This all started about 3 years about just prior to our second child being born. Tiffany was in the last trimester of her pregnancy and sex had become extremely uncomfortable for her. My dick would feel like a knife in her with how her body shifted things around. This of course led to a lot of sexless nights and me being left to figure it out myself. Also, as some background information my wife Tiffany and I have been together for over 15 years, we are high school sweethearts. So we are quite comfortable sexually with each other now.
During one of these nights I was in the basement watching the baseball game and Tiffany being very pregnant was in bed. I began to playfully sext her and noted that it was tough for me and if she could help me out. Tiffany agreed, and I started asking her dirty questions and asking for nude pictures. The one question that started everything was “Have you ever masturbated to someone you know?” Tiffany responded with a “Nope, never!” I couldn’t believe it. I couldn’t believe that she never thought of anyone. She explained that she felt gross for some reason masturbating, and when she did it was always to porn. She immediately probed me and asked if I had. I responded with “lol of course I have, I’m a guy though”.
Without any hesitation she followed up with “who”?
I responded with “lots of girls to be honest over the years” I could see that she was typing something, going back and forth trying to figure out what to say or sorting out the feelings of what I had said. I was frankly I little worried I’d upset her.
Finally she responds with “Who was the last girl that we know who you jerked off to?”
I had to give that some serious thought. I immediately knew who was in my mind and why but should I tell her? Was this a trap? Is this emotional cheating? Maybe it was my hard dick talking but I responded truthfully to her and told her it was her friend from out east Charlotte. I explained that I found Charlotte kind of trashy but hot in a slutty way. She seemed to be the girl that would fuck someone on the first date and I knew from Tiffany telling me herself that Charlotte had been unfaithful to a few of her boyfriends in the past and screwed around. After sending it I kind of instantly thought I was screwed, what was I thinking saying all of this to her. As the seconds tick by Tiffany responds with “that actually turned me on a bit, I wasn’t expecting you to say her”.
We go back and forth over the next 15 minutes getting even dirtier swapping pictures of Charlotte that turn us on and what features we each like. I ask Tiffany if you were to fuck her how would it happen. She responds with “ it would have probably happened at our old condo. It would have been so easy with you at work. As she didn’t have a boyfriend at the time and she was such a slut, she would have been begging to be fucked”
I responded with “ I want you to look at the picture of her that turns you on the most and cum thinking of fucking her” a minute goes by and she sends a message for me to come upstairs and feel how wet her pussy is. My mind is blown at this point and I am so turned on. I can’t believe what has just happened. I go upstairs and feel that she is absolutely soaked. I immediately start to finger her and cum over her tits.
Over the next few weeks Tiffany and I cannot get enough of our dirty texting. I text her girls that we know and have her order them in the order of most fuckable to least. Over that time and more of the same above we come up with a list of four girls that we regularly get off to together and also she is fantasizing about. Two are friends of hers and mine, another is a old coworker, and the one we have currently got off to the most is her old boss.
Her old boss is by far the most naughty one of them all. I remember clearly originally texting her name to Tiffany asking her to rank her. Tiffany immediately shot it down and would not even consider her. Her old boss Susan was 20 years older than Tiffany and was almost like a good friend more than a boss. Susan though was quite good looking herself for her age, blonde hair, blue eyes, pretty face, nice body for her age, and of course a good pair of large tits. I still remember the night before Tiffany got off to her for the first time. We were driving into town to get some groceries and out of know where Tiffany mentions she cannot believe how I mentioned her old boss Susan and how that was so “offside”. I apologized but the wheels in the back on my head started turning.
Later that night Tiffany and I are in the middle of fucking. I’m slowly fucking her from my side grabbing her tits and making out with her neck. Tiffany is getting really hot as I am dirty talking at that point about Charlotte. As I am pumping my cock inside and out of her I say “I know you want to talk about your old boss Susan and that you want to eat her soft pussy out”. I can feel a change in Tiffany’s body, she starts to become extremely hot and I can now hear how wet her pussy is with each pump of my dick.
Tiffany responds with “oh my god, I do! How did you know it’s so fucked up!”
I respond with “I knew my dirty little slut would. You want to lick her soft pussy and suck her big tits don’t you?”
She moans “ I want to lick her pussy so bad. I’d love to suck her big tits” Tiffany then turns me on my back and starts to ride me. I keep describing how she wants to fuck her old boss and she gets closer and closer to orgasm. Right before she explodes in pleasure I grab my phone and ask her if she wants to cum looking at a picture of her old boss. I was a little bad and saved one prior to us fucking. Tiffany says in desperation as she moans “I want to see her, I want to cum thinking of fucking her” I show her the photo and she starts to convulse in a orgasm that seemed to last 15 seconds. She then rolls off me and has the biggest naughtiest smile. It was incredibly hot.
We continue to do this today, not all the time but quite a bit. Changing up who we are thinking of but mainly circling back to Susan. Tiffany has even admitted to me getting off by herself to these thoughts. I don’t know where this will take us but my god it is fucking hot.
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