Confessions From Boarding School #1: A Cheating Weekend

This is the first in a series of posts titled “Confessions From Boarding School” wherein I will be detailing everything that happened while I was at boarding school. Due to concerns surrounding privacy, certain names have been changed to protect the identities of the people involved.

As I have mentioned in my ‘My Name Is Vexacus And I Have Depression’ post, I have mental health problems, but that is only part of what this post is about. This post is also about Li, the girl I have mentioned in my ‘The Story Of The One That Semi Got Away’ & ‘How We Got Rid Of Our School Bully’ posts; it is also about another girl I knew at boarding school, Kara (Not her real name). What this post is about, I am ashamed that I did it but as now Li has passed away, I can tell the story about how I betrayed Li with what I did with Kara.

The incident in question took place during the ‘Special Weekend’ of the winter of 1997. Before we go any further, I feel I should explain what the ‘Special Weekend’ was to avoid any confusion. The ‘Special Weekend’ was a school-originated holiday where those that could go home for the weekend did so, particularly those who lived in Bristol or Birmingham. With a majority of the kids gone, the weekend was made a bit ‘extra-special’ for those of us that lived to far away to go home for the weekend.

On that Friday morning, I found out that Li would be going home for the weekend to attend a family funeral, so my weekend started with me saying goodbye to Li and telling her that I would see her after the weekend. After I gave her a quick kiss goodbye, I watched her get in the car and drive away. Now I will fully admit that I was a little heartbroken to see her go home for the weekend, but I fully understand why she had to go home and I also took solace in the fact that I would see her again on Sunday afternoon when she came back to school.

The rest of the day at school was average at best; Matthew and I did as little work as we possibly could on Friday afternoon. We spent the rest of the school day just clowning around and throwing pencils erasers around the class at each other. Unfortunately, my high-spirits were dampened by Creosote; the gardener had used it to wipe out some particularly nasty and persistent clumps of weeds near out class. The stench of the creosote made me feel like I wanted to blow chunks.

And finally, the school day ended we could not wait to get back to my room get out of our stinky school uniforms which were sodden with sweat and wreaked of creosote, and into more relaxing clothes. At tea, which was our evening meal, we found out who would be at school over the weekend, and there were not many people left over the weekend. Including Matthew and myself, there were seven of us left in school for the Special Weekend.

One of those people that would be left in school for the special weekend was Kara, who through the power of hindsight, I can now see that she was a total bitch. She was the type of girl who if she liked a boy would go after him whether he had a girlfriend or not. And as my bad luck would have it, I was to be seated next to her for tea. The evening meal went despite me feeling unwell. During tea, Kara told me that since I was feeling unwell if I needed anything that all I had to do was ask and she’d do it.

Now under any other circumstances, I would have told Kara to “Get stuffed” in stronger terms but alas I could not as I was at the tea-table and there was staff around. I told her I didn’t need any help and that all I needed was peace and quiet and maybe to lie down in my room for a while after tea was done. When the evening meal was over, Matthew and I volunteered to clear the dishes away and set the table for breakfast. Now I can assure you that we did not volunteer to do this because we wanted to be helpful; rather we did it so we could wax lyrical about our favorite topics; Dr. Who, Star Wars, and Power Rangers.

It also gave me some peace and quiet away from Kara, who Matthew pointed out to me after the fact, that she was flirting with me. A half-hour later, we had done the dishes and set the table for breakfast so we headed back to our group’s living room, where much to my annoyance I saw Kara. It turns out that as there only seven of us left in school for the weekend, it had been decided that St. Pats living room would be used for those of us left.

I had hoped I would not have to see Kara until the following morning but I was annoyingly disappointed. As I still felt unwell, I was in no mood to argue or complain about it. Opting to sit at the back of the living room so I could play checkers with Matthew in peace and quiet, I had hoped that Kara would leave us alone; I was wrong. No sooner had we started our game, she sidled over to us and sat at the corner of the table under the pretense of watching us play checkers, but both Matthew and myself why she was really there; to flirt with me.

Because I still did not feel well I put up with Kara’s flirting for as long as I could. But after 45 minutes, I’d had enough and wanted to tell her to “Slag off”, but as in the dining room, I couldn’t say what I wanted as, by this point, Mr. Grimms had entered the living room. I got up and told him that I still did not feel very well and that I was going to go lie down in my room for a while.

He glanced back at the table where I had been playing checkers and knew why I really wanted to go lie down in my room. He said he’d come to check on me later and would wake me up when supper was ready. But before I went to my room to lay down, Mr. Grimms had the school nurse come to the living room and give me some medication. The nurse told me that the medication would help me sleep. And so I took the medication, thanked Mr. Grimms and Nurse for their help, then I went to my room where I enjoyed a couple of hours of blissful peace, quiet, and sleep.

