Meeting the Maddisons Ch. 05

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She had the two of us sit in the living room while she got ready for her fashion show. We sat there patiently on the sofa while she got changed. It was taking a very long time. I put on some music, and dad and I sat twiddling our thumbs on the sofa while we waited.

When mum finally emerged we were both stunned. She looked absolutely amazing. She could have just stepped from the pages of a high fashion magazine which specialized in sexy clothing. Her long dark hair was done up high, with strands hanging down her cheeks framing her lovely face. Her dark eyes flashed as she gazed boldly at us, her lips red with new rich lipstick.

But it was what she was wearing that really knocked us over. Two thin straps over her shoulders held up a loose cream coloured diaphanous gown. The straps extended so low on her breasts that it left them exposed right to the point of her nipples. The cleavage in front plunged four inches below her breasts. The dress hung from the nipples, gathered in tightly at the waist and then fell down to her ankles. But it was the see-through quality of the material that excited me most. You could just about see right through it, but not completely. It left a little bit to the imagination as she stood there, tall and proud. Through the thin material you could make out the bottom curve of her heavy breasts, her nipples and areola, her chest, flat belly and navel. The material cleverly seemed to thicken slightly as it reached her lower belly, a pattern radiating out in a silver starburst which dragged your eyes to the join between her legs. There was no doubt when you looked closely you could just make out her shaved pussy through the material.

Mum took a few steps and twirled. The dress split all the way up the side past her hip. Every time she took a step or stood with one leg in front of the other everyone could see through the slit that she was naked under the gown. From the side you got a complete profile of her breasts, only the nipple was covered. It was the most revealing dress I had ever seen, even more revealing than the black plunging dress Laura Maddison wore to that dinner which started this all. Mum was in extremely high heels. They were silver, adding elegance to the way she carried herself.

One of the good side effects of our new sex life was that all of us were working very hard to make our bodies look their best. I'd put some muscle on my shoulders and was working on my abs. Dad was also much fitter. But best of all Mum was working hard at the gym to perfect her body for us. She'd lost that little bit of bulge on her tummy she'd had when I first saw her naked at the Maddisons. Her stomach was now hard and lean. She'd also slimmed down her hips, bottom and thighs with vigorous exercise. So when she stood in this incredible revealing gown she looked even more naked than when she had no clothes on. She turned around to show the back of her gown and my heart leaped. The back scooped right down to her hips and revealed the two little dimples just above her ass, but the diaphanous material allowed everyone to clearly see her ass crack.

Dad and I stood and broke into applause. Mum did a mock curtsey and looked radiant. We strode over and hugged and kissed her.

"You are absolutely stunning Gloria," dad said. He was almost weeping with pride as he held her hands and stood back to admire her.

I was just standing there open mouthed. Mum looked at me and laughed. She dropped dad's hands and held her arms wide to embrace me. I was wrapped in her arms hugging her, my chest against her warm breasts. When she let me go I couldn't help but reach out to heft both her breasts, slide my hands down her stomach to caress her belly and softly stroke her shaved pubic mound. I turned her around, slipped my hand onto her breasts from the open side and then held both her ass cheeks in my hands, squeezing them.

"Now, now, don't damage the material," she chided with a laugh.

"Gloria, I'm not even going to ask how much this gown cost. It is worth every cent. You are absolutely ravishing. Men will cum in their pants when they see you in public in this gown. I'll be so proud to have you on my arm. All the other men will be thinking how lucky I am to have such a breathtaking woman with me."

"And mum, I'll be so proud to tell people you're my mother when we go out with you looking like this. Dad, we'll have to take mum to the ballet or opera or something classy with her dressed in this."

Dad nodded his agreement, still gazing in wonder at his ravishing wife.

"Thanks dear," she said. "But do you remember I had someone helping me with the shopping? She helped me get ready tonight." She called out to the bedroom: "Come on out, I think the boys want to thank you."

We looked to the bedroom door and out came Alison Maddison. I was surprised to see her. I hadn't seen any of the Maddisons since the last visit turned into an orgy of two families.

"Alison, how great to see you," I cried and raced over to hug and kiss her.

"Thanks so much for helping mum. She looks incredible. Where did you find that amazing gown?"

"I've been shopping with my mum for years. I'm not one to dress up myself, but I know where the sexy gowns and dresses are. Mum taught me how to dress to highlight your best features, and it's pretty obvious what Gloria's best assets are," she laughed and reached over to kiss mum's breasts, first the left and then the right.

