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Cross Dressing Again

2589 words | 1 |5.00
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I had the house to myself for the first time in years and I rediscovered something from my past that I didn’t realize I needed.

I’m an adult male in my 40’s now. I got kids and a suburban home and all that other American dream crap. My wife and I barely have a sex life. Some of it is because of our work schedules, some of it because of past transgressions, and some of it because even though we say it from time to time, we don’t really love each other. It left me rather like a caged animal. I crave sex but nothing ever happens.

As a kid I developed earlier than most. I began noticing girls at the age of 7. I also noticed my older sister and my mom. Those are very different stories for a different time. However, noticing my mom is where all this started.

When I began to notice my mom as being attractive, I knew it wasn’t normal. I think now as an adult, it probably is completely normal. But, thinking that it wasn’t, made me ashamed and I developed an obsession with my mom. I remember being 8 years old and eavesdropping on my parents having sex. I would spy on my mom in the shower, or I’d hide in her closet and watch her undress. I went to any length to see my mom sexually.

Around the time I was 10 I began dressing up in her clothes and masturbating. I did that all the way thru high school. Going as far as dressing in her lingerie and using her dildo on my ass. My thinking wasn’t on a homosexual level. I thought that since I couldn’t have sex with my mom, I would dress up as her and pretend I was her being fucked by me.

Once I got into girlfriends and stuff in high school some of this went away. When I met my wife we had great sex. Quality and quantity. After we got married it all turned to shit. After years of neglect my sexual creativity when away and I became a boring old man.

My wife’s grandmother passed away and despite us living 900 miles away 4 states over she decided she didn’t want to miss the funeral. So, we packed our bags and caught an early am flight.

After the funeral my wife decided that her and the kids were going to stay another week to help out with things and give our kids some time with their distant family. I couldn’t get the time off work so I headed home.

As I walked in the house I realized that for the first time in years, I had the entire house to myself. Ever since the pandemic, my wife has worked from home and she’s always around. I couldn’t believe how great it felt.

As I began to scroll thru porn sites looking for something to jackoff to, I happened upon a transgender site. I certainly had cranked my shaft to some tranny porn in the past but as soon as I began to scroll thru it, I started remembering all the cross dressing I used to do with my moms and sisters clothes.

My wife and I are about the same height so I began to wonder if I could fit in her clothes. She’s a curvy woman so I liked my chances.

I started with a pair of panties. They were snug but they fit. I wasn’t stretching them out. The bra had the same result, tight fit but I got it hooked. I put on one of her sweaters and that fit quite well. Her jeans were not so well. After removing the sweater, I tried one of her dresses. It was tight getting on and off but it worked. After I took it all off and put it away I immediately went to the bathroom and masturbated.

I laid awake that night thinking about dressing up in my wife’s clothes again. Sure enough I turned on the lights and dressed up. This time it was just a pair of panties and this black lacey see thru teddy she had. As I stared at my self in the mirror I was gross looking to be honest. I was a hairy dude. Not freakishly hairy just an average amount of hairy.

After another quick tug of my cock, I went to bed. The next day all I could think about was getting home from work and putting on some women’s clothes. When I got home I put on a pair of my wife’s panties, an old t shirt and her favorite sweat pants. I just relaxed around the house all evening and when I went to bed I wore her favorite nightgown she sleeps in.

That night I had a very lucid dream about me as a woman and my wife was a man and she was fucking my ass. I woke up and I had came in my sleep. My wife’s panties I was wearing were soaked in my cum.

As I was getting ready for work I showered and noticed my wife’s razor. I shaved a small strip on my thigh and rubbed it. It felt amazing! I didn’t have time to just start removing all my body hair that morning which I would’ve if I did, but I did start with my beard. All day at work I stroked my chin and admired how soft and smooth it was.

No joke, within 30 seconds of walking in the door that evening, I was naked in the bathroom. I shaved every hair on me from the shoulders down. The truth is, it took me like an hour and a half. I got a new respect for my wife complaining about shaving her legs. When I finally finished I rubbed this girly lotion my wife uses all over my body. I picked this one because when my wife uses it, it turns me on. I went to bed that night in the same nightgown as before and masturbated 3 times.

The next night I started to get more and more into what I was doing. I started wearing this purple wig my daughter had for whatever reason. I didn’t like that it was purple but I did like the illusion of longer hair. I also started wondering what it was like to have a cock in my mouth and ass.

I knew my wife a couple of vibrators so I started going thru her drawer to find them. Interestingly enough, one was missing. She had brought with her on the trip. The two she left behind was a “rabbit” if you know what that is. The other was just a realistic looking dildo. It was about 8” which is about my size btw. It had a suction cup on the bottom so I stuck it to the wall and pretended to give someone a blow job for about a minute or so until I shot a wad of cum on the floor. Later that night I did it again but this time I shot my cum all over the dildo then sucked it off and pretended some guy was cumming in my mouth.

The taste of my own cum was something I had tried once or twice before but this time I actually liked it! I spent another day at work dreaming of being a woman for a day. That evening I did the same as the previous night. Only I did it 5 times! Lying in bed that night I was trying to talk myself into putting that dildo in my ass. I admit I was scared. 8” is pretty big.

