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This story all began to start during late high school and just to be clear I was over 18 when I had sex with my neighbor for the first time. I was also 18 when my neighbor first saw me naked.

I am a mix of white and Fijian and my skin complexion is more like a caramel brown. My hair has a medium to long length, black color, and my looks weren’t half bad, but somewhat feminine. However, my body was always extremely feminine.

Nice, shapely thighs which were also thick but not too much, stomach and waist were slim and I wasn’t muscular so it really illustrated a girly appearance. Arms were pretty average and again, not muscular. I took my mom’s height at around 5’4 which I am still mad about to this day. My penis is pretty average at this time as well, about 5.5 inches, but I was a grower so it looked pretty small soft. However, my ass was just straight up fat. Nicely shaped, showed through the khakis I would wear to school, and was something that was always on my mind, but I would still call myself straight at this time.

Talking more about my neighbor, he has been around and has watched me grow since when I was in the 1st grade. He is an old, nice, and pretty tall man at about 5’11-6’0. White guy with gray hair and about 60 years old. I never really had a relationship with him and I would just do the casual greet and leave in the mornings.

Fast forward to the middle of high school which is when I began to experiment. I was still straight at this time, but with my success rate with girls being a big fat donut, I decided to test with the waters to see how a girl would feel like when being fucked. At first, this was just for fun and jokes, but then I found myself becoming more into this. I was taking photos and videos of myself posing and pretending to ride somebody. I was moaning and using this rolling stick that I had for track and giving that a blowjob. I also made accounts of hookup sites and texted with random people showing pictures and videos of myself.

What was really getting me off though was the thought of me getting railed and giving blowjobs and people praising and seeing I looked so cute from it. I still wasn’t interested in men and the thought of visualizing another guy that was fucking me turned me off so much.

However this all changed really soon when I got moved into my brothers room because he was moving out for college. I got a bigger bed, a full wall mirror, and, the important thing to this story, a big window facing my road and the other buildings.

I didn’t think much of this window at the time and was excited that I got a bigger bed and a larger mirrors so I can make more poses of my ass. I also found some old lube which my brother probably used to fuck girls, but I just used this as lube for my ass and a chance to practice anal for the first time.

This fateful night, I bought a dildo, about 5-6 inches long, on a gift card just for this occasion and I managed to hide it from my parents. I was really excited to try it and see why girls were always screaming on the internet in pleasure from other cocks. I still didn’t understand the difference because I was still referring to girls being railed in the pussy, not in the ass which was completely different and this difference really showed.

It hurted when I put the lubed up dildo in my ass and wasn’t pleasuring at all. I still forced myself to do it because I was so horny about the thought of me getting fucked even though it hurted. I am glad I did because once I got used to the feeling, the power of the g-spot brought pleasure like no other. I had to stop because I was moaning so loud and thought that my parents were going to hear me and settled on waiting for a day that everyone was out the house.

The day finally came and as soon as everyone left. I jumped on my bed, stripped down my close, started recording, and fucked myself in all positions imaginable. I was riding it, thrusting inside missionary, doggystyle, with one leg up, standing, and bent over backshots. I would even stick it on to my mirror and bounce my ass on and off from it. It was one of the best days of my life and when the moment finally came, I had one of the most pleasurable ejaculation of my life cumming hands free.

This was such a great experience until I came back to the real world. For context, I finished by riding the dildo on my bed which is faced directly next to my window that was wide open. Now there is on one window that can see into mines perfectly and when I came back to reality, I see my old neighbor who has seen me grown up since 1st grade staring at me and after closed his blinds.

I was so embarrased and started freaking out. What if he told my parents? Was he watching me that entire time? Should I go over and talk to him about this? I had no clue what to do and I just decided to ghost him everyday and act like nothing happened.

He started to act so weird around me after that. He’d gave strange glances at me with this weird face and I was just so embarrassed that I got caught red handed like that. Luckily he didn’t tell my parents or anything about what happened, but I know he told his friends (I’ve talked to him about this after we’ve became fuck buddies).