I nudged dad. "With Alison here do you think it's a good time to bring out our surprise for mum?"

"Good idea," dad said. I raced off to the cupboard where we'd put the dildos and butt plugs. I brought them back and laid them out on the coffee table. Alison gave a small squeal of delight and held up the largest one, stroking it and stretching her fingers around the five inch diameter.

"Oh God, if I could take this one I'd have that gold medal in my hands."

We told her about Sally and the advice she gave us. Alison was keen to meet her.

"Maybe she can get me some cut price plugs. I need some more anal stretching. But these are for you Gloria. Do you need some help with them?"

"I've never used anything like this," mum said taking the massive plug from Alison, looking at it in awe.

"Mum, we got these for you because you know how I love your ass. The more open and wide it is the more I like it. I hope dad will be able to fit in there some day, but it'll take some real stretching before you can do it comfortably and enjoy it."

"Well, of course I'll try, dear. But as for this monster......"

"It'll take a long time for you to be able to take that, Gloria," Alison said. "I couldn't take anything like that, and I've been working hard at stretching my anal muscles for years. I saw a woman take something that big at the last Sex Olympics. It blew everyone away."

Mum couldn't resist a challenge.

"Just how long have we got till those Sex Olympics start?" asked mum.

"Only two months," Alison replied. "There's no way you could stretch enough in that time to take a monster like this."

"Wanna bet?" mum said, tossing the huge butt plug from one hand to the other.

"Holy Shit, Gloria," Alison said, shaking her head. "You'd be crazy even to try it. Look, I've been stretching for years and the maximum I can take is a two inch plug."

I picked up the pack that had the steadily expanding plugs.

"What about these Alison? Would these be good to start?"

She examined the plugs and thought.

"There's only one way you could stretch enough in that time Gloria. You'd have to wear butt plugs like these all day, using a bigger one every time you can fit it in."

She looked at mum still in her stunning gown.

"You know what Gloria? A plug can also be a fashion accessory. I'll get something from my bag."

Alison returned with a butt plug that had a diamond covered ending that would be seen sticking out of the anus. It was about an inch in diameter.

"Let's see if it could work," Alison said, and lifted mum's gown over her bottom.

"Hold this up please, George."

Dad held up the soft material, leaving mum's ass bare. Alison had her lean over the chair so her ass stuck out. She put some lube around the end of the plug and slowly inserted it into mum's asshole. Mum flinched only a tiny bit as the three inch wide bulb of the plug slipped past her sphincter. She was getting used to her back passage being filled. Maybe she could eventually take that massive butt plug after all.

The diamond covered ending of Alison's butt plug snuggled between mum's ass cheeks. Alison told mum to stand up straight and lowered her gown over her ass. The diamond head of the butt plug glittered through the diaphanous material. It made her look even more spectacular. Everyone who saw her from behind would be wondering what that glittering object was between her ass cheeks. Some might recognize it as a butt plug, and either stare in admiration or back away in embarrassment.

"I think that completes the outfit perfectly," dad said.

"I agree, mum. Thanks ever so much Alison. That was a great idea. Hey, I hope you don't see mum as competition for your anal sex award at the Sex Olympics."

"No Jim, of course not. It's a competition after all. I'll just have to work harder."

Dad and I really wanted to make love to mum after seeing her in her amazing gown. Unfortunately Alison couldn't stay as she had to go back to uni. It was a long languid evening of threesome sex. First dad licked mum's pussy, while I watched, kissing and caressing mum's breasts. Dad then got mum on top and fucked her slow and lovingly while I licked her ass. When he came and withdrew, mum lay on her side facing dad. I got behind her and gently inserted myself in her ass. I was pleased there was little resistance now, her sphincter welcoming me inside. Mum kissed dad long and deep as I slid in and out of her asshole until I too came deep inside her. Mum turned her head back and kissed me, smiling contentedly. We all felt so happy and close, and drifted off to sleep.

The next morning Mum inserted the inch wide butt plug and wore it all day. Dad and I could see it between her cheeks as she walked around the house. On the second day her sphincter was stretched to the extent she picked out a larger one that was an inch and a half in diameter to insert.

At the end of the second day as we finished dinner I told mum I was keen to see what a difference the plug had made.

"Mum your sphincter has been kept open with an inch and a half wide butt plug all day. How does it feel?"

