The Pleasures of Wor Travel

At 47, I had my first gay sexual encounter. For decades, I knew I was interested in experiencing sex with men. I'm definitely not gay, but have reached the conclusion I am decidedly bisexual. I still find women attractive, but steamy encounters with men was something I decided I had to act on. I've previously written about my first encounter which was essentially a surprise threesome. It wasn't what I was out there searching for, but it was what I got. It was incredible and still arouses me when I think back on it.

I don't hook up with guys with any regularity. When I get the itch, I scratch it.

I've chosen to write about the instances that leave a mark. Something beyond the routine quick fix. To scratch the itch, I maintained a Sniffies membership. As everyone experiences with that platform, it was a mixed bag. Sometimes you find a hookup, other times its just guys on there teasing around.

I had an opportunity on the horizon as I was going to need to travel to Tallahassee for meetings with legislators and state agencies. I'd be up there for four nights and surely by the third or fourth, I could find an opportunity.

After arriving at my hotel, I got settled in and popped open my laptop. It was time to update my sniffies profile so that I could put my bait out there. I felt like I wanted to be the giver for this experience and to keep things simple.

I updated it to read: "It's all about your cock. Come to me and let me service your cock until you finish. Reciprocation is not necessary. Clean and well groomed is a must. Please be at least 30."

My profile photos have remained the same since I first opened the account. Shots of my cock and my asshole. And one pic of a dildo in my ass.

The bait was cast, so I decided to take a shower and get cleaned up. I was trying to be realistic that the magic might not happen that night, but I should be ready if it would.

I took a shower and took my razor with me in the shower to clean things up. I keep things clean shaven downstairs, but some maintenance was necessary. I got my balls perfectly smooth and for good measure decided to clean up my taint and ass. I was advertising for a blow and go situation, but it feels sexy to be clean shaven back there.

I came out to the computer and there were three new chat requests. I opened each one, and to no surprise, every one of them started with the typical "Hey". The third one on the list was an anonymous cruiser who sent a picture of his cock. It had great form. The photo was taken when it was hard as a rock. Didn't look too large, guessing about 6 to 6.5 inches. It had a nice upward arc that was appealing. I'd respond here first.

"Hey, nice looking cock. Do you need some help with it this afternoon? I'd me more than happy to take care of that swelling for you."

It was cheesy, I know. I'm not too experienced at this.

About 5 minutes pass and I get a response back.

"Definitely on here looking for some 'service.' What are you thinking? Let's see if we are looking for the same thing."

I replied, "I'm serious about what the profile says, I really want to focus on someone else's cock. I want to suck you long and slow and gradually increase until you are fucking my throat. I've never handed over control to a guy and let him do that, but I want to try. At the end, I want to taste your cum. Every last drop."

I sent the response, and it sat out there for a couple of minutes.

I was beginning to worry I had lost him that quickly.

He responded. "That sounds pretty awesome, but I think I'm looking for a little more tonight."

I knew I was losing him, so I quickly responded.

"I'm not saying that I'm not open to more. What did you have in mind?"

"I want to be able to fuck you any way that I please. Whether it is your throat or your ass, it's mine for the night. Your cock is irrelevant in this transaction. Your role is to please me and do whatever it is I want. You have the right to object, but know that it is a turn off for me and you said this is about me. Do you have that in you?" he replied.

Wow. That was a lot to take in.

Was I willing to give someone control to that degree? The idea frightened me and turned me on at the same time. I knew I had to decide right now or the line may go stale.

"I'm open to it. But, let's figure out what the non-negotiables are first. How old are you? Are you okay using protection?" I typed back...trying to regain some level of control of the direction this takes.

"I'm 24 and I'm on PrEP. I do not want to use protection, but see my prescription bottle below. I take it as prescribed and was only prescribed it after passing the screen," he replied almost immediately. The reply was followed a minute or so later by a picture of a prescription bottle labeled Descovy and of little blue pills in his hand.

A couple of challenges here. I had stated that I wanted someone over 30. He's claiming he is 24 years old...that's a full 6 years shy of my target. Second, I've always required protection to fuck me. He's telling me he is on PrEP, but I have to trust that he's actually on it. I have to dive deeper.

