Billy let’s Jim in on a discovery in his mom’s room.
“Jim, I think she’s lonely.”
I’d just watched Mrs. Drake as she was leaving for work. I often watched Mrs. Drake as she was leaving.
“Doesn’t she like, see guys yet?”
“No, I think she wants to but misses my father.”
“Too bad. She’s kinda hot. For a mom.”
“Hey, that’s my mother you’re talking about!”
“No disrespect, but don’t you notice how she doesn’t seem as old as she is?”
“No, I don’t look at her like that.”
“I do, kinda.” He gave me a look that said I was out of line, but then Billy was one of those kids who couldn’t help telling the truth, like it was impossible for him to bullshit you.
“OK, maybe, sometimes.”
“I like her butt. It’s not real big like the other moms and her boobs jiggle when she’s doing stuff around here.”
“Aw, do we hafta talk about her like that.”
“Think about it.”
That was the end of the conversation. We went on to whatever else we did all day. It was summer, between grades in high school and there was a lot to do. Playing ball, hanging out with the other guys, trying out our best lines on the girls we’d really began noticing in the past year. Mostly they laughed at us. We weren’t the coolest kids at school, but we weren’t at the bottom of the list either. I was about 5-8 at the time, kinda skinny, but maturing. I had dark brown hair and just the lightest bit of hair starting on my chin. Billy was similar, maybe a little taller, with lighter hair.
It was a week later. We were hanging out at his apartment, getting out of the 95 degree heat. Mrs. Drake was at work. It seemed she was always at work. I guess it took a lot to support the two of them. At that age we didn’t consider such things. Billy could have had a summer job, but his mom said, “maybe next summer. Be a kid one more year.” That’s the kind of mom Mrs. Drake was.
Billy was kind of excited. He had been since I got there.
“Billy, what’s up? You’re bouncing off the walls.”
“Dude, I found something, some things, but you gotta swear not to tell anyone. Promise?”
“Yeah sure, you know you can trust me.”
“I mean like the biggest promise. Swear it.”
“OK, I swear.”
“Come with me.” I followed Billy across the kitchen into his mom’s bedroom. We never went into her bedroom. She never said anything but we knew it was off limits, so if Billy was taking me there it must be important.
“Jim, I was putting away clothes and maybe I got snoopy and maybe I shouldn’t have opened this drawer and maybe I shouldn’t have pushed around the clothes in there and well, I know you think my mom is hot for a mom…”
“What is it Billy?”
“I found pictures.”
“Yeah so there are pictures on the wall out in the hall.”
“Of Mom, and Dad. When they were young. Like before I was born. They’re naked.”
“Holy shit, you found pictures of your mom naked when she was young?”
“Probably not too much older than we are.”
“Oh wow, can I look?” We were old enough to know better, but young enough not to be able to resist.
“I guess, but really, you still swear?”
“If you’ll let me see photos of your mom naked, I’ll swear to anything.” He handed me an envelope. I was tempted to spill them out and take it all in, but I decided to go one at a time. The first was in a small bikini. “Wow, she was so hot. Look at those tits!”
“Jim, be nice.”
“But look, look at her body. Billy, forget she’s your mom.” Billy looked and admitted she was hot. Billy’s mom is a little shorter than us. At 18 or 19 she had long slim legs, and a perfect hourglass figure with breasts that were high and firm. I was getting a tense feeling between my legs. The next couple were more typical beach type photos. Someone had taken one of Billy’s mom and dad together. He was a couple inches taller than us and looked a bit more muscular. Billy looked a lot like his dad. Then the next photo was different. Billy’s mom had her top off and her arms across her breasts. She looked almost shy and embarrassed. The tease had me squirming just a bit. Holding my breath I removed the next photo, and there they were.
