Lisa, Scott and Me Pt. 06

Note to reader.

I hope you've been enjoying this series as much as I've enjoyed writing it.

Part 5 was difficult to top but I've always had a thing for the stern and brutal Headmaster type, and I thought it would be fun to try and bring this fantasy to life.

Hope you enjoy x

My girlfriend had turned me into a cock whore.

Plain and simple.

I lay on the bed, having been fucked senseless by Scott and his friend Peter for the last two hours.

I had their cum oozing out of my bum recovering from another pounding from their two huge dicks.

They loved to share me and Lisa loved to watch me being fucked.

I looked across to see her finishing herself off with a dildo buzzing inside her soaking wet pussy.

We had come a long way in only a few months.

Lisa's confession that her ultimate fantasy was to watch me suck a cock had spiralled into me being fucked and even gang banged as we brought more and more of her fantasies to life.

We had met Scott, a gay escort, online and we had become great friends with him and his friend Peter who was in exactly the same line of business.

Over the last few months Lisa and Scott had planned and plotted lots of sex adventures for me.

The girl who loved to whore out her boyfriend's bottom had become well known and very popular amongst Scott and Peter's circle of friends.

I adored Lisa and loved pleasing her and to be honest I loved my new life being used and abused for my beloved's pleasure.

Lisa loved me and was so grateful to me for going along with her increasingly eventful plans and allowing her to push our boundaries to new levels.

'I love you so much for doing this for me my darling,' she would tell me.

With her and Scott, I knew there would be another adventure around the corner.

Peter had taken a particular shine to me much to Lisa and Scott's amusement.

That afternoon Scott had called to see if we were in as they had something to discuss.

Lisa had excitedly accepted and an hour later they arrived.

We hadn't got to the end of a cup of tea before Peter had started to grope me and the four of us had ended up in the bedroom.

We all cleaned up and gathered back in our kitchen.

'So come on then you two. What did you come to discuss before my boy's gorgeous bottom distracted you?' Lisa asked them.

Peter jumped in.

'We have a very good friend, Derek, who you met at the cocktail party.'

'There was a lot going on that night, but you might remember him,' said Scott, 'about my age, nice looking, bit of a silver fox.'

'Big cock?' laughed Lisa.

All the gay guys there were naked and all had very big dicks.

'Well he is the deputy head at St Winifred's College in town,' said Peter, 'very much hoping to become the Headmaster when the current man retires later this month.'

St Winifred's was a very expensive all girls private college. It was one of those very traditional schools.

'So where do we fit in?' asked Lisa.

'Well the Headmaster at St Winifred's is a chap called Charles Taylor, Sir Charles actually,' said Peter getting to the point.

'We both know him a bit. Pompous old sod but a filthy fucker.'

'Sir Charles is a bit of an old perv and up for all things very naughty. Derek told him about the cocktail party and he's totally obsessed about meeting you,' said Scott.

'Won't stop talking about it,' said Peter.

'Poor old Derek is trying to get the old man's support with the board of governors to get the top job,' said Scott wincing a bit, 'so he's asked for a bit of a favour.'

'Sir Charles wants Derek to set up a private drinks retirement get together in his study at the school,' said Peter, 'it would be us four, Derek and Sir Charles' PA Alison. He doesn't do anything without her apparently. She runs the place, and his life by the sound of it.'

'Derek and Alison want to meet to discuss the possibility,' said Scott. 'They are good friends and are both keen for Derek to get the job.'

'Sounds like fun,' said Lisa unsurprisingly, ' there's something about a naughty old perv.'

'Like me you mean,' laughed Peter.

'Just like you,' laughed Lisa.

'We could take you over to the school tomorrow to meet with them,' suggested Scott.

'They are fretting a bit. They would love it if you said yes.' Peter was pleading a bit.

'Let's go and meet them.' Lisa gripped my hand. 'Ok with you my darling?'

I nodded and smiled knowing that she was excited about another adventure incoming.

The next day Scott and Peter picked us up first thing and drove us into town.

The school was set in amazing grounds and had a long drive leading to the entrance.

It was a Sunday but there was a lot of people around. Sports were being played and the boarders were out and about as it was a sunny day.

Scott parked right outside and as we got out Derek ran over to greet us.

He was very traditionally dressed in a shirt and tie with his teacher's gown draped over it.

'Welcome to St Winifred's. I am so grateful that you agreed to meet with Alison and I. Come through and we can arrange for some coffee.'

