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Ali Teaches Anal

Category: Anal Sex
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This time when I woke up the birds sounded like they should have. I opened one eye, good, my own bed. Something warm and smooth against my back, actually two somethings. If I wasn’t such a cynic I would swear they were my wife’s boobs. If you remember from our first story we normally sleep in separate beds. Evidently after our first experience with anal sex the night before she decided she wanted more snuggling.

I tried to ease out of the bed without bothering her, but a hand grabbed the back of my boxers and a muffled voice inquired,”where do you think you’re going?”

“To start the coffee and make you some breakfast in bed.”

“You nice man. Could I interest you in a little kissy, huggy before you go?”

“Of course. What if it goes further?”

“It can go where ever it goes. It won’t hurt my feeling if it ends up with your cock in my mouth and your tongue in my pussy.”

I’m still adjusting to the new Ali. The old one would never have said cock or pussy, much less perform that act. Oh she would happily let me eat her, but returning the favor was alien territory. The new one is all too happy to do exactly that.

“Just remember, you managed to get more cum out of me last night than I thought I could produce in a week. I’m just saying if you want a repeat of last night you might want to give it a rest.”

“Poor baby, you wouldn’t consider giving me what I need and letting me owe you a BJ would you?”

“I thought you’d never ask.”

Twenty minutes later Ali shuddered and squealed as I gave her hard little clit a long hard suck. I love her scent when aroused and nothing makes me feel more connected to her than being right here when she cums. Don’t get me wrong, her blow jobs started out pretty weak, but now they’re world class as far as I’m concerned. That’s good too, but this is better.

After twenty more minutes of snuggling and kissing, she really enjoys her own scent on my face, I was off on my previous mission. When I returned I half expected to find her in her own bed, but surprise, she was sitting in mine reading a magazine and still naked. I must have stopped in the door with a shocked look on my face.

“What? If you don’t like it I can put some clothes on.”

“Don’t mind me, I’m still getting used to the new Ali.”

“Try to keep up sport. And make sure you eat some of that too to keep up your strength.”

She’s always concerned about my health, or is that stamina? When we finished I left her in there and took the tray back to the kitchen and cleaned up from breakfast. Ali is particular about her kitchen and I was trying to keep the good feeling going by cleaning to her standards. Something I haven’t always done.

When I walked down the hall to my bedroom Ali came out of hers wearing that tiny black bikini I love so much. She said, “I’m going to take a little sun by the pool, will you rub some lotion on my back?”

“Sure, let me change and I’ll be right out.”

The pool is our favorite thing about this house. It’s a full twenty five yards long so swimming laps is much more enjoyable than in a shorter pool. But the best feature is the sun cabana. When you go out the french doors to the patio it’s just twenty feet to the opening in the back of the cabana. It’s made out of redwood and canvas, and it’s u shape leaves room for up to six people to sun in privacy from the neighbors on both sides. The cows in the pasture behind us can see in, but I’ve never noticed any of them staring when she suns nude.

Today wasn’t totally nude, she had the top off and the bottoms pulled into the crack of her gorgeous ass. After I attended to her back I made sure her butt was also covered. I’m the only one allowed to blister her behind and make it red.

A voice called from the Murphy’s side of the yard,”ahoy Clarkes, permission to come aboard?”

Ali said.”that’s Meg, let her in.”

I knew who it was, we just saw her getting boned by her boyfriend in her back yard last night. Right after Ali got boned in her backyard. I leaned back and pushed the button that released the magnetic lock we had on the gate to Murphy and to Burns on the other side. We figured it would be handy when we invited folks over to the pool. It was.

I could hear her sandals clicking on the concrete before she came into view. Meg is one of a pair of fraternal twins. Her sister, Mary, looks more like their father, Meg looks like her mother. She was what most red blooded men would call statuesque. At 5′ 11″ she towered over most other women, but her proportions were perfect. Wide shoulders, a slender waist, and equally spectacular hips. Top this off with perfectly formed c-cup breasts, porcelain skin, dark curly hair to her shoulders, and a face beyond pretty. Men stared at her no matter how she dressed. To be fair it wasn’t their fault.

