My name is Drew, and this is my true story of how I went from BI to Gay.
I am currently 43 years old and this story starts less than 2 years ago. I work as an Executive for a company, I am single and very very discreet in the closet bi man. I started to have these experiences when I was in high school, and have had oral, JO, 69 and topped, couple years ago I started to bottom, and have been leaning more towards that. Less then 2 years ago I had a cruise planned with a girl I was dating at the time, right before we were to leave, we broke up, instead of canceling I decided to go alone and enjoy the time away. I have been on many cruises, so I know what to expect and was not worried about being alone. Little did I know how life would change on this 7-day cruise.
I left out of Baltimore about 2 hours from where I live and once, I got on and unpacked I strolled around the boat, had a great dinner and then went to shows. Looking at the activity paper for late things to do, I noticed there was a welcome party at a bar for LGBT guests. As I said I am very discreet in the closet but at same time alone this week and very Horney and thought maybe I can meet a friend with benefits for the week, its not like I would know anyone on the boat. I knew the area where the party was, I figured I could sit in the back close by to see who is there but on the fence if I did see someone, I could say I wasn't sure what was going on. As I was sitting there it looked like any normal gathering, nothing to tip off people were gay, after about 15 min a man came and sat next to me, around my age nice looking. He asked was I there with anyone, and I replied with a no was just hanging out. He said he was there this week with a friend not dating just a FWB and they were looking for another FWB for the week for some roleplaying. I said it sounded hot, he then reached over and placed his hand on my leg and asked if I was more of a dom or sub. I said I was a BI discreet fag bottom, sub and winked at him, he then asked was I interested in playing with him whose name was Rob and his friend. I said yes, and we left the party and went back to there suite. On the way there he said his friend will be back to the room in 30 min but we can start. Once he opened the door and we went in we kissed immediately, after a min he broke the kiss and asked if I was really a fag, I said yes, he then pushed me down to my knees opened his pants and said suck my cock fag, I gladly obeyed. After about 10 min he helped me up and we both stripped and then climbed on the bed, he said his friend would be back soon, and would want to fuck my ass, was I up for that and their game. I said yes but what game, Rob went on to say his friend wants to fuck another who doesn't know who he is. Excited as hell I said ok, Rob then lubed my ass and fingered me to get me loose, he then goes in front of me on the bed while I was on all fours and fed me his cock again. He then reached behind him and presented a blindfold one you sleep in, so I couldn't see his friend, still thinking with only my dick I said OK and he placed it on me. I sucked him for another 5 min before I heard the door open, Rob said to continue sucking, I then heard a voice say good you found someone, and Rob said yep a nice fag for us for the week. Rob continued to hold my head and said to me keep sucking don't stop fag, he then told his friend I was lubed and ready to go. I heard clothes being taken off, and a condom being opened, and then I felt a cock rubbing up and down my ass, then man then said u want to be fucked fag, Rob pulled his cock out, and I yelled out fuck my ass sir. For the next 20 min I sucked on Rob's cock, and was fucked from his friend who I didn't know what he looked like with the exception that his cock was thick and big, during this they called me fag for getting fucked by a total stranger. Finally, Rob came in my mouth and the friend came in the rubber, I fell on the bed and the friend said I can leave, I got dressed quickly and Rob said he would look for me tomorrow, I left went back showers and passed out for the night.
The next day I got up ate and sat at poolside, early afternoon, someone comes up to me and its Rob, we shook hands and he said he and his friend enjoyed last night was I interested in more playing, I said what do you have in mind, and with that he said follow me. We wend back to the suite, and once inside he asked that I blow him, I pulled of my shirt and shorts, got on my knees and blew him. For the next 10 min he held my head and fuck my mouth until he came hard in my mouth. Once he was done, he grabbed lube and started to lube me up like the previous night, I asked are you going to fuck me, and he said no he was going to go get his friend who wanted to fuck me again. He tossed me the blindfold and said put on he will go get him and he will see me later. I put the blindfold on and go on all fours, less than 10 min later the door opened, and I heard good your ready, I heard the clothes strip, condom open and he then asked what I wanted, and I said please fuck me hard, to which he did for the next 30 min. Like the previous night once he came, he said I can go, and he then went to the bathroom, I went back to my room showered and fell asleep on the deck till dinner.
