Evolution to Denial 01

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Ted's messy dating life needs to change.
5.8k words
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Part 1 of the 3 part series

Updated 06/16/2023
Created 04/24/2023
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Am a pretty smart guy, but its taken me a long time to find happiness. Had a typical dating life growing up. High school fumblings, college hookups and a live-in girlfriend. Plus a series of the same through my first decade of work. But never really happy. Just lived the life expected of me. Except never got married, to my parents' chagrin. Always attracted the emotionally needy, unstable, young women looking for a daddy and lover. Always with emotional turmoil.

By thirty had achieved all I needed professionally. Computer programming was my thing from my earliest years. And video games. Typical nerd. Except socially I could attract women, just never stable ones. My confident nice guy persona seems to attract the neediest ones.

Sarah was the perfect example. I work for a major NYC investments firm as a systems designer and manager. Somehow got assigned to the intern program. It made sense for computer engineering students. But I had to sit on the panel that decided on all. So marketing, sales, and administrative interns too. They rotated through all departments. Sarah was selected as an admin intern.

As a manager my main worry was non-engineering interns. Female engineers, even young student ones, knew how to handle hormonally charged nerds. It was all those other young women. Most of the guys in our little geek palace are egotistical and socially offensive. In small groups they can go way over the line. Despite constant monitoring inappropriate things still happen. All the HR training and a couple of firings in previous years didn't stop it. Hormones seem to trump smart. But short of a rape conviction good computer guys could always get a new job

Sarah was nineteen and smart as a tack. Pretty with black hair and dark brown eyes. On the short side she's thick and curvy. Guaranteed to get male attention. Although she got the admin intern slot I heard the sales folks were courting her. Smart and attractive always works in the financial world. Her last two weeks of the summer internship were in my group. I make a point of touching base with the interns daily even if just in chat. Her first week went smoothly.

Hottest Monday morning of the summer found her waiting for me in my office. The second I saw her knew we had trouble.

"Sarah how about we ask Ms Hawthorn to join us?" She is our Director of Administration.

"Ted let's not please. I don't want anyone fired. But you need to stop them. If they did it to me..." She let it hang.

"I know Sarah. Be assured I will slam whoever stepped out of line. Fired one two years ago."

"You know as well as I do they can always get another job. How many geek engineers post sexually explicit crap? Probably half of them at least." Like I said smart young lady.

"Tell me what you can comfortably. I'll break a few arms quietly." She smiled. Easy to see how these idiots got charged up.

"An account slipped into my DMs. Knew it was fake right away. Am sure it is somebody here. Linked me to these." She handed me her cell. Scrolled through a series of porno pics with her face superimposed. Cock in mouth, face covered in cum, cock in ass. Typical boy shit. Deliberately not done well. Covering their tracks.

"Am so sorry Sarah. Unlikely we can prove who did it. Can guess which two or three it was. Are you ok?"

"Yah not the first time it has happened to me. Stupid incels." Gen Z has such an evolved set of values and attitudes. It was not going to throw her.

"You can skip this week if you want."

"No fucking way. Gonna make them squirm."

"Admire your strength and poise. Here's my cell. Anyone blinks call me. I guarantee to pick up."

"Thank you Ted appreciate your support. Maybe we can work together again someday." We shook hands. Off I went to pound some nerd heads.

The next Saturday was when life headed off the rails to crazy land. Again.

Text. "Ted drinks Anytime Thx :)" Did she ask for a date? Is she supper mature for nineteen? Christ more than ten years my junior. But my balls twitched. Very attractive young woman. And my animal brain flipped through those pics.

"Sarah thx no Mngr"

"Not anymore. Review is in :) Tonight @9?" My brain burped. What the hell she was right. No longer had any power over her. WTF you never know she could be the one.

"k" She sent a spot to meet.

The bar is a cozy dark romantic spot in the East Village. As I approached it phone buzzed. She directed me to the back corner.

"Ted you dress up nice." Said with a big smile. She remained seated as I joined her. Was wearing a frilly top with plenty of cleavage and could see top of her bare tummy. Sexy as hell. Drink time flew by. She's charming and funny.

Conversation covered her family and university life. Told her about my little family. Just my parents and me. She gave a little pouty look and told me I needed a wife and kids.

Surprised me when she signaled for the check and insisted on paying. Was momentarily disappointed. As we walked out I prepared to end things with a 'hope we can get together again' line. Admired her ass and thick thighs.

