Gretchen The Geek
Şub 5, 2023 // By:analsex // No Comment
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Gretchen had been in band with me since 4th grade. She had been a homely, gangly, nerdy little redhead most of that time and, while we were friends, I’d never really thought of her in any way but as a friend.
In the first two years of high school, she took a lot of harassing over her looks and I’d made more than one asshole apologize for making her cry. Yeah, she had a hook nose that was too large for her face and she didn’t have much in the tit department, but she was a genuinely nice person and I liked her. Even a few female classmates, who were initially put off by her looks, accepted her once they got to know her. Until Bree, that is.
Bree was a hottie that moved to our high school when I was in my senior year. She was blonde, gorgeous and stacked. It was reputed that her folks had moved here because she’d been caught fucking either the football team or several of her teachers. Nobody knew which story was true and she would just smile when asked about it.
I got her as a lab partner in our physics class, gaining glares from Gretchen. Bree had me wound around her little finger and everyone saw it but me. Part of it was the way she dressed; usually in a tight, sheer blouse, push-up bras, a leather mini-skirt or tight shorts and stockings with garters and stiletto heels. She knew how to dress to show off her assets, that’s for sure! She was mean and rude to others while she flirted and teased me all semester long, but I found her entertaining.
At my 18th birthday party, Gretch made snide comments about Bree that caused a rift between us and she quit speaking to me for a while, which hurt because Gretchen’s 18th birthday was in April and I wasn’t invited, though I dropped off the present I’d bought her. A month later, when Gretch was still not talking to me, I asked Bree to Prom, even though I’d promised Gretchen I’d take her. Instead, I bribed my cousin with $200 to take Gretchen instead.
We did all the usual prom things — going to dinner, renting a limo, going to the dance and then heading out to the lake shore afterwards. After that, I had the limo drive the four of us to a nice hotel. We had adjoining rooms for the rest of the weekend.
I slowly undressed my blonde goddess and she did the same to me. If I hadn’t been so horny, I’d probably have stopped at that point. Why? Well, you know how some people look much better dressed than they do when they’re naked? Bree was one of those. Oh, she was a hottie and a flirt but, without all the support of her high-fashion, snooty-retail-store clothing and makeup, she had saggy tits with big, ugly (to me) nipples that pointed downward, instead of out. The left one also seemed oddly smaller than the right. I don’t know how to accurately describe it, other than to say that the product inside didn’t match the promise of the packaging. I’d never seen a more asymmetrical looking woman in my life!
She must have been used to guys just falling all over themselves to get into her pants because Bree just laid there as I tried to make love to her. Oh, she sucked my cock, which was the best thing she did, but wouldn’t let me lick her pussy, wouldn’t let me touch her back hole and just laid there as I thrust into her. It’s not like I didn’t know what I was doing. Hell, I’d had sex with a girl babysitting my brothers and she’d been in college at the time. I’d also had three girls that went “all the way” with me because they were military brats. It was, basically, “goodbye” sex because their fathers or mothers ended up stationed somewhere else in the world.
I tried to spice things up with Bree by holding her arms down during sex or turning her so that she was on top of me, but she fought and complained, saying that her legs were getting tired or she’d get a cramp or something else. Whatever it was, she certainly didn’t live up to her vampy reputation.
We laid in silence on the bed after she let me cum on her belly (promptly jumping up to wash off in the bath). We were drinking rum and cokes, my intent being to try and loosen her up a bit for the next round of sex. We could hear music playing in Gretchen and Marco’s room. Then we heard a shriek and laughter as the headboard banged against the wall. Pretty soon there was more of a regular banging that started off softly and then became more and more frantic. Bree started to laugh.
“I can’t imagine anyone wanting to fuck that little troll!” she said out loud, the alcohol loosening her tongue.
“Gretchen is not a troll!” I said, defensively, “She’s one of the nicest people I know.”
“More like she’s one of the ugliest people you know!” countered Bree. “She’s not half as hot as I am!”
This conversation was starting to piss me off, especially since we could hear her moaning and calling out “harder! HARDER!” Here I was, sitting here with what I thought to be a hot chick that would be the fuck of my life and the one I should have been with was next door, getting it from my cousin. I began to mentally kick myself.
