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To the outside world I was your normal boring 44 year old male accountant in kaki slacks and a pullover top. The kinda man women want after they sow their wild oats with the band members, the bikers and the body builders. But for me, while the outside was pure boring vanellia the inside was a raging crossdressser who adored pretty silky panties, tight bras, and the highest CFM heels she could find. My account with ebay was over $600 this year in purchases of the prettiest things I could find. Since I can't pass as I am 5-9 and 165lbs I had never been out of my townhouse. Well ok I wear pretty panties everyday and sometimes a well concealed flat bra. But had only shared "Jin" with one friend I had met online. He had the same interest as me - we both liked pretty clothes, heels, makeup ...... all the femmine stuff. We were good friends, I could trust him and I would sometimes leave work early, shower and get all pretty and then cook a fantastic and romantic dinner for us. Sometimes he was "him" and other times it was just 2 women having a girls dinner. One night at dinner she (Cindy) told me that the local gay bar ROOSTERS was having a DRAG BINGO night the Monday before Halloween. She really wanted to go and was working hard to convince me to go with her. After all its near Halloween, we won't be out of place if we get stopped while driving, it's a gay bar and we will be safe there, and WE NEED TO GO OUTSIDE SOMETIME. I stared at my lipstick prints all over my martini glass and started to ponder the possibilities. After all what if somebody saw my car - or if I recognized a man from work - worse yet what if a man recognized me dressed like a woman wanting "it". She countered she would drive and no one would recognize us with makeup and wigs on, plus she pointed out my 20 outfits in my closet that EVENTUALLY somebody needs to see. It took us 2 weeks to figure out how get away with this safely and we decided to go. I selected a vee neck blue print dress that went to my knee, a blonde wig, stuffed bra, pantyhose, makeup, earrings, rings bracelets and a pair of nude color Brash CFM pumps with 6 inch heels. Under the cover of darkness she picked me up and off we went. I was panting as I knew we were either going to get arrested, or I was going to have a stroke and wind up in an ambulance/hospital. But we made the 20 minute drive and pulled into the parking lot only to find it full and we had to park across the 4 lane road in a bank parking lot. Oh great, now I have to walk across 4 lanes in a dress and these heels, but we did and got safely inside. All the bartender boys were in very pretty drag, and there were maybe 5 others crossdressed. We got seats at the bar, ordered drinks and toasted our "outing". Nobody even gave us a second glance, we were treated like regulars. Bingo started a little later - so I took a long strut around the place showing off my dress and then went to the little bois room and freshened my face. Bingo was starting so I wiggled back to my seat and found an attractive man had taken the seat next to me. I focused on the bingo- it was fun, but then the stranger leaned over and whispered in my ear that I missed a number. That certainly startled me, then he did it again with another number followed by telling me how attractive he found me. My eyes grew wide and I lost track of bingo and asked if he was hitting on me? "Yes" he said rather snugly as he placed his hand on my back," How could I not considering those pretty legs and those heels, let me get you another martini". I lost track of everything but him after that. He told me he had a nasty divorce and couldn't trust women and found crossdressers a good alternative, but he was all top. He nibbled my ear, massaged my back and then my inner thigh - My eyes were glazing over and I grabbed Cindy and drug her to the powder room to talk. I told her I had never felt like this before, my hormones were raging, I wanted....... No I NEEDED to go home with him. She gave me a rubber from her purse and said just call her if I need anything / anytime. But I had to agree to share every intimate detail with her. I came back to him, and said lets go, but first you have to show my friend your drivers license, he kissed me (there in the bar in front of everyone) then showed her his license, and with his arm around my waist we walked out to his car. We arrived at his place and pulled into garage, he opened my door, I swiveled, stood and he again kissed and I melted into his arms. No need for more drinks or coffee, or small talk. But I rushed to the bathroom to freshen up, some more deep red lipstick, and just make myself pretty as I could for this man. I returned to him and he had his camera out saying how delectable I looked. I spun, turned, twisted and blew kisses as he snapped away. Tossing the cam aside he came to me we kissed and felt each other all over. He unzipped my dress and it fell to the floor, his hardon was ragging in his pants. Still with my heels on I took his shoes off, then his shirt, and