Tony C.

I majorly fucked up last month. Why do we do such self-destructive things to ourselves when we’re single?!

Tony was an associate of mine who works in Australia. We happen to be at the same location last month for a conference and I thought it would be good to connect with him. We have a mutual friend named Adam, who actually introduced the both of us. For the past few months, Tony has be highly flirtatious and interested in me. However, the distance between Australia and the USA helped to prevent any bad consequences from happening.

Tony, after all, is a high ranking government official and it would be bad press for him to be discovered with someone like me. Also, he’s practically married to a gentleman for the past several years. I blame Adam for feeding the fires and telling me that Tony and his partner were on the rocks.

Rule #5: DO NOT play around with a married man, gay or straight.

I broke this rule. During a break at the conference, I invited him to my hotel room. He obliged and we soon connected.

Either he was tremendously guilty by the experience or appalled by me, for the rest of the conference he avoided me. Of course my self-esteem just shattered at that point. All I could think of was what was wrong with me. I couldn’t even look at him in the eye. Poor Adam didn’t know what the hell was wrong with me.

I couldn’t let this out at all. So, I’m keeping my secret here. For the Universe to judge. I am doing penance for all the wrong things I’ve done. I cannot do shit like this ever again. It’s not healthy for me to go after someone unattainable. I must hate myself that much to keep torturing myself.

When do I start to love myself? I think when I’m able to let go of my fears and accept myself as who I am. I’m getting older, not getting prettier – it’s the way all things go.

Fantasy #1: The Doctor

I’ve always had a knack at picking the most handsome and sexiest doctors in the city. In fact, each one of my practitioners are drop dead gorgeous!

Today, I am fantasizing about one of those doctors. He’s my eye doctor. Married with 2 kids. He’s a year younger than me with beautiful blue eyes and light brown hair. He has an amazing personality and is definitely suckable. (Fuckable, yeah, that too, but I’d rather be receiving him than giving it to him.)

I imagine us up close and my hand just touches his knee and brushes his thigh gently. He’ll look at me and I’ll smile at him…

The rest of the story…I will leave up to your imagination.

Hook-Up Guy #6: Andy

Stats:

  • Where did we meet: Craigslist
  • Age: 26
  • Height: 6’2″
  • Weight: 90 kg
  • Ethnicity: White guy, light brown hair
  • Position: Top/Straight
  • Penis Size: 7″ Uncut
  • Best quality: Accent

Andy was an Aussie from Sydney. He was a curious married guy who wanted to do some mutual j/o. I obliged. In the room, he was a little nervous. He had turned down my first invitation, but his libido got the best of him and he finally succumbed. 

He was a relatively attractive gentleman. He was working late and told his wife he was having drinks with friends. I wondered how often he did this “after work” thing. He told me that he only played around with a guy once “a long time ago” and has been curious ever since. 

We laid in the bed next to each other fully clothed. He was dressed in a full business suit & tie. He removed his jacket and tie and we watched television and chatted for a bit. 

He proceeded to touch my groin. I was fully clothed still and thought: He must be telling the truth! He is new at this! I smiled at him. I found him attractive, but I wasn’t really aroused. I just let him massage me, still wearing my pants. I moved my hand to his groin and proceeded to massage him the same way with his pants on. He obviously was more into this than I was.

After about 20 seconds, he said: “Ah, fuck it.” And quickly pulled off his pants and underwear. He originally didn’t want any skin-on-skin contact, but I could tell he was so horny and that this opportunity for him wouldn’t come again any time soon.

He was raging hard. His uncut cock was fully stretched. He laid back and let me touch him. He quickly unbuckled my pants and pulled down my zipper and I felt his hand wrap around me. He stroked.

And I stroked. Not more than a minute and he asked me to slow down/stop because he was close to coming. He was definitely a virgin for gay experiences. I wondered if his wife got him this excited.

I paused a moment and then continued. It was about 2 more minutes when he told me he was about to cum. He moaned. I stroked him and he exploded all over my hand. 

I got up and went to the bathroom to grab a towel. I came back and cleaned him up. At this point, I didn’t really feel like getting off at all. Something about a nervous straight married man who is too excited to hold on – didn’t really turn me on. I cleaned up and put on my clothes.

He did the same. But as he was doing this, he kept apologizing to me for being so lame and boring. He also nervously started telling me how he’s glad he got this out of his system and that he’s not going to ever do this again. He kept saying Sorry to me. Yeah, I definitely wasn’t turned on at all at this point.

He thanked me and went on his way.

The moral of the story is: don’t be the first guy for first-time curious straight married men. Let someone else initiate them to sexual awakening. Maybe after 2 or 3 times, they’ll be more comfortable and the sex could be more satisfying…at least for me!

