Adventures in Modern Dating

We came up with generic first names, vague job descriptions, and admitted to using a dating app. If pressed for more, we would plead for privacy until we were certain we were getting serious.

I had to play that card first. I had gone over Saturday to help make more room for the attachments Dad bought for the mower. Mom cornered me in the kitchen.

"Tell me about Cassie. What's she like?"

"Her name is Callie, Mom. She's nice, she works at the university hospital. I'm sure April has told you everything already."

"So when do we get to meet her?"

"Damn, Mom. We've been on two dates. We're having fun getting to know each other. We're not even exclusive right now. I like her and I'm not going to screw it up going too fast too soon."

"Is your sister serious about this boy?"

"Daniel, Mom. I think she likes him but I don't know how much. You'd have to ask her about that."

"Tell me about this app your sister said you were using."

Once again, I stuck to our prearranged script, leaving out the nature of some of the questions. Dad walked in during my explanation and threw in a few questions of his own. There was something different about his mood that seemed strange, almost like he was proud.

Mom then gave me a mini lecture on not leading Callie on if I wasn't serious about a relationship. I knew Mom was just being a mother. She worried about our happiness and even though we were adults, she would always be our mother. That didn't make it any less irritating.

April's text after dinner made me laugh out loud. "OMG. Kill me."

Mom volunteered April to help with cleaning up after dinner and did everything but tie her to a chair and torture her for information.

I found out about the interrogation on the following Tuesday, when April showed up unannounced at my apartment. I took Sunday to take care of laundry and cleaning since I had spent all day Saturday helping Dad. April had been radio silent all day Sunday and Monday. I left her alone, I had the feeling she needed space to think.

I was wrong.

This time her knock sounded like she was kicking the door. The minute I cracked it open, she barged in and flopped down on the couch.

"Why aren't you talking to me?" Bark was too gentle a term for her tone.

"Excuse me?"

"I haven't heard anything from you since Saturday. Why?"

"Texts work both ways, you know. You texted me when you got up Saturday morning so I thought I would wait until I knew you were up. I was cleaning and doing laundry Sunday. When you didn't text, I thought maybe you wanted some space to think. So I gave you some. If you had sent anything, I would have answered you."

She sat back, still upset but I think she got my point. "I would have appreciated a 'hey, I'm here if you want to talk'."

"Again, that shit cuts both ways."

"Okay, you made your point. It's time to boyfriend. I'm not happy with Mom." She described in vivid detail Mom's interrogation techniques.

"She's Mom. Apparently they do things like that. Boyfriend?" I sat down next to her and she leaned against me.

"We held hands and hugged, so yeah. She's acting like she thinks my boyfriend is going to take advantage of my innocent nature because I don't have dating experience."

"If I wasn't the one dating you, I'd be worried about the same thing. There are a lot of predators out there. And you're green, not innocent."

"She also said that I couldn't count on you to watch out for me because we won't be able to double-date all the time, your girlfriend won't go for that and it's not fair to you to expect you to babysit me. I am too innocent. Never been kissed, at least for real." I glanced at her out of the corner of my eye but her expression was neutral.

"Under normal circumstances that would be true. We need a new plan. You think the parents would buy our dates had a schedule change, now have to work weekends, so we can only date on Monday, Tuesday, or Wednesday?" I was grasping at straws, throwing out the first idea that came to mind and letting her riff on it.

"Yeah, as long as we don't say that our dates are on the same night. They won't know if you're home or not and I can just come over here and hang out. I like the way you think."

"Desperate times call for desperate thoughts." I had enjoyed both dates and didn't want to give that up any time soon.

"I love a man who can think under pressure." She grabbed my hand and held it while leaning against me. "I'm going to hang out here for a while and then you can send me kicking and screaming back."

We sat for a few minutes, enjoying each other's closeness. I disentangled myself to warm up leftovers and we ate dinner on the couch, watching some romcom on Netflix.

As soon as the movie ended, she got up and pulled me up after her. "I need to get back before she sends a search party."

I walked her down to her car. She unlocked the door, I opened it, and as she stepped forward to get in, she kissed me directly on the lips.

