Sissy All Dressed Up At A Rest Area free porn video

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Sissy all dressed up at a rest area
So, i had a bit of a scary encounter recently. But it was totally worth it =].

I was driving from my home town to the town where i go to school. It is a windy little road that goes right through a big slice of nowhere, with very minimal cell service. And it was night time. I had been all dressed up and hoping to find someone at a local wildlife area that is an OK place to find guy sometimes, but no dice. I am pretty shy, and don't go to places like that much, i am almost relieved not to have seen or been seen by anyone. It was getting late and i had school the next day, so i got in my car, still dressed, and decided to just start driving there.

Now, being that i am not 'out,' i do not usually dress in public, but it was night time and i figured i could change on the way somewhere. So i am driving. Enjoying being dressed up as cars drive by. But an hour or so into the drive i decide i should pull off and change. I pull over at a rest area, not a truck stop or anything, just a bathroom and some signs talking about the area and a parking lot. It is like 2am and i haven't seen any cars in awhile so i get out, kinda take my time leaning in to grab my phone and my change of clothes. Once i have what i need i start to walk over to the bathroom. While i am walking, i hear a truck coming around the corner, and my heart was racing. Half of me wanted to run and get in the bathroom before the truck saw me, but some part of me made me keep walking over at the same pace. Now, i should clarify, i wasn't dressed in like... skinny jeans and a t shirt. I was dressed really slutty. I had the skirt and stockings on from this picture, and a little thin black zip up sweatshirt. And as i am just getting to the door and walking in, i hear the trucks brakes come on, and it turning onto the gravel entry to the rest area...

Sissy all dressed up at a rest area


I am not going to lie, i was terrified. I was cursing myself for not running. I am a small person, by myself, in the middle of rednecklandia dressed like a slut, and some guy in a big diesel truck has seen me. So i go in the womens side of the bathroom and lock the door and i am standing against the door with my heart racing. I am holding a tiny useless little pocket knife in my hand and just waiting, scared, knowing i am probably no match for some big redneck. I hear the door of the truck open and a guy walk over.. and stop. Sounds like he is pretty close outside the door. I pretty much was holding my breath. Waiting. Must have been about 10 minutes of silence. Finally he speaks, in his sort of redneck drawl.

"Hey, you ok in there? Seems like you been in there awhile... "

I was silent.

"You know, im just tryin' to make sure you are ok. A girl dressed up in a cute little skirt in the middle of the night and all, by herself."

Shit. He definitely saw me that's for sure. And god damn he sounds like a creep. I don't know what to do. Wow, i have never really experienced what it is like to be a girl all dressed up walking home or something... fuck its scary that's all i can say. He is probably a horny asshole and might just stay here until i come out. And if he finds out i am not what i appear, he might hurt me. Maybe i could tell him from in here with it locked.. but then he might hate me for it and mess up my car or something, knowing i can't come out and stop him. This stupid little pocket knife is a joke.

"Oh come on girl, i saw you in that little skirt with pink fuckin' frilly socks, *chuckling loudly* you ain't dressed like a prude. Are you tryin' to come out and play or what?"

Holy fuckingg shit this guy is really blatant about it! Fuck. Well id rather him mess up my car then mess me up, so i guess i should just tell him. He is clearly ot going anywhere...

I am trembling and scared and my voice is cracking, but i manage to reply to him "I.. you don't want to play with me, i promise.." im breathing so fast and blushing hard at being forced to tell this stranger about what i am.

"Oh come on, i saw you, you were a hot little number in that slutty little outfit! Don't you tell me i don't want to play!" he laughed loudly. Not really menacingly or anything, just loudly. I was very embarrassed, being called slutty. Although some part of me was a little bit proud.

"I.. am not what you think i am. i mean like. *sighing* Umm. Im just like. dressed? Like dressed up?"

There was kind of a pause for a few seconds.

"You mean like.. you are a guy dressed up like a fuckin' girl?"

"Ah.. yeahhhhh.." I closed my eyes, head leaned back against the door and waited for his response.

An even longer pause went by.

