Lisa, Scott and Me Pt. 07

Dear reader. I took a short break from this series to work on another series, so apologies for the delay in part 7.

As always it's better if you read the previous parts first, but I always try and recap a little for new readers who want to read this as a one off.

The series seems to have a good following and I love reading your comments. Any suggestions are always taken into account.

Enjoy part 7 with the naughty trio, where the Headmaster makes a return.

It was a rainy Wednesday evening and I was face down on Scott's huge bed, recovering from another pounding.

I could feel the two huge loads of cream that had just been pumped into me, dribbling from my ravaged bottom.

I lifted my face from the bed and saw my beloved Lisa spread eagled in a chair, finishing herself off with a dildo, screaming her way to another huge orgasm.

This was what my life had become.

She had turned me into a cock whore, and she loved it.

Just over a year ago my girlfriend, Lisa, had horrified me when she'd confessed to having fantasies about watching me suck a cock.

We had a incredible sex life and I was up for anything, but performing with another guy for her was not on the table.

A few weeks later she announced that she had found Scott, a male escort in his mid 50s, on the internet.

She made appointment initially for a taster session for me and then another session where she could watch.

It drove her crazy.

It made her horny beyond belief and she wanted to keep pushing the boundaries.

It wasn't long before her and Scott, who had become great friends, were having me fucked, spit roasted and gang banged by lots of his big dicked friends.

Lisa and I were in our early 40s, pretty fit regular gym goers.

She was a big girl, not fat as such but voluptuous with big tits and a nice round bum. She was extremely pretty and totally gorgeous. I was smitten with her.

Scott was older than us, in his mid 50s. He was in great shape with a huge 8 inch cock.

The other men that Scott introduced to our sessions tended to be older dominant guys, always very well endowed. Lisa and Scott had decided that was my type, and I guess they were right.

I had become their cock slut. I loved it and they knew it.

Today's session had been with one of Scott's clients, Barry. He had expressed to Scott his desire to try out his dominant side in a three way with a sub.

Scott definitely doesn't do submissive so he had spoken to Lisa about using me for this two hour session.

As always Lisa agreed but on the proviso that she could watch.

Barry was delighted that Scott had been able to procure a willing sub so quickly, and happily agreed for Lisa to attend after Scott explained to him the situation.

I guessed Barry was around Scott's age. He was slightly taller than Scott, around 6'3, and was pretty ripped.

He was another big dicked bully and he had at least 8 inches like Scott but was definitely a bit thicker.

For the last two hours I been used and abused by the pair of them.

I'd been spanked, spit roasted, throat fucked and my poor arsehole had been shagged senseless.

Lisa had wanked herself silly watching these two dominant hunks destroy her man.

They had finished off by unloading their thick spunk into me. First Scott and then Barry happily had sloppy seconds, spilling his cream into me and telling me what a filthy whore I was.

'Wow,' said Barry, 'that was seriously intense. Unbelievable actually. Thanks Scott. I loved having an audience,' he smiled at Lisa.

'Glad you enjoyed it Barry, obviously ticked your fantasy boxes,' laughed Scott. 'I knew you'd love these two.'

'Fuck me,' puffed Lisa, 'I think I came twenty times. You two really gave my baby a seeing to. Are you ok my darling?'

I rolled over onto my back and offered her my 7 inches of rock hard meat. 'I'm horny I pleaded.'

'Oh baby. We've forgotten you. Poor you. Do you want to give it to me?' Lisa climbed onto the bed and took me in her mouth.

'Let me help,' said Barry, joining Lisa on the bed.

Barry gripped my dick and slowly wanked me into Lisa's willing mouth.

I groaned at the pleasure of it and the upcoming release that was long overdue. I was so horny after the fantastic hammering I'd taken.

'Is that good my darling? You've been such a good boy letting the boys use you. Give me your lovely cum baby.' Lisa matched Barry's slow long strokes with her mouth.

'Oh god,' I shouted as my orgasm started to overwhelm me, 'here it comes baby.'

I let myself go and shot an enormous load into her mouth, bucking in Barry's hand.

Lisa loves swallowing my cum and she gulped it down like a pro, licking her lips.

'Goodness darling. Those balls were full. Is that better?'

'That was amazing,' I assured her.

'You're both amazing,' said Barry, finally letting go of my cock.

'They are indeed,' said Scott. 'Shower anyone?'

We all walked naked into Scott's wet room and cleaned up.

Barry dressed and said his goodbyes, pleading with us all for a replay of the day's events very soon.

