Against All Odds Pt. 01

She started to cry again as I was still looked stunned. She could tell I was bouncing all this around in my head. Finally, she stopped, grabbed my face, looked deep into my eyes, and said, "I love you with all my heart; I only want to be with you and only you!"

I pondered this for a bit - knew I was deeply in love with her and asked her a very pragmatic question. "OK, I will guess you are quitting the Sugar Baby business?"

"I made that decision weeks ago, but I'm still extracting myself. Some of my Sugar Daddies were infatuated with me, and I didn't want to hurt anyone more than I had to. So, I was super honest with them and told them I have met someone and fallen hard."

She then paused and continued, "I need to find another job. The hours at Cathy's are not enough to cover rent and living." She could tell I had not said anything about "us." She was correct; there was still some conflict in my head, but through all of that, nothing changed how I felt for her.

"OK, I still need some time to wrap my head around this as I'm a bit jealous at the least, but the thought of losing you terrifies me," I said. I then made up my mind, at least in concept. "So, let's do it then, move in with me at the Loft. Official, full-time girlfriend."

She started crying more, but it was strange as it was half happy and half sad, or so it seemed. She stopped and looked at me, "I would love to, but please, we can't ever make this like you are my sugar daddy."

I laughed - and said, "How about just exclusive boyfriend then unless, of course, you have a kinky "daddy thing" you have not told me about."

Melissa just jumped on me, hugging me and kissing me. It was an obvious yes. We got up, and Mel was bopping around. There were many hung-over people, and Cathy was up but not ready for happy Hayseed that early in the afternoon. They were off and talked for a while. She needed to give Cathy time to find another roommate, and Cathy was double-grilling Mel about moving in with me. I found out much later that Cathy was happy for her but kept giving me the evil eye, saying, "You better take care of her and not break her heart." There was also darkness behind her eyes. She was also in Love with Melissa and knew this would limit their time together.

I had an internal sweat session. What was I thinking, I thought. I just asked a 21-year-old, ten years younger than me, to move into my Loft. I knew people thought she was too young. Yet, we had both navigated this already, and there was no denying we were way beyond lust. I guess I was just scared shitless that I was going to eventually get my heart broken. I had never loved anyone, even close to how I felt about Mel. I was cursing my shit luck that the "one" might just be a young woman. One thing is sure: if I ran for the hills at this juncture, I would regret it for the rest of my life. Fuck it I thought. I am going to love her fiercely and enjoy every possible second. She was just that wonderful to be with, and this was way beyond the fantastic sex or how fucking hot she was. I would still love this woman if she was old and fat. I sighed inside my head. I was in it to win it. I would let Love drive the bus. I smiled and opened a morning beer to celebrate.

Melissa wound down her relationships with her Sugar Daddies. She laughed as I had so many questions as this scenario, at least in my head, allowed me to ask these questions. I think there was some Hotwife kink here, but I had no clue what that was at that time. All in all, I couldn't get enough of Melissa. She officially moved into the Loft, and we got along fantastically. It was like what we were already doing. It was just official.

We upgraded my crap car for an OK car that Mel could take to work. The Loft was my office, so having a car was a weird luxury. We loved picking out that silver sedan from the tiny used car place down the street. I was on cloud nine. My job was going exceptionally well, business was great, and I was having the time of my life with Melissa. I had always been a sexual guy. Adventurous to a point, horny all the time, and had a deep kink giving pleasure. I was fundamentally self-centered, but sexually, it was the opposite. I was completely capable of receiving, but ecstasy was always elevated when my partner was left tingling in release and pleasure contentment. I was also a voyeur, and watching pleasure was part of that kink.

We got into a pretty fun routine. Mel worked part-time at the weed store and was looking for other work. We usually had a mid-week party night, and then weekends were full-tilt fun in the city. I was drinking more, and it seemed coke was also becoming a regular thing instead of occasionally. I'd had some bad experiences in the past, especially in a very toxic relationship. So, even though I was a happy drunk, I was deeply wary of my penchant for addictive behavior. We did a lot of coke together, but I could tell Mel was hiding her personal stash from me.