“Well, I happen to like her,” I almanbahis said, casting glances at the wall. “We’ve been friends a long time and I don’t like hearing people put her down!”
“Oh, fuck yes! Suck on my clit, you bastard!” we heard through the wall.
“Gawd, listen to her!” snickered Bree. “She sounds like a hooker!”
“Lick me more! YESS! THERE! OH FUCK, I’M GOING TO CUM ON YOUR FACE!”
“EWWW! She’s letting his tongue down there?”
“You should try it, you might like it,” I mumbled, feeling the booze hitting me, as well as my cock getting harder. I was really wishing it were me next door.
“What was that?” said Bree, jumping up and looking at me.
“I said it sounds like they’re having more fun that we are!” I groused.
“What’s that supposed to mean?” she shrieked.
“I mean…” Hell, what did I mean?
“Fuck you, Randy!” she screamed, throwing a pillow at me and then trying to scratch me with her nails.
“Get the fuck off me you psycho cunt!” I yelled, pushing her off me. She picked up a lamp and threw it at me, then anything else she could find. I jumped off the bed and was about to push the adjoining door open when Marco opened it for me.
“What the hell is going on?” he said, then ducked as a crystal glass tumbler when sailing past his head. I pushed him into the room and closed the door behind us as another glass hit it and shattered. I looked over at Gretchen and did a double-take. She was in a cute little teddy that made her look magnificent. She had a better body than I’d thought!
There were more screams and crashes from my room and then we heard people rushing down the hall. Marco opened the door and poked his head out to watch.
“It’s the cops!” he whispered back into the room. There was a knock on the door and Bree opened it. It was hotel staff and a police officer.
“What the hell’s going on here?”
“My boyfriend left me!” wailed Bree, falling to the floor dramatically and spasming into wretching sobs. They finally had to call an ambulance and take her away because they couldn’t get anything out of her. I borrowed a robe from Marco and went out into the hall to talk to the police. A couple more officers arrived and one looked at Bree.
“Oh, I know her!” he said.
“So do I,” said one of the EMT’s, snickering.
They took my statement and told me to come down to the station again in the morning. The hotel staff asked us to leave, but we convinced them, via my credit card, that things would be fine. Her little “fit” had cost me close to $1300, though.
“What the hell was that about?” Gretchen asked after everything settled down.
“Well, she’s not as much of a tramp as everyone seems to think she is,” I said, then relayed the events of the evening, but leaving out her cutting remarks.
“She got angry because she heard us?” asked Gretch, amazed.
“You have any of that rum left, cuz?” asked Marco
I poured us each a strong R&C, and we watched TV for a bit. I kept sneaking looks at Gretch, who hadn’t bothered to either change or cover up. She and Marco snuggled and tickled each other, then began to kiss and neck. I felt as if I were intruding, so I told them I was going to bed. When I got up to head off to my room, I thought I saw a hurt look in Gretchen’s eyes.
The following week, Bree didn’t appear at school. When she did come back, she was all over me again, apologizing and begging me to take her back, but I didn’t want to have anything to do with her anymore.
The next thing I know, she’s dating Marco and Gretchen isn’t talking to me anymore. With finals coming up, I didn’t have time to worry about it.
Four days after graduation, dad got laid off from work, killing my plans for college. I’d received a small scholarship, but not enough to pay for it all. Pop suggested I go into the military instead.
I joined the Navy and became an electronics technician. On my first ship, I made rank quickly and my division officer and I became quick friends when I found out we were from the same general area. He saw some pictures I had in my locker from Prom and took one down to stare at it.
“Who’s the blonde?” he asked, examining it closely.
“An ex-girlfriend of mine from high school,” I told him. “Why, does she look familiar?”
“That depends. Is her name Bree Miller?”
“You know her?” I asked, shocked.
“Yeah. I went to high school with her in downstate Illinois,” he responded. “Her daddy was some sort of political big-wig and was trying to keep her out of trouble.”
“What… sort of trouble?” I asked cautiously.
He smiled. “What did you hear?”
“Well, depending on who you talked to, she was either caught screwing the entire football team or screwing half the faculty of her high school.”
Barry laughed. “I wish it were that good!”