Lisa and I stayed for a glass of wine and sat in Scott's lounge chatting.

'I had a text from Sir Charles,' announced Scott.

'Sir Charles?' questioned Lisa.

'Sir Charles Taylor. The Headmaster. Well, the retired Headmaster now.'

Sir Charles Taylor, or the Headmaster as he liked to be called was the recently retired Head of St Winifred's, the very expensive private school and college in town.

For his retirement we had done a good turn for one of Scott's friends, Derek and had met the Headmaster in his study one night for a particularly naughty session.

In return Sir Charles had recommended to the school board that Derek, the deputy head at the time, succeed him when he retired.

'You know that invite to his house in the country?' said Scott.

'I remember,' said Lisa. 'He said there were some people he'd like us to meet.'

'He has something planned in just over two week's time and wondered in we are free. Friday 28th I think. He wanted me to check.'

'We can do that. Can't we baby?' Lisa was very eager.

I nodded.

'Shall we call him?' asked Scott.

'Great idea, lets see what the dirty old bastard has up his sleeve,' laughed Lisa.

Scott rang the Head's mobile on speaker.

An almost instant response.

'Scott. I was hoping you'd call. Do you have that naughty pair with you?'

'Hello Headmaster,' Lisa and I said in unison.

'Jolly good. How are you both? I've missed you.'

'Good thanks. How is your retirement?' asked Lisa.

'Very nice thank you Lisa. Still managing to get up to plenty of mischief you'll be pleased to hear,' he chuckled.

'Not surprised to hear that,' laughed Scott, 'how are you getting on without Alison?' he asked.

Alison was the Head's PA at St Winifred's for many years. She used to arrange all his 'adult connections' as she called it.

Despite his age (mid 60s) the Headmaster had a monstrous sexual appetite. He liked both men and women but submissive guys were his absolute favorite.

'My wife helps me find willing participants online nowadays. Olga, my housekeeper is also very helpful. We have regular visitors I'm pleased to say. The house is very secluded and private so it's perfect to be honest.'

'So what did you have in mind for us Headmaster,' asked Lisa excitedly.

'Well, I mentioned to Scott in my text, that I'm having two of my old school governors and their wives over for dinner on the 28th. They both retired at the same time as me and when I told them about my retirement soirée with you, well they have been badgering me about meeting you ever since.'

'Sounds like fun,' said Lisa, 'do they have similar tastes as you Headmaster? And understanding wives?' she laughed.

'Oh my dear. Yes they do indeed. On both counts. Unfortunately for your boy they are built similarly to me. In the trouser department that is,' he laughed away to himself.

The Headmaster was built like a horse. Ten inches of thick meat.

'Wow. I don't think we need much more persuading do we boys?' said Lisa.

'I'm in,' said Scott.

'Darling. Do you fancy an evening in the country?'

'Of course baby,' I said. Like she was going to take no for an answer.

'Splendid. The others will be delighted.' The Headmaster had his party arranged and his special guests in the bag.

'You will keep him nice and horny for me, won't you Lisa,' said the Head.

'Of course, Headmaster.' said Lisa, 'and stretched, by the sound of it.'

'Oh yes dear. My colleagues are big boys and like me they will want things to be extremely rough,' the Head warned.

'I'll keep his bottom plugged and his balls full sir,' said Lisa.

'Good girl. Perhaps a strap on would help to get him ready for his impending punishment,' he suggested.

'I like it,' said Lisa, 'consider it done.'

'I'll text Scott the address immediately. My guests will be having an early supper so that we are ready for you around 8.00 on the night. Is that Ok?'

'Perfect,' said Scott and Lisa together.

Another adventure was booked. Lisa was beyond excited.

Lisa was good to her word and after a few days fucking like rabbits as usual, 10 days before the big event I was on a cum ban.

'I want you lovely and horny for the Headmaster and his guests baby.'

She was on heat though, and I was eating her wonderfully willing cunt, morning, noon and night.

My hole was plugged with butt plugs of significant sizes to make sure I was ready for the big dicks coming my way.

She had ordered a strap on the minute we'd got home from speaking to the Headmaster at Scott's.

At most bedtimes she'd emerge from the bathroom with it on and a bottle of lube in her hand.

'Come on baby. Lets have you on all fours ready for my big dick. You'll thank me for it later. I need you ready for cock.'

As the big day approached she was more excited than I'd ever seen her. We had done some pretty crazy things in the past year since meeting Scott, but the Headmaster was another level. He was a dirty old man, but a brutal fucker with an ridiculously large cock.

