Escort First Time

WARNING: If you don't like stories where the cheater gets away with it or gets forgiven for it, this story and many others in my catalog are not for you. Unless otherwise labeled, my stories are FICTION no marriage has been endangered to create this story. This is not our universe though it has similarities. STD's are not an issue in this universe, unless they feature in the story line. I don't care if you think every infidelity should end in divorce, or you would divorce. Your morals are not a part of my stories.

Constructive comments about how to improve my stories are appreciated

EDITED - I tried to incorporate some of the comments to improve the story

ESCORT - First time

Google is sending me into a district that looks wrong. I am expecting residential. This is industrial. It does not help my nerves. I pull up to the address, it is an automotive detailing shop. The door has a sign. Phone this number for access. It feels wrong, I dial the number. "Is Rodger in?"

"Sorry, there is no Rodger working here."

"Sorry, wrong number."

I go back to the text message with the address. I typed an 8 into Google Maps when I should have typed a 3. I correct Google, 15 minutes. I am going to be late. I am shaking with nerves; can I go through with this?

The correct address is a middle-class bungalow. I walk up and ring the doorbell. I am shivering in the heat. I hear someone coming and the door opens. A gust of Air-Conditioned air surrounds me.

"Rodger?"

"Yes, you are Destiny?"

I am about to say Donna, then remember, it's my escort name. "Yes" I may need to rethink my escort name.

"Come in."

He looks old, I know he said senior in his messages booking me, but I am 38. My father is 65. He looks older than my father. Maybe escorting is not for me. But I am here, I step in and he closes the door behind me. I see he is wearing slippers, so I slip my heels off. Barefoot I am 5'9". He is taller than me. At least that, if he had been shorter, no that is my nerves talking, I had boyfriends shorter than me.

"You are gorgeous, you look just like one of my daughter's friends."

I am not sure how to take that, is this some kind of role play fantasy? He points at an envelope on the vestibule table. I pick it up, and check it, $350 just as agreed. I put it in my kit bag.

"Let's go upstairs."

I follow him upstairs to the bedroom. Pictures of him (younger) with a pretty blonde woman, and two kids. Where is she? But I don't ask.

He points to a door. "Washroom"

"Why don't you get undressed while I freshen up?" I head into the washroom.

I undress, and dig out the lube. I am dry, he does nothing for me, so I slather the lube on making sure to get lots into my pussy. It stings a bit, I shaved today. Have not done that in a while.

I walk out. He says "My wife died two years ago, cancer, this will be my first time with an escort, and the first time since well before she died."

OK, I feel a bit better about the pictures on the staircase.

I pull a condom out of my kit bag. He said "Your ad said no condom if I have a recent clean STD test."

I said "Yes let's see it." He opens the bedside table drawer and pulls it out. It is over a month old, well before my advert. He has been working up to this for a while. A bit of relief, I hate condoms, and really love it when my husband cums in me.

I put the condom back in my kit bag. "There is an extra charge for no condom."

"How much?"

I had been advised by a friend who did escorting and who helped me to prepare for this. "What would you pay?"

"Double? An extra $350."

"That would be acceptable." Jenny had said try for $250, but $100 is common. "Very good, scoot up to the center of the bed please."

"Do you want it now?"

"You look trustworthy, before I leave is fine." I didn't care, I would have done it free, except Jenny said I had to be firm. Particularly about the recent test. His was a bit old.

He shuffles over. I get the lube out of the kit bag. I climb onto the bed next to him apply lube to his penis and start a hand job. He stiffens up nicely. About the same as Tom, a touch bigger than 6 inches. Girth was a bit less than Tom, but he isn't fully erect yet, so both could improve. "Good, I was worried you might have ED."

"I do a bit, but I took a Cialis a couple of hours ago."

"How do you want to start?"

"Let's start with cowgirl."

I smiled, "I like cowgirl."

"I thought you might, it was Laura's favorite. Laura was my wife."

"Regular or reverse?"

"What?"

"Forward cowgirl or reverse cowgirl?"

"Oh, regular, forward."

I straddle him and guide him into me. I maybe overdid the lube; it is leaking out around his penis. Then, my pussy wakes up, I can feel him in me, and it feels good. Maybe this escorting won't be as bad as I thought. I lean forward so my clit rubs on his pubic bone. It feels good. I start bouncing up and down slowly and then gradually increasing the pace. Just as I would do with Tom.

He reaches up and fondles my breasts. Today they were at the bigger point in my cycle. I vary between D and DD depending on where I am in my monthly cycle. It is a pain; I keep having to change bra size. He rubs my nipples and they respond to his touch. That bounces down and excites my pussy. With the bouncing on my clit, I can feel an orgasm building, and I moan. He is clearly pleased to hear me.

