tagIncest/TabooNailing The First Stuckup Virgin

Nailing The First Stuckup Virgin

byimhapless©

For those who didn't read "Planning To Nail Two Stuck-Up Virgins," a one paragraph summary:

I'm Brian, a 19 year old hockey player, mature for my age, obsessed with nailing Lisa and Carolyn, two stuck-up plasma-hot 18 year old prick tormenters in my high school. I enlisted the help of my 23 and 22 year old provocative cousins Jen and Ginger who taught me to find a woman's G-spot and then gave me real-life fucking experience and training until they thought I was a 10. Their plan was for me to fuck Madeline and Faith, the mothers of friends of Lisa and Carolyn, respectively (Cherry and Julia are the daughters), and make sure their daughters found out about it. I've done that, and am now ready to start executing the plan.

I couldn't thank Jen and Ginger enough for their help. Even if the ultimate goal of nailing Lisa and Carolyn wasn't achieved, I had so much fun fucking Jen, Ginger, Madeline and Faith, I was already one of the happiest men alive.

While Jen and Ginger were proud of my accomplishments so far, like a good hockey coach they weren't satisfied with just a "conference championship" -- they wanted me to win the "State Championship." There was almost a month left before school started and they told me there was no reason to wait until then. So they made me join the community swimming pool (I don't really swim worth a damn -- I like my water frozen), went with me to purchase bathing suits, and gave me my marching orders.

When I went to the pool the next Saturday, as I walked in I immediately saw two of Lisa's friends, Ginny and Sue. They smiled at me, I said Hi, and as soon as I walked past they began texting. I found a shady spot and sat down.

It wasn't long before Cherry and Lisa showed up. They were so close it seemed like they were joined at the hip, and did everything together. I couldn't believe what happened next.

Cherry, Madeline's daughter, walked over to me wearing the skimpiest bikini I had ever seen, with no cover-up. Cherry is a very good-looking woman, just having turned 18, though not as hot as Lisa. But she does have her mother's best features -- at least as far as can be determined without an intimate inspection.

"Hi Brian, I haven't seen you here before."

"Well I just joined."

"Why are you sitting in the shade?"

"Because I burn easily and I plan to be here most of the day, so I wanted to minimize my exposure to the sun."

"You know you can put sun block on."

"Yeah, but I like to lie on my stomach, and I can't reach my back."

"I'd be happy to help you with that."

"That's really nice of you Cherry. I probably will take you up on that later. Do you have sun block on?"

"Not yet. I just got here. I have the same problem you do -- would you mind applying it to my back?"

"I guess -- but aren't you here with your friends? Can't you ask one of them?"

"Ha, ha. I would Brian, but we are always playing tricks on each other, and I don't trust them."

"What do you mean?"

"Well last week Lisa and I put sunblock on Ginny's back but we did it in such a way that we put no sunblock in the shape of letters on her lower back. By the end of the day 'SLUT' was very visible in red. Lisa, Sue and I laughed so hard I thought we would split our guts open. Ginny took it in good humor but vowed revenge."

"Ha, Ha. You're a little devil aren't you? I can see why you don't trust them. All right, bring your sunblock over."

As Cherry went back to her lounge chair she didn't walk. She sashayed, wiggling her ass like a fisherman dangling a lure. When she returned she lay on her stomach on the lounge chair next to me. After no more than two minutes of small talk it was "bombs away."

"So Brian, did you enjoy fucking my mother?"

"What are you talking about? Who told you I fucked your mother?"

"Lisa and I saw you doing it."

"What? How could you?"

"We did. We saw you gently stroking in her, and then when she screamed for you to fuck harder we saw you pounding her."

Jen and Ginger had prepared me for this -- we actually went through a Q & A practice session; God I love my cousins! So I stopped applying sunblock, took off my sunglasses, removed Cherry's, put a fake embarrassed look on my face, and continued.

"Geez, Cherry. I hope you haven't told anyone about this. I mean, that was just between your mother and me."

Cherry got a wicked smile on her face. "Well it looked like she really enjoyed it -- 'best fuck ever' I heard her say. Now answer my question; did you enjoy it?"

"Look Cherry, anything I say to you can't go any further, OK?" [Yeah, right, Ginger assured me Lisa and her friends were incapable of keeping secrets.]

"Sure Brian, anything you say."

"I'm not the type to kiss and tell; I never talk about my exploits. But yes, Madeline was a wonderful sexual partner. I loved it!"

