Sugar Journals: Jessy & Elias

This is the second story in the Sugar Journals series. Every story is a stand-alone work. All characters are over 18. Please leave feedback and vote. I hope you enjoy the story.

***

"You should really consider this, Jessy."

I put away my phone and took off my earbuds when I heard my roommate Cindy speak, but didn't exactly hear what she was saying.

"What?" I asked.

She turned to me, and from the screen of her computer, I could see she was at that site again.

"Come on, you know. There are some cute guys looking for transgender girls to be their Sugarbabes."

Cindy had really gotten into this sugar dating thing a couple of months ago, and after a few more or less successful dates, she had finally found some guy who had started to support her in exchange for companionship and regular access to her pussy. They had only visited some nightclubs and stuff like that, but she seemed to like the guy, and he was generous to her.

Ever since, she had been trying to get me to join the site as well, since there seemed to be men looking for girls like me.

"They are just looking for the experience. Someone to fulfill their fetish, and I don't want to be anyone's fetish." I had told her that several times, but she kept insisting that the guys on that site were looking for more than just sex. That might be true for cis girls, but in my case, I just wasn't as convinced.

I didn't have a problem with sex. I loved it, even though I wasn't experienced. My problem was whether the relationship, or whatever one would call these arrangements, was just about them fucking me.

I was sure I would enjoy being a companion for a handsome man and even go to bed with him if there was mutual infatuation in the air, and I would be able to better my financial situation. But just sex? No. That would be too close to being a prostitute.

"I don't think they want to take someone like me on a holiday or parties where they could be seen with a transgender girl, and I don't want to be anyone's fuckhole for one night."

Cindy turned to me, her gaze mortified, and silently protesting my rude words. She was clearly upset. She had had two dates where the guy had dumped her right after the sex, and my words, even when not directed at her, must have hit a sore spot in her.

"I didn't mean it like that, I'm sorry." I rose and went to her. My thoughts were quick, and my mouth often quicker; that was partly because I was used to all types of nasty comments, and I almost always was quick in my nasty comebacks.

"I'm truly sorry. I sometimes speak without thinking." I hugged her. She was my best friend, and I didn't want her to be angry with me.

"Now show me what you have found." I gave in to her eagerness to show me her latest finds and cheer her up. Her mood improved immediately.

"Take a look at him... and him," she started to show me pictures of guys that she thought were a match for me.

"No, no, no..." I kept repeating as Cindy scrolled through the profiles. Some of the guys didn't have any pics and didn't have any information except that they were looking for a trans woman with a big cock. That told me enough, and I discarded them immediately.

"Wait! Wait. Go back. No, the one before. That." One profile had caught my eye, or to be more specific, the picture.

It was the only one where the man wore a suit. His face didn't show, but still the picture gave me a warm feeling. It was taken in front of a sunset on some expensive-looking skyscraper balcony, probably somewhere in Asia.

"Click the profile," I said to Cindy, who smiled with satisfaction.

I was thrilled to notice that this man had invested in his profile text. Cindy read it to me aloud.

"Seeking a vibrant and engaging companion to share life's experiences. As a 36-year-old investor deeply committed to trans rights advocacy and a proud supporter of related organizations, I find immense fulfillment in both my professional and philanthropic pursuits. I'm looking for a transgender woman interested in joining me for various events, from cultural outings to social gatherings. While connection and shared experiences are paramount, I want to be clear that companionship comes before sex. If you are a dynamic individual with a zest for life and a genuine spirit, I would be delighted to connect.

"Wow, that sounds good," Cindy said when she had read the whole thing. I had to admit, it was the first profile where the picture and the text had made an impression on me, and believe me, I had gone through several in these past two months.

"It must be a fake profile, or if it is not, every trans girl on this site wants him. Besides, I'm probably too young for him." I noticed I was trying to convince myself more than Cindy.

"But you like his profile?"

"Yeah, I guess so."

"So, why not send him a message? It won't cost you anything."

I was skeptical. Still, I had to admit that even though I had let Cindy believe I wasn't interested in finding a Sugardaddy, the thought of finding one had crossed my mind more often these days. I was struggling with student loans and money. Navigating life without my family's support due to the expenses associated with my transition, and all the things I wanted to have for myself, had drained my account.

"I'm not sure I want to create a profile there."

"You don't need to. I can send him a message; we can just attach your photo to it." She was excited.

"Please, Jessy. Do this for me."

"I don't understand why this is so important to you."

"Maybe because I have paid the last two rents, when you have used your last dollars to do your nails, and besides, I want you to have some fun too."

She was right. Cindy had paid my half of the rent, and I had invested my money in trivial things, but still, I hesitated.

"Fine. Send him a message. He won't answer anyway."

"We'll see about that," Cindy said and started writing to him. After a few minutes, she showed me a picture where we were together and told me that she would attach the pic to the message.

"Whatever," I said, and jumped back on the bed.