"Shit man.. you even sound like a girl!" Laughing, a little awkwardly. Wow. He doesn't really seem mad.. i don't hear him breaking things or even walking away.. "And.. you sure did look cute in that skirt... I mean.. im not fuckin gay or anything, but any chance ya wanna come out and show me?"

I was silent for a long time. What the fuck. If i go out there... maybe he will just laugh it off and i can go. But.. nobody is here and who knows what he MIGHT do... But he also might get mad if i DON'T come out, and mess with my car or something. He did sound genuinely interested, and not mad when i told him i was a boy.

"Come on baby, im not gonna bite!"

Finally, i just honestly said "I don't know. I am really scared." Immediately i started cursing myself for admitting that, thinking maybe it gave him the upper had or some bullshit. I don't know.

"Oh come on girl, Let me just see you up closer, you have me all curious about you now. I just wanna see ya and then i'll leave ya alone. I gotta get home and get some sleep anyway."

Finally, i gave in. I had no cell service.. and he wasn't wanting to take no for an answer.. and he didn't seem that mean anyway. Plus.. there was probably some part of me wanting to show off... just like what got me into this in the first place!

"Okay.. i am coming out. Please don't be crazy.. or something.."

I straightened my skirt and made sure my lil dicklet was hidden (because, yes, i was hard as a rock =]) and pushed my long curly red hair back. My heart beating in my throat, i reached for the door and unlocked it. I pushed up open slowly. Feeling my face turn bright red before it had even moved open an inch.

He was about 10 feet away as i stepped out under the halogen lighting outside the little cinder block building. He was about 6'2" or something.. pretty blocky kinda guy. Probably an oilfield guy. Brown hair, carhart pants, and workboots. I was probably visibly shaking as i looked at him. He didn't move at me or anything, just looked and kinda started to grin at me.

Finally he said "Wow, you really do look like a girl. And a pretty hot one too!" He laughed, seemed like a friendly laugh. "Hey, don't worry i'm not going to hurt you or anything... but do you mind if i come a little closer?"

I sort of mumbled that he could, not knowing what else to do, so he walked over to me. He looked at me head to foot... god he looked like he was staring at everything he could possibly look at.. because he was. He walked around me.. and i felt a really creepy sensation on the back of my neck as he looked at my backside. I could just feel him staring at my ass. I heard a sort of swishing sound, and then felt warm air on my ass, and i realized he was squatting down and looking at my ass. Oh. my. god. That was such a weird mix of feelings. But i ddin't turn around. I stood there like a shivering statue.

"So ah.. ya got a name?" he asked, seeming to have stood up again.

I wasn't going to tell him my really name so, feeling kind of stupid, i said "Umm.. Ashley?"

He started laughing when i said that. I felt really horrible. He was walking around me, examining me like a freak, and laughing hard at what was in front of him.

Suddenly i felt a hard slap of a rough hand on my little scantily clad ass. It was like an upward aimed slap, coming up below my skirt to land right on my ass, with only a little black lace in its way. I jumped so fucking high with a yelp, and turned around staring angrily at him. But before i could say anything he started apologizing over and over, between laughing of course. I didn't have any words. I wanted to be mad at him but fuck. I was so horny. And he clearly seems to like what he sees.

"Wh.. why did you do that. I mean. You know. I am.. not a girl..and stuff.." I was bright red. feeling really stupid. And he was still laughing at me.

"Oh shut up, you are a girl!" He said... "Come on.. are you sure you don't wanna play? Here let me show you something, since you are out here dressed up like a.. well you know!" *laughing* He unzipped and pulled his pants down. Then his briefs. And his cock poked out.. and god damn he was hard as a rock too. and.. very nice looking hehe. It looked like 7 or 8 inches at least. Not massive but just about the perfect size. and Thick. And it had a sort of massive head on it.. a real mushroom tip. And i was staring wasn't i. Fuck. I looked up at his face.. he was grinning at me, and waiting for me to react. I looked back down at it. So close to me.. almost in my arms reach. just pointing right at me.

