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 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 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 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.

It easily fell out of the flimsy women’s thong. I nudged my balls out the other side just for fun, leaving only a thin bit of lace around the base of my cock. I glanced over my shoulder to be sure Jennie's attention was elsewhere and tugged my knob to a semi erect state with a dirty grin on my face. That is my kind of pervy behavior.

Tucking my dick back under the lace veil, I admired her legs. When Jennie turned I wanted her to know I was looking at her. To cover my stare I commented on the difference between our legs, complimenting her shapely curves again.

What I left out was letting her know that I wanted to lick every inch of her legs, rub my dick on her and leave streaks of my cum oozing down. Of course I wanted photos of all of that as well. I reminded myself to focus on reality.

We posed for our first photo. The video had to be stopped and I snapped a shot of Jennie before setting the timer. Ten seconds was plenty of time for me to stand beside Jennie. We both stood leaning our butts against the counter when it took the shot.

Jennie was much more at ease than either of us expected. She put it down to how I was dressed. She just could not get over how strange it was, but it amused her.

We took a number of shots in the kitchen and sitting at the dining table. I suggested we just talk conversationally rather than about the shots, but asked her to change her position in some way between them. We had many similar shots with legs crossed different ways or facing a slightly different direction.

Feeling like she was comfortable enough to try, I got her to move her chair and we both faced the camera. As I set the timer my eyes were drawn to her thighs in the hope of seeing up her skirt, but she never gave me a good view. I took my time making some adjustments while squatting behind the camera. This was a deliberate attempt to flash her since I knew my dress would not cover me.

Jennie made it clear when she noticed. “Lace knickers, very stylish.” Trying to be discrete, I checked to see if she was looking and I thought she was eyeing my cock. The lace thong I chose for this occasion did very little to support it and absolutely nothing to hide it. Knowing that she was looking at my cock caused it to twitch as a little more blood flowed into it. I apologized to her for not being ladylike yet did nothing to hide myself from view.

As I stood to walk back beside her with the timer counting down I was glad that Jennie was not flustered by my exposure. If she knew the thoughts in my head she might have been more concerned.

Taking photos became easier as I took more of them. We ended up talking about people from our time working together while I went back and forth between the camera and posing. Sensing the time was right, I asked Jennie if she would pose standing in a few. She obliged as we got some I had specifically wanted.

The first few were simple. I stood behind her while we both spread our feet a bit. Mine were wider than hers, and I hid my face behind hers so it could be believable that both subjects were women if the rest of the photos were not there for comparison. We took another with our sides to the camera and me behind her. I always like to get different angles on legs. I asked if we could repeat that one while I stood really close to her. Jennie said it was fine and I set the timer again.

Setting the timer doesn’t take much but a press of a button on the back and then I press the shutter button. There was no need to let her see I was rubbing myself while pretending to take more than the necessary time to do this. I got back behind her again. We were both facing the camera and I still had one hand slyly rubbing my cock. “Mind if I hold your hips?”

“No,” it was as easy as any answer had been. The camera flashes a red light as the timer counts down and the speed doubles for the last three seconds so you can tell when it will go. Just as it took the photo I leaned against her and pulled back on her hips. It wedged my mostly hard dick into the crack of her ass for the shot. If only we were naked.

To my surprise, Jennie did not react. I anticipated being told it was inappropriate. Nothing. It gave me the courage to try something else.

“What about a James Bond style photo. Sometimes the girl is below him, with her arm around his leg or waist.” Jennie was not quite sure how it would work, so I told her to be like Bond first. Although I could not recall a Bond pose where he had his legs apart, I asked Jennie to do that. I knelt behind her right leg and put my face against her hip. I put my left hand on the inside of her thigh and my right down on her calf. Her skin felt great. For the first time, the ten second timer was much too fast for my liking. Ten minutes would have been fine with me.

