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."

"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 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.

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 was 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 it 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.

"Insane!" I barked.

She blinked. "Oh come on. It's not that bad. Don't fade on me now, Champ."

"No!" I panted, trying to explain. "Dave ... insane!"

Dave was the guy she had gone with for ten years. They had never lived together, because in our town you just couldn't get away with that kind of thing. But she had spent a lot of nights away from her house ... if you know what I mean. She never let him sleep over, as far as I knew, because she had nosy neighbors, but he lived on a small farm outside of town. Then one day she announced that Dave had broken up with her. I had thought he must be an idiot then, and had just voiced that now.

Her eyes searched my face and she got that smoky look again.

"Why thank you, Champ," she purred. "That makes me feel really good."

"I don't know if I can do this," I said, completely honestly.

Damned if she didn't sit down next to me, like we were just going to chat for a while.

"Are you still going with that nice blond girl? What's her name? Cheryl?"

I wouldn't have characterized the relationship I had with Cheryl as "going together." While she had been my girl friend (as opposed to girlfriend) for a couple of years, Cheryl had made it very clear that she knew there was life after high school, and after Granite City too, for that matter. And all that meant that she wasn't going to allow any hanky panky that might screw things up and keep her in town. I wasn't all that good with girls anyway, so I just kind of went along with things. I liked her, and there was no pressure, so she was fun to go do things with. But that seemed like a lot to explain, so I just took the easy route and nodded.

"Well, then, all you have to do is imagine that I'm Cheryl. You like seeing her naked, right?

I was thunderstruck. Here was an adult asking me to not only admit that I'd seen my girlfriend naked (which I hadn't), but also to casually admit how routine it was!

"It's not like that!" I choked out.

"Well, of course she's a little shy with you," said the soon-to-be-naked woman sitting beside me, completely misunderstanding my last comment. "That's only natural. I mean the only reason I feel so comfortable like this is that it's you. I used to change your diapers. Surely you don't think I let just any man see me like this."

My mind wrestled with the idea that the whole purpose of taking these pictures was so that a whole mess of men could see her like this.

"Think of the money, Bobby," she cooed in my ear.

I'll be completely honest with you. At that point, I couldn't have cared less about the money.


My knees were working again. I was bent over, looking through the viewfinder of my camera. My thumb was on the cable release. I figured maybe it would be better to see her this way, rather than by looking directly at her. I watched as her hands came up to the top of her suit and fiddled with the floss. The yellow spots fluttered down and away from breasts that made me salivate, even through the viewfinder.

Her breasts were perfect ... round and full, with a little sag, but not baggy, you know? Her nipples were an almost shocking red color. I think it was that that made me stand up and look right at her. I realized the nipples were the same color as her lips. She saw my eyes going back and forth.

"I put lipstick on them," she said softly. "Is it too much?"

She was so calm about this. I think maybe it was the combination of that calm demeanor, and the lipstick on her nipples, that did something to me, because all of a sudden I felt completely at ease. She was still drop dead gorgeous. I still wanted her more than life itself. But suddenly that was all okay.

"We'll take shots both ways," I said, my voice suddenly stronger than it had been for the last half hour.

Don't ask me why, but I put my spare memory card in, so these shots would be separate from the others. I talked her through a bunch of poses. She looked good bending over, with those breasts hanging, because you could see her nipples really well against the sheet. They stood out half an inch, maybe, but it was hard to tell in the front on shots. When I was satisfied I said, "OK, now the bottoms."

She hesitated only enough that I noticed it, and realized that she might not be as comfortable with this as she was letting on. I knew she had teased me, and something in me wanted to tease back for some reason.

"Come on," I said softly. "Don't chicken out on me now. I've been waiting to see this for years."

That smoky look came back into her eyes and her fingers flicked at the ties of her bottoms. They fell straight down and she kicked, catching them on her toe and flinging them to one side.

"This?" she asked, her voice deep.