Then talk so direct even Jen and Ginger hadn't prepared me for it:

"Well I would have thought that her pussy wasn't tight enough for a really good fuck, Brian. Wouldn't you rather have a teenage pussy to fuck?" After a good 60 seconds of staring at my dumbfounded face like a cobra would its prey Cherry went nuclear: "Like mine?"

After another 30 seconds I finally regained my composure. What snapped me back to attention was thinking "Ginger and Jen invested hours of their time in you moron; don't disappoint them. Rally!"

Staring back at Cherry as intently as she was staring at me I was proud of my way out of it.

"Are you a virgin Cherry -- be honest."

"Well I haven't had a dick in my pussy before if that's what you mean."

"That's exactly what I mean. Cherry, don't you think it would be an insult to your mother -- who I like very much -- to have me fuck her virgin daughter? Plus, how do you know you'd like it?"

"No I don't think it would be an insult. We swap underwear."

"That's a little different than sharing the same cock."

"Is it? Both contact our pussies. Anyway, I could tell by the gentle way you handled my mother before she begged you to fuck her hard that you'd be gentle with me, so I wouldn't be apprehensive, and I know I'd like it."

"Have you discussed this with your little co-voyeur Lisa?"

"Maybe."

"Listen Cherry, you're being direct with me so I'm going to be with you. I've never fucked a virgin before" [so not true, I thought] "and I don't want the first time to be the daughter of a woman I enjoyed sex with, in case something goes wrong. Maybe if I fuck your co-voyeur Lisa and everything goes OK with that I'll fuck you too. Or would you have a real problem with me taking both of your virginities?"

After another long pause as Cherry started to get up she said "I'll talk to Lisa."

I grabbed her arm and gently pulled her back down onto the lounge chair, and continued. "You do that, but first I'm going to finish putting sunblock on your back and the back of your legs."

She only smiled in response. With that I straddled her on the lounge chair, and gave her as much a back massage as sunblock application. I was hard by then, and there is no doubt her ass crack noticed my hard on -- in fact she flexed her ass up into it. After I finished with her back, I knelt on the side of the lounge chair and applied sunblock to the back of her legs, making sure to go all the way to her crotch and touch her mound. As I was finishing I left a finger in contact with her mound for a good fifteen seconds. As she moaned I quietly said to her "Actually Cherry, I hope this does work out. I'd like to see if your G-spot is in the same location as Madeline's."

I then stood up, said "I've got to do something about this hard-on you've given me," and went and jumped in the pool.

After doing my poor imitation of the Australian crawl and breast stroke for a couple of laps, I returned to my chair. I couldn't believe it, but within five minutes Lisa came over to me.

"Hi Brian."

"Hi Lisa." Some small talk; then I pulled a Cherry:

"Say, Lisa, did you and Cherry really see what she said you did?"

"You mean watch you fuck Ms. Johnson?"

"Without admitting I did it because I don't tell anyone about my sex life, yeah."

"Uh-huh."

"Why?"

"I don't know. We never saw anyone getting fucked live before and wanted to see what it was like."

"What did it look like?"

"It looked like a lot of fun. Ms. Johnson sure enjoyed it."

"You know you've almost never talked to me before Lisa. Why are you talking to me now?"

"Well -- I'm kind of embarrassed."

"Shit, Lisa, I'm not going to tell anyone anything you say to me. I know how to keep my mouth shut and I will. I think you know that by now."

"Well, I'm kinda tired of being a virgin. But I don't want to have a bad experience my first time like some of my friends have; I'm a little scared. And, well, uh, Cherry and I could tell from the way you handled Ms. Johnson that you wouldn't hurt us."

"Wait. Are you actually asking me to take your virginity?"

"Well -- shit this is hard -- I'm not good at this -- yeah. I don't want some clown who doesn't know what he's doing, that's for sure."

"I don't know, Lisa. Since you get hit on all the time I guess you don't know that guys are particular too. I'm not just a stallion out to stud you know."

Lisa diverted her eyes downwardly. I lifter her head up so she had to look me in the eye: "I'm not a booty-call. And I'm quite certain that you'd back out even if I agreed."

"I, uh, well, uh, I don't think of you as a booty call. I like you. I promise I won't back out."

After another long pause as I stared into her eyes. "Okay Lisa, listen. You and Cherry have to promise not to talk about this with anyone, especially Cherry's mom. Promise?"

