Eventually Carl and Maggie join us and we all sit naked around the table, eating sandwiches and enjoying each other’s company. Carl seems to be memorizing Nicole’s tits, like I’ve just been doing with Carolyn’s. I’ve since shifted my attention to Maggie’s, comparing the smooth curve of her sizable globes with Carolyn’s and again concluding that they could almost be twins.
After dinner, Carl and Carolyn say goodbye, leaving Nicole, Maggie and I to decide how to spend the rest of the evening. We haven’t bothered getting dressed and I’m anxious to follow through on Nicole’s invitation to fuck her in the ass. I’m not sure she’ll go through with it if Maggie sticks around, but it would be rude to ask her to leave. I pull Nicole down on my lap on the couch and start kissing her and fondling her tits. Maggie, sitting in a chair opposite us, gets up and starts getting dressed.
“It’s time I left you two kids alone.” She says, sorting through her clothes, which are heaped in a pile under the window.
“Please stay a little longer, mom.” Nicole says, surprising us both. “I promised Nick that he could do me in the ass.” She explains. “I’ve never done it before and I was hoping you could help me do it so it doesn’t hurt.” She says pleadingly.
“Of course, honey.” Maggie says, excitedly. “Are you sure you want to do this?” She asks Nicole, raising her eyebrows at me questioningly. I shrug and shake my head, indicating that the transmitter had nothing to do with this.
“Yeah!” She says. “I’m sure. Watching you take both Nick and Carl was so fucking hot!” She says, excitedly. “You really seemed to get off on it. Does it really feel that good? I always thought it was something girls did that for their boyfriend’s pleasure, not their own.” She says.
“Oh, you are in for a treat, honey.” Maggie says, smiling. “It is not like getting fucked in your pussy and I don’t do it very often. But it can be an amazing extra stimulant to your lovemaking.”
“I’m ready to try it.” Nicole says. “You ready, Nick?” She asks me. I harden my cock and nod my head.
“Ready when you are, Nicole.” I tell her, as she moves off my lap.
“Let’s go into the bedroom.” Maggie says, grabbing the jar of lubricant. “I think it’ll be easier on the bed.” Maggie leads the way, and Nicole wraps her hand around my cock, playfully leading me into the bedroom, like it’s a leash. I can’t believe it! Not only am I going to finally fuck Nicole’s ass, but her mother is actually going to help! Un-fucking-real!
I make my cock hard, while Maggie applies ointment to Nicole’s asshole. Nicole is on all fours, with her ass right at the edge of the bed. I watch in amazement as Maggie’s finger disappears inside Nicole’s tight puckered hole. I’m surprised at how comfortable Maggie seems with this. Maybe today is some kind of turning point for them.
“The trick is to relax your sphincter.” Maggie tells Nicole as she works her lubricated finger in and out of Nicole’s ass. With her other hand, Maggie is reaching under Nicole’s stomach and starts stroking her wet pussy. “The other trick is to be very aroused when you do this. I think all the fucking you’ve done today will help this go pretty smoothly.” Maggie says.
“Okay, now relax, sweetie.” Maggie says. “I’m going to put two fingers inside you.” With the fingers of her left hand rocking in and out of Nicole’s pussy and her thumb rubbing across her clit, she starts working two fingers of her right hand into Nicole’s tight ass.
“Relax now, Nicole.” Maggie instructs, as she twists her fingers, screwing them into her ass. “Put more lubricant on my fingers, Nick.” Maggie says and I get the jar and smear a gob onto her fingertips. She pushes the lubricant in first, and then corkscrews her fingers in behind it. With her other her fingers buried in Nicole’s pussy and her thumb still massaging her clit, she starts gently finger fucking her ass.
“How does it feel, honey?” Maggie asks.
“Weird, but okay.” She says. “Your thumb on my clit feels great, but my ass just feels full.”
“Okay, we’ll take it slow.” Maggie says. “Get ready Nick.” Maggie says to me. “I think she can take it now.” I step up behind Nicole and make my dick as thin as possible while still keeping it very rigid. Maggie rubs lubricant all over my cock, twisting her hand up and down my shaft. She’s taking her time, while continuing to stimulate Nicole’s pussy.
“Be gentle with my little girl, Nick.” Maggie whispers, kissing me on the mouth, as she continues to smear lubricant all over my cock.
“I will.” I promise, positioning my cockhead against Nicole’s furrowed opening. Maggie has moved up on the bed beside Nicole and is continuing to stroke her pussy.
“Concentrate, Nicole.” Maggie says. “You have to relax your asshole.”
“I’m trying!” Nicole snaps, leaning away from me, as I try to push my cockhead into her tight opening.
“Don’t pull away, sweetie.” Maggie says. “Hold still so Nick can push himself inside you.”
“I’m scared.” Nicole answers. “Maybe this isn’t such a good idea.” She says, as I hold her hips with my hands and push my cockhead into her asshole.
“Oh fuck! It hurts!” Nicole yells. “Take it out, Nick! Take it out!” I start to pull back and Maggie shakes her head.
“Think about it, Nicole.” Maggie surprises me by using the trigger. “Ignore the pain and relax your sphincter.” Nicole is instantly quiet and her asshole relaxes around my cock, allowing me to push farther into her snug opening.
“Keep going Nick.” Maggie says, rubbing frantically at Nicole’s clit. I can’t believe Maggie is so adamant that I get my cock in her daughter’s ass. I inch my cock deeper into Nicole’s ass, little by little, while Maggie plays with Nicole’s tits and keeps her clit stimulated. After several more push and pulls, I finally get it all the way in. I hold still, letting Nicole catch her breath and get use it being there.
“How does it feel, Nicole?” I ask her, as I hold her hips and start gently rocking back and forth.