Fast forward to late senior year, I was still using my dildo and it began to be increasingly more fun and pleasurable. What happened that day was still deeply engraved into my mind but it didn’t bother me too much. I was still claiming that I was straight, but looking back in it now, like come on I’m gay. What straight person gets caught riding a dildo by his neighbor and even then, continues to use it like really?

I was still looking for more, however. In the past, I would create accounts on hookup sites to gaslight people and make them say things about how much they want to fuck me. Now, I was getting ready to have my first actual fling for a guy. In my mind, I was still testing of course and still straight.

I went on a hookup site known as silverdaddies and created an account posting pictures of my body and ass to get people more interested quicker. I was scrolling on peoples account, sending horny texts and I got a lot of guys interested in me pretty fast. I guess I was still gaslighting because they all asked me to hookup and then I stopped talking to them there. But this all stopped when I saw someone named Bruce. Now my old neighbors name was Bruce, but I didn’t think about it until I saw his pictures.

He had pictures of his body and face on his account which was shocking to me. Silverdaddies was supposed to be a gay hookup site and I always assumed that he was straight. He didn’t live with anyone but he was so masculine so I thought so. And speaking of masculinity… his pictures were so hot.

I always saw him fully clothed but with his shirt off, he was actually pretty ripped for his age and it kind of turned me on. His looks wasn’t that hot, but they weren’t bad and to be honest, he began to become more handsome the more I looked at his picture.

The devil on my shoulder told me that I should message him and even though I was hesitant, I decided to do so. Now, I should’ve made a different account with a completely different profile pic, probably from the internet so I could be anonymous, but I decided that he won’t recognize me with these pictures of my body. I was so wrong.

I sent him a message basically saying that I think your cool and we have a lot in common so we should get to know each other more. It took him a day to respond and when I say his response I was shocked. The first words I open up to is, “I’m guessing your Jaiden. Lets take this to email.” I was dumbfounded and mind you that I never put my full name, I always had some unrelated username. He knew me from my body that I showed to him like 5 months ago. And the worst thing about it was that I had put my email and to make it public so he could email me.

The next day I received a lengthy email from him regarding that fateful day. The contents of this email basically stated that he was extremely sorry for looking at me doing my business and the dangers of silverdaddies. He was also curious about if my parents new about my sexuality.

I responded to him very quickly talking about how embarrassed I was about the entire incident and that my parents don’t know. I also made a case that I was straight and that I was just experimenting. He came back to me saying that having dildos and doing stuff like that can be okay, but being on sites like that is kind of breaks that line, if you are actually looking to get laid.

I explained that I wanted to experience sex with a man just one time and I was still kind of stalling and gaslighting on this site. He told me that I should not do this and find some other way like tinder. I didn’t like this because tinder were more for dates and not hookups, I also have to show my face and no butt pics which I didn’t want to do.

I managed to switch the topics on why he was on that site and don’t you know the dangers. He explained that he was older and more knowledgable to notice signs of a dangerous person. I ended up just saying okay and called it a night

A couple days later, I went up and emailed him back again saying that I really did mean everything on my original message to him saying that I liked him and his body was amazing. That he was super attractive and things such as that.

It took him a while to get back to me, but he started saying things that I would have never thought he would say. He was being honest and saying that the day he caught me pleasuring myself was so hot to him and I am sorry if that makes me uncomfortable. I reassured him that it actually makes me horny instead and I ended up saying something crazy asking if he wanted to see more?

Surprisingly, he said he’s fine with that. I sent him a bunch of photos and videos of my ass and it bouncing up and down from the bed and he started praising me so much about how thick I was and how I was truly blessed. Along with that, he sent a photo which shocked me which you can probably guess what it is.

When I opened the photo, I was mesmerized. It wasn’t crazy big like in the pornos, but I wouldn’t even what something like that for my first time. It was about 6-7 inches in length, but it was so much thicker than the dildo I had. Not only that, but he was cut and his cocked was so nicely shaped and he had such a big type. It absolutely defeated my penis in every way which made me so much hornier.

I told him all of these things and even sent him a video of me sucking my dildo and saying things like what I would do to that meat of his! He then sent a video of him stroking it and told me to come to the window if you want, but you don’t have to. I immediately raced up the stares and saw the blinds unusually open and with him fully naked stroking his fat cock.

