I was always curious sexually from a younger age but never really acted on anything until I was almost out of high school. Went camping with my best friend and skinny dipped which eventually led to us swapping head two or three times. We grew up in a very rural area and were very much considered “country boys”. Being young and naive to the way we were raised being gay was looked down upon and we just didn’t know any different at that point. (I am aware of our extremely closed minded values at that point now that I am older). We justified it as just a couple horny friends helping each other out and convinced ourselves it wasn’t “gay” since we weren’t attracted to each other or other guys and we didn’t feel any emotional connection over it.

Fast forward quite a few years and I hadn’t done anything else sexually with a guy but the desire and fantasy was still there. In my mid 20’s I was living alone somewhat far away from my hometown and closer to a larger city. I didn’t really have any friends or family close and was enjoying that freedom. Being older and more mature I realized that there was nothing wrong with being interested in exploring sexually and what I was taught growing up was not only wrong but very limiting to myself from a mental and emotional aspect. So with that I promised myself I’d try new things and not allow myself to judge myself (or anyone else for that matter).

Maybe a year into living on my own and enjoying this new open mindset I decided to really pursue trying to explore myself sexually and then try to have some fun with guys. There was an adult toy store right down the road and although I never tried out the booths in the back I did frequently visit and started buying toys fairly often. I discovered right away that I enjoyed anal a lot and for a year or two practiced fucking myself more and more. Eventually I learned of hands free orgasms and the idea of cumming from anal stimulation only was very exciting. I didn’t get it right away but with plenty of practice and increasingly larger toys I finally had my first hands free anal orgasm. It was nothing major but once I knew it was actually possible I was hooked. By that point I had multiple toys but my favorite was a massive 9” pink cock that was very girthy with plenty of veins. It was firm enough I could really bounce on it hard but the texture was just soft enough to give just a bit so it wouldn’t really hurt like some other toys I had.

At that point once or twice a week I was really going at it starting out slow opening myself up more and more and working up to pounding out my ass hard and fast for a few hours at a time. Full strokes letting the head almost pop back out and then slamming all the way down to the balls would hit my spot perfectly. Being so full I could feel it in my stomach just behind the base of my cock was a very exciting and eye opening experience every time. I felt so opened up and loose it felt like my ass and cock were one. Every time that big pink head would bottom out just behind my cock inside my stomach it felt like my cock and balls would open up and allow cum to just flow freely with every stroke, almost like pumping a well handle. I was having full blown leg shaking orgasms to the point I would drift off mentally and almost blank out, eyes rolled back in my head just trying to stay coherent enough to keep thrusting. Quite frequently in the middle of these orgasms I would tense up and uncontrollably push from my stomach out and start shooting massive spurts of clear liquid with every stroke. It felt like I lost control of my bladder but while what I thought was pissing the orgasm would intensify by 10 times more than was already happening.

After enjoying several of these massive “pissing hands free orgasms” something clicked in my brain and I realized that this was basically the same as “squirting” that girls are capable of as it wasn’t piss but it wasn’t straight cum or even pre cum. Either way I embraced it to the fullest and would enjoy it several times a week at that point.

Having been in that apartment on my own for a couple years at that point I started the hunt for someone I could actually try to have some fun with in person and maybe hopefully experience the real thing instead of toys. I was still very shy and nervous about showing that side of myself to anyone as I thought it would be somewhat embarrassing that a big burly country guy like myself enjoyed such a thing. I had cruised Grindr for a while and had some good chats with guys that helped me ease my nerves and further accept that there was nothing wrong with myself or the things I enjoyed. I also realized just how many guys were “in the closet” themselves and also enjoyed most of the same things. As luck would have it a guy popped up on Grindr and I realized he was in the same apartment complex as I was as his location was on and he was just a handful of feet away from me. I knew there was another guy that had recently moved in and not seeing anyone else that close before I figured it had to be him. We would talk outside after we both got home from work quite frequently and eventually we figured out we both smoked weed and we started hanging out at each others apartments on the weekends here and there. I don’t think he knew I was on Grindr as my location wasn’t on and I had never actually messaged him on there. Either way one night after a few beers and some smoking it was pretty late in my apartment and he casually mentioned he was bi. He mentioned it so quickly and non chalantly and just kept on with his story I could tell he was very comfortable with the fact and himself.