I swallowed. Remember that long thin spot of yellow that covered her pubic hair?

No it didn't.

There was no pubic hair to cover.

"Damn," I sighed.

"Potty mouth," she accused. "How should I pose?"

"Lying down, on your back, with your knees spread" I sighed. I felt myself blush, but by this time I realized somehow, that my lecherous comments weren't offensive to her.

"Why, Champ," she cooed. "Are you having naughty thoughts about me?"

"Let's just say that if my mother knew what I was thinking about her best friend ... I'd be grounded until I was thirty."

"You do have a silver tongue when you want to," she sighed. "I have a confession to make."

"What's that?"

"They don't really want nude shots for the contest."

"Oh." My mind whirled. "So ... um ... why... ?"

She walked over to me. The camera was between us until she lifted the tripod and moved it aside. Then she was inches in front of me, in all her naked glory.

"Because, Bobby, if I don't get laid, I'm going to go stark, raving mad, and there's no man in this town that I can let do that ... except maybe you."

I don't know why my brain was suddenly able to deal with all this, but it was.

"You'd let me do that?" I asked.

I saw her eyes fill up with tears. "Oh baby," she whined. "I need you so bad right now. You've grown up to be such a hunk, and I know I shouldn't do this, but every time I look at you I get so horny I need a car battery to keep my vibrator going, and you're going to graduate and go away and I'll be stuck in this town forever. At least I can get my bell rung one more time before you go ... please?"

This was a little bizarre. I mean Connie was a hottie, and she really could have any guy she wanted. And that made it seem a little off that she wanted ... me. Don't get me wrong. I was all for it. But it just didn't seem possible.

So I tried to make sure I wasn't having some kind of wild dream, or mental episode.

"So there was no contest?" I asked.

She blinked.

"Of course there's a contest," she said. "Except for the naked part. They didn't really ask for nude photos. Just the evening gown and swimsuit shots. I was hoping that you'd get excited if I got naked in front of you."

"I've been excited by you since I was fifteen," I said. "And you didn't have to be naked."

Her smile was brilliant. "And that is why I have found you so irresistible all these years."


"Good grief," gasped Connie, as she tried hard to get enough air into her lungs to stay conscious.

"What's wrong?" I asked, breathing hard myself. "Didn't I do it right?"

"I ... completely ... forgot ... about the ... stamina ... of a young ... man!" she panted.

That made me feel pretty good. Of course I was feeling pretty good anyway. I wasn't a virgin anymore, and she had squealed and taken skin off my back with her fingernails five different times since I got naked with her and she adopted the pose I had suggested.

Let me tell you, by the way, that there is nothing cooler than a good looking naked woman ... on her back ... legs spread ... reaching for you ... and saying, "Hurry Bobby. I need you bad!" Nothing!

OK, maybe when you slide your prick in her and her pussy walls flutter and move and squeeze and her arms go around you and she groans in that special way that tells you she has just been made really happy ... that's cooler. There's nothing cooler than that, though.

Then again, I guess it's pretty cool when she pants faster and faster and her voice gets higher and louder until she squeals and says she's cumming and that she loves you and for you please not to stop. Yeah ... I have to admit that's about as cool as it gets.

Except for the part where your balls feel like they're going to explode and there's this overwhelming sweet pain in your cock and you're blubbering like a little girl and she puts her lips right by your ear and licks it and says, "Cum in me, Bobby. Spurt in my pussy, baby." I mean that's killer cool. Especially when you get to do it three times.

I rolled over and looked at her heaving breasts. The lipstick was all gone now. It was cherry flavored, and I love cherries, not to mention sucking on her nipples. Now they were just pink, on a slightly darker areola that was still a little swollen. I really liked sucking on them.

"Can we go again?" I asked.

Her head rolled toward mine. Her eyes looked kind of big, and I could see white all the way around her irises.

"If you don't go home in the next ten minutes your mother is going to send out the cavalry looking for you. I had to promise you'd be home by eleven."