Chris D

ImageI forget who said “Hi” to who first, but it was back in May when I met Chris D. Yes, it was during one of my random Grindr browsing. I noticed that he was within 200 feet of me and so I suspected he was a neighbor. And i was correct!

Our first “meeting” was for coffee at the Starbucks down the street from the apartment complex. He suggested it first and so I thought – this would be cool to meet a new friend who is also a neighbor. We met down in the lobby and the first thing I noticed was how tall he was. I think his profile said 6’1″. Damn. But besides that he was definitely quite adorable!

A recent transplant from Washington, D.C., we soon hit it off chatting about his former home. For work, let me just describe him as a Director for IT systems and management. Brilliant guy. I immediately detected the “geek” streak that I’m so drawn to. That first coffee meeting was awesome! He was a gentleman and very cool. I asked a few minor probing questions about his former relationships and found out he was single too.

Fast forward to July. Chris D and I have hung out several times, going to restaurants, a couple of bars, having brunch and even watching the 4th of July fireworks together. I’ve known him for almost 3 months and yet, I still don’t really know him. I’m a little nervous to ask him about the more personal questions in life. I appreciate his friendship and feel that I don’t want to ruin anything by having a serious tone of conversation.

I could see him definitely being my type. He is my type. But I’m so wary right now. (See entry on “Vulnerability”) He’s kissed me a few times as what I describe as a “European” good-bye. But then again, my therapist did point out: How many good friends do I normally kiss good-bye?

My radar tells me I’m not his type and that I am just a good friend for him. If he were to ask me out for something more serious, I would definitely consider. For now, I think I’m just going to lay low and continue my hunt elsewhere.

Hook-Up Guy #5

IMG_0604

Stats:

  • Where did we meet: Grindr
  • Age: 26
  • Height: 5’10”
  • Weight: 138 lbs
  • Ethnicity: White guy, dirty blonde
  • Position: Top
  • Penis Size: 7″
  • Best quality: Body and cock

He told me his name was “Tom” but I highly doubt that. This was a straight guy with a girlfriend who was really nervous to meet, but I could tell he was super horny. Being discreet was extremely important to him. He works for a non-profit supposedly. Really handsome and sexy guy. Very fit. Very tight body. Beautiful abs and a gorgeous cock.

To this day, I still crave him and would love to hook-up again. The one cool thing I remembered was that he wanted to undress me slowly and so I let him. I could tell he was very into me and got immediately aroused. This session was definitely a quickie. He couldn’t hold on too long at all. This is a noticeable trait for a “straight” guy. It’s so hot and exciting for them that they last 10-15 minutes top.

I was in a rush anyway, so I was happy he came pretty quick.

Yep, I still wonder about “Tom” and his wonderful cock. Sigh.

Hook-Up Guy #4

One weekend I decided to respond to an ad on Craigslist. Married White Male, alone for the weekend, wife was away on travel. He seemed nice via e-mail, but was your typical “straight/married” guy who wouldn’t send photos for fear of getting caught.

So, I went over to his house in Lower Queen Anne, near Kerry Park. The house was a gorgeous home with a beautifully landscaped yard. He had a rather large dog which was overly friendly and wanted to play with me.

Stats:

  • Where did we meet: Craigslist
  • Age: 40 (but looked way older)
  • Height: 6′
  • Weight: 185 lbs
  • Ethnicity: White guy, light blonde (or grey)
  • Position: Top
  • Penis Size: 6″
  • Best quality: Gentleman qualities

What freaked me out a bit was that he said he had a furnished basement and he lured me down there. Stupid, I know. But when hormones overwhelm you, all rational judgment gets locked away. In retrospect, he could have been a serial killer and I could have easily ended up on the evening news.

But fortunate for me, he was just a horny married man who wanted to fool around with a guy before his wife came home.

And so, fool around we did. From what I recall, he had a decent body, but he definitely was older than what he was describing on his personal ad. This turned me off big time. There comes a point in a man’s life when you can no longer pass for a certain age. My time will come; your time will come; and his time came and went.

He looked 10 years older than the age he was describing himself as. But this was a “rare” married guy wanting to get off – so for the interest of all gay men – I made sure to give him the best experience possible that his wife couldn’t give him.

When all was said and done. I thanked him and went my merry way.

The funny thing is that married men having gay sex is not actually a rare thing. It happens quite often, more so now that gay culture is so widely accepted. This guy was an executive with some free time on his hands. He probably has two kids that he’s raising on top of all this.

You’re probably telling yourself: a married guy with kids having gay sex has got to be gay. Well… yes and no. The difference with a married guy having sex with a guy and a gay guy having sex with a guy most often has to do with the heart. The married guy was just probably going through the physical act without caring about who I was. It was the lust, libido and the heat of the moment driving him. For a gay guy, there is all that, plus a tiny connection/attraction to the guy they are having sex with. For convenience sake, I will describe this as a “heart connection”. Even though its tiny and insignificant for some, the connection is there. It’s what draws you to that hot guy in the first place.