I really respected that a guy like that so similar to myself didn’t have a problem with his sexuality and wasn’t ashamed of it in the slightest. I eventually worked up the courage to tell him I thought that was so cool and I decided to tell him I had always been pretty curious myself but hadn’t really acted on it much at all or explored it much. He was super cool about it and although he expressed he never would have guessed I was the kind of guy to have such interests, he was also very reassuring that there was nothing wrong with it and it was totally normal. At that point my nerves had eased and I relaxed quite a bit, I had finally told someone and it felt really good. Our conversation became really chill and we started talking about our sexual interests pretty much exclusively. I told him the very few experiences I had had years before and he told me quite a few stories of encounters he had had even up to very recently at that point. We were both obviously horny by then and decided to pull out cocks out and watch some porn. I showed him my personal stash and we put it up on my flatscreen tv and were just stroking and talking about what we thought was hot or what we didn’t like. An hour or so into stroking and edging he calmly asked if I wanted to cum and with a nervous laugh I said of course lol. He asked if it would be ok if he got down on his knees and sucked my cock and I couldn’t resist the offer. Although it wasn’t my first time getting head from a guy it was by far the best and most exciting because he was very comfortable with himself and his skills. Not only that but I didn’t feel any guilt or anxiety about it and it didn’t feel weird or wrong. He was nice and slow but very thorough. I had my balls tied pretty tightly with a couple cock rings and he would pull and squeeze on them just right while slowly taking my cock all the way down to the base and working his tongue very nicely. It must have been 15 or 20 minutes of the best head I had ever received and I was in heaven. Eventually my legs began to shake and he must have felt me tense up because he squeezed my balls very firmly, pulled down on them just to the point it almost hurt and throated my cock completely. With a few short bobs of his head the head of my cock was firmly against the back of his throat and I came so hard for what felt like 5 minutes.

After a brief period of me recovering and exclaiming how great that was he thanked me and said he was happy to help. I was so comfortable with him that although I hadn’t given head in so long and hadn’t really thought about it much anymore, I asked him if I could return the favor. Surprisingly he declined and explained that he was really only into being the one to service a guy and that him getting me off more than satisfied his needs. I was somewhat shocked but also extremely impressed that he was that confident in knowing what he wanted and liked.

I explained to him how much I respected him and his sexuality and how much I admired him for it and hoped I could eventually be that confident with myself. We would hang out usually every weekend and it often ended up with us watching porn and him draining my balls just about every time. Eventually I worked up the courage to tell him how I had been trying to explore myself more and more and I told him about my toys and how much I enjoyed anal. He laughed casually and explained that he also enjoyed anal just as much. He explained how he felt good knowing that he could please a man and that that was why he enjoyed giving head so much. He also elaborated on the fact that allowing a guy to fuck him and use him only multiplied that pleasure of knowing he could make a man feel great. I was thoroughly enamored with the way he explained how it felt to be used for another guys pleasure and how that in itself brought him pleasure. I wanted to experience that so badly at that pointed that I asked if he would give me the opportunity to let him fuck me. Unfortunately again he declined as he just wasn’t into being a top or being “dominant” in any way. Again I respected the hell out of that and his confidence towards it so I had to accept it and move on.

For a year or so we continued to hang out and occasionally he would still suck my cock better than anyone ever had. We were comfortable talking about fucking ourselves with toys and would swap stories of our recent orgasms and how much fun it was. For some reason looking back on it I should have asked him to help hook me up with someone that would use me the same way he would get used but I just never did. I don’t know if he was exclusively playing with me but he never told me about having fun with anyone else in that time period. I would like to think we were both satisfied with each other for that period of time but honestly I don’t know and it didn’t matter. Eventually I ended up moving away from him and we just slowly lost contact. It sucked but such is life and I was just happy for the things he helped me understand and enjoy.

