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Halloween Flirt By Alice Barry I was just going to stay home and have a quiet night by myself when I received an email from my friend Debbie to come to a birthday party at her home on Halloween. I had been to her birthday bash before. She goes all out encouraging outrageous costumes for her Halloween birthday. I think I was invited because of my reputation for fantastic desserts, not for my friendship. Debbie and I had dated for a while several years ago, but it never went anywhere. I guess she just did not excite me. For days, I agonized over my costume. Should I dig out the tried and true ninja suit? Could I get away with a dress? Perhaps I should go to Wal-Mart and pick up a cheap mask? In the end, I decided that I would bite the bullet and go in drag. The dilemma in my mind was that the other people at the party were ones that I knew from a singles group. Would I be giving my friends information that they had no business possessing? There are gossips in that group that would love nothing better than to embarrass me at just the right moment. I began several weeks ahead assembling my outfit. I pulled out three dresses to choose from. Two were black, one ankle length and the other right at my knees. Somehow neither seemed dressy enough for the occasion. The other dress was one that I had picked up on eBay with no clear idea when I would wear it. Of shimmering blues and turquoise, cut with an un-even hem so that the left comes up mid-thigh and the other side is almost to my ankle; it is a sexy outfit. All the undies were in the closet. New hose would be added. Need to think about blue eye shadow to match the dress. Now what to do about shoes? My 3" pumps were not the right color. Why mess up the illusion with black heels. I popped out to eBay to see what looked good. I fell in love with a pair of 4" Lucite heels. Would this be over the top? Maybe I need to mess up the trail a little bit. I called Debbie to ask about borrowing some shoes. I knew that hers would be way too small. "Hi, Deb. Wonder if you can help me out." "Sure, Bill. What can I do for you? You are coming to my party, aren't you? What are you making this time?" "I am thinking as coming to the party as a woman, but I am having trouble finding shoes. I was wondering if you could help me." "If I can, I will. What size do you need?" "A ladies 10." "I would like to help but I only wear a 7, I'll ask around and see if we can help you. So what are you bringing? That pecan pie like last year? Or the rum cake from the year before?" I sighed, "Whatever I decide will be spectacular. It will be a surprise until I decide. See you in a few days," yes, I thought, she only wants me for my cooking. The Day Halloween came on a Saturday. I had all day to prepare. In the morning, I made my cake. I decided to make a Pavlova since I had never done one for this group. The meringue seemed to take forever to dry out but the effect was worth it. Taking a long bubble bath, I shaved my legs, even though they did not need it. I patted dry and dusted on body powder. I glided the pantyhose up my legs, admiring the sheen in the mirror. Rubbing my legs together sent a chill through my whole body. I just love that silky feel. The panty girdle came next to flatten my slight paunch. Better not to show love handles tonight. The bra came next. I decided on the Playtex Cross your Heart to lift and separate. Even with that, I could simulate a little cleavage. I dropped the cheaters down inside and pulled loose skin to achieve the right effect. It was time for a little makeup. Some blue above the eyes to bring them out. A little color in the cheeks to harden the lines. Deep red lipstick to make the lips look kissable. What was I missing? Should I paint the fingernails. Would it be too much? I had already done all this, what would a little more color do? I painted my fingernails with a deep red to match the lipstick. After letting it dry, I went to finish dressing. Settling the dress over my head and pulling it into place, I looked almost perfect. I got my wig off the shelf and tugged it around my nape. A little brush here and there and my breath was taken away by the image in the mirror. The shoes off eBay were a perfect fit and really made my legs look good. Moving to and fro, I decided that a touch of dark eye shadow would emphasize the cleavage. I felt pretty! It is a long drive out to Debbie's house. Better verify my route; don't want to get lost looking this good. Take the cake out to the car, wow, it is chilly out there. What kind of coat is going to look not too silly with this outfit? The drive was uneventful. I drove slower than I usually do. Would not want to explain my attire, even on Halloween. I went in the house carrying my cake. I got some quizzical looks. Nobody recognized me. I was as nervous as a leaf; I knew I would have to speak eventually. As I placed the cake on the table, Debbie came up behind me. "WHO ARE YOU?" Debbie