The Reason I Am Still Going To Go For Older Men

Originally this post was called In Praise of Younger Men.

But then I actually had something like intercourse with one and I realized my mistake.

It all started when one young man emailed me on OkCupid. He was 21 and I am 24 and although the difference is years is not large, the difference in technique is very much apparent.

I am sure that there happen to be young men who are very good at sex, but this guy was not one of them.

We first met over drinks and when I saw him I was very disappointed by his choice in clothing but I knew he had come right from work so I held my tongue.
He was very confidant, which is a turn on, but he didn't really strike me as someone I would really make an effort to see again.

After Christmas I was bored so I agreed to meet him again and we spent the afternoon hanging out near my apartment. Again he dressed like shit and I chewed him out for it.

I admit I am superficial and care about clothing choices more than most people, but I generally don't give people shit for what they wear. He showed up FOR A DATE wearing dirty black jeans and an oversized hoodie.

And yet, I still had him back to my place?

He actually invited himself over, and I think I dug that... I have no idea. I was also horny as fuck.

I actually had myself convinced that he would come over and we wouldn't do anything but hang out. But then we were making out and in my head I was telling myself that I would ONLY take my top off. But then I had my bra off. And then my pants. And then I was naked...

This first encounter included no penis-in-vagina intercourse, it was all making out and hands and mouths.

He was amazing with his hands! And then he was even more amazing with his mouth! And when it got so intense I tried to squirm away and he growled and grabbed me and dragged me back towards him.

And then he used his hands again and he made me cum so hard I had my first experience with female ejaculation!

This is why this post was almost called In Praise of Younger Men. But then he came over again the other night and we had sex...

Now, I can understand that sex is one of those things you can improve on, and I would certainly love to help him do that if I was actually interested in persuing anything with him. But I was clear that this was a sex thing, and so it makes no sense for me to continue with it if the sex is shit.

Foreplay was great, as with before. I wanted him on top and he pre-warned me that he wouldn't last as long on top. I figured that it would be okay and he was probably just nervous.

NO.

He layed down on me so our entire torsos were touching. He couldn't figure out if he was in or not. He talked SO MUCH to the point where I had to tell him to shut the fuck up. He did not pump, he wiggled. He had no leverage. He came in 3-4 minutes.

I was gracious and laughed it off and then made sure he did a good job on me before leaving.

He did an excellent job with his hands but it didn't make up for the terrible sex.

He's been texting me constantly and I've been giving minimal responses. I've lost interest and feel no draw.

My co-worker said I'm like a dude. I get bored once they put out.

Guy #2, Round two

Earlier in the week I had an interesting evening in which I fucked two guys in one night. The first guy was shit so I felt the need to make up for it by welcoming a second one into my bed after kicking out the first.

Guy #2 gave me a rough first impression but quickly changed my opinion of him by impressing me with his wit and interesting stories.

Before he left my place the next morning, a Tuesday, we agreed to try to get together on Friday as we both had the day off.

There was a litte bit of texting over the next couple of days and then on Thursday night he called me at 1:30am and we had a 1.5 hour phone conversation that felt like it lasted 5 minutes.

I really liked talking to him! He was funny and sweet and entertaining. At one point I was getting very sleepy so he offered to tell me a story. He started with "Once upon a time..." and I cut him off abruptly and told him to come up with something less crappy.

There was a pause and he started to confess to me...

#2: "I'm freaked out..."
Me: "Why? What's up?"
#2: "...I think I really like you but I know you don't want anything serious. I am afraid I am going to get hurt."

I didn't say anything for a minute because I had now idea WHAT to say. I just met this guy! He then started probing and asking questions about it, and I don't know what was happening, I am going to blame it on how tired I was, but I almost started to cry.

This was frustrating. I see crying as a huge sign of weakness and I have a super hard time when even those close to me see/hear me cry, nevermind some strange dude I just met!

He could tell I was uncomfortable and so he changed the subject and eventually let me go to sleep.