"Two things. I'm concerned because you are younger than my sniffies profile asks for. Why does a 24 year old want to do this with someone who is pushing 50? Second, I always use protection. How do I know that you aren't sending me pictures of someone else's prescription and a random hand holding pills from the internet?" I replied.

After a couple minutes of thought, he responded.

"I'm a graduate student at FSU. I'm into older guys and I like to flip the script and be the one dominating them. I guess it's a power trip. I spent my younger years following the directions of older men, and now I want to be in charge. With regard to the PrEP, look at the pictures below and tell me if this is enough to provide you with comfort."

He sent two pictures. One was his driver's license with his face covered, next to the prescription bottle. It showed his name with a Miami address and the name on the prescription matched.

The second picture was another of his cock, but this time it was only a little hard and his hand was next to it holding the same blue pills.

The ball was in my court. Time to say yes and tell him where to find me...or time to run and not take the risk.

I thought quickly about it and I was just too intrigued to let the risk deter me.

"I'm in. When can you meet? You can come to my hotel," I said...as I felt a twinge go through me...excitement and fear at the same time.

"I've got commitments until about 8 o'clock. That will give you enough time to go to the store and get what is necessary for you to get cleaned up. When I get there, I want you to be douched and ready. You're going to be mine until I'm done with you. If you do not already have lube, go to the store and get some. I prefer gun oil, so I suggest you go to the adult store on Apalachee to get that," he replied.

I shared my hotel location and room number with him. I disconnected from sniffies and sat for a second imagining what might be ahead of me.

It was 4 pm, so I had some time to get the things done I needed to. I departed for the sex shop with clear directions on what I needed to get. I had not brought anything to douche with because my intent was just to give head while here, but I guess I just signed up for more.

I got to the sex shop and found the gun oil on the shelf. I then grabbed an enema bulb and realized that it is abundantly clear what I'm up to when I go to the register. What the hell...grabbed a butt plug as well and headed to the register. I exchanged awkward pleasantries with the clerk, paid with cash and got out of there.

Given what was in front of me, and the fact that he was so direct about what he wanted, I thought it could be a long and interesting night. I veered the car into a walmart and went inside to grab some Immodium. If there were multiple rounds that evening, I didn't want my douching to fall short of a long evening of fun.

With a night of fun coming, I decided to opt out of having dinner. I returned to the hotel and looked at my watch. It was 6:00. Still a lot of time, but I could feel my nerves already building. I decided to stop at the bar in the lobby and have a couple of drinks.

I pulled up at the bar and made some smalltalk with the bartender and ordered an Old Fashioned. I figured if I knocked back two of those I would be feeling good and ready for some fun. So, I sat and sipped my drink while watching the news. I ordered another and sipped my way through it as well. I was starting to feel a buzz come on and the anxiety was lifting.

Looking down at my watch, I see it's now 6:45. Time to go prepare. I got to my room and did what was needed. Put on some gym clothes and now the wait.

The buzz held, so it didn't feel like long until there was a knock at the door.

I opened the door and he stood in front of me. I was pleased to see he did not look younger than the age that was on his license. I'm just not into that. He was a decent looking guy. Filled out, not chubby, but definitely not a gym rat. As you would expect of anyone still in school, he was wearing a tshirt and jeans with a hoodie and was carrying a backpack. He said his name was David and I invited him into the room.

He came in and sat at the desk chair. He shared with me that he had done this a few times before and usually does it when the legislature is in town because the population swells with a bunch of guys who will be leaving soon.

"I could really use a shower, do you mind if I use the one in here?" he said.

I obliged and he began getting undressed.

He said, "Before I shower, you should get undressed. There's something we need to do."

I began getting undressed, wondering what he was referencing. Quickly, we both had our clothes office and he was digging through his backpack.

"You said this is about my cock. I want to make sure that's the way it stays," he said.

I looked in his hand and saw he had a chastity cage.

"I've never worn one of those."

"It'll be a new experience for you," he quipped. "Sit down on the bed."

