Caught Cross Dressed Part 2 free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
"As Pippa is now completely unable to move her head... I think that we should begin with her eyebrows." Alice told the others.

The others each nodded their consent, and Alice began her work on me. My already thinned eyebrows were plucked pencil thin, and were shaped into a high arch over my eyes. Once this had been completed, Alice tattooed over them, making them a permanent feature of my face!

The tattoo gun still in hand, Alice began working to give me my permanent 'eye-liner' ...by blackening the areas around my eyes with a solid line of black ink. Long, thick, 'long-lasting' lashes were stuck over my natural one's, and were lengthened even further, as she covered them with special 'super-lengthening' mascara! The result of all of her work was that my eyes stood out amazingly... immediately drawing other peoples gazes directly to my face.

Alice changed the colour of the ink within the tattoo gun, swapping it for a deep, blood red... I felt her starting to work on my lips, reshaping and outlining them, so that they would be perceived as being full and shapely, as if I'd used a lip-liner. Alice changed the colour of the ink once more. This time, she chose a bright, scarlet-like 'Ferrari' red. This was the colour with which she covered my lips, careful to remain within the lip-outline that she'd shaped onto my mouth earlier.

I was now certain that I was in deep trouble! The 'feminising' make-over that I'd just undergone was largely of a 'permanent' type. Unlike the times when I'd fulfilled my crossdressing fantasy in the past, I'd be unable to return to being a man once it was over.

'How am I going to return to work on Monday?' I asked my self.

'What will my friends and family say when they see me like this?' I wondered.

'Can it be that Helen and the others intend to keep me 'force-femmed' forever more?' I considered, finally!

"Okay Alice. Now, I want you to pierce both of Pippa's ears, her left nostril, her tongue, and her belly-button. She's to wear large hoops in her ears, so pierce each ear with three holes... I think a stud through her nose, and a bar through her tongue and her belly!" Helen said.

"Shall I do her nipples too? We can replace the falsies over the piercings... but, if you decide to remove them at any time, her titties will still be sexy!" Alice queried.

"Great idea! Yes, let's do it!" was the unanimous reply.

I tried to protest, but the gag stopped me from doing so. Susan noticed, and said:

"I think that Pippa's trying to tell us what a good idea this is!"

All of the women laughed at this.

The piercings didn't take long, and I was soon decorated through each of my new holes. I'd only left a little pubic hair on my body when I'd depilated my body, but I was still a little surprised when Alice waxed me there, leaving only a thin strip above my cock! Next, she removed my wig, and shaved my head... totally bald, before replacing it on my head, and gluing it in place with some strong adhesive.

"She's ready now ladies. Shall we get her dressed again?" Alice prompted the others.

"Yes, let's!" Helen replied.

"You should make her wear your leather studded collar, Helen." Susan told her daughter.

"Oh yes! Good idea." Helen agreed.

I was released, and ordered back into my feminine attire. My gag wasn't removed, and once I was dressed, the collar was placed around my neck.

"Would you like to stay for Pippa's 'initiation' Alice? We would love for you to join us, in becoming one of Pippa's Mistresses!" Susan enquired.

"Yes, I'd love to. It would be an honour and a privilege." Alice responded.

"In that case, Alice... would you and Karen be so kind as to restrain our 'novice' slut? I'd like her tied down... face down, and bent over this large, leather armchair. Tie each of her arms to one of the wooden legs at the front of the chair... with her waist bent over its back, and then separate her legs, using the ankle spreader bar. Set the bar to its widest setting, and secure each of her ankles tightly, using the leather ankle-cuffs at each end." Susan instructed.

"Yes... and then would you use this to lubricate her arsehole? I have a little surprise in store for our new 'toy' girly. Mother and I will only be gone for a few minutes." Helen added.

Mother and daughter left the room, and I heard them climb the stairs, as they went into our bedroom... in search of God knows what! Karen and Alice followed their instructions, and I was soon bent in position, bound and helpless over the leather chair.

I felt both fear and excitement course through my body, as Karen drew my panties to one side at the rear, and began to lubricate my arse ring with large dollops of KY jelly. I jumped, as much as was possible... bound as I was, as I felt her pushing the lubricant up into my arse with her finger. At first there was only one, but I soon felt my anus being stretched, as two... and then three fingers penetrated my rear!

I couldn't believe it, as I felt my cock hardening in response to this stimulation... I felt both elated, and yet shamed and humiliated, at my inability to stop my cock from becoming hard... throbbing wildly, as I grew a rampant hard-on! I knew that this obvious response would only further incite my women captors... but I was completely incapable of controlling my growing exhilaration! Apprehension and horror flowed through me, as I realised that my prick had enlarged to the point where it was now touching Karen's fingers, as she finger fucked my rear end! I could feel it rubbing against them, through the fabric of my Cache-Sex!

At this very moment, I heard the door opening, and Helen and Susan entered the room. Karen blurted out:

"Just in time girls... look at this! Pippa's got an engorged clitty! The dirty little slut is enjoying being fucked by my hand! She's even trying to rub her clit against my fingers!"

"Excellent," Helen gasped, "because this is what I've brought down to surprise her with!" I was unable to see what she'd brought with her, but I heard Alice and Karen gasp... and then giggle at what they saw.

"Who wants to go first girls?" Susan asked, "How about you, Karen? Didn't your 'boss' try to fuck you at the Christmas party? I think it would be ironic if you were his... sorry, HER first, don't you?"

"Oh, yes please... may I? Can we get it all on video?" Karen replied.

"Good idea." Susan said, immediately retrieving the digital video camera from a draw... and placing it to one side, on a tripod... and switching it to record.

"Shall I show Pippa what's in store for her?" Helen asked.

"Why not?" Karen agreed.