***

Studies and exams kept me busy the next week. I was a freshman at Vassar College in Poughkeepsie, New York, studying cognitive sciences, which I found intriguing as I was navigating my own journey of self-discovery. I had also picked up a couple of Film Studies courses, which we shared with Cindy, since I loved storytelling and visual expression.

Cindy kept checking her messages on the site every few hours just to find out that the fantasy man hadn't responded to her message. I was keeping up my 'I told you so' face, but inside I was a bit disappointed as well. Maybe deep down, I wanted to have someone who would take care of me.

I was just leaving campus on Wednesday when I heard Cindy yelling after me.

"Jessy! Wait! You got a response from him."

I turned to look and saw Cindy running towards me with a wide grin on her face, holding on to her phone.

"Weren't you supposed to be in class?" I asked because at first, I didn't realize what the hell she was talking about.

"Yeah, but this couldn't wait. Look at this. His name is Elias, and he wants to meet you." She opened the Sugarbabe site and read the message to me.

"Hi Jessy, I am sorry about the delay in my response. I have been in Europe for a few days on business, and I have not had the time to check my messages here. I liked your picture and introduction, and I would be happy if we could get to know each other. I'm going to be in New York for the next two weeks, so I hope you find the time to meet me. Elias."

"Oh, he is so polite, isn't he? And in Europe for business? He has to be rich." Cindy sighed out loud. I had to admit he sounded like a polite and smart man.

"So, what now?" I asked, knowing very well that I would need to decide if I truly wanted to meet him. Cindy looked at me like I was a moron.

"What do you mean, what now? Now you answer him and arrange a date with him." She typed an answer to him and gave my phone number to Elias.

He called me that same evening, and I must admit that the good feeling his profile and message had given me became stronger when we talked on the phone. We talked for almost an hour, and it was surprisingly easy to talk to him; we seemed to have a lot of common ground on many things. He invited me to meet him on Friday evening at the local wine bar. I have to admit I was excited, nervous, but excited.

***

The wine bar was already full of people when Cindy dropped me off in front of it. I felt like my pimp had hauled me to meet an important client, and I might have mentioned that to her.

"Fuck you, Jessy," she laughed as I climbed out of the car trying to smooth down the dress she had practically forced upon me -- a simple black number that somehow managed to feel both elegant and a little too revealing. I wasn't used to wearing anything like this, but Cindy said that if I wanted to be Elias's Sugarbabe, I needed to show him I could dress elegantly. She was right, of course.

When I entered the bar, I scanned the room with butterflies in my stomach. Elias had said he'd be wearing a dark blue blazer. Then I saw him. He was sitting at a corner table, a glass of red wine in front of him, and he looked even more handsome than I had imagined. I was relieved. He stood as I approached, smiling warmly.

"Jessy? It's lovely to meet you." He rose to greet me. His voice was pleasant, not very masculine, but I liked it. He extended his hand, and the grip was firm but gentle.

"Elias, hi." I think my voice sounded just like I felt. Uncertain of what I was doing. He gestured to the empty chair opposite him.

"Please, have a seat. Can I order you a drink?"

"A glass of white wine, please," I replied, feeling my initial nervousness ease slightly under his warm gaze.

As we waited for the drinks, an expectant silence fell between us. He didn't stare or make me feel nervous, which I appreciated. When the waiter returned with my wine, he raised his glass.

"To new acquaintances," he said, looking into my eyes.

"To new acquaintances," I replied, taking a hefty sip from my glass.

The conversation flowed surprisingly smoothly. He told me about his work in the field of green energy innovations and investments, and his passion for furthering social justice and trans rights. He even mentioned the Anchor Community, an organization I had been associated with when I started my transition. He wasn't married and didn't have children, and despite his commitment to his work, he desired companionship, and that was the reason he had been exploring the possibility of a sugar relationship.

"So you have been on these dates before? Or is this even a date?" I asked.

He smiled at my question. "I don't know if this is a date. Let's call this a first meeting between possible friends, but yes, I have met a couple of girls before you." I was glad that he seemed to be plain-spoken.

"I guess you haven't found what you have been looking for since we are here?" That was way too obvious, I thought right after the words had left my lips.

"Can I be honest?"

"Please, I would be offended if you weren't."

"The truth is, a lot of the girls on the site seem to present themselves as a bit, how would I say it, different than they are in reality. I don't want to sound like I'm all about looks, because I'm not, but I think anyone who says that looks have no meaning is lying. And also, some of them were a bit pushy. Don't get me wrong, I'm all pro-intimacy, but not right away. There needs to be mutual attraction before anything could happen."

His words felt too good to be true, but I tried not to show too much excitement. I knew very well that most girls, Cindy included, edited their photos heavily, something I had never understood.

Then I told him about my studies and quickly found out that we shared a common interest in film. He asked a lot of questions, and to my surprise, he truly listened to my responses. I soon found myself relaxing in his company, which was a new experience for me. I had feared that our age difference would have been more obvious, but it wasn't.

