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Nice Guys Finish Last - Pt 1

The MILF at work piques my interest and a relationship develops.
Gabrielle was a doll. She was tall, good-looking, and smart. She was also funny. I had a crush on her within a couple of weeks of our first meeting. When I told her I enjoyed the company of attractive women with a brain, she sort of scoffed.

“Brains, huh?” she snickered.

“That's right,” I asserted. “You can't have much of a conversation with a boob.”

“I don't think that's what they're for,” she deflected.

“Of course not,” I countered. “Just making a point.”

Eventually the occasional jousting intrigued Gabrielle. She began to confide in me about a number of challenges in her life. I heard how her ex-husband had been skipping out on child support payments and ducking court hearings. She told me about an outing that led to a confrontation with an older man that left her disconcerted.

“He told my friend he'd like to fuck me,” she whispered. “Do you know what a MILF is?”

I nodded. “I do know. You should be flattered.”

“He said I was a MILF.”

“The background is that a MILF is experienced and knows that sex is fun. She's supposed to be past the stage of using sex to manipulate a partner.”

“How do you know all that?” Gabrielle asked.

I chuckled. “I've had the occasional encounter with a MILF.”

“You think I'm a MILF?”

I was stymied. Of course Gabrielle was a MILF. But, if I admitted that, she'd think my only intent was to nail her. “I think there's much more to you than being a MILF,” I said. “Are you considering taking him on?”

“Absolutely not!” she stated unequivocally.

“Just take it as a compliment, then. He thinks you're hot.”

“It's kind of insulting, though. I mean, I'm more than a fuck machine.”

I agreed and we parted.

Her kids were her primary concern, of course. She worked two jobs to make sure they had the necessities. Gabby also attended the local community college, seeking to improve her skills for a different, higher paying job. I caught her studying in the lounge one day.

“I'm proud of you,” I told her.

“You are?”

“Sure. Two jobs and school. That's got to be tough.”

“Hmmm,” she hummed.

“What is it? What are you studying?”

“Fucking algebra,” she said.

“Whoa! Sounds like a challenge.”

“Who adds an 'a' and a 'b', or divides an 'x' by a 'y' much less?”

“Those are called variables,” I said.

“You know about this shit?” she asked.

“A little bit. You need some help?”

“Oh, hell yes! The teacher is like an Arab or something. I can hardly understand him.”

We worked together for a half-hour or so. Gabrielle closed her books, stuffed them in her locker and went back to her work station. I got an email a little later that just said, “Thanks for helping me with my Math.”

“Any time,” I sent back.

We ran into each other occasionally over the next two weeks. I'd casually mention her studies and ask how they were going. She would usually reply that she was slogging her way through them. I reminded her I had some experience as an educator, to any time she needed some help, I'd be glad to work with her. My remarks were usually met with a superficial thank you.

One day she was grinning as she walked into the break room.

“Hey!” I called out.

“Hi,” she said, her grin showing the little snaggle-tooth thing I found quite attractive.

“Glad to see you in a good mood for a change,” I told her.

“One of the IT guys?” she said, beginning her tale. “He was working on installing an anti-virus upgrade. Real quiet like he says, “I like your boobs.”

“He didn't,” I said, sounding aghast.

“Well, I told him, 'Excuse me?' And, then he pointed to the floor. 'Your boots,' he says. 'I like your boots.' I almost fell off my chair laughing.”

“I'm not surprise you were shocked,” I said, grinning. “I mean, you don't really show them off.”

“My boots?” she asked.

“No,” I answered.

“Oh, well,” she grinned. “I don't want to make a spectacle, if you know what I mean.”

“They are nice, though,” I told her.

“What?” she said as if offering a challenge.

“Your boots. I like your boots.”

The look she gave me was uncertain. “I thought you meant...”

It was my turn to laugh. “I'm forward,” I told her. “Not that much, though.”

“You're a funny guy,” she said.

I just smiled.

The next day, Gabrielle walked into the break room and sat perfunctorily next to me. “Can I ask you something?”

“Sure,” I said. “My life is an open book.”

“What do you want from me?”

I was taken aback. I shrugged. “Nothing, really. To be friendly. I don’t need any more enemies. I hope I can count you among the friends, Gabrielle.”

“Okay,” she said, standing up. “My friends call me Gabby,” she said and feeding quarters into the soft drink dispenser. When she sat back down she steered the conversation into mundane topics of discussion such as the challenges of the job and her need to find new daycare facilities for her kids.

“Not having any kids,” I remarked, “I'm pretty much unqualified to give you any advice in that arena.”

That night I got a friend request on Facebook from her. I responded in the affirmative adding that I really didn't utilize it very much.

