Against All Odds Pt. 01

There was no place we wouldn't fuck. We often went to a bar a couple of blocks away called Detox, get loaded, laugh a lot and then stumble home. On many nights, I was so horny for her that I would drag her into an alley and fuck her hard and quick up against a wall. This was primal, with no goal of making her cum, just urgent hard sex with the danger of being caught.

Melissa and I became almost inseparable. She had to spend time at Cathy's and was vague about her work hours. Whenever I asked her about it, Mel smiled, batted her eyelashes, flashed her beautiful brown eyes and told me not to worry; she would return soon. She texted me constantly when she was gone, and the breaks were needed to complete my work. I was on cloud nine, and there was no doubt I was head over heels in love with this woman. She was all I could think about whenever I was away from her.

I often pondered our age gap and our differences in life experience. Melissa was super streetwise, had tremendous empathy, and a heart of gold for anyone she felt as a friend. On the other hand, from a book-smart perspective, she was young and hadn't graduated High School, and my circle of friends could be intimidating. I was a classic poser intellectual stoner, and since many of my friends were creatives, this trait was shared among us. Nevertheless, everyone loved Mel, and in the end, everyone knew she was special.

She was also oblivious to how enchanting she was, standing there in a black cocktail dress, CMF shoes, a scotch and a cigar while talking Formula One, field dressing a deer, how her football team was doing or deep dive into the latest pot strains or cannabis edibles. Talk about being charismatic and hot all at the same time. Most of my friends had crushes on her. She was a natural salesperson and never knew it. Cathy did, which was one of the main reasons she worked for her. She became many of my male friends' confidants, airing their concerns about relationships. Melissa listened so profoundly; she genuinely cared. The best part for me was even though guys would flirt and even blatantly hit on her, she left no doubt I was still her number one. At least that was when we were together in the city, hanging in my circle of friends. I had yet to meet or hang out with her crew. The friends she had close to where she lived with Cathy. When I was on the road, she would sometimes stay in the loft, but most times, that was when she would return to her place at Cathy's.

I was good with all of this. I had just gotten out of two relationships, one shitty and the other OK. I didn't want to fuck this up, but at the same time, I tried not to have any expectation of where the two of us would get to. We were deeply in love, but when I look back, I realize we kept our feelings to ourselves for fear of creating a conflict. I thought we were exclusive, and most of that came from how she treated me and my deep desire to only be with her. I still always wondered what her life was like away from me at Cathy's store and the house she shared. I would soon find out.

Cathy and Melissa at the Skunky Bud Emporium

A customer had just left after Melissa had closed them on some much-needed paraphernalia to go with their super skunk weed. Cathy loved that "Hayseed' was so good making customers believe it was all their choice. If Melissa was not too stoned or going overboard with the blow, she was a formidable sales maven! Between the two of them, the shop was infamous. Two hotties that knew their shit made coming into the store an exceptional experience. This was especially the case with men. Once was enough in most cases for them to become regular customers. Cathy was voluptuous and had a fantastic rack. She was not runway pretty, but she oozed sensuality. She could pore that on like syrup on hot pancakes. Most of the men that came into the store would be putty in her hands. Then, to have Melissa there, with her runway-worthy legs, perky breasts and Elfish beauty, there was usually a stag line from opening to closing. The girls had a blast playing the game, making the day faster.

When the door closed with customers leaving the store was momentarily empty, Melissa turned to Cathy and said, "I'm in Love, Cathy, head over heels in love."

"What, with the old guy?" Cathy said, knowing full well who she was talking about. Mel had spent most of her time at his loft lately, and Cathy was jealous. She enjoyed dominating the "Hayseed" and pushing her up against the wall in the office and making her squirm, but she really missed having her at home. She loved fucking her boyfriend, knowing Mel was in the next room. Cathy's boyfriend, Colin, was a one-woman guy. He knew the girls liked to play but was adamant when he was there, it was about Cathy and him, no open shit. Cathy was OK with that; Mel and her would never cross that line. This didn't stop Cathy from being over the top loud when Colin was fucking her.

"Yes, Dave! I love him more than anyone in my entire life," said Mel, "I'm terrified to tell him how much," knowing that when they were together, it was apparent what they shared. She just wanted to be with him as much as possible.