“Wow, look at those Billy.” I held the photo towards my best friend. He seemed to be debating with himself but gave in, nodding in agreement. Billy’s mom was sitting, leaning back on her elbows, with the two nicest tits I’d ever seen just sitting there on her chest. Round and firm with nipples sitting up on the tips. Mid sized areola and nipples big enough to show up in the photo. She was smiling at the photographer, who must have been Billy’s dad. I could have stared at that one all day. Without realizing it my free hand readjusted myself in my shorts. I glanced over to see Billy trying to do the same without using his hand. It kept getting better. Next the future Mrs. Drake was naked, with her legs crossed to hide the good parts. Her head was back and she seemed to be laughing at something very funny. Maybe it was Mr. Drake taking a picture naked because the next was of Billy’s father with his cock standing out proud and firm. “Hey, your dad had a winner there Billy.”
There were a couple more photos with Mr. Drake posing, giving us a side view. They must have had a timer on the camera because the next, as we got near the bottom of the pile, was of Mrs. Drake standing sideways next to Billy’s father. You could see the side of her left boob and the curve of her ass. She was holding Mr. Drake’s cock in her hand, her head on his shoulder. Finlly I got to the final poses. Billy’s mom was facing us, striking a pose and there is was. Well, what we could see was hair. Trimmed a bit, but yep, pussy hair, I was rubbing my hand along my pants. I really needed to rub one out looking at photos of Billy’s mom.
“Billy, I hope you don’t mind, but I gotta.”
“Yeah, you mean you don’t need to?” Billy was going to deny it, but Billy being Billy, he nodded. He simply said,
“Don’t mess up the photos.” I propped them against the dresser. Then I took out my cock. I looked over and noted that Billy took after his dad in other ways. Lucky kid. I was doing ok for myself but not like Billy. We mostly kept to ourselves trying not to think about stroking our cocks next to another guy. I was staring at the naked pictures of Billy’s mom. I suppose he was too. When I came, it was hard and fast and made a mess of my shirt. So I used my shirt to clean up and asked Billy if we could do laundry. When I looked at him he was wiping himself off and I noted that his soft cock was still pretty big. He said ok to laundry so we put that in, washed up, then went to put the photos back. That we were standing naked doing this didn’t seem to bother us. As Billy was putting the envelope back under Mrs. Drake’s underwear he made a face, reached further back and produced something I wasn’t familiar with.
“What’s that Billy?”
“I think it’s called a dildo.”
“Dildo, I’ve heard of them but never saw one. It’s what women use on their pussy?”
“Yeah. I guess to like get off alone?”
“When they’re lonely?”
“Poor Mrs. Drake. I wonder if she looks at the photos and uses it?” We’d been looking at photos a long time. Longer than we realized. Billy had turned the base of the dildo and we heard it humming.
“It’s vibrating.” I put out my hand.
“Let me see.” I’d grabbed it by the tip. The vibrations were obvious. Figuring, what the hell, and maybe subconsciously knowing just where it had been, I touched the tip of my cock with it. “Oh shit.” It sent sensations up my body. My cock instantly responded. I tapped it on Billy’s cock to show him.
“Oh wow, that’s wild. I wonder where Mom puts that?”
“Where do you think goofball. It’s long and straight like a cock.”
From the doorway,
“What are you two doing in my….oh my god! Boys, you’re…oh.” I turned. I was holding a dildo in my hand, my cock was erect and Billy’s mom was standing in the doorway looking like she’s been hit by lightning. Billy had the good sense to cover up. “What are you two doing?” Billy as usual just started blabbing the truth.
“Sorry mom, but Jim was saying the other day how you’re hot and all and then I accidentally found the photos and I showed him and we got excited and we found that thing and I’m sorry and Billy’s sorry and well, sorry.” Mrs. Drake looked at me. I noticed that her eyes drifted down a couple times.
“And what do you have to say for yourself?”
“Sorry, but kind of not. You were very beautiful.”
“And still hot?”
“Oh yeah. And sorry you’re lonely. I wish I could help.” Oh shit, did I really say that out loud? She looked down again. Sighed.
“You probably could from what I see.” Now Billy added his two cents. But more like 5 bucks from my point of view.
“It’s ok mom. If you need to. Better than using that.” Wow, what a friend!
