First time escorting….[FM]

I have been intrigued for as long as I can remember by escorting and sugaring. It really hit home for me when I worked at a casino in food service and got approached more than a few times by older gentlemen offering things. A fellow ice cream scooper was already sugaring and told me all about what she while trying to recruit me. I never really did anything until a bit later when I broke up with a boyfriend who moved out and left me with a lot of bills to pay on my own. That’s when I decided that I could make a lot more being a sugar baby. I posted here on Reddit as well as Seeking Arrangement and got quite a few hits, but it felt like a lot of guys weren’t being serious. The ones that were serious felt like they were trying to bargin which was a hassle.

I did meet a few men for dinner but nothing really came of those other than one who told me I would be better off escorting. I asked him a lot of questions which he kindly answered for me. I already had some photos that I used to create a website from a template I found and then posted an ad on TER. Again, I got quite a few hits, though this was significantly different. I zeroed in on one man who had written quite a few reviews as I knew this would help me create future business. We emailed back and forth a bit to get to know each other as well as verifying his references.

This was the first place that I paused as one girl said that while harmless, he could be very clingy, even showing up at one girl’s location without having an appointment scheduled. I thought long and hard about moving on, but I had so much invested with this guy plus he promised me a review. We nailed down a time and were all set to see each other. And then I chickened out. Despite knowing that I could do this, something held me back and I ghosted “Ben.”

I thought long and hard over the next few days about if I had made the right decision. I decided to apologize to Ben and see if maybe we could try again. Much to my surprise, he agreed to meet me for coffee beforehand and then we would walk to the hotel room. He told me to wear something casual that I had on in one of my photos, a flannel and jeans, but to bring a few outfits that he wanted to see me in. When the day came, I swallowed my nervousness and met him at a local Starbucks. He was mildly attractive with a nice head of hair and was dressed nicely. He was used to being the alpha male and it showed in our conversation. At some point, Ben told me it was time to go – not if I still wanted to. The difference turned me on and made my decision easy.

He put his arm around me as we made our way to the hotel. As we made our way through the lobby, I just knew that everyone knew why we were together. Once in the room, we sat at the couch and he presented me with a few gifts that he had brought for me based on the interests I listed on my website. It was thoughtful, but it made me think back to the one reference’s comments. After more small talk, I asked him if he wanted to take a shower. He proceeded to the bathroom while I hid the envelope he presented to me upon getting up.

I made my way into the bathroom after I was sure he was in and pulled the curtain back to tease him. I think I said something along the lines of how are we doing in here. Ben wasn’t the least bit bashful and I watched as he soaped his cock hard. When he was done, I handed him a towel and he told me to change into my dress before meeting him in the bedroom. After slipping into my dress and heels, I tool a good long look at myself in the mirror. There was no turning back so I smoothed the front of the dress and made my way into the next room.

Ben and I locked eyes as he approached me buck naked. His cock was pretty hard as he bent down to kiss me, slowly at first and then he put his hand behind my head and slipped his tongue into my mouth. As I relaxed, my hands touched his back and then one moved to the front and I started stroking his cock which caused him to moan into my mouth. Ben broke the kiss, and told me I was being a naughty girl as his hands reached under my dress and began teasing me. When I began to get wet, he confidently announced that I was really enjoying our “date.” He told me to slip my dress off which left me standing before this man old enough to be my father in a matching bra and panties set and heels.

He kept telling me how much he had been thinking about this moment. I had as well. Ben’s hands were stroking my body all over very gently until he moved to my breasts. He teased my nipples which were erect beneath by bra and then told me to free them. I turned around and teased him by taking my time and slipping the bra off very slowly. I was so turned on at this point that a wet spot was apparent on the front of my lacy panties. Ben kissed my neck and I could feel his hard cock pressing against my cheeks – it felt good to be wanted by this man who had seen many experienced escorts. His hands slipped into my panties as he reached around and played with my clit. Ben was good with his fingers. I would find out later on that wasn’t the only thing he was good at.

He slipped my panties down my legs and I stepped out of them. Ben nudged me forward and put his hand on my back indicating he wanted me to lay down on the bed. Once down, it felt like his eyes were burning a hole into me. He ordered me to open my legs and show him how I touch myself. It was a surreal moment and I am convinced it was the most turned on I have ever been in my life. Ben watched me and seemed to instinctively know when to kneel between my legs and begin kissing his way to my clit. The eye contact we had maintained failed me now as I closed my eyes and my head went back. The idea that this man wanted me so badly and was so good with his tongue brought me closer to having an orgasm – something I never expected to happen. My hands went to my nipples where they played and pulled at them – when Ben inserted a finger, I dropped one to his head and pulled him in harder as I came on his face.

He knew I wasn’t faking, mostly because he was so cocky. Ben made his way up to where I was on the bed and he fed me the finger he had inserted into me. I was still coming down, but he wasn’t going to give me a break. I sucked on it as provocative as I could. Ben asked if I was ready to taste his cock – I bit my lip and smiled at him as I made my way down. I teased the head of his cock and licked the sides up and down before taking it into my mouth as Ben moaned his approval. I gave it everything I had as I was trying so hard to impress him. He was thrusting up into my mouth and seemed to be getting close to erupting, but he stopped himself.

“I’m ready to fuck the shit out of my prize.”

“How do you want me?”

“Face down, ass up”

Once in position, he played with my pussy and my ass as I gyrated to his movements. I reached onto the table beside the bed and grabbed a condom that I flipped back to him (rookie mistake as I should have applied it). He suited up and rubbed his stiff cock up and down my opening before pushing in slowly. He teased me with slow strokes before grabbing my hips and going balls deep into me at a faster pace. In his emails, Ben had told me that he wanted me to look over my shoulder at him while he was fucking me from behind so I did as I rose up onto my arms. He grabbed a fistful of hair – something I love. It caused me to unleash my dirty mouth.

“You are dying to empty those balls into me, aren’t you?”

He grunted and pounded me hard.

“Give me your cum, daddy.”

“You naughty slut.”

He slapped my ass hard.

“MMM, daddy, put this naughty slut her place.”

He pulled my hair as he thrust hard into me. I could tell he was close.

“Cum for me, daddy, there’s more where that came from.”

He pulled my hair one final time as my head snapped back and he drained his cum into the condom.

To be cont….

Source: reddit.com/r/gonewildstories/comments/cbtxmd/first_time_escortingfm