Married, Sexless, Curious

I am your average profession business guy and travel most weeks to different parts of the country. I live in a sexless marriage and the majority of my sex life depends on porn and occasionally a few toys. My Fleshlight is my favorite and it goes with me on most of my trips.

I felt lonely most of the time over the last 10 years but never had an interest in cheating. I would occasionally would look at the online ads but never really had the nerve to make that connection. I did enjoy reading the ads and looking at the pictures. The fantasy was often enough to bring me to a great orgasm.

One day I found an app on one of my kid's phones that allowed you to anonymously make a confession.

I downloaded the app and enjoyed reading the posts. Some were asking for advice and some were dark secrets.

One night I was staying at one of my regular hotels in Nashville and had just come back from dinner. I was about to search for some porn and take care of business when I saw that app on my phone. I opened it and started scrolling through when I read one that simply said "Married, sexless, curious"

Curiosity got the best of me and I clicked on the message link. I sent this random person a reply "Hi, in the same boat".

To my surprise, a few seconds later, this person responded. We chatted about our frustration and types of porn we liked. I found out that he was married about 15 years and had never been with anyone other than his wife. It sounded exactly like my story. He asked me how I handled things with a smile emoji. I couldn't help but laugh.

I told him that I would usually end my night with porn and a toy.

When he responded he told me that he also relied on different types of porn but was curious about the toy.

I sent him a picture of my Fleshlight. He had never seen one and was very interested. He asked a lot of questions and said he had bought a sleeve in the past but was disappointed.

On the app, it tells you how close someone is from you and it said he was 200 feet away.

I was in deep thought when my the app chirped and he asked if was still there. Before I could reply, he asked what hotel I was staying in. I thought about it and then replied the Hyatt near the airport.

He responded that we was in the same hotel. Excitement and fear both set in and I really wondered if I should keep chatting.

I wasn't sure where this was going but we kept chatting anyway. We went back to types of porn we liked and talked about a few sites.

I don't know what came over me but in the middle of the conversation, I asked him if he would like to try to flashlight.

There was a long pause and I thought my new friend had been pushed a little too far.

It reminded me of my younger days when the guys would stay over and we would end up looking at my dad's magazine collection. We would end up jerking each other off or messing around.

I had about given up hope when the app chirped

"Sorry, I my phone rang. I would love to try it. What room are you in?"

I responded with the room number and He replied that he would be up in 10 min.

I was so nervous I was shaking. I had hooked my laptop to the tv already and already had my favorites playing on the screen.

I paced and kept looking out of the peep hole. After about ten minutes, I heard the elevator chime and then a knock at the door. Was I ready for this? Should I open the door?

My shaking hand opened the door and was greeted by another good looking business guy holding two 6 packs of cold beer. He had on shorts and a t-shirt. I said come on in and it was like meeting a friend for a beer. His name was Mike and said he thought the beers would help. We were on our second one and I was feeling more comfortable. He saw that I had the computer hooked to the tv and asked to see what I liked. I clicked on my favorites and we started watching and joking around. The toy was on the sofa. He picked it up, unscrewed the cap and was amazed how it looked. He put his finger inside and he loved the way if felt.

I told him that you only used water-based lube and put the bottle next to him. We opened out third beer and started watching a video where a guy was fucking a girl in the ass.

I told him that my Fleshlight felt like anal and was amazed by how good it felt on my dick the first time I tried it.

He looked at is again and I saw the look on his face.

" Go head and try it" I said. I felt like a used car guy.

He stood up and dropped his shorts. He was semi hard and was only about 4" long.

I grabbed the toy and squirted some liquid into the entrance. I handed him the lube and told him to put some on his dick. He was stroking his cock and I kept watching. I was rock hard but still had my shorts on. I handed him the Fleshlight and told him to slide the head in once he was hard. He wasn't fully hard so he was having a little trouble. I assured him it was ok and it was probably me being in the room. I asked if he liked another kind of porn. He asked if it would be ok to put on some tranny porn. I loved it as well and knew just the site. On the tv was guy and young girl. She was undressing him and strated sucking his cock, he then lifts her dress and he sucks her smaller cock. He said that this was great and had never seen it before.

I continued to watch him more than the movie when he finally slid his cock in the toy. He said it was really tight but was a little hard to stroke. I was trying to tell him about the cap when I just leaned over and said let me show you. I turned the top so it reduced the suction started stroking it for him.