Again being in a new place with no friends close I was back to bouncing on my big pink dildo and cruising Grindr trying to work up the courage to find a guy I was comfortable enough to have some secret fun with. A year or so in and I hadn’t had any luck or I was still too scared whichever one it may have been. My interests in porn were evolving and so were my curiosities. I was still enamored with the thought of allowing a man to take me for his pleasure. Eventually I stumbled into the world of femdom pegging, feminization pegging, cross dresser and sissy porn. By then I knew I enjoyed the aspect of doing something I “shouldn’t”, something that went against the ideas of what society thought was “normal”. I enjoyed the thrill of being a masculine guy but having a secret side that liked to be the one getting stretched out and pounded until I came the same way girls do. Seeing guys dressed up in bras and panties and wearing lingerie while being treated like a girl was just so hot. The thought of it turned me on so much and only made me want to experience that feeling of making a man feel good so much more.

I couldn’t resist the urge to get some women’s lingerie for myself and I really didn’t want to wait for them to show up if I ordered them online so I decided to do something I figured would be a little wild and exciting. I thought no one knew me here so why not go to a local store and get some for myself in person and that’s exactly what I did. I went to the local grocery store that I knew had a clothing section and I picked out what I thought would be a super fun and exciting outfit for myself. I found a couple nice pink pairs of panties, one a Lacey thong and one a pair of hot pink boy shorts (I think that’s what they are called) with black Lacey trim. Next I went to the bras and picked out two that I thought should be able to fit me although I had no clue how to size a bra lol. One was hot pink with black trim that matched the one pair of panties and one was purple lace. Just having these in my hand had me so nervous but beyond excited. I’m sure if anyone seen me they had questions but none ever said anything and I didn’t care either way. I thought that these two outfits would be enough to satisfy my excitement but just before I walked to the counter I passed the yoga pants. I couldn’t pass up the thought of trying them on so I found a pair I liked and snagged those up too and off to the counter I went. Surprisingly the cashier didn’t bat an eye and off I went back home to try on my new outfits.

Back home I laid everything out on my bed and admired my purchases. Through a slip up on my part they were in the background of a snap I had sent to a female friend and she immediately caught them. I had to make up a story quickly so I decided to go with I had accidentally took someone else’s bag at the store, they must have left them in the carousel and I just happened to grab them. Unsure of whether she bought it or not I made a joke about becoming a crossdresser and she laughed it off not believing I would ever be the type to do such a thing. I loved that. Knowing that my exterior image was the exact opposite of what I was into was a major turn on. So just to push the issue a bit and continue the joke I put on the yoga pants and sent her a snap. “Damn these things are comfy as hell, I see why you women love them so much”. She laughed and told me to quit playing and that was it, I had pushed my luck enough and also unbeknownst to her showed my secret.

That excitement tipped me over the edge and I just had to get the bra and panties on too. I slipped the thong on and as soon as it cupped my balls and I felt the lace between my ass I was so turned on. Next the bra, only the purple one fit but it fit so perfectly. The way it cupped my breasts and pulled them up and together felt so hot. Finally I slipped back into the yoga pants and stepped back to admire my ass in the mirror. It actually looked amazing and feeling that thong tight against my cock and balls and firmly between my ass cheeks underneath was perfect. I made some poses and took a handful of photos trying to look as sexy as I felt in that moment. Scrolling through them seeing my body look so feminine and sexy had me rock hard and ready to be pounded so out came the 9” pink rubber cock immediately. I set up my phone to record and with the yoga pants pulled down just below my ass I pulled the thong to the side and slipped right down onto my dildo stretching out my ass and slowly working in all 9 inches. I was so turned on and the excitement of my new adventure had me so horny I came in my panties within a few minutes.

Watching my video a short while later was even hotter than seeing the photos so I slipped on the boy shorts which surprisingly accented my ass even more and enjoyed a good edging session watching myself take a good pounding as a cross dressed sissy. I was in love with everything about it. I ordered a few more pairs of panties and a couple bras almost right away. I even got a Lacey kind of lingerie dress and another pair of yoga pants. The thrill of my new found kink was so exciting and having pushed the limit earlier I decided to try something else that would hopefully match the excitement. With my pink panties pulled up tight I slipped back into the yoga pants and tossed a shirt over top of my tits still pushed up in the purple bra and decided to head down to the community laundry room. It was late at night so I didn’t expect anyone to come in but just the possibility of being seen had my heart racing. I made two trips up and back down but unfortunately the closest I got to being spotted was someone walking by outside and I don’t think they noticed.

