It was all so confusing...
There I was, freshly 18 in time the summer with everything ahead of me!
Like every 18 year old guy I was invincible. I knew it all and was eager to prove I've done it all (even if I hadn't). It was late may and my neighbor had invited us to his summer kickoff cookout. It had been nothing special in the past just burgers and dogs, sodas, beer. He had a few backyard corn hole boards and horseshoe pits but it wasn't an exclusive invite to say the least. He typically invited the surrounding neighbors and most just stood by their bordering fences and talked until they'd retreat back inside. Most of the actual party guests were friends of his from work or his family. His daughter Kelly also would have friends there which is what peaked my interests the past few summers.
Kelly was my age, in fact she was graduating with me in a few weeks. We were as close as neighbors could be. We had both lived with our parents our whole lives and still both resided in our childhood homes. I thought of her as a sister, sort of. She was 5'1 100lbs highlighted hair tan blue eyes, definitely a 10 by most standards but I never took a chance. Her cousin Pam however, who was equal to a sister to her, was my crush. Pam was blonde about 5'3" 120 lbs full B cup breasts and a very nice butt if I had to admit. Pam was also a year older then Kelly and I but still hung out with Kelly like they were classmates. Kelly's parents were average parents at that age. Her dad was a show boat and her mom a hen. Pam's father was also single and the brother of Kelly's dad. Pam's mother had left Mr Todd (Pam's dad) a few years ago for another women. The remained clow but were often gossiped about. Mr Tom was a fan favorite though. A true crowd pleaser. He seemed to know and like everyone and was absolutely hilarious. He always showed up late and with his friend Mr Tom. Mr Tom was his age, around 58-59 and was also very nice. He wasn't as loud or funny but always polite and friendly.
Anyways... This cookout was going to be my last shot at Pam! I could feel it was now or never. Next summer I'd be 19 and I would have to have somewhere better to be than my parents house for a cookout. I decided a few weeks ago I was going to openly drink at this thing. My parents knew I drank and so did Kelly and her parents. I never had any major issues with being drunk so noone seemed to mind when I grabbed my first beer from the cooler.
Walking over to Kelly and Pam with a cold beer trying to fight the urge to smile, opened up the door they were looking for and they immediately ran to the cooler.
As the day went on and the drinks flowed conversations led to games and games back to conversations. It was around 5 o'clock when I finally got Pam alone at a picnic table. short lived though as our awkward joking was interrupted by Kelly and her guy friend. But it was ok. It had the makings of a double date. We exchanged jokes and the jokes became dark then dirty then somehow became "what ifs". After a while we got to the most juvenile game of the day, truth or dare. After a few rounds of truths things were heading in the wrong direction. I didnt care who Kelly had a secret crush on in middle school or about who her friends first kiss was. I knew I had to get things moving in a more steamy direction and soon.
"Truth or Dare, Pam" Kelly blurted out
Damnit! I said to myself. It was supposed to be my turn but I'm not going to argue with a semi drunk 18 year old female at her own house, especially since her dad could still kick my ass.
"Ummm boring, I pick dare!" Pam said, looking as bored as I was.
The first dare! I thought. Finally! This would surely take the lid off this game, it had to!
"Ummm ok, you have to... Ummm... Kiss Bruce. On his lips, with tongue," Kelly smirked.
Yes! I thought. Did Kelly know I had a crush on Pam? Was she helping me out? Or maybe she was just protecting her own love interest and wanted Pam out of the picture. Either way her it was. I had to be cool.
"Ok," Pam didn't object.
Leaning in as if she's been waiting for this dare she kissed me aggressively. She made every first move. Her lips forced mine to follow her tongue explored before mine. She was absolutely leading the way and I loved it.
After a few seconds it was over and Pam simply shifted back and sat upright as if nothing ever happened. Me on the other hand, had to blink and refocus before my intentions were on full display here.
"OK, guess I'll ask Bruce a question" Pam immediately said while still adjusting in her seat.
"Noway! I'm taking the dare!" I exclaimed eager to keep the thrills coming
"Haha yes!" Pam said smiling ear to ear. "Finally some fun!"
She clearly had a plan for me.
"Bruce, I want you to flash my dad's friend Tom."
Shocked, I was speechless.
"WHAT!?" I objected
"Yea. Go. You have to. It's the rules." Pam said smirking but clearly serious.
"Umm we're at a family cookout that's weird" I began to rationalize
"Nope. Go into the pool house, take off your underwear put your shorts back on then walk upto him with your zipper down."
Pam had obviously planned this. I was confused and turned on but even more confused because I was turned on. My gears had just shifted from Pam to now Mr Tom? What?
Now when I tell you I've never had a gay or even bisexual thought I meant it. I had never even thought about it at all. I knew I was straight. But in that moment I wanted to rip my shorts off and show Mr Tom my penis more than I wanted a 2nd kiss from my longtime crush currently sitting 2 feet away.
