All expenses paid

“Congratulations! You’ve been selected as a lucky winner of an all expense paid trip to Maui where you’ll stay in a resort hotel and spend at least one night with a pornstar!

You’ve been selected to spend the evening with the ever beautiful Lacy. We’ll give you a no limit credit card to use in and around the resort as you woo her with an evening of relaxing, drinking, eating, and more ;) she’s waiting for you!”

The first time I read it I thought it must be fake. I get spam emails like this all the time. There’s no way it’s real. But I didn’t delete it. A few days later I was watching some porn and Lacy came up as a suggested video and I watched it. I had forgotten how hot she is. Watching her take some guys massive cock had me going. I loved watching her petite frame just get pounded. Down I went into a rabbit hole of Lacy. Watching her get lovingly caressed by some and absolutely destroyed by others. I then had a moment of clarity and remembered the email! I don’t know if it was the jerk session endorphins or what but I said fuck it and decided to play along with the little email.

It asked the normal questions and took all my basic info. They said an agent would reach out in a few days.

The next day I get a call from Ashley. She had this sweet confident voice the kind that sends men into battle. And there I was, putty in her hands. With a little more info and a deposit (I guess it’s worth paying for a trip to Maui). She had me scheduled for my trip 2 months down the line.

Now I was still skeptical but I figured a trip to the islands would be nice. Work has been stressful ever since the divorce and I really needed a break.

The flight was average. The attractive flight attendant asked me about my trip and I made up some BS line about it being for business. The guy next to me didn’t want to shut up about his real estate investments. I just wanted to sleep, knowing that if Lacy was actually there I wouldn’t want to be doing much sleeping. I sneak away to the bathroom to get away from mr. Realestate. It might have been the anticipation, or maybe the need to fall asleep, but when I was in the bathroom I pulled out a few saved photos and gifs of Lacy and finished myself off. Does that count as the mile high club?

We finally land and we’re met by these beautiful islanders who give us lais and welcome us to their home and the resort. It’s everything Ashley told me it would be! And if it was true up to the point that means she’s inside waiting to welcome me. I walk in and sitting at a desk in the lobby is Ashley! She’s not quite as hot as I had made her out to be in my mind but she was still a fine piece of work. Very confident. She told me that the stars would be there tomorrow and tonight was a chance for me to meet others at the resort. Apparently there had been 10 or so winners, 6 men and 4 women. Each were paired with a pornstar the following night. Apparently I was a little late and most of the others had already eaten and are paired off back in their rooms.

Ash told me I was the last to show up and she was going to take down her table and get some dinner, and invited me along with her. I of course helped her take down and get everything back to her room with her. She looked exhausted, about ready to collapse. She confessed she’d rather just stay in, so I offered to get us room service. We shared a wonderful conversation and had a great meal! Some local sea food or something. She wanted to take a dip in her balcony hot tub but my suit was back in my room, before I could justify myself she has stripped down and was helping me get out of my own clothes. At that moment she was the most beautiful women I had ever laid eyes on.

We spent about 30 minutes in the tub, drinking wine, laughing, generally enjoying our time together.

As I was getting dried off she kissed me. Totally out of the blue. She said it gets so lonely on these trips and she just wants to spend the night with a man. She hugged me and laid her head on my chest. How could I say no? Next thing I know she’s on her knees blowing me. I fee myself getting solid in her mouth. She pushes me onto the bed, and keeps sucking and stroking. The next thing I know she’s edging me further up the bed as she’s getting on top of me and grinding her shaved pussy along my cock. It feels so good teasing me. Right when I’ve had enough she slides herself down my shaft. It’s no easy task on the first attempt but she was soaking wet and ready to go. She rode my cock for what felt like and eternity as a watched her beautiful breast bounce up and down.

She screamed my name and told me she wants it deeper, harder. So I stood up, and took her from behind, doggy style, hearing our bodies clap together got me so close to the edge. She could sense I was about to cum so she quickly pulled away and got back in front of me. She stroked my cock until I came all over her face. She begged me to kiss her and I obliged, how could I not? We both jumped in the shower and got back into bed with each other. I didn’t make it back to my room until the next morning.

At brunch I met the others in the group, it looks like everyone paired off in couples except for on MFM threesome. Everyone seemed happy. Ashley and I shared a few knowing looks and enjoy the group activities through the day.

Finally it was the evening. And the pornstars finally show up! Lacy and I are paired off and we went to one of the restaurant. She was probably not that into the conversation but I didn’t care because this was my dream girl and if I played my cards right I’d fuck her tonight.

She fawned over my stories and I laughed at her dumb jokes. She was pushing the drinks and trying to get us both over the edge.

Eventually we get back to the room. She strips out of her evening dress and is in the most beautiful set of black lingerie I’ve ever seen. She tells me they usually have strawberries and chocolates in the room for us. And said she like to lay in bed with her men eating the treats while we get each other turned on.

I was already ready to go but I would take it at her pace. We eat a little and she wants to kiss, so we kiss. She taste so sweet, our bodies on each other. She orders me to take off my clothes so there I am butt naked, making out with my favorite pornstar in lingerie.

Now we really get into it. She kissing me, I’m kissing her. I nuzzle her neck and kiss down her body. I caress her ass and breast. She tells me I can pull the panties to the side to get a better feel. Eventually she’s ready and strips everything off. She mounts my face and suddenly we’re 69ing.

I hear the door lock open, and the door creak open. My face is buried in her ass and there’s no was I’m pulling my concentration. I suddenly feel a familiar hand grasp my cock and here Lacy kissing someone. It’s Ashley! Apparently they’ve done this before…

Now I’ve got two beautiful women servicing me. Ashley’s stroking while Lacy sucks and rides my face. I hear Lacy ask how it felt, and ash just gushes over me and brags about how good it felt.

Now they want to know who I think feels better so Lacy lays on her back, legs in the air and let’s me enter her. Holy shit, she felt perfect. I was worried she’d be looser but she get firm and wet. Ash straddled her and pushed her ass against my chest implying she wants me to take her from behind again. I pull myself out of Lacy and enter into Ash. It was beautiful. The varied feeings of their beautiful pussies was exactly what I needed.

We spent the next half hour exploring different positions and trying each other. My favorite was when they were 69ing and I took Lacy from behind while Ashley licked my balls and her clit.

They knew I’d cum soon so they got on their knees in front of me and begged for my cum. I couldn’t decide who to finish on so I just shot at both of them. They were plastered and then began making out and swapping my cum. It was the most beautiful thing I’ve ever seen. We took turns in the shower this time and all jumped in bed together. I had both girls on either side of me.

I didn’t think it could get any better then that…but that’s a story for another time

Source: reddit.com/r/Erotica/comments/mn0634/all_expenses_paid