How I Bagged a Cougar
Lubrican
How I Bagged a Cougar
By Robert Lubrican
Bookapy Edition
Copyright 2011 Robert Lubrican
2nd Edition edited 2023
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Rights to cover art purchased at iStock.com
* * * * * * * * * * * *
I was working on the last term paper I'd have to do in high school when I heard the back door open and close, and the voice of my mom's best friend, Connie rang out.
"Hey! Anybody home?"
I heard my mom's voice answer and bits of conversation, though I couldn't understand what was being said. I didn't think much about it until I felt a presence at my bedroom doorway. I looked up to see Connie standing there, leaning against the door jamb. She and Mom had been best friends ever since they were in junior high. I thought Connie was a year younger than Mom, but I wasn't completely sure.
Connie and I had one of those strange kid/adult relationships that sometimes happen. When I was born, she was my first babysitter. She was over at my house all the time, to see my mom, and I had mowed her lawn since I was about eleven. She had gone to picnics and concerts with us. So I saw her more than just about any other adult. Except for some of my teachers, maybe. The point is that she was the only female adult in my life other than my mom who I was really familiar with, and who kidded around with me, and talked to me for more than two minutes at a time.
Of course that meant she was also the only female in my life who I had time to really study as my male hormones kicked in.
So, when I looked at her I felt the familiar tingle in my groin that I'd been feeling every time I'd seen her since I turned fifteen. I think that was when my ability to have really good fantasies kicked in. And, believe me, Connie was easy to have them about.
Of course I knew I'd be in trouble if anybody knew I sometimes imagined her naked. She wasn't married or anything. She'd had a boyfriend for something like ten years and they had broken up. But she was an adult, and I was a senior in high school. I might be only three months from turning eighteen and being able to vote. And there might only be three weeks left before graduation. But that didn't mean squat to my parents in terms of me claiming to be an adult too. My folks wanted me to go to college. I wasn't so hot on the college idea. I mean I didn't know what to major in, or anything. But, if I went, maybe then they'd believe I was grown up.
But back to my tingle. Connie was just staring at me. Her arms were folded under her breasts, which kind of put them on display, you know? She had nice ones, even bigger than my mom's, which were as good as any I'd ever seen in a Playboy. Not that she knew I had seen them, but one time when she was wearing just a robe, dad had snuck up behind her, pulled it open, and cupped them. I was down the hallway, so they couldn't see me, but I could see them, and I got a clear view of him holding them up. All I could think about was that I sucked on those when I was a baby!
I tried not to look at Connie's breasts. I was kind of tongue tied.
"Hi Champ," she said. She'd called me Champ ever since I won the hundred yard dash when I was twelve. It was the only race I'd ever won.
"Hi," I said weakly.
"Guess what," she said.
"I don't know," I replied.
"I didn't ask you what you know," she said, smiling. "I told you to guess what."
"How am I supposed to know what to guess?" I asked, frustrated. My cock was getting harder and harder, and she was teasing me.
"What's gotten you all riled up?" she asked, standing up and dropping her arms.
I couldn't very well tell her that she was what had me all riled up, so I just looked away.
"Nothing. I'm trying to write a paper. It's my last one and it isn't going all that good."
"Well its Friday night, you goose," she said, laughing. "You shouldn't be doing homework now. You should be out kicking up your heels. Save the homework for Sunday night."
"I like to get it done so I don't have to worry about it," I said, only glancing at her.
"A laudable sentiment," she said gravely. "But I need a favor, and your mom said it was okay for me to ask you."
"What kind of favor?" I asked.
"I need you to come to my house and take some pictures."
I looked at her. "Pictures? What of?"
"Not 'what of'," she said. "Of whom."
"Whom of?" I asked.
She laughed.
"Me, Silly."
* * * * * * * * * * * *
I'd joined the photography club at school when I was a freshman. Since then, my folks had gotten me a really nice camera, a Nikon D3 100 SLR. That means single lens reflex, but that's not important unless you're into photography like I am. Suffice it to say it's a good camera that takes really quality shots. I had saved my allowance and lawn mowing money, and gotten more lenses and filters and a good flash unit for it, so it was a decent setup. I'd even had a couple of my landscapes published on one of the Farm Bureau web pages.