I’m not sure what I would have done had I been spotted but a part of me would have loved the embarrassment I think. Eventually I made some friends at work and one time I did slip up and leave some panties out on my bed while one of them was over. I really didn’t realize it until he left but he never did mention them. I would occasionally sneak them in random snaps with my female friends and I often would wear them and the yoga pants and snap them and only one of them ever caught on. Thankfully we were very close and very open with eachother and she didn’t make me feel bad about it at all. Eventually I confided in her that I was new to it and enjoyed doing things that I wasn’t supposed too sexually. She understood being away from anyone I knew and agreed it was a good time to explore myself. Within a few days she knew everything and I was frequently sending her photos of my clothes and toys and describing the things I was into. There was nothing sexual about our conversations she was just genuinely intrigued by the things I found fun and exciting. It was honestly a breath of fresh air to have someone know my secret fully and not have to be ashamed about it again.

Fast forward a few weeks and she was telling me how much she liked older men and how hot they were to her. Just the way she described them with their “dad bods” and their chest hair and their ability to take control had me hooked on the thought as well. I told her how I agreed that did sound hot and she told me to go for it and try one out. I told her I was always too nervous to actually follow through and my previous encounters just kind of happened. She encouraged me to just have fun and enjoy myself while I had the opportunity. She re affirmed the fact that no one there knew me and it wouldn’t matter if it was awkward or weird afterwards.

With those words of encouragement back to Grindr I went and after a week or so of talking to different guys and getting to know them I had become pretty comfortable with one in particular. Not only was he very easy to talk too but he was almost everything I was looking for as far as a no strings attached friend with benifits goes. He was a divorced 49 yr old country dad that was wanting to be discreet as well and just have fun and explore. I was excited but still super nervous and thought about bailing again but my friend again re assured me if I was comfortable with him and if I really wanted to do it that I should. I showed her one photo of his body and she agreed that he was very attractive and her type as well. For the first time she actually showed me part of her sexual side and said she would let him do bad things to her if I didn’t lol. So that was it, I set up a time for us to meet and told myself I wasn’t going to back out.

The next weekend we met up at a bar and had a few beers while watching a ball game and just chatted for a couple hours. I asked if he smoked weed and he said yes so I offered him to follow me back to my place and we’d smoke and see where it went. Both of us in our cars and heading back to my place I was so nervous. Part of me hoped he just bailed but I knew if he didn’t that this was it, it was actually going to happen. Sure enough we made it back to my apartment complex and he actually pulled in too. When he got out we had a quick chat about how both of us were a little nervous but excited. We both agreed if we weren’t comfortable there was no pressure and could call it off at any time. With that up we went and made it into my apartment.

A quick smoke session later we started chatting about our kinks and interests and I knew we were both horny as could be. I explained to him I how his body was exactly what I liked and I’d love to see his hairy chest and belly so he pulled his shirt right off. I told him how nervous I was and that I’d never actually showed this side of myself to anyone really and that that was part of the excitement for me. He happily assured me that he was also in the same situation. With that I offered to put my porn stash on the tv and he accepted immediately. He scrolled through and I could see him getting hard in his pants. I was shaking nervous but I mustered up the courage to get down in front of him and ask if it was ok to undo his pants. A quick nod and a smile and with that down I went.

I rubbed my hand up and down his chest and ended down at his zipper undoing his belt. Down came his zipper and his bulge showed immediately. After a little rubbing I undone the button on his boxers and got my first look at his beautiful cock. I pulled it out and tucked his boxers underneath his balls and just admired it for a second. It was so meaty and dense just the feel of it was manly in itself. He was around 7 or 8 inches and so perfectly thick I loved it. I told him I hadn’t had a man in my mouth in years but being down on my knees with his beautiful cock in my hands had me so excited to try again. He nodded and told me to have at it so with that I took him at the base and wrapped my lips around his head. Just feeling his thick firm head and the heat it produced touch my tongue was amazing. He was so hard but the softness of it was very intriguing. Up and down slowly I did my best to take him in as much as I could but there was no way I could get much more than half way down his shaft. Every time I would reach as far as I could I could feel him throb and swell in the back of my throat and that sent shivers down my spine.

