{F}irst time escort {M}ania

The other night I did a nsfwama where I mentioned in it that I had a fantasy of becoming an escort.

I got a ton of responses from my AMA and had a ton of fun talking with a bunch of different people.

One of the messages I received had the title,

"I'll pay you $1000 for one night."

I'll be honest, this got my attention. In the msg "John" explained how he was a 23 year old virgin who's never even kissed a girl.

I messaged him back and explained that so far it's just a fantasy and wasn't even sure I could go through with it. We talked back and forth for a couple more hours and we seemed to click pretty well. In the back of my mind that $1000 still lingered. Easy money I figured but I was pretty sure the guy was gross or something and that's why he's never been laid.

I decided to turn up the pressure a bit just to see how far down this path I could take myself.

I asked him where he was located and when he was looking to have our "date."

John responded that he lived in Milwaukee which is about 4 hours from me but he would be happy to take a road trip and was hoping to do this Sunday before he had to go back to work.

I told him to send me a pic of himself holding his drivers license so I could protect myself. Actually I just wanted to makes sure he wasn't gross.

He sent the pic and relief came over me. He wasn't gross, not quite my type but not repulsive. He had dark hair, wore glasses and seemed tall and lanky. I prefer the more muscular guys but for a grand I couldn't be too picky.

We talked more and agreed on a time and location about 20 minutes from my apartment for the next day.

When I woke up Sunday my nerves were already in full force. I've done some crazy stuff but this was on a whole new level. About 3 hours before our 10pm meet up I started to get ready.

I wore my tightest form fitting pink dress, made sure I was freshly shaved, make up on point, and hair done perfectly.

The time came for me to leave, I was excited and nervous. Everything inside me told me to stop but I pressed on.

I drove away and straight to the hotel. My knees felt weak as I walked up to his door. I stood there for about 30 seconds before knocking, my stomach full of butterflies.

I got up the courage and knocked on the door. John answered the door and invited me in. I was trying to hide my nerves but I knew John could tell.

We sat on the edge of the bed and had small talk for a few minutes. I looked around the room and noticed a stack of cash on the little table in the corner.

I stood up sand walked towards the money. I asked John if that was for me? He told me it was. I walked up to it and pick up the cash. The power it gave me was instant. It was like shooting some kind of drug in my veins. My confidence soared as I counted out the $100's and put it in my purse.

With my new found confidence I walked back over to John. I stood over him as he sat on the edge of the bed. I took his hands and placed them on my bare legs. Now I could really see his nerves as his face got flush and a bead of sweat formed on his forehead.

I slowly slid my dress off and stood in front of him in my bra and panties. I turned around so he could get a look at my ass. I unhooked my bra, letting it fall to the floor.

John started rubbing my ass through my panties and that is when I noticed how fucking wet I was. I mean it was literally leaking out of me.

I turned around and johns eyes and hands went straight to my boobs. He played and pinched my nipples as I let out some exaggerated moans. It did feel good but as a working girl I decided to put a bit more into it.

I told John to stand up which he did. I leaned in and kissed him hard, wrapping one leg around him and grinding my pussy up against his cock. I could feel the hardness of it struggling to push through his jeans.

I pulled his shirt off and kissed my way down his skinny chest. I unbuttoned his pants and let the drop to the floor. I clawed and scratched at his underwear trying to get them off. I was acting like I was desperate to get him naked.

I dropped his underwear to the floor and his cock sprung out, bouncing up and down. It was nice, probably 6-7 inches with decent thickness. Plenty to work with I thought.

I sat john back on the edge of the bed and scooted my way over in front of him on my knees.

I lightly brushed his cock with my fingertips before wrapping my hand around it and giving it a couple strokes.

John gave out a nervous sounding moan which made me start to believe that he's never had a girl touch him. I lubed his cock up with some spit and went back to gently stroking his cock. After about 10 strokes John grabbed my wrist to stop me. He apologized about 1000 times and told me he was so close to cumming. I told him to breath and relax.

After a couple minutes and asking if he was ok I continued on. Once again after a few light strokes he grabbed my wrist again stopping me. His other hand grasping the base of his cock desperately trying to stop it from cumming. He was way too worked up.

I stood up and jumped on the bed to sit and talk for a bit more….trying to get him calmed down.

Realizing now that he was truly a virgin I decided that maybe if he just got that first orgasm out of the way, we could get on with the performance.

I told John my plan and laid on my back. I told him to straddle me around my stomach. He climbed on top of me and I'm serious when I say that his cock was literally leaking cum like some kind of dog in heat. Never seen that happen before.

I told him I want him to cum all over my tits and I started stroking his dick. Once again after just a few strokes he started to moan wildly.

Within second I felt the first stream flow through his cock and hit me in the neck. I was a bit startled at the force his cum was hitting me with. Soaking my tits, stomach and next.

I led john to collapse next to me and told him I was going to go clean up. I made my way to the bathroom, looking in the mirror with this strangers cum all over me and wondering if I'd made a huge mistake. I cleaned his sticky mess off of me and went to freshen up my lipstick. I saw the $100 bills in my purse and once again my doubts were erased.