I got the memo and started striping down from head to toe and got my dildo to start showing him my “skills”. He had so much stamina and it took him like 20 minutes to come which was just me fucking my ass and sucking my dildo for 20 minutes. I was honestly was tired but seeing his load was so worth it. I was far away but I can tell it was a big one and I started to wish that it was on my face.

We went back to gmail and I exchanged my number with him. We then started to talk about that little jerk off session and talking about how gifted I was to have that perfect ass. I then praised his dick and stamina while also wishing that he put that load in me. He told me that no way I can be straight and saying stuff like this and I was so horny that I said, “I’m only gay for you daddy <3” exactly like that.

Another week went past and I couldn’t get over his cock. Just seeing it like that, I knew I needed to experience that in action and it was the experience that I needed. I sent a really risky text saying if he would be up for a one night stand, preferably at his house. He instantly responded and said hell yeah. I was so excited that it was finally happening! I was about to be fucked for the first time and by that beautiful cock of his!!

I told him what time my parents usually get back from work and we had about 5 hours where I was alone at home and when I would walk to his house. Next day, I got up early so we could have all those 5 hours. I dressed normally and I didn’t have anything arousing to wear, but I tried makeup for the first time. It was unnoticeable but it made me look even cuter. I didn’t prepare my ass and wanted him to experience my bare tight hole

After, I nervously walked over to his house and rang the doorbell. He opened that door and my jaw completely dropped. He was completely naked already with his dick hanging downward looking about 8 inches and thick as usual. His muscles perking and tight as ever. I was actually frozen until he grabbed me by the shoulder and guided me inside.

He said sorry for being butt-ass naked and he put some shorts on. He made some tea for the both of us and we actually had a genuine conversation about our lives. I was talking about how boring highschool is now as a second semester senior. The teachers don’t even care anymore and senioritis is hitting hard for me. I also talked about college and where I was going but that was all I included because those in-depth questions make me mad.

I switched the topic and asked about what is going on in his life. He talked about how boring his life is and that nothing is really happening. He also mentioned that he was a track coach for middle-schoolers which was a hard hassle for him. I stepped and said that I actually do track and long distance running so I said maybe he could coach me sometime as a little flirt.

He smiled from that and complimented me on my makeup. I didn’t think it was going to be noticeable, but I thanked him and said it was my first time so I tried. He reassured me that it was good-looking and I was too. This definitely set the mood for the transition and more flirting.

After chatting for a little while, he gave me a tour of his house. It was very similar to mines, but I acted interested in everything he was showing me.

We then went down to the coach and we began to binge watch some netflix. At this point, I didn’t think that we were going to have any sex today, but to be honest, I was fine with this. I was still wrong, however, and as the show we were watching progressed, we started to chat more and I was talking about some of my stories on these hookup sites. I specifically talked about how I used to use my roller stick to act like I was sucking someone off and this one guy online bullied me about it. He also told me some of his where he had this one gay guy that he had to kick out for screaming so loud from sex.

This kind if scared me because it felt like I was about to be apart of that group too, but I strongly said that they were so unexperienced and I would never do that. I was lying my ass of because I know that given his dick, I’d probably be screaming louder than them.

The show progress and it honestly got more interesting, I decided to get more comfortable and he told me that I should lay my head on his lay to get more comfortable. I did, not knowing that I was putting myself into such a vulnerable position. Like 30 seconds after laying my head in his lap, I felt something growing on his pants and I soon as I felt it, his hand gently started to rub my back.

He commented on how smooth my skin. He also said that my tights shorts made my ass really poke out. I was giggling in return and he started to lower his hand down to my butt in which he started massaging under my shorts. He noted that I had no underwear on and I came back saying that you don’t either.

I then gently pulled back his shorts revealing his half-erect cock. I looked up at him from his lap and he had the cutest smile on his face. I went back down and started to stroke his cock. It started to grow even more and I began to start licking the precum from his tip. His hands massaging my ass was so good and honestly was relaxing.

