Another Sexy Story

A beautiful tale of a young man's journey from school yard bully to feminized sissy slut..... presented in a slow, sensual pace that is captivating and familiar....

"That's right, Stephanie, get his cock nice and wet. Your pussy is going to be really tight if this is your first time" She was speaking loudly, obviously loud enough for the customer to clearly hear. His hips thrust forward more, eager at the idea of fucking a virgin. 

Sugar's hand had slipped down towards my butt. Hovering just long enough to scoop more cum into her hand she expertly pulled my g-string to one side and started to caress my arse. 

 "This is your pussy". She whispered in my ear, "Just like a girl you have a pussy solely so men can fuck you. Always remember that". Sugar rubbed a finger across my arse slowly. "As you suck him, remember that his wonderful cock will soon be inside you. He is going to use your pussy to make his cock cum. He likes being in your mouth but I am sure he would like to cum inside you with his lovely cock. Would you like that Stephanie? Would you like him to fuck you tight virgin pussy?

I moaned, a sign that that is what I wanted. And I wanted it so badly. Somewhere deep down I felt that I would become a complete girl if I was fucked. It didn't matter that I could not see the guy. I did not even know what the guy looked like even as I slurped over the end of his magnificent cock. I wanted him inside me. And Sugar was helping me prepare lubricating my arse with warm cum. 

"It's time" Sugar whispered "Turn around darling".

The full sexy reading material found here.

The Consequences of Anal Training

i lay on my back, legs in the air, the gusset of my lace fringed panties pulled aside. my eggs delightfully trapped in the cute cotton, while my chubby sissy stick poked out the top enough to rub and fondle. Her wet lips caressed my thigh as she licked my clean underside, lubing me for the main event.

A small tickle, a tiny bit of touch, barely perceptible."You're loose."

"MMmmmm...." was all i could reply. my sissy thoughts racing immediately to the constant pounding my rubber Daddy delivers to my needy pussy almost daily.

"Why are you so loose?" Some soft rubbing inside. She is humping my leg slightly, i can feel the warmth radiating from her sex.

"You make me hot *sexy smile*" The safest answer.

i hunch my hips and open my cheeks trying to feel a bit more of that amazing thumping inside my hole. It's not enough. Reaching around, i feel her index finger curled, she's only using her middle finger. A little proding and manipluating, and i get her first two digits inside.

"Mmmmmm" My pre flows over my crown, wetting and allowing my sissy fingers to rub it shamelessly. Opening my eyes, i watch her breasts heave and she humps and rubs her quim harder on me, her arm thrusting as she works my bitch hole.

i hump up and down, showing her my need to fuck. It's not enough. Another reach and i have three fingers opening my cunt nicely. That's it. That's the  magic.

Rubbing, rubbing my clitty. Eyes slitted. She's fucking me. Fucking my hole. i am muttering the most faggiest of utterances. "Fuck me. Fuck my Pussy. Oh, Fuck, Thats Right.. Fuck Me, Oh Fuck, Fuck My Puusssyyy!" i cum hard. Over and over. Six, seven hard loads. Not a spurt - that doesn't seem to happen anymore. It's more like a flow. A flooding overflowing the constraints of my piss hole. Flowing over my swollen head and over my squeezing fingers.

She keeps me penetrated as i come down. my sissy hips hunching up and down slightly, my hole still spasming less and less. With a steady pull, she empties my hole as she climbs over, rubbing her sex into the mess on my belly, quickly shrinking clitty and my poor abused panties.

Staying doggy style over me, her tits in my face, i service her digitally, the way she prefers - wishing the whole time i could lick her clean.

---- A short time later ---

"So..... why were you so fucking open?"

"i don't know.... i guess i needed it."

"Are you gonna wear your girly panties today?" <sneer>

"i dont know." i didn't.

------------------

Last time i i removed my hair... well.. last few times.... i've been making the clean area larger and larger. What started as only shaving my clit and eggs, has progressed to the tops of my thighs to just bellow my bellybutton, with a sexy patch above my pricklette. Last time i even shaved a small ring around my nipples. As i am quite hairy, it is noticeable, however its a small ricng of clean area, so not hugely different.

i hope my strategy of slow but consistent limit stretching is working on her. So far... no blow ups. But then again, her history is to take take take then explode. i hope that doesn't happen. How long will this take?

My First Anal Virginity

Once upon a time.....

My ex wife and i were swingers. We didn't call it that, but looking back, there's no denying it. We would frequently use the phone flirt lines that were so popular in the early nineties. They were normally free for women, so we would get the number she would leave the greeting message, and then we would suck and fondle each other as we spoke with guy after guy after guy, and occasionally a girl.