I just stood there, caught completely off guard. "Are you going to close the door or what?" I closed the door silently, too stunned to speak. As she backed out, she puckered up again and blew me another kiss before driving off. She looked extremely pleased with herself.

A couple of minutes later, my phone chirped with her text tone. "3/3, it's official."

I texted back, "Don't text and drive!" I got a rolling eye emoji in return. It did make me smile.

After that, I made it a point to text her every day. She was apparently making it a point to respond promptly. I found the setting where we could change our available dating days and our next date was scheduled for a week from the Tuesday she came over. We went over our cover story a couple of times during the week just to make sure we had it down.

According to April, Mom had eased up on her questioning during the week. That's because she was saving it all for me on Saturday morning. Thursday's dinner had been inquisition free and I kind of expected it.

"What does Cassie do that she has to work nights on the weekend at the hospital? Is she a nurse or something?"

"It's Callie, Mom. She does patient admissions or something administrative like that. People go to the hospital outside of regular business hours."

"What does Daniel do? April said he explained it but it went over her head." That little shit.

"He works for that big insurance company downtown, I think he's a property insurance adjuster or something." I tried to think of something that would sound complicated to me and that was the best I could do. "Trees fall on houses all the time."

"Why is getting information out of you two like pulling teeth?" She was beyond exasperated.

"Because neither one of us has had very good luck with getting dates. We have somebody we're seeing that we like and we don't want to jinx it. For the record, we haven't met their parents, either. We're just taking it slow. We're not trying to hide that they're drug dealers or serial killers." I was patient during my explanation, trying to sell our caution. It seemed to pacify her, at least temporarily, and I would take that.

Thankfully, Mom put her weekly interrogation on hold during dinner, giving me time to update April on the additional details I had to add to our "dates" profiles. April volunteered to clean up and I volunteered to help her. Mom stared at us for a moment or two before thanking us. Dad still seemed to be on a happy streak, so I guessed that whatever was going on at work was good.

"Sorry about that. She hit me with that question the other day and I went completely blank. That was a nice save." April bumped me with her hip as she rinsed dishes and I loaded the dishwasher.

"Thanks. I don't think we're going to be able to do this all the time. She seemed suspicious."

"Well, you never, ever do this until somebody puts a gun to your head. I'd be suspicious."

"Fair enough. What's up with Dad? He's been happy a lot lately." That bothered me for some reason. He wasn't characteristically unhappy as a rule but he was a project manager for a software developer. There was always some catastrophic bug or deadline issue going on.

"Some project at work is doing better than anybody expected. He told Mom there might be a major bonus this year. She wants to go to Vegas if he gets it." She grinned evilly at me and my stomach felt fluttery.

"That would be cool. It's been a few years since they went." COVID had put a damper on a lot of plans. It would give Mom something else to fixate on besides our love lives.

"I hope we get to go, too. We'll have fun." The way she pronounced the word fun did more funny things to my stomach.

We finished loading the dishwasher and washing the pots and pans that were used for dinner. We were standing next to the sink when I succumbed to the urge, slipped my hands around her waist, and kissed her on the lips.

Her arms looped around my neck and she whispered, "About fucking time." Then she kissed me back, lips parted and gently sliding her tongue between my lips. When we came up for air, it was obvious she wasn't wearing a bra, her nipples were poking out more than I had ever noticed before. She moved against me and I realized that I was poking her with something significantly larger and firmer.

"I guess you liked that, too." She slid against me a couple of times and then pulled slightly away.

"Nah, collecting the boyfriend tax. It's a law." I really needed to get my cock pointed somewhere less uncomfortable.

April reached down and gently squeezed my erection. "That's some tax collector you got there, sir." I could feel it leak precum and miraculously become even harder.

I shifted it to a more comfortable position while she watched with curiosity. "Stop that. I need to go out to the living room and I can't do that if you keep playing with it."

"Really? Have you seen these?" She cupped her breasts and lifted them slightly. "I need to go put a cover on them now, thanks to you." They were still out proudly. I really wanted to brush my thumbs against them to see her reaction but kept my hands on her hips instead.