After about an hour, the conversation shifted slightly. Elias leaned back in his chair, his expression became more serious.

"Jessy," he began, "as you know, the nature of our meeting is a bit unusual. I want to be transparent about my intentions and also want to understand yours."

I nodded, and I could feel my heart start pounding. This was the part I had been curious and apprehensive about.

"Like I mentioned in my profile, I am seeking companionship and shared experiences," he continued. "That remains my priority. I genuinely enjoy connecting with interesting people that I am attracted to."

I interrupted him rudely. Me and my big mouth, I thought, but said it anyway.

"You are attracted to me?" I smiled shyly.

"Isn't it obvious?"

"I don't know. You are hard to read."

"Well, let me be clear then. You are one of the most attractive girls I have ever seen, and I would be happy to have you as my companion."

Wow, that was straight talk, I thought, and couldn't help but blush a bit.

"Thank you. I don't think anyone has ever said anything like that to me."

"Okay, now that we've got that out of the way, I would like to hear your thoughts."

I took another sip of my wine and gathered my thoughts. I was glad that he hadn't led with the financial aspect of the arrangement, but I had to bring that subject up.

"Thank you for being so upfront, Elias," I replied. "For me, the idea of companionship and shared experiences sounds good, and it would definitely be fun to share something like that with you, but I'm at a point in my life where I'm juggling studies and trying to manage my transition independently, and I need to ask about the other part of this arrangement."

I had to try to read his expression before I continued.

"I wish this could help me with the financial stress, but not make everything feel like... just a business deal."

He paused, obviously processing my words. "I also understand that there's an implicit understanding of... support. Fortunately, I am in the position to offer financial assistance to someone whose company I enjoy. This is something I would be happy to discuss openly, if you are comfortable."

Fuck, he knew how to speak and was quick-witted.

He leaned forward slightly, lowering his voice, after all, we were at a bar.

"What are your thoughts on what that support might look like? Are you thinking more in terms of covering specific expenses, or something more regular?" He asked a straight question and deserved a straight answer.

"Honestly, I haven't thought this far yet. The idea of regular support would be incredibly helpful with things like rent and student loans. But I also like the idea of being able to experience things, like going to a concert or a nice dinner, without constantly worrying about the cost."

"When and if you are with me, I will of course take care of all the expenses. What comes for the other things, I find them reasonable also. Like I said that I'm financially in a position where I can offer you the things you mentioned."

His gaze was reassuring, and I trusted him more all the time.

"What would you say if I offered you a monthly allowance to help with your regular expenses, and then also cover any costs for specific outings we might enjoy together? Would that feel comfortable for you?"

I looked at him in amazement. I hadn't expected anything this generous, and it must have been written all over my face.

"If I'm reading you correctly, you would be satisfied with this arrangement?"

"Yes, that's more than generous. I don't know what to say." I gathered my thoughts for a moment.

"What about... are you waiting for me to..." I didn't have the courage to finish my thoughts.

This was unbelievable. I was usually too straightforward, but in front of him, I felt like I had lost the ability to say things directly. Fortunately, he understood what I was referring to.

"You mean if I expect sex from you in return for the support?"

I nodded and looked at him expectantly.

"Let me say it like this: I hope that our relationship evolves so that we both want to experience that level of intimacy together."

I smiled at him. "I like the way you put it. It's not that I don't like sex, but I'm not very experienced, and I wouldn't feel comfortable knowing that I have to do it for the money. But I also want you to know I'm not at all against it, if... like you said... we both want it."

I must have been all red by now. I could feel the blood flowing in my face.

"I understand completely. We will see if it comes to that. No pressure, right?"

"Right."

We talked for half an hour more before he had to go. An important meeting on Saturday morning. We agreed that he would call me and we would make arrangements for our first proper date. Before we departed, he kissed me softly, and I have to admit it felt really good.

***

When I got back to our apartment, Cindy was waiting for me in the kitchen. Before I even had time to take my clothes off, she was all over me with questions flying.

"How was it? He was amazing, right? You plan to see him again?" I waited for her to let out some of that steam that seemed to have built up inside her.

"I think you have been more nervous than I," I laughed at her.

"Don't tease me. You are important to me, Jessy. I just want to know that everything went well." She was such a sweet-hearted person. I hugged her.

"It went really well. Thank you for taking care of me. I liked him a lot, and he said that he's attracted to me. He kissed me also."

"Really? That's great. So, you are going to see him again."

"I guess so. He said he will call me next week."

"Wow, what about the... You know... the financial part?"

When I explained to her what Elias had said to me, she was dumbfounded.

"I can't believe it. That's just... Jessy... That's just crazy."

"I thought so too, but he genuinely seems to want this."

We ended up talking late into the night about what Elias might suggest to me when he would call, and I have to admit I had gotten excited about all of this.

***

He called me on Monday. I was just cleaning up the kitchen after we had spent the weekend messing the apartment up with Cindy.

