The Early Steps of an Odd Couple – Part 2


Louisa and her mother Judy lived four streets from my Mum Cathy and me. She and I went to the same school but only met for the first time during our final year. We hit it off straight away and soon realized that we both had gender dysphoria—Louisa was a boyish girl while I was a girlish boy. We became best friends and supported each other through many trials and tribulations.Outwith school, we began meeting at Louisa’s home on Saturdays, when we began cross-dressing. This allowed Louisa’s male persona ‘George’ and my female identity ‘Louisa’ to come into being. We stayed within the house and garden at first. Eventually, we went out to a local park where ‘George’ spent quality time with boys in a local park while I mingled with girls of my age.Our adventures went undiscovered until one fateful Saturday afternoon. ‘George’ and I headed back to Louisa’s home after a great day in the park. As usual, ‘George’ took the back lane to the house so that nosy neighbours did not see him. In contrast, I put on a show for them by going down the main street to the front door. As I let myself in, I wondered if I was there before ‘George’ because the house was quiet. You could have heard a pin drop.As I headed towards the front room, the silence was broken by a voice, my Mum’s voice.“Well, come on in, sweetie. Let us see what you look like.”I found ‘George’, Mom, and Cathy sitting together on the sofa. My Mum gave me a steely stare, and I immediately wanted the ground to swallow me. I tried to speak, but no words would come out.“My, my, you are a picture. I can hardly believe that you are Louisa’s twin. We need to have a very frank talk.”Mum grabbed my hand and dragged me through to a spare bedroom. As we sat side by side on the bed, I could only imagine my Mum’s anxieties after finding her son en femme. To my surprise, she had a puzzled and anxious expression rather than being angry and incandescent as I would have expected. Her following words were to be both astounding and a relief.“I am sure you are shocked by this turn of events. You both did your best to keep things under wraps but forgot one important thing – Mums always know when mischief is afoot. Also, you did not know that Judy and I were best friends at school and kept in touch while we grew up, married, and had you and Louisa. But then, sadly, we lost touch when she moved away. She has been back here for some time, but we only recently met again by chance and rekindled our friendship.”“During a recent get-together, I told Judy about the sudden improvement in your behaviour and to my astonishment, she said that Louisa’s attitude was also better. But, of course, we could not think of this as anything but just a coincidence. After all, you had not seen each other since you were babies.”“As the weeks passed, curiosity got the better of us. We knew that each of you said you go to the park on Saturday, so Judy and I decided to meet at a café near the park entrance and watch the passers-by. Lo and behold, there you were as a couple. Happy to find you together, we decided to leave you to your fun while we did our shopping and then waited in the house for your return.”“Judy and I were delighted that you and Louisa had become friends and were looking forward to greeting you. But we had no inkling about the nature of your relationship. So, we were both completely taken aback when ‘George’ entered the sitting room, just as much as ‘he’ was to see us. To add to this confusion, I now find that my son is ‘Louisa’. So, tell me, how did this cross-dressing come about?”I told Mum the whole story, well, a slightly sanitized version. She laughed when I described my pantie flash incidents. In contrast, she appeared shocked when I told of my antics with the girls in the park. But then she broke into a broad smile.“I did the same at your age, probably even worse. You are only young once.”“Well, there is no question you have been happier and better behaved since you began cross-dressing. Of course, you have always had a few girlish traits, but it looks like they are just the tip of the iceberg. Could it be that you are a girl in a boy’s body?”I was astounded that my oh-so-traditional Mum could even acknowledge this possibility, let alone ask the question. I struggled to speak but eventually said, “a few weeks ago, I was just a boy who did not fit in. Now, I know I have a feminine side. Am I a sissy or a girl in the wrong body? I do not know, but I need to find out.”“I have lived a long life. I know that most individuals are unmistakeably male or female. Still, some cannot be so easily pigeonholed – tomboys and jane girls are the obvious examples. I remember two girls at Secondary School who had distinct masculine traits. They were harassed and bullied mercilessly by their peers and eventually succumbed to the pressure. They then went on to live and act according to the accepted gender norm. Sadly, no one noticed the damage this caused to the girls – they were emotional wrecks and ended up having sad and lonely lives. I will not let that happen to you. If your inner being is female, I accept it. I will do everything possible to help my daughter/son have a happy and fulfilling future.”