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Reality By: Rachael Free Why am I compelled to continue dressing in women's clothes? I'm a man. I shouldn't be wearing sexy bras, panties or dresses but I just can't seem to stop. Sound familiar? Well let me tell you a little story of how I started and where I am now in my life. My first memory was when I was 4-5 years old. I was supposed to be taking a nap in my parent's room and I wasn't really tired. Looking at my mother's dresser I saw all sorts of things including her red lipstick. Back in the 50's red lipstick was the norm. I got up, opened the tube and rubbed it on my lips like I had seen my mother do many times before. I smiled but realized I looked a mess. Putting the tube down I tried washing it off quickly when my mother came in to check on me. I turned to her with the red lipstick still smeared over my face. She laughed and took a wash cloth to clean me up. I followed her to the kitchen where she proceeded to tell her friend she was having coffee with as they both broke out in laughter. I was crushed and humiliated as I slumped in a chair and watched TV. I wondered what she told my father that evening. The next memory was with a group of girls and guys in my friend's back yard. One girl took a box of clothes from her mother intended for donations and we all tried on dresses, tops, panties, bras, slips, skirts and even high heels. Laughing together, other guys were doing it too but I seemed to enjoy it a bit more and felt a tickle in my stomach. Being dressed in a 50's housewife dress, with all the underwear too, sent a chill down my spine. I didn't know what it meant then but do now. I got caught once in my sister's panty drawer holding up her garter belt. I had seen her with it before and was mesmerized with the unique item. I never tried it on but wanted to so bad. I then jump to middle school where my sister would put her cheerleader outfit in the clothes hamper in the bathroom. I would turn on the fan and put on her panties, tights, bra and cheerleader skirt and top and act like I was a girl. I came close to being caught several times and realized I couldn't do this much longer. I was about my sister's size and my mother's things were way too big. I next remember finding my mother's slip and panties that had fallen off the washing machine and quickly scooped them up and hid them. I was now in high school and about her size. When my parents would go out for the day I would put them on with a pair of her pantyhose, put on a bra and the sexy slip and then one of her dresses. Her heels were a bit tight but worked. My sister's things were too small for me now. I would prance around the house and made sure I put everything back before they returned. That was about it until I moved out of the house into my new job after college. My body got very big and nothing of hers fit me anymore so I purged everything. I didn't dress for many years. I met a girl and got married but she was much smaller than me. I could only steal a pair of panties now and then when she was out but that was about it. I got to travel though and would frequent porn shops and purchase magazines primarily about CD's, TV's, TS's and transsexuals. This went on for quite some time until I got the urge to buy a few things online. The internet just was at the beginning and I could order things and have them sent to a PO Box I had for my business. I bought a pair of gorky high heels, some panties, a bra and a frumpy dress. To me I was back and dressing made me feel wonderful inside. This went on for years gathering a few things, purging the old stupid stuff and adding more things to my wardrobe. JUMP TO THE PRESENT....... My kids are all out of the house, graduated college and on their own. My wife is a professional business woman and works every day. I have my own business and get to travel by car a lot a few days at a time. This gives me more time to dress and be my alter ego. I have two travel bags I take on road trips and two others stashed so no one could find them back at home. I only take them out when my wife is a way for a few days while I'm at home. Ebay is a good friend of mine and I can buy lots of things really cheap if I take the time to search out deals. I'm dressed right now in a very sexy black lace bra with my forms glued in place. I hate just putting them in the bra cups. I like how they feel attached to me as I try on bras before I dress. My silky pink panties, with a panty liner so I don't mess up my skirt or dress, go over my gaff to help smooth out my front. I love pantyhose over stockings to feel nice and secure. Not having much leg hair helps so I don't have to shave them. I'm also wearing a cincher too so I can mold my waist to give me an hourglass shape. I have a very silky full length slip on too so that my clothes feel nice and silky. Today I chose my red secretary outfit so I can do office work in my den. The skirt is mid thigh length and the jacket has shoulder pads, a narrowed middle section and then flares out a bit to accentuate my curves. I chose a short blonde wig today. It gets warm in my den and long hair makes me sweat a bit so a cute shoulder length wedge works. I have a 4" pair of red heels on too. After many years I can walk like a natural girl in heels and with a little wiggle, feel like a real lady. Knowing that I'm alone all day and won't answer the door I go all out and put on my makeup. I have gotten very good at putting on foundation, powder, blush, eye shadow, eye liner, mascara, and of course lipstick. I sprayed myself with and of course sexy perfume. Finger and toenail polish would take too much time so I leave that for weekends I'm alone. I am wearing pearl clip on dangly earrings, a pearl necklace, pearl bracelet, a woman's watch and some fancy elastic band rings. There, I feel sexy and very feminine right now. Today Rachael will do all the office paperwork including typing a report, filing and playing with other girls on-line. Many of you in my same position probably have thought about telling your spouse. After many, many years of dressing, my wife would either kick me out of the house and divorce me immediately, expose me and humiliate me to my family and friends, or do a "Bobbitt" and cut my man bits off at night. She would never accept my little hobby even though I'm totally harmless. So here I am. Totally closeted but relish the opportunity to make myself feel pretty and feminine whenever I get a chance. I hope you liked my little rant.

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Intimate Relationship With Matured Women

HI, This is Ram .I am an IT professional working in reputed company, living in Bang , smart, energetic aged 31 yrs married since 3 yrs and enjoying life at its fullest extent.I am reachable at have been a silent follower of this site since more than 2 years.I had posted a story around 6 months back in one of the sex portals.I have got few responses for my story appreciating it and out of them, it was one of the mail from a beautiful women which was very interesting which lead to a intimate and...

