black dick... Loads of rings will adorn your fingers and your pretty wrists will be covered in loads of loudly jangling bracelets, their noise, along with that from your large chandelier earrings will proclaim to everyone that a proper little sissy is coming their way..." Just imagine the creamy pink of your little virginal sissy lips engulfing my throbbing nine inch cock, letting my meat slide all the way down your tight little throat before I shoot a full manly load of hot white cum into your belly.

Part Two: The Carpet Guys Koni Gets Ruined

anal Konicum 2017-10-09

Looks like you've had some fun with my guys." With a chuckle Mike then asked, "Are you satisfied with their work?" I just gazed at him with a stoned stupid vacant look on my fucked up face and Mike said, "shit boys, you got her stoned didn't ya?" They snickered and Richard said, "She asked for this boss." Mike looked at my bimbo face, coated in sticky cum and his eyes looked down to my limp little clitty which had a clear string of fluid drooling from it and onto the inside of my black stalking covered thigh. I hung there upside down pinned to this man with his big cock head wedged inside my slutty mouth and my weak little sissy body quivering from head to toe; Mike pulled me off and dropped me to the floor like a used wet rag.

Slutty Sissy Used in a Cheap Motel Part 1

anal cumslutchloe 2017-10-05

He came in and sat on the bed and immediately started taking his pants off while I got down on my knees in front of him. I love it when guys want to start of immediately with fucking, so I asked him in my most submissive girly voice what position he would like me to get into. His cock slid balls deep into me and he started to fuck me nice and slow, pulling almost all of the way out and then jamming it back in as deep as he could go. I was deep throating his entire cock and getting him nice and ready to use my cum lubed hole and he was hard as a rock.