“I do not know what to say. I thought that you would be furious, but instead, you understand my dilemma.””Mum is not so bad after all, is she.”I kissed Mum on the cheek. “I am so sorry for the hard times I have given you. Thank you for being so understanding.”Judy appeared at the door. She came in and sat beside me while Cathy went through to Louisa. I retold my story to Judy and assumed that my Mum had heard Louisa’s tale.”Louisa has always been a tomboy, but it never occurred to me that she wanted to be a boy. Seeing how happy and confident she is while dressed in your clothes says everything. I know that life will be difficult for Louisa if she chooses to live as a male and even more so for you if you are to be a female. Still, it must be your decision. I will do my best to support you through the good and bad of your chosen paths.”I had just kissed Cathy and thanked her when Mum and ‘George’ appeared at the door.”Judy and I need to have a chat. In the meantime, you and George need to exchange clothes.”We headed to two bedrooms to undress. But, of course, our Mums kept a discrete eye on the proceedings. They nodded approval taksim escort when they saw we had both put on pyjamas before coming out of the rooms to exchange our main clothes.The journey homeward was a little edgy and quiet, but Mum and I chatted once we were indoors. Mum wanted to know if I was cross-dressing just to please Louisa. I repeated that it was my choice. Before trying on Louisa’s clothes for the first time, I had never remotely considered the idea. However, once I did, I was surprised to find that I was at ease while dressed as a girl. Even more, the comfort and happiness I then felt while mixing with girls my age sealed the deal. I belong amongst them rather than with rough and tumble boys.“Well, Judy and I have both been convinced by you and Louisa. She and I need to work out how best to support you, so let us have a good night’s rest and visit her and Louisa tomorrow.”  I slept like a log, and the sun was up before I awakened. I showered, got dressed, and then had breakfast with Mum before we headed off to Judy and Louisa’s home. They let us in by the back door, and after the usual greetings, Judy said, “Cathy and I have much to discuss today, so you two should get ready and go out for some fun.”Louisa and I went to our respective bedrooms. We undressed, still hardly believing that our Mums approved and encouraged our cross-dressing. I was down to the buff and folding up my clothes when Mum came into the room to collect them. I do not know why I blushed, but I did.“No need to be embarrassed. I have seen it all before.”I went even deeper red when Judy came through with Louisa’s clothes and an additional package. She opened this box, took out a strange object and applied adhesive to it. Then, Judy pushed the head of my cock into a sheath on the device. Next, she placed the triangular gadget over my privates and held it in position until the adhesive had set. What was going on? What had she done to me?Judy handed me a mirror, and I gasped at what I saw. Where my willy and balls should have been, I now had a triangle of short hair. Furthermore, this fuzz continued into my crotch, where it ended encircling a small pair of pink lips. I now looked like Louisa down there. But, of course, I could not say a word because Judy did not know I had seen Louisa’s pussy. I was still mulling this image when I spotted Judy holding a pair of pink panties. I stepped into them. As usual, I quivered while they were pulled into place. Then, Judy ran her finger under the elastic of each leg and tugged it into a position to ensure that my knickers did not ride up. “Good, you look perfectly female. Your boy bits are hidden, and you have a small mound of Venus in keeping with a girl your age.”“Oh wow, you are right. Down there, I am exactly like other girls.””Now, when you inadvertently show your panties, not even the most eagle-eyed boy or girl will suspect you are anything but female. Do not scowl at me. I know you will try your best not to reveal them, but it is inevitable. Even at my age, I occasionally fall afoul of the accidental knicker flash. The embarrassment will never disappear, but now you can be sure your secret is safe. Of course, from now on, you have no choice but to sit or squat to pee. Another quirk of girlhood you must accept.”  