finally his pants - as natural as any woman I took hin in my mouth as he stood there moaning. He reached under my bra and started tweaking my nipples - driving me so far over the edge I worried I would bite him. We stopped and went for the bed, where I lost my shoes and bra. I kept him in my mouth as he kept working my nipples except when he sucked and bit my nipples for long periods. I was mostly on my back when this happened and I swear I arched up so much only my head and heels were touching the bed - pure ecstasy. Break time as I needed water . When I returned he had the lube out and told me to get on all fours, he pulled my panties and hose down and started to loosen me. He slipped on the rubber, wiggled it at my pussy, positioned it for entry, and bore down on my back. With one hand on my nipple firmly playing with it, my eyes rolled as he entered me. OMG my brain was getting stimulations from all over - I was trashing about but he had mounted me and was riding me for all he was worth. The initial pain was quickly replaced with the smooth stroking pleasure he was giving me - and of course my nipples were now bright red and oh so tender. I was in a place I had only dreamed about being - this was exquisited. After 20 minutes he needed some wine left me there feeling empty, lonely and sad all at the same time. Returning he saw me pout and offered me some wine and said we weren't done yet, and I should take off my pantyhose and lie on my back face up. He again worked over my nipples sucking and biting until I couldn't take it anymore and then he put my ankles on his shoulders, folded me in half and stared deep into my eyes, as he slid my thong aside and again penetrated me. My eyes rolled again and soon I was mumbling and sometimes yelling out OH YES, YES, fuck me, deeper, harder. His arm muscles were bulging as he held my ankles down and apart. His balls were slapping my cheeks, he wasn't gentle this time, more like a male pig there for his own pleasure . I didn't care, I was dripping fluid from my own lil thing - dripping it into my thong. He was staring deep into my eyes as I felt a rush, got lightheaded, and completely came in my thong - totally untouched! He slowed and asked if I was ok ..... I was on cloud nine. He buried his tongue in my mouth as I felt my panties dripping my seed . He then went back to pounding my tush until I felt him tense up and start grunting and I could feel him fill the rubber with his warm seed. He wanted me to know he was the Alpha male and I was there for his pleasure (little did he know ). I laid there consumed in all these new emotions and feelings I was experiencing , I felt so satisfied and soon fell asleep with his arm over me. At 4am he woke me with coffee , saying he would drive the princess home before it got light. I was a wreck, and looked like shit. But the coffee helped me pull myself together and I did the makeup, hair, and clothes as best I could. He drove me home with little conversation. I felt so used, cheap and ..... well "satisfied" is the appropriate word, all the time he had a wide grin on his face. He didn't ask for my number and I didn't ask for his, as I thought how could you just use me like that. He later thanked me for a fun tight, and under the safety of darkness I made it unseen into my townhome and collapsed on the bed fully clothed and crying as I called my friend to make sure she made it home ok. Well she did but she wasn't alone ........... and needed to put the phone down so she could put something else in her mouth. Oh goodness TMI ....... I finally fell asleep after thinking and tearing a little about "HIM" not asking for my number after a few hours. I had taken the next day off, woke up, tool a long hot bath (to wash off all his smell) and slipped into some wickedly tight ass shaping jeans, a wife beater top, some ballerina flats and just a touch of makeup (no mascara as I knew I was still teary eyed) and of course a wig. Later making a large chicken ceaser salad I called my girlfriend to join me for dinner. As I had several hours I did to much thinking, and crying. How could he be so uncaring? We had a perfect evening, he was all gentleman, successful, attentive and "oh SO GOOD". I thought "what a jerk" and I will never do anything like that again. Later Cindy showed up in her boring man clothes - and we trashed men for a while as we ate. Then the doorbell ran and I got up- Cindy said I needed lipstick. Oh yea. The delivery boy was startled not sure of what I was - but he handed me a small bouquet of pretty flowers and saw my eyes light up, and said "You must be special to some man". What ????? did he just think I was a woman - maybe I do pass - or he was gay. Cindy grabbed the card off the flowers and we went to the sofa. She said Mr Right had some feelings after all, and I felt all creamy inside and blushed a bright shade of red. She then began reading "It was a great evening and I enjoyed meeting you both mentally and physically. When can I see you again? Love Rob Ph # 555 1212 I came to with Cindy slapping my face as I had fainted.

