I like younger women but I also **love** a good challenge. I started talking to her a few weeks ago She was very shy in the beginning but after a few days of texting, she tells me that she has a long time BF. They are very serious and live together. I assumed my chances were short. She is 24 years old, 5’5 long brown hair, doe eyes, and an amazing size 5 body. As we talk more, I realize that she is not happy with her BF. I am someone that she finds very attractive, but has never been with an older guy, but “Has daddy issues”. I am not overweight but not fit either. I am active, but I also am 37 and sit most of the day. I am the opposite of her BF who is 26, and works construction & hits the gym.
I still think it is “too good to be true”. Maybe I am being played, maybe she is not who she says she is in the pictures. We talk on the phone a few times and she sounds like who I expected. We exchange some pictures including a few PG ones, but no nudes. She is nervous, and I am not a “dick pic” guy. After about a week, I start pushing for a face to face meeting. She didn’t want to meet up because she didn’t know what to tell her BF as to why she was not going to be home AND we scared that someone would see her in public. All her friends know him, he talks to them, and she couldn’t help with a good story. Well, we landed on a “Babysitting” Job. I even had to text her real number to pose as the father who needed my kids watched.
We worked that out, then onto the date. I can’t convince her to meet at a restaurant, so we settle on the meet at an upscale hotel. We eat dinner at the restaurant, and if we “Click” then we go upstairs. I had to drive about 90 mins to meet her so I decided to get a room anyway. I wanted her to come up, but no pressure.
I arrive about 1/2 hour before the date and check-in. I go up and get ready. She texts me that she about on her way. I head to the lobby and sit down in an oversized chair. I let her know I am ready. I wait. Nothing. She says 10 mins later that she arrived. I wait. 5 mins later, I ask if she is coming in soon. Nothing. I wait. 15 mins later she walks in, and I give her a hug. She looks amazing. Hair straightened making her small frame look even thinner. Black cocktail dress, cut short, with a low cropped top. Good balance of cleavage. We walk into the restaurant and start by ordering a bottle of wine, and an appetizer. I try to make myself appear as open as I can. Not crossing my arms or legs. I sat in the seat next to her, not across. We start talking and I see she is starting to get more comfortable. By the time we are getting to dinner, she is good. Smiling and laughing. As I am finishing my food, I excuse myself to the restroom, but I lean in and give her a quick kiss as I walk away with my hand pressed on her back. I come back, and we talk some more. After about 15 mins more, I say “What would you like to do now?” she pauses and says “I am not sure. What did you have in mind?”. I smile and say “Honestly, I like you, and I want you to come up to my room”. She says “What are the expectations?”, “None, I just want to talk more in private and kiss you more,” I say with a smile. She says she will be back she wants to Facetime a friend.
For the first time in this whole process, I am nervous. I want to fuck her BADLY! I know that a friend can make or break this. I assume she is going to tell her this is a VERY BAD idea and remind her that she has a BF and that I am 10+ years older than her. I sip my wine, and wait and wait. She walks back and looks even better. I can tell she put on more perfume and she sits down. I wait for her to speak……..Finally. “No expectations right?” she says, I quickly say “NONE!”. I grab her hand and head to the elevators. I am not going to let her think about it too long. We get on the elevator, doors close, and I press her against the wall. I put on hand in her hair and starting kissing her. 2 or 3 kisses in, and her mouth opens wide and our tongues are touching. The doors open and I let her walk off first. I adjust my cock as it has already started getting hard as AF form the kissing while I watch her sexy little ass walk. I let my hand gently touch its I walk off and grab her hand as we walk to the room. We arrive at the room, and I give her a quick kiss as I unlock the door.
As we walk into the sitting room(The suite was like a living room area, and the bedroom), her friend starts to facetime her again. She sits down the sofa and asks if it is okay to answer. I say sure, and I go into the bathroom off the bedroom. I can’t hear her talking, but I wash up. I walk back out a few moments later and she is still talking to her. I sit over in the corner so that her friend can’t see me on facetime. They hang up 2 mins later and I join her on the sofa. I say the I am glad she is less nervous, and I start kissing her again. This time I am letting my hand run all over her the tights she has on. They are black too. I start pushing her dress up, and when it gets too high she pulls it back down. We talk for a few mins, then kiss more. This goes on for about 20 mins, with the touching getting more sexual. “I thought you said you had no expectations,” she says after I had been touching her ass as we were making out. “I said, I have no expectations, but that doesn’t mean that I don’t have a wants,” I say with smile. “I want you…I want you ALL of you and I have for weeks” I say. I think that was the moment she decided she was IN!!
