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Transgender Erotica: My Transformation with My Wife Volume 1, base on a true story.

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Transgender Erotica: My Transformation with My Wife Volume 1

Tiffany Song

Copyright © 2018 by Song All rights reserved. This book or any portion thereof may not be reproduced or used in any manner whatsoever without the express written permission of the publisher except for the use of brief quotations in a book review.


It was 2006, a day in April; I can't remember exactly the first day of the rest of my life begun but begin it certainly did. And for my wife, Joanna, it also meant a massive change. I was back in England from a business trip to Canada, to Vancouver to be precise, and I had been back four days since being over there. It was a business trip but Vancouver offered other pleasures, particularly as for crossdressing and I had stayed on for 48 hours to enjoy this and take advantage of the excellent shops and services. Yes, I had been accompanied by a female friend who enjoyed crossdressers, not that any penetrative sex had gone on by me least. I won't go into all the details here, except that I had lived as a woman for the 48 hours, staying in one of the City's top hotels. Even there, no eyebrows were raised. This friend I had met in Edmonton on another trip and we had e-mailed each other and she volunteered Vancouver as it was her home and she knew the scene well.  Joanna had rumbled me though; she had had her suspicions for some time, and now there was also some evidence. She knew that I was seriously, or "unhealthily" as she would describe it into lingerie as any shop or good photo would get my attention and this, coupled to a number of other factors like our sporadic sex play and when it happened that my performance probably wasn't all male, led to her building a picture of me. So, there in our study, on my day back she confronted me. Nothing aggressive, in fact very open, a want for understanding and considering. This was so like her. I have been into crossdressing from an early age. I grew up in a feminine dominant family and my first experiences involved being totally crossdressed was with a teenage boy friend of mine in his sister's lingerie. And he was the first boy to take my anal cherry. My first true female love was older than me and she loved me to dress. She was also naturally pretty dominant in bed and loved prolonged oral, sexual servitude and the worship of her rear; hence, apart from being properly taught how to oral, I was introduced to facesitting and inhaling the aroma of her panties. My second girl-friend enjoyed the occasional crossdress session but wasn't as in to it as other enjoyments such as anal and watersports. The need to dress has always been there, though there have been different levels of intensity during my life and, I suppose, with whom I was partnered. And, yes, I went through the "accumulate and lose it" process of many a crossdresser. I have always enjoyed wearing female attire and being in a pair of panties has always been the bare minimum. However, the chance to go the whole way and completely transform was one that I truly enjoyed and, in doing so, I felt that I could make a complete psychological shift when fully dressed. I had a number of enlightening experiences over the years with both male and female friends. Joanna and I were, I think it fair to say, best of friends. We had been married for ten years up to 2006 and there was much to be commended in the marriage, culminating in two children, as well as an overall happy house when it came to life at large. Joanna had chosen to be a housewife with occasional work from home to earn pin money for herself and, in doing this, she had built up a substantial clientele and a sizeable income. She was very bright and well read and had a range of interests outside what we shared together, such as cooking and wine. However, sexually, I had always found her prudish and thought that she saw sex as being more for reproduction. We had never really shared major interests, fetishes, wants, whatever, though she usually did enjoy being oralled. However, rampant, prolonged, imaginative sex was not usually on the cards; it was usually fairly conventional pre-play and building up to the one orgasm for each of us; that she normally achieved and despite me being not massively endowed at just less than 6 inches fully erect. The subject of sex just wasn't discussed between us. Therefore, I hadn't really shared my other side, my feminine side, with her partly in fear of a 'kick-back,' partly a lack of understanding and, like a lot of folk out there, I repressed it except for situations behind her back, Vancouver being one of these sessions. And to be fair to her, I didn't really understand what drove her sexually, if anything, despite having asked at various times over our marriage. Let me describe Joanna to you. She is a year younger than myself, mid40s, 5 foot 3 and dark shoulder length hair, not a 'stunner' but attractive with lovely eyes. At this time her body shape was rather pear shaped body 38c, 28, 40. Her breasts are pretty pendulous with large purplish-pink nipples and well defined aureoles. Her skin has always been very pale almost milk like and slightly freckled. Her bottom was very full but to be fair to her, by then she had already shed an awful lot of weight, having come down from a size 16 to 12 and she continued to do so. She used to weigh 12 and a half stone and by 2006 had