The following is a true story. The names have been changed to protect those involved.
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At the time of this story I had been dating my boyfriend Mike for about four years. We were both 21 and had been together since high school. We were each other's first and only and I always thought that was really special. I loved him a lot, we got along great, did a lot of fun things together, and the sex was good. I realize now that I really didn't have anything to compare it to, but it was still good. Even though things were good, after four years, I was starting to get a little bored. I still loved Mike a lot, but it was at this point in our relationship that I realized the parallels between us and my parents and I didn't want us to go down the same path.
My parents had a similar start as us. They had met in high school, got married a few years later, and started a family really young. Fast forward approximately 30 years and they always fight, they haven't slept in the same room for over 10 years, and I highly doubt they have had sex in the same amount of time. This is no way to live and I'm not sure why they didn't get a divorce, but it was probably because of me and my older sisters. At 21 I was the youngest of three girls. My older sisters were 27 and 29 at the time. For the most part my parents kept up appearances for us, but we could all tell that they fell out of love and stopped having fun a long time ago.
I don't know what triggered it, maybe it was because I was getting a little bored with Mike after so much time, but even though I still loved him, I started to fixate on the similarities between us and my parents. The main thing that ruined my parents was their early start. I'm not sure if they realized it then, but I could tell by their actions that they felt like they had been held back and resented each other for it. As far as I know, they had only been with each other and never experienced what it was like to be with someone else. Without going into details, I think that over the years they both suspected each other of cheating for this very reason. I was starting to realize that life is too short to limit myself like this and end up miserable like they are.
This is when I decided I needed to do something to prevent this from happening to me. I didn't want to end up like my parents, feeling like I missed out. I wanted to know what it would be like to be with someone else. Life is definitely too short and although I really loved and cared for Mike, I started to feel like I needed to experience more, and soon, while I was still young and had the chance. To do so I had to come up with a plan so he wouldn't find out because I didn't want to lose him in the process.
I started to think about a plan, but instead of starting with how, I realized I needed to start with who I wanted to be with. I had to figure out exactly what I wanted first and that would help me decide if I really wanted it at all. As I thought about it, I realized I definitely didn't want to pick up some random guy. I knew it wouldn't be good with someone I didn't know or care about. I'm an emotional person and I needed someone I had a connection with, someone I cared about and trusted. I wanted the experience to be one of not only lust, but also passion and if possible, love. Otherwise it wouldn't be worth the risk. This narrowed the potential list greatly.
It couldn't be any of my guy friends or my boyfriend's either, they were too risky and I wasn't really attracted to any of them. They were also too much like my boyfriend and the whole point was to experience something new and different. The prospects were really starting to thin out and I hadn't really even started.
Where could I find someone I knew and trusted, that would be fun to be with, and would keep the secret? I racked my brain of all the guys I knew, but no one fit that criteria and I came up empty. I started to get frustrated, so I really started to expand the list of potential guys to ones I knew through other people like my sisters. My older sister Kim was in and out of relationships and wasn't seeing anyone at the time, so she was a dead-end. I never liked any of her guy friends or boyfriends anyway. She always seemed to attract the wrong guy. My eldest sister Anne had a few guy friends that I thought were cute, but I never had a chance to get to know them well enough because of our age difference, so that was a dead-end too. My last resort was through her long-term boyfriend Keith. Since they had been dating for so long he had some friends that I got to know, but they were not my type and I didn't really know them well enough to trust them. Another dead-end.
Anne and Keith had been dating since I was 15. Over the years I really got to know and trust him. He was part of the family. He had helped me with my homework in high school and some of my college work too. He always jumped at the chance to help me. He was a genuinely nice guy. At a few points over the years, before I met Mike, I had a crush on him and even fantasized about being with him, but I had always put it out of my mind because of my sister and eventually Mike. However, this recent realization about my parents and the trouble I was having finding someone made it harder and harder to put him out of my mind. I ended up thinking about him more and more. It eventually got to the point where every time I tried to think about alternatives, I always ended up thinking of him, which I tried to convince myself would obviously not work.
