THREE WAY FUN

Back about 2007

It was a very frustrating evening being online only to get rejection after rejection; or even worse, being lead on by game players.

So I decided to call my buddy up to see what he was up to. This was one of my close friends but every now and then when something "arises" we would get together and mess around.

I called him up to see what was going on. "I'm a little busy tonight," he said. Right then and there I knew he had a meeting with some guy. "O.k. who is he?" I snapped. Laughing he explained that he was meeting a guy that was another buddy of his. To my frustration I sadly told him to have fun. There was a pause on the phone and then he asks If I wanted to see if his friend minded an additional friend. "Sure!" I said, hoping that he would say yes.

After getting the ok, He gave me the address to where they were. He told me to just come in and lock the door behind. So when I got there and did as instructed. I walked toward the back of the house to the bed room, and there they are on the bed in a 69 position sucking each other. My friend was a good looking White guy in his 40s at the time, nice body with an incredible ass. His friend was a 30 something Black guy with a nice cock and booty that jiggled with even touch of my friend's hand.

So I get naked and join in on the fun. That night we all took turns fucking each other. My buddy and his friend tag teamed me, Me and my buddy tag teamed the other guy. Its was a very good time. When I got home, I checked my messages and found three messages from guys interested in hooking up. Oh well! I had a great time regardless.

BROKE THE DRY SPELL: CHERRY RE-POPPED

LINK: JER

Wednesday Sept 24, 2025

Consider my cherry re-popped.

The last time I was fucked was back in 2023 according to my entry POPPED!  Before that was about 10 years ago.

It's like having the nerves of a young virgin all over again.

"What if it hurts too much?"  

"What if I'm unable to satisfy him?"

"What if I get..."

"Preeeeg naaaant!"🫣 😉

Of all my concerns, my biggest one is the effect of the Cujo pills. 

I swear those prep pills make me feel like I can start foaming at the mouth at any second not to mention the horrible things it does to my stomach.  But I've checked all the boxes to make sure everything is clear.

"Right?" 

About 2:00pm

I had promised myself that during my exodus, I would not spend any more money on hotel rooms solely for hooking up unless it is for someone in my designated circle that I know would be worth it.

Since Jer discussed how he would like to top more and I wanted to reopen the door for bottoming, I decide to chat with him about the possibilities.

I'm unsure what his response would be when I invite him over to the hotel taking the answer to the proposal was left open and unclear.

I decide I would rent the room regardless of his decision and use it for a little get away if it doesn't work out.

He responds by letting me know that he will be available close to 2:00pm

2:15pm

I can't help but being a little nervous about what's going take place.  It has been 2 years since being penetrated.  Although it was fun, it didn't last very long as the guy was pretty thick and more eager than I was ready for.  Before that was 10 years.  It's been 15 years since Jer and I  have seen each other naked, so the nerves are jumping.

Plus, those damn Cujo pills!

I prepared as appropriately as I could.

Even though I fasted appropriately, there is always that question in the back of my head if I'm fully prepared.

I take a few moments to relax and get all of the distractions out of my head before he arrives.

He gets to the hotel. 

Jer, a White guy in his mid 60s, still looks good.  He is balding on top and he keeps his sides tapered very close.  He has a thin goatee.  I would describe his body type as an endomorph with more muscle than fat.  He has broad shoulders and a wider frame but not really fat.  His body is solid standing about 5'8".

 A bit has changed for the both of us. We both have extra pounds on us.  It doesn't seem to bother neither one of us however.

We chat for a brief moment.  It is not long before I get on my knees and start blowing him.  He begins to stiffen in my mouth.

He is not assertive when it comes to getting blown.  I actually grab his wrist and prompt his hand on the back of my head to signal that it is okay to get a little aggressive.  He does begin to gyrate his hips back and forth, pumping his cock in and out of my mouth.

One of the main reasons I chose Jer is because I know he would be attentive to my needs and that he wouldn't want to hurt me. But I also remember when he did used to fuck me, he was an animal in bed.  I'm looking for that animal right now.  My mouth can take it.  I don't know if my ass can, but I am definitely looking for that beast to fuck my throat.  

That beast is not there. 

That is totally fine.  I'm just enjoying being the recipient for a change.   

As I am sucking his cock I can taste his precum.  

He precums a great deal and I love how it taste. The funny thing is I can feel the precum oozing out all three of the holes in his dick.  He has his pee hole of course.  He also has the two holes where his Prince Albert was just minutes prior.

He is all the way hard now.  

I want him in me.

"You ready," he ask.

He lubes his dick as I lube my hole.

"I guess we'll see how far we will get," I say with very low expectations.

He gets on his knees, on the bed and lifts my hips up to find my butthole.

He pushes the tip in just enough.  It feels very uncomfortable.

"I don't think this is going to happen today."  I say to myself.

He pulls back. 

We try again. (Why I didn't think about this earlier: This would have been the perfect time to teach him The Butt Clock technique that I learned from Somebody . )This time I try some breathing techniques as I push my hole out.

Slowly his dick goes in a little deeper.

I close my eyes on the third try.

The next time, I try the invader with my eyes open.  I look at his solid body migrating closer to mine as I am on my back with my legs spread open.

"Oh!" I exclaim.

I feel the tip inside.

He comes to a halt.

"Are you okay?"

"Yeah,"I reply.