come down to 10 and a half stone and today she weighs 8 stone, having reduced her body sizes back to when she was a late teenager. We met at postgraduate, I was studying a practical science and she focused on Advertising and Communications, an area that she has continued to work in, albeit from home at this time. We both grew up near London and live close to her parents and family; mine is not that far away. Joanna has always been pretty logical, more so than me, and took a rational appraisal of situations rather than getting herself emotionally wound up, and this held her in good stead in the family and with her work. She was/is pretty liberal in her politics. Dress-wise, she has always been fairly conservative, always neatly turned out and made-up. With the second child, and the start of the weight loss, she started to wear more slacks and polo tops out for work, with less make-up than before – a stark but beautiful look. Around the house, she wore more plain tops and track bottoms, practical she said for handling the children. Throughout her marriage her underwear had always been very conservative and she had very little frilly, sexy, wear despite me having bought her the occasional ensemble which largely remained in the bedroom drawers. Neat underwire plain bras in white, black and flesh accompanied by plain matching panties. The same too for nighties as she definitely preferred pyjamas.  Underneath she was quite bushy and her pubes extended down to her anus and with a hint of them in her bottom crack. She had never shaved. Her labia were prominent and so was her clit when stimulated. She was pretty strong on her aroma. However, play down here was fairly limited with the occasional oral session, little finger play, and I understood that she didn't masturbate and certainly there was no toy usage. Again, a couple of vibrators remained buried in the bedroom dressing room, well away from the risk of prying eyes and fingers. The one thing I did enjoy was her scent and I had a 'thing' for her used panties and would occasionally borrow an aromatic pair from the laundry basket which always ran of 'fairly' full. I guess I should give you some idea of myself. I am 5 foot 7, weigh 13 stone and have fairly wide shoulders, a sizeable bottom but nicely defined legs and a neat waist. I have always been clean shaven, don't sport an enormously hairy body, little nipples, small hands and as mentioned I am not huge underneath. My hair colour is a dark ginger bordering on brown and quite distinctive. My job required a lot of travel but I did have the advantage of being able to work anywhere and especially from home when I was back in the UK. I had typical male interests in sports but then I am also artistic and creative. I had no issue with doing my share of household chores by the way and actually enjoyed the mundane tasks. I was working away in the study in the morning; it was about 11am when Joanna came in. She had been out for the school runs and then had done some shopping and saw a female friend for coffee. She came in and turned the leather reading chair we have in the study to face the desk and sat down. "Matt, I have something serious to discuss with you and I want some candid answers and the truth." I looked at her and stopped doing whatever I was working on, a spreadsheet of some sort. "Yes, honey, you look serious. What is it?" "Well I came across these in your luggage." From a bag that she had brought into the study, she firstly pulled out her panties. "I know these are mine and I have had my suspicions that you have been enjoying my panties for some time. I ran a count this time you were away and knew I was a pair short." I am sure I went red. "However, whose are these? Are they yours?" And she pulled out a pair of black panties I had and a pair of stockings. "I think that you need to explain. But before you start, I did a little investigative work on the computer and it didn't take me long to find some of the sites that you have been looking at, especially pertaining to Vancouver stores. So what is it all about?" She remained collected. I briefly thought and realised that this was an opportunity to confess and take the gamble. I unloaded that yes I was a crossdresser and had been for some while. And that Vancouver had been an ideal location, though no mention of Simeone as that would have been the red flag to Joanna. I went on about my interests and how far I would dress. She listened intently, no comment and just the occasional clarity question and "Go on – just tell me." I talked for probably twenty minutes and then came a barrage of questions. "Have you had a man on this trip or before?"  "No honey, not on this trip and not in a long while. Let me explain my history here. And I am Aids free, well at my last medical, as you know." I explained my early history with both sexes and how the crossdressing had started as a result of these early girlfriends. "Well, you need an Aids test soonest, for my satisfaction" was Joanna's conclusion. "Tell me about your crossdressing more."  Another twenty minutes on what I liked in particular (panties and nighties especially), style of dress and lots of prompt questions. "What did you do with the clothing and did you have any falsies etc?"  