Love Story From Bi to Gay

Hello, Literotica world, my name is Mike, and this is an experience of my life over the last 8 years. For those who don't believe it, that's your opinion and I am not here to please you, but it's something I wanted to share. I am not a writer and just sharing this, as best I could remember based on my experiences.

A little background I am currently 47 white male, I was always into girls and dated throughout school and married in my mid 20's but divorced after about 10 years because I didn't want kids.

I had my first bi experience when I was 18 in college and continued to hook up discreetly with guys all the time. When I started it was mostly j/o, mutual oral, and finally me topping because the guys I was with liked my thick cock. I would find guys back in the day on AOL chat rooms and then graduate to Craigs List. I preferred to find a regular guy for ongoing hookups vs looking for new guys and I did but it didn't last. I enjoyed giving oral a lot, and wanted to bottom, but never found the right guy and when I did I chickened out.

Now on to the reason, we are here, about 8 years ago could be longer I am bad with time I belonged to an established massage company where I was getting monthly massages, I had a woman for a while and tried some guys with the hope maybe I would get a little extra but it was always professional and nothing ever happened, well until I met Kenny.

The turnover of the place was high for masseuses, so it was hard to keep a regular one but I did enjoy getting a massage so I was trying to find one that was good to be my regular go-to one. I booked Kenny mostly because he had an opening and figured I would try. When I got there for my appointment I waited in the seating area to be introduced to Kenny since it was my first time meeting him. At the time of my appointment, we were introduced and we headed back to the room, on the way back like I have done in the past I checked him out, and once in the room, he asked me what I wanted in a massage I was able to pick up that he was gay, which excited me. He left the room and I undressed and hopped under the sheet as I waited for him to come back to start the massage.

Kenny came back in and started the massage like any other masseuse, and like any other masseuse I used for the first time the thoughts went thru my head would this be the time that I might get something extra? Kenny kept it professional keeping the sheets on the parts he wasn't massaging but when he got to my lower back he asked me did I like my glutes done, I was never asked this before. I said yes, as he massaged them over the sheets, this drove me crazy. Kenny then did the back of my legs keeping the sheets covering my ass but he went higher up my thighs than any other masseuse has done in the past, causing me to wiggle with excitement.

Finally, when he was done with my back he held the sheet for me to turn over onto my back so he can do my front. As I was doing this I realized I was very hard and it would be visible, but I didn't care, and once I did lay down and the sheet was fixed you could see my cock standing up. Kenny never said anything and just did his job giving me a massage as normal but when he got to my legs as he did to the back he massaged them higher than I ever had in the past causing my cock to stay hard. At one point I opened my eyes as he was rubbing my legs and my cock was tenting the sheets we looked at each other for a couple of seconds, then I quickly closed them. Kenny finished up the massage and asked me how it was I said great and said there was a hot towel there on the side and I could get dressed and meet him outside. As soon as he closed the door I pulled the sheet back and jerked off, it took less than a minute for me to explode all over my chest, this was the first time I did that in the room after a massage. I used the towel to clean up and dressed and met Kenny outside the room as he walked me out, and he said he hoped to see me again, and I said defiantly.

I booked another appointment with Kenny, I believe it was for two or three later, and it was also for a double session. I sat in the sitting areas like last time until Kenny met me and took me back to the room. Once in the room, he said it looks like you are treating yourself today with a double session, any areas you would like me to focus on. I told him all over like last time, and he then said to get undressed and lay down as he left the room. I did as instructed, but instead of putting the sheet all the way up, I left it right above my ass, hoping to send a signal of some sort. Kenny came back in and pulled the sheet up depressing me and started the massage like previously. He worked my back and shoulders, but I felt the sheet exposing the top of my ass and it excited me.