"Nightcap Ted?" That caught me short. So self assured. Confident and assertive.

"Sure where?"

"Your place." She flagged down a cab. Shocked me when she gave the cabbie my address.

Nightcap was a sleepless night of sex. Started in the elevator with several long kisses she initiated. Had never had such a forward woman. She waltzed into my condo stripping her way to check out the nighttime view.

She kissed me again rubbing my crotch. Stepped back and stood feet apart letting me see everything.

"Better than those porno pics?"

"Fuck yeah." She stepped back in and started to take my shirt off. Slapped my hands down making clear she'd strip me.

"You can have me just like those pics and a lot more." Dropped to her knees and gave me a great blow job. Swallowed and looked up at me smiling and licking her lips. Pushed me over to the couch and sucked me again. Fluffing me to another erection.

She bent over the dining table and urged me to fuck her hard doggy style. This is where I worry a little. My dick is not the biggest. Maybe five inches but it is thick for that size. She quickly convinced me it was nice for her pussy. We fucked again on the bed missionary.

As dawn approached she fluffed me again. This time she grabbed margarine from the fridge. Laid back on the dining table and made a show of lubing her asshole. Her knees spread and back by her face. Just like the porno pic.

"I want you to own my ass. It's so tight need you to stretch it out." Fifth time made it easy to last. Must have been over thirty minutes. Seemingly proper young lady kept up her dirty mouth egging me on. By far the kinkiest girl I ever had sex with.

After I came in her ass she shocked me. Right back on her knees and licked my cock clean. Smiled up at me submissively. Yuck.

She popped up, grabbed her cloths, bag, and shoes and headed for the door. Tried to stop her at the door.

"Its ok I'll dress in the elevator." Gave me a peck on the cheek and strode out.

Sunday afternoon the phone buzzed. Pic of her naked from behind looking over her shoulder at the camera. Captioned "You can own it."

Texted her back "Yes." She arrived a few minutes later. Spandex tights with a tube top over a sports bra. Another sex session followed pretty much the same. Four more cums. Damn this teen just made me finish nine times in under twenty-four hours.

Last weeks of summer were amazing. Going out she was a fun, intelligent, flirty companion. At home a tigress. Amazing sex. As we talked intimately Sarah made it clear I could have anything I wanted sexually. Sex with her had already stretched my boundaries. Kinkiest I had done before was a threesome. That was with two escorts on vacation.

Our last summer evening together Sarah dropped the I love you. My feelings were strong but not there yet. So young. Did promise to visit her at school homecoming weekend in October. Over the six weeks interlude we had nightly video call jerk off sessions. And a few early morning ones.

Homecoming was awkward. Thirty-one year old guy hanging with a bunch of college girls, at an all girl school! Sarah's mature stable veneer cracked immediately. Nervous as hell from the moment I arrived. Almost desperate to have me accept her friends. Alone practically begging me to say I love you. Felt bad. Knew my mistake in the first few hours. Had another clingy needy one. Put her off by saying we needed more time. Due to her age and she was in college.

Second night after a pizza movie party we all got high. Fun and funny group of very smart young ladies. High as a kite and the only guy amongst six girls was great. Sarah hung all over me. Then came the surprise.

Janie, her best friend, announced "Time for a game of truth or kiss my pussy." They all laughed at my shocked reaction. Several chimed in saying it was not really sex. And they always played it together. Admit I wanted to see them kiss each other's pussies. Wondered if any of them were gay.

"You're Sarah's partner. If we ask you she'll pay the penalty if you pass or lie. Questioner rotates. Can question anybody. As the oldest at twenty I always start." Janie grinned right at me.

"Ted is Sarah's asshole tight?" Sarah gripped my arm tightly.

"Yes it is."

Sarah asked a cute little blonde if she wanted to have a threesome with us. They all burst out laughing and girl turned beat red.

"No I could never."

The game focused on us. Trying to entice or shock me and embarrass Sarah.

"Ted have you ever fucked two girls in a threesome?" Asked by a thin plain brunette.

"Yes once." Sarah seemed surprised. She received a few teasing comments.

Janie "Sarah how many inches is Ted's cock?" Sarah looked at me as I blushed. She slowly shook her head no.

Janie stood and stepped in front of us. Sarah unzipped her jeans and pulled them and the panties down. Leaned forward and gave the clit a kiss. Girls clapped.

