My Perfect Wife free porn video

My Perfect Wife by Amy Brett I'm a financially and mentally stable, large, strong, masculine guy. I've been a contractor for the last few years after working my way through the trades - masonry, plumbing, electrical, roofing, framing, and finishing at different times. I suppose I'm not quite as toned as I was at some times of my life, but even just estimating jobs, helping when my employees need it, and jockeying these guys around keeps me in pretty good shape. Even at 42, I still have 26 inch biceps, a 44 chest, and a 34 waist on a 6 foot 2 inch frame that I keep right around 190 pounds. The graying hair on my chest and chin is dangerously close to being matched by the hair on my head but I can still lift more and outwork the majority of my employees. I was married directly out of high school and had two kids. But my work schedules made her feel like I was ignoring her. I was often dead tired and I know I contributed a great deal to our breakup. I wanted peace and quiet that two kids and a wife couldn't provide me. I also wanted a few beers before taking my very pretty wife to bed for a good fuck or, at least, a nice blowjob before sleep. Reality pretty much took care of things. We were divorced when I was 32 and neither of us looked back. I see my kids occasionally still but my ex remarried happily and really isn't the tiniest bit interested in me or what I'm doing. I'm interested in her only to the extent that she was once my friend, as well as my wife, and has far more effect on the kids than I do. I'm still busy, though not as busy as I was when we divorced. I still have the same needs and wants. Off and on, I find a woman who interests me enough to date. Many were a one night thing and a few were interesting enough to date more than once. But universally, they wanted a homebody husband, disliked beer drinking to one extent or another, had limited sexual needs, or, the worst, had children or badly wanted them. Other things bothered me about the women I dated (or the one I had married). They tended to talk too much. Few were interested in even some of the things I was interested in. None could simply watch a football game, sit back, and enjoy a beer or two. None were the least interested in my business or the difficulties I encountered every day. Understand too that I have and have had lots of male friends. I work with large groups of men every day and enjoy their language, stories, interests, and virtually everything else. I am NOT gay and have never touched a guy to do more than put an arm around his shoulders if he'd had some kind of disaster in his family or to put my fist on the end of his nose if he challenged me. Since I was having such abysmal luck with women and still needed someone, I guess I may have been toying with the idea of having a gay fling. At least, one night with a six pack of beer stashed safely inside, I got on a chat for gays. I watched several guys talk to each other about things I could never identify with. In fact, I was ready to bail out when a square popped up on my computer screen that said "Amy" wanted to talk to me. I accepted the connection. I said hello and got a reply in kind. Then she apologized for interrupting me to which I said she was more than welcome since I couldn't stand what I'd seen on my screen. She apologized again and said I probably wouldn't be interested in her either then. Ignoring that, I began asking about her. I learned that she was 5 feet 6 inches tall, weighs around 125 pounds, has dark brown hair that's moderately long, and green eyes. She was also 32 years old, unmarried, and a business manager for a small company I vaguely knew about. It didn't surprise me at all when she said she would love to be some masculine guy's wife and take care of him any way he wanted. I'd heard that before. We reviewed the things we enjoyed doing: movies occasionally, football, the same kinds of music, summer camping, chilling to the TV for a few hours, good food either at home or out, and sex. I asked her what her ideal was for sex and, totally amazing, she told me she'd prefer once a day or, at most, every other day but with some "special" occasions when the time was available. When I asked her what her favorites were, I was completely floored. She told me she loved oral and anal sex but loved sex in all locations and positions if she was "surprised." Like most women, she said she enjoyed kissing and touching and just cuddling. Strangely, I enjoy those things too but have found many of the women I've been with can get frustrated with it. Okay. So I had to know how she preferred to dress. After we got over the standard "how my man wants me," she told me she loved high heels, stockings, and short skirts but had jeans for rougher activities and shorts for warm weather. So this might not be the perfect match for me, but she sure as hell peaked my interest. I guess my excitement somehow came across in what I was typing to her. That's when she said she'd like to meet me, too, and whether I would be most comfortable going to her apartment, having her come to my house, or meeting at some neutral place like a bar or motel. And that's also when she brought me back to reality and the almost forgotten memory of where I had been chatting. "You know, if I meet you in a public place, I'll have to dress in my normal guy clothes?" Shit. Of course. This was a gay channel and, though I'd somehow thought this was a woman I was talking to, it was a guy who liked dresses. I thought seriously about just turning the computer off. Then I considered telling "her" I'd forgotten about being in a gay channel and just apologizing before I left. Then I realized that one of my requirements - not being interested in having kids - would be an absolute in this case. Laughing at myself, I told her it would probably be a good idea to meet for a beer and signed off. *** Right down to the moment I drove up in front of the bar (motel lounge actually) where we had agreed to meet, I vacillated between going and simply forgetting about it. I was sure that whatever decision I made, the guy would understand. Finally walking into the lounge, I had decided that neither of us had committed ourselves to anything but having a beer and there is certainly nothing wrong with having a beer with another guy. The bar was just off a large lobby and boasted four tables and a bar with six stools. Obviously not one of the local gathering places. Two businessmen sat at one of the tables and two individuals sat at the bar with an empty chair between them as they chatted with each other and the young woman bartender. Another man sat alone at a small table away from the other people with a glass of beer in front of him that had been lowered about half an inch but had sat there long enough to lose most of its head. Even as I stood there looking around the room, I knew I could just turn around and leave. He certainly looked harmless and didn't show any obvious signs of being a swishy gay. With a fairly rapid look, I saw he was wearing jeans and a long sleeved shirt, he looked comfortable leaning on one elbow on the table while his hand touched the edge of the beer glass as he stared into the amber liquid, and his face was clean shaven and unblemished but unremarkable. His dark hair was pulled back into a masculine pony tail that I saw all the time on the guys I worked around. Mentally shrugging, I walked to the table. He looked up and smiled before smoothly standing to shake my hand. It was a firm handshake though I felt a little tremor as I returned it. As with many guys I worked with or contracted with for work, my hand was bigger and, I'm sure, much more callused. In this case though, my hand engulfed his much smaller one. He said his name was Andrew as I introduced myself, took the two steps to the bar to put down a five, and ask for a beer I saw on tap. The bartender started filling the glass as I returned to the table and sat down