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.

This all happened when I was sober.

Let me preface this story by saying that before this summer my sex life was slow. No...slow isn't the right word....It did not exsist. I had started working really hard at online dating and decided to try to whore it up a little and see what happened.

One night Houston and I were chatting and she kind of dared me to have sex with four different guys this summer, and I agreed. NOW I realize that four does not seem like a big number. I could have had sex with four guys in a week EASILY because getting laid is easy, but I didn't want to just have sex with anyone. I wanted to feel it out and meet up for a drink and find guys who were worthy, which is funny because I realized how rare that is.

Until this weekend I was up to three guys, all of which I had seen more than once. I had had sex almost once a week and was fairly content with my progress, but I also felt a sense of urgency because Houston was leaving town to go to school in a week and that was my deadline. So I kicked the online thing into high gear.





Last night I did something that I would never have imagined would happen in my bed EVER. I am in shock at myself for my behavior, but also impressed, and maybe a little disgusted. Oh my god. I can't decide whether to brag or feel shameful....I have noooo idea....

Last week I had started texting this boy named Jesse. He texted me quite a bit from the begining which was sort of clingy but I didn't mind because it gave me something to do while at work and he seemed nice. We had agreed to go for drinks on Monday night.

Monday night rolls around and he texts me all day that he is nervous and excited. I didn't really feel anything going into this date...I had already kind of realized that I wasn't interested but I wasn't going to write him off without giving him a real chance.

We met at 9:30 at a local lounge and he was kind of awkward but I had no problem keeping the conversation going. I knew I wasn't interested, but I had my goal of four men on my mind and I guess I let that dictate my actions for the next part.

We decided to go for a walk after having a couple of drinks and I suggested we go to a park because I felt like going on the swings. On the way to the park he insisted I hold his hand and he stopped a couple of times to kiss.

When we get to the park I go for the swings right away. He was such a poop and was all awkward and embarrassed about swinging. So I just ignored him for a while and swung as high as I could. Then he suggested we go sit on a nearbye patch of grass.

We sit down and he starts at it right away. I just let him do his thing, which was licking under my chin. He also did this thing where he opened his mouth as wide as he could and stuck his tongue out as far as it will go, and then he crammed it down my throat. I would never like to experience that again.

At one point while he was kissing my neck he moved towards my ear, and the next thing I knew he had his tongue in my ear and was tongue fucking it. It felt very wet and all I could think about was how I looked forward to using my q-tips when I got home.

Then I made the mistake of agreeing to bring him home.

I know I should have let it end in the park, and I really have no explaination for why I let him come back to my place.

He insisted on having the lights off and he refused to take off his socks. He went at my boobs like a baby, as though he was expecting them to start lactating. He licked me down like a cat, but never once went between my legs (he licked my face from neck to forehead with a very wet tongue). He must have never heard of the clit. He had no idea.

When he had sex with me he could have been using his pinkie finger...it was small. It was thin and it was short. I used my hand on myself and eventually pretended to get off because I just wanted it to be over.

After he pulled out I felt sorry for how shitty he was and I went down on him. THIS IS THE MOST HORRIFYING PART: I was sucking his little dick, which I could fit in my mouth no problem, and I barfed. I barfed on his cock and he has no idea. It wasn't much and it happened right as he started to ejaculate so I just used kleenex to wipe everything up.... And then I tried not to laugh hysterically.

As soon as the mess was cleaned up I said something like "I don't mean to kick you out, but I should get to bed." I got dressed and escorted him out.

Now, what I haven't yet mentioned was that all while this date was happening, I was already planning what I could do to make this night better.

As of Monday morning I had been texting another guy who didn't seem like my type but was nice and funny. I knew Guy #2 was off work and would be coming through my area of town around midnight and so when I went to the washroom right before Guy #1 and I were leaving the bar I texted him and suggested a walk...

In the parking lot just as I was about to get inside Guy #1's car, Guy #2 called. I answered and made plans to see him when he got to my area. Guy #1 could have heard...I don't know. After I hung up I told Guy #1 that it was my roommate.

After Guy #1 left I immediately ran upstairs and finished barfing. I am all class. I know this. Then I brushed my teeth and my hair and touched up my makeup and left to meet Guy #2, who was waiting for me.

As I was orchestrating all of these events, I couldn't help but laugh at my behavior. What I did last night was something that would have made my jaw drop had any of my girlfriends done it. I kept stopping and laughing at myself.

