I'm going to be honest I have no idea where to write this but i just want to get it off my chest as my entire life feels like on big secret.
I'm currently 20 and turn 21 this year. 5 years ago I never ever would've questioned my sexuality and I have always been bought up to never turn gay with my dad being totally against it to the point I heard it a lot growing up. So I was always straight and always thinking about girls.
That was until 5 years ago when me and my best friend who is gay btw which its self has never bothered me and my dad actually likes him but he would never be okay with his own son being gay (me) , anyway me and my bestfriend were getting changed in my room to go out with some friends when I walked in just after having a shower (i had 0 problems getting changed infront of him. Im comfortable in my own skin and we've known each other for many years). I took my towel off and leant over to grab my boxes. Thats when he randomly came out with "I'm surprised for a straight guy , you fully shave smooth" We both laugh and I say "why you looking anyway" and he just said he glanced over not expecting me naked 😂 I laughed and just said "i prefer to be smooth" then he said well don't take this the wrong way but you have a very twink body for a straight guy. We both laugh and I jokingly tell him to "piss off" 😂 we laugh again.
The next night however, when i was alone in my room it did get me thinking and I just started searching up twinks. Which lead me to twink porn which I noticed made me hard. I was confused and just turned it off. However, again my curiosity got the better of me and within the next week I was having myself off to twink gay porn.
Everytime i came i would be ashamed but i was choosing to watch it more and more. Each time I would end up further down the "rabbit hole" prostate porn, sissy porn, pegging etc.
Each time i became less and less ashamed until i eventually got curious enough to try fingering my ass. It felt weird but I liked it. However, after again I felt disgusting and this really put me off it for a long time (around 18months).
So in that time I never did any of the above again and was enjoying time with girls in them 18months. Now we have a neighbour whos in his 40s and lived here all my life. I would regularly help him in the summer with his garden for money when i grew up and then eventually when i had an apprenticeship I just did it for free. He was a nice guy and we got along very well. It was around mid 30s and after we finished he asked if id like to chill with a beer and in his hottub. I of course said yes. (He has a full setup in his backyard and its proper great). We were having a great time into the evening and after 4 beers the conversations become more sexual (not uncommon between me and him). He then asked if I had ever had any gay thoughts. I declined and laughed but he then said "you know if you had I wouldnt tell anyone" so i laugh and tell him what i used to do.
He told me I shouldn't be disgusted and just because my family disagree doesnt mean i shouldnt enjoy what feels good. So we laugh and he started talking about looking into getting a dildo, prostate vibrators and telling me some tips. It was embarassing and funny and helpful all at the same time. For the first time in my life it felt like someone was truly looking out for me properly and respected me for who i was. The conversation
Started to make me hard asf and when I went to get up to grab my beer from the side he noticed and said "someones enjoying the conversation" we both laugh and I apologise but he said "its normal, and its okay. Trust me you're allowed to be turned on by these thoughts"
Not long after that i go back home and immediately start fingering my ass but a mixture of the beer and the conversation made me go mad.. forced gay porn. 2/3 fingers and had myself off. It didnt take long for me to cum but after i didnt feel so guilty. The next day I ordered a 7 inch dildo with decent girth on amazon as i wanted it asap.
The next day with quite a bit of lube I fucked myself crazy for over an hour. I didn't wank during this. I just put on sissy porn on my tv and fucked myself. I was honestly in love by the feelings it gave me. I didn't feel guilty and it didnt feel wrong. I wanted it and i loved it.
Over the next year I ordered 2 more dildos , one that was black and super big (around 10inches with 2.5inch diameter) and one that was 8 inches. I still also participated in straight sex and went through phases where dildos would disgust me but overall the more i resisted the more i did it. One time i did get close to being caught when using a dildo which worried me and lead to me finding good hiding spots for them.
During this time I got super close to my neighbour as it was nice having someone to speak to as i didnt want my gay bestfriend to know. My neighbour did a lot of reassuring too.
Now last summer, I started getting into chasity when i rid my dildos as it felt that little bit mote exciting. I also brought myself a pair of female pants.. again it kept disgusting me but I still kept doing it. My feelings were all over the place at this time. I felt totally straight but enjoyed all this other stuff i was doing whilst the constant feeling of disgust was all over my mind.
However, one weekend last summer i did the usual go round my neighbour help him with the garden and we sat speaking about everything. He order pizza for us (this was quite normal that we'd spend most of saturday well into the night together) after 2 beers I told him about doing chasity and wearing pants. He was extremely surprised at first but said i had nothing to be ashamed of. Which made me feel somewhat better.
Pizza arrived and we were eating when some peperoni fell off onto my white top 🙄 I took my top off at it was 36 outside and warm in his living room + the stain all over my top i didnt want it getting worse. Now i have a very slim build and I sense him looking over when i was topless. So i laughed and joked "do you like what you see" he laughed and said "whats not to like about a young lad in your living room just in shorts" then he quickly said "joking" so we laughed but the entire conversation did get me thinking if he really did like what he saw. I had a 3rd beer (him 4th) then cleaned up.
