Chapter 22: February 1

Katie had let me know earlier in the week that Becky still had some lessons for me, so I was up early again today. I had no clue what the lessons would be about, but since I’m still new to being sexually active, I just assumed I didn’t know everything I needed to know yet. Using my fingers in Becky and Katie, and finding their G-spots, had been a revelation.

Becky called Mom right before ten and asked if it was okay for me to spend the day there, and Mom had Dad drive me over. Mom’s only condition was that I come home by dinner time. I wonder if my parents actually look forward to me being out of the house. Maybe it gives them a chance to run around naked or have the Kowalskis over. I don’t know. Part of me doesn’t want to know.

Dad let me out in front of the Schumans’ and was driving away by the time I knocked on the door. Becky let me in, delivering a blistering hot kiss the moment the door closed behind me. Before we even left the entryway, she cautioned me that today’s lesson was going to be about ass play. She said we weren’t going to have anal sex, but that we would use tongues, fingers and toys to give each other pleasure via our butts.

Licking her asshole sounded like about the ickiest thing I could ever do, and I told Becky that. She said we would both be squeaky clean, so it wouldn’t taste bad. She said it wouldn’t even as strong as licking her pussy. She told me she really loved the way it felt when it was done to her, and I might just love it, too.

“Just try it,” she told me. “If you really can’t bring yourself to do it, or you just don’t like it, we’ll stop. No still means no.”

I agreed, reluctantly, to try, so we stripped and stepped into the shower where we washed each other all over with special extra attention to our butts. It was kind of fun teasing Becky’s butt hole with a soapy finger, but I wasn’t so sure about it when she did it to me. I felt like it was kind of gay. Still, I tried to keep an open mind.

Once we’d rinsed off and dried, we moved the party to Becky’s bed, where we started off with regular oral sex; that is, I was eating her pussy. After a while, she lifted her legs and pulled them back as far as she could, exposing her anus to me. Her asshole was a little round ring surrounded by a crinkly area and the skin in the deepest recesses of her crack was darker than her pussy lips. There wasn’t any hair there, and I asked Becky about it.

“Did they wax you here, too?” I asked as I trailed a finger along her crack.

“Sure did,” Becky said. “Normally I’m pretty hairy back there. How does it look?”

“Smooth.”

“Have a taste,” she urged, and I obeyed. It reminded me of my first experience with oral sex, where I was so afraid I’d taste her pee, except this time I was afraid I’d taste something much worse. I didn’t. The reason for that is all the juices from Becky’s pussy that had run down across her asshole. She was clean otherwise, so it wasn’t bad at all. The texture was interesting. I laughed a little when the idea hit me of what the texture was.

“What’s so funny?” Becky asked.

“It’s like licking a rubber cheerio,” I told her before going back to licking her little ring and taking an occasional swipe at juices that were oozing from her pussy.

“Stick a finger in my pussy,” Becky panted. “Get it wet so you can push it in my ass.”

I pushed my index finger into Becky’s depths to gather up some of her lubrication, bringing a finger-full of the goo up to her little pucker, where I started to push my finger in. I could feel Becky’s ring flex around my finger to let me in, but she was incredibly tight. I only got in about as deep as the base of my fingernail when she asked me to stop for a second.

“This is going to take a lot of extra lube,” she sighed. “Let me get it.”

She pulled out a drawer on her nightstand and retrieved a little bottle of clear liquid. When she handed it to me, I read the label on it and discovered it was called ‘Astroglide.’

“There’s no such thing as too much lube when it comes to anal play,” Becky said as she got back into the position she’d started from. “Squirt some on my anus and spread it around, then coat your finger really good with it and we’ll try it again.”

I did as she directed, using enough of the Astroglide on her asshole that it was in danger of running down her leg. My finger was likewise well-lubricated. When I told her I was ready, she told me to push into her firmly but to go slow. I pushed again, and she flexed again, and soon my finger pushed through until its full length was buried in her behind. My girlfriend’s mother was panting as I held my finger deep in her rectum.

“Whew! Geeze,” Becky grunted. “Just hold still, John. I need a minute to get used to this.”

“Are you all right?” I asked, concerned that she might be in pain. “Am I hurting you?”

“Not exactly hurting,” she panted, “but it is a little uncomfortable. Just wait, and I’ll tell you when you can move.”

