The night that opened my heart

Now I know you all want the juicy details. The inside scoop..what kind of adventures I have been getting into this summer. I know my first two blogs seemed a little heavier. So I thought maybe we should add some fun stuff here. The second most voted for blog was a RECENT companion story… so here we go..

The day I met him. I was traveling from Asheville to Charlotte, it must have been one of the first times I drove over there. It was about a two hour drive, and I had an appointment to meet a new gentleman. I remember my heart was pounding so hard, I was super nervous going to a hotel. I had done my first few appointments but they were at peoples homes. Going to a hotel brought back that rush I had when I used to escort in Miami. Thoughts like, am I over dressed? Is the front desk person going to notice me, will they be able to tell I’m an escort? Am I being paranoid? Maybe they aren’t thinking that at all, but just because I know I am assuming everyone around me knows. My date gave me directions to a side entrance so he saved me a little bit of stress walking through a hotel lobby.

I got into the elevator, phew safe. Got out onto the floor I needed to and headed to the room. Walking slowly looking at the numbers, it was like a countdown of distance. Every step I took I knew I was almost there and the build up of meeting this new man was about to reach its climax once he opens the door. I knocked, he answered with a smile and let me in. I giggled and stumbled in very ungracefully, super nervous but trying not to show it I started with my hello, asking how he was, and quickly finding and sliding the envelope into my purse so I could get that part out of the way. I remember how relieved I was once I was in the room, and how excited I was to meet this professional man.

He was my escort fantasy, the clean business man in the nice hotel room. Middle aged, but boyishly handsome. I was so excited, I remember strutting around him playfully, poking my butt out, looking back and giggling. Right away we were both happy, I ended up in his arms and we shared our first kiss. We started to pet and hold each other, slowly learning each other’s lips. I was grabbing the back of his neck and his hands were on my waist as we enjoyed a long session of kissing and connecting.

After that we had 3 hours of fun and passionate love making. I remembered I was excited that he had a big feller in his pants, and he was very powerful in bed. Deep thrusting, eye contact, and telling me sweet poetic things while he was inside me. After we finished several rounds we then laid in bed and talked. I loved talking to this guy, he was deep and could articulate very well. So we easily flowed in conversation together. I remembered that I explained my tattoos and for some reason told him about the African spirituality and other religions I took interest in. Which was strange because that is something I never bother explaining to people because they always judge. With him I felt the need to talk, talk, talk.

I felt so good after that day, it was exciting taking the small road trip, and getting to connect with someone new. I was so turned on by the fact he looked like an innocent man that in my day to day life I would never think he was capable of such a sexual side if I saw him passing in the street. So I went around after that looking at every professional man I saw, imagining what they were really like, imagining if I had them alone in a room. Who they would really be under those business suits.

I didn’t think I would ever see him again. I didn’t think I would see anyone twice. I assumed it would be like the old days a new person every time. Though, he contacted me. He wanted to see me again. I was so flattered someone had called me back, I thought “Wow I thought I talked way to much about a lot of weird shit.” I was for sure he wouldn’t call me back, that I was to much energy or something. That wasn’t the case , in fact I had intrigued him. He wanted more of me.

This is where I started to feel really spoiled, and like I was finally living the luxury VIP companion fantasies I daydreamed about when I looked at all the girls on their sites and social media. I was invited to a special date with him. First a massage, and then dinner at a nice restaurant on a lake. Then we would go for a ride on his boat!

I was so excited, the third professional massage I have ever had in my life. It had been YEARS since I had one though. He wasn’t there but he sent me to one. Which was fun, like my master was sending his little princess to get spoiled before summoning me. I got an amazing relaxing massage then went to meet my date.

So nervous of coarse, and with the usual train of worrisome thoughts running through my mind. Did I wear an appropriate outfit? Should I cover my tattoos? My uber was dropping me off and was trying to figure out where he was dropping me off I remember him oohing and aahhing saying I was going to a real nice place. As I got out I saw, and got excited. To see the water and the boats! I walked towards the entrance and there were a few older gentlemen with silver hair and beards standing at the front talking and for some reason I thought they worked there so I asked them, “Is this the entrance? Do you know which way is the bar?” They smiled so big and said sorry and no, I giggled and said, “Oh my I am SO sorry I thought you worked here!” Grabbing his arm to apologize and then running away in my heels laughing. I just remember seeing their still, smiling faces walk me strut away. I walked in through the entrance and towards the bar in the back. My heart was pumping and the place was full of wayyyy older people I was like great, I stick out like a sore fucking thumb.

Once I got close to the back I saw him, standing by the bar. All cleaned up with his hair combed to the side, in a suit and buttoned up shirt, with the biggest smile and twinkle in his eyes. That moment felt like I was walking into prom. Which I didn’t go to my prom by the way. So this was a special moment for me. I greeted him and we hugged tight. He sat me down at bar table and got me a drink, we hung out and talked for a while. Eventually we moved to our table and sat down for dinner.

We talked and talked, just spending time together and talking was really awesome. We were blending, getting to know each other. Furthering our relationship. I was new to my luxury companion journey this summer and just started, I wasn’t used to the idea of getting to know someone more yet, and I appreciated it a lot. I remember at one point I finally took my cover off, I exposed my arms and all my tattoos. I was nervous because I didn’t know if he was okay with that. I could see other people from other tables looking over at me. I was trying to look down or straight at my date ignoring anyone who stares. Again worried, omg do they know? Can they tell ? It was my first public date with a suitor and I was more than anxious about it.