I explained that over the years I had wasted a lot but from this recent trip there was a small stash at my office and yes, I had a pair of silicon falsies which weren't cheap. "Well I am glad about that, but really I am a little annoyed that you have wasted quite a bit of money no doubt on your alter ego." This was the nearest that she had got to being annoyed. "Ok, what about your fetishes, I know about your love of panties and used ones, what else have you experienced or fantasise about?" So I gave her a snapshot of my interests. Once more, Joanna took in, all rationally, the information and asked specific questions such as about straps and whether I fancied being taken by men, by women, by her and how. "What about the children as for whatever, they are not to know about this?" "I agree, until we have clarity of direction" "Well, Matt, I want to think about what you have said and do some of my own research work. I may ask you questions at various times, some of which may be somewhat convoluted but bear with me. I also want you to write me a long letter outlining what you have told me, but especially to focus on what you see happening in the future if this is allowed to continue. I am irked I will say, not by the dressing but that you did not have the confidence to tell me about this earlier." "However, to be fair, I have not been that open about my needs to and that is something we need to address both in terms of our life at larger, and especially sexually. There I have failed you I admit." "Let's go and get some lunch." And that was it for the day, in fact for two days as Joanna went away to do her analytical thing. I put the letter together for her and sent it over to her by e-mail the following morning. Writing had always been a powerful way of communicating between us. The day after I got my test done and arranged for the Doc to send Joanne the results. Questions then started to emerge ranging from my balance of sexuality and experiences with men and women, then to my happiness with work, and onto even my preference of styles for lingerie and dressing. Also, how I felt about household chores, money management, family – all rather disjointed in structure and lacking any reasoning at this point. Then she asked to see my silicon breasts so I brought this home from my storage at work and she took them off to closely examine them. This was all over a period of another five days though by day 6 she was saying, "Look be patient with me, I am getting there as to should we continue this and if so how. By the way, I am not going to divorce you for being a deviant – yet!" This was the first positive sign emerging. The second sign came on Day 9 – I had a quick overseas overnighter on Day 8 to make and I went as a male! I got home on Day 9 evening and Joanna was there, but no kids. "Honey, my parents have the kids tonight. Let's have a good dinner as we need a long chat. Go and make yourself comfortable and unpack" I came through and dinner was well on the go. Joanna handed me a glass and toasted "to us." Dinner came up – a simple tagliatelle with bacon, cherry toms, red onions and a green side salad, freshly dressed. Joanna started up, "Look I meant what I said about not wanting to divorce you. I have been pretty mad at you and as I indicated this is not about you dressing, rather that you have never told me and I have been mad at myself too, for not unloading to you." "I have done my research work and you know I am pretty thorough and I have been into many aspects of crossdressing, transvestism and trans-sexuality. My opinion is that you fall heavily into the middle camp." "I have no basic issue with this if you are honest with me and I will be with you. The first thing we need to discuss is your job and your happiness at this – as you know my income has been increasing rapidly and I think we could consider a role reversal if you wish work-wise. I wouldn't mind going back to work and you could contract from home. The kids would love it." We discussed this at length and also covered a lot of home items. It was decided that I would aim to work more and more from home and take on a lot of the household chores whilst Joanne would start working more outside the home, take over the day to day finances, but investments would be mutually decided on. In short, we set a goal of moving to household income being 70:30 from her instead of me within two years.= and if we could achieve this possibly inside 12 months and thereby accelerating my move into being a house/husband wife.  "Then my second major point is just how bi are you and especially when you are in female mode. By the way I know that you are negative and clear of any STDs" We discussed this at length and that I truly saw myself as a 'bottom,' or very much the femme in the act, and towards the submissive. "Ok that is clear, and I want to own up to some things now. I feel ashamed that I have never shared with you any of my sexual cravings or leanings. I'm also ashamed that I put on so much weight pre and post our marriage and that hasn't helped with my sexual confidence either." There are three things I have been wishing to explore, Matt, and have never had the confidence to open up to you. Firstly, I had a wonderful lesbian relationship in my final year at school with one of my teachers and this continued through 1st year at University; I have long craved to have another girlfriend – this doesn't mean that I don't love you." We explored this and Joanna's history. And I can say it was a shock. "Secondly, our sex life hasn't been that great in the past and that I would like to pep up. I have had for some time quite a few dominant thoughts and want to take much more control in bed with you. This could work well with what you have unloaded to me, so yes I am prepared to go along with your dressing. Some