He had fucked us both in his study the night of his retirement and if he had two more like him with 'understanding wives' who were going to be in attendance, it sounded like it could be very interesting indeed.

On the day we were all deliberating what to wear. Scott suggested we go smart and we both wore suits without ties and Lisa put on a tight fitting black dress with stockings and suspenders underneath.

She finished the outfit off with some black patent stilettos and some bright red lipstick.

'I'm posh but a little slutty,' she announced as she walked into the living room where Scott and I were waiting to leave.

She looked fantastic. The dress showed off her huge tits brilliantly and her beautiful round bum looked amazing.

She kissed me.

'Are you ok baby? I'm so looking forward to this but I'm conscious that these guys are dying to fuck you and it could be a bit rough.'

'I'm fine darling,' I kissed her back, 'to be honest I'm so horny, I'm up for anything.'

'Oh god, me too,' she jumped up, 'lets get going boys, I can't wait any longer.'

Scott drove us out of town towards the Headmaster's house which was about an hour away.

'I've been talking to Derek and it seems that this country house is more like a country estate. A family heirloom apparently. I think Sir Charles Taylor lives in a bit of a stately home,' said Scott.

'How exciting,' said Lisa, 'we'll be with aristocracy.'

Scott's sat nav took us to a drive with some iron gates that were open.

There was a sign for 'Longfleet Manor'.

We all gasped as we drove up the driveway to the house through the grounds. It was vast plot of land with the main house set in woodland at the end of the drive.

We parked up outside.

'My god,' said Lisa, 'this is some place. The Headmaster is sat on some serious real estate here.'

Scott walked up to the door and rang the bell.

It took a while but the door eventually opened and we were greeted by a stern looking lady. She was wearing a pinafore type work dress that looked like uniform with white trainer shoes. I guessed she was in her mid 40s. She had short hair, and a fuller figure. She spoke in an Eastern European accent.

'Good evening. I'm Olga. I am housekeeper. Sir Charles is expecting you. Please follow me.'

She ushered us in and closed the door behind us. She beckoned us to follow her and spoke as she walked.

'They are in drawing room having brandy. Please follow and I take you to them.'

We walked past the huge staircase to the left and down a long hallway. The house was really impressive, lots of art on the walls and antiques dotted about the place.

Olga walked fast and we struggled to keep up. Lisa tottered on her heels holding on to my hand.

Olga stopped at the doorway to the drawing room and announced our arrival.

'Sir Charles, your guests are here. Shall I bring them through?'

Olga beckoned us into a huge room, elaborately decorated, with an open fire at the front of it. Sir Charles and his guests were sat on sofas near to the fire.

The men wore dinner suits with black tie and the ladies were in black, very expensive looking evening dresses. They all got up as we entered and the Headmaster walked over to greet us.

His slender, bony body actually suited the tuxedo. He did look every bit the retired Headmaster. His thinning grey hair was greased back, and his spectacles rested on his nose across his rosy cheeks.

'Welcome. So good to see you all. Thank you for coming tonight.' He hugged Lisa and kissed her on each cheek, before shaking hands with Scott and I.

'Thanks for inviting us,' said Lisa, 'this must be your wife?'

'Where are my manners. Let me do the introductions. This is Sarah my long suffering wife,' he joked.

Sarah was surprisingly pretty, given that the Head wasn't much to look at. Probably 10 years his junior, she was very glamorous. A slender lady, she looked great in her black dress which fitted tightly showing off some pert breasts that had a diamond necklace between them.

'Welcome to you all. So nice of you to join us. Charles has been so looking forward to seeing you again,' Sarah spoke in a very posh voice, as expected for the lady of the manor.

The Headmaster continued the introductions.

'These are our very good friends, Andrew and his wife Felicity, and Jeremy and his wife Helen.

They all waved and said a multitude of welcomes.

Andrew was a tall slender man like the Head, around 6'4. He had a good head of grey hair and was quite the 'silver fox'. His wife Felicity was slightly bigger than Sarah, you could immediately see that she had large breasts and again she was much younger than her husband.

Jeremy was much shorter than the other two, but very a very stocky, powerful looking guy. His grey hair was cut short and he had a tidy beard. Again he was clearly mid 60s like the other two. His wife Helen was slightly taller than him, she was a much bigger lady, both breasts and bottom were very big and she filled her dress nicely. I guessed she might be the youngest of the three ladies.

