Nailing Two Virgins – The Finalebyimhapless©
For those who didn't read "Planning To Nail Two Stuck-Up Virgins," and the sequel "Starting To Execute Plan To Nail Stuck-Up Virgins," a short summary:
I'm Brian; as this story starts I'm an 19 year old hockey player, mature for my age. I'm obsessed with nailing Lisa and Carolyn, two stuck-up plasma-hot 18 year old prick tormenters at my high school. Over the summer before my senior year I enlisted the help of my 23 and 22 year old provocative cousins Jen and Ginger. They taught me how to find a woman's G-spot and then gave me real-life fucking experience and training until they thought I was a 10. I fucked 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 fucked Lisa and Cherry, with one looking on while I fucked the other, and both were fantastic. Now the challenge is to nail Carolyn.
Since Carolyn and Lisa seemed to be in competition to see who could be the most stuck up prick tease in school, I hoped that Carolyn would find out I had fucked Lisa. To increase the chances -- not because it was really satisfying (ha, ha) -- I fucked Lisa four more times before school was to start the day after Labor Day. Each time she wanted to have Cherry along, and of course to be polite I fucked Cherry too. I hoped I wouldn't ruin a good thing by also fucking Cherry on her own six or seven times without Lisa's knowledge (including once during the lunch break at my summer job), but 18 year old Cherry was the sweetest teenage pie (pun alert!) I had ever had, and I simply wanted more of it!
School started without me knowing whether word had gotten to Carolyn about me fucking Faith, her friend's mother, and Lisa, and I was having a hard time coming up with a plan to test Carolyn. I did see her a few times the first two days school was in, and she looked hotter than ever. If possible --and it may not have been -- her enormous tits looked even bigger than last year, and I wondered how she could remain upright considering how slim she was.
As I went out to the senior parking lot the third day of school -- only seniors could drive to our school -- I looked toward the rear of the lot where it appeared a girl was crying. I went over to see if I could help and was shocked to see that it was Carolyn.
"What's the matter, Carolyn?"
"Oh, I'm sorry for you to see me this way," Carolyn replied through her sobs. "I'm trying to pull it together."
"Is there something I can do to help?"
"Maybe. You see Blake took care of stuff like this, and now he's gone..." she continued, now almost hysterical. Blake is her older brother -- a year older than me, who was a running back on the football team, virtually identical to me in size and build. Blake had graduated in the spring. He and I were always pleasant to each other, but not really friends.
Without any sexual intent on my part I comforted her, as she cried into my shoulder. While I wasn't really hugging her, I did notice something massive on her back, and instinctively moved my hand away from it when I came into contact with it. I hoped she didn't notice my flinch.
After a couple of minutes Carolyn did pull it together. "I'm so sorry to act like a baby. But I really miss Blake. Last week he left for a college two thousand miles away. We use to drive to school together, and he always knew what to do when this stupid car didn't work right."
"Maybe I can help. What's wrong?"
"It just won't start. And I've got to get home for the dogs since my parents are out of town."
"Let me see," I said, taking the keys from her clenched fist, purple from her painful clutching of the hard metal objects. The gearshift was a little loose, that's all, and not fully in "Park." I fiddled with it for a second, turned the key, and the engine roared to life. I explained the problem to Carolyn as delicately as I could, trying not to make her feel stupid.
She wiped away her tears, said "Thanks, Brian. I'm sorry you had to witness my meltdown," got in the car, and smiled and waved at me as she drove away.
I was both proud of and miffed at myself for being a total gentleman and not taking the opportunity to further my "Nail Virgin Carolyn" desire. [I didn't really have a good plan yet, so I'll merely call it a desire.]
The next day at school before classes began Carolyn came up to me. As far as I recall, this was the first time she ever initiated a one-on-one conversation with me.
"Brian, thank you again for yesterday. I'm still totally embarrassed."
"Don't be. You'd kick my ass any day in history or literature, I just know a little more about cars."
"That's really nice of you to say. To enhance my embarrassment, I wonder if there is something else I could ask of you?"
"Sure -- I'll help if I can."
"I wasn't through with my meltdown by the time I got home yesterday, and wiped out our mail box post as I turned into the driveway. I got a new post, but I don't know how to install it, and my parents will be home in two days. Can you help?"
"Sure, I'm good at manual labor. Should I come over today?"