My date went to the bathroom so I started to scarf down my food. I was so hungry but I was eating like a bird in front of him. For some reason I was embarrassed to take to big of bites in front of him. So I stuffed my face before he came back, when he did I told him how I ate a bunch and he laughed. I think he thought it was super cute but was encouraging me to eat and not worry about it. He just couldn’t understand though, I was way to bashful.

We finished dinner and he took me to the boat. We walked from the restaurant to the dock. I remember strutting in my heels, and he put his hand out to help me step into the boat. I am sure everyone on the outdoor eating area was watching us board our little ship. Again I felt exposed in front of people in public on a date, thinking everyone knew what I was. A part of me was excited about it and was hoping I was filling all the older men’s minds with fantasies seeing this other older man on a date with this young little blonde woman. I love to tease, and I constantly fantasize..I just can’t help it!

We got on the boat and hit the lake. It was sooo beautiful, and so much fun. I hadn’t been on a boat in a while, and never on a lake always in the ocean. We floated around and enjoyed the sunset colors. He cruised out to a little spot that was secluded and dropped anchor. This was our spot for the night. He lit candles all over the boat and pulled out chocolate covered strawberries and champagne. Such simple gestures made it so romantic and that much more over the top. This guy really wanted to give me a great experience and I loved the effort.

We got naked and had a blanket to cover us while we played just in case someone showed up. It was so yummy to go back and forth with passion, exchanging our energy and pleasure. The air was so perfect neither hot or cold, and I loved the sound of the water and slow rocking of the boat. I remember squirting and cumming, with him whispering in my ear to look up the sky while I came. He always said the right shit. Reminding me that mother earth was surrounding me, and the beautiful sky and universe over me while I was cumming free on the boat. The stars were starting to peek out and I would search for them while I kept cumming. It felt so good, so cleansing.

This was also the first night I ever pegged a man. He asked me if I wanted to. I didn’t know what to say I was shocked, it wasn’t something I really wanted to do that bad, but I never done it so I wanted to. I am all about doing things just to try and have the experience, to say that I had done it. He pulled out a new strap on he bought for me and our special occasion. I was so excited, it was really dark and rocky so I didn’t finish putting it on me properly. I had him bent over the seats on the back of the boat, lubed up before I tried to put it in. I was so scared because my own ass was so tight and it would take me a while to relax for anal. So this poor man, how could I do this to him. He was willing to be there for me though, to be my toy to try something new on. He gave himself up to me like that, showed his vulnerability and I didn’t over look it. I was so grateful he was ready to try this experience with me. I put it in him slowly and did a few thrusts. I kept asking if this was okay, if it hurt or not, if he was comfortable. He was fine, so he said, so after a few moments I felt confident. I ran my fingers up and down his back, squeezed his ass, and pumped him a little harder.

It was SO MUCH FUN! I felt this weird primal, powerful feeling. Even though being a woman, I felt slightly masculine in that moment. Well I did have a phallic object strapped to me, ha. I was dominant, on top, and in control in that moment. Sexually I was the one putting my energy into someone. It was a very different feeling than being a woman and taking it, instead I was giving something to someone, inserting something into their body. I had worn a strap on with women before but never men. I still don’t know what to say, it was the perfect mixture of dominance, connection, trust, friendship, and release. He gave me power over his body, which was precious to me because I was always in his role, receiving. That day he gave me a new sort of confidence.

It was really short, like five minutes maybe even less. I think we both knew it was not something we wanted to do for long, but it was more of having the balls for us to try this sexual activity neither of us have ever done. After that I was giddy and in shock I did it! He was so sweet, so excited for me haha. I was excited how fun and easy going he was. How exciting he was, brave he was. Which he also jumped into the lake which I was way to afraid to do. But he did it without hesitation and it was fun to watch, I was all around amazed by this man. I mean he let me fuck him in the ass, AND he just jumped into a lake! These were exciting points for me, as I lived very sheltered growing up, and being young I am still trying new things.

It was getting late, and time to head back. This is when I got a little sad, I did not want our adventure to be over but it was time. He pulled anchor and we headed for the dock. I was sooo so sad to leave him, that night I fell for him. From the longgggg conversations at dinner, to the fun play time free and nude on the boat under the stars and crescent moon, I felt a new deep connection I hadn’t felt before.

The whole way back he sat in his chair in front of the wheel and steered the boat. I crawled over and sat there at his feet and wrapped my arms around his legs and put my head in his lap. I stayed there kissing his knees and thighs, laying in his lap with the blanket wrapped around me covering myself from the wind. We got to the dock, he took the sex toys and what not and threw them in a trash can. Get rid of that wild evidence, hehe. Then I sat in his SUV while I watched him get the boat out of the water and onto a trailer on the back of his vehicle. It was actually turning me on watching him do this, something super masculine, seeing a man work with his machinery. As corny as it sounds, I loved it. I was fucking someones daddy, and that made my pussy wet. He was now my man in charge, taking care of something for me for our date. He gave me a ride back to my airbnb, we kissed good night, and parted ways. I remember laying down and I was SO wide awake. It was 2-3 am and I knew I had to wake up early and check out, but I laid there and re-ran the night in my mind over and over.

I would never forget such a powerful night, the first time I connected really deep with a suitor. A new strange relationship for me, but it totally changed my world.. and opened me up to accepting new deep connections with my suitors. He showed me how to love outside my marriage, he opened up my heart to be able to care for others, for more. Which has led me to be able to have many more amazing connections and experiences this summer. So I will never forget him , or this night, and I hope he doesn’t either.

emily monroeComment