Ryan's Story
"Charlie Ayers was a year younger than me, but we were the only two boys who lived on our street, so we did everything together. His father was in the Coast Guard and was assigned to a ship that would go out for a few days at a time, but then when they were back in port, he normally worked nights. Except when he had days off, he was usually gone at night. Charlie's mom was Maureen and quite buxom. She almost always had a blouse with a big vee of cleavage showing, her boobs were my favorite masturbation fantasy. Sometimes when I was there late into the evenings or when I was spending the night she'd get ready for bed and come back out wearing her robe. I never saw anything more than when she was dressed, but just knowing that she had some kind of nightie underneath, and sometimes the robe would be a bit looser than other times and I could see her upper chest and a hint of nightgown, or some bare leg... I expect she knew I had a crush on her.
"There was one evening when Charlie and I had been up to my house, and got to horsing around, and we finally pissed off my mom and she told us to get lost for a while. We'd then gone back to Charlie's, where we were watching television. They had a moderately small house, just three bedrooms and a single bathroom. Charlie's mom was the only one home and didn't know we'd come in. We were in the living room, I was sitting in a chair that could look down the hall, when Maureen came out of the bathroom where she'd been taking a bath, totally naked, to walk to her room. There was nothing she could do. By the time she looked up and realized I was there, she was halfway to her bedroom. She gave a little shriek and tried to cover herself with her arms, but it didn't matter, I'd seen everything. Charlie was sitting where he couldn't see down the hall and probably barely heard her shriek and asked what that was all about, and I just said we'd startled his mom, that she hadn't realized we were there. I didn't tell him that she was naked.
Like I said, I'd had a crush on Maureen for quite some time, and I'm sure she knew it. She had a fantastic hourglass figure; big boobs and big round butt both. Seeing her naked was all it took for me to pop a boner, but at least I was sitting in the chair with my t-shirt untucked, so it didn't show. It was just a few minutes later that she came out of her room wearing her bathrobe. She didn't say anything, just looked at me momentarily as she walked past us and into the kitchen. There was something about the look and the bathrobe. I don't know what it was, but I immediately wondered what she was wearing under the robe and being a normal teenage guy, I was rock hard imagining what was, or wasn't, under her robe.
The kitchen was around a corner from the front room, so she disappeared from view. I could hear her puttering around but couldn't see anything. After a few minutes I asked Charlie if he wanted a drink and went to the kitchen myself. Maureen appeared to be making some tea, but she was really waiting for me. No sooner had I stepped in and out of sight of Charlie than she reached over and grabbed my hand and pulled me closer so that she could whisper to me.
"You can't say anything to Charlie," she whispered, so just I could hear.
"About what?" I whispered in return.
"You know about what, about seeing me." I suddenly realized that she was nervous and did what I'd never done before. I reached for her robe, gripping one side. "Ryan," she whispered, but didn't stop me as I slipped my fingers deeper between the folds. When she didn't stop I kept inserting my fingers until I slipped my hand inside onto her bare breast. I'd fantasized about her being naked beneath the robe, but never really thought it was true, but now - here she was, and I just knew she wanted this as much as I did. I pulled my hand back out to the edge of the fold and then slipped it down to the belt that was holding it closed. I began to loosen the tie, and although she again whispered, "Ryan, you can't..." she didn't make any attempt to stop me as I pulled her robe open.
"I can't
what?"
I whispered back, "tell Charlie about seeing this?" I ran my eyes up and down her naked body. "About seeing these?" I said as I reached up with two hands to fondle her breasts. My fingers found her nipples and she twitched as I pinched them.
"He can't know."
"I know," I whispered back, letting my one hand slide down her body and cup her sex. She had a full bush, and I let my fingers play in her hair, not being sure enough of myself to do anything else.
"You coming?" Charlie hollered from the living room. "Can you bring me a coke, too?"
"Yeah, sure," I hollered back, letting go of her body and stepping over to the cabinet to get glasses. As soon as I stepped away Maureen retied her robe. I grabbed two glasses, got ice out of the freezer and then poured us cokes. I turned back with a glass in each hand and stopped in front of Maureen. Reaching over I set one glass on the counter and slipped that hand inside her robe onto her breast once again.
"Your hands are cold," she whispered, saying nothing about her son's friend molesting her.
