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I’d like to take a moment to apologize if anyone likes fancy detailed story telling, I will do my best to make this entertaining and very hot, but given that this my first time writing about an experience of mine, please be patient.A lot of this may seem cliche but it is genuinely what I felt and what I’ve gone through so please try to enjoy.

So this all began around the time when I had recently turned 18, I just your typical high schooler, I was on the soccer team, i had a good social life, a good set of friends, nice family, I wasn’t the most fit even though I was in a sport but I was reasonably fit. I was and still am about 5’8 nearing 200 pounds so yes a bit stocky but nimble and proportioned, but back to the story at hand, I was very active on social media as most young people are. A lot of people tend to follow other people on social media regardless of knowing them or not, and I had come across the profile of what appeared to be a girl.(who for the sake of this story I will change her name) she went by the name Ariana and she was absolutely gorgeous, great body, cute face, very curvy, a 10/10 in my book. So I started following her and she would post a lot of very provocative pictures with very sexual captions and things of that nature. After having followed her for a while, my social media started recommending that I follow this specific person who also followed Ariana’s page, and I noticed that the profile belonged to a guy (changing the name to protect their identity) named Juan, but Juan had a very striking resemblance to Ariana. Like exact facial features like a little dot on the right side of her lip, and the same touched up eye brows, and a couple of freckles on her face. So I followed Juan and eventually I come across an image that was posted on both profiles of a bed covered in rose petals with candles around it with a caption implying that they had a romantic evening, and that’s when I figured out that Juan was Ariana. Eventually she went on to delete all social media pages that had her shown as a guy, and she only kept all the Ariana accounts.

This of course sparked my curiosity, I knew it was a guy now, but that didn’t bother me, in fact it just made me more interested, the thought of Ariana living this little slutty life, where she was having guys fuck her and giving blow jobs and meeting up with her guy friends for more freaky fun was just such a turn on to me. But again while I was interested in the idea of being with a cross dresser/tranny, I couldn’t help but have my brain shift in an even more unexpected direction. What would it be like to be in her shoes, of course I brushed this off almost immediately I just thought to myself “how could I think this, I like girls, and trannys/cross dressers are basically girls too” and it left me again in this state of confusion and I was questioning everything, I was questioning my morals and everything I was taught while growing up(I grew up in a pretty religious home, but I never identified myself with religion) I wasn’t exactly the most attractive male, but I wasn’t ugly either, I got a decent amount of attention from girls but seeing the way guys would just flock to Ariana, not caring that she still had a penis, not concerned with any of that made me want, no, crave that level of attention. But again I pushed all that to back of my head and I paid it no mind for a while. I continued to live my life normally, and then one night when I was watching porn, I was typically a fan of lesbian porn, but I started watching regular straight porn, and I just couldn’t help but notice all the pleasure the girl was receiving. Obviously I know a lot of it is exaggerated for the viewers pleasure, but I also thought about all the stuff I’ve heard in my life from girls about “dick appointments” and getting their guts “rearranged” so I know there is enjoyment to sex atleast a little bit. And then of course I start looking at the cocks in these videos and I can’t help but wonder what it would be like to have one in my hand, and to go as far as to put it in my mouth and maybe even go a step beyond and have it inside of me. Then I further dive into that Ariana fantasy of mine, and I watch tranny porn, but my favorite became cross dresser porn. The thought of all these men, who must’ve gone through the same mental battle as me, just gave into their urges and are now living their fantasies and dreams and enjoying every second of it, some seem to enjoy it more than the actual girls and of course I can’t help but see that, and it just pushes me over the edge and I finally let curiosity get the better of me. I had heard about people using craigslist for meeting up for no strings attached fun and I had gone in my share of times just to look at the pics women would post in the women for men section, but now I was going into unfamiliar territory and I went into the men for men section and it was just a different world. All these terms I didn’t know about, I didn’t know what bottom and top meant, I didn’t know what asl meant, I was a pure person among everyone in this forum. I just scrolled through a bunch of the ads but I couldn’t work up the courage to message anyone. So I decided why not let somebody message me, so I eventually worked up the courage to make a post, I took some pictures of my body, I shaved to make it look more smooth and feminine, and I took some pictures of my ass, because I really wanted to try being a bottom. After a while of getting some responses here and there, everyone seemed to be attracted to the idea that I was a first timer, and many people were saying they would love to pop my cherry and take my virginity. But of course I got nervous and anxious and scared and I backed out meeting with anyone.