"So, is this going to get serious?" said Cathy. "I've been hoping this was just a phase and was waiting for you to switch to a new boyfriend. Colin has a lineup of friends that want to date you, and some of them are freaking hot as fuck." implored Cathy, "I think it's time I met Mr. wonderful, and Colin wants to meet Mr. "Daddy Warbucks," too. "Colin thought he was a new sugar daddy and not a real love interest, so he is super stoked to see what all the fuss was about." Cathy pondered for a minute and was going to suggest Mel make Dave her full-time Sugar Daddy. Still, she knew well enough that Mel needed to separate those dynamics, and it was obvious she was head over heels in love and even suggesting the Sugar Daddy thing would kill her.

"Yeah, I'm getting antsy about that," said Mel, "I think I need to stop seeing my clients. It's getting tricky keeping them happy when Dave is away, and I feel shitty and have no desire to be a 'sugar baby' anymore. The money is great, but I only want to be with Dave."

"Are you going to tell him?" asked Cathy.

"I don't know," said Mel, "I know I should if I want to stay honest, and I want to be with him more and more all the time."

"OK, then it's settled; time to meet Dave," Cathy said emphatically. "When is he back?"

"Friday morning."

"OK, time for a party at our house and to break some hearts," said Cathy. "But only if he passes the test."

"You have to be nice and tell Colin to stop that Daddy Warbuck's shit," said Mel, "Please don't ruin this for me!"

Cathy smiled, but in all this, she just loved Melissa. They had a deep connection, and she was smart enough to know her feelings. She knew Mel had some growing up to do but also wanted her to be happy. From her standpoint, she's never seen Melissa as smitten as she was with this Dave guy. If it ever went south with him, Cathy would be there. Mel had already texted Dave, and he agreed and said he was looking forward to meeting her friends.

"Silly, silly man," Cathy said with a smile as two young guys came in and nervously looked at the two of them. The girls were so hot they had difficulty completing a coherent sentence. Mel helped them but also smiled inside. She was both happy and nervous, letting Dave into her world. She was scared shitless about the Sugar Daddy thing but had already made her mind up. She would tell Dave, and if it didn't blow things up, she would phase those relationships out and tell him how she felt about him. She had almost dried up intimate moments with her clients since they started dating, so they knew something was up. She was a nervous wreck, but the predominant feeling was excitement about being in love with Dave and dreaming of where it could go. He rocked her world sexually and had become her best friend. They shared so much, and she knew it was only scratching the surface. She was indeed in love.

Dave Goes to the Party

I got home early Friday morning from Nashville. I had hoped Melissa would be at the Loft, but she and Cathy were getting ready for the party, so it made sense she stayed there. When I got to the Loft, it became apparent I was not living alone. Melissa's clothing was starting to pile up in the bedroom, and I made a mental note to get one of those free-standing metal things for hanging stuff. There were some dishes in the sink, a coffee cup, plus a bong on the living room table. The bathroom was small, and it was easy to see the accumulated female things. It made me smile.

I made coffee and sat at my desk doing my expense report. A chore I avoided to the point of not doing them. I also wanted to write a quick report for the office. This trip was exceptionally and I did a ton of business. I texted Melissa to tell her I was back in the Loft and couldn't wait to see her and meet her friends tonight. In honesty, I was nervous. This was a big step. I'd heard so much about Cathy and was deeply curious to meet her. I was also worried about being in my thirties, as the party would be mostly young twenty-somethings. No biggie, but I still thought about our age difference.

I got a text from Mel, "Hey babe! I'm glad you're home!" then my phone rang. It was Melissa.

"Hey," I said, "fuck I missed you!"

"Meet too, babe. I can't wait to see you tonight. Sorry, I was not there to jump your bones this morning. You know how much I love it when you get back all horny to see me."

This immediately made me hard, but also, hearing her voice made my heart flutter double time. She told me how excited she was and wanted to know when I was coming to the party. She wanted me there early to meet Cathy and Colin. I told her I had some work to finish and would leave at around six. I asked what to bring, and she replied, "just you and some beer you like babe." Then she said, "Oh, and some of your black hash, Cath and Colin would enjoy that as it's not easy to get."

