As I was driving to Cassandra's work to pick her up at the end of her shift for our date, I got a text message. I hit the button on the screen in the car to let a slightly robotic, female voice read it to me.
"Did you at least bring a condom?"
It was from mom. She was worried I might get horny and mess things up on the first date. I sighed and ignored it. Another message a few seconds later, and I hit the button again for the voice to read it loud, expecting it to be mom again.
"Go around the back. Cass."
I pulled into the parking lot by the 7eleven where she worked extra, not yet living fully on her photographer business, and drove slowly around the building. Cassandra was just locking up the back door and gave me a wave. She was wearing a similar outfit as the one I had seen her in before, with worn jeans and a white blouse with the sleeves rolled up. Her piercings, nose and ears, reflected the light from a lamp above the door, and the big tattoo on left her arm was halfway visible. I pulled up, turned the car off and got out to say 'hi'.
"Hi, I'm Nick."
"Hey good-looking," she smiled and gave me a hug, much to my surprise. "I've been looking forward to this all evening. Let's go!"
We got in the car, making small-talk and getting to know each other. She directed us to a bar close by that she knew would have good music, nice drinks and an overall good vibe. She wasn't wrong, but it was a bit more crowded than I had hoped. After failing to have a conversation because of how loud the place was, we gave up and hit the dance floor instead. The DJ mixed upbeat songs with slow tempo love songs and I got to embrace Cass in a cheek-to-cheek dance before long. She looked nice and smelled nice.
"Want to kiss me?" she asked, speaking close to my ear to make sure I heard her.
I nodded and we kissed, swaying to the music. Everyone and everything but her faded away and our embrace tightened. Her lips were soft and gentle. I felt her part her lips against mine and her tongue sliding ever so softly against my lower lip. I parted my lips too and our tongues started a sensual dance on their own. To my surprise, she also had a pierced tongue, with a metallic stud adding an extra level of excitement for me. I wondered how a blowjob from her would feel like and suddenly my pants started to feel a bit small.
"You're really hot," she almost shouted just as the song ended and everyone around us heard her loud and clear.
Cass turned two shades of red and looked very embarrassed. I just smiled and brought her to the bar for some refreshments. We spent another hour or so dancing and drinking. I held back on the alcohol but had a really good time nonetheless.
Afterwards, on our way back to the car, Cass looked really happy and very tired. I had my arm around her and it felt great. Everything about her felt just right. I drove her home while we had a fun, easy-going conversation about her being a photographer and what her goals in life were. I told her about my studies and my own aspirations to be an engineer.
"This is me, right over here." She guided me to her apartment building. "I had a really great time tonight. There's just one thing..."
"What?" I asked, and I pulled up to the curve.
"You gotta tell me what your purchase was for... I don't want find out ten dates in that you have some perfect relationship with some rich ass girlfriend and you're just playing me."
I could understand her worries. We did meet as I bought condoms and lube from her. I decided to roll with my new life-motto and just tell her the first thing that came to mind, the truth.
"Actually, that was for my mom. My stepmom. She was very busy and asked me to get it for her."
Cassandra turned to look at me, trying to see if I was joking, being ironic or just crazy. She seemed to think I was ironic and got upset.
"If you can't answer, I guess we're done."
She started to get out of the car and I had to think fast.
"I swear it's true! I can call her up and she'll confirm it!"
Cassandra turned to me again, more surprised than mad. She crossed her arms and tilted her head.
"Alright."
Fuck, I thought. How was I supposed to call up Hilda, ask her to confirm the purchase and not have her spill the fact that she and I were sexual partners. I took my phone out and dialed her number. The phone was connected to the car and the speakers filled the car with the sound from my phone.
"Yes?" Hilda answered sleepily.
"It's me," I told her. "Sorry to wake you up. I just wanted to check if you needed anything from the store. I'm in here now and it's just about to close for the night. Maybe more condoms or lube or something?"
"What?" Hilda said, still too sleepy to really hear me.
"I'm at the store. Do you need any more condoms or lube?" I tried again, cutting to the point.
"Uhm..."
There was a long pause, and I was super-nervous how she would reply.
"Nah, we're good for now. Maybe in a week or so... Thanks for picking that up for me, though."
"Alright, thanks!"
I hung up quickly and took a deep breath, hoping that Hilda's confirmation was enough for Cassandra to not cut ties with me. She gave me a surprised look and a slow nod.
"I'll be damned. Your mom's pretty open about that stuff, huh?"
