My very first bisexual [MMF] experience

I am a 33 year old straight male but I have been having sexual thoughts about men and wanting to have sex with men at least for the last 8 years. I have only ever slept with women and I have never confessed this part of myself to anyone due to the shame and guilt that I felt about it because of my cultural background. Let’s just say that I am from a place where homosexuality is not tolerated and it is punishable by death. I watch bisexual MMF porn every now and then but I have never had the courage to act on it and try it in real life. There were times that I felt so ashamed of my fantasies that I even had suicidal thoughts. So all my life I have kept this part of myself buried deep within me and never told anyone about my deepest, darkest desires. Until I met her…

I met her (27F) at a massage parlor in Sydney. Let’s call her Isobel (fake name). She is by far the most stunningly beautiful woman I have ever met. She is tall, blonde, drop dead gorgeous face with a seductive smile and luscious pouty lips. She has the most perfect figure with huge round boobs with rosy pink nipples to match, and a very full and firm ass. The first time I saw her my jaw almost dropped to the floor. I was confused why this vision of perfection was working at a massage parlor instead of walking the runway as a super model. The first time she gave me a massage I felt like I was in heaven. She always starts of her massages by giving a very slow and sensual massage with lots of kissing and teasing and then slowly turning things up until it culminates in a blissful happy ending.

I started seeing Isobel on a regular basis and felt more and more comfortable in her presence. Every time I was with her she made me feel very safe and I felt like all my worries and troubles disappeared with her touch. Whenever I felt stressed or miserable I went to see her and she always made me feel so calm and relaxed. I don’t know what came over me but one particular night while she was massaging me, I told her about my bisexual fantasies. Instead of sounding disgusted like I was expecting her to, she sounded very encouraging and told me that it was a perfectly normal feeling to have. I felt relieved that she accepted me for the way I am and decided to tell her the whole truth.

I told her that I was going through a porn phase where I was watching a lot of Hypnotube videos and fantasizing about me becoming a sissy slut. Again, she told me that it was normal and I felt like a weight lifted from my shoulders. She asked me to show her one of the videos and I showed her my favorite porn clip on Hypnotube where it’s a compilation of gorgeous women encouraging men to be more feminine and suck big cocks and get fucked by big cocks. She loved watching the clip as I could tell when I touched her pussy when we were watching the video and she was dropping wet. When she gave me happy ending that night, she talked to me exactly like the girls in the video. From then on, every time I visited her and it was time for me to cum, she would talk dirty to me and tell me that I was a sissy slut, and how she wanted me to suck big cocks for her. I loved every minute of it. She was my goddess and loved being her slut.

This went on for about 4 months as she slowly encouraged me more and more to embrace my feminine side and coaxed me into giving into my fantasies of sucking cocks. I felt so close to her in a way that I had never felt with any girl in my entire life. I was really attracted to her and adored her, but at the same time I felt like we were 2 slutty best friends talking about cocks and our slutty fantasies. We talked about having a slut competition to see who can suck more cocks. One day I finally told her that I was ready to take the leap and turn my fantasy into reality. She was very supportive and helped me to find a website where we could find a suitable guy for my first time. I looked around in the website for a couple of weeks and finally decided on a guy (28M) who I found to be quite handsome. He was very muscular and shredded with 6 pack abs and tattoos covering his whole body. Let’s call him Brian (needless to say that is a fake name as well).

The night before I was supposed to see Isobel and Brian together I could not sleep at all. I had never been so anxious in my life. I knew there was no going back from this experience and I was not sure if the reality would live up to my fantasies, or if I would even line it. But knowing that Isobel would be there to hold my hand gave me some comfort. The time finally came late at night for the appointment and I met Brian for the first time in person. He looked even better than his photos. Together Brian and I went to see Isobel. As soon as she opened the door and saw us her face lit up and she could not stop giggling. I felt so embarrassed knowing what was about to happen and my face turned red. I could hear my heart beating loudly through my chest. I could not speak or make eye contact with either of them. Isobel gave me a big hug and told me that it’s all going to be okay. I felt very safe in that moment knowing that my angel was there to watch over me.

She told me to take a shower and lie down on the massage bed. After I showered and lay face down naked on the massage bed, they both started massaging me slowly at the same time. I felt a man’s touch for the time and realized how firm it feels to be touched by a man. She then asked me to turn over and I saw that they had both taken off all their clothes as well. Seeing Isobel naked never got old as she was so sexy. But I stole a few glances at Brian’s rock hard abs at the same time and realized that he was quite good looking as well. Isobel was massaging my legs while Brian was standing next to my face. I saw that Brian was already hard and his cock was a good solid 7 inches. I felt very insecure about being smaller than him in size but also felt excited to be at such close proximity to another man’s cock for the first time. I looked at Isobel and saw that she had that seductive and naughty smile on her face. I could tell how much she was enjoying this. She told me to to touch Brian’s shoulder, arms, and abs and feel how strong he his. Next she asked me to gently touch his cock and and tell her how I felt. I told her that it felt really nice to touch his smooth cock. She asked me if I would like to suck his cock and I said yes.

Isobel asked me to get up from the massage bed and asked Brian to lie down face up with his long hard cock pointing straight upwards. Isobel and I sat down on the bed on either side of Brian’s legs and our faces were very close together to Brian’s cock. She told me to first touch his cock with my fingers and stroke it a little bit to see how a cock feels. It felt strange touching a cock that was not mine. She then kissed the tip of Brian’s cock and asked me to copy what she was doing. I kissed the tip of his cock and felt the smooth skin of a man’s penis for the first time on my lips and tasted a little salty precum. She then showed me how to lick his penis up and down his shaft and then lick his balls. I watched closely how she was doing it and tried to imitate exactly what she was doing. I really wanted to impress Isobel with my cock sucking skills. I wanted her to be proud of what a good little slut I was.

