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A Weekend With Janine

Posted by: Age: 24 Posted on: 3 comments
9 likes 13 views Category: Masturbation Male-Female Tags: Male-Female, Masturbation Male-Female, MILF, lingerie

Working for my hot "Aunt" Janine one weekend led to an unexpected jerk off session.


This story happened a few weeks ago and involves my parents’ friend Janine. Janine met my mom about 15 years ago at work. Janine is 40 years old, never married, has no children, and works at a public relations company. When I was growing up, she visited my parents’ house at least twice a month. I think of her like an aunt. When my parents are being difficult, I can always go to Janine for help or advice. She is very open minded and I can tell her anything. My car was towed months ago for not paying some speeding and parking tickets. I am 24 years old, have a low paying job, and live in an apartment with some friends. I did not have enough money to pay rent and get my car back. I did not want to ask my parents for money, so I asked Janine and she gave me the money. When I told her recently that I still could not pay her back, she suggested that I repay the loan by helping her at her house for an entire weekend. I promised to do whatever she asked that weekend. On Saturday, I did housework at her place all day. Janine has a new one-story house with a backyard pool and tall privacy fence. I weeded her flower beds, cleaned the house, moved furniture, and brought some stuff from the garage into the attic. Just before I left, Janine told me that tomorrow I would be her cabana boy and take her out to dinner (though she would pay). I arrived at her house late morning the next day. We ate lunch and talked about my job and girlfriend. She then asked me to prepare the pool deck while she changed into her swimsuit. I quickly went into the guest room and changed into my tight swim trunks and polo shirt. If I was going to be her cabana boy, I wanted to look the part! I then went outside, prepared the pool deck, and waited for her. When Janine came outside, she looked amazing. Janine is about 5’3” with big boobs, long brown hair and an average but curvy body. I had thought that Janine was pretty, but she is not the tall and athletic type that I am most attracted to. She came outside wearing a straw hat, sunglasses, and a bright red bikini. I saw Janine in a swimsuit years ago, but this swimsuit was much different. The bikini bottom was a high-rise thong that showed off her flabby ass! The bikini top was large enough to support her big tits, but there was still a lot of cleavage. I had never seen Janine like this. She was hot! Janine confidently walked over to the patio furniture, had me move the deck chair under the umbrella’s shadow, and then sat down. She smiled at me and said: “What a handsome cabana boy!” For the next few hours, she read under the umbrella while I cleaned the pool and got her drinks. Janine eventually closed her book, stood up, asked me to move the deck chair into the sun, and started putting lotion on her body. When I turned around after adjusting the deck chair, her bikini top was off and she was rubbing her huge saggy tits with lotion! Her tits flopped around as she applied the lotion. She had almost no tan lines, so I guess that she usually tans topless. I had never seen boobs that big in person before! They were gorgeous and my dick went hard almost instantly. When she finished rubbing her chest, she turned to me and asked me to apply lotion to her back. While she was talking to me she looked down and saw the big bulge on my swim trunks. After I applied the lotion, she sat in the deck chair on her chest to tan. I had a great view of her flabby ass. A few minutes later, she turned over to tan her front. I just stared as her big tits soaked in the sun. After tanning, Janine went into the pool topless. She asked me to join her, so I took off my shirt and got in the pool. When I was in the pool, she asked if my erection earlier was about her. I told her that it was. She smiled and asked me if I masturbate when something like that happens. I told her that I jerk off a lot. After a brief silence, Janine told me that she played with herself every day, either right before bed or in lingerie while watching porn. The thought of Janine touching herself made me so horny. After about 15 minutes in the pool, she got out and asked for a towel. She then went into the house to shower. Janine asked me to clean up the backyard, shower, and get dressed for dinner. Strangely, she asked me to not masturbate. I did what she asked. After my shower, I wrapped a towel around my waist and walked into the guest room to change. About 30 seconds after I entered the guest room and closed the door, Janine suddenly opened the door and walked in. I was startled at first and yelled out that I was undressed. Then I looked at Janine. She was in her lingerie! She was wearing a black garter belt, nude stockings, shiny black stiletto heels, and a sheer black robe. The robe was closed, but you could see her body well through the robe. She had KY and a glass dildo in her hand. Her hair was done and she was wearing jewelry. She said: “Be quiet and do whatever I say like you promised.” She then walked over and undid my towel, exposing my cock. She handed me the KY and said: “Now show me how you stroke your cock.” She then undid her robe, sat down on the edge of the bed facing me, spread her legs so I could see her pussy, and smiled at me. She had a landing strip and her pussy already looked wet. After she sat down, I quietly started jerking off using the KY. I wanted to cum in front of her so badly. For the first minute or two she smiled mischievously while staring at my cock. Then she leaned back and started touching herself. After another minute she inserted the glass dildo into herself. Watching Janine fuck herself as she moaned loudly made me jerk off even faster.  Seconds later we both came. I grunted as cum shot out of my dick and onto the carpet. Janine yelled as her muscles contracted. A few minutes later, we both became alert again. Janine stood up, smiled, asked me to finish getting dressed, and then left the room. When I went into the kitchen a few minutes later to wait for Janine, I was surprised to see her already there. She had only put a bra and dress on since the guest room. She was still in the lingerie and heels! When she saw me, she said she was hungry and wanted to leave for the restaurant. The rest of the day was normal. We talked like nothing had happened. It was hot that Janine was wearing the lingerie she fucked herself in, but I remained calm in front of her. When I dropped her off at her house, she smiled, kissed my cheek, and thanked me for a great day. I have not seen her in person since that weekend, but I think about Janine a lot now because she is my new favorite jerk off fantasy!   

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