Carol's Cravings; Paul's Pleasures

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"He'll get there, don't worry," I replied. "Remind me to take you to our local fetish club the next time you come for a play date. They've got a glory hole there. It's where Richard learned to suck cock to completion."

I pulled Richard's arse cheeks apart and nestled my cock up against his star shaped pucker.

"Ease your way in gently at first," I advised, bucking my hips so that the tip of my cock penetrated his arse. As I pushed gently, Richard's bum hole expanded and swallowed up my thick rubber cock before closing around it as my thighs came into contact with his arse cheeks.

"Right, I'm in deep now," I explained. "Although you can't see it, obviously, my cock is now pressing on his prostate."

I began to saw in and out of Richard's arse.

"As I fuck him, my cock stimulates his prostate " I continued with my tutorial. "I'll carry on for a few minutes, and then when he's gaping, we'll use our fingers to milk him."

Carol watched, fascinated as I continued to peg Richard whilst he sucked on Paul's cock. After a few minutes I pulled out and my cock glistened with Richard's bum juice.

"Ever done arse to mouth?" I asked Carol with a grin. Wordlessly, she shook her head, but dropped to her knees obediently. She took my cock in her mouth expertly, and began to clean it up. I patted her head affectionately, and eased her to her feet.

"Good girl," I whispered, giving her a deep, open mouth kiss. "I love arse to mouth myself!"

I took hold of her hand and put her index finger inside Richard's gaping arsehole. Then I slid my own finger in beside hers.

"Here we go," I said, and together we sought out Richard' prostate.

"Feel that?" I asked and Carol nodded.

"That's what we're looking for," I told her. We make him cum by doing this."

I knew she could feel my finger doing a 'come here' beckoning motion, and I nodded my approval as I felt Carol's finger begin to copy my movement.

"This is my preferred method of milking him," I continued. "Four times a year, I use different methods. For my birthday, and for his birthday, I use my hand and I wank him, but always to a ruined orgasm. He' duty bound to tell me when he' about to cum, and I let his cock go. He does cum, of course, but it is without continued stimulation."

"On our wedding anniversary, I use my mouth to make him cum, but I always kiss him straight away afterwards and he gets his cum straight back, and he has to swallow it, of course."

"That's only three times," Carol said in a puzzled voice. "I thought you said that you milked him differently on four occasions?"

I winked at her and smiled.

"I give him a real treat on Christmas Day," I replied. "We always have Christmas pudding after our Christmas lunch. I take mine with brandy sauce. Richard gets his with homemade white sauce, which I extract from him by using one of my vibrators on his cock and balls. It never fails to make him cum, and his homemade sauce adds a lot of flavour to his pudding."

Carol looked at me in what I took to be admiration.

"You are such an inventive woman," she said. "I think I'm going to try every one of your methods, as well as this traditional method, of course."

"Speaking of which," I replied, "this one is going to cum in double quick time with both of us stimulating his prostate. I'll finish him off, if you can get his cum glass out of my shoulder bag, please."

Carol withdrew her finger out of Richard's arse and scrabbled around in my bag, eventually coming up with a small glass tumbler.

"Is this what you were looking for?" she asked, and I nodded.

"Hold it underneath his cock," I instructed her. "Don't worry about spilling any. He oozes rather than spurts when I milk him like this. It comes out slowly rather than shooting out everywhere. Ah! There she blows! Look! He's starting to cum."

Carol watched in fascination as I milked every last drop of cum out of my cuckold. It took a good ten minutes to drain him, and she caught every last drop in his cum glass.

When I was satisfied that Richard's balls were completely empty, I withdrew my finger and Richard stood up. Like me, he knew the next step in the operation. Carol, however, did not.

"But he's still hard," she said in amazement. "You've milked all that cum out of him, and his cock hasn't gone down at all. In my admittedly limited experience, whenever Paul has cum after fucking me, his cock goes all soft and floppy and is, to all intent and purpose, useless for a couple of hours."

I smiled at my naive pupil Hot Wife.

"Milking isn't the same as fucking," I explained. "It's the cuckold's prostate, not his cock that gets the stimulation. What we've done here is to manually, or digitally, to be perfectly correct, extract Richard's cum whilst ignoring his cock. He's been drained, but he's had no cock stimulation. I imagine it leaves the cuckold feeling very frustrated. Am I right?"

This last question was directed at Richard.

"It used to leave me extremely frustrated when you first started milking me all those years ago," Richard admitted, "but it has been so long since my cock was inside your cunt that the feeling I get these days is one of a release of tension in my balls. They are not so tender now, and they are already starting to look more normal."

