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Amy complained, "Awww. Bummer. I feel so empty. You don't want- OH!" She had to cry out because seconds after he pulled his erection out of her pussy, he pushed a finger into her asshole. It slid in surprisingly easily, because that hole was heavily lubricated.
He noticed that someone had thoughtfully left a bottle of lubricant by his bedside as well. It made him feel good and very pampered, as if silent, secretive elves were taking care of all his needs behind his back.
"Oh, ALAN!" she cooed lovingly as she wiggled her ass enticingly. She greatly enjoyed the feel of his finger sliding deep within her rear hole.
He got off on her obvious excitement and roughly grasped and fondled her big ass cheeks. He only had one free hand to do that at the moment though, which was frustrating because he wanted to touch every part of her wide yet firm ass at once.
He went deeper and deeper into her rectum with his middle finger with each pass. After some minutes he had it in as far as it could go. Still, even with all the lubrication, the fit was tight.
Her asshole was also quite active, spastically clutching and clenching around his finger as he probed her.
Eventually he wanted to switch to putting two fingers in, but he encountered difficulty even though her hole was looser than usual. He noted, "I see you've prepared yourself."
"Yep! I've been wearing butt plugs, like, ALL the time! School is such a drag 'cos Mother said I couldn't wear one there, but I wore one even during the whole Dr. Fredrickson thing. I drank some wine earlier to help me relax. And I just had an enema and even-"
"Whoa! Too much information. Boy, you're tight. UGH!" He wondered why her asshole wasn't more open if she'd been wearing butt plugs so much. In fact, a good deal of time had passed since she'd taken the latest one out, so it wouldn't mar her display as one of his "desserts." Since then, her hole had tightened up again.
"Aims, can you pull your ass open with both hands for me? You're so tight I need to use my other hand to help get a second finger into you."
"M'kay," she dreamily sighed. Reaching around with both hands, she cupped her buttocks and slowly spread them open for him. She shivered in excitement as her big ass cheeks parted.
He felt the ripples of her excitement as her asshole fluttered around his buried finger. While slowly pistoning the finger he already had inside her, he tickled and teased the outside of her anus with gentle strokes and feather light touches from his other hand. Gradually, his technique started to pay off as her anus relaxed and reveled in the attention rather than tensing up and clutching at the finger already imprisoned in her exquisite tightness.
He kissed up and down the cleft between her spread buttocks as he slowly fingerfucked her asshole. That made her sigh and moan and pull her ass cheeks wider and wider. He finally felt she was ready for more and managed to push a second finger into her.
She responded with loud and very excited groans as she arched her back and thrust her hips back onto his fingers. In fact, she kept pushing back until they were as deep as they could go. Her whole body shuddered as her asshole throbbed and pulsed around his fingers.
He was able to piston his fingers in and out, with some effort, but the resistance he encountered made him wonder, How on Earth will I be able to get the width of my dick inside this tiny hole if my two fingers can barely make it?
But for the time being he just enjoyed himself and pistoned with his fingers while kissing her all over her back. He could tell she was thrilled too from her increasingly sexy moaning.
Even though she was normally very relaxed, she seemed both excited and nervous right now. He figured her excitement was as bad as her nervousness was for making her ass tense up. He ran the tip of his tongue up through her ass crack in a single tickling swipe, which made her squeal with glee, but also tighten up a bit more in surprise.
He hoped that fingering her asshole with two fingers would help her get used to being penetrated enough for the main event yet to come. Meanwhile, he tried to do everything else he could think of to get her to relax. He had her lie face down with a pillow under her hips to raise them up. While he kept working his fingers in her ass, he massaged her back with his other hand and nuzzled his face in her neck. He cooed, "Aims, I want you to know something. I love you so much. Whatever happens, it's cool. Even if we don't get it in-"
"We're going to get it in!" she hotly interrupted. She sounded extremely determined and shoved her ass back onto his fingers as if to underscore her resolve.
He felt her whole body tense up at the same time, and thought, Well, that backfired. What now, genius Romeo? If only Heather knew just how clueless I really am when it comes to anal sex, she'd probably laugh in my face. I read a little bit in those sex books I bought, true, but none of them had anything to say about an asshole like this one. If I try my dick now there's no way it's going to work. Dang!
While he pondered that problem, he kept at what he was doing, pistoning, and massaging, all the while cooing happy things almost directly into her ear. He said, "Aims, you're the super bestest girlfriend ever."
She laughed. "Hey! You sound just like me! YOU'RE the superest!"
"No, you are! You're the super duperest!"
"No, YOU are! You're super double duper!"
Before long, they were laughing and teasing and tickling, and generally having a really great time. The more Amy laughed and giggled, the more her anus eased its clenching.
He felt it almost seemed a shame to interrupt their playing around with the anal sex. However, while he wasn't rushing things, he was also aware that Suzanne was waiting for him. So, once he had Amy as relaxed and soft as mush, he plotted his next move.
He called out, "SIS! HEY KATHERINE! CAN YOU COME HERE?"
It took a while, but Katherine did come. He thought she was just across the hallway in her room, but in fact she'd been downstairs in the basement, jealously watching and masturbating to the video of action in his room. So she was a bit flushed and disheveled. She popped her head in. "Yes, Brother?"I think you should take a look at
"Good. You're here. Big Pleasure Pillows Sis, can you do me a favor? I'm having a bit of trouble fitting in. Can you get me a variety of anal dildos from the underwear cabinet or wherever they may be? I'm thinking of using those as a kind of stepping stone."
