Planning to Nail Stuck-Up Virginsbyimhapless©
I was obsessed with nailing Lisa and Carolyn. They were 18 year old stuck up virgins who teased all of the guys in our high school. I have to admit it, though -- if anyone ever had reason to be stuck-up based upon looks alone they did.
Lisa was blond, blue-eyed, lanky, very light complexion, as big a perfect bubble ass as a 5'7" 125 pound woman could have, perky tits, absolutely killer thighs, and fashion model face. Carolyn had medium length black hair, brown eyes, a dark complexion, a set of knockers way too big for her 5'3" 115 pound frame, and a face and look that defined "sultry." They didn't get along with each other probably because they were competing for the title of the school's biggest dick tormenter. They both considered it doing you a favor to talk to you.
Getting in the pants of these little shrews wasn't going to be easy, even though I considered myself a hot shit. At 19 I had just been elected captain of the hockey team for next season and was sure to be pre-season all state. I had matured physically early and had already had more than my share of tail by the summer before my senior year, but wasn't even close to nailing Lisa and Carolyn.
I decided to devote a considerable portion of my free time during the summer to develop a plan. For that purpose I enlisted the help of my two female cousins, Jen and Ginger, 23 and 22 respectively, both single and living together in a small house at the outskirts of town. They had always been great friends and advisors, and one time on a family vacation when I was 18 on a dare Ginger gave me a hand job.
Both Jen and Ginger were sexually aggressive and not bad looking. Their faces certainly weren't movie star beautiful, but their bodies were top notch, and their attitudes supreme, at least as far as this teenage boy was concerned.
When I told them what I wanted they gave me a list of factual information I needed to gather about Lisa and Carolyn and told me I would have to do whatever they told me to in order to succeed, and to do a month's worth of favors for them as payment after they tutored me. I readily agreed.
Most of the information they had me gather was to be expected. Some surprised me, however. The most surprising was a list of all of Lisa and Carolyn's female friends who had single mothers, their addresses, and as much about the mothers as I could find out. Fortunately I had a good relationship with the school busy-body, who also happened to be the daughter of the school secretary. In exchange for one condom-fuck she gathered all the information readily available.
I had a job during the summer, normally 8 a.m. to 4 p.m., Monday-Friday. Cousins Jen and Ginger had me come over to their house every day after work, and much of the day on Saturday and Sunday, for about a month. God how I loved those times, and look back on them with great fondness, because I didn't just receive "classroom instruction" but on-the-job training.
They revealed their plan to me. Fuck the mothers of at least one friend of each of Lisa and Carolyn, and do it in a way that the daughters are sure to find out about it. I didn't just have to just fuck them, however -- it had to be one of the best fucking experiences (more than once was great) of their lives. The on-the-job training had to do with both interesting them and then fucking them senseless.
After identifying four potential targets, we started on-the-job training. I remember my first conversation with Ginger about it like it was yesterday.
"So Brian, Jen is going to teach you how to interest the targets and how to fuck them subtly but so their daughters find out. I'm going to teach you everything you need to know about pleasuring them."
With my eyes as wide open as a snake's, and my zipper almost popping, I astutely responded "Okay."
"So first, do you know what a G-spot is and how to find it? It is what will separate you from her other experiences."
"Uh, actually, no. Gee, I thought that was a myth."
"Not every woman has one, it is sometimes hard to find even if she does, but if you do find it and know what to do with it you're golden."
Another brilliant response by me as I was now slobbering: "Oh."
May Satan take my soul if I lie, with that Ginger led me to her bedroom, undressed, spread her legs, and said "Start looking." This blew my mind, but I promised my teachers I would do what they said so I reluctantly (yeah, right) did as I was told.
As I started fingering Ginger she directed me as to what to look for and how to do it. "Gentle but purposeful; look for a rough patch; likely near the top of the pussy, about two knuckles deep."
I found hers after about 3-4 minutes (I could have found it faster, but I was having lots of fun and I wanted it to last as long as possible). When I contacted it she told me how best to stroke it. The next 10 minutes went something like this:
"Move your finger like in a -- aaagh, oh shit that feels good -- come hither motion. Oh God, that's it -- ooooh, groan -- gently for a couple of minutes, then harder. Oh shit, shit, shit, yes that's it. Now put in a second -- yelp -- finger; uh, oh, yeah, do the same -- aagh -- with it!"
