I was an only child brought up in the late 1940s on an isolated croft, miles from the nearest town. None of my age lived nearby until I turned eighteen, when the Smyths and their twins, Brenda and Brian, moved into the area. Brian joined an all-boys class, while Brenda joined the co-ed class I was in. Indeed, she and I shared a desk, which was good for me because we were an academic match and fared far better together than on our own.
Brian wasn’t the studious type. Instead, he was into sports in a big way. However, we found we shared an interest in hill walking and gradually became friends. After listening to lurid tales by older boys, pubertal curiosity took hold, and we began playing with our boy bits. At first, we confined ourselves to wanking, but, as our confidence grew, we engaged in a whole range of sexual techniques before we finally engaged in the ultimate in boy-on-boy. That intimate act changed our relationship completely; for up to then, we had shared our sensual activities equally, but now, for coitus, Brian was always the top while I was the bottom. We all intents and purposes became boyfriend and girlfriend, but I had no complaints as I was very satisfied in my subservient ‘female’ role.
Our loving times lasted for six enthralling months but ended when Brian started dating Jenny, a girl from school. This move was inevitable because we both accepted that our intimacy was just about preparing for the real thing. However, by that point, I had fallen in love with Brian. So, no matter how I rationalized our changed situation, I desperately missed him and fell into a blue funk.
I moped around for the following month and essentially lost interest in everything. Then, out of the blue, Brian sought me out. “Can we meet at the usual place tomorrow morning?”
I was confused by this turn of events, but also delighted to have the chance to meet him. “Saturday will be fine. I will see you then.”
Brian nodded, said, “I look forward to it,” and went on his way.
The next morning, after telling Mum I was going hiking with Brian, I made my way to the clearing where we used to meet on sunny days, and my heart fluttered when I saw he was already waiting there. We did not waste time with words; we just took each other in our arms and settled into a luscious snog. Before long, we were down to the buff and making out amongst the long grass like a pair of excited first timers. Once we were both on fire and ready for the main event, I prepared to assume my usual position as bottom when Brian shocked me by saying, “No, no, today I want you to ride me.”
I was dumbfounded, and a few seconds elapsed before I could say anything coherent. “Did I hear you correctly? You want me to top you. Are you sure about this? You have always been terrified of penetration.”
“Yes, that is exactly what I want.”
“What has changed your mind?”
“Jenny and I are getting close to sealing the deal, if you know what I mean.”
“I understand. So what?”
“Well, have no doubts, I am more than keen, but I also want to be absolutely sure it is a pleasure for her. I am scared I will hurt her by being overly boisterous, as I must admit I have been many times with you.”
“Yes, you were, but the fact that you now understand that goes a long way to solving the problem.”
“That is true, but I do not think it is enough. You once told me that you believed every boy should be a bottom at least once so they could appreciate the risks and demands of taking cock, as well as its great joys. To understand the sheer courage required to put yourself completely at the mercy of a boy and his ravenous cock. I now know I need to experience being the receiver rather than the giver, so I can learn to control myself around Jenny and do my best for her. Who better to learn from than my best and most trusted friend?”
“Jenny has already changed you, and for the better, I would say. Of course, I will do what you ask. I would not be much of a friend if I did not. I promise I will be gentle, but I guarantee you will be ridden to bliss. However, I do have one request. Once I have taken your boy pussy’s innocence, I want you to screw mine one last time.”
“Oh, that is a challenge I am more than willing to take up.”
“Good, how about we do this just like the first time you rode me; doggy style in the middle of the stream.”
“Brilliant. What better than to relive those great times, except that I will be the bottom, and you will be the top.”
Brian and I kissed, cuddled, and petted for a while, so that we were fully aroused and ready. But then Brian suddenly pulled back.
“What is the matter?”
“I have just remembered that when we made love for the first time, it was just after we had both been thrashed by dad. Despite the heat and pain still searing through our bums, we got clear messages from your fanny and my cock that they felt left out of the action and were more than eager to rectify that. Of course, once they had made up their minds, we were unable to resist, nor did we want to, and the intercourse was out of this world. How about we do everything like on that first occasion?”
“I do not know how that would be possible. I certainly have no wish to be belted by your dad again.”
As Brian took off his belt, he said, “Silly boy, no need for dad, we spank each other.”
“Oh my, I never thought of that. Okay, let us do it.”
I got onto my hands and knees and said, “Right, you spank me first.” This was not bravery. My thinking was that it was best to go first and get it out of the way, but in doing so, I would find out how hard Brian would be and arrange his punishment accordingly.
Oh boy, Brian was as vicious as his father. From the first scorching kiss of the belt on my bottom to the last, he gave it his all and turned my bum fiery red, just as his dad had done 6 months earlier. I could have been angry over the pain he inflicted on me, but I was not because Brian knew no better; he would have been regularly punished as badly or worse by his dad. Mind you, understanding did not convert to leniency. I made absolutely sure that his rear got the same searing lesson as mine. Needless to say, we then took some time to recover and let the acute pain in our bums settle. During this period, my cock began to stir, and my bum ring started to quiver. One look in Brian’s gleaming eyes told me he was getting the same sensations. Moreover, he realized it was time to answer their call.
Brian got up, walked into the stream, and got into position with his bottom underwater and his head and chest above it. I could see that he was nervous, maybe even a little frightened. I was also apprehensive of topping Brian for the first time, but soon realized I now had no choice in the matter. I was now under the control of my penis, which was twitching in eager anticipation, and certainly in no mood to be denied. So, I quickly stepped into the stream behind Brian, kneeled between his legs, and clasped his waist.
