Sharing Sherry with Friends Pt. 02

"Yes, Mike's lubing up her arse now, getting her ready to receive his cock," I heard Brian describing to my wife.

"Cathy asked me if there was anything special she could do for him and I told her that anal sex was the only thing he wanted that I drew the line at," I heard Sherry explaining to Brian, just as Cathy had told me. "I never told him what she was planning, I wanted him to get a nice surprise tonight. Looks like he's about to get his treat."

I smiled across at my wife, "It is a nice surprise honey, but watch out honey, I could find I like it even more than I expect."

"Yeah well if you do, we'll have to have a few more of these nights so you can do it with Cathy because I'm not doing it." She turned her head around to the man that lay body-to-body up against her back, arse and legs, "Brian, no complaints about where your cock is resting right now because it does actually feel nice, but just so you know, it won't be going any further. I don't do anal."

"No I'm cool, I know your feelings on that," Brian confirmed, "Cathy warned me."

Cathy was still up on her hands and knees waiting, and perhaps getting a bit impatient while the three of us talked. "Come on, are you going to do it?"

"Yes, yes I'm with you," I reassured her and slipped around to get behind her, my knees sliding in between her knees. I looked down to see all her good bits spread before my eyes, openly presented for me to choose like a smorgasbord. Ignoring her pussy from where traces of my creamy cum still seeped from her labia lips, I used my hand to position my cock so that the rounded head was lodged right at that crinkly anal ring. I ran both hands caressingly and softly over each arse cheek, attempting to have her relax her sphincter and her anus.

All the while, I watched my erect cock wedged at her anal entrance, its size -- not that mine is that big -- looking huge in comparison to that tiny pucker, marvelling at how this miniscule opening was going to somehow permit the head and the shaft to squeeze in through. Then I took a firm hold of Cathy's hips, watching as I began to push gently. There was resistance, my rounded head denied. I applied a bit more pressure, saw just my cock-head swallowed inside that tiny opening.

"Oh my God!" gasped Cathy.

Considering she claimed to be such a fan of anal sex, I was surprised to hear her loud and expressive reaction ... had I been too quick to push forward? Was she not ready? I was a novice at this, "Are you okay?"

She took a couple of deep breaths, "Yes!" she managed to gasp out, "you took my breath away, I forgot you're a bit thicker than Brian. Don't worry, it's okay."

"Would you prefer to forget it about it then?" I offered, extremely disappointed at the prospect that I might have to give up when I was this close to having my first anal sex since my teenage years.

"No of course not, I promised Sherry and I want to do this for you Mike. I'll be good, just give me a moment."

"You don't have to do this babe," cautioned her husband from the other side of the bed.

My wife chimed in too, "No Cathy, Mike will understand, don't do anything that might hurt."

Damn them both, just shut up and leave it to Cathy and me. Who needs their advice, we are the two trying this out? Fortunately, Cathy had a mind of her own, "No, I can do this, it's not like it's that much thicker, I can cope. Are you ready stud ... give me some more?"

I traced my fingers over her bare arse cheeks again, trying to relax her. Then, once more taking a firm hold of her hips, I pressed forward. At first, I made no more progress, but then I saw -- and more importantly felt the tightness -- of half of my cock shaft following my cock-head out of sight up into the arse of the woman on her hands and knees in front of me.

My God, how did an opening so tiny manage to accept the width of my erect cock?

This time Cathy just grunted as she took the width of my erection deeper into her anus.

Two more pauses and two more firm thrusts and I could at last look down on her arse and not see any of my cock, my public hair now pressed against the smooth pale skin of Cathy's bum ... my cock completely embedded in this dark place.

"Oh my God!" I heard my wife gasp expressively as she watched my cock disappear inside her long time friend's arse in side profile. "I can't believe you've taken all of him inside you! Oh Cathy, are you ok?"

This sexy woman beneath me was undaunted, "I'm fine Sherry, it feels really good now, I do like doing this you know."

"Did you start with Brian?"

"Oh no!" explained Cathy, "I was doing this with guys long before I met Brian. I'm an old hand where anal is concerned." Then she turned her head back around to me, "I'm ready when you are, let's fuck Mike."

