Chapter 6: Some Good Advice And A Chance Encounter

June 22, 1981, Chicago, Illinois

I wondered what I had missed, but any question in my mind was answered by looking at Charlotte’s curvy form and very nice breasts. If I had a chance at THOSE, then I wasn’t going to turn her down. But, as with Gudia, I didn’t have any rubbers with me because I hadn’t even considered the possibility. If it was somehow going to rain pussy, I needed to be better prepared! Even if this was just dumb luck, I STILL needed to have some ‘just in case’.

“Sure,” I replied to her invitation.

I followed her along the walk behind the house and then up some stairs to a loft apartment very similar to the one I’d rented about five miles north. Charlotte turned on a window air conditioner unit and pointed to the couch. I sat down and she sat in a chair and we finished our ice cream as cool air began driving the heat and humidity from the room.

“So your goal is to be rich?” Charlotte asked.

“As a means to an end, yes. I want to have a nice house and a nice car, and to be able to take vacations. And eventually to have a family. But that last one is a long way off.”

“Defensive!” she laughed.

“Sorry, but I’m only eighteen.”

“Me, too. What I said before is true, but I’m just interested in having some fun before I get tied down with a husband and kids.”

“Wait, didn’t you say that was your goal?”

She laughed, “Long-term, like yours. Gotta have as much fun as you can handle before you shackle on the ball and chain, right?”

“I’m getting SERIOUSLY mixed messages here!”

“Do YOU want to get engaged and married and have kids right this minute? Or even in the next three or four years?”

“Hell no!”

“Me neither! Wanna have some fun?”

“Fun is good,” I grinned.

“Glad to hear it! And you chose the right sister, by the way.”

“Oh?”

“I’m WAY more fun than Candy. I promise!”

“So it’s a competition?” I grinned. “I should have fun with you, and then with her, and give scores like the judges in the Olympics?”

Charlotte laughed, “I don’t think they have THOSE kinds of competitions in the Olympics!”

“No?”

“I can see it now — ‘Next on ABC Sports, Synchronized Screwing! USA versus Sweden!’.”

We both laughed hard.

“I don’t think you could get that on TV!” I said.

“Can you imagine the old biddies whose heads would explode?”

“That said, I wouldn’t mind being a judge of the Swedish Girls Synchronized Screwing team!”

“Hot blondes with nice boobs?”

“Exactly.”

“What about black hair and nice boobs?”

“I suppose,” I said with a theatrical sigh. “I think I’d have to check them out first.”

Charlotte laughed, got up, pulled her polo shirt over her head, dropped it on the chair, then reached around and unhooked her bra. She slipped the straps off her shoulders and dropped it on the chair to join her shirt.

“38Ds! Will they do?”

“I believe any answer other than ‘yes’ would lead to my immediate death! But I don’t have rubbers.”

“Candy has a case, I’m sure! Let me check.”

She went over to a nightstand by the bed, opened the drawer and pulled out a box.

“Yep,” she smirked. “An unopened box of a dozen. Think that’s enough?”

I laughed, “I’ll do my best.”

“Then let’s see what we have to work with!”

She walked over to me and unbuckled my belt, unbuttoned and unzipped my jeans, then pushed them and my briefs to my ankles. She pushed me gently back onto the couch and grasped my quickly hardening dick in her hand. She gently stroked until I was fully hard.

“Let’s see how long it is,” she smirked.

She lowered her head, opened her mouth, and slowly began taking me in. I’d had exactly two blowjobs from Bev, and while I’d enjoyed them, she hadn’t been thrilled to do it. Charlotte on the other hand, seemed eager. She continued sliding her lips down my shaft while sucking gently. I was shocked when her lips touched my public hair, as Bev had never gotten more than halfway down before gagging. Charlotte sucked hard, then began moving her head upwards, sliding her tongue along my shaft. She lifted off completely and looked up with a smirk.

“Like that?” she asked.

“Absolutely!” I breathed.

She winked, then took me fully into her mouth again. This time when she moved upwards, she kept the head in her mouth and swirled her tongue around before engulfing me once again. I felt her fingers on my sack and she traced my balls as she bobbed. I knew I wasn’t going to last long with the intense pleasure, so I tried to control my breathing. I wanted to cum, but I also wanted to feel her lips and tongue for as long as possible.

I didn’t look at my watch, but it seemed like five minutes before I knew I could no longer control the intense pressure. I groaned and a spurt of cum flew from my dick. Charlotte swallowed and rose up, keeping just my head in her mouth, stroking me with one hand and sucking hard and swirling her tongue as she swallowed several strong spurts. After the last one, she bobbed a few times, then released me.

She surprised me by putting her hand on the back of my head and pulling me to her for a kiss. Before I knew it, her tongue was in my mouth! I recoiled, breaking the kiss.

“Charlotte!” I spat, thoroughly grossed out by what she had done.

She stood up and glared at me.

“What? You came in my mouth and that’s OK? But you won’t kiss me afterwards?”

“But you had my cum on your tongue!”

“So? If you EVER want another one of those, deal with it! If you’re THAT grossed out, you can leave! I won’t object to kissing you after you eat me! Or don’t you do that because you think it’s gross?”