She was wearing a dark green bikini top only slightly larger than the one on the concrete next to Ali, and had a white terry cloth wrap around cover up clinging to those fantastic hips.

“Hey Mr. C, Mrs. C.”

“Hi Meg,” said Ali, “you know, you’re twenty two now, why don’t you call us Ali and Jerry?”

“I guess so, it seems a little weird since I’ve known you since I was little.”

I couldn’t resist,”well, you’re certainly not little now.” That got a giggle from her.

She frowned, “can I talk to you guys about something?”

“Sure,” we chorused.

“I need some sun too, can I join you Mrs…I mean Ali?”

“Sure, and Jerry can rub some lotion on you back if you need.”

“I definitely need.”

I liked the sound of that.

She unfastened the cover up and twirled it off. I almost gasped out loud in surprise.

Her bottoms were one of the incredibly revealing thongs I had seen in pictures but never in person. The patch over her snatch, sue me I’m not a poet, was a triangle that had to be barely covering the top of her slit. She must have been totally hairless to wear that. When she laid down her perfect, but hardly tiny, buttocks were on display.

She rolled to one side and looked up at me in my chair,” would you do the honors?”

Would I? I would, except right now there was no way to hide my righteous wood. I figured, wtf, I saw her naked and fucking her boyfriend last night, she had to know what her body did to us guys. I knelt on a folded towel next to her and saw she had unfastened her top but unlike Ali hers was under her. Her delicious boobs squished out the sides, I love side boob shots.

When I squirted some lotion on her naked back it must have been cold because she jumped, causing the boob on my side to jiggle quite fetchingly. Us old guys like terms of that kind. I’m betting the one on the other side did too. Simple physics. When I started rubbing it around she moaned. Fetchingly. All right, I won’t use that one again.

I was about to get up when she rolled away from me exposing most of the tit on my side and it’s apparently erect nipple, “Mr…Jerry, I haven’t gotten much sun so far this year, would you put some on my, uh, bottom? I don’t want to burn.” Thank you, God.

Out of the corner of my eye I saw Ali was watching to see what I would do next. Silly woman. I only had one choice here. I hated to do it but I was the only one available. Another cool squirt of lotion got a delightful jiggle out of those orbs.

I used both hands to spread the lotion evenly and swore I heard a soft groan or two as I made extra sure the lotion was spread smoothly and evenly. The I went over it again. Darn! Some of the lotion had run down into the crack of her fantastic ass. I had to go in after it. When I slid my middle finger down after the slippery lotion I ended up going all the way to where I shouldn’t have gone. That drew an actual moan.

Ali was now giving me the evil eye. I just looked at her and shrugged. I do a really good stupid look. It may be genetic.

“So what did you want to talk about, Meg?” asked Ali trying to shut me down.

“This is kind of awkward, but I saw you guys last night, and I know you saw us too.”

That got Ali’s attention. She sat up and looked at Meg. Meg turned her head so she could make eye contact with Ali. I confess, I wasn’t looking at Ali’s eyes.

“I’m not complaining,” she went on, “what you two did was really hot. By the time Chad got there I was already beyond wet. Then knowing you were watching drove me crazy.”

“So what was it you wanted to talk about, dear.” Ali was trying to sound calm, but I think she was starting to get a little damp.

“Well, as you no doubt figured out I’m not on the pill. Chad refuses to use condoms, he’d rather pull out than use them, but I’m worried that he will cut it too close and I’ll end up pregnant. I saw what you two did and I thought maybe that would be a solution for Chad and me.”

“So you want some tips on doing it?”

“What I was hoping was that since you and I already have a history, sex wise, you might be willing to sort of share Jerry with me. Like, for my first time. Chad can be a little out of control and I want someone who can be careful. And gentle.”

Wait, wait, wait! What did she say? A history with Ali? Sex wise? Ali was looking at me with worry in her pretty eyes.

I said, “shouldn’t Jerry have some say in this?”

Ali rolled her eyes, “are you saying you might not want to do it?”

