Sissy Cheryl, how it began

[Sissy Cheryl]

As I sit here just watching the TV I am wondering how this all happened. "Well its been something else", I thought to myself. Crossing my long smooth legs I sat back and thought of how this all became this way. "Never!", I muttered to myself as I let my right hand go to the hem of my mini skirt and let my long painted red nails slide into my blueish tiny pantie and begin to fondle myself. "Hmmm",I moaned as I lifted my black high heels up so they were resting on the cushion of the couch and my long garter belted thighs were opened. "I can't believe I have be came this!", I sighed as my fingers now gently touched myself.
Just over 3 years ago I had been like many of my peers, now though , after my ex had done the transformation of me she had done I had totally changed. "Oh god that fills good" , I slowly and gently swung my hips as my soft delicate hand wrapped around my semi erect little dick. While my right hand incircled my now growing dick my other hand reached to my left for the didlo I had laided on the couch earlier. Taking it on my hand I guided it towards my sweet red lips and letting my tonuge
slide out , licked the big head of the black large dilldo.
"Pop, pop", the thick head popped in and out of my pouted mouth as I bathed it with my salvia. "hmmm" , my throat moaned as I tried to take at good 2 or more inched of the hard rubber dick in between my excited mouth. Stroking y now hard dick i could feel the excited urge that had made me become what I was.
"POP" < let the thick dick slide out of my mouth and I excitedly held it firmly between oth myhands and guided down betweenmyspread wide legs, down past my pulled backlittle panites, past mystiff little dick, beyond my soft thighs and just next to my smooth shaved ass. "This should help", my heaving chest caused my legs to shake as I spit on my hand and lubed the big cock for it entry nto my tight white shemale type asshole.
Spreading mylegs as wide as possible I urged the big head to my snug ass. "Ohhh, oh god yes!", I siged as I felt the head start to try and invade this sissified butt hole of mine. "OH god yes, fuck me", I closed my mascara covered eyes and alowed my self to dream of how this all began as I pushed the big 8" rubber cock further into my tigh spreading ass.

 

[Sissy Cheryl]

"God damn you got a nice pussy", the man fucking my plump pretty wife moamed as he stroked his dick into her rapidly, causing her to buck uncontrolably. "Jesus Christ, oh Jesus !", Lynn babbled as he swiftly feeled her open pussy with his long dick. "Thats it thats it, dick me good , fuck my married pussy!", lynn urged him on.
We had been married for just about a year when we decided, at my urging , to give swinging a try. At firt Lynn was not too happy about the idea. Besides the fact that I would be with other women she didnt feel she was that attractive. Lynn was and still is a bit on the plump side. She stands about 5'2" and wieghts in the range of 125 and up to 130lbs. Yes a slight bit chunky that was true , but she made up for it with a huge set of 38D brease, a nice round chuppy ass and shapely legs to match. In a mini skirt and a reveeling top she could appeal to just about any man.
Yes, fuck her good", I said under my breath as I sat on the floor watcing her pussy gaping open from the large dick entering it. "God she looks good", I contniued mythouhgs as I unzipped my pants and pulled out my own dick and stroked it in unison with there fucking motions.
"Give to me, give that dick and cum in me!!", she babbled as his back tensed and his dick now pounderd furiously into her slick pussy. "Oh my god, oh my god!!", she cried as I looded between her thick thighs and saw the first trace of cum dripping out of her filled with a strangers dick. "Oh yeah take it you hot little bitch!", the man riding my sweet wife gurgled as he now sank his dick fully into her and began to flood her eager pussy with his potent seed. Yes fuck her!", I muttered as I now was stroking my own stiff dick as I started to cum in unison with there fornication. As they slowed down there fucking ,Lynn glanced over at me. There I was with my pants around my ankles, my dick in my hand spewing my thin cum onto my legs.
"You liked,huh", she smiled at me as the man on top of herpulled his now limp dick out of my wifes wet and spoiled pussy.
"Yeah" I sheepishly said I quess i did", I was embarrassed by her seeing me playing with myself. Now this wasn't the first time we had meet with a single man for a little fun. On the contray at first we meet with couples but Lynn wasn't too keen about watching me with other women. So we diecided that it woudl be best if we stuck with only men. She seemed to not mind that and I had now gotten use to wathcing her giving up her charmds to other men, no matter if they were single,married, or what age they might be. However this was th efirt time I had gotten so excited that I had pulled my dick out and played with myself in her presense when she was with someone else. Usually I just watched and at times took videos and pictures. I never joined in as she seemed to enjoy playing the role of a married ***** or a wife whos hubby wasnt' givning her what she needed. She would dress the part well too. In a very brief little skirt or dress,high 3+" heels, a thin top and rarely if ever any panties she could show off that thick body magnificently! "Ohhh' she maoned as he got off her, my god you made love to me wonderfully!", she reached up and put her arms around her most recent bed partner.
"so much better that he can", she smile and looked my way. Awkwardly I started to let go of my still hard dick as she kissed her lover and looked at me.
"Now don't be ashamed", she grinned as she turned towards me.
"Why don't you come over her on the bed and show us both how you play with that silly dicko f yours", Lynn smiled and looked to her parter. "Yeah that sounds cool", he spoke towards me. "Yeah bring that little dick over her and show your wife why she prefers me",he laughed as Lynn snuggled up to him and made roon for me on our queen size bed.