Derek ushered us into the school entrance and through to a lounge area where we met Alison.

She really did have the school secretary look about her. Dressed in a tight white blouse and blue skirt, with business heeled shoes. She wore glasses and her hair up and was plainly pretty. I guessed she was in her early 50s like Derek.

She seemed awkwardly embarrassed.

'Hello. Thank you so much for being here,' she said sheepishly and quietly. 'Please come and sit down. I've arranged for some privacy so we won't be disturbed.'

We sat on some sofas and Derek took the lead.

'I'm not sure you remember me from Scott's party? But I definitely remember you. Best party ever Scott,' he said smiling.

'I think we do,' said Lisa. 'There were a lot of guys though.'

'You did very well that night young man,' teased Peter.

'The Headmaster loves things like that and that's why I mentioned it,' said Derek.

'He has asked that for his retirement present he'd like Derek and I to arrange a private get together in his study this Friday evening.' Alison said nervously.

'Believe me. That study has been busy over the years,' said Derek, 'Sir Charles is very naughty man. Alison's PA job is mostly setting up things for his dick to do.'

'He is a very horny old man,' said Alison 'and he's very proud of that dick. He likes to get it out whenever he can.'

'Have you told them?' Derek asked Peter and Scott.

'Not yet,' Peter laughed, 'thought you could bring them up to speed.'

'It's quite the thing,' said Alison.

'What is?' asked Lisa.

'His cock,' said Derek. 'He's huge, and for an older guy he's always hard.'

'It's incredible actually,' agreed Alison. 'The guy is always bloody horny, but Derek's right his penis is extremely large.'

Lisa's attention perked up.

'How exciting, have you all tried it out? Sorry to ask, but I'm intrigued.'

Everyone nodded.

'He's very dominant,' said Alison 'and it's difficult to resist that thing when he wants to use it.'

Derek laughed. 'That's one way of putting it. Alison is often in the firing line, but he loves guys, which is why he was so keen when I told him about Scott's new friends.'

'He's useless with IT so he has me on gay sex sites all the time. He uses his study as a meeting place for all sorts of stuff. I arrange it all for him,' said Alison.

'What's he into?' asked Lisa.

'He's a Headmaster, and loves to play that role,' said Derek.

'The guys I set him up with are always submissive and want to be spanked and dominated. That's his general type.' Alison said. 'He's quite popular. When people see his photos. You know. The size of it.'

'Obviously you can understand why he's so keen on arranging something with you,' said Derek.

'Obviously,' smiled Lisa.

'What do you think?' said Scott, 'we would love to help Derek and his quest to be the new Head at the school.'

'We'd love to help him, but also it could be fun,' said Peter, stroking my thigh.

'Being summoned to the Headmaster's study sounds like fun darling. Don't you think?' Lisa had that glint in her eye again.

'Can we say 6.30 on Friday evening?' asked Derek.

'I can make sure that two of my most trusted head prefects are on guard so that we aren't disturbed for the evening,' Alison offered.

'Sounds like we have a date,' said Peter. 'The headmaster is going to love you.' He squeezed my leg.

'Oh he really will,' smiled Alison, 'you're very much his type.'

'Perfect,' said Lisa, 'we will see you Friday, I'll get my school uniform ready,' she laughed.

She wasn't joking.

As usual Lisa was excited for the event and Scott and Peter were picking us up just after 18.00 ready for our 18.30 rendezvous with the Headmaster.

When she emerged from the bedroom, dressed for the evening she was a sight to behold.

She had on a very tight white blouse, which barely contained her fantastic tits and no bra. She had chosen an extremely short plaid skirt and black stilettos.

'You are actually in school uniform,' I laughed.

'I thought the Headmaster might like it. Don't think these knickers are school approved though,' she lifted her skirt to show me her skimpy white g string, which barely covered her bald snatch.

'I think you should wear a coat over that lot. We'll get arrested if you're seen entering a girls school like that.' I warned her.

'Don't worry baby,' she laughed grabbing her long overcoat.

Scott and Peter arrived promptly and we made our way over to the school.

'I'm reliably informed that the Headmaster is very excited about tonight,' said Scott chuckling.

'According to Alison he hasn't shot his load all week to save himself. Which is unheard of,' teased Peter.

'How exciting,' said Lisa, 'I'm glad I wore my school uniform now,' she undid the coat to show the guys.