Sarah retaliated her next turn. "Janie have you been spit-roasted?

"Many times. You know my boyfriend loves it." Christ. She was proud of it.

We got passed a few times and once Sarah asked the thin brunette if she wanted to eat Sarah's ass. Girl said yes. Damn would love to see that.

Next turn the brunette.

"Ted have you pissed on Sarah yet?" WTF. I would not answer. She pulled her pants and panties off and pulled Sarah's face into her crotch. Got me hard. We got passed several more times.

"Ted did Sarah clean your cock after, with her mouth, every time you fucked?" From a heavyset chick. Sarah buried her head on my shoulder. I hesitated.

"Do you want me to answer Sarah?" She shook her head no. Not sure why cause that seemed to be a yes. Girl stood and lifted her skirt and Sarah kissed it through the panties. Janie's turn again.

"Sarah do you want to be Ted's wife, slut, baby momma?"

"Yes I do." She couldn't look at me.

The thin brunette "Sarah whose boyfriend fucked your ass doggy style as his birthday present? While she sat on your back kissing him?" Damn.

"Janie." No one seemed surprised. Like they all already knew and it was just for me.

Janie "Ok we're done. Unless Ted wants to show us what he's got? Come on Ted. We need to see what we get if we say yes to Sarah to have a threesome." Giggles and I was now rock hard.

That ended the party. Got two blow jobs before we slept. Sexually satisfied but really uncomfortable with the whole thing. Happy to leave the next morning.

Sex part was thrilling but no way was I going to continue with this girl. A roller coaster I did not want to ride.

At home spent the week trying to figure out how to let her down. Did not want to lead her on but worried she would flip out. We had no calls that week. Just some texts. I was putting it off till the weekend.

Friday night was working on a pizza around seven when the door buzzed. Christ it was Sarah. She drove down to see me. Almost a three hundred mile drive on a Friday.

Pecked me on the cheek and stripped as she walked in. Tried to stop her but she insisted.

"Sarah please let's sit down and have a talk."

"No. Fuck my ass first. And I'll eat your ass." She laid on the carpet face down and reached back to spread her cheeks.

Disaster. Try to reason with a naked woman begging to be buggered. Finally convinced her we were not going to have sex. Wore her down and said she had to dress before we talked.

"Ted I'm dropping out of school. You are what I want. Let's get married. Already trying to get pregnant stopped taking pills after we first hooked up." Fuck me batshit crazy.

"Sarah no. You're too young and need to finish college. Maybe another man would be better for you."

"No. I love you. You do not understand. No other woman will give you what I will. My love is unconditional. I'll do anything. Anything you want."

"Sarah the sex is great but maybe you are too kinky for me. And there is so much more to being a good couple."

"I know and you can train me to be whatever you want." WTF again. Train her?

"Sarah you need to grow more before you make a lifetime commitment."

"No. I'll be your family. Give you babies. Be your maid. Your total slut. You can whore me out to your friends. I'll find women for you. Any sex you want any way you want it anytime." She was sex obsessed.

No sense boring you with more. Hours later had to kick her out. Tried to get her a ride back but she refused. Upset and crying she finally stormed out. Long night waiting to hear she got back to college safely.

Spent weeks in a total depression. Friends and coworkers all noticed. Many reached out. But I just stayed quiet in my funk. Plowed through at work but at home mostly just slept. Hid things from my parents too. Pretended to be cheerful when we chatted on the phone.

Early December got the disaster call. Massachusetts State Police. My parents had died in a highway crash. Last straw. Called in and told Ms Hawthorn. She offered anything work could do for me. Told her I could handle things. Then curled up. Didn't even eat for a few days. Turned the phone off.

Knock at the door. Ignored it. Hadn't buzzed anybody in. They kept knocking. Went to see who it was. Shocked to find Janine and her wife Carla at my door. How did they get in the building? Why were they here?

Janine is one of our company's founding partners. Impressive lady who worked her way up in the 80s before women were common on Wall street. She was my mentor at work. Powerful, and scary when crossed. Nobody, even other partners, fucked with me after she made clear I was on her team.

"Ted you can see it is us open up."

"Uh ok give me a few minutes."

"No open the door now."

"Janine I'm in my skivvies." Not to mention unshaven and no shower for several days.

"Open the door now." Said like a Marine commander. Carla walked past me with a small pat on the shoulder. Janine closed the door and swallowed me in a motherly hug. Broke down crying.

