Mistress Valeria Pt. 01

Background:

This is based on a true story and honestly will be about 90% correct right from my memory. I mean why not write as close to the truth as I can when the truth is a plenty good story. I did try my best to edit this and if it is a hit and I write more then I may get someone to help me review it but for the mean time this is just purely writing to remember a fantastic night that would give me a mistress I had only previously dreamed of.

Chapter 1. Noticing Her and Reaching out

As a young man in my mid 20s, I spend most of my time working or resting from work. This leaves little time for me to meet women or date really as it feels like more energy and effort then I want to use. Not to mention I have put on some weight since my varsity sports days so I am more than a little self conscious about how my body looks. I am however, a 5'10", dirty blonde hair, blue eyed confident business man, with big strong legs from my football and soccer days but had now grown more of a dad bod with a beer belly. As you can imagine, if I wasn't out dating then in this time of my life I was watching a lot of porn as I am young man with a constant need for sex. I have been watching porn for so long that for the most part just normal sex in porn doesn't do it for me anymore. This constant urge to find the new hot thing eventually led me to watching porn with transwomen and wow was that the best, most exciting thing I had ever seen. From the women dominating to them being super slutty subs, I was hooked. I even started getting into forums of people telling their stories meeting transwomen and some more fictional hot stories. I will let you know this interest never led me to be into guys in any way. I love the feminine side of women too much, with their hot curves of asses and tits. However, by my early 20s I was into the porn enough, and the stories, that I had to try something in person to feel out this exciting taboo.

This story focuses on my first time with Mistress Valeria and the build up but she was not my first. A few years back I had met an escort, she was an asian transwoman beauty that helped me get comfortable and we met a few times with me mostly the top but I did try out a submissive role with her to no real enjoyment. I then saw a hot Latina who you would swear was a biological woman but once you saw her tumblr vids taking guys, it was clear she had a fat cock that she loved to use. I let her kind of top me but she was not into it much at all as I was not much an eager bottom. Over the years I saw maybe one or 2 more transwomen all with little to no interest in me as they were escorts and I had admittedly made them a fetish without getting the super sexual feelings in person other than the taboo of it all. Then finally came Mistress Valeria and wow would my entire world change.

One day while on an escort site I saw the beauty that would grab my full attention. While scrolling through the trans escort section I stopped and stared at one picture labeled Mistress Valeria. Her picture was her laying down facing the camera, her tits uncovered all be the nipples, her white/blonde hair pulled back into a ponytail, and her glorious lips covered in a delightful red lipstick. Now any woman looking like this would come off stunning but seeing Valeria like this, her massive firm tits larger then my head, and knowing she had a cock hidden, I was left in a trance. Once I was able to stop staring I opened her ad and I was treated to more amazing professional photos, all looking classy and yet slutty. Nothing showed her cock but it said she was my height and had a thick 9.5 inch cock, not to mention a large ass as well and I am quite the ass man.

I was immediately intrigued as all previous transwomen I had been with I had purposefully chosen shorter and smaller and with cocks closer to my 6.5 inches, well not to mention I had seen photos of their cocks but her's was a mystery. I just had to know what Mistress Valeria's fat cock looks like. I immediately saw she was taking reservations for next week and emailed her. My email started out innocent enough, requesting to see her the first evening she was in town and mentioning I was flexible to see her any time in case that was already booked. I hid my complete infatuation for now as I didn't want to start professing myself to her before we even met but I could just tell from everything I read and saw that she would be a whole different experience for me.

Chapter 2. The Build Up

I had emailed Valeria on Sunday and had to wait 4 days to see her and each day felt like an eternity. I could not stop going back to her ad and staring at her pictures. Imagining myself being suffocated between her tits or under her ass. I wanted to rub my cock on her lips, tits and ass as well but of course I mostly had to see how big and fat her cock was. I was so intrigued I was actually excited about being a bottom for this goddess. I wanted to please her like the porn I had seen and submit to her every whim. Going over it in my head constantly at work made it impossible to focus. I had to leave work early a few days just so I could masturbate. I was definitely a mess and I had not even met her yet. I even emailed her a few more times to confirm she didn't need to screen me and to find out her location. She gave me bare minimum information and that drove me more crazed into her mystery.

Finally, it was the day I was going to meet her. I had set up plans to see her at 8 pm so I could go home shower and get all ready to see her. This included a few drinks to calm my nerves as the idea of sucking her cock and possibly taking it deep in my ass was making me super nervous. Not to mention the taboo of seeing an escort and meeting a woman for the first time always had me on edge. I showered and thoroughly washed everywhere including my ass to make sure I looked very clean and smelled great for her. I took one more shot of bourbon then washed my mouth out and headed out the door. I had my AC on full as I drove as I could feel my nerves making me heat up. I texted that I was on the way to her location and it would be about 15 minutes till I arrived. It took everything in me to not speed and keep it cool as I made my way towards her.

