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

anal stacielana69 2018-11-15

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.

Slutty Sissy Used in a Cheap Motel Part 1

anal cumslutchloe 2018-09-29

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.


anal tvsllutmichelle 2018-09-11

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.

A Sissy's Lifestyle

anal nancyvasquez 2018-08-11

I squeezed his cock through his pants and said, "Sweetie - give me a minute to freshen up." I headed to my booth and quickly stripped completely nude - even the bikini. When I first began hanging out in that arcade, I used to walk around completely nude, high heels only. I didn't think much of it, but about 2 minutes later the manager of the modeling studio came back and told me, "You can't be walking around the corridors like this - you have to be in a booth if you're going to be naked." Anyway, that's a little background on what my life is like, sucking cock and getting fucked in the adult arcade.

my transformation

anal elisatv 2018-08-07

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.

Femberly: Worth the Trip

anal hobbnobb77 2018-07-20

I wasn't surprised that the warm body next to me was a handsome young guy completely naked except some of my red lipstick smeared all over his cock and balls, and i started thinking back to my child hood. He asked if I wanted to go back to his place for a nightcap ,I smiled and slid my hand over his very hard cock while whispering in his ear that I wanted to very much, but first go by my rental house and let me throw some clothes in a over night bag. I pushed him onto his back, not want to waste a second I started licking his cock thru his shorts getting them nice and wet, I bit the elastic band of his underwear and slid them down, down, and off.

A Sissies Tale....The Neighbor p2

anal LynLorre 2018-07-19

He laughs a little and says" Your clitty needs a licking" and sticks his tongue out and start flicking and licking my small head.My little cocklette bounced around as he tongue lashed it and i gave a moan of pleasure and said"You wanna try my sissy pussy next?"He stop licking and replied"Thought you'd never ask" and layed down on the bed and stroked his cock a couple times and said"Here's a nice spot to sit little girl".I smiled and opened my night stand and grabbed a bottle of slippery stuff and with a girly stance i said "Where gonna need this big boy" as i looked as his thick meat.I squirted a nice amount in my hand and rubbed and stroked all over his cock then rubbed the remaining on my tight sissy hole.I turned around and backed up to him putting his legs between mine so he could have a nice view of my round shaved ass.I took a hold of his whopper and pulled it towards me as i lowered myself to it.He said in a heavy voice "Thats so hott,Love the reverse cowgirl.I pressed his throbbing mushroom head against my sissy hole and slowly i felt it slide in.I took a quick breath and waited for the small bit of pleasing pain to stop as my tight hole loosened around his this head.

His Fantasy Brought To Life

anal ksha 2018-07-18

"Yes mistress," Stefan managed to moan as Alisha slapped his ass again. Within only a few minutes Stefan managed to moan out, "I-I'm going to cum mistress." Alisha promptly turned up the massager to full, and Stefan let out a stream of cum. She moves her mouth next to his ear, "You better get ready Stefanie, I'm going to fuck your ass all night till you are just a limp pile on my couch." These words made Stefan shiver with excitement as Alisha slapped his ass once more. As time went on and Alisha fucked him even harder and faster, Stefan felt a warming sensation in his cock.

Continued Sissy Date

anal MatureBrownMan 2018-07-16

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.

Thunder in Hell - A Dirty Western

anal rebelmanXXX 2018-06-30

“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.

Becoming a Sissy Part 4

anal snoozer2000 2018-06-29

My cock exploded with rope after rope of cum landing on her face, lips, in her eyes and hair, but like a good sissy her mouth stayed wide open to collect as much cum as she could. With that sissy, still in six-inch heels, went to her handbag and took out some lube and what looked like a bigger butt plug than the one already embedded in her ass. She turned her head to me and said "sissies ass is ready for daddy, can I have your cock in my ass now please" there was a whimper in her voice, I understood again the joy I was going to be giving her when I reamed her ass. I felt like I was finally getting the respect and worship that I deserved, that thought drove me wild and I started to plough into Sissy's ass.

First time stallion continued – A Black stallion

anal dirtyjenna 2018-06-23

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.

Street Walking Sissy Boy!

anal nancyvasquez 2018-06-14

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.

Being Caught....A Sissy Dream

anal LynLorre 2018-06-01

Still sucking and stoking the blonde mans meaty hard on.I felt the brown haired man move up behind me,i felt his thick package smack against my ass.I spread my legs open to match his cock height.I felt him feeling up my shaved sissy ass as he pulled my satin thong to the side and pressed his cock against me.My body shuddered when i felt him press the warm tip against my sissy pussy.I quickly took a glob of spit off my mouth and reached back and rubbed it on my tight fuck hole.I heard him spit just after and i could feel it slowly run down to my hole.He pressed against me again and i felt the warm head slide in my boi-pussy.I pushed back towards him and pulled back to get the spit lube worked in.We both did that a few more times till he was all the way deep inside me.He stared to fuck my sissy hole slowly with firm thrusts to get my tight hole to loosen up a bit.The Blonde man who's cock i was still worshiping with my warm mouth was making moans of pleasure and telling me "That i was a good little cock sucker...mmmm..

A flower for my Mistress

anal waraxe13 2018-05-29

'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.

Whos the Boss

anal mrdexs 2018-05-17

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.

Saturday strapon date night for my sissy.

anal nicksphilly 2018-05-16

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.

Becoming a Sissy Part 10

anal snoozer2000 2018-05-14

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"

The Long Road To My First BBC part five

anal proudman2 2018-05-13

I wanted to feel like a woman with a mans cock buried inside my body. This is exactly what I would have felt like if I would have got caught walking into the motel last night. "You one of them faggots that like to suck dick?" "Hey, you like some big ole black cock?" he said trying to apply some authority to his tone. So I replied " no I'm not a faggot, and yes I love to suck cock and lots of it" "now as to black cock I don't know if I'm going to like it since I've never had the opportunity before" "but I've been dying to try one, that's for sure".

Devina in trouble

anal Devinatv 2018-05-08

"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.

The Making of a Sissy - Part Twelve

anal midsummerman 2018-04-16

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.

Clara Bow's Academy For Would-Be Ladies Part

anal midsummerman 2018-03-21

“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.

Crossdresser's First Anal Orgasm

anal ksha 2018-03-11

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.

Time Spent with a Sissy

anal 2018-03-09

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.