Planning to Nail Stuck-Up Virgins

I have to admit, her tits were really nice. Plump without much sag, large areola and oversized firm nipples. They were so inviting I started sucking on them, eliciting pleasure groans from Madeline.

After sucking each tit for about five minutes I removed Madeline's panties and ran my fingers through her full but thin bush. It was no surprise that it was a different color than the hair on her head. What was a surprise, however, was how nicely trimmed the bush was, how prominent her pussy lips were, and what nice, creamy, thighs she had!

Once I ran my hand over her gash a few times while staring into her eyes I said: "Don't you want to see what I have for you?"

Her smile grew bigger as she slowly undid my belt, button, and zipper, and pulled my pants down. My hard on was poking through the flap of my boxers. At first she probed the exposed part of my cock with her fingers, like she was checking whether or not it was real, and then pulled down my boxers, which I quickly stepped out of.

I laid Madeline on her back on the mattress, and expertly went on a quest for her G-spot. I intentionally took my time finding it but when I did I immediately went for the kill. Using everything Ginger and Jen had taught me, I so expertly abused her bundle of nerve endings that she was soon writhing around, pulling my hair and moaning loudly. After I knew she was on the verge of a precipice I started sucking her clitoris while continuing to work over her G-spot. Within a minute she had an earth shattering climax, and clamped her pussy on my two probing fingers.

I lay next to Madeline as she recovered, playing with her tits and pussy lips, and kissing her lightly on her cheeks and forehead. Then my cell phone rang once -- only once. That meant that Ginger had seen Cherry approaching the house. ("My God, Ginger and Jen had to be mind readers to know that Cherry couldn't stay away after getting that text -- remind me never to try and fool them," flashed through my brain.)

Now I went to work. Positioning Madeline on her hands and knees and so that both of us could be recognized by someone standing at the door to the bedroom, I stroked her pussy a few more times and then buried myself in her balls deep. I started slow fucking her. While she was indubitably enjoying it, after a couple of minutes she started begging me to fuck her harder; but I needed to wait. Soon after she started begging I saw two heads reflected in her mirror peering surreptitiously around her doorjamb. I slow fucked her another minute or two until she was almost screaming for me to fuck her harder.

Then I started pounding the shit out of her. In addition to moving in and out I was occasionally rotating, and with my hand closest to the door massaging a tit. I took one last glance in the mirror to confirm the heads were still peering around the doorjamb and then started grunting and groaning as I discharged a colossal load of joy juice into her. She started shaking and screaming and then started whimpering. Playing her part better than if I had scripted it, interspersed with her whimpers were "Oh my God that was amazing," "Holy shit," "the best fuck I ever had." After that last statement I pulled out of her, lay on the bed, and rolled her on top of me, stroking her ass and the side of her tit closest to the door, as I continued to kiss her while stealing glances into the mirror.

After another couple of "Oh Wows" from Madeline I proudly and loudly proclaimed "I'm not done with you Madeline; we're gonna fuck again in about ten minutes," causing her to lift up her head, look me in the eye smiling, kiss me on the lips and say "I don't have any nerve endings that are still functioning, but fuck away whenever you're ready."

After that I could see the heads move away from the doorjamb, and I got a shit-eating grin on my face.

While I could have left then since my mission was accomplished, I have to say I truly enjoyed fucking Madeline and saw no reason to leave. I told her I had to make a couple of calls and out of her hearing called my parents to say I would be crashing at Ginger and Jen's house, called Ginger and told her she was a genius and that it went perfectly and asked her to cover for me if my parents called because I was spending the night.

Ginger's response: "You like that mature pussy, huh?"

My reply: "Not nearly as good as yours, but I want another go at it."

Ginger just laughed and said "I'll cover for you."

I went back to bed and fucked Madeline again as running through my mind was the delicious thought that both Cherry AND Lisa had seen us fucking and heard Madeline praise my abilities. I also woke her up in the middle of the night and fucked her a third time, and then ate her in the shower we took together the next morning when her pussy was too sore for another fuck.

When I left about 10 a.m. on Sunday Madeline said smiling -- not teary eyed -- "I feel better than I have in twenty years Brian."

"You are one amazing fuck Madeline," I replied, then French kissed her good-bye.

WOW! One down, one to go.

The next target approach was as disastrous as the first was smooth. I've suppressed all memory of it so don't ask. At least that gave me time to close up loose ends on my arrangement with Madeline.

I called Madeline up and told her that I had lost my job because the company I worked for had gone bankrupt. Jen had already called her to tell her that so she wouldn't try and contact our fictitious company to buy cabinets. I then said "I hope we can still be friends."

"Brian you didn't tell me you were a rising High School Senior."

"It never came up, Madeline. I didn't think it mattered. How did you come across that?"

"Well I think you know my daughter Cherry."

"You mean you are the same Johnson as Cherry Johnson?"