demanded. I turned around and gave her a smile. Debbie looked deep into my face and burst out into a deep guffaw, "I do not believe it! You are beautiful. Hey, girls, come see what Bill is wearing this year." Suddenly I was surrounded by 5 lovely ladies ranging in age from thirty-five to fifty. A few guys joined the throng to see what was going on. They all spoke at once. "What made you pick this costume? Who helped with your makeup? Where did you find this outfit? Have you ever done this before?" "I just thought I would see what it is like," I explained, "I got some other friends to supply shoes and stuff." "Well, try to make yourself comfortable. I see that you outdid yourself with dessert this year, too." I could not get comfortable. The girls wanted to inspect everything in my costume. I heard whispering in the corner and glanced over to see what they were saying, "did you see the eye shadow between his breasts, and this is not the first time." Another was saying, "I have to find out where the shoes came from, I want some." And still another, "you see that walk? It is so practiced!" I ignored the whispers; what else could I do. I drifted into the den to talk to my friend Mark. Somehow with Mark I felt less conspicuous. We talked about this and that for over an hour, until it was time to serve up the desserts. Of course, I was again the center of attention when I was cutting the dessert I brought; but at least in that setting, I am used to being the center. With plate in hand, Mark and I went out to the family room to chat and eat. I thought it was interesting how close he sat to me considering we were the only ones in the room. We were having a good time and it was a while before I noticed Mark's hand on my knee. Mark talks with his hands so a casual touch does not send up any danger signals. After about a half hour I start to wonder if everyone is avoiding us. No one else has even stuck his or her nose in the door. Mark's hand is playing with my nylon clad kneecap and it is becoming distracting. During a lull in the conversation, I mention that everyone seems to be staying away from us as if they could catch something. Mark says, "Maybe we look like we don't want to be bothered?" "Actually I thought it was kind of nice, just sitting here talking," I replied. "Would you be upset if I had asked Debbie to give us some privacy?" "No, but why?" I must have sounded really dumb by this time. "I saw you at another party and was asking Debbie who you were. Thought I would like to know you better." "You mean..." I must have looked shocked, "!!" "Tonight you are looking really cute. Better than I imagined. Are you shocked?" "Maybe not shocked, a little surprised. And Debbie was in on this?" "Remember when you and Debbie were dating several years ago? She called me one night crying. She did not know what was wrong with her. The two of you went out for six months, how many times did you kiss her?" "All the time. I always kissed her when I picked her up and took her home." "Bill, are you totally oblivious? How many times did you kiss her on the lips? Did you ever try to get in her pants?" "Oh, that!" I stammered, "I was trying to be a gentleman." "For six months. I told her you were either gay or a eunuch. Which is it?" "I didn't think it was so obvious." "That is when I decided I wanted to make a play for you," Mark said as he reached over to grab my head and plant his lips on mine. All of a sudden, my body went limp. It was as if the weight of the world had been lifted off my shoulders. I did not have to pretend around Mark anymore. I kissed him back and let his hand slide up my thigh. "Uh, Mark, um, do all of our friends know what is going on in here? Can I ever show my face again?" "What do you say we go see what is going on in the rest of the house." Mark stood up and offered his hand. It seemed only natural that I accepted his hand and continued holding it when we walked into the kitchen. Just then, I saw my lipstick smeared across Mark's lips. There was no hiding. All of our friends were smiling. Several guys put their hands up to 'high five' Mark. Mark was beaming; a silly grin was plastered across his face. Mark whispered in my ear, "Want to go to my house for a drink or something?" stopping long enough to nibble my neck. All I could do was nod. I thanked Debbie for a wonderful evening while Mark went to get our coats. "Be nice to my brother and call me tomorrow and tell me everything. We really need to talk." "Your brother? Talk? Everything?" Home I followed Mark to his house a couple miles away. The whole time, I was reliving all the conversations of the evening. I was thinking about the hushed whispers I had overheard. As Mark brought me in the door, he mashed his lips to mine and thrust his tongue against my tonsils. My arms went around his neck and I never wanted that moment to end. Eventually Mark pointed out the bathroom and asked if I needed to freshen up. Sashaying across the room, swinging my butt as suggestively