True to his word, Mr. Grimms woke me up when supper was ready, and much to my surprise, I felt a whole lot better than when I went to sleep. He also told me that he checked up on me a few times while I was asleep, telling me that aside from a few mumbled curse-words I was fast asleep. Now even though I knew she’d still be in the living room, I was still annoyed to find Kara sat at the table as I did not want to put up with her flirting and incessant offers to help me and get stuff for me if I needed it.

Seeing as I was feeling better, I felt as if I could hold down more than the single cup of tea and slice of toast that I’d had for the evening meal. Sitting at the back of the living room with Matthew, I had hoped I’d have been able to eat my flapjack and drink my coffee in peace and quiet with my best friend but as you can probably guess I did not get that. Kara soon sidled over to us and sat at the corner of the table next to me. Matthew tried not to let it show that he was doing his best to not laugh, but as he was my best friend I did not slap him with a flapjack.

I tried to ignore Kara but as she was sat right next to me as close as she could get, it was a little hard to ignore her. She made small-talk with Matthew and flirted with me as much as she could without making it too obvious. Now up to this point, the maximum edge of Kara’s flirting had gone no further than sitting close to me, resting her head on my shoulder and putting her arm around my shoulder; but during supper, she went one step further. When Mr. Grimms turned his attention to fixing the TV volume, Kara put her hand under the table and onto my leg and rubbed it. Now I will admit that this caught me off-guard, but before I could tell her to stop touching me, she quickly moved her hand onto my crotch and squeezed it.

I looked at her and she simply smiled before getting up from the table and sitting in front of the TV. I asked Matthew if he saw what she did and said that indeed he did and asked what I was going to do about it. I told him that given the fact I was still somewhat drowsy from the meds Nurse gave me I said that I’d leave it for now and tell the staff in the morning. It was when I went to get up from the table that I had what is called a ‘Head Rush’. Matthew managed to grab hold of me and guided me to a spot on the couch, which unfortunately was next to Kara.

Seeing that I was still woozy, Kara put her head on my shoulder and said she’d keep me safe until I felt better. Given how the couch was placed in the living room, Kara could and did put her hand on my leg without being seen. I must have dozed off because when I woke up, Kara was cuddled up next to me on the couch. I looked at my watch and saw that it was 9:30 pm and I’d been asleep for at least an hour. Matthew of course did nothing to wake me up as he thought it was funny.

As I tried to get up from the couch without waking Kara, I noticed that the top button of her shirt was undone which at the angle I was sat at allowed me to get a quick glimpse of her cleavage. I moved my gaze away from Kara and managed to get up from the couch without waking her. It was then that I realized that the button on her shirt could not in any way whatsoever have come undone on its own; meaning that she had to have undone it herself.

Now as I mentioned previously, the problem with Kara was that she was a bitch and the type of girl who if she liked a boy would go after him whether he had a girlfriend or not. And much to my embarrassment I only realized then that it became clear she was flirting with me as she obviously liked me. Before the Special Weekend, Kara had never shown any interest in me, and the reason she was trying it on with me because Li was not at school over the weekend.

Thankfully 9:30 pm was when we all had to go to bed so I quickly went to my room. When Matthew came in a few moments later, he told me that Kara wanted to know where I had gone; wherein I jokingly told him that if he told her where I was, I’d slap him with a wet fish. He said that he said I’d gone to bed early as I was still feeling a bit off; which was the truth. I got changed into my pajamas and went to the bathroom to fill my juice bottle since the sink in our room was not working.

I was confident that I would not see Kara again until morning as she would have been in the girls’ bedroom section of the girls’ group St. Andrews; and once again I was wrong.

As I was about to enter the bathroom, Kara called out to me as she had been waiting just inside the doorway to the bathroom; wearing her pajamas and dressing gown. Now I was annoyed; I wanted her gone and out of my way so I could refill my juice bottle and go to bed. I remained as polite as I could and told her to get out of the bathroom or I’d call Mr. Grimms and she’d get in major trouble for being in St. Pats bathroom and out of St. Andrews past bedtime.

Kara said that she wanted to talk to me without the fear of being overheard as we’d not had any privacy for the rest of the day. I told Kara that I was still not feeling well and was not really in the mood for her flirting which is when she made her move; she kissed me. It was easy to say that I was caught off guard by this, if I’d not been feeling unwell then I would have seen this coming but since I wasn’t I didn’t. For a few moments, I did not stop the kiss as I was still caught way

off guard.