"I'd say they were tiny, rather than normal," Carol giggled and Richard blushed. I'd had enough of this explanation lark. I handed him his cum glass.

"Re-cycle time," I told him. "You know I hate waste."

Richard took the glass from me and tipped the contents into his mouth. He savoured the contents and then swallowed before sticking his tongue out and licking the glass clean. Carol watched, open mouthed.

"Oh, fuck!" she breathed in an awe struck voice, "that's something Paul is going to be taught to do. It's so hot, seeing your cuckold swallow his own cum!"

I grinned and nodded at Carol's strap on cock, which was sticking out obscenely from her harness.

"It's time, I think," I said. "Where do you keep your lube?"

"It's in the drawer of that bedside table," replied Carol, nodding at the appropriate piece of furniture. I opened the drawer and took out a brand new tube of lube which I opened, squirting a goodly dollop onto my fingers. I handed the tube to Richard.

"Lube Ms. Carol's cock," I instructed, "and do a good job. She doesn't want to rip her cuckold's arsehole to shreds!"

Whilst Richard set to to lube up Carol's cock, I rubbed the dollop of lube on my fingers all around Paul's tight, virgin pucker. Gently, I eased my index finger into his arse, coating the inner walls of his bum with the slick, slippery lube. Paul moaned as he felt my finger penetrate him, but I ignored that and continued to spread my lube inside his arsehole.

My finger found his prostate and I rubbed it a couple of times. To my experienced eye, his cock reacted to this internal stimulation, and twitched a couple of times. I was satisfied that Carol would be able to locate his prostate easily enough when she had finished pegging him.

I looked over at where she was standing, and saw she was ready for action. Quickly, I released the cuffs holding Paul's ankles and I hauled his legs upwards and pulled them apart. Holding them in position, I told Carol that it was time to take her cuckold's arse cherry.

"Help Ms. Carol, cucky," I instructed Richard. "Line her cock up with her cuckold's arsehole."

As Carol nervously shuffled into position at the foot of the bed, Richard took hold of her cock and guided it into position. The slick, glistening tip nestled snugly against Paul's star shaped pucker.

"Now this is going to sting a bit, cuckold Paul," I told him matter-of-factly. "I suggest that you breath normally through your mouth. If you hold your breath, it's going to make you more tense, and it will hurt like fuck."

I looked at Carol and winked at her.

"Ease your hips forward gently, sweetie," I told her. "I've lubed inside his arse, and your cock is nicely coated. You'll feel some resistance as you go in, but just take things slow and steady until you're right in him. Then we'll talk about how to peg a cuckold."

Carol nodded and jerked her hips forward. Paul wailed.

"Gently now," I advised her, "the tip's in. Just ease the rest of your cock in slowly."

Carol did as she was told, ignoring the wails and moans that her cuckold was making. When she was fully in him, and her thighs were resting against his arse cheeks, I lowered Paul's legs onto Carol's shoulders. She grinned at me.

"I'm doing it!" she crowed. "I'm actually pegging my cuckold!"

I leaned over and kissed her.

"Now start to fuck him," I suggested. "Begin by just rocking back and forth on the balls of your feet. That's right. Now get a nice steady rhythm going before pulling out a bit. Ease your hips back slightly. Good. Now push them forward again."

I watched carefully as Carol started to move in and out, back and forth. Everytime she pushed her cock back into Paul, he let out an agonised wail. Carol smiled as she got into a steady rhythm.

"Can I go a bit faster?" she asked, and I nodded.

"Faster and harder, if you like," I replied. "You've opened him up beautifully. Those little blue pills will prevent him from cumming too soon. Give him a good pegging for about fifteen minutes or so. Then we can think about milking him dry."

"I feel a bit guilty," Carol said breathlessly. Pegging is quite a vigorous activity, and this was her first go at it after all.

"How so?" I enquired.

"Well, I'm really enjoying myself, and you're just sitting and watching," he replied.

"Don't fret " I smiled. "Richard knows he has to do his duty after being milked. Watch."

I moved off the bed where I had been sitting and sat down on the bedroom chair which was positioned conveniently in the corner of the room. Richard followed me over, and sank to his knees as I opened my legs.

Putting my legs on Richard's shoulders, in a similar position to which Paul's legs were balanced on his Hot Wife's shoulders, I nodded to my cuckold, and he dipped his face between my gaping thighs and started to worship my cunt. I winked at Carol, who giggled, gave me the 'thumb's up' sign of approval, and continued to peg her cuckold. The room echoed to the slap of her thighs against Paul's arse and the slurping sound of Richard licking and sucking me towards a lovely orgasm.

I eased Richard's face away from my cunt, and stood up on shaky legs. He really was an excellent cunt worshipper, and his red, shiny face bore testament to the gorgeous orgasm his tongue had just given me.

