So I was curious about being with an older woman and finally started to turn the fantasy into reality when I turned 18. I would go up to older women at stores, clubs, and in public. But I had no luck. That was until I met an older woman, Lisa.
I messaged Lisa on a Saturday and booked an appointment for the following Monday. I was excited for this cause this might be the solution to my pain. I went to Lisa on Monday and met with her. We talked about my pain and she took me to the table instantly. She wanted me to strip down to only my boxers since she was going to use oil.
Lisa began rubbing my back and I could feel how gentle her hands were. She finished rubbing my entire back and I instantly felt relieved. I thanked her and paid her for her work.
I began seeing Lisa twice a week after that appointment. Lisa and I began forming a relationship and we started being more open when talking. About a month passed of doing the massages and Lisa and I were talking more open. She would often talk about how she was feeling and about her work. Lisa would also compliment me often.
I was in the best shape at the time and she’d always say I had a nice body. I started to get risky with it and would flirt with her too. I would say she looked really good or that her outfit looked nice. She had a curvy figure so I’d always stare.
One night I was feeling risky and decided to text her. I told her that I could not keep my eyes off her during the session to which she replied “you’re too sweet.” I told her how her outfit really looked good on her and she responded immediately asking if I meant it. I left it at that and decided to get more flirty with her for the next session.
So I go over to Lisa’s place for my session and could already feel the tension. Lisa was wearing a shirt that showed some cleavage and pants that made her ass look so round. I got a chub for the entire session and told her she looked sexy. Lisa blushed a bit and smiled. We chatted in such a flirty way the entire session. She asked me if I had a girlfriend and I said no. And I asked her if she was into younger guys. She took a second to respond and I thought I ruined my chance but she said yes in a seductive way.
That same night we texted a lot and she sent revealing pictures. We planned going to her place the next night. I got to her place the night and was super nervous. I knocked on her door and saw her in a tank top and sweat pants. I could see her nipples through her shirt and started to throb. As soon as I walked in, we got to business. She was a passionate kisser and loved teasing with her tongue. Soon she was on top of me making out.
I pulled her tank top down and started kissing on her tits. Then she took my shirt off and told me to take her pants off. I obeyed and immediately saw her bright pink panties. I took my pants off and started to rub against her. I took her panties off and my boxers. She got on all fours and I began to eat her from the back. Her pussy looked so good. She then told me to fuck her in a demanding way. I did not hesitate and slowly started to slide inside her doggy style.
Her pussy was tight and wet. She took control and was throwing it back. Her round ass looked so good jiggling. I then got under her and she got on top and began riding me. My cock throbbed with each stroke because her tits were in my face. I was about to cum when she got and started sucking my cock. Her lips were so soft and she knew how to pleasure me. I started telling her that I was about to cum and she instantly started deep throating my cock. I came so hard in her throat and she enjoyed every drop.
After fucking we cleaned up and I headed out to go home. she texted me saying it was fun and that we should do it again
Source: reddit.com/r/gonewildstories/comments/w0vu77/my_19m_first_time_with_an_older_woman_57f_mf
How many more times did you two connect?