A New Family Summer Tradition

I was a regular kid in high school. I wasn't popular or athletic and didn't excel in academics either, I was just average in about everything. The only thing I was really bad at was girls, I sucked at talking to them and could never get a hint on when one was interested. This was the reason I was still a virgin when I was an eighteen year old about to start senior year.

I had gone on dates, made out with a few girls and even gotten a hand job and fingered the last girl I had gone out with, but that was it. After those experiences I always found it hard to talk to the girls again and so I never did. I'm pretty sure they thought I was an asshole so I had given up hope about getting laid before high school was over. I didn't know at the time that everything was about to change the summer before my senior year.

My parents had gotten divorced when I was young so I lived with my mom the entire year except during the summer. It was the only time I spent with my dad who was always busy traveling with work. Summer was the only time he was supposed to be able to take care of me, but even then he would be gone for a few days and I was on my own in his house. My mom didn't know about this and I was happy to keep it this way as I enjoyed being on my own, playing video games, eating fast food, and watching my dad's adult movie collection.

I was surprised to find out things were going to be different that summer. My dad picked me up at the airport and told me he had to leave for a few weeks this time and that he was sorry. I started to tell him it was ok, that I was used to being alone and that I was not a kid anymore, when he told me I was not gonna be alone. Apparently he had a new girlfriend who was living with him and she would be there if I needed anything.

My dad had had girlfriends in the past but none had moved in with him, and usually they had no interest in meeting me. This time I was gonna actually spend the entire summer with one and I wasn't very excited about the idea. That was about to change fast.

I met Cindy right when we got to the house and she did not look like anything I had pictured. She was in her mid twenties, which was surprising as my dad had never dated anyone below forty before, had strawberry blond hair, and was actually really hot. She reminded me of one of the cheerleaders from the University I was planning to attend, but with a more innocent look to her. She introduced herself, and said she hoped we were going to be great friends and have a great time together until my dad returned. She was really nice and seemed a bit nervous, so I smiled at her too and said we surely would. At least I was going to enjoy jacking off that night thinking of her, and more than that in the future, but I didn't know that yet.

It started shortly after my dad was gone. Cindy would walk around the house just wearing a large t-shirt and her undies most of the time. She acted all normal but it was hard for me to hide the fact I was hard all the time, pun intended. Seeing her bubble but and sexy long legs made me want to masturbate right then and there, which I couldn't, but it meant a lot of trips to the toilet during the day. One day, she got out of the shower just wrapped around in a small towel that barely covered her privates. I was seating on the couch and saw her walk to my dad's room and I was instantly hard. She left the door of the room slightly open, and could see her reflection on the mirror of their closet. She was brushing and drying her hair when her towel suddenly fell leaving her pussy and boobs visible to me through the mirror. She had perfect breasts , firm and medium size and a fully shaven pussy.

I knew it was risky but I couldn't help but pull my cock out and start stroking it as I kept looking to her reflection. She didn't seem to notice and continued to do her hair. Suddenly, she moved and I couldn't see her reflection anymore, the door of the room fully opened and Cindy appeared standing in the middle. It was so sudden than I was caught with my cock in my hand, there was no denying what I was doing. Before I could say any excuse, Cindy walked towards me smiling and asked me if I needed help. I was too shocked to reply, but she smiled again and sat next to me, grabbed my cock and started to slowly move her hand up and down. I couldn't believe what was happening, her hands were so soft, the way she was stroking me was gonna make me cum so fast, I could feel the pressure building up in my testicles.

Cindy looked at me and without saying anything she bend down and kissed the tip of my cock. The feeling of her lips made me shake of pleasure, she smiled and slowly started licking the head of my dick, I was in ecstasy. After a few licks, she took it all in her mouth and started sucking on it, I was ready to burst and knew I was not gonna last much longer. Right when I was about to tell her I was about to cum, she decided to take the full length of my cock all inside her throat. That was it, this drove me over the edge and my dick exploded inside her mouth. I pulled out immediately fearing she would be upset for not warning her, but she looked at me, swallowed, and took my cock back in her mouth to clean every bit of cum that was left. Once she was done, she winked at me, kissed the tip of my cock and went back to her room.

I didn't know what to do, I couldn't believe what had happened. I should have probably followed her, or at least said something, but I didn't. The following day, I was afraid things would be awkward, but she acted normal like if nothing had happened, so I did the same. A couple of days passed and I thought it had just been a one time thing when one night I heard Cindy moaning and calling my name asking me for help.

At first I thought she was in pain, that something might had happened to her, so I went to her room and knocked asking if she was ok. She immediately replied saying she needed my help and to come in, she sounded out of breath, and it seemed she was having difficulties breathing. I rushed in worried that something could be wrong with her, but what I saw left me speechless. Cindy was laying down in the bed fully naked, her left hand was caressing one of her nipples while the right one was busy with her pussy. She looked at me with pleading eyes and said: "I need you to repay me the favor now, please..."