"Promise." [I was actually counting on that not being worth the ink used to print it.]

"OK. I'll think about it. Call me tomorrow afternoon or evening and tell me if that is what you and Cherry really and truly want. I'll tell you then if I agree to it. If we agree, though, there is no backing out!"

I couldn't believe it. Despite how hot Lisa was, she almost never smiled -- certainly not at me. But with a smile bigger than I thought she was capable of she replied "Thanks Brian. I'll call you tomorrow. What's your cell number?"

Lisa and Cherry left soon afterwards. About a dozen other girls came up to me in the next three hours I stayed at the pool, flitting around like little hummingbirds, including some of Carolyn's friends who had never really talked to me before. Ginger and Jen were right. News of me fucking two moms to top notch orgasms had spread like wildfire throughout the teenage girl network.

I called my cousins to report that things were working out perfectly, and I would make arrangements for my first conquest tomorrow. Ginger's response: "Great Brian. Since I don't have a date tonight why don't you come on over to make sure your plumbing is in good working order." Ginger found out it was as I fucked her twice that night.

One thing I forgot to mention. My cousin Ginger is a nurse. Now that she knew I would be nailing virgins, she felt obligated to give me a short course on hymens and their relation to G-spots. I thought it was TMI, but she said I needed to be prepared. I never even thought about it with the only virgin I had fucked to date, but that was before I even knew that a G-spot is real.

"The three main types of hymens are annular, separate, and cribriform, in order of how common they are. Normally, each must be broken before the G-spot can be located. Also, unless the girl really is anxious for it, you don't want to try G-spot stimulation right after breaking the hymen."

"Is this really necessary Ginger?"

As she grabbed my balls and lightly squeezed she continued with a diabolical grin -- "Have we steered you wrong so far you little bastard? Listen up."

"Okay -- don't squeeze my nuts -- I promise to take in every word."

In the next 15 minutes I learned more information about hymens and how to handle them than I thought existed; and Ginger convinced me that the girl I fucked who I thought was a virgin really wasn't. Bummer. But I was ready now.

About two seconds after noon on Sunday (I told Lisa to call Sunday afternoon or evening -- I guess she was anxious) my cell rang. Of course it was Lisa, on speaker, with Cherry next to her. It was clear to me that this was going to be a package deal. While I had set my sights on Lisa, I had no problem fucking Cherry at the same time.

"I want you to understand that the first time may be more painful than pleasurable, and it is possible that there will be bleeding."

"We understand," Lisa and Cherry blurted out in unison, like Tweedle Dum and Tweedle Dee.

Arrangements were made. Ginger and Jen helped out again by offering their spare bedroom the next Saturday morning. Cherry and Lisa insisted that their first time be together. I thought "What the hell -- it will calm them down and it will make it just that much better!"

When the time arrived I was as excited as I ever have been. I purposely had not had sex or masturbated for three days so I would have a full charge. Also Ginger gave me two "morning after" pills which I told Lisa and Cherry I would provide since they were not on birth control, no one wanted a pregnancy, and there would be no condoms.

Based upon their history, I thought Lisa and Cherry might be nervous and flighty. But probably because they saw me fucking Madeline, and they were together, that wasn't the case -- they were simply excited, like I was. Both were dressed very provocatively. I was commando, just a T-shirt and shorts.

After we chatted a few minutes, they took a quick tour of my cousins' small house to see that no one else was there, I informed them there were to be no photos or videos, and I gave them sodas to drink. We went into the spare bedroom and locked the door.

I took off my clothes first, revealing a raging hard-on -- maybe the biggest I've ever had, and certainly the most active since it twitched every minute or so. They were mesmerized by it.

As I gently took off Cherry's clothes I told her that she was going to be a spectator the "first period." I kissed her body parts as they became exposed, including gently running my fingers around the circumference of her breasts, and drawing my fingers lightly over her bare shaved mound. I couldn't help but think to myself that her tits were a younger version of Madeline's nice rack, with similar large areolas and pronounced nipples.

After I sat Cherry down in a padded chair I approached Lisa. As I stared unblinkingly into her beautiful alluring eyes I resolved that sometime -- likely not today since I probably would have to be gentle, but sometime -- I would fuck her raw. After staring at her a few minutes with my hands on her shoulders and arms, I got behind her and disrobed her from the rear. I lingered on each breast and on her ass, stroking with enough force to stimulate the nerve endings, until she started oohing and panting.