I immediately sought out Brian’s bum crack and pushed my cock between his buttocks. It quivered with delight as those still hot buns clasped it, and when the tip nuzzled Brian’s pussy ring, both trembled in expectation. Their message was loud and clear: we are ready, let us do this, and do it now. In spite of this encouragement, Brian’s tight outer ring fought forcefully against the intrusion. However, it was no match for my determined penis, and Brian squealed when his outer and inner sphincters suddenly gave way, allowing the head of my cock to burst into his pussy.
As expected, Brian’s acute distress was short-lived, and he was soon sighing and moaning with pleasure as my dick made merry while it burrowed into the depths of his fud, snuffling out and teasing every sweet spot in its path. I was thrilled as his fanny frantically squirmed and squeezed around my shaft while I buried it to the hilt again and again. Indeed, I was soon in La-la land as my nether regions were engulfed with increasingly entrancing sensations during every thrust. I was blown away, and Brian was purring like a contented cat. Now I knew why Brian was so happy as a top.
As I rode Brian, I was shocked to suddenly hear a clamoring voice in my head. “Now is your chance, let yourself go, ravish his fanny and screw him stupid. You know you want to.” With each stroke, this commotion got louder and louder, and, to my horror, I actually came close to giving in to it. Thankfully, just as I was about to go caveman on Brian, my conscience took control. While I continued to ride Brian, I did so with sensitivity and love.
As a result of this shock event, I realized that Brian would also have had to fight these carnal demons. So, despite his occasional sessions of rougher-than-usual sex, he was at all times with me, showing great restraint by ignoring those devilish voices in his head. This meant that Brian did not need to be a bottom to understand the need for self-control and care for his partner during coitus; he already practiced it. Nonetheless, I did not relent, for that would be a waste. After all, having his fanny ridden to a frenzy by my enthusiastic cock was certainly going to reinforce Brian’s already good instincts about intercourse, or that at least was my convenient excuse. In truth, by then, I had one and only one motivation. I had long wanted to ride my best friend, and now he had given me that opportunity, I was going to pillage his fud and screw it to bliss, no matter what. To hear Brian’s delighted sighs and squeals as my cock went berserk inside his fanny was all I wanted. Any other indirect benefits were a nice bonus.
As my cock began closing on the point of no return, I remembered an important delaying tactic learned during the course of countless wanks, and blow jobs. I slowed down the action. As I expected, my dick now pulled back from the brink of eruption, while still remaining hard and eager. To my surprise, this move did not give any respite to Brian’s pussy. It remained highly agitated until I restored my earlier thrust rate. Brian gasped and moaned in rhythm with every stroke as his fanny went into a new, breathtaking frenzy. This slow-down-speed-up approach worked for me one more time, but this left Brian almost moaning and groaning incessantly before I sped up the pace for the third time. As I did so, his fud went frantic, he lost the plot, and my cock decided it would not be thwarted. Even as I slowed my thrust rate, it erupted like a volcano. Brian and I shrieked and howled in unison as my shaft went berserk inside his pussy; spasming, pulsing, and pumping like mad as it delivered a massive load of spunk.
As we remained coupled, enjoying every last moment of climax, Brian spoke first.
“Oh my, you are a real stud. You have taken me to seventh heaven. Why did I let my stupid fears hold me back for so long? So much sweet pussy action I could have enjoyed. Oh well, it is what it is.”
“I am glad the ride was great for you, for it certainly was for me.”
“You deflowered my fud with gusto and gave me immense pleasure, for which I am grateful. It is just a pity I did not allow you to do so sooner. However, now for my part of the bargain.”
Without further ado, Brian stood up, walked around behind me, got into position, and straightaway bulls-eyed my bum crack with his erect cock. There should have been no surprises as he had already topped me many times before, but straightaway this occasion felt quite different. Brian’s shaft was thicker, hotter, and more intent on its task than usual, and my fud was practically begging his huge weapon to spear it. Neither was disappointed. I was soon sighing with joy as his dick drilled and stretched my fanny as never before. Ever keen to try new tricks, he masterfully copied my slow-down-speed-up technique two times and got me to a point where I was gibbering and feeling that I could take no more, when, for a third time, he upped the pace and began screwing me hard again.
Nothing could have prepared me for what happened next. I lost the plot and screamed when Brian’s dick suddenly went berserk. My whole body quaked, and I howled like a banshee as his madly spasming cock then turned my fud to jelly and filled it with masses of hot spunk. These carnal reactions were so intense that I became delirious and almost passed out. However, once Brian’s climax went through its wild peak, I soon returned to an even keel, albeit still enveloped in a euphoric sexual haze.
I was still gasping when I was eventually able to speak. “Oh wow, if I am a stud, you are the superstar. You have shagged me good and proper and satisfied me no end. Thank you is all I can say, but it is nowhere near enough.”
“My pleasure, only glad to be of service.”
“I do not know about you, but I need to rest for a while.”
“Me too.”
Brian and I now got up, walked from the stream into the middle of the tall grass, and lay down amongst it. We cuddled up together and snogged until exhaustion took over, and we fell asleep in each other’s arms. Judging by the Sun’s position in the sky, it was around midday when we slowly awoke. As we gazed into each other’s eyes, an irresistible desire took hold.
“Today has already been great fun, but since it will be our last time together, I think we should make it even more memorable and special.”
“I agree.”