"God, I love your breasts. You are bigger than Laura. She was a B cup. I have always wanted to try a girl with bigger breasts. I love it."

I increase the pace, and feel him arching his back, trying to thrust deeper into me. Then I feel his penis stiffen and I know he is about to cum. The first spurt hits my cervix and I cum. The orgasm clamps down on his penis, trying to milk it for all the cum available. I push down onto him and moan, quite a bit louder than last time. Another spurt and a third.

I allow myself to fall forward onto him, careful to keep him deep inside me. "That was good."

"I agree, it is over 10 years since I came like that."

"I am here for an hour, lets see if we can do that again." I start rotating my hips to see if I can keep him hard.

"I would like that."

He starts to soften a bit then the hip movement brings him back up. "What would you like to try next?"

"How about Doggy?"

"Sure, but I don't do anal."

"No problem, Laura wouldn't either."

I lift myself off him and assume the position next to him. I like doggy, but it is harder for my partner to hit my G spot.

He slides into me. My pussy knows this position and starts to quiver. God, it feels good. I think I am going to like being an escort. Tom has been gradually reducing his sex schedule over the last 10 years, and I need more than he now offers. I have talked to him about it several times, things improve for a week or two then slide back to the problem state.

Roger increases his pace, and I can feel another orgasm starting to build, I let out a little moan.

He takes a while to cum, and this time my orgasm is milder. As I clamp down on his penis it is driven out. Pity, I would have preferred him to stay inside while I came.

He collapses on the bed, panting. I collapse beside him, panting.

After a minute I roll over so I am partly on him, and my leg is up against his penis. He fondles my breast.

I ask him some questions to get him talking, and then let him ramble, inserting appropriate comments. After a while, I start stroking his penis. He looks down at my hand. "Optimist", I laugh, he laughs, I am starting to like him.

After a while he starts to harden again.

"What would you like to try this time?"

"It is something I never tried with my wife, never knew how to bring it up."

"OK, let's hear it, if it is not too kinky, we can do it."

"Missionary, but with me standing beside the bed."

I broke out laughing. "Rodger, that is not kinky. I am sure your wife would have agreed, and probably have enjoyed it."

I shuffle around to put my pussy at the edge of the bed, and pull my knees back. He gets off the bed on the other side and walks around. His erection is standing at attention.

"It would help me if you held my leg so I can play with my clit while you are fucking me."

I release my right leg and he takes hold of it. He is a bit tall for this position. "Grab a pillow and put it under my bum." He grabs one of the pillows, I lift my butt and he slips it under me. "Another one.", the second pillow has my pussy at just about the right height.

I reach down, grab his penis and guide it into me. The two pillows have rotated my hips a bit and I feel his penis on my G spot. G spot and clit, this is going to be epic. Normally I get one or the other.

He starts his strokes. Then reaches down and grabs my breast, using his thumb to rub my nipple. I worry about his balance, but he is using the bed as a brace.

I start rubbing my clit and his pace starts to increase. Then I wrap my legs around him so I can pull him in deeper with each stroke. That frees up his other hand and he reaches forward and now has both breasts in hand, and both nipples being excited. G-spot, clit, nipples, G-spot, clit, nipples, I am starting to build for an epic orgasm. I pull with my legs to guide him into a faster stroke.

I am trying to hold an orgasm to let it build a bit longer. Then I feel his penis stiffen and I know he is cumming. He cums and I let the orgasm go. A real bone shaker. I clamp him into me with my legs. We are both really loud.

He spurts three times, and I use that to roll the orgasm around again. Finally, we are spent. Both lying on the bed.

He looks over at me. "My god that was an amazing orgasm. I don't think Laura ever came that hard."

"I am lucky, I have good orgasms."

After a few minutes he asks "How much time left?"

I sit up dig into my kit bag and find my phone. "Ended 15 minutes ago. Do you mind it I have a shower?"

"No, take your time. What do I owe you for the extra time?"

I grab my kit bag and head for the washroom. "I enjoyed myself, let's call it even. I am worried I cannot afford your rate." He laughs.

I let the shower run for several minutes and use the portable shower head to rinse my pussy out, I do not want Tom to know what I have done today.

I get dressed and he is waiting for me, with another envelope. "I really enjoyed today. Here is the second $350 for no condom." He hesitates. "And another hundred for giving me the best sex I have had in decades. Thank you." He leans over and kisses me on the cheek.

"You are welcome, and thank you." I don't count it. I put in my kit bag and leave. $800, this will go a long way to balancing the household budget this month. It will hold off bankruptcy for a couple of weeks. If only Tom could find another job. If only Tom had not blown my inheritance.

Now, I really, really want to be an escort. All I have to do now, is persuade Tom that it is his idea. I do a three-point turn to get the car facing back the way I came. I tell google maps to take me home.