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'If you could have anything in the world,' my wife said to me, on my fortieth birthday, 'what would you choose?' 'Anything at all?' I asked. 'Absolutely anything. Imagine anything was possible, that you had all the money in the world, that you could have anything that your heart desired.' she said. 'I think....I think I'd like to have sex with a man.' I replied. 'Really?' she gasped. She sounded both surprised and excited. 'You said anything in the world.' I pointed out. 'That is so hot!' she...

Bisexual
4 years ago
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Percolate Installment 4

Sherrie lazily shoves her work books to the side of her bed against the wall. She stretches her arms straight up,straining a little. The muscles in her arm pits shiver in a sexy supple way that reminds me to look to her leg for that delicate little shivering morsel of a muscle between her shin and calf.Sherrie peels her maccosins off with hre toes then flexes her toes ,which press little knobby protruberances against her pure white cotton socks.Sherrie's elegantly delicate ankles silk...

2 years ago
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Nisha aunty ki mari chut aur gand

Hi I’m Arjun 25yrs fit male in bombay, I have come to mumbai from UK I lived in the UK for 6yrs, all this began when I came to mumbai to study and spend time in India. I will use hindi from now since its one long that all readers can understand. May jab bobmay tha tab ek room rent pay rakhatha, it was in a society aur samne ek family rehti thi (husband and wife) tab say maine Nisha say batein karna shuru kiya, (thats her name, she’s 36yrs with excellent fig and fair skin) Nisha ko dekhke hi...

Incest
2 years ago
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Me and my Dad

I should start at the beginning: friends call me Lola, which is short for Lotus Larsson. My father is Swedish and my mother Japanese. I live with my daddy and my lil’ s*s. She’s a cute 18 y/o and I am three years older, and not so cute anymore. Haha, just joking. A few days ago sister told me that she, by accident, saw dad in his room and he was having a hard-on. Sitting at the computer, he was stroking his penis. She and I are very close, and we talk about all different things. She was upset...

2 years ago
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photographing the sister in law

Hi, this is a short story about what happened when my sister in law asked me to take some pictures of her for a calender for her husband. I am a photography enthusiast and love taking portrait pictures. A couple of years ago, my sister in law was asking for ideas about what to get her husband for Christmas that was a bit different. She didnt have much money and they had had a tough year so she wanted something special. SO I suggested a calender of her. I said I could either take the pictures or...

Masturbation
3 years ago
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How Deep Do I Go

How Deep Do I Go? By Deanna Lea Life in the seventh grade was a living Hell. That's why I had hoped the summer away from home would be a welcome relief. Mom agreed, and allowed me to stay with Aunt Addie on her farm in Kentucky. Aunt Addie was a tall very pretty woman who ran the farm without a husband. Since she had no children, having one war worn, soon to be eighth grader, spend the summer with her would be a time we would never forget. I have always been a mama's...

2 years ago
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Other Side Of Best Friend 8211 Part 2

Hello Everyone, I’m Arya back with another set of incidents that happened in my life over the past few months which are exciting and fun-filled, also sex filled. Before I start thanks to all those who have mailed me their valuable comments and opinions on my previous writings, and for those who are reading mine for the first time, I’m from Hyderabad and 22 years old, well-built 6’ft tall guy. For those who want to chat with me or give their opinion on my writings can contact me on Please not...

2 years ago
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My Prelude To Jeanne

I never shared that my story, "She Finally Did It", posted August 4 is actually true. Of course, I changed the names to protect the guilty.The story that I share here is the prelude to how Jeanne and I met. And yes, it is the gospel (probably the wrong word to use here) truth.As I alluded in "She Finally Did It", my wife was widowed when she and I met via an online dating service. I was divorced since the early 90's. As a single guy who really was pretty tame before divorcing, I let it all fly...

3 years ago
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My First Bang When I Was 18 Years Old

Hi ISS readers. My name is Divya and I am an ISS reader from 1 month. On reading these stories, I became very excited and now I tried to write my own story as I have no one now to share my experiences. First I have to tell you my family story first. I am older daughter of a lonely couple in Vizag. My father is working in a doctor’s clinic as an attendent as he doesn’t have educational qualifications. But he tried very much to get me and my younger sister in a good position. He helped me to...

2 years ago
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Terminator The Sarah Connor Chronicles

I am Sarah Connor. In the future my son will lead mankind in a war against Skynet, a computer system designed to destroy the world. It has sent machines back through time to kill him, one to protect him. Today we fight to stop Skynet from ever being created. To change our future. To change his fate. The war to save mankind begins now... The future has not been written. There is no fate but what we make for ourselves. I wish I could believe that. My name is John Connor, they tried to murder me...

2 years ago
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Ahriman The Evolution of a Serial Killer 12

Introduction: Part 12 Please read parts 1-11 to understand the story, especially before voting. The doorbell woke him with a start. He looked around the room, but Kaneez and Samil were both gone. He bolted out of bed and raced down the stairs. Kaneez and Giolla were in the kitchen, Kaneez cradling Samil, their eyes wide and frightened. He was pleased to see Giolla had not removed the dildo from her cunt, but he had no time to reward her. He stormed toward them and hissed, Downstairs! Now! Not a...

4 years ago
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Gary GingerChapter 2

~One Week Later~ Gary knew he shouldn't have answered the phone but he always made the mistake of answering it without looking at the caller ID. "Gary. You will be meeting your mother and I for dinner this evening at eight o'clock at my house." Gary's grandmother, Ava, was on the phone sounding demanding as always. "Hi grandma," Gary said cheerfully. "Don't hi grandma me, you just show up for dinner. You're mother says you don't want to go back to school. Is this true...

