Not Crossing The Line

When I was a kid I had a book called, ?What Do People Do All Day?? It made a start at teaching me about the variety of jobs that exist in the world. As an adult I feel it would be equally beneficial if there was a book as simple as that one which answered the question, ?Why do people do the things they do?? Part of the trouble is that I often do not even understand my own motivation, particularly for those things I feel uneasy about sharing with others. For my normal side, I married an attractive, petite brunette and am very happy with married life. Our sex life has never been particularly adventurous, which occasionally means I get led astray while using the Internet. My preference is to blame porn, but I have to admit that sluts are really hot. A woman who may not catch your eye normally can dress and behave in particular ways and capture my attention for long after I have stopped looking at her. This is probably why I feel disappointed that my wife never looks or acts like a slut. She rarely wears heels and on the occasions she does, the outfit is a long skirt or dress. The ideal would be something that barely covers her ass and tits. Over the years, my frame of mind while watching porn shifted from simple enjoyment of what I saw to fantasizing that my wife was one of the participants. Strangely, I rarely imagined myself in them, which I put down to wanting to see my wife from angles you cannot see when you are the one fucking her. During a phase which lasted about two years, my primary interest when searching for porn was to find women with beautiful faces and a cock in their mouth or covered in cum. Reality was always clear in my mind. My wife would never allow me to cum on her face, but I still imagine it frequently. I also wish I could experience being out with her wearing less than a respectable woman should wear to experience the reactions of men who see her. I guess I like the idea of knowing another man wants to fuck my wife. An unexpected side effect of my surfing habits was that I began to consider some cocks nicer than others. I fall into the stereotype of enjoying the sight of a large cock making a girl open wide and also the dark skin of a black man in the mouth of a pale woman, preferably with some bright slutty lipstick. This side effect led me to consider what it was like for these women. I found myself wondering what it is like to have something in your mouth that you cannot (and hopefully don?t want to) bite off. What is it like to have a cock sliding back and forth between your lips? How does it feel when he cums in your mouth or on your face? Well, I went through the self discovery phase, questioning everything and finding out what appealed to me. I found that I wish to experience things to have a better understanding of them. I tried giving a blowjob. It was kind of fun in a naughty way, but also weird and it did not give me anywhere near the arousal that thinking about women does. Another facet of the woman?s perspective hit me a few years later. Eventually, I decided that if my wife would not dress like a slut then I should try it myself. There are a few items of clothing which I keep hidden. I started with a simple pair of black heels and miniskirt from Asda. I did not have the nerve to go into a women?s clothing store. I got the size wrong and had to exchange the skirt for a smaller size. I tried them on at home while my wife was out and enjoyed it. My interest grew as did my boldness. I never try the complete crossover to appear to be a woman. I doubt it would be possible, certainly not with my own güvenilir bahis skills. What I like to do is get photographic evidence of my crossdressing in a public setting. I say ?setting? because I make damned sure no one will actually see me. There are still mixed feelings in my views on this. Looking like a slut is my goal, and it gives me a huge adrenaline rush when I am out somewhere public. If I knew that no one would be able to identify me or tell I was a man I would love to go somewhere like a mall where many people could see me. I would like to be able to go to a club and have guys check out my legs and wish they could fuck that slut. The trouble is, interaction with other guys does not appeal to me. So, what does that leave? Another wishful dream is to meet with all of the attractive women I know who sometimes show off their legs and get a group photo of me with them where we all look like sluts. I admit, the primary reason for this is actually to get them to dress like sluts so I can hang around with them, stare at their bodies and fantasize about having sex with them. That is yet another thing that will never happen. But, then I had an idea. What if I just asked one woman? Who could I ask? There is one woman I worked with a few years back who could be a possibility. We never did anything socially that was not a work related function, but I had a number of fairly personal conversations with Jennie and we did have a level of trust established. She also knew that I considered her beautiful, yet I never tried anything inappropriate and did not make innuendos in her presence except on rare occasions. What can I say about Jennie? She is blonde, which is not my first choice, but it is long and straight and it does look nice. She is usually smiling, which is a big factor for me. There is an occasional twinkle in her eye, one I think is just about causing mischief but I like to interpret as her thinking about something sexually inappropriate. One of the things that made me notice her in the beginning was that she nearly always wore heels at work. Her frame is quite slim and she had a habit of wearing clothing that hugged her body. She was not too revealing, but it gave away her shape which has no flaws from my perspective. For a petite woman she has also a great bust. What is most noteworthy for me personally, is that her waist and hips make what for me are the most amazing curves in the world. Her slim waist contrasts wide hips perfectly. Maybe it is just the primal urges of procreation, but I never could resist watching her walk away. The challenge took serious consideration. After numerous attempts to write a message explaining what I would like her to do I discovered a problem. The difference between what I want her to do and what I think she might be willing to do could not be much farther apart. It was always clear from the way she talked that even though her partner thought marriage was pointless, that she would not go behind his back. And there is also the fact that I do not actually want to cheat on my wife. Aside from those issues everything was fine. Several draft emails were written. The worst failed to get across any hint of my true interest while the best somehow included my asking if putting my tongue in her ass would count as cheating. I felt the correct approach might lie somewhere in the middle. In the end, I sent a note asking how she was doing and indicating that I would like her opinion on something I would prefer to discuss on the phone or in person rather than by email. Eluding the main issue was güvenilir bahis siteleri sure to capture her interest. It did the job. The