Guy #2 was shorter than I expected, probably my height of 5'8 or 5'9. He dressed kind of gangsta, but all his clothes were new and clean. The conversation was easy. We didn't even have to think about it.

He told me about how he works at group homes for troubled teens and that he got into it because he was and addict and came from a broken home with a junkie mother. He also told me about how his fiance and 1 year old daughter died in a car accident 6 years ago. About how he was homeless because he hit bottom after that. And a million other sad things. He was the most positive and well-adjusted person I have ever met. He could take any situation and talk about how he took something positive from it.

We strolled around for an hour, stopping to sit on random benches. Eventually, on a bench in a churchyard, we started making out. He was good. I spent a little time batting his hands away because I still had this idea in my mind that I hadn't decided to meet up with him for sex. I know that it was something I kind of wanted, but I was in denial and insisted that I did not behave like this.

Eventually I relented, and I was glad I did. We got a little carried away and he ended up missing his last bus home. I invited him over, not because it would have been a drag for him to get home at this point, but because I did find myself drawn to him.

Over the course of the night we had sex four times, and it was awesome. It was so relaxed and we laughed so much. He showed me all the tricks he could do with his body, such as when he had a hard on he could make it dance and bob up and down. It was so hilarious and I laughed so hard at it, which made it go soft again. Then he made it talk to me. He could also bend his fingers back until they almost touched the back of his hand and he could pop his eyes out of their sockets...which I would NOT let him show me. He had lots of scars on his body because he was run over by a car as a child.

He also tans, which I made fun of him for even though I tan too. We compared tans and laughed at ourselves for being so vain.

I feel a little guilty for being dishonest with him about Guy#1 when it seems like he was willing to to tell me anything...but I do not regret my choices. I see no point in regret, especially when I made the sober decision to do this.

I didn't sleep until he left at 6:30 this morning. We were both so tired but neither of us could sleep because we both had too much to say.

Old Fogey: Part 2

Last week I had my second encounter with Old Guy. It was amazing.

This time I just went straight to his place after work. Why waste time with small talk and drinks?

We got down to business right away. When we stopped for breaks he would sing and at one point he even danced.

This is his favorite song right now, he sang it very loudly and it was hilarious to see him dance naked like the guy in the blue jacket:



After going at it for a while we were laying in his bed chatting and he told me about how he had pierced a woman's nipple with three syringes a couple of weeks ago. Ick.

He tells me stupid shit like this to try and shock or impress me or something. He also told me about his MDMA trip the previous Friday and his coke binge a couple of nights earlier. He definitely does not act like a 43 year old. He acts like a complete idiot.

We did discuss keeping this arrangement going for a while. Which I am pleased about. The sex is seriously amazing. Gentle at times, and rough at others. And LOTs of making out.

After a while we got up and walked around his apartment before getting dressed. He went to the kitchen and I was in his living room checking my phone. All of a sudden I hear this WHOOSH! WHOOSH! WHOOSH! noise and I look up to see him going full force on his elliptical machine. Sandwich in one hand, the other arm flailing to keep balance, and his junk swinging like crazy. I nearly died I was laughing so hard. It was magic.

Shortly after that I stepped into the bathroom to tidy myself up and upon pulling my hair back I noticed THIS beast on my neck:



It is super sore, and tender, and horrifying. No makeup will cover it. It looks grey and splotchy and ridiculous.

I had left marks on his neck too, but none were as bad as this.

At the end of our romp, he walked with me back to my neighborhood and after parting ways I went and got myself a monster of a burrito to regain my energy.

Breakin' it down!

I am confused by the men in my life. Let me list the current list for you, and me.

Old Guy: The guy I sexted and then had awesome sex with. Texted me this morning to arrange a "play date" and suggested that this time around we be more "Reggie and Veronica...and less Betty and Archie". I have no idea what it means but I am excited.

Moonpies: This is a guy I have been texting for weeks. He seems normal and hilarious and I am going out for drinks with him next week. I like him because we both agree that caesars are practically gazpacho and are appropriate to drink at all hours of the day.

Mr. T: This guy and I had sex last week. It was shit but I want to give him a second chance. Call me stupid.

Mr. WE: This is the guy that seemed to forsee a future between us. I disagree.

The Jock: I gave this guy my number the other day and he won't stop effing texting me. I may go for drinks with him tomorrow....and I might sleep with him....

Andre: I have no idea who the fuck this guy is. First he tells me his name is Andre then he says it's Greg. All I know is that he is black and banging a black dude is on my summer sex checklist.

