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First Time Handjob Holiday

Posted by: Age: 18 then Posted on: 3 comments
12 likes 208 views Category: Masturbation Male-Female Tags: Male-Female, Masturbation Male-Female, handjob, milf,

I've read a lot of 'first time' stories so I thought I'd add mine.


I've read a lot about peoples 'first times' and felt like I should join in. It's a memory I still jack off to this day. I was 18 at the time and it was my mother friend. It began when my moms friend would flirt with me. At first it was just joking and in front of my mom, however looking back I realised there were many moments when 'my mom wasn't home yet'. I remember enjoying the flirting but not really seeing it for what it is.

Let me fill you in on what she was like, lets call her DD. DD was in her 30's. She had long straight brown hair. She had a very large set of breasts. She didn't show them off all the time but when she did my mom would always joke about it and tell me to look away. One summer DD had asked my mom to go with her to a villa in Spain. Someone in her family owned it. My mom instantly agreed and we all went. At first it was a lot of hanging out, heading to the beach. Just relaxing. They would both sunbath topless around the villa. it wasn't a big deal as in Europe you grow up around topless sunbathing. However I did enjoy seeing DD put lotion on her tits. I spent a lot of time jerking off.

One day my mom had decided to go into the town. DD and I stayed at home. I was having a shower and thinking about DD. I purposely left the door unlocked and slightly open. From the corridor you could see straight into the shower. I began stroking my cock. I didn't want to cum, I just wanted to make sure she saw me hard. Then I saw movement. DD shouted 'I can see what your playing with in there!' My heart pounded. I pretended I couldn't hear 'What?' I shouted back.

DD stood in the doorway in her bikini bottoms. She watched me stroke my ridged cock. She started playing with herself with her hand down her bikini bottoms. With the other hand she rubbed her nipple. She then stopped and told me to get out the shower. Without hesitation I did as told. She looked at my cock and said 'you are so hard!' Next she kneeled down, spat on her palm, grabbed my cock and began stroking. I am un circumcised so the head of my cock is very sensitive. She pulled the foreskin back and worked it. My body twitched. I think she thought I'd done this before because when I shot multiple ropes of cum over the shower room floor and her, she was a little surprised.

I told her that was my first hand job. She smiled and said 'fuck that's hot'. We both knew my mom might be back soon but it didn't stop her from carrying on the fun. We kissed and her breasts pushed up close to me. I was getting hard again. She went for the baby oil by the sink and proceeded to rub it on her hands then began to caress my balls and shaft. It felt amazing. She kept saying how I'd turned into such a 'big boy'. I'm not huge but it felt good to hear. She poured more baby oil on her hands and I felt a finger move to my asshole. While she worked my cock her finger entered my ass.

There was so many new feelings happening. Her hands worked my length. I was about to cum. She said 'be a good boy and cum on my tits' with that, I exploded. Her finger stayed in my ass. It tightened. The feeling was so intense. She milked my cock as her finger stayed in my ass. She gently pulled it out. She kissed me and said 'damn I want to fuck you now'. We knew we'd be pushing it if we did that. My mom was due home and we didn't risk it. She would continue to jerk me off and show me new things not only for the rest of the trip but also once we got home. I still know her and she still flirts. We haven't done anything in years but it's hot knowing she gave me my first handjob.

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