So here I was, lugging all my stuff into Connie's house, which was on the other side of town from where we lived. I was born and raised in Granite City, just like my parents ... and Connie. She led me into the den and said, "How about in here?"
I was lost.
All I knew was that I was going to be taking pictures of her. I didn't know what they were for, or what style of pictures she wanted or anything.
"What for?" I asked. I was still kind of tongue tied. My cock was still half hard. Connie had a fine ass, and I had been watching it all the way into the house.
She turned to look at me, one eyebrow raised. I realized she had on bright red lipstick, just like I had seen in a commercial the night before. I remembered wondering what kind of woman would actually wear bright red lipstick like that, because I couldn't think of any woman I'd seen in real life who did. Now I realized I knew one ... and I was with her!
"'What for' what?" she asked.
"The pictures," I blurted. "What for?"
"Oh!" she said brightly. "Well ... it's a little awkward, I suppose. I didn't explain it all to your mother. She wouldn't understand. But you're all grown up and almost a man, and I know I can depend on you to be ... um ... discreet ... right, Bobby?" She only called me Bobby when it was serious.
I had no idea what she was talking about, but I wanted to please her so I nodded.
"Excellent!" she cooed. "They're for a new dating site I'm trying out."
"Dating site," I parroted.
"Yes, you know ... a place to find a date?" She grimaced. "Of course you wouldn't know anything about that. A handsome young man like yourself would never have to resort to a dating service to meet girls."
"Dating service?" I asked, confused. "You're using a dating service?"
Her face went still. "Yes ... why?"
I might not have been the best when it came to dealing with girls ... women ... but I knew the danger sound when I heard it, and it was in her voice when she said that. She confirmed it by going on.
"I suppose you think that's a complete waste of time ... that I'll never get a date."
I felt a rush of blood suffuse my face. My tongue came untied. Unfortunately my brain wasn't up to the task of governing my now loose tongue.
"Are you fucking crazy?" I blurted.
Her frown deepened, and I suddenly realized I had dropped the F bomb on an adult. And a woman to boot.
"I had no idea I was such a hag," she said stiffly.
My brain farted again.
"Damn!" I moaned. "You're anything but a hag."
Her eyebrows relaxed a bit. She looked interested, suddenly, instead of mad.
"My, my, but you have developed a potty mouth. What do you mean, exactly?"
I reviewed what had slipped out of my mouth, thanks to my loose tongue and farting brain. Basically, I had suggested that my mom's best friend was as hot as I thought she was.
I was doomed.
"Exactly?" I croaked.
"Yes, Robert," she said, taking a step closer to me. "If I'm not a hag ... what am I?"
I thought furiously, but I didn't have a lot of time before I responded.
"You're the kind of woman who for sure doesn't need a dating service to get a man's attention," I said. It didn't quite come out like I thought it would. I closed my eyes.
"Why thank you!" she chirped, to my astonishment. "I knew you'd understand and be supportive. But this dating site is having a contest and I want to win it, and I need you to take the photographs for me for that to happen." She smiled brightly.
"Contest," I said.
"Yes," she said. "It's a contest to decide who's the sexiest new member to join this month. They're going to pick a male and a female winner, and those two will get to use the site free."
She had just told me I was going to be taking "sexy" pictures. It should be instructive for you, in terms of understanding how rattled I was at that moment, when you understand that I responded with: "But you don't need to do that to get a date. You could have any man you want!"
Her smile was brilliant.
"I knew this was a good idea," she said. Then she put one hand on her hip and struck a pose. "Did I mention there's also ten thousand dollars for first place? I'll split it with you if I win."
* * * * * * * * * * * *
Twenty minutes later my brain was back on track. Not only was I going to get a chance to see Connie in "sexy" poses, whatever that meant, but there could be some real money in it too. I think it was thinking about what I could do with five thousand dollars that got me functioning again. I could get a car! But I had done enough photography and entered enough contests to know there were rules and protocols, so I asked her to pull up the site so I could see them.
"We don't have time for all that, Champ," she said breezily. "Your mother said I can have you until eleven, but then I have to send you home."
"I have to know what kind of photos we're supposed to take," I insisted.
"That's easy," she said. "There are three sets. One is in evening gown. One is in swim suit. And the other is ... nude."
I blinked. "Oh shit," I whispered.