"That's an understatement," I nodded. "Satisfied that I'm not trying to cheat?"
"I guess," she uncrossed her arms and relaxed a bit. "But things just went from possibly bad to possibly weird."
"I know, I know," I nodded. "I promise, I'm not some asshole just trying to score a side-piece. I really like you, actually."
"Actually?" she laughed. "Like that would be surprising? Well, fuck you too."
I laughed too and the tension in the air evaporated. She gave me a final kiss before leaving me with a promise to text me the next day. I drove home, wondering how Hilda managed to give such a good answer to my question.
I got a text message from her on the way home.
"What was that about? Did I answer okay?"
"Yes! Thx" I managed to reply.
I was home shortly after and Hilda was waiting for me in the kitchen, sipping on a cup of tea. I told her all the details of the date and how the call saved me from getting dumped before the relationship even had a chance to start. In her comfortable robe, no makeup and just sipping a cup of tea, she was just my mom again and I enjoyed that old side of her. We talked for a good while, and I took a shower before going to bed.
I was sitting on the patio the next morning eating my breakfast in the morning sun when Hilda came out to join me.
"So," she smiled, "Susan's expecting you in about an hour."
"Yeah, I know. Got any final advice?"
"Well, I think Susan's eager to catch up on some unfulfilled fantasies that she's been having for a long time. Her husband, Mike, has never really satisfied her to a meaningful degree, sexually."
She paused, sipping on some coffee.
"She told me once," Hilda continued, "that her boyfriend in college treated her like shit, like he owned her. She absolutely loved it in the bedroom, but not outside of it, of course. Mike is kind of the opposite, always nice to her. She's been missing that bad boy in the sack for almost twenty years."
"Alright, so I should be shitty to her?"
"Not like physically or mentally abusive. Just kind of... take what you want. Let her know what a big, dominant dick is good for."
"I'll try," I replied, worried I would screw up. "Should I use like, dirty words and stuff too?"
"Oh, most definitely! Call her names, like slut or cheating whore and stuff like that."
We sat quite for a bit before she continued.
"You should let her give you a safe-word when you get there. Something that, if she says that word, will let you know it's enough and you need to stop whatever you're doing. Okay?"
"Yes, of course. A safe-word. Smart."
"That way, you will also know that if she doesn't say it, she's into whatever you're doing. And one more thing..."
"What?"
"Don't feel bad about Mike. He's been fucking his secretary for years. He told your father once when they were drinking, and he told me. Susan probably knows, but she hasn't said anything so don't mention it, okay?"
"Fuck Susan, don't feel bad. Got it!"
About an hour later, I parked in front of the Johnson's residence and headed up the stairs to their huge front door. I was a bit nervous but my semi-hard dick gave me confidence and I rang the door bell. A few seconds passed before I heard footsteps approaching inside. Heels on tiled floor. The door opened and Susan appeared.
She was wearing a robe and open toed high heels. Her hair was in a tight pony tail high on her head. Quite heavy makeup, making her look very sexy and ready for action. Multiple shades of eye-shadow with bold colors and dramatic blending. Well-defined and filled-in eyebrows, with a sharp and precise shape. Generous application of blush and bronzer, adding color and dimension to her face. Ruby red lips with a defined lip liner to create a sharp outline of her luscious lips.
"Hi Nick, come on in!" She opened the door more and let me inside. "Sorry about the cover up robe, I wanted to make sure it was you."
She closed the door behind me and let her robe fall off her shoulders to the floor. She had a black, half-cup, wet look corset and matching string panties on underneath the robe. The half-cups only supported the lower third of her large, soft tits. Her nipples for sticking straight out in the open. I could understand why she didn't want to open the door in that outfit. My jaw dropped and she gave me a big, proud smile. I would do my very best to give this woman what she wanted, I thought.
"Is this all for me?" I asked, trying to play it cool.
"Yes, sir," she smiled.
Sir, I thought. I'd never been called sir in my life until then. My cock hardened and I agreed with it, I liked her calling me sir. I also remembered Hilda's teachings about always communicating clearly.
"I like that. I really like that. You look like the incarnation of the best erotic fantasy a man could ever have."
"Thank you, sir," she grinned and slid her hands over her tits, teasing her nipples to harden even more. "I feel like that too... I feel so sexy and naughty."
"Now, before we do anything," I said with a more serious tone, "is there anything you don't like? Do you have some sort of safe-word or something?"
She moved her weight from one foot to the other and put her hands on her curvy hips while thinking for a moment.
