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Shamus and Smitty

I’ve had all weekend to figure out how to post this entry, I was tempted to use a filter or make it friends only. I was tempted to ask certain people to skip this one, but in the end, I’ve decided to leave it public. Just a warning, This entry is about gay sex, if the idea of thinking about me having sex with other men seems unpleasant, you might want to skip this one. If ever there was an entry where I felt naked in front of the class this is it.

Previously on Monkey! Monkey! Monkey! The Sexy Trinity!

Two teens talk late into the night after Mike spends a few minutes crying
Mike: Eric, you life is perfect
Eric: uh, no it isn’t... I’m gay.</a>
Mike: I think I am too...
Mike fucks Eric without lube then distances himself from Eric and treats him with disdain. Eventually they will become friends again.

Enter Mike’s brother Shamus... Who is depressed about the breakup with his longtime boyfriend Smitty.
Shamus: Have you come out to many people?
Eric: No, just two people, three now.
Shamus: You look tense let me give you a massage.
Eric: Sure!
Shamus: Your shaking, I don’t’ think you’re not ready, calm down. No one’s going to hurt you.

Shamus and Smitty have gotten back together and they have become my first gay friends. I began to relax and come out to more people. The shame I felt about being gay started to melt away. They have been together for three years now and I looked up to them as role models. Shamus was the kind of person you instantly wanted as a friend, quick witted, funny, caring, and the life of the party. Smitty was the kind of person you wanted to get in bed instantly, an underwear model who’s glimmering eyes and smile winked á la Erik Estrada.

Smitty lived just a block away from me behind the hospital I was born in... At this time it was a rehab center but is now a mental ward, I find this immensely amusing. Because I now had gay friends who lucky for me were positive role models I started to hang out with them more and more. After a party at Smitty's house and everyone had gone home and Shamus had passed out, Smitty and I started a very deep conversation. He told me lots of intimate details of his relationship with Shamus, how they first met, fell in love and eventually all about his frustration. Smitty was at that time the only person I had told about the horrible experience I had with Mike, Shamus' brother. I didn't tell him everything but he knew enough and it seemed like I had a great weight lifted to have finally been able to talk to someone about it. I was really happy that Smitty and I were bonding and sharing. I felt I finally had someone to talk to.

As I sipped my Long Island Smitty continued to tell about how he loved shamus but he was inexperienced and curious. He wanted to sleep with other men but didn't want to leave his love. "I think a good solution would be to have a threesome," he said.

"That sounds like a smart solution to me. How does shamus feel about that?" I asked.
"He thinks it's a good idea, I just don't know how to ask someone." He replied. I laughed as I said, "You're asking the wrong person, I've only had sex once, I have no idea how you would ask someone."
"No", Smitty said sternly as he looked me directly in the eyes, "You don't understand, I am saying I don't know how to ask someone." He leaned forward and I was still confused. He continued to stare at me until I started to respond, "but I... Oh.... Oh." and a big smile spread across my face as what he was really asking finally dawned on me.

Shortly after the realization we went for a dip in his hot tub and he put his hand on my leg, gave is a squeeze as his other hand wandered around my chest. We continued to talk as he continued to run his hand over my body. I began to explore his.

< TMI alert >
Somehow cock size came up in conversation I'm now pretty sure it was a plan for an opening to grab my dick. I said, I didn't think I was very big. I didn't compare to the guys in the videos I had seen, but I was really thick. Really he said as he reached under the bubbling water and wrapped his hand around me. "My god" he said "What are you talking about, you're huge!" Sadly I had to tell him he wasn't exactly grabbing just my dick. I have low hangers and in the hot water they were even lower. He had a hold of me all the way down to my taint. He decided he needed to measure me with his mouth and disappeared under the water. When he came up, he seemed happy enough with my dick and I felt a lot better... In more ways than one! Once my measurements were taken we decided it was getting a little too hot in the hot tub and decided to cool it, and I went home with a smile on my face.
< /TMI Alert >

A short time latter I got a call from Shamus and Smitty and was on my way over to Smitty’s house once again. I had another long Island while talking to Shamus about my, uh, conversation with Smitty. He basically said he was cool with all of this and wanted to make sure I was as well. We would take it a slow as I wanted. It had been about two years since my last botched encounter with Shamus. I had worked through some of my issues with sex at this point and was happy to hear they were willing to let me decide the speed. I think it calmed me more than the Long Island. Shamus then laid down the simple rule, never without him. What Smitty and I did the other night in the hot tub was cool this time but not ever again. This was not a problem.

Most of the night is now a blur, a happy blur. There are laid that I know I will have perfectly preserved forever while other things are already gone. We played Naked Twister it was a nice way to warm things up. Shamus did the spinning and Smitty and I did the naked twisting. We played around for a while before we all headed to the hot tub. Once again Smitty disappeared under water and was amazing me with his ability to hold his breath when my heart stopped. Shamus was facing me and saw the startled look on my face, He turned to see Smitty's sister squinting and stumbling towards us.