I kissed the nape of her neck turned her around and squeezed her as I French kissed her, my cock burying itself in her stomach. Then I lay her at the edge of the mattress, moved her legs widely apart, and worked her clit over with my tongue. I used this time to inspect her hymen -- a rare cribriform type, which meant it certainly would hurt and bleed when penetrated.

By stroking her thighs and licking her clit I brought her to an orgasm. Not an earth-shattering one, but definitely pleasurable for her, causing her to moan and her breathing to quicken.

As I relaxed while waiting for her panting to subside, I scanned her entire body. This really was a fucking hot woman! Almost every part of her body was perfectly shaped -- like she had stepped out of a magazine after being airbrushed.

I wanted my penetration to be face-to-face so I shinned her up the mattress so that her ass was on a towel I had strategically placed there. I held her arms down, and while keeping her legs apart with my hips brought my dick into contact with her hymen. I stole a glance at Cherry, who was rubbing her clit and staring wide-eyed at us.

I so wanted to just jam my cock up her hole and start banging at 100 mph, but I resisted the temptation and just slowly circled my hips with my cock in contact with her hymen. After a few minutes of this I told her I was going to penetrate her and then started pushing in. I felt her hymen give bit-by-bit as the little bridges of skin forming a web over a central opening started to pop. Lisa was grimacing, but not screaming or crying -- she apparently really wanted this.

Finally the last little bridge gave way, and I popped into her. She winced in pain, and I could feel a little liquid that I knew was blood, between us. I just stayed in position in her without moving, talking to her softly: "I'm through now. I'm not moving until you tell me to. There is only a little blood. I know it hurt but in 10 minutes you'll have forgotten all about the pain," etc. Even though I wasn't moving my dick remained rock hard -- it liked where it was!

After about 5 minutes Lisa got a smile on her face, said "I'm not a virgin anymore, am I?"

My response "Technically, no; but now you need the fun part."

"Okay -- fuck me, but not too hard unless I say," she moaned back since I had already started slow grinding.

"You got it; you control the tempo girl," I groaned.

I have to say, it lived up to my expectations. As I was slow pumping and grinding in Lisa I realized that my obsession with fucking her had many different facets: she seemed unattainable and that was a real challenge; her spectacular body would be fun to explore even if she was a bitch; I really wanted to control her, if only for a little while, because she was so stuck up she seemed to lord control over everyone; and I would achieve stud status by nailing her, with no need for self-promotion!

I felt an enormous buildup in my balls. I was too excited. I wasn't going to last until she had an orgasm. I would have to go with a different scenario, using all of my G-spot training. Knowing the surge was coming, I quickly lifted both of her legs on my shoulders, pumped deep and hard four times, and then the blast occurred. She started shaking and moaning loudly as shots of seminal fluid were erupting into her vagina.

While she was enjoying it, I knew she wasn't climaxing. After the last stream left I quickly pulled out, spread her legs wider, and with the fingers of my right hand went after her G-spot while sucking her clit completely into my mouth. She was alternately pushing my head and pulling my hair and yelling "What the fuck" until I hit the magic bundle of nerves. As I started abusing it, she started gasping for air and soon she went limp and was literally whimpering as all of her nerve endings were overloaded by a massive orgasm.

While I was still very gently stroking her clitoris with one hand, and kneading a thigh with the other, I looked at Lisa's gaping non-virgin gash. It was beautiful. I looked over at Cherry, and she was literally frozen, with her mouth open and her eyes as big as hockey pucks as she saw cum leaking out of her friend's cunt as Lisa dissolved into a happy puddle of protoplasm. I got a big shit-eating grin on my face and mouthed "You're next," to Cherry, which made her instinctively start rubbing her clit again.

Once Lisa was completely motionless with a big smile on her face, I kissed her on the lips, got up, picked up Cherry and carried her the few steps to the bed. I lay between Lisa and Cherry, snuggling both of them waiting for my cock to rise again and engaging in pillow talk. Lisa didn't have much to say -- she just kept repeating "I don't believe it -- wow that felt good."

Cherry was full of questions. I never really knew her that well until a few days ago, but she was turning out to be about the most direct and inquisitive person I had ever seen. Questions like "So how does your dick feel after a fuck?" "How long does it take you to recover?" "Do you like older women better," and on and on, always staring at me with wonderment. Then the questions changed:

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