It dawned on me that both Bev and Gudia had happily kissed me after I’d licked them, but that didn’t change how I felt about what Charlotte had just done.

“No, I do that. But...”

“But what?” she asked. “If you aren’t man enough to kiss me after I blow you, put on your pants and leave. I thought you were fun, but I guess I was wrong.”

“And you do that with every guy? And they don’t object?”

“If they do, they never get it again. That was true from the first time I blew a guy when I was fifteen. He acted like I had the plague afterwards so I dumped him before he got my cherry. That went to a guy who WAS willing to kiss me after I blew him. And he said it was worth it! He loved the extremely tight fit, and you’re thicker and longer than he was, so you do the math! If you want to play with these boobs, and fuck like bunnies for a few hours, kiss me again. If not, then like I said, get dressed and leave.”

Charlotte put her hands on her hips which really made her gorgeous breasts stand out, seeming to defy gravity. I wanted to get my hands on them, and my mouth. And if she was telling the truth, I wanted to screw her, too. But did I want those things enough to kiss her again? I had been totally grossed out, but was it THAT bad, compared to what she was offering?

As I thought about it, I realized that at least at THIS point, there probably wasn’t any left, which meant I could kiss her without having to actually do the thing she insisted I do. And I’ve had time to think about it before it happened again. Having sex with Gudia had flipped a switch and with more on offer, from a girl with awesome breasts, I couldn’t say ‘no’. Not now, anyway.

I stood up, pulled Charlotte against me, and kissed her deeply, suppressing the upwelling of disgust, which, fortunately, passed quickly. I broke the kiss and we quickly removed each other’s remaining clothing. We dropped down onto the padded area rug, and Charlotte used her mouth and hand to get me hard.

She reached over, tore open the box of rubbers, extracted a single foil packet and ripped it open. She quickly rolled it over my erection, then straddled me. Positioning the end of my dick against her pussy, she rubbed it back and forth, then ever so slowly lowered herself onto it. She wasn’t kidding about being tight, as her pussy gripped me like a vise. It took perhaps two minutes before she worked my entire latex-covered shaft into her.

“I’m glad she bought lubricated rubbers,” Charlotte gasped. “That thing is long AND thick!”

She shifted so that her amazing breasts were over my face and I happily took a large, protruding nipple into my mouth and began sucking. Charlotte ground against me for a moment, then began slowly sliding up and down, squeezing her muscles to make the fit even tighter. I switched breasts, and Charlotte began moving faster, both up and down and back and forth, then pushed down hard, ground against me and groaned loudly as her pussy squeezed my dick even tighter.

To my surprise, she sat up and lifted off. She lay on her back and tugged on my arm.

“Fuck me hard!” she gasped.

I moved between her legs, positioned myself, and slid fully into her. Charlotte wrapped her legs around me and we began, as she had put it earlier, fucking like bunnies. Her first orgasm had loosened her enough for me to fuck her hard and fast, in the way Bev and I had done it, and within three minutes, Charlotte had cum again, and I filled the rubber with jets of cum which I thought might blast it off.

We caught our breath and then I carefully grasped the rubber and pulled out. I’d only ever used one them on a few occasions, at first, before Bev went on the Pill, then when she had missed a pill one month. That had been enough to learn how to use them properly, as we didn’t want ANY chance of her getting pregnant after being foolish that first night. I looked around, found a box of tissues, pulled off the rubber, wrapped it in a tissue from the box, and dropped it in the trash can.

“Not bad,” Charlotte said. “How long before you can go again?”

“Maybe ten minutes,” I replied. “Sometimes faster, with encouragement!”

Charlotte laughed, “Then lie on your back. Eat me while I suck you, and when you’re hard, we’ll do it all over again!”

I did as she asked, and she turned and lowered her pussy to my face. I pressed my tongue into her, and she took my flaccid dick into her mouth. Less than ten minutes later, she was riding me again. We completed the cycle, and after a third round, she led me to the small shower where we washed up, our bodies slipping over each other’s in the tight confines. I spent considerable time lathering her breasts, causing Charlotte to laugh, and spend considerable time lathering my dick. That led to a blowjob in the shower, and a kiss that nearly made my dinner come up.

We got out of the shower, dressed, and Charlotte sprayed some air freshener around the room, and used a soapy towel to clean up the spots we’d left on the area rug. Once she was satisfied, we left the apartment and began walking back towards the Sox Park L stop.

“I had fun tonight!” Charlotte said when we arrived. “See you at work tomorrow!”

“Me, too,” I replied.

We exchanged a quick kiss, then I dropped a token into the turnstile and headed up to the L platform. I sat down on a bench to wait for the next northbound train, wondering if I actually wanted to see Charlotte again. I’d obviously see her at work, but her last kiss, after the blowjob in the shower, had turned my stomach. She clearly hadn’t swallowed, and her mouth had been full of my cum.