"I'll call her and tell her I'm fine," I said. I leaned over and licked a nipple. "Besides ... we didn't finish taking the nude shots."

She smiled. "I told you there aren't really any nude shots."

"Yes there are," I said. "There is no way I'm going to college, or anywhere else, without a full set of them."

She frowned. "I'm not too sure I like the idea of photographs of me all naked floating around loose in the world."

"I have to have them," I said. "I mean if I'm ever broke, and on the skids, and homeless, I can probably get thousands for them, and get back on my feet."


Women have no sense of humor. And you'd think that if I rang her bell so thoroughly, that she'd be happy enough with me to overlook one bad joke, you know?

But she made me get dressed and go home. She was holding a big wad of Kleenexes between her legs, and kind of wiping the inside of her thighs, complaining about the mess I made, and how she hadn't planned on that, which sounded kind of goofy. I mean she admitted that she got me over there under false pretenses just so she could get her bell rung, right? So why was she complaining now?

I found out when she shoved me out the door. Just before I left she kissed me (go figure) and handed me a foil packet. It was a condom and she said, "Put this in your billfold, in case we can't get together here the next time."

"What?" I was confused.

"Just keep it with you," she said and shoved me out the door. She was still naked.

I really didn't want to go home.


I was pretty sure my mom would take one look at me and know exactly what I had been doing with her best friend for the last three hours. And I don't mean taking pictures. In fact, it turned out that it was a really good thing that I had put the nude shots on the extra card, because the first thing my mother did was grab my camera and demand to see the photographs. I was also glad I'd put the original card back in the camera.

Apparently she had told Mom about the contest, and what the pictures were for, but had left the rest kind of vague.

I started off with the gowns, of course. Mom agreed with me, even though I kept my mouth shut.

"Good Lord, what was she thinking?" muttered my mother as the shots flickered past.

Then we got to the first bikini shot and she got kind of pale. She looked at me closely.

"I shouldn't have let you go," she moaned. "That must have been hard on you."

"Why?" I asked. I mean it hadn't been that hard.

"She was almost naked!" barked my mom.

Now I'm no fool. I know the right response to some things.

"Come on, Mom," I said, making it sound like I was horrified. "Get a life. She's old!"

Like I said ... women have no sense of humor. I got sent to bed.

Maybe it was because Mom is the elder friend.


Connie could be in movies. Not because she's beautiful. I mean she is, but she's a whopping good actress too. The next time I saw her, she acted like nothing had happened at all. She didn't pay me any attention, like stopping by my room to say hi, or wink at me or anything. She came in the back door, just like always, yelled, "Yoo hoo!" and got in an argument with my mother about modesty and what constituted being a tramp and things like that. I didn't hear it all, but it went on for a while and I knew better than to stick my nose out of my room.

It didn't matter, though, because they came to me. My mother had confiscated the camera and they had an argument about that too, before they showed up in my doorway.

"Bobby?" My mother's voice sounded too sweet. "Connie is actually going to send in those awful photographs. It has to be done online, though, and neither one of us knows how to do it. Could we impose on you to do that for her?"

I put down the graphic novel I had been reading and said, "Sure. No prob."

Connie was looking around the room like I wasn't even there. I took the camera from Mom, and got the cable to plug it into my computer.

"Can we hurry, please?" asked Connie. "The cutoff is in an hour. If I get them in after that, I'm disqualified."

"We'll get them done before that," I said confidently. "What's the web address?"

She thought for a minute and then came over to me. "I can type it better than recite it," she said, and pushed me to one side. She bent over the computer and I stared at the front of her blouse. I saw my mother moving in my peripheral vision and looked at the screen. Connie glanced at me. I couldn't help but look back. She has gorgeous eyes.

"So I'm old?" she mouthed at me. Then she stomped on my foot as she stood up and moved back.

"There," she said.