"You are dressed like a slut. You know it. You could have heard me coming around that corner and you didn't. You want to be a slut, be a slut!" He stepped forward and put his hand on my shoulder, gently pushing down. And i kneeled. Still looking at it. Getting red again but i didn't say anything, i just kneeled on the cement in front of him, and looked at the big, warm, thick, and somewhat veiny penis in front of my face. Cock. Fuck. And then he put his hand behind my head and pushed his hips forward.. and my lips opened for him without me even thinking. Oh my god i had a big creepy strangers cock in my mouth. Under a halogen light in front of the rest stop bathroom by a road. It was warm. And big. And amazing. and my tongue was NOT shy or scared it seemed. It raced all around the big mushroom head.. sliding underneath the edges of the head... tickling the underside of his cock tip. I slid my tongue to the front of it and felt around for the hole.It always seems stuck shut when i try to find the hole hehe, but i pressed around until i felt it, and toyed with it with the tip of my tongue. I always love trying to taste the hole when i suck for some reason.. i don't know! Don't judge me XD

I sort of snapped back to reality a bit.. feeling more comfortable. I could hear him now, groaning. "mmm thats good... fuuuuck. wrap those pretty pink lips around my cock.." i looked up with my mouth full and saw that he was looking right at me. Not blinking. Staring. Wow... he must genuinely think i look like a girl because he is not closing his eyes or imagining anything.. he is looking right at me while i look up at him with my mouth on his cock. Then he grinned down and firmly pushed his cock into my mouth.. hand still on my head. My heartrate went up very quickly... and i felt the cockhead on my throat. Now, don't get me wrong, i love doing my best to deep throat. But i have never been the queen of that shit. I have to work at it. And i gag a lot. And i can't stay with it all the way in very long, assuming i get it in there. And he had a big cockhead... i mean. i have sucked some BBC that just wouldn't even fit at all and the head of his cock is about that big.

He kept pushing. Ow. FUCK. he kept going, as i moaned and tried to pull my head back.i could feel the head at my throat.. feeling like a solid wall with no chance.. but then he sort of just.. jerked his hips and made a noise *UUgh!* just a bit.. and i felt it. The edges of that big mushroom popping into my throat... and sliding in.

*MMmmm!* i yelled into the cock, feeling a single tear going down my cheek. I gagged a couple times, but he held me. His cock made a great seal in my throat, and after a couple of gags, i managed to settle my reflexes. I have never gotten that far...


"OHHHHh my GOD hahahha" He laughed down at me "You... are a fucking faggot. You know that, right?" he was grinning down at me. All i could do was push back against his hand and glare up at him... not entirely sure if i was mad or grateful for the push and the training. I will admit i WAS a little proud of myself...

Finally he let me push myself off and i sat there.. leaning forward against him, his sloppy slippery cock against my cheek.. just panting and letting all of the saliva drip out. I was saying "Oh my god.." over and over i think. Can't remember too well. I think i stayed there panting for at least a minute. im sure he was just staring down at me with a big smile on his goofy ass face. Ohh my god i have never had my face FUCKED... not like that. And he is so big... god damn this is hot.

Then he interrupted my thinking. he firmly grabbed my curly hair and pulled my head upright. "You better not be sittin there feelin sorry for yourself, you dressed like a fuckin whore and now you are gettin what you wanted right!" The whole time he was holding his cock and slapping it on my face. He continued "And i know you could have pushed back harder or maybe hit me if you REALLY wanted me to stop. No, you loved it.. you little fuckin faggot slut!"

He may have been right. But what i don't think he knew was how much i like being slapped in the face with cock... maybe its my weakness or something lol. Its just... like my submissive side... just loves it. Kneeling in front of a guy and not moving while he does the ultimate sign of putting me in my place. Fuck. I think i started grinning while he was doing that.. just a little. I know that right around the time he said 'faggot' i suck my tongue out... He laughed his ass of. called me some more names. and then said i had better spit on his cock, (it got a little dry swinging into my face hahaha) so i did. And this time totally willing i took this strangers cockhead deep into my throat. He had his hand behind my head again, and this time i reached up and sort of squeezed his fingers around my hair. His face lit up. He grabbed my hair hard and started fucking my throat really hard. My eyes got huge as i wondered what i had gotten myself into. He gave me a break here and there, but fed me his hard cock for awhile. Sometimes he made me lick his balls with it in my throat. Saying disrespectful things the whole time lol. I don't remember exactly you know. But lots of calling me faggot. Saying stuff about how his wife doesn't ever suck, but i suck like it was what i was made for lol.