"They have these things you can wear, I think they're called padded bras. You might want to look into that."

She kissed me slowly and purposefully again. "If I start wearing a bra now, they're going to know something's up." That broke both of us up.

April headed upstairs to fix her pokies and I headed to the hall bathroom to fix mine. It didn't take long to blow a huge load into a handful of tissues. I could still taste her on my lips and that was all I needed to get the job done.

She still hadn't come down when I went into the living room and grabbed a spot on the small couch. It was out of Mom's field of vision so I could play with my phone without getting yelled at. Dad was on his work tablet, deeply engrossed in whatever it was he was reading.

When April finally came down, she had changed both her shirt and her shorts. She was also a little red in the cheeks. She arranged herself so that she was leaning into me but could sit upright if Mom happened to turn in our direction. She felt very warm.

"You okay?" I tried to keep my whisper low.

The smile that accompanied her nod spoke volumes. Great, now I was stuck with visions of April masturbating in my head. "Wonderful."

Mom's questions during the commercial breaks were innocuous, centering around making sure we washed everything and put the pots away after we dried them. There were no more dating questions. Dad did his annoying Mom thing by asking questions about her shows while she was trying to watch them, which was actually fun to listen to tonight for some reason.

I spent the next two hours fighting down the urge to put my arm around April and just cuddle while we watched TV. We both had trouble keeping our hands to ourselves, giving in to light touches and caresses when we were sure nobody was looking.

When it was time for me to go home, I helped Mom pick up the den, gave both Mom and Dad their usual hug, and headed toward the door. As usual, April was waiting at the foot of the stairs. "Text me when you get home." She was also highly amused about something.

I did as instructed, after putting away the usual leftovers Mom sent with me. I undressed and got into bed, texting April "Good night."

A minute later, I got a reply text. More accurately, it was a video. April was reclined on her bed, her phone apparently in a stand at the foot, pointed at her midsection. Never taking her eyes off the phone, she slowly slid her left hand up under her shirt and started teasing her nipples. Her right hand snaked down inside her shorts as she spread her legs further so I could see the outline of her hand as she started teasing herself.

"Welcome to the girlfriend experience. Try not to hurt yourself." The huskiness of her voice made me even hornier than I already was. It didn't take her long before she was panting and squirming. Every now and then, a whimper would escape her lips. When her pace picked up a little, I came. I couldn't actually see anything, she never exposed herself, but something told me that she wasn't faking it at all. I was just finishing up shooting into a sock when her head rolled back and she whispered, "Oh, Paulie -" as she shook while her legs clamped together and her toes curled into the sheets. It took her a while to recover enough to stop the camera. I kept a still from that video in my camera roll, face flushed, pupils wide, untamed hair framing her face post orgasm with that amazing smile. That has always been my favorite picture of April.

I used to hate it when she called me "Paulie" because it was usually followed by "Numbnuts", a takeoff on one of the characters from The Sopranos. This time, "Paulie" started making me hard again.

That was the best night's sleep I had had in a very long time. I was also rock hard when I woke up so I set up the phone, sent her video to my tablet, and recorded my own show for her.

It was difficult but I edged until her climax. When I came, it was like I was watching her video for the first time. My load seemed to go everywhere.

Before sending the video, I texted her a note to be careful where she opened it.

I had just gotten out of the shower when April video called me. I sat down on my towel on the edge of the bed.

Her face was flushed and her breathing a little labored. "Bastard."

"What? You tease me, I tease you back. Those are the rules."

"That wasn't fair."

"The fireworks aren't as effective under cover. Besides, you felt me up already so you might as well get a look at it."

"No, calling me 'baby'. I didn't know I liked that. You're not allowed to call me anything else from now on." I wasn't even aware I had done that. Upon further review, I had done it several times.

She looked down at the screen in her hand. "Do you always cum that much?"

"Inspiration had a lot to do with it."

She smiled sweetly at the camera as the sheet slid down slowly, exposing the top of her breasts. "Stay inspired, Paulie." The video call ended before she exposed them completely.