"Could you? About 4 this afternoon?"
"It's a deal." "Thanks, Brian," she said, as she pulled my shirt toward her to give me a peck on the cheek, and then immediately turned and scurried away. Of course those monster tits contacted my abdomen as she kissed me, making me instantly hard.
I have to be honest. That day went really slowly. I kept trying not to think about the possibilities that afternoon, but all I could see in my mind were Carolyn's prodigious boobs, and her beautiful olive-skinned face. It was a total humiliation when I couldn't even tell my geometry teacher what a "conic section" was. [I should just have thought "tit."]
I didn't want to appear too anxious so I arrived at Carolyn's house a few minutes after 4, and was greeted at her door by two large but friendly mutts. She had on as skimpy a top as someone with her endowment could get away with, sheer enough that I could definitely see there was something on her back.
Carolyn showed me where the new mailbox support was, and I located a post hold digger and pick in her garage. As she looked on, I removed the remains of the old post, put in the new support, and attached the undamaged mailbox to it. It was good to go! As she was looking on, Carolyn actually chatted with me in a completely friendly manner -- not the slightest hint of the condescension I thought was her trademark.
I tried to make eye contact with her when we were chatting, but I guess I didn't do a good job of it. It seems that instead I was looking at the anatomical wonders on her chest -- what a surprise! After I was done she invited me into her house for something to drink. When inside she hit me with a one-two punch.
"I guess I should have worn a different top today -- I hope my boobs didn't distract you too much," she laughed. Before I could close my mouth and think of a pithy reply she continued with a devilish smile: "I noticed yesterday you flinched when you touched my back. I guess you've never seen a real support bra before. I need it to stay upright and to prevent my flopping tits from putting an eye out if I have to run."
I was totally dumbfounded, flabbergasted, and stunned by her directness. I was at a complete loss for words for one of the few times in my life. Then Carolyn started laughing as hard as she had been crying the day before. A big smile enveloped my face, I grabbed her, turned her upside down, and playfully swatted her ass a couple of times while she continued emitting gleeful, teasing sounds. Who knows what would have happened if the dogs hadn't started barking wildly, and jumping and slobbering all over me.
After I put her down and things calmed down I said "You are such a tease, Carolyn, you know that? Every guy at school longs for a look at those boobs of yours, but I'll bet no one has ever gotten one."
Still smiling Carolyn surprised again when she said "You've been so nice. Is that what you want? To be the first to see them?"
As I involuntarily nodded my head like an automaton, Carolyn unbuttoned her top, took off what had to be what she called her support bra -- the sturdiest looking garment I had ever seen -- and put her hands on her hips. Her only word: "There!"
She not only had the largest tits, by a considerable margin, I had ever seen live, they were larger than any truly attractive tits I had ever seen in print, movies, or on a computer screen. Also, she had puffy nipples surrounded by large areola. While her tits had to flop some because of their size, they were surprisingly erect too.
I instinctively reached out my hand and placed it on a puffy nipple -- softer and more luxurious than the finest satin. Carolyn said nothing; she just stared into my eyes with a sly grin on her face, for a good ten or fifteen seconds. Trying to bring me back to reality she said "Can you come over tomorrow and help me again?" As she said that she moved away and wrapped an afghan from a nearby couch around her shoulders and chest.
Continuing in my stupor I replied "Sure," or something to that effect, and she responded "See you around 4 again, then," as she ushered me out the door.
When I got to my car I just sat in the driver's seat for a good five minutes alternating my thoughts between "What the fuck just happened?" "My God those were the most incredible things I have ever seen in my life," "Help her with what?" and "Am I dreaming?"
If the day of our first planned meeting seemed like it took a year before it was 4 p.m., the day of our second planned meeting took a decade. It didn't help that on two separate occasions when, as I was talking to Lisa or Cherry, Carolyn appeared in the background beaming at me with a big shit-eating smirk.
I couldn't help myself -- I didn't give a shit if I appeared to be too anxious or not -- I arrived at Carolyn's house at 3:45. No dogs greeted me at the door. Carolyn opened it wearing a slinky robe with no other visible signs of clothing. I tried some small talk -- "Where are the dogs," but before the words left my mouth she put the index finger of her right hand up to my lips. Gazing into my eyes she said: "Brian, I know what you want. I want it too. The only communication we need is body language."