 

[Sissy Cheryl]

As I nervously stood up I awkwardly walked towards the bed they were sharing. "Oh com'n, Lynn disaprovingly said to me, take that tee shirt off and get naked!", she grinned at me as i did as she asked me to do. Stripping down I got on thebed withme legs crossed trying to hide my nakedness and small dick from ther gaze. "Ok, get it hard honey", Lynn smiled at me as she held onto her tall partners semi hard and much bigger cock. Leaning back I began to play with myself as I watched her storking his manhood to erection once moer. "Ohh, ohhh, I moaned lightly as my stiffening little penis rose and became somewhat firm once more. "look at that, Lynn grinned as she leaned up and kissed her newest lover on his big dark lips, Its onlyhalf as long as ou are", she smiled as she then lowwered her pretty face to his bulging shaft.
It was neerly too much fo rme to bear. In All the time we had been doing some swinging, which had been about 5 years there were a few thiings she had said she would NEVER EVER DO and not to evre ask her to or else. Tonight she was breaking two of her main vows to me and I wa shocked. She had never in the 10 or so years I had known her ever put her cute mouthof mydick. She said it was a disgusting idea and there was no way she would ever do that. She had given me hand jobs of course but her mouth was off limits.
The other thing , which I had always tried to get her to do was have sex wih a black man. Growing up in Alabama she found that the worst thing a white women could do. To her if a white female had sex with a black man she had to be the worse type of tramp and ***** that ever exsisted. Pulling vigoursly on my now enraged dick I looked excitely at her as she lowered her red lips and her floppy big titties dangled above this black mans cock and she started to suck his meaty cock. "Jesus, I moaned to myself as I watche my lovely wife do something she had never done before, she going to blow him!", my eyes widened as I watched her head bob up an down on his now shiny throbbing prick . "Hurry up, shoot that little dick of yours off!!", she lifted her head fromhis cock and urged me to cum, you like?", she lifted hef left leg up ******** to meher hariy opussy that was dirpping the black mans seed on to the sheets, building up a pudfdle between her chubby legs and smearing her big wide ass as well.

 

[Sissy Cheryl]