"Hi, gorgeous," he started and immediately made me smile.

"Are you free on Friday again?"

"For you, of course."

"I was thinking that we might go to this fundraiser at Hudson Valley. They sent me an invitation to their annual event a while ago since I have at some point supported their Preservation Society. I had already declined, but my other planned engagement was cancelled, so I thought, why not go there and ask you to join me."

"A fundraiser? I've never been into one. What's it like there?"

"Quite boring actually, but there is good food, people to meet, and of course me." He laughed lightly at his words. "I thought it might be a good way for us to get to know each other better and explore if this is something you would enjoy doing with me on a more permanent basis."

He had clearly thought this through. I hesitated for a moment, and he must have guessed what I was thinking about.

"It is just a few hours, and I'll return you to your home before you know it."

Okay, so no sleeping together, but I didn't want my response to sound like it was a relief to me. I liked Elias a lot, but I needed more time to clear my thoughts about us going physical.

"That's not what I was thinking," I lied smoothly, "I am only concerned that I don't have anything to wear for such an occasion."

"That's no problem. I'll give your name to one of my associates at Bergdorf Goodman. You can go there, and they will provide you with everything you need."

I almost dropped my phone when I heard him say the boutique's name.

"Oh, okay... that's so generous of you. Thank you, Elias. I would be happy to go with you."

When Cindy got back home, and I told him where Elias had offered to take me, she was exhilarated.

"Where is it held exactly?" she asked.

"I don't know, he talked about some old mansion overlooking the Hudson River."

"A fancy party in an old mansion? That actually sounds kind of cool."

"I don't know. I like the idea, but there are probably a lot of uptight people there. I don't know how I will fit in all of that."

"Don't worry. He will be there with you. He wouldn't have asked if he wasn't sure that it's a good place to keep your first official date."

Cindy was probably right, and I trusted Elias, but still, I was nervous.

***

Thursday, right after we had finished our Film course lecture, we headed for Bergdorf Goodman. I had asked Cindy to join me.

When we entered the revolving doors, I took her hand. The garments the mannequins were draped in were breathtakingly beautiful, but I could almost hear them shouting that I wouldn't be able to afford anything fancy here.

"Wow," Cindy breathed, "This is... something else."

"Let's ask for Lena," I whispered to her, and we headed for the counter. Elias had said to ask for her, and that she would know what I would need. A nice-looking lady in her thirties was at the counter when I asked if Lena was working today, and she immediately pointed to another woman organizing the shoe shelves.

"Hi, I'm Jessy," I said when I approached her, and she started smiling.

"Nice to meet you, Jessy. I'm Lena. Elias called me earlier this week and said you would be coming. Please come with me." She guided us to this larger fitting room at the back of the store.

For the next hour or so, she kept bringing me different dresses and shoes to try on. We were having a blast with Cindy since this was a surreal experience for us to have a personal shopping assistant to look after our needs. Elias had told Lena about the event, and she knew what type of outfits to bring.

"Have you noticed there are no price tags on these clothes?" Cindy whispered when Nora left the room for the tenth time, and I was trying on my fifth outfit.

"Yeah, I did notice... maybe I should ask, just in case. I don't think I can afford to buy even the zipper on this dress."

When Nora came back with another outfit and a pair of shoes, I asked her. "We were wondering how much these dresses cost... because." A friendly smile appeared on her face, and she stopped me.

"Don't worry. Elias will take care of the bill. He gave specific instructions to give you anything you need."

Cindy started to giggle, and I nudged her with my elbow.

"That's very kind of him, thank you." I looked at Cindy, who still couldn't believe what Nora had said.

We ended up choosing a sophisticated white silk blouse and colorful wide-leg trousers. At first, I thought it would be too casual, but Lena assured me that a young woman like me could wear something like this. I didn't ever see the price tags, but when I bought shoes to match and a purse to go with the outfit, I was sure that the sum was substantial.

***

Thursday went by quickly since we had a few super interesting lectures at school, but still, my thoughts were mostly elsewhere. I couldn't stop thinking about Elias and our date on Friday. I was afraid of how people would react to me at that fundraiser, even when I was with Elias.

Cindy tried to convince me not to think too much and trust him, since he would have much more to lose if my being transgender turned out to be a problem for someone. After she had assured me multiple times that everything was going to be okay, I still had to try on the outfit several times, because I still wasn't sure it would be fancy enough.

Friday was hell. I left school early, and I was close to throwing up. I even thought about calling Elias and cancelling the whole thing. If Cindy hadn't been there, I wouldn't have gone at all. Because Cindy was a smart girl, she had bought a wine bottle for us, and when I drank a couple of glasses while preparing, listening to Cindy's final instructions, everything seemed to calm down inside me.

We were looking from the kitchen window when Elias would arrive. He was supposed to pick me up at six. When the clock struck one minute to six, Cindy's mind exploded.