That night after dinner, I looked for Rob all over the ship trying to see him with the friend, but never saw him. Later that night around midnight I went back to the same bar because they have a nightly LGBT gathering after I was there who comes up to me but Rob, he said his friend enjoyed fucking me earlier but was tired tonight and since it was an early port day tomorrow, he went to bed. He then asked me was I interested in hooking up with them in port, I asked what they had I mind he said they rented a cabana at the pool that was private, if I was interested stand at poolside around 11am he would find me, and that was the night.
The next day I hung out at the pool looking at the cabanas hoping to see Rob and the friend, but they were off the ground and couldn't see in them. At 11am I stood at poolside and Rob found me and said let's go, we then climbed up the stairs to the cabana and went in, once inside he asked me to strip and handed me the blindfold. He then pushed me down and fed me his cock to suck, after a couple min I heard the door, and voice say good he is here. I was then helped to a couch in the cabana where I sucked Rob and was fucked by the friend. At this time, it was the hottest scene I ever was part of, here I was on vacation on an island, in a cabana hearing many people around, loud music, and getting fucked hard by someone I have no clue who he is and sucking on another, on top of that we were all very sweaty. We mush have been in this position for 30 min, until we all came and collapsed. But this time the stranger said I can relax just leave the blindfold on. I asked what time it was, and Rob said almost noon, he then said he was going out for a swim and sun, this left me alone with the other whose name I don't know, and I can't see him. After 5 min he talked and asked did I want to sit on a lunge chair on the deck of the cabana, I hesitated a little and then he said where the chairs are positioned know one would see you, I then said yes. Once we sat, he asked was I having a good time, I said I was enjoying the time off and the action with you guys. We then talked for a couple min about of lives he asked what I did, and where I lived, he lived in NYC which was about 90 min from me. I then asked him was he gay or bi, he said he was gay out of the closet, I then asked him why the blindfold for me. He went on to tell me he had fantasies about being a Dom and fucking someone who had no clue who he was, he said he wasn't a good dom but enjoyed the power part of me not knowing who he was. He then asked was I ok with it, and I said yes, it's different and hot and will be a good memory. At this point he was rubbing my leg moving closer to my crotch, he said I was hot, and his type and he will remember this week also. I then felt his face close to mine and he stared to kiss me and rub my cock. I know he said know one could see us but I didn't know if it was true, I felt like we were making out in public, we must have kissed for 5 min while he rubbed my cock, he then said I want to fuck you again. He then pulled me up led me to the back of the cabana where we were before but this time, he led me down on my back held up my legs and fucked me bareback. It was so hot, and then he started to kiss me with passion while we fucked for the next 20 min until he pulled out and came on me, he then took my cock and sucked me until I came in his mouth, he then shared a kiss where we shared my cum. I laid there sweaty and tired, he said wait we had to go since it was time to get on boat, he said relax for 5 min and he would see me later. After 5 min I pulled the blindfold off I was all alone, got dressed and went back on the boat. I went to the deck and passed out for a couple hours missing dinner.
