Part One.
I had worked at Stonecliffe School for 3 years as an assistant caretaker. My boss was an old guy who had worked there forever. He was nearing retirement and I was due to replace him soon and I was very happy about this. I had always enjoyed the job even though the pay was lousy, partly because there was never much to do. But mainly because Stonecliffe was a Private All Girls School! And it was stuck out in the country which meant all the students and all the staff lived on the grounds in various houses and dormitories. They provided me with a small flat but the Head Caretaker job came with a house and I hoped to be in it pretty soon.
Every day I would see around 200 teenage girls of all types. They ranged from young and innocent, all the way up to young and filthy! In my 3 years there I must have been propositioned a hundred times. In my defence I am only 26, not bad looking and in pretty good shape. It’s a cliche but when you do some gardening in a t-shirt on a hot day, it becomes a spectator sport! Including all sorts of shouts and whistles. But I’ve always been a good boy. I was always firm but friendly in my declines, leaving the odd girl in tears and always leaving me with a raging hard on! I’m a red blooded male and turning down these hot young girls was getting harder to do.
Pretty soon things progressed for me and I became Head Caretaker. I moved into my new house and even started a relationship with a teacher from the school. She was called Julie and she was a science teacher. But she was no geek. She was 32 and she was tall and elegant with a great body and a gorgeous face. She was also pretty filthy in bed and we got up to all sorts. Because all teachers lived on the grounds, we were never far away from each other and explored the whole school finding new places to have sex.
One evening we were taking a walk looking for a new spot to fuck. As we passed round the back of a dorm we heard some girls chatting loudly followed by a scream and a girl pleading. We approached the window to see what was happening and through a crack in the curtain we could see 4 girls in a small bedroom. One of the girls was on her back, her arms were pinned down by two of the other girls and she was trying to get free. The final girl was obviously the leader and was giving instructions to the two others. I recognised the girls in charge as being final year students but not the girl being restrained. Julie was in front of me, pressed up to the window, engrossed in what was happening. I wasn’t sure if she would react and maybe go into the room to help out the girl in trouble. She was off duty but still their teacher. She didn’t move so I pressed up behind her for a better look.
The ringleader was a girl called Sarah. She was a final year student and was hugely popular with everyone, teachers and students, and her popularity meant she was the also the ‘Head Girl’. She was also red-hot. Squeezed into her school uniform she was 18 years and 5’9″ of future supermodel material. I had watched her closely over a few years and had several wanks thinking of her but she had never approached me so I never got to know the disappointment of having to refuse her! Her two friends were also beautiful and sexy but not quite as smoking hot as Sarah and so they took there place on the pecking order as her lieutenants. To my shame I didn’t even know there names. They were holding down the unknown girl with real force waiting for the next instruction.
Sarah positioned herself between the new girls legs and pushed them apart. She spoke to her helpers who started to pull off the blouse and bra of the helpless girl. Sarah pulled off her skirt leaving just a pair of white pants covering a clearly frightened girl. Julie and I had stood watching for a few minutes in silence when I felt a hand move towards my crotch. I instinctively moved my own hand onto Julie’s thigh and started to slide it towards her pussy. She pressed back into me and whispered that this was some kind of initiation and the new girl was Emma who had only joined the school a week ago. Julie slid a hand into my pants and quickly found my cock as I pushed aside her knickers. Her pussy was already wet as my fingers slide over her slit and teased her clit. We slowly masturbated each other waiting for the show inside to really kick off.
Inside, Sarah had the new girl, Emma at her mercy. As her friends held Emma down, covering her mouth to stifle her screams, Sarah slid a hand inside her panties and soon located her target. She slowly rubbed Emma’s pussy as her friends laughed and groped the new girls body. A tiny pair of panties were soon ripped off by Sarah and she joined in the laughter as she fingered Emma’s clit. This was obviously Emma’s first lesbian experience and I wondered if it was her first anything with anybody. She looked scared but it wasn’t long before she had stopped writhing about and had closed her eyes. Her complaints had stopped and when one of the helpers moved her hand from her mouth and replaced it with her lips, Emma reached forward and joined in the kiss. Sarah moved down the bed and replaced her fingers with her tongue bringing a loud groan from Emma.