I showered, manscaped and tried to get my receding hair to work better. I just decided to wear a hat, a clean white T-shirt, my jeans and my fav Doc Martens. I had been growing a Goatee recently, and it was cool. I went downstairs and grimaced as I took the car out of the magic spot. The Loft only had a handful of places to park a car, and once you got one, I tended to leave the car and not drive it. When I returned, I knew I would have to do the street park dance. I had no clue when that would be, as Melissa hadn't said anything. I prepared for the weekend and put the overnight bag in the car.

Cathy and Melissa lived in a suburb very close to the city. It was a rough part of town, but the house was on a nice street, and it felt like a college hang. There was no problem getting parking as I was there early. I had purchased two cases of beer because I had no clue what her friends would like. I knew that a good party should always have enough booze, and I was highly motivated to ensure that happened.

I rang the doorbell, and Melissa opened the door and almost bowled me over. I nearly lost my grip on the cases of beer. A guy ran up and grabbed the cases. He was about the same height as Mel, with a great full head of hair and a wide smile.

"Hey, you must be Daddy Warkbucks. I'm Colin, Cathy's boyfriend. Is this beer all for you?"

"No, it's for the party; you can never have too much booze if you want to have a good party," I said.

Colin just smiled and said, "That's cool, man. Make yourself at home. Mel's been freaking out." He then kind of paused, scrunched his brow and added, "yea, and Cathy wants to meet you too, but don't worry, she can be icy, and you won't know what's coming but don't worry, she's mostly fair. Good luck with Dave ...." With that, he was off to the kitchen, and then Mel threw herself into my arms and planted a huge kiss on me. I almost fell. In the back, I could see a girl with a bodacious body, big curly brown hair and eyes that I swore could see through walls looking right at me. I knew it was Cathy. I blinked, took a gulp, and just told myself to be me - and have fun.

I was early, so not that many people were there yet. When I was introduced to Cathy, I was smitten right away. I don't think she ever knew this, and when I say smitten, I don't mean it sexually. She was just a force to reckon with. She just oozed sexuality, assertiveness and smarts. It was obvious she was fiercely loyal and close to Melissa. I could also tell that Melissa turned her on, but I quickly noticed that it was more like a closeted Dom thing, exploring her bisexual curiosity with a close friend mixed with her kinky need to control things. It was an utterly intoxicating mix, and it was evident that she and Mel played sexually. I didn't know to what extent, but I knew I had no say in this play. In fact, I didn't think they had total control of their dynamic. It was electric and probably driven by some deep stuff for each of them. Two of them in a room together and doing nothing outwardly sexual would make everyone horny. All of this was pondered on a quick subconscious level. The outcome for me was that I was resigned to the fact I had no choice but to trust Cathy. She would have Melissa's best interest at heart, even if that was not hers. I knew that she was tough, flawed, and honest at her core. I liked her immensely.

Melissa was the hottest woman at the party. She was tall and on the skinny side but was wearing a short little black skirt, and her legs went for days. She had on a meshed halter top, perfectly snug to contour her very perky breasts. Her hair was all ringlets and flowing free, and her smile was like a white neon light beaming happiness all around her. It was obvious at least three guys were trying to control themselves and be impressive. Stoned but impressive. It was fun to watch. She flirted perfectly, leaving each of them horny and flustered. One would think I would be jealous, but my recent epiphany about Cathy had instilled in me a pretty hefty reality check. It could only be me; the relationship was still new and unlikely enough, given our age difference; we worked, or we didn't.

I was taking all this in, smoking a hash spliff, and Cathy looked at me and said, "So, you know you have Hayseed all goo-goo-eyed. What makes you so special?"

I blinked and passed the spliff, coughed a bit, looked at her and said, "I have no fucking clue, but I thought maybe you could help me with that."

Cathy laughed, and her eyes quickly pierced me for a split second. She looked over as this super good-looking guy, tall, in shape and with dirty blond dreadlocks, was chatting with Mel. For a split second, I thought I saw him adjust his package on purpose. Cathy interrupted that thought and said, "You know, you are breaking a bunch of hearts here tonight."

I blinked and said, "Well... we both know it could also be mine." Then I looked at Cathy, smiled, and continued, "We both know, don't we?"

"Know what?" Cathy asked.

"She has something special inside, and you and I can see it. We both know she has some life shit ahead of her to realize it," I replied. Knowing this was a bit of the hash speaking but also me being poetically honest. I could tell this was not something Cathy was expecting. She just looked at me and smiled.