I was still soaked and my panties had turned in to a mess. I removed them and headed back out to the bed. John stared at my pussy as I climbed in next to him.

I asked him if he'd like to try eating my pussy. He shook his head yes so I laid on my back and spread my legs. John made his way between them and started exploring my hole with his fingers.

My pussy had become so hungry to be touched at this point. I could tell I was going to lose control.

Suddenly I felt his tongue land directly on my clit. I let out a loud moan as this was exactly what my pussy needed.

I grabbed the back of his head and guided his tongue right where I wanted it. He went wild on my pussy! Lapping it like a dog who was dying of thirst.

His tongue dove inside me, went up and down from my clit to my asshole…working everything. I realized at this point that you don't have to be attracted to someone to enjoy getting your pussy licked.

It took a bit of time but after he stuck his finger inside me and I held his head right on my clit, I felt my orgasm build up inside of me.

I started talking dirty at this point, trying to channel my inner pornstar.

"Oh baby right there…you're gonna make my pussy cum!"

"Don't stop, make me cum PLEASE!"

I was grinding my pussy hard up against his face as the first wave rippled through me. I arched my back and let out my loud guttural moan that I always do when I cum.

He kept gently tonguing me as the waves of my orgasm finally came to a stop.

"Wow, you're really good at that!" I told him.

"Are you ready to fuck me yet?" I asked

He nodded yes and reached into the drawer next to the bed to grab a condom.

He started fumbling with the small package as he tried to get the condom out.

I grabbed it from him, opened it and slowly rolled it onto his stiff cock.

He positioned himself on top of me and struggled to get his covered stick into my hole.

I reached down and grabbed his cock, guiding it inside of me. I squeezed my pussy tight as he pushed himself all the way in.

He didn't have much skill or finesse and just started pumping away. It still felt good as having someone inside me always does but some of my moans may have been forced ?

We went for about 10 minutes when suddenly he went soft inside of me.

"Did you cum?" I asked.

He explained that he hadn't but had never used a condom before and said he wasn't getting much sensation.

Now in my "normal" life I would of been thrilled. In this situation though I wasn't sure what to do.

He asked if he could take it off. My mind raced. Figuring that he's a virgin and I'm on the pill, I decided to use this to my advantage.

"No condom costs a lot more." I told him

He asked how much and once again my mind raced. Good fucking question I thought. The first number to pop in my head was $250 and that's what I blurted out.

He didn't bat an eye and asked if I wanted it now.

"Of course" I said.

"Pay before play" I laughed.

He got up and got dressed. Raced out the door and to the ATM machine in the lobby.

I laid there in the bed trying to reflect on all that had happened so far.

It hasn't been a terribly bad experience and I know I should probably feel ashamed at what I was doing but honestly I wasn't ashamed at all.

I was excited. Money = power and at that moment I had both….with more coming.

I've had plenty of sex with random guys who the only thing I saw in them was that they were hot. Why not have sex with someone for just the money?

By the time I was finished reflecting on all this John had returned. He handed me $260 all in 20's. I asked if he wanted his change and we both kinda laughed.

I told him to take his clothes off as he stood next to the bed. I laid across the bed on my stomach and when his pants hit the floor I started working his cock with my mouth. It instantly went hard and I knew from earlier that I better stop while I was ahead.

I told him to lie down and I was going to take care of him.

I straddled up on top of him and rubbed the head of his cock along my entire slit. This got my juices back flowing and I slowly worked him back inside of me.

"There…does that feel better?" I asked

I didn't move as I kept him all the way inside of me. He let out a couple of moans and I knew just from that how good it felt.

"I'm going to start moving really slow now. Are you ready?" I asked.

He looked at the ceiling and nodded yes.

"Make sure and tell me when you're about to cum. If you cum inside me that gets real expensive!" I joked

I lifted my hips up slowly. Feeling the entire length of his shaft as it pushed against my walls until I felt his head at the opening of my hole.

He reached up and started fondling my boobs as I slowly lowered myself back onto him. I gave out a big moan as I buried him to the hilt. I continued this same rhythm for a few minutes.

"You want me to speed up?" I asked.

He nodded again and I sped myself up. Pulling him out of me and slamming back down. Each thrust a little faster.

He grabbed hold of my little ass and held on tight. He was giving out little whimpers as I slammed my pussy down on his cock.

Only maybe a minute later he cried out

"I'm gonna cum!"

I hoped off his cock, still straddling him and started jerking him off, using my own juices as lube.

Only a few strokes later he blasted his load all over. His entire body convulsed as streams of his cum shot all over.

I laid down next to him and gently brushed my fingers along his arm as he calmed down.

He thanked me as I got dressed and I thanked him as well.

Walking back out to my car I wondered if I'd regret this at some point. All I knew was that I was $1260 richer and I had an orgasm.

"John" if you read this I'm sorry I didn't ask if you if it was ok. You did great for your first time and I really did have fun ?

Source: reddit.com/r/gonewildstories/comments/36dh0z/first_time_escort_mania