'Amazing as always,' laughed Scott.

We pulled up outside the school entrance and walked into the school to be greeted by two girls.

They were obviously seniors, I guessed around 19 years old. Both were in their school uniform.

'Good evening,' said the first girl confidently, 'Alison has asked us to take you up to the Headmaster's study. Can you follow us up please.'

We climbed two flights of stairs before walking down a long corridor, before entering an office which was clearly Alison's.

'Alison will be out to meet us in a minute,' said the other girl, ' would you like to take a seat, and shall I take your coats?'

The guys both laughed as Lisa took off her coat to reveal her outfit and handed it to the girl.

Both girls smiled knowingly as if this kind of thing was not unusual in the slightest.

With that Alison entered the office.

She looked completely different from the other day, in full make up. She wore a smart black cocktail dress, with black tights or stockings with black stilettoes.

'You're here. I'm so glad. Derek and I were worried you might change your mind. Thank you for coming. He's looking forward to meeting you both.' Alison was clearly relieved to see us.

'Lisa you look fab. School uniform? He will be pleased.'

'I thought it was appropriate,' said Lisa 'it's been a while since I was sent to the Headmaster.'

Alison laughed. 'I see you've met Matilda our Head Girl, and Bethany our head prefect. They are completely trustworthy. They often assist me with the Headmaster's shenanigans.'

'I hope they are well rewarded for it,' laughed Scott.

'They have the run of the school. They can pretty much do anything they like, can't you girls?' Alison smiled.

The girls both nodded and smiled.

'They will be on guard for the night so that we'll be undisturbed. They'll bring us drinks when we need them. There's champagne in the fridge girls, can you bring some for the guests please.'

The girls went off as instructed.

'Derek is in with the Headmaster so we'll be called through shortly. I was instructed to give them Viagra with their five o clock cup of tea so you're in for a long night,' Alison smiled at me.

'My boy is nice and horny and ready for anything,' said Lisa kissing me.

It was true I was really horny, knowing I was about to be ravaged in the Headmaster's study was a big turn on.

Peter stoked my leg and his hand found his way up to my hardening cock.

'He's very horny. We have a nice hard dick here already,' he had his hand round it.

With that, Derek appeared, eyes drawn straight to Peter's hand on my cock.

'Goodness you are ready,' he sounded pleased, 'the Headmaster is ready for us to join him. If you'd like to come through.'

Alison and Derek led the way and we followed them into the study.

It was a huge room quite dimly lit. The focal point was the Headmaster's huge mahogany desk in the middle of it.

It was difficult to see much behind that as it was dark, but you could see that the room opened out more.

The Headmaster himself was a surprisingly tall man, around 6'4 and very lean. His cheeks were rosy and he wore black spectacles.

He and Derek were both in teacher clothes, shirt and tie, pin striped trousers with the gown draped over.

'Welcome all, thank you so much for joining us this evening. It's splendid to have you all here.' he spoke in an extremely posh voice.

'Thank you for the invite Headmaster,' said Peter, 'long time no see.'

'It's certainly been a while Peter, hello Scott, you two have brought your new friends to see me.' He took Lisa's hand and kissed it.

'What a pleasure to meet you my dear, Lisa isn't it?'

'That's right. It's lovely to be here,' Lisa shook his hand as he towered over her.

'Derek. You weren't exaggerating,' he said putting his hands on me, what a fine young man,' he was stroking my bottom as he looked me over.

'Thank you for allowing us to have him, my dear,' he said to Lisa still touching me, 'this really will be a pleasure.'

'Right. Can we have him stripped please and then we can sit and sip some champagne and discuss our exciting evening together. Scott and Peter can you do the honours?'

Scott and Peter were more than happy to oblige while the others sat at the Headmaster's desk.

They undressed me and walked me over naked, my 7 inch rock hard dick was at full mast for all to see.

'My goodness. What a fine specimen,' the Headmaster looked me up and down, 'this will be such fun.'

'Did you see that Lisa has worn school uniform for the occasion Headmaster?' asked Derek.

'A splendid effort young lady, and thank you. It's very fetching indeed. Sadly it doesn't meet school guidelines, so it will have to come off I'm afraid.'

'Take it off?' Lisa queried.

'Completely off please,' repeated the Head, 'Alison can you assist. If you're wearing panties you may keep them on for now and of course the sex shoes must stay on.'

Alison helped Lisa off with the blouse and the skirt, leaving her in the skimpy white g string and her high heels.