The next day we agree to meet in the early afternoon. We grab some sandwiches and quickly scarf them on my balcony before getting down to the important stuff.

He's good at fucking. And kissing. And at one point he compared his nuts to the engine of the Titanic.

We did that for a while and then he had to leave to babysit his nephew.

After he left I was unsure of how I felt about it. I thought about him on and off into the evening until I realized that that was it.

I am probably never going to see him again, and I'm content with that. Although, his stamina will be missed.

Drunken Encounters: Part 2...The Time I Was Sober

My goal was to have sex with Mr. T within a week of our first encounter but due to a bad cold and severely sore throat, no thanks to Old Guy, I had to postpone until last night.

I went over to his place and brought a couple of beers with me to break any potential tension. He seemed impressed by this and we drank them while watching Iron Chef.

He was sweet, he liked my dress and when Iron Chef was over and I was choosing a movie for us to watch he commented on how he liked that I hadn't stopped smiling since I got there. He said it was contagious and made him happy.

We talked about work and tattoos (he has many) and his mom and he seemed kind of nervous because he kept getting a stutter. He would talk about stuff we should do in the future, like dates and stuff. He also invited me to join his birthday festivities tonight.

We started to watch Austin Powers and I slid in next to him so we could cuddle a bit and after a while he started tickling me and he managed to get my dress up to grope my ass. Then he mumbled something about being quick because his roommate was going to come home from band practice soon. So I suggested we go to his room.

He refused to turn the damn light on because it was so messy, or something, and I knocked some shit off his book shelf because I walked right into it. We made out which turned into vigorous dry humping which turned into me going down on him. Which turned into sex.

He didn't once touch my vag, which I find baffling. He didn't want me to make any noise (which I found VERY hard!) just in case his roommate came home and heard. And when Mr. T came, I didn't even notice. He was soooo quiet and I had to ask him if he did or not and he said "yeah...It's your fault!" (a joke?) and then passed me my dress and bra. Actually he first suggested HE wear my dress, something he had mentioned twice already the first time was when he told me he liked it and the second time was when Britney spears came on TV and he said he wanted to make a music video dressed in her bikini and my dress...

Then we got dressed right away and as we were leaving his room I could swear that he tiptoed out to the living room tentatively just in case his roommate came home and he hadn't heard. So weird.

Then we resumed watching the movie. I sat right next to him but this time there was no cuddling. Soon his roommate DID come home, with some other dudes in tow and they did a drug deal. As soon as the guys walked in Mr. T turned into a bit of a bro. He was louder and showy and the stutter and nervousness were gone.

Soon the guys left, but the roommate stayed and it felt kind of awkward. I left right away because he was tired and had to work at 7am.

The goodbye was kind of awkward. He hugged me and kind of gave me a peck on the neck/shoulder and told me to text him.

I am not going to put much time into puzzling about this one. He was doing really well at the begining but the sex was disappointing. I'll see how it goes. No one is being written off just yet.

In other news, I plan on fucking Old Guy again this week. Fingers crossed!

Drunken Encounters: Part 1 of *HOPEFULLY* Many

Last night I met a strange man on a street corner and suggested he ravish me on a dark boulevard.

I say strange because although he and I have been texting quite regularly, we had never met in person. Let's call the man of this encounter "Mr. T" as his name starts with a T and he is a big guy who is kind of intimidating looking due to the fact that he is the singer of some probably crappy hardcore band.

This encounter came about after a series of drunken text messages that started with me saying

"I'm shit faced. I'm in a cute dress. I'm close by. What are you going to do about it?"

And ended with my dress up to my waist and his hands on my ass.

I would rate this encounter PG. If your children had watched they probably wouldn't have been too disturbed by what they saw.

Also, I didn't notice at the time, but some mild facebook stalking revealed that he has a winnfield moustache(according to the chart below).


My goal is to have sex with him by the end of the week.