Finally! A real date!

After classes I went back home to get ready for my date. Turns out the sluttiness of what I was going to wear was relative to what I was going for originally. Basically, if I was going somewhere where an outfit wouldn't really be considered that slutty, I had to amp it up. My original decision was a very short dress with straps and a slit down the side. But then I thought that would probably be fine if I went to a club or something. Instead, I put out some X pasties, a fully seethrough crop top and a pink micro skirt with no panties. Then I slapped on some platform heels.

"Amanda!" I called from the bathroom, doing my makeup. "I need you to change into the outfit I put on the bed!"

"Okay!" She said. She went over to my room and took the dry cleaned outfit I had laid out. "Are you sure about this?" She said while looking at the item. "This is positively modest compared to what you have me wear."

"Yeah, well, I want you to impress Diana. Today act like an actual chauffeur." I grabbed some lip balm and started applying it. "None of this back talk or questioning. We're going to be a real duo. Now put it on."

"Hey if you keep giving me actual outfits to wear, I'll be the best employee ever," She said.

It was freezing when we met outside the math building. That's what I get for dressing this way. Diana was already there, waiting for me. She was dressed like she normally was for class.

"What are you wearing?" She asked me the second I showed up. "That leash is quite a statement."

"Yeah, yeah, I know." I said. "I lost a bet." That seemed to calm her down.

"Now, what do you have planned for me?" She asked.

"Oh, I have a whole night planned!" I said. "Just you wait."

We walked over to the car. Amanda opened the back door. She was wearing an actual chauffeur's outfit this time, one that covered her up. Still no inner shirt, just a blazer and a push up, showing off her cleavage. We both got in and she started to drive to a predetermined location.

"Where are we going?" Diana asked me once we got on the road.

"Chatte excitée," I said, naming the most expensive restaurant in the area.

"Oooo, that's fancy." Diana said. "I don't think I'm dressed for a reservation there." I put my arm on the headrest behind her.

"Oh, I don't have a reservation," I said.

"You don't have a reservation?" She said. "There's no way we're getting in there without one."

"Don't worry," I said. "I bet you I can get us in without a reservation or waiting. If I do, you have to go in your current outfit without worrying about it. Deal?"

"Deal," Diana said.

Of course, miraculously, they had an open spot. I felt so... naked walking into a fine dining establishment dressed like I was. I should've brought multiple outfits. Instead I just chose an outfit that would be appropriately slutty anywhere.

"So, tell me about yourself," Diana said once were seated.

"What is there to say? I like art. I hate engineering. I mostly play dominoes in my free time," I said.

"Dominoes?" Diana laughed. "What are you, 60?" I laughed too.

"Yeah, yeah," I said. "I've heard it all before. I bet you'd love them though. How about you and I go swing by my pal's place on Monday and show you how to play? If you don't love it I promise I won't ever bring it up again. If you do, we'll make it a regular thing."

"You don't have to avoid bringing up what you like just because of me," She said. "But sure."

We had very pleasant conversation for much of the night. Diana was so interesting. She was originally from Long Island, New York but moved out here to the boonies because she wanted it a taste of rural life. I have no idea why anyone would want that. She had traveled on vacation a lot growing up so she knew about all these different places I had only heard of. She was definitely out of my league, but because I promised the date would be great she was eating out of my hand.

I had already used a bet to make it so we got free food before we showed up so that Diana wouldn't think I was cheap. I asked her to wait in the car while I resolved the bill, then slapped a truly gratuitous tip down because hey, I wasn't using the money to pay the restaurant, might as well pay my server.

Once we are done we gave Amanda a break and walked down the street together, looking at the soft light from the lampposts. It was to die for.

"So, are you having a good time?" I asked with my head in the crook of Diana's neck.

"Honestly it's been stellar. You're so kind and the dinner was so amazing." Diana said. She moved get out to get my head off her shoulder and stood up right to look at me in my eyes. "But it'll take more than that to be my best date ever." She said with her hands in mine.

"Well then, why don't we have Amanda take us home?" I said. "I want to show you just how good this date can get."

"Lead the way," Diana said.

I told Amanda to drive home after dropping us off. I didn't really want an audience in my house for the next part. I practically dragged Diana up the stairs I was so giddy.

I was so happy that the slutty condition only kicked in when I was dressed. I had a couple ideas of what it would be like to be slutty while nude and I didn't like any of them.

"Turn around," I told Diana. She complied. "Put your hands on the bed." She did.

I pulled out the brand new strap-on I hadn't even had time to test. I carefully put it on, lining up its protrusion with my entrance. Maybe I should have started with a one-sided one. But still I wanted to see if I truly didn't like penetration or if it was just the wrong person. I lined up the other end of the strap-on with Diana.

"I bet that once I start you'll orgasm on every thrust, and once we're done you'll need like 10 minutes just to have higher brain function return," I said.

"What do I get when you lose?" Diana said playfully.

"If I lose you get to turn this around on me. If I win, you have to truthfully admit that you are a lesbian and I'm the best fuck you've ever had." I said.

"Well it's not going to be hard in meeting my first fuck is my best one," She said.

I was taking aback. I was her first time? I didn't want to make a big deal out of it; I'm not some 50-year-old who actually thinks virginity is a real thing. I was just surprised the girl as hot as her hadn't gotten some during college yet. Then again, I was pretty hot as well.

I finally stuck it in and started thrusting. Immediately I heard the moans. Diana was trembling. After only a couple she lost strength in her arms and collapsed on the bed, face first. I kept going. She was having the night of her life and it was definitely affecting me but I was still far away from my orgasm. So I continued.

I ended up trying a bunch of different things. There was just the jackhammering as quickly as possible, but there was also taking it slow, doing a little curve while I hit it, smacking her behind, a bunch of small changes that I had no idea what effect they had because I had magiced my way into the best sex ever. The vibrations of Diana fucking seizuring on the dildo really did wonders for me. Eventually I found myself get close. I slipped a hand underneath the strap on and started rubbing my clit. Pretty soon after I came. Hard. Once I got one orgasm I felt like I should probably give Diana a break. I slowly pulled out.

"You good?" I leaned over to ask.

"Hummaduma," She stuttered.

"Okay, so no," I said. I grabbed her by the waist and pulled her higher up on the bed. Then I laid down next to her. I cuddled with her while she slowly came to.

"Oh God," She finally said, panting. "I— I- I. Is it like that all the time?"

"It can be," I smirked. "So what do you say, best date ever?"

"One hundred percent." She put a hand on my thigh. "Thank you for having me. Can I stay the night?"

"Well our driver left for the evening so yes," I said. "You don't have anything in the morning?"

"Just my D&D group that doesn't meet 'till 1," She said. God she was hot.

"Well then, wanna get some shuteye?" I asked.

"Totally," She said. And with that I flicked off the lamp on my nightstand and we cuddled until we both fell asleep.

Author's Note: I took a break! I kind of had to. At first it was just I had a busy day but once the imaginary line of deadlines disappeared I decided to chill a little bit more, so I took another day off. This will be more common. My first nine chapters were all written ahead of time with significantly less obligations. Not only are my obligations increasing but now I have to actually write the chapters. I will try to keep up daily but it's very likely that there will be one or two day breaks in between. And eventually I might just stop updating! This story does not have an end in sight so I don't know how long it's going to last. Thank you for your patience.

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