Janine is around sixty, tall and slender, quite beautiful. A trail blazer in many ways. Carla is, as they joke, her trophy wife. A dark haired Latina in her thirties. Medium height with a classic curvy figure. Always thought of her as a cross between Salma Hayek and Penelope Cruz. Gorgeous in every way. Socialized with them many times including several dinners and parties at their penthouse.

Janine sat me at the table and pulled her chair next to me. Held my hand tightly as I sobbed. No words spoken. Carla brought my bathrobe and stood me up to put it on. She busied herself cleaning things up around the condo.

"Ted am so sorry. We're going to get you through this. Remember your parents want you to be healthy and happy. We will be with you and take care of everything. I'll take care of work. Carla's going to work you through burying your folks. We have a personal attorney if you need for their wills. And she has a company we've used that can manage their estate for you." Dammit I didn't want their millions.

Weeks were a blur. Carla was my constant companion. First week they would not let me stay alone. Spent it in their guest room. On reflection realized they were worried about suicide. They had a counselor visit to talk me through the grief process. It was mid January before I was back on my feet. Parents and work had been the two pillars in my life. Jumped back into work.

Even the geeks at work were kind and deferential. Everybody bent over backwards to help me recover. Am so grateful I work in a place where majority of people really care about each other.

Avoided anything social. My small group of friends were mostly old college buddies and a few from work. They tried to get me out but I put them off. It didn't feel right to have fun with my parents dead.

Early February Janine messaged me we were going to a dinner at a restaurant Friday. Assumed it was just her and Carla. Surprised to find we had a small private dining room and found several of my best buds there. Beer and pizza at a very upscale place. Just like Janine. High class and classy always.

Early on Janine excused herself leaving Carla as the only woman. The guys started to relax and open up. Carla made it easy. She joked around with the guys. A real man's woman. Except the lesbian part.

Got thoroughly drunk. College friends reminisced about parties, pranks, and my history dating the crazy girls. They closed us down and several of the guys took me home. Couple of them stayed the weekend. Finally came out of my hole a little.

On a warm early spring day Janine and Carla took me on a long walk in Central Park. Janine took charge of the conversation.

"Ted till now we've stayed out of your personal life. You are on the wrong track. Now your parents are gone. Your friends let us know, in their way, that you need help. Socially you are a mess. The attractive nice guy who always ends up with disastrous girls. Damn it you can't even hook up with a gold digger. Time to open up and let us lead you. Readjust your thinking and get you to the right woman."

"Janine and I are sure how you can find love. But you need to trust us. Learn how to be with a confident stable woman. How to be the man she desires. Love her and fulfill her needs. Then you can find happiness."

"Ted you need a take charge leader. Not some desperate bunny manipulating you." That part made perfect sense to me.

"I think a nice bitch on wheels." Carla laughed at her own thought.

"Uh why would I want a bitch?"

"The right kind of bitch. Yes you do. Time to put up or shut up. Let us help you." Janine stared me down as she said that. I acquiesced.

Carla chatted with me the next few weeks. Came over one night and we looked through an escort site to see what kind of looks I liked.

Janine talked to me about abstaining from sex. Told me no hookers or escorts. And to stop masturbating. Shocked me. Told her I would try. She snapped to just do it.

Carla set me up on a date. No info, not even a name. Just the restaurant and time on a Saturday evening.

Hostess led me to the table. Introduced myself. She was a heavyset brunette with a peasant face. Waved me to sit down.

"May I ask your name?"

"No. I'll tell you if you earn it. I'm only here for the free dinner. Doing a pity date as a favor." She smiled at my stunned reaction.

Waiter arrived a moment later. Hadn't even picked up the menu. Before I knew what was happening she ordered for both of us. She ordered lobster and a bottle of wine.

"He'll have the vegetarian salad. No dressing. And just water. Needs to watch his weight." Waiter just let that pass.

"So Ted are you just a loser? Closeted gay? What's the story?"

"That is uncalled for."

"Tough shit. Feel free to leave. Your report card is already bad. Do not make it worse." Stayed quiet.

Food arrived. Quietly ate the salad. She wolfed down the lobster and wine. Punctuated by a long dialog about things she wanted and her interests. Plus some strong opinions about news stories. I did not even try to interrupt. Although I really wanted to call her out about some of her stupid shit.

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