We cuddled up and made out until we were hot, bothered, and ready again. Then, we shagged each other to ecstasy four more times. By late afternoon, we were euphoric and mentally out of it. However, our cocks wanted more and were not to be thwarted. So, carried along by physical lust, they filled our insatiable pussies with three more loads of cum before the moon was high in the sky.
Now, balls drained, cocks spent, and fanny’s satiated, sheer fatigue overtook us, and we fell asleep, only stirring again once the sun appeared over the horizon. Boys being boys, one of the first things we did was to check out our tackle. To our great delight, we found that our balls had, in the main, replenished during our period of rest. Equally important, our penises stirred and stood to attention when they were touched.
Although neither of us was mentally all there at this point, the lust for each other was still strong. So, there was no doubt over what was going to happen next. We petted until we reached the boil and then, in complete physical and emotional synch, we made slow, pure, and satisfying love. Unlike our wild sessions of the day before, we took our time and gently took one another to bliss. Three times our cocks orgasmed like mad in our delighted pussies, even though there was little or no cum to spurt by the third time.
Brian and I now lay down together amongst the grass and cuddled up. We were satisfied beyond belief and were almost as one, because we were physically and psychologically in complete harmony like no other two boys in the world.
We both knew that our coital time was up. So, we soon fell asleep in the sunshine, only to reawaken when the sun was near setting. We got up, washed in the stream, dressed, and then unsteadily made our way from the clearing. Only then did we see that our vigorous activities had created a de facto crop circle amongst the long grass. I remember wondering what speculations there would be about its origins if it were discovered. It was, and the rumors about it were hilarious.
Brian and I slowly and gingerly made our way home, with many stops to rest, cuddle, and smooch on the way. We shared one final long snog before going our separate ways.
“Goodbye, my friend. Take care and good luck.
“Same to you, the best pal ever.”
Mum was already asleep when I reached the house, so I went to bed straight away and slept like a log for almost one and a half days. I only woke briefly when Mum brought me lunch and then an evening meal. Luckily, I did not blush when she said, “You and Brian must have had a hectic weekend, for you to be so tired.”
“Yes, we somewhat overdid the hiking.”
Mum already knew and accepted that Brian and I were intimate. So, the meaning of my statement held no mystery for her. She did not voice any disapproval; she offered only supportive guidance.
“I understand, but you must remember not to overdo the exercise, or the fun will go out of it. Also, remember to use some soothing lotions to ease your special aches.”
I nodded and said, “I will take care, Mum.” After she left me, I went to the bathroom, found some salves, and applied them to my tender boy pussy. I sighed and mentally thanked Mum as they had an immediate soothing effect, allowing me to sleep more comfortably that night.
I returned to school on Tuesday, and life more or less returned to normal, except that over the following two weeks, I got the belt from several teachers for daydreaming in class.
Miss Brand, nicknamed Battleaxe, caught me in a mind-fade for the umpteenth time and told me to go to her room at the end of the day. The class went quiet because everyone knew I was going to get the tawse on the bottom. Even so, most sniggered as I left for her room at the end of the last class.
Battleaxe wasted no time on preliminaries. The moment I entered her office, she said, “You know exactly why you are here. Shut the door, take off your trousers, and bend over my desk.”
These moves were exactly as expected, but what came next was a shock, to say the least. I gasped in horror when, instead of getting a tawse from her desk, she went to a cupboard and picked out the Senior Girls’ cane.
“I am very disappointed by your lack of focus and application in class, but I see that this cane now has your undivided attention. I think that it is time that you received its full behavior-correcting message. I am sure that will put an end to your daydreaming.”
I was now scared because while Battleaxe could give the belt to boys and girls, she was only permitted to cane girls, and then only on rare occasions. All boys and the most recalcitrant girls were always dealt with by the headmaster. So, this situation was highly irregular. However, there was no point in complaining, because that would only make things even worse. So, I accepted my fate.
Battleaxe swished the cane a couple of times before moving behind me. My heart then sank as she said, “Oh-no, we cannot have these taking the edge off the cane’s message” before pulling my underpants down to my knees. I gasped as the cane then thudded onto my now exposed bum and screamed in pain as the red-hot stripe it left behind released its full fury into my buttocks. Just as my distress was peaking, I was surprised to hear a girl’s voice.
“He is getting the cane.”
From the mutterings that followed, it was obvious that the rest of the class was close by, savoring every tidbit of my downfall. My punishment was especially captivating for them because while we all had felt the kiss of Battleaxe’s tawse, I was the first to be caned by her.
Battleaxe probably heard the audience and may have decided to make the lesson memorable for them as well as me. Just as the agony of the initial hit reached its peak, she unleashed an even more breath-taking strike to my rear, followed by three more at intervals timed to ensure my rear endured the maximum distress. Last but not least, she unleashed an angled blow that relit all the parallel stripes covering my bottom. I howled like a banshee as it was now engulfed with unbearable pain.
Battleaxe was certainly a master of the art of caning and deserved her nickname. I had been spanked many times before, but the pain she inflicted on me was orders of magnitude worse. She broke me, and to add salt to my wounds, most, if not all, of the class heard my demise.
I stood up expecting a drawn-out lecture about sorting myself out in class, but that did not happen. Miss Brand, now seated in her chair and looking unnervingly serene, said only a few words.
“Your daydreaming in class stops right now, and you go back to your studious self or else. It would hurt me greatly to cane you again, but I guarantee I will do so if it is necessary to keep you on the straight and narrow. Now, off you go.”