Outside, I had been playing with Julie’s pussy, enjoying the feel of her hand as the sight inside unfolded. I had been surprised when Julie didn’t stop what was happening and was even more surprised when she started to wank me. My response to her touch was automatic but I had been concentrating on the action inside and almost forgot I was being played with! I moved things on by unbuckling my trousers and pulling down my pants. Julie slid off her knickers and I moved closer to her and found her wet pussy with my tip. I made sure we both had a good view of the action and slid my hard cock into her. We fucked slowly and quietly, we had been undetected so far and wanted to saviour the action.
Back inside and the action had notched up. Sarah had her face buried in Emma’s pussy. From our position we could only see Sarah’s hair and head moving about but we had a great view Emma and I could see why they had chosen her for an initiation. She was cute rather than gorgeous but you could tell she had something. I was immediately attracted to her and was watching her face closely as her new friends introduced themselves. Sarah was obviously doing a good job because Emma’s hand was in her hair pushing her face down. The helpers were kissing each other and kissing Emma and nipples were being licked in a three-way frenzy. It was the hottest action I had ever seen and my speed increased as I continued fucking Julie. My fingers reached round and found her clit and I started rubbing it as the action inside started to reach a climax. Our timing was perfect, inside Emma let out a loud moan as the first wave of her orgasm hit her. Sarah’s licking was frenzied and the helpers had a breast each and were sucking Emma’s hard nipples. A second later and Julie let out a quieter groan and I felt her pussy contract as her orgasm started. This was my cue and I was bang on time too. I kept my eyes on Emma as I came inside Julie, each thrust timed with Julie’s pussy tightening. Inside, Emma was mid orgasm and was in ecstasy. Her head was thrown back, leaving her whole body exposed to her three sexy new friends. They continued to tongue and rub Emma till her orgasm subsided and she lay still, trying to recover herself.
Outside, Julie and I had started to get redressed, I was still in shock at the nights events and looked thru the window as our viewing was finishing. Julie joined me at the window and we were just about to head off when I saw something. One of the helpers had produced a strap-on dildo from her bag and was handing it to Sarah. Once again Emma’s face started to look worried and Julie noticed it too. She pressed hard up to the window to hear what was being said. My hearing has always been bad so I left it to her. I watched as Sarah waved the toy in Emma’s face, they were talking but it was mostly Sarah and she looked back in bossy bitch mode. She put the toy in her own mouth demonstrating her excellent cock sucking technique before putting it back in the bag. Then all the girls got up and Emma was helped back into her clothes. Julie and I left the scene and heading back to my house.
Back home Julie told me what she had heard the girls say at the end. Sarah had told Emma that tonight was the warm up and next week she would be using the toy on her. Emma had confessed that she was a virgin but was willing to try and this had pleased Sarah more and she had sucked the toy telling Emma she would be doing this too. Julie told me she was not happy with what had happened and was going to have a word with the girls tomorrow. She said fair enough an initiation was something many people had to do but Emma had done hers and now it was being unfairly extended. She said she planned on taking action.
The following evening when Julie arrived at mine she was very excited. She told me that she had spoken to Sarah and Emma separately and had explained what she had seen. I’m pretty sure she left out the part about us fucking while watching! She had threatened them with expulsion and they had both been very sorry, promising to do anything to avoid trouble with the school. Julie said this had led to the next thing and I would be pleasantly surprised before the end of the week. She told me she couldn’t say anything else but I would find out. We spent the evening fucking and my mind was racing, thinking about what my surprise might be.
The following evening I got the first part of my surprise. I wasn’t expecting to see Julie because she was doing some after school tuition and so I had a quite night planned. At about 7 I heard a knock on my door so went to answer it. I opened it and was greeted by the sight of Sarah, the Head Girl and ringleader from last night, who quickly pushed thru the door and closed it behind her. She knew she wasn’t supposed to be at my house and didn’t want to get spotted. As I said before, Sarah was absolutely gorgeous. Her mother had been a model in her youth and she had inherited her good looks and was destined for greater things. She was wearing her school uniform but the blouse was a few sizes too small and the skirt barely covered her panties. She was a sight to behold and I had to catch my breath before asking her what she was doing. She looked very shy as she told me that Julie had sent her to me as a punishment for the other night. I pretended not to know what she meant and she shyly said she had been caught being naughty with another student. All the time she looked very embarrassed and her cheeks were flushed red. I asked her what she had done and she smiled at me, saying she couldn’t say anything about it.