Judy picked up a padded bra, fitted it on me, and then covered it with a white blouse. So much for keeping a low profile. I now had the prominent cleavage of a maturing girl. Boys will be fixated by it and desperate to get a glance down my shirt. But, of course, this would keep their eyes off my face, which was no bad thing.At first, I thought that Judy had made a mistake because a tiny section of the bra was still showing above the blouse. But then I realized that Judy was teaching her dear daughter a simple but essential feminine ruse. Any boy spotting the apparent mishap would be mesmerized like a deer in headlights and incoherent.Judy finished dressing me, fitted my wig and then did my make-up, even to the point of painting my fingernails. As she was doing this, I spotted a remarkable thing. Judy was smiling like a Cheshire cat. It took me some time to figure out why. She undoubtedly loved Louisa but must have been frustrated by her tomboy ways. Now, in ‘Louisa’, she had the girly-girl daughter she craved – one to pamper, fuss over, and train in womanly ways, and she was savouring every moment.I wondered if my Mum was having an enjoyable time with her more macho son ‘George’. He told me later that she did bill and coo over her boysy boy. Indeed, she had gone above and beyond and found a prosthesis that imitated cock and balls. It even allowed him to pee standing up if he wanted. One thing was sure, ‘George’ now had a pronounced boy bulge and a macho swagger that was not there before.As usual, ‘George’ headed out of the house by the back door while I left by the front. I carefully made my way up the main street but became apprehensive when a group of boys approached me. They became increasingly boisterous and loud as they got close. Suffice it to say, ‘giving them a show of my lovely titties’ featured extensively amongst their jovial verbal requests. Fortunately, it was all bravado, and they walked on by and left me alone. Fewer people were in the park than on Saturday, but we knew some of them. So, in no time, ‘George’ joined a group of boys, and I was sitting with Jane. She and I were talking about nearby well-hung talent when she suddenly made me blush. “I see that you have caught Sally’s eye. She is only that demonstrative with a girl when she wants to take her to bed; believe me, that is a treat not to be missed. I was naïve and clueless before I met her. Still, I lost that innocence and discovered the joys of sex in one amazing afternoon between the sheets with her, and I am so grateful for that.” “Were you the only one?” “Oh no, I was just the first. Sally has sexually awakened many more girls since then. But, sadly, she beds you only once and then moves on. I do not know the reasons for this but am happy with the great gift she left us. If any of us is depressed or stressed, we know the cure – we take that friend to bed. It is amazing how all their fears and sorrows disappear during an invigorating girl-on-girl session.”Jane then made me go the brightest red. beşiktaş escort “You are hot. I would love to get you under the covers.” Although Jane continued talking, I paid no attention to what she said because she was now openly flirting with me. Her lips were puckered and inviting. Her breasts were pert and heaving up and down as she breathed. Also, the flash of her panties revealed the distinctive wet spot over her feminine jewel. I gave in to temptation, slid beside Jane, and kissed her pouting lips. Soon, we were getting to the boil in a tight and passionate clinch. Then, Jane broke off, pushed me to the ground, lifted both our skirts and then lay on top of me so that we were pantie on pantie. Next, to my astonishment, she began rubbing her mound against mine. Jane purred contentedly while pussy juices began to seep through her knickers and onto mine. This moistness prompted me to seek out its origins. My fingers quickly found the critical location on Jane’s knickers and started massaging the underlying pussy lips. Soon, Jane moaned steadily as my fingers became wet with fanny nectar.At this very moment, we heard outraged voices.“Stop that disgusting behaviour at once and come with us.” My heart sank. Jane and I had been caught in all our carnal glory by Mrs Fowlie and Mrs MacDonald, the guardians of the play area. They kept good order amongst their charges through corporal punishment, as my bottom could well testify. My buttocks winced as I contemplated the incredible pain about to be inflicted on them because of our misconduct.Jane and I were dragged into the guardians’ office.”You have been grossly indecent in a public area. The only suitable penalty for this crime is the maximum tariff with the extra-heavy tawse – six strikes on the bottom from each of us. We know this belt should only be used on boys, but your disgraceful behaviour has more than earned it, and there will be no mercy just because you are girls. Your tushies are going to burn. We will, however, make one allowance if you accept this punishment. We will not tell your parents as we usually would.”I sighed with relief at this statement. I knew the pain caused by the guardians would be nothing compared to the extra agonies Mum’s hairbrush would inflict on my bare bum if she found out. But why were the guardians showing some leniency? Only later did I twig that the erotic antics of Jane and I had brought back fond youthful memories for the guardians and partly tempered their approach.Jane and I were quivering like jellies but eventually managed to speak. “Yes, we accept.”