Uncle Toby's Memoirs

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

The following Sunday saw us all on our best behaviour as the vicar made one of his occasional visits to join us for supper. We engaged him in an earnest discussion of his younger days as a missionary, and he went away well pleased with our respectability. I was worried, however, that his visit might have stayed the momentum of our little group. I needn't have worried.

I had begun to suspect that Betty was the ringleader of the girls, and the following Sunday supported this hypothesis. Soon after we arrived from church Betty said "I suppose I might as well get it over with!" She began undoing her buttons as she looked around at each of us in turn. Each of us glanced away in embarrassment as she looked in our direction, which led to some giggling from all the girls. To our surprise it was Alexa who started the girls clamouring for skin. The losing boy that week had been Harry, who required a sharp elbow from Bertie to propel him into action.

That evening brought considerable rewards. Betty seemed to know which movements would cause her dress to gape open, and she didn't shrink from making these movements. Her breasts were probably the smallest of all the girls, and her bra was the same standard white cotton, but the views were generous.

The following weeks revealed Bea and Vicky in turn. Since the winning and losing of the points competition mostly depended on the whim of the teaching staff, it helped that they appeared to prefer to share the honours around, rather than have any house become either too complacent or too discouraged. We had been looking forward to Vicky, as she appeared to have the largest breasts of all the girls. Unfortunately neither Bea nor Vicky had the same inclination or ability as Betty to have their dresses gape open, but we weren't entirely unrewarded. The situation was no less exciting, and my masturbation sessions were now very frequent. The only restraint I was showing was to avoid messing up my sheets, confining my activities to the toilets.

The following weeks brought repeat showings of Bea and then Betty. By this time all of the boys had taken turns being shirtless. I am sure there was a unanimous desire to raise the stakes to see more, although it didn't follow that everyone was prepared to show more. As I have previously mentioned, there was a degree of competitiveness to our games. There had been the occasional mention of introducing more of a boys versus girls element to our competition. This was mentioned more often by the girls, funnily enough. The reason for this was that the girls typically ended up with more points overall in the inter-house competition. However, we were all too intelligent to take this seriously. Because they were separate schools, it followed that the awarding and deducting of points would never be consistent, and none of us could really pretend otherwise.

As it happened, a level playing field was looming on the horizon. In those days New Zealand was still firmly attached to the apron strings of England, and many of the private schools had their students sit the English A-level exams. Because the New Zealand school year runs from February to December, the English exams happened just over halfway through our school year. This put us under a great deal of pressure, and our competitiveness came to the fore, leading to a great deal of bantering on our Sunday evenings with the girls.

The arrogance of the upper classes is bred into each generation at a young age, and even the shyest amongst our number didn't seem to consider the possibility that they would lose. The exams came and went, and we now faced several weeks waiting for the results. The confidence of each gender remained high that they would prevail, and negotiations intensified to determine the forfeit for the losers. There was no doubt that the stakes would be raised. The conclusion was not unexpected given the circumstances. It was agreed that the losing team were to strip down to their underwear for the duration of our supper.

Our exam results arrived on a Thursday, and the boys gathered together to calculate our overall performance. Our confidence became dented in the cool light of the numbers, and it suddenly occurred to us that maybe the girls would beat us. It was with a fair degree of nervousness that we prepared for church that Sunday evening. I for one had made sure I was wearing my newest and cleanest pair of underpants, and I'm sure the others had made similar preparations.

At church we could see that the gravity of the situation was weighing just as heavily on the girls, and I was comforted to see that they didn't appear confident. As it transpired, they had every reason to be nervous because they had lost a very close contest. Their average marks were just four points lower than ours. All of a sudden I was going to see not just one but four girls in just their underwear. We managed to stifle much of our external rejoicing, but our excitement was real and evidenced by carefully concealed erections as we sat and watched the girls deliver on their promise.

The girls huddled together, no doubt to encourage each other, before they lined up with their backs towards us. Their hands went to the buttons of their dresses, then in unison they slipped their dresses off their shoulders and allowed them to fall to their ankles. We were greeted by the sight of four backs crossed by white bra straps, and bottoms and legs covered by white half-slips. There was much nervous giggling as the girls provided their own count-down before turning to face us. The sight was wonderful as we gazed at the row of breasts encased in their bras, ranging in size from Betty's small pair to Vicky's much larger pair. Peter let out a whistle, while the rest of us provided encouragement in the form of applause.

While a bit smug in our victory, we were nonetheless very appreciative as we waited with patience for the anticipated second step of the stripping, when the half-slips would be removed to give us our first look at their knickers. However, it became apparent from the girls' actions as they sat down that this wasn't on their agenda. Our initial polite suggestions turned to furious protests as it became apparent that they didn't intend to remove anything more. They had obviously prepared their position in advance and they argued it like seasoned lawyers. They reasoned that half-slips were underwear, so they had already stripped down to their underwear. We argued and pleaded, but to no avail.