She looked amazing. Her enormous tits hung beautifully and her fabulous round bum ate the g string.

'Much better,' said the Headmaster, 'now where's that champagne?'

Alison walked over to the study door and called out. 'Beth. Matilda. Champagne now please.'

The two young girls brought in a tray each and served us.

I was sat naked with an erection and Lisa was sat in her panties and heels, but they weren't visibly shocked at all.

'Thank you ladies. We'll need more refreshments in an hour please,' advised Alison.

The Headmaster stood up. 'Girls we require total privacy in this study tonight. Is that understood.'

'Yes Headmaster,' the girls replied in unison.

'Good girls. We'll see you in an hour.'

The headmaster was now holding court at his desk with us sat around him. He sipped his champagne and spoke.

'Lisa, I'm given to understand by Derek that you enjoy watching this dear boy getting fucked by big dicks?'

'Yes Headmaster. That's right. I do.'

'I also understand that we are ok to do pretty much anything we want with him? Is that correct?'

'Correct Headmaster.'

'You probably know already that I like it very rough and I know the other three guys that will be fucking him tonight like the same.'

Scott spoke. 'He's been involved in some pretty serious gang bangs. There's no safe words Headmaster.'

'This whore is very obedient,' said Peter, 'he does as he's told.'

'It can be as extreme as you like Headmaster,' Lisa reassured him, 'he's your whore for the night.'

'That's excellent news. You also know that I like to be in charge. Is everyone clear on that?'

'Yes Headmaster,' everyone said in unison.

He came round to the front of his desk and sat on the end. I could see his dick was hard and it had formed a huge tent in his trousers. He was clearly proud of it.

'Lisa, over on the table behind my desk there is every type of dildo, butt plug and implement to assist you with your pleasure while we use your man. Alison will also be available for anything you want. I can assure you she is very capable in that area. OK Alison?'

'Of course Headmaster.' Alison looked at Lisa and smiled.

'Of course unlike my three colleagues I like boys and girls, so if my cock isn't in use then you may decide to try it for size. I don't think you'll be disappointed. Would you like to see it my dear?'

'I think it may burst out of your trousers if you don't release it soon Headmaster,' giggled Lisa.

The Headmaster unbuttoned and unzipped his trousers and let them drop to the floor and then slowly rolled down his Y fronts allowing his hard dick to spring out.

'Oh goodness,' said Lisa.

It was a beast of a thing. A monster. At least 10 inches and serious thickness. A huge pole of hard meat.

He had some serious pre-cum leaking from the head.

'Alison I'm leaking. Would you like to clean me up please,' he ordered, 'I would take that lovely new dress of yours off if I were you, this will be very messy tonight and you don't want to ruin it.'

'Of course Headmaster,' Alison got up as instructed. 'Lisa could you unzip me please.'

Lisa unzipped her and she dropped the dress to the floor. She had black stockings and suspenders on which looked fantastic with her six inch heels. She had no knickers on at all and her hairless pussy was on full display.

She dropped to her knees in front of the Headmaster and took him in her mouth licking and swallowing his leaking pre-cum from the huge head.

'Bra off as well please Alison,' he ordered.

Alison unclipped her bra with him still in her mouth, to reveal some very impressive tits. Nothing the size of Lisa's but they hung nicely and naturally.

'Thank you Alison. That's clean enough. I haven't ejaculated for a week in anticipation of this event,' he announced, 'bloody thing is drooling for this whore that you've brought me.'

'Derek do you want to undim the back room please and gentlemen I think it's time we disrobed ready for action don't you.'

Derek went across to the light fitting and with a few twists lit up the area at the

back of the study.

At the rear of the study you could now see another room, which was obviously usually shut off. Today it was all open plan and the partitions folded away creating one large study and sex room.

There was a huge bed, a table with sex toys and lube and another table of BDSM equipment, paddles, restraints, blindfold and gags.

It was a serious playroom.

'This area is usually shut off but the girls have been working hard to get everything ready. Tonight this is our fun room,' the Headmaster proudly announced.

The guys quickly got naked and I could see that they were all rock hard and ready to fuck.

The Headmaster had a thin and bony body, but his height and his enormous cock made him look intimidating and powerful.

'Right gentleman. Bring this whore over to my desk and I'm going to begin with a severe spanking. Alison my paddles please,' the Headmaster was going to show me who was in charge.