Date with Tanner and isolating Becky

This was the weirdest double date I'd been on. Let's start with my ex-boyfriend, Tanner, on my left. My tiny boy-toy. At 5'5” and only an inch taller than me, what he lacked in height he made up for in good looks and confidence. What else was good... he liked to recreational with me. I was the financier, blowing some inheritance, but I needed his connections to buy the stuff. When the funds ran out, I dumped him to date someone that could be a provider. He was acting heartbroken, but I suspected he just missed free .

His best quality: he was turned on when I fucked other men, which I did often. That's how I met the man sitting across from me, John. The opposite of Tanner, but best friends. They were both 28. He was about 6'5”, tall, and black. A medical doctor, highly successful, great with women, so much class. And great in bed with the biggest cock I'd ever had the pleasure of having inside my body. I was hoping so much to get laid by him tonight. I'd been in a threesome with these two men before. John made me come like crazy, and Tanner liked to go second, enjoying the submissive “barely there” feeling inside my loose pussy. I only agreed to this date as a possible reconciliation with Tanner to get a shot at sex with John again.

The problem with my plan was the bitch sitting across from me. The half-breed Indian, tall and gorgeous and very judgmental. She looked down on me, and not just literally. It killed me that John was into her. He was a player and never settled, but I could tell this one had his heart, even though they could never be together. I'd overheard some stuff on our last visit at his house. She was to enter an arranged marriage, and she and John didn't even have sex. She didn't have sex at all. The stuck-up 23 year-old, highly successful tech executive was still a virgin! They dated, I guess you could call it that, but John still had sex with other women, and Becky dated but didn't go all the way. Weird. But I could tell now he was into her, and there's no way his virgin princess would allow him to fuck me while she was around. The bitch was cock-blocking me.

The thing I hated the most about her was that I was attracted to her. I'd only been with a few women, but this one held my appeal. I'd shared a harmless kiss with her at John's house while I was naked and she was dressed right before she ran off to a date with another man. I was still pissed about that. She could look down on me already, because she was over 6 feet tall also, and so buff, like she stayed in the gym all the time. Her tits were a lot bigger than mine, and her captivating green eyes from whichever parent was the white one were so exotic with her darker Indian features. She was so hot without even trying. Tonight she sported an amazing ass hidden behind a skater skirt that was a size too big, and no style in her perfect, glossy black hair. Full lips, but no makeup. That plump lower lip that I wanted to kiss and bite. Dorky glasses. A generous rack that sagged just enough in her bra to let me know she was blessed naturally. God damn it, I fucking hated her. She was so sexy without even trying.

She wouldn't even look at me. I know why. After I dumped Tanner, the leggy slut went to his apartment and sucked his dick to make him feel better, and John had encouraged it! Apparently the giantess nymph was horny as hell and did oral all the time while refusing to spread her legs. Stupid. I lost my cherry at 13 and had been with countless men since. I couldn't relate to this fake chastity bullshit, and therefore I looked down on her for it. Plus she blew him so well he bragged about it to me and John.

So she gave him world-class head. As a virgin! I guess her pussy was too special for any man, yet she could wrap her filthy lips around my man's cock and raise the bar for me. Bitch probably did anal too and pretended she was still a “virgin”. I hated most that her fake-innocence game was working on John. He seemed to value her more because she didn't put out, and I hated that. She had the one thing I could never have: innocence. I wanted so bad to take that away from her, to spoil her purity, to pop her cherry.

You probably would surmise from the above, correctly, that I had some growing up to do. The woman sitting across from me had tons of desirable traits. I just couldn't see past the superficial, because I was so shallow myself. Let me admit, I was far from perfect. I was 19 and perhaps a bit immature. I dropped out of college due to the influx of inheritance money. I ate decent and worked out a little, and the habit wasn't totally out of control yet, so I had pretty much a perfect body due to genetics. Perky, medium sized breasts, padding or firm in all the right places, and a pretty face. I never thought about tomorrow, that was me.

“What are you looking at?” Becky asked John. We'd had a few drinks. This was a good bar that was convenient to our places. I followed her gaze and smiled. The bitch was jealous. John was scoping out a sandy blonde at the bar. He didn't look away when she accosted him, and I loved him for it. He was all man, and she didn't own him. “That's Tess Jansen,” Becky continued. “I see her in the gym sometimes. She's famous in Crossfit. Third place at the Games, came out of nowhere.”

The girl was very fit. She had bare shoulders, and they were impressive. Her midriff was exposed, and I could see the muscles popping out of her tight jeans. I was young and reckless, but I could read people. Navigating the illegal trade and lots of sketchy sex partners required these skills to survive. Becky was used to John dating around, but I could tell that this Tess person was getting under her skin. They occupied the same niche. She was fit like Becky, but even more so. She was younger and probably on a fake ID to get in the bar, just like me. She looked innocent, like she'd just come out of bible study and changed into slightly tighter jeans for a date.

“You don't have a chance. She's too young, and she loves Jesus. It's on her Instagram,” Becky said, confirming most of what I had deduced already.

“Oh, he's got a chance for sure,” I said, fanning the flames of her jealousy. Becky shot me an irritated look, which I ignored. Fuck off, bitch. “And she's all alone at the bar, waiting to be noticed.”

“I'm going to say hi,” John said and left to go talk to Tess. He came back a few minutes later. Apparently Ms. Jansen was waiting for a date, and sure enough, said date arrived soon after.