"Fine." I blurted out trying to sound more like a good sport than an eager participant.
"OH and face away from us we want to make sure he sees it. We'll be watching from here" Pam announced the rules as I walked away.
I arrived at the pool house which was actually just a shed with patio furniture and a mirror leaned against the wall. I shut the door and began to unbuckle my belt. 'Am I really doing this?' I thought. 'Why is this so important? I could have easily ended the game there and made a move on Pam. We had just made out I'm halfway home with her already'. I dropped my shorts, stepped out of them and tucked my thumbs into the waste band of my boxers. 'I am really going for it' I sighed as I lowered my boxers to my ankles. I stood up and looked at myself bottomless in the mirror. I wasn't bad looking. No serious tanlines, not really hairy. Infact I tended to keep my pubic hair completely shaven. I had brownish blonde hair so even my leg hair wasn't overwhelming. I have a pretty good looking dick too. Circumcised, about 7". In that moment I convinced myself I was doing this for Pam to see it and not Mr Tom. I stepped back into my shorts and began to pull them up over my naked lower half. I slid them all the way up and buttoned them buckled my belt and began to zip up. 'OH wait' I said to myself. I have to keep my zipper down while walking out otherwise it'll be too obvious. I lowered my zipper and looked at my situation in the mirror.
Thinking about what was about to happen I got excited. Too excited.
"Shit!" I said aloud. I had an erection. How could I walk zipper down across the yard with this? I began to panic. It's one thing flashing your genitals to an unsuspecting man it's abother to walk with a boner that may or may not pop put for 30 or more adults who aren't involved. For a second I thought I should just admit defeat and go out with my head hung low. As I stuffed my boxers into my pocket I realized, I wanted this. I wouldn't be able to sleep if I didn't figure this out.
I know! I'll hold onto it from inside my pocket until it's time! Reaching my left hand into my pocket I grabbed my throbbing hard on and pulled it to the side. I took another look in the mirror and convinced myself it was concealed enough even with the crack in the zipper you couldn't see it. I grabbed the door with my right hand and stepped back out into the evening sun.
I looked immediately at the picnic table where this all began. There was Kelly her new Bf and Pam laughing and oblivious to me exiting the pool house but it didn't matter. I was still doing this. It had only been 5 or so minutes but it felt like an eternity had passed since the dare was issued. No turning back. I scanned the yard for Mr Tom. After only a second I seen him. On his phone away from people sitting on the beer cooler. This was perfect! I'd just have his and only his attention as everyone else is carrying on and in their own worlds including my table of misfits.
I began my approach. Still holding my erection in my left hand my heart was beating. The type of excitement that makes you feel like your floating. Closer and closer I could hear Mr Tom wrapping up his call.
"OK, OK. Talk to you soon. Goodnight." Ending the call and leaning to his right Mr Tom slides his phone into his back pocket.
"Hey Bruce! How's it going?"
"Good Mr Tom just thirsty ya know?" I cleverly replied as he was still sitting on the cooler.
"Guess I'm in the way huh?" He chuckled. "Wait, how old are you?"
"21" I laughed back as I knew he was joking. My pocket was soaked and my left hand was wet. I was seconds away from take off. As soon as he blinks I'm letting go I just need an opening.
"OK, Bruce, we're all 21 today I guess. Wink wink" he said smiling
"Let me help ya out here and grab ya something, it's the least I can do since I'm blocking the whole cooler, what are you drinking?"
"Whatever, I'm not picky beer is fine" I said
He leaned forward and looked between his legs as he opened the cooler to retrieve my beverage. I let go and my penis sprung out of my shorts like a spring. I looked over my shoulder quickly to see if I had Pam's attention and saw she was indeed watching. I turned back after confirmation and continued the dare. After 2-3 seconds on moving ice to find a cold bottle of Corona Mr Tom let go of the lid and sat back on top. As he looked up at me to say something, his eyes stopped. He was face to face with it. Pausing for what felt like minutes his eyes were wide. I stared at him and just took it all in. This was an adult man, almost 40 years older than me looking at my penis. He's not my a relative, he's not a doctor he's just another man. I instinctively leaned back and arched my back as to stretch which pushed my erection even further out of my shorts.
Returning to my relaxed posture I noticed Mr Tom hadn't moved. He hadn't stopped looking. What should I say? What should I do? Luckily he snapped out of it.
"Ummm... Well here ya go" sounding guilty he handed up the beer that started all this.
"Thanks Mr Tom" not knowing what to say I reached out to take it.
As our hands met on the bottle Mr Tom reached out with his pointer finger and rubbed my hand. He then looked up at me and met my eyes.
"Did you need anything else?" He asked
