by Jamie Knight
“You’re not ordering me?” I asked a bit aloof.
“If you don’t wanna do it…”
“No-no, I do. I guess. Yeah, you know, it’ll be fun,” I decided.
And it actually was kind of fun. To speed the process, Jack cooked the sausage ahead of time on the grill to give it a smokey flavor, while I chopped up several of the other ingredients. Then Jack came in from his patio and started cooking down some of the onions and peppers. Eventually, all our separate endeavors were brought together in one big cooking pot. Then we let it simmer for an hour.
While we waited, we played another four games of chess. This time it was an even split in terms of the wins.
“You’re getting better at this,” I teased him.
“Well, a good teacher learns from his student,” he countered. “Eventually.”
I was finally beginning to relax. Maybe I had been too hard on Jack. This was a new experience for both of us in some ways. And everything with the pandemic and work just added to the stress. Perhaps we both only needed to chill out and not react to every little thing.
On the fourth day after work, I found Jack on the couch watching “Courtroom: Chicago”. It was a drama about lawyers in the court system in Chicago from the ’90s. It only lasted two seasons and was considered a joke in lawyer circles. The law research on the show was absolutely abysmal. The writers would literally make up laws just to hammer in plot points. I had had a professor in college that showed one of the episodes and made the class try to catalog every mistake.
“You down for a little binge-watching?” offered Jack. “We could make some popcorn.”
“Not a Tiger King fan?”
“I watched some, but no,” he replied. “This, however, fascinates me. I mean, how do people in Hollywood get real-life wrong?”
We made some popcorn and got some beers. Jack decided whenever one of us called out a mistake on the show, the other had to drink. We were two episodes deep, and we were quickly running out of beer.
“I’m going to have to switch to popcorn,” I said, my head swimming so much. “I can’t even keep up with all the mistakes on that show.”
“Did you see when the lawyer handed the judge cash for bail? What the hell was that all about?” laughed Jack. “He just put it in his pocket!”
“Yeah, I mean, I guess if you’re going to get it that wrong, might as well make it fast,” I joked. “But seriously, look at the female lead. She looks like a streetwalker! What kind of lawyer would wear that out in public, much less in front of a judge!”
“And in these shows, everyone’s abnormally handsome except Jerry Orbach,” Jack pointed out. “That poor guy. He’s the one character actor in a sea of beautiful faces. By comparison, he looks bad.”
“But he’s the one good actor on this show!” I laughed. “Some of those gorgeous dummies, Jesus, that blonde prosecutor?”
“Wow, is she hot!” laughed Jack. “I honestly couldn’t tell you what she said half the time.”
I frowned and punched him playfully. The banter between us was suddenly good. Maybe it was the beer, perhaps it was the terrible 90’s show, I could feel Jack and I mending the bridge between us.
“And how about that scene when they bring in the killer?” recalled Jack. “He looked like Hannibal Lecter from Silence of the Lambs.”
“I know. I’ll bet that show came out around then or right after,” I surmised. “These writers are just terrible. They’re not even original!”
“Yeah, and the guy was just a suspect in a hit and run! Why would you do that to your client? Who does that?”
After a few more terrible episodes, we finally called it a night. I staggered up to my room, flopped down on the bed and called Isabella.
“Hey, guess what?” I started.
“You’re happy again? I can tell in your voice,” Isabella guessed.
“Yeah, I’m pretty happy,” I admitted. “Jack and I spent the evening watching Courtroom: Chicago.”
“Ooo! That’s a good show.”
“No, it’s not! It’s terrible!” I laughed. “It has so many mistakes.”
“Well, I’m not a lawyer,” Isabella bristled. “But I could watch that Latino judge all day. God, he’s just carved out of bronze. I’d love to see what was in his legal briefs, if you know what I mean.”
“Bella,” I laughed.
“It’s good to hear you laugh again, babe.”
