My Rocky Relationship with Girls

Story Info
Nerd travels that bumpy road to happiness with girls.
3.4k words
4.49
10.9k
5
2
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
darvon86
darvon86
28 Followers

I put all my stories in Humor and Satire. I like to write romantic comedies, or as other authors here call it comic romance. But I put them in Humor because they are meant to be comic and light hearted, even if they contain scifi and fantasy, or group sex, or mind control, or whatever. I also realize that some of the categories are to allow people to avoid topics, so if I ever write comic incest or comic non-consensual I will make sure to put them in those topics to warn the reader.

*****

My name is David Williams. Gordon Shepherd is my best friend and I have known him since we were college roommates at Cal Tech. We were both Math majors, and although I look like what I am, a computer nerd, Gordon looks like a GQ model. Gordon is handsome, with a fun, outgoing personality, and was always smooth with the ladies since the first day I met him. And at a place like Cal Tech, you can imagine how he stood out. I, on the other hand, fit the nerd profile exactly. Skinny, non-athletic, glasses, and really, really shy. If I had it my way, I would have stayed in my room for the whole 4 years. Somehow Gordon and I really bonded. Underneath those GQ looks, he had a really sharp brain, although his focus was more applied math than my focus on theoretical math. We stayed roommates all through college.

Gordon spent most of his freshman year knee deep in pussy. He would be seen around campus with all the hot girls at CalTech (not that many) and tons of girls from UCLA (I have no clue how they kept showing up with him on campus. There must have been a shuttle bus or something). I spent a lot of that year in the library, not in my room, sock on the door and all. Luckily CalTech's main library is 24/7, and by my second semester I also had keys to the AI lab and a couple of other places to retreat and study. When Gordon and I hung out, I would coax him in to telling me his exploits. Gordon wasn't bragging, I lived vicariously through them and really wanted to hear about it. Many of the girls that I saw Gordon with became a focus of my frequent manual excursions into auto-erotica.

But Gordon was a good friend and made it his college mission to get me laid. I don't know if I mentioned it, but I was really, really shy. I was 6 sigma shy in the already socially retarded atmosphere which was the male portion of the CalTech freshman class. Forget pussy. In high school, I had never so much as touched a girl. No dating. No kiss. No nothing.

In college, same ol' same ol'. Not that I didn't see a lot of pussy. One night staying in our place while Gordon entertained was equal to a week of Internet porn surfing. By our second year Gordon and I shared an apartment just off campus, so the sock came off the doorknob permanently and I stayed in to study and work even when Gordon came back to the apartment with company. And Gordon was always careful to steer the extra hard-bodies my way. He was always getting his "friends" to ask me to make Gordon's threesome into a foursome. I became adept at politely saying No Thank You to drunken Swedish twins trying to take off my pants. I had fearsome social issues and I couldn't get myself to say Yes Thank You. Subconsciously I didn't believe I deserved to have sex and feared I was making the girl uncomfortable, even when she was naked and trying to pull me into the orgy in the living room. Nowadays I can't believe how pathetic I was, although I can still feel the echoes of that fear inside.

And I stayed unfucked, despite Gordon's best efforts, all the way through graduation. Gordon went to Stanford to pick up his MBA and I followed to Palo Alto to pick up a quick double doctorate in Math and Computer Science.

When I graduated I had several papers and a couple of patents in neural networking, and synthetic logic. I was courted by all the big boys, but I decided to be employee #4 in a little company in Greater LA with a funny name. Jarvis.

4 years later and Jarvis was on every smart phone worthy of the name. "Jarvis please tell me the best sushi in town." "Jarvis please phone the dentist and get me an appointment when I have an opening." "Jarvis please remember to send flowers to my Mom on her birthday". Jarvis Industries, stealing (and then buying for stock options) the name of the AI personal servant to Iron Man, finally made AI work the way people expected AI to work. Every man, woman and child all had their own executive secretary in their pocket, able to directly interface with the other Jarvis' in everyone else's pocket. Jarvis ran our lives.

After only a year on the job at Jarvis, I could see where we were headed and got Gordon in as the #64 employee and the 2nd guy in Marketing. Two years later Jarvis had over 2,000 employees, and both Gordon and I were very well off, options-wise.