Conveniently once I started college, the way my school schedule worked, I would have the house to myself most of the week in the mornings because some days I didn’t have class until in the evening, and my parents also wouldn’t get home until I had to leave for class so I had the perfect opportunity and one morning where I just woke up in absolute heat and I edged myself so far, I worked up the courage to invite somebody over, I made another post, saying it was for right now and describing my scenario again, “18 year old bottom boy virgin hosting looking for first time” and I got a couple of messages here and there but there was one guy that was very sweet and kind in his messages. His name was (changed for the sake of the story) Robert, he said what many others had said that he would love to be my first time and that he wanted to pop my cherry and make me feel good. Given how turned on I was already, I have him my Kik username and we messaged there and I almost backed out of again out my fear and shyness but I buckled down and committed, and I typed in my address and as soon as I pressed send I knew there was no backing out. He said he drove a white car, and that he would be there in about 15 minutes, i took a shower before he came, made as good of an effort to clean “down below” for what was about to come. I was so nervous, I was shivering at the thought of what was about to happen. Eventually I see a white care pull up in front of my house, and there’s no doubt about it, it’s him, so I go outside and open the gate for him and he comes inside. He was really cute, similar body build to me, but a little more fit, he had gorgeous eyes, and these big inciting lips with his hair slicked to the side.

So we go inside my house and we have a little bit of small talk, he asks me if it’s really my first time and I tell him yes, and he tells me he’s excited and that he hopes that I like what’s about to come(no pun intended) and we walk to my room and he squeezes my ass as were walking and I jumped and my heart just started racing. Once we get to my room I close the door and I’m stuttering and shaking and of course he notices and he asked me what was wrong and I just told my I’m just so nervous and that I’ve never done anything like this before, I was just completely freaking out, and he pulls me closer to him and he looks me in my eyes and tells me to relax and suddenly he kisses me. I’ve kissed a decent amount of girls all throughout my life up until that point but this kiss just had so much passion and intensity behind it, and I felt all of my worries and anxiety flow out of me. I started kissing him back immediately and it just felt so right, our tongues playing with one another and his big lips on mine felt incredible, he started grabbing my ass while he kissed me and I just felt like his little slut. I was melting in his warm hands, and I wanted him to take me. We just stood there making out for a while, and he undressed me while we’re kissing and he guides my hand to his cock over his shorts and that was the first time I ever felt another mans cock in my hand and it was incredible, I couldn’t wait to actually feel it in my hands and not just over his shorts. He worked his way all of over my body, he kissed my neck and he sucked on my nipples and this just drove me wild, I had never felt so turned on in my life. And all of this built up to where he sat on my bed and he told me to pull his shorts down, and I obliged happily. I pulled them down to reveal his 7 inch thick monster and everything just came so natural to me, I knew the moment it popped out I wanted it in my mouth, and I started sucking on it and it was more amazing than I ever could have anticipated. Hearing his moans and him telling me I was doing a good job only made me want to pleasure him more all the way to completion. Stroking his cock while I swirl my tongue all around it, playing with his balls and sucking on them, it all felt so good. I had edged almost to full on climax and he stopped me and said that my job wasn’t over yet, and he told me to lay on my bed, I have pulled out some condoms and I didn’t have lube so I just gave him a bottle of lotion and I told him to please be gentle, and he told me not to worry, which was reassuring but again I was still very nervous, but I thought back to all the porn I have watched and I knew it should be an enjoyable experience. He lotioned my ass up along with his cock, and I felt him rub against my tight virgin hole and I knew what was coming, everything I had experienced, all my thoughts and emotions led me to that point, and I was as ready as I could ever be. He started pushing into my tight boy pussy and i felt the head going and the pain almost seemed unbearable, it felt like something was about to tear and I immediately pulled off of him and I sat there in pain for a couple of minutes he asked if I was okay and I said yes, I told him I didn’t think it would hurt that much, and he told me that we just have to wait for it to stretch and then it will feel good, I was scared once again because I just thought what if it keeps hurting, and we tried one more time and I felt the head enter and the pain started again but this time he didn’t keep pushing he just let the head sit there and I felt my muscles relax more and more and eventually he started thrusting slowly in and out in a steady motion and that pain just turned into pure pleasure, once all that pain went away, I felt like his little toy and my only thought was I want him to use me, and that he certainly did, he picked up the pace 100% and was going in and out of me so fast, he did me doggystyle, missionary, he let me ride him, and a bunch of other positions I never knew about and eventually we both climaxed together and I had never came that much in my entire life. We just laid there trying to catch our breath and we kissed and cuddles some more and then eventually he left and we said out goodbyes. We messaged again later that week and for whatever stupid reason I thought I had a change of heart and that I wasn’t gay and that I just satisfied my curiosity and that I didn’t want to do that again. I told him sorry I just realized I’m not gay or bi or anything like that, but thank you for that experience. He of course called me out and he told me that we could not have had that level of passionate sex for me not to be gay, or atleast bi, and I just told him that i realizes I was straight and that was that, and he said that it was fine and he understood, and he said that if I ever wanted to have with him again, that his username would always be the same and to not be a stranger, and now you may be wondering where will this story end, and the answer is somewhat expected, here I am four years later and I still see Robert on a regular basis for some naughty fun and that was my story of my first fling that changed my life.