You see.... even though i was still in denial about being a sissy, she kinda knew it... perhaps it was the way i liked her to peg me with candles, or the ass-play that i didn't mind... idk. *giggles* She was quite the little repressed bi-sexual herself as well. While i'll prolly never know the truth (she was a g'damned dirty liar - but that's another rant for another day) when i met her, she had had a couple of mild lesbian experiences, but loads of fantasies - fantasies that i actively cultivated as we screwed each other like 20 year old rabbits tend to do. She was also fascinated with watching two men, as many girls are i guess, and she saw her chances to fulfill both our fantasies.

The phone lines were a good way to meet like minded individuals and arrange for casual meetings... the 'Craigslist' of its day. To my dismay (not really i guess, cause i went along...) the lines were dominated by guys (surprise!) but we found, many times, the guys had / knew of girls , or were just fronting for the ladies... and couples were always looking for other couples.

i guess, at that - at that time - i was prolly closer to hetero with bi leanings (for comparison, i would say today, i am gay with bi leanings, hehehe). So, i didn't mind the guys. i tended to be slicker with the ladies too, understanding them better. Many times, i was tasked with keeping the other guy to keep calm and relax, let the ladies get acquainted, wait for the right time. More than one idiot ruined the whole thing by being too eager. But once the action started, it would be girl on girl, boy on girl, swap partners, etc. Sometimes a guy would be adventurous and reach for my dick. Sometimes i would 'help' my wife by guiding his cock inside. If there was enough alcohol... eventually i'd be licking and tasting... sucking his dick... satisfying urges deep within that i still couldn't admit to myself, much less anyone else... but at that moment... i didn't care.. i would find myself lost in lust.....

~wheww~ excuse me.... *giggles and blushes*

So..... fast forward a bit. We were good at the game. We now had numerous regulars. A constant stream of girls wanting my wife, a few who would fuck me as well (wife loved watching me fuck... actively encouraged it and thoroughly enjoyed it). There were at least twice as many regular guys though, a a couple of couples. This whole deal went on for, idk, 3-4 years? All of the guys were at least somewhat bi, to varying degrees. That was key for her. One time we met a friend of a friend... who actively admitted he preferred guys, but didn't mind playing with girls too. And he brought a video camera.

This guy kinda intimidated me.. even though i was a bit heavier, hairier, and overall more manly than he. His openness about loving dick, his constant efforts to get me instead of my wife, idk why it scared me, but it did. Drink drink drink. Camera comes out.. not without many promises of total privacy... but it also was a turn on to think that he would play the video for our mutual fuck friends too. Smoke, Drink, Smoke, Drink...

Thankkies Jack :) You're a great friend!

So there i am. Missionary on top of my wife. Fucking away on the living room floor. The camera is on, recording every thrust and grind. Its a slow fuck, her legs around my hips, as i grind into her mons, kiss her face roughly, not moving very much. you see... guys tongue was working us over at the same time. I would feel him bury into my asshole, lick around my balls, then id see her smile and wiggle, he must have been giving her the same.... i remember her spreading my cheeks as he started on my hole exclusively.... fucker ate my ass for like 45 mins straight.... at least it seemed like that. It felt good, but strange. I was hung up on the fact that a guy was worshiping my ass. idk... i was young.... i didn't wanna stop... but at the same time... i wished he was a girl too....idk.

It wasn't until we stopped fucking, when i kneeled up, she kinda led me over to the sofa, pushing my shoulders onto the cushion, as he approached from behind that i realized.... he had been lubing me up!

i was mortified. i started to protest. He was calming and soothing, promising to go slow, to not hurt me, just try it, see if you like it. She was on my other side, stroking me, telling me how much she wanted to see it.. how hot it would make her, to do it for her, stop being a pussy..... and be a pussy.

Trembling, i went down. On my knees, face in the seat cushion, i expected the worst. Probably because of that, he had a bit of a difficult time getting in. It did hurt a little.... but not much. i know i exaggerated the fact, mainly to save my pride, but also to get him to back off before it hurt more. Before i knew it.... i was being rightly fucked.

Ummmm... not sure about this......

NNNNNN!!!!! More Lube!

Oh fuck... i.. uuuuhhhhhh... i.....never... knew.... oh yeshhhhhh!!!!

A man was inside my asshole, using it to get off in. He took my virginity, and was masturbating his load out with my virgin ass. omg. omg. omg. i heard myself moan like a sissy, embarrassing me further. Wife was right next to me, oooohing and ahhhing. She would stroke my dick a bit, but not enough. Stroking... in and out of my ass. Eventually, she got down and under me to suckle my limp dick. idk if she wanted a closer look at my subjugation, or if she was legitimately trying to please me, but at the time, my head wasn't accepting. i didn't know what i had, i didn't know what i was getting. God how i wish i could have that moment back....

