When I was 14 my Mom sadly passed away. It was in 1986, two years later when I was in high school that my Dad remarried a woman named Maxine. She was a young voluptuous attractive woman with short well-kept hair and really beautiful creamy soft skin. She was 27 years old which made her 11 years older than me and 12 years younger than my dad. I got on very well with her and with my dad often away on his overseas business trips my new step mom became the guardian who had the task of managing the house as well as taking care of me. We got on very well and seemed to have a lot in common with regards to the music we enjoyed, movies and other teen stuff that she seemed to be so familiar with. It was during this time that I met a girl at school in the same grade as myself named Daniella. She liked people to call her Dani for short. Being a guy of 15 which made me the same age as her I decided to ask her out on a date one Saturday evening, the coming weekend. The plan was for us to go watch a movie and have a milk shake afterwards. She agreed to come out with me on a date and I now found myself madly in love and excited about our upcoming Saturday evening date at the Mall.
When I got home after school I told my stepmom Maxine about my upcoming date for Saturday evening with Dani and she seemed really excited for me about my plans as well as asking me all questions about what we were going to do that Saturday and wanting to know everything about Dani. “So what are your plans for your Saturday evening Date Neil”? she asked curiously. “Myself and Dani are just going to meet at the mall and watch a movie and then go for a milk shake afterwards” I replied. “That sounds like a wonderful evening for a first date and I’m happy to drop you off at 5pm and fetch you at 10pm or so” she replied. “If your evening ends earlier then just give me a call from one of the phones at the Mall” she continued. These were the 1980’s, so long before we all had smart phones. When Saturday finally arrived I woke up excited and headed off in the morning to football practice. When I returned in the early afternoon I showered and got ready for my evening movie get together with the beautiful Dani who I couldn’t wait to see. It was then that I went into the kitchen to grab a soda that I saw my stepmom Maxine. I confirmed that we were still on for this evening and that she would drop me off and fetch me afterwards and she said yes. Then came the shock at 5pm. She came into my room and said she no longer thought it was a good idea for me to go meet up with Dani and that I should rather stay home and do some homework and studying for the upcoming exams. I felt myself break out in a bit of a panic. “No! Please Maxine I must meet up with Dani at the mall, she’s expecting me. Why have you changed your mind about taking me?” I said with tears forming in my eyes. I had a picture in my mind of Dani standing outside the mall waiting as it was getting dark and her thinking I had flaked out on our date plans. “I just don’t think this is a good idea” Maxine replied with a big scowl showing on her face as she looked away refusing to look me in the eyes. “What if something goes wrong? It’s better for you to stay in tonight. With your dad being away if something happened he’d probably always hold it against me” she said. “What could possible go wrong”? I asked. “You’re a teenage boy and I know what boys can get up to. I don’t want something happening between you and this girl Dani” she replied sternly, still with the big frown on her face. “What could go wrong Dammit!!” I shouted “You might get up to mischief with her and next thing she’ll be pregnant” replied my stepmom who I was now starting to hate. With that she left my room and shut the door. I sat alone in the late afternoon gloom wondering what I was going to tell Dani. Should I just sneak out the window and hitch a ride to the mall. But then I’d be in mega shit when I got back. My now hated awful stepmom would tell my dad when he returned in two weeks and I’d be in his bad books as well. I sat with my head in my arms for what seemed like forever when I suddenly heard my bedroom door open. There stood Maxine, her face now calm and looking normal. She started to talk. “I’ll tell you what. I’ll take you to the mall to meet Dani for the date the two of you planned but I first need you to do something for me” she said. Handing me a small glass cup she continued “In this cup I want you to give me your semen now before I take you. That way I’ll be at peace and know that you won’t have any ideas or sexual feelings when you’re with her tonight” I felt horrified that my stepmom would ask me to do such a thing! “There’s nothing to be ashamed of Neil. I know that most guys your age are doing this so if you want me to take you to meet up with this girl tonight then I need you to fill this cup up with your sperm. You’d better hurry as it’s already 5.30 now and you planned to meet Dani at 6.15pm so that doesn’t give us much time” She left the glass cup on my bedroom table and then left the room. The crafty bitch! I thought to myself. The ways she’s willing to embarrass me like this but what could I do. Either quickly wank off for my stepmom now and give the bitchy Maxine what she wants or risk Dani thinking of me as a flaker and an unreliable loser not pitching up to meet her. So, now or never I thought. I droped my jeans and undies and started wanking as quickly as I could. Thankfully it went well. After about 10 minutes of pumping and thrusting my cock I finally shot my load into the glass cup Maxine had left. For a second or two I thought I might just fill it up or it might overflow but thankfully that never happened. I felt tired, angry and depressed afterwards. At 6.10 my stepmom knocked on my door. “Have you finished? Ready? Can I come in and collect the glass cup”? “Yes!” I shouted back. She came in and picked up the cup. Looking at the milky thick white fluid I had produced with a smile on her face. “OK Neil, lets get going” I hardly said a word in the car as we drove up to the mall. Feeling tense, bitter and angry and thinking I’d better put on a happy face when I see Dani for the movie. Maxine was calm and relaxed while she drove me. “I’m very proud of you” she said with a serene smile on her face. “And don’t worry, your dad won’t know of this. This is just between you and I. What you did is a good thing giving you and Dani protection and ensuring just a nice platonic evening ahead “ We got to the mall. I got out of the car without saying a word and stormed off. I heard Maxine shouting after me “See the two of you at 10. Bye. Have a nice evening” The movie evening went well although Dani noticed I was a bit quiet the whole time. At 10pm we waited outside for my stepmom Maxine to arrive and she came 10 minutes later. I noticed she had this big smile on her face when she saw the two of us waiting. We got into the car and she drove Dani home first dropping her off at her house before the two of us drove back home to our place. I never said a word.