I switched the tempo and started to suck on his cock back and forth in which he responded to massaging my anus instead and putting his fingers inside. We increased the speed and he knew exactly where my g-spot was because I was about to cum from his fingers! I kept sucking harder and he gave me a heads up that he was about to cum in which I deepthroated his cock and swallowed all of his cum.

That was completely exaggerated because I did do that, but coughed it all up. He came so much in my mouth that I couldn’t handle it. His cum tasted salty and also had a slight sweetness to it which turned me on so much as I thought he might have bad tasting cum.

I looked up to him and said, “I win!” because I didn’t cum first. He chuckled at that and took his fingers out of my ass saying that he wasn’t done yet. I looked back at his cock and was honestly shocked that it was still hard and long. When I would cum, I would be out for like 2 hours!

He then decided to go wash up the mess he made on the and insisted that I can continue watching the show. I still decided to help and while I was bending over getting the last cum stain off the coach, he came behind me and slapped my ass. There was so much power behind it and my cock immediately jumped up from it!

He saw how excited I was from the first slap and he began giving me a flurry of smacks on the ass and I was moaning so loud that I know the neighbors in the other houses could hear me. He slid my shorts even lower to my ankles and helped me to take off my shirt!

It was then that I decided that I was going to be gay and after he finished taking off my shirt and pants, I said to him that I want him to pound me as hard as he can today and jumped onto him to start kissing him. He immediately caught me, and started gripping both my ass cheeks as my meat and his rubbed against each other.

His tongue tasted so good and I was ready to get pounded by him. He carried me to the bedroom and immediately started to eat my ass out. I was moaning loudly again but I tried to hold it in. I didn’t know that he was going to be soo good with his tongue! I leaked so much cum from his tongue and he flipped me over after he was done.

He leaned over to the nightstand and grabbed some lube already set before I came, and rubbed some on my ass. He told me that he will be slow because he knew it was my first time with an actual guy, but one he slid his dick inside of me, I knew that this wasn’t going to be my only time with a guy!

He started with a few slow and gentle thrust and I used both my hands to squeeze his face cheeks and told him while moaning to show me what it feels like to be a bitch. He let out a smile and started to fuck me so hard that day!

We did all position. He was fucking me in missionary while my legs were wrapped around his body. He gave me fast backshots. I was riding him. I was bent over on the bed with one leg up. He also started to pick me up and pound me with hands on his shoulders. I came in like the first 3 minutes of this flurry and he kept telling him to keep going despite that I already came. It felt so good even after I came and he was hitting all the right spots with his thick cock that my dildo could never do.

He lifted me around the house and started going to different location in it. He brought me to the bathroom to fuck iver the sink counter. He brought me back to the couch fucking me with my back arched and head down into a pillow. He brought me to the table where we had tea and I kind of knocked over some cups breaking it, but he didn’t care and thats what made this experience even hotter! He also brought me to drying machine which was still on and my ass while vibrate from his thrust and the machine. To this day, I have never experienced more pleasure than this.

He came multiple times inside of me and I was honestly getting sick from his pounding, but me being fucked was so hot and I asked for this!

It was almost time before my parents got here and he brought me back to the bedroom and had me sat on the window with my ass being pushed to the outside world. He told me that what if my parents saw me like this and I genuinely didn’t care so I dumbly slided the window open (it had the protective screen so I couldn’t fall) and I started moaning really loudly saying how get he is fucking me. People definitely heard this and he laughed and closed the window.

As he came closer to finishing me, he plopped it out and I got on my knees to take a cumshot on the face. We were finally done and I was completely exhausted and honestly couldn’t which meant that I couldn’t even walk back to my house. He guided me back and took a shower with me (I was still grinding up on him and kissing him). After that, he went back and my parents didn’t notice that I got fucked for 2 hours straight by our neighbor.

This didn’t stop, we started texting even more after that day and he complimented me on how good I took that piping. I honestly wanted more and I began to go over to his house for more poundings every day.

He would also start to come to my house during these periods and we would fuck on my mom and dads bed, in the patio, in my bed, and in the kitchen. It was an unbelievable and outworldly feeling and I was never caught.

To this day we are still fuck buddies and now that I am in college, I just drive over to his house and we meet together. I am still looking to become more than fuck-buddies and hopefully that we can become boyfriends!