Our Friend Anne

Thanks for the feedback on my first story. In this one, Anne learns more about Jack and Jill's sex life and some of their kinks. I hope you like it.

*****

In the morning, as the house began to awaken, my wife rolled over and snuggled up against me. Her firm legs interlocked with mine, and her soft breasts came to rest against my back.

"Mm, that was pretty great last night," she whispered in my ear.

"It was. I was sorry I ended it when I did," I replied, as I felt her body warming my backside. I pushed my butt back and more firmly into her lap, seeing if there was any interest in enjoying a little more now.

"Oh stop, big boy," she said, getting up to go check on the kids. "You are going to get more than you can handle from Anne and me later today."

Great, I thought, now I am fully aroused. I adjusted my pajama pants and went to brush my teeth. Clean mouth and calm cock, I headed downstairs.

There I encountered my oldest, aged seven, sitting on the couch and watching TV.

"Hi Maddie," I said, waiving to her as I made my way to the kitchen. No response. Which, to be fair, is exactly how I was when watching cartoons at seven.

Entering the kitchen, I encountered Anne who, based on the great aroma filling the room, had apparently gotten the jump on making coffee - well based that and the cup she was sipping as she sat perched on the counter.

"Hi Jack," she said. "She came down a minute ago. I wasn't sure if it the TV ok."

"It's fine," I answered. "A few cartoons on weekend mornings never hurt anyone. Besides, it gives me a chance to do this."

I crossed the final few feet of the floor to the counter and leaned in to give her a kiss. She kissed back, putting her arms around my shoulders and embracing me for a tender moment.

I broke away and snuck a quick glance at Maddie, who was still focused on the TV. Shit, I needed to be more careful if I didn't want this to blow up in my face.

"Do you want some coffee?" Anne asked as she hopped off the counter and went over to the coffee maker.

"Yes, please," I said, as I started to think about what to make everyone for breakfast.

"Black, no sugar, as I recall."

"Yes, you have a good memory. Hmmm, milk, right?"

"Well sure, but you could tell that from my coffee cup right next to you on the counter," she said, teasing a bit.

Damn, she was right, I thought as I looked down in front of me. Having this beautiful woman here, ready to act on years of pent-up desires, was impacting my thinking.

"Well, I guess I'll have to find a better way to show how much I care," I lamely tried to tease back. I got to work.

I made a light breakfast, just some fruit, eggs, yogurt, and toast. We were meeting up later this morning with our bigger circle of longtime friends and their families, but the kids (and adults who had put in a nighttime workout) would need something before then.

Anne excused herself to go change and everyone descended on the kitchen just about when everything was ready.

We all sat at the kitchen table, sharing our meal and chatting mostly about kid things like what they had watched this morning and who they were excited to play with at the brunch.

As we talked, I felt a foot slide up against mine and began to stroke it a very non-kid fashion. Looking down under the table, I realized it was my wife. I don't think we had played footsie since the first or second year we were dating. I was more surprised when my other foot felt something slide up against it and began the same routine. I looked down and saw Anne was using her foot against mine.

I looked at my wife. I looked Anne, wondering what the odds were that they would both spontaneously initiate the same sexy game. My phone buzzed in the pocket of my pants. I pulled it out.

It was a group text with Anne and Jill.

"We decided to let you in our chat," Anne wrote.

"We've been texting all morning, coming up with good ideas. Like playing footsie," Jill added.

Of course they had.

"We promise to make today about you," Anne texted.

"Yeah, so try to keep up," my wife added as they both cracked a grin. My kids continued discussing the finer points of morning children's programming.

--

I rushed to get ready when breakfast was done and soon we were on the road to the house of the friends who were hosting.

When we pulled up, we saw we were there a little late from the cars lining the street in front of their house. We all piled out and were soon in the door, giving hugs and making hellos. Anne having been away for a while was the center of attention. I eavesdropped on her as I entered the room, shaking hands and greeting friends.

"Oh, you know. Not much, mostly just working and trying to stay busy," I heard her tell one old friend. "Move back here? I don't know, I guess for the right reason."

She stole a glance at me at that moment, as we made brief eye contact, I saw a warm glimmer pass through them.