"It was difficult at first dear, but now I'm really comfortable with it. I think in a week or two I can go up to the next level."

We hadn't told mum about Sally and her club coming the next night. It was to be a surprise. I didn't know what to expect, but I knew mum's ass would get a work out.

"Mum, I'd like you to try an even bigger plug tomorrow?"

"Why dear, what's the rush?"

"I just want to see how far you can go – no limits remember."

"Yes, but I also said I'd do things my way. I'm not quite used to accommodating this one yet. Alison warned me against going too far too quickly."

I looked disappointed.

"You teenagers are always so impatient. Come over here Jim."

I got up from my seat and stood next to mum. Dad was listening as he cleaned the dishes. Mum pulled down my shorts and kissed my cock that rapidly rose to full erection. She stroked me as she talked.

"Jim, you have to be patient with women. Never force them into something they are reluctant to do. Some day you will have a girlfriend and you have to treat her properly. I do things like stretch my sphincter for you because I love you deeply, and I know that's how you want me. It makes me happy to give pleasure to you and your father. But if I don't jump immediately to your wishes, don't get upset with me. No woman wants a bully or a petulant boy. Do you understand me?"

"Yes mum," I said. "Sorry mum."

"Good, now let's move into the living room. George, join us there when you've finished."

Dad waved his agreement and mum led me into the living room. She stripped out of the short dress she was wearing over her naked body and I saw the butt plug was still in her ass. Mum opened the drawer on the small table beside the couch and pulled out the large tube of lube we kept there.

"Pull out the plug please Jim, then smear this over my sphincter. Do it gently and slowly. No tugging."

Mum lay face down on the arm of the couch, placing her ass right at my dick level. I grabbed hold of the butt plug and pulled gently. The bulb inside her was larger than I expected and I had to really exert some strength to get it through her sphincter. I jiggled it side to side and exerted a steady pressure until bit by bit her sphincter expanded to allow the bulb to get through. It was the first time I'd seen her ass expand in reverse to let something out rather than opening to let me in. Her sphincter had to stretch about three and a half inches before the plug suddenly emerged. I was very impressed. I didn't realize how much she had to stretch her ass to absorb these plugs. I'd made the mistake of just thinking about the diameter of the plug where it stayed stretching her sphincter all the time it was in. When it came out mum's ass was gaping at least two inches.

"Mum, I didn't realize how wide you had to open to get this plug inside. That is an amazing achievement. I'm so proud of you," I said and I bent over to kiss her face.

"Put your cock in right now Jim, don't waste time while I'm all open and loose for you."

I did just that, sliding into her ass and was thrilled to find there was no resistance whatsoever. Her ass was as open as her cunt. Dad came in at that moment and sat down next to mum. She turned to face him and he kissed her.

"She's getting really open now dad. It's so easy to slide into her ass after she's had the butt plug in all day. I think she'll be able to take you up there soon."

"That's great Jim, well done. Thanks so much for being so brave and stretching yourself for me Gloria," dad said kissing her deeply.

I fucked her steadily in the ass. Mum didn't move, just lay still, offering her ass as an open passage for my dick. This was a good position, me standing and her lying on the arm of the couch. I began pounding her harder until I came deep inside her. I pulled out and saw her gape was around two and a half inches, even larger than before. I kissed mum on her back and collapsed into the nearby armchair.

The next day I noticed mum had indeed chosen the next largest butt plug with a two inch diameter. She'd be more stretched than ever for Sally's visit with her club members that evening.

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3 Comments
Foxterot7aFoxterot7aabout 1 year ago

This story is developing in a logical manner. I especially liked the way the mother explained to Sam that she was going to do her thing her way and why she was doing it. Finally, this story is walking a couple through the proper way to introduct anal sex. Likewise, it is demonistrating how and why it is necessary to take your time/be patient while expanding into anal sex play. The one important element left out of this story, is the sanitary (pre and post) requirements required of anal sex in order to aviod infection, physical harm and/or psychological harm inadequate preparation can cause.

AnonymousAnonymousover 5 years ago
Amazing

Loving how the story unfolds

digdaddyrichdigdaddyrichover 12 years ago
Fantastic chapter

Getting mum's back side stretched out is really hot. It seems it like she is willing to do anything for her son, and in giving him a good stretched out ass hole is hot.

Jim and George are very lucky guys to have a woman like Gloria, that is dedicated into giving them sexual pleasure and willing to be their slut..

A great story, thanks for the read.

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