I pulled my hips back and watched my cock slowly reappear from inside her anus until only the head was held captive by the tight grip of her anal ring, the shaft glistening in its coating of gel. Then I began to push my hard-on back into her arse, this time managing to slide in slowly in one movement all the way back to the hilt.

So continued my first anal fuck in years, Cathy lowering the upper half of her body by dropping down onto her elbows, her arse tilted upward to receive my constant thrusts. Could I cum so soon after the previous one that seemed so voluminous? I didn't care really, the euphoric feeling of orgasm would be great, but I was just relishing the difference of being inside the tighter confines of a woman's arse, so different to being in her vagina. This was incredibly tight and really hot, the KY was helping, particularly when I grabbed the tube and squeezed a little more on my shaft on one of the out strokes.

Upright on my knees behind the woman bent forward in front of me, my hands on her hips to hold her steady for each forward thrust, I began to feel that I might be able to cum. I quickened the pace of my thrusts, Cathy must have recognised the signs, "Are you gonna cum?"

"I think I might," I confirmed, feeling it was more possible on every stroke.

"That's good, I want you to fill my arse the way you filled my cunt."

I was grunting and panting now, signalling to the others that I was nearly there, "Oh yes, oh God Cathy, your arse feels so good ... so tight, so hot. Oh yes, I'm there, I'm gonna cum!"

I humped hard into her arse, feeling the cum surging up from my balls and bursting through my cock tip, filling her arse, but knocking Cathy forward, her face and shoulders flat on the bed as I spasmed my cum into her arse.

"Oh, that was wild," I enthused as the last drops of cum drained from my cock, deflating now. When its size had halved, I pulled back and watched my cock slide wetly from her anus. Her opening stayed distended for a little bit, my cum bubbling up out of her. I continued to watch fascinated as her anal opening slowly shrunk. What a fantastic experience!

"You look like you enjoyed that darling," came my wife's voice.

"Oh, you better believe it!"

"That's good, because it's likely the only time you'll get to do it," she added with a laugh. "Even though Cathy looked to enjoy it too, I'm afraid watching you two do it hasn't persuaded me," then turning her head around to Brian behind her, "Sorry Brian if you thought watching them might get me to relent."

"You really don't know what you're missing," I heard Brian tell her.

Cathy's body flopped down onto the bed completely, but despite looking exhausted, she still managed to contribute to the debate, "Brian's right Sherry, I did need to take a moment to adjust to Mike being thicker, but with Brian, you'd take him in so easy. Go on, give it a go honey, I guarantee you'll love it."

I assumed that Cathy and Brian might have pre-planned this joint verbal barrage on Sherry to persuade her to change her mind about anal. If that was so, Sherry shot them down quickly, "No, it's not for me I'm afraid ... sorry guys."

"Hey Mike buddy, toss me that KY tube, eh," asked Brian.

I hesitated, did he not hear how adamant my wife was? I didn't want to help him pressure my Sherry to do something she didn't want to. My wife looked anxious too on hearing Brian ask me for the gel, "What for Brian, I told you I'm not doing it?"

"No, I know you're not and I respect that, I promise you I won't try to put my cock up your arse, but please, just for me, try my finger in there ... one finger only."

Still kneeling behind the supine body of Cathy, I looked across at my wife. I could see how apprehensive she was so I bought in too, "Only if you want to honey," letting her know she had my full support, but inwardly hoping she might try it because of where it could lead to later when they were gone.

She was wavering, "Let me see how thick your finger is," said Sherry. Brian brought a hand around her and she examined his fingers at close hand. "This one, only use this one."

I picked up the KY and threw it across to Brian. He had to sit up behind my wife so he could use both hands to squeeze the KY onto and around his index finger, the one that Sherry picked. She must have considered his middle finger even too thick for her liking.

He rolled Sherry further forward so that she was nearly face down on the bed and pushed her left leg forward and bent, spreading her arse cheeks. His free hand roamed softly over the smooth skin, relaxing her and we all heard my wife sigh from his gentle touch.

"Umm, that's nice!" she conceded, probably intending for Brian only to hear her, but all of us being close on the one bed, Cathy and I heard it too. Brian brought his other hand onto her arse too, the one with the lubed index finger and he pushed that up against her anal ring, circling it gently a couple of times.

"You ok with this?" he checked.

"Umm, I am so far!"

