Hey let’s do it like we’re friends….

There’s one guy I’ve been strictly platonic friends with since I was 16, so for 8 years we’ve been friends. He is my Oldest Guy Friend (OGF).

OGF and I have an incredible amount of sexual tension between us. So thick you really, truly could cut it with a knife. When we’re around each other, we flirt shamelessly. Our friendship has always been like this but it’s always been harmless fun.

Even after many drunken nights, we never even kissed although once in a great while one of us would try for something. The other one, the sober one, though would always be the “voice of reason.” After all, we have such a good friendship – why mess with it?

I have had numerous reasons for never hooking up with OGF despite the fact I truly do sexually desire him – more than I have desired most people, honestly.

These reasons included:

1. He is my Oldest Guy Friend. Strictly platonic too for years. He is someone I come to for advice on other men.

2. He has been quite the man-whore, hooking up with something like 90% of his female friends. I loved teasing him that he could never have this.

3. He once had sex with a good female friend of mine. And I actually saw them by accident! A mental image that has been burned in my head! And I love to tease him about this hookup relentlessly since he regrets it. He says he did it for me and my best friend. Wow – thanks! :p

4. He has issues with emotional intimacy, I believe.

5. I was afraid if I finally experienced him in such a way I would fall in love with him and it would break my heart that it would not be reciprocated. See above.

6. I didn’t want to take away this lust and wanting. Maybe, with him, the wanting would be better than the having and it would be better to never experience him than ruin my fantasy of him.

Reasons to hook up with him:

1. It would be so thrilling to finally experience him on a level we’ve joked about so often.

2. He is really sexy.

3. He thinks I’m really gorgeous – he has told me I have the face of a movie star. So there is mutual sexual desire and attraction.

4. I’ve always wanted to just give in to my desire for him. I have had countless sex dreams starring OGF.

 Well, on Saturday, he was out to celebrate his last night in our city – he’s moving across the country for school. And to live with his gf (he has cheated on her before). So I joined him and his friends. I was very excited to see him but sad about him leaving.

I had a very fun night flirting with OGF and his friends. OGF was bragging to everyone how I must have the skills sexually. He always does this when he’s drunk. So, I deduce, he has wondered how I am in the bedroom. And that curiosity is mutual. For sure. I spoke to one of his friends I’m supposed to go out with again (we went on a date once but there was miscommunication and he “bowed out” – he thought I said I had a boyfriend). Due to his profession, I will refer to him as Trainer. Also, I drunkenly madeout for the first time with another of his friends who I’ve known for almost as long. I didn’t tell OGF about this for some reason. He had make a joke about us taking a long time to go back to his house when I “jokingly” asked him for a peck on the lips – he said he wanted to make sure I hadn’t given his friend a BJ. I laughed and acted as if nothing happened.

When I got back to OGF’s house I was very drunk by this point. I was flirting with Trainer. Later, he offered to take me home but I declined – I wanted to spend more time with OGF because I didn’t know when I would get to hang out with him again. Trainer insisted he would not try anything sexual with me but I assured him this wasn’t my concern. I just wanted to talk to OGF.

Trainer left and OGF and I prepared for sleep. I have spent the night with him before and nothing but cuddling occurred so I didn’t feel any hesitation joining OGF in his bed. And changing down into my boyshorts and his t-shirt in front of him. It’s true – I wanted him to feel slightly turned on by me but I had no intentions of anything else.

We were lying in bed chit-chatting about some guy who I recently dated and all of sudden – he kissed me. Our first kiss, ever. After eight years. I was so confused and excited. I mean, I was laying there kissing my oldest guy friend. Someone I love (as a friend, it’s true). Someone I desire.

At this point, I thought the voice inside my head would be yelling, “Stop! What are you doing? This is crazy!” but nothing like that was being said. This also has nothing to do with my being drunk since because of my sexual guilt, this voice never shuts up usually during sexual encounters.

But honestly, it just felt right.

He then went down on me. I’ve never let someone do this to me before I’ve first given them head. It’s a boundary thing. I don’t like feeling so vulnerable in a beginning encounter. But, I just wanted it. And for the first time, I was just going with want I wanted.

Later, I reciprocated while he held my hand. I thought surely, I would get him off from this. I still had no intentions of having sex with him. I was sure this would go under the “everything but” category.

He then though moved me off and starting kissing me again. Passionately. I’m not surprised by how well we kiss together. I told him I felt he was getting too close to having sex with me. And he pleadingly said my name saying we didn’t have to do anything I didn’t want to. The way he said my voice was filled with so much emotion it made me feel assured I wasn’t making a mistake. This wasn’t a casual meaningless encounter even if we aren’t in love.

I asked him to put on a condom just so I felt safer with him being so close to me. He did so and we kissed a little more and then all of sudden with no words exchanged, he entered me.

And here I was, having sex with my #2, and it was with OGF. I thorougly enjoyed myself while we had lingering sex. It felt sweet but not romantic and that was all I needed to get me over my second person hump (pun definitely intended).

T. Rex – “Diamond Meadows”


August 8, 2007. casual sex, dating, Oldest Guy Friend, platonic, sex, sexual guilt, single, T. Rex, trainer, Uncategorized. 4 comments.