“I'm on here all the time,” came her quick reply.

“Maybe I'll make it a habit to hang around here more often,” I sent back.

“OK,” she typed. “C U tomorrow in the break room.”

The next day I asked her how the daycare search was going.

“It's solved,” she said. “My Mom says she'll take the kids when I have to work or go to school.”

“That sounds perfect,” I told her. “I'm glad it worked out.”

“Yeah,” she replied. “I may even get to have some sort of a social life now, too.”

“That would be nice,” I told her.

“You know I haven't been out on a date in nearly two years?” she confided.

“That's a long time,” I admitted. “What would you like to do?”

“Nothing much. Couple of drinks and dinner, maybe.”

“That sounds simple enough,” I agreed. “You have anybody in mind?”

“Yeah, I do. It's just, I don't know if he'll ever ask me.”

“Why not?”

“Because we never talked about dating before. It would kind of take things to a different level.”

“Well, Gabby,” I smiled at her, “we're beyond the Victorian age. You have the right to ask him to take you out, you know.”

“Would you?”

“If it was me, I'd ask.”

“No,” she said, her dark eyes focused on the floor. “Would you take me out for a couple of drinks and dinner?”


“Oh, God,” she moaned. “I knew it. I knew this was a mistake.”

“No, Gabby, stop,” I said softly, covering her hand with my own. “You misunderstand me. I'm just a little surprised. I figured you'd have men lined up ready to court you. I'd be delighted to take you out on a date. Are you sure?”

“You're the only guy I can trust who's not going to press me for a quick fuck on the first date.”

I laughed. “By the second, though, I'm definitely going to be ready for you to put out.”

She chuckled. “Yeah, we'll see. You're not serious are you?”

“Of course not,” I said. “I come to you devoid of expectations.”

“Can you do Friday? I've got a class Saturday, so it'll have to be early.”

“How early? Five? Five-thirty?”

“Yeah, five-thirty sounds good.”

“Okay,” I grinned at her. “I'll pick you up at five-thirty and plan to have you in bed by nine. How's that sound?”

“Like you want to take me to bed by nine,” she said.

“Don't forget,” I joked, “you are my favorite MILF.”

“Oh, shut up!” she demanded. “I promise that I'm not fucking you on our first date.”

After the date I took her home. I let her out of the car and walked her to the door.

“My Mom's here,” she said. “You better be on your best behavior.”

She opened the door and I followed her in. I met her mother, who checked me out. She asked how I'd met Gabrielle and I told her at work. She seemed suitable unimpressed. Gabby led me back to the door and walked out onto the front porch with me.

“She'll come around when she finds out how intelligent and funny you are,” she said.

“I don't know,” I said. “Somehow I think nobody's good enough for her baby girl.”

“She'll like you,” Gabby assured me. “I do.”

“Thank you for the reassurance,” I said. “Guess I'd better go.”

Gabby grabbed my arm. “I told you I wouldn't sleep with you on the first date. But, let's try this,” she said, lifting her lips to mine and pressing them gently. I'd be a liar if I didn't admit to feeling the stirrings in my loins.

“Nice,” I said in a whisper after she released my lips.

“Yes, you are,” she mumbled. “You're one of the really nice guys.”

“Thank you,” I joked with her. “You do remember the adage that nice guys finish last.”

“Hmmm,” she said. “We'll see. Someday we just might see.” She gave me another light kiss on the lips and we parted.

Gabby and I didn't see each other until Tuesday. She walked into the break room and sat opposite me.

“How's your Mom?” I asked.

“Cranky,” she said. “I tried to tell her it was just a date, but she's sure I'm going to fuck up my life again.”

“Are you?”

“I'm trying not to,” she said. “That's why I didn't come in here yesterday. I wanted to give us some space.”

“That's fine,” I smiled. “Makes sense.”

“I was miserable. I missed seeing you.”

“I missed seeing you, too,” I said. “I've come to realize our little visits make my days. When I don't get to see you I get to feeling lonely.”

“Poor baby,” she said, her hand seeking out mine. There was a tingle of electricity when we touched.

“You feel that?” she asked.

“Sure did,” I told her. “I was wondering if you did.”

“Oh, fuck!” she exclaimed, sounding dismayed.

“What?” I asked, somewhat alarmed.

“You know what that means, don't you?”

“I, uh. No, I don't. What does it mean?”

“It means we're going to fuck sometime real soon. God! I don't want to screw this up!”

“Whoa, girl!” I laughed. “Take it easy, there. We don't have to do anything you don't want to do.”