Our dealer was my gay landlord and part of our loft party crew. Jesse, or JJ as we called her, loved Mel. They would often go out when I was away. I knew Melissa was a classic "Fem Treat," Jesse loved having her with her. I had some concerns, but not really. At this point, our fun was just off the hook. We played hard and worked hard. We also started taking road trips in the silver sedan. I got to meet her parents. They lived in a small town on a lake, and on that first day, her cousin was there, and we actually knew each other. I passed that test as well. Obviously, her parents could tell we were in Love, and they were happy for Mel.

Melissa's Other Job

It was Monday morning the week before the party at Cathy's. I was at Dave's loft, and I was still in bed. I could hear Dave on the phone doing his thing in the studio. Music played softly, and the old wooden walls sounded muffled and musty. I, on the other hand, was all warm and glowing. We had spent an epic weekend together.

I remembered coming down on Friday afternoon, and since I had a key, I let myself in. Dave was at his desk, but in a flash, he swiveled in his chair, launched himself and had me wrapped in his arms, twirling me around with a massive smile.

"Fuck I missed you!" he said.

I hugged him back and got horny quick. He then gave a super sensual long kiss. I could feel his passion as he tried to get as close as two people could while standing up. We just fit together so well, and his cock was hard pressing right against my pussy. I was instantly wet.

After the kiss I was breathless, "I missed you too, babe, but I was here Monday if you don't recall."

Usually, I would take him right to bed, but I'd recently been with a client, so I was trying to stall somehow.

He was one of my longest and most regular Sugar Daddies. I'd spent Thursday night and this morning with him. He had taken me to a formal event. Cocktail dress, dinner out, then an evening with me on his arm. I knew I would have a conversation with Joe about ending our arrangement. I was so in love with Dave I knew I had to tell him about how I made money. Dave and I had never talked about being exclusive, but as much as I thought "maybe" he was seeing other women, I also "felt" he was only with me. That made me glow inside. I was so in love it almost hurt. Fuck I thought. I was such a slut. I was already starting to limit my time with my clients and trying not to be intimate with them. Some were not that serious, so I had already cut ties. For the others, I was delaying, trying to figure my shit out. The income was not insignificant, and I knew I would need to find a second job. Cathy was not busy enough to have me full-time, and I wanted to be closer to Dave's loft.

My client, Joe, was a very successful Asian businessman, and he had a thing for young, leggy brunettes. He was not very tall, but he wanted me to wear heels whenever we went out. I towered over him, but that turned him on. He was nice to me, lavished me with gifts and some fabulous nights on the town. He was cute, and sex with him was easy. He seemed to be hard all the time. The wind blew, and he had an erection, but it was also really small, so you just didn't notice. When we did have sex, or I gave him a blow job, he would cum quickly. Yet, always after that, he was very sensual with me. He would massage me, wash me with a soft, warm towel and just bask in being with me in bed. He never wanted seconds. He was a gentleman and, by far, my least demanding client. He was kind of kinky, too, but in strange ways, like my feet, or especially my legs in stockings with high heels or reaching up to kiss me. He liked it when I was dominant. One time, I thought he would like the whole cuckold thing. Telling him about my other men and how much bigger their cocks were or how they fucked me for hours, but it did nothing for him. It was all about worshipping me, and he was extremely comfortable with his small cock and quick sex. I think he felt that showing love was everything but sex. My pleasure at dinner or a night out was more important than my sexual pleasure. He enjoyed having me on his arm and the occasional intimate moment. I was sad to have to end the relationship.

The night before, at the gala event, I was off to the side by myself while Joe was getting us more champagne. Then, this hot guy sauntered up and started hitting on me. Quite well, I must say. He was tall and lean and had dark hair and dark eyes with a very noticeable bulge in his dress pants. I was immediately amused. I was with Joe, which meant I was 100% exclusive to that. As the guy was posing like a porn peacock, Joe walked up with two full champaign flutes. The guy was totally dismissive of Joe. He was trying to swat him away like a bothersome fly while intently trying to get me to notice his obvious arousal. I was amused even though he was one of the types I liked, but Joe was surprisingly masterful in these moments.