"Jack, tell Mary about how you got rid of that mole in the backyard," Jill said, grabbing my arm and pulling me into a conversation.

Later, as we sat in a circle of chairs inside as the kids played in the backyard, I heard one friend ask, "So Anne, how has it been being back in town?"

"Oh pretty good," she answered. "Jill and I have been catching up. Jack's been very nice about it .We went out to eat last night. Nothing too exciting."

"Yeah, we are going to go after this for a massage and spa time," Jill added in.

"By the way, I got your text" our friend, Rachel, piped up. "We can totally take the girls this afternoon. Sorry you've got to work, Jack."

"Yeah, it's too bad," I said, wondering what she was talking about. Jill had been busy with that phone this morning.

Soon it was time for the meal, and before you knew it, the event was winding down. Our kids went off with Rachel, her husband, and their two boys.

"Ok, Jack's going to go drop us at the spa now, but just text to make sure we are home before dropping off the girls, " Jill said to Rachel, as we wrapped up our goodbyes to the others at the gathering.

"I didn't know you had a spa things planned," I said as the three of us got back into the car.

"Don't be silly," Jill laughed. "We just needed a little more freedom to take care of you this afternoon."

"Oh, I wasn't sure if that was really going to happen, or if you were just teasing around," I replied as I pulled the car onto the road and headed home.

"Are you kidding? After last night, I think both of us are looking forward to giving you a little of the tender loving care you deserve for being such a good boy," Jill said with a note that was both playful and suggested some serious planning was now in motion.

I checked out Anne in the review view mirror and she nodded her assent. "You're a pretty special guy Jack. And now that Jill is into sharing you, there are a lot of things we are looking forward to doing."

"Really honey, are you sure that is how you feel?" I asked, worried that somehow I was going to manage to mess this up and ruin a marriage in the process.

"Uh, yeah," she said pointedly. "Let me read you some of the texts we shared this morning before we added you to this chat."

"Make him fuck and suck us like last night, but switch each time one of us comes."

"Tie him up and blindfold him, and see if he can figure out whose breast is in his face"

"Or whose pussy it is."

"Or have him decide which pussy taste better."

"Make him massage both our pussies at the same time," Anne added in from the back seat.

They were clearly scrolling around, making me wonder how long it would take us to work through this list and how long I would be able to keep my focus and the car on the road.

"We each take turns fucking him with strap-ons until we've milked his cock dry."

That last one brought it to a point, as I reached over to put my hand over the screen of Jill's phone. Our eyes connected and she saw that I had reached the breaking point of the sexual teasing I could endure. After all, she knew where that one placed on my all-time list of sexual fantasies.

Jill turned to the back seat, her and Anne sharing recognition they had pushed this as far as they could - and both burst out laughing. I soon joined, with us laughing and smiling the rest of the short distance to the house.

As we entered, Jill told me, "Why don't you go upstairs and get yourself cleaned up."

For us, that meant some ass play was on tap. I guess they were looking to really take care of me, as that was one of our special treats when we had the time and privacy.

I made the way to my closet, where my cleaning kit was stored. I grabbed it, and got to work, stripping down and then letting the enema enter and exit my body.

I leaned against the bathroom sink as I worked my cleaned asshole with lube and gradually slid a butt plug into place so I would be ready when it was time.

Making my way to the bedroom, I saw Jill and Anne had decided to dispense with clothing for the rest of this summer afternoon. They lay naked on their backs, Anne on top of Jill and shifted down so her head was cushioned into the crook of Jill's neck. They had been talking quietly and as I entered the room they beckoned for me to join them.

I lay down next to them on my back and Anne rolled over onto me - chest to chest. Jill rolled over on her side and pulled my mouth to hers. I alternated kissing Jill and Anne. A few times we all kissed together in a mashing of our lips or a circular pattern of pass the kiss. That led to couple of extended lip locks between Jill and Anne. They seemed to enjoy it, but weren't willing to halt the show to truly explore this new experience.

My right hand worked its way over Anne's body, massaging her ass, breast, shoulder, and scalp. My left began playing with Jill's breasts and migrated down to begin working the folds around her snatch. As her labia grew with arousal, I began stroking the sensitive skin around her clit, soliciting a soft moan in response.