Faster and fasster I yanked on my now ready to erupt dick as she again sucked on that bigger black cock , with her eyes glancing at me as I furiouls tried to lose control.
"Ugh, ugh, oh god!, my hips humped up off the bed as I felt my balls start to release my creamy cuminto the air, FUCk, ah FUCK!!", Ibabbled as my dick shot cum out and it cascaded onto my dick shaft, coating it with my own cum seed.
"Well look at that ,Lynn smiled , as she took her free hand and ran a finger across my coated with cum shaft. Using her hand she smeared some of my seed onher fingers and putting it near her mouth began to taste it.
"No, that wouldn't be correct. she stopped just short of putting her finger in her lovely pouting mouth, here , you lick it , I dont taste cum, you know that, scolded me she pushed her wet finger towards mymotuh. "Lick it clean!", she demanded . Leaning forwrard i let go of mylimp peter and nervously opened my mouth as she stuck her finger in it. "Slurp, lick", I licked my residue off her long nailed finger . "Sohow does it taste!", she spoke ot meonce Ihd lcened her finger off. "Its, its ok I nervously siad as she took her hand away from my mouth and lowered it to between her thick thighs.
"Try this, she slowly siad to me as he pushed two fingers into her pussy and came out with a huge gob of the black guys cum which had been deposited in her love tunnel just moments ago, open wide!," lynn wass smile from ear to ear as she shoved her smelly cum laden fingers towards me.
"Ok," I agreed , not know what else to do, mMymouth quivered as her fingrs entered my mouth and I used mytongue and throat to get every drop of that cumoff her fingers.
""SO how does it taste?", my wife asked mes she withdrew her now clean fingres out of my mouth.
"Its awful thick and salty tasting,much more than mine is",I embarrasingly admitted.
Leaning on all fours to me Lynn hd her big thick juciy ass in the air and her large tittes swaying down. "you got that right,its thick and tasty and very very potent as well, thats why we havent had any baibes,its not me its your usless seed!", she lashed out at me.
Com'n Lover, she looked at the man who was getting behind her upturned asscheeks. Feel my married white pussy with some more of that precious baby seed, she grinned a wicked smile,'.
Now get off this bed of mine and my man her and you just watch how a real man takes a women like me!", she threw her head back as he started to slide his long dark shaft onec more into Lynn's willing open pussy.

 

[Sissy Cheryl]

Yes,god yes, fuck me Tyrone baby!',she now was babbling his name as she shoved her big fat ass to his ramiing cock as it slid into her with no effort at all. Lynn had a tight pussy ,but this mans cock waas making it sick and wider than it had ever been. "
"Get you scarwny ass out o fher so I can fuck her better!", the man said to me menacingly. "You heard him, leave,my wifes panting breath spoke to me as she looked my way go into the living room or somethng for god sakes!!", her blazing lust feeled eyes told me. Quiclkly I got up and scurried to the bliving room,closing the bedroom door just a bit.
Even in the living room I could here the noises of them fucking hard. He was pounding her hard or makeing the bed move so much the bed was rocking and the groaning she was making was unbearale to me to fathom.
After about 20minutes of listening to there noises ,I had to see what was going on. Naked I tippy toed towards the bedrorm and peered into the bedroom thru the door I had left slightly ajar. "Wow!', I exlciamed to myself, as I stroked my tiny hardenig dick, shes on top !", I muttered as I watched her pushing her chubby body onto his lean dark body. She wa swinging those massive hips and her ass was a blur as she rode him franticallys. "Suck 'em, go ahead suck them hard!", Lynn was lowering herself lower as this strange blakman was using his hand and mouth to tweak and suck on those big 38's of hers, making them extend out lower. "shes cumming!!",I was amazed, as I saw her now furiously pumping on him.
"AUG<AUG< FUCK ME!!",she rasied her head and her body shook as this man , this blackman who until only a couple of hours she did not know,emptied his thick warm gooey seed in my wifes eager pussy like a fire hose.

 

[Sissy Cheryl]

"AGH, god , oh god!!", my short little wife was screaming as she threw her hari back and slammed her big white ass hard onto this mans erupting meat as she wiggled and thrashed upon him. "OH Jesus Christ!", she wa babbling as his cock sprayed its warm seed in her open and eager pussy . "Ahhh' ,she sighed as she collapsed on him and her legs spead to allow his dripping and still enlarged cock to slither out of her yanwing pussy hole.
"Wow, that was fantastic!', she lifted herself up on her hands, leaving her giant tits to hang down close to his chest.
"What do you think your doing spying on us!", Lynn turned her head to catch me peeking at them. "I , I wqas just wanting tos ee if you two were done", I stammered.
"Sure you did,you just wanted to see how a real man fucks your wife,huh!", she pracitaclly spit the words at me as I retreated to the
About 15 minutes later they came out of the bedroom to the living room. ""No," I mumled to myself. Lynn had put on her white nitie , the one she swore she would never wear as it was her wedding nitie, "How many more things ae going to change ", I glanced at her as she walked Tyrone to the door. "Good night sweetie ", she got on her tippy toes to reach his neck. Being so short and hm so tal lit was a impressive sight! "Leaning dowwnTryone cupped my wies big ass firmly in strong black paws.
"Now remebre what I said ", he smile at her as they both turned to look at me sitting on the couch naked,
"Don't worry, Lynn hugged him, next time it will be even better!," she again kissed him as they both looked my way and laughed .
"See you then", Tyrone said as he gave Lynn a soft smack on her rump and left our place.