The dreaded First Date "WE"

This evening I went on a date with another man who is twice my age.

The first experience was with Old Guy, and that was sexually charged from the start.

With this guy we exchanged just a couple of emails with no flirting and plans for dinner were made.

Dinner was nice. We had sushi and he paid, which was nice because I never go on actual dates (usually I just meet them for a drink, where I pay for myself, and then either we go our own way or I go to their place or whatever).

At dinner he started telling me how much I will like the town he lives in (he lives just outside the city) and how I can ride my bike there and go fishing and how I will find his condo so comfortable and how he is going to get furniture so I can be comfortable on his balcony.

I changed the subject to antiques and mentioned that my dream is to have a whole entire wall of books in my future home.

He started going on about "WE" as in

"Oh yeah! That would be amazing! But when WE have guests over We would have to hide all the stupid books WE actually like to read!"

He used "WE" a lot in terms of him and I and the future.

During dinner he was honestly very sweet and funny, but I didn't find myself attracted to him in a sexual sense and there wasn't much flirting at all so I was kind of surprised when he went in very confidently for an open-mouthed kiss at my front gate.

It was alright. I really like kissing so I was open to it, which may have been bad because it gave him the wrong idea.

He then suggested we go for a walk, so I told him I would walk with him to his car BUT WOULD GO NO FURTHER. So we walk to his car.

On the way he stops in an alley and starts kissing me again and this time he goes for a boob grab. I swatted his hand away.

We keep walking and he holds my hand.

We get to his car and he says he will drive me the block back to my place. So we kiss some more and before I can stop him his hand is down the front of my dress! I smacked it and told him I was surprised at him for being so fresh.

Then he goes on about when we will see each other next and I manage to put it off because my work schedule is bonkers (and I have another date next week with a guy I am actually interested in).

He then tries to convince me to go with him back to his condo and I say no, and he says he will fly me home in a helicopter, and I told him I needed to go home. (It was really hard to say no even though I don't really want to fuck him!)

Basically, I have no idea what I am doing. I am really stupid and need to not kiss men that I have no interest in.

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!

foreshadowing!!

Regarding the successes and failures of my online dating escapades:

"It was like you stepped out that car and right into that hallway" - Muffy

full stories soon! 

My Menz

This is going to sound entirely ridiculous but I need to write it out so I can have some recond of the influx of men in my life. I have gone from none to an excess. I plan to fuck all of them.

I will arrange them by age.

Garrett
Age 24
This guy is recently separated after a two year marriage. He gets anxious in social situations and does not do well with flashing lights or large crowds. He has tattoos, a pierced nose, and multiple stretched piercings in his ears. He is a maintenance guy and is recording his own album in his apartment. I hate the music. He had never even heard Led Zeppelin until he was 18. He is awkward but cute and sweet. I want to fuck him.

Tyler
Age 26
I don't know much about this guy except for the that he is a ginger, likes to ride bikes, and does crafts. He seems cool and we are going to go for a bike ride in the next week. I have always wanted to fuck a ginger.

Graveyard Guy
Age 38
I have only met up with him once since we reconnected last month. He texts me about wanting to eat me out almost daily. It is honestly boring and exhausting at this point. He recently suggested the idea of a threesome with another guy. This feels like a bucket list thing. Anyway, I am sure I will have sex with him a few more times before summer is over, even though he annoys the shit out of me.

Old Guy
Age 43
This guy is divorced but thankfully has no kids. He is a total old hipster dude that wears Ben Sherman, listens to 60's rock, and has many tattoos including on his hands and neck. He wears fun hats and thick framed glasses. I am super excited because I have such a boner for both tattoos and old guys.

Basically, I am going to whore it up with the help of internet dating websites.

The First Wave

Online Dating – Week 2

Status: I AM SO OVERWHELMED!!!

The first wave of men has been largely undesirable.

No! I don’t want a sugar papa!

No! I don’t want to tell you if I wear dresses and scarves sometimes!

No! I don’t want to think about what it would be like to be wined and dined by someone much older!

No! I don’t want you to come over and touch my feet!

No! I don’t want your phone number IMMEDIATELY!

No! I do not want you to be callin’ me pet-names!

No! Your spelling is atrocious!

No! JUST NO!

I Want:  Sexy Uglies!

