A BIG thank you to SillyEmily for the editing!
--------------------------------------------------------------
It all started innocently enough. We were both at a High School marketing group's event. We were from different schools but were put into the same group when we arrived. You were a redhead girl from the middle of the state, and I was a dark brown hair boy from up North near the lake.
We hit it off right away and the time went by quickly and we became fast friends. Throughout our Senior year we would meet up at several events. We'd be at the same marketing competitions, seminars, and leadership training.
Fast forward 20 plus years later. I am just randomly looking through my Messenger app when I see a pending message request that​​ I'd never looked at before from you. The message asked if I remembered you, as if the pretty redhead girl that I'd held hands with and that had always been a memory could ever be forgotten.
So, even though it had been 3 months since the message was sent to me, I responded saying that I did in fact remember you and was happy to hear from you. I had a message back from you the next day and we went back and forth catching up. You were married to your HS sweetheart and had two boys while I was married to my college sweetheart and had three kids, two boys and a girl.
We talked regularly over messaging apps and text messages often. Most often talking during the day as we were both less busy when we were working. Some conversations while at home, but the main time was when we were both at work. As we became more familiar with each other we became good friends. Such good friends that we weren't telling our partners about it.
We were talking about EVERYTHING, often complaining about our spouse's treatment of us. You shared how husband loved to show you off in public and even took you to a swinger's club but would get jealous when you were the center of attention. Meanwhile I'd complain about how my wife was barely interested in sex and when we had sex, I had to do all the work and how bland she was.
You and I both wanted to swing with others and then go home and use that to expand our sex lives at home. ​​Eventually we began to share pictures and videos of each other and our spouses. It began with just the normal Facebook pictures but eventually lead to pics of ourselves totally nude and even having sex with our partners.
The videos of you moaning while getting railed always turned me on. We even began talking on the phone and having many steamy discussions explaining things we'd like to try which eventually led to talking dirty to and about one another.
After eight or nine months of continued expansion of the relationship your husband found out and shut us down. You went about repairing your relationship and I went back to my life. I tried to contact you many times but failed, and eventually gave up on ever talking again.
I honestly became depressed because I lost such a good friend and because my marriage wasn't good. I was one of those "staying for the kids" people. My wife and I never communicated, when we did it wasn't good, and we mostly stayed busy to avoid each other. I'd stepped out on her a few times as I was trying to find ways to connect with people again since it wasn't ever happening at home.
Everything changed one day when I woke up to a message on a Saturday morning. Your husband had passed away the night before and you needed a friend. I spent almost the entire day talking with you both via messaging and on the phone. We arranged for me to come and see you the next day even though you lived two hours away and we were in the midst of Covid.
​​I made up a story for my wife which allowed me​ to go two hours away on my own and ​​I was off and met you about 40 min from your house. With the Covid closures ​​we decided to meet in a parking lot and just talk in your car.
In your car I provided you ​​with a shoulder to cry on and I held you for quite some time. Yet somehow after all of that and our discussions about everything we ended up kissing. I asked you if it would be ok and you told me that if I didn't start soon you were going to. (It didn't take a rocket scientist to feel the sexual chemistry between us.) With the kissing came some fondling by both of us.
My hands roamed to your covered breasts, and I could tell you were enjoying it. You were feeling my erection through my shorts. As our mouths and tongues explored one another I got my right hand under your shirt and freed your left breast and massaged it as you moaned. I unlocked my lips long enough to get a taste of your rock-hard nipples.
However, I couldn't leave your lips for long, so I covered your perky breasts and made out with you once again as my right hand explored further south. I reached inside the top band of your leggings and found you were pantie less and smooth cunt. You were moaning as we kissed, and my fingers were exploring your lower lips. Your breathing increased and were close to cumming - but just couldn't get there.
You explained later as we talked on the phone on my way home that the chances of getting caught kept you from reaching that orgasm. Apparently, that was also the only thing that kept you from sucking my cock right there and then.
I vowed to be there for you however I could over the next few weeks. We were back to our normal friendship, and I was helping you make decisions with the funeral and even livestreamed the funeral and the celebration of life from home. We talked whenever we had time and I helped you get through deciding on meals, walking into a store by yourself, handling your in-laws and so much more.
We also had numerous sexual talks which often lead to one or both of us masturbating to the other's descriptions of what they were doing to themself or what we'd want to do to one another. You also had several breakdowns, and I was there for support any time I was needed. And during all of that we got closer and closer.
Eventually we decided to get together again but due to the forecast for lots of rain the day we were to meet and the pandemic we were not sure what to do. We kicked around meeting up at a hotel and eventually decided to do just that in a town in the middle of our two locations. I told you repeatedly that nothing needed to happen and that I just wanted to be there for you and be able to sit with you.
We both took the day off work and met at the hotel late in the morning. You had booked the hotel and so after checking in you had me meet you at the elevator. As soon as the doors closed, we were making out! We gathered ourselves enough to be able to walk down the hall to the room.
The second the door closed we were making out again! Eventually we made our way to the sectional and were really making out and our hands were all over each other! My hands were mauling your breasts through your shirt while also traveling down to get a handful of your ass.
I don't know who stripped the other person of their clothing first, but I know that you were down on your knees in front of me with my cock in your mouth quickly! Your cock sucking skills were on full display as you looked into my eyes while licking my cock head. Then you got a little smile on your face and swallowed my cock almost whole! I almost blew my load right away, but I wanted to last longer so I made you stop so I could get to your pleasure.
We made out for a minute or two while I took off your jeans and began to play with your pussy. I knew from our previous conversations that you'd had your pubic hair surgically removed and so I knew I had to get a closer look. My mouth was attacking your pussy in no time. I was nibbling and sucking on your pussy lips which caused you to moan like crazy.
Your hands were pulling my head even more into your pussy and I was fully enjoying your juices flowing into my mouth along with the sweet smell it was emitting! I was in heaven and apparently so were you as you were pounding your fist into the cushions while also flooding my mouth with your juices.
Eventually you pushed me away and told me to sit on the sectional. I wasted no time in doing so and you mounted me right away. You were so tight and smooth, and I was in heaven. I had your ass in my hands, your swaying breasts in my face, and my cock in your pussy. You were yelling out loud how thick my cock was and how it was stretching you out and how badly you'd wanted it in you! I was battling to hold out until you gripped my balls and stroked them and told me to shoot. And shoot I did! We both got off together at that moment and you collapsed on me. We kissed and enjoyed the afterglow for a few minutes.
After a few minutes we cleaned ourselves up and went back to talking. Eventually we both ended up in bed talking again about that last experience, discussing how long we'd both wanted to do that, and you kept complimenting me on my cock thickness while I explained how much I enjoyed your smooth, soaking wet pussy.
Again, the talking led to kissing, which led to making out, and eventually led to fondling each other again. My hands were squeezing your breasts and playing with your nipples. You were stroking my cock and making sure he was alive again -- which wasn't a problem as I was in bed with a beautiful woman.
I eventually laid you on your back and worked my tongue from your mouth to your breasts and back down to your sweet pussy. ​​You didn't allow me to keep going for too long, as you looked me in the face and told me you wanted me in you again right now!
So, I moved up your body until my cock was lined up with your pussy and stuck it in between your moist folds again. I was buried in you right away and you were pulling my ass forward as we made out! I was pumping in and out of you like a jackhammer and you were moaning like crazy! It wasn't long before you were screaming again and with that, I shot my cum inside you again. I kept going for a few minutes before finally deciding that I needed to leave your pussy for a bit.