"I can't fucking believe this. This is like a Cinde-fucking-rella fairytale or something," she said when his limo, driven by a chauffeur, pulled in front of our apartment building."

"I'm taking a shitty Uber to my next date with my Sugardaddy and you get picked up by a limo. I want to trade, Jessy," she pleaded with me.

"I think you would need to grow a pair of you know what to get him," I laughed.

Suddenly, my confidence, which I had been close to throwing up earlier, shot through the roof. I hugged her goodbye while she was trying to convince me to ask if Elias would have a friend interested in a cis girl.

***

The mansion where the fundraiser was held was amazing. A three-storey old building right on the banks of the Hudson River. When we pulled up in front of the mansion, I couldn't believe where he had brought me. I wasn't used to anything like this. The limo driver opened the door for me, and when I saw Elias extending his hand and smiling affirmingly, my pulse went up.

"Ready?"

I nodded, but my eyes were glued to the huge stone building. It felt like stepping onto a movie set.

"I'm nervous, Elias," I admitted and squeezed his hand.

"Don't be. I won't leave your side, and believe me when I say, everyone here is wonderful people."

When we were walking towards the entrance, I suddenly felt super aware of the situation, and I held his hand even tighter. I was afraid of how people would react to me. When we got inside, some of the guests turned to look at us, greeting Elias, and I felt panic rising its head again. The fact that he seemed totally relaxed holding my hand in front of everybody eased my pulse a bit.

We moved slowly through this huge hall, past displays of handbags that looked like they belonged in a museum and jewelry that sparkled so much it almost hurt my eyes. Everything felt so expensive and important. The only thing that I felt didn't belong was me.

He took me to meet this older woman and introduced us.

"Eleanor, this is Jessy," he said, keeping his hand on my back.

"Jessy, this is Eleanor Ainsworth, a pillar of the Hudson Valley community and one of the most dedicated supporters of the Society."

Eleanor had amazing silver hair and a kind smile. She made me feel welcome.

"It's lovely to meet you, my dear," she said, her eyes looking right at me.

"I've already wondered when Elias will find a woman in his life." Her gaze was warm, and it actually made me feel a little less like I didn't belong. I liked the way she talked. Elias glanced at me, and I smiled. Eleanor wouldn't probably even know what a Sugarbabe was.

"That's a beautiful outfit, dear. That style looks so elegant on you."

"Thank you, Mrs. Ainsworth," I managed, feeling a little flush of warmth on my cheeks.

As the night went on, I started to breathe a little easier. Elias was really good at making sure I wasn't just standing there awkwardly. He got me a fancy drink with a little umbrella, pointed out these old photos on the walls and told me a bit about them, and even gave me a little smile sometimes during the really long speeches.

Dinner was at this huge round table with tons of flowers and candles. I ended up talking to this younger couple who worked with kids for the Society. They were actually really nice and asked me about college and what I thought of the Hudson Valley. For the first time all night, I felt like I was just talking to normal people.

Later, when the orchestra started playing this really pretty waltz, Elias turned to me.

"Would you care to dance?"

I hesitated. I've never really done proper dancing before. But the way he looked at me, all gentle and encouraging, and the music was so pretty, I just nodded. As we moved across the shiny floor, with all the soft light from the chandeliers swirling around us and the other couples gliding by, I felt this weird sense of calm.

When I looked up at Elias, his eyes were soft. It wasn't just the Sugardaddy thing at that moment. It felt like just us, sharing something special in this amazing place.

When he pulled me close, I whispered to him, "Elias, I really can't dance," but he just smiled.

"Just follow my lead," he said affirmingly.

I pressed myself against him, and he led in the rhythm of the music. At first, it felt like everyone's eyes were on us, but when I looked around, nobody was looking.

"Don't worry about them. Just concentrate on us," Elias whispered to me, and I concentrated on feeling him close. I have to admit it felt good being close to him. During the second waltz, I dared to look him in the eyes, and he made me blush. I hadn't really been this romantic with any other man before.

"You know Jessy," he started, leaning toward me, lowering his voice. "I would really like to kiss you."

My heart jumped a bit, but when he returned his eyes to mine again, I kissed him. First, gently, but when the kiss went on longer, I surrendered to him completely. I knew this wasn't the proper place to make out wildly, but if we had been alone, who knows where it would have led?

I got aroused. I didn't get hard or anything like that, but just aroused. Elias, on the other hand, did get hard. I felt his cock pressing against me and I liked it. I was so happy that I made him horny and not just horny, but I felt he wanted me in every way.

We danced a few more pieces before Elias led me to Eleanor again, and we got to say our thanks for the excellent evening.

When we got back to his limo, we started making out in the back seat. He took me to his lap and we kissed. His hands traced the curves of my body, and the touch was electrifying. I felt his erection pressing against my crotch, and I would have liked to touch it. Take him in my hand and just feel him out, but then he popped the question, and I froze.

"Would you like to come to my place tonight, Jessy?"