We went through all the shots. By "we," I mean my mother and Connie. They argued about which gown shots to send in. My mom was trying to be nice, but it was pretty clear she hated them all. When it got to the bikini shots mom stood back.

"They're all pornographic," she harrumphed. "Any of those will do, but mark my words, they'll sell them to the internet and pretty soon every man in town will be drooling over them."

I almost said not every man ... but I controlled the urge.

When we were finished my mother insisted that I delete the pictures from the camera memory card. I think she was sure they'd eventually corrupt me. If only she knew. Then, her mission complete, she preceded her friend out of the room.

In a flash, Connie was leaning over me, her hand in my lap. She grabbed a handful of balls and squeezed.

"Old?" she hissed.

"It was to misdirect her," I gasped.

She let off the pressure and smiled brightly. "I know."

Then she kissed me quickly and left the room.


Mind you, Connie had said she wanted to get her bell rung "once, before I left." And, being a teenage boy, who believed that adults mostly told the truth, I was pretty sure that "once" had already happened.

Still, I took the time to go back to the website I had uploaded the pictures to. I had to join to look at the pictures or vote, so I used my dad's name. I looked at her competition, and picked the one I thought was the worst looking, and voted for that one. Then I also voted for the most dorky looking guy. Of course to a person my age, almost all forty year old men look dorky, but I didn't want her to win and get lots of offers for dates, and if she did, I wanted the male winner to be someone she hopefully wouldn't be interested in.

If I couldn't have her any more, then I didn't want any other guy to have her either. I know. It's sad. But it's how I felt.

It turned out she was just a good actress, and had pretty good self-control.

She waited the appropriate time and came over again, looking downcast. She announced to my mother that Mom was right and she was wrong, and that the web site had suggested she retake the gown photographs in dresses that were "slightly more up to date." They also said that such gowns could be rented from a bridal store. In no time she had my mother commiserating with her, instead of saying, "I told you so!"

And suddenly I was detailed to go take more photographs. My mom made sure to explain that only the dress shots needed to be retaken. I think she was happy when I said, "Thank goodness. I don't want her to feel bad ... but she's kind of wrinkly, you know?"

I might have overplayed it a bit. My mother started sniffling and wiping her eyes.


Connie wasn't stupid. I mean she knew what had happened the last time I got home with the camera. So there really were new dresses, even though the story about the site asking for more shots was pure bull. And we took pictures of her in them.

This time, though, when she changed dresses, she didn't leave the room to do it. She just got naked and put on the next one. She took her time too, teasing me.

When I had taken the last picture, I teased back.

"Okay then. That should do it. I'd better get home so I can get these downloaded and act like I'm sending them in."

Ever been tackled by a naked woman? It's really quite fun. She tried to tickle me, but it was no contest, because she was naked (and ticklish) while I was not. So I kissed her, and she kind of lost interest in the fun and games thing. She started undoing the buttons of my shirt, and pulling at my belt and stuff like that.

I stood up and got naked. It was so cool, watching her watch me. Her eyes glittered, and she licked her lips. She looked ... I don't know ... eager, maybe? It made me feel good. I know she stared at my cock when it was uncovered. I was already rock hard, of course. I started for her and she put up a hand to push at me.

"Condom!" she barked. "Mamma is ovulating tonight, and we don't want to make a little Champ in my belly. Oh no. Get that condom I gave you and put it on."

I stared at her, thinking about what she had just said. Honest to Pete, I had not even once thought about what all that spunk I had shot into her might be capable of doing to her. It was kind of scary. I got my billfold out of my pants, and got the condom out that she had given me. I had no experience with condoms. It must have been obvious, because as I fumbled with it she said, "Give me that!" and snatched it out of my hand.

The next thing I knew, I was lying on my back with one of her hands around my stiff prick. The fingertips of that hand were holding one part of the circle she took out of the packet and her other hand pulled on it and slipped it over the tip of my cock. I didn't understand what she was doing at first, because she was pulling down on the skin around my shaft with the gripping hand, while still trying to keep the fingertips of that hand on the condom.