Helen walked around in front of me, and showed me the item she'd brought down from our bedroom. My eyes bulged, as I saw the strap-on dildo that was in her hands. A 9" Latex cock, attached to a harness!

"Strip off then Karen..." Helen urged, "And then put this on!"

Karen came round in front of me, and began a sexy striptease, further stirring my rampant cock, and causing me to wriggle in my bonds!

"He wants to be a girl... so... let's show him everything that a girl must do! I seem to recall that these were my words when we caught you." Susan added.

"Yes," Alice piped up, "And let's face it... men always expect their women to service their cocks!"

"It'll be my pleasure to show you how we do it, Pippa." Karen finished.

Naked now, Karen slipped into the strap-on dildo, as Susan tightened it around her waist and hips, buckling it shut onto her groin. My eyes were transfixed, as I watched her Latex penis sticking out before her, as rampant as could be. It was as raging a hard-on as I had ever seen!

Panic swept through me, as Karen returned to my rear. Helen looked over to Alice, and said:

"I have another of those, right there..." She pointed to someplace behind my back. "Would you like to be the next to take part in her training? I was thinking that Pippa's first lesson could be 'The Spit-Roast...' Are you up for that?"

"I'd love it!" Alice replied, obviously excited at the prospect.

"Strip off too then Alice..." Helen urged, "And then put this one on for us!"

Alice too came around to face me, teasing me further as she removed her clothing, item by item... as provocatively as she could. I felt my pleasure rising, as the anticipation of what was to happen to me rose ever more!

Once more, I stared, as Alice slipped into the strap-on dildo... and as Susan tightened it around her waist and hips, buckling it shut onto her groin.

Susan approached each of the women. She handed each one a pair of high-heels, requesting that they don them, and explaining that naked women always looked far sexier in heels. She followed this by whispering to each one, and confirming with each of them what she had planned for them to do.

"Make sure that you get all of this on video, Helen. The girls are going to wear these Ballroom masks, so that they cannot be recognised... but, try to get Pippa's face in shot as often as you can, okay?" Susan said.

Alice and Karen complied at once... donning their masks, and thus hiding their identities from the camera. The ball-gag was removed from my mouth, but was immediately replaced by Alice's Latex cock. I felt my panties being moved to one side at the rear, and Karen gradually began to enter me, pushing her strap-on, gently into my arse. Slowly, I felt her filling my rear... pushing in the cock-head first of all, and then little by little, moving the shaft in and out of me!

I felt the skirt of my mini-dress being pushed up, over my hips, thus exposing my bum-cheeks to view. Karen withdrew the dildo from my backside. I suddenly felt something slapping my cheeks! I tried to yelp, but Alice was still fucking my mouth with her fake dick, and I only managed a muffled:

"Mmmmmmphhhhh!"

"'Pippa must be punished for lying...' I think these were the words I said to my daughter, weren't they Pippa? I also seem to recall saying to Karen: 'I hope that you will be willing to help my daughter and me to teach her perverted husband... Your 'kinky' boss... a lesson that he'll never forget!' Do you remember that Pippa? Well... you are about to receive a lengthy bout of 'corporal punishment' for lying to Helen! A punishment that I believe to be fitting to your 'crime.' A punishment that you are in the perfect position to receive, and so... A punishment that we will administer right now! Alice, until it's your turn, you will continue to make Pippa give you 'head.' This will ensure that she cannot scream, or become too noisy! Once it becomes your turn... Karen will swap places with you, so that Pippa's cooperation is assured."

"Pippa's punishment will consist of her arse being spanked by each one of us." Helen took over the instructions, which mother and daughter had obviously discussed in length whilst they'd been alone upstairs. "I've decided on the order that I want us to use. I will go first, spanking him with my hands... Karen will be second, and will use a leather belt. She will then swap places with Alice, filling Pippa's mouth with her strap-on. She will be third in-line, and I thought that she should spank him with the back of her hairbrush... a nice touch, as she's a beautician! My mother Susan will take last place, and she will use her favourite implement... one that I felt many times in my youth... One that she will fetch in a moment from the tree in my back garden... A bunch of young, bendy birch twigs!"

"How many strokes can we give him... sorry, 'her...' each?" Alice asked.

"Karen, I'll allow you to choose. A minimum of six. A maximum of twenty-four... EACH!" Helen presented my P.A. with the choice.

"A simple choice then Helen. Twenty-four strokes each! Ninety-six in total! Pippa deserves every one of them, I think!" Karen chose.

"Let's get changed first, mum." Susan and Helen left the room. Karen pushed her Latex dick back inside me, and began to pump it in and out of my arse-pussy... much harder than she had before!

About ten minutes later, the door opened, and I heard them return. They strode around to face me, and I was shocked to see them both dressed in leather 'Catwoman' outfits... their faces masked... their bodies covered in skin-tight leather, and with each of them wearing thigh high boots that must have sported at least 8" heels!

Once again, I felt Karen slide out of me. This time though, Helen took up her position behind me. Her hand began to administer my spanking, each stroke falling slowly, and each slightly harder than before! By the twelfth stroke, my arse cheeks were aflame! Still, I was unable to scream! The next twelve fell, covering both my cheeks... and the insides of my thighs!

I noticed that Susan had taken her place by the video... and realised that I was now the star of the show. This was evidence with which they could surely ruin me... or with which they could blackmail me into doing whatever they wanted... forever more!

The whipping came next, as Karen used her belt to administer her strokes upon my bare arse! This time, my bum was hot and red by the sixth stroke... the backs of my legs by the twelfth, and my inner thighs by the eighteenth! The last six were administered to my lower back, and by the end of it, I was sobbing... as tears ran down my face!

Karen swapped places with Alice, and began face fucking me with her dildo. She pushed much further into my mouth, forcing me to 'deep-throat' her latex dick!

Alice obviously relished the idea of spanking a submissive, crossdressed 'sex-slave' with the brush that she regularly used on her clients at work.