That night I went to the bar again Rob was already there, he said he heard we had a great time at the cabana after we left, I agreed. He said that his friend was tired and went to bed from the long day and said he wanted to hook up with me after dinner tomorrow night if I was interested, I said I would be, he said good come to the room around 10pm, he will be in bathroom, you can strip and lay in bed. Well the next day I did just that went to the room door was open, closed it and said I was here and yelled out and said good strip down and put the blindfold on and lay on my back. I did just that and within min he came out laid on me and we made out, slipped into a 69 until we both came in our mouths. We then positioned each other where he was holding me, we talked of how hot that was and within minutes we were both hard again, and he slipped his cock in my ass, we must have fucked for an hour, until he said he was about to cum, and then he pulled out and came on me. We laid there and fell asleep for about 30 min until he woke me and said I would go since Rob needed to come back, he then kissed me and said same time tomorrow and went to the bathroom. I got up dressed and went back to my room. The next night was the same thing. Then the next day was the final full day, I started to think about the week, and how great it was, then Rob met me at the pool deck, and said If I was up for it the friend wanted to meet me at 9pm in his room, I told him I would be there. At 9 like the other nights the door was open I walked in and said I was there he said good, get undressed and go out on the deck. Having a similar deck, I know no one could see you so I was fine walking out there naked, so I stripped, applied lube to my ass, grabbed my blindfold off the counter and went out there and waited. It was a great night perfect weather with a cool breeze and all you can hear was the waves. About 2 min later I heard the door open, he kissed me and then turned me around, my hands were on the rails and he was behind me, he then removed the blindfold and said look ahead, he then rubbed me and kissed my neck while his hard cock poked at my ass, at this moment I felt something I never felt before for a man, yes I have been with men for years but I was BI, and it was only sex, here I was feeling something for a man I didn't know what he looked like or his name. he continued to rub me, he then said he didn't want to fuck me tonight, but he wanted to make love to me, I then let out a moan and said please do that make love to me, he then slipped his cock in my ass. For the next 15 min I looked out at the ocean on a deck naked while this man who was making my heart melt tonight made love to me, he was kissing my neck the whole time, and jerking me off and the said he was getting close, I then said to please cum in my, he let out a moan and said let me know when I was close, a min later I said I was about to cum he continued to jerk me off and at the same time came in my ass. We stayed like this for another min until his cock slipped out. He then said let's keep the mystery up and close your eyes to which I did, and he turned me around and we shared a passionate kiss, he then said it was an amazing week, and went inside. I went in after him and got dressed and left. I went back to my room showered and went out and sat at a bar and drank, around 1am I went back to room laid down and was upset it was over. I awoke the next morning, and there was a paper slipped under the door it read, Drew I had an amazing week you said we don't live far from each other maybe we can work something out, call me next weekend your friend Steven, with his cell number. I was happy, confused figured I had a week to think this out.
I got home that Sunday afternoon, very tired but started back up with a very busy week at work, that didn't give me much time to think about Steve. That weekend went out with friends, and hooked up with someone I knew a woman, who I went back to her place and had a sex filled night. I left the next morning, and went home, I thought about my night with here, and for the first time I thought how I didn't feel the same with her as of having sex with a woman. My mind then wondered to Steve and our week, which got me hard which led to gay porn online. That night I thought more of him and decided to call him to see what he had in mind. So, I called him he picked up and said hello, I said Steve and Drew for the cruise, he seemed happy and wanted to talk, asked if he can call back in 10 min so he can talk in private. 10 min later he called back, said he was happy I called, went on to say he was thinking all week about our time together and wanted to know did I want to meet him. I said how will this work, are you and Robe together and he said no they really were just friends. I said Ok, but you said your out of the closet gay, and I am in the closet bi, Steve said I am aware, but believes our last couple nights he felt something coming from me that it was worth trying to see what was there. All I can say was oh, he said he understands and doesn't want to push anything, but I was right he was gay and wasn't looking to hide anything. He said think about it for a week, but if I was interested come to NYC next week, he will be at this bar name which he gave me on Fri night from 8 to 10, we then hung up. I looked up the bar name and was right with my thinking it was a gay bar, I wish I can say