How I Bagged a Cougar

by Lubrican

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa, First, Pregnancy, .

Desc: Romantic Sex Story: Like most eighteen-year-old males, not quite yet out of high school, and with no idea what I wanted to do with my life, I didn't really think anything exciting would happen to me. Then my mom's best friend asked me to take some pictures of her to send in to a contest she wanted to enter. And something. exciting. happened. Then I had to go to college early, and lost my last summer of freedom, so I was pretty sure nothing else exciting would happen. I was wrong about that too.

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 eighteen, and able to vote - 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 was, I sucked on those when I was a baby!

I tried not to look at her 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."

.... There is more of this story ...

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Story tagged with:
Ma/Fa / First / Pregnancy /