"Just stay right there," I request as I begin to breathe deep.  I don't want him to pull out.  I want my hole to get used to the intruder inside me.

We lock eyes.

As I focus on the eye contact, I feel the shaft going deeper.

"I'm going to go slow." 

I work on pushing out to open a bit more.

I feel every inch as he slowly digs to the base.

"Fuck.  You're inside me!"

"Well, yeah!" He laughs as if that was the silliest thing he's ever heard.

He slowly lifts his hips back and pushes forward.

He continues with this movement building up a rhythm. Lo and behold, he's fucking me!

Click here to continue reading.

GIVING IT SOME THOUGHT

 September 16, 2025

                   Tuesday

I wrestled with the idea of calling Jer, a friend that I have known for over twenty years now.  Sometimes it is months even years that we go without communicating.  There's no bad blood.  It is just how life plays it for us.  

He is pretty handy with fixing things.  Boss and I know we can always call him to fix it, whatever it may be.

August 11, 2025

When Boss was in rehab, I called him to see if he would help me assemble a mobility device for Boss.  He came by with no delay even though he is about an hour out from us.

We chatted.  He shared that he is seeing a guy but they were taking things very slow for now.

We first met at a gay men's group when I first started discovering the gay community, support groups for newbies dealing with their identities and learning to be more comfortable with who I am.

He was kind enough to offer me rides home from our meetings and social gatherings. 

We became friends and would share about what was going on in our lives. (This was a little before I met Boss.) 

We both were attracted to each other but were hesitant to cross that line out of fear of making things awkward.  

One evening he gingerly tipped toed around the possibility of us getting together.  I remember being so giddy and thinking to myself, "I thought he'd never ask."

From then on we were the true meaning of friends with benefits.  We had a unique chemistry.  We were both versatile although more than not he would end up topping me.  I was more than happy to oblige.  Of all the guys I have been versatile with, he is one of the few that I would be more than content bottoming for.  He just knew how to lay it down.  As a matter of fact whenever we would get together I would automatically assume the position.  There was just something about the size that fit perfect. Not so big that it was too much for me but still big enough to allow me to enjoy it thoroughly.

About a year after Jer in 2003, Boss came into the picture.  As we were getting to know each other Boss became familiar with some of the people in my circle.

Time goes by.  Things change, people change and we go our separate ways.  Eventually the play time we used to have stopped as we got into our own relationships.

Fast forward to this year, I called him up to help out with assembling the device.  He came up and helped out.  We chatted about the new guy he is seeing.

He is pretty content with what he has even though they are taking things slow.  His one complaint is that his new partner is not as versatile.  Jer bottoms mostly all the time for him.  His partner hardly ever bottoms for him.  Though Jer doesn't make a fuss about it, I know he is an ass man.  He shared with me that if he would just give it up more that he would be most content.

As we were putting working on the project we caught up on some of the play we have been getting into.  We are pretty much the same with our views on hook ups.  He is so much more content with his guy. But there is always that occasional meet up. 

I found myself getting somewhat turned on by our conversation.  It took a while for me to admit it.  But, I figure it was now my turn to gingerly tip toe and make my confession.  He smiled and reached to feel the bulge in my pants.

"Yep. Conversations like that will do it to you." He said with a smirk.

We finally finished up.  Ready to bring the device up to the facility, made plans to load it in his truck.

Before we walked out the door I asked him to follow me down the hallway. 

I stopped and reached out to feel the bulge in his pants.

"Do you mind?"

"No.  Go right ahead." He replied.

I got on my knees and took it out of his shorts.  I remember that he hardly ever wear underwear making it much accessible. 

I began sucking it getting it semi hard. I didn't get it all the way hard; just enough to give him a taste of what he's been missing out all these years.

"We got to head up to the center so we don't miss Boss's physical therapy,"  I interrupted.

"Well, now look at what you done.  Got me all hard.  Hope I don't start leaking," he said.

"Well that's what you get for not wearing underwear!" I laughed.

That is as far as it went.

September 16, 2025

I gave Jer a call.  I had that day in my mind.  

I shared with him that I was very much interested in getting together with him some time if he was up for it.  I just wanted to make sure that it wouldn't interfere with what he has going on with his new interest. 

He shared that one of the reasons why he never felt inclined to hit me up was because he had much respect for Boss and didn't want it to be weird for any of us.  The ironic thing is that Boss asked me in the past and recently if we ever fucked around. Actually if we ever dated steady.  I was honest with him and told him we didn't date.  It was more of a sexual thing.  Boss actually mentioned that he really likes Jer and if there was anyone he felt most comfortable with me playing with; it would be him.

Boss knows I enjoy meeting other guys occasionally for sex and kink.  But for him to give his explicit okay for Jer means he holds him in the highest regards.

When I did bring up the proposition,  there was a dead silence for a few seconds.  My heart stopped. I just knew I went over that appropriate line.  He did say that he would give it some thought.

He repeated that he is content with where he is now.  I shared with him my point of view; How I would love to be more versatile as a bottom and how difficult it is to find a top that will top, someone who is patient enough to take their time with me and who I already have a good chemistry with. I also reminded him that his desire to top more with my desire to bottom more is a perfect combination.

He again mentioned that he would give it some thought.

It did sound a little promising as he did throw out a few dates available on his calendar.  Time will tell.