I don't know what happened when he asked the question. I wanted him, but still I froze, and even though I was usually so ready with my words, I couldn't get even a single word out. Because I didn't answer anything, he continued.

"It's okay. You are not ready," he said calmly, and before I knew it, the limo stopped in front of my apartment, and the driver opened the door for me.

"I had such a wonderful time with you tonight. Thank you," he said, pressing a kiss to my cheek.

"Thank you." It was the single phrase I was able to say before the door closed.

***

As I watched him driving away, I knew I had made a mistake. Fuck, why was I so unsure of myself? I had wanted him so much.

"Thank you? What the fuck, Jessy." I said to myself out loud.

His touch and kisses had felt so amazing, and I had turned him down. I dragged myself upstairs to our empty apartment. Cindy had gone to have fun with her Sugardaddy and wouldn't be back until morning.

I went to shower to clear my mind, and all I could think about were his lips against mine, and soon I noticed I was getting aroused again. I didn't usually masturbate a lot, but after I got out of the shower I went to my bed and started to fondle my cock slowly. All the time, imagining Elias naked next to me. I had felt his hard cock against me when we danced and kissed, now I was ready to let him have me, but it was too late.

I reached for my nightstand and took my dildo and some lube. I slid the dildo over my rosebud, before pushing it inside, imagining it was Elias who was entering me with his hard cock. I moaned out loud.

With my other hand I stroked my cock that was getting hard. God, how I wanted him here now. I pushed the dildo all the way into my ass and clicked the vibration on. I didn't need anything else. My penis started to push out liquid to my stomach as I sighed in orgasm.

I fell asleep blaming myself.

I woke up around noon when Cindy came back home, still a little bit drunk. When I explained to her what had happened, she practically told me I was an idiot.

"You turned him down? The few guys you have brought here to fuck you have all left you in tears and now when you have the chance to spend a night with a man who adores you... You do what? Tell me again, please."

"I just couldn't make myself say yes." I tried to defend myself.

"Call him! Call him now and explain and apologize," she yelled at me and headed for the shower.

I tried calling Elias, but he didn't answer. I left him a message on his voicemail, and he called me back that same evening. He was on his way to the airport.

"Hi, thank you for calling me. Listen... I want to apologize for my behavior. I don't know what went into me, I guess I panic a little when you..." He stopped me before I had a chance to explain myself any further.

"It's okay, gorgeous. You don't need to apologize. It wasn't a good place for a first date, I didn't think it through. I rushed things."

"No, no... It was perfect, Elias and you were perfect, but I just... You know, when you dropped me off, I wanted to call you and ask you to come back."

He thought for a minute, but then said, "What would you say if we make the second date a bit more private? Just the two of us. I'm on my way to Asia and won't be back until the end of the week, but maybe we could have our date then?"

"I would love that... wait, what? You really want to see me again."

"Jessy, I can't wait to see you again."

The way he said it almost brought tears to my eyes. "Really? You don't know how happy that makes me, Elias."

"So it's a date then? I will call you when I know more about my schedule, but don't make any plans for the weekend."

"I won't... I'm all yours and I mean it this time."

When we ended the call, I was all smiles. I hadn't screwed up everything and I promised myself to leave all my insecurities at home when we would see each other the next time.

I didn't hear from him until Friday. I had been waiting for his call every day, and when he finally reached out, I nearly felt angry for making me wait. But then it hit me--I wasn't his girlfriend; I was just a Sugarbabe. We agreed that I would come to his apartment on Saturday evening for dinner and a private date between just the two of us.

***

When the taxi stopped in front of this modern skyscraper that pierced the Manhattan skyline on the Upper East Side, the nerve-wrecking feeling that I didn't belong hit me again. The doorman let me in after I had told him where I was going and guided me to a private elevator. Imagine that, fucking private elevator, I had never heard those even existed.

Stepping off the elevator into Elias's penthouse was like entering another world, a serene bubble high above Manhattan. The first thing that hit me was the view -- an absolutely jaw-dropping panorama through walls of glass. I didn't even hear when Elias greeted me.

"You okay, Jessy?"

"Oh, yes. I'm sorry. The place is just so... so... I don't know... surreal," I said as he took my coat.

Elias laughed. "Yeah, it's a bit too much, but in my line of work, I need to keep up appearances."

Then he hugged me, and the good feeling he had given me a week ago returned immediately. We kissed softly. He took my hand and showed me the apartment.

Elias showed me his office, a surprisingly calm space considering the deals he orchestrated from there, and it had that same inspiring view. The terrace was a real showstopper. As I was standing out there, so high above the city's relentless noise, I felt like I was removed from it all. Being up there felt like I had my own private perspective on the world.

We moved to the spacious living area that was perfect for conversation, then to the dining area where Elias had already set the table for us. The dining table had been placed against an incredible backdrop. The kitchen was a masterpiece on its own, built from steel and stone, and felt less like a place to cook and more like a piece of art.