As we went through the stages of grief at this trick, we eventually reached the bargaining stage, and we discovered that the girls were open to this. Their terms also appeared pre-prepared. They demanded we concede that half-slips were underwear, and that they would reveal nothing more that evening. They also demanded that in future, the losing boy from our regular house points competition would strip down to just his underpants, and that the other three boys would go topless. In exchange, the losing girl would strip down to her bra and knickers.

While this deal actually required us to make more concessions than they would, we readily accepted. We had just seen girls in bras for the first time and already we were desperate for something more at any cost. The following week this cost was paid, primarily by me. My house was starting to sink, and I was struggling each week to keep us from coming last. That week it had seemed unavoidable, and I would be the first boy to remove my trousers. I donned my newest pair of underpants before nervously heading to Evensong with my uncompassionate friends.

It was always difficult to pay attention at church when our minds were on the after party. There were frequent glances across the aisle - meaningful glances of which we frequently didn't know the meaning. We had long ago given up looking to see who was carrying the supper as the girls often had another girl carry it just to throw us off the scent. It had become our little tradition to have an announcement of sorts once we were safely ensconced in our room. Harry had great delight in announcing that I was the losing boy of the week, while Betty announced that Victoria was my female equivalent.

Betty reminded us unnecessarily of the agreement we had made the previous week, when the boys had conceded to all going topless. We removed our blazers and began unbuttoning our shirts. Vicky didn't appear to require any special prompting or support from the other girls as she too began to undo her buttons. As we peeled off our shirts she removed her dress at the same time, allowing us to see her bra and half-slip. Then, to our surprise, Vicky immediately removed that also.

We were now in early spring, and the girls were all still wearing stockings as part of their uniform. I knew a little bit about stockings and the garter belts that held them up, but I was blown away by the sight of them in real life. Vicky looked incredibly sexy standing before us in her white bra and knickers and the white garter belt holding up her brown stockings. Her breasts were large and her figure was shapely like an hourglass. Her knickers were what young people today might call full briefs or "granny pants", but such were the fashions of the day. She looked hot. She smiled at us and asked coquettishly if she was expected to remove the stockings and garter belt. Harry answered for us all when he replied that she looked fine as she was.

By getting her stripping out of the way so quickly, Vicky had neatly put me on the spot as seven pairs of eyes now turned to look at me. I had made no attempt to curb my lustful thoughts as I watched Vicky undress. I was highly conscious that I was fully erect, and the others were never going to tolerate any delays on my part. I had no choice but to kick off my shoes and begin removing my trousers. Doing it sitting down would only have invited scorn and ridicule, as all previous stripping had been done standing up. I pushed my pants down and stepped out of them.

The status of my erection had evidently been pre-discussed earlier by the girls, as Bea's comment of "I told you it would be" seemed to sum it all up. To my great embarrassment my excitement was obvious to all. My torment was by no means over, as it was still my job to help Vicky prepare the tea. Working in close proximity with her in her underwear maintained the tension, as did the attention of all the girls, particularly as they delighted in sending me on extra errands for more milk or sugar, just so they could watch me move about the room.

As the supper finally drew to an end Vicky and I were given permission to put our clothes back on before walking back to school. I had been painfully erect for over two hours by the time I was safely closeted in the toilets and able to give myself some relief.

My house continued its downward slide, putting me on display again the following week, this time with Bea as the other victim. The week after that I managed third place, meaning that Bertie was the one serving supper in his underpants. Vicky was in her underwear again that week, and I certainly appreciated the opportunity to admiring her figure while still somewhat clothed myself. All the girls were pretty, but Vicky was in a league of her own. I was also pleased to note that Bertie's erection was as obvious as mine had been the previous two weeks. Not that I was at all interested in his erection, I hasten to add. It was just that I was glad that another had responded in a similar way to the same situation.

One week later I was again the loser. This time the loser for the girls was Betty, who continued to be the most daring of the girls. As we prepared the supper she bumped up against me several times, seemingly secure in the knowledge that she was tormenting me.

The following week gave me another respite, as it was Harry and Alexandra who had to make the supper in their underwear. Alexa was the last of the girls to show her knickers, and her shyness only served to accentuate the situation. We had been creating a world of our own on these Sunday evenings, but the realisation was never far below the surface that our actions were so perverted from what was expected of our station in life. Simply, her shyness reminded us how naughty we were. The other circumstance of note that evening was that Harry was not in the least bit erect, for reasons that remain completely unknown as I naturally never discussed it with him. There was much whispering amongst the girls but nothing was said out loud. The look of extreme embarrassment on his face discouraged open communication.

My house continued their notorious ways, and I was again doomed to exposure seven days later. To my consternation the girls were starting to express some dissatisfaction with the repetition. Peter had so far escaped removing his trousers, and the girls began openly stating that they wished his house would soon have a bad week. Peter smiled shyly, obviously pleased.

That evening stands out in my memory as the evening Betty surprised us all by wearing black underwear. Young people today will have no comprehension of the significance of this. Black underwear in those days was certainly a more "adult" option and against the rules of schools like St Hilda's. In fact, the girls seemed just as excited as the boys, and they bombarded Betty with questions about how she had managed to possess them. It transpired that she had been saving her money and had snuck into the shops during her weekend at home. We also noticed that the fabric involved in her underwear was slightly less than the usual uniform attire, revealing more of her lovely upper slopes.