This married guy’s heart connection is most likely with his wife. He had none with me. So, no matter how many times he’s hooked up with men; his wife, ironically, still has his heart. Is it still cheating? Hell, yes. But that’s not my problem.

I’m just here to get off.

C.J.

ImageI met C.J. while browsing Grindr. I convinced him to meet me after work and he agreed. Well, actually, he agreed after he got himself drunk after Happy Hour with his friends/co-workers.

C.J. and I immediately hit it off. It was a definite rarity for me to click so quickly with a guy. Perhaps I was horny, perhaps he was drunk, perhaps it was a combination of both – whatever it was, we hit it off big time.

Sexually, the passion and intensity was potent. I’m not sure if we’re 100% sexually compatible, but the mutual attraction was enough to send sparks flying. He disclosed he was a “bottom” which not a surprise for me.

On that first encounter, we woke up several times and had sex about 5 times over the span of 6 hours! Not bad at all!

Stats:

  • Where did we meet: Grindr
  • Age: 29
  • Height: 5’7″
  • Weight: 136 lbs
  • Ethnicity: White guy, dark brown hair and brown eyes.
  • Position: Bottom
  • Penis Size: 5″
  • Best quality: Personality; Cute Looks (reminds me of Daniel Radcliffe); Stylish dresser; smart

C.J. and I have had encounters several times over the past few months. What I appreciate most is that our friendship continues to grow. However, I realized in May that this is a relationship that can only stay in friendship. I don’t think we can be friends with benefits any more. I feel that it’s not fair for him (or I) to be in a long distance relationship. I’ve since encouraged him to meet guys and go on dates. I know that he likes me and he knows that I like him. Unfortunately, we aren’t in the same space for a relationship to develop. I still want to make friends and meet people – I think he’s more prepared to start a longer term relationship.

He’s been single for almost 2 years and he knows what he wants. I’m still trying to get there.

I think this is another one that will find his soulmate very soon. It’s funny how I’ve met a couple of really great guys that I least expected to meet. The good news is that I hope they remain my friends for years to come. Maybe my role is to help nudge them in the direction and path of their next chapter. Butterfly effect and all.

C.J. was supposed to meet me and I was supposed to meet him. The added coolness factor is he passed my “dog test” and my dog adores him. How rare is that!?

C.J. is such a cutie and I know he’ll find someone perfect. Did I mention how much he looks like Harry Potter?!?! Adorable.

Hook-Up Guy #3

Back in February, I did a crazy thing. At least it was more libido-driven rather than using my rational mind…

So, I fired up my Grindr around 6:00 pm in the evening and connected with a young guy named Ryan who was visiting Seattle. He was busy celebrating his “birthday” and so was getting the evening started with friends. He said that he would text me later to see if I was free to hook-up. I told him that was fine, but that I had a flight to get ready for at 5:00 am that next morning.

Around 1:30 am, I receive a text from him and he wanted to hook-up with me. He was staying with his friend in Belltown, only about 5-10 minutes away. So, in a half-asleep/half-horny state, I invited him over.

Stats:

  • Where did we meet: Grindr
  • Age: 19
  • Height: 5’10”
  • Weight: 138 lbs
  • Ethnicity: White guy, dark brown hair and brown eyes.
  • Position: Bottom mostly, I think.
  • Penis Size: 6.5″
  • Best quality: He wore glasses and resembled a cute Geek.

He arrived after 2:15 am and we sorta hit it off. We started making out on my couch when suddenly he turns to me and says: “I need to pee.” So, I excused him and he went to the bathroom to do his business. A moment later, we were at it again, making out on my couch. About 5 minutes later, he told me that he had to pee again. So off he went to pee in the bathroom. Now I was fully awake and getting irritable. Ryan was obviously drunk and wasted – and quickly becoming a HUGE turn-off for me. We continued making out and he kept passing out. I sighed and got him off to quickly end the whole thing. He turned to me and asked me if I wanted to get off. I said “Nope.”

He proceeded to get comfortable and was about to fall asleep. Severely irritated, I never let anyone sleep over, let alone a one night stand. SO, I woke him up and told him that he had to go. He looked at me and frowned. I could tell he was obviously tired, but I wanted him the fuck out of my apartment. I told him that I’d call him a cab and he was happy about that. Unfortunately, I only had $2 in my wallet for cab fare. I gave him the $2 and sent him on his merry way.

By then it was close to 3:45 am in the morning. Lessons learned here was: Don’t get tempted with twink meat no matter how horny you are. The folly of youth is only going to make you realize how old you are and how you can no longer tolerate stupidity. Ryan was a $2 whore who didn’t even make me come.