“Yeah, well, Jack was really trying,” I said. “You were right. I needed to give him a chance. He’s just been so sweet this week, and I feel like he cares about me, ya know? It’s not just about the sex. We haven’t done anything in a week.”
“I had a feeling if you kept your panties on for a while, different things might happen,” she joked.
“Hey!” I bristled. “You replace the batteries on your boyfriend yet?”
“No can do. All the stores are closed. Fortunately, I’m cheating on him with my shower dildo and my hand,” she admitted. “Unfortunately, the Amazon food items are getting very weird. The only bread I can order are tortillas, so it’s been a lot of tuna out of a can for me.”
“This pandemic will be over soon.”
“Yeah,” Isabella agreed, not really sounding like she did.
Chapter Sixteen - Sandra
Things got back to a new normal around the house. We weren’t having sex, but we were clicking as a team again. Even the guys on the Zoom meetings seemed to notice that we were working well together.
That night, we played board games like Settlers of Catan and Terraforming Mars. They were exciting games. Simple, but with complicated outcomes and strategies, not at all dissimilar from chess.
Then I had a terrible thought: What if this was all a ruse? What if the only reason Jack was kind to me was that he painted himself into a corner with Jake? Then he springs the fake engagement, knowing that I would go along, and now he has to play things out until he’s in the clear.
Could he be that Machiavellian? I had known guys that would go to great lengths just to get laid. Indeed, Jack had particular tastes. He couldn’t have sex with just anyone.
Then again, Jack was handsome and rich. If he really wanted a beautiful woman to tie up, most women would just put up with it. Certainly, Isabella seemed like she wouldn’t mind.
Was that what I was doing? I told myself I wanted to explore this lifestyle but was I lying to myself? Maybe I was the one that was being deceptive and didn’t even know it.
I had read about Jack for years on the Manhattan socialite webpages. He seemed to be having a glamorous life dating models and actresses. Was that all I was at the end of the day? Another lonely star fucker?
No, I wouldn’t believe that. Jack and I had a bond. Maybe it was just too complicate to be put into words. Perhaps I was just too deep inside the relationship to gain enough perspective.
After a few more days of being wooed, I was having fun, but I don’t think Jack wanted to have sex anymore. I made my own innuendos, but he turned me down at every possibility. After a few days, I decided to call Isabella again. She was the only one that could see straight. I gave her the lowdown.
“First you want to have sex, then you don’t, and now you do,” she charted. “Do you not see the mixed signals you’re sending out?”
“I know, but it seems like we’re getting along fine now,” I pointed out. “Why wouldn’t he want to?”
“When did the trouble start?” she said a little condescendingly.
“After we had sex,” I responded.
“Exactly. Sex with other people just ruins everything,” she proclaimed. “Trust me. I’m getting great at getting myself off. I’m thinking of buying a ton of cats now.”
“Are you being serious? I can’t tell anymore.”
“Honestly, I don’t know,” she laughed. “I’m getting a little stir crazy in the apartment. I’m thinking of going outside. I don’t care if I get the COVID anymore.”
“They said the masks were bad at first. Now they’re saying they’re good! I don’t trust these people!” she snapped. “Sorry, I just really need some cats or batteries.”
Isabella sounded like she was starting to lose it. I pictured the apartment rife with empty food containers from takeout. She had told me she got to be afraid of taking out the trash, and the garbage was full. That was over two weeks ago.
“Don’t worry, Bella,” I soothed. “This is all going to be over soon. They’re saying by the end of May at the latest. But what do you think I should do about Jack?”
“You have been sending him mixed signals,” she noted. “Send him a clear one. I wanna fuck!”
“What? You mean just say that?”
“No, I was talking about me. You think our doorman’s married? Or discreet?”
“Bella, he’s like sixty.”
“A sturdy sixty,” she corrected.
“You’re no help. I’m gonna go,” I announced.
“Please, do me a favor,” she asked. “Just go have sex with Jack. Trust me, he wouldn’t go to all this trouble if he wasn’t into you.”