across from him. He started the conversation by perceptively noticing that I looked tired. It had been a harder than average day and I acknowledged that I was tired. Somehow he started me talking. My biggest problem of the day had been with a guy I'd contracted with to redo some rooms in his house. It wasn't too unusual for a client to press for more than I'd agree to do and I certainly couldn't give away things that took both labor and materials without an addition to the costs. I was a little surprised that Andrew came up with a couple of very good ideas to avoid the problem in the future and one very important one concerning the specific client I was working with then. That started us off with a good basis and our talk revolved around our work while we drank that first beer. The conversation lightened when he said something about the football game the next Sunday. We kidded back and forth since he was a fan of the team I was hoping my favorite would beat. We discussed quarterbacks (which is pretty superficial) but I found he knew as much or more than I did about the safety/receiver match-ups and the weaknesses of the two teams. It seemed that the beers and conversation had loosened both of us up. My thoughts went back to the original reason for meeting him and I felt my own unease return. "You don't seem ... gay," I said. He didn't. Maybe the way he moved, particularly his hands, were a little ... softer, I guess you'd say, than I was familiar with. But he wasn't the least bit swishy and he didn't lisp or meet any other of the other gay stereotypes. He took me by surprise again. "I'm not," he said directly and sipped at his beer. "I'm completely heterosexual. When I'm a man ..." he gestured toward what he was wearing "... I'm masculine. "But when I am wearing a dress and high heels, I look in the mirror and see a woman. I feel like a woman and I act like a woman. I'm not gay. I'm not a man in a dress. I'm a woman and I'm feminine." He was quite convincing in what he said but, looking at this reasonably masculine guy, I couldn't see a woman there. "You do that often?" "Yes, I dress and I enjoy doing that a great deal. But it's particularly obvious to me then that there is something missing from my life. Even now, sitting here talking to a nice guy about business matters and football, I know I need a friend. As a man I need a friend." He looked down at the table and spoke very softly. "When I have a dress on, I know I need a man. To ..." he sighed "... complete me." "So ... then you change personality completely? You are this other person?" "No," he said as his eyes returned to mine with the denial. "No. I'm the same person with the same interests. I just feel and act feminine. "It's so hard to explain. Even to myself." Since he'd acknowledged the difficulty of understanding, I decided just to move on. "I've seen pictures of what they call shemales," I said. He nodded and pursed his lips. "Some are very pretty but it seems like they wear too much makeup and tend to favor really tacky clothes." "Yes," he said. "I'm not a shemale and I think I'm pretty conservative with my tastes in clothes. I like short skirts because my legs look good in them. But extremely high heels are tremendously uncomfortable and really don't look good when you have to stumble around on them. "I try hard to do makeup but it is a talent. I don't know how successful I am but I never overdo it." For a very long few minutes, I sat there thinking as I watched him stare nervously into the remaining inch of beer in his glass. My words ended up being the thought I'd formulated. "I guess I wouldn't understand without seeing it," I said. I couldn't believe the transformation that came over his face. In a transition that went through a dozen little changes, he went from scared and nervous staring into his beer to very bright and smiling as he looked back into my eyes. *** I knocked on the apartment door pretty close to 9 the next Friday night. I knew now that I could at least enjoy talking to Andrew and was not the least concerned that he was some kind of weird fag. In fact, I rather looked forward to talking to him in a more private setting where I wouldn't feel so self conscious that someone might overhear. If someone had, it probably wouldn't have bothered me particularly but, liking him, I didn't want to embarrass him. His apartment was in a decent part of town but the building was a completely unremarkable cheap mass market construction in a totally simplistic design. I could have drawn a floor plan of the building before I walked in the front door. There were four identical apartments only different by ground or balcony access and whether they were the right hand version or the mirror left hand version. Inside, there would be a small living room with a visible kitchen, two bedrooms toward the back, and a small bathroom between the kitchen and first bedroom. It probably sounds like I'm making excuses but, when the door opened, I honestly thought I'd inadvertently knocked on the wrong door. I guess it showed on my face because the quite pretty woman holding the door open to me smiled broadly. I was still thinking that I had either knocked on the wrong door or was at the wrong building in the complex of identical buildings when she called me by name when she asked me to come in. It was still with some doubt that I went in and moved far enough to the side that she could close and lock the door behind me. "Thank you for that," she said in a soft, fairly deep but completely feminine sounding voice. My mind struggled to remember what Andrew's voice had sounded like. "Please come in and make yourself comfortable," she said. "Would you like a beer?" "Yeah. Uh yes I would please. Thank you." She turned and walked through the room into the kitchen I'd predicted exactly. Her walk through the room gave me a chance to see her sensible two or three inch high heels with their ankle straps and small toes, the sides of her feet visible. Her steps were, like a fashion model's, almost directly one in front of the other. Her calves were slightly muscular but nicely shaped to long, soft looking thighs, all encased in sheer stockings. The short, full skirt looked like it must be made of silk or something nearly as light weight as it moved as if it had a mind of its own around her mid thighs. The way she walked moved her petite ass in an alluring way from side to side that flipped the skirt at each step. The waistline of the skirt was below her narrow waist and neatly held the hem of the silky white blouse. The front of the blouse I'd seen on the way in was a puff of frills something like tuxedo shirts I'd seen and refused to wear. The back was plain and a lacy looking bra strap was visible through it. Her dark hair looked longer than what I'd seen tied up in that boy ponytail, dropped almost to the top of the bra strap. When she turned back to ask if I wanted a glass with the beer, I more closely inspected her bright red lipstick, professionally done eye makeup, and the stylish front of her hair. Dangling earrings dropped from her partially visible ears and a tiny necklace glistened at her neck Her bare arms were long, thin in a feminine way, and not the least muscular even carrying the beers and her glass. She handed me my beer, curled the leg nearest me up so it pointed generally in my direction on the couch we shared in a way I'd only ever seen a woman do, more or less faced me, and poured her beer into the glass. She smiled very sweetly and gestured in the familiar toast. "Uh, what do I call you?" "You don't remember?" she said in a teasing way, her eyes sparkling. "Oh. Of course. Amy," I remembered from the first time I'd talked to her on the computer. Talking with Andrew in our first meeting had been difficult at first but easier as I found him to be a perfectly normal guy. Talking to Amy over the next hour was far more difficult even though we'd established enough mutual interests to give us