"I'll always think of this moment, when I use this brush to style my ladies' hair."

Her strokes were by far the hardest that I'd been given until then. She hit me on my cheeks and on my inner thighs, applying each stroke firmly and rapidly... The entire spanking taking less than a minute!

I hadn't realised that Susan had left the room, until I heard the door opening upon her return! When it did, I realised that I really was about to receive a 'birching' with the twigs that she'd brought in from outside.

Alice came into view, and began fucking Karen with her strap-on! Much to my horror and my disbelief, I felt my cock begin to harden once again! This didn't go unnoticed, and I heard Helen point it out to her mother:

"You'd better punish this slut properly mum, because she's getting all excited again!"

"Don't you worry darling," Susan replied... "I'm gonna take my time with this one! Do you think that this deserves 'double' strokes, ladies?" she asked.

"Ooohhh, yes!" Helen replied, as the others nodded their consent.

'Forty-eight strokes...' I thought, 'I don't know if I can take this!'

Slowly, and with much precision, Susan began my birching! On her twelfth stroke, she moved away, and whispered something to my wife! Helen nodded, and Susan returned... only to rip my knickers off, leaving my throbbing 'clit' hanging down beneath my body! I'd expected her to continue birching me, but before she did, I felt her brushing something the length of my cock... and across my balls. She pulled it away from my body, and showed me what she was using! I tried to scream, but Karen was still gagging me with her fake penis...

"AAAAArrrghhhh... MMMMmmppphhhhh!" I screamed into my gag!

She began to brush my sex organ again... but, this time I knew what she was doing it with! A large bunch of stinging nettles were in her gloved hand, and my 'clit' and balls began to burn furiously!

To my great surprise, the effect this had on me was to increase the stimulation that I was feeling! I began to get even harder than before!

"Thrash her some more... the dirty slag's enjoying it!" Helen called out.

Susan returned to my birching, and bit by bit, I received my final thirty-six strokes!

My punishment over, I was released from my bondage, and made to stand in the corner of the room, with my hands on my head! The four women gathered together once more, whispering animatedly amongst themselves. They pointed in my direction a few times, as they decided how to proceed from this point onwards.

"Pippa... Strip off your dress. We are going to make you wear a different outfit... You look too much like a 'Dominatrice' in leather, so we have decided to dress you in an outfit that is more befitting your submissive status!" Susan demanded.

Complying with my orders, I stripped to my underwear, and waited for my new clothing to be given to me. Helen handed me a pack of folded clothing. I looked at the items that she had handed me, and I blushed... seeing that it was a sexy 'French-maid's' outfit... one that I had purchased a few months before, as a gift for Helen... from the Anne Summers 'sex' catalogue! It consisted of a very short, black satin dress, with a white apron, which covered the skirt of the dress at the front, and had a small bib across the bust area... and, which had a lacy, frilly maid's hat for me to wear! The skirt barely covered my groin... showing the lacy tops of my hold-up stockings, and about an inch and a half of skin, at the top of my thighs!

Susan handed me a pair of thong panties, which barely held my manhood between my legs, and told me to put them on. Alice forced my arms behind me, and cuffed them together, with handcuffs that had pink feathers around the wrists!

"Karen, why don't you attach this leash to Pippa's collar, so that you can lead her around? We wouldn't want her trying to escape when we take her out in public now, would we?" Helen said.

"There is a choice of leather, or PVC clothing in Helen's bedroom, girls. I think that you should choose some, and get dressed. We'll be going out soon, and you can't leave the house wearing only heels and a strap-on!" Susan told Alice and Karen.

Grinning, they both went upstairs to dress.

"Now for your surprise punishment." Susan said, "We're going out for a drink at the local pub." I couldn't believe my ears, they had to be joking, and they were winding me up and trying to scare me. They were succeeding too. "You will obey our instructions to the letter, slut. Don't for a moment think that we might hesitate to punish you, just because we're in a public place. We would and we will, should you falter in your obeisance. Should you outright refuse us anything, we may be forced to let slip a little something regarding your true gender!" The trap was complete; nothing could make me disobey them now.

"Before we go, I think we need a little keepsake of how pretty you look." Said Mistress Helen as she pulled out her camera and snapped off a couple of pictures of my female persona.

"Don't forget the video camera, Alice." Slipped in Mistress Karen as she pulled open the front door.

"Just one last thing that you should know, Pippa." Said Mistress Alice glibly. "The pub that we're going to is a Biker's Bar. I don't think that they'd be too impressed if they found out that you have a dick hidden between your legs. Let's go girls." She smirked at my patently obvious horror, as I was lead into the street.

Blushing visibly through my make-up, I considered running away and ending this horror but remembering the photos soon put paid to that idea. I couldn't believe that this was actually happening to me. My mind was racing with fright as I though of the serious assault that would surely come my way, if and when I was discovered! I shuddered involuntarily at the scene in my mind!

"There it is." Signalled Mistress Alice, as she pointed to the next corner on the street. "It looks like it is pretty busy too, if you stop to consider the amount of bikes that are in the car park."

The place was loud and rough looking with a large car parks both front and back. The rear car parks lead into a garden area that was dark and seemed woody, with trees surrounding the drinking area. My mind raced as my wife turned and said to us all:

Same as caught cross dressed part 2 Videos

2 years ago
  • 0
  • 33
  • 0

Crossedressed In best friends mom clothes 22

Part 22The taste of cum and her sweet saliva was so good. Feeling her soft tongue twirl around mine was just the best feeling. I was for real kissing the women I had a crush on for a while now. It was magical. Mmmm, I open the buttons on her beige silk shirt and pop one of her big breasts out of her black bra. We stopped kissing and we were both breathing heavily from the excitement."Wow, Caroline...you're a really good kisser. Please untie me, sweety!"I got up and untied her hands and feet...

