My Life As I Know It free porn video

My life as I know it. This is an attempt to put into words my life as a crossdresser from the very first day it happened to today. It ends with what my future may be. Any male who cross-dresses will always remember their first everything they do. I remember the very first time I ever tried anything on that a girl wore. In my case it had occurred just before I started grade school. Prior to trying on something for the first time I never had considered doing anything like that, I had no desire to do it and just gave in. No, I had no inkling that this was about to happen to me and that it was the start of a lifelong thing. I had one sister, and three brothers. My sister was in school but since I had not started school yet I was still at home. I was walking back to my room and for whatever reason as I passed my sister's room my head turned and I looked in. I cannot ever remember doing that before. I stopped as I saw sitting under her bed were a brand-new pair of shoes our mother had bought for her but she still really had not started to wear. They were black and white saddle shoes and she made a big stink about not wanting to wear them. I quietly walked over to her bed and leaned down to look at them. What was the big deal with these shoes they looked fine and I knew that other girls wore them and thought what was her problem with them? I then reached down and grabbed the second she, holding them up and turning them every which way. Now the part I don't understand but still remember very vividly. While still holding my sister's shoes I walked out of her room with them and into my own bedroom. I sat on the side of the bed away from my door and looked at them more. I then pulled one of my shoes off and slipped one of her shoes on me. I laced it up and just looked at it. I was wearing a pair of blue jeans. I put my leg down and then put on the other shoe. I then stood up and walked a little thinking she must not like them because they must feel bad but they didn't. The felt ok. I took a few steps and once again remember thinking the same they felt just fine. Right at that time my mother walked into my door way and told me it was lunch time and I should come to the kitchen. I was afraid I was going to get caught and be scolded as I took something of my sister's and didn't ask. I also felt embarrassment. I also felt a stirring that my young brain had no way to comprehend, but it felt good. I heard my mother again to come for lunch. For a brief moment I thought just go but it was if I knew I shouldn't and quickly changed back to my own shoes. I also put her shoes back under her bed and didn't think about it again that day. The next day I also was walking back to my room but this time I hadn't even gotten to her bedroom and the shoes crossed my mind. As I stepped past her door, there they were. I felt the stirring again in my pants but kept walking to my room. I held off for a few more days but as I am sure you figured out, I took them again and once again put them on. I got the same stirring in my pants and was sitting on the floor playing with something, possibly a toy truck. As a boy of my age would do I decided to lay down on the floor and look at the truck imagining I was driving it, using my imagination. As I was on the floor originally on my side I then rolled face down. The stirring still was there but now pressed against the floor and now I got an intense feeling. Remember at this age I had no reference on what was happening. But now all these years later I really do believe it was a prepubescent reaction in my groin and not knowing what the feeling was but knowing I really liked it. I then found I got it when I wore my sister's saddle shoes. I knew now what it took to get that good feeling. Fast forward a few more years. I was now in grade school and my sister had her first communion. For that she got a very feminine white dress as all the girls wore back then (this was the 60's). One day during the summer I was sitting in the kitchen when she came in and told me to follow her. I did, and she went into her room. There on the bed was her first communion dress. I was confused what she wanted. She then told me she wanted me to put on her dress. I expressed my confusion and said why would I want to do that. She then said let's do it just for the fun of it. I guess I must have still been quite innocent at that time and with some further prodding my sister had me dressed up in her first communion dress. Once I had the dress on she had me change out of my boy underwear and she gave me a pair of her panties. I turned away from her as I made the switch. She then had me sit on the bed and put on a pair of white knee sox and then a pair of her white patent leather Mary Janes. Lastly, she held up gloves for me to put my hands in and the affixed a vale to my hair. She then had me stand up and walk to her floor length mirror. I can remember as I stood, I felt the skirt and petticoat swoosh on my legs. I got a tingling felling, like goose bumps. But then I felt that stirring again but even more so. By now I knew that boy's thing could get hard but obviously