But even through all our success, Gordon still had a mission to complete. By then I was 29 and still never been kissed/dated/fucked/blown/[your sexual goal here]. He kept dragging me out to singles bars, industry mixers, and any kind of social group. I went on "double dates" where he arranged both girls. I always managed to leave in the middle and not finish out the date (of course, Gordon would always pick up my slack and finish both of them later that night). In one of those "Co-ed Adventure" groups that Gordon kept dragging me to, I met Courtney.

Courtney was way out of my league. Heck who am I kidding, any librarian is way out of my league. Courtney was way out of my species. Courtney was special. Now she was a high-income sales professional for a German robotics company. In high school and college (UCLA) she was a high-jumper , but not in the top ranks. All high jumpers are "cut high" and she had impossibly long, sleek legs. They made her almost as tall as I was, and that was without heels. With heels she was taller than me. After college she kept fit by her passion, dance. She had taken years of ballet as a young girl. But in her teens, her hopes of going further were met with the facts of life, or for her, the facts of hormones. She bloomed, and kept right on blooming out of ballet. Tall girls make great ballerinas, but not with D cups.

She had the hot bod with her long legs and great tits, But her best attribute was her face. Model perfect, with green eyes that had gold specks. Her damn eyes were hypnotic. Definitely a 10 or at least a high 9, and that was on the California scale.

And somehow that made it easy for me to talk to her. No chance to succeed meant no chance to fail meant no stress for me. And for Courtney, she got hit on by every guy she met, which meant that she had a void for "male-friend" which I filled since I never even thought to flirt. Actually, I didn't know how to flirt. We became adventure buddies and were always paired up in the kayak or the sailplane or the belay. And strangely enough Gordon completely struck out with her. Which was not common for Gordon as your typical handsome, young, articulate, multimillionaire in Los Angeles. But he soon saw she was becoming my friend and backed off. Later, through me, Gordon also became a friend to Courtney. And as soon as they started talking as friends, Gordon brought up his long-held mission. Courtney was fascinated at Gordon's attempt to get me a girl. It was "Challenge Accepted".

And instead of just throwing hot bodies at me, Courtney took the route of instructing me how to be a "player" or at least a guy. She dragged me to exercise classes, which for her was yoga and spinning and dance. For Courtney, that meant hot Bikram yoga classes. Which in LA means hot Nude Bikram Yoga classes. She helped me start to feel comfortable with my body. She shopped with me and worked on my grooming.

Also, for some reason I found it easier to talk to Courtney about sex than I did with anyone else, even easier than with Gordon. She clinically taught me how to do foreplay, eating pussy, fuck, everything. All with the slant of pleasing the girl. And all by only using the Internet and talking me through things. No touchee. Actually somehow that didn't even occur to me. Courtney wasn't in my fantasies. She was my buddy.

She taught me how pick up girls, from a girl's perspective. And then took me out to clubs and role-played. And then she became my wing man. Let me tell you, having a supermodel as a wing man works wonders. Soon I had dates, and kisses and even...sex!! And I recounted all my exploits to Courtney and Gordon. They both encouraged me and provided post-game analysis.

After a few months Gordon took all three of us out to a very fancy restaurant to celebrate my going into double digits in bedpost notches. We drank and ate and laughed. We went clubbing and finally ended up in a swingers party on the beach in Malibu. Gordon attracted his usual harem which he pounded. Courtney also racked up the studs. I even fucked a few nubiles in front of Gordon and Courtney. Gordon and I actually DP'd this amazing girl from Cirque de Soleil. I was now officially a guy.

Even though the party had wound down, I couldn't sleep. It was dawn and Gordon was passed out in the big party room sleeping among a group of girls from Reykjavik that I met last night. Courtney was no where to be seen. So I found my pants (or somebody's pants that looked like mine), rolled up the cuffs and went walking in the surf. About a mile down the beach I spotted Courtney in a t-shirt and running shorts sitting in the sand, looking out to the sea. She didn't hear me and I watched her. She looked sad. It looked like she had been crying.

"Courtney, what's wrong", I sat down beside her.

