Kelly's Diary 073 - My 1st Escort Job - Dreams of His Daughter - Cover

Kelly's Diary 073 - My 1st Escort Job - Dreams of His Daughter

Copyright© 2024 by Kelly85

Chapter 4: The Hotel

Erotica Sex Story: Chapter 4: The Hotel - Oh my God, I was SO nervous! What the hell was I thinking anyway? I must have been crazy to do such a thing. Did I really think I could be an escort without being a whore?

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Masturbation   Oral Sex   Prostitution  

Upon our arrival at the hotel, Greg dropped the car off with the valet and we entered through the main lobby. No sneaking in the back door or otherwise trying to hide; instead Greg offered me his arm and we entered like two lovers returning from an evening out on the town. Even so, I imagine we got more than a couple of looks given the age difference between us. The guys most likely were wishing they were Greg while the women probably considered me as slut - or worse and Greg as some dirty old man! No matter, we got into the elevator and went to his floor and then to the room without hardly a word between us.

Standing outside his room while he got his pass key out, I felt a tingle through me as the realization of what was about to happen slowly sank in. I was about to cross a boundary that I never had thought I would. It was impossible now to say I was just being a slut when he was paying for sex. Then again, I guess technically he hadn’t paid me anything - yet at least.

Suddenly I felt the weight of the truth on my shoulders, like someone had dropped a truck on me. No matter how I had tried to avoid it until now, the fact was that I was most likely about to be paid to give sex to a man who, no matter how nice he might seem to be, ultimately wanted me only for my body. Now if THAT didn’t make me a whore, something I’d always HATED to be called, then what did?

I didn’t have any more time to contemplate it as he held the door open for me to enter. I looked at the threshold and once again I thought about how if I stepped over it there was a label I would have to wear forever afterwards - whore. Was I really willing to go through life knowing I’d prostituted myself, even if only once?

In a way it was like giving up my virginity again in that once done there was no way to ever go back to the way things were before. No matter who knew or didn’t know about tonight, deep inside I’d always know what I really was - a girl who had been willing to sell her most precious asset - herself.

Taking a deep breath, I stepped over the threshold and it was done. When I entered the room it was like the burden dropped from my shoulders. With that one simple step forward I accepted my fate and new role. Now that my decision had been made it was just a matter of going through with it. On the way over in his car, I’d been rehearsing this moment in my mind so I would be ready but now everything blanked out and I couldn’t remember any of the clever things I’d thought of saying right now.

Greg was staring at me now but hesitating as if he was unsure what his next move should be. I took charge as a good whore would, stepping back and falling back on the bed, letting my dress ride up such that most of my legs were exposed. I gave him my best sultry look and then started the game...

“You know Greg, I bet you would love to see Mandy laying here like this, wouldn’t you?”

Greg’s eyes widened as he replied, “What do you mean? She’s my daughter for god’s sake. Why are you talking about her now?”

I smiled wider saying, “You can’t fool me Greg. I could tell how much you love her from the way you looked when you talked about her. Wouldn’t you love to have a chance to show her just how much you really want her?”

Greg was looking confused. I was making an assumption that he actually had those feelings for his daughter and from his reaction I was pretty confident I had read him right. Still, at the same time he was struggling with years of repressed feelings and upbringing.

Finally he rolled his eyes and sighed, “God forgive me but yes, I would. But I could NEVER do something like this with her ... no matter what.”

“I understand ... so let me be her tonight Greg,” I offered softly, “Let me be Mandy tonight. Forget who I really am and put her face in your mind when you look at me.”

“Huh? What do you mean?”

“Here’s what I want you to do Greg ... I want you to leave the room for a few minutes. I’ll get in bed like I was her asleep at home in her bedroom. Then you come in and do with me all the things you’ve always wished you could do with Mandy.”

Greg hesitated so I pushed just a little but more, knowing he was close to the edge. “You know the feelings you get when you see her sleeping at night. You know what you’ve secretly wished for when you see her in her bikini. You know how jealous you feel when she comes home and you know she’s been fucked by some young kid from school. This is your chance to act out all those feelings and fantasies you been forced to keep inside of you all these years. Let me be Mandy tonight Greg.”

Greg smiled finally and shook his head. “God you really are something Kelly. How did you know I felt about her that way?”

I just shook my head, not willing to go there. “It doesn’t really matter, does it? What’s important is tonight you can fuck Mandy. You have your little girl for your very own once and for all. Let me be Mandy tonight for you.”