"This is very different," she muttered.

"Different?" I prodded.

"Dave didn't have a foreskin like you," she said. "If I trap the foreskin, I don't know if you'll feel things or not. But I can't pull the foreskin back and pull the condom on at the same time."

So she taught me how to put a condom on while she held my foreskin in the uncovered position. I know this doesn't sound very romantic, but you have to remember that a good looking woman--who I was going to have sex with--was playing with my prick. So romance wasn't all that important at that particular moment.

It looked kind of funny with that thing on it. When I got it on, she still wasn't happy, because she said the tip was too tight. So she pulled at it until there was a little empty bag right at the tip, which made it look even stranger. But then she kissed me, and started rubbing my cock while she demanded that I suck her nipples again, and pretty soon she was pulling me on top of her.

It didn't feel the same. I couldn't feel the heat as much. And things felt ... I don't know ... maybe too slippery? But I could feel her breasts against my chest, and she was making those awesome moaning sounds that told me how happy she was, so I had a good time anyway. I do know one thing. With that condom on, I didn't get the urge to spew in her for a long time, and so she got to have a lot of orgasms. Finally she went limp and then lifted her head to whisper things in my ear again. They were nasty things, and I couldn't believe my ears.

"Cum in me, Bobby," she hissed. "Shoot your spunk in me, baby. Get me all knocked up and fat with your baby."

I thought about the condom, and what she'd said about not wanting there to be any Bobby Juniors. It was a little confusing. But her fingernails dug into my ass and she got all wild, saying how much she wanted to feel me shooting in her and stuff. And it got me excited, and when I came it seemed to go on and on for a long time. This time I was out of breath too, and I kind of collapsed on her. I knew I was heavy on top of her, so I rolled over onto my back.

"Ohhhh," she complained, reaching for me. She rolled onto her side and looked down and said, "Shit!"

"What?" I panted.

"The fucking thing broke!"

I lifted my head. My cock looked really funny. It was all milky looking, and the condom was still around the shaft, except that the foreskin was poking out of the latex where it had torn or something.

"Shit!" she yipped and she bounced out of bed, running for the bathroom.

I didn't know what to do. The condom looked kind of slimy or something, so I pulled it off my cock. Then I didn't know what to do with it. So I got up, holding it out away from me. I wondered if I could just put it in the trash can, or whether maybe it was supposed to be flushed or something. I went to the bathroom to ask Connie. I mean we had just had sex. That's kind of intimate, you know? So why would seeing her in the bathroom be any different? She was sitting on the pot with her legs spread, wiping at herself and muttering. She yelled at me, saying she was on the potty, which was obvious, but I figured out that somehow her being in the bathroom was different than lying there spread open in bed, so I backed out.

I didn't know what to do. She had yelled at me, so I didn't feel like I could ask her anything. So finally I got dressed and, condom in hand, I left the house. I went around back, to the bushes along the alley, and tossed the condom over them.

Then I walked home.


My dad is a member of the Rotary Club, and they offered me a scholarship to go to the state university. My parents wanted me to go, so there wasn't much I could say. Not only did they give me a scholarship, they found me a place to live and a summer job in Clinton, where the university is located. Dad said it would give me a leg up on the other freshmen, and that kind of thing. All it meant to me was that I was going to miss out on my last summer of freedom. I would only have two weeks after graduation before my folks would take me to Clinton and get me set up, and I would start my job.

This was all announced at supper, two days after the condom broke. Connie hadn't been to the house since then, but happened to pick that night to drop in. We were used to that. She ate with us all the time. So she was there when they broke the news.

Connie got all weird about it, of course. She said, "How wonderful!" all perky and stuff, but her eyes weren't smiling along with her mouth. The rest of supper seemed normal, but after supper, while Mom and Dad were trying to figure out what to watch on TV, she pulled me into the hallway.

"You're leaving!" she said, looking like she was about to cry.

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