At one point i heard a truck coming, a big one. i started to struggle to hide but he held my hair hard. "No no no, your not goin anywhere, this is free advertising! you know you want it! Say thank you! hahaha"

I didn't want it lol. i was terrified and embarrassed all over again. I heard a semi horn pull, and saw the truck driving by really slow. He yelled out at us "Damn, you got yourself a REAL cocksucker!" then he accelerated and continued.. Must have had a schedule.

Finally he let me go again. I yelled at him for making a show out of me. He laughed. And then he said i should get up. I did. he put his hands on my shoulders and turned me toward the wall and pushed me so i had to catch myself on the wall. Then his hands were all over my ass. Pinchnig, squeezing, smacking, exploring... i felt like i was being m*****ed. I mean. Well. I guess i just stood there.. and allowed myself to be m*****ed lol.

"You know im going to put my cock inside this tight pink little faggot fuckhole of yours."

"I know."

He chuckled at my quiet response, and grabbed my black lacey crothless panties, and pulled the crotch hole open wide, ripping it until it was a pair of gaping-crotch panties lol.

"Hey dont rip-"

"Shut up." i recieved an abrupt spank. I squealed. I shut up.

I felt my saliva being pressed into my ass on his cock as he lined up.

"Alright Ashley. Remember, im just treating you the way you dressed up to be treated."

Before i could say anything he had his hands on my shoulders, and thrust his cock into my ass. Not all the way... but he got that big fucking head in. I am the annoying sissy who makes you go in slow and moans and it hurts etc... so yeah. I screamed like a bitch. And he put his hand over my mouth.

"Shut the fuck up bitch! I know you aren't a fucking virgin, whats your fucking problem!" He pulled his cock out and spit all over it. Then he fucked me. He grabbed my hair and fucked me. He pulled otu and spit more a few times, thankfully. He said that this was what i get for dressing like a whore by myself in the middle of nowhere. He was right lol.. fuck i was dumb. And it was starting to feel good. And fuck i don't care i think im glad i did it!

He pulled out and walked to his truck without saying anything. "Wh... WHere are you going?" no answer. He laid a blanket down on the truckbed and came back. he pulled me by the hair to the truck and helped me into the bed. He turned me facing the tailgate and pushed me onto my knees, and i realized i was very glad for what he had done. "Omg thanks for getting the blanked that cement would hurt!" He just laughed and said oh shut up, i just did that because im gonna be on my knees behind you, after you suck my cock again that is!" Then he put my face on his cock, and i allowed him submissively to fuck my face again. I was getting worn out. But at least i knew id have put a lot of new saliva on his cock for when he fucks me. Omg. Thats my logic at this point. Fuck i feel like a fucking sex object.

And then he got behind me, his back to the truck cab, and grabbed my hips. I felt that big slippery head push into my fucking pussy. It was so slippery now. So big. So.. in charge of me.

"Fuck yeah! take that big MAN cock you little sissy boy! You will never fuck ANYTHING like im fuckin your little bitch ass right now!"

I heard a noise, maybe another vehicle, and i realized i was being fucked doggystyle and facing the road.. i started to sit up to look and he did something that still surprises me... He hit me. right in the back.. i mean i dunno if i would call it a punch but the fist was closed... i collapsed my arms and my face was back down against the truckbed...

"You know what 'face down ass up' means im sure, so fucking do it hahaha"

I lay there a bit shocked, still loving the cock though.. and just took it. big cock sliding in and out. And there was a crackling of rocks. and an engine stopping. and a door opening.

"Damn, you got that little fuckslut trained huh! I mean.. don't take that wrong, but i mean.. it doesn't look like thats your girlfriend the way your fuckin her hahaha!"

It was a new voice. but i didn't move. My back was still tingling..

"Hahaha this ain't my girlfriend no!! HAHAHA" he was laughing so hard.