Then the fun really began.
"Now while -- wow, holy shit -- doing that, lick my clit and grab my ass with your other -- fuck, ah -- hand."
After taking a deep breath she actually got off a complete sentence without moaning or groaning. "If I start shaking or screaming I'm climaxing; once I come down from that you poke me."
I followed Ginger's instructions with more enthusiasm than I ever have done anything else in my life -- even hockey! My tongue was working like I was a starving man licking an ice cream cone. My hand on her ass was massaging it and I even inadvertently stuck a finger on her rosebud, causing her to jump but not complain. And my two fingers in her cunt were beckoning her to come to me with all the intensity I could muster. I was a man on a mission.
I was probably as proud of anything I had ever done in my life when I caused her to shiver, shake, and scream as an orgasm ripped through her body like an F4 tornado. In fact I was so proud, admiring my work (since she was shaking so much I had to desist actual activity and just touch and gaze) that I forgot the last instruction. After Ginger started coming down from her high she mumbled "Get your fucking cock out of your pants and poke me you moron."
I immediately pulled my pants and boxers down to my knees, my cock was already so stiff and hard that it hurt, and I plunged it into her dripping wet cunt burying it completely. Now it was my turn to scream. Shit, no other fuck I ever had (most were with condoms) felt 1/10th as good as this first penetration.
After I pumped for a short while I got more instruction from my now almost-cognizant cousin: "That's it, now put my legs one at a time on your shoulders. Oh yeah; oh fuck yeah. Ohhhh. Now rub my clit with one hand while you knead a thigh with the other and while you bash the fucking shit out of me!"
I felt like a one-armed paper hanger, but did the best I could. I have to admit holding onto her creamy thigh, rubbing her now fully erect clit, and pumping with all I had, left me no time to think but just enjoy the moment. I rocketed a load into her! It felt over-the-top fantastic, and I started to slow down.
"What the fuck are you doing Brian, keep pumping and rubbing, I haven't come again yet."
So I did what I was told for another few minutes until she started shaking, shivering, and screaming again, so hard that she literally expelled my dick from her pussy as I was on a backstroke.
We lay next to each other, sighing, then giggling, then cooing, for 10 or 15 minutes. Then Ginger got into classroom instructor mode.
"Do I need to put on my clothes so you'll concentrate, or can you just listen?"
"Well, uh, I, uh..." came stammering from my lips as I stared alternately at her pink nipples and her leaking cunt with a pool of mixed bodily fluids puddling beneath it.
"Okay, Einstein, I'll put on my clothes. You too otherwise I might be tempted to clean off your dick, and that lesson is for another day."
"Holy shit, when's that?" I mumbled to myself as we both were getting dressed.
Once we were fully clothed, Ginger proceeded to tell me everything I did right, and wrong. She didn't mince words. "To make the plan work you gotta be the best fuck these mommies ever had" she was happy to interject every three minutes. "I guarantee that the more she enjoys it, the more you will. You're off to a good start. Today you were already an 8, in the top 10 of guys I have had sex with. But you're going to be a 10 before I get through with you."
What else could I say but "You're the boss Ginger."
"Oh, and one other thing, once you get used to me and you get to be a 10, you're going to have to find Jen's G-spot and fuck her good too, so we can see how you can adapt."
I'm not sure since my boxers were already fully covered with bodily fluids but I think I came again in my pants as soon as she said that.
Since I had such a sexy, willing, ebullient, experienced instructor like Ginger, I progressed quickly. After about two weeks of G-spot massaging, eating, and fucking, she pronounced me a 10. Then on to the next phase. "So she can't possibly forget her fucking experience with you, you need to do her a second time within an hour of the first."
At that particular point in time I hadn't tried that before, especially since I had always just fucked and not stayed through the night with someone. But I knew I could since I often masturbated at night even after fucking Ginger in the afternoon. So the next Saturday we went for our first "double header".