Miss Brand grinned as I struggled to redress. I assumed she was amused by my difficulties in pulling my drawers and trousers up over my very sore bum. However, as I was doing so, I realized all my tackle was on full display to her and wondered if this was the cause of her delight.
I took my leave and headed to the boys’ changing room to recover in peace. No chance, every boy from class was waiting for me, insistent on seeing my stripes. I knew that I had no choice, so I gave in and dropped my pants and undies. I am glad that I did so, because the lads drew back in shock at the devastating evidence before them.
“Oh man, a caning like that would have destroyed me, but you look to be coping with it. Good on you. You are not a sissy after all. One thing is certain, from now on, I will do my best to make sure it never happens to me.”
“So, say we all.”
Luck was with me, as the lads did not realize just how bad a shape I was really in. However, I got a boost from the fact that my painful demise had given me some street cred amongst them and might also improve their general behavior in class; a bonus for Miss Brand.
The boys then left me to rest and recover, but my travails were not over. As I was about to head off home, two girls from class, Mary and Jane, grabbed me and dragged me off to the nearby sports pavilion, where the remaining nineteen girls, including Brenda, were gathered. Judging by their eager eyes, there was no doubt that they, like the boys, wanted to see my stripes, so I gave in straightaway and lowered my trousers and underpants.
From the sudden loud, excited gasps, it was clear that this was the first time most of them had ever seen the male downstairs in the flesh. They eagerly circled around me, taking every opportunity to ogle, ooh and ahh, and even make toe-curling comments about my tackle. Eventually, albeit reluctantly, they turned their attention to my stripy rear, and, like the boys, agreed they must do everything to make sure they avoided the cane.
The happy mood in the room then changed dramatically as the girls began chattering amongst themselves, and I was stunned by a frequent comment.
“Battleaxe is a star. She has shown us that boys are not all-powerful and can be cut down to size by a ‘weak’ female.”
I then cringed as one strident voice said, “Yes, and maybe we should take the chance to reinforce that message and put this male in his place.”
Had I not been the center of attention, I would have been amazed at how quickly the pack mentality took hold, and these otherwise sweet lasses became a baying mob. Soon, there was a unanimous, raucous agreement that they wanted revenge for the distress boys had caused them. All their original shock over my stripey bum went out the window as they decided I would be a whipping boy.
The girls then formed a single-file queue, while Mary and Jane held me in the center of the room. Then, one by one, each girl moved behind me and smacked each buttock before going to the back of the room. The individual hits were not excessive in themselves, but the combination of nineteen of them on each cheek of my already caned bum had me squirming and moaning. So, my whole bum was glowing bright red before last but not least, Mary and Jane took their turns. They clearly had a lot of anger to vent, because their strikes were eye-watering and left me in no doubt.
The girls now left, giggling and laughing as they went, leaving only Brenda and me in the pavilion. I was now relaxed because she had already spanked me. Big mistake. That had been as a class member; now it was personal. She now told me, in no uncertain terms, just how angry she was with me for being such a jerk over the last two weeks, for getting myself into teacher trouble, and most of all for leaving her alone while I spent the weekend with Brian. She now set our friendship aside, took a hairbrush from her bag, and let loose on me with three formidable smacks to each cheek. She finished off with a final, especially brutal strike that crossed over both buttocks and relit every tender spot on my bum, leaving me howling and moaning in pain.
At this very moment, we were shocked to see Miss Brand standing in the doorway. What is more, she was smiling. “My, my, I was wondering what was going on when I saw your very happy classmates trooping out from here. Now, I see that you girls have been enthusiastically reinforcing my special lesson for George. Thank you, I am sure his daydreaming days are now over.”
Miss Brand then grinned like a Cheshire cat. “I hope you all took the opportunity to eyeball and appreciate the male anatomy on show. I certainly did. It is very interesting to find that boys are not as all-powerful as they pretend to be. Their preening manhood is no more than an ornament if they have no access to pussy.”
I did not say a word, for Miss Brand was obviously an innocent. She was correct in her assessment of the flawed dominance and submissive dynamics of the usual male-female relationship, but obviously she knew nothing of the joyous possibilities of boy-on-boy.
Miss Brand then left, saying, “Take care, see you both tomorrow.”
Brenda put the hairbrush back in her bag, took me in her arms, and for the first time ever kissed me on the lips.
“Well, that was unexpected. I am sure you do not feel like it at present, but your painful adventures have done a lot of good today. The girls will now be little angels for quite some time, now that they have quenched their built-up frustrations. Do not worry, those minxes will tell no one, for they know that would only bring trouble from the Puritans and take away their joy. Anyway, no one will believe them.”
“I had no idea that boys made life so miserable for girls. My rear is hurting, but if that has helped out, it is a small price to pay. Do you think Battleaxe caned me for the same reason?”
Brenda smiled. “Yes and no. The main reason for the caning was your misbehavior, but choosing to do it herself rather than sending you to the headmaster, as expected, suggests she had additional motives. Miss Brand likes you and maybe wanted to protect you from the brutality of the Senior boys’ cane. However, I have been told she is being given a hard time by some male colleagues, so, given the opportunity, she, like us, may have decided to expunge some of that frustration on you. That would explain why she is now so happy.”
“Oh well, only time will tell if the distress her cane caused my bottom was worth it.”
“You know why I spanked you, and you fully deserved it. But I must also thank you for providing the answer to a question that has niggled me for a long time. Mum always says that it hurts her more than me when she gives me a thrashing, but now, thanks to you, I know that is untrue, as I am sure that your bottom will agree.”
