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By *wishes OP Man
6 weeks ago
Sheffield/Chesterfield area |
The footsteps in the hallway told me that the Colonel was coming to join us. They made their way across the sitting room and paused outside the door as Jim said sternly "Wait there until I tell you to come in Anne".
What the heck! Who the hell was Anne? Jim went and sat behind the desk and pointed to one of the armchairs. I sat back in it, and I still remember the old leather creaking as I leaned back and tried to make myself invisible in it.
"Come on then Anne. We're ready for you now"
Into the room stepped an elderly lady with blonde hair, in a long loose summer dress. She was wearing white mid height heals and carried a matching bag on her shoulder.
"So do you like how I look for you today?" spoke the familiar voice of the Colonel.
"You look very lovely. I hope what you've got on underneath is as nice too" Jim answered.
I was well past shock by this point and fully immersed in what I had been allowed to become a part of. In fact my cock was already made stiff by the scenario and at the thought of what might happen next.
"Come and stand in front of the lad and give him a good look then" Anne complied.
"Now give him a twirl" she twirled in front of me, her dress floating up and out a little as she did it.
"Did you bring the bottle?"
"Yes James"
"Get it out then and after you've used it give it to the boy"
"Yes James" she said again.
Anne reached into her white bag and took out the small brown bottle, then opened it and inhaled deeply and repeatedly. She then passed it to me quickly and moved to the desk to lean on it with both hands. I took a deep lung full and watched with horny focus and wonderment at the scene in front.
Jim ordered sharply "Get that dress off and show him what you're wearing."
The dress hit the floor to reveal a tight '50s style girdle and stockings underneath with the now very familiar cock sticking out in front. I was so horny at the mixture of sensations that I was feeling ready for anything.
"This young lad got fucked by the Colonel yesterday. Today he's going to punish you for it Anne and take his revenge."
"Get yourself bent over this and don't move unless told to"
"Yes James" replied Anne as she bent over the huge desk.
"Come on lad. Give her what she needs"
Jim passed me the cane. I stood up not really having any idea how to do the next bit, and gave Anne a few lighthearted taps on her girdle wrapped arse.
"She can take a lot more than that boy, and I'm sure you can give it. Put your arm into it."
I paused, hesitated, the weapon hovering in the air at shoulder height....then let go with a sudden swish of the cane. It whistled through the air and struck Anne's arse with real force.
She squealed, gasped and sighed in one breath.
"Again boy. Only stop when you've had enough."
Anne moaned slightly at his words, and I could sense the fearful pleasure she was experiencing.
I let go again... and again... and again. Each blow accompanied by gasps and squeals from my subject.
Jim was feeding her from the bottle and had taken out his cock, stroking it while sitting back in his chair, commanding the scene.
After a minute or so of using the cane I was starting to become anxious about the distress I was causing Anne. Even though her bum was largely covered by the girdle the repeated strikes of the cane had left some growing and intensely red marks.
"Don't worry boy. It's nothing new to her. She needs it and is at her happiest when let her have it."
Is barely spoken a word since I had entered the house and realised that both Anne and I were completely under Jim's control.
"Time to join her now boy."
I must have looked terrified.
"This isn't for you though" he said pointing at the cane still in my hand.
"This is". He gripped his cock tightly and made sure I got the message.
I stood up and moved quickly to the desk, bending over it.
"Ah....you're keen today aren't you" he said noticing the absence of dawdling uncertainty I'd shown the previous day.
He stood up and walked around the desk to stand behind us both. I felt his hands roughly reach around my front, undoing my belt and shorts, and forcefully pull them down and take them off me.
"I'm going to get you ready then you are going to fuck Anne"
"OK Jim"
"Spread your legs for me"
I did it willingly now, eager and keen for being whatever he wanted me to be, and doing whatever he wanted me to do.
Suddenly a wet hand started feeling and probing my, lubing me, getting me loose. I spread my legs further for him.
"You are a good lad. I knew you would be. We've had our eye on you for a long time.
Who knew how easy it would be to finally have you like this though."
"Take a deep breath and hold it" the bottle was under my nose again.
A sudden swish and a sharp scream from Anne told me the cane was back in play again.
And another.
And another.
And another.
Far more forceful and hurtful than mine had been.
"Shut up bitch and stop whining"
"Here boy, put this on her arse" he said, passing me a small bottle of lube.
I did as I was told.
"Now get behind and fuck her"
My head was still spinning from the vapours. I was desperate for sex so was very happy to finally get the chance to fuck someone.
My teenage hunger for sex, the scenario, the vapours took over.
I got behind Anne and placed my cock at her hole, sliding deeply into her in one or two smooth thrusts.
Anne gasped and moaned as my cock filled her completely.
"That made her sound like she does when the truncheon is in her." Jim said laughing.
"Just fuck her now boy. Don't hold back."
I got stuck in to my work, needing no encouragement at all.
Pounding my young cock in and out of Anne, enjoying fucking like only a teenager can.
Then the bottle was back under my nose.
"Breath deep and hold it"
He was behind me now, and through the haze of the vapours I could feel the soft head of his cock at my well prepared arse.
He eased it in.
Even though I'd been fucked once before, it was two years earlier, and not by something this big. It hurt. I flinched and tried to pull away but was trapped between the two of them.
"Breathe out lad" he said.
As I did he forced his way into me pushing me deep into Anne.
Suddenly the pain and resistance disappeared as the vapours, lube and relaxation allowed him in.
The next few minutes was a frenzy of fucking, moans and gasps as we all lost ourselves in a lustful tangle of need and sex.
My hole was clenched tightly on Jim's cock as he used me.
"I should have had you a long time ago" he said.
"Definitely worth the wait though"
I could feel my orgasm coming and just let it happen. Jim heard and felt me coming and dumped his cum up me in several huge jerks, crushing me against Anne and driving my cock as far up her as possible.
We separated in an exhausted panting mess, all looking at each other. The tension broke with a spontaneous shared moment of laughter and _miles.
Jim stepped across to me and pulled me to him. He kissed me passionately then turned and did the same to Anne.
Then it was time to get cleaned up and tidy up the scene of the fun time we'd just shared.
I wish there was a happy ending to my time with these two remarkable men. Sadly not though.
30 minutes later I was back home in a massive argument with my Dad. By the end of the day I was homeless and hitch hiking to go and stay with my mum. Although I did return to the village again several years later, I never saw or heard from either of the two gents that I'd shared a few beautiful weeks with.
It does sit in a suite of my favourite memories though and I still feel blessed to have been able to experience it all.
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This sounds good. 