"Yes."

"Wow, I didn't know. I never saw you at school or hockey games."

"That's because I rarely go to the school and have never been at a hockey game. Anyway, a couple of days after our 'meeting'---"

"You mean our over-the-top fuck session?"

"Ha, ha. Yes you could put it like that. Anyway Cherry was looking through her yearbook at the kitchen table asking me if I thought various guys in her class were cute when she pointed out your photo. I almost fainted right there."

"Ha, ha, well what did you say?"

"When I regained my composure I said 'He's not bad.'"

"Not bad, huh, ha, ha."

"Well what did you want me to say, 'He's a great fuck?'"

"Ha, ha. Guess not."

"Well after that I said 'Why are you asking me about this Cherry?' She just smiled and said 'No reason.' You haven't told anyone have you Brian?"

"No, I don't kiss and tell. Plus, I didn't know until this conversation that you were the mother of someone in my Class."

"Well, I am embarrassed that I had sex with a High School boy, although you certainly don't look or act like one. I can't repeat it."

"Look, Madeline -- how about just once more and I promise, promise, promise I won't bug you again. I just need to get in you one more time."

There was a long, pregnant pause. "Just once more. Tomorrow night, Cherry will definitely be gone from 7-9."

I really enjoyed fucking Madeline again --"Mature pussy really is nice if she is representative," I remember thinking to myself -- and we mutually gave it up after that.

Back to the next target -- Jen and Ginger didn't let the disaster get me down. They put me after the backup target -- Faith, the mother of Julia, one of Carolyn's friends.

Faith took a little more work than Madeline. But unlike Madeline, I had no trepidation about fucking Faith, and not just because Madeline had turned out to be fun. Faith had a perfect bubble ass, slim waist, and a face bordering on beautiful.

My initial hook on Faith was that she attended spinning classes three times a week without fail. [For those unfamiliar with "spinning" it is a stationary bicycle exercise class with a leader, music and light settings, and sometimes videos, to keep things interesting.] I joined the class, and quickly got to know her, and rode next to her for the 2nd through 4th classes we took together. Like Madeline she had no clue I was in High School. I had gotten chummy enough with her that I asked if I could get a ride from her if I ever needed one, and she could from me, and we exchanged phone numbers.

The 5th class we were to be together was on a Saturday of a weekend she had told me Julia was going to visit her father (divorced from Faith) in another state. That morning I sabotaged -- in a manner easy to fix -- her powered garage door opener motor, and her car was stuck in her detached garage. I waited for her call, and smiled to myself when it came.

I picked her up, we had a pleasant chat on the way to class, fun there, and I told her I would look at her garage door when I dropped her off. I also told her that I might have to drop out of spinning because of my "work" schedule, and was pleased to see disappointment on her face.

When we got to her house I immediately fixed her garage door motor "Just a loose wire" I told her. She invited me inside for a drink. She didn't drink booze, only healthy stuff, so I was wondering what needed to be done to suppress her resistance. I needn't have worried.

Faith pretended to get a cramp in her right calf. I immediately went over to her and started massaging it. She liked it -- lots. I then made up some bullshit like if your calf cramps sometimes a thigh cramp can't be far behind, and she gladly gave up her thigh to me.

To make a long story short, within 10 minutes of me touching her thigh we were fucking each other's brains out in her shower. By rubbing her G-spot and clitoris I gave her three more orgasms, and I fucked her twice more, before I left the next morning. God I was learning to love mature pussy; no games, whining, "will you still respect me," any of that shit.

Letting Julia know about this was also more complicated than Cherry's situation. But our intelligence came through once again.

On Wednesdays Julia always took her lunch break from her summer job working for the Park Service at a particular park bench. I cut out of work just a little before noon, and got to the bench next to her bench a little before she did. When Julia arrived I called Faith and had a conversation on the phone that I made sure was not too loud as to be obvious, but loud enough for Julia to hear. Uttering her name over and over again, I told Faith that I had had a wonderful time, that sex with her was remarkable, and made sure to say things like "I knew you would like my action on your G-spot." I could tell Julia -- while looking straight ahead and quietly eating a sandwich -- was taking in every word.

After the call I got up and walked past Julia, and pretended to do a double take when I saw her and stammered:

"Oh; hi Julia."

"Hello Brian."

After I slowly walked past her I turned and with a puzzled look on my face asked "Julia, I know that this is an odd question, but what is your mother's name?"

With half sneer and half smile she responded "Faith."

I gave an Academy Award performance by putting my hand to my mouth -- looking scared and speechless -- then just mouthing "Oh," and slowly turning and walking away.

The advance work was now complete. Would Jen and Ginger be right? Would this open up the stuck up vixens' thighs so I could cram my dick into their virgin cunts?

--Stay tuned for "Executing a plan to nail two stuck up virgins" which will be in a different category since no more significant incest.--