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How it Began
21/12/2023
I was a quiet shy kid in my childhood and my sister was two years younger than me. When I was younger, my sister had invited a friend to our house for a sleepover.

It was late and my parents had gone to bed. My sister and her friend were in her room and I was in my room just down the hall.

It was very late and I was watching a late night horror movie on tv. I hear my door nob turn and the door open slightly. Then Cindy sticks her head out and tells me she can’t sleep and asked if she could join me.

I was a little startled and only had my underwear on. Before I could say no, she walked in and closed the door. She walked over to my bed looking at my present condition. I was embarrassed and tongue tied.

She climbed into my bed and asked what I was watching. I told her it was a vampire movie and she responded, great, I love them. She was wearing a short night gown and was very cute.

I wasn’t the slightest interested in her. As we sat quietly watching the movie, she shocked me with her next question. She asked if I had ever seen a girls vagina. I was embarrassed and didn’t respond.

She later said she would show her vagina if I let her see my penis. Again I was embarrassed and replied no. I had never seen a girl before because my family was very private.

I had no experience with anything like this before and was ashamed, I knew very little about girls. I had heard stories from some of the boys at school but had no experience myself.

I told her she had better leave my room. She then said something that put the fear of god into me. She said if you don’t let me see your penis, I’m going to tell your sister you tried to play with my vagina.

The thought of my sister telling my mom scared me so much that I pulled down my underwear and let her see me. She leaned in for a close look and then reached out and grabbed my penis. I sat there while she began playing with me. She looked into my eyes and asked if it felt good.

To my surprise it felt really good and my penis was hard as a rock in no time. I admit I have played with myself before and it felt good, but this was a way better good. The more she rubbed my penis the more excited I got and pretty soon I was feeling light headed and starting to pant.

I was in a place I had never been before. She eventually stopped and said now it’s your turn. I had no idea what to do. She pulled up her gown exposing her vagina and asked me to rub it. I wasn’t sure how, so she took my hand and guided it.

I didn’t know what a vagina looked like until this very moment. She guided my hand so my fingers were rubbing up and down her slit. She then asked me to stick a finger in her. Didn’t know where to stick it so she again guided my fingers.

I slid my finger in and out slightly and began feeling some wetness. She eventually laid back and reached for my still erect penis. We lay there for minutes slowly playing with one another with our eyes closed.

I was having feelings I had never experienced and didn’t know what was going to happen but I felt as if my dick would explode. All of a sudden she stopped and said that was enough and she needed to go back to my sisters room before we get caught.

She climbed down and slipped out the door. I lay there still worked up with my penis still throbbing. Eventually I began to calm down and my penis collapsed. I pulled up my underwear and lay there wondering what had just happened. The next morning she acted as nothing happened. But I never forgot. It was about a year later I was sleeping over at my best friends house.

His parents were out of town so his aunt was staying there for the weekend. His aunts name was Vicky and she was his moms younger sister by several years. She was actually in college.

Anyways, one night I was on the floor on a sleeping bag because he only had one bed. Sound to sleep when all of a sudden I was waken by a familiar feeling. I had been having a dream when I woke and realized it wasn’t a dream.

There lying beside me was Vicky and she was stroking my raging erection. She only had a T-shirt on and looked into my eyes and smiled. I didn’t say anything and just lay there allowing her to do as she pleased.

She then did something I had only heard about. She began licking and sucking my penis. It felt absolutely wonderful. My first blowjob by a woman twice my age. She stopped and whispered into my ear asking me to play with her pussy. This I knew so I began to work my hand down to that area when I realized something is different.

I found a huge clump of hair and I couldn’t find the slit or hole. After a couple minutes, she laughed and said what are you doing. I was embarrassed that I obviously didn’t know what I was doing so she moved my hand down lower and there it was.

She was very wet and I began to rub her like the inexperienced virgin I was. She finally said, let me teach you how to please a woman. She placed her hand over mine and manipulated it as she masturbated using my hand to play with herself. She was amazingly wet and hot and the smell was making me drunk.

She was pushing my fingers deep inside herself and then asked I slid my hand into to her. As I pushed my hand in as far as I could and pulled it back out she let go and said don’t stop. She then gave me orders to go faster and harder with more force. My whole hand was practically inside her as she began to shake violently making loud moaning noises. I thought she was going to wake my friend. She eventually stopped shaking and gave me my first kiss telling me how wonderful I was.

Not really knowing what happened, I was pleased she was happy. She then removed her T-shirt and let me play with her large tits. She asked me to suck her nipples which I did. She then crawled on top of me and lowered her pussy onto my still hard penis. She began to slowly move back and fourth. The sensation was incredible and she asked me to suck her nipples.

I felt like I was on fire and had no idea what was happening to me. She again started to squeal and collapsed on me. She rolled off and said I was wonderful. She asked if I came. Didn’t know what she meant so she explained to me about orgasms. I hadn’t had one, no cum present. But I guess I did lose my virginity.

This happened again about two years later but this time she was married. I did finally have my first orgasm with ejaculation. She told me I was better than her husband and we fucked several more times over the next year. She was my first and I was in love with her. They eventually moved away after she got pregnant. During that time Cindy had been hanging around my sister again. We were having a bbq one evening and she was present. At one point we were left alone outside and I decided to ask her about our first experience. She was very pretty and had filled out nicely. I was smitten for sure. She said she remembered our play so I asked if she would like to repeat it. She said she would and gave me her number.

I called her a few days later and we planned our date. My parents were away and my sister was with another friend for the weekend. She came over and we didn’t waste much time. We were both more experienced and fucked for hours. She was way tighter than Vicky and my dick was way more sensitive. I came quickly but rebounded just as fast. The evening was wonderful. We were hooking up weekly. I was falling hard for her.

Then after a hot session she sprung something on me which caught me by surprise. She told me she had a boyfriend and he fucked her better than I could. I asked in what way. She said he has me in size and endurance. She then was brutally honest and told me my penis was small. This was news to me. I did notice that her pussy wasn’t as tight as it use to be. We continued having sex behind her boyfriends back but we had slowed considerably.

We eventually stopped after she moved on with a new beau. After high school we ran into one another at a party. We were both drunk and ended up back at her apartment. We started to dating again and I asked her to be my girlfriend. She said she really had feelings for me but wasn’t sexually pleased by me.

I was so in love with her and wanted her to be my girlfriend, so I caved and offered her an open relationship, where she could have sex outside the relationship and I would remain loyal to her. She finally agreed. I moved in and many years later, here we are. Hotwife and Cuckold. Blissfully in love and married.


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