as I could, I retreated to the bathroom. I slipped off the dress and carefully hung it on the door. I struggled out of the pantyhose wishing that I had sprung for the garter belt. I pulled a pair of lacy, thong panties out of my handbag and slipped them on (never know when you are going to need a spare). Keeping the wig, bra, panties, and heels on, I went to recline on Mark's bed. I glanced over and Mark was struggling out of his costume, it seemed to be difficult with a boner in the way. When Mark was down to his briefs and socks, he joined me. For the longest time, we just stared into each other's eyes. We could not decide who should make the first move. I finally ran my fingers up Mark's body from his six-pack abs to his hard pecs. A shiver followed my fingers. Mark reached up to cup my breasts. I saw surprise in his eyes when he realized that they were mostly real. "Tell me! Did I just cop a feel of the real thing?" "Are you going to be upset with me? A lot of the tissue is really me." "What did you do to get these?" "Absolutely nothing. They just started growing went I was in high school. The doctor said they would go away naturally. He was wrong. I hope I am still what you were expecting?!?" Mark reached back to unhook my bra, "I never thought I would need to have this skill. I came out so long ago; you are my first 'woman'." "You are Debbie's brother? I thought she was an only child." "Actually we are not related by blood. I have always been the brother figure she cried on when things weren't going well. Sometimes I have cried on her when I was so lonely." "Oh, Mark. I don't want you to be lonely anymore," I was starting to tear up as I said it. "I feel funny calling someone that looks like you ? Bill. Got any suggestions?" "Actually I call myself Billi when I am 'dressed,' do you like it?" "Oh, Billi, come closer. Let me drink in your beauty." Moving up face to face with Mark I felt the heat of his erection pressing into my belly. My body was on fire and I was ready. "I can't wait much longer," I cried, "I need you inside me!" Mark did not need further encouragement. His briefs came off and a condom went on. Grabbing a tube of K-Y he pressed it to my hole. I wrapped my legs over his shoulders and prepared to become his love. Gently the head passed my sphincter and soon the whole length was resting in my bowel. With every little thrush my prostate was excited and I knew I could not hold out much longer. Just as Mark began to spurt, I had a mind-numbing orgasm followed quickly by three more. I never wanted to leave Mark's arms. I was happier than I had ever been in my life. Whatever else happened, I knew that Mark was perfect for me. Morning After Sunday morning, I did not want to get out of bed. I was perfectly happy to stay intertwined with Mark; but he was not there. I found his note on the pillow. 'Dearest, I really enjoyed myself last night. I love you very much and want you to share my life. I ran out to get us bagels and will be back soon. Kisses and more kisses, Mark' The bedroom smelled like sex. I dragged myself to the bathroom to get cleaned up before Mark returned. The phone rang as I was looking for something to wear. I could not decide whether to answer it until I heard Debbie speaking to the answering machine. "Hi, Deb. Mark has run out for a few minutes. Anything I can do?" "Ah, you are still there? Guess things went well?" "Debbie, was I setup? Everything went way too smooth." "You remember when you called to ask about borrowing shoes?" Debbie asked. "Sure, you didn't have my size." "Bill, I don't know many guys that know their equivalent ladies shoe size. You didn't say, 'what is a man's 8 like?' you simply said ladies 10. I knew you already knew your size." "That's not enough," I protested, "to think I might find Mark irresistible." "No, but his gaydar had been going off for years." "Was I that transparent?" "Mark had been trying to get to know you for years but the setting was just never right. Once he saw your outfit, he said, 'get us alone for 30 minutes and I will do the rest,' and apparently it worked. How do you feel?" "I am in love. Mark and I had a great time last night. Oh, I think I hear him coming in." "I'll go. Call me later and tell me all about it." "Later, goodbye" As I hung up the phone, Mark walked in carrying a large platter of breakfast snacks. "Who were you talking to?" "Oh, Debbie called to see how things went. She wants a report later." "She is going to want a play by play report. Should I tell her everything?" "Tell her more than she wants to know and maybe she won't ask again. Tell her what our favorite position is." "Billi, you are evil. Are you going to tell her what it feels like going in?" "She already has her opinion of me. I slept with you before the first date. What do you want to do today?" "I think we need to take you home to get something else to wear, and then we can screw the day away. Sound like a good plan?" And that is exactly what we did. Happy Halloween!