He looked at me. “We called her ‘Psycho-bitch.’ She was reputed to have put a hit on some of the teachers when they refused to improve almanbahis giriş her grades, and turned down her offers of sex. Instead, they reported her, so she put a hit on the principal of the high school too. Then she claimed they… um… sexually assaulted her after school, but the girl was actually still a virgin, so she changed her story to anal sex.
“Fortunately, the teachers and principal had an alibi for the dates she gave the police, as they were at a meeting with the Superintendent as well as with other teachers. And, the hitman she hired was actually an undercover State Trooper.
“The girl’s not right in the head. A friend of my dad’s is a psychiatrist up at the hospital in Chicago where she got put away in her freshman year. He was her doctor there, which is all he could tell me. I heard from others that she got put into the padded room for a while.
“When she got out, she was arrested again after she tried to choke her mom to death when her parents wouldn’t buy her a car. Then she was arrested a third time after the cops found out about her paying three gang-bangers she was fucking to kill her parents and everyone that had wronged her.
“Daddy had enough money and clout to keep it shushed up, but he couldn’t fix what was happening inside her head. They moved down into my town and she started school all over again.”
“I was a senior then and she was almost 18, but in her freshman year and went all goth, wearing leather and acting tough and shit. She got the crap kicked out of her a bunch of times, but she had a rep of spreading her legs for anyone that was willing to pay her for the privilege.
“In her sophomore year, she reputedly was in a few porno’s and made a lot of money. The school found out and tried to get her arrested for it, but since she was 18, there wasn’t much they could do, other than expel her. Daddy had to act fast, so they moved again. I guess to where you lived.”
“Whoa,” I said, flabbergasted. “She was little Miss Fashionista in my school. Still dressed like a porn star, but…”
I told him about my prom night and how she’d begged me to take her back after that.
“All during the time I was in boot camp, she would write me all sorts of letters, send me naked pictures via email and even tried to sneak onto the base to see me. When I wouldn’t have anything to do with her, a Puerto Rican buddy of mine from the Navy told me he’d like to do her. I gave him the address and phone number and soon she was off my back. I got assigned here and never did find out what happened to her after that.”
Barry snickered. “She’s in jail.”
“Murder. From what I heard, she killed your buddy when he tried to break it off with her.”
I was shocked about that and didn’t know what to do, so I tried to get into contact with Gretchen. All of my calls went unanswered. My letters were returned and my emails ignored. Her parents moved while she was in college and I lost track of her.
The Navy got me started in correspondence courses for college and I got most of my crap classes out of the way. By the time my 4 year hitch was up, I’d earned an Associates in computer technology and was one year away from a bachelors.
Once out, I switched majors twice and earned a dual degree in business administration as well as one in medical electronics science. I then went to work in sales for a laser medical technology firm that provided high-tech equipment for plastic surgeons.
I was in a doctor’s office one afternoon to see about selling him some new equipment when a red-headed woman entered the office, dressed in an expensive business suit. When she sat down and took off her sunglasses, I gasped.
The woman looked up, squinted at me in that familiar way and then smiled briefly.
“Oh. Hello Randy,” she said in a friendly, but not warm, manner. I stood up and went to give her a hug, but when I touched her shoulder, she felt stiff to me, so I backed off.
“God, it’s been what, eight, nine years now?” How have you been? What have you been up to? Are you married?”
She smiled that fleeting smile again. “No, I’m still single. I mean, who would want to marry a geeky troll like me?”
I looked shocked. “You were never a troll!” I hissed, “I don’t care what that psycho-bitch, Bree Miller, said!”
“She said you told her that!”
I shook my head. “Man, she really was a psycho-bitch!”
“What do you mean?”
I told Gretchen about my conversation with Barry while in the Navy. She gasped over Bree’s fate and then I told her about the rest of the conversation on Prom night.
“Gretchen, I’m so sorry! I should have taken you as my date. I really should have, and I honestly feel like shit that I didn’t. I’m really sorry.”
She smiled and some of the frostiness seemed to be dissipating. “Well, it wasn’t a complete loss. Your cousin, Marco, was quite good in bed!”
I smiled sadly at that. “I heard you weren’t bad either.”
There almanbahis yeni giriş was a long, awkward silence after that. Gretch had this faraway look on her face and then it dropped and she smiled at me for the first time in almost a decade.
“Want to have dinner with me after my appointment?” she asked.
