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My Hook up Story with an older woman - Kensington
Monday, 24 August 2026
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City:
Kensington, Gauteng
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I’ve been both with woman my age (35-40) and matured women (50 plus) and I say confidently say, mature women give the best sex. I’ve been with older women since my high school days, my first was my English teacher, ever since I tasted her mature pussy I never looked back. So let me tell you about my story with Thandi, she a 58 year old corporate woman who is divorced and lives in Kensington area. I met Thandi in Braamfontein at some government offices. She was there for a meeting and I was there to deliver some files. The minute I laid my eyes on her, i immediately felt a certain way, ahe was the type of an older woman i would go for. She was a perfect BBW, on the day she was wearing this dressed that perfectly fit her showing off her big sexy booty. I knew I had to make a move on her l, it was now or never, chances of me seeing her again were zero. Ad we were both waiting for the lift to go downstairs, I smiled at her and said, you make that dress look good, she laughed and said thank you, I knew this was my opportunity, I told her my name she told me hers, her welcoming smile gave me courage that I can make a move on her. We both got into a lift, as there were people in the lift i just kept eye contact with her, I could tell there was chemistry between us, she kept on smiling. We both got off the lift and immediately I ran to her and asked her for her number. As I approached her, I smiled and said to her “ look chances of seeing you again are zero and I would really love to have your contacts” she smiled and said young man you the same age as my son, I smiled and said, there is no age restriction at the coffee shop… I just wanna have coffee with you… at this point I could tell she already liked me.. she gave me her number.. later that night I text her. We got to know each other more… as the conversation progressed. There was this sexual connection that was developing. she asked me what I was doing, I told her that I chilling in bed, thinking about her… she asked me what was I thinking about exactly, I told her that I could not stop thinking about her sexy booty and how much I would love to give her a massage right now. She laughed and told me I don’t waste time, as we just met today and already Im offering her a massage. She told me that she was too old enough to be my mother for me to give her a massage, I told her that In my experience in the presents of chemistry age disappeares and that I can feel the chemistry between us was developing, I how much I would like to be with her. I could her in her voice that she really loves the moment and the chemistry that was developing. She told me tagt she really liked me and how I approached her, that showed respect and she appreciated that and that I made her feel wanted and appreciated. She said she hasnt been made to feeel that way for a while. I tease her by saying i can actually make you feel in ways that no one has ever made you feel, she laughed and said, don’t say something that you can not follow through on. I dare her to aske me, she laughed and asked, what you want me to say, I told her that I can give her the best sexting experience ever, that I can make her come over the phone. She asked, are you that good? I said, try me. She laughed and said, please stop teasing me, im getting too excited now. She asked that if we can talk tomorrow, as I did not want to come across too pushy i obliged. At this point my dick was had as a rock.
Fast forward, i received a WhatsApp message when I woke up around 6:30 saying Im working from home today, our conversation last night kept me up.. i would really love that massage… I text her back and told her will be there at 08:00 and asked her for her pin location. I got myself ready as soon as i could. I requested and uber made my way to her place. Got there, she opened the gate for me. I went inside, I was welcomed by a smile, her welcoming smile got me excited, she offered me coffee. I smiled and said, Im pretty sure you desperately need that massage. She laughed and said, definitely, she asked me to follow her to her bedroom. Ad I walked in she closed the door behind me. The lights were still on as the room was still dark. Her intentions were clear, she wanted to fuck, as I walked in she pull down her gown, I was exposed to her naked body, gosh she was sexy, a perfect mature body that I love, her pussy was clean shaved, she was curvy with big booty. I dream booty for a young man to explore. She said come here, as I approached she grabbed me a kissed me, l retuned the passionate kiss. I grabbed her big booty and pressed her against my dick as I was kissing her, she looked me in the eyes and a grabbed my dick and said I want this inside me. She took off my shirt as I was taking down my jeans. As we both got naked, we got onto the bed, I continue kissing her while I was between her thick thighs. She rubbed my dick against her virgina entrance, I could feel her getting wetter. I continued kissing her while playing with her virgina, she was mourning with joy. I could see in her eyes and she was enjoying every stroke with my fingers. I could feel her thick mature thighs vibrating with excitement. At this point I was also excited with joy, I have me pleasure seeing how much joy i was giving her, the look in her face gave me joy, tge feeling of me making this older woman felt this way excited me, it gave me more energy to pleasure her even more.
I stopped and reach my Jen’s for condoms, as put the condom on, she was laying on bed with her thighs wide open. Got back on the bed, got on my kneel before her virgina, opened her legs wide and started rubbing my dick on her virgina while playing with her breast. The joy on her mature face was telling, as she got wet, I penetrated her slowly, I could feel her warm juicy pussy as I thrust her slowly in a missionary position (by the way I love missionary) as go deeper inside her I could feel the joy in her mourning, she was enjoying me inside her, she grabbed me towards her and she started thrusting me upwards. We were both thrusting each other. Her virgina was dripping with juicy with every thrust. Our bodies were so thighs to each other that we both grabbed each other so tight. She asked me to turned her around and fuck her from behind, I started bounding her big booty, with my every pound her booty was clapping, and the view of her booty clapping got me even more excited, I pounded her harder she was screaming with joy, asking me to fuck her even harder in Zulu, “ngidle baby, elakho le khekhe” I could feel I was coming, I pull back a bit as I wanted to enjoy her more, I flipped her back to my favorite position the missionary.
We kissed all over again, she grabbed my dick and slide it in her. As I thrust her again, she was matching my thrusting rhythm upwards, I grabbed her thick booty as I was thrusting her deeper, and she wrapped her leg around me. Her virgina was wet and I was feeling my come getting closer with my every stroke… My stroke rhythm increased as I was getting excited, she could feel i was coming and she grabbed me harder and continue to thrust me, her mourning was getting louder and she was screaming saying, come for me my babe, come for mommy, my is enjoying your dick, mommy loves your dick, her words got me too excited and I pounded her harder as I was coming…. As I was coming she continued thrusting me till all my load was gone. She kissed me and smiled and said, I want more, i said we have the whole day… she smiled and said this is going to be a great day.
…. The next story, Work trip with her…-