this was an easy choice but for the next week I was unsure what to do. I kept saying don't do this your just BI, but then I would think of our last night and then questioned did I have feelings for this guy, was I gay? That Monday I met a friend a girl FWB and had a night with her, the next day it felt like the previous weekend different. Then that Tuesday night I called up a FWB gay man I have been with, closeted gay went over and like other times we made out sucked and he fucked me, but this time I didn't hurry out, we chatted afterwards which led to another fuck session something I never did before. I went home even more confused and until Friday afternoon, I wasn't sure what I would do, but finally I decided what the hell I am doing it. I packed a bag and drove into the city, well NYC on a Fri night of course too forever, but finally made it there and went to the bar at 8. I was a very nice classy gay bar in Manhattan, dimly lit, and I just sat at a back table waiting for Steve who I had no clue what he looked like. I ordered a drink, and couple min later he walked up to the table he said Drew, I looked at him and said Steve, and he said yes, I got up and we hugged and then sat back down. We talked, and he thanked me for coming and meeting here, I told him how confusing this all was I am not gay, but then again, I am at a gay bar in public meeting you a gay man who I spent the best sex filled week ever with. He smiled and said life is strange, I then really looked at him and for the first time said wow this man is hot. We continued to talk learning more about ourselves finding out he was only a year older than me lived in the city and was a lawyer. As we talked his chair got closer to mine, he then held my hand and I never moved, I looked around and other were doing the same or talking, no one was there to judge me, so I just let it be. After 5 more min of talking having another drink and him holding my hand, he did it he moved in and we kissed, it was a long passionate kiss, with his hand moving to my leg crotch area. So again, here I am a very discreet bi male in a public bar with a gay man kissing like you can't believe. Finally, we broke the kiss, but he kept his hand on my leg and crotch, and he said I think your warming up, I winked and said I believe I am. He then said he had a room reserved at a close by hotel in the city, he said will you spend the weekend with me making love, I quickly said yes, and we left holding hands, I told him I had my car and said lets take it to the hotel I can leave there for the weekend, so we drove over to the Plaza hotel, I said what don't you live in the city, he said yes but a nice weekend where we were pampered. Well we got there he checked us in, went to the nicest room I ever say, I have stayed there before and know the prices, and this was expensive room. Once we got in there, we just embraced each other kissed, and made love all night, in the bed, shower, and couch. I awoke the next morning with room service getting brought in will all kinds of breakfast food he ordered. We ate showered and fucked in the shower and then went out on the city, any caution I had to being out with a gay guy was gone, we acted like a couple all day, went to a nice dinner and back to the hotel fucking each other all night. Sunday morning was the same, as Saturday but after we ate, we made passionate love, until we had to leave for late check out. I pleaded with Steve to let me split the cost and he said no his pleasure. He then walked me down to the valet to get my car and when it arrived, he kissed me out in the open and said to call him, he then walked got in a car and left. Driving home I thought about the weekend and couldn't believe it I lived a gay weekend with no regrets. I called Steve that night and told him I had a great weekend, and that I wanted to see him again. He asked was a serious and I said yes, I have feelings for you and want to pursue it. He said good can I spend another weekend with him in NYC at his place, I said I could I was traveling on business from Monday till Thursday and just had calls Friday morning and then could come into the city. He said good I will make plans and let's chat Thursday to finalize but call or txt if I want during the week.
Well during the week, we txt since I was traveling and he was busy, Thursday night he asked me for my address and I gave it to him and he said he would have a car pick me up at noon his treat, we went back and forth about it and he wouldn't take a no and said to let car take me in and just relax. Well at noon a car picked me up and drove me into the city, the driver seemed to know Steve and said I must be a good friend, to get this treatment, I asked does he drive a lot of Steve's friends and he said no just usually Steve or clients for meetings. We got to the city at 2pm, and I was dropped off at a high-rise tower in beautiful place in Manhattan. The driver grabbed my bag and led me to the doorman who said this is Mr. Smith's guest, yes, I changed the last name. The doorman grabbed my bag and led me to a Penthouse apartment and let me in. I went in and looked and thought WTF whose place is this, I txt Steve and said I am here whose apartment is this, he txt back and said good I was there, He had a surprise for me coming around 3:30 so make myself at home shower, and someone will be at the door at 3:30 have a robe on, he will explain the apartment later.