Greg’s cheeked puffed out as he let out a deep breath. Then he seemed to make up his mind as he turned and left the room without another word. Once the door was closed I quickly stripped down to nothing and went in my purse to bring out a the sheerest and tiniest nightie I owned, slipping it on and then following it with the matching panties. Looking in the mirror I could see the flimsy outfit hid absolutely nothing but that was the whole point!

Looking at the gaudy comforter on the bed with disgust, I pulled it off of the bed and tossed it in a corner. There was no way was I letting it touch me after some of the shows I had seen on TV about hotel room hygiene! At least the sheets had supposedly been washed since the last people had stayed in the room.

With that I snuggled under the blanket and pretended to be sleeping just as the door unlocked. Greg was back. I kept my eyes shut as I heard him entering the room and latching the door securely behind him. Hopefully he hadn’t transformed into some ax murderer! I could hear his breathing grow heavier as he moved towards the bed, seeing me in bed with my dress laid out over the small sofa. I could hear him whispering to himself, talking himself into doing what I had urged him to do.

“Oh Mandy,” he whispered in a louder tone, his voice husky with lust.

A chill of anticipation ran through me as I wondered what he was thinking right then. Had he ever been in a similar situation as this before? Had he ever ventured into his daughter’s room and seen her sleeping like this, wanting so bad to pull down the covers but knowing he never could? Looking at me now, was he seeing the escort he’d hired or was he visualizing his cute daughter instead?

The covers were now moving on my legs as he lifted them to see my lower body. I kept my eyes tightly closed, pretending to be sound asleep and totally unaware of what he was doing. The cool room air chilled my exposed legs as the covers were pulled completely off of them until I was lying there with nothing covering me but a flimsy nightie and panties.

I was laying on my back with one leg straight and the other bent upwards to allow my pussy to be seen more easily. Greg’s breathing was getting heavier as he must have been standing there staring at my all but nude body. Then I felt his fingers softly running over the skin of my lower leg, lightly touching me from my ankle up to my knee. Slowly they worked their way upward, first on the top of my upper thighs and then ever so slowly moving down between my legs. I could feel goose bumps rising as the soft flesh of my inner leg responded to his caresses. The fingers gradually gave way to his hand until his entire palm was softly massaging my inner legs, first one and then the other and then back again. God it was making me soooooo horny!

Finally in the middle of one of his motions he made a sudden detour and softly ran his finger across the thin panties that were barely covering my shaved pussy. I moaned softly as if dreaming in my sleep, moving my hips ever so slightly in response to his touch. Encouraged by my subtle response, his finger began to rub me through my panties. When he hit my swelling clit I jumped just a little to signal to him that I liked it there. Fortunately he could take a hint and he lingered in my more sensitive spots. I could feel my pussy getting wet and I knew my panties must showing some dampness by now.

Greg pulled my panties over to one side, exposing my smooth pussy. I shaved every day to keep it looking clean and smooth like it did ten years before and I knew he must have been turned on to see me look like a little girl down there. His exploring finger started at the top of my pussy and worked its way down, teasing my clit and then spreading me apart until his fingertip was running little circles around the opening to my cunt.

I was soaking wet by now and he would spread my wetness around, even moving up to my clit and wetting it with my pussy cum. Suddenly it plunged into me and I involuntarily gasped as the pleasure it produced rippled through me. He hesitated for a second, afraid to “wake” me and then pushed it all the way into me. God this was so sensual and erotic!

While Greg was fingering my pussy with one hand, I could hear him fumbling with his pants with the other. His belt buckle came undone and then I heard his zipper lowering. With a loud thump his pants hit the floor and I knew he had to be standing with his cock exposed right next to me. It was so tempting to open my eyes to see his erect dick but I kept them closed, pretending to still be asleep.

With his other hand he pulled up my nightie to expose my bare boobs and then I felt the tip of his cock rubbing against my nipples. He was still fingering me as his cock moved in circles around my breast, teasing my hardened nipples and then running around the soft flesh again. Once again I wanted SO badly to open my eyes and watch but I kept up the facade of not having a clue what he was doing.

After playing with my boobs his finger came out of my pussy and the wet digit began to take play with my nipples as well. His cock started to rub against my cheek then and finally I felt the head rub against my lips. Well, enough was enough when it came to the comatose routine so I parted my lips just enough to allow his dick to enter.

As his cock slid into my mouth I finally opened my eyes and looked up at him. Pushing him out with my tongue and lips, I smiled and whispered huskily, “Oh daddy, I’ve always wanted you to do this!” and then took him back in my mouth and started sucking him in earnest.

When this story gets more text, you will need to Log In to read it

 

WARNING! ADULT CONTENT...

Storiesonline is for adult entertainment only. By accessing this site you declare that you are of legal age and that you agree with our Terms of Service and Privacy Policy.


Log In