“Haven’t you been listening? That’s what I want to do.”
“Oh, then he’s just making you wait,” she assured. “That’s what he does, right? Makes you anticipate so you’re nice and wet by the time he starts doing it.”
“That is true,” I agreed. “Okay. I’m really going now. Bye.”
“Bye.”
I hoped this lockdown would end soon, or I’d have to put Isabella in an asylum. Or at the very least, I’d have to try to get her a boyfriend. It’s a shame I couldn’t just order one up like a pizza. That would be interesting.
The next night, Jack showed up in my room with the Scrabble game. I hadn’t played Scrabble since I was in the eighth grade, quite frankly. I was just getting out of the shower when he walked in. Fortunately, I was wearing a towel.
“Oh, hey,” he greeted. “Sorry, didn’t realize you were, uh, just getting out. I brought Scrabble.”
“Oh, sounds good,” I agreed. “Let me get dressed, and we’ll play. Sorry, I was just feeling grimy.”
I turned around to find some clothes in my drawer, holding the towel against me with one hand. Fumbling with my panties, I dropped them on the floor. As I bent to pick them up, Jack was suddenly there, helping me pick them up. He took them from my hand, tossed them aside, and stared deeply into my eyes.
“I want to try something I haven’t tried in over a decade,” he whispered.
“What?”
He pulled me close and kissed me. It was a real kiss! It was long and deep and sensual. I immediately dropped the towel to put my damp arms around him. He held me too, and I felt the strength of him against my body.
This wasn’t like the sex we had had in the past. There was a different kind of warmness and gentleness to it. His warm body against mine made me feel safe and protected. I never wanted to leave that feeling behind.
Moving to the bed, we continued to kiss. He started unbuttoning his shirt, and I helped him get undressed. I unbuckled his pants, and he struggled to continue to kiss me as he took off his clothes. Soon, we were both naked, lying on the bed, kissing passionately. The skin on skin contact was a significant turn on.
“Oh, Jack, I’ve longed for this,” I whispered. “Don’t stop.”
“Sandra, I don’t want to,” he whispered back. “My sweet girl.”
We explored each other bodies with our hands. I rubbed his hard, muscular chest as he gently caressed my breasts and kissed my nipples. I could feel his cock growing and poking into my stomach. I reached down and stroked his growing head. I could feel the vein with my fingers as it pumped blood to further engorge his cock.
Then he took his fingers and gently started playing with my folds and fingering me as he kissed me. Almost immediately, he built me to an orgasm. I had to pull away from his lips for a few moments just to catch my breath as he long, manly fingers explored my pussy.
“Jack,” I gasped. “You’re making me cum. I cum so good!”
I gushed all over his hands and could feel the tension melt out of me. I shook from the orgasm. Since I was wet with desire, he lifted one leg and slowly started to push into my pussy.
“Oh,” I squeaked. “Yes, that’s it.”
“So hot, so warm,” he muttered. “Oh, it feels so good.”
Jack started to slowly move in and out. His cock spread my walls. My pussy quivered in joy. I glanced down to see his dick go in and out of my pussy. My eyes were rolling back in my head, it was so good.
Shifting positions, I laid on my back. Jack took my legs up. He put my ankles on either side of my head and started pumping in and out of me. Oh, God! It was so good! I was shaking with multiple orgasms now, unable to hold back.
“Oh! Oh, yes! God, yes! Jack! Jack!” was about all I could say.
Soon, my sounds became less coherent. I was just grunting and squealing in pleasure as his cock rubbed my insides. It was a feeling I wanted to never end.
Then we changed positions. This time he got behind me, but instead of pulling my hair, he leaned over. I could feel his chest on my back as he fucked me from behind. The additional warmth alone got me off, and I was just shaking and orgasming. His thumb was positioned right near my head. I sucked on it eagerly as Jack continued to fuck me senseless.
