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At The Pool – Kaylie’s First Time


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My Daughter Set Me Up

A late bloomer catches up quickly

Ever since my wife left us, I’ve spoiled my daughter Kimberly, “Kim”. Not that she wasn’t already spoiled before, as she was an only child. But I just found it more and more difficult to say no to anything that she asked for, for anything that she wanted to do, or anything that she did. So when she announced that she, or rather I, would be hosting a pool party and sleepover at our house for her high-school graduation, I gave in.

Fortunately, the crowd turned out to be a little thinner than I imagined it would be, all graduating seniors and mostly couples; about twenty or so altogether. I agreed to play “bartender” and cook, to make sure that no alcohol would somehow be introduced and so that no one would burn themselves on the grill. And, the group behaved for the most part, although after the sun went down a few of the couples tried to sneak in some “grab-ass” in the pool when they thought that I wasn’t watching.

Now, I’m not a prude, nor did I expect that any of them were still virgins. I knew for a fact that Kim wasn’t, since I caught her and several different boyfriends in the throes more than once after she turned sixteen when I’d come home from business trips early. Still, I didn’t want anything going on that would get me arrested, or sued.

As I said, the group was mostly couples. But there were a few that came “stag” or “doe”. One “doe” was Kaylie, Kim’s best friend in elementary and middle school, but whom I hadn’t seen in years. She didn’t seem to fit in, and my recollection was that she was not only very smart, but also very athletic, which was something quite different than Kim and her current friends. My guess was that she invited Kaylie in honor of their past friendship.

As the evening wore on, and things seemed to settle down, I decided that just because the kids couldn’t drink was no reason for me not to. So I was on my third beer when Kaylie came over and sat next to me. Unlike the other girls, who were all wearing the skimpiest of bikinis, she was wearing a full tanksuit that came up to the top of her chest, and a wrap around her waist, leaving everything to the imagination.

“Hey, Kaylie. Long time no see. How have you been?”

“Okay, Mr. R. Glad to be done with school.”

“How old are you?”

“Eighteen.”

“And do you now have a high school diploma?”

“Yes.” She paused, then blushed. “With “honors”.”

“Well, then call me Jim.”

She smiled, showing me a mouth full of braces. “Okay, Mr. … I mean, Jim.”

“Now, which one of those hunks out there is yours?”

The smile left her face. “None, actually.”

“None? How can that be?”

She got a sad look on her face. “I’ve never had a boyfriend. I’ve never really dated, at least not one-on-one. I guess that between my brains and my brawn, guys were just never interested in me. Plus, like I’m the only senior that still has braces, and no tits or ass to speak of.”

“Stand up.”

“What?”

“Stand up,” I repeated. She stood. “Now, take off the wrap and turn around.” She hesitated, then complied.

I was expecting some flat-chested girl with no shape in her butt, but was pleasantly surprised. She had a cute, well-formed tear-drop ass that appeared to be firm, sitting on top of two really nice legs. And while she certainly wasn’t testing the tensile strength of her bathing suit material, her breasts were actually quite nice looking, and firm looking, as well. Plus, I guess that my scrutinizing had some effect, because each tit was topped with an obvious “pokie”. “Well, this may be the three beers talking,” I said, “but I think that you have a cute ass and nice tits.”

She turned to face me.

“Really? You’re not just saying that?”

“Nope. You’ve got a sexy body.” She giggled. “Hell, if I was a guy your age, I’d be all over you.”

She blushed again, giving me a full shot of her braces again. Her face was cute, although she probably had a little more acne than she wanted. Still, she was, all in all, a pretty girl. “Maybe it’s the braces, then,” she said. “Mom made me wait until I’d finished any sports where I might get hit in the mouth. She didn’t want to pay for them twice. I guess guys are afraid of getting cut by them.”