I got Jennie to do a similar pose with our positions reversed. She did another sat in front of me with her knees up to her chest. I got a glimpse of her black underwear in the process as well.

I tried to get her to pose with me behind her holding her tits, but she did not go for that. What she did offer was to swap it around. She reached around me and held my stuffed bra. I claimed I had blinked, a lie, and asked to take it again. This time, with her completely behind me, I lifted my dress and got the shot with my erection on display. “Thanks, Jen,” I said, safe that she would not understand the true reason for my thanks.

One of my long standing desires was nagging at me. “Would you mind something that is a little bit,” I hesitated, unsure what to say, “different?”

“That depends what it is.” It was a fair answer.

“Would you let me take one of me kneeling behind you and kissing your butt?”

Jennie laughed, which suited me. There have been so many times I wished I could touch her butt and kissing it was just as good, if not better, than using my hands. It was a delight to hear her accept. My cock was already twitching with excitement as I stepped toward the camera. I was even more thrilled when I turned back and saw that she was leaning forward with her elbows on the kitchen table and one leg forward. The curve of her butt was a spectacular sight.

I knelt and put my lips against one butt cheek and waited, listening for the timer. No point waiting until the last second this time. The shot was done. I backed away slowly, admiring her butt and her bare legs. My face was so close to her thighs and her pussy, mere inches out of view, that it had my dick throbbing. “Can I get one more?”

I returned to the camera. My heart was pumping like mad and I was becoming a little unstable in my heels, even though I normally had no trouble in them. I had to ask, “Any chance of one on a bare cheek?”

“Yeah, right!” She sounded mocking. “Not with the camera.”

Initially disappointed, this was better than a photo. “Okay,” I agreed. I pressed a different button and watched the display for it to start recording video. The red light did not flash as I approached Jennie again.

She slipped her skirt up a couple inches. Seeing the bottom of her butt, those sexy curves exposed even partially, was so sexy I could hardly contain myself. Jennie pulled her skirt from the top until about half of her butt was exposed. I leaned forward to kiss her bare skin. This time I put my lips nearer the middle. My cheek was caressed by her left butt cheek as I placed my lips on her right one. My hand gripped my cock fiercely at the same time.

It was like a dream. I kissed her butt not once, or even twice, but dozens of times. Each kiss was in a slightly different place. I covered both cheeks in kisses and even put a few right in the middle where only the sides of my mouth touched her.

Jennie did not mind when I placed a hand on her butt, nor when I gave it a gentle squeeze. It caused her skirt to move and I pushed it farther out of the way. Her whole butt was exposed except for the thong which disappeared between her cheeks. My fingers slid under it and down, pulling it out and to the side.

All I got from Jennie was a gentle, “Hey.” That was not going to stop me from enjoying the best ass I have seen. I spread my tongue and gave her a nice long lick right in her crack. It was the most intimate I have ever been with anyone’s backside before. With no objection and Jennie remaining still, I repeated it. The third time I slowed down as my tongue crossed her anus and circled it with the tip. I got a very gentle moan from her.

This was not something I had practiced before, but I wanted Jennie to enjoy it. I leaned back to admire Jen’s butt briefly. Her small sphincter was puckered up like pink lips. I reached out with a firm tongue and licked around it a few times, waiting for another little moan before I pushed it into her.

As my tongue entered I heard a better sound, quite feminine and definitely pleased. It was a higher pitched, short and quick moan followed by a quick sucking in of air. I pushed my tongue deeper and heard another much the same. It was clear that both of us enjoyed this.

I put an arm around her thighs to pull her close. Her butt pressed against the sides of my face. We definitely crossed the line beyond mere friendship, which we should not have done, but I could not resist Jennie, not in this position. She had my favorite waist and hips ever and now that I had seen her ass there was no way I could pass up the opportunity to put my tongue in her anus. I continued to lick and poke into her hole. Jennie continued to enjoy it.

Her butt clenched a little as she straightened up. My heart sank as she stepped away. Was she upset? She did not say a word or even turn to look at me. It must be embarrassment.