He knelt down in front of me and used the key to open the cage. He grabbed my balls (I let out a little moan from the contact...he didn't even acknowledge it) and began pushing them through the ring. He pushed my cock that was starting to move into its container and then locked it on.

David took the key and walked over to the closet. The room safe was open and I saw him put the key in and heard him entering a code.

"Now, only I can take that key out of the safe to free your cock. I'm going to shower. You wait here for me."

I looked him over as he walked to the bathroom. His cock was partially engorged, so I know that I've already started doing my job. I loved the shape of his body. A little bit of extra meat on the bones and a nice supple ass. Strong legs.

He entered the bathroom and shut the door. I could hear the shower come on and I could feel my cock pressing against the cage. It wanted to get hard in anticipation of what might come next, and it was uncomfortable as it pushed the cage. However, it was clear the device was winning. I filled it, but went no further.

I lay on the bed looking down at my caged penis and realizing that I cannot get to the key if I wanted to. It was unnerving and exciting at the same time. I've never been owned like this. Am I sub at heart? While I waited, I pulled the plug and gun oil out that I bought earlier. Removed the packaging from both and put some oil on the plug. A couple of steady pushes and I pulled it into my ass. I placed the gun oil on the nightstand next to the bed.

After a few minutes of reexamining my role in life, the shower turned off. A shiver went through me at the sound. I hear some rumbling around in the bathroom and then the click of the door knob.

David walked out of the bathroom with a towel around his waist and sat in the desk chair.

"Come over here," he commanded.

I got up from the bed and walked over to him.

"I think you have some work to do," he stated as he pulled the towel to the side.

I dropped to my knees and reached out to grab his now flaccid cock. Leaning forward, I pushed my tongue out and brushed the tip of his cock. I then dropped my head down and extended my tongue to the based of his balls. Slowly snaking my tongue left to right, I moved up his sack and to the base of his shaft. Turning my tongue straight, I slowly lapped it up the length of his shaft and scooped my mouth over the head at the top. I began a bobbing motion and could feel his penis engorging as I went.

In no time, his cock was hard and I was bobbing my head up and down on it. He was letting off soft moans as his cock progressed to being rock hard. It was just the right size to completely fill my mouth and throat, without being overly challenging.

I dropped all the way down and felt it slide into my throat. I've practiced this a lot and have suppressed my gag reflex pretty well. My chin was now pressing on his scrotum and I held his cock in my throat. In practicing, I developed the habit of counting my mind how long I hold it, so I have a target to get better. I held his cock there for 10 seconds and then pulled back and quickly did repeated bobs all the way down his cock. After about 10 bobs, I finally lightly gagged. This drew a bunch of saliva out and things started getting sloppy.

I kept at it for a couple of minutes, pushing the head of his cock repeatedly down my throat and listening for the moans. My cock was pressing hard against the cage...clearly loving the work I was putting in on David.

David says, "Get up, we're moving."

I stand and he leans in and kisses me. I'm not normally into that, but I'm really fucking turned on. I open my mouth and let him in. It was short with about four or five quick flits of his tongue into my mouth.

"Lay on your back and hang your head off the bed," he directed.

I climbed on the bed with my feet extending across the foot of it. I dangled my head off the edge and was well aware of what was coming. I haven't done it before with a guy, but have tried with my wife's fuck machine. I'm hoping I can perform better here than I have in those attempts. I'm in it, so it's coming whether I like it or not.

David moves forward and lays his cock across my face. I lean my head up and tongue everywhere I can make contact. He pushes forward and his balls are over my mouth and I'm looking up at his ass. I lap his balls and he reaches down and pushes his sack into my mouth. I gently sucked with a pulling motion with one of his balls in my mouth. A new experience for me and I was so turned on. I didn't feel pressure from the cage anymore, but I was so mentally aroused by the scene.

After a few sucks of his right nut, he pulls it and drops the other in. I repeat on his left nut, but choose to add some dramatics with moans and slurping sounds. He responds with moans of his own. After a somewhat extended treatment, he pulls back and pushes his cock downward.