some common ground. The problem wasn't finding a topic or disagreeing wildly. It was her obvious interest in me as a man and, as far from the things we talked about as you could imagine, my realization that she was physically a very interesting "woman." I found myself listening to her voice (which still didn't seem the same as Andrew's) or enjoying the extent of stocking covered thigh she unselfconsciously displayed or wondering about the long well manicured red fingernails or concentrating on her animated red lips. I could see a few masculine gestures or movements creep through. I could see just the remnants of the Andrew I'd met before in her face. But mostly I watched her hands dance in front of the frilly blouse in a way that no man I knew could. I kept losing track of the conversation as my mind moved around to "What next?" "Am I comfortable with her?" "Should I ...?" "Or should I ...?" Maybe she saw my quandary. Maybe she simply got tired of waiting for me to say or do something. Maybe it was simply a spur of the moment thing. She had just gotten fresh beers for both of us and sat mine on the end table beside me, leaning on the arm of the couch at my side. She stood there in that position over me for a bit longer than was needed and met my eyes. Apparently she made a decision. Now, I'm sure the decision was all or nothing. We'd been verbally dancing around each other since I'd arrived. Both of us had been thinking about what might happen next. She was the one to make the decision that men feel they always make to bring things to a head. Standing straight in front of me, she extended her hands like I'd seen women do to get a guy to dance with her. Since there was only low background music on, I didn't think she wanted to dance but accepted her invitation to stand up. As I stood, she raised her arms to my shoulders, leaned against me, and lifted one knee just enough that I felt her leg against the outside of mine. I had very little choice but to put my hands on her small waist. The skirt and blouse she wore was as silky feeling as they had looked. "Okay. We've talked. You've been sitting there undressing me with your eyes and I didn't see much disapproval. Now you can feel that I'm real. So what do you think? Am I a woman?" "You didn't say that the perfume you're wearing is fantastic and you certainly smell like a woman," I said with a smile. That's when I made some kind of decision. She just smiled up at me as I slid my left hand up between her shoulder blades and the right to the small of her back to pull her little body hard against me. Her eyes glittered as I slowly lowered my mouth to her lips. As our lips touched, hers opened with a sigh and her hands at the back of my neck pulled me harder into the kiss. As her eyes closed, I noticed that even that close, her long lashes and soft green eye shadow looked good. As my tongue slid into her offered mouth, she moaned with pleasure. We stood, locked together that way, for a very long time. My upper hand slid across her bra strap as the other found her waistband and then down to the rise of her little butt. Her body squirmed against me and her kisses intensified, sucking my tongue or following it back into my mouth when I thought to ease our excitement. Her hands vibrated with excitement when our extended kiss stimulated something new in her. I could feel the rise of breasts against my chest and wondered passingly how that was possible and I hadn't noticed when talking to Andrew before. Then her stocking sheathed leg moved up the outside of mine in a feminine gesture I'd always thought of as one of the most sensual a woman could make. I was so hard it was almost painful and my balls ached for release. I'm sure she could feel it against her stomach and may have even been squirming against me just right to further stimulate me. I cupped her tight little ass in my hand and felt the muscles move as she used her leg to stroke up and down mine. Simply out of breath, I broke the kiss and put my head against the side of hers, breathing in the scent of her clean, feminine smelling hair. She had her head back and was panting as her hand rubbed the back of my hair. "You are ..." she gulped oxygen "... a wonderful kisser." I chuckled. But then I straightened and looked down into her smile as her hand moved down until it found the bulge in my pants. As if exploring totally unknown territory, her fingers teased through the material from the base upward along it until she reached the head at the side near my belt. It was uncomfortably bent and wasn't getting better as her hand traced its shape. She groaned and I'm not sure whether it was a sound of pleasure or fear. Smiling even more brightly, she slowly sank to her knees in front of me. She looked at the front of my pants from close up then back up at me as if for permission. I didn't stop her as I may have been able to do but I wasn't going to force her either. All I could do is stand there and hope I could stay standing if she did was she very evidently intended to do. She continued to look up at me as her fingers delicately undid my belt, struggled a little with the fastener at the waistband before it released, and then slowly moved the zipper down. The lightweight material, the pockets filled with change, keys, and billfold, dropped past my knees. For some reason, I was pleased that my loose boxers weren't providing support for my cock which was still straining upward and to the side. Concentrating now with her tongue peeking out between her red lips, she lifted the waistband out before pulling downward, something a different kind of woman would never think of doing (just as few would be in the position she was in then, thinking it too demeaning). She was gentle and careful as the elastic waistband moved down to show her the head of my cock. She licked her lips in a very distracting way for me. Her fingers went to the sides of my boxers and pulled downward until the waistband finally moved down my butt. Impatient now, she tugged more firmly until they moved to my thighs and my cock sprung toward her face. She might have bounced away or gasped or any number of other reactions. But she did none of those things. She stared at the tip of it from a perspective only a couple of inches away and her mouth opened as if in awe of it. "Is it okay if I suck it?" she asked with a childish look in her eyes like I would probably tell her no. I'd almost forced my wife to do that a few times and she hated every second, as far as I could tell. I'd had women do it a couple of other times but never with any real interest in more than getting me hard. I couldn't help laughing but, I hoped, added that I'd love it before she would feel hurt. She smiled up at me from that position on the floor that women seem to feel too demeaning to even consider. Still somewhat tentative, her prettily red painted lips kissed the tip. We both chuckled as it bounded away from her of its own volition. She grabbed the shaft more firmly and let her sweet little pink tongue go out to trace the shape of the head slowly. It was one of the most sensual things I'd ever seen, only topped by the combination of sight and feel when she took the whole swollen head into her lips. That's when she actually sucked at it and her eyes softened with real enjoyment and relief that I wasn't stopping her. Of course, stopping her was absolutely the last thing I would have considered. As she seemed to just fall into sucking and licking my head, her hands seemed to find every sensitive spot - one very gently on my balls and the other still clasped around the shaft, gently stroking. Her hand seemed so small it covered only a little more than half of its length though fully around it. She very thoroughly worshiped the head with lips and tongue, sliding it in and out while licking and sucking. She was in no hurry at all but already I knew that this was the best blowjob I'd ever gotten and all she'd have to do was get a