I took his cock nice and slow for several minutes just enjoying everything about him and his thick dense manhood. I remembered having my balls tugged and squeezed so I did my best to recreate that. They were so big and tight they felt like they weighed 10lbs. As soon as I pulled on them he let out his first moan and throbbed in my mouth at the same time. That feeling was so intense and I instantly knew that was what it was like to make a man feel good for real. I told him how I felt and that I truly enjoyed that feeling, knowing I was making him feel great and that’s what I loved. He happily assured me it was really hot to him as well.

With that I told him to take his boots off while I removed the rest of my clothes and then slid his pants down to his ankles once he sat back down. Back in my mouth went his cock while I was there completely naked and vulnerable for him to see. The feeling of my cock and balls dangling and the air on my open ass as I sucked his cock was very humbling to me for some reason. I was completely open for him to see and I was there to make him feel good. In that moment it hit me again that this was what I loved. I was his to use and I was ok with that. I remember thinking that not many guys would be capable of humbling themselves to the point of allowing themselves to be some other man’s pleasure and I was proud of that. I pulled up and described my feelings to him in that moment. How all of this was kind of new to me but I truly did enjoy feeling humbled by him and how I never expected to be in this situation in the years before.

He understood and assured me he was happy I was capable of it loving every minute of it. That reassurance and positivity had me throbbing with excitement and I told him to go lay in my bed while I got ready to really show him my secret side. Into the bathroom I went and slipped my matching pink thong and bra on with my tightest yoga pants and my purple Lacey lingerie dress over top. I know for a fact I had never been more nervous up to that point in my life but I was too far in to go back on it and way too horny to not do it by then.

Into my room I went and the lights were off but I could see him laying there stroking in the light of the tv. Standing in the doorway I told him how nervous I was and that no one had ever seen me like this before. I told him again I never thought I’d be here having fun with a man let alone about to do what I was getting ready too. With that I stepped into the light of the tv and crawled onto the bed with him. I told him I enjoyed being a rugged masculine guy but behind closed doors this is what I truly enjoyed and this was my gift to him. I let him know he’s the real man here now, he’s the one in charge and it was all about him now. It was time for me to give myself to him and for him to take my masculinity away however he wanted too and that’s what I wanted to happen.

He didn’t say a word as I bent over on my hands and knees and he began to rub all over my ass. Up my back and down around my tits he rubbed me so smoothly yet firm at the same time. Slowly down came my yoga pants and again he rubbed all over my ass. Spreading my cheeks slowly and again the wind on my hole brought back that vulnerable feeling I enjoyed so much. For the first time he spoke and all that came out was a low muffled “god damn”. I felt him get closer spreading my legs open as I could hear him living up his cock and I knew what was coming next. He pulled my panties to the side and pressed the head of his cock right against my hole and began to push forward. Instinctively I pushed out and almost instantly his cock popped right in. That first time he stretched my ass and slid in was an extremely intense moment. It was the first time I actually had a real cock inside me and a very surreal experience. So many things were running through my head I almost began to cry but I held it in. I did my best to calm myself and try to relax as much as possible while he slowly slipped in farther and farther. He would go in and just pause then a little farther and another pause and just kept repeating that process for what seemed like forever. After a minute or so he pushed one final time and I could feel his balls against me and I knew he was all the way in.