4 years ago
  • 0
  • 21
  • 0

Crossedressed In best friends mom clothes 21

Part 21My whole body felt warm inside when he talked that way about me. He knew that I had a tiny dick from the start, and I was treated like a princess. I totally blushed “Th...Thanks...Ehm!”Then the waiter came with some ice desert with some strawberries on the side.“Can I ask you something, Caroline?”“Sure!” I picked up a strawberry and put my dark red matt lips around one. Mmmm, they were juicy and full of flavour. It tasted so good; I closed my eyes as I took another bite.“God, you’re so...

2 years ago
  • 0
  • 21
  • 0

Crossedressed In best friends mom clothes 20

Part 20We stepped out of the car and inside. Such an old yet classy place. Noah came with the suitcase. Lauren was talking to the receptionist and was handed 2 keycards. She turned around and gave me one.“Here, Caroline. The room number is on the card. Do what you like. I need to go with Jonas and Noah to their tuning factory to check up on some things. It's very important that this racing deal goes smoothly. So don't wait up for me!”I nodded “Ok miss. What about your suitcase?”“Take it into...

3 years ago
  • 0
  • 36
  • 0

Crossedressed In best friends mom clothes 19

Part 19I woke up rested and feeling great. I went to bed late and woke up around 16:00. Luckily for me it was Saturday. I have just been in the shower, and cleaned my pussy good from Jan’s cum. As I was done with that, I turned on the TV and made myself a cup of coffee and saw my phone had received a text message.Afternoon Caroline. Put on some burgundy red nail polish. And do your makeup in the same colour theme. And put on some white opaque pantyhose.I went to the bathroom and took my...

2 years ago
  • 0
  • 28
  • 0

Crossedressed In best friends mom clothes 18

Part 18As I walked out of her office, I found my way to the elevator and went down again. I left the building and thought about her gorgeous nylon feet that I’d just massaged. I smelled my fingers and crossed the road to my parked light pink ‘Royce’ outside the cafe. I was so freaking horny thinking about her pretty nylon toes. I saw a girl with her friend taking pictures of my car. I unlocked the car and was about to get in, but then I thought ‘I’ve got black tinted windows all over’, only the...

4 years ago
  • 0
  • 45
  • 0

Crossedressed In best friends mom clothes 17

Part 17Well a text was showing on my TV again...That was fun to watch. Seeing Jan cum in his pants was kind of a surprise to me. He ran out like a little boy. I know how much he loves those pantyhose of yours. He was in your apartment while you were taking your driving licence.“What...? What do you mean?”Look at this.A video clip was showing onscreen. Watching Jan enter my apartment. There were multiple camera angles following him across the living room and straight into my bedroom. I saw him...

3 years ago
  • 0
  • 35
  • 0

Crossedressed In best friends mom clothes 16

Part 16He turned around and saw me sitting there on the bench with my champagne. He got a beer from the fridge and sat back down on the chair. He opened the beer and it foamed over. He drank from it and looked happy. “So I’m gonna tell you, Caroline...it was fun playing along, but did you really think you were the dominant type? Inside, I was laughing of that foolish attempt. How pathetic! I feel so tipsy about now, and you teasing me all night, made me so fucking horny. I think I’m gonna take...

4 years ago
  • 0
  • 29
  • 0

Crossedressed In best friends mom clothes 15

Part 15Oh god, this could not be happening!“Mmmm...aren't you a cute little girl?” She got a tight grip in my light pink hair, and pulled my head back. “I see why my useless thing of man wants to fuck you! Harrold, you need to pleasure this girl. Or can you not even do that right?” She looked at Luis, just laying there in the middle of it all, with his big black cock out, but she didn't care. “Does it feel good while my husband is fucking your tight little pussy?”Harrold got turned on, and...

4 years ago
  • 0
  • 26
  • 0

Crossedressed In best friends mom clothes 14

Part 14“Candy it is!”We had been driving for around 2 hours, mostly on the highway.“I'm getting hungry. Let's take a break!”“Yeah, I could really use a coffee too!” I said.“Good! Let’s hold at the next gas station!”After 10 minutes of driving, we turned off to the gas station and found a place to park. He quickly jumped out and got my heels for me, and opened the door for me again.“I got you, Candy! You just sit there with your feet turned to me!”I turned around on the seat. The car was pretty...

1 year ago
  • 0
  • 45
  • 0

Caught Crossdressing by my wife

Caught Cross-dressing by my wifeCaught cross-dressing by my wifeI have always been a cross dresser and enjoyed it. When I got married I put all my special clothes in the basement and lived a normal life. One day I was home from a trip early and found my wife was doing the laundry. There on the top of the pile were her pink knickers. I remembered I loved the feel of silk on my body. She left the room and I picked them up and I was running my hand across them and soon I was feeling and rubbing my...

3 years ago
  • 0
  • 44
  • 0

CrossDressed Fairy Tales 3 The Adventures of Pierrot

Cross-Dressed Fairy Tales Part 3 By Dawn DeWinter In parts 1 and 2, Sherry and Sadie, two married men, went to a lesbian bar on their "girl's night out." There they came into the clutches of Mike and Big Sue, and are in danger of being raped - or worse - if Sherry cannot keep Big Sue entertained with "original" stories. This task has just become a mite more difficult with the arrival of two more people. Can they too be kept satisfied? Part 3 is based on Pinocchio, the story of the...

3 years ago
  • 0
  • 20
  • 0

Caught cross dressed part 1

My name is Philip. I am married to a beautiful woman called Helen, and a few days ago... I did something very stupid! My wife, her mother, her beautician, my P.A. from work, and any of their friends, (in fact, anyone that they choose,) are now completely in control of my life. They are my Mistresses, and I am fully subservient to their every desire. In fact, I am now nothing more than their sex-slave!Recently, whilst I thought that my wife was visiting her mother, and would not be back all...