“Well, that is a shame that you had to wait, but I think that they make you look cute.” Now, that was definitely the beer talking, but she seemed to accept the compliment just the same. “However, if you want to attract the guys, you need to get something a little skimpier than that tank suit. Just an observation.” Man, what was in those beers?

She blushed again. “I’ve got a bikini with me, but these other girls look so much better, and I’m not here with a guy, and …”

“Okay, I get it. So maybe today wasn’t the day to flaunt yourself. But, at least think about it.”

“I will, Mr. … Jim.” Armed with a little more self-confidence, she left me, and her wrap, behind and went over to a group of kids. She seemed to be having a good time, and I thought nothing more of our conversation.

Even though they were all over eighteen, I decided that the best course would be for the boys that were staying the night to all sleep in the living room, and the girls to sleep in the media room. I parked myself in the den, which you had to pass by to get to either. There was some grumbling, mostly from Kim who seemed to be particularly aggressive in her contact with her boyfriend and was probably hoping to get some “alone time” with him.

The guys went out almost as soon as they agreed on who would sleep where. But the girls were up for quite a while, and I could hear whispering and giggling and such for at least an hour before they calmed down. I knew better than to go talk to them about it, as one time I asked Kim during a sleepover what they could possibly be talking about that was both funny and yet required whispering. “Oh, you know,” she said, “the usual girl stuff. How big is his cock? Did he cum in your mouth and did you swallow and how did it taste? Does anal really hurt as much as it seems like it should? Should I get my clit pierced? Stuff like that.” She laughed, and I never asked again.

Everyone but me slept in until about ten. I made up a breakfast buffet, and most of the kids left after eating. By about noon it was just Kim and her boyfriend, Kaylie, and two other couples. Everyone put on bathing suits and headed to the pool. I was happy to see that Kaylie had decided to go the bikini route this time. And, that by doing so, she confirmed my appraisal from the night before. She had a cute, tight little body. I felt a tingle in my balls.

The kids swam for a while, and I couldn’t take my eyes off of Kaylie as I sat on a chaise by the pool, keeping watch. Fortunately my sunglasses disguised, somewhat, where I was looking. But I had to keep shifting to hide my semi-hard condition, and I know that Kim could tell exactly what I was doing. She gave me that sly smile that she has before turning back to her friends.

We had lunch poolside, and then everyone left but Kim, her boyfriend Alex, and Kaylie. They decided to do some sunbathing, and spread towels on the lounges before slathering their faces, chests, stomachs, and legs with lotion and laying back after setting an alarm for one hour. With nothing better to do, and looking a little paler than I like, I decided to join them.

When the alarm went off, it was time to turn over. First Kim applied lotion to her boyfriend’s back, and Kaylie did mine as we lay face-down on the lounges. She seemed to pay a lot of attention to my thighs, especially the inner parts where they met my ass and crotch. By the time she was done, my erection had begun to return.

I tried my best to conceal it, but Kim could tell. She just smiled as the two girls lay face down on their lounges. That’s when Kim upped the ante. She reached back and untied her bikini top. “Don’t want any string lines,” was her explanation, but I suspected otherwise. Alex was way too eager to put his hands on her. But, before I could say anything, Kaylie reached back and untied hers, as well, giving me a good look at some “side boob” as she gave me that “me too” look before arranging herself on her towel.

I can’t begin to describe the feeling of rubbing lotion into this nubile young thing. I started at her neck and shoulders, making sure that I had thoroughly applied the sunblock as I moved further down her firm, yet pliant flesh. When I got below her arms, I couldn’t resist the urge to rub her sides, especially where I knew her breasts were. I got brave, moving my fingers slightly underneath, causing her to sigh.

I was so mesmerized by what I was doing that I almost didn’t hear Kim tell me that she and her boyfriend were going inside. When I did look up, I could see that he had a rather impressive boner tenting out his swim trunks, and Kim was barely covering her breasts with her untethered bikini top. She gave Kaylie a big grin and a wink, and then headed to the house.