didn't know why. It just happened every now and then and it was happening right now. As I stood at the mirror looking at myself looking like a catholic school girl dressed for her first communion, I could feel my groin become very hard, it had to be sticking straight out but with the dress and petticoat you couldn't tell. But as I walked a few things happened. I could hear the hard heels click on the hardwood floor as I made my steps. I could feel the skirt and petticoat on my legs and it felt good. And I felt my thing sticking straight out with the petticoat brushing against it through the panties as I made each step. My sister then told me to follow her out of her room and she took me back into the kitchen where my mom was. My sister told my mom to meet her new daughter. My mother turned and I could see the surprise in her face but then that look softened. She then walked to me and gave me a hug telling me she couldn't call me by my name dressed as I was. She then said when she was pregnant with each of us they had two names chosen, a boy's name and a girl's name. She said of course I knew my boy's name but that had I been born a girl they had chosen the name Jennifer. She said I didn't look like a Dan right now and more like a Jennifer. My mother then told me, "Jennifer please sit it's lunch time." My sister sat down and we had lunch. After about being dressed like that for about an hour I was allowed to change back into my own clothes. My sister told me I made a pretty girl and if I ever wanted to be Jennifer again, she'd like to enjoy her sister. Thankfully by the time I was changing back my thing had softened once again and I was able to redress without my sister noticing that. I think I would have died from embarrassment. All of my experiences up to this point started me noticing girls as I am sure most boys do but I think unlike most I also noticed what the girls wore. And with noticing what they wore I also liked some things and not others. Then I started to wonder what it would be like to wear something like that. I also started to question why did boys and girls wear different clothes than each other. Remember this was in the still stone age of the pre-internet days, those were a few decades away. But as I grew up, progressing through the grades both the boys and girls grew up. Girls started to wear more adult clothing though not like a woman, say a teacher would. Lady teachers often wore dresses and high heels. High heels. I started to notice those and wondered how could someone walk in those. Women made it look easy but with such a pointed heel I could see their feet, in particularly the back of their feet wobble a little when walking. While growing up I started to dream vivid dreams of wearing girls clothing. When I dreamed this, it wasn't as if I had any thoughts as to it being right or wrong but that it felt good. When I woke from one of those dreams, I'd be somewhat sad because I knew that it wasn't ok for boys to wear girl's clothing. Who made those rules up I don't know but I didn't think it was fair? By now it was more common for girls to start wearing pants more so than dresses as they once did, but of course the day never came for it to be ok for boys to wear dresses. Years later after high school I went on to further my education. My sister became a nurse and my three brothers went to other jobs but they never went to further their education. Once I secured a job travel was a part of it. Still no internet yet at this time, that was still many years off. I had bought a few Playboy magazines, even read some of the articles. I of course would look at the ladies but also found myself wondering what it would be to dress as they did (and no I'm not talking about the nude photos) and have nobody question it. While looking through those magazines I found an ad for a smaller monthly book or magazine however it would have been described as. It was called Variations. I couldn't find it where I bought a Playboy. One day after work I knew of an adult book store a few miles from work but on my way home, if I drive through the city. One day I parked and went in. It was my first time in such a place. I saw a rack with Playboy's and Penthouses, and then saw the Variations magazine, it was a smaller publication, not quite pocket size more like a reader's digest size book. I grabbed one, a Penthouse, Playboy and then started to walk around. Yes, I was nervous as this was my first time in such a place and with no history under my belt, I didn't know what to expect. As I walked, I saw that they had specialty magazines, all wrapped in plastic so you could see the covers but not what was inside. They were arranged in sections. There was a section for Gay books, Dominant and Submissive, Bondage, etc. As if by chance I turned and I was standing in front of a whole rack on crossdressing. I really had not heard of that term yet and if I did it wasn't that much. But what I saw were men dressed as women in all of the magazines. I was nervous to touch a magazine, all sorts of thoughts went through my mind. One was if I picked one up and was seen looking at it someone would immediately