I broke the kiss and pushed her back, telling her that I had a girlfriend in Li and that I would not cheat on her. She said to me that since Li was not at school for the weekend, we could have some fun without her ever having to find out. She also told me that there was no harm in two people enjoying the company of each other as we would be causing no harm or problems. Once again I pointed out to her that I had a girlfriend; Li and that there was no way in hell that I would ever cheat on her.

And as I walked away to go and squeal on her for being in St. Pats bathroom, she asked me what harm it would do? Li would never find out if neither of us told her and what we did would only be known by the two of us. Kara also pointed out to me once again that what would be the harm in two people who like each other having some fun without Li ever having to find out.

While Kara was a bitch, she was an average-looking girl, at least to me, and I’m embarrassed to admit it but I found myself stealing glances at her chest. Kara had noticed this and said that if I was not attracted to her then I would not be staring at her chest. I was embarrassed that she had caught me staring at her chest and there was no way I could deny it. She then did something else that I did not expect her to; she undid her dressing gown and took it off at which point I almost had a fucking heart attack.

Her chest was small but nice and I had to make sure I didn’t drool. She asked me if I liked what I saw and I remembered just stammering and stuttering at the sight of the half-naked girl. Kara smiled and pointed to my pajama bottoms, where if I was lying down, I would be “pitching a tent”; she said I obviously liked what I saw.

I tried telling her that a half-naked girl would get any straight man aroused but she seemed to know I was trying to cover myself, which is more than can be said for her. Despite not wanting to admit it, I had to admit that Kara did indeed look good which she seemed to know. She stepped closer to me and we kissed; it was then that I was overcome with lust.

I let my hands roam over her almost naked body. I felt a brief pang of guilt over what I was doing; had a girlfriend I loved yet here I was in St. Pats bathroom with Kara. The lust soon erased any guilty feelings I had. A few moments later, we broke apart and Kara suggested that we go back to my room so we could get in bed. I said that sounded like a good idea if not for the fact I shared a room with my best friend Matthew.

I suggested that we could do it right there in the bathroom, to which she said that I “Was very naughty” for suggesting we do it in the bathroom. She pointed out the nearest bath cubicle, stating that we could go in there for more privacy. I agreed and told her that the new bath has not yet been put in and that we’ll have plenty of room. We went into the bathroom stall and found that the new bath had indeed not been installed yet so we did have more room.

By this point, Kara was totally topless and I felt as if I was going to have the aforementioned heart attack. Now, this is where I was overcome with another feeling, not lust or guilt; nerves. I was as nervous as I had ever been up to that point and there is a simple reason for my nervousness can be summed up in two simple yet obvious words: Getting caught.

As you can expect, I did not want to get caught in the bathroom with Kara and get expelled for doing with her what we were about to do. She could tell I was nervous but so was she. As I took off my dressing gown and pajamas, she removed her pajama bottoms and we both stood before each stark bollock naked. We kissed for a few minutes before we laid down on the floor.

Kara used a roll of insulating foam as a pillow; I laid down on top of her and she wrapped her arms and legs around me and then we precoded to have sex. I’ll spare you all the juicy details of exactly what we did but I’ll say this; it was good, very good to be precise. I do not remember how long we long that we lasted but it was around 5 and a half minutes.

After we both climaxed, we just laid there in silence for what seemed like many hours but was in fact just a few minutes. Kara told me that she’d had so much fun if it was not already obvious by what we had just done. I was overcome with a crippling sense of guilt over what we had just done. I had a girlfriend and very much loved Li, yet I had just betrayed her by doing what I have just done with Kara. I told her that I felt guilty over what we had just done, that I loved Li, and that what we just did we never should have done.

She smiled and asked if I’d enjoyed myself to which I said my enjoyment was irrelevant; I had just cheated on my girlfriend with her. Kara smiled at me again and said that what we had done was perfectly normal for people who liked each other and that it was no business of anyone else, including Li. And as much as I hated to admit it, Kara had a point that what we had just done was no business of anyone else, including my girlfriend Li.

We laid there in silence for a few minutes before Kara said we’d better get dressed and get back to our respective bedrooms. I just laid there and watched as Kara got dressed, I watched that lovely little pajama-covered backside of hers swiveled and swayed as she hurried out. I laid there in the bath cubicle for a few more minutes before I got up off the floor and put my pajamas and dressing gown back on. I waited a few minutes before quickly leaving the bathroom and returning to my room.

And so my fellow pandas, there you have it. The story of how I betrayed my girlfriend for a quick screw with another girl. I’m not proud of what I did but the past is the past and it can’t be changed or taken back.