“Not at all. But I should still be consulted. Like when you two were having your history, sex wise.”

“I was hoping you didn’t notice that. But as they say, that’s history.”

“I think there’s still more history to be made there.”

“Are you talking about what I think you are?”

“I think you know you’re going to have to be paddled for ignoring our agreement.”

In a tiny voice Ali replied,”I know.”

“What are you saying?” exclaimed the lovely Meg.

I answered, “Ali and I had talked about her exploring her interest in having sex with another female. I’m not opposed to her doing that but it’s supposed to be in the open and possibly even with me watching. She knew if she broke that agreement there would be a price to pay.”

“I thought you said something about paddling.”

“I did. That was part of the agreement.”

Meg’s eyes had a bright shine to them, “I feel bad that I’m the cause of her being punished. Is there anything I can do to stop you from doing that? I would do most anything.”

This wasn’t helping my super hard woody, which was now leaking pre cum in copious amounts.

Ali spoke up,”that’s not necessary dear. It’s all my fault for not stopping things before they went too far.”

“But I have to do something. I’ll take the paddling for you.”

I had to try hard not to hyperventilate.

“No dear, I’m ready to pay for my mistake. It’s a matter of trust. I need to do this to regain Jerry’s trust.”

“Then I want to be punished too. It would never have happened if I hadn’t kissed you that day. So what about my request?”

“Are you sure you’ll still want Gerry to do that after being paddled by him? He won’t hold back and he swings a mean paddle.”

“So you’ve done this before?” Meg was positively drooling over the idea.

“Several times,” said Ali,”I’m afraid I’ve been a bad girl on more than one occasion.”

I had to jump in,” You should know what you’re asking for. It sounds real sexy getting your butt paddled, but it’s pretty painful. The pain turns Ali on, and we have some of our best sex after. But it may not be for you.”

Meg replied, “I hear you. But I’m getting damp just thinking about it. The last time my Dad took a strap to Mary and I it almost made me cum. I think the pain gets to me too.”

I asked, “how long ago was that?”

“When we were fourteen. Mom caught us naked together while I was showing Mary how to masturbate. Actually we were trying to figure out what lesbians were all about. Mom was afraid we were becoming perverts, so she had Dad strap us good. I had welts on my legs and ass for a couple weeks.”

“That sounds terrible,” said Ali, “but our paddling doesn’t leave any welts or bruises. It will definitely leave you red and sore though. What do you think, babe?”

I answered, “it sounds like if she wants it she should get it.” I stood up, no longer concerned about the sequoia in my pants, and headed for my den where the punishment would be given. We originally chose this room because it’s in the center of the house and also because I had the walls insulated when the house was built. I was concerned about having a quiet place to conduct business, I run my internet business almost exclusively over the phone, but it keeps sound in as well as out.

Ali, still topless, and Meg followed. I sat on the ottoman at the foot of my recliner and waited without speaking while Ali chose a paddle. We have several, including a two handed model from a fraternity that Ali bought at a yard sale. We had yet to really make use of that one, apparently that was going to change.

When Ali pulled out the two hander Meg gave a little gasp. I thought she might be getting cold feet until I looked at her crotch. The green material was soaked through. Maybe she really did enjoy the pain. Normally I spank Ali’s bare bottom while she lays across my legs, but obviously that wouldn’t work with this paddle.

I only thought for a second, then pushed Ali over to the desk, took the paddle from her and bent her over onto the desk. When she was settled I pulled down her suit bottom and left it around her ankles.

“So my dear,” I growled, really getting into character,” how many do you think you deserve?”

“Well ah, I don’t ah, maybe only a couple with that paddle.” she said in a rush.

I had in mind at least six, but didn’t tell her that. Without another word I stepped to the side and wound up then delivered about a 60% effort. The holes in the paddle made a hiss, which was her only warning before the paddle smacked her exposed butt. The sound was louder than I expected and Ali stood straight up, her mouth open in a silent scream.

Then she said, “oh my god, oh my god, fuck, fuck, fuck that hurt.” I pushed her back onto the desk.