I could only nod and concur. “Yes, I saw no signs that you were suffering, before, during, or after you let loose on my bum, so I concur with your understanding.”
“Good. Now let us go home.”
Brenda picked up my underpants, held them out, and I stepped into them. She was transfixed momentarily by my junk, but gasped and quickly lifted the drawers up into place as my cock began standing to attention. Next, she helped me on with my trousers and shoes, and we snogged for a while before leaving for home, where, now in charge, she explained to Mum that I had been caned by Miss Brand.
“Well, if your favorite teacher did that to you, it must have been well deserved. You had better get off to bed and lick your wounds.”
I heard Mum talking to Brenda before she left. By then, I was lying on my stomach on top of my bed, with my glowing buns warming the cool air in the room.
I could hardly believe what my prim and proper Mum then said. “Oh my, your red, striped bum brings back so many bad memories of being caned at school. No need to look so shocked. I was a mischievous youngster back then, when the cane was the go-to instrument of punishment for even minor infractions. So, I was on the receiving end, on occasion, from the headmaster, but most often from female teachers. He was harsh and no-nonsense but fair; his punishments were measured, matched the seriousness of the transgression, and were on the skirt or, now and again, on the knickers. That was not the case with female teachers, especially if they disliked you. Then, it was always knickers down and an unwarranted number of brutal hits with the Senior Girls’ cane. There was one particular teacher who regularly took great delight in caning me for even the most trivial of supposed infringements.”
“Oh my, but why did they get away with that?”
“In those dark days, teachers were like gods who could not be questioned. If we argued, we knew that was just the excuse they or other colleagues needed to cause our bottoms even more pain. You probably will not believe this, but Miss Brand’s six of the best seems quite considered, focusing on correcting your behavior rather than unjustly causing you severe pain. This will pass. Hunker down and do everything she asks from now on, and believe me, things will be okay.”
The fact that Mum had endured the same, or worse, and understood how I felt was reassuring and helped me get to sleep, albeit with my bottom still warming up the room. I decided not to say anything about the girls’ actions because that information would have greatly upset Mum. The fact that they spanked me was not a real problem; in fact, she would probably have approved. No, it was because these ‘innocent’ girls saw and took every opportunity to ogle my male tackle in all its naked glory. This was no earth-shattering event, but in the eyes of the strict moralists, it would be considered a first step on the road to wreck and ruin. Mum was not an adherent to these crazy ideas, but would have been afraid of the repercussions if others found out. So, I decided to rely on the girls saying nothing untoward.
I was still stiff and sore when I got up the next morning, but I set off for school anyway. I decided it was best to tackle any situation head-on, rather than put it off. Thankfully, everything was quiet and tickety-boo. Peace reigned in class; the boys had a bit more respect for me. The girls just smiled and said nothing about the events in the pavilion. The only quirk was that individual girls, even the shy ones, would occasionally pat me on the bum when they were sure no boys were looking. I accepted this ploy because I knew they had suffered far worse at the hands of boys.
Miss Brand must have seen some of these incidents, but clearly paid no heed. Indeed, she was unusually mellow and tolerant. Two weeks elapsed before anyone in class felt the kiss of her tawse. Even in the weeks that followed, she used the tawse far less than before. Indeed, it was almost a whole month before Brenda and I were acquainted with it, for talking in class.
I saw Brian occasionally, but we just chatted. He and Jenny were getting closer, but had not yet done the deed. Brenda and I continued to work together on schoolwork and other projects. I should have twigged that things were going too well, for that is usually when they are likely to go pear-shaped. So, I was shocked when they did, especially since Brian was the indirect cause.
Brian and Jenny had been walking out unchaperoned for some time, and many other boy-and-girl couples began following their example. These actions infuriated the firebrand moralists who held sway over the relatively conservative area. They demanded that their version of respectability be restored; unmarried couples were not to be allowed out together unless supervised at all times. Stupid, I know, but sadly, they got their way.
At first, this edict had no effect on Brenda and me, because we lived out of town. However, all it took was one sour-faced besom seeing us together for all hell to break loose. We were forbidden to be together without close supervision. I was in despair, but our Mums, bless them, came up with an ingenious, albeit scary, solution to the problem. They concluded that two girls out together would not raise any moralist eyebrows. So, just when I thought my life could not be more complicated, they suggested that I dress as a girl and become my ‘Cousin Ann’ at weekends and during holidays.
Naturally, I was totally opposed to this idea. “No way, never going to happen.”
“Well, if that is the case, you will have to be on your own, because you and Brenda cannot be seen together.”
I soon realized that I would truly be on my own; Brian was now otherwise occupied, and while the other boys in class respected me more than before, they still did not want to associate with a wuss.
So it was that next morning, I found myself in Mum’s bedroom being kitted out in clothes Brenda’s Mum had left the night before. The first thing that surprised me was just how happy Mum was while dressing me as a girl, even though she had always insisted that everything I wore be distinctly masculine. Indeed, I could not get over the fact that she was practically beaming like a Cheshire cat while she now fussed over me. All very strange.
Naturally, I felt uneasy and a little scared about dressing as a girl, but to my astonishment, these anxieties disappeared when Mum fitted me with a bra, knickers, and knee-high socks. Moreover, to my surprise, my feelings of well-being soared as she completed my transformation, with a camisole, blouse, half-slip, and skirt, along with a shoulder-length wig, kitten-heeled shoes, and light makeup. I was stunned to see that the image in the full-length mirror was unmistakably that of an eighteen-year-old lass who resembled Brenda. So, it was that Mum’s niece ‘Ann’ came into being.