Though I'm devoted to hockey I like to use baseball clichés. I pitched a no-hitter in the first "game," and still got a win in the second one. A 10 and an 8 was Ginger's assessment, although for the first time I thought she was lying, because she sure acted like I gave her a great orgasm the second time, and when we were finished so much cum was leaking out of her pussy she needed to stick a hankie in it, and replace it twice before I left. But do you think I was complaining? Hell no! She was by far the best fuck I had ever had, and doing her twice in a row was heavenly!
After another week of "double headers," she said I was ready for on-the-job training with Jen.
Jen had not just been sitting on her thumbs during my training with Ginger. In addition to being regularly serviced by the two fuck buddies she had, she was doing extensive research for me, and had more information about my targets and their daughters than I thought was possible.
My first session with Jen was like a Sci-Fi experience. While Ginger liked me to be in control during sex, and Jen is laid back in normal life, I found out that when sexually aroused Jen is a wild woman -- a licentious, unrestrained, berserk sex maniac!
Our initial "consultation" started out clinically enough. Like Ginger, she undressed, spread her legs, and assigned me the task of finding her G-spot, although she insisted that I get naked ahead of time too. Her G-spot was smaller and more deeply and mysteriously positioned than Ginger's, but I went after it with even more determination than my first time with Ginger. Jen had always been somewhat of an unattainable vision to me. I masturbated thinking about her many times, and while she was always flirty and jovial with me I never envisioned I could ever hook up with her in the real world.
Though I was no expert at the time, I had seen my share of live pussies and loved porn so I thought I knew what an ideal vagina looked like. That misconception was dispelled when I saw and starting probing Jen's. Smooth big lips that she seemed to have muscle control over -- almost puckering to invite me in; a hooded clit that grew to an inch in size when stimulated; more snug than a virgin I had fucked.
I finally found, and then abused, her G-spot. It took more stimulation than Ginger's before she started freaking -- but when she did, she took freaking to a new level.
I had no sooner started to lick her engorged clit while still stroking her G-spot then she started emitting low guttural sounds. Before I knew it she had rolled me onto my back and was sucking my dick while I was still violating her clit and G-spot. She was like a goddamn vacuum cleaner she exerted so much suction. I never thought I could possibly get that hard.
Without warning she spun around, literally stabbed her cunt with my dick by leaping on top of me, grabbed my nipples and started twisting them, and moved her pelvis in so many directions at the same time I couldn't begin to figure out what the hell she was doing. All I know is that she was twisting, rotating, bouncing up and down, sliding forward and backward, and God knows what else all at the same time. My mind was literally blown as she erupted into an orgasm like she was Mt. Vesuvius.
Even through her orgasm she kept gyrating. After a full minute of this I knew I needed to try and take control, so I pulled her chest onto mine (wow her big soft tits felt good against me) and started pummeling the crap out of her. After only about ten strokes (the most energetic of my life up to that point) I ejaculated in her tight cunt, sending her over the edge again. While I continued to hold her chest against mind her ass was moving all over the place, and she was literally sucking ever milliliter of cum out of me.
I was drained. I thought we were done as she finally calmed down and we lay chest to chest and my dick popped out of her. But within twenty minutes she had rallied, sucked me hard as a rock, and descended upon my upright cock yet again. This time it was even wilder.
After we mutually pounded each other for about five minutes, she started rolling back and forth while we miraculously stayed mated. I couldn't believe that she was strong enough to move me back and forth, although I didn't put much effort into resisting. About the fifth roll she started climaxing, and literally rolled us off the bed, both of us landing on a side. She had already knocked the comforter and blankets off the bed so the landing was softened, and she didn't let our little flop dissuade her in any way. She kept gyrating, pumping and screaming, until I spurted some more wads of my cream into her.
Once we both recovered she gave her assessment. "You did a real nice job, Brian. Four or five more sessions and you'll be ready for anyone and anything."
When she said that I just smiled. Going through my mind, though, was "Shit, she might kill me by then -- but at least I will die a happy and fulfilled man."
Once my on-the-job training with Jen was over, I was hurting so badly I had to take a few days off from fucking and masturbating. Then my cousins gave me all the intelligence about the first target, and disclosed the other potential targets. I had, to my knowledge, never met any of them, although I might have seen them before.