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Halloween Party by Suzi (Johnson) Thomas "Hi, dear," my wife said when I walked into the house, "how was work?" "Not bad," I replied, "we landed that new account, so the boss was thrilled. What's new?" "We're invited to a Halloween party, a costume party, at the Peterson's Saturday night. Do you want to go?" In truth, we hardly knew the Peterson's, having been introduced by a friend of a friend, and we usually didn't really celebrate Halloween. "I guess so, sure, why not," I...

4 years ago
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Halloween Delight Part One

Halloween Delight; Part one: When I was young, I was only allowed to play in the basement. The upstairs was off limits to me as a play area. I could play in my room, but that was it, other than the basement. This was fine with me, as I found a lot to play with down there, and it was all mine. When I was either 5 or 6, I found a box full of dresses. They were from the late 1800's or the early 1900's and made of silk. They had full skirts that flowed to the ground and long sleeves....

4 years ago
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Halloween Cheerleader Fantasy

Halloween is supposedly a good time to be a TGirl, a time of year when society seems OK with a guy dressing and acting like a girl. Several times on or around Halloween I have walked through Macys or a mall and had salesladies call out "Nice Costume". Or, I as I go into a 7-11 or supermarket, and a couple walks by, the woman will smile and say to her boyfriend, "Hey, next year, let's dress you up as a girl". What's that all about? On the other hand, if my wife and I are invited to a...

2 years ago
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Halloween Spirit

Halloween Spirit By Morpheus I stood in the middle of the office floor, looking over the cubicles and office walls which had all been covered with Halloween decorations. The company of Danner, Dyson, and Dexler...or DDD as most people called it, had always supported holiday cheer, almost regardless of which holiday it was. But since Halloween was Mr. Dyson's favorite holiday, it tended to get a little extra attention. Today was Halloween but most of the employees were thinking...

3 years ago
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Halloween For LIfe Part 2

Anna felt bad about abandoning Jordan like that. She did think that they would be able to have a spa day together. She had no clue they would separate them like this. As she walked with her stylist she confided in her. "My sister is just a little nervous about who works on her hair, and face. We're new around here and she just doesn't want anything real drastic done," Anna explained. "Could you just pass that information along to her stylist so that she'll feel a little more...

3 years ago
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Halloween Humor

I often read jokes that make me laugh. Then I think about what a good and humorous story they could make. So I decided to write about a few of them. I hope you get a chuckle out of it, or at least a smile. A big thank you goes to Mistress Lynn for taking of her time to edit this story. **** Roy and Martha Simmons had been married for over forty years. Even though they were still in love, Martha always considered Roy a cantankerous old fool. Of course, Roy always felt Martha was an airhead,...

2 years ago
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Halloween and Batman

Just a short non-erotic story for Halloween. If you’re looking for sex, it’s not here. For the rest of the readers I hope you enjoy it. A big ‘Thank You’ to Estragon for making it a much better read. * I’m what most people would call a normal, non-descript type guy. I’m 5′ 10′, weigh 160 lbs. I’m not overly smart, but not dumb either. I’ve always been on the somewhat quiet side when it came to girls. In school I was the guy you never remembered in class. You would have to look in your...

4 years ago
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Halloween cd crossdresser

TinkerbelleMy sister , Candy, and I were fraternal twins, but looked nearlyidentical. Pretty much the same height weight and build. In high school,she was always teased about having small tits and I was always teasedbecause I was small, thin and had a big ass for a guy. Because of this wewere extremely close. Best friends really. We spent nearly all our timetogether.After college she became a consultant and I became a math teacher. Becausewe were so close, I spent lots of time at her house...

3 years ago
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HALLOWEEN MOM

HALLOWEEN NIGHT - OCTOBER 31st 2007 It's hard to believe it's been a year since that fateful night. Almost impossible to comprehend the changes that have occurred in my life, in my outlook on life, on who I've become...on what I've become...on the horrible things I've done...I'm going to drink from her breasts tonight...those beautiful orbs that are filled with thick, delicious creamy milk that her body has manufactured for my sister. Then I'm going to make love with her...unmasked at last.I...