"Well shit. Mind if i get some head then?" The new voice asked. It wasn't directed at me.

"Yeah man, this little bitch will suck you like a fucking whore! Well thats probably obvious hahaha"

He pulled his cock out and put it between my legs.. and he slpped it hard up against my balls. I yelped and sat up, and he grabbed my hair and held me there looking forward. There was the new guy. much younger. probably in his mid 20's. He was very eager looking and had his cock in his hand. It was pretty impressive as well. A bit longer, but definitely a bit thinner too. He hopped onto the tailgate and was kneeling in front of me. I felt the man behind me, whose cock was now back inside me, put hit fist against my back. just holding it in the same place he had hit me.

"What do you say ashley?" he said firmly.

I got the message. Panting and a little dizzy, seeing this situation play out around and on me... but i quickly said "I.. please can i suck your cock?"

They laughed and i felt my hair being handed over and my head being taken over by the new guy. He was sort of slowly putting his cock in my mouth. I did my usual.. playin with the hole of his cock and getting to know it.. and then the man behind me slammmed me forward, taking the thinner cock easily into my throat.

"OOOhho my god what a whore!"

"Yeah, thats what im sayin, don't be afraid to really give it to that little faggots face!"

"Haha.. wait WHAT?"

"Yeah... oh you thought it was a girl? no its a fuckin sissy faggot boy! but dont worry man keep goin. I was feeling weird at first but i have been fuckin this bitch for awhile now.. and i feel great man. Its like.. im makin SURE this little faggot doesn't think he is a real man, and makin sure he, or she.. or fuckin it doesn't try to fuck our women! Come on help me train this little fucker!"

He had let go of my hair. But i was sucking. Hard. Working his cock with my tongue and lips. Then he grabbed my hair and looked at my face... laughed and said "Fuck it!" And started fucking his entire length into my face. He fucked me hard, but pretty quickly he was cumming. I pushed him back so the cum shot into my mouth, and i swirled it around. I have always loved cum and im not gonna miss out on it!

The man behind me must have loved watching me eagerly taste and swallow cum willingly, because he put his hands around my neck and fucked me harder than ever. "You god damn faggot! You tried to make me go away earlier and here you are guzzling cum without even being told!"

"AHh AHhh aaeeiii!! AHH! omg IM SORRY! Please forgive me! Ah FUCK! UH UH oh omGGGDDD! YES! FUCK ME DADDY!"

"Uhhh Uhhh yeah take it bitch! NEVER say no to men! Never say no you stupid slut!" Then he pulled out and came all over my back.

I was in a daze. They picked me up and carried me to my car and sat me on the trunk. They talked and joked.. and eventually they both drove away. After awhile i stood up. Panties torn, around my ankle. cum all over me. i felt something on my back and reached back to find a 10 dollar bill with a phone number on it... sticky and covered in tasty cum.

=]





I may have exaggerated some parts hehehe. But definitely not all of it XD

Published by AshleyXmith. All credit belongs to her.

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SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

4 years ago
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Sissy All Sorts

SISSY ALL SORTS by Throne Paul Lockes couldn't believe it. His father's second wife, Tanya, wanted to control the family's money. She had made a good start by dazzling the wealthy patriarch with her sexual creativity, marrying him, and keeping him more than happy. But now she wanted Paul out of the way, so she had drugged him and when he halfway awoke his longish hair was dyed yellow- blond, he was wearing panties and high heels, and she was calling him Goldie. Along with all that,...

1 year ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA. Auntie...

1 year ago
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Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

4 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
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Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
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Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
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Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
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Sissy Farm 20

20 Sissy farm List of Characters. Me. Michelle A Natural transvestite sissy. Janice My Younger sister Aunty Bev Janice and My mother's Sister. Mistress Janet Headmistress of the young lady's academy Doctor Shirley Williams. My endocrinologist. Miranda. A very effeminate Sissy sales assistant. Miss Stern Miranda's mistress who owns the shop. Peregrine AKA Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James AKA Auntie Jamie Peregrine's...

1 year ago
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Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty...