little more serious with the stroking and she'd get a nasty surprise. Like some before, that was when she stopped stroking at all and I thought it was probably over. Resolved but disappointed, I still thought it was as good as it came. Then she really took me by surprise. Her lips still around the head and her talented little tongue making shapes on it, her hands moved to my hips. I looked down at her pretty face and smiled as she looked up at me. As if that was a green light for her, she strengthened her hold on my hips, opened her lips slightly for a cool breathe around the wet head, and dove forward until I felt the head hit the back of her mouth solidly. I know I groaned loudly. It was the furthest my cock had ever been in anyone's mouth. As I expected, she moved back out again quickly but, not expected at all, she dove back onto it and twisted and turned her head until it went in further. I gasped with real disbelief. But, if that wasn't unbelievable enough, she moved her head away slightly and plunged down onto my cock until I felt her lips kiss the base of it and I felt the head go down her tight throat. For the first time in my life, I was being deep-throated. Just to make it more unbelievable, she began moving out and in and out and in so her throat stroked my head as her hands clutched at my hips to oppose any movement of mine away from what she was doing. I tried to moan my eminent release before I literally drowned her, but nothing coherent came out of my mouth. I exploded down her throat and expected her to fly away from me. But she didn't show any sign that I was filling her with my cum. She just lengthened her head's in and out movements, taking every ounce of cum out of me. Just before it got painful, she stopped the fucking movements with the head just inside her lips. When I could open my eyes, she was looking up at me with a pleased look as her tongue moved around and over my very sensitive cock head. Finally, I couldn't stand it and held her head while I pulled it out of her lips. As it fell limp, she turned her head and hugged my legs, her cheek against my pubic hair. "That was ..." I started but she interrupted. "Thank you for letting me do that. I wanted it so bad." She hugged tighter. "Was it okay?" Literally staggered by the whole thing, I dropped onto the couch. She let me go of course but looked at me hurt. "Sweetheart. That was the most outrageous thing anyone ever did for me. Nobody ever..." "Really? It was okay?" I actually threw my head back with the biggest laugh I'd had in years. I started to tell her again but, instead, I motioned her toward me and, when she knee walked onto the couch next to me, I took her in my arms and pulled her against me hard. *** "You know what?" I asked her as I realized exactly what I intended to do. "I've never done this but I'm going to show you just how great you were." I didn't ease my hold on her much but eased her back until she was laying on the couch next to me. One of her knees was against the back of the couch with the lower leg along mine. The other was more or less standing off the side of the cushion. Stroking the calf alongside my leg, I eased it up until it was against my side before I moved forward a little and let her straighten it a little behind me. Unlike what she had done to me a minute before, I had considerable experience with a woman on her back near me and knew exactly what I was doing as I ran my fingers up and down her inner thighs. I didn't have huge amounts of experience, as guys sometimes do, but I thought I had my share of getting around the bases. So far only my wife had resisted my movement from kisses to intimate touches to serious licking and sucking to a good fuck. Strangely, her long term resistence to moving from one base to the next may have dragged me into love and marriage. I did fuck her before we were married (as I think every guy should) but it was a near thing and damned difficult. What I'd done in the process was get very very good at working at it logically and slowly. Just a step forward before she stopped me again. Another step. Yes, another step. Cue the Rocky theme. If there was something different about this situation, it was that Amy was more willing than my wife, even the last time we'd made love. She squirmed and grinned with the feelings my fingernails on her stockings were driving through her sweet little legs. She made it obvious that I was doing good things to her as I traced up and down from the hem of her skirt to her knees. She was twisting and moaning with just my touches. I couldn't help but see the contrast with virtually every woman I'd ever been with. They might enjoy this for a minute. Some would sit up and want to back it off to kisses. Some, like my wife, would get up, take my hand, and lead me into the bedroom. In that case, it would be a complete change in direction that usually ended up in bed, in the dark, and with completion. But it hadn't necessarily been the direction I'd been heading when I started. Amy let me take it where I wanted to go. Her legs strained with excitement and visible goose bumps as I traced the shapes of her legs all the way to her ankles and up to move her skirt slightly upward. Sometimes I kissed the inside of her thighs. Once she lifted her leg behind me and I kissed her calf. My fingernails traced the shape of the outside of her sweet legs. I found the hollows behind her knees and she gasped. My fingertips found the top of her stockings and she stiffened as I found naked skin but teased her by moving all the way down the length of her legs again. "Do you know what I'm going to do?" I asked her. She squeaked an answer but it wasn't coherent. "I'm going to find your little panties soon. Not for a minute or two minutes but in time. Then my fingers will touch your tiny clit. Maybe I'll rub it until you have your first little orgasm right through your panties. But then again maybe I won't. Maybe I'll rub it until you're so close you think it's unstoppable and I'll stop it. "Then I'll pull your cute feminine panties down - I know they are the most beautiful you could buy for me - and I'll see your clit there in its little nest of pubic hair. Then I can really touch it and watch you squirm. But that's not the best part." I let the suspense build a moment. She knew what I could do and couldn't be surprised. But she seemed to be loving what I was saying to her. "I'm going to lick your little clit and suck on it until you squeal with your need to cum. But I'll stop. Then I'll do it more. And stop. You'll beg me but I'll wait until I think you can't stand it any more. "Then I'll make you cum so hard you won't think you can live through it." My fingers had been moving up and down her legs, finding the top of her stockings each time, moving her skirt up slightly at the top each time. Now I could actually see the white lace of her panties between her spread legs. She was squealing with every movement and her center was pumping up and down steadily. Finding it more than a little difficult to go slow, my fingers went up the outside of her legs to the narrow waistband of the bikini panties, dragging her skirt up with them. I had an odd moment of dislocation. I could see the front of the panties and between her legs. What it looked like was a slightly larger than normal Mound of Venus. It was not what I intellectually knew was there. I moved her skirt up as high onto her stomach as the waistband allowed without any sign of protest. It seemed bizarre that my wife and all but one woman I'd ever been with would have stopped me right there or jumped on to moving to the bedroom. As I'd done (without being able to see what I was doing) with several women, my fingers moved across the lacy front of her panties, feeling the swelling beneath. With a finger along each side of it, I stroked her. It took less time than I'd planned before I had to see better what I was doing. When I moved to her hips and found the