A year into his relationship with Tanya, Alvin asked to meet me alone for a drink after work. I thought this was an unusual request, seeing as he and Tanya were inseparable. Nevertheless, I agreed to see him. When he arrived, I noticed that he was really nervous, so I asked him what was wrong. Looking extremely embarrassed, he confided that he lacked sexual experience and was afraid of disappointing Tanya in bed.

I later learnt that Alvin hadn’t really dated anybody seriously after me and had only had sex once, with a woman he was seeing casually at the time. He admitted that that experience had been a disaster and had made him question his abilities as a lover.

Alvin was desperate not to make the same mistake with Tanya and begged me for advice. I know it seems strange or even inappropriate to be discussing sex with my ex-boyfriend, but Alvin and I had grown to become close friends who could talk about anything and everything.

My heart went out to Alvin that evening – in his recounting, Tanya had told him that sex was very important to her. They had a strong emotional bond, but Alvin was freaking out about the possibility of coming across as not knowing what to do in bed. So before he got sexually intimate with Tanya, he wanted some advice on how to please her.

My conversation with Alvin revealed more surprising details – he didn’t know much about the female anatomy or how to bring a woman to orgasm. He’d also never performed oral sex on a woman. I was beyond stunned. I knew that Alvin was a sheltered guy, but this took the cake.

I honestly wanted to see my good friend happy in his relationship, so I did something I never thought I’d do – I offered to teach Alvin how to have sex. I explained that it would be a no-strings-attached arrangement and made it clear that I wanted nothing in return. I also got him to promise to never tell Tanya about our arrangement. It took a while for Alvin to accept my offer. Naturally, he didn’t want to be unfaithful to Tanya, but I told him that it was just sex and he was doing it to help his relationship.

Teaching Alvin how to be a better lover was a clinical affair. Initially we both felt embarrassed but as the ‘lesson’ progressed, we became more comfortable with each other. I explained and showed him all the various female hotspots to him and allowed him to touch them. Then we kissed – quite passionately, to my surprise – and had protected sex a few times. I took Alvin through four or five different sex positions, explaining how each one would turn his girlfriend on. I also told him how to read her body language to figure out what she needed and how to tell if she was aroused enough. Alvin was very attentive and open to discovering my body. At first he fumbled quite a bit, but as the night went on he managed to get into it. We were done in about an hour.

When the ‘lesson’ was over, I did feel somewhat guilty because I had, in a sense, encouraged Alvin to be unfaithful to Tanya. But I convinced myself that it was for her benefit, too. And besides, Alvin and I weren’t in love with each other and we knew that we would never get physical with each other again. I must say that things were a little awkward between Alvin and I after we got dressed. We didn’t know what to say to each other and hurriedly left the hotel room – he first, because he was paranoid about being spotted leaving the hotel with another woman. I left 30 minutes later.

Alvin contacted me a couple of weeks after our sex lesson. He admitted that he’d felt weird after leaving the hotel and didn’t know what to say to me. He had spent a lot of time thinking about our encounter and trying to get over the fact that he had cheated on Tanya. But he added that, once he’d gotten over the initial emotional discomfort, he could say that he enjoyed his experience with me and thanked me for helping him. He also mentioned that he learnt a lot that night and hoped that it would help him be more sexually confident with Tanya.

Somehow I sensed that our sexual encounter changed things between us, but not for the better – we had crossed a line from which there was no turning back.

A few months later, Alvin called to tell me that he and Tanya were engaged. I was genuinely glad for them. They make a fine couple and it thrilled me to know that they wanted to spend the rest of their lives together. I was invited to the wedding but I turned down the invitation; as happy as I was for my friend and his soul mate, things between him and I just weren’t the same anymore.

*Names have been changed.

Text: Melissa Wong/Her World

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