3 years ago
  • 0
  • 28
  • 0

Crossdressed By Friends 8211 Part I

I have been cross-dressing since the age of 15. I like to wear saree, suits and lehngas. This is a story about me getting dressed up by my friends when I was doing my engineering. My group in college consisted of 3 guys and 3 girls. The girls were all staying at their places and I had rented out a place in the city with my relatives. Two of my other friends used to stay in the boys hostel. This incident happened in the third year about a month before the exams when the guys had gone to their...

Gay Male
2 years ago
  • 0
  • 23
  • 0

Cross Dressing Cock Slut Party

Sadly this wonderful story is just a fantasy, but who wants to make something similar a reality!?!The evening had taken a while to arrange, but had finally arrived. All 5 guests turned up within 15 minutes of each other and as they did, I fixed them a quick drink and showed them into the living room to get to know each other. Alan was a suited businessman in his mid thirties. Dave and Brian were dressed casually in jeans and Tshirts and both in their mid forties. Jeff and Keith were my age,...

2 years ago
  • 0
  • 31
  • 0

Caught Crossdressing by Aunt Sharon

Caught Crossdressing by Aunt Sharon Story by Kresha Matay "I wonder where Brad is? He knows you're coming, you'd think he'd stick around. Oh, I hope he'll turn up soon, otherwise you'll have to drive back in the dark." "Rita, don't worry about the boy so much. Brad is like every other sixteen year old boy. He's probably driving around with his friends looking for girls and forgot I was coming!" "Well, aah, I don't think so!" His mother stumbled to say. "That's something you and I...

1 year ago
  • 0
  • 49
  • 0

CrossDressed Fairy Tales Snow White and the 7 Trolls

Sherry and Sadie, two married men, have a girl's night out at a bar. The evening goes badly and, like Sheherazade, who related the 1,101 tales of the Arabian Nights, they end up in great danger, desperately spinning stories to protect their derrieres. For material, they transgender fables they have read, hoping that their captors won't know the original. Will this strategy work? It will depend on you, the reader, because Sherry and Sadie will soon run out of ideas unless you...

3 years ago
  • 0
  • 18
  • 0

caught cross dressed part 3

The next few days felt like a lifetime for me. I couldn't sleep at night - every time I closed my eyes, all I could see were replays of myself, dressed like a whore, being strapped to a padded sawhorse while it fucked me from both sides. Everything I ate and drank had a horrid aftertaste of that bastard's cum - it was as if that taste was permanently embedded in my ataste buds now. The back of my throat was sore so it hurt to speak and my pussy... no, my ass, as I had reverted back to calling...

4 years ago
  • 0
  • 143
  • 0

Xena Versus The Spartans

It was a time of horrible raids by terrible marrauding hordes, which caused untold misery, fear and poverty in all of Pelopones. It was a time when Xena and Gabrielle were needed by all the towns, before it is too late, but she was nowhere to be found. The century before had been a good time for all, under the Cooperation Accord of Olympia, there was piece between all the polises, and Xena could concentrate on petty crime and feuding Gods. But now Xena had been on a mission in Asia for years,...

4 years ago
  • 0
  • 21
  • 0

The Cross She Bore

Memories are sometimes not to be trusted. In looking back on the past, what one believes to be a memory is in actuality what one prefers to think the past was like. We do this unintentionally -- whether as a defensive mechanism or the result of the layering of visions of the past, one on top of another, until the distant past is obscured. For Rebecca her fascination with the cross and with the practice of crucifixion seemed in retrospect to have been acquired at an early age. Now as a single...

3 years ago
  • 0
  • 18
  • 0

How I started Cross Dressing and other first times

I love to cross-dress! I love everything about it!Like most of us cross dressers, I love everything about ladies undergarments. I like seeing lingerie in ads, in stores, on models, on TV, on women, on men and of course on me! I love the feel when I am dressed up. I love the taboo of wearing them. I love the thrill of being “underdressed”, which is wearing lots of lingerie under your manly clothes, when I go to work. I especially love the incredible horniness and lack of all boundaries...

4 years ago
  • 0
  • 22
  • 0

Cross Dressing Led To Sexual Heaven 8211 Part 1

Addiction lets you do anything.. I addicted to cross dressing, addicted for the femininity.. Hi, I am 24 old close door part time cross dresser from Mumbai, regular reader of ISS. Narrating my own story for first time. I am good and beautiful looking, 5’3” height, perfectly slim as like every “women” wants to be and every man feels to hold, as I kept it with having exercises and yoga because I feel sexy with it.. I started cross-dressing when I was only 12. I haven’t knew it was called as a...

2 years ago
  • 0
  • 17
  • 0

My Dream Of Cross Dressing Came True

This is my first story so please don’t mind and few pieces are real in this story. I will start with story rather than boring you and when I was a kid, I used to love smell of woman’s bra and panties and when that smell turned me into cross dressed I did not realize. By the time I hit my puberty I was very excited about cross dressing and used to cross dress whenever I used to get any chance to cross-dress in private. Soon after and I joined an engineer college which was mostly dominated by...

Gay Male
2 years ago
  • 0
  • 35
  • 0

Not Quite a White Knight Book 1Chapter 10The XCross

Bondage and sex machines usually take a lot of time and co-operation to set up. But that is not my style, so my machines were selected for me to use alone with a guest, and quickly. I led Gracie to the machine I decided to use next. The cross is a standard in many playrooms, but usually these require three strong people working together to use effectively, and they often injure somebody getting the occupant into position. Plus they never do what you expect. A lot of risk for not much...