I woke up that morning and decided I was going to do my fantasy and be a woman for a day. First I made up an excuse that I had to pick my family up at the airport which wasn’t really the case for 2 more days. So now I had the day off work! I started by taking a shower and going over my entire body again with a razor. This time it only took 15 minutes or so. As I got out I applied that lotion all over my body again. I put on that purple wig and tied it in a ponytail. I put on a pair of my wife’s panties, a bra, a pair of her sweat pants and a t shirt. Then I just sat around watching tv and relaxing. Every now and then perusing porn sights until my cock was hard and I would quick rub one out.

By noon I had masturbated 4 times. I knew I had to slow down. That last load of cum was just a few dribbles. I took a nap because I had lost a lot of sleep this week. When I woke up it was almost dinner time. I started to get ready for the evening I planned for myself. I started with putting on some makeup. Just a bit of lipstick and eye shadow. Grabbed my favorite pair of my wife’s panties. The sexy red lace thong! My cock barely fit inside and at the first rush of blood to my dick, I popped out of it. I slide a pair of my wife black stockings up my leg. They were old and she never wore them. She had them for years and I saw her wear them twice. They were unbelievably buried in her drawer. I decided against a bra and wore a red dress with spaghetti strap’s instead. It was snug and my bulge was extremely noticeable but I didn’t care the least. I knew if I were to leave the house or post pics people would say I was ugly as fuck but standing in the mirror I didn’t care. I was so hot and so turned on.

I made myself some dinner and ate it and then watched an episode of my wife’s favorite show, Tru Blood. Frankly it was awful but it had some nudity in it. I was now lost in the illusion that I was my wife.

I went into our bedroom and pulled out her 8” dildo. I stuck it to the wall and began sucking it off. I pretended it was my cock that my tongue was swirling and it was my wife lips wrapped around my shaft. I slowly removed my dress one strap at a time and it fell to my waist. I began to play with my nipples as I continued to slobber all over this cock. In my mind I had beautiful C cup breasts. Every pinch of my nipple sent a sensation thru me that I had never felt before. A little bit painful but unbelievably erotic. I had just made my decision to fully commit.

I stood up, slide the dress off my waist to the floor. Pulled my panties down as if I was seducing a man. Say on the edge of the bed and did the same as I slid each of my stockings off. I stood up, grabbed the dildo by the shaft and squeezed it as I kissed the wall like it was my man. Pulled the dildo from the wall and went into the bathroom.

I ran a hot bath and laid down in it. The warm water relaxes me and I felt so much better. I closed my eyes as one hand gently stroked my cock and the other began toying with my asshole. I slid a single finger inside as deep as I could. I was shocked at how awesome it felt. I hadn’t had anything like this since I was 17 or 18. I worked up to three fingers and knew it was time.

I stuck the dildo on the back of the tub. I squirted some soap on it since I didn’t have any lube. Got on all fours, reached back and pressed the dildo against my ass. I gently leaned back until the tip of it popped inside my hole.

“Oh god, holy fuck!” I yelled out as my chin sank to my chest and I got a face full of bath water.

As I rubbed the water out of my eyes, I slowly began to push back feeling the dildo go a bit deeper. Then a little further and again further. I reached back to get an estimate of how deep it was and my asshole was nearly touching the base. It was at least 6” inside me! As I pulled away I let out an even louder yell.

“Oh my god! Oh my god! Uh!” I yelled loud enough that if there were someone else in my house they would’ve heard me.

Going in felt good but coming out felt amazing! I began to slowly rock back and forth. Each time trying to push it in as deep as I could. Noticing it was sliding in and out very easily after about a minute I began to really get into it. I was rocking back and forth, splashing water all over the floor. My cock and balls splashing against the warm water tickled it just enough that suddenly I felt I was gonna cum. My arms felt wobbly as the cock continued to slide in and out of me and the sudden urge to explode came over me. As I looked down I got an image I’ll never forget. Between my legs I could just barely see the balls on the dildo and my cock shooting a fresh load of cum streaming thru the water. A few more spurts came out before I finally relaxed my hunched over back and fell forward a bit. The dildo slipped out of my ass.

“Oh fuck!” I screamed one more time as the pulling out completely felt the best!

I laid in the bath for about 10 minutes before I noticed my cock getting hard again. With the dildo still being in the same place, I got back up on all fours and put it back inside my ass. I had tightened up a bit so it took a few soft thrusts to get it back. I proceeded to have sex with that dildo in every imaginable position over the next 15 minutes. Finally, while straddling the wall of the bath tub in a reverse cowgirl like position, I began stroking my cock and immediately I exploded all over my leg.

I cleaned up as best I could and put my wife’s dildo away. I put on some of her pajamas and went to bed. The feelings I felt that night were insane! First, I was exhausted physically. Riding a cock aggressively for 15 minutes getting out years of frustration came really wipe a guy out. But 2, as I said I felt 50 pounds lighter. Like I had wiped out years of sexual frustration and a weight was lifted off my shoulders. And 3, I was so surprised with myself at how quick all this manifested and how quick it progressed. Also, I was surprised how far I had that dildo inside of me and I wanted more!

I had one more night alone and basic did the same thing. It was so refreshing the first time and was equally as satisfying the second night. My problem was, how we I going to be able to continue things like this with my wife and kids coming home tomorrow?

More to cum…

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1 Comment

  • Reply [email protected] ID:1eb5z42y4fwx

    I love the story and can definitely relate. I relish the times I am alone so I can finally be a girl again. It feels ao right.