She turned around and started sobbing and then BANG. She hauled off and slapped me hard. Then she got up and ran. I ran after her, but Courtney being a former track athlete I couldn't catch her. Luckily the beach started having small smooth boulders about the size of basketballs embedded in the sand. Luckily I tripped. Luckily my head hit a rock and knocked me out cold.

When I opened my eyes I saw Courtney's beautiful eyes looking worriedly at me. I was lying on the ground with Courtney kneeling over me. Her hand was stroking my cheek.

"What happened?"

"You tripped and hit your head on that rock underneath your head."

"Earlier on the beach...why were you crying?"

"I ...I was jealous." she stated as she started to help me sit up and get my head off the boulder. "you didn't even touch me although you fucked all of the girls at that party."

"But you aren't a girl, you're my buddy..."

When I opened my eyes, I saw the acoustic tile ceiling and that little beep...beep...beep that television uses to tell you the scene is in a hospital. Gordon was standing at my bedside.

"Well look who's back from the dead", Gordon exclaimed with a smile.

"Where am I?"

"You are in UCLA Medical Center. You have been out for about 6 hours, it's noon."

"What happened?"

"You hit your head on a rock. Twice. The paramedics brought you here, but the MRIs are all negative. You will live."

"Where is Courtney, she was crying on the beach, ran off and I chased her."

"She is outside and she is really upset. She says she caused you to hit your head...twice. Wait...She was crying BEFORE you hit your head? What did you say to her?"

I looked away. "Nothing..."

"Then what was she crying about." Gordon eyes narrowed. "Was it the party?"

"Yeah. How did you know?"

"What an idiot.", Gordon sighed. "You fucked all those girls in front of her."

I was confused. "But wasn't that the plan? Weren't you guys trying to get me to fuck a bunch of girls?"

Gordon shook his head. "Us "guys"??? I have to work on your training. The ones with the bumps on their chest are girls not guys. Courtney has bumps."

Gordon continued, "Courtney trained you. Didn't you notice she was a girl in those yoga classes? Didn't you get an erection when you saw her naked?"

I blushed. "Well at first a bit, but I learned how to control it better."

"David, when she was training you in sex, didn't you say she used her body to illustrate things?"

"Yep."

"And even though you told me there was no touching, you didn't get an erection?"

"Nope."

"So David, all this time she was flashing you her tits and pussy and you treated her like Wikipedia. And when you got to a "Guy/Girl" party with her, you were a "Guy" with a penis for every Girl there, but not Courtney? Why didn't you fuck Courtney you idiot?"

"Because she is my buddy..." I stated lamely.

"I am going to have to recheck those MRI scans."

"But Gordo, YOU didn't fuck Courtney at the party...because she is your buddy."

"Sigh...I didn't fuck the ever so fuckable Courtney because she is not only a girl, but she is YOUR girl. David, don't you know the Bro Code?"

The light bulb started to dimly glow in my brain. "Oh... And all that time she spent with me trying to get me comfortable enough with women to date..."

Gordon finished my thought. "...Was because she wanted YOU to ask HER for a date. To kiss HER. To fuck HER. She might not have started out that way, but you don't think it didn't get that way? Open your eyes stupid. Geez, you say you went to CalTech?"

I thought a bit and then calmly said to Gordon, "Can you send her in please. By herself."

"Now you are using your head, bro."

Courtney came in and slowly walked to the side of the bed. She had been sobbing and barely had it under control. She tried to talk but just hiccuped and stuttered.

I whispered in a low, cracking voice, "mumble mumble mumble.."

She looked at me and softly said "What? What was that?" she leaned down.

Even more quietly and raggedly I spoke "mumble mumble mumble".

Her eyes were pleading and she whispered "I can't hear you. Say it again." And leaned in so close her breath warmed my neck.

I quickly raised my hands behind her head, grabbed her body and drew her into a passionate embrace. I kissed her long and deep, holding her through all her surprised struggle to not to tip over and fall on me. With one arm I brought her onto the bed and her feet off the floor. With the other I ripped her blouse open and the buttons flew everywhere.