2 years ago
  • 0
  • 21
  • 0

Cross

Darren closed his eyes and rested his head in his hands for the umpteenth time that day. How could he have been so stupid? He’d always been the careful one out of every crowd he’d been involved with. Coming from a dirt poor background, he knew the smallest thing would mar his reputation and he would be screwed for the rest of his life. His whole life, he had been a straight A student. Before graduating high school a month ago, his scholarship at Princeton had already been confirmed. One night...

Gay Male
3 years ago
  • 0
  • 14
  • 0

Caught Cross Dressing by my daughters friend

I stop suddenly as I here a noise downstairs. No-one is home I am thinking whilst my heart races. Everyone is away for the day. I have phoned up to check. Both my wife and daughters are in London shopping so who the hell is that in my kitchen. I look over into the full length mirror and catch a glimpse of myself. The door is over to the corner of the room and as I walk I pass the mirror properly. Even in my panic I look at myself and think. Hell I look good. The reflection is myself dressed up...

1 year ago
  • 0
  • 74
  • 0

BiSexual Cross Dressing Cuckold

My bride to be cheated on me as a girlfriend, again when she was my fiancé, and thereafter as my hot wife for 23 years. I guess the stars aligned for us.Me-For some reason I turned to slutty, tight black satin gloves in bed, without ejaculation, a year before I accidently discovered masturbation and gushing in the bathtub. I was 12 the first time I ejaculated, rubbing my cock with slippery shampoo. An overwhelming surge of floating and pleasure washed through my virgin boner as my sudsy palms...

4 years ago
  • 0
  • 34
  • 0

My Road to Crossdressing part 2

I had dressed up since I was a teenager but it was only occasionally. Usually, it was just lingerie and it was always for me and just for masturbation. It was about ten years ago that I decided I wanted to go further and start using makeup and breast forms and wigs etcetera.Quite by chance one day, I rang an old friend just for a chat. I found out that he had rented his house out while he was travelling. The person on the other end of the line was a woman, or so I thought. We got talking and I...

Crossdressing
3 years ago
  • 0
  • 19
  • 0

Cross Burning For Dummies

To “Hardcore” Hardaway’s way of thinking, the three snot-nosed young farts standing just inside the door to his cluttered work shed didn’t look good for much, most of all a Klan job.At first, they’d tried to act cocky, like this wasn’t no big deal. But none of ‘em said a word after seeing the cross he’d put together that afternoon. Now he was back out here trying to teach these whelps a thing or two while the half-finished can of beer he’d left inside went flat.Why in hell did Jack Tidwell, who...

Humor
4 years ago
  • 0
  • 22
  • 0

Karl to Kayla Cross Your Heart

This is my first attempt at this so, please be kind with your reviews. Email your comments to me at '[email protected]' Karl to Kayla - "Cross Your Heart" By Kayla Eastcock Eatscock My name is, or should I say 'was' Karl Eastman and it all began one evening while I was at work. I am an average looking 26-year-old guy. Short, sandy-brown hair, blue eyes, 5'10", 145lbs. Okay, so I was a little thin, no big deal. Over the past few months, I had developed a bad habit...

1 year ago
  • 0
  • 18
  • 0

A Proud Cross Dressing Gay Male Who Enjoys Sex Free Sex Stories and Adult Erotica Stories

When I was 12, I went to shop for shoes with my mother. I would walk around the store, making my mother laugh out loud. The onlookers at the store, would often look at me in astonishment and wonder, “How is this little boy handling pencil heels so well”?. My mama knew it back then that I was born different and she fought the world to make me who I am today, a proud cross dressing gay male. It was my first prom and I was nervous. I was worried that I will be made fun of at school, but my mama...

Cross Dresser
1 year ago
  • 0
  • 16
  • 0

My neighbor blackmailed and fucked me for Cross dressing

I had recently moved in a townhouse unit in Oklahoma. Still trying to adjust to the new neighborhood, I was also doing my best to keep my hobbies a secret. You see, I am a cross-dresser by passion. But my new neighborhood is strictly catholic and I can imagine the uproar my fantasies might stir. My next-door neighbor was an old man in his 60’s. He looked younger and stronger than his age. But, my secret unfolded and the neighbor fucked me for cross dressing. Within a couple of days of...

Cross Dresser
2 years ago
  • 0
  • 17
  • 0

Aunty cross dressed me

I’m James from Mumbai. I am a very sexual guy 26yrs old. I love to cross dress and love to be like a woman while having sex. After reading this story please contact me on Any woman who fantasize of man dress like a woman to fuck her can also contact. Lets me begin the story. This happened in the month of January 2009. I had started surfing the net on a very regular basis at my work. One day I went to a social network site and just typed out girls who wanted there an to dress like woman and...

Incest
2 years ago
  • 0
  • 29
  • 0

Cross Dressing Lover

The weekend started off the same as any other for Dhiren. He threw off his drab male work clothes with alacrity and stepped into the shower. He shaved his face, legs and pubic area as was his custom, then, after turning off the tap, moisturized his legs, stepped into a pair of lacy pink panties and hooked on a matching bra. The feel of the light, soft, feminine fabric had always been a thrill to Dhiren, ever since that fateful day when, aged fourteen, he found himself alone in the house all...

Gay Male
4 years ago
  • 0
  • 21
  • 0

The Priest Teaches His FlockChapter 10 Sally Rides the Cross

Father John hadn't even said hello to Sally. Pulling her along the corridor again, Sally knowing that they were going back into the basement again. She shuddered when she saw the cross. It was huge, standing over eight feet high, four feet wide, made out of heavy wood. It was a little strange for a cross, it looked like it was upside down, the cross piece lower down the upright, not near the top like a normal cross. At least the altar was gone, but she feared the cross, not sure what it...