Looking back... it was all about her desires....

Thats right you bitch! At least make me feel good too!

OMG...she's sucking me! I'm being fucked!

OMG! She's watchin me get breed! omg, my dickie is so small... i wish he would just cum and be done now!

And then..... he came. He came inside my cunt like a dirty rag. He didn't ask. He didn't use a condom (although... all of our playtime was condom free). He just used my hole. *BLUSH* it was sooooo embarrassing. He pulled out, she wanted to examine me... but i was having none of it. Running to the head, with my fingers over my hole... i sat and let his semen dribble from me. I was sooo humiliated. Of course, i didn't come out until i knew he was gone.

OMG i think he came in me!

A fucking MAN CAME INSIDE ME!

Get it out! Get it out!

Wot does this mean? Am i a faggot now? Am i truly gay forever? A: Yes.

Today.... i would have wiped then sucked out his last dribbles, and eaten his faggot fuck hole as i wanked all over myself in thankfulness for his attentions. The difference age makes...

That was my first time. i haven't been properly fucked in many years since....many years. While my dildo has loosened me... i feel like a virgin again in my mind? Do you think that's okay to say? Can i call myself a virgin again nows?

Panty-wearing princess - EXPOSED!

I mentioned recently that i had been discovered by my missus as a panty luver. Here are the details for anyone who loves to witness a humiliated sissy.....

I told you all about my recent dip into depression. During this time i did try to deny myself the joys of my secret sissy life. What an exercise in futility!   Sure enough... it wasn't too long before i swung the other way and became obsessive again.

I started to wear my panties obsessively everyday. In my home, under my boy clothes, out in public,  no shame, no second thoughts, i was satisfying my inner gurl no doubt . The thing is.... i would get more and more relaxed about the whole thing, i started to get forgetful, and making stupid mistakes.

Observant readers might remember that i have mentioned before how i would on occasion forget i was wearing them, and then, attempt to get into bed, or get changed for bed, in front of my missus. The only thing that would save me was the sudden realization that i have girly pink lace on my bum, and the fact that she wasn't really observant herself. Lots of quick excuses to go to the bathroom, and a quick change was the method for escaping these near misses.

More recently, i would be home, wearing, and forget to change my undies before missus came home from her workkie. Like a good sissy, i would always greet her shortly after her arrival home. During a quick hug, she started to grab at my bum (unussual for her) or occasionally my clitty. More often than not... i would at that moment realize i had forgotten to remove the panties, and i would think "Can she feel the lace, or the leg holes around my cheeks? Can she feel how my clit is trapped tight in the girly front panel?" This of course is followed by panic, a quick excuse to step away, and a quick change in private, lest she fully discover. You may recall, how i had been wondering if she secretly was offering me her girly shirts and tops and panties too that way she would leave them around our bedroom, on my side / furniture.

So, i focused on being smart(er) and would try to slip the panties off as soon as i heard her walking throught the front door. Sometimes, she would walk right up the stairs to see me, so i had to be quick. My method was such: i would slip one leg out of my pants, then the panties, pull my pants back on quick so as not to be caught 'with my pants down' (pun intended :P ) and then, safely, slip my panties down the other (clothed) leg in relative hidden safety. A couple of times..... i forgot to follow through with the last part (removing the stuffed fabric from my other leg - panties bunched around one thigh inside my pajama pants).

Can you see where this is going?

So, one day, a few weeks back at this point, i thought i heard her pull up out front. I slipped the panties down my leg, pulled my pants up, and went into the front bedroom (ours) to look out the windows - sure enough... her car was there. I went down to greet her like a good bf, and everything was fine - or so i thought.

She came upstairs eventually, entering the bedroom. Across the hall, in my office, i heard the bellow that made me grow cold and panic..... "WHO'S PANTIES ARE THESE!?!?!?! THEY ARE NOT MINE!"

*gulp*

I ran into the room, shutting the door quick as everyone else was home. She was holding a the pair of black bikinis with pink trim and silver hearts. They had been in a small pile on the bedroom floor, near the window i was spying from. They must have fallen down my leg to escape off my foot - because i FORGOT TO ACTUALLY REMOVE THEM FROM MY OTHER LEG! ((stupid ass!)) ((And just so you understand a bit better... i'm a partially paralyzed girl, so... i don't have the same skin sensations as all of you - it IS feasible that i could have no idea that fabric is sliding down my leg, tangling my foot, etc)) A quick debate in my head regarding my options.... i knew there was only one... come clean.