She finally started to kiss back and her hands started mauling my body. With one hand she grabbed a wad of my disposable hospital gown and ripped the entire thing off my body and threw it in the corner. As I pulled her on top of me I accidentally pulled my IV line out of my arm. I hardly noticed and DIDNT stop. I got her running shorts to her knees and attacked her sex with my fingers as she kicked the shorts off and to the floor. She climbed on my now crystal hard cock and sank down to my balls. She started to piston up and down frantically.

Later I learned that Gordon has stood guard at the door and stopped the nurses and doctors from running into the room when my readings had flat lined because Courtney had ripped the sensors off my body.

So... eighteen months later...

The wedding was beautiful. Courtney, her mom and her UCLA friends worked so hard and made it spectacular. Gordon rented out The Magic Castle, where he had been a member since college and was now on the Board of Directors.

After dinner, the table with the wedding cake was wheeled out. The cake was the usually magnificent piece of art that most wedding cakes are, but the piece de resistance was right beside the cake. Unbeknownst to Courtney or I, a couple of days after I got out of the hospital that old romantic Gordon went back to the beach and dug up that rock and stored it, expecting that he would need it in a year or two. He told me about it a couple of weeks ago so I was prepared, but Courtney screamed and her eyes became so big and she started to sob. She looked at me all doe-eyed, but I shook my head no and pointed to Gordo. She ran to him and leapt into his arms, smothering him with kisses until I wondered if I needed to change the name on the Honeymoon suite reservations. But I knew who was getting the last kiss from Courtney that night so I just grinned from ear to ear.

Later that night ... an hour or two before dawn...

Courtney and I decided weeks earlier that since the party would run late we would stay a couple of days in LA before leaving on our Honeymoon. We reserved a suite for two days before getting on the jet for Australia. When our limo left the reception the party was still rocking, but we were ready for bed and left for the hotel.

When I carried her across the threshold and into the bedroom she got another surprise. There on the floor at the foot of the bed was our rock. Apparently Gordon had snuck it out from the reception and got it here.

Courtney made short work of our clothes. They flew everywhere. I grabbed her and held tight as I pulled her on top of me on the bed. Passion ensued. Then I had to have her on the bottom and rolled us until I was on top. [insert sex scene here]

She cried that she wanted to be back on top so I rolled us over again. However the bed ran out at this point and we teetered on the edge about to fall off.

All at once Courtney realized that we were going to fall and then her eyes went wide as she realized we were going to fall off the FOOT of the bed, onto the ROCK. I had realized this immediately and I rolled to the bottom to protect Courtney. My head hit the rock with her on top as she screamed. My eyes closed and I went limp.

However... remember that we DO live in LA, the land of make believe. And Gordo knows (and has fucked) a LOT of people in the movie industry. Including a lovely young artist who makes fake boulders for movies. Things were progressing just as Gordon and I had planned. OUR rock was still back at the party where Gordon would see it home. THIS rock was a beautiful copy made up of some high-tech foam whose name I was told but can't remember. Needless to say, that after faking a coma and letting Courtney scream for a second or two, I opened my eyes,grabbed her to me and proceeded to pound her hard on the lovely deep pile carpeting of the suite.

After about 5 seconds of bliss, it dawned on Courtney that she had been had and she was fit to be tied. But all those yoga classes and weight training sessions served me well. Struggle as she might, she could not escape. I fucked on relentlessly. Eventually she calmed way down. Especially after her first orgasm. I actually released her after her third. We relocated to the bed.

And I am very happy to say that by dawn, Courtney was the one driven unconscious, not me.

And I didn't even have to use the rock.

darvon86
darvon86
28 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
2 Comments
ReapTheEvilReapTheEvilalmost 7 years ago
I have not seen this take before.

Although I disagree with the category this was put in, I cannot deny that this was a pretty nice short story. Thank you.

AnonymousAnonymousabout 7 years ago
This was neither romantic or funny

So now what? No where to go with this drivel.

Share this Story

Similar Stories

High School Harem Pt. 01 I'm the only guy in an all-girls school...in Erotic Couplings
Oh Brother He always seemed to come out ahead.in Romance
And Then There Were Two Spring Break with my sister and her friends.in Romance
That's What Friends Are For Justin's best friend Samantha will do anything for him. in First Time
Revenge of the Nerd Hot girl experiences hot nerd.in Erotic Couplings
More Stories