Tall, broad, scruffy, deep voiced, meaty, stallions that are more Beast then they are Prince – that are charming and arrogant, with twinkles in their eyes – that look like they could have a woman for breakfast at dinner.

I don’t think that it is too much to ask for, because I am already sacrificing my lust for post-secondary educations and science.

There are a few promising options amidst the garbage.

I’ve been messaging regularly with six guys. Two are boring, so I will not bother describing them unless those conversations become more magical.

Bachelor #1: Donkey Kong

DK is 28 and a classic example of a Sexy Ugly. He’s tall, broad, and has big hands. He kind of looks like Donkey Kong (in one picture). He is arrogant, charming, and flirtatious without being gross (this is something that the men of pof have a very difficult time with). A quick look through our emails might suggest that we are enemies – Him, suggesting I do his laundry, and me, questioning if that’s his real age and making fun of him for having no post-secondary. I am concerned that underneath the fun-douche there is a real douche.

He makes me nervous in a good way. He’s older than anyone I’ve ever dated, and I find that thrilling. He’s been really vague about his life, but from what I gather he has some kind of job for the government, drives a car, and lives in a house. I am hoping its not lives-in-a-house-with-HIS-MOM situation. We’ve exchanged phone numbers and will probably talk this week.  

Bachelor #2: Scarf

Scarf is 24, tall, seems eccentric, and my gut tells me he is pof’s version of a bar-star. We’ve exchanged adventure stories (he used too many adjectives, in my opinion) and we’ve razzed each other a bit. He’s started being more flirtatious, but I am not 100% into it.  I just can’t shake the bar-star theory!

Bachelor #3: Race Cars

Race Cars is 24, really tall, and cute. He is more cherub-ish than he is a sexy ugly, though. Muffy has had some previous interaction with Race Cars, and discovered that he is/used to be (?) a race car driver and has his own ridiculous website (or something).  He hasn’t mentioned his former race-car driving life, but I eagerly wait for it to come up.

Bachelor #4: Lumberjack

Lumberjack came out of nowhere.  He is 22, and the shortest of the bunch at 5’10. I am not super keen on dudes that use the instant msging part of the website as a first attempt at contact, so I was not pumped when he did. Much to my surprise, we had a perfectly nice conversation. At first I didn’t feel into it at all, and made him do all the work, but then he got really funny/interesting (ie: he mentioned he was a lumberjack), so I decided to engage a bit more.  It turns out that we probably have a lot of people in common because he plays rugby.  When he asked for my phone number I told him that I don’t give it out right away, but I encouraged him to shoot me an email. Before he logged off he sent me a few jazzy/blues songs, and told me he’d be emailing me soon.

Bachelor #5: The Friend

I made plans to go for a walk with my friend this week.  We’ve known each other for like 6 years. I may or may not have a bit of a crush on this pal, but because of weird history stuff I’ve felt really uncomfortable with having said crush. A few weeks ago he came to a party and told me I had sexy hair, invited me a concert, and asked me to go see a movie. HOW did I respond? “I cut my hair with meat scissors”, “No thanks, I don’t like that band.” And my personal favorite: “I don’t really go to movies often b/c I am poor, so I usually just wait to rent… and if I can rent, I may as well just download it and watch it by myself. Like a date with myself.”

I am stuck in a web of my own friendzone. Recently, he’s revealed to me that he’s being celibate for the summer, so I asked him if he was free for a walk.

He has a pof too. He just msged me to say that my profile kills all future boners, and “see you on Wednesday”. I told him that I was happy to assist him on his quest for celibacy.

Even though I don’t think anything will actually happen here, I think its good to keep some variety.  He is the douchiest guy I know, and sometimes that’s all a girl really needs to cut the estrogen in her life and balance out the incoming testosterone.  He’s included as a bachelor because I am not horrified at the thought of hooking up with him, and because he had the audacity to msg me on pof.

OH AND, update regarding Dimples:

The date was fine. We clicked over conversation, but I wasn’t feelin’ it. He’s so little! He was really funny, charming, cute, all of that good stuff, but when he hugged me at the end, I didn’t like that he felt so small in my arms.  I gave him a mix cd (an awesome mix cd). That night he texted me to say he didn’t get a chance to listen to it, and the next day he emailed me to tell me it was “wonderful” and asked for the song list. I sent it and haven’t heard from him since.

On one hand I am annoyed that I didn’t get a mix cd from him, but on the other hand I am somewhat relieved. I liked hanging out with him and talking, but I couldn’t imagine myself having sexy-times.