She grabbed me by the hand and led me into the living room, making sure that the front door closed behind me. She removed her robe revealing her flawless Mediterranean skin, those astounding puffy nipples, streamlined thighs and ass, and a crotch shaved except for what appeared to be a smiley face of hair above very prominent pussy lips.
My dick hurt from jamming itself into my pants zipper. But not for long. In less than a minute she had my clothes off, I was lying on my back on a blanket she obviously had spread on the living room rug, and she was partially on top of me, and partially to one side. As she stroked my steely shaft and planted kisses on my shoulder and neck, I started sucking and manhandling her tits.
Just gumming and massaging those phenomenal zonkers was one of the most pleasurable experiences of my life. I likely would have continued for days -- but she had other plans. Suddenly she lifted her ass in the air, straddled me, and held my cock vertical (it didn't need much help) as she slowly lowered her cunt over it, emitting a loud moan every time her luscious lips engulfed another centimeter.
Once she was fully loaded she clamped her thighs to my hips and started thumping the shit out of me. She had a fluid pelvis motion, a fluid pussy, and fluid chest movements. As she was literally bringing me to tears of pleasure, she started moving her nipples in circles. I couldn't fucking believe my eyes! It was "erotic" with five capital Es! She was filled with raw passion!
As astounding to look at as those rotating nipples were, I needed to touch more than I needed to look, so I rubbed her nipples and areola with the palms of my hands as she continued to bounce up and down.
It didn't take long after I started palming her boobs before I was ready to blow. She sensed it and I swear squeezed my cock with her pussy as she started to scream "Blast me full Blake, flood my cunt, Oh Shit, Blake!" We had over-the-top essentially simultaneous orgasms. Mine continued for as long as any orgasm I could remember, stopping about a minute after she collapsed on my chest, panting, and planting kisses all over my face between moans of "I've missed you so."
Once the height of my orgasm passed my brain started working again. "Blast me full Blake?" "Oh Shit, Blake?" "I've missed you so?"
Holy Fucking Gonads, Batman! I was a surrogate for her brother! She was no virgin -- just a first timer for someone outside her family!
Funny. I was bothered about being used as a surrogate for about five nanoseconds. Then I realized this was so much better than fucking a virgin. I had almost passed out from the pleasure; WOW she knew how to move that thing. There were half a dozen ways in which it was the most satisfying sexual experience of my life. As long as she pleasured me like that I could give a shit whether she thought she was fucking me or Blake.
I never told her she yelled out Blake's name then, or on numerous other occasions.
So I did it. I nailed Lisa and Carolyn. One was a very satisfying virgin -- the other a surprising experienced fucking machine! I got my second virgin in Cherry (dare I say I ate Cherry's cherry?). Now for the Epilogue.
I continued fucking Carolyn about twice a week until after about three months Blake flunked out of school and came back home. She was still very nice to me after that, always going out of her way to be pleasant, and even let me keep photos of her consummate bazoobs. But once Blake returned her cunt belonged to him. She never said so because I don't think she ever knew she called out Blake's name when I was fucked her, but I gracefully stepped aside.
I fucked Lisa another four or five times (alone -- she no longer needed Cherry to be with her) until she got enough sexual confidence to go after the son of our city's richest resident. She was never particularly warm to me in public, but if it was ever just the two of us she always thanked me for her "education," and told me how much she loved it. I'm sure she and the rich kid will end up married someday.
I continued to fuck Cherry whenever it was convenient, even after she got a steady boyfriend, until I left for college. After that I lost track of her.
I'm now in my junior year in college on a hockey scholarship. There has been only one constant in my sex life since the summer before my senior year in high school, and since I started college she is the only woman I have fucked.
I continued to take "spinning" classes, except during hockey season, throughout high school, and my classmate continues to make my head "spin" every time she visits me at school (which except for hockey season is almost every weekend). During the summer we live together. Not only is Faith's mature pussy exactly what I need to be fulfilled sexually, she doesn't inject drama into my life, doesn't make demands, and is more fun to be with than any other person I have ever met.
I'm in love with Faith. She's in love with me. She tells me that a 43 year old woman can't marry a 23 year old guy, but that she'll fuck my brains out until I find someone to have kids with. But if I could reverse her tubal ligation, I'd make her marry me.
I'm sure this wasn't the epilogue you expected. But life is strange!