"OK, sweetie," I said softly to Carol. "I think it's time for you to have your first practical milking lesson. Pull out of him. Richard will see to your cock,don't worry."

A breathless, slightly sweaty Carol did as she was told. Richard immediately slipped her cock out of its' harness and started to clean off the residue of lube, which was now mixed with Paul's arse juice. We ignored him.

I took Carol's hand and she extended her index finger.

"Do I need to lube my finger?" she asked, and in reply I nodded at her cuckold's recently pegged arsehole, which was still gaping, and offered easy access.

"I guess not," Carol answered her own question, and she slid her finger into the wide hole her cock had recently created. She frowned in concentration as she blindly felt for Paul's prostate. Her face broke into a wide grin when she found her target.

"Got it!" she said proudly, and as if in confirmation, Paul's cock twitched and seemed to throb in approval.

"Good girl," I smiled encouragingly. "Now remember how we stroked Richard. You make the same finger movements with Paul. The effect of those little blue pills won't last much longer, I suspect, but just in case, I'll sit on Paul's face. He needs to experience the taste of a cunt that's recently been brought to orgasm!"

I reached into my bag and brought out my pipe. It was already charged with my favourite aromatic tobacco, so I slipped it between my lips, climbed on board Paul's face and lit up. Soon I was enjoying the mellow taste of my tobacco and the feeling of Paul's tongue in my cunt.

Carol had been rubbing Paul's prostate for about ten minutes when I noticed a bead of pre cum ooze from his swollen mushroom head. I put my pipe down on the bedside table and climbed off Paul's face. He sucked in fresh air, his face red and shiny from being sat on for so long.

"He's close, sweetie," I informed Carol, "I'm just going to do this."

I leaned over and clicked the ratchet on Paul's mouth gag and removed it. He licked his dry lips and smiled gratefully at me.

"Thirsty?" I asked, and Paul nodded wordlessly.

One of the side effects of smoking a pipe is that it produces a lot of saliva in the smoker's mouth. I dribbled a thick string of smokey spit into Paul's dry mouth, and he swallowed and licked his lips again.

"Thank you, " he croaked, and I turned my attention back to Carol.

"Keep going," I encouraged her, "and when he starts to ooze, don't stop stroking. It'll take a while to drain him."

"What are we going to do with his cum?" Carol asked. "He's never tasted cum before, as far as I know, and I'd love to train him to re-cycle his like Richard does. But I don't have a cum glass for him like you do for Richard."

I thought for a moment, and then beckoned Richard over.

"You can snowball the first mouthful," I told him, and Carol looked on in amusement and amazement as Richard took Paul 's throbbing cock in his mouth. Just as I was beginning to explain to Carol what 'snowballing' meant, my cuckold gave me the 'thumb's up' sign.

"He's starting to cum," I told Carol. "Keep going with your finger. This will probably take at least a quarter of an hour."

Carol did as she was told, and eventually Richard pulled off Paul's cock, and turned to face Carol and me. He carefully opened his mouth and we could see that it was full of cum. I nodded to him, getting to my feet as I did so.

When they initially contacted me, having read some of my stories on Literotica, both Carol and Paul hinted that they were both bi curious. So I had no hesitation in telling my cuckold to carry on, and dispose of the cum Paul had deposited in Richard' mouth.

Carol gave a gasp of amazement as Richard dipped his head and kissed Paul, whose cock continued to ooze cum. I noticed that when their mouths met, Paul's cock twitched and another thick bead of cum appeared at the tip of his mushroom head.

I winked at Carol again and cocked my leg over the prone cuckold. Thanks to the worship I'd recently had from my own cuckold, my cunt was still slick and I impaled myself on his stiff cock.

As I sank down onto it, a deliciously wet sounding cunt fart echoed around the bedroom, and Carol and I grinned at each other.Still working her finger on her cuckold's prostate, Carol leaned over and we kissed, deep and wet. As far as I could work out, all four of us were really enjoying this play session.

My previous estimation wasn't far out. It took another ten minutes to drain Paul, during which time, Carol and I devised a plan to re-cycle the rest of the cum that had been milked out of him.

I lay down on the big bed, next to the now drained cuckold, and Carol went down on me. She cleaned up my cum drenched cunt, much to the dismay of my own cuckold, who loves eating fresh cream pie. But unlike Richard, who always swallows when he's on clean up duty, Carol filled her mouth and then went to kiss her cuckold. She did this three times before she was satisfied that all Paul's cum had been cleaned up out of my cunt and 'returned to the original owner' as she put it.