I did not have long to adjust to this new persona because Mum and I soon headed off to Brenda’s home. Although this was the obvious next step, I still quivered anxiously at the thought of meeting others while dressed as a girl. I was unable to concentrate and stumbled many times along the way, but with Mum’s guidance, I eventually mastered walking in small heels by slowing down and taking shorter, daintier steps.
Brenda and Brian were in hysterics when they first saw me, but both quickly settled down and accepted me after I explained why I was cross-dressing. Brenda kissed me on the cheek. “Thank you for being so brave for me.”
Brenda’s dad, James, who had severely thrashed me once before, just muttered some oaths about me being a sissy and left the room. In contrast, Brenda’s mother, Jane, was very supportive. No surprise there, since she and Mum hatched this plan, and she provided the girl’s clothes.
Before long, Mum, Jane, Brenda, and Ann were heading off into town to do some shopping. After all, I needed to get used to being a girl in public and, equally important, to have girls’ clothes of my own to wear.
At first, I was okay, but as we neared the first groups of people, I became increasingly nervous. It was one thing to pretend to be a girl amongst friends, but something entirely different to carry it off amongst strangers. However, I need not have worried, because no one paid me any particular attention. Cross-dressing was not common back then, and Mum had done such a good job that I did not look out of place. So, passers-by only saw two mothers and their teenage daughters out shopping.
I did cringe when we first met some of Mum’s friends, but, without a doubt, they accepted me as her niece. Indeed, they seemed happy that I was staying with her.
“Looking after a girl is much more fun than a troublesome boy. Enjoy time with your niece, and you get close with your aunt, young lady; there is so much you can learn from her.”
In my primmest voice, I said, “Thank you, I will. She has already taught me so much.”
These convivial interactions continued as we met further friends of Mum and Jane, and even when we met two of the sour-faced do-gooders who were so indignant about boys and girls being together unsupervised. Despite their haughty demeanor, they still chatted kindly with us, and I had to stifle a chuckle when I wondered how they would have reacted if they realized I was a boy.
My heart sank when Brenda was spotted by some boys from our class at school. Thankfully, luck was with me, and I was accepted, without question, as Mum’s niece, Ann. Soon after, we met some girls from the class, including Jane, and everything seemed to be okay. But as we were about to move off, Jane whispered in my ear, “We know who you really are, but your secret is safe with us. If you want to risk being out as a girl just to spend time with Brenda, that is good, and we will look out for you.”
Jane was gone before I could say anything, but that moment set the stage for what was to come. Ann was a secret amongst the girls, and whenever I met any of them while en femme, they were very supportive and often offered tips on dress, hair, and makeup.
When I later asked Brenda about this, she said, “Firstly, you accepted their punishment with good grace. Then, even knowing about how badly boys treat girls, they see that you are still prepared to be a girl to help me. Moreover, now that you have come over to the fem side, you are no longer a threat, and they now just want to help you blossom.”
We spent the rest of the day going from shop to shop, looking at and trying on umpteen items of clothing, some of which left me bemused and mystified. However, by the end of the day, we all had full bags of women’s wear to carry home. I was tired and somewhat relieved when we arrived there. We relaxed for a while, had a light meal, and afterward, Brenda and Ann put on a show of their new clothes for our Mums.
As Jane and Brenda were about to set off home, Brenda said, “I will be here about nine o’clock tomorrow morning. We can go to the park and work on that assignment on local plants and flowers.”
“Okay, that will be good. See you then.”
After they left, Mum said, “You have had a stressful day, so you had better have a good night’s sleep to be ready for tomorrow.”
Mum followed me through to my bedroom and helped me hang up my girls’ clothes. Then, to my surprise, she opened a mystery package and handed me a pink nightdress with matching panties. “If you are going to be a girl all day tomorrow, you may as well get used to the idea overnight.”
I stepped into the panties, put on the nightie, slipped into bed, and pulled the duvet over me. Now I realized that Mum intended this to be a complete feminine experience, for I was quickly swathed in the aroma of perfumes she had applied to the bed linen. As I succumbed to these feminine fragrances, Mum kissed me on the cheek and said, “Goodnight, sleep tight, sweetie.” She had not done so for many a year, and I could not help but notice that she was smiling from ear to ear as she switched off the light and closed the door behind her.
I fell into a very deep sleep and was eventually woken by Mum to prepare for the day ahead. Still in my nightdress, I went through to the kitchen, and we had breakfast together. Then, Mum took me through to her bedroom, where she had laid out my clothes for the day. After I took off my nightie and knickers, she fitted me with a padded bra, panties, and knee-length socks. Then, she took me across to her dressing table.
“Watch closely what I am about to do because you must learn to do it for yourself.”
Then, Mum fitted me with a shoulder-length wig, before applying light makeup on my face and blush-rose on my lips. Finally, she helped me with a full slip and dress and finished off putting me in Mary Jane shoes. As I looked in the mirror, I saw an eighteen-year-old girl and a happy and contented one at that.
I was just gathering my notepad, sketchbooks, and other essentials for the day when there was a knock at the door. Brenda and her Mum had arrived. After some small talk, Brenda and I headed off while our Mums continued to talk. I was feeling quite content as we made our way to the park, but just as we passed a group gathered at the entrance gate, a gust of wind flipped my skirt and slip, exposing my pink panties to all and sundry. I went bright red and howled as the males shouted their loud and crude appreciation.
