Monday morning
The alarm went off and someone was stroking my cock. Carolyn was spooned up against me from behind and she was kissing my neck. Ellen wasn't in bed with us, it sounded like she might be in the shower. I turned around and pushed Carolyn onto her back and slid up into her.
"Good morning my dear."
"Good morning Don, I missed you last night. Please give me a Donnie special."
"One Donnie special coming up."
I pounded into her hard.
"Yesssss, that's the way, fuck me, fuck me hard."
I slammed into her as hard as I could.
"Fuck meeeeeeeeeeeeeeeeeeee."
I left my load in her belly.
"Thanks Don, I needed that."
"My pleasure, my love."
She kissed me tenderly. "You are a special man Don. I love you so much."
"I love you too milady."
At lunch that day Crystal and I mutually flirted with each other for a minute or two, but she had lunch with her lapdog, I mean my co-worker.
When I got home at 5:30 I was surprised to find Ashley in the living room.
"Hi Ashley, where's Stephanie?"
Ashley stood up and walked over to me. She was looking damn fine. Her shorts were skin tight and she had some sort of mini-blouse on that was clinging to her tits very nicely. There was also a lot of pale pale skin on display.
"Hi Don, Stephanie's busy, I'm actually here for you. I'm your constitutional. I hope you're not disappointed."
I licked my lips lasciviously and leered at her.
"How could I be disappointed honey, you look absolutely delicious."
Ashley blushed her full body blush. I pulled her in for a passionate kiss and grabbed onto her ass for dear life.
'HHHhhmmmmm, I'm not sure what magic powers you have, but I just came," she said.
"Let's head to the bedroom shall we?" I replied.
My hands were all over her body as we made our way to the bedroom and she was getting redder and redder. We fell into a 69 and I was licking her cunt like there was no tomorrow. I was pistoning my fingers into her ass furiously. She came again and my face was drenched in pussy juice. We switched positions and kissed each other hungrily while I kneaded her titties.
"Please fuck me Don. I need your cock inside me."
"With pleasure my lady."
I slid my cock in her missionary style and let her do the most of the work. If things worked out the way I hoped I would be cumming in her ass and I had to be careful not to come too soon. She bucked at me pretty hard and then she came loudly.
"OOOOOOOOOOOooooooooohhhhhhhhhhhhhhaaaaaaaaaaaaaaaaahhhhhhhhhhh."
She looked at me adoringly and kissed me. I tapped her knee and she quickly got on all fours. I spit into her asshole and slid two fingers in.
Ashley turned around and said, "Stephanie tells me that there is nothing better than the feeling of your cock in her ass. Please be gentle Don. I've never done this before."
I spit into her again and then pushed in.
"OOOOOoooooooooooooohhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhh."
"How's that honey?"
Ashley looked back at me. There were tears streaming down her face.
"It huuurts."
I tried not to move my cock in her and caressed and licked her back.
"Just give it a minute or two."
She smiled at me weakly and then moved her ass around a little.
"AAAaaaaaaaaaahhhhhhhhh."
I hadn't even slipped all of my cock into her yet and she was still crying.
I played with her cheeks and she moved around a little more. I pulled out slowly and eased my way back in.
"OOOOOOOOoooooooooooohhhhhhhaaaaaaaaaaaaaaaaaahhhhhhhh."
I moved up to kiss her neck and lick her ear. She was moaning and still crying.
"Do you want me to stop honey?" I asked.
She shook her head.
"It's got to get better doesn't it?"
"I'm not sure honey, but every other lady I have tried it with has enjoyed it."
"Go ahead and give it to me then."
I pulled out and pushed in again with more force this time.
"AAAAAAAaaaaaaaahhhhh, slam it into me Don."
Who was I to argue with a lady? I slammed it into her. I stopped worrying about Ashley and pounded her hard.
"AAAAAAAaaaaaaaaaggggggggggggggghhhhhhhhhhhhhhhhhh."
I kept on pounding and pounding and then I left a quart of cum in her ass. I collapsed and then I was surprised to see Stephanie rush up.
"Out of my way Uncle Don," she said.
Stephanie was licking the cum out of Ashley's ass. Stephanie was still off limits. So I grabbed my clothes and left. I wasn't really sure how Ashley was doing at all.
Carolyn was in the living room.
"How'd it go with Ashley? Did ya get her anal cherry?" she asked with a sexy grin.
"Things were going great and then, yes, I fucked her ass. I'm not sure if she liked it at all. She was crying. Stephanie is in there with her now."
I must have sounded worried because Carolyn got right up and dashed into the bedroom.
Carolyn came back in a few minutes frowning.
"Ashley is pretty shook up."
I got up to head to the bedroom and try and help. Carolyn pulled me back down.
"You can't help her Don. She needs Stephanie right now."
I was feeling terrible about the whole thing.
Carolyn said, "I had a similar thing happen to me when I was only 19, except the man who took my ass had no empathy for me at all. I was just another notch on his belt. I never saw him again and I never had a girlfriend like Stephanie to look after me. I'm sure you were gentle, weren't you?"
"I didn't do anything differently than I did with you or Ellen or Stephanie, but Ashley was crying after the first penetration. I asked her if she wanted me to stop, but she had heard such glorious things about it from Steph that she asked me to keep going and then she pleaded with me to do it harder. There wasn't much I could do, but I feel so guilty."
Carolyn kissed me tenderly.