All four of us sated to a greater or lesser degree, (both cuckolds were still sporting hard cocks), I declared the play session to be over, and we all went back downstairs for a nice restorative cup of tea.

Paul provided an ice pack from the freezer for me to apply to Richard's still stiff cock. It isn't all that impressive even when he is hard, but his cock lock is so small that he has to be flaccid before I can get it back on him after he's been milked. When he was safely back in chastity, I sent him into the kitchen to help Paul prepare our tea.

The two cuckolds returned from the kitchen, one bearing a tray with the tea pot, cups and saucers and the milk jug, the other carrying a tray with a delicious looking Victorian sponge and four plates. They found their respective Hot Wives chatting animatedly about what had just gone on. Both of us were smoking our pipes, and Richard and Paul's eyes sparkled with delight. They both share more than the desire to be cuckolded. The pair of them also share a huge smoking fetish.

Paul took the role of mother, and served Carol and me with tea and cake before doing the same for Richard and himself. We allowed the two cuckolds to sit next to one another on the sofa as we all ate and drank our tea and chatted.

Paul raised an interesting point.

"I know I speak for Carol as well as myself when I say that I am honoured to be cuckolded by her and you, Olwen," he began. "We've talked about your and Richard's lifestyle, and we both want to emulate it, if we can. But as happy as I am to be made to watch you fucking Carol, when you've both finished, there's no cream pie, is there? I would love Carol to give me a fresh, hot cream pie occasionally."

I puffed on my pipe and looked at Carol. She took her own pipe out of her mouth and spoke.

"You're the first woman I've ever been with, Olwen," she said shyly, blushing deeply. "I know now that I really am bi-sexual, and I want to carry on being fucked by you. But I love cock too. Can a Hot Wife and her cuckold still have sex?"

"Of course you can, sweetie," I smiled. "That's the beauty of this lifestyle. There are no hard and fast rules, other than those you impose on yourselves. You can get yourself a boyfriend and have some mind blowing sex with him, and then come home for Paul to reclaim you. Richard and I used to do that until we decided that a policy of total denial suited us better."

"Richard still gets to eat cream pie on a regular basis, and he worships my cunt at least once a day. That's what pleases us. If you and Paul want to operate as Hot Wife and cuckold, and still fuck one another, then that's fine. They tell me that some men really enjoy 'sloppy seconds' Paul!"

Richard and I left soon after that, but not before we had made another date for a play day and training session. Carol and Paul would be coming to us when they returned from their holiday in Florida. I told Carol that I expected to see a pair of beautifully sun tanned tits, or she'd be going over my knee for a good spanking.

I saw that she was in something of a dilemma when I told her this. She wanted to go over my knee, but she also seemed go like the sound of getting her tits sun tanned. So we reached a compromise. Carol would get a tan on her tits and I'd put a different type of tanning on her arse cheeks when they next visited.

We also agreed that we would all visit Richard and my local fetish club when they were at our house. There were always chances for a Hot Wife to get herself noticed and picked up for casual sex. Both Carol and Paul seemed delighted at that prospect, and as they waved Richard and me off from their front doorstep, I had no doubt that as soon as the front door closed, they'd be back upstairs and fucking like bunny rabbits. I had a similar plan for Richard and myself. The only difference being that I'd be the one fucking my cuckold, not the other way round!

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3 Comments
DaddysgirlflDaddysgirlfl7 months ago

Olwen, your descriptions are, as usual, vivid and exciting. I learned a lot in this training exercise... I may just put some of it to good use. I'm off to look for a second part to this! Well done as always, my friend.

amadeuseroticamadeuseroticabout 1 year ago

I wholeheartedly agree with the statement "there are no hard and fast rules other than those you impose on yourselves."

However, I wonder why Olwen and Richard (or any couple for that matter) would impose a rule of lifelong denial of pleasurable orgasms and penetrative sex for him, just because his dick size is below average.

There surely are ways of putting his equipment to good use.

For example, he could be the initial lube provider by injecting cum with his tiny cock, so the next guy can enjoy the sensation of a cummy cunt that is not yet worn out.

Or he could provide anal training for inexperienced women who are scared of big cocks in their arse.

He could also practice tribbing, the way women rub their clits against each other.

So many possibilities ...

IstrokeCIstrokeCabout 1 year ago

Another excellent story from Mistress Olwen. What I particularly like is the matter of factness you always bring to these tales of cuckoldry and female led marriages. Discretion means that we have no idea really how many of us are enjoying this wonderful lifestyle , with all its varieties. I suspect though that it is much more widespread than is perhaps thought. And I’ll bet many many times more would love to try it out! It’s a lucky couple who get tutored by such an expert as Olwen!

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