4 years ago
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Sissy Velina

I walk into the living room of my master. I am completely sissified and wear a very frilly sissy maid outfit. My 6" white leather peep too high heels have thick leather straps around my ankles and are closed with medium sized padlocks. I wish I knew where my master holds the keys. On my lightly sun tanned and smoothly shaved legs I wear white sheer seamed stockings and with a nice lace band at the top. At the back the pink seams end with large pink girly satin bows. Just above my...

3 years ago
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Sissy Rules Reads like a proper job description

(Found this on the internet... #65 seems especially made for me) Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows...

1 year ago
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Sissy Rules

Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows big fake titsRule#14: A sissy is a pro cock suckerRule#15: One is...

2 years ago
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Sissy Julian Chapter I Beginnings

Here we go again. Some boys simply are sissies. This is the story of one of them. It is not a story of discovery, although there is much of that, but rather a tale of a lovely boy's trip to self-realization, albeit a tad 'forced.' If lots of frilly sissy boy and girl outfits, super swishy behavior and a little sex, not to mention dominant women, are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fictional fantasy work. No references...

1 year ago
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Sissy Crissi Chapter 3 Leroys Turn

Chapter 3 - Leroy's Turn But Leroy had been left out for too long. Eager for his turn, I had no sooner finished pleasuring my Mistress when I felt his hands reach up under my skirt and start pawing my panty covered ass. Standing behind me, Leroy bent down and lightly held the back of my thighs in the palms of his large hands. He slowly slid his caress upward, off my stockings, across my garter straps, up to where he cupped my round bottom in his palms. He then placed his fingers...

4 years ago
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Sissy discovers Part 5

Part 5 of the story about Sissy and her sexual awakening ****************Brad did not hesitate when invited to go over to Lisa’s. Sissy was not surprised. What young male would not want to hangout with a girl who flaunted her nude body in front of him only hours before. They decided to take the pontoon boat over as it is ten minutes by boat and almost 40 minutes by car. Evening cruses was a family specialty and Brad was good at handling the boat. As they pulled up to Lisa’s family dock Sissy...

4 years ago
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Sissy gracie Life begins anew

Sissy gracie, Life begins anew Chapter 2 As i stood to dress.. the first guy asked me.."So cunt.. you are wearing sissy clothes underneath and all lockedup. Do you have other clothes .. other sissy clothes?" 'ohh Yes Sir' i replied... "Good .. tomorrow.. bring the key.. and wear more.. i want to see you all sissified...... no pants.. just sissy clothes.. prissy dress.. stocking.. high heels.. make up... make your tits look big...... do it up...... and I will hold your key...

4 years ago
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Sissy thoughts 2 Questions From Sissies

1. I am about to have my first experience as a sissy with a Man! How can I make it more special for us both?A: How wonderful! You are at the very start of your new sissy life. It will of course be special and memorable, but to deepen the reprogramming of your still-forming sissy mind, try dressing as a sissy schoolgurl. Not only will it drive your Man wild with lust, but the symbolism of your costume, and the reality of the loss of your virginity will combine to kickstart stronger, more...

2 years ago
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Sissy Farm Chapter Twelve

Sissy Farm - Chapter Twelve By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA....

3 years ago
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Sissy discovers Part 4

the continuing original story of a young girl finding herself****************************Breakfast was filled with the usual mumbles of ‘good morning” and banging of pots, sizzling bacon and gurgle of juice being poured into tumblers. Sissy and Brad avoided looks at each other at first, and then Sissy sat down across from him at the table and patted him on the head saying, “what’s the matter grumpy?” in an exaggerated baby voice. “Nothin’ - hand me that fruit will ya?” He replied and gave...

3 years ago
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Sissy School Part 2

SISSY SCHOOL - PART 2 By Missy Crystal I followed Mistress Mary back to her office. She left me standing in the middle of the room and sat down behind her desk. After ignoring me for a few minutes, she looked up and said, "I told you that you would be severely punished for disobedience." Crap, I thought to myself. I already have six strokes of her leather paddle coming. What did I do wrong? My face dropped. She smiled, "but I can also reward, when I am pleased with your behavior. You...