As he continued the massage he worked on my arms, as he pulled my one arm from the table and massaged it, my hand made contact with his crotch area. This could easily have been an accident, but it kept happening, then when he moved to the other side to do my other arm the same thing happened. At this point, my cock was very hard and I could feel myself leaking precum all over the sheet, I was also wiggling from the excitement causing the sheet to move to expose more of my ass to him. My cock was telling me to grab his cock, but my brain was telling me no, don't make the first move. My cock won out and I grabbed his cock and started to rub it thru his pants.

At this point, he stopped rubbing my arm and started to rub my ass as the sheet was fully removed from that area, as I continued to rub his cock thru his pants. As he was rubbing my ass his fingers found my hole and he started to insert a finger, which was causing me to moan into the table so no one could hear us. Now he moved away so I couldn't touch him but he continued to work on me, getting me to get on my knees with my ass up as he continued to finger my ass, and also stroke my cock. I was doing my best not to cum, I did not want this to end. As he was doing this he turned my head and kissed me as he fingered and stroked my cock, what a hot scene.

I felt like I was about to cum, and pulled away and lay back down, telling him I didn't want to cum yet. As he moved in front of me I moved my hands toward his cock rubbing them and trying to work his pants off, which he helped with. As soon as his cock was free I took him in my mouth giving him the best blow job I could until he grabbed my head and shot his load in my mouth with me swallowing it all. At this point, we kissed again, and he pulled his pants up and told me to lay on my back so he could take care of me. I listened and Kenny gave me the best blow job I ever had up until the point, swallowing it all and then finished giving me my massage, we didn't say anything else and acted normal.

A couple of weeks later I found my way back for a massage with Kenny, and as soon as I was in the room and the door was closed we started to kiss and rub each other thru our clothes for about 2 minutes. He then broke it off and asked what was I looking for today with a grin, and I said the same the last time, he said to get undressed and he will be back and left the room, what a tease I thought.

I got undressed and hopped on the table and just covered my ass for when he came in the room, and as soon as he came in I pulled the sheet down exposing my ass. He came in washed his hands then came to the table and pulled the sheet up covering me, and depressing me as he started the massage. He started to massage me as normal or I thought until he pulled the sheet down exposing my ass, rubbing between my cheeks and pushing a finger in my ass driving me nuts.

This drove me to my knees giving him access to finger my ass and stroke my cock if he wanted and kiss me passionately. This went on for a couple of minutes until I stopped him telling him I wanted his cock in my mouth badly. Kenny had me get off the table and put me on the floor on my knees as he lowered his pants and I took his cock in my mouth. I sucked his cock for about 5 minutes until he pulled out and pulled me up, kissing me. He then broke the kiss and said can I fuck you bare, I have always wanted to be fucked, but always practiced safe sex, but here I was hornier than I ever was in a massage room with this guy offering to fuck me. I told him I wanted this but have never been fucked before and was afraid to be too loud and people might hear, he said it would be fine as he kissed me and turned me around bending me over onto the table.

Luckily Kenny didn't have that big of a cock, it was nice but perfect for the first cock to fuck me. He kissed the back of my neck as he fingered me more, and then when I guess he felt I was ready he started to push his cock into my ass. I guess he must have put stuff on his cock too because it slipped into me easily. I won't lie it hurt at first, but it wasn't horrible and he took his time until I was used to it, and then picked up the pace. I recall him pulling my head back as he fucked me from behind and we kissed me breaking the kiss and telling him to fuck me hard something I always wanted to say. He pushed my head down as he grabbed me and started to fuck me hard, being as quiet as possible I was pleading with him to fuck me. with my cock rubbing on the sheet and the fucking I was getting I exploded all over the end of the table. I was in a post-orgasm bliss and didn't even realize he pulled out when he helped me up and kissed me. I recall asking did he cum and he said yes, and I said where and he said deep in your ass. I fell back on the table laying down exhausted and now a little shocked at these events, he dressed and cleaned up and the time was up so he left the room and I cleaned up.

I could feel the cum leaking from my ass, and as I drove home and showered I thought about what I did thinking it was wrong. A couple of weeks went by and the guilt turned into amazing memories that I wanted more of, I started to jerk off to what happened and wanted to see Kenny again so I booked another appointment, a double session again.