You could tell immediately that they were all from the upper classes. Their demeanor and accents were all very similar, but friendly and welcoming all the same.

The sofas in the living room all faced each other and the Head gestured for us to sit down. There was a glass table in the middle with their brandies on, and I spotted some Viagra packets.

'The boys are having after dinner brandy and Viagra,' laughed Sarah. 'I'll get Olga to arrange some Champagne for us.'

Olga came into the room like she'd been waiting to be called.

'Yes Sir. Madam. Can I help?'

'Are the waitresses still here Olga?' asked the Head.

'Yes Sir. I ask them to stay on late today. Natasha. Sofia. Here now please,' she shouted.

Two girls wandered in. They wore the same uniform as Olga, both looked to be in their mid 20s.

'Could you ladies bring some champagne for the ladies and our new guests please,' he instructed.

'Yes sir,' they said in unison, and wandered off.

'Will that be all for the moment Sir?' asked Olga. 'I will make sure that the room is ready for you. When will you be going through?'

'Oh we'll have some drinks and chat for a while first before the fun starts, thank you Olga. There is one more thing actually.'

'Of course sir, what must I do.'

'Could you maybe ask your girls to lose the uniforms? To get everyone nicely in the mood.'

'You want them in underwear or naked?'

'Well. Naked if it's possible Olga.'

'I ask,' said Olga and left the room like he'd asked her to do the washing up.

'You are naughty Charlie,' said Helen adjusting her large breasts a little.

'I'm sure they won't mind indulging us,' said the Head laughing. 'I'm sure Lisa won't mind.'

'Of course not Headmaster,' she laughed, 'I would expect nothing else.'

'So Lisa,' said Sarah, 'I'm intrigued. How long have you been letting dirty old men like these use your man? He's a fine specimen. I'm surprised you want to share him.'

Lisa giggled. 'He's gorgeous isn't he. You wait until you see him naked. I had a fantasy to see him with another guy and then I found Scott. He helped me bring the fantasy to life. After that it's got a bit crazy. Boundaries have been adjusted.'

'I've heard there are no boundaries,' laughed Andrew.

Jeremy adjusted his crotch. 'Charles said he was an amazing find. He wasn't exaggerating.'

'You won't be disappointed,' said Scott.

With that Natasha and Sofia walked in with the champagne. They were naked as per the request. They had left their white trainers on.

'Thank you ladies. This is a treat,' said the Headmaster.

The girls served the drinks. The men made sure they got a feel as they did it.

'Can we see?' asked Felicity. 'Can we see him naked Lisa?'

'Darling. Are you OK to undress? I think you're quite popular with our new friends,' Lisa grabbed my hand and gave me a look.

I stood up and saw Olga approaching with a hanger for my suit.

I handed her my jacket and started to undress.

The naked waitresses didn't seem to be phased. I guess working here they saw plenty of sights.

Olga took my jacket, trousers and shirt and I just stood in my Calvin Klein trunks. I was incredibly horny and realized that I was already rock hard.

'Pants too baby,' Lisa gestured for me to take them off so I stepped out of them to leave myself naked in the middle of the room, all eyes on me.

My 7 inch dick was as hard as it could possibly be and exposed to the group. I felt my face go red as everyone ogled.

'Goodness,' said Andrew, 'Charles you really have excelled yourself this time.'

'My dear,' the Head said to Lisa, 'you have kept him horny for us. Well done.'

'Those balls are huge,' said Helen. 'Can I have closer look and maybe touch,' she asked Lisa.

'Go on baby,' Lisa ushered me over to where Helen sat with Jeremy.

I stood in front of them and Helen took my cock in one hand and cupped me in the other.

She squeezed are caressed my balls.

'My god. They are huge. They must full. Goodness he's leaking,' she exclaimed, as she watched pre cum drip from the tip of my erection.'

'Why don't you clean him up darling?' said Jeremy to his wife.

She looked up at Lisa, almost asking for permission. Lisa nodded and Helen slipped down onto her knees in front of me and softly licked the tip clean of the leaking fluid, before sliding the whole dick into her mouth.

I groaned. Her mouth felt amazing and her huge tits were virtually on display as the bulged in her dress.

'Careful Helen. He's ready to blow,' warned the Head, 'we don't want any accidents,' he laughed.

She took me out of her mouth, swallowing the pre cum and licking her lips.

'Sorry Charlie. Getting carried away,' she giggled.

'Dirty bitch,' teased Felicity, 'stop hogging him and send him over.'