We had two more drinks. I waited, but nobody proposed that we bounce somewhere for sex. Without the possibility of sex with John, there was no reason to stay here with Tanner. I might as well go to the home of the rich guy waiting for me that none of these people knew about. Then John bid farewell to Becky and went to the bar! Tess' date was gone, and he was going to try to close. I had to laugh. Becky didn't say anything, but she looked annoyed. When Tanner asked if I wanted to leave with him, I said no. He got annoyed and left in a hussy. Suddenly I was alone with Becky. I took a hard look at her. The virgin was nipping out, still looking sexy as hell without trying, and clearly wasn't sure what to do next. My pussy tingled at the possibilities.

“You guys sure have a weird relationship,” I said.

“Just friends,” Becky said.

I laughed. “Whatever. He has feelings for you, I can tell.” Becky looked at me and smiled. Build up trust, then take advantage and seduce her. “But that won't stop him from sleeping with your gym buddy tonight,” I added with an evil smirk.

Becky scoffed, then recovered. “He does his thing, and I do mine. What are you guys doing now?”

“Tanner left. I'm getting an Uber.”

Becky and I walked out together, and I plotted how best to persuade her to continue the night with me. We had already kissed once, and I knew she was at least curious. Plus she had nothing to do now, because her non-boyfriend was trying to score with another chick. She paused right outside the door. “Becky,” I started, clasping her hand in mine and smiling up at her, “Would you give me a ride home?”

She waited, then glanced down at my hand. I leaned up and stood on my toes. She actually bent down, knowing what was coming. Our lips met, just for a peck. It was a decisive moment, and she reacted perfectly. She disliked me as much as I disliked her, but there was a physical attraction. Well, I was attracted. She was either attracted, just curious, or some combination. We were in public, although maybe only a few people noticed the kiss. I squeezed her hand and smiled. “Please? I want the company.”

“Um, okay. Sure. Just a ride home,” she added warily, and waited for my nod. We compared addresses and realized I was out of her way, but she didn't seem to care. I climbed into her surprisingly large diesel pickup, which was totally hot that she had that by the way, and we left.

Five minutes in, and that large, vibrating engine was already stirring up my loins and making me horny. I broke the ice by sharing that with Becky.

“I don't mind it either,” she laughed.

After a minute of silence, I said, “You don't like me.”

“Huh?”

I had caught her by surprise with my bluntness. “It's okay,” I laughed. “Tanner is John's best friend. I get it.” I went on to tell Becky about how Tanner had pretty much mooched off of me for the last year until my inheritance ran out. Becky was a career woman climbing her way to the top. I hoped she could relate to a woman wanting to cut off dead weight. “He's a good guy, but I had to do it.”

Becky nodded. I didn't have her respect yet maybe, but she was beginning to see my perspective. God I hated having to impress her and justify myself to her so she'd sleep with me. But I was up for the challenge.

My hand settled on Becky's thigh, and she didn't protest as I rubbed above her knee, just peeling back the edge of her skater skirt. “I'm jealous of these long legs,” I said.

“Thank you,” she replied. “Turn here? Downtown?”

“Yes. I think you're beautiful, Becky. I like that you are so tall and fit.” Becky smiled, unsure of where I was going with this. “You have beautiful eyes and skin. I think whatever mix of races you are has mashed up perfectly. Nobody has your look. Or these sexy, strong legs,” I added.

“Wow, thank you so much, Rory.”

I then told her about Omar. He was a rich man of Arab descent. More grown up than Tanner, in his early thirties. After a full battery of STD testing that he insisted on and paid for, I had spent the last few weekends with him, giving him whatever he wanted sexually in exchange for a great party life and the necessary recreational that were now a part of my life. “I know it's not an arrangement you'd go for, but he's very respectful, and we have a great time in bed.”

I was expecting her to mock me, but Becky gave an exasperated sigh. “Who am I to criticize? I have no clue what I'm doing with John. We can't be together, but we can't stand being apart...”

Her voice trailed off. I offered no comment, since I didn't want her to know I knew more than she thought I knew. She put her hand on mine on her thigh and smiled. She was finding common ground, and that was a good sign. We both had strange situations with men.

“Holy shit, he lives here?” Becky asked. We pulled up to one of the high-rise buildings downtown. I directed Becky into the parking garage beneath the building. And suddenly we were all alone, parked in a dimly lit garage. There was an awkward moment where neither of us went to open a door. I moved my hand further up her thigh, only a few inches from her crotch now. I could feel the straps of a garter belt, and I tried to imagine what the tall goddess looked like in her underwear. I damn sure was going to find out.

“Is that a garter? Nice,” I said. “I know you didn't expect to be here tonight, but, well...”

She did not object to my touch, and I leaned towards her. Becky leaned into my kiss, and I had about three seconds of perfect contact with her soft, moist lips. When our lips parted with the lewd kissing sound, she answered. “I thought I'd be...”

She paused, and I answered for her. “Uh huh, what you thought was he'd not be fucking that Crossfit chick. Good for him. My gain.” I went in for another kiss when she smiled. This one lasted longer, and it was amazing. I waited for her to take the next step.

When her mouth opened to deepen the kiss, I backed off and chuckled. You want more? Earn it. “Becky, come up for a drink. I'm so hot for you right now. You didn't get all dressed up for nothing did you?” I teased. I snapped the strap on her garter playfully. That is what I was referring to, not her lame outer clothes.

“Okay,” she answered immediately with a grin.

I was expecting a rejection or a little more indecision from her. I knew this seduction was a long shot. But Becky was not acting at all like a timid virgin. We took the elevator all the way to the penthouse. Omar owned the whole floor, so I had to use a keycard just to activate the button in the elevator. When we entered, I knew she was impressed. There was a large panoramic window giving an incredible view of the city. He kept the place immaculate and modern in taste.