It was over a month since my last encounter with Kenny I was very excited to see him and very honry. He came out to the seating area and took me back to the room and as soon as we were in the room and the door closed I started to kiss him passionately while rubbing his cock. Like last time after a couple he broke it off, but I just fell to my knees and fished his cock out of his pants and took him in my mouth blowing him hard. I did this for a couple of minutes until I stopped getting up and said to him I need you to fuck my brains out now.

I then walked over to the table pulled my clothes off and bent over like the last time, as he followed grabbing whatever lubricant he had and roughly putting it on his hand in fingering me to loosen me up and pushing his cock in me and fucking me hard as I wanted. We both didn't last long with me coming like last time from my cock on the sheet rubbing, and him in my ass again.

We both cleaned up but we were only 10 minutes into a 100-minute massage so he gave me my massage. It felt great, and I believe I fell asleep for about 10 minutes when I rolled onto my back when I woke up I asked him how long we had left and he said 15 minutes. I asked him if he wanted to fuck me again, he pulled the sheet from me, and with me, on my back, he pulled me to the end putting my legs on his shoulders and pulled his pants down. Using his cum already in my ass he easily pushed his cock back into me for the 2nd time that day, as he looked at me and fucked me for the next 15 minutes until we both came again. We cleaned up kissed and I left.

This became a regular thing with Kenny for a while each month, where I would see him for a massage and we performed oral on each other and he would fuck me. I tried to see him outside the massage place but he said he had a partner he lived with and he couldn't.

After Kenny introduced me to being the bottom I always wanted to be I knew I wanted to be fucked more. As I mentioned I wanted to see Kenny more but could only see him for massages. I was still very discreet so it was hard to meet others. I was divorced and dating girls at the time and also traveling for work and would often try to hook up on the road when I could.

On one particular trip right after becoming a bottom I was there for a week and decided to stay thru the weekend with the plan to meet someone and play all weekend. I met someone online who was a top we exchanged pictures and agreed to meet in my hotel, which I booked for the weekend away from work. Where I stayed for work that week and decided to stay was not a place where we had an office but some of us were in town for a conference with everyone leaving Wed and I stayed thru the week. This guy and I talked all week about what we were going to do really getting each other excited, but when Friday came he went dark and I never heard from him. I was pissed, I thought he was real and was really looking forward to this weekend.

That night I went online trying to find someone and had no luck but while online found a gay bar that was close by walking distance. I was in the hotel bar and had a couple of drinks I was looking forward to a hot weekend, so between being honry and the drinks I had, I decided to go. As I walked to the place I felt confident about staying discreet since I didn't know anyone in this area and there wasn't a work office around.

I arrived at the place for the first time at a gay bar and it was just like any other bar just all guys, but it was still early, and not many people were there. Those that were there were older, and nice but not what I was looking for. I had some drinks and talked but nothing came of it. After about 2 hours there I felt a hand on my shoulder and someone say my name as I turned to see an employee from my company.

His name was Matt about 5 years younger than me, and someone who was at the same event but obviously didn't fly back home, he worked in another department, and he was someone I knew was openly gay. When I saw him I must have had the most nervous look on my face and was so frozen I didn't even say anything for a bit. He talked first about casual things to calm me down until we both grabbed a drink and went to a table to talk. Finally, he brought up the elephant in the room me being there, I knew there was no hiding it and he just said so I guess your Bi and somewhat discreet about it, and I just shook my head yes. He said he respected that and my secret was safe with him.

We continued to talk and he mentioned the reason he stayed in town was he had a college friend who lived close by that he was looking to catch up with but he had to work so plans fell through, that's what brought him here tonight. I explained my situation of how I ended up there also as we ordered more drinks. As we ordered more drinks and I began to get more comfortable with Matt, he noticed this and took this as a sign, and started to make a move on me. first, it was the sex talk, followed by a hand on my leg. At this point, I was buzzed, honry, and confessed to this gay guy I knew I was Bi. Finally, it was Matt that said I know why you are here, and what you are looking for, so let's go back to the hotel and just have fun, as he said this his hand grabbed and rubbed my cock thru my pants. I did not need any more convincing, as I put my hand on his hand that was on my cock and said let's go.