I grabbed Smitty hair firmly and pulled him off of me, I still smile when I imagine the annoyed look on his face turning to shock and embarrassment as I turned his head to face his sister. Lucky for us she was really drunk and seemed oblivious to what she interrupted. As she stumbled off he was still in a bit of a panic... "She must know what we were doing, She had to walk over the twister game!" This caused both Shamus and I to laugh at him. But now, whenever I see a Twister box or mat I think of sex. Really good sex.

Nothing ever goes perfectly and I always make mistakes, but I learn from them. Shamus and Smitty were very sweet and offered me jewels of information as they thought of them. I learned what things were called and what they felt like. "Rimming is fun, but you need to be very careful who you do it to. Rimming can be very dangerous to your healthy if you do it to the wrong person." I didn't do any rimming and I wasn't exactly very fond of being on the receiving end either, I was a little freaked out by it.

Eventually it came time for me to learn more, Shamus called me over to watch him fuck Smitty. "Isn't this hot", he said in his sweetest voice as he slowly pulled in and out. It was I had to agree. I enjoyed watching, I had only seen the smallest amounts of gay porn at this point in my life. To this day I cannot help but think sloppy seconds is really hot. When it was finally my turn, it was time for my first real mistake. I had never topped anyone and had only been topped once, which was not a pleasant experience. So everything I knew about fucking was learned from porn. And those porn guys just shove it in, and that's what I did. Smitty screamed, and I began my parade of apologies. A few minutes of resting and education on how anal sex really worked and he was ready to try again. I took my time and paid attention to see how quickly to proceed. After things were going smoothly I told Shamus to put on a condom and Smitty grabbed my arm and said, "Oh, no I think I have enough inside me already." "No," I said, I wanted to be a lucky Pierre, although at the time I wouldn't have known that term, "I want him to fuck me while I fuck you!" Shamus assured me it wouldn't work and he just continued to watch.

When Smitty said he was becoming a bit sore he asked if we could flip. And we did. I really enjoyed being fucked a lot more this time although it was still a bit uncomfortable. I was stupidly tightening my ass because I thought it would feel better for him. I've learned a lot since then.

While I was enjoying myself immensely I was beginning to grow tired. So were Shamus and Smitty. "Are you close?" Smitty would ask me several times thought the night, but I never was. Shamus had dropped out and was leaving it up to Smitty to finish me off. We took a few breaks but each try I didn’t come any closer to reaching that peak that young boys are supposed to reach so easily. What was wrong with me? It seemed the more I wanted it the less likely it was to come. Heh, pun. Eventually I just past out on Smitty’s chest. I awoke a few hours latter in the wee hours of the morning, stuck to Smitty’s chest. I peeled my cheek from his flesh. I saw the early lights of dawn coming through the window and realized that I hadn't told my parents I was spending the night anywhere. Since I was always out and my parents gave me tons of freedom, I always let them know where I was spending the night. So I panicked at the idea of my dad seeing my bed unslept in and not knowing where I had gone the night before. I snuck out of Smitty’s house and back into my own.

The next day I was trashed, I felt hung over. I had only had one drink at the beginning of the evening and was never drunk. I deduced I had a Boner hangover. While drood may have the hands free superpower, which is a very good power. Mine is a little less controllable. I stay Hard as a rock as long as my brain is excited. I don’t loose my erection after I climax, and as long as something is going on I will be completely unable to make it go down. Thank god I also have the ability to pee with an erection! Well I was so excited that night I kept an erection constantly for probably 6 hours. I was in pain and I had some seriously blue balls. But I was happy. I finally had a nice sexual experience. My first threesome, and I still have never been kissed, by a boy that is... Something that wouldn’t happen for another year.

When I spoke with Smitty latter he was pissed at me for taking off but got over it quickly. We got together a few more times and eventually I was able to cum in front of Shamus and Smitty. It would be quite some time before I figured out I had harbored a strange guilt over a joke my father had told me. But still to this day, If I don’t feel completely comfortable in my surroundings I remain cum shy. This is what single handedly ruined my chances at being a famous porn star or hooker! Damn.

Everybody's Changing - Keane - Hopes And Fears


( 16 comments — Leave a comment )
Dec. 13th, 2004 07:40 pm (UTC)
Perhaps in part because I don't know the full cast of characters, this is just a really hot story for me. No fraughtness. Just hotness. : )

I stay Hard as a rock as long as my brain is excited.

This is one of the really, really hot parts, btw. : )

Dec. 13th, 2004 07:58 pm (UTC)
agreed. for me the mind fuck is always much more intense. if i'm not turned on in my head my body starts to shut down...
Dec. 13th, 2004 08:04 pm (UTC)
Much hotness. I can understand all of the emotions that roiled around with it too. But damn, I really shouldn't read stories like this at work.