I looked over at Brian’s face and saw that he had his eyes closed and his head tilted backwards. It looked like he was really enjoying himself. Isobel then took all of Brian’s cock into her mouth and bobbed her head up and down Brian’s long and thick shaft. She took Brian’s cock out of her mouth and held it out for me and I knew exactly what I needed to do. Brian’s cock was glistening with Isobel’s saliva and smelled so delicious. I took all of his cock into my mouth and sucked as deep as I could until I felt his cock touch the back of my throat. I kept sucking his cock with all my energy and felt like I was in a trance. All I could hear were Brian’s moans and Isobel’s delighted squeals of excitement watching me suck cock like a girl for the first time in my life. She asked Brian if I was doing a good job and Brian said I was doing really well. Isobel told me what a good little cocksucker I was and felt so proud of being her little sissy slut. She rewarded me by bringing her face closer in so that Isobel and I were both sucking Brian’s cock at the same time, and we started making out and taking turns to suck Brian’s cock.

I wanted to impress Isobel even more and told her that I was ready to get fucked. Isobel looked surprised that I was willing to go all in on my first time but she went along with it. Brian got up from the bed and I lay face down again. Isobel came and stood next to my face and kneeled down so that she could whisper sweet nothings in my ears. I felt the cold lube on my ass as Brian gently fingered my asshole and tried to stretch it out for what was about to come. Isobel told me to breath and relax as I could feel Brian put a condom on and position his cock above my ass. Isobel told me to take a deep breath and exhale, and then I felt the blinding pain.

I felt pain like I had never felt before in my life. I was in agony and I clutched Isobel’s arms really tight. She kept telling me to breath and relax but the pain was unbearable so I kept clenching my body tight instead of relaxing. Brian barely managed to get half of his cock inside my ass and I had to tap out. I asked Brian to stop and he pulled out immediately. I felt really disappointed as I wanted to show Isobel what a good little slut I was and I felt like I had let her down. Isobel kept telling me that it was okay and how she couldn’t do anal on her first time either. I made up my mind that I was going to do this for Isobel no matter how much it hurt and I asked Brian to try again. He put on a new condom and this time coated the length of his cock with lube and emptied the rest onto my asshole. I held onto Isobel’s arms again as I felt the tip of Brian’s cock on my ass. I felt the blinding pain again as he slid in. But Isobel kept stroking my hair and caressing me and she kept telling me to breath. No matter how much it hurt, I held on knowing that I was safe as my angel Isobel was there with me. I was almost ready to give up again from the pain when I felt something give in and Brian’s cock slide deep into my ass. The pain had stopped.

Brian fucked me slowly at first with a steady tempo, and then kept increasing the speed until he was thrusting into me like a jackhammer. With each thrust I moaned and groaned while Isobel gently caressed me and told me how impressed she was and what a good little slutty girl I was. The pain was gone now and it had been replaced with a hint of pleasure as the full length of Brian’s 7 inch cock went in and out of my previously virgin ass. I wanted to go even further and asked Brian to fuck me doggystyle. So I raised my ass up and Isobel slid beneath me and lied down facing up. Brian kept fucking me as Isobel hugged me tightly and looked deep into my eyes. It was the most erotic moment of my life as Isobel hugged me and Brian fucked me from behind.
After a while, I felt really tired from all the pounding my ass was taking and asked for a time out.

I got up sat down next to the massage bed. I could tell how attracted Brian and Isobel were to each other since the beginning of the session and asked them if they wanted to play for a bit while I rested. They obliged very happily to my suggestion. I had to admire Brian’s stamina. After fucking me silly for a good 20 minutes he was now fucking Isobel with the same speed. Isobel seemed to be really enjoying Brian’s cock as well as she was twisting herself into positions that I had never seen before when I fucked her in my previous sessions with her. It was really impressive to see 2 professionals perform, I felt like I was watching a live porn competition and they were the finalists. They were that good!

Brian said that he was getting close to cumming and Isobel already knew about my fantasy so she asked Brian to get up and asked me to kneel down. I knelt down on my knees on the floor in front of Brian’s cock as Isobel jerked him off quickly and aimed his cock at me. Brian made a loud groaning noise and came as I felt ropes of hot, sticky cum hit my chest and run down my body. I felt like such a dirty little slutty whore in that moment. I looked up at Isobel and saw how proud of me she was. It made me so happy to be Isobel’s slut.

Brian then cleaned up and the 3 of us chatted for a bit as he got dressed. Isobel and I were still naked and I couldn’t stop hugging her as she chatted with Brian. He thanked us both for the experience and gave us both a big hug before leaving. I stayed with Isobel for another half an hour when we both just lied down on the bed and she stroked my cock, whispered to me in her sweet voice, told me how well I did that night and what a good little slut I was and made me cum. I felt like I was on Cloud 9. What I experienced was even better than all my fantasies and I was so happy and grateful for sharing this magical experience with my angel, Isobel.

I saw Isobel a few times after that experience up until she resigned and left the industry. She had told me beforehand that she was going to quit and I am really happy for her. But I felt really sad that I never got the chance to say a proper goodbye. I have missed her and thought about her every single day since the last time I saw her.

My dear Isobel, in the very remote chance that you are reading this, I just want you to know how grateful I am to you for accepting me without any reservations for the person I am. You changed my life in more ways than you will ever know. I will be forever in your debt for saving me. Thank you so very much. I wish you all the happiness in the world. I hope you are enjoying the life of your dreams and living life to the fullest wherever you are right now.

Source: reddit.com/r/gonewildstories/comments/t2mnab/my_very_first_bisexual_mmf_experience