We left the bar and walked back to the hotel, both of us staying at the same one, nothing really was said. We ended up in his room and as soon as we were in the room he had me up against the door kissing me, and rubbing me as he pulled my clothes off. We made our way to his bed where we both hopped into a 69 until we both came in each other's mouths with both of us swallowing. We lay there for a couple of minutes until we started to rub each other's cock again and started to kiss, I then went down on Matt again sucking his cock and getting him nice and hard again. While I was sucking him I was wondering was Matt, a top or bottom, well it didn't take long for me to figure out when he said he wanted to fuck me.

Matt grabbed some lube and rubber, put me on my knees on the bed, and fucked me good. He had a bigger cock than Kenny's, and since he came already he lasted a while, fucking me from behind, then fucking me with my legs on his shoulders, We must have fucked for 30 minutes before we both came, showered, and then fell asleep.

The rest of the weekend until Matt and I flew out Sunday afternoon we spent it in the hotel and fucked the whole time, it was an amazing weekend. We were both on the same plane since we lived close to each other, and we were able to sit next to each other on the flight home. Matt was currently signal, and we decided to see each other with him respecting my discreteness.

Over the next couple of months what went from a couple of nights a week to every night a week that we saw each other. I was not seeing any girls anymore, and I was enjoying this in-the-closet relationship with Matt. In the house, we kissed a lot, performed oral and he fucked me all the time. after a month I asked him to stop using the rubber as I enjoyed feeling his cum in me. By the way, I still saw Kenny once a month.

I think it was over 6 months that I was seeing Matt when he came to me and said he was enjoying our time and was really starting to have feelings for me. He told me that deep down your gay and asked that I come fully out and be in a committed relationship with him. I was caught off guard a little but at the same time understood where he was coming from. I told him I needed to think about it, and he said he understood.

I did think long and hard about it for the next week, and then talked with Matt, but I told him maybe he was right that I wasn't Bi anymore and maybe I was gay but I was not ready to come out and be in a relationship and enjoyed how things were with us. I then told him I understood that he wanted to be in a real relationship and if I couldn't be I understood that this might not work, and hoped we could be friends. Matt hugged me and said he enjoyed the time with me, we kissed and had sex one more time before we ended our relationship.

It was hard going from getting fucked almost every night to not getting it again, and I was also very confused, was I gay? I tried to date girls again and quickly found out I did not enjoy it and wanted to be with men. I still saw Kenny once a month for that fix but it wasn't enough. I would hook up with randoms again and Matt even introduced me to a discreet friend but it didn't last because he moved away. This went on for a year or so until Kenny quit and I never heard from him again.

I started to think if I made the wrong decision with Matt, and maybe should I have fully come out, at this point, we were causally talking at work, but he ended up meeting someone and was in a committed relationship and then ended up taking another job.

With Kenny gone I still had a membership and booked with a new person, I decided to stay with men and ended up with a guy named Scott. From the moment I was introduced to him, I thought he was hot. He gave me a great massage but I was spoiled with Kenny, and I probably came unprofessional trying to get him to touch me more. I recall squirming, pushing the sheet off a little, and showing a hard-on when I was on my back, but nothing happened with him.

Scott gave me a great massage and decided to stay with him as my masseuse realized what happen with Kenny was a once-in-a-lifetime thing. I learned Scott was gay through the small talk we had before massages. Massages with Scott got even better, nothing sexual but he did massage all of my body except with cock and ass, and he went right to the edge almost teasing me but not doing it. Each time I had a hard-on and it showed when I was on my back but I didn't care, he had to notice it and also didn't care. I kept thinking of Scott when I jerked off, wishing things would go to the next level as they did with Kenny, I was in a drought with hooking up with guys so I was hornier than ever.