Brenda giggled at my discomfort, but then said, “Strong breezes are adept at flipping skirts. For every girl, the first public flash always concentrates the mind on learning how to control your skirt. Now that trauma has happened to you, I will teach you how to try to prevent it.”
“So, this has happened to you?”
“Of course, and just like you, I went berserk at first. But then, after the third occasion, I realized that older, more experienced girls did not overreact to the reveal. They only brushed down their skirts and moved on as though nothing had happened. That instantly killed off the raucous male mood. So, I learned to copy those girls and quietly move on from a flash, and it works.”
“I am not sure if I can do that.”
“Just keep your chin up, you will. Pantie exposure is always mortifying whenever it happens, but as you now know, it is not the end of the world, and you can get over it.”
“Oh well, if the occasional undie flash is part of being a girl, I will just have to accept it.”
“Good on you. Sadly, you will have many more challenges. But take it from me, being a girl is fun.”
We made our way through the park, found a small clearing, and set about documenting and sketching its unique nature. Those tasks may not seem fun to many, but for Brenda and me, it was a pleasure. Although we concentrated on preparing our notes and sketches during the day, we did have a few refreshment breaks, and during these, Brenda helped me improve my bearing and persona as a girl. During this fun training, I realized that, for reasons I could not understand, I was now willingly going beyond just cross-dressing and beginning to embrace girls’ ways in a broader sense.
Brenda and I gathered up our things and headed back home after a successful day. For the first time ever, Brenda and I held hands as we walked home. It felt like the natural thing to do. Still, I did go bright red when, at one point, she leaned in and kissed me. “Ann, you are going to be a very sweet girl and my very best friend.”
Once home, I found that Mum and Jane had transformed my plain bedroom into a girl’s one, complete with a dressing table, pink/floral bed linen, and hints of perfumes wafting in the air. My wardrobe and drawer unit now contained mainly girls’ wear, with only a small part set aside for my boys’ school clothes.
“What is going on?
We think it would be best for you to be a girl full-time, except when you are at school. So, we decided you should have a girl’s bedroom, one where you can learn and experiment with girly things, like clothes, hair, and makeup. I am sure you and Brenda can share and learn so much together.”
It would be the understatement of the year to say I was dumbfounded by these developments, but I was equally pleased with Mum’s ideas because I now knew I had her full support and encouragement in developing my feminine side. So, I agreed, and Mum, Jane, and Brenda smiled from ear to ear. Who would believe that, thanks to the meddling moralists, I was now close to being the daughter that Mum always wanted, a second daughter for Jane to fuss over, and the sister Brenda longed for. As this sank in, I realized I was very happy with that.
As Jane and Brenda headed home, my heart sank when Brenda reminded me that school was tomorrow. That meant I would have to get back into my rough and shapeless boys’ clothes in the morning. Mum must have seen my dismay, for she said, “There is nothing you can do about that, but you can still be a girl overnight.”
Mum led me through to my now oh so feminine bedroom, undressed me, and had me put on a pair of pink panties. Then, she sat me at the dressing table, took off my wig and placed it on a stand, before carefully removing all of my make-up.
“The boys at school will give you a bad time if they see even a hint of cosmetics.”
“That is true. They will be ‘very sympathetic.”
I then put on a pink nightie, slipped into bed, and pulled the covers over me. While I succumbed to the feminine fragrances surrounding me, Mum laid out my school clothes for the next day, tucked me in, kissed me on the cheek as the night before, and said, “Goodnight, sweet dreams, honey.” As she closed the door behind her, I saw that she was again smiling happily and realized that Brenda was correct. Mum was in seventh heaven to have a fem-son to train and fuss over.
Although the events of the day spun around in my head, I quickly fell asleep and had to be woken up by Mum to get ready for school. Another surprise was that she now fussed over me and helped me properly and neatly dress in my boys’ clothes, just as when she dressed me as a girl. Obviously, her fem-son was to be prim and proper whether dressed as a girl or a boy.
In the following weeks, I was a girl every night after school, and full-time at weekends and during any holidays. I could not have been happier. The only downside was that, despite my best efforts to hide them, I now had a number of obvious female mannerisms and became an increasing target for school bullies, who wanted to toughen me up and see the error of my ways. Fortunately, my new persona was up to the test.
Brenda and I settled into a routine over the next weeks and months. We continued to document the changing flora and fauna in our favorite park and further afield during the holidays. We were readily accepted as two young ladies by all who stopped to admire our drawings. Even Miss Brand, who recognized me immediately, was fully supportive.
One day, we were relaxing in the sun in a forest clearing after completing our work when an intriguing thought occurred to me while watching Brenda. She was a beautiful, sexy girl, but we were no more than friends. Although Brian and I had been lovers, I liked girls but had never made any moves on Brenda. Moreover, while talking to other boys or me, she never did so in a come-on or flirtatious way. At the time, I decided not to dwell further on this, for I was content with our platonic friendship, and dim as ever, never for a moment thought that Brenda was not.
Things came to a head one week later when we had been in the park all day. She was very quiet and, if anything, a bit grumpy. I had asked her several times what was wrong, and she kept saying, “Nothing”. Finally, as we packed up, she snapped. “You keep asking me what is the matter. Well, surprise, surprise, I want us to be more than just friends; I want us to be a couple. I thought that being out and about as girls would free us from prying eyes and allow us to get close and personal, but no. Do you only care for Brian?”
My jaw dropped. “You mean you have known about Brian and me all along? I am so ashamed that you saw us together. Why did you not say anything?”
