I’m a straight man but sometimes I just wanna be a woman.
When I was a kid I discovered sex very early. I was 6 or 7 the first time I caught my parents having sex. I would spy on them anytime I could. I was 8 when I started masturbating and 11 when I lost my virginity. Her name was Crystal and we didn’t really have sex since I didn’t penetrate her, (I wasn’t even sure how all that worked at that age) but I rubbed against her and ejaculated on her.
When I would watch my parents I would always be fixated on my mom. One, because she had an outstanding body and I was enjoying seeing a naked woman being fucked, and two, there was a part of me that was curious what it was like to be fucked.
The older I got, the more my curiosity got me. It started with snooping thru my moms drawers and feeling her lingerie and underwear. Then I began to wear it while I would masturbate. Mom had a slim body and her clothes fit me fairly well. A little tight in some areas but I could still get into them.
When I was 16, my parents went on a vacation to the Grand Canyon and left me home alone for a week. Periodically an aunt or uncle would call or stop over to check on me but for the most part I was left alone. I spent the entire week in women’s clothes except when I left the house but even then I wore her panties and a bra. Even just sitting around the house I’d wear my moms pants and shirts. I slept in her nightgowns and underwear. I felt unbelievably comfortable.
In no way shape or form do I wish to become a woman. I love having a dick, I was blessed with a good sized one at that. But wearing women’s clothes made me feel relaxed and comfortable. I felt like myself which is a hard thing to come by in life.
By the time I was 17, I had my own women’s clothes that I bought for myself. I hid them in my closet so no one knew about them. I would go to the mall and buy them and sometimes the clerk would ask why I was buying them or who I was buying them for. I’d lie and say it was for my mom or girlfriend. I knew what fit me now and I was buying more and more every month. I had an entire wardrobe hidden away.
I was so excited when my parents decided to go away on another vacation because I could wear my clothes and not my mom’s. They left for Niagara Falls and I immediately ran to my room and put on a pair of sexy black lace panties with a matching bra. I also put on a pair of tight jeans and a tank top and just sat around playing video games.
That first night I was snooping through my parents drawers, since I had my own clothes now I hadn’t been snooping much. But I decided why not, it had been a while and maybe mom had bought something new that I would like that looked good on me as well. To my surprise, I found something that intrigued me even more than a pair of panties or a silk nightgown. I found my mom’s dildo!
I had been dressing up as a woman in secret for a couple years now and I had always wondered what it was like to have a dick in my ass. Of course I had heard all the stories of how it hurts but I thought this was my chance. I had a whole week to work up the courage to try this!
I had shoved a finger or two in my ass before in the shower and stuff and that wasn’t that bad but I knew this dildo was going to be a lot harder than a couple of fingers. Fortunately I knew my dad had an old porno magazine that I remember seeing an article about anal sex and how to make it easier. So I read it!
I went to my mom’s drawer and pulled out the dildo. It felt like a real dick surprisingly and was about 8”. Really the only difference with my dick was that it was a bit thicker than mine. I was still VERY nervous about what I wanted to do with it so I just started slowly. I had a whole week, no rush right?
I went to my closet and got my favorite piece of lingerie. It was a silky black dress looking thing that was tight around the chest area but frilly see through towards the bottom and came with a pair of black silk panties to match. Mom’s dildo had a suction cup below the balls so I stuck it to my bedroom door about waist high. I got on my knees and started to suck it. I had no idea how to give a blowjob but I had gotten my share of them, albeit from teenage girls that still didn’t really know what they were doing. So, I just did what I thought I would want done to my dick.
It was awkward at first but once I stopped worrying about what someone would think if they caught me, I relaxed Manx started enjoying it. I began to stroke my cock while I sucked and came instantly. I was so turned on when I was done that I kept sucking even though that dildo wasn’t going to cum in my mouth.
The second time was about an hour later and I did exactly the same thing but this time when I came, I shot it all over the dildo then went back down and sucked it pretending it came in my mouth. Wow! That got me so hot!
I slept in that same lingerie and panties. As I laid in bed I told myself that tomorrow was going to be the day I tried putting it in my ass.
The next morning I woke up, showered and got dressed. I went casual this day, no bra, tank top and a pair of comfortable sweat pants. I decided I wasn’t going to eat at all today because I didn’t want to make a mess if you know what I mean.
After thinking about it all day and clearing out my bowels, I was ready. Nervous as fuck, but ready to try it. I brought the dildo, which I had now named Josh, for some reason, into the bathroom. I got naked and ran myself a bath. When the tub was half full I climbed in and shut the water off. Despite it being hot water, I got chills as I entered the tub from the nerves I was feeling.
I stuck “Josh” to the back of the tub and got on all fours and started sucking it. All the while I was toying with my asshole with my fingers trying to relax and loosen up. I had two finger in and it was going well so I tried a third. It went in. Now is the moment of truth.
I turned myself around and backed against the dildo. As the tip pressed against my hole for the first time I got another chill down my spine. I was so nervous but I wanted this so badly! I looked down and noticed I had streaks of cum in the water that had escaped my cock. I was so turned on that I had came without even touching my cock.
I reached back and grabbed the dildo. I put the tip in the right spot and started to sit back. It didn’t go in at first so I put a little more weight back and the tip popped in. I let out a loud moan, so loud that I thought the neighbors heard it.
“Oh wow!” I moaned as I started to sit further back and pushing it deeper inside of me.
Once it was mostly inside me I just sat still for a minute and breathed. Then I noticed my hole was relaxed and it was sliding in and out perfectly! I started to rock back and forth now. Oh my God it felt so amazing! I was being fucked.. so to speak. My cock was so hard but I already came. There was no way I was going to cum again so soon. I just kept rocking back and forth, the cock in my ass felt to good to worry about my cock right now.
I wanted to try something else now so I pulled the dildo out. I was so relieved to see no poop on it! I put the dildo on the rim of the tub sticking straight up. I straddled the rim, one foot on the bathroom floor and the other still in the tub. “Josh” slid back inside my ass with no resistance. I started bouncing on it. My cock was still rock hard but now I had a better view of it sticking straight up at me while I bounced. I just started stroking myself. It felt so amazing! Within a minute or two, I felt it, I was going to cum again!!
I sat down on the dildo pushing it balls deep inside me and shot a load up and back down onto my hand. The feeling of cumming while there’s a cock in your ass is second to none! I couldn’t believe how incredible it was! I just sat there with that cock 8” inside me. I was exhausted and unbelievably satisfied!
When I finally did have the strength to stand up both my knees buckled. I was so weak. I dried myself, cleaned up the best I could and went to put on a nightgown. I slept like a baby that night. I repeated this every night that my parents were gone.
On my 18th birthday I went to the sex shop and bought my own dildo. 3 of them actually! 6” that vibrates, and 9” that has a suction cup like mom’s and one of those double ended ones so I could put one in in my mouth and the other up my ass.
I spent a whole year ignoring women and just dressing up in their clothes, fucking myself in the ass. The dildo always works but after a year, my curiosity started getting the best of me.
I wanted a real cock…
To be continued…
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