think I was interested in crossdressing. Sure, I was but nobody else ever knew that, not even a stranger. I had a plan. I grabbed one of the crossdresser magazines and put it in between the Playboy and Penthouse magazine. I very nervously walked up to check out my purchases and the guy behind the counter looked like some biker dude. Great, this wasn't going to go well I thought. He rang it all up told me the price, I handed him the cash, he gave me my change and slipped the magazines into a paper bag. I was out of there. Next concern was walking out of the place with an obvious purchase in my hands. I made it to my car, heart beating away. The magazine Variations was very eye opening to me. There were terms that even I as a young adult in my early 20's had never heard. I guess I got an education in kink from that magazine as I'd read up on something and think that was interesting. But I went back for more. Eventually I'd go in and buy several magazines on crossdressing and read them cover to cover. There were some limited ads in the back from stores out of state of course that actually catered to men who cross-dressed. The carried shoes, dresses, lingerie, and so on. I thought that it sucked they were so far away but then I thought if they were close by, I'd be spending money in them. A few months later things lined right up. I had to fly out to Los Angeles for work on a call to a defense contractor. They actually made a huge part for the Space Shuttle at that facility. I went thinking it might take days to sort out the problem but it turned out to be something pretty easy and got them up and running quickly. I stayed for the day, into the evening. That night I tried to get a flight home but ended up spending a whole extra day out before my flight home. I had written down the name of one place in the LA area called Lydia's TV Fashions. GPS didn't exist we navigated by map back then. I plotted out a path to get there. Once I got to that location it appeared to be an old motel which had been converted to small businesses. I remember Lydia's was on one end with a State Farm insurance office in the next "room" over. I thought that I am safe no matter what happens next. I'm 1700 miles from home, nobody I know is going to see me or know what I am going to do. I took a deep breath or two and got out. As I stood out of my rental car another car pulled up and two guys in suits got out and went into the insurance office. I walked into the crossdressing store. As I opened the door and walked in I was greeted by someone. She asked if she could help me. I saw a display of high heels and asked if I could see something like this in my size. Not knowing what "my size" was. She told me to have a seat and remove my shoes. She then measured my feet and said she'd be right back. She came out with two boxes. One pair of black pumps with a 4" stiletto heel and one in red. Looking back on it I think they were made by Pleazers. She gave me little footies to put on and then asked me how experienced at heels was I. I told her I had never tried on a pair ever and was from out of town. She calmed my fears and slipped my feet into the black pair first. She then grabbed my hands with hers and said to stand and she would help me balance. I stood and almost fell over. She told me that's normal and that I needed to practice but it would come to me quickly on how to walk in high heels. She then had me try on the red pair. I ended up buying both pairs. She placed my purchases in a plastic bag, gave me my change, I always paid in cash as I never wanted it to show up on my credit card for whatever reason. I also bought a few pair of nylons to go with my new pairs of heels. As I stepped out who was coming out to their car, the two guys in suits. I could tell they both gave me a longer look than was really necessary. I almost expected them to give me some crap but it never happened. I drove back to my hotel room and then next day flew back home. I put my purchases in my suit case but casted away the boxes. I can remember when I got home and opened my luggage there was an inspection tag from airport security. I eventually learned that there was a place in Chicago, only an hour away that sold high heels. I saw it in one of the crossdresser magazines. I took a day off, took some cash, and drove to Chicago. I ended up buying three pairs of high heels. I found that I really liked stiletto heels. I also preferred pumps. I once bought a pair of Italian stiletto black pumps that were fantastic to look at but with a six-inch heel they were impossible for me to walk in. I found that I could handle up to a 5 ?" heel but that was my limit. Work consumed a lot of my life. As by now I considered myself a closet crossdresser, even though I had never dressed fully up as a woman, it impacted me. With work I put in a lot of hours which wasn't conducive to building a relationship with a lady. I prefer women by the way. I also read where men who cross-dressed and hid it from their wives later regretted it as it eventually came out somehow. I knew I could never lie like that to someone who I loved and thought rather than having to deal