The initial target was Madeline Johnson. She was the divorced mother of Lisa's best friend, Cherry. According to my cousins the lowdown was that she hadn't had a boyfriend, and likely hadn't been fucked, in several years, but had recently joined a health club to improve her muscle tone. Apparently Ginger got so much data by fucking Madeline's personal trainer just once that it was considered TMI for me, and I was only given the relevant parts.
To be honest I had a great amount of trepidation. Also, although Madeline was not bad looking by any means, I wasn't sure I wanted to fuck her. But there is no way I would even attempt to back out after what my cousins had done for me.
On a Saturday afternoon Cherry had already left for an overnight at Lisa's house. Jen had several days earlier pretended to be from a home improvement company having a blockbuster sale, and offered to send someone out to give Madeline an estimate on redoing her kitchen cabinets. I showed up at Madeline's door about 5:00. Jen and Ginger had made sure my outfit was perfect for the occasion, and had instructed me in detail how to approach the situation. It turned out to be easier and better than I thought.
Madeline was obviously impressed with my looks and clearly lightly flirted with me within two minutes of my arrival. I pretended to take all sorts of measurements, asked her all the right business questions while putting them in a flattering form such as: "I might not recommend a fully decorative knob for most people, but for a young in-shape woman like yourself, with an obvious appreciation for aesthetics from the way you've decorated your house, I think a brass decorative knob would be best."
Fortunately her cell phone rang once during the discussion, so Madeline retrieved it from her purse. It was Cherry with a quick question. After a 30 second discussion she signed off, apologized for the interruption, and placed her cell phone on the kitchen counter.
After a business discussion she asked if I wanted a cup of coffee. Then some wine (I looked like I was 22 or 23 even though just 19). I told her I liked older women -- teenagers and early twenties women didn't appeal to me. I asked if I should leave since I was sure her date would be arriving any minute. She started moving her legs apart as we sat and chatted. I would occasionally touch her bare arm, and felt it flinch or quiver. After we chatted and drank (her quite a bit, me very little) for two or three hours she went over to a cabinet with the supposed purpose of getting another wine glass to switch from white to red and said "I'm having a little trouble reaching it, Brian."
That was the type of cue my cousins told me I needed to pick up on and run with. I went over, got behind her and with her between me and the cabinet reached up and got the wine glass, moving my hard-on over her ass as I did so. She moaned. I grabbed her by the shoulders and turned her toward me.
"I've never been this direct before, Madeline, but I've also never been this turned on before. I need to make love to you, Madeline." With that I passionately kissed her on the lips. As instructed I broke off after about 20 seconds to give her time to protest.
"No Brian, we can't do that. I'm old enough to be your mother."
"Leave my mother out of it. I love your look and feel," I continued rubbing my hands up and down her body. She half-heartedly tried pushing me away. Then I planted a French kiss on her while pulling her ass toward me with one hand and kneading a tit with the other. The first part of the game was over; now for the fucking and expose‛.
I had already put the text "now" in my cellphone. While kissing Madeline I pressed the "Send" button, transmitting a text to Ginger, and then lifted Madeline up and carried her up the stairs asking "Where's your bedroom" while nibbling the nape of her neck.
"Oh, Brian, I don't think we should do this -- to the right at the end of the hall on the second floor -- I don't want you to be disappointed."
I made sure to leave her bedroom door wide open when I carried her inside and placed her on her mattress.
While I was disrobing and probing Madeline, on my quest for her G-spot, Ginger entered the house and used Madeline's cellphone to send a text to Cherry that read: "Be sure not to come back into the house the next two hours." Then Ginger left and waited in her car, parked across the street.
When I got Madeline upstairs I slowly took her clothes off, kissing her passionately after the removal of each article. After I removed her bra I took my time tracing my fingers over the entire circumference of each breast, and then played with both nipples lightly twisting and pulling on them. At first she only intermittently looked me in the eye, obviously playing mental ping pong with whether she should let herself go, but after about the fifth light twists and pulls of her nipples, she stared straight into my eyes with a sly smile on her face.