**”Well, I am yours Daddy”** she says with a large smile. It takes me a moment to let those words settle in. I push her over on the sofa, and start kissing her legs and move my way up her legs. I finally get a good feeling between her legs and WOW was she damp. I grab her tights and pull them off. Revealing a small tight blue thong that is wet and sticking to her pussy. I spread her legs wide open and start rubbing my thumb off the fabric as I kiss her belly piercing and as I push her dress up. She pulls it off over her head and I kiss her 32B breasts while still in her baby blue bra. I stop teasing between her legs to kiss her some and unhook her bra. I pull it off and kiss each breast softly. I lick each nipple and give them a squeeze. I then work my way back down her body and slide her thong off, finally getting to see her pussy. It glistens in the soft light and is very wet. I waste no time licking the outsides and then while one hand on each leg pushing her WIDE open, I just slide tongue in all the way. I spend a good 10 mins, licking and kissing every inch of her tight pussy. At this point, I am still dressed and my cock is throbbing and pressing on my dress hands. I can’t take it anymore, and stop and move my cock to her face. I undo my belt and pull my dress pants and boxers down in one motion. My rock hard dick springs out and is now over her face. She grags it with both her hands and slides it into her mouth. She slides her tongue all over the head and bottom. As I bend over to get the right angle she kisses my balls and cups them in her hand. I start slowly sliding my cock in and out of her mouth. Letting her guide me. I feel her tongue just sliding over the bottom of my shaft. I can barely hold it together, so I pull out and tell her that I want her completely naked on my bed. I sit down on the sofa to undress and watch her walk her beautiful ass into the other room. I quickly unbutton my dress shirt and pull off my undershirt. I get my pants and socks off. I stand up, and stroke my cock a few times as I walk into the other room.
I walk into the bedroom to a sight I hope I never forget. She is at the end of the bed on her knees. Ass pointing straight in the air, legs shoulder-width apart. She has one pillow and her face is in it. I walk over and stand between her legs. I bend down and lick in one motion from the bottom of her wet pussy to her pink asshole. Then I stand up and slap her ass. “Is this good Daddy” she lifts her head and looks at me with her large round eyes. “This is great,” I say. I put on a condom as I slide my thumb into her pussy. I lean over and grab a handful of her hair, and with my other hand, I grab my dick in my hand and press it against her pussy. I start sliding in and she is squeezing my cock on the way around. I slide all the way in and I start to hear her moan into the pillow. I pull out all the way and do it again. Ater the 3rd time, she yells “Fuck my Daddy PLEASE”. That is all I needed and pull her hair and slide myself into I start picking up the pace over and over again. Slapping her ass every 10-12 trusts. I can feel my dick starting to throb. I try my best to change the speed, but between how tight she is and the moaning and the sight of her in this angle, I can’t take it. I pause and “Yell rollover” she quickly throws herself on her back and I rip off the condom. I stand between her legs and stroke my dick. She sits up and sticks her tongue out. I start to shoot my load all over her chest and some hit her face. I unload making a huge mess. She sits up all the way and grabs my throbbing dick and pushes it into her mouth and starts to lick every inch clean.
She then climbs up the bed and pulls the covers down and we climb under the sheets. She presses her ass on my dick and I wrap my arms around each other. I fall asleep like that.
I wake up at 12:30 and tell her she might want to get up. She is in shock that we fell asleep, and we quickly get dressed. She watches off the cum quickly with a face cloth. I walk her to her car, where we exchange a few long kisses. She texts me 30 mins later that she is home but her BF is pissed that the babysitting job went so late. We both had a good laugh.
We are working on date two now.
Source: reddit.com/r/gonewildstories/comments/fg1ky6/i_convinced_her_to_cheat_on_her_bf_mf
Awesome story! Very exciting to hear the date went so well. Gonna give. A follow and hope for updates
Great story, hopefully round 2 is just as much fun!