I had been on a dating site for a while that connected older men with younger guys.
To be honest, I'd been on the site since I was young, younger than the legal age for the site, and I lied to all the men I'd meet on there about my age.
I always knew from a young age that I found older men attractive. The way they dressed, the way they smelled... the mystery of what they looked like naked.
Sure, I'd had a few flings with girls at my high school that went nowhere. And I even met another boy my age but it was awkward. I knew what I really wanted.
But, I never had an encounter with any of them until I turned 18. It was a mix of nervousness and living with my parents. I was a ball of hormones and testosterone, ready to explode at a moment's notice.
I won't go into the first few encounters here. I'll save that for another time. Besides, it's kind of a blur now... I met a lot, perhaps too many, guys my freshman year of college now that I was free to do whatever I wanted.
When I was about 20 years old, I had gone on a few dates with a guy named Rick who was in a sexless marriage, as tends to be the case with many of the guys I used to meet. The dates were simple ones: going out to eat at a nice restaurant (he was rich), seeing a movie. One time he took me to an arcade... which felt like a true daddy/son date, even if he wasn't that into it.
One day I checked my email and found a note from him: "I was thinking we could go on a camping trip next weekend. We've had some fun on our dates and I thought we could take things to the next level. Interested? If so, call me... I have some other ideas to run by you, but I wanted to see if you were interested in the first place."
I remember that my heart was beating really fast. A camping trip meant being alone in the middle of nowhere with a guy that I only kinda-sorta knew. But, I figured I'd hear him out, so I gave him a call on the landline in my dorm when my roommate was in class.
"Here's what I was thinking," Rick said on the phone. "I have two friends who are also currently dating younger guys, around your age. I was thinking they could come with us and we'd each have our own tent."
"Our own tent?" I asked.
"Yeah, Walt, our own tent. For one night. My wife thinks I'm going camping with a buddy."
"You mean we'd sleep together in the tent?" I asked, naively.
"God, you are so innocent, aren't you? Yes, we'd sleep together in the tent."
I was skeptical... what did this mean, exactly? We would share a tent, but what else?
"You mean, like, sleep together sleep together?" I asked.
He laughed.
"I'll be direct," he said. "There would be some rules you'd need to follow."
He then went on to make his proposal. The rules were:
Absolutely no clothes allowed while we were on the campsite. He
assured me that we would be far enough away from anyone else that no
one would see us naked, except each other.
Sex was required, whenever he asked. He explained that he would never
try to have sex with me without my consent, but if I was going to
agree to come along on this trip, he did not want to be turned down
if he made a move. It would be our first time having sex.
If the other men wanted to have sex with me, I was to comply with
that as well. Rick explained that they might find me attractive and
that he would find it wrong not to, as he put it, "share." He had
already sent them my (g-rated) pics.
All expenses and cooking would be covered by the 3 older men. The
younger boys would not be allowed to pay even a dime.
No posting, texting, or telling anyone about the trip.
Now, Rick had never seen me naked before, and I was a little body conscious; I am extremely hairy for a younger guy, and sometimes it can be a turn off to older men. So I was a bit hesitant about that.
The sex part sounded good to me, maybe even more than good. I was attracted to Rick. He was the type of older guy that I had dreamed of... at 63, he had a large frame, always well-dressed, with a nice tummy. Big thick beefy legs. It looked like he could squat quite a bit of weight if he were at the gym.
And he was very sweet to me. The only physical thing we'd done was kiss at the end of our dates, and we made out for a few minutes during a movie one time. Judging by the lump I could see in his pants, even in a dark theater, I was in for quite a treat. And, also, perhaps some pain... Rick was a total top, he had told me. I was intimidated, but every time I thought about the idea of him fucking me, I got rock hard.
I had to really think about the idea of the other men being able to have sex with me if they wanted. What if I wasn't attracted to them? What if they were weird and creepy?
And not posting at all about where we were going? What about safety? If these men tried to kidnap us or kill us, nobody would know where we were.
I decided to call Rick back up and agree to the trip... only if he accepted a few conditions/revisions to the plan.
The six of us would need to meet ahead of time to have some kind of
public meal/meeting. That way, I could assess the other guys to see
if they were attractive/cool.
I needed to tell a friend or family where I was going in case of an
emergency. I wouldn't tell them who I was going with or what it was
for... but for my safety, I needed someone to know.
Thankfully, he agreed to both of these terms and a group meeting was arranged at a local diner, a few days before the trip.
I took a shower that morning before I left to meet up with the group. When I got back to my room, I took a quick pic of myself on my webcam, smiling sweetly, with the front of my towel open.
I sent the pic in an email to Rick, with the text "See you soon!" and a heart emoticon.
Then, I got on the train to go meet the group.