with that I just didn't date anyone. Life went on. Worked a lot, traveled a lot and ended up putting on weight. Not good. Lost the weight then put it on and off and on, and then off. This time it stayed off as I really watched what I ate and got into a good exercise routine. When I was overweight, I didn't do much in the way of my crossdressing desires. But when I finally lost the weight, I was not just slim I was thin. I actually weigh 20 pounds less that I did what I graduated high school. With my new found body and not traveling all that much anymore my crossdressing desires started to resurface. I knew enough to know never to purge as so many did, I didn't need to I was single and living on my own. But now the internet was out and the embarrassment of going in person wasn't as necessary to buy adult magazines as I once did. But now I had thoughts of going shopping again. But not driving a state away to a store that caters to crossdressers but at a real women's clothing store. This was uncharted territory for me. Reading up on the net how others did it I read where some would call ahead and ask for a manager or owner and just be honest and ask if they had any problems with a man shopping in their store for themselves. I started by calling a resell shop thinking they might for some reason be the most probable in it being ok as they are independently owned and a small business. Business is business. The very first place I called I ended up talking to the owner. She was very pleasant and when I asked if it would be ok for me to come to her store to shop for clothes for myself, she replied that she was perfectly fine with it and even suggested a few days and times that the store was usually dead. She then told me that other men shopped there and there was nothing for me to worry about. I got off of the phone thinking this was really easy. In my mind I went through various replies I could have gotten and this was better than anything I could have imagined. The very next week I took Tuesday off. The owner told me Tuesday mornings was pretty much shopper free and would be a safe time for me to come, at least for my first visit. That day I took a shower, cleaned my self up, as in hair removal. I didn't want to try on a skirt or dress with hairy anything. I put on a pair of panties, nylons, a garter belt and a bra then dressed up the rest with male attire. I wore socks over my nylons. I decided to bring a pair of high heels along in a bag in case I just felt like trying something on properly. The store was located in one of the outlying old suburbs of the city I generally lived in. I lived in a newer suburban city located further out so I had to drive into town. This particular area was that city's "older downtown area with store fronts in the first floor of two- and three- story buildings. Right behind the buildings is an alley and past that public parking lots. I found a spot behind the store. Some of the stores have a rear entrance and this one did as well. While I was on the phone the week before she told me where to park and that she had an entrance both on the street side and the back-ally way side. As I got out, I grabbed the bag that had my black five-inch pumps, took a deep breath and walked up to the door. As I opened it I heard the old time bells that rang as the door opened. I saw a lady about my age sitting at the check out counter. She looked at me and smiled, saying welcome. She got up and approached me. I told her I was the person who called her last week and said I was a little nervous. She calmed my fears and told me that a number of her good customers are men who like to dress up so no need for me to worry. She then asked what was in the bag, I told her a pair of heels in case I needed them. She told that was good and then asked if I knew my sizes. I told her I had lost a lot of weight and actually weigh less than when I graduated high school so I have no idea what my sizes were. She then told me that she could measure me up and help guide me to my sizes. After being measured up she showed me the section where I could find styles that would fit me. She asked if I had a look that I liked. I told her I liked classy not trashy, and also liked the professional look as well. From that she started showing my various outfits. Skirts and blouses, and dresses. She then showed she had several skirt suits that might interest me as well. I ended up trying countless outfits. I chose a few pretty dresses, one in red, one in black and the last in aqua blue. All three were very pretty. I bought three different skirts. I found that I seem to like pleated skirts the most, and a few blouses. Then I started looking at several skirt suits. I ended up buying two suits. Both high quality and looking almost brand new. One was in black and the other in beige. When I put on the black suit I also put on my black pumps. When I came out dressed like that the store owner told me that I looked great in that. Sure, she was the store owner but she didn't say that in any of the other outfits I wore. I told her I absolutely have to buy this. She then asked me if I wanted to wear it home. I wasn't in