“Aren’t you going to do my legs, Jim?” I looked back down, and Kaylie had half-turned toward me, giving me a good look at most of her right breast.

“Um, yeah,” I replied, as she lay back down and I squirted a stream of lotion from her right ankle, up her leg, to the edge of her bikini bottoms. I worked my way from bottom to top, making sure, once I got past her knee, that I gave her inner thigh the same attention that she had given mine. She was squirming by the time that I got to her ass, and had spread her legs to give me better access to the junction of leg and vulva. I teased her along the edge of her bottoms, sliding a lotion-lubed finger just under the hem of the material.

Then, just as it seemed to her that I was going to make full contact, I took my hand away and applied a trail of sunscreen to her left leg. I repeated what I had done to her right, and by the time I got to the gusset of fabric covering her pussy, it was wet enough that it was almost translucent. Better still, it was so tight against her labia that the outline was clearly visible.

There was no doubt that she was aroused, and the stiffness of my organ made it clear that I was, too. The only question was whether anyone would make the next move, and what would happen after that. That was when Kaylie undid the ties holding the front and back of her bottom together and slowly lowered the back, exposing her cute ass. “I think you forgot a spot,” she said, her voice made husky by lust.

I squeezed some lotion onto my hands, then began massaging those two firm globes of flesh. I traced a finger down her crack, over her anal star, then across her leaking lips, which were still pursed tightly together. I didn’t even consider that she was anything other than a virgin as I slipped my finger between the folds of flesh, causing her to shudder as I found my way to her love bud. She began to slowly rock her hips as I slipped back and forth between her clit and her perineum; each time pushing further into the sopping gap between her labia until I found her opening.

I paused, not sure if I should continue. “Please, Jim, don’t stop.”

“Are you sure?”

She turned over so that she was now resting on her elbows on the chaise, facing me, her legs open, completely naked. Her neatly trimmed pussy glistened with her love dew, and the dark pink nipples on her breasts looked hard enough to cut glass. “Was it the beer talking, or do you really think that I’m sexy?”

I stood up, revealing the erect state of my manhood. “It wasn’t the beer.”

“Then I’m sure. I’ve wanted to lose my virginity for a long time. I want you to take it.”

The look in her eyes, a combination of sincerity and lust, told me that she knew what she was doing. “Okay then,“ I said, as I knelt back down between her legs, keeping them spread. I used my finger to once again tease the wet crevice of her sex. She tilted her pelvis up, urging me to push my finger into her untested orifice. Instead, I went for her clit, gentling circling the sensitive nub with my fingertip, occasionally applying direct pressure.

“Oh my god,” she moaned, “that feels so good.” I kept at it, amazed at how much wetter she got the longer I teased her. “God, I can’t take it! Oh god! Oh god!” She started bucking her hips. “Please stop! It’s too much! I’m … I’m … I’m CUMMING!” she screamed, as her orgasm overtook her.

She shuddered and shook, grasping her breasts as the intensity of her climax claimed control of her senses. I took advantage of the distraction, and as her pelvic movements slowed, thrust my middle finger into her tight, virgin vagina. She screamed again as her body registered this new intrusion. “Yes! Yes! Finger my pussy!” I obliged, gently pumping my digit in and out, slowly stretching the circle of flesh protecting her most intimate entrance.

She kept kneading her breasts, pinching her nipples, as she ground herself against my finger. Her whole body continued to tremble, as apparently her orgasm never quite fully subsided. I searched and found the nerve-laden coarser area inside, and concentrated my fingering to that area. She was gasping for breath, moaning “Please, Please, Please,” over and over as her juices continued to flow freely.

Her trembling turned to bucking, and I could tell that she was close to another full-blown orgasm. I pushed against her clit with my thumb, sending her over the edge again. “Oh fuck! Oh, fuck! I’m cumming! I’M CUMMING!” She thrashed about as I kept my finger buried deep in her pussy, feeling her tight walls of muscle contracting as her climax ran its course.