4 years ago
  • 0
  • 26
  • 0

Crossover

Crossover Janet L. Stickney [email protected] There was never any doubt that I was going to be a girl someday. I mean, from early on I would wear pale lipstick and eyeliner with my hair usually braided. Then came the Crossover week and I was able to dress like a girl from the skin out, complete with hips and boobs. My father was a drunk that never cared what I did, and my mom was long gone so how I dressed was never an issue. I work at a small shop that makes and repairs video...

1 year ago
  • 0
  • 44
  • 0

CrossDressed Fairy Tales Rapunzel

Some familiar fables transformed for readers of transgendered tales. In part 1, Sherry and Sadie, two married men on a "girl's night out" visit a lesbian bar and go home with Big Sue and Mike, two women who are dangerously upset to discover that they've been seduced by two cross-dressed males cheating on their wives. Like Sheherazade in the Arabian Nights, Sherry decides that the only way to protect their -- um, posteriors, is to entertain Big Sue with fabulous stories. ...

4 years ago
  • 0
  • 134
  • 0

A Cross Dressing Fantasy ndash Chapter 5

A Cross Dressing Fantasy – Chapter 5In the low light of our bedroom, late on that Friday night after Beth had transformed me from a former cross dresser into her new girlfriend she had asked if I liked being her girlfriend. I did not hesitate for one second, “Yes Beth,” I said lying naked against her naked body, “I love being your girlfriend, something inside of me seems to have changed and this seems so natural and I feel complete.”My crotch was wet with my cum and her creamy arousal but I was...

4 years ago
  • 0
  • 31
  • 0

Young Cross Dressers Secrets

Young Cross Dressers Secrets *Sandy was busting at the seams to tell someone some very exciting secrets she was keeping. She couldnt tell anyone she knows. She decided to tell them here. __After reading My Bra and Panties are Missing, my own real story kept nagging at me to be told, but I wasnt sure how. I decided to change all the names and write a story all about this secret world I stumbled into. I started getting very horny just thinking about all that had happened&hellip,. __My story...

1 year ago
  • 0
  • 17
  • 0

Dogging Cross Dressing and Porno

This new friendship proved to be fun and fulfilling, the girlfriend and the wife quickly became best buddies and the location of our nights together changed to her house. If we had nothing organised and they were free we spend Fridays or Saturday evenings in each other company. Usually just talking and drinking but more often than not some form of sexual encounter. Even vanilla fucking was done in each other company and the girls enjoyed playing with each other exploring the lesbian side of...

2 years ago
  • 0
  • 27
  • 0

Confessions of a Sex Crazy Cross Dresser Part 4

Hi Everyone, I hope you like these chapters, please let me know if you want the next two. Chapter 7: Triangle of Fun I slept great that night with a full stomach of drink, food and Peter’s cum. I woke up on Friday and thought this is going to be a hell of a weekend. I played around with my cameras and had finally figured out how to use the self timer on the 35mm and how to use all the options on my movie camera. They were both relatively new as I bought them in Phoenix, just before moving...

2 years ago
  • 0
  • 21
  • 0

Confessions of a Sex Crazy Cross Dresser Part 4

Hi Everyone, I hope you like these chapters, please let me know if you want the next two. Chapter 7: Triangle of Fun I slept great that night with a full stomach of drink, food and Peter’s cum. I woke up on Friday and thought this is going to be a hell of a weekend. I played around with my cameras and had finally figured out how to use the self timer on the 35mm and how to use all the options on my movie camera. They were both relatively new as I bought them in Phoenix, just before moving back...

Crossdressing
3 years ago
  • 0
  • 48
  • 0

Crosstraining

Cross-training Belladonna "Are you ready, pet?" "Yes, mistress," George Bloom responded as Celene knocked upon the iron door. George heard the loud clink of the old fashion knocker upon the door as he pulled at the hem of his short skirt. He anxiously waited for the door to open, hopeful that he would not be noticed by those passing by on the street below the staircase leading to the porch he was standing upon. George had never been to a Dom-sub party like the one that his...

3 years ago
  • 0
  • 44
  • 0

A CrossDressers tale

You may think of me as Fiona, and I am a cross-dresser.A story by Erica inspired me to pen my saga of cross-dressing. I am also a recovering alcoholic, with a few days over 19 years without a drink as I write this, and I suppose the two tales are intertwined to some extent. Not that I am a saint by any means, a lot of people with a lot less time have a better sobriety than I. But I learned that alcohol is a poison to me, so I avoid it. I just do irrational things when I add alcohol to my...

2 years ago
  • 0
  • 30
  • 0

First Time a Cross Dresser Gets Laid Pt 1

Mark was a shy guy who had always found it difficult chatting up girls. There was always some reason. He didn’t like their hair, or their body, or their look, or their personality, or his family would not approve. His upbringing was very conservative, old fashioned and his stoically minded, overbearing, controlling parents, forced their ideology on him. This had left its mark on him and he was a nervous, timid person. Any idea of an alternative life style was just not something he could do or...

First Time
3 years ago
  • 0
  • 30
  • 0

Rex of Great Cross Chapters 1 and 2

The town of Great Cross was named for a towering monument that never existed. The founders had talked of making a bid to become the state capital, and the cross was meant to be a declaration of their ambition. The ambitious talk was more fun than the actual work of building would have been, however, and no great cross ever materialized. The town reached a stable population of about four hundred, which varied up or down by only a few dozen as decades and generations came and went. Few who...

2 years ago
  • 0
  • 22
  • 0

Bound to the cross

I had thought about being a helpless damsel in distress ever since I was a teen.   But, the years had passed and I had never had the opportunity to actually live out my fantasy.   I had talked to a few close friends about it and they all seemed to say the same thing.   I was sexually repressed and the thought of being under someone’s control was my way of coping with the fact that I was really afraid of sex, of voluntarily being intimate with a man.     I had been looking at articles and...