He slowed down, and I didn’t think I could cum anymore. We were both panting heavily. Jack slid out. Still hard and not spent. I turned and pushed him down on the bed. Lying on his back, I mounted his thick cock, sliding down while leaning on my ankles. I proceeded to bounce up and down on him.
From my position on top, I was in perfect control. I could maneuver his dick wherever I wanted inside. I put it in the best place and just kept bouncing to hit that perfect spot inside me.
I had been exhausted, but now I felt energized. I felt like now I was fucking Jack. Yes, his cock was penetrating me, but the control made it my cock.
“You like that?” I asked. “You like to get fucked like this?”
I was raspy. Sweat was dripping down my body now. It drenched us both. I put my hands on his chest to steady myself and continued to bounce up and down.
“Yeah,” he whispered. “Oh, yeah. Just like that.”
Then I decided to try something I had never done before: Reverse cowgirl. Spinning around, I proceeded to bounce up and down at a different angle. This hit different parts of my pussy, and I immediately started shaking.
Jack grabbed either side of my hits and helped me bounce.
“Fuck! Fuck! Fuck!” I gasped.
I couldn’t believe the sensations I was feeling. No, I wasn’t a virgin anymore, but I had never explored my sexuality. Not like this. Yes, the rope and bondage had been new, but trying new positions just for me? That was different too.
“Oh, my God,” grunted Jack. “I think I’m going to cum.”
I slid off and started sucking him off. It wasn’t enough that I would feel it. I had to see and taste his cum. This moment now was what I needed. There was no more accurate gauge of a guy’s attractiveness toward you than to see them cum. You know they are getting off. It’s honest and real.
He exploded, shooting a blast of cum past my face and over my head. A streak of seed was left across my eye and forehead. Then another pump and I had leaned forward, catching the next squirt against the roof of my mouth. Its salty, warm goodness filled me with joy. Then I put my mouth over the head of his cock, sucking out the rest as it pumped down my throat.
“Oh! Oh, fuck! Holy fuck!” Jack exclaimed. “Jesus fucking Christ, that’s good!”
No more of his seed would be wasted. I sucked out the rest of it until his dick started to go a little limp. Then I tickled his cockhead with my tongue, stimulating him a little further. He shuddered in joy, experiencing post-orgasm quakes. It gave me great pleasure to see the expressi
ons on his face.
“Good girl,” he whispered.
Chapter Seventeen - Jack
The next three weeks were like a honeymoon between Sandra and me. While the country started tearing itself apart over the virus and then riots, we were locked away from it all. We’d occasionally talk about it, but mostly we were too busy getting lost in each other’s eyes.
When I awoke in the morning in Sandra’s bed with her head on my shoulder, it was an experience that I began to enjoy significantly. I had something to look forward to, and she had the comfort and protection she wanted. She didn’t know it, but it had been over ten years since I gave myself to someone like this. It was a big step for me.
Still, I had avoided having her come to my bedroom. I wasn’t quite ready for this morning bliss to happen there, but baby steps. For a moment, I thought I had lost her or pushed her away, but something deep down told me we’d end up together again. That I was just fighting against the inevitable.
The work had slowed but hadn’t stopped. Mergers are a complicated business, but because most of our smaller clients had stopped doing business altogether. It was somewhat easier to push the merger ahead, even while working from home.
“How you been, boss?” greeted Kelton. “You know, you’ve been unusually cheery these pay few days?”
“Have I?” I asked. “Guess that’s because the merger is almost over.”
“Well, that and your engagement, I assume.”
Word travels fast even when no one’s going to the office.
“Congrats, by the way,” Kelton added. “You guys pick a date yet?”
“No. I thought things were settling down, but now with these riots…”
“Yeah, it’s crazy,” added Kelton. “People are marching everywhere. I mean, it has to be that so many people are out of work too, right? It’s like a perfect storm.”
“The lawsuits that will come out of some of this,” I thought aloud. “We’ll have plenty of business in the coming years. DeBlasio has lost his damned mind.”