3 years ago
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Petting the Teachers PetChapter 5

“Now, where were we?” Professor Lawton approached Lindsey, still holding his cock in his hand. She was still on all fours on the bed, having just been fucked hard by Professor Johnson. In contrast to the 58-year-old Professor Johnson, Professor Lawton was much younger, probably early thirties, with wavy blond hair. He was tall, thin, and wore wire-rimmed glasses. He would definitely be considered attractive, in a “nerdy” sort of way. He approached Lindsey and guided his cock into her supple...

4 years ago
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Guy on the Road

About 15 years ago, I was dating my husband‘s boss, Guy, from the construction site he was working on. We had been dating for about 5 months and one of the first weekends we went away together, we took a trip to Santa Cruz for 4 days. We were pretty pent up and eager to be together even before we got driving, so the prospect of spending the next 4 hours focused on driving to our destination was frustrating to say the least. We spent a good 20 minutes debating exactly how to handle the excessive...

4 years ago
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A Journey To Bed

Hello Iss peepz, Am Juss trying to share my fantasy with u…Hope u will like it…do reply me So let me start my journey to Bed…(pls applaud if u like it) I am 27 and she is 25 ,once I was traveling in train one evening from Bombay to Ahemdabad, I had my seat and took out a book to read(it’s my hobby), train not yet started, a good looking lady came with luggage and searching for her reserved seat, I prayed god to give her reservation number opposite to me, I was blessed she sat opposite to me. I...

4 years ago
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Big RedChapter 6 Unexpected Developments

It seemed like the days surrounding the July 4th holiday had become the timing for Paul Cooke to spring big news on Pete. It was then that he first contacted Pete with the first contract offers and it was then that he told Pete about Memphis picking up his option with a substantial increase. "Hey, Pete, how's it going?" "Good, Cookie. How about you?" "Great. Couldn't be better. Say ... you and Brenda going to be around early next week?" "Yeah. Bren's knee deep in paint colors...

2 years ago
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Night of the Rubberdolls

“It’s settled, ladies,” announced Phil ‘Mandi’ Reeves on the three-way call.“I’m so excited,” replied Doug ‘LeeAnn’ French.“Me too,” added Gary ‘Sylvie’ Barber.“Me three,” giggled the fifty-two year-old Mandi.The three ladies were all avid rubber doll crossdressers. They had each been involved separately in the fetish, but made the acquaintance of one another over the course of the past two years. Mandi, who in her male life was a sales manager, was recently divorced and offered up her spot for...

2 years ago
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A Series of TabooChapter 31 A Flake

Inspired by https://i.imgur.com/MtBfaGl.jpg Byron watched as his ex-wife worked her tits into the large cups of her industrial strength bra. At 35, she still kept that hourglass figure. Too bad she was such a flake. “Will you talk to him? I mean, if Bill ever catches him...” Bill would do nothing except maybe whine, Byron thought. Even at 15, their son could lay him out with a single hit. Her husband is not what you would call a manly man. One of the many reasons his ex still comes around....

1 year ago
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Change Part Two of the Brandt Family SeriesChapter 18

JR turned and saw flashing blue lights on a white and green SUV that was racing to catch them. He recognized it as a Border Patrol vehicle, which was common in this area. “It looks like it, but it’s the Border Patrol so you’re not being pulled over for any traffic violations. There’s the next exit in about a quarter of a mile. Turn your right blinker on, take the exit as before, but pull over to the shoulder as soon as you can.” “I’m scared,” she admitted. “I’ve been pulled over by the...

1 year ago
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Me and My Sisters First Time Home Alone Part 1

100% fiction! Ever since I was a young boy, I have been heavily fantasizing about my sister. So, when my time finally came, I couldn't resist writing the story. First, let me describe my sister. Her name is Angela, and she is 19. She is in college, and loves to go to parties. She is about 5'4", has wavy brown hair, and medium sized boobs. What she lacks in boob size, however, she makes up for with her nipples. She has pointy pink nipples, the perfect proportion to her boobs, that are...

Incest
3 years ago
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Gone With the WindCh 5 Kyle Palmer

March 15th, 6:39 PM CT, Mile 210, 5 miles west of Burlington, IA Bob Benjamin was on his first solo run driving a train. All his effort and his time, all the schooling, all the training, all the assisted runs with the experienced engineers had come together to this point. This was his dream, to be an engineer on a famous passenger train, moving hundreds of people to their destination. Not only was this a glamourous job, to Benjamin; this was a decent paying job. The perfect convergence of...

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