"Are you always naked under your robe?"
"No."
"If I'm here, from now on you will be. For me."
"Ok."
"Wow," Irene said, "You seduced your best friend's mother? What did he say?"
"I wouldn't say I seduced her, if anything she seduced me. I just took advantage of what she wanted."
"Yeah, but what did Charlie say?"
"Charlie never knew."
"Really?"
"Really. Although he was the excuse for me to go to his house, from then on it didn't matter if he was there or not, I was "going to Charlie's" in case my parents wanted to know. I was always "hanging out" waiting for him if he wasn't there, at least whenever Maureen was home. She worked during the day, but she was home every night."
"And you fucked her ass?"
"Yeah, that's all I fucked. She wouldn't let me have her pussy, she said that was for her husband only."
"Just once?"
"Huh?"
"Just once? You fucked her just once?
"Oh no. We had an affair for about 2 years before her husband got transferred and they moved. We had sex probably 3 times a week, whenever we could." He paused. "The first time was a day or two later. Charlie and I used to go camping, hunting, fishing - we did everything together. We had some girlie magazines, and whenever we went camping, we'd take those along, masturbate at the same time and talk about who we'd like to do it with. When it was the school year, there was never enough time to go into the woods, so we'd pitch the tent and camp in his backyard, or mine. Once I started having an affair with Maureen, we almost always pitched the tent in his backyard. Camping had always been just an excuse to get out the girlie magazines and masturbate without a chance of getting caught anyway, but from that time on, it was a way for me to get together with Maureen, right under his nose. Charlie slept like a log, and his little sister did too. Once he went to sleep,
nothing
would wake him up, it was even hard to wake him in the mornings, so when I left the tent, he never knew. That night I knew I wasn't sure what was going to happen, but I knew when I went in that the opportunity was there. I waited until he was sound asleep, and then went into the house, supposedly to go to the toilet.
"I did go to the toilet but left the door ajar, so I could hear Maureen if she approached, but it didn't work. When I was peeing, I suddenly felt a presence, and when I turned, Maureen had pushed the door the rest of the way open and was standing there watching."
"I thought I heard an intruder," she said as she just stood there watching me. She was wearing a nearly see-through nightie. It wasn't sheer, but I could see the color of her nipples through the cloth, and I rapidly got a tent in my boxer shorts. All I was wearing was a t-shirt and boxers, so it was obvious that I was getting hard. "I see it's a friendly intruder," she said, and stepped forward to reach for my cock. As soon as she touched it, her eyes got big and she said, "Oh my God." She slipped her hand inside my shorts, gripping my cock, and said again, "Oh my God!" I reached up and fondled her breasts, two handed this time, and when she didn't stop me, I lifted her nightie and slipped my hands under. A moment or two later I lifted it up and leaned in to suck on her breasts, and she just helped, pulling it completely off, leaving her in just her panty.
"We'd dropped her nightie on the floor, but she told me to pick it up and bring it with me. I followed her to her bedroom, and... I had sex for the first time.
"We did virtually everything. She gave me my first blowjob; although a girl that I dated for a while had given me a hand job a couple of times, I'd never had a blowjob before. She showed me how to finger her, and go down on her, and then when we were ready to fuck - she said no. She let me put my fingers and tongue into her, but she drew the line at my cock in her pussy. But, she said that if I wanted, I could have her ass. She had some lubricant, and had prepared herself earlier, but still added more and had me fuck her ass.
"It turned out she really liked anal, she would cum like a banshee, but her husband wasn't really a fan of it. At first, she was a bit unsure about me, saying she'd never had a cock so big before, especially in the back door, but as long as I started slow - she loved it. I fucked her ass regularly, for more than 18 months, before her husband got transferred and they moved away."
"You like anal sex? Do you want me to do it with you?"
"Truthfully, not really."
"But you did it all those times with your friend's mom?" Ryan nodded. "And you didn't like it?"
"I didn't say that. I said I don't really want to do it with you, I much prefer something that's more naturally slippery," he grinned, his hand dipping down between her legs. She made no effort to stop his caress. "I did it with her all the time because that was all she'd let me do, but I'd have taken her pussy if she'd have let me.
"Good."
"Good what?"
"Good, I wasn't looking forward to it, but if you wanted to, I would have."