waistband, she moved her legs closer together to allow me to pull them down. Another contrast. When I had them onto her thighs, she lifted her knees and encouraged me to move them the rest of the way down her legs, to her ankles, and off. Now I could hardly wait to see what I'd uncovered. Obviously wondering what my reaction might be, she put her legs down straight and tight together. I couldn't see a pussy between those tightly clasped legs but I wondered a little if there might be one. Yes there was a dislocation. Looking low on her tummy, there was something that looked like a cock but it was so different from anything I was familiar with as to be somewhat confusing. Maybe four inches long at the most, it looked longer because it was very narrow and surrounded by nothing. As I pushed her knees apart to try to get a better view of it, I saw the little cock stand up with a slightly wrinkled hint of a scrotum below it. I couldn't see the pussy I half expected to see. I also couldn't see even a hint of pubic hair. I have to tell you that I've never been in the slightest doubt about being gay. I'm not. And I am not the slightest interested in children of either sex. But, I suppose, what I was looking at seemed to belong to a young boy wearing stockings and a skirt. After just saying I'm not gay or interested in kids, it's even less understandable why I dove down and took that little cock in my lips pressed against the top of my mouth as I extended my tongue over what might have been a scrotum. I'm not sure if it helped or just added to my dislocation when she squealed like a little girl and lifted her legs over my shoulders. Her little body arched and twisted as her hands went to the back of my head. Her squeals of pleasure continued as I licked and sucked and moved on her for the next few minutes. Then she froze and moaned. I noticed a slight flavor at the back of my mouth and peripherally thought she was having an orgasm. She was panting and even pushing at my head after a few minutes but, as bizarre as it sounds, I continued sucking the loose mass and licking between her legs as I stroked her stockings. When I backed away, I looked down at what I had left and saw more of her smoothly shaved tummy over an area of loose skin that looked very much like a clitoris and labia. Her eyes sparkled as I'd seen other women's after orgasm and her smile was beautiful and grateful. I pulled her skirt back down over her, leaned down, and kissed her gently. A few minutes later, I held her in my arms and gave her a kiss as we stood in her opened door before I left. *** Two days later I called her. Andrew answered but turned me over to Amy fairly quickly. Her telephone voice was soft and feminine in a fairly deep, dark tone somewhat reminiscent of one of the 1930's movie femmes fatale. Strangely, she thanked me first for not being mad that she'd wanted me so badly and, after we'd stumbled over that odd statement for a while, thanked me for sucking her "clit" and giving her that wonderful orgasm. We talked about inconsequential things beyond that for a while before we hung up. A few days later, I called her again. She'd told me the first time I'd called that she would never ever call me unless I specifically told her to. Since that would protect me from embarrassment at work, it was a good idea. Again, Andrew answered and loudly called to Amy. What a fantasy he could build, I thought with a chuckle. It took a minute before she picked up the phone. After the hellos and exchanged pleasantries, I asked what I was interested in. "Amy, would you be comfortable going out?" Not really. "Why?" Because some child or sensitive person might see and be offended. "What kinds of things will you do with me?" She'd love to make dinner for me or even just have drinks together. Anything. She had liked me a lot and wanted anything I wanted. Anything. "You want me to fuck you?" I asked with a little chuckle to soften the statement. Maybe she wouldn't be offended by the question or just laugh it off. "Oh, honey. Please don't tease me," she said with a hurt sound in her voice. "You mean you do?" There was a long near silence punctuated by her heavy breathing, as if she were trying to get herself under control. "Yes," she said finally. Softly. "Anything you want." It sounded very strained. "In your bed?" "Yes." "Over the arm of the couch the second I walk in?" I asked. "Oh yes. I'd love that." "Would you have an orgasm for me?" "Many. I'd have orgasm after orgasm." "I don't have to buy you candy and flowers or take you to dinner and a movie?" She laughed out loud before saying no. "No jewelry? No rings? No wedding ring first?" There was another long silence with the panting breath. "Please don't tease me," she said softly and with great feeling. "That's my dream some day. But I know ..." Another long silence. "I'd love for you to fuck me any time and any way you'd like." "I want to," I said and then realized that it was very true. She turned me on more than any woman I'd been with. "Come over. Okay? I want to prove it to you." "I can't tonight. I have an early day tomorrow." "After work?" she moaned, in distress. "Maybe. But Friday would be better." It sounded like she might cry. "If that ... yes. Okay. I'll make dinner for us. About 5?" "I'm never sure when I'll be able to get away. We'll say 5 but it might be a little later." I stopped to think. "What can I bring with me?" "A six pack if you want. I'll make something good. Maybe wine if you like it too." I hung up after we'd settled on the time. *** Maybe I was reacting like a teenager but I found myself thinking about Amy all day and wishing my way through what I needed to do. Purposely trying to restrain myself or possibly apply a little discipline, I held back from leaving work early and knocked on her door only a few minutes after five with a relatively expensive twelve pack of imported beer in my hand. "Hi," she said with a huge welcoming smile on her modestly made up face. I nearly gasped as I looked up and down her stylish short black cocktail dress, long looking sheer stocking covered legs, and cute high heels. Her arms were bare except for a modest bracelet and the top of the dress exposed her shoulders and much of her chest. Strangely, I thought my dockers and polo shirt were totally underdressed. Moving close to me, she took the beer from my almost numb hand and turned to take it to her refrigerator. "Should I open a couple of these or just bend over the arm of the couch," she said with a smile. I laughed and let go of any remaining hesitation. "I'll restrain myself," I said, wondering a little if I could for long. She nodded and took two of the beers out of the case and opened them before returning to the couch. She put one on each of the end tables, along with a glass for hers, and stopped there looking at me. Then she burst into motion and almost jumped into my arms and pulled my mouth down to hers for an extended kiss I didn't resist at all. "I'm so glad you came again," she said when we broke the kiss a minute later. "How could I resist," I said, only then knowing that it was completely sincere. "I was going to watch the news," she said. "Probably pace around the room like a caged tiger." She blushed and held her little hands in a very feminine gesture in front of the rise below the neckline of the dress. She was completely balanced on one high heel and her other bent leg as she stood there in front of me. I nodded approval of the news and sat down on the couch as she turned it on, curled one leg so she was nearly sitting on it, and sat down very close beside me. I moved to put my arm on the back of the couch but, when she rested her head on my shoulder, it just seemed natural to put my arm around her as we sat watching the news. I sipped at the beer and split my attention between the television and her very pretty and nearly completely exposed leg which nervously flexed and rose and fell. I wasn't so deluded that I didn't