I shared the story of how I met my friend in the last story. For simplicity going forward I will refer to him as John (Fake name obviously).

I will share some relevant information I discovered about John during our early discussions as it becomes relevant later. John had 3 children with his ex-wife and their relationship was not great afterwards. When the kids got older and moved away it was just the two of them and he discovered she was having an affair with a friend of theirs. She has since married her affair partner. 2 of their kids also have young kids of their own. All of these people are involved in John's life. John says he was quite depressed and was just kind of going through life on autopilot at this point. Overall his life was not in the best place. When I messaged John he was looking for someone his own age for a serious relationship. I encourage him to keep doing so, and will not interfere if he does meet someone. John stressed that he was happy to enjoy his time with me and have fun while looking for someone to spend his life with.

After our initial meeting, I could see myself continuing to see John, so I decided to make a mental list of what I hoped to accomplish with this situation. I don't think I ever wrote this list on paper as I was too scared of this list being discovered. the list was as follows:

1. Learn about my own pleasure and how to make myself orgasm with a partner to make sex more enjoyable for me.
2. Gain confidence and the ability to be more assertive in sexual relations.
3. Learn how to pleasure others better in order to make sexual relations with me better for my partners.
4. Explore any kinks I am interested in to discover what kind of things I enjoy.

You may think these are silly or naive, but keep in mind I was 18 and in high school at the time. On to what happened next.

I made a plan to go to the local sexual health clinic to get an STI test the next day after school. The clinic I went to is free but it is a "you will hear from us within two weeks if there is an issue" situation. John was evidently a little more eager than I was (he also had more disposable income). John had gone to a clinic that will email you full results within 48 hours. John sent me information on his vasectomy on Tuesday and said he would provide the STI results by Thursday. I let him know my results would take longer and advised of the timeframe. He told me that due to my limited sexual history (which I had shared with him) and how concerned and aware of STIs I was, that he would be willing to move forward before my results came in. We made tentative plans for Friday. I advised my parents of my intentions to have a sleepover with my best friend, and figured I would go there whenever I left John's. I am 100% honest with her, as she is with me, so she knew everything about where I would be and who I would be with. I feel this is important for everyone as it helps to keep you safe.

Sure enough, on Thursday John sent me his results showing he didn't have anything. I had my own phone and paid for it myself with a job I had at the time if anyone is wondering why I was bold enough to send and receive messages with John. I confirmed I would see John on Friday afternoon and continued with my day.

The next day, I had butterflies all through my day of school. I was nervous all over again. Less so than I was the first time. I hoped with each time, I would become less and less nervous. Finally school was over and I headed over to John's extremely nervous and excited. I got there and pulled into John's garage. I entered and John reiterated how gorgeous he thought I was. This excited me and I was quick to start stripping in what I thought was a sexy way to entice John. Evidently this worked as I think he stripped faster than I did. We kissed and touched a little, then he told me to sit and slouch on the couch. He kissed down from my mouth, paying a great deal of attention to my nipples which got me super excited. John then slowly moved down to his knees and brought his head down and OH MY GOD! I had never really been eaten out before. His tongue running over my clit was AMAZING. He licked and licked and slid a finger inside me. This felt incredible and it wasn't long before I orgasmed. John was not deterred and kept going. I had never been making noises like this or squirming like this. This was by far my best sexual experience up until this point in time. I had always felt like it was greedy or selfish to ask a partner to go down on me, but John needed no encouragement. After I don't know how long and several more orgasms, John started to slow down, suspecting his tongue/fingers were tired, I said we should switch places. John was quick to go with my suggestion and soon I was standing over him sitting on the couch.

I lowered myself to my knees and grabbed John. I rubbed him in my cleavage and against my nipples. John was leaking precum all over me which was so hot! I got into position and nervously brought my mouth down onto him. I had tried this before, but always felt like I didn't know what I was doing and wasn't very good. John let out a moan as I started to bob up and down on him. After a few minutes John said that I should kiss and lick up and down the shaft and around the head. I was very eager to please, so I did this without hesitation, thankful that John had trimmed his pubic hair since the last time we had seen each other. John said I should hold his balls in my other had and I did so, being very careful to try not to hurt them. I had asked John to give me pointers so it's not like he was being rude or disrespectful to me. After another 5-10 minutes John suggested we go to the bedroom to try 69ing.

We got up to the bedroom and John laid on the bed. I got on top of him and started to blow him. I really enjoyed pleasuring him while he pleasured me. I enjoyed this, but the position wasn't my favorite. After a few minutes I asked if I could try riding him. John said he was happy to do whatever I wanted to. I got off of him and turned around. I straddled him and slid him up inside me. Feeling a dick with no condom on it was also pretty amazing! I had never had unprotected sex before. I wanted to just try different motions riding to see what I liked. John was very patient while I tried different things. It turns out moving back and forth or trying to grind down in circles was what felt the best, far better then bouncing up and down on the shaft. I asked if John would be ok if I touched myself while I was on top of him. He eagerly said yes, and I reached down to rub my clit. This was an incredible feeling and soon I was orgasming over and over again all over him. Looking at Johns face I could tell he was loving this. I decided it was time for his turn. I leaned forward over him and my boobs hung down over his face. He eagerly tried to suck my nipples as I bounced my hips up and down on him. I was trying to make John cum but my hips were pretty sore by this point. I told John this and asked if there was a different position he would like. He asked my to stand and lean forward over his bed which was high. I did so and felt his tip pushing and rubbing against my lips. I think I moaned and told him to fill me up which he was quick to oblige. He started to pound me hard and before I felt the pulsing and the sudden influx of cum into me. This also felt amazing and I had one final orgasm when he did this.

After this we laid in bed naked chatting for a bit. John admitted to masturbating several times today in order to last longer when we had sex. I asked if everything I did was alright and John reassured me that he enjoyed it and that I was welcome to continue to use him to explore. We showered together and he eagerly washed me down before I headed back to my best friends place.

This was what happened during our second encounter. I won't write a story about every encounter as that would take way too long and probably be very boring. I will post a few different stories though as some are very notable. These include when I helped John get revenge on his ex wife, as well as what is by far my most extreme night. That is a long story and took place not very long ago so I will have to make my way to that one.

Hopefully someone finds my story enjoyable or helpful. I will continue to post these as I enjoy writing them out. I will leave the story here for now though. I welcome any questions or comments but do not wish to meet up or share photos or nudes with anyone.

Thanks and I will be back.