The school year was rapidly drawing to a close. We were already studying hard for our final exams. By our calculations we only had three more Sunday nights together, and the last of those would be in the company of the vicar, meaning that we had only two more chances to play our risqué games. Prior to our last get together we would all be having school exams - an internal set of exams that would determine who would get academic prizes as well as providing valuable practice for the real exams to follow. Naturally, these practice exams were the ideal fodder for our games. Our penultimate evening together ("hosted", incidentally, by Bertie and Bea) was almost entirely spent by negotiating the wagers to govern our final hurrah.

That a person or persons would be naked was established early in our discussions. We had been so close for so long that anything less would have been a certain anti-climax. The girls had made an early attempt to wager only their breasts against male nakedness, but we were prepared for their tricks and resisted with determination. The girls capitulated. I suspect they too were mindful that this was an extremely rare chance to see some nudity, and they weren't going to miss out. The discussion moved on.

The experiences of the mid-year exams were still in our memories as our only previous boys against girls competition with clothing at stake. Alexa spoke about the unfairness of that arrangement. She had obtained better results than anyone else in the room, but had still been among the losers due to the lower results of the other girls. This observation had some impact on our discussions.

The other important consideration, which was first raised by Betty, was that the losers would in reality receive a double punishment. Not only would they be exposed to the winners, but they would miss out on a golden opportunity to see what they desperately wanted to see. This observation really hit home. I knew I would be devastated if, having come so close, I ended the year without seeing a naked woman. Looking around the room, it was apparent that others were thinking the same thing.

It was Alexa who proposed the solution. The competition would still be boys against girls, with the losing team stripping naked. The exception would be the person with the highest marks out of all eight of us. That person would remain clothed even if their gender was the losing gender. However, in addition to the losing team having to strip, it was proposed that the person with the lowest marks on the winning team would also strip naked. According to these rules, whatever the outcome, everyone was guaranteed to see at least one person of the opposite gender naked. These rules were promptly accepted by everyone.

As our evening came to a close, and Bertie and Bea began to put the rest of their clothes on, Betty suddenly had an idea for raising the stakes with an additional penalty. As things stood, we wouldn't know until the following Sunday evening which team had won or lost. However, the person with the lowest marks from each team would be certain of going naked no matter which team was victorious. Betty's forfeit idea was simple but deliciously naughty. The losing boy and the losing girl would come to church without underwear. As I have stated earlier, all of us had a certain amount of built-in arrogance. None of us seriously considered that we might personally be the loser. While I was never going to be dux, I figured there was every likelihood that I would do better than at least one of the other boys. Since everyone was also thinking the same way, Bettys idea was agreed to by all.

The practice exams finished on Wednesday, and we had our results on Friday morning. We gathered together on our way to lunch to compare our marks, and it transpired that Peter was the loser. I guess the girls had been praying to the right deity, given their frustration that Peter had not had to remove even his trousers in their presence at any stage during our year together. Peter was the shyest of the group, and he took the news badly. We tried to think of some encouraging or reassuring words, but we failed. I'm sure Bertie, Harry and I were all thinking about whether or not our overall marks would be sufficient to beat the girls.

I was expecting to study for my finals during my weekend at home, but I had trouble sustaining my concentration. Sunday evening was the appointed time to see my first naked woman. At least one pretty girl would be shedding her clothes, maybe even three or four. I was in a state of excited agitation when I gathered with the others in my hostel room before church. The others were similarly affected, with Peter the worst of all of us. He had had the whole weekend to dwell on his forthcoming exposure. His agitation was worsened by his not wearing any underwear, in accordance with the agreement with the girls. Despite the heat of the afternoon he was frequently asking our opinion as to whether or not to wear his blazer. He was unable to calm a recurring erection, and wanted to know whether or not the blazer concealed anything, or whether it just attracted attention. I'm afraid we were of no assistance. He kept it on and ended up being the only boy in the school to wear his blazer to church that evening.

If the presence of a blazer were a reliable indicator of the lack of underwear, then the sight of Vicky wearing hers was a sight to gladden my heart and further excite my loins. The fabric of St Hilda's summer dress was quite thin, so she had obviously felt the need for an extra layer to conceal her lack of a bra. Our nervous anticipation continued throughout Evensong as our thoughts were far from religious. Finally the service was over and we practically dragged Peter and Vicky up to the Sunday school parlour.

When we arrived, there was some debate around whether or not we should determine the overall results first, or whether we should have the hors d'oeuvre of Peter and Vicky stripping first. The vote was six to two!

The boys had arranged themselves in a semi-circle on one side of the room, and the girls were arranged in a mirror image. A low table with a plate of biscuits provided by Vicky was all that separated us. I could see Peter and Vicky's eyes meet across the table. Their look indicated camaraderie while at the same time conveying an eager desire to see the other naked. The rest of us, postponing all thoughts that we might have to follow suit, eagerly awaited the show. Vicky and Peter kicked off their footwear and stood up to face one another.