Well I followed his orders looked around, took a shower found a robe, and at 3:30 the bell rang. I opened the door to find a man there with a bag and massage table he said Steve sent him for me to relax and enjoy. I let him in and he said lets do this in the master room, I took his lead and went into the room he setup the table and I took the robe off and laid on the table while I received the best massage of my life, for the 2nd half on my back he did an amazing job rubbing me down and making me relax, that was until I felt his hand on my cock, I said hey stop, and he just looked at me and said Steve said the whole treatment which meant this so close my eyes and enjoy. Well I just laid there closed my eyes and he gave me the best hand job I have ever had until I came, he then cleaned me led me to the shower and washed me down dried me and led me back to the bed. I looked at the clock and it read 5:00 he said Steve would be here at 6:30 have a good night and left. I must have dozed off and was awoken by my cocked being sucked, It startled me a little until I realized it was Steve, I picked up my head and said dude what the hell he just cut me off and said quiet he has been waiting for me and moved up to kiss me, he was naked already we kissed and then his cock slipped in me and we made love for the next hour, with him coming in me, and me coming without my cock even being touched. As we laid there, he looked at me and said he was falling for me, I just smiled and kissed him. I looked at the clock and it was almost 8, he said let's clean up and order in. I said ok as he asked if Chinese was good, he then ordered hoped in shower while I laid in bed, and then I went and took another shower. After that I met him in one of the rooms in this palace, I asked him whose place this was and he said a friends he was able to get for the weekend, I then said what was up with the massage he said what did I mean, I said the happy ending, he smiled and said to me that's the just part of it an ending to a relaxing massage, its not sex just enjoyment to finish off. With that the food arrived and we ate then sat on couch, he told me he was glad I came to the city again, and how did I feel. I said I thought abut him all week, and no one else, he started to rub my leg and I was getting heard again, he said good. He then asked was I willing to go out in public again like last weekend, holding hands at times and kissing, I pulled him in and kissed him with passion, and then said yes, I am, and then said I think I am gay and want to be with you. He then kissed me with passion and undid my robe, he then did something for the 1st time he moved down on me and ate my ass out, it was the most amazing feeling I ever felt, he kept eating me out and opening me up with his fingers, I was going nuts, and said I want you to make love to me, he pulled away came up to me and we kissed which tasted sweet, as he slid his cock in me. He stopped kissing me but counited to fuck me, and looked in my eyes, he said tell me again what you think you are, and I said I don't think, I am gay, and with that he came in my ass. We kissed and then he led me to the room, and we go into bed, we just went right back at kissing, and rubbing I was still hard, but he was soft but growing again fast. He said it again to me that he was falling for me, but this time I stopped kissing him and said so am I, I am gay not Bi, and I love you, this made him fully hard again and we made love for the next hour until we passed out and slept. In the morning I was woken by his mouth and led to the shower where we washed and fucked, we then got dressed and left to go out, out on the street, he took my hand and looked at me, he said was this ok, and I stopped walking and kissed him right there on the sidewalk with people all around us, and said yes I am gay. He smiled, and we had a fun day going different places and acted as a couple. We ended up a dinner at a nice casual place and talked about where this relationship can go. We agreed that the weekends could work for now, but he said he wanted something more if it worked out, He asked about my job, can I work from the city, which I could if I chose to move. He then said he wants to be open with me and no lies and wants us to be exclusive to each other. I agreed and said what about the massage with a wink which he smiled and said that's part of it, but we will only do together. We then left and went back to the apartment, once inside we fucked hard for a while and then collapsed and dozed off for a bit since it was a long day, about 2 hours later we awoke showered and went to the couch had drinks and watched tv, then he said we need to talk. He said he has told me one lie, but there is a good reason for it, wanted to make sure I really wanted to be with him, I said I did what's up, he said the lie was a simple one that this apartment was his. I must have ben in shock, and said what how, he said he was a lawyer but was a partner in the firm with money along with family money. Enjoys the good life but in the past men wanted him more for money than his lover. I must have been in shock and said oh well I don't like rich guys so this wont work, we then burst into laughs and with that we had a hardcore fuck session on the couch, and in other rooms for the next couple hours until we passed out and slept. The next morning, we awoke, and talked about everything and was a fine, I just said to him nothing has changed I feel the same way I told you last night, he then said well fuck it lets take the leap move in with me since you said you love me. I said deal, we then sealed it with a good 69 until we came. Later in the day a car took me home, and we started to plan out things.
I was able to keep working at my job better, yet we had an office in the city and since I was moving, they offered me a C level position, I was already an executive at an SVP level making 250k but was promoted to a C level making 350k. I sold my house for a nice profit and moved in with Steve a year ago. Like Steve I am out of the closet gay, but we don't flaunt it, if someone ask, we tell them the truth. I feel like I am living in a fairy tale world, every other weekend we are on a helicopter going to some party or function, and we have everything we want, and most of all I am in love with Steve and enjoy being gay.
Life is too short. Be happy and do what is in your heart.