 

[Sissy Cheryl]

Sitting on the couch , I nevosuly looked at Lynn as she approached me. "Well did you enjoy finally seeing me with a black man?", she smiled as she sat next to me, Its what you always wanted to see, right, me letting a black hung man fucking me wildly", she purred towards me as she grinned .
"yes, yes, I did", I looked into her blazing eyes," I mumbbled . "If I had know how good it would be I would of agreed a longtime ago", she laughed as she ran her fingers over her plump thigh and touched her hairy furry pussy.
"So , so what were you talking
about", I stammered as I held my now rising dick in my hand.
"If you must know, i was telling him he could come over and fuck me again, Tuesday night and that you would help!", she stood and strted to walk to our bedroom. "How can I help??", I nervously spoke.
"Oh you'll see, she smiled over her shoulder, now come on in to the bedroom, I need you to clean up my wet dripping well fucked pussy!", she grinned and headed to the room with me follwoing her.

 

[Sissy Cheryl]

As I entered our bedroom, I was surprised at how quickly Lynn had gotten herself into the bed. Standing in the doorway the sight that greeted me was unbelievable. Laying across the bed sideways , with he short somewhat thick legs pulled up and resting on her elbows she beaconed to me. "See that, she pointed to her shiny slick pussy, that what he did to your wifes tight little pussy ,honey, he destroyed it, made it big and open like a women should be form sex!', she was smiling broadly as she teased me.
"Whattya think?, she continued to grin at me as her fingerr went to her pussy and slowly she slide it in herself, looks good doen't it!", she laughed towards me. "Come over here and taste it baby, see what it realy looks like and taste like now!", she demanded as I slowly was transfixed by the sight of my wife laying on the bed inviting me to taste and fill her warm spoiled pussy.
Inch by inch I slowly like in a dream wandered to her laying there. "Oh god, it looks so good", I though to myslef as I found myslef getting on my knees beween her legs and getting right up to her dripping pussy hole.
"Thats it honey, put your tongue in me and see how hot he got me", she moaned as she let her head fall back and with one hand reached for the back of my head and pushed me into her pussy. "Lick it, lick good, she muttered as my tounge voluntarily licked at her steamy mosit pussy. "Ohhh yes , that's it, oh og yes'she was moaning as I looke dup from my ating to see her grabbing ahold of one of her massive 38" tits while my tounge now began to taste the cream between her lips. "Slurp, slurp", my mouth feverishly licked her insides of its potent cum that he had left in her now open pusy. "He fucked me good, oh god did he fuck me good, baby!', she looked down at me between he spread thighs.
"Huh huh", I mutteded as my face buried itself between her open legs and enjoyed the smell and taste of her rcently mounted and stuffed with cock's pussy.

"Get it all, com'on get it all"!' Lynn wailed as she lifted her chunky legs high and shoved her ass into my face forcing her pussy to engulf my face fully. "Thats it , thats it!!", she mutttered a she wiggled her big thick ass faster and I could feel her pussy now starting to flood my mouth with her juices as she came hard.
Slowly she relaxed and as she did she pushed me away from her moistness. "Now go get me towel", she glared at me. tommorrow your going to have to do something different for Tuesday to be fun for us all. I noticed how you liked the taste of his cum off my finger and from the way you just ate me you like it in bigger doses as well". "Well starting tomorrow and Tueday you are going to learn much more",she spoke harshly to me, "now get me a towel and lets get to sleep", she barked at me as I went to retreive the towel she wanted.

 

[willsrvu]

Nice Cheryl. Can't wait to see what the wife has in store!

Thanks,
will :bj::yumyum::lick:

 

[whtcuckold]

Great Story:bj::lick:doing what a good sissyboi should do

 

[Sissy Cheryl]

Yes I am always willing and ready to please a black male! Dressing like a girl is awesome and letting men use my painted lips like a pussy or putting me on all fours, pulling down my tiny panties or thong, pushing my short skirt over my hips to ****** my tight round smooth ass for ther hard big black dicks to ravage me good is what i am made for.
will be treying in the next few:bj: days to finish telling how I became such a sissy for men.
Kisses
Cheryl:bj:

 

[Sissy Cheryl]