1 year ago
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Halloween Party

Spells 'R Us: Halloween Party By Bill Hart The Lambda's Halloween party was tonight. Just about everybody, who was anybody, on campus would be there. CeeJay Larson hadn't picked out a costume yet. But then, he hadn't figured on being invited at all. His fraternity was the butt of some really weird rumors, so he'd been almost shocked when he and a couple of his brothers received invitations. He was looking for something unique. What he seen so far rummaging through through...

3 years ago
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Halloween Parties Last Call

"Halloween Parties Last Call" We were in Dennis' apartment at the end of the evening of the Halloween party. Everyone had left but Dennis wasn't finished with me just yet. "Walk like a lady for me, go on Tim!" he said ordering me to strut and mince around the living room in front of him like I was some kind of a tart! I really didn't want to but did what he asked anyway. He was studying my Halloween outfit, a complete housewife/drag affair that was over the top with too much...

3 years ago
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Halloween Trilogy of Transformation

Halloween Trilogy of Transformation By Julie O Edited by Amelia R. On All Hallow's Eve strange forces sometimes come together and change people's lives forever. Sometimes the person is seeking change, sometimes they are forced, and sometimes it's just a trick of nature. Chapter 1 Greg Jenkins was sitting in the break room of Bolton Incorporated, an international...

4 years ago
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Halloween Revenge

Note: not to be read by anyone under 18 This story is a mix of fiction and a true event that had happened on a Halloween night not too long ago Enjoy! Halloween revenge! For the last few years my girlfriend Chris I have been going to Halloween parties of friends, we have always chosen costumes with themes and went with it! Nurse, Doctor, Vampire, Witch, Zombies But this year was going to be different Chris said she would pick the theme. In September I had finally...

4 years ago
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Halloween All Saints Day and Beyond

Halloween - All Saints' Day and Beyond Authors Note: Halloween Getting what is Deserved I had intended to be a one-off standalone story. Feedback and comments posted or emailed have encouraged me to at least consider continuing the story of Olive and Samantha. Thank you all for the constructive comments, I do appreciate all the feedback received Thanks also to Cressar for his time in editing, commenting and tweaking this story --- --- Halloween - All Saints Day and...

1 year ago
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Halloween After the Party X

Halloween: After the Party- X Author's Note: Seems that there was room for a sequel by request. I was nervous as I approached the door to Starbucks. I could see my hand shaking as I reached for door handle. I don't know why I was so nervous; it was a first date, sort of. I mean we had already spent some time together. I had no problem at all spotting Terri sitting at one of the little tables. She appeared to have been here a little while already. She had a cup sitting on the...

4 years ago
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Halloween Part Three

Halloween Part Three: Chapter Four: Back to School It was only after I broke off my kiss with their sports teacher that I remembered who and where I was. Oh my god! What kind of example was I setting to my daughters as a father or was it as a mother? In fact was it as a man or a woman? It was easy to think of myself as a woman standing here amongst the other mothers dropping their kids off at school, dressed as a French Maid. I must have secured the sexiest teacher in school...

3 years ago
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Halloween and the Goblin

The young attractive couple, Kate and Dan, had recently purchased the huge old Victorian house. They knew it would be a huge renovation project but have plans to operate it as a bed and breakfast. Dan was an architect and Kate an Interior Designer which enabled both of them to work out of the house. It was the grandest house on the block but sorely in need of restoration. Three months before Halloween they had moved in with their two huge but loveable Rottweiler's, Amadeus and Rolf. Amadeus...

4 years ago
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Halloween Costume Malfunction

Louise had her ear leaned up against her brother's door, hearing his muffled voice through the wood. "Let me see," she called back through. "There's no way I'm going to a party like this. Just forget it." "It's not that bad. Open up and let me see." Frustrated, Louise pressed her skull into the wood, considering popping the lock briefly, and even more briefly, considering letting her brother off the hook. A few seconds later, the knob clicked. Louise stepped into his...