“Good, now get to either end of the desk and assume the position.” As Jane and I settled in place, facing each other across the desk, Mrs Fowlie took two belts out of a drawer. I will never forget the look of absolute horror on Jane’s face when she saw the extra-heavy tawse for the first time. This reaction was understandable because she knew that even the hard boys feared it. What would it be like for her?Mrs Fowlie walked behind me and lifted my skirt over my back while Mrs MacDonald did the same to Jane. I was so entranced watching Mrs MacDonald getting organized that I was unprepared for Mrs Fowlie’s first strike on my rear. I screamed as the belt’s venom was unleashed, and searing pain spread throughout my bum. Jane’s shrieks quickly drowned out my howls as her bottom endured its first sizzling strike. After that, we both wailed nonstop as five more brutal hits torched our bums.Jane and I sighed with relief when the guardians then stepped back. We knew this respite would be short-lived, but any interlude that avoided further pain to our behinds was appreciated. Through my tears, I saw the ladies whispering together behind the table. By concentrating hard, I picked up the gist of their conversation.Mrs MacDonald said, “Have you seen how wet the girls’ pussies are getting?”Mrs Fowlie replied, “Yes, I am very jealous. It can hardly remember when my muff last got hot and bothered.”I struggled to figure out what they meant. I knew that Jane’s panties were stained in the appropriate place, but what about me. My knickers were damp from Jane’s overspill but would have no distinct marking. Then, a memory cell kicked in, and I realized that was not necessarily so. I recalled that my sheathed cock had quivered and tensed up as shock waves from the belt surged through my bum. Then, amongst all the pain, there was a moment of localized bliss when fluid suddenly rushed along the shaft and spurted out. With nowhere else to go, these juices would have trickled down between my faux labia and onto my gusset. As six strikes of the belt did their worst, it was no wonder Mrs Fowlie saw an increasing wet spot on my knickers. If Jane’s pussy also squirted after each hit of Mrs MacDonald’s tawse, who could blame the ladies for assuming that we were climaxing? “Hmm, I know exactly what you mean. I wonder if we can we rectify that.” “What do you mean?” “We could offer the girls an alternative to six more belt strikes.” “That is sneaky, but yes, I like the idea.” With that, Mrs MacDonald grabbed my arm and dragged me to an armchair. She sat down and told me to kneel in front of her. As I got into place, I noticed that Jane was doing the same before Mrs Fowlie.Both ladies then spread their legs to reveal their underwear. Then, in unison, they said, “girls, you now have a choice. Munch out our pussies or brace your bums for another six lashes of the tawse.” Our pained bottoms made that selection easy. However, it immediately presented me with an unexpected problem. Unlike the elegant panties Louisa, Jane, and I wore, Mrs MacDonald’s were bulbous heavy-cloth knickers with legs almost reaching her knees. While they gathered everything in and were undoubtedly cosy, these undies lived up to their ‘passion killer’ moniker – they immediate quenched sexual thoughts or temptations in the viewer. I glanced over to Jane and saw she had a rabbit in the headlights stare. Clearly, I was not the only one unsure as to how to tackle these drawers.I decided just to make things up as I went along. I slid my hands under Mrs MacDonald’s skirt and ran them up the legs of her bloomers until my fingers were over the sought-after sweet spot in her crotch. Despite the cloth’s thickness, I recognized that her vulva was bulkier and more prominent than Jane’s dainty flower. Despite this, the vintage pussy lips were as sensitive and responsive as Jane’s. They trembled and quivered with delight, and Mrs MacDonald moaned when I teased them through the cloth.Mrs MacDonald trembled when I cupped my hands over her mound and sighed as I slid my fingers over her hips until they reached the waistband of her knickers. I hooked my fingers around the elastic and began pulling downwards. Mrs Macdonald instinctively raised herself sufficiently that it could pass under her bottom. I was astounded that these bloomers did not behave like my usual panties. They did not slip down as I tugged on the waist. Instead, they turned inside out and were completely back to front by the time they passed over the tight leg elastics. As the elastic finally moved down, they revealed the characteristic ring marks on each leg. Mrs Macdonald exhaled as a cold draft swept over her loins when I pulled her bloomers entirely off.To my utter astonishment, I next did an inherently feminine thing. Instead of dropping Mrs Macdonald’s knickers to the floor in a rush to get to the main carnal task, I took care of them. First, I unravelled them, folded them, and then safely placed the bundle on a small table near her chair. Mrs MacDonald smiled in appreciation of this but also gave me the clear steer that I should now get down to more animalistic matters.The inside of