"Did you do the cooking?"

"Yes, I like to cook, and I thought this occasion required a personal touch."

He still had a way with words. "I like the way your mind works," I replied, smiling at him.

Elias had prepared a wonderful dinner, and he served white wine with it. We talked about everything, and he never mentioned anything about our last date and the misunderstanding. He had the skill to make me relax, and I truly enjoyed his company.

When we had cleared the dishes from the table together, I knew I didn't want to wait any longer. I took his hand and kissed him right there in the kitchen. He pulled me to his arms and pressed me against the table. When our tongues touched and his hand was caressing my face, it felt right to let everything happen.

When he started to nibble my neck, the most sensitive part of me, I moaned and I got excited immediately. Because of the hormone treatment it wasn't as easy for me to get an erection anymore, that's why I couldn't believe it when I felt my cock stiffen just from the kisses.

"Don't stop," I sighed in his ear and pulled him closer.

I felt his hard cock pressing against my own and I lowered my hand, gently feeling out his hardness. I don't remember ever wanting someone so much.

"I want you, Elias." I moaned as he ate my neck. "Take me to your bed."

He led me to his bedroom, and we practically ripped each other's clothes off. When he was trying to open his trousers, I kneeled before him and pulled his pants down. I didn't want to waste any more time getting his bare erection in my hands and mouth.

When his cock sprang free I admired it for a while. It was adorable, like a twin of my own, maybe only a tad longer. Smooth, silky shaft felt so good in my hand, and I wanted to taste him.

"You have a beautiful cock, Daddy," I said with an aroused voice. Cindy had told me to call him Daddy, and it turned me on.

"I have dreamed of this moment ever since I saw you at the wine bar, babe."

"Dreaming about me... stroking you?"

"No, about us... making love."

Fuck, again he said just the right words. I didn't answer, instead, I kissed the tip of his cock and guided him into my mouth. I got so aroused when I sucked him. He was gentle and didn't try to push it too deep or fuck my mouth. He just caressed my hair and neck, moaning cutely.

I stroked him, kissing his belly and shaft. I fondled his shaven balls and even his ass. He didn't resist, and all I could see from his eyes was enjoyment. When his breathing got heavier and it seemed he was sliding towards orgasm, he pulled me up and we kissed.

"Let's go onto the bed," he sighed.

He laid down and was slowly stroking himself, watching me as I took off my bra and showed him my breasts. My tits were small hormone-breasts, since I had never wanted to take implants. My nipples were hard and protruding. I saw from his gaze that he loved what he saw, and it made me blush.

I lowered my thongs and my half erect, shaven cock sprung free. I stroked myself in front of him. Letting him enjoy the view.

"You look stunning, Jessy." Was all he could say when I climbed onto the bed next to him.

"I can't believe you are here with me," he said softly and made me smile shyly.

"I can't believe you wanted me here with you."

Then he moved between my legs and started to slide his hands slowly from my thighs, over my belly, all the way up to my breasts. Our eyes never left each other.

"I love your body," he whispered as he slid his hands downward to my half-erected cock, taking it into his hands gently. He caressed me with both hands. He fondled the shaft and my balls, peeling the foreskin back and examining every inch carefully.

"Oh my god, that feels good," I sighed as I watched him lower his head and take me into his mouth. I almost didn't believe it. None of the guys I had had sex with had ever given me oral sex, even when I had wanted it so much.

"Ooh, fuck..." I had to push my fingers to his hair just to feel the movement as he sucked me. I was getting fully hard.

"Take it slow, Elias." I managed to say when he swallowed my whole shaft, sliding his hands to my breasts, teasing my hard nipples. It felt amazing. No one had ever been this gentle with me. I could feel how the tip of my penis touched the back of his throat, and all I could do was moan and hold on to his hair.

Then he pushed my knees to my chest, opening me up, and slid his tongue to my rosebud all the while stroking my cock slowly. It made me shiver. He licked me smoothly, exploring my anus. He pushed his tongue inside me and made me tremble in excitement.

"I could just lick and suck you all night, gorgeous," he sighed breathlessly, seeing how much I enjoyed what he was doing. He was clearly preparing me for his cock, and I was more than ready to take him inside me.

"No one has ever done that to me before. It feels unbelievable when you do that... please don't stop."

He made me feel more of a woman than any other man. I really felt like he was licking my pussy and I could feel myself getting wet from his saliva. When he slowly pushed a finger in me, I was already close to an orgasm.

"I want you inside me, Elias." I moaned, massaging my breasts.

He rose to his knees, and when he pressed his engorged organ against mine, they really looked like twins. I think we both laughed a little. It felt so good when he poured some lube and stroked us slowly. I pressed my hands over his and we caressed our cocks together.

"I want you... I want to feel you in my ass, Daddy."

He took a hold of his dick, rubbing it over my anus, spreading the lube, before he entered me. I squeezed his legs with my fingers when I felt his hard organ sliding inside me.