*giggles* Toe lover alert! Shamefully, i realize now i should have painted them for that photo session :P

"The-They're.... mine."

"WHAT? What do you mean?!" she asked through slitted, disbelieving eyes.

I explained.... they were my panties. I liked to wear girls panties. I used to try hers, but i didnt want to ruin them, so.... i thoughtfully went out and bought my own. (Trying to gain points for being considerate.)

Of course... she had lots and lots of questions. The first and foremost was.... Why? Do you want to be a girl?

The moment of truth.

I wish i could relate a story of how i came out, was honest and truthful, how i have begun my life as a fully realized cross dresser, with transgender leanings, but... i didn't. I am nothing if not a scared, frightened, cowardly sissy.

So, i lied.

Without trying to replicate the entire humiliating convo, the short story is this: i own panties and wear them because they make me feel good, warm and nice inside, they make me feel 'pretty', sexy, and... kinda girly. (All true of course.) No, i don't wanna be a  girl. (Lie.) No, i don't want to be with men. (Lie.) No, i'm not gay. (Lie.) No, i don't want to be like those 'man-ladies' she sees occasionally on TV. (Lie. Have i mentioned how prejudiced she is against gays? Like, not the extreme 'God hates...' kinda way, more like 'Ewww, i bet she likes girls', or 'Yuck, why does he have to flaunt it, put it in our faces', if she sees two men kissing or getting married or some such.)

So, i lied. Lots. (Yeah, i know - i've betrayed myself, my inner girl, and everybody like me that is dieing to come out - i feel guilty enough about it, so please don't shit on me because of it.)

And... she accepted it. She's confused, no doubt. I admitted to wearing / liking / wanting panties, but i denied EVERY logical reason, explanation, next step that she asked about. OMG - what a humiliating conversation. I stood there with my hands behind my back, head looking down, blushing hard as she quizzed me. I felt aroused and shamed and excited and relieved, and embarrassed and so much like a pitiful sissy.... it almost made the whole experience ... idk... exciting? Not in a fantasy way... more of like.... for a moment... i truly felt like a little girl, submissive to my missus, how i like to feel.... even if she is too clueless to realize, or capitalize on that.

Up side? She accepted my weirdness... and even agreed to wash them for me (as my boy does mine and his wash... so Dad's panties cant really go in my wash) so at least now they're cleaner than before when i had to sneak-hand-wash them in the shower. Now i can wear whenever i feel like. Although, she doesn't want me wearing them outside, for fear of being caught (like the 'car accident / clean undies scenario), of course... i still do.

Down side? She's really curious, and kinda, idk, accusatory? That's prolly not the correct word for what i mean. It's like, her tone of voice has some hidden accusation, some kind of condemnation behind her words. i still wear and have the same habits. It's still kinda shameful, so i don't flaunt it - old habits die hard. She will ask 'Why havent you worn you girly panties lately?' or ' Are you being girly today?' Yeah, it makes me feel uncomfortable. No more than answering tough questions from a Misstress in SL, but still... because its RL, and my missus... there's a certain amount of further humilaition.

Between my panty wearing.... and the recent changes in our sex life.... she HAS to know what i really am inside.

A dirty, kinky, cock loving, submissive, sissy slut!

Maybe, if i play stupid long enough, maybe she will think that i am in denial, and force me to accept and admit the truth. God i hope so... that would make life sooooo much easier.

OH! Two posts in a week!

Been holding onto this webpage for a few pays now.... i like ALL of this guy's vids. I couldn't pick just one to show you, so i thought this may be better. Click the link and sissify yourself faggots!

peternader Xtube profile page!

And now, small sample of your sissy destiny for your wanking pleasure :)

True Sissy Confessions... Or... Overdue Training Update

This summary is not available. Please click here to view the post.

Maybe.... A Little Demonastration Is In Order?

my SL friends and family may be wondering at my recent, shall we saay...'enhanced?'... fasination with ballbusting. While this sissy has never shied away from expressing her desires for some light C&BT (cock and ball torture for those not in the know), this was usually limited to ball stretching, slapping, cock and ball binding, and maybe the occasional self-sounding.

Now i desire to be PUNCHED in the balls... HARD!

i think  it was this vid that did it...

Yeah... just watch it, trust me :P

She Took my Cummies Away From me :(

IDK if ya'll have been payin attention or not, but at the top of the page you can see a counter keeping track of times between my cummies (both gurl and boi types). Mainly.... its a way of self-reinforcement of proper sissy behavior. i quickly discovered that when i had to update my boi cummies more than the sissygasms, that i felt like i was being bad. It became easier to enforce my self denial that way.