I was a little confused by the events but that changed quickly when she dropped to her knees and started to unbutton my jeans. I tried to pull away from her but she pulled me back and told me I had to let her carry out her orders. I figured this was all part of Julie’s surprise so I let her continue. She dropped my trousers and then started to rub my cock through my pants, it was hard in seconds as her small hands gently worked their magic. In no time she had pulled my pants down and she started to kiss and lick my cock like a professional. I put my hand on her head and encouraged her to take more which she did. It was obviously not the first time she had sucked a cock and pretty soon was slurping away like her life depended on it.
Sarah continued to suck me expertly and I could feel the first stirrings on my orgasm. She had done a great job but I didn’t want to come yet so I stopped her and lifted her to her feet before kissing her passionately. She initially responded but then pulled away telling me she was only supposed to suck me off. Now it was my turn to be her boss. I kissed her again and started to grope her breasts which she seemed to enjoy. I told her she was here to pleasure me and if she disappointed me I would tell Julie and she would expel Sarah in an instant. She must have believed me because she leant in to kiss me and she started to wank my cock again. My hands worked their way down her body and soon found her panties which were already getting damp from her excitement. All this time we had been in my kitchen so I grabbed Sarah’s hand and dragged her upstairs before throwing her on my bed.
In seconds I had stripped Sarah and was using my tongue on her nipples, exploring her beautiful toned body with my hands and mouth. My tongue soon found her clit and I felt her body shake as I teased it with my lips. I alternated between licking her clit and her wet slit. Julie had a nice pussy but the sweet taste of Sarah’s was something else. Her juices were running down my chin as she pushed down onto my face. She let out a squeal as her orgasm hit and I played with her clit keeping her orgasm going. I climbed up her body and she kissed and licked her own juices off my face. My cock was still hard and I eased it to her pussy lips keeping my eyes locked with hers. A cheeky grin ran over her mouth and I took this a my cue to enter her. I pushed my hips firmly and Sarah let out a cry. She was no virgin but she was very tight and I doubt she had taken a cock as big as mine before.
I knew that this was supposed to be a punishment for Sarah so decided not to let her get away easily. I fucked her hard, loving the feeling of her tight pussy. I held her arms above her head and sucked on her nipples as I slammed into her pussy. The tempo was increasing and Sarah was struggling to keep up with my speed. I used my body to hold her down firmly and increased my speed, I was getting into my rhythm and could feel my balls slapping her arse with each hard thrust. Sarah was lying back with her face twisted in a mix of agony and ecstasy, her mouth was open and she was groaning loudly but she never complained. After a few minutes I lifted her up and turned her around. Her perfect ass was now in the air and she spread her knees to give me better access. I pushed her head into the pillow and entered her again. I started slowly with long thrusts but pretty soon I was pounding away with all my might. This time my balls were hitting her clit and she responded with a moan each time. I was getting close to coming and so I pulled out and rolled Sarah over. I put her hands on my cock and she got the idea. She used her soft hands to finish me off and I came heavily, shooting several spurts over her heaving breasts. I collapsed on the bed as Sarah ran to the bathroom to tidy herself off. She came back in smiling and laid on top of me holding me tight and sighing with pleasure. I lay holding her still in shock at what had happened. I quickly regained my composure and told Sarah to get dressed as it was getting late and she shouldn’t even be here. We got dressed and went downstairs. Sarah started to leave but turned back and kissed me on the lips before thanking me and quietly leaving.
After Sarah had left I sat for a while trying to get my head together. Julie had obviously sent Sarah for my pleasure but I don’t think I was supposed to fuck her. But my girlfriend had sent another girl to pleasure me and this meant she might send Emma, last nights victim!, to pleasure me as her punishment. The following day I saw Julie and she had a huge smile. She asked me if had enjoyed my surprise and did I have enough energy left for her! Well I always had time for Julie and soon we were fucking frantically with the image of Sarah burning in my head. All was quite for a few days and I wondered if my next surprise was coming at all. Sex with Sarah had been amazing but I was hoping to get my hands (and mouth and cock!) on the virgin Emma but as the weekend loomed it looked like my chance had gone because most of the older girls went back home for the weekend.
Would I get my chance? Find out in part 2