Debbie and I had an ongoing relationship with Cassidy; that girl was really a lot of fun. We had threesomes as well as one-on-one dates, by one-on-one, I mean Debbie and Cas and myself and Cas.
We were now sharing her girlfriend; our new relationship has been going on for over a month now.
The one thing that I knew Debbie still wanted was the the other guy thing like we had with Steve. I would like for her to have that as well. I don't mind saying we had a lot of fun with him.
I had thought of a birthday surprise for Debbie, and I was discussing it with Cas.
Cas happens to be friends with Andy, the guy from the band that we sort of knew.
I brought up Andy during one of our alone times, just after we had sex, my cum still oozing from her pussy. Cas was on my left side, hugging me, her head lying on my chest.
I ask her, "Cas do you still see that guy Andy from the band?"
She looks up and said with a smile, "I do. Why are you jealous?"
I say, "Maybe." Then I kiss her.
I then say, "Do you two still get together?"
She said, Yes, we still do from time to time."
I ask, "Have you ever been with him and another woman?"
She says, "She hadn't, but I would really be into it."
Then she says, "Is this about Debbie? She told me all about the friend that you shared her with. It sounded like you guys had a lot of fun."
I smile and say, "Yes it was a lot of fun, and her birthday is coming up on Saturday, and I know she is attracted to Andy. Do you think he would be into her? If he is, do you mind sharing him with her and her with him?"
She answers, "No, I don't mind at all, but how would this work? Would you want to be there also?"
I say, "No, this would be you three. It would be a present for Debbie from you and me. Plus, I'm sure Andy would prefer it that way."
She says, "You are a pretty cool guy, you know that. Letting your wife play like this. I would think you would want to see it, being it would be the first time and all."
I say, "I would, but I want this to be special after all. She would be free to do whatever she desires with him and you. I find that really hot and I'm not ashamed to say so."
She smiles, kisses me, then asks, "Should I call Andy?"
I say, "Sure, but in a little bit." I point to my cock which is now rock hard again.
She smiles and says, "Mmmmmm you naughty boy, you got me horny too with all this talk, but I want to do something different this time."
She then reaches over to her nightstand and pulls out a container of lube. I notice it was full and unopened.
Although I had fingered and licked her, I had not yet fucked her in the ass, and I guess she finally wants me to.
That said, what she tells me next really surprises me.
She says, "I have never done it in the back before, just been fingered. I want you to be my first. Your a really nice guy, and I really like you, and I know you will be gentle."
I say "Wow, I am really honored. Are you sure you want to do this with me?"
She says, "Yes I want you to be my first, so we will always have something special between us."
I say, "Cas, I would love to be your first, and I promise I will be very gentle and stop if you say so for any reason. Just let me know."
Cas smiles and hands me the lube with a wink, then gives me a passionate kiss. She then proceeds to get on all fours, spreading and tucking her legs in, head on the pillow with her ass sticking out for me.
I did not think my cock could get harder, but it does. I regret thinking that this should have been a done deal for her; she seems well experienced so to speak.
I really do like this girl.
I move behind her to the back of the bed. She had clearly thought how she should be positioned for easy access to her asshole. She is positioned perfectly.
I start by using my tongue, and I lick her asshole to help relax her. She quivers as I slide my tongue inside of her butthole. She starts to sqeeze my tongue while it is inside, pushing it out. I stick it back in, and she relaxes, moaning slightly at the sensation.
I sit up, and I hope that I have started to relax Cas's asshole a little. I remove the cap off of the bottle of lube and I peel the seal off. I put the cap back on and pop it open. I apply some to my fingers and rub it around to warm it up.
I tell Cas, "This may be cold," and I apply it to her anus. She flinches just a little. I rub the lube on her butthole and let a finger slide in. She moans a little as I start to fingerfuck her asshole.
I slip in a second finger to help loosen her up. She moans a little more. She starts to squeeze a bit, causing me to ask, "Are you okay?"
She says, "Yes, It feels good."
I tell her to make sure she tries to relax when the big event starts. With that I pull my fingers out and add some more lube to them, then I apply it to her asshole.
She squeals a little, saying, "That's cold!"
I apologize as I move the lube around to warm it up.
I reinsert two fingers inside her ass, and I fingerfuck her a bit while using my other hand to play with her pussy. Her pussy feels very wet.
Cas moans as I touch her clit, and I notice her asshole relaxes as I play with her pussy. This may help later.
I continue doing this a while to loosen her up. I may not be the longest cock around; I'm only about Seven inches, but it is on the thicker side.
I pull my fingers out of her ass, and I ask her, "Do you want me to try now?"
She says, "Yes, I want you to."
I say, "Okay, when I'm putting it in, you should play with your clit. I noticed you relax more back there when I was touching you."
She say, "Okay I will."
So now I take the lube and apply more to her ass and a put a fair amount on my cock. I get in position behind her, and I place the head of my pre-cum oozing cock against her butthole.
Cas gives out a sigh of anticipation when I make contact.