“Oh no. No. I couldn’t.”
“Has it really been over two years Mrs. Drake?” Billy walked past me, kissed his mother on the cheek, then left the room. I stood cock still bobbing, holding a dildo. Mrs. Drake walked to me and took the dildo. She put it back in the drawer.
“Do you really think I was pretty?”
“Better than any girls I’ve seen at school. How old were you?” Mrs. Drake sat on the end of the bed.
“Just 19. Scott was 20. We went to the beach for the weekend. We were having fun and when he suggested the pictures I said ok without thinking.” She patted the bed and I went to sit down next to her. My cock sticking up in front of me. She looked down at it. “We’d only recently been, you know, doing it.” She sighed. I tried filling the silence,
“You were quite a couple. And as a guy who likes girls I still have to say, he was packing pretty good.” She laughed.
“Oh sure. Scott was impressive. But he was smart and funny as well as sexy. I do miss him. All of him.” She’d let a few tears run from the corner of her eye. Seeking to console her I put an arm around Mrs. Drake. She rested her head on my shoulder. “Are you smart and funny, Jim?”
“I try to be.” Now I let my hand wipe the tears from her cheek. “Mrs. Drake? Do you need companionship? Just until you find someone to be with?”
“Call me Ruth.” She turned her head and kissed me. Then she moaned as her hand wrapped around my cock. I may not have been as impressive as Scott, or even Billy, but I thought I was man enough. Not that I had any experience that way. She kissed me again. I was kissing Billy’s mom. She was holding my cock. So I put a hand on her breast. “Let me.” We were kissing but I felt her unbuttoning her blouse. Then her hands moved to her back. I reached again and found the bare flesh of her right breast. It more than filled my hand. Those tits that I’d watched shake as she set the table were not in my hands. “Not quite like they used to be.”
“Remember, I thought you were hot before I saw those photos.” She smiled, then went back to kissing me. When she let her tongue search for mine I was lucky not to spurt in her hand. Mrs. Drake, Ruth, was slowly stroking my cock. She pushed my head down slightly and i knew what she wanted. I wanted to also. I began kissing and licking her tits. Her areola had stretched a little, the nipples were hard, waiting for me to suck and bite them. She let go of my cock long enough to push down her skirt and underwear. As I reached a hand down we fell back on the bed. My hand went over the soft bulge of her stomach and down to the thick hair below. I let my fingers wander until finding her thick lips, the inner lips pressing through. She gasped as my fingers pressed and pulled, her moans louder as I sucked at her tits, fingered her pussy. We scooted up on the bed. My hands wandering, following her wide hips, the bigger curve of her ass than I’d seen before. My cock was hard and ready. “Ruth, do you want to?”
“I shouldn’t but I must. I hope Billy forgives me.” I was between her legs, looking down at her, the way her tits lay flatter, her short hair falling back, her unsure smile, similar to the one from the first nude.
“I think Billy is happy for you.”
“A dream come true.” She held me to her as I penetrated her wet pussy. It may have been awhile but her body was responding in the old familiar ways. I closed my eyes and took in the feel of her pussy accepting my cock. Ruth closed her eyes, maybe remembering the past. Remembering her first time. I settled into a steady rhythm, her ass cushioning us as I pressed forward, her tits shaking with each thrust. She was murmuring, maybe saying his name. I didn’t mind. She needed this, I was grateful for it. She began to lift her hips asking for more. I responded bu holding her ass and going faster and harder. She had a hand on her pussy just above where my cock was driving into her. She moved it frantically then called out in sighs and shreiks as she came. She begged me to give it all to her and I soon answered her, cumming hard inside. When I was done I lay alongside Ruth. We held each other. I noticed she was smiling. I propped my head on my hand,
“I’m happy you’re happy.” She looked over at me,
“Thanks Jim. You were wonderful.” I was even happier. Given my relative inexperience, making a grown woman satisfied was quite a feat. At least I though so.
“If you want, we could do it again sometime.” Now I was smiling.
“I’d like that, a lot.”