Mrs MacDonald’s skirt was now like a black abyss. I wondered what secrets or traps could be hidden there but finally plucked up the courage to slide my head between her knees. My cheeks flushed, and her thighs quivered when they touched for the first time. Also, my nose twitched as it encountered her intimate scents. They bewitched me, and I soon went into brain fog. Therefore, I was taken completely unawares when Mrs MacDonald clasped the back of my head and pulled it towards the target. As a result, my nose ploughed into her lush lady garden, and my lips bulls-eyed her vulva. As I latched onto her labia, she tightened her thighs around my head to ensure I could not pull back.Mrs MacDonald moaned as my lips and tongue began to caress and tease the nooks and crannies of her pussy. When I clasped my hands behind her buttocks and locked myself onto her fanny, she loosened her grip on my head. This gave me more freedom to explore and stimulate her fanny’s maze of creases. She gasped joyfully when my tongue uncovered her clitoris and miaowed like a cat as I gave that sensual jewel my full attention. Once her fanny was hot and quivering with glee, I plunged my tongue deep into the vaginal opening and licked every sweet spot I could find. Mrs MacDonald’s thighs tightened around my head again as her whole body began to shudder and buck. She shrieked as years of pent-up sexual frustration were salved as her fanny went frantic and flooded with love honey. The flow almost overwhelmed me but trapped in position, I had no choice but to sup up every sweet drop, much to Mrs MacDonald’s joy.Mrs MacDonald’s pussy eventually calmed down, and I took this as my sign to withdraw. However, she pushed my head back onto her crotch when I tried.“Stay where you are. That was the warmup. To complete your punishment, you must make me climax again.”I went back down on her muff and got straight to work. Again, every crease of her fanny became engorged, hot, and highly reactive. This time took much longer, but eventually, I sensed that she was closing on climax. So, I plunged my tongue into her love hole and licked and lapped like mad. In no time, Mrs MacDonald went over the cliff edge – bucking and shrieking, she orgasmed, and love honey inundated her fud. Once more, she moaned gently as I lapped up every incredible drop.This time when I pulled my head out from under Mrs MacDonald’s skirt, she did not stop me. I was blinking in the light when she said, “You have completed your dues with me and very agreeably if I may say so. Now, go and pay your debts to Mrs Fowlie while your friend joins with me.”I crawled on my hands and knees over to Mrs Fowlie while Jane moved behind me. She looked flushed and dishevelled but soon went to work on Mrs MacDonald.Mrs Fowlie was red-faced and breathless but keen for more action because she pushed my head under her skirt as soon as I was in front of her. My nose was immediately engulfed by the ripe erotic odours of her hot pussy. Also, the vulva’s eagerness for action was evident immediately after my lips latched on. Ever up for the challenge, I took Mrs Fowlie to two highly vocal and earth-shaking orgasms and, on each occasion, supped her voluminous and tasty Bree.Mrs Fowlie and Mrs MacDonald were now beaming with sheer delight. So they should be. After an eternity of doing without, they were bathing in the unique euphoria that followed multiple pleasing orgasms.”You two look like you have been dragged through a hedge. Go tidy yourselves up in our bathroom and then head home.” Jane and I quickly headed to the restroom. Once inside, Jane took me in her arms and kissed me. Hints of the ladies’ pussy juices were still evident on our lips, but they only added to the piquancy of the moment. Eventually, we broke off, brushed our hair, checked our make-up, and tidied our clothes before leaving the hut. We walked away, hand in hand, but we were still hungry for each other. So, we went into a thick cluster of bushes and began snogging again. Jane slipped her hands under my skirt and inside my knickers while we made out. My bum tingled at her touch, and I quickly made the same move with her. We both shivered as we felt the intense heat and pain still in our rears, but it did not diminish our ardour. Indeed, we held each other even closer, and our shared passion went through the roof as we recalled the unbelievable events of the day.“Oh, Jane, you are hot. I am so glad you still want to be with me despite getting you the tawse.””Do not be silly. I was just as guilty of bringing about that agony as you. I have never had so many amazing bodily highs and lows as we have experienced today. I want more and them to be with my girly boy.”My jaw dropped, but Jane winked. “I have known since the first day we met. You almost carried it off, but I have three brothers, so I spotted small but obvious signs. Do not worry; no one else knows. You have obviously been practising because there is no overt evidence that you are not a girl. I want to hear your story, but most importantly, I want you as my girlfriend.”