Prologue:
The following is a continuation of "Welcome to the Group", and I highly recommend reading it prior to.
As always, comments are welcome as long as they are constructive.
*****
After I announced Amber and Teresa wanted to be ass-fucked by Walter and David respectively, both broke out in a big smile. Everyone else applauded to the fact they agreed to do it "center stage" so the rest of us could watch. But Amber still appeared a bit hesitant since she was new to the group. Just the opposite for Teresa who was raring to go and chomping at the bit.
Seeing Amber was I decided a little encouragement might be needed..."Okay you two, it's showtime. But if you want to back out Amber, I'll be glad to take your place. I can understand being somewhat reluctant with everyone watching. But take it from me, if you have any exhibitionist tendencies as you shared with us earlier I can guarantee from my own experience you won't be sorry. Most likely the opposite. But if you are afterwards, feel free to chastise me for it. But I doubt you will."
Teresa added her two cents also..."Lacey's right Amber. Same here for me the first time. I was nervous as hell with everyone watching. Somewhat embarrassed too in front of my husband. But once into it, it was a big turn-on. Trust me, like Lacey says you won't regret it. Now let's get on with it. I'm dying for David to ass-fuck me with his fat cock."
After she finished, Amber grabbed Teresa's hand before they made their way to where Walter and David were. Then as if planned, both wrapped their arms around them respectively and gave each a long kiss before leading them to the mattresses on the floor.
The rest of paired up and sat spaced around the large U-shaped sofa so we'd have plenty of room to get frisky. Roger and I paired up, Bill with Cindy, which left Rita and Debbie to watch together.
After Walter and Amber reached the mattress she put her arms around his neck and whispered in his ear. Walter first laughed before whispering back in her's. Come to find out later, Amber informed him both Teresa and I praised him for his ass-fucking skills and she hoped he would be as good as they claimed. Walter responded by thanking her for setting such a high bar and hoped she wouldn't be disappointed.
She then whispered in his ear a second time, which was to inform him to be gentle since it's been a while since she was last fucked in the ass.
After some heated kissing Amber dropped to her knees to take Walter's semi-hard cock in her mouth. But only his cockhead. After she sucked and licked it for a few minutes Walter was rip roaring hard. His cock was standing out straight except for being slightly bent in a downward arc because of its long length. And it was also bobbing up & down ever so slightly.
Amber then proceeded to get on her knees and elbows with her legs spread. Coincidentally it's my favorite position also for anal. Resting on my elbows and forearms versus my hands, which positions my ass at just the right angle for anal. Once she was, and with Rodger and I sitting only a few feet away, it was the first time I got a good view of her asshole. And like everything else about Amber, it was near perfection. She had the bumhole of a twenty year old. While her asshole was a bit on the large size in comparison to us other ladies it still had beautifully defined anal ridges and a very light skin tone. Not as dark as the anus and labia of most women our age. Large as it was, it was obvious she would have no trouble taking Walter's large cockhead initially. Plus it was nearly hairless except for a few wisps of fine blonde hair from what I could see.
As for Teresa, she didn't waste any time getting into position. When her and David reached the mattress she went straight down on her hands and knees and began wiggling her ass.
Once both were, Cindy was kind enough to place some lubricant next to them. No doubt David would need it, although Walter might not since he most likely would go down on Amber's bumhole first.
Once Amber was in position, and Walter on his knees behind her, he did exactly as I expected. He bent over and began licking Amber's asshole in small circles and then up & down like a dog lapping a bone. As he did Amber began moaning ever so softly.
"God, that feels so good Walter...please don't stop."
Which he didn't, and wouldn't as he was enjoying it as much as her. If anything his licking became more vigorous. Eventually he probed her bumhole with his tongue. And deep as he could. When he felt she was ready for anal penetration he first used a finger and ever so slowly inserted it deep as he could. Then two fingers after which he began to gently finger fuck her.
Amber eventually blurted out..."While I'm loving you fingering my asshole Walter, it's time to do me with your cock."
To be on the safe side Walter lubed his dick with the lubricant Cindy provided. After it was he held Amber's hip with one hand and with the other placed his cock against her asshole before slowly plunging forward until it popped in. And as expected, very easily.
As it did Amber let out a soft moan before saying..."Oh wow...now slide that long piece of meat deep in my ass Walter."
Slowly but surely he did until his pubic hair was tickling her anal ring. After which he grabbed both hips and began a slow but steady humping motion. All while with-drawing backwards until only his cockhead was still embedded in Amber's asshole before plunging forward nearly balls deep. Very long and continuous strokes, which didn't take long to put a smile on her face.
As for David and Teresa it was a much different scenario. David at Teresa's request avoided any oral foreplay and simply lubed his cock and Teresa's asshole. Once both were he placed his cock against her anal orifice and began inserting it. Since David's cockhead is cone shaped and the same diameter around the glan corona as his cock shaft it initially entered Teresa's bumhole fairly easily. But once the full diameter of his cock began stretching her anal sphincter it was a different story.
You could see the pain on Teresa's face as she gritted her teeth. David sensing she was stopped to ask if she was okay.
"Be lying if I didn't say it was hurting, but please continue. I'm sure I'll be fine once your cock is fully inserted and I get use to its girth."
So he did and ever so slowly until all five inches of his dick was embedded in Teresa's ass. After which he paused to ask again how she was doing.
"Doing fine David. I think I'm past the worse part so you're good to go. But slowly please."
Which he did with a very slow and almost lazy humping motion. After a while the look on Teresa's face changed from one of discomfort to a more normal facial expression. Slowly but surely any pain she first had turned into a more pleasurable sensation. And slowly but surely she began participating by gingerly humping backwards each time David humped forward.