Well.... i had gotten up to ten days with no boi cummies.. and i have recently been abusing my pussy more and more in my lust frenzy. i knew (from past experiences) that soon i would be prime for either a large hands free spurt... or i would be able to have a real good cummie as i was playing online with my beautiful clowny fiance`. (Check out my SecondLife posts for more info). i made a promise to myself.. to nicolette... Clowny gets my load... or the VERY least (if i just couldn't wait), a proper sissy self-milking.

Enter the missus.

Hehe... keep reblogging this and lets keep this slut locked up!

Shawna the Bizarre Sissy: Chastity: As of right now I have 18 days of Chastity left.  But that number is ever evolving.  I have several different determining factors that cha...

The Problem With Sissygasms

....is the fact that while they are sooo wonderful and calming... at the moment.. the drive to be fucked never leaves. The desire to be railed until your back pussy gapes and hangs open stays with you.

i Love the clench, the shudders, the sweats, the soft moans, the grind, the heat, the pounding, the racing heart, the waves of pleasure, the girly way it makes me feel. i love everything about sissy (anal) orgasms.

Except the non-relief from my lust.

i continue and continue to fuck myself soo hard, my arm and wrists hurt. i keep chasing the boi spurts that will never come. i shudder over and over, blessed with the ability to gurlcum easily and in multiples. i Love being pounded with a thick unforgiving cock with deep strong pounding strokes as my pussy spasms hard and my cunt clenches down hard and squeezes. When it seems to fade, that's when another ride may take me back to the peak. Up then down, then back up again, over and over, till im left a quivering mess.

The only way i stop is when exhausted, to tired to fuck myself anymore, the threat of being caught, or after all the hot water in the shower is gone. And just when ive relaxed, and lowed my heart rate... what do you think... my greedy hole craves more.

i have literally done myself for multiple hours straight, and then again an hour or two later.. because i am insatiable.

Sissy Needs a Playmate

Are you a sissy?

Are you a sissy lover?

Are you on the East Coast USA? Philly area?

Would you like to play?

This sissy NEEDS a regular... friend. she should NOT be sucking strange dick after strange dick after strange dick and swallowing multiple strange loads. It's too dangerous.

This sissy is looking for a friend. Someone ...close. Someone to help her feel girly. Someone to appreciate her girly mind. Someone to help her shop, and dress, and maybe... assist with her makeup.

If you are a lonely Daddy looking for a regular dump... then drop me a line.

If you are a Mommy looking for a sissy to serve You... then drop me a line.

If you are a sissy gurl too and want someone to share with... maybe someone to guide... please... drop me a line.

This sissy is very submissive. This sissy desires to serve. This sissy has much to learn.

A Mommy who will laugh as She trains my pussy and owns my mouth and humiliates me is one dream. A Daddy who will use my form for His pleasure, who will treat me like the slut he knows that i am, is another dream. A sissy gurl friend i can ask questions of, who wants to share, who wants a loving sister to cuddle and have fun times with, is the dream trifecta.

i...need... to feel like a girl. To have others treat me as a girl. To be desired as a girl.

me... in my dreams

Hit the Jump for my sissy resume'

My Sissy Snack Bag

i don't know where i saw the phrase first... was somewhere on my regular blog visits.... 'sissy snack bag'. i was enthralled by the idea.

Makes my mouth water... for real.

The Sissy Pilot: a reveiw

Sara over at 'Saragirl's Sissy Confessions' is the author of many wonderful works of erotica, the latest of which, The Sissy Pilot i've recently read.

This book is captivating, every page absorbing me into the life of little wimpy Dana, and his hot but neglected wife, Tiffany. It starts out typically enough for the genre, establishing the unfortunate predicament Dana has gotten himself into. He has managed to find himself out of work, living off of Tiff, and with the resulting lack of self esteem, finds himself not being able to perform his manly duties - either out of, or even inside, the bedroom.

Of course he loves her very much and has no desire to see her burdoned.... or unfufillled in any way. What a delicious little set-up.

Soon enough an offer for steady employment falls into his lap.... with one small catch. He MUST appear in everyway, in look and actions, as a beautiful woman. His need for any employment being so strong, and this being a peice of erotic fiction... im sure you can guess what happens next.

The progression from unwilling self-important man to broken sexy unsure sissy is mesmerizing. Every unsure step he takes into the world of crossdressing is a sexy tease into the submission you as the reader can see coming a mile away. In fact... even though the nubile young wife is supportive, and justified in her every manipulation... even to the point of reluctant (or not-so-reluctant) domme.