"Ah. Okay. Just a sec." As she walked off, she thought, Grrr! Martyr sister has to go do the dildo fetching errand while brand new E-cup sister gets to have all the fun. Why did I have to volunteer to give him a break this morning? Everyone else gets a big welcome back fuck full-on production, and I just get a quickie under the table. No fair. No fair! Still, I shouldn't blame this on Aims. She can't help it if he's making her feel so great. Grrr! ... "You're the super duperest." When is he going to say things like that to me?
She came back and rather testily handed Alan several dildos.
He could see she was moody, but he quite literally had his hands full with Amy.
Katherine spun on her heels and left the room. Despite being irked, she couldn't help herself and went downstairs to watch them on video some more.
He said to Amy, "Okay, I've heard this is easiest if we do it doggy-style. So get up on all fours on the bed."
"M'kay!"
Wordlessly, he pulled his fingers out and replaced them with a rather small and soft jelly anal toy. It went in all right, so he started sliding it in and out. He was amazed at her reaction. She'd been loving his fingers, but now she seemed practically beside herself with ecstasy. Soon she was gasping, panting, and moaning as if she was in the middle of a wild fuck romp. He joked, "Aims, save some of that excitement for when I actually get a real dick in there."
"I'm sorry Brother, but it feels SOOOOO GOOOOOD! I think I have kind of a ... a thing for ... anal... Brenda- OH! YES! ... Mmmm! That's so good!" She was too carried away to be able to tell him what she and Brenda had discussed the night before, which was just as well since that was supposed to be a surprise and he had no clue that Brenda had been in the Plummer house recently.
Experimentally, he reached forward and touched her clit.
Amy let out one of her ear-splitting screams and came in a massive climax. She was so overwhelmed that she fell forward into the bed, completely limp and spent.
Again, he was a bit chagrined by the intensity of her reaction. If she's enjoying a tiny little dildo this much, then my dick is liable to kill her. This is nothing like the way I anally deflowered, say, Heather or Mom. This is an intense struggle! A battle!
Luckily, the climax seemed to have greatly relaxed her. In fact, now she was so limp she could hardly even sit up on her own. So he pulled her down to the bottom of the bed and had her lie up against it on her belly. Her ass hung out over the edge and her knees rested on the floor.
"Aims? I'm going to give it a shot now. I think it'll go fine. Okay?"
"M'kaaaaaayyy." She was so relaxed that she even slurred her speech.
He put more lubrication on his hard-on and around her sphincter. Then he pulled her ass cheeks wide open, put his cockhead up against her asshole, and paused.
He prayed, Please, God, make this fit! I'm going to be so bummed if I can't fuck her this way. She'd obviously love it so much. But if it doesn't fit now, with her as limp as a puddle of goo, it never will.
He said, "Aims? My dick is up against your hole. I'll hold still and let you push back, okay? That way you can go as fast or slow as you want. Do you think you can do that?"
"Mmmm hmmm..." Her voice was so relaxed that he feared she was falling asleep. But she was far from sleepy. Slowly but steadily, she lazily rocked her hips back and forth while Alan kept a firm grip on her plush buttocks, holding them apart.
She pushed back again and again, but the progress could only be measured in millimeters. Finally, she said, "My love, I think we're going to have to do this together. You push forward, I'll push back, and then maybe we can find the right rhythm. Don't hold back. I can take it! Push!"
So he pushed, in time with her efforts.
But she suddenly began to yelp at each syncopated thrust, "Ouch. Ouch! Ouch! OUCH!"
He stopped pushing, but he didn't pull back and lose any of the hard-won progress his cock had made. They rested while the tip of his boner kept her twitching asshole slightly dilated.
When she had mostly recovered, she said in a cute voice, "That was far too ouch-y." But then, after some more deep breaths, she said with great determination, "I am not going to give up. Don't even THINK about stopping now, my favorite boyfriend!"
All the while they rested, her ass had been slowly relaxing and adjusting to accommodate the large intruder. So when they started pushing again, it was a bit easier, and they made a little more progress, slowly but surely.
But his cockhead still hadn't gone in yet. That was the widest and most difficult part; although both knew it would be relatively smooth sailing after that.
They gathered their energies for one big effort. They wiggled and pushed and screamed for what seemed like ages. Just when Alan was about to give up and concede that his erection simply didn't fit and could never fit, there was an unexpected "whoosh" sensation. His cock slid into Amy a good inch or more before it stopped again when her asshole clamped down hard with a vice-like grip on his intruding meaty shaft.
Amy's head came up off the bed, her back arched, her eyes grew as big as milk saucers, and her mouth hung wide open. She gasped for air in great gulping lungfuls as though she couldn't breathe. Her whole body reflexively recoiled away from him to try and escape the painful penetration of her asshole, but her position with her ass hanging off the bed didn't allow her enough room to pull away.
He hooted and hollered, pumping his fists in the air even as he continued to press his cock in deeper. "It's in, Aims! It's in!"
"You- OW! You don't have to- ah! ... tell me!" She panted between heaving breaths. "I can- huh! ... feel it, unngh, so big! Oh!" She buried her face in the bed, clenched her hands into fists and pounded them into the bedsprings like a drum major, making the entire bed vibrate. Her whole body kept jerking as waves of pain lashed outwards from her powerfully pulsing asshole, which kept trying to expel the enormous erection that had stretched her decidedly small anal sphincter to its limit.