“That's just it,” she sighed warily. “I do want it. I want to feel you pressed against me. I want to feel you inside me. Didn't you feel the humming when we touched? This is so going to fuck us up.”

“Does it have to?” I asked her.

She looked into my eyes. “That's why I don't want to. But, I do. God! I'm aching for you.”

I laughed. “Good! I like that.”

“No, but I can't. I mean, I can, but I shouldn't. But, God, I want to!”

“You remember our talk about MILFs?”


“Well, this is just MILFdom at its peak. You know about your own sexuality. You know what you want, and you know you have the choice to do it or not.”

“What the fuck are you talking about?” Gabby demanded.

“The spark between us, what does it tell you?”

“We're going to be good together.”

I nodded. “Okay. And you want to feel that spark down there between us, right.”

“Yeah, I guess so.”

“Come on, Gabby,” I scolded gently. “Be honest with me.”

“I just know it's going to be good. We've got that spark. It's like we're meant to be together, you know, fucking.”

“You see? You see how easily that word comes out of you. That's because you understand all that it is and all I means. It's nothing mysterious or secretive.”


I wagged my head. “You want to find out if the reality lives up to the expectation.”

“If it doesn't, though. That'll completely fuck us up. I don't want that.”

“You can leave that to me, sweetheart,” I consoled her. “I'm going to make sure that it is everything you want and more. We're not only going to be good, we're going to be spectacular.”

“How do you know that?”

“Because I'm going to do everything I can to make sure it is. But, there's no hurry, okay? I want you, too. But, I can wait. I may not want to, but I can.”

“So we're going to be spectacular?”

“I promise.”

“Then I don't see why we should wait.”

“See, that's the MILF in you. Waiting is a function of trying to control the situation. Because you know what it can be like, you're not inclined to wait. Why delay the gratification?”

“Hell if I know,” she said.

“There you go,” I told her.

“Unless you just want to get into my pants.”

“Since we met,” I admitted.

“Then what?” she said.

“What do you mean?”

“What happens afterwards? Are you going to fuck and run?”

“Could be,” I said. “You think that's the kind of man I am?”

“Oh, shit,” she spat out. “I don't know.”

“That hurts,” I told her. “After all the time we've spent together, you don't know me any better than that?”

“I don't want to think you are,” Gabby said. “That's why it scares me. Once you fuck me, maybe you'll just move on.”

“Of course, the possibility exists that it will be so intoxicating I'll become addicted and be unable to extricate myself.”

“I guess,” she said.

“Okay, then,” I proposed, “let me ask you the same question you asked me a week or so ago.”

“What's that?”

“What do you want from me, Gabby?”

She looked like I had slapped her. “I..I..I want you...I want you to be around for awhile. I want you to not just make this a notch in your gun. I want to be more than a quick fuck for you.”

“Okay,” I nodded. “So, do you want us to become a couple?”

“That's...yeah, I'd like that.”

“How about friends with benefits?”

She worried a thumbnail. “Yeah, that'd work, I guess.”

“It would give you time and opportunity to hook me for good.”

“Is that...I mean would that be a bad thing?”

“Only if that is your intention,” I asserted.

“But you suggested it,” she protested.

I shook my head. “I suggested the situation, not the rationale, not the reason for it.”

“What does that mean?”

“It means, if you are going to use sex to trap me into something I don't want, into a situation I don't want to be in, then that's manipulative.”

“You could do the same thing,” she argued.

I laughed. “Uh, I don't think so. Being the MILF you are you can bed any man who strikes your fancy. I don't have that same option.”

“Don't sell yourself short, baby,” she sniped.

“How often do you think that spark you felt happens? I can tell you, it's damned infrequent. In fact, you maybe the only woman who has told me outright that you want me to bed you.”

Gabby sat, looking at the table where our hands remained joined.

“What are you thinking?” I finally asked her after several moments of silence passed.

She reached up with her other hand and let it join the other so my hand was clasped between the two of hers. “I'm thinking, fuck it. Let's do this and see what develops.”

I nodded slowly. “I think that's a good option.”

Gabby squeezed my hand. “Listen to me, you son-of-a-bitch,” she said. “If you fuck me over, I'll have your balls in place of the fuzzy dice on my rear-view mirror.”

I couldn't help but laugh. “Fair enough,” I responded. “But, I don't think that will be a problem. I think I'm planning on hanging around as long as you'll have me.”

“What about my kids?” she asked.

“One step at a time, sweetie,” I said, putting my free hand atop hers. “Most kids find me entertaining and adorable.”

“I can see why,” she said. “Oh, shit! Look at the time. I'm late!”

“Me, too,” I acknowledged. “Back to the salt mine.”

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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