However, when i was at the sink with him drying the pots. I felt him brush against my ass very close and could feel his dick which felt hard and it felt big. I thought it was accidental at first until he did it again but this time stayed just that little longer. I felt myself start to get hard which really confused me i ignored it and then started to walk back to the living room when he noticed my boner and he questioned it and i said sorry and he laugh and said its fine. We then went into the living room when he noticed me covering myself with a pillow and he then says "you dont have to hide you know" I laughed and felt at ease. We have another beer and carry on the conversation about chasity. This only kept me rock hard. To the point he said.. you know we could always watch some porn together and i could show you the good stuff. I laugh and said sure "okay" still laughing. He then stuck on gay chastity porn which looked so hot. After a while he asked if i was enjoying it i said i was and he said why dont you play with yourself then. We both laugh and he says "im being serious" so i took a sip of my beer and say "okay then" and started stroking. We were sat quite close and i could see him keep looking to his left at me. He then asked if it was okay if he did the same and i said "its your house so of course its okay"
At this point my mind had a mixture of "wtf is going on" and "his dick is so big" and i couldn't keep my eyes off it which made me feel so guilty. He noticed me looking and said "would you like to touch a real dick instead of your dildos" i said no and laughed but he said "its okay you know" so i said "okay" and came over to stroke his cock which made him start stoking mine. We were then sat next to each other and looking at each other when he started kissing me. It was at this point all self respect left me and he had his hands all over me, grabbing my neck, chest everything. He then held my neck and snogged me until he said "get on your knees now" so i nodded as I felt a rush from being told what to do. I then started sucking him. I kept thinking "this is wrong" "stop" and i felt guilty still but just as i was thinking it was wrong he held the back of my head and started guiding me. He was a big guy and i was just a skinny boy. So he easily forced his entire shaft down my throat until i was choking but i couldnt stop him and at this point i was hard from the domination and wanted his dick. The straight thoughts had left me and when he was done face fucking me. We went to his room and he rimmed me. He then got out some rope and told me how he was about to tie me to his bed and i couldn't stop him. So i didn't. I let him tie my arms to his bed and he lifted my legs with his arms and rimmed me. He then started fingering me which felt incredible and he knew how to do it better than me. I did keep thinking however that i wasn't sure if i wanted to be fucked. But all he heard was me moaning. He then got up and grabbed some lube and then i realised what was about to happen. My heart was racing and i wanted to tell him to stop as he applied the lube and fingered it into me i kept moaning. He stroked my dick at the same time which only made me moan more. I then looked down at how hard and big he was. All i could feel at this point was guilt and kept saying "wtf am i doing" and i was about to say "stop i dont want this" but thats when i felt it. His big warm head split my hole open with ease and i let out the biggest moan as i felt his entire dick slide inside me and thats when he said "good boy.. take that dick" i looked at him and that was it. I gave in and my ass relaxed. Which made it easier for him. He kept pouring more lube every few strokes. I couldnt stop moaning and after a few minutes i was being pounded. He then grabbed my boxes and put them in my mouth and tightened the ropes and wrapped my ankled together. At this point i realised the reality of my situation. I was gagged, lubed, fully tied up. I couldn't go anywhere, couldnt shout out and i was fully at his mercy and control. This made me more horny and he went to town on me. Telling me i was made for dick, i was a gay boy and then told me "everytime you come round mine, you will wear your chasity and panties or i will tell your dad about your dildos" all this dirty talk made me beyond horny and i then felt it.. my first hands free cumming expierence and it felt like nothing else i had ever expierenced and i moaned into my gag and he noticed it and not long after that he finished inside me. My legs were shaking like mad at this point.
After he let me shower and we spoke about everything downstairs. I went home and i felt disgusted especially as i was very stretched which i could feel and his cum was still dripping out of me.
I then didnt go round for a while after but i did speak to him about what happened and that it shouldnt have.
He was okay with that but told me "he is always there if i need him"
It was then 6months after. So last december. I went round to talk to him about it all.
I had barely played with dildos or any of it and stopped watching gay porn.
He apologised but i told him he had nother to be sorry about.
It was then when i told him i wanted to try again. I told him i kept being confused but at the end of the day i always came back to the same conclusion and was back doing it.
He said okay but we can go slow.
So that night we had gay sex, i sucked him and it was slower but just as good.
This then became regular for 3 months. Until march this year when we started doing other things.. he made me one night wear my chasity and panties. He had also brought a skirt, thigh highs and a girl top which was very sissy like and had the black spade on. He ordered these so my dad and family wouldnt find out. When i arrived i got changed and he made me walk around his house like that for a few hours whilst we did our usual weekend chilling out. That was until evening when he made me essentially his whore. I was bent over on his bed. Wrists tied to the top head board and my ankles to the bottom of the bed. Still wearing everything mentioned. He then put a blindfold on me and gagged me. And said the words "I'm going to make you a good sissy slut" this thrilled me with excitement. I started to feel lube on my ass as he pulled the pants to the side and he insert his cock. He then destroyed my ass. Dirty talked me and i could do nothing but take it. He then finished inside me and i coild feel his big load dripping out of me. He then reinserted himself and told me he wasnt done and carried on using me with the faint whimpers into my gag from me i eventually starting cumming from my chasity and he heard my moaning so he lifted my skirt and saw telling me that i was a good sissy.
He used me for over an hour before I was finally untied. I had 2 loads of cum in my ass and he introduced me to a butt plug which he told me to wear before getting in the shower so i did.
After when i went home I felt amazing. I was still locked and had a butt plug on with my panties. All the guilt had gone. We have since made this regular. I have had straight sex too in this time which leads me to having confused and guilty thoughts on occasion but i have pretty much carried on.
So yeah.. i dont really know where this leaves me but my family know nothing about it and my dad would kill me if he knew and I do sometimes feel guilty and it does sometimes feel wrong. To everyone else im still straight so i just leave this as a secret part of my life.