I was looking for a temp gig to fund a trip to Europe before starting university. Jessica, my interviewer, was nine years older than I was 20 then Real life cougars, but I was instantly drawn to her — she was petite, with a hot body and an attractive face.
The interview proceeded professionally and I left, thinking nothing of it.
We spoke briefly about the position but somehow veered off-topic, chatting casually about our weekend plans. On the spur of the moment, I even asked her to join me at a club with my friends but she laughed and said no. Later that night, after a few drinks, I ended up drunk dialing her. Surprisingly, she seemed relaxed about the whole thing. When I did start work, we continued our casual relationship via SMS, even Real life cougars she was my boss.
We bonded easily over common interests like music and outdoor activities, and quickly built a tight friendship. We would send flirty text messages to each other throughout the day at work and late into the night. This lasted for about two weeks before I plucked up the courage to ask her out for drinks. We ended up kissing that night. Despite the age gap, there was definite sexual tension and I was really attracted to her. Plus, she was fantastic company — outgoing, funny and spontaneous.
She would pick me Real life cougars in her car, but always at a distance from Real life cougars office — she was very careful because she was holding a senior position at the company. I remember her flipping out when I added her on Facebook, terrified that our colleagues would notice.
We eventually progressed to having sex at her downtown apartment she rented her own place with a housemate. Sex with her was hot and steamy, and soon I was spending nights over. Despite all the time we spent together, we never had The Talk.
For a guy, it Real life cougars the perfect arrangement Real life cougars she was hot, the sex was great and there was no commitment. Even though I constantly offered to pay when we went out, she would always pick up the tab, even if we were at a high-end restaurant. She would always send me home after a date even though we lived on opposite ends of the island. She had no qualms about doing things usually expected of the man in a relationship — paying the bills, driving us around and constantly having me over at her house.
Three months into the relationship, things got even more serious. This was in the last few weeks before I left for Europe. Yet, on some level, both of us knew the end was near. I was going away and the age difference meant that we were never going to be a serious item.
I think the whole situation worked only Real life cougars the premise of a definite cut-off point. We eventually decided that things needed to end and met up to awkwardly say our goodbyes.
But the night before my flight, Jessica asked to see me. When I met her, she passed me an envelope, asking me to Real life cougars it only when she had left. She told me to have fun in Europe. I called her up, asking what the money was for.
She told me to keep the money in case of an emergency, as I was travelling on a shoestring budget. I never used the money and I transferred it back to her after my trip. Looking back, she was an amazing person.
Besides being successful and confident, she was also warm, kind and sincere. And even though things were mostly physical, I learnt a lot from her self-assured way of life. My relationship with Jessica Real life cougars a change in me. Being with older women quickly became something I enjoyed.
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My cougar magnet days had begun. There was the divorced Real life cougars of a former tutor, two doctors I met in the US while on a university exchange programme, a corporate high-flier — these are just a few. All of them were more than eight years older than me. My wildest encounter was with the doctors in the US.
I met two of them on a night out and ended up sleeping with both the same night. Among all these women, Jessica was the exception — we were a couple in everything but name. With the other women, it was mostly physical. Some were one-night stands, and almost all the women made the first move.
My friends, who used to taunt me about my secret relationships, were left with their mouths agape. But they often have had no time for love, and some had recently ended relationships when we met. And they also wanted no-questions-asked sex.
The simplest explanation I can offer: No boyfriend or a husband in the mix, nor a girlfriend on my end. My latest squeeze, Rebecca, is a successful healthcare executive in her early 30s. We met a year ago and she is a prime example Real life cougars the type of confident cougar that I easily reel in.
I first saw her at a fancy hotel bar which has the reputation of being flush with social escorts.
I noticed her immediately, no thanks to her sexy red dress. When she came up to my table and started chatting, I immediately put my guard up — more so when she asked me to dance.
Smitten by her brazenness, I spent the rest of the night trying to get her to dance with me. We eventually exchanged numbers. When I got there, she had a bottle of champagne waiting. She said she just felt like having a staycation. Yes, we definitely stayed in that night.
She sent me a text a few weeks ago that was uncharacteristically needy — asking why I never asked about her day. Though she texted me soon after, telling me to ignore the message and that she had been drunk, things have been slightly weird since. This story was originally published in the February issue of Her World.
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