Without being phased at all, Joe stood right up in the guy's face. He was only at shoulder height. The differences were startling, but Joe's confident presence made the guy hesitate. Then Joe simply said, "Stephen, I'm sure you can find a dozen women here tonight that would want what you're obviously selling, but your boss and I think it would be pretty stupid if you pissed me off." Joe did not flinch and continued, "In fact, your boss thought it would be a good idea for us to introduce ourselves." The guy was still off balance and looked like he was bristling for a showdown, but then Joe continued, "Hello Stephen, I am Joe Wong, and this is my date, Melissa." He slid in next to me and handed me two full champagne flutes while putting his left arm around me. Stephen's bulge disappeared, and his face went pale so quickly that I couldn't stop letting a little giggle escape my lips. He almost missed seeing Joe's outstretched hand.

The guy looked mortified and said, "Oh shit, Mr. Wong, so nice to meet you," while quickly completing the handshake. "I..er..did not realize she was your date... I'm eh .. sorry to have interrupted." Joe was just smiling, and I knew his little cock was hard as a rock, even though no one would notice. It always surprised me how much a confident man can be an intense turn-on. Here was this small man, five foot five at best, barely weighing a hundred forty-five, soaking wet, dressing down a stud. It was a complete turn-on. "It was a pleasure meeting you, Stephen," as Joe obviously dismissed him. He made an exit, with his proverbial tail between his legs and I could see Joe tip his glass across the room to an older man that was trying not to laugh. Joe just smiled while Stephen came up to the older man. The old man was laughing at him. They both went off to the bar. Joe knew Vlad would turn this into a teaching moment.

"Melissa, would you be okay if we left now? I am pretty excited, and I would enjoy some time alone with you."

Mel cringed inside a bit, but after what just happened, it would be cruel to tell him now. I will talk to him later, she thought.

"Oh yes, let's get out of here, Joe." she paused and whispered to Joe, "That was hot, you know!" He just smiled and looked down and grabbed his stiff cock and winked at me, and giggled.

Joe and I made the rounds, making sure to politely check in with all the important people. It was apparent Joe was a well-respected and feared man. I had always wondered what he did for real. He said real-estate development, but something told me he had other irons in the fire. Even though I was just twenty-one, I had been around the street enough to know when to ask nothing, hear nothing and most of all, say nothing. Joe was beaming the whole time, and I knew he was still hard. The last people we said goodbye to were Vladimir Tkachenko and his nephew, that hot guy Stephen. As Joe walked up, you could see Stephen get pale again and look down at his feet. I was smiling, and Vlad was beaming.

"Joe, it was so nice to see you here," said Vlad. "Melissa, you're beautiful as always. I hope my nephew Stephen did not insult you or say anything inappropriate." I looked at Joe and winked.

I quickly replied, "No, he was a total gentleman. He just wanted to show me something and ask how I thought the party was." I smiled at him as he blushed. The whole scene was turning me on, and my nipples were rock hard and totally visible, jutting out of my little black dress. Joe and Vlad just looked at each other and started laughing. We said our goodbyes, and on the way out, I turned to Joe and asked him, "What the fuck was that all about?"

Joe smiled and grabbed me to hold me close. I could feel his cock against my thigh, and it was so hard it was actually showing. He looked up at me and said, "Vlad told his nephew he saw you checking him out and that he should go talk to you."

I gasped and said, "You know I wouldn't do that," to which Joe quickly said, "Yes, yes, I know that Melissa, and so does Vlad. He told me how stupid his nephew was and that he wanted to teach him a lesson." Never hit on a woman when you don't know why she is there and who she may be with. You observe first. He continued, "We both watched as he grabbed his cock and sauntered over to you. We chuckled together as we knew you would be amused. Vlad also knows I get off dominating a room with guys like his nephew."

Vlad told Joe, "He's young, hung and dumb, Joe, but he's, my nephew. I thought you and I could have some fun with him." Joe was Vlad's most significant business partner. As much as Vlad was rich and a typical alpha male, also with an infamous cock, Joe was the silent assassin and indeed had big dick energy. Their respect for each other was deep.

"The rest, you got to witness, Mel," said Joe. "It made me very excited."

We left as I thought that young, hung, and dumb thing had its merits, but not tonight. I also needed to be honest with Joe. He would expect nothing less.