Even Cathy lifted her head up to watch as Brian gently applied some pressure with that one slippery finger, initially drawing a startled "Ooh!" from Sherry, but gamely she didn't try to stop him ... her sphincter had halted his progress.

He pushed against her tight sphincter once more and the three of us got to see the sight of his fingertip disappearing up into my wife's anus. "You still alright?" his concern was reassuring to Sherry and he pushed his digit in deeper.

"Oh my God!"

"Anything wrong?"

"No, it's okay, I'm just surprised how it feels."

"Do you like it?"

"Um, yes, strangely I do, it's nice Brian."

"Can I leave it there?"

"Yes please!"

I was amazed and delighted, maybe I was seeing the initiation of my wife into anal sex. He was sliding his single finger slowly in and out of her anus and Sherry was lying there on our bed, letting him, seeming to enjoy this new experience. Although I had actually kissed her and fingered her arse once before, just after we first met, we had drunk a lot of wine that night so maybe she'd forgotten.

Cathy raised herself up alongside me to whisper in my ear, "What she needs right now is to have a finger in her cunt ... get over and put yours in. With Brian's finger already loosening up her arse, she'll really get off on your finger. I'm sure you know what to do to make her feel good. Believe me, she'll love it!"

I took Cathy's advice and rolled over alongside Sherry, she had her eyes closed so she never saw me coming. I licked my finger and wiped it on the sheet to make sure it was clean and brought it under Brian's hand to lightly touch her wet outer labia lips. Her eyes flew open when she felt the touch of another finger probing her so intimately, "Mike, what are you doing?"

"Shush, you'll like this," I told her as my finger pressed through the wetness of her pussy and found the opening to her vagina.

Sherry looked like she wasn't game to close her eyes again, as if she needed to watch us to make sure we didn't do anything she didn't like. But when I pushed my finger up inside her vagina and my fingertip found her g spot on the upper wall, she closed her eyes as if not seeing -- only feeling -- would make the delicious sensation up inside her body more intense. It must have, she emitted a long contented sigh. Brian, seeing what I was doing, maintained his similar finger fucking motion in and out of Sherry's anus.

Sherry straightened her legs in a natural reaction to the multiple pleasures she was experiencing with my middle finger pushing in and out of her vagina, working her g spot while my thumb circled her clitoris and in behind, Brian's index finger pushing in and out of her anus. Her breathing quickened and became loud, she lay on her right side, probing moving fingers in both openings. I leaned in and kissed my wife, our mouths twisting in heated passion as my finger and thumb brought her to a cresting peak of intense pleasure. Then a pulsing, throbbing orgasm overcame her, the muscles around her vagina and anus clamping tightly on the twin digits that had just sent her body soaring.

"Oh, that was so amazing," she managed to tell us all when she came down from her peak and she kissed me again, open-mouthed and passionately, "Thank you darling!" then rolled away from me, forcing my finger to withdraw from her pussy. She rolled over completely, turning away from me, slipping into the arms of her lover for the night, His finger had slipped from her arse by her movement.

I lay on my side, excited from what I had just done to my wife, now watching Brian fold an arm possessively around her back hugging my wife to him. "Oh thank you Brian, that was such a nice surprise. I can't believe it felt so good to have your finger in my arse."

"And my cock will feel even better," I heard him tell her quietly.

"Umm, I still don't know about that, but we'll see, maybe some time. I guess if I ever try it, and I'm not saying I will, but if I did, it would have to be your cock ... while I love Mike very much, I think for that I'd prefer to go for the thinner model." My wife lifted her head and turned it around toward me, "Sorry darling, it's just not going to happen between us."

"Yes I heard you tell Brian why. So I guess I'll just have to stay friends with Cathy then," I responded, rolling back over into her arms.

Chapter Eight

"What do you want to do now?" my wife's old school friend asked.

"I think we might go take a shower. Not only have we worked up quite a sweat tonight, but I'd like to clean my cock after having it in your arse, make it clean for our next fuck whenever you're ready."

"I'm always ready where a fuck's concerned, it's up to you to keep getting it up Mike."

"If we shower together, we might cover the getting up thing at the same time."

Cathy agreed, rolling out of bed and heading for the en suite bathroom ... me intentionally dropping back a few steps behind so I could enjoy watching the sexy way her arse moved as she walked, barefoot and naked. That shapely arse that my cock had just intimately penetrated.