"It's hard not to love, isn't it."

"Yup, fucking hard not to love."

We both laughed, and then got into a couple of very tricky discussions about a variety of subjects. I was stoned, Cathy was stoned, and I had difficulty keeping up with her, but it was fun. Then, just before she left to mingle with the growing and much drunker crowd, she got close and whispered in my ear. Her hair tickled me, and I could feel her presence dominating me. It made me shudder.

"You break her heart, and I will kill you!" With that, she walked away, leaving me stunned just standing there. I took a pull on my beer, raised my eyebrows like Spock and thought to myself, I think I just passed the Cathy test.

The party ended up being a lot of fun. Cathy's boyfriend kept calling me "Daddy Warbucks." His friends could not decide whether to be stoned or drunk. They ended up being both. One guy kept falling Mel around like a lost puppy. He was nothing like the other "hot ones," as Cathy would describe them. This guy was shorter than Mel and a little pudgy, but she had flirted with him just being herself. Full sweet smile, fun and listening to everyone. Later, when Mel had me in her bedroom, he kept barging in. We were in complete semi-undress mode, but she kept it super friendly with the guy, asking him to leave us alone. He kept coming, and I eventually chased him out of the room. We had sexy drunk and stoned sex; it was late, and we'd both had some lines of coke. For whatever reason, coke made me super hard, and I could last forever. We tried making as little noise as possible, but I think Melissa wanted to give Cathy some payback.

After passing the Cathy test, it was pretty decided; we had both fallen in love with each other. So the next day, we were in bed, and Melissa looked deep in thought. After telling her I loved her, she said the most fearful words men dread hearing.

"Sweetie, we have to talk."

"OK," I said. "What's up?" This can't be good, I thought. Perhaps some of the 'hot ones' from last night had tempted her, or she snuck away. We had not discussed being exclusive, but it just felt that way.

"I want us to be official," Mel said. "I love you so much it hurts, and I can't imagine being apart."

Holy crap, I thought as my smile hurt my face and my heart skipped three beats trying to catch up with itself.

Then she said, "...but I need to tell you something, and I am terrified to do it."

I thought, OK, she has other boyfriends or another love interest. So, I said, "Look, Mel, I love you, and I mean I love you a lot, so you can tell me anything."

She then looked down and said, "Look, I don't make a lot of money at Cathy's place and over the last couple of years, I have had a steady string of relationships with my "Sugar Daddies."

"Your what?"

"Sugar Daddies, I'm a Sugar Baby; I have relationships with older men in return for ..."

I interrupted, "I know what it is, Mel, I'm just trying to get my head around it."

I was not devastated; instantly, I could see how successful she would be doing this. Her vibe would be perfect. We had never discussed exclusivity, and I had always wondered why she always had money. In the beginning, she was adamant to the point of pride, that we split things as much as possible. I also travelled a lot and trusted her if she wanted to stay at the Loft. I was always trying to be a pretty easygoing guy. The last thing I wanted was for her to feel pressure. My mind was racing; how many Sugar Daddies did she have? Did she have sex with them? Did I get sloppy seconds? Was she going to ask me to be her new Sugar Daddy? That thought gutted me more than her having sex with someone else.

"OK, what does 'official' mean to you?" I asked sheepishly. "Do you want me to be your exclusive Sugar Daddy?"

"Fuck no!" said Melissa, as tears started to form in her eyes. "That's not what I am asking," she said.

I immediately realized that was a shitty thing to say, but my brain was whizzing, and my heart was pounding. I took a deep breath and said, "Look, Mel, I'm sorry I said that. I know I love you too much, and I believe you love me too dearly to even consider that." I paused for a second and asked her, "So, have you been sleeping with just me or me and your Sugar Daddies?" I continued quickly, "I mean, it's really none of my business except that I had this feeling we were kind of official, if not exclusive, but just never discussed it."

Mel sighed and said, "I don't sleep with all my clients. It's complicated, but intimacy is part of it, just not love. Initially, I fell for you hard, Dave, and being with my clients was fucking me up. So, I slowly pulled the plug on being intimate but continued going on "dates" with them. Mostly when you were away....and even at the beginning, I never gave you sloppy seconds; I just couldn't do that."