The waking up stuck to someone created a wonderful image in my head and reminded me of my first time and first boyfriend. I'll have to post about that sometime.
Dec. 14th, 2004 06:35 am (UTC)
Thank you.
I got into a bit of trouble reading drood's Bioporn... by the HR woman no less. although I'm not sure if she really knew why I wouldn't getup and help her, I'm sure she knew something was up.
and waking up stuck was one of my favorite parts too.
Dec. 13th, 2004 08:32 pm (UTC)
This entry is about gay sex, if the idea of thinking about me having sex with other men seems unpleasant, you might want to skip this one.

Unpleasant? You? The idea of you having sex with other men?
Only problem I had was with some typos otherwise it was pure hotness which I think you are, by the way.

I was in a threeway once and was never able to get it up. I blamed it on the drugs that someone had brought to the situation (krank) which it may have been but it was probably more psychological. There was something about there being more than one person, one of whom I wasn't interested in, that kept me bottled up.
I spent too much time on my knees on a hardwood floor that night. It took a week for them (my knees) to get back to normal.
Dec. 14th, 2004 07:10 am (UTC)
I have quite a few people reading who are not as interested in mansex as the rest of us. My friend Eugene who I've known since Jr High, knows all the people mentioned, is straight and pretty religious. He is übber cool, but I thought I should warn him and probably a few other people like my straight female coworkers.

Of course now I am tempted to go back and look for the typos... But at this point it's silly. Thank you for the compliments. I'm glad you enjoyed my post.

From what I have heard very few men can get it up when on speed under the best circumstances. But even more if you aren't into the guy, magic is not going to happen.
Dec. 15th, 2004 11:23 pm (UTC)
Straight, pretty religious, and very very afraid of any of my homosexual tendencies
LOL. Thanks for looking out for me, though.

"My eyes! The goggles - they do nothing!"
Dec. 13th, 2004 08:35 pm (UTC)
And, incidentally, if I ever get around to posting stories of my first few sexual experiences, you will discover that I never kissed the first guy I had sex with, nor did I ever cum during any of our adventures. I didn't cum until I was with my 2nd guy....

I am not generally cum shy now, though.
Dec. 14th, 2004 07:17 am (UTC)
I think it just sounds funny that I didn't kiss the first three guys I slept with. makes me feel like Drew Barrymore, the drunken preteen, not the one from the movie where she goes to high school at 30. Just kidding.
Dec. 14th, 2004 04:00 pm (UTC)
It is unusual, but not unheard of.

Speaking for myself, I was not ready to kiss a guy at 14, although I was ready to take a guy's cock in my mouth. I was not afraid to explore my sexual attraction to the male gender, but I was very afraid to explore my emotional attraction. I knew that some boys went through a "phase" of same-sex exploration, and had no problem letting myself go through my phase. Kissing another boy would have been entirely too intimate for me, though.
Dec. 14th, 2004 04:58 pm (UTC)
I had a very different experience because my first boyfriend was also my best friend who I had a deep emotional attachment too. In fact our sexual relationship started because he decided it was time to kiss me...

So Kissing has always been part of it for me. I've seldom had sex with someone without kissing them.
Dec. 26th, 2004 05:41 am (UTC)
What a fun story. It put me in a pleasing kind of mood. Everything resolved except for the coming problem, but you cited the resolution to that which I had to read.

Your a good storyteller.
Dec. 29th, 2004 09:02 pm (UTC)
Ya know, I really enjoyed reading your story. For the honesty and the emotion, in large part. I need more of that with my sex. =)
Dec. 30th, 2004 06:58 pm (UTC)
Thanks. I'm getting better at these posts that are very revealing. I am always a little fearful when I post them, but it has never come back to bite me in the ass or really embarrass me too much. If you would have told me last year I would have put this part of my life on the web I would have said you were crazy.
Dec. 30th, 2004 10:48 pm (UTC)
I may give it a try, you set quite an example. I have alot of emotional unpleasantness associated with my stories, which I usually contain, out of fear of distressing others.
Dec. 30th, 2004 11:14 pm (UTC)
I actually went through quite a bit of soul searching and emotional turmoil before I posted about Mike, the guy who took my virginity. I was so traumatized by the whole situation and had promised him I would keep it secret.

I think a few people that read my journal think I am constantly having the worst things happen to me, but the truth is my life is pretty charmed. I think I have less bad things happen to me than most, I just have the courage to talk about them. I try to keep my journal more about the exceptional things rather than the day to day tedium. It just seems the traumatic are easier to remember that the positive things. I really do need to try to post more of the good stuff. I think a couple of people are about to send me disaster relief money or something.

Balance and moderation are my compass for life.
( 16 comments — Leave a comment )