Emotional Hangover

Whew… what a night! I had date #2 with the hot banker I met online. I went to the birthday party of a friend from high school. Not surprisingly, I was bored out of my mind so I left early. I called the banker and he was still at work… midnight on a Saturday! I invited him over and he said he would get here around 1.

He came in and we drank a few beers and chatted for at least an hour, maybe two. Then we proceeded to the bedroom for activities. Of note is that the activities were way less tame than what I normally engage in.

Afterwards, we took a lengthy shower together during which we talked about gold! The banker was skeptical of my cynical belief that gold is going to the moon. Nonetheless, I enjoyed the chat immensely. This morning there was more talking and more bedroom activities.

What’s amazing is how appreciative and generous and real he seems to be. Even though he claims to be “bi”, he admitted to me that he is not attracted to 95% of women. Later, as we were cuddling, he told me that he knows he must be gay because he is enjoying this “way too much.” He also told me many times how hot I was and what a great body I had. As someone who has always been a little self-conscious about being skinny, I loved the compliment!!

After a euphoric couple of hours this morning, the tiredness hit me and I started to contemplate what all of this means. It’s so predictable that after an extended period of having a blast, I feel like shit the next day. Usually it’s a combination of alcohol, lack of sleep, and quiet that causes it. Nonetheless, it was a fantastic evening and I hope there are many more to come!

Trouble

Since the age of 14 or so, I have been having sexual relationships with two friends from school. Each of which was purely sexual and never was there an emotional element. After all, we were straight!

One of the guys is now engaged to be married to a girl, the other one is living in Chicago and is still very closeted. I'll save the commentary about my friend who is getting married for another time.

From age 14 onward, until only about a couple of years ago, just about all of my sexual experiences were done in secret, and often in the woods. I remember how turned on I used to get by sneaking around... I still get a little bit of that thrill with one of these guys -- the one who lives in Chicago. For the last few years, we have hooked up over the holidays when we are both in town to visit our families. Usually, our activities are quite tame. This time however, we have been flirting over IM about doing other stuff.... So, this winter, I plan to have a Brokeback Mtn. style evening with an old friend... in the woods... I can't wait!!

More info about the new boyfriend

I have been “casually” dating a guy for about two months. As I have mentioned here before, he’s not exactly my type. Nonetheless, there are many things I do like about him so I think I should elaborate.

I am a tall, thin person and I like someone who is bigger and taller than me. The current boyfriend is considerably shorter than I am and also quite small. When we’re lying around in bed or on the couch, it seems that both of us want to be cuddled. It made us laugh once because both of us were trying to position ourselves in the interior position on the couch while we were watching a movie.

So that’s strike number one against him. Strike number two is more a reflection of my own vanity. Having only recently come out of the closet (gradually over the last 2 years) I think that one thing holding me back from getting into relationships is my desire to only date someone who is better looking than I am. I want to introduce a tall, great looking guy as my boyfriend. Thankfully, issue #2 is getting much better. I have introduced this boyfriend to many of my friends and I notice that I’m caring less about this than I once did.

There are some great things about the relationship -- we really get along well and we certainly are attracted to each other. Also, I’m learning that it can be fun to be seeing someone. Even if I’m just going over to his place to watch TV, it’s comfortable and nice.

Instead of just going with the flow, I think that one of these days I will have to make a decision. For example, he wants to take a trip with me over the next couple of weeks. I feel like a trip – alone – means that things are going to get more serious. I don’t know whether or not to go on the trip and just relax, or if I should not go on the trip because I don’t want things to get more serious. It sounds like a silly question but this is the quandary I find myself in now.

New Boyfriend Background Information

I have been seeing a guy for about a month and a half. We get along really well and there’s a good amount of sexual chemistry. As the weeks go on, we are spending more and more time together. It is a good thing, but it has me pondering how I should proceed.

Problems: He’s not my type. I am looking for a guy that is bigger and stronger than I am. This guy is neither – he is short and slim. Also, I’m not all that into him…I’m not “gaga”.

So, at this point, I would say that this is probably the most serious relationship I’ve ever had. I’m just not sure how much more I should pursue it if, in my mind, I don’t think it will work out.