rules in a minute though." "Thirdly, you aren't hugely endowed, though your girth is pretty good and I love your oral on me. I haven't had that much experience with other men but would like to enjoy some new real cock if I can. Now this maybe a shock to you, just as your dressing is to me, and I will only do it with your blessing and when you are ready." I probably did look stunned. Joanna opened another bottle of wine and poured fresh glasses. "Now the basics and rules and they are simple." To summarise, I have no issue with you dressing and for me, I may well indulge too in my dome play. However, we should be careful with the kids. They are too young at the moment to know our details. So, I don't want you going around in a skirt or a nightie, or with make-up on when they are around but if they away on a sleep over with friends or our parents and relatives, I have no issue. You can wear panties if you wish all the time and I would suggest you wear female jammies at nighttime. We can go out and buy some if you wish and, yes, I would like to go shopping with you soon. Secondly, we tell each other about potential partners and we will be frank to each other about our experiences with them and preferably sex should not be in the house, unless we, and I emphasise we agree and invite them and the children are away. We should also clear any partner for cleanliness. And as to partners, I have no problem in helping you if you help me meet my desires. If you want to be cuckolded, that is no issue and I have enjoyed researching that aspect, let me say. However, I would like to push ahead on finding a girlfriend soonest." We then covered minor stuff and cleaned up the dinner stuff. Back to what happened after our long dinner chat; well nothing. We went through to the bedroom, cleaned up and cuddled together and kissed, nothing more. In fact, nothing happened for a further two nights until the kids were off for a sleep over. Little was said and we lived as husband and wife, in thought and in dress, going about our daily work and chores, as well as family. On the third day, I was at work when Joanna called, "Honey, we have the night, in fact the next two nights to ourselves. The kids are having a sleepover tonight at their friends. Emma and Sammie, and tomorrow they will be at my parents. All the logistics have been arranged. I think we can come to full agreement over the future and put this all behind us, so could you try and be reasonably early tonight, for me. And if you could get the day off tomorrow or work from home, that would be really nice" "Could you pick up a couple of bottles of wine on the way home, and also these food items?" She listed them. "And could you pick up some depilatory cream, your favourite brand as I don't use it normally, and you are better versed in that area, (laughingly said). I love you, by the way" She put the phone down. So, I did the shopping on leaving the office and headed home. It was about 6.15 when I pulled into our driveway. We have three old cottages spliced together on the edge of the village. Apart from being quite chocolate-box, in nature and warm, the property was away from other houses and gave us welcomed privacy. I entered the house and the fire was lit, the place was snug; it was rather a raw evening. Joanna emerged, glass of wine in hand for me, and gave a long kiss to say hello. She was dressed as she often was in a black rollneck, black pants, black low heel shoes and with a gold necklace and bangle on. Her hair was pulled back with an alice-band and her make up was minimal. A touch of gloss and a little eyeliner.

"Hi honey, missed you. How was your day?" We sat down and covered our respective days and what had happened as well as the logistics for the kids. "Let's eat pretty early – I have dinner prepared."  So we went through and ate in the kitchen-diner. Conversation continued with more "facts of the house" and then turned more to our comfort levels of Joanna working out of the home and me as a house husband, and in Joanna taking over the day to day financials. She was far better organized than me for this so, in fact, I was more than comfortable with this happening. After dinner, we went through and sat by the fire and had another glass of wine. Nothing had come up about our sexual direction, orientation or plans but then if over these 36 hours, we covered all our bases and got our lives rolling forward, I was fine with that and best not to push Joanna after all I had put her through. "OK honey, tell you what. I am going to the study and read for a while and I will get ready for bed in the main guest room, so I don't disturb you. I will come to bed later but I want a good read." Later, she told me she had downloaded some crossdressing and lesbian erotic stories for her continued education and to excite her and this was a surprise for me as she seemed to enjoy written pornography. "I want you to go through to the bedroom now; yes I know it's only a quarter to nine but you probably have plenty to do. Firstly, I want you devoid of hair from the eyebrows down, not a single stubble and that's why I wanted you to pick up your favourite cream today." I looked at her and asked "Are you absolutely sure?"  "Oh totally, honey, I also want you to dress in what I have laid out and follow the instructions that I have left. Now off to the bedroom with you and take your time, I need perfection." We duly went our separate ways and on entering the bedroom, there on the bed was laid out a new Barbara matching black lingerie set, a 38C bra, deep garter belt, stockings and hi-side matching panties, all smooth on the rear and the front panel, but a hint of lace on the cups and side panels of the suspenders and the panties. Next to the lingerie was a ¾ length silky black nightie with thin straps and a bodice lacy front. There was also a small note on top of a brown envelope that asked me to open the envelope when I was ready. I went into the bathroom and on her counter was laid out her make-up and a note to use what I needed. Next to the make up were my silicon falsies and a note asking me to ensure that I fixed those on for her. Finally there was an enema solution and a third note asking me to clean myself out for her. It took me the better part of an hour and a half to prepare, firstly the enema and then the depilatory cream and then I took two showers so to take away the residue and then the smell. I then used a moisturizing cream on me to soften my skin and further scent me as being feminine. I then commenced my make up, applying nail varnish – I am lucky in having a steady hand, and then fixed my breasts on. This was followed by the foundation cream, eye liner and shades and finally a darkish red lipstick of Joanna's which hadn't been used before. All of this was highly exciting with the anticipation of what was to come and being able to transform for her. I came out into the bedroom and slowly put on the lingerie; it felt wonderful. Fortunately I am not massively endowed so with the panties holding me in, my bulge wasn't too tent-like. Finally I slipped on the nightie and went into the bathroom and put on some Van Cleefs and Arpel perfume of Joanna's, something I had bought her from duty free. A dab on the ears neck and just above my breasts and my panties line. Back into the bedroom, I opened the envelope that she had left me. Inside there was a second note, "Call down to me when you are ready, so I guess now, and I will come up at some point." I did as requested and shouted down that I ready for her. "Firstly, open the small brown envelope and wear the contents" Inside there was a gold necklace with an engraved 'tag' saying "I am Joanna's girl" This, I put on. "Secondly, I now want you to open the zip-bag in this envelope and take out the smaller black hi-side panties inside. I want you to put them on your head, crotch to the nose and inhale my aromas – and I have worn them for two successive days." "There is a second pair in there, a full black brief. You are to put these on as well but the other way round, so with the leg holes pointing back, so as I want to mask you. And then you are to climb on the bed, lie there and await my arrival and contemplate my intense scents." I waited for about 30 minutes deeply enjoying Joanna's intense, but familiar, scent and the thought of what was to happen.  Suddenly I sensed that she had entered the room; I could just make out her form through the black material of the back of the brief panties. She watched me and went around the bed. The TV came to life with the sound of provocative sex sounds coming from girls. She came over and climbed onto the bed. I could feel her standing close to me and then over me, closely inspecting me; suddenly she pulled off the used panties and she was there just about right over my chin with her front pointing down the bed towards the TV. She had a grey and white tank top on and what appeared to be a white male thong or small jockstrap. "Do not move at all, Do not say a thing." She played with herself, obviously lightly massaging her clitoris and then running her hands down over her cunt to provocatively toy with her anus, and onto her bottom cheeks. She had never played with her bottom and had repelled any suggestion of anal sex with me in the past. On the TV were two girls embraced in a 69 which was what she was watching. Then she slid her thong provocatively off and continued her finger massage gradually opening her legs and showing me more of her sights in their glory and better than I had ever seen her, especially when she bent over, opening up her anus for me and inserting her finger.  She tantalisingly lowered her bottom slowly down onto my nose and I could smell her anal sex and her pre-cum; her scent was pervading the room as it was that potent. My tongue was ready for pleasing her cunt, "Matilda, Mattie, Now please my cunt."  Joanna pressed her vaginal entrance area forcefully onto my tongue. She was already soaking wet and very aromatic, a familiar taste but much stronger and wetter than normal. She was controlling my breathing and which area I could please her. This was the first time I had ever been queened by her. What a wonderful sensation and she started to use my tongue and nose as built in sex toys to pleasure her. She came quickly and two strong, juddering orgasms hit her, gushing her cream into my mouth. She had never cum like this before at any time in our marriage. Joanna didn't wind down as she normally would do. She moved off me and went to her side table drawer. She pulled out what turned out to be a purple femdoe (can highly recommend them). She inserted the bulbous attachment into her vulva and then moved back to me with some lub that was applied by her fingers to my male vagina as she called it. She took the priapus part, moved it passed my panties and into me. It wasn't long with her deep fucking before we both had very substantial orgasms which left us collapsed together, that's the beauty of the femdoe that both of you strongly feel the sensations. What a wonderful night was underway.