next day I got a friendly reply from Jennie including her mobile number with plans to arrange some time to talk. Not wanting to rush things, I took my time before I tried to speak to her. The first four times I had written a text to Jennie my heart raced so fast I didn?t dare send it. Two of those times I ended up wanking while looking at photos of her, for the second I resisted for long enough to put on a skirt and heels before tugging out streams of cum in Jennie?s honour. Then I sent a message asking if she was available to talk anytime that afternoon. It was a Saturday and I had time to myself. The reply came quickly: Yep. Free now. Shit. I was not mentally prepared nor would I ever be. A few minutes to calm myself were necessary. Preparation was both physical and mental. One hand gripped my cock while the other held my phone. I stared at her message and kept reading: ?Yep. I?m naked now.? ?Yep. Free to fuck now.? All this went through my mind as well as imagining what Jennie looked like naked until I released my inner pervert and flushed it away. This should give me half an hour to remain normal before my hormones are sufficiently replenished to fully appreciate Jennie. My clothes were back in position before I rang. ?Hey, how are you?? It had been more than a year since we spoke. Her voice never crossed my mind, but as soon as I heard it I half melted just listening to her. Luckily, my social responses kicked in without requiring too much concentration. We started a normal conversation in which I did not comment on her body, make any sexual comments or even grab my dick. During a pause in our conversation Jennie breached the subject by asking what was so sensitive that I wanted to discuss with her. Natural habits led me down a self deprecating line indicating some insecurities that I wanted to share with someone. I told her I chose her because she was a little outside my regular group of friends but someone I trusted much more than most. It put her in a receptive mood. When I eventually spit out the words to tell her I occasionally crossdressed she said, ?I?d love to see that.? From that point on there was only one thing to do: Don?t fuck it up. As the discussion continued Jennie became genuinely curious and asked questions. At one point she asked, ?Are you gay?? I told her that I was not and that I was actually aroused about letting her see me like that. I wormed my way around to telling her I wanted to get a photo of myself with real women. She knew what I was getting at and reminded me that she does not enjoy having her photo taken. Selecting a couple photos of myself, I sent them to Jennie. She understood why I had blurred my face because my concern had been clear throughout the conversation. Keeping this activity a secret was a priority. Jennie asked for a little time to let it sink in. That was fine with me because my anxiety level was running high. A few days later I got a text: What kind of photos are you hoping to get? My heart leapt. Jennie might actually agree to it. First, I explained my slow methods. Always on my own, I have to set my camera up with a timer for each shot. Getting the position right should be easier with her in view as I prepare them, but I said I would like to shoot many because I never know if they will turn out good. Jennie asked more directly what I wanted her to do for them. "Just be your usual gorgeous self," I started. Then I told her iddaa siteleri I would like her to also be in heels and showing her great legs. My impression was that she was reasonably comfortable with the idea so I mentioned that with my own clothes I preferred the skimpiest things I could find. We arranged to meet on a weekend when we both had time to ourselves. I would bring my bag of ladies clothes but arrive dressed normally. That was in both our interests. It kept me from worrying about being seen and kept her neighbours from thinking a weirdo had come to visit. She moved since the last time I had been to her place so everything was new to me. As expected, my nerves were on edge as I approached her house. Jennie smiled immediately, gave me a big hug and invited me inside. Walking in front of me, I was grateful to see that sexy hourglass figure before me. Jennie was wearing a tight black skirt and black heels like she wore so often to work before. When she turned around my gaze was still below her waist. "Are you sure this isn't just a ploy to photograph me?" How could I deny that? Unjustly. "I forgot just how good you look. Yes, I would love to just have photos of you, but I know you would not want to do that. I am grateful that you are considering any of it." We checked out her house to plan where to shoot photos. I asked that we avoid the front room because she has a large window viewable by people walking by. This left the kitchen and dining room for use. We discussed a few casual poses like standing in the kitchen or seated at the dining table. "Why don't you change and we can try it out." She sent me upstairs to change in the bathroom. Since Jennie usually wore black patent heels I decided to wear similar ones. My dress was a bright blue party dress which was very short, definitely shorter than Jennie's skirt. Under that I wore matching black lace underwear and padded the D-cup bra. The challenge had been finding a skimpy dress with a high neckline to hide my fake tits. The final piece was a short black wig, the disguise to hide my gender only at great distances. Nerves hit me as I prepared to leave the bathroom. This was the first time I would let someone I know see me this way and I had no idea what to expect. When I started back down the stairs Jennie came to look. "Wow, that looks great. Nice legs,? she nodded looking at my legs. ?Although, I'm not sure who it should appeal to, since you're obviously a guy. I think I see your point about not going out in public." "I lean towards the slutty look. Do you think it qualifies?" Jennie laughed. "Maybe. It's shorter than mine." "Do you have anything slutty short?" The question got out before I could stop it. She smirked and flushed slightly before hinting, "Maybe." She followed me and gave me a compliment, ?I did not expect you to be so comfortable walking in heels. I guess you wear them a lot.? I admitted that I have worn them a lot, just not in public. Soon we came back around to the subject of photos and the kinds of shots I was interested in capturing as I got out my camera and tripod. The naughty side of me sprang to life by starting to record video without telling her. It was at the entrance to her kitchen with dining room in the background. We stood close as we talked. I explained my appreciation of legs, including hers specifically, and how I like different shots. In the process I managed to caress her calf to indicate that it was one of my preferred curves on a woman. Mine are more muscular than ideal, so hers were far better. I think she knew my touch was unnecessary but at least I got it on camera. Jennie offered me a cup of coffee. Although I am not a great coffee drinker I said yes to this just to give her something to do. The reason for this was so I could turn my back to her and pull out my dick.