lady mode as far as my hair, make up, and nails. I was a man in a lady's suit. But I loved how it felt and couldn't believe how thin I was and could actually fit in it. And just like that I said ok. I followed her up to the register and checked out my purchases. Then she asked me if I want to relax and chat for a while. She said customers on a Tuesday usually don't start till midafternoon. She left the doors open but I followed her to the back where she had two living room chairs. She asked me if I wanted a something to drink, coffee or a soda. We sat and chatted for close to two hours. It wasn't lost on me that here we were she was wearing slacks, blouse and sensible shoes. I was dresses for success. We talked about each other's history. She told me she was married one time but it didn't work out when he cheated on her. She had no children. I told her I never married, in part because of work but also my dressing habit. I said it's one thing for me to deal with it for life but I couldn't see making a lady who I was supposed to love to then deal with it as well. And I certainly wasn't going to hide it as that would be lying through omission. Before I knew what was happening, I was at ease and was actually having a good time talking with her. I almost forgot how I was dressed at times but not for long. It's hard to ignore you're wearing five-inch-high heels and a pencil skirt for very long. She then asked if I was seeing anyone, I replied I wasn't. She then asked if I would like to go out for dinner one evening. She said however I dressed was ok with her. I really liked her in the short time we had been together and just said I would like that. I knew that I would dress in male attire as I wasn't that "out" with my dressing. It was time to get going as customers would start showing up soon, it was already past 1pm. I got up, she handed me my bags, followed me to the rear entrance and she actually held the door for me as I walked out wearing a black skirt suit and my pumps. She gave me a peck on the cheek and said she's call me later today to make a date. I walked out to my car not really thinking of how I was dressed. I put my purchases in my trunk and drove home. By the way her name is Linda and later that evening she called me. As I answered the phone, she told me who it was. She then asked me if she was talking to Dan or Jennifer. I had told her my female name and how I got it. I replied that she was talking to Jennifer. She then asked what I was wearing. We talked and talked for several hours. We made a date for the next evening. I told her I hope she's okay with Dan being there. Linda said she would be fine with Jennifer or Dan. The next night we went out. We ended up dating for two years. Linda was totally cool with my dressing up and she also knew that I didn't want it to be all that there is to our relationship. It had a place and it wasn't all of the time. I think that even though she's fine with my dressing she also likes her man as well. We did end up getting married. No, I didn't dress as the bride though it crossed my mind, but knew better. Linda even said if I wanted our wedding could have two brides or she would even be the groom. I told her I could never see myself ever being that out to those in real life especially my own family. Our wedding was great. We had about 100 people at the reception. Most were over 50 as we too were over 50. We had a memorable wedding reception. A nice sit-down supper, open bar for the whole night, and an actual band. In our dating we hit a few night spots some with live bands. One band was popular in the city and was great at playing what today is known as classic rock. Between sets we talked to one of the band members and asked if they ever played a private party. We then said as in a wedding. They never had but as they were a popular band, they also weren't cheap. One thing about working a lot of hours every week for decades it pays very well. Also, when you work a lot of hours you don't spend money. So, paying for the wedding wasn't hard at all. We also own outright both of our homes and cars. It was a wedding to remember. We went on our honeymoon to California to the wine country. It was great. Life has been good for us. We ended up selling both homes and built a new home, our home. Linda at times likes to have Jennifer around because sometimes she just likes to have a lady's night. Most of the time though she wants her man. A few close couples we know, who are kinky, know of my dressing up. Linda also is the more dominant one in our relationship. It's more of a Female Led Relationship (FLR) than anything. She's not my "mistress" she's my wife, but she makes most of the big decisions in our life. I'm fine with that as it's nice not to have all that stress. Thankfully I never get the dreaded male pattern baldness so I have a full head of hair. Not even any widow's peak. I don't travel for work anymore. Linda loves to play with my hair and prefers that I wear it long. At work it's not a big deal as I keep it in a ponytail. I've also found that men with hair loss never say anything about my hair being long as it brings the subject to