We both met with the doctor. I sold him the equipment and Gretch had her appointment.
I was surprised that she invited me to her apartment rather than going out, though. She gave me her address and phone number and told me to be there at 7. When I arrived, I was impressed. She’d done fairly well for herself and had a nice condo on the fourth floor in a residential area of the city. It was smartly furnished and tastefully decorated. I made appropriate noises and congratulated her on her success as she let me in.
Gretchen told me to ‘dress casual’ and I had, wearing black dockers and a blue silk shirt. She me at the door dressed in tight, low-rise, skinny jeans that buttoned at the fly. She also wore a white cotton top that clung to her curves beautifully, revealing she hadn’t bothered with a bra. She invited me in and I admired her tight little ass as she walked in front of me. She looked… good.
She looked damned good!
And I’d been an utter fool to not see that ten years back.
Over dinner, I asked what she was going to see the doctor about.
“Oh, that. I’ve finally made enough money to get my schnozz fixed and get breast implants,” she said, putting her hands under her tits and pushing them up. “Maybe after that, guys will start noticing me.”
“Hell, Gretch! You don’t need to do that! I think you’re just fine the way you are!”
She snorted in derision. “Yeah, right. Until a hot blonde enters the room. Then suddenly, I’m ‘Gretch the geek. Gretch the troll’ again!” The bitterness in her voice surprised me.
“Not at all, Gretchen,” I said, softly and sincerely. “You’ve always been the kindest, most caring, loving and beautiful person I’ve ever known. It’s why I’ve always…”
“Oh, spare me the violins,” she interrupted, half-chidingly. “I know what I look like!”
I got angry as I remembered each and every time I’d defended her when other’s said mean things.
“Goddamn it, Gretchen, I said I was sorry about all I did! I made a fuckin’ mistake, okay. And, just because I did, doesn’t mean you have to!”
She looked at me, her mouth open in surprise.
“Where am I making a mistake?” she finally said.
“By changing the way you look!” I spat. “Some guys happen to like small boobs, you know.”
She gave me a raspberry. “Oh, yeah, sure. Until they see these, then they laugh!”
Gretchen surprised me by pulling up her top and showing me her naked chest. Her breasts were two small, slightly globular swells, each capped by a pale-pink nipple. I stared at them, my cock getting harder, even as a tear rolled down my cheek as I realized all the pain that my stupidity had put her through.
“See? They even repel you!” she cried, pulling her shirt down.
“The fuck they do!” I said in a husky voice, standing up to display the obvious hard on in my pants. On a whim, I asked, “Show ’em to me again! I dare you.”
Gretchen gasped as she saw my hard, throbbing tool pressing against the fabric of my slacks and slowly pulled her blouse up and off.
“You… you do like them? You actually like small tits?”
“Gretchen,” I said, walking up to her and running my hands up her arms to pull her to me. “One thing I’ve learned is that some people look good in clothing and some look much hotter out of them!”
“Yes. And damn, if I remember correctly, you have a really hot body!” I said, blushing, but bending to give her a brief kiss on the lips.
Tears were pooling in her eyes as she threw her arms around my neck, passionately kissing my lips while rubbing against me. Then she hugged me tight and began to lightly beat on my back with her fists.
“Damn you, Randy!”
“Why? What did I do?”
“You are YOU. I intended to take this slow, to torture you for all the shit you put me through all these years… but then… then you come back into my life and all these feelings come rushing back and…”
She kissed me hard, with passion, our lips pressed together for several moments until we both opened them slightly, our tongues tentatively peeking out to test the other before they practically intertwined, our passion growing with every second.
We crab-walked down to the bedroom, comically scattering pieces of my clothing all through the hall.
We both fell onto the bed, kissing as if neither of us could get enough and wanted to devour the other. Gretchen still had her jeans on, while I was only in my boxers. My hands caressed her cheeks, combed through her hair, slid down her neck and then my palm was at her breast, feeling the stiffness of her tiny nipple as it stood proudly at attention for me. There was just enough to her breast that I could squeeze it and then pinch the nipple with my thumb and forefinger, making her suck in her breath a little. We both smiled at each other and I went back to teasing the little nub with the palm of my hand.
“I love how that feels,” I said to her.
“Do you?” she breathed.
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