Then she got down on one knee. I thought she was picking something up, but she put both knees on the floor. She had her back to me as she leaned forward. Her body got lower and lower until she rested her head on the floor. Her ass was up in the air. She pulled her skirt up and her panties down, baring her ass to me again.

I had my doubts but since she had not spoken I felt I should not speak either. My only course of action was to assume she wanted what I wanted: for me to fuck her in the ass. I had to stand up. My cock was already harder than it had been for months. Jennie had often had this effect on me, yet she never knew it. I wanted her to know that now.

I spit on my hand and rubbed it on my cock. Still in heels myself, I carefully stepped closer to straddle Jennie’s upturned ass. Squatting over her was more difficult than normal. With my heels on, I had farther to go to get my cock down to her ass. There was no way I wanted to take off my shoes though. There was something extra sexy about wearing heels and being dressed like a slut while I butt fucked Jennie.

My dick rested against her anus. Jennie made no sound or movement. I pushed down. The head disappeared. She let me in and gasped. I continued to bend my knees, letting my weight bring me deeper inside her. I backed out a little, twice, before the full length was inside her. My weight rested on her butt, squashing my sack until it pulled tight around my balls. I lifted my body slowly and let it down again. The safest option to please Jennie was probably to be gentle and kind, so I resisted the temptation to pound her ass as hard as I could. Besides, I was wearing heels. The last thing I wanted was to topple over and create an anal sex accident. No doubt, that would destroy her mood. Smooth and steady was the answer. My dick felt the love of her anus, gripping me tightly as I slid back and forth. It was heaven on a stick, my stick and her heavenly ass. She turned to look up at me, “Are you okay?”

The question did not make sense. For a moment I felt confused. My vision was blurred, so I blinked a few times. There was Jennie’s butt, right in front of me. It was half covered by her skirt and she was leaning on the table in front of me. One of my Jennie fantasies had taken over my thoughts and I lost track of the real world. My first thought was disappointment that I still have not fucked her in the ass. Then I saw her looking around at me.

“Yeah, I’m fine.” The only trouble was that I was a little more than fine. My dick felt as good as I had imagined it did and I was about to cum. That is when I noticed I still had a firm grip on myself. There was no preventing it now. Cum was on its way. I had to act fast.

My thoughts had been so distracted that I had no clear plan at all. I had to get up, but didn’t dare let my dick swing free while cumming. I held it against the side of my thigh as I stood up, to be sure Jennie would not see it. She turned around as I was getting up which left no chance to move it. I put my knees together so tight that it held my cock in place between my thighs. I tried to stand up. Having an erection made that a little difficult. I could not stand up straight and nearly lost my balance. The awkward movements of catching my balance while wearing heels and keeping my knees attached to each other must have looked bizarre.

“Do you have a cramp or something.”

Saved. A cramp was a brilliant idea. Better than admitting I was just a pervert caught cumming when he shouldn’t be. “It’ll be okay in a minute.” I looked at Jennie. There was concern on her face. My perverse mind thought how hot she would look with cum on her face instead. That is when it started. I stood with my feet slightly parted, pointing together so my knees could be held firmly. My thighs were at an angle so my torso could be upright and my elbows held me up on her kitchen counter.

It still felt great as each spurt came out. A warmth formed between my thighs and I knew there would be a considerable mess there. Of all the times for an extended release, this was the worst, yet it seemed never ending. My dick kept twitching and I felt more release between my legs. I could not contain it. I felt it start to trickle down my left leg. For now, it was out of Jennie’s sight, but it would not stay that way. How was I going to get out of this? How long before she would smell it?

Jennie seemed worried that I had not moved for some time. I hoped she still believed it was a cramp. There was no way out of this. I needed her to go away, leave me an opportunity to run upstairs and clean myself up. As long as she was right there watching me I could not do it. I had to think of something fast.