hair and men with male pattern baldness don't like to talk about hair, ever. With longer hair Linda likes to fuss with it. It's amazing how feminine she can style it with a blow dryer, curling iron, and hair spray. I have remained thin and if you didn't realize it that men or women who are thin basically carry their weight the same. So, it's easy to look feminine for me. Linda has some really nice curves. She has a cute rear and ample breasts. She often likes to joke about me getting breast implants when I finally retire. I've admitted to her, before we got really serious, that I often questioned if I had gender issues beyond dressing up. I told her with a lot of self-evaluation about my life I knew it was more than just dressing but that I had no desire to transition to being a woman with the final bottom surgery. I told her I'd miss "him". Often in bed she liked to rub my chest tweaking my nipples at times. She liked to tell me it's not fair that I got her breasts to play with but she didn't with me. One time I made a comment that I wished I had a pair of breasts for her to play with as well but we have to deal with what we got. She got a sly smile on her face when I said that. I have one year to go now till I retire. Linda is in the process of selling her shop to her general manager. Her manager also knows about Jennifer and has always been fine with it. Linda and I periodically take time to have conversations about whatever comes up. Often, it's light hearted sometimes more in depth. We have talked about moving out of state once I retire. We've talked about the southwest or Florida. This past conversation was intense. Linda said that I know that she's never had a problem with Jennifer and sometimes wished Jennifer could be around more. She said she knows Dan and Jennifer are one and the same but she said she's really gotten to enjoy being with Jennifer a lot. When I dressed as Jennifer and we had sex Linda liked to peg me. As a part of that she also liked me in chastity. It was a mind-blowing experience that has grown into me spending more and more time locked in chastity, even in Dan mode. Linda has started to talk to me about what my thoughts are if I had breasts of my own. She's decided to have me undergo electrolysis. I have no more male facial hair. I never had much chest hair but now I have none. They are working from the top down. Next is my genital area. Linda wants me to have a landing strip and nothing else. She goes with me to my appointments periodically to tell the technician what she wants done. The technician is kinky in her own way and has zero problems with us. She said so long as I put it in writing with my signature everything is open. Right now, we are leaning on moving away. As much as I was close to my siblings as we've gotten older and had our own families (they not us) kids, grand children and great grandchildren we don't see each other all that much anymore. Some are living out of state for a long time already so there really isn't anything family related keeping me here and Linda was an only child. We've talked about me possibly living openly as a woman once I retire once we make the move. It would open up possibilities for us. I could get breast implants, and she knew I often fantasized about this. Maybe even get a legal name change to Jennifer. She knows it interests me. She's told me that she's sexually attracted to Jennifer and in some ways even more than Dan who she said she is fine with spending the rest of our lives together with me not living as a woman and only dressing up as has been the case. We are only a year away from me retiring. I am giving really serious thought of making the move and leaving Dan behind. Honestly living my final years as Jennifer is very appealing, Linda knows that. If I had to make the decision today, I would say I am leaning to taking the walk on the wild side and leaving Dan back here when we move. It would be a great feeling to open my closet and dresser and not find anything remotely male to wear. The one thing Jennifer never has worn are women's slacks. Jennifer is a girly girl in that she's very feminine in what she wears. She loves high heels, a lot. She loves wearing skirts and dresses a lot. She loves make up a lot. As that date one year comes closer day by day, I can see Dan's day's are likely winding down. Jennifer is feeling good that she may likely be able to spend her retirement finally out of the open able to wear whatever she wants to wear with nobody thinking it's odd or out of place. I really think that Dan's days are winding down. Linda is also getting excited about the possibility that her favorite girlfriend will be there in retirement. For my birthday this past year Linda bought me, Dan, a pair of black and white saddle shoes. I had not worn a pair since I was so young. Honestly the shoes are unisex but it's all in the eye of the beholder, I guess. Though once she had me put them on she told me that these were a pair off the women's shoe selection in Amazon. We then went out to a movie, with me wearing the girls style shoes that got me started down this path in life. I am loving it to be honest.