I sat there for a couple of minutes while Becky got used to the sensations of my finger up her butt. While I waited, her internal muscles kept clinching on my finger. It was uncomfortably tight. I couldn’t imagine what that kind of squeezing would do to my dick if I ever managed to get it in there.

“OK, try to move your finger in and out a little,” Becky told me as her breathing settled down. “Go slow!”

I did as she directed, slowly moving my finger in and out about an inch at a time as Becky kneeled in front of me.

“Try playing with my clit a little,” she directed.

I used the thumb of my other hand to rub her pussy and clit while I kept slowly moving my finger in and out of her ass. It felt like it helped her anus to loosen up a little, but it was still really tight, and I could tell Becky was uncomfortable.

“Do you want me to stop?” I asked her.

“If you don’t mind,” she said. She sighed in relief as my finger slipped out of her backside. She let herself slide down to lie on her stomach.

“Go wash your hands,” she said, “and bring a washcloth to clean me up, if you would.”

I got up from the bed, stopping to kiss Becky’s cheek as I headed for the bathroom. I washed my hands really well, making sure there wasn’t anything icky on my index finger or under its nail, and then wet a washcloth in warm water to take back and clean up Becky’s backside. When she saw me coming out of the bathroom, she got back up on her hands and knees so I could clean her up.

“Wipe up, away from my pussy,” she told me. “We don’t want to get anything in my vagina.”

I washed the lube off her, moving the cloth in upward strokes like she told me to and told her when I was done. She flipped over and sat cross-legged on the bed.

“I’m sorry I couldn’t give you the full experience of anal sex,” my girlfriend’s mother apologized, “but I’ve never been able to take anything bigger than a finger back there.”

“You were really tight,” I nodded. “I don’t think I could have gotten my cock in there.”

“Probably not,” she replied. “Thanks for taking it slow and making sure I was alright. That was sweet of you.”

I shrugged. “Rule three says, ‘Pay attention and see what works.’ It could also be ‘pay attention and see what doesn’t work.’”

“That’s why I’m sure my daughter is in good hands,” Becky smiled. “You’re not going to mistreat her.”

“I try my best not to hurt her. Or you.”

“I appreciate that, John,” Becky assured me. “Which is why I’m not worried about you and Katie working on this set of lessons. I have no idea if Katie will be able to enjoy any of what I’m trying to teach you today, but I want you prepared for things.”

“Okay...” I said, “So, what if Katie and I decide to try anal sex? How should we go about it?”

“The big thing is to go slow and be gentle,” Becky cautioned. “Stop if it’s too painful. Use lots of lube, too. You’ll probably want to start with a finger or two, or a small toy so she’s not as tight when you try to stick your cock in there. It’s probably a good idea if she has an enema before you start, so there’s no nasty stuff in there. Condoms would be a good idea, too.”

“Sounds like it takes a lot of preparation,” I said.

“It can be painful if she’s not ready,” Becky nodded. “It might be painful anyway. That’s why you should go slow.”

“Anything else you can think of?” I asked.

“Don’t ever switch from her ass to her pussy,” Becky said. “It could cause some nasty infections.”

I nodded.

“There’s a little bit more I want to teach you,” Becky said, “but this is a good place to take a break. I actually do need you to do a couple of handyman things today, so let’s get those chores out of the way. I’ll take you to lunch when you’re done and we can talk some more.”

After a quick shower to wash the lube off our butts, we got dressed and I dutifully changed three or four lightbulbs and moved a couple of heavy storage tubs to the attic for her. It took less than an hour to do everything on her list.

We were on the early side of the lunch hour and the hostess seated us in a remote corner of the diner, so Becky brought up the subject of anal sex while we waited for our food.

“I’ve tried it before,” she admitted, “and it was too painful. Even your finger was uncomfortable, but I thought it was worth the discomfort to give you the hands-on experience you’ll need.”

“I’m sorry if I hurt you,” I said.

“Apology accepted, but it was more of a stinging sensation than actual pain,” Becky said. “I will say, though, that you rubbing my pussy made it a lot easier to take.”

“Yeah,” I nodded. “You loosened up some when I was rubbing you.”

“File that away for future reference,” she chuckled. “I don’t know how Katie is going to react. She may like it and want to try letting you put your dick in there, a finger may be too uncomfortable for her to take, or the whole idea may just put her off. You’ll have to play it by ear next Saturday.”

I nodded.

“I’m going to remind you again to take it all very slow and use lots of lube,” Becky said, “and stop if it’s hurting her. This is one time when no really means no.”