“How was I supposed to ask my best friend about him being my brother’s lover. I did not want to stir up a hornet’s nest, and besides, I saw you were happy together. After some sisterly pressure on Brian, he told me you were practicing for the real thing. So, when he and Jenny began courting, I thought my chance would come. The spanking I gave you was not because you left me alone. I was jealous that you made love to Brian instead of me.”
“I am so sorry, in all the turmoil and challenges of learning to be a fem-boy, I have temporarily lost sight of the basics of the boy part. Of course, I want to be intimate with you; the fem-boy/girl combination could be particularly interesting. How about we start afresh?”
I saw from the beaming smile on Brenda’s face that this was exactly what she wanted to hear, and “Oh, you naughty boy” were her only words before we settled into an intense smooch. As our hands began to wander, we were soon canoodling in just our bras and panties. As we warmed up, we took off each other’s bras and were surprised to find that our boobs were very similar, small handfuls that were highly responsive to caressing fingers. We were soon sighing and purring with a delight that then went through the roof once we were enthusiastically suckling one another’s nipples.
I now kissed my way down Brenda’s abdomen until my lips touched the waistband of her knickers. As I hooked my fingers around it, she lifted her rear to allow her panties to slip down below her pussy. My nose was now engulfed by the sweet scents of her mound of Venus and drawn towards her fud. I was now in unknown territory, but remembering how I used my lips and tongue to stimulate Brian’s cock I let them loose on Brenda’s prominent fanny lips. That did the trick, for she was soon moaning and groaning as her labia engorged, and in no short order she was shrieking with joy, and her whole body quivered when her vagina spasmed and flooded with juices. She purred with delight as I lapped up every drop, for her love honey was far tastier and satisfying than any mouthful of cum.
I now moved up alongside Brenda, and we settled into a snog. She got quite excited as she hoovered up the remnants of her pussy juices from my lips and tongue, and then became highly aroused when my cock stood to attention, having been awakened by her fanny’s wetness soaking into my knickers.
My cock sprang free and nestled on Brenda’s beaver after she pulled down my panties.
“We have waited far too long. Take me now. I want to have you.”
My penis now quivered in eager anticipation as it sensed the moistness of her vulva. However, despite this moment being every boy’s dream, I hesitated.
“What is wrong? Am I not good enough?”
“Oh no, far from it. I am having to struggle hard to keep myself from going Barbarian and ravishing you here and now.”
“So, what is the problem?”
“I have no protection; I do not want to risk you getting pregnant, just for the pleasures of intercourse. That would be unfair to you.”
“Oh, is that all. You and Brian did not worry about that when you were rogering one another.”
“Well, you know why that was possible.”
“No need for too much information, but what is good for the gander can also be perfect for the goose.”
“Are you saying what I think you are?”
At first, Brenda said not a word. Instead, she took a tube of olive oil from her bag, handed it to me, and then got on all fours, so that both her pussies were on display.
Then, she said, “It is up to you now. My anal pussy is ready.”
I was still dithering, but my cock was ready to go, so I lubed it with the oil and poured some into Brenda’s bum crack. Calling upon all my practices with Brian, I touched her bum hole with my cock and then gently but firmly pushed against it. She shrieked as the head burst into her, but then began sighing as my shaft delved deeper into her and was finally buried to the hilt in her soft, alluring ass. The thrilling sensations now surging through my cock were out of this world and far more intense and pleasurable than any I had enjoyed with Brian. In fact, I could not help but think that, amongst all the recent upheavals in my life, this one was meant to be, all along.
Brenda was soon groaning and moaning in rhythm with my steady strokes. To keep my cock from shooting its load while also keeping Brenda’s fanny in a frenzy, I performed the slow-down-speed-up trick I had used on Brian. It worked even better on Brenda, for she was gasping and freaking out when I sped up for the third time. We both squealed as my cock went berserk, erupted, and then did a geyser impression as it filled Brenda’s anal fud with lashings of hot spunk. To my utter surprise, Brenda now screamed for a second time as she climaxed, and love juices trickled from her vulva. Needless to say, we were both grinning with joy at our carnal achievement as we cuddled and fell asleep.
Of course, like kids in a sweet shop, we could not contain ourselves. So, we took each other to bliss once more that evening, and on many occasions during the weeks that followed. I used the many skills I had perfected with Brian to take us both to seventh heaven. So, while sketching remained a weekend pastime, it was no longer the main one.
I recalled Brian once mentioning an older lad who sold something special for the weekend, so I eventually tracked him down and bought a couple of packs. Once Brenda and I were hot and ready the following Saturday, she looked on completely bemused as I fitted a Johnnie over my cock, but was soon squealing with absolute joy as I then deflowered her pussy and eagerly screwed it to climax. Needless to say, we used a whole pack that wonderful day, but on Sunday Brenda said, “Yesterday was out of this world, but save your rubbers for another special time. Use the rear entrance today.”
So, it has come to be that we enjoy anal coitus most of the time and protected pussy intercourse when the mood takes us. Brenda loves both front- and back-door sex, but if anything, she prefers the back door, because she finds that bareback is more of a thrill than being taken by a sheathed cock. I am more than thrilled and satisfied either way, and happy to safely enjoy and share the pleasures Brian and I perfected while practicing for the real thing. As for bareback front door intercourse with Brenda, I can wait.
The last few months have been unbelievable. I have gone from enthusiastic boy-on-boy with Brian to being a cross-dresser who finally became his sister Brenda’s lover. Confusing, to say the least, but I am happy as a fem-boy, and looking forward to the interesting challenges and opportunities ahead.