wonder if she had real breasts held in by the moderate sized bra whose strap my hand contacted. I still reveled in how perfectly she could be so totally feminine in her movements and even her voice. As we watched the news, we each had comments on events. I consider myself pretty non-political unless something the politicians did affected my business and she seemed to feel the same. Both of us hated criminals and had unfortunate experiences with people we worked with. I'd had to turn in several workers who had tried to steal tools or were doing drugs at work. She had similar experiences with people who worked for the same company he worked for. Even though I was thinking about what would happen and when it would be most appropriate, I wanted to see this woman as a whole person. Of all things, I didn't want to simply think of her as a sexual object since, in fact, I wasn't sure that was even possible. During one commercial, I turned her across my lap, put my hand on her stomach, and thoroughly enjoyed an extended kiss that she did everything possible to make as good as possible. She was, without a doubt, the best kisser I knew of and responded and participated in it more than any woman I'd been with. In short, she loved to be kissed, loved having my hand explore her side or rest on her stomach, and loved to stroke the side of my head or my neck. Her lips and tongue were soft and sweet and very active. It was difficult to back off after a few more minutes of news to follow her to the table where she served a nice, simple dinner. Sometimes a special meal is good but I guess I'm mostly a meat and potatoes kind of guy. The most important thing is that it tastes good and there is enough to fill the gap from a hard day working. I try not to use both hands to stuff the food in and take time to chew the bites, I can't say I'm well suited to high society dining either. What she served was perfect, in my estimation. We sat drinking our beers and talking after dinner. The conversation ranged from the Saturday college football games to the things we'd seen on the news before moving to how we had spent the day at work. Then I just couldn't keep from learning more about her. "Are you comfortable in that dress?" I asked and she smiled and nodded. "There's no doubt that you look wonderful in it. I just ... I don't know." "Yes, I like the way it makes me feel very much and you really validate it for me. Just the way you look at me is wonderful. But when you touch me and ..." she blushed "... kiss me. It makes me feel the way I want to feel." "You want to feel like a woman," I said. "When I put the clothes on, I feel like a woman. But ... I can't explain it. When you look at me and like what you see. Or when you put your arm around me. Then I don't have even the small amounts of doubt about really ?being' a woman." I nodded at that. I understood the distinction she was making in spite of wondering just a little why a man would want to feel that way. That, I thought, was something in her and probably something I could never understand completely. Strangely, since I wouldn't have considered it just weeks before, what I was feeling was that she was absolutely perfect for me in spite of the facts of the situation. "I just have to ask," I said, thinking maybe it was really none of my business, "but your, uh, breasts ..." She laughed. "I have been taking hormones for about a year but it's a slow process. I started developing a few months ago and I probably have about A-cup real breasts now and the nipples have grown a lot and are very sensitive." "You can hide that under a regular shirt?" I asked. "Yes. So far. I hope they'll get bigger and maybe ..." I thought she meant that it might get to be a problem sometime. "You look bigger than an A-cup," I noted. She smiled and nodded. "At first I just padded them with Kleenex or socks but that didn't feel right at all. Then I bought some prostheses - breast forms - women use after they have a mastectomy. "Then, when I started to develop, those didn't fit right so I got some silicone enhancers that I'm wearing now." "Not those implant things, right?" "No that's a whole different thing. I don't want surgery." She bit her lip. "Any kind of surgery." "You mean even if you have double D's, you don't want to ... well ..." "No. That's called sex reassignment surgery, by the way, and I'd never want that. For one thing, hormones in high doses can lower your interest in sex. Having all the normal testosterone producing, uh, things cut off can take it away completely. Worst of all, SRS isn't good enough that you can feel very much in most cases. And I love to feel everything. Or ..." she sighed "... I think I will." "What do you mean? You think you will." "I'm ... I don't want to scare you," she said looking into my eyes. I smiled back but wondered what I didn't know that would scare me away. "I'm a virgin." I'll admit that I just sat there staring and my mouth was probably wide open. My mind leaped from one thing to another to another to another as I stared at her bent head. "You mean ..." "Okay. Not quite. I was with a girl in college. We even got engaged for a while. It's just..." she looked very nervous and studied her hands at the edge of the table. "You've never been with a man," I stated flatly. "Well, I guess you could tell I had a little experience sucking," she said. I laughed because if she hadn't she was certainly the most talented beginner I could think of. "But you've never been fucked," I said, finally figuring it out. She blushed and went back to looking at her shaky hands. I waited for her to say more. Any woman would simply gush words at that point. Either making excuses for the fact at her age or claiming to be ready or even asking for things to move on. Possibly even explaining why it wasn't going to happen. "Losing your virginity is a very big step," I said as if I was speaking to an 18-year-old girl. "Have you thought of how it's going to happen?" "Soon. I hope anyway," she said with a chuckle and squirmed in her chair. "It never crossed your mind where it might happen or what position or anything?" "I think I've thought of every possible thing. Wishing," she said with a little laugh. "But mostly what I want is for you to take me the way you want me, in the place you want me, and whatever else." "As long as I do it," I laughed and she joined me with a massive blush. "God I hope you do it." *** She sat there displaying every evidence possible of a fearful but expectant teen before her first kiss. I sat there plotting. First, I wanted it to be the best possible experience for her. Since I knew the physical problems that were likely of putting a fairly large object into a fairly small opening, I certainly didn't want it to be a painful experience any more than a younger girl's introduction to sex with a different but potentially as painful entry point. I also wanted to see what I was doing and allow her to see as much as possible. For one thing, sex is a sensual experience and vision is the primary sense behind only the sense of touch. So the lights needed to be on. Next, I knew she was totally female in this role and I wanted to ensure she could preserve her feeling of femininity as much as possible. In fact, it was at least as important to me. I wasn't sure I could maintain a hard-on if I could tell I was with another man. In fact, the thought sent shudders of homophobia through me though I'm not particularly anti-gay. I'm not gay and don't want to be but I hate the persecutions that some guys actively pursue against gays. It makes me nervous seeing two men kiss but I don't want to take a hammer to them either. Another concern was the simple mechanics of the whole thing. I thought it was possible to do anal sex from the front, probably with the help of a pillow under her or with her on top and able to change the angle of entry. Even by standing at the side of the bed rather than being on top of her. A small problem with