I was quite nervous over the next couple of days waiting for what Lynn had eluded to. "How can I help and make it good for all of us?", I mused at work over those days. "hhmmm", quess I'll have to wait", I continued my thoughts the day of the meeting. "
"He should be her sound!", Lynn spoke as she paced in our living room. She had on a powder blue little skirt that with her hips hugged tightly on her excentuaing her shapely but thickish thighs that were nearly totally visible under the shortnes of the skirt. "Heck", I thought to myself, shes wearing a new garter belt to match the color of the skirt!", She wasnt the type to wear things like that and had seldom put one on unless I had begged, but here she was in a pair of 3+' high heels, a short skirt and a garter belt to match! The most amazing thing was the shearness of the top. She had this thing about not wanting so to show too much cleavage. "Isn't the top a bit revealing , I quizzically said to he as I noticed how low it hung and how translucent it was."" I , I can see your nipples", I studdered as I look at her pacing the floor and her ass wggling and her breast swayed.
"Well of course it is, do you like it?, I hope he does , I put it on to excite him more", she smiled at me as she continued to pace. "He said he would be hear by 8 and its almost 9 pm", I could see the concern in her voice . "Ah, thank god , that must be him!", her vioce erupted at the sound of the doorbell. Scampering faster than I had seen her move in years she wiggled her plump juciy ass to the door.
"Hi!", she blabbered as she opened the door and seeing him standing there threw her arms around his neck as his black paws went to my wifes round full butt and he fondled those two twin cheeks of hers. Stretching up she had to sstand on her tippy toes to reach aroundhis neck and in doing so her big round bare ass was totally ******* to my gaze. "God I am getting a hard on," I realized as I looked at how the garter belt accentuated her bare asscheeks. "Now, she looked back at me sitting on the couch, the fun can begin', she continued as they both entered the living room.

 

[Sissy Cheryl]

Sitting in teh chair in the living room I couldnt take my eyes off the two of them as they eneterd the living room. "I am so glad you finally got here!", Lynn stammered as they sat down on the love seat and she snugglled extremley close to him.
"Damn you look good tonight, Tyrone smiled as his hand went to her thighs sticking out from under her abbreviated little skirt, spread those juicy things baby", he demanded as his hand now rode up her opening thighs and his fingers now touched her hairy blond snatch. "I'd love to !", Lynn breathelessly responded as she practically squirmed further into her lover
Leaning forward she rested her one delicate hand on the front of his pants and stretching up began to kiss his neck while his hand now started to finger her tight but growing moist cunt. "Jeez, you feel awlful hard?, she smile up at him, may I?" she cooed as her tiny fingers began to unzip his pants and she fumbled to retreive his manhood. I watched to complete delight as well as amazxement as her body wiggled all over the place as his hand was now fingering her eagerly and her legs were wide apart showing her stocking encased legs up to her white upper thighs.
"Ohhh, she moaned as her hand finally grasped a hold of his stiffening shaft and she pulled it out from his pants,mmm, it looks so nice", Lynn's eyes were ablaze with desire as she began to stroke his stiffening cock in her long nailed fingers. "Well if it looks good, maybe you should taste it women", he laughed as he placed his free arm around her and guided her towward his enraged black meat.
Standing up abruptly tyrone dropped his trousers and stood in front of my wife with his nearly erect cock dangling in front of her wide eyes.
"Damn , I thought to myself, I can't see anything now", I muttered as Tyrones muscular body was blocking my view of Lynn sitting on the edge of the couch staring at his offered shaft. Getting up I wandered to the side of the love seat just in time to see Lynns lovely lips open up and lick the purplish head of his cock.
"Pop, pop", I heard the the undenable noise of her puckered lips as his cock head enterd he stretching mouth and then leaving slightly so to make her lips open wide to allow its escape. "My god its huge!, I excitely muttered to myself as Lynns fingers now encircled his long shaft, hell she can't even wrap her hand around it !", I was shocked to see has his thick meat just was too much for her hand to encompass.

 

[whtcuckold]

Damn Girl you should have been a good sissy and held it and mmmmmmm :bj:licked it for her getting that big head in your mmouth is what all we sissies need:bj: nothing like a Big Black Cock in our mouths mmmmmm

 

[Sissy Cheryl]

as soon as I have a moment free time I will finish what happened next. And as far as being a good sissie I learned the art of doing just that from within moments of this last line and so much more