"That's pretty good, but I think I would come much quicker with your mouth," said Jill. "Anne got that last night, so she can get you ready while I have my turn."

Anne showed her approval of this plan, getting off me and waiting for us to reposition.

Jill lay back again, spreading her legs and exposing her sex. On hands and knees, I dove in - kissing and licking the sensitive spots I had just been working with my fingers.

Continuing to work her lips and around her clit, I felt Anne's hands guiding me to move my knees as she spread me more open to receive. With my head down in my wife, I couldn't see much of what she was doing - the surprise of the physical sensations making them that much stronger.

I began to work the top of the clitoral hood down to the taint with long, slow strokes. I felt Anne's hand close around my hard cock and bring it to her mouth. She worked it over gently, exploring its texture on the tongue for the first time. She then shifted and I realized her head was lying under my chest and stomach as she began to work my dick in and out of her mouth.

Anne reached out a hand and brought it around the back of my thigh to get better leverage. She succeeded and switched to sucking me deep and then slowing letting me slide out as she worked the bottom with her tongue. I shuddered so vehemently that Jill murmured her approval in response.

We continued like this, me gradually bringing my focus to the areas surrounding the clit as Jill drove on toward orgasm.

Anne let me slide out and withdrew from under the bed. "Let's see about getting this guy ready," she muttered to herself, apparently all business now.

I shuddered again as she slotted herself behind me and, grabbing an ass cheek in each hand, brought her face down and began working her tongue across the contours where my ass tightened around the plug.

I continued working Jill's clit, trying to help her arrive. But I was overwhelmed by the sensation having the crinkles of anus licked and worked over. Anne continued for a while, trying to get the skin to relax so she could glide her tongue between the plug and my ass. Having little success, she shifted to gradually working the plug to slide in a circular motion and adding her tongue to the mix to begin further loosening me up.

My cock began to twitch each time her tongue penetrated around the rim of the plug and for a second I worried I might come. Luckily, Jill restored my concentration.

"I would love to join her in giving you all this love, but first can you help me come?" She asked, gently lifting my face out of her lap to look me in the eye.

She was right, the sensations coming out of my ass had put the rest of me on autopilot for a second. I renewed my assault, working my tongue around the top of hood and then sliding it down, around, and up to work the hood from the underside.

I felt the plug begin to loosen as Anne succeeded in creating a sufficient gap and lubrication to break the seal with my rectum. She began twirling the plug smoothly in a clockwise motion with one hand, as her other hand came down to stroke my cock.

I added my thumb to the mix, working firmly on the base of the clitoral hood and soon added another finger to gently work Jill's anus - ensuring good lubrication all around.

That did it, as I felt her own personal earthquake hit Jill. I wasn't the only one in this relationship that got off on a little ass play.

She pushed me away from her as the sensation became too much. But as I looked up at her, she quickly recovered and declared, "Right, back to Jack's time." I stayed in my position on all fours on the bed, as Jill went around to join Anne.

I quickly felt the plug come out with a slight tug and heard Jill complementing Anne on her work. "You really got him loosened up," she said, as I felt two sets of fingers begin to play with the shrinking gap between my anal folds.

I couldn't tell who was touching what, but almost immediately heard the zipper of the bag we keep our gear in. It was actually a black nylon traveling case for your high-end kitchen knives and utensils. I guess fancy chefs use them sometimes, and I found one online that was perfect for all our toys and supplies.

With a pop of a lid, I could feel Jill smearing lube on and inside my ass. I knew it was her because of the familiar pattern of movement that was how she got me ready to play. Soon I was gasping as both of them alternated using their lubed fingers to work deep inside me and then withdraw.

There was another rustling and I wondered where there this was going next. The case included six strap-ons, four two-sided and two one-sided. A couple of harnesses. A number of other butt plugs, including my personal favorite - the one with a fox tail. Several variations of vibrators and other stimulation devices. And all the supplies we needed to keep the fun going.

As Anne stroked two fingers in my ass and brought her other hand down to work over my cock, I saw Jill out of the corner of my eye. Turning, I saw her synching up the harness with the short end of the two-sided, six-inch black matte dildo already fitted inside her. Noticing me looking at her, she tilted her face just a little and cocked an eye as if to say, well, this will be something new.

