My Midlife Awakening Pt. 04

In my previous part, I explained how I had sex with a woman for the first time, if you are just reading this story from this chapter because it is in the Lesbian section I would at least recommend reading the 2nd half of Part 3 to explain how I get to this part of my life.

After I got back from vacation I had no interest in hooking up with men and fantasized about women nonstop. I looked up lesbian porn for the first time and read stories about lesbians, and made up my mind I wanted to be with a woman again, but how, I wanted to stay discreet. When I first got back from vacation I kept my distance from Jodi mostly because I felt she would drag me out to hook up again, and I didn't want that, but I finally met her for drinks and to see if she can help me. We met and I confessed ever since my Darna hookups I was obsessed with hooking up with a woman again but was unsure how, and asked if she knew anyone. She laughed making a joke asking what did she think she was a pimp. But she did have a friend a married friend, with kids who was also very discreet, and she could see if she was up for meeting me. A couple of days later Jodi text me that she was up to meet me for coffee, and see where it went from there. Jodi hooked us up by introducing us on, text and we set up a meeting.

Jane and I met for the first time at a Starbucks, she was mid 40's attractive soccer mom type. We chatted for a bit about everything until the conversation turned to why we were together. There was an attraction and we both wanted the same thing, a discreet hookup, with no strings, so we made plans for my house the next day.

The next day Jane came to my house, I wanted this but was also very nervous it was different this time compared to vacation. I welcomed her in and we sat on my couch and made small talk, both of us nervous, until our hands met and Jane made the first move by kissing me. This broke the tension as we made out and eventually removed our clothes, while we performed oral right there on the couch. Afterward, Jane left, but I was hooked and this is what I wanted in my life, sex with a woman. Jane and I would go on to see each other a couple of times a week for a couple of weeks before she stopped it, and explained this was her MO and not me.

With Jane gone and knowing I wanted to be with only a woman now, but still wanted to be discreet it was hard. I looked online for hookups but was very nervous to try, I still went to the gym and was not checking out men anymore but checking out women, and it's when I met Kayla that changed things for me for the better.

I would go to the gym and check out women, but not openly flirt since I was discreet. This one girl there who I thought was very sexy was there when I was there all the time, and I guess I started a lot at her, and eventually, she approached me and started to talk to me. It didn't take long for her to ask me out, and she didn't hold back but asked me out on a date, I told her I was straight, and she grinned and said seriously. I said I was and she said you have been staring at me for a while now, and it's obvious you are not straight maybe still in the closet. This caught me off guard and made me nervous and just said sorry if I sent you mixed signals and walked away.

I went home nervous but excited, and my excitement took over as I masturbated quickly thinking of Kayla and what could have been. I didn't go back to the gym for a couple of days because I was nervous from my interaction but after thinking of it I decided to go back on a Saturday. I saw Kayla and watched her from a distance, she was very sexy about 5 foot, with dark hair, and I had no clue what her ethnicity was, but I wanted her, so I planned to leave as she left the gym. I walked out behind her and said hi, and said sorry about the other day and she said that was alright, and then I told her she was right, I was checking you out, but this is all new to me and I am very discreet, I couldn't believe I just told this stranger this. She smiled and said she can respect discreetness, and that must have been hard for you to say. She then said you up for having a discreet encounter, and I jumped at it and said yes when, and she said now follow me back to my place.

I followed her in my car to her place, not nervous horny, and very wet, I got out of my car and followed her inside. Once inside she took control kissing me and removing our clothes and she guided me to the shower so we can clean up from the gym. We spent a lot of time in the shower going down on each other, before going to her room where she was in control and didn't have the lesbian sex I was used to being gentle but we fucked. Performed a lot of oral, she had a lot of toys and used a strap-on to fuck me. We must have fucked for hours, passing out sleeping waking up to order dinner, and then fucking again and talking a lot. I learned she was 31 openly Bi but preferred women. I stayed most of Sunday where we did most of the same fucking all day using the toy,'s oral, and the strap-on what a weekend.

Kayla and I continued to talk and worked out together at the gym, we would remain friends only as I was not up for an open relationship, but she knew a lot of lesbian women and was going to set me up with a discreet lesbian she knew. She set me up with Sarah who I met for drinks, she was 28 and very attractive. Sarah explained to me that she dated guys but deep down she always knew she was a lesbian and has finally come to terms with it. She was still discreet and not open because of family and work but was looking for a committed relationship.

Sarah and I besides are differences in ages clicked and hooked up and started to date discretely for the next couple of months. The sex was amazing, we got along perfectly and kept this discreet. We both had strong feelings for each other and started to fall in love, but that was until Sarah dropped the bombshell on me that she wanted to have a full-on gay relationship and embrace our love for each other. I thought about this and couldn't come to terms with it and Sarah left me. I was hurt but understood her decision.

I didn't know what was next for me I needed to make a life decision embrace being gay and not care what people thought, or continue down this road and be hurt like I was with Sarah.

I decided I needed to go away on a vacation that would open me up for change again.