"Don't freak out, Champ," she said, her hands coming to my shoulders. "Nobody will ever find out you took them. Your mom will never know. They're just for this contest, and nobody in this one horse town will ever see them."
"Naked?" I whined.
"Come on, Bobby," she wheedled. "You're a big boy now. It won't be that bad. I thought you said I was pretty. I might not stand up to the girls you've probably seen in their birthday suits, but you did say I was pretty."
I still didn't think it was time for me to inform my mom's best friend that I routinely dreamed of her naked, on her back, legs spread and arms open wide in welcome, as I hovered over her, ready to ram my rampant prick in her soft, clasping pussy. She had replaced almost every girl I'd ever fantasized about. Should I tell her that?
No. Definitely not time for that yet.
"You are pretty," I said. "That's kind of the problem." I blinked. That had actually come out pretty good!
Her hands stopped on my shoulders. They squeezed gently.
"You'll be fine," she said. "Just take the pictures ... and everything will be fine."
* * * * * * * * * * * *
Actually, the evening gown session wasn't all that bad. Mainly because she had awful taste in evening gowns, and seemed to think that poofy and lace was all the rage. She had two gowns and both of them made her look like she weighed at least fifty pounds more than she actually did. Of course that didn't bode all that well for the money, and of course that loosened my tongue again.
"Do you have anything more form fitting?" I asked, after I finished shooting the second dress. "Something that would complement your figure better?"
"My bikini will do that," she said, frowning slightly.
I heard the danger sound again. "Got it," I said.
She left the den and I fiddled with the sheet that I had hung up as a backdrop. I rearranged the extra lighting. I had made my own hair light and it was working well. She had the perfect hair for it, that shiny reddish brown hair that a hair light gives golden tints to.
When she came back into the room, I just stood there, shocked.
We have a municipal pool, which is where everybody goes swimming, so I had seen Connie in a swimsuit before. She had several suits she wore there, one of which was a bikini. It was white with flowers on it.
But that wasn't the bikini she was wearing now.
This one was bright yellow. Well, it was either bright yellow, or I was seeing spots from the flash.
Because all that was covering her body were yellow spots. There were two spots up high and a longer, thinner one down there. She spun in a circle and the spots disappeared completely. Man! She had a fine ass!
"What do you think?" she asked, her voice high. "Does this show off my figure?"
If I'd have been listening to her tone of voice, I'd have heard nervous. Instead, I think I might have drooled just a little bit. I know I didn't say anything, because my mouth wouldn't work.
She laughed. "I'll take that as a yes." Again, if I'd have been listening on a deeper level, I'd have heard relief in her voice. But all I could concentrate on were those yellow spots.
The spots were actually triangles of thin cloth, attached to dental floss that held them artfully across her body, covering her nipples and her pubic hair. The back was only floss, and damned little of that. I snapped my fourth shot and realized I was stiff as a board in my pants. But she was looking right at me, so I couldn't do anything to adjust things. And she was good at looking at me, too. You know that look that the Playboy models have? That look that says, "Want me? You can have me." She had that look. I stopped worrying about the frumpy gowns. Any man who didn't vote for this as the best was fucking blind.
It was as I took a shot of her looking over her shoulder at me, eyes smoldering, come hither look making my balls ache that I fully realized I was going to be doing this with her naked.
My knees got weak, and I left the camera on the tripod and sat down.
"Is that enough?" she asked. Her right hand came up to her right breast and, right in front of me, she squeezed the nipple through the cloth. I realized she wasn't even aware she'd done it when she said, "I want to make sure we have enough shots, so we can choose only the best ones to send in."
"We have wonderful shots," I panted.
"Okay," she said, frowning again. "If you're sure."
"I'm sure," I wheezed.
She stood, feet together and arms hanging at her sides. She looked a little nervous.
"I guess I should take it off now ... huh."
I think my response was something like "Methumbrtang." I have no idea what I said.
Her eyebrows arched. "Are you all right?"
I got out one intelligible word.
"No."
"What's wrong?" She stepped toward me, and suddenly that nearly naked body was only a couple of feet away. I had been using a 28mm lens, zoomed in, which meant she was ten or twelve feet away as I took the pictures. Now I could almost smell her. I did see a sheen of sweat on her skin. Probably from the supplemental lighting. I could also see her nipples through the cloth of her top. They looked huge.