I blared some rock so as to keep my mind off of her to just rest my mind before I was going to be overwhelmed with her presence. I knew this was going to so exciting that I had to breathe and keep my cock soft before it would rage hard for an hour. I parked out front and texted that I had arrived, and Valeria told me come on up to the room, that she was ready. I opened my car door and slowly walked through the hotel lobby, acting as if I belonged. I waited slowly for the elevator to come down then as it slowly went up. My heart was beating out of my chest and my body felt numb as I walked around the corner and saw her room number. I paused for a moment, taking it all in and then... I knocked.

Chapter 3. The Wait Was Worth It

Mistress Valeria opens the door and I slide inside and turn to get my first view of her. I stop dead in my tracks. Her smile melts me immediately and she says "Hey babe." I say "Hi" back trying not to come off too nervous and give her a hug. Her massive tits crush into my chest and they are magnificently firm. We share a brief kiss that leaves my heart beating out of my chest. We turn and walk into the room and she takes a seat on the bed and me next to her. We speak briefly as I try hard to listen to her words while completely checking out her body. She is wearing a tight small shirt showing huge cleavage and small shorts to leave little to the imagination.

We kiss again and I mention, "I am usually more of a top but I am thinking I want to be a bottom for you."

She gives a sly look and says, "okay babe we will take it slow." I kiss down her neck and start freeing her tits from her shirt. My god they are perfectly massive and firm and I can't help but play with them and motorboat them. After a little time I look up and give her the eyes saying its time to see her cock. I stop breathing as I slide off the bed to the floor and unzip her shorts. I slowly slide her shorts down and her glorious cock comes into view. "Holy shit," I say under my breathe. My mouth waters and I grip her cock. Its the biggest I had ever seen in person. I slowly stroke up and down as I take her all in. Mistress moans slightly and I decide I need to taste this monster. I slowly lick the head and take it into my mouth, before I lick down both sides of her cock. Her balls are also enticing and I spend some time sucking and licking her balls.

At this point I am drooling but I want some more. I stand up and undress myself and I request she sits on my face as I love eating ass. We re-position on the bed so I am laying on my back. Mistress Valeria slowly brings her ass down to my face, until I am completely suffocated face deep in her crack. I was in heaven, smelling her musky aroma and taking her ass with my tongue. As I get going and she starts moaning, she decides to suck my cock and wow I was brought to an even bigger high. She takes my full cock in her mouth and tongues around my cock head. She then inserts a finger into my ass and I moan loudly at the intrusion. In just 2 minutes she has me almost cumming everywhere and I force her to slow down while I keep eating her ass. Once I feel her mouth cant be on my cock anymore before I cum, I get her to sit up and face fuck me some so as to prepare for her to fuck me. Her fat cock makes me gag as I cannot get more than 3 inches down my throat.

I spit and make her cock slimy and I can feel my ass tingle now thinking this huge cock must get inside me. I push her out of my throat, look up into her beautiful eyes and say, "Please fuck me now." Mistress pulls me to the edge of the bed and grabs the lube to lather up her cock as she sticks 2 lubed fingers into my ass. I groan out in slight pain and pleasure. As I mentioned in the beginning, I was inexperienced in any anal so I was just hoping to take some or half of her glorious cock. She slides her fingers out and says, "mmh I'm so ready to take this tight little ass." She slides her cock head up and down and slowly pushes it inside. God I am so tight she can barely get her head into my ass. Mistress notices this and decides to just use the head of her cock to create pleasure and pressure on my ass and starts jerking me. I'm in a perfect scenario of pain and pleasure as my balls build pressure.

I ask her to fuck me and she shoves slightly more cock into me while stroking me and I bust all over myself in great ecstasy. We both stop and breathe heavily, Mistress brings me a cloth to clean up and offers me a shower. I clean off and can't stop smiling as this was the best I had ever had with a transwoman and significantly enjoyed sucking and taking her cock unlike before. I walk out of the shower and we share some pleasantries before I dress, pay and leave. While the experience was clearly amazing, I didn't realize how incredible until while driving home all I could think of was pleasing that glorious cock. I was actually hooked, and addicted to her massive member. I thought uh oh this is new. I felt the need to text her thanking her for the amazing time. I went home and went to bed dreaming of that cock and how I could get it again.

The end

I hope you enjoyed part 1 of this series. There is definitely a follow up as I have seen Mistress 4 times now and the story only gets better each time. In fact it went so well I see her 2 nights after the above story as I was so addicted. Look into part 2 when it goes up and hopefully you will be hooked enough to get to where I turn into her true boy toy slut.