That was FAR different from the small amount on her tongue the previous time. I felt she’d done it intentionally, to gauge my reaction, and I’d managed, just, not to throw up or react in any negative way. Just the thought of it now caused my stomach to rumble. I loved her breasts, and the feel of her extremely tight pussy, though I would rather have felt it without a latex barrier. Fundamentally, if sex was a requirement for a happy life, and in my opinion it was, then Gudia was a FAR better choice.

I marveled at the luck I’d had, minus those kisses. I’d been in Chicago less than a month and already gotten laid with two different girls. I knew guys back home who had multiple girls, but other than Bev, no girl had shown much interest. Of course, the fact that I worked all the time and basically had no money had been a huge factor. Here, it had been plain dumb luck that I’d run into the architecture student, Anala, who’d introduced me to her friend, and Charlotte, who had been the first female hired in the mailroom.

The train arrived and I boarded, heading for a downtown station where I could switch to the Milwaukee L without a transfer, which I hadn’t purchased. My mind went to what I could do to meet some guys. A shooting range would be perfect, but Chicago seemed to be insanely anti-gun, so that wasn’t likely. Not to mention I’d left my .22 at home, and there was no way I could afford to buy a handgun.

I sure wasn’t going near a church, and I’d never learned to play chess or golf, both of which attracted lots of guys. Martial arts didn’t really attract me, and other than using my uncle’s weights, I wasn’t interested enough in working out to join a gym. I wasn’t old enough to drink now that everyone had started becoming insane about the drinking age, so going to a bar was out. And I couldn’t afford to take even one class at a Junior College.

I changed trains at Lake Street, and twenty minutes later, I walked in the door of the townhouse.

“Hi, Jonathan,” Uncle Alec said as I came in the front door.

“Hi.”

“Have a good time?”

“I did.”

“Glad to see you making some friends.”

“Me, too,” I replied. “I’m going to go study a bit, then head to bed.”

“‘Night.”

“Good night.”

I went to my room and pulled the binder from the shelf and began reading about ‘clearing’ and ‘settlement’.

June 23, 1981, Chicago, Illinois

While riding the L into the city in the morning, I thought about how to handle Charlotte. I’d decided I didn’t want to see her again, but I was going to have to work with her. The last thing I needed was a confrontation in the office, or even an adversarial relationship in the mailroom. I got off the L at Grand Avenue, and walked east towards Michigan, knowing I’d have to say SOMETHING to Charlotte, but not what to say.

“Morning, Boss!” I said, walking into the mailroom and seeing Mr. Nelson.

“Kane,” he replied with a nod.

I punched in and picked up a stack of envelopes which had arrived overnight and began sorting them for the morning delivery. Charlotte walked in a minute later and Mr. Nelson asked her to come to his office. As soon as they left, I went over to Nick.

“What’s up?”

“Exactly what I said. Bill Mertens asked to interview her for his secretary job.”

“With no experience?” I asked.

Nick laughed, “Are you kidding? With that chest and that cute butt? That’s all the ‘experience’ she needs! You know why Julie Harris was REALLY fired, right?”

“You know me, I keep my head down and my mouth shut.”

“I told you the other day what goes on. Put two and two together.”

“Yeah, I got it. So what happens?”

“He talks to her, decides he wants her, and she gets the job.”

“But doesn’t she need to be able to type or take whatever it’s called? Shorthand? They taught that stuff in my High School.”

Nick shook his head, “None of that matters if she takes care of Mr. Mertens. It’ll work itself out.”

“Weird,” I replied.

“Do me a favor, sort Charlotte’s overnight stuff. I doubt we’ll see her for a few hours. I’ll do her rounds if need be.”

“On it!”

I grabbed the stack of envelopes for the 34th floor and sorted them into Charlotte’s cart, marveling at my good luck of so far not even needing to speak to her. I finished sorting the overnight deliveries, just as the cute secretary from Personnel came in with a stack of envelopes to be delivered. I took them and quickly sorted them, then let Nick know I was going on my rounds. He’d do Charlotte’s rounds as soon as Mr. Nelson came in to sit at the desk.

When I was on the 35th floor, I saw Charlotte in Bill Mertens’ office and wondered how she was reacting, given what her sister had said the previous evening. I wondered, too, what might happen if she turned down the promotion. Strangely, I felt bad for her, despite my decision to not continue a relationship with her. In fact, as I thought about it, the entire system at Spurgeon bothered me. I wanted to get laid as much as the next guy, but the idea of effectively requiring sex for a woman to keep her job bothered me.

I finished my rounds, returned my cart, then went back to the 35th floor to check and restock supplies. By the time I finished, Charlotte was back in the mailroom.

“Ugh,” she groaned just loud enough for me to hear her.

I couldn’t be rude, really, so I answered her.

“Fun interview?” I asked quietly.

“God, he’s disgusting,” she spat. “Candy was right about him. The salary is more than double what I make, but there is no way I’d fuck him for ten times what I make!”

“So you turned down the job?”

“He told me to think about it and give him an answer tomorrow. I’ll talk to my sister, but I can’t imagine I’ll take it. Maybe you think it’s weird that I’d fuck you without us going together, or whatever, and then refuse to do it with him, but having sex with a good-looking guy who’s my age is way different from having sex with an old fat guy!”