“Meg!” She jumped. “Come over here and hold down on Ali’s back, I don’t want her moving around.”

Meg’s dark brown eyes were the size of saucers, but she moved across from me and put both hands on Ali’s creamy back. The paddle was long enough to hit both buttocks at once, so both orbs were already a light pink, with white dots where the holes were.

I stood back and decided that was probably just the right effort with this paddle, more might be too much, and cause her to use our safe word before I was done. I delivered the next five in a steady rhythm, not letting her catch her breath in between. By the last one Ali was screaming at the top of her lungs and crying. Her ass was a nice solid red. No safe word and pussy juice was coating both thighs almost to her knees.

Meg realized she should let Ali up and when Ali stood Meg took her in her arms and held Ali’s face against her soft boobs while Ali still cried, even hiccuping like a small child might. Meg kissed her tear covered cheeks, saying soft comforting things. The two of them together was totally hot.

After a couple of minutes of this I gently pried Megs arms away and moved Ali to the other side of the desk, “do you still want to receive your punishment, young lady?”

Meg looked a little shaken, but nodded in agreement. She pulled down her own sodden bottoms and kicked them to the side before laying those luscious tits down on the desk. Ali had some idea what it was going to take to control this large woman so instead of using her hands she lay the top of her body across Meg’s back.

I stood back and waited for a full minute. Anticipation was part of the game. When I began once again I got into a rhythm and delivered all six smacks in short time. I might have gotten mesmerized by the way her buttocks jiggled when I hit them and accidentally hit her a seventh time. No extra charge.

When Ali let her up they were once more in each others arms crying then kissing. Before I could say anything they were on the floor in 69 position with Ali on the bottom.

Good old Ali was already spreading Meg’s ass cheeks and fingering her tight brown pucker. Which was apparently driving Meg crazy. I quickly went to Ali’s room and grabbed the special lube. I dribbled a little onto Ali’s fingers, which she then used to lube Meg’s anus before pushing a finger in. Meg made agreeable noises so as Ali worked two more fingers into Meg’s ass I squirted a good amount of the lube on my rock hard cock. It was going to take a miracle to keep me from cumming as soon as I entered her.

When Ali pulled her fingers out I pressed the head of my cock against Meg’s slightly slack opening. It looked like she was somewhat relaxed so I took a chance and pushed the head in. Meg’s head came up and she shouted,”oh fuck!” I waited for a few seconds, totally fascinated by how it looked with just my tip in her distended anus. Finally I had to have more. Everything was slick enough that there was no reason not to just bury myself in her, so I did. Meg groaned loudly, exclaiming,”holy shit, he’s so thick it feels like he just stuck a baseball bat in my ass.” I heard my wife’s muffled voice,”stay there until she cums, let her get used to it.”

So there I stayed. I was going to cum anyway if I moved. I was trying everything to hold back. I even pictured my harridan fifth grade teacher naked. Oops, that might have been too much. I was so distracted I almost didn’t notice that Ali had Meg to the boiling point. Meg came with a howl, and came, and came. This girl had the most amazing orgasm I had ever witnessed. I was inspired now.

Despite all my thoughts it only took a half dozen long, slow strokes in her hot, slick anus before I tensed up and shot everything I had deep in her bowels. Ali must have still been working her magic on Meg’s clit because as I was finishing Meg lit off again. I can’t even imagine how wonderful it must be to have so many orgasms in one session.

Meg evidently was returning the favor as Ali quickly added her voice, “that’s it, that’s it, ohhh fuuccckk, yes yes yes, oh fuck keep doing that with your tongue, YYEEESSS!” I knew she was really getting with it because of the way her legs twitched and extended. When Meg rolled off Ali onto her back both of their pussies were red, open, and wet. Oh, and Meg’s top was pushed up revealing those luscious tits with her dark, swollen nipples.

I went to my room to shower and when I came back the girls were gone. I found them back in the cabana sunning topless and face up. I caught just the end of a conversation, Meg was saying,”… but never until I came. Just once I’d like to do that with a cock in me there.”

It was going to be a great summer.

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