After many more attempts at finding someone else, I reluctantly kept coming to the conclusion that Keith would be the perfect person for this as much as I didn't want to admit it. Sometimes the answer is right in front of you and you just don't see it, or deliberately try to ignore it. Unfortunately, this answer was my sister's boyfriend. However, I really cared about him and I knew I could trust him. I knew he cared about and trusted me too, so deep down I knew it could work as much as I tried to convince myself otherwise for obvious reasons.
Keith was a good looking guy. He was a little over six feet tall, had brown hair, and a nice athletic build. Being older, more mature and experienced was exactly what I was looking for too. I had also heard that older guys are better lovers because they aren't selfish and take their time. The more I thought about it the more I thought how much fun it could be. But I was so conflicted.
If I really was going to go down this path, I needed a way that I could pull this off without hurting anyone. Since we both had a lot to lose if it got out, I knew that if I got Keith to go along with it our secret would be safe. Neither one of us would want it to ever get out. My intention was to have this experience to make sure I didn't end up missing out like my parents did, to explore myself and someone new and in the process have fun and experience life in a different way while I still had the chance. My intention was not to do anything that would hurt my sister or my boyfriend. They could never find out, so my plan had to be perfect.
I figured I wouldn't have too much trouble convincing Keith. I had a few things going in my favor. I am about 5'3" and at the time I was around 120 lbs, had long dark hair, and a perky build. I had caught him looking at me a few times over the past few years and I was fairly certain he'd be interested. I was also 21 and he was 29. I was pretty sure that he wouldn't mind being with a younger woman, especially after being with the same person for so long. I know I was a little bored and it had only been four years for me. There is also the sister fantasy that guys have, which I hoped would work in my favor. The allure of the forbidden nature of this act wasn't lost on me either. From the moment I decided that I definitely wanted to do this, or at least seriously think about it, I got really excited. Sometimes I would get so excited thinking about how it might happen I would end up masturbating. I would fantasize about every detail of how it would be and end up so engrossed in the fantasy that I would have the most amazing orgasms. I also felt energized and alive when I was around him too, knowing that he had no idea what I was planning. I would flirt with him a little also, just to test his reaction. I loved the feeling.
It took me a few months to figure out how I wanted to go about doing it. I went through many different scenarios in my head, but I couldn't quite get something nailed down that wasn't complicated. Plus, I always got excited while planning and would end up day dreaming about how it might happen instead of actually planning. If I was alone, I almost always ended up getting aroused which would completely throw off my concentration.
I finally decided to keep it simple. Simple is always the best way to go. Keith lived with my sister in a house fairly close to me. I was still living with my parents at the time. Every once in a while I would stay over their house in the guest room just to get away from my parents. I decided that the next time my sister was away on business, I would simply make an excuse to stay over, like I had to get out of my parent's house or I had a fight with Mike. The excuse didn't really matter because I knew Keith would let me stay, he always enjoyed having company. Once I was over I would see how things went and just work my way from there.
My sister travelled fairly frequently for her job. I spoke with her and found out that she'd be travelling in a few weeks. That few weeks seemed like an eternity, but they finally passed and the time arrived. We lived in the suburbs of New York City and Anne would be in Florida on business for a few days, so I began to prepare. I got really nervous and excited knowing that the time was near. I made an appointment to get a bikini wax so that I'd be ready and I ended up waxing everything. I had never done that before. When I got home, I looked at myself in the mirror and felt so sexy. In the days leading up to it, I couldn't keep my hands off myself thinking about what might happen. Would he think I was sexy? Would he want me? Would it be awkward or comfortable? How would he feel inside me? A new person to kiss and touch, what would it be like? I had only been with Mike...I was overwhelmed with lust. All of my senses were heightened. I felt so energized and alive.
When the day arrived I was even more overwhelmed, extremely nervous and excited. I couldn't stop thinking about it. I couldn't concentrate at work. My heart was constantly racing all day. I had to leave work early to go home and calm myself down. Around 6 PM, when I knew he'd be on his way home from work, I finally built up the courage and called him. This was the first of many big steps...