that there would be no way possible to ignore her more masculine body features. So the best position, at least to start, would be from behind. In addition, I personally couldn't even guess how much it would hurt to have something put up my own ass. But I knew any muscle could be relaxed with a little effort and thought. If she was upset, she was going to clench her muscles and it could even be impossible. But worked on a little, she would relax and at least make it possible. And the value of lubrication was absolute. She had to be lubricated thoroughly and so did I. Finally, I'd heard of taking a woman over a table or chair or the arm of a couch but that didn't seem the best way to lose your once in a lifetime virginity. The same went for the middle of the living room carpet or even a couch. I vowed to myself it would be in her bed. As just a point of simple courtesy, I wasn't going to take her virginity, get up, and leave either. I knew, without a doubt, that she had thought most of this out for herself when she first contemplated it or during the time since it first crossed her mind. But I knew she wanted me to take the initiative - to be the masculine to her feminine. She would insist I make the decisions but I knew she wouldn't do anything that would do serious damage to either the illusion or her little body. All I could do was hope I wouldn't step over any lines she had made to herself and, more important, that I could make this a memorably positive as possible. I was not jumping into this with my eyes closed and I didn't think she was either. I stood up and held my hand out to her. *** "Is your bedroom good?" I asked and got my answer in the form of a broad smile. So far, so good, I thought. She turned on the overhead light when we got there but quickly moved to a bedside light before going back to turn off the overhead brightness. I thought it was a romantic amount of light that would also provide enough light to see what I was doing. While she had taken care of the lights, I kicked off my shoes and pulled my shirt over my head. It was pretty rewarding when she walked up in front of me with her hands clutched in front of her waist, looked at my hairy chest and bent one leg in that characteristically feminine way of hers. "How about you find us some good lubrication of some sort?" I said and she actually shivered before racing out of the room to the bathroom. I wondered that she hadn't prepared for this a little more but took it that she wasn't that sure of me or, unbelievably, hadn't thought it necessary. If it was me, I knew damn good and well that I would have thought of it. While she was gone, I stripped off my pants and socks but left my boxers. Just the thought of what I intended to do had me hard. She returned almost at a run and threw a tube of KY jelly on the bed to the side of where I was sitting again. "You're so ... masculine. Hairy. I never did ..." But I stopped her back in the position in front of me and close enough I could have closed my knees on the sides of her thighs if I'd wanted. "Are you proud of your tits? I mean the real ones; not the helper things." She sighed. "They're small but they aren't like ... a man's." "Good. Come here," I gestured even closer and her legs were against the insides of my thighs. My view was directly even with the rise in the front of the pretty dress as I reached behind her, found the dress's zipper, and slowly lowered it all the way to the rise of her little butt. Intuitively, she knew I wanted to take the dress off her and just stood there biting her lower lip while I smiled up into her eyes. I put my hands inside the opened back on the strap of her bra and small of her back to rub gently there. If I thought it might relax her any, I would have been very disappointed. She stiffened like a post. Enjoying the anticipation a great deal and really wanting to heighten the experience as much as possible for her, I slowly moved one of the dress's straps off her shoulder and leaned forward to kiss her chest just above the bra's edge. She sighed with pleasure but was ready when I moved the other strap from the other shoulder. The top dropped to the bend of her arms at her elbows and exposed the black lace bra she was wearing. I could see the slightly veiled shape of her small nipples surrounded by a little more than an inch diameter circle of darker skin. Her long upper eyelashes flickered over her closed eyes and her tongue traced her reddened lips. Guiding her, I moved her hands to her sides to let the dress drop to a precarious hold on her hips. Her quickening breathing lifted and lowered her bra covered breasts as goose bumps covered her arms and stomach. She had a little bit of belly but she also had a waist that broadened to nice hips. Maybe she didn't have a Barbie Doll set of curves but damned few women do. She also didn't have a shape similar to the men I work with or the hard stomach muscles you might expect. With a flick of my wrists, the dress fell from her hips and showed me a matching pair of bikini cut black lace panties. I could see the slight bulge of what I knew she carried between her legs and, low, equally slight shape of a scrotum. Those features were easy to ignore as I did, not wanting to spoil the illusion she wanted to form. I kissed her stomach and she gasped and lifted one foot to tiptoe. One of my hands went to the front of her bra covered left breast to squeeze slightly while I used my finger and thumb to tweak the other nipple. I rolled it for a moment as I watched her react to what I was doing. Looking up and down her partially exposed body, I saw the lacy tops of her thigh high stockings and vowed to myself I would keep them on for the things I planned. "I want to take your bra off now," I whispered into the silence of the room. She shifted from one foot to the other nervously but signaled her agreement. I steadied her with one hand while the other went to the back fastening of the bra and easily popped it open accompanied by another of her gasps. I didn't know if I needed to catch whatever the enhancers were but, as I moved to the bra straps on her shoulders, she put her hands under the bra and caught it as it went down her arms. At that point, I couldn't be concerned with whatever she was holding because I was busy looking at nicely shaped, youthful looking breasts topped with cute, perfect, hard little nipples. She shifted a little to drop the bra on the bed near my side. I didn't give her time to think about anything as my finger and thumb found one nipple as my hand under her arm pulled the other to my lips. She squealed as I took it in my lips and licked across the hard little nubbin. Her hands came up to the back of my head but neither pushed me away and pulled me against her. They vibrated in the back of my hair as I took it into my mouth slightly and sucked lightly. Backing away slightly, I used my finger to flip across the wet nipple. Then her hands tightened on my head and one knee came up dangerously near my nuts. I switched to cover her other nipple, licking and sucking slightly. Wanting to take advantage of the moment, I put my hands on her naked sides and pulled her breast tight to my mouth where I could nearly envelop it in my opened lips. She squealed again and tried to pull me tight to her but I resisted and left the moistened breast to give the other equal attention. I pushed away then and looked up at her face. "You liked that, didn't you?" "Oh y-y-yes," she shuddered. "We'll put that on the list of things to do later then," I told her with a chuckle and she took a shuddering breath as she opened her eyes a little. "But right now I want to fuck my little girl." From her forehead to her breasts, she flushed brightly as she again shifted from one foot to the other. Using both hands, I guided her to the side. She nearly tripped but caught her balance quickly. I got to my feet and headed her toward the bed. "I want you to crawl up on the bed," I told