3 years ago
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It Was Just Meant To Be

‘Yes Tim,’ I spoke into the telephone to my friend, partner, occasional helper and drinking buddy. ‘You rang earlier. What can I do for you on this bright and sunny day?’ ‘You might think it’s bright and sunny, Sam,’ he groaned back at me. ‘But I’ve got myself in a bit of a pickle, and could do with some help mate.’ What? Sam got himself into a pickle? Another one? Nothing new there. I could just picture the poor tortured soul, sitting there without a hair in place and his big, black-framed...

2 years ago
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Kritika Me 8211 Part II

Hi ISS readers, this is my first story me and my hubby are writing together It is our real story. My name is Kritika, First about myself, I am 33 years Post graduate divorcee when this incident happened . I was working as Asst. Manager for MNC in New Delhi. I was staying as Paying guest near gk I am divorced with in 7 days of the marriage. I have put my profile in Shaadi.com for my second marriage. I got in touch with a guy named Kumar 36 Years working as Sr. Project manager in MNC software...

2 years ago
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My two best buddies

Mere do jigri dost ne mom ki Chudai ki Hello dosto this is Tanmay Deshmane from Jaipur. I love this site and I also told about it to my other friends mere 2 dost bhut ache dost hai, hum teeno sath sath khumate ek hi school mai jate hum 3 no ne isi sal 12th class pass ki hai. Mere dosto ka name Sachin and Vishal hai hum teeno sath mai hi beth ker kai bar indiansexstories per sex stories padte the aur hum teeno ko hi aunty ke sath sex wali stories bhut achi lagati thi stories pad ker hum aas pass...

1 year ago
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BlackAmbush Emily 08042018

You know an update is good when you’re fapping so much while editing it, you’re not sure you’re gonna hit the deadline. Such is the case with busty blonde Emily. Luckily there isn’t much to edit with a beauty like Emily. I do take out my voice during sex scenes whenever I have to give direction. Nobody likes some off-screen male dude talking during sex. There’s no need to point out how goddamn hot this girl is, you see this for yourself. So just a few quick notes:...

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2 years ago
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Black Mailed TeacherChapter 5

"All right, class, that's it for today. Remember the test on Friday will cover the fourth and fifth chapters in your text."' There were sundry groans of dismay but she'd expected that. Any time a test was announced always produced the same reaction. She had come to believe it wasn't possible to produce a kid without a built-in fear of tests. She remembered what she'd always felt like the day before a test and guessed all these kids felt the same way. They all filed out while she...

4 years ago
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My USAF Group Jerk Days

There is not much debate that all men enjoy jacking off, and most of us continue to do so as long as we are able. And it has been my experience that many, many males, straight, bi, gay, whatever like to masturbate together.I first began with a group of classmates after gym in junior high, but really got into it while in the Air Force with a group of buddies.The first time there were 4 of us who rented a couple of hotel rooms just off base one weekend when we were going through tech school in...

1 year ago
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If the Spirit Is WillingChapter 3

Bill walked down the unplowed street, a knit Sabres hat on his head and a blue winter jacket half unzipped. A few inches had fallen over night, not enough to close school if it hadn't been a Saturday but enough to make the day off much more fun. Well ... after he and Dad had shoveled the driveway, that is. That had been gotten out of the way early, though, and now the rest of the day was his. A car was coming up the road behind him, and Bill took a look back to make sure it wasn't aiming...

1 year ago
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Stefan Damon Part IV

Chapter 1: Unexpected Visitor “What the hell?” I screamed at the shocked looking Human standing in front of me behind the open door. Matt didn’t answer a thing. “How did you, get HERE?” Matt, stunned just stared. After a few minutes of awkward staring, the guy finally answered. “Jeremy was with Bonnie, and there was like, spells and fire and smoke and then some big ray of light opened up! Jeremy just jumped in there! I didn’t know what to do so I waited for Bonnie to go and just followed...

2 years ago
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Horny Professor

Dave was a Professor at a University in Texas. His classes usually ranged from about 200 - 300 students per class. He was in his early 40's and married. He and his wife had been married for about 15 years and they used to have sex often. Nowadays,they both had busy schedules and their sex life had slowed down to about once aweek. He would jerk off occasionally to keep his stress down, but his sexual cravings had increased over the past few years. Lately, he was having lustful thoughts towards...

2 years ago
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She Knew My NameChapter 6

All too soon summer was over and it was back to school. Ellen was a senior and I was a sophomore and just turned fifteen. Ellen was pretty cool for the first half of her senior year. We were fucking a couple of times a week. She would let me sit with her at lunch and told everyone I was her friend. She never said boyfriend in front of her friends. I didn’t question her because everything we did at her house was a secret. I may have been a bit disappointed but I certainly was not going to...

4 years ago
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A WellLived Life 2 Book 10 BridgetChapter 16 Deals and Promotions

September 21, 1996, Chicago, Illinois “Uhm, sorry!” Molly said, quickly recovering. “I shouldn’t have said that! It just kind of slipped out!” Sensei Jim laughed, “Steve?” “I’d say her reaction was warranted, Sensei. We did use an unconventional testing method!” “Steve is going to take this and have Kara stitch the dojo name into it, similar to his. Kara will use his as a template.” I had checked with both Ailea and Mitsuko, and neither of them did any needlework, nor did their mothers....

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