Joanna did something that she never had done before. Whenever, we had sex, she would immediately head to the bathroom and clean herself up. She also tried to avoid wet spots on the sheets and, if there were any, I was to sleep on them. That night, she rolled off me, took out her femdoe and gave me the bulbous end to suck so I took in her very sticky, heavy vaginal cum. She jumped out of bed, put her boy-thong back on and then pulled out new heavy cotton-striped pyjamas that had a fly and a string cord. She had me cuddled into her, still in my lingerie and nightie. "I like doing this, the other way around. I wish we had done this sooner. Let's talk about it in the morning though."  We were soon asleep and the first thing I knew was Joanna nudging me. I woke up as she climbed back on top of me, having taken off her pyjama bottoms and her thong. The first thing I really knew were her delicious globes coming back onto me and, once more, presenting her anus and cunt for my service.  "Mmmmmm, just clean me up, I need some more pleasure" Back to my tongue, nose and mouth work on her encrusted love areas I went, taking her in and obviously pleasing her. Her hands worked their forward and played with me through my panties and she referred to my cock as my boy-clit, bringing it up to its maximum. She lent forward, opening her pussy further to me and teased me through the fabric of my black panties. I felt her orgasm starting to rise, and once more her pre-cum was pretty copious in its quantity that went into my mouth. She moved forward on me, turned around and slid her hands under my panties to release my clit into her cunt. "Fuck me, my girl Mattie."  She rode up and down on me as I matched her movements from under her. She allowed me to feel her breasts under pyjama tops and soon she was climbing her sexual mountain to orgasm in the high clouds. She stayed on me for probably fifteen minutes as she wound down.  "Mmmmm, that is a really nice way to wake up. Let's go and get some coffee" She jumped off the bed, "And then we can shower and I so want to feel your breasts." Joanna slipped her thong back on and her jammie bottoms. She handed me a negligee and we went through to make some coffee and sat at the table. She held my hand." "I really prefer you as a woman, you know. It really is the sort of 'in-between sex' that appeals to me. That was the best sex of our marriage so far; well for me it was" "For me too, and I really thank you for your tolerance over this" "Don't worry and don't be stupid; you probably haven't seen anything yet." And she smiled and winked at me. "In fact, I am of the mind that if we had been without children, I would fully transform you and have you living 24-7 as my wife. And I mean that." She continued, "For example, I would love you to have real breasts and a better girly shape. However, do not get me wrong, you are pretty convincing already, given your legs, your smallish hands, the 'curvature' that you have and, luckily, no real Adams Apple showing." "Thanks, Joanna"  "However, with the kids, we are going to have to find a balance in all of this and that will mean some 'novelty' in our approach. " She smiled again, and drunk some more coffee. "And on that score, we need to get showered and dressed as I want to take you shopping today. I thought we would head to the discount area at Banbury and then we can take on Oxford or Reading. Yes, I want you to go as a female and you will be ok as both places do get a lot of tranny clientele apparently. And you are with me." We went back to the bedroom and stripped off. Normally, bathing together rarely took place, though we also had a large tub and had had some family baths. But showering together, I really had to strain the memory as to last when. Joanna slowly stripped down, taking her pyjama bottoms and her thong off. I had a close look at it and it was indeed more like a male jockstrap.  "I really like wearing it, Mattie, and wouldn't mind getting a couple more today as well as plain back or white briefs, or boy briefs. What do you think?"  She then took off her pyjama tops. "And I thought I would really try and find some 'restraining' bras to flatten me out a bit. Obviously I am a C cup so complete flattening is out, short of surgery and I have given that some thought by the way. I took my bra off last to tease Joanna a bit. She came across and closely inspected my breasts. "These are nice on you." She inspected them closely and felt them on me, coming from behind and cupping my breasts against me.  "Come on into the shower, I want to wash you and you me. Here are shower caps by the way." Putting them on, we entered the shower and soon the hot water was streaming over us. "I love you naked with no hair like this", as her hands roamed over me, focusing inevitably on my boy-clit and also my anus.....