4 years ago
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Halloween Fun Followup

After a serendipitous hookup with Roxanne on Halloween night, I was quite smitten by our unplanned intimate exchange. Roxanne had babysat for Janice and me on several occasions and while she was very cute, I had never entertained any untoward thoughts about her. Now, after our Halloween hookup, my mind was full of all types of inappropriate thoughts and designs.I didn’t quite expect to fall into an illicit relationship with an eighteen-year college freshman who also happened to be our family...

Office Sex
4 years ago
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Halloween Curse

Mom always said I had to learn things the hard way and she was usually right. In retrospect I had it all: I was the captain of the cheerleaders, I was dating the high school quarterback and I was at the top of my class academically. To make my blessed life even more envious to most, I come from a very wealthy family and I am very, very pretty. My long black as night hair, aqua blue eyes have gotten me the attention of many boys and men; my long legs have also been a great attention...

2 years ago
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Halloween Day School

On Halloween, no one was surprised when I went to school as one of my favorite female final fantasy characters. The guys walk to school together and to my surprise they kept sneaking in little ass spanks while we walked. They had dressed up as home made transformer characters so they acted like they were attacking my ass. I had to hide my love for it and kept telling them to “quit it” all the while trying to keep my boner from growing in the short skirt. Math first period, usually puts me to...

4 years ago
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Halloween Frat Party Nightmare

Introduction: I am headed to by boyfriends Halloween Frat Party with my roommate. Shes going as a slutty cheerleader, while Im a sexy witch. She seems really eager to go, probably because shes a slut in real life, but Im going just to support by boyfriend since hes setting up this party for his frat. This is a free Halloween Special by EFon. Follow the links at the end to get a free mobile version. tags: public outdoor sex, monster rape, cheating, college party, accidental drug use, strange...

3 years ago
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Halloween in Shibuya Part II

Masa held my hand as we navigated through the mass of humanity in the Shibuya Crossing toward BIC Camera, one of the largest shops near the station. We walked along the sidewalk feeling like salmon swimming upstream. After a couple of minutes, Masa pulled me into a tiny side street barely 10 feet wide—more like a wide paved path. We passed dozens of postage stamp sized pubs and eateries stacked from the ground to higher floors, each with its loyal clientele. Halfway down the block, Masa pointed...

Fetish
3 years ago
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Halloween CD Slut

Halloween. It's just an excuse to go out drinking with friends like anyother night, only this time in a ridiculous costume. And since my friendsand I definitely like to party, it makes sense that I dress up for theoccasion.This year, I decided to surprise the guys by dressing up as a girl. Atcostume shops they have a thousand different "sexy" costumes. Sexy cat,sexy cop, sexy pirate...I always loved it when I saw girls wearing thesecostumes, so I thought it would be fun to put one on myself. I...

4 years ago
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Halloween sissy slut

Halloween. It's just an excuse to go out drinking with friends like anyother night, only this time in a ridiculous costume. And since my friendsand I definitely like to party, it makes sense that I dress up for theoccasion.This year, I decided to surprise the guys by dressing up as a girl. Atcostume shops they have a thousand different "sexy" costumes. Sexy cat,sexy cop, sexy pirate...I always loved it when I saw girls wearing thesecostumes, so I thought it would be fun to put one on myself. I...

4 years ago
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Halloween Disguise prestory by DanaWu

an original story by me. its not true more of a fantasy...this story starts october 14th. first of all i am a 23 year old boy, i just moved to a different state to go to college, i dont have many friends and have only been her a couple of months.today was like any other day, had to wake up early and go to work for a couple hours before school. julia, one of the first people i met here, approached me today and told me about an "awesome" party tons of the students have every halloween. she tells...

3 years ago
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Halloween Delight Part Two

Halloween Delight Part Two: In part one, I got the chance to fulfill a life long dream of going out in public dressed as a girl with my buddies on Halloween. I got more than I dreamed of when my best friend, who supported the idea, picked me up for lunch and seeing me already dressed, began to treat me like a girl. Lunch: Even though Carl and I had been friends for a long time, he looked upon in a different light. He was seeing me as a girl, not as his friend. I knew he...

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