1 year ago
  • 0
  • 17
  • 0

Bound to the cross

I had thought about being a helpless damsel in distress ever since I was a teen.   But, the years had passed and I had never had the opportunity to actually live out my fantasy.   I had talked to a few close friends about it and they all seemed to say the same thing.   I was sexually repressed and the thought of being under someone’s control was my way of coping with the fact that I was really afraid of sex, of voluntarily being intimate with a man.     I had been looking...

BDSM
4 years ago
  • 0
  • 20
  • 0

Judith on the Cross

Judith is one of those lapsed Catholic girls who always wants to get back at her upbringing. She hates the self-righteousness, the paternalism, the hypocrisy. Before she could even spell those words or deconstruct the messages, she was a fervent non-believer. But the hidden messages of The Church still have a powerful resonance to her. A religion built around death. One that had dispensed it in quantity, too, through most of its history. It had an undertone of eroticism, a fascination for her...

2 years ago
  • 0
  • 15
  • 0

Fall Cross Country Fall of a Marriage

My name is Mike Cosby. I'm about 5'9" 170lbs relatively fit and trim and my sandy blond hair and green eyes kind of stand out. When I was in college and in high school, I was never the biggest guy around so I went into some of the peripheral sports. Instead of basketball or football I ran track and cross country. Running cross got me respect in school if not star status. Even for cross country and track, I was never the star on the team, but also never the dog. I was a solid middle of the...

3 years ago
  • 0
  • 45
  • 0

Beastly Isekai Tales of the CrossBreeding SlutPrincess 1

The Guildmistress eventually calmed down, a few deep breaths away from lucidity. She eyed the cursed woman, making absolutely sure no apparent disgust appeared on her face, otherwise the poor thing would lose it. She knew Livia would break the second she hear it, just like she herself had so long ago; it had taken her nearly two decades to fully accept it. But this was different - it was too much to bear for a poor soul. Her life, their lives were in danger; she had a job to do. "Livia,...

1 year ago
  • 0
  • 23
  • 0

Aunt Convinced me for a cross dresser romance session Free Sex Stories and Adult Erotica Stories

Hi, my name is Sam and I am a 26-year-old, slim physic cross dresser. I am a fashion designer and have a thing for female clothing. Not only I love designing female clothes but I also enjoy dressing as a girl. Coming to my story, this incident took place some years back when I was around 20 years old and had cross dresser romance session with my real Aunt. With fair and curvy physic, I can look more girly than a girl with my cross dressed attire. On one weekend, I went to my aunt’s place...

Cross Dresser
3 years ago
  • 0
  • 23
  • 0

True tales of submission and crossdressing Chapter Two William

Introduction ------------ Following on from my first instalment, here is another true story. As before, I have tried to remember events as accurately as I can, but of course all speech is paraphrased. I hope there are people out there who enjoy reading this, and perhaps it will inspire people to go ahead and indulge their fantasies. Whatever your kink, there's probably someone out there who will be into it too, and it's not a crime to enjoy life! Curiosity... ------------ So...

3 years ago
  • 0
  • 31
  • 0

CrossFeed

Cross-Feed --------------- This is the first story I've written in a while. I have started several stories, but put them on the back burner because I just can't find a good ending for them. I always want to get a story 'just right'. Anyway, here's my latest installment. There is really no TG or cross dressing in it, but I feel it belongs in the genre in a weird sort of way. I hope you like it. --------------- He was a stallion, and she rode him hard. He did not...

4 years ago
  • 0
  • 29
  • 0

True tales of submission and crossdressing Chapter One Meisterin

True tales of submission and cross-dressing : Chapter One - Meisterin It is my intention to write a series of true life stories, detaling various encounters and adventures I have had. I know the site's called "Fictionmania", so I hope my contributions are not unwelcome. The stories are not as racy as most of the fiction posted on here, but remember than these stories are real, and described to the best of my memory (of course all speech is paraphrased). Hopefully the fact that these...

4 years ago
  • 0
  • 28
  • 0

Story Treatment TerriTerry and the Cross Time Pirates

"Satirizing reality, since time travel is impossible! and we needed to make a few bucks" Terry and the Cross Time Pirates is a twisted reality show. The plot line fills in what they are trying to do in bits and pieces that are made up situations involving advertisements that bookend the show all being for none existent products and events. A skewed sense of absurd paradoxes presents this crew of would-be crooks trying to run a scam and make lots of money off of it, but they are also...

3 years ago
  • 0
  • 19
  • 0

forced to cross dress on Halloween

Halloween is a great reason to show your submissive side and cross dress for your mistress. Other than writing these articles and stories, I also enjoy dominating my partner.This Halloween was no exception and I wanted to share this exciting day with you. Below you will find a story that is heavily based on the events that took place in my house this year.***I could tell he was anxious. Informing him about the Halloween party raised a lot of questions on his end which I skillfully either...

4 years ago
  • 0
  • 34
  • 0

Crossdress dreams come true

A seductive CD fulfills some of my secret fantasies. And I bring him pleasure into the bargain.Jeez, you bust your ass all year to be among the top sales people so you can get invited to the annual conference. Supposed to be in Hawaii or Vegas or somewhere exciting. And what happens? The company needs to save some money and holds it in the city where it's based. Cincinnati. For fuck's sake. I nearly didn't bother but there'd been some lay-offs already this year, so I decided I should go. You...

2 years ago
  • 0
  • 30
  • 0

Friends With Benefits 8211 CrossDressing

Hi sexy people. Hand shake to guys and boobs shake to girls. I appreciate your comments on my previous stories. I’m going to narrate one more story which could be few people’s fantasy – Cross dressing. So let’s get started. Well one day I was hanging out with my fellow colleague Sindhu. We were quite close, as in, we have had sex couple of times earlier. But we were not committed. In fact she had a boy friend who was still a virgin. That means Sindhu never had sex with anyone else. We were not...

Porn Trends