Once he was there he took another pause and asked me how it felt. I told him it was more amazing than I expected it to be and that I loved it and I was ready for him to take me now. With that he pulled out to the point I felt his head stretch my hole again and right before it came out back in he pushed slowly balls deep again but this time he didn’t pause. Right back out he went and then immediately back to the base of his cock and he repeated this over and over. All I could do was let out a small breath/gasp every time he would bottom out. I realized with that I was super tensed up and needed to relax more so I brought my head and chest down to the mattress and did my best to relax as he continued to open me up. I went limp and just completely gave up with my ass in the air and just focused on feeling him inside of me. His pace was somewhat slow but very rhythmic and he was making full strokes every single time. I was just laying there taking it all in feeling every inch of him open me up inch by inch and just continued to relax more and more with every stroke.

Within a few minutes I was in heaven and wanted to know how he felt so I asked him if I was doing good for him, if he liked how I felt. He told me it felt amazing and he wanted to take as much time as he could inside me to savor every bit of it. I told him I’d love that and to take his time I was in heaven. I began to moan for him and tried to express how much I loved being taken by him. I was starting to feel like this was where I was supposed to be, this was what was right. I tried to push out and grip his cock every time he would thrust back into me and I think he noticed because he began to give me a series of “mmmmms”. I was focused on trying to make this as pleasurable as I could for him. He began to pick up the pace and every thrust got harder and harder. I couldn’t help but let out a moan each time and the harder he pounded the more the pressure built up inside of me. Eventually I was letting out a constant guttural growl the whole time and I couldn’t stop it no matter how hard I tried.

I had experienced this guttural moan/growl before while bouncing on my dildo but nothing to the level of this one. I knew what was coming and I knew there was nothing I could do to stop it. I did my best to vocalize I was going to cum for him and it didn’t faze him one bit, he just continued to pound and pound and pound away. The pressure finally hit what felt like a peak and my legs began to shake while I just laid there moaning like a possessed female the whole time on the verge of blacking out from the pleasure. I shot rope after rope of cum which almost immediately turned into clear liquid with every stroke of his. I tried to mumble “im cumming, im cumming, omg I’m squirting like a girl, please make me a girl daddy” but I couldn’t tell you if it came out in English or not. Either way I collapsed down onto myself as I could no longer control my body while he just kept going.

He rolled me over put my knees to my chest and slipped right back in what felt like even deeper than before and went right back to pounding away. My panties were soaked, my hole was as open as it had ever been and my cock was now limp. He reached down spread my legs and ripped my panties open in the front exposing my limp little cock just flopping away. He grabbed me by the balls and squeezed so hard I thought I was going to pass out. I had no choice but to let out a high pitched squeal in pain but I wasn’t going to tell him to stop. He asked if I still liked being the girl and a high pitched yes came out as he squeezed even harder and thrust as far into me as he could. All of a sudden the thrusting stopped and I could feel his cock throb and throb and throb while I got really warm inside. I realized he was filling me full of cum and again so many thoughts filled my head at once. I was so overwhelmed with pleasure and pain and yet at the same time I realized exactly what was happening and processed it all so quickly. He dropped my legs looked me in the eyes and told me that was the best pussy he had ever had as he slipped out of me and collapsed beside me.

I laid there as his cum ran out of me just processing everything for a few minutes before I finally got some words out. “That was amazing” was the only thing I could form. A few minutes went by and I just began thinking out loud how I had actually done it, I had actually let a real man turn me into a girl. I was the bitch and I actually loved it. I let a man take my pussy and even fill it up. I just rambled for a couple minutes incoherently taking it all in. Finally I turned to him and thanked him for everything he done. For allowing me to give myself to him and allowing my biggest fantasy to come true. He affirmed that he indeed had a great time and was glad he followed through with it too. He said that even his ex wife couldn’t take dick like that and he was hooked for sure and absolutely wanted to make it a regular thing. And with that he cleaned himself up and headed out leaving me still lying there processing everything.

That was the first time but certainly not the last as we would hang out and repeat the process once or twice a month for about two years until I eventually moved away. I do miss having fun with him but that night certainly gave me the confidence I needed from that point on to just go with it and if it felt good and felt right then there was nothing wrong with it. It took me almost 30 years to finally get over myself and get out of my head but I am comfortable in who I am and what I like now and I’m not ashamed of it. I strongly reccomend any man out there to follow through with your curiosities and do what you enjoy while you can. You’re the only one holding yourself back. To hell with what anyone else thinks.