It's time. I'm here. There's no escaping where this cock is headed. I open my mouth wide and he slides it in. I feel it push into my throat and he holds there. My instinctive counting starts again and he hits 15. My stomach clenches and I feel the gag take over. I feel my ass expel the plug as the gag clenches everything. Slobber pushes up the length of his shaft and he pulls out.

I get a chance for a breath with just the head in my mouth and he pushes it in again. This time only a couple of seconds, then out. I can handle that...but here it comes again immediately. No hold this time. Back out....back in. Five fast hard strokes....gag again. Massive slobber makes its way up onto his cock. He pulls out of my mouth and it is dripping on my nose and eyes.

He reaches down and aims in again. Three full thrusts and then he pulls back and gives me a reprieve. Short strokes for probably 15-20 times...my throat rests.

Without warning, it goes all the way down again and holds. Counting....I hit ten and he pulls back. Fast thrust back down. In and out, in and out, in and out. It kept going. I'd gasp through my nose on each pull out.

The onslaught is so heavy now, I'm unable to think and take a read on how I'm feeling through it. All of my focus is on his cock and keeping myself breathing when I have the chance. Thinking back, it was almost trance like.

He continued the thrusts. 4-5 times where his clean shaven balls were squeezing against the bottom of my nose and then out for a breath. This rhythm went on for a few minutes and then the ante went up. I felt his cock push into my throat at least ten times and then I gagged hard. Fortunately nothing was in my stomach or that would have been it. Really slimy saliva pushed out of my throat and around all sides of the base of his cock, running down his balls and onto my face. He recognized the gravity of that gag and pulled all the way out, allowing me to gasp for air and calm my muscles.

He stepped away from the bed and grabbed his backpack. As he picked it up and turned to face me (with my head still hanging off the bed), I saw his cock at full salute and glistening with my slobber. The clarity then came back as I recognized just how fucking turned on I was. I did that to his cock. It's red from pushing into my throat and that wet and sloppy cock is his prize.

He unzipped the bag and pulled out a dildo. It was girthy, but nothing crazy...a real cock styled dildo. He grabbed some KY he had in the bag and placed it on the dildo. Leaning over me again he noticed the plug sitting near my ass. He leaned back and looked at me.

Laughing, he snickered, "I had no idea you even had that in."

He grabbed my legs and pulled them toward him. I felt him pushing the head of the dildo against my ass while his balls and taint were above my mouth. While he pressed, I extended my tongue and swiped it across his perineum. I returned his moan as I felt the head of the dildo slip past the entry to my hole. He continued to push slowly until it was in all the way. As he reached the point of full insertion, I moved back to his taint and began fluttering my tongue across it. He started sliding the dildo in and out slowly as I continued on him. I kept pulling my tongue back in my mouth and out to get it sloppy and wet. First pushing hard with my tongue, then light, listening to him continue to groan. I can feel how hard he is as his cock rubs against me as he lightly thrusts with each lick. At the same time, I can feel him exploring my insides with the dildo.

He begins picking up the pace on the dildo and pulls his hips back.

"Hold your ankles," he commands.

Doing as I'm told, I reach up to grab my ankles. Ensuring he keeps full access to my ass, while he continues to push and pull on the dildo.

Once I'm in position, he uses his left had to push his cock back to my mouth. I eagerly open my mouth and he slides it in. Not deep, but he begins fucking my mouth again. Each stroke just touches the back of my throat. I'm practiced enough that this does not create a reflex for me. He matches his thrust with the thrust of the dildo...which gives me an opportunity to breath with every other motion.

After a couple of minutes, my hole is feeling really good. He's clearly pressing it toward me because it is sliding over my spot with every push. My mind is lost...I'm just in this moment, right here, right now, with sensations at both ends of my body.

He continues pumping his cock into my mouth and begins pushing further and crossing into my throat. Entranced in the moment, I relax my throat and he begins sliding in with little effort. Four pumps...pause...breath. Four pumps....pause...breath. The dildo did not pause, I continued to feel it pushing on my prostate and I'm incredibly turned on.

As I faded in an out of the trancelike state I found myself in, I realized my cock is no longer pressing on the cage....but I'm incredibly turned on. My cock is just no longer part of that transaction.