He moaned and I decided to use the techniques I liked myself. I went slow at first and then a little faster. I tightened it a little and told him this is where it felt like anal. He was still moaning but said one day he would like to try anal. I thought everyone had and was a little surprised.

On the next video, the guy was fucking a tranny and another other one started finger the guys ass. I could tell he liked what was on the video so I started to touch just below his balls. When he moaned I knew I could go a little further. The lube was all over so I coated my index finger and started pressing on his anus. I had done this to myself many times and used a dildo quite often. Mike was sliding his body down trying to get my finger inside his ass. I slid it in and it went in easily. As my finger went in out, I knew he was getting close to a climax. I reduced the suction and picked up the speed. I wasn't many strokes later and I felt him climax. I slowed down till he couldn't take it anymore and eased the toy off his cock. I was covered in lube and cum. I had never thought about how this would make me feel but I was rock hard and thought about sucking his cock. I chickened out, got up to wash out the toy and grab my new friend a towel. He said it looked like I needed some relief as well. I laughed and said I will. As I brought him the towel, he was still sitting on the couch. He looked up at me and said that he had never done anything like this before. I told him it was the same for me. He then reached up, grabbed my shorts and pulled them to my ankles. His right hand wrapped around my cock and moved his mouth to the head. I wasn't sure what to do or say until I felt his mouth. All I could do is moan.

He started to suck and stroke me at the same time. It felt great and since it had been 17 years since my last bj, I wasn't complaining.

I knew I wasn't going to last long and told him. This only made him keep going as his hands started squeezing my ass. As his fingers moved closer to my hole, I reached down, grabbed the lube and coated his fingers. As his finger slid in, I told him I was going to cum. He only kept going until I exploded in his mouth and could barely stand up when he finally let go of my cock and finished swallowing.

He reached over grabbed two beers and handed me one.

We both laughed a bit about what happened and how hot it was in the room. We both stripped and sat back down to recover.

We talked and opened up more about what we did on our own. We both said that we had dildos and would fuck our own ass on occasion.

We talked about work a bit until porn came back into the conversation. He asked if I had any dildos with me. I opened up my bag and pulled out a 5" silicone one I liked to use. After he played with it and compared it to his, he asked if he could give it a try. At this point I had had enough beer and told him that I would help him. I lubed up the dildo and his ass. I pushed it into his ass with my finger to make sure that there was plenty.

I rubbed the tip on his hole and teased him a bit. I told him to relax and push back as it slid into his butt. It is a smooth dildo so it went right in. As he took a deep breath. I paused until he was comfortable.

Once he said he was, I started going in and out. His cock was rock hard and precum was on the tip. I was staring so hard and couldn't resist. I leaned down and sucked him into my mouth. He grabbed my head and guided it up and down as I pumped the dildo in and out of him. I wasn't sure if I would let him cum in my mouth but I didn't want to stop either. I pushed the dildo harder and harder and started to feel him swell in my mouth. He started to buck and felt the cum shoot from his cock. I kept sucking until he slowed but he told me to keep the dildo in.

After he caught his breath, he told me to stand up and grabbed the lube. I was so hard and the lube felt great. He stood up and bent over the couch, he pulled the dildo out and looked back at me. I walked up and pushed my cock into his ass. I am larger than the dildo so it was still very tight. I pushed all the way in and held on to his ass. Once he was ready, he asked me to go slow. I started pushing in and out slowly untill I felt him open up.

We both looked on the tv and saw a guy we fucking a sexy tranny in the same position. He said it would be hot to match the video.

As the actor fucked her ass. I did the same to him. The guy in the video fucked her in a doggie position then pushed her flat on the bed. I did the same and the feeling was incredible. I knew I was going to cum soon due to who tight the new position was.

I told him I was going to cum and he said he wanted me.to cum on his face and mouth. I pulled out and straddled hhim as he rolled over. I stoked my cock about 10 more times when the first shot hit his forehead and hair, he grabbed my cock and placed it in his mouth and sucked me dry. I sat there for a minute catching my breath. He had slipped up and I could feel his hard cock rubbing on my ass.

I grabbed the lube, coated his cock and my ass. I was still in the same position so I was sitting on him. I slid back and guided him in my ass. He was barely 5" so it went in easily. I sat on it and asked him how he liked his first anal. Mike said is was better than he imagined and started to push into me. I rode him until he he came in my ass.

My room now smelled like sex and lube. We realized that it was also 3 am.

I was glad to hear he was in town one more night and we planned to meet the next day for dinner.

I will tell you about the second night later.