As she once again began to calm, I stood, dropping my swimsuit as I did. I was naked in my backyard and had the strong feeling that my daughter could see me, watching what I was about to do. But I didn’t care. Kaylie lay limp as I knelt back between her legs. I lifted them and placed them over the arms of the lounge, giving me better access to her sopping portal. Kaylie managed to rise back up onto her elbows, only to catch a glimpse of my raging hard-on.

“Oh, god, it’s so big!” Now, I’m not porn-star big, but I am bigger than normal, especially in length. She looked worried. “Will it fit?” she asked.

I ran the circumcised knob at the top of my shaft through her labia, causing her to shiver. “Don’t worry, it will fit.” I found her entrance and pushed the tip just up against it. “It might hurt, though.”

“I know; Kim told me about it when she, well …”

I shook that thought out of my head. “I’ll be gentle,” I promised.

“No, I don’t want gentle. I want to be a woman. I want to be fucked.”

I couldn’t believe what I was hearing; but at the same time the thought of ravaging this girl, of forcing my cock hard and deep where no man had been before, of shredding her hymen in the process, was a major turn-on. “Are you sure?” I asked, giving her one last chance to forgo the pain.

“Yes. Fuck me! Fuck me hard!”

I made sure that my cock was lined up, then pushed as hard and fast as I could. My god but she was tight; wet, hot, and tight. I was able to push past her resistance, balls deep, but I knew that it had to hurt her.

“Aiyee!” she screamed, as tears sprang from her eyes. I stopped, holding myself in place as she whimpered, then cried. I started to slowly pull out, hoping to give her some relief. But she wrapped her legs around my ass and held me still. “No, don’t,” she pled between soft sobs. “Please don’t.” I could feel her cunt contracting my shaft, then releasing, as she tried to accommodate my prick’s presence in her pussy. “It hurts, god it hurts. But I figured it would. Just let me get used to it.”

Then she did something totally unexpected. She put her arms around my neck, pulled me down, and kissed me. At first, it was soft, but then the pressure of her lips on mine was so hard that I could feel her braces through her lips. Suddenly, her mouth opened and my tongue instinctively plunged in. She moaned into my mouth as she sucked my tongue deep into hers. Her inexperience was evident, but her enthusiasm more than made up for it. I didn’t even mind the braces.

As our tongues continued to battle, I slowly started pumping her, using a slight rolling of my hips to slide in and out an inch or so at a time. She winced the first few times, but then started rocking back, wordlessly letting me know that she was ready for more.

I increased both the tempo and force; she used her legs to keep me from pulling too far out. “Unh! Unh! Unh! Yeah, just like that!” she groaned, as I gave her short, fast thrusts. “Yeah, that’s it! Don’t stop!”

It had been a long time since I’d been with a woman; even longer since I’d fucked such a tight, hot box. She was so wet that her pussy made these soft, sloshing, sucking sounds as I worked her cunt. My balls were soaked.

I was trying to not cum, so didn’t notice right away when her rocking became a little more frantic. “Good! So good!” she cried out. “Yeah! Keep going! Fuck me harder! Yeah!” She had released her legs’ grip on my ass, pulling them back to her shoulders, giving me full rein. I was able to pull back farther, and drive in deeper, harder, faster. Soon she was panting. “Oh god! Oh god! Like that! Like THAT!” She went crazy, her first fuck-induced orgasm wracking her body as she cried out in ecstasy, “FUCK! FUCK! FUUCCKKK!”

I pulled out, afraid that I’d lose it and pump her unprotected pussy full of my baby-batter. My cock was twitching and throbbing right at the entrance. She came down far enough to realize what I had done. “Why did you pull out?”

“I didn’t want to get you pregnant.”