Today was going to be tough to get through. I got myself off once more before I left for my parents. April was nowhere to be seen and didn't show up until just before dinner. She also didn't change clothes when she came back.

I soon knew why. She was at the sink after dinner, rinsing out her water bottle when I came up behind her and hugged her. She thrust her ass back into my crotch as I slid my hands under her shirt. She had on a heavily padded bra. I loved how soft and warm her skin felt and her hair smelled divine.

Just to be mean, I whispered "Hi, baby" in her ear. Her moan was low but it made my cock twitch just the same.

"Hi. If you'll excuse me, I need to take care of something so I can be polite company later."

"What if I want you to suffer?"

"Are you familiar with blue balls? Want some?"

"Hell no."

"Then be a good boyfriend and help me move my dresser."

She wasn't going to have to ask twice. Going up the stairs, she rattled off a list of things she wanted to accomplish before I went home. I could hear Dad laugh in the living room.

Once inside her room, she didn't bother to close the door, we would hear anybody coming up the stairs. We embraced again, kissing slowly and deeply.

Standing in front of her mirror, she lifted her shirt so I could unhook her bra. Lifting it carefully, I saw April's breasts for the first time in all their natural beauty. They were the perfect definition of perfect.

I ran my hands lightly up her sides to cup them and she pushed back into me. I brushed my thumbs over her nipples and she moaned as they became firmer under my fingers.

"Oh, God, that's good." She grabbed my right wrist and slid my hand down her stomach and into the waistband of her pants, under her panties, and my fingers drifted through her pubic hair and into a very warm and damp valley.

I was careful to gently massage her lips and folds with my fingers before approaching her clit. She had leaned forward to brace herself with both hands on the dresser as I rolled and pinched her nipples while gently stroking her clit. Her ass was grinding against my cock just right.

"Oh, Paulie -", and she came, trembling in my arms, her head rocked back against my shoulder as I held her upright. As soon as she could stand on her own, she turned around and undid my belt and pants.

"Girlfriend experience, part two," was all she said before kissing me and slowly spreading all the precum I had leaked around the head of my now achingly erect cock. We continued to kiss as she started slowly stroking.

It was awkward, she had obviously never given anybody a handjob before, but I'm here to tell you she was still amazing. I gave her plenty of warning and she wrapped it in a pair of silk panties and finished me off, gasping for air and fighting to stay on my feet.

I was completely surprised to find our little tryst had lasted less than twenty minutes. We spent the next ninety minutes rearranging her furniture to her satisfaction.

By the time I went back downstairs, we were back to our normal, nonhorny state. I hung out with my parents, complaining that she couldn't decide what she wanted where and that I didn't think we actually moved anything after all. They couldn't have cared less.

She came down, dressed in her usual T-shirt and shorts, and complained that I complained too much and good help was hard to find.

Mom and Dad put up with us for a while and then sent me home with the usual leftovers. April headed upstairs before I was out the door.

She texted me on the way home. "Sorry, didn't want to overdo it."

I put everything away and texted her back. "Good call."

I could still smell her on my fingers and it wasn't long before I was blowing a load into my trusty sock. I slept like a baby after that.

Monday and Tuesday flew by. We texted back and forth frequently, keeping it family oriented. We didn't get any further instructions about our date until just before our scheduled time.

April showed up at exactly seven, letting herself in with what used to be my spare key. She had dressed to go out like we had agreed she should do.

Our instructions arrived simultaneously, a few paragraphs on the usual relationship progression, including the timing of the first kiss, the petting stages, and sex.

At this stage of dating, it was time for a private night in. We ordered a pizza, she opened a bottle of wine I bought for her, and we settled on the couch to watch a couple of movies.

"I told Mom I would probably spend the night with Daniel." She was very nonchalant with that announcement.

"Jesus, April. Now she's really going to want to meet him." I almost choked on my pizza. "A little warning would have been nice."

"I know. I have a plan. We're going to break up tomorrow morning. You're going to have a fight with Callie about being available for me while I get over my break up. We'll continue to hang out and we can do whatever we want when we want."