My Youth
Chapter 15: Caroline - Part 7

Copyright© 2016 by Hellraser

Coming of Age Sex Story: Chapter 15: Caroline - Part 7 - Recounting growing up and certain indiscretions along the way

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa   mt/ft   Ma/ft   Teenagers   Consensual   BiSexual   Heterosexual   True Story   Incest   Mother   Brother   Sister   Daughter   Group Sex   Anal Sex   Analingus   Cream Pie   Double Penetration   First   Fisting   Oral Sex   Safe Sex   Sex Toys   Squirting   Tit-Fucking   Voyeurism  

Caroline went to the bathroom to check out the douche bag. Sure enough, she found a small, smooth tip on the end of the hose. Returning to her mother, she leaned over to whisper in her ear. Mary smiled at her and took her hand, leading her into the bath and closing the door. It didn’t take the head cashier at Wally World to figure out what they were going to do. I let myself into the kitchen and helped myself to the coffee maker. Wonder of wonders, there were still three doughnuts left.

I was finishing the last of the doughnuts about 30 minutes later when Mary came in to join me.

“Caroline is in the shower. She’ll be out shortly.”

“Why did I just KNOW she’d be taking a shower. How did the enema go?”

Mary giggled as she spoke “You KNEW she was going to get an enema when she went in with me, didn’t you?”

“We’d had a small conversation about preconceived ideas and she was totally shocked that you prepared yourself for the eventuality that you’d be having anal sex. If she went though with it, I knew she’d want the shower. It’s a no-brainer. She’s still convinced most of the human body is dirty.”

“We talked while she waited for the bag to empty - anything to take her mind off the cramps. I told her that gets easier with practice. You really covered a lot of ground with her, but I’m sure she understands it all.”

“Time, exposure and experience. You didn’t learn it all in one night and neither will she” I said.

“In this case, I think it was the rimming that moved her towards wanting to try something up her ass. I hope she can relax and learn to enjoy it. I damned sure do.”

“Let’s do her together. We can keep her mind occupied until it’s a done deal.”

“Buck, let me ask you something and don’t be afraid to answer, ok?”

“Depends on the question, Mary, but ask anyway.”

“Do you think I come off as, what do you call them, a ‘pain slut’?”

“Bad analogy, but you pet a dog, it licks its lips to show it likes the affection. Other times, you wrestle around with it and play rough and the dog enjoys it just the same. Why should humans be all that different?”

“Are you sure you aren’t really 50 years old” she asked, “you know so damned much about people.”

“I read a lot and look at all the dirty pictures. Seriously, none of this shit is original, it’s human nature and you’re a product of your environment. Your mama or your grandma told you something and you either took it as gospel or you found out if it was fact or fiction. I bet your mother told you NEVER to touch yourself ‘down there’.”

She about rolled on the floor laughing. “If my mother knew half the stuff I do now, she be spinning in her grave.”

“I’d say, for the most part, you turned out pretty ok. I’ve learned to like how open you are with your daughter, damned sight more than I’ve gotten from MY parents. Hell, they haven’t slept together for as long as I can remember.”

Caroline came out of the bathroom freshly showered and perfumed and floated into my arms, carrying a bottle of baby oil. “I want you to do to me exactly what you did to mom. You get the once in a lifetime chance to get my anal cherry.” She was in a bubbly mood and I sure didn’t want to burst her bubble. I took her hand and led her over to her bed. I was getting tired, but I think I had at least one more shot left before I passed out from lack of sleep. Maybe I needed a shower to perk up. But then again, sleeping beauty has had two naps where us old folks struggled along on adrenaline.

Caroline made one bounce and came to rest on knees and elbows wiggling her ass like a puppy. Her mom went to her front and started pulling on the girls little nipples, getting a few moans from her as she enjoyed the attention. Caroline enjoyed getting rimmed, so that’s where I started. Circling her tight ass with my tongue she wiggled with delight. Her mom managed to get under her and worked on her little clit while Caroline played with her mother’s larger one.

When her ass began to relax and lose the tight clinch. I poured a trickle of baby oil down the crack of her ass, working it into her tight pucker. She didn’t seem to notice. Baby oil isn’t my favorite type of lube ... it’s not all that slick but it was what I had to work with. Actually, referring to the present time, Astrolube and the like wasn’t prevalent yet. Olive oil was a preferred lube or KY jelly. I generously coated my semi-hard cock and stroked some life back into it. I got a finger in her ass and so far, so good. As she loosened more, I could add second finger and pour some oil down the crack between them. When her ass let me work those two fingers in and out with some ease, it was showtime. My free hand poured oil on my dick, then rubbed it all over. Pulling my fingers out, I eased the head of my cock in and stopped. She soon got used to feeling full. I’m sure her mother had described the gamut of feelings she’d experience as she took her first dick. She was tight, but not cripplingly so. Easing oh so slowly in, I watched inch after inch slide down her poop chute. I finally bottomed out and started the slow trip back until only the head remained.

“OH, HONEY! Stop a second - I need to get used to this!” she cried

Mom had other ideas. I felt her slide under Caroline until she had her head under her raised pussy. From Caroline’s hunching, I knew Mary was working on her clit. Imagine my surprise when I felt pressure on the UNDERSIDE of my dick. Mary had worked her fingers into her daughter’s tight pussy. I could feel her fingers move through the thin membrane separating me from her pussy. Caroline started to move and if I didn’t get with the program, I’d be out in the cold. Grabbing her hips, I made a full stroke until my balls rested on her ass cheeks. She hunched back at me. I withdrew and made an even harder thrust and Caroline met me halfway with a backwards move of her own.

 
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