1 year ago
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Sissy Cruise 3

"We are going on a Caribbean cruise, in two weeks time......." stated my wife Penny. "Oh......Okay," I queried. "With Samantha and Tim," she finished. "Oh really." Samantha is a new friend in my wife's life. They have known each other for a couple of months, but they are already quite close and always scheming together. My relationship is mixed. It seems that the only time she talks to me is to point out my faults which is somewhat annoying. However she is very domineering...

4 years ago
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Sissy New Year

Sissy New Year I remember heading out to a New Years Eve party with a group of my friends from work. I remember stopping by a bar for a few, pre-party shots--well, several pre-part shots. I even recall the super-hot transvestite hooker that winked at me as we left the bar. I don't remember anything else after that. Which explains why I was so confused when I work up a few days later, blindfolded, tied up in a strange bed, with something hard lodged firmly up my ass and a big...

1 year ago
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sissy rules

A sissy must wear panties. He does not own any male underwear.A sissy may wear a bra and pink or brightly colored tights or leggings.A sissy must sleep in lingerie. If he does not have any, he must sleep naked.When alone, a sissy must dress as a girl. Good sissies wear lipstick while alone.A sissy always keeps himself free of facial hair, and is otherwise well groomed. He must always be presentable, ready to please. Good sissies shave their legsEvery morning after he wakes up, a sissy strips...

4 years ago
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Sissy New Year

Author's note: My stories generally featured a lot of forced femme, bondage and kinky sex--you know, the stuff that I keep hoping will someday happen to me. That is still true for this story, but this time around, the author in me decided to spend a bit more time developing the characters before commencing the full-on sissy sex orgy. I also wanted to write a story where the characters are well intentioned instead of simply being a rogue's gallery of perverted bastards. With that in...

3 years ago
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Sissy Farm Chapter TwentyOne

Sissy Farm - Chapter Twenty One - By: Beverly Taff List of Characters. Me, Michelle: A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Doctor Shirley Williams: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine, AKA. Uncle Penny: My transvestite uncle. (Aunty...

3 years ago
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Sissy Tammy

Sissy Tammy It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a child I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games. My...

2 years ago
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Sissy Julian Chapter VI Growing Pains

Sissy Julian - Chapter VI, Growing Pains by: sissystevie Yes, 'tis I, back again. If I can remember how to post this thing on FM. I came across a partially completed additional chapter to this saga, which I abandoned for personal reasons eight years ago, and thought why not? Thus, spurred on by some of your wonderful comments, I completed the chapter and may well complete the saga. There are just too many wonderful kinky - and romantic - moment to come. If you want me to...

3 years ago
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Sissy 101 Intro to Sissy Sluts

Sissy 101: Intro to Sissy Sluts One week before my freshman year at college, I received a letter saying that my class schedule changes had been approved. That struck me as odd because I hadn't requested any changes. Without explanation, I had been un-enrolled from two of my general studies classes. I was now signed up for SISGEN101 and SISHYP161--whatever that meant. I went online to the university's website. These classes weren't even listed in the general course description...

3 years ago
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Sissy Farm Chapter Nineteen

Sissy Farm - Chapter 19 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

1 year ago
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Sissy in the making

Chapter 1 Jim arrived at the North Carolina motel Saturday afternoon as he wanted to make sure everything was in order for Mistress Cleo's arrival on Sunday, as per her instructions. He had gotten the suite to insure there was enough room and comfortable for his new found Mistress. A Mistress he had never met, but already under her control. He began to lay out the items he was instructed to bring, maids outfit, bras, panties, stockings, and every female garment he thought might...

3 years ago
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Sissy Caught at Work

Who ever goes to work thinking "today my life is going to completely change forever". I certainly didn't think that when I got up this morning. I thought I was heading for another typical day at work, full of boring meetings and sipping coffee. Little did I know... My day started like any other, 5 mile run at 6AM, shower, get dressed and headed to work. The only twist is what I'm wearing under my clothes. I love to wear girl's panties. I wear them all the time to work, and today is no...

2 years ago
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Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

3 years ago
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SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

3 years ago
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Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

2 years ago
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Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

2 years ago
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Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

2 years ago
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Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

4 years ago
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Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

3 years ago
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Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

2 years ago
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Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

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