I turned on the water, adjusting the heat and flow and stepped in, turning to hold my arms out for Cathy to join me. She grabbed the soap first, reaching straight for my cock, lathering it up and using her soapy fingers to get me hard again. Almost as an afterthought, she ran the soap over the rest of my body in a hurry before I took the soap from her and diligently lathered her naked body. My priority was between her arse cheeks and in and around her pussy.

When we had exhausted the fun of having a shower together, I turned the water off and grabbed a thick bath towel to rub Cathy's body dry first, then she dried me too. Cathy ended up on her knees to dry my feet ... from down there, she attempted to look up at my face, but she was unable to see beyond my renewed hard-on.

"Umm! What were you saying about having missed out on a blow job? Mike, having a night with me means you don't miss out on anything you want."

Cathy took my hard shaft in her hand and stroked it affectionately, then she closed her lips over the head of my cock while still kneeling on the bathroom floor in front of me and used her tongue teasingly to stroke the eye slit through which I pee. My God, that felt good. Then with her hand stroking my cock forward and back, she sucked more and more of my hard shaft into her mouth. She was a good cock-sucker and in any other circumstance, I would reach out to hang on to some nearby piece of furniture right where I stood and let her bring me to a shuddering climax.

I thought of still having the rest of the night stretching ahead of us. I had already cum twice and a look at the bedside clock confirmed it was only near midnight. At 42, how many more times could I cum and recover to full erection in one night? As sexual as Sherry and I were, we usually stopped at one a night. If my cum ended up being in short supply for the rest of the night, I wanted to save my last to blow inside her vagina before breakfast.

My body thrived on the attention that Cathy's luscious lips and tantalising tongue dealt on my cock but reluctantly I chose to pull her head away ... pull is not a strong enough word. I literally needed to prise her mouth off my cock, so determined was she to complete the task, blow me and drink my cum down her throat.

She looked up at me annoyed when I managed to get her lips off my cock and I held her head steady, 2 feet away from my body. "I'm sorry to stop you, don't get me wrong, it was awesome ... but that's just it, you are so good that I could cum in no time. This night is still young, I want to preserve myself for much more before Sunday dawns. In case the next is my last, I'd like to save it to cum in your cunt."

My vocabulary was littered with profanity when I was younger, but being married to Sherry all these years, I had cleaned up my language to avoid her dislike of some of the cruder descriptions for sexual parts. But my wife wasn't in this bathroom right now and I found myself reverting to using Cathy's way of talking.

"Cathy, I want to go down on you next, but not here on the bathroom floor. Come on, let's go sink into the comfortable mattress so I can lick you out."

She still looked disappointed that I had deprived her of completing a fine blow job for me, but her demeanour brightened once I proposed applying my tongue to her clitoris.

I opened the bathroom door and started back out into the master bedroom, my hand trailing back to bring Cathy with me. But we quickly stopped, hearing the heavy breathing of our spouses even before seeing them ... Sherry sitting astride Brian's hips cowgirl style, his cock pushing up inside her vagina. The panting, gasping sounds of peaking sexual arousal pouring from my wife's lips indicated just how near she was to climaxing, riding her new lover but very much in control, rising up and down on his shaft. From the light of the bedside lamps, I could see the changing expressions on her face reflecting the feel of his cock as it reached into the deepest recesses of her vagina.

I quickly reached back to shut off the light from the bathroom. I didn't believe that Cathy and I had been unreasonable when Sherry and Brian had their first fuck, yet he had tried to blame us for talking and distracting him ... his shallow excuse for failing to get past an early ejaculation.

I wrapped an arm around Cathy and pulled her to me against the wall, "Shush, let's not give Brian another excuse for cumming too quickly. Let's just hang here by the wall and watch them until they're done.

"Ah ... ah ... ah ... ah ... aaaah! ... aaaah!" Sherry was in complete control of the action this time and she came loudly as she rode cowgirl on top of Brian's vertical cock. How long had they been at it this time, had she already cum? We didn't know having been in the shower followed by Cathy's brief blow job on me.

My wife had stopped riding Brian when she came, her body flopping down onto his chest. When the waves of pleasure subsided, she lifted her head to check with him, "Should I keep going, do you want to cum?"