“Oh, fuck!” she exclaimed, as she grabbed my cock and pulled it back towards her newly deflowered vagina. “Don’t worry about that. I’m eighteen; I can always get a “morning after” pill.” I pushed back inside, deep, taking her breath away. She stared into my eyes. “Fuck me until you cum in me. I want it all.”

I pulled out again. “In that case, turn over and get on your hands and knees.” She scrambled to comply, sensing what was coming next. I lined my cock back up with her pussy and drive it home, as deep and as hard as I could.

“Aiyee!” she screamed again, this time because the tip of my spear bounced off her cervix. I rocked her forward, using her knees as a fulcrum as my shaft slid half-way out, then pulled her back hard, impaling her for a second time and eliciting another cry of pain. “Why does it hurt like that?” she cried out.

“You said that you wanted it all. I can go deeper from behind. I’m hitting your cervix,” I explained. I expected her to tell me to stop; instead, she started pushing back as I pulled her back. The cries of pain changed to guttural grunts as her ass slammed into my abs, shaking with the force of impact as I continued to batter the entrance to her womb.

The heat and grip of her pussy, along with the thought of how wanton Kaylie had become once I’d penetrated her for the first time, was taking its toll. “I’m gonna cum!” I warned as I sped up.

“Yes, cum in me! Fill my pussy!”

With one last push, as hard and as deep as I ever imagined, I let loose. “Aargh!” I yelled as I splashed rope after rope into her most intimate, her deepest, recess.

“Oh god! I can feel it! I can feel your cum!” she cried out in reply, as she climaxed yet again.

I held her against me, still buried deep in her cunt, as I slowly regained normal breathing. Kaylie had collapsed slightly, her face now buried in the lounge cushion. She was still panting, and her vaginal walls were squeezing my softening shaft in time.

I pulled out with a soft, squishy sound, slapping her on the ass as I did so. She gave a sharp yelp, but made no effort to lower her ass; instead, she remained on her knees, her ass sticking up, her legs spread wide so that her swollen, freshly fucked pussy was on full display as blood, sperm, and pussy juice ran down both her legs.

I was still a little foggy, but could swear that I heard clapping. I turned to see Kim, a big grin on her face. “Well done, Dad! Well done!”

Kaylie finally collapsed fully, laying on her side as she looked back at me and my daughter. I stood up, my half-hard cock dangling down, coated with the dregs of our deed. I should have been embarrassed, but then I saw the look that passed between the girls.

“It hurt a lot more than you said it would,” Kaylie said, turning completely onto her back. Our juices still oozed from her slit. “But you were right, it was worth it. I just wish that you’d told me about the pain deep inside.”

Kim looked confused. “What do you mean?”

“When your Dad was all the way in, he hit my cervix. It stung like a mother-fucker. And, when he came, it felt like he was squirting hot lava against it.”

Kim turned a little red. “I guess none of my boyfriends were, are, as long as my Dad, then, because I’ve never had that problem. I’m sorry, I didn’t know.”

Kaylie smiled. “No worries. It may have hurt, but it made me feel like I had been really, truly fucked. That he was as far in as he could be. Like I’d be knocked up for sure if you hadn’t given me that “Plan B” for later. And happy that I’d taken it all.”

I couldn’t believe the conversation that I was hearing; that my daughter and Kaylie had conspired to get me to take Kaylie’s virginity, while Kim watched. And, to top it off, that she felt that the pain was a badge of honor. But what happened next was equally unbelievable.

“Well, if it feels that good, I guess I need to get a boyfriend with a bigger cock.” Was I hearing my daughter correctly?

“Or,” Kaylie replied, “and this is just a thought …” She was staring at my cock, which had started to get hard again. Kim glanced where Kaylie was looking, quickly grasping what her friend was meaning, and smiled. “I don’t mind sharing, Kim.” Kaylie looked again, noticing that I was now fully hard. “And, it looks like your Dad’s up for it.”

 

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