She finished getting everything in place and moved back behind me and out of view. I put my head down to focus on the sensation to come.

"So it is important to get the angle right when you first get going, kind of like how it feels when a guy comes into us," Jill was instructing Anne. I guess no man have ever explored pegging with her before. "Do you want to hold his cheeks to make it easier for me to line it up?"

Anne didn't say a word, but I almost instantly felt my globes being grabbed and separated. Jill shuffled in behind me and I felt the tip tapping against my sphincter.

As I felt the coolness of the lube covering the rubber cock, Jill brought her hands up to below my shoulders. She began guiding me down as I took a deep breath, and bearing down a bit, pushed myself back into her as she pushed into me. I felt most of the head slide in.

Jill and I backed off as Anne continued to softly squeeze my buttocks and keep them open so she could see what was happening.

Through her touch, Jill began again to pull me in and, as I relaxed further, felt a good third of her cock slide in. From there we picked up a slow back and forth pace until I was fully impaled. Anne disengaged as Jill leaned over and play whispered to her, "If you let him eat you out, we may need a beach towel to clean up the puddle he'll leave on the bed."

"Damn it, woman. Sharing all of my inner secrets on our second date!" I exclaimed in fake outrage.

We all looked at each other for a second and burst out laughing - Jill still buried in me. Even if this most intimate of moments, it was nice to know we could keep up the playful banter that had made our friendship so enjoyable over the years.

After a few seconds, she renewed her pace - pulling in and out with long, slow strokes. Her hands came down to use the tops of my hips for leverage. I began to lean back into her a bit at the start of each stroke to bury her a little more deeply.

Anne came and sat in front of me, her legs split wide - giving me a direct eye line to her pink seashell. Moving her feet closer, she scooted her butt towards me and began positioning herself to let me eat her out.

But as I leaned my head forward to initiate contact, Jill picked up the pace and I misjudged. Although I was able to compensate to avoid a hard impact, it ended up my chin made contact with her sex instead of my mouth - leaving a wet smear down the bottom of my face. Anne and Jill chuckled, and I smiled.

It took a little practice, but I learned to anticipate how Jill would be riding me and to lean my body back to counterbalance. Kind of like you learn the rhythm of the motion on a ship or a subway train. I also figured out how to use my hands to let Anne's body slide along with me when Jill was reaming me with a particularly hard stroke.

We fucked several minutes this way - Jill setting the pace and me in heaven as I checked an item off my sexual bucket list. The only reason I didn't come was that my almost painfully hard cock was getting zero attention.

As Anne arrived, she exclaimed, "Oh fuck Jack, don't stop." I stayed working her over as I felt her orgasm sustain and then subside, continuing to take it in the ass from my wife.

Anne lay back and Jill suggested we change it up, to give Anne a try.

Anne's attention came back into focus and she lifted herself up onto her feet. Jill removed her harness, and then her and Anne began busily selecting her inaugural strap-on. They chose a bright turquois, seven-inch narrow, one-sided dildo. Jill helped her fit the harness and dildo right, and turn on the bullet vide positioned to ride just above the wearer's clit.

Anne turned it on and jumped a bit. She looked at me and smiled with excitement.

I got back down on my hands and knees, wanting to help her learn how to properly peg someone. After all, it isn't like guys don't have to learn what it means to properly fuck someone. Jill moved her into position, adjusting her hips and stance to position for effective thrusting.

Luckily the workout my ass had already received made it easy for Anne's cock to slide in. In about halfway, she just stopped. I flexed my ass around it and heard her give a little gasp of surprise as the dildo and the vibe pushed back against the nub of skin above her clit.

Looking over my shoulder, I saw her give me a look of mock outrage and felt her push hard into me - covering most of the rest of the depth in three fast strokes.

She began working it around, testing how she could pull it in and out and how to position her hips and body to move it around inside me. She even pulled in tight and tried to reach around to also start jacking me off. Jill stepped in, touching her hand and saying "Why don't you focus on taking care of his ass - there's a lot to learn. I'll take care of this thing."