"Oh, my god, you feel so good," I sighed, and he leaned over me and kissed me. He started to fuck me slowly and I was stroking my cock. His shaft felt unbelievably good inside me.

"Just like that, fuck me slowly, Daddy." I moaned. After a minute or so, I couldn't hold it anymore. His movements were so gentle and loving that every push of his cock made me feel like I was in heaven.

"I going to come... fuck... I'm sorry," I managed to say before my cock pulsated, pushing out clear liquid onto my stomach.

He looked at my throbbing cock. He took it in his hand and caressed it slowly, making my orgasm last longer. All the time sliding slowly inside my ass. His gentle movement and closeness made me come again, and my muscles contracted strongly.

I guess I must have squeezed his cock inside me since he came too. I felt his cock spraying warm cum that filled my ass. He collapsed on top of me, breathing heavily. All the guys I had been with before had always fled straight to the shower right after they had come, but not Elias. He looked me straight in the eyes and kissed me.

"That was so perfect, baby," he sighed, still out of breath, and I pulled him closer, kissing him again. We stayed like that for a long time. Just exploring each other's lips gently, hands caressing face and neck. I wanted more of him.

We rolled over and when I was top of him I started teasing his nipples gently, then his belly, before taking his soft cock into my mouth.

"Oh, my god, Jessy," he moaned as I took him in again and again.

I felt how he started to get hard, and it aroused me. I let my hand slide on his shaft, sucking just the tip and then taking him as deep as I could until he was fully hard. I licked all the way from his balls to the tip of the cock, keeping my eyes on him.

"I want to ride you, Daddy." I cooed and squatted over him, straddling his beautiful meat.

I took him in slowly, leaning backwards, and started sliding up and down his shaft. His cock filled me completely, like it was made for my ass. I could feel him getting harder with each entry, and when he reached for my breasts, the moment was perfect. Sex had never felt like this with anyone.

When I leaned forward, still making love to his cock he took my head between his hands pressing our foreheads together. We just stayed there. I, moving slowly along his shaft, looking deep into his eyes.

"Kiss me, Elias," I pleaded with him. I wanted to feel loved.

When he started to kiss me this unbelievable feeling of warmth filled me and I didn't even notice it at first, but my half-erected penis drained fluid to his stomach once again. I blushed and giggled a bit, but he just took hold of my erection and stroked me gently while I continued to ride him.

When I started to moan louder, I guess my expression must have looked like I was experiencing pain, even when all I felt was immense pleasure, he asked me.

"You good, baby?"

"I've never felt better... I can't believe how deep you are in me, but my legs are getting tired."

"Turn, babe. I want to take you from behind."

When I got on my fours and offered him my ass again, he didn't hesitate to eat me. He licked my ass and pushed his tongue inside me all the time fondling my cock and balls.

"Fuck me, Daddy... I want your cock inside me... fuck me."

"You have a beautiful ass, Jessy." He grinned as he teased my hole with the tip of his cock.

"It's all yours, Daddy."

He started to slide inside me slowly. Letting his cock almost slip out before entering my trans-pussy again, all the time his hand caressed my ass and my skin gently. Then he reached down and took a hold of my penis, squeezing it softly in his hand. His cock inside me and my penis in his hand made me moan and mumble. I couldn't help it, I was hard again.

"Push it as deep as you can, Daddy." I pleaded him cause his organ inside me felt so fucking amazing. All the lube made me feel like I was getting wet for him, and it aroused me even more.

"Fuck me hard... I want you to fuck your Sugarbabe." I pleaded and felt him taking hold of my hips, starting to pound me harder. I bit the pillow and clenched my fist, pushing myself to him, trying to get him deeper inside me.

"You are making me come again, Jessy," Elias moaned still fucking me hard.

"Come in my pussy, Daddy. I want your cum." I tried to say, and I guess he did understand me since he stopped and spun me to my back, pushing my legs to my chest.

"I want to look into your eyes as I come inside you."

His words felt good, and they made me smile. He was so sweet. This was nothing like I was used to being treated. We were in the missionary position again, and he was making love to me with long strokes and kissing me.

"I want to feel and see your orgasm, Daddy."

When he started to fuck me harder, I had to grab his arms and I couldn't keep back my loud moaning. I wanted him more than I have ever wanted another man.

"Oh, my god, how good you feel, Jessy."

"Please fuck me, just like that."

When his orgasm started and his movements slowed down, he pressed his lips against mine and we kissed passionately. I fondled his neck and pulled him closer. I never wanted this moment to end. His pulsating cock, the sprays of sperm inside me and his closeness was almost too much to handle. At that moment, I felt like I was ready to fall in love with him.

Elias and I made love several more times during that night, and I got to sleep in his arms until morning. Not only had he made my life so much easier with the arrangement, but without knowing it, he had given me many new experiences I hadn't even dared to dream about before.

How could I prevent myself from falling in love with him? I didn't know that.