When we got back to his place, he just attacked me. It was so not Joe. He was strong for his size, and by the time we made it to the bedroom, most of our clothes were off except my stockings and heels. His little cock was so hard, it looked threatening. He picked me up, threw me on the bed and ravaged me. He knew I loved breast play, but tonight, it was all about his urgency. He went down on me with a vengeance. I had planned not to have sex with him tonight, but I could tell this was special for him. He was always good at pussy eating, and I even felt that tingle. Nothing like what Dave did, but I tingled. The whole night was making me tingle. I was wondering for a split second if Dave had fixed my inability to have an orgasm as I really liked what Joe was doing, but then he stopped. He got up. His cock was pointing straight up, almost flat against his belly. It was super red, like it was on fire. He grabbed one of his expensive Japanese condoms, and tonight, it looked like it was a tight fit. He looked at me as he pushed my long legs up to my shoulders. I still had the heels on. Joe licked the shoes and caressed my legs. He then pulled his super hard cock down from his abdomen, pointed it at my pussy and rammed it in as hard as he could. Then Joe proceeded to fuck me hard and fast.

It was intoxicating how turned on he was, and again, I had the tingle. His thrusts were short and quick, and he was not slipping out. Usually, I like to be on top so I can make sure he stays all the way in. Not this night. Little Joe was big Joe right now, and he was starting to sweat, huff, puff and fuck the shit out of me. He even had a bit of Dave's bump and grind going, and the tingle kept coming. He started to go even faster. It was a bit uncomfortable and distracted me. Then, with one mighty thrust, Joe roared as his cock exploded. I could feel his little cock twitch and jump, hot and throbbing. I was taken aback and added my best fake orgasm to the mix. I was screaming, "Fuck me, Joe, Fuck me". He just kept cumming, and then he thrust once and froze. For a split second, I thought he was having a heart attack, but then he exhaled and collapsed on top of me. My legs were still in the air with this little man resting his head on my shoulder, panting and heaving. It was very erotic.

There was a no-kissing thing for me and my clients, but knowing this would be the end. I grabbed his head and kissed him deeply. This took him by surprise. I simply looked him in the eyes and said, "That was wonderful, Joe," to which he said, "I'm sorry, Melissa, I don't know what came over me." He caught his breath and got up and told me he was going to take a shower. I knew he liked to do that solo unless he asked me to join him. I took off my high heels and my stocking, then put on a silk robe. He always liked to have some scotch neat after sex, so I went to the living room to set that up. He had expensive taste, and I enjoyed his collection. As I chose a bottle, it was now, or never I thought. I packed my things and laid out my clothes in case he asked me to leave.

Joe and I sat down in the living room. The showers seem to cool his tempo and sexual urgency. This was normal Joe. I took a shower after him, and then I joined him in the living room, wearing my silk robe and my hair wrapped in a towel. Joe handed me my scotch on the rocks. We sat and sipped our drinks. He was a very perceptive man, so he knew something was up with me.

"Melissa, what's on your mind?"

He was never a man of many words, and I respected this, so the truth was all I had. So I put my drink down, took his hands and looked him in the eyes. I said, "Joe, I've met someone," I paused as he kept looking at me and continued, "And I think it's becoming pretty serious."

He looked at me and smiled. He reached in, hugged me, and simply said, "I'm happy for you, Melissa."

I could tell he knew this meant the end of our relationship. We had always discussed that emotion was something we avoided, but I could see tears welling up in his eyes. He was still smiling, but I could tell he had feelings for me. He got up and refilled our scotch, and he asked me about Dave. He wanted to make sure he was not an asshole. It was hard to keep my evident enthusiasm for Dave muted, but Joe took it all in stride. In the end, he knew this day was coming. Usually, he told me, it was never an issue with his "girls," as he called them, but this time it was different for him. He got quiet and politely asked me, "Melissa, can we spend one more night together?" He was blushing as he did this, and I didn't have the heart to say no.

My response was quick: "Joe, you've always been kind and respectful of me; of course, I will."

We finished our drinks and went back to bed, and at no time did he ask me about sex with Dave. He just melted into my arm and made super slow love to me. It was sweet and soft, and nothing was urgent about it. As usual, he did not last that long and after, he fell asleep with a smile on his face. In the morning, we woke up and he made love to me again. Quite well, I must say, and it was obvious he was letting his emotion show, and that was always something I keyed in on. He lasted much longer than usual, and his eventual orgasm was loud. I added another one of the best fakes I could muster.