her and watched as she sinuously climbed up. "Why don't you pull a pillow down a ways so you can put your head on it without running into the wall." She did it as I got onto the bed behind her, deciding then that though it would probably be possible to fuck her in the missionary position, this first time would be better from behind. She has a beautiful little butt. "Put your knees together. I'm going to pull your panties off now." Almost panting, she did as she was told and I moved my hands to the sides of her panties. Unable to keep from caressing her cute hips and bottom, I took a moment to do that before my fingers went to the waistband at her sides and carefully moved the material down to see the little crack between her ass cheeks come into view. The panties stuck a little between her legs before I lowered them across the lace tops of the stockings to her knees. She lifted enough for me to get them below her knees and then lifted her high heels so I could take them the rest of the way off. "Is this what you want?" I asked softly and she nodded her approval. I picked up the KY jelly and flipped the top open as she rested her head and shoulders on the pillow, her back arched forward to lift her cute little butt high. I positioned myself to her left side slightly. I didn't want the distraction of what I would see between her legs but I needed to see what I was doing, too. "Spread your legs a little, sweetheart," I told her as I got a good bead of the lubrication on my middle finger. She moved her knees apart and her little ass cheeks opened for me. Concentrating, I touched the tight pucker of her asshole with the tip of my finger and watched her hump forward away from it. "Just relax for me." I used a little of the lubrication on the little opening and edged the tip of my finger to open her just slightly. She moaned. Transferring a little more, I spread it around slightly and re-entered her until my fingernail disappeared. Turning it inside her, I took it back out and put the rest of it on the opening before putting it back in, this time past the first knuckle before turning it from side to side and feeling how thoroughly it was spreading along the beginning of that opening. Another squirt from the tube and I could press it past the second knuckle. She squirmed in place as I moved the end of my finger inside her little pussy. A little more of the lubrication let me press my longest finger all the way into her until I held her almost like a finger in a bowling ball. Pulling it back and applying more KY, I slowly slipped my index finger in alongside the middle until the were both in her as far as the rest of my hand allowed. She gasped and humped her little butt up to it as I started stroking in and out of the tight opening. When I spread my fingers, I was a little surprised there was no resistence to doing that at all inside the opening. Thinking purely mechanically, I thought the only real impediment seemed to be the tight circle of muscle at the opening. For several minutes, I finger fucked her with the two fingers until her center was rocking and she was moaning with pleasure. She shivered when I pulled most of the way out, applied some more KY, and added a third finger. When I pushed them into her again, her mouth opened wide and she began oo'ing and ah'ing. I was more or less doing a boy scout salute inside her, moving in and out, wider and narrower, and twisting from side to side. I thought the muscle was as relaxed and she was as ready as was going to happen. Her face buried in the pillow, I scrambled around with one hand to push my boxers off my legs while continuing to finger fuck her with the other hand. Showing myself my coordination, I squeezed another gob of KY into my palm with the same hand and stroked in on my cock. Knee walking up behind her and between her calves, I stopped stroking and slowly pulled my fingers out of her before carefully aiming the head of my cock at her opening and gently pressing forward. Luckily, she hadn't had time or thought to tighten herself and, with a quick, "Aaa," from her lips, I popped into her. I'm really not sure that she knew she had just lost her virginity to me at that moment but I think she realized it as I ran my hands up her tensed sides to her armpits and then back to her hips. With that solid hold, I pressed forward gently but steadily, somewhat surprised that my cock slid into her with little resistence until I felt the tip contact something well inside her and she tensed around my like a hand clamping shut on the hand of a baseball bat. It wasn't uncomfortable really but the power of it took me by surprise. The fact that this normal action had little effect undoubtedly affected her more. After all, however I thought of it, she still had something fairly large up her ass when normally anything close to that big would be expelled as quickly as possible. I retreated a little and gained a sigh of pleasure from her before pressing forward again steadily until her little ass was firmly against the front of my legs. Strangely, thinking of what she was feeling more than of myself, I wondered if my pubic hair tickled where it touched her ass. Whatever she was feeling, it drew out an extended moan so long I wondered where the air was coming from to propel it. She gasped air back in explosively when I retreated slightly and pushed back to that furthest deepest place inside her. "Are you okay?" I hissed, realizing I was short of breath too. "Yes," she squeaked and humped up toward me somehow. I couldn't have possibly gotten further into her than I was but somehow it felt like it. Wanting to be as gentle as possible with her, I restrained myself as much as I possibly could, slowing the strokes out and into her as much as I could stand. But she ruined my attempts when she started humping up to me and away at a faster rate than I had intended. Unable to resist her squirming ass around me, I began fucking her in earnest, perhaps pulling as much as half way out and back into her. Somehow, she lifted her calves and I felt her high heels lock over the back of mine. Her arms over her head, she pushed back hard onto my cock, taking more with each of my thrusts until she started wailing loudly. If she wasn't cuming, I didn't know what it was. But then I realized she hadn't been as her body lost all coordination and her voice changed to a gargling, mewling sound. Her wild movements and equally wild sounds drew the cum out of me more effectively than anything I could remember. In shot after shot, I filled her with it to the accompaniment of her moans and groans of enjoyment. Somehow, she had flattened herself to the bed and I was laying on her trying to breathe again when the climax had passed. Unbelievably, I felt like her little pussy was sucking at my softening cock as I found her neck, the side of her chin, and the corner of her mouth to kiss. "Thank you," she sighed. "Oh, you are most welcome," I said with a chuckle. I tried to think if any woman I'd been with had ever thanked me for fucking her and couldn't think of one. *** It seemed to take a lot more to draw my cock back out of her body than it normally would and, when it finally flopped free, she surprised me by turning into a little explosion of activity under me, twisting to the side with a hand slapped to her little bottom, and staggering off to the bathroom. Duh, I thought to myself in my young coworkers' lexicon. Stretched open and filled with a torrent of cum. I didn't even want to think of what it might look like coming out but I knew it wouldn't make a positive decorating statement on her bed. I was laying on my back with my head cradled in my intertwined fingers, completely relaxed, when she climbed back onto the bed next to me and put one leg across my belly, her little breasts against my chest and side, and her arm across me. Her lips found my chin to kiss me. "Thank you so much. I can't tell you what this - how sweet and gentle you were