First Time Crossdressing For A Man [TM]

Hello everyone,

This is a crosspost r/gaystoriesgonewild. I’ve been a lurker here and have a few stories of my own that I could share but never have. I got a pretty good response on the above sub so I figured I would post here too! ? what follows is copied from the original post:

Now I know that the whole sissy fetish isn’t for everyone in this sub, or even really that accepted in the gay community at times. That being said, for me, the appeal to the sissy fetish is much more about the humiliation aspect of the kink than anything else. As this story will explain, I never knew how much I really enjoyed being so submissive.

What follows is entirely true, and I will never forget it:

A little about myself. I was 20 years old in college at the time. I was about 165 lbs and 5’9. I had always enjoyed dressing up from an early age. When I was much younger, I vividly remember stumbling upon transsexual porn and becoming instantly infatuated. I found myself wanting to dress up and wear sexy lingerie. When I finally moved out of my parent’s house at 18, all bets were off. I had roommates, but would almost instinctively close the doors to my room every night and slip into some sexy clothes and play with myself. I went to local sex shops and bought tons of outfits over time, dildos, heels, pink chastity, the whole gambit.

By age 20 I had a whole wardrobe of outfits, wigs, dildos, heels, etc. I had toyed myself enough to be able to ride a dick without having any discomfort and only pleasure. I posted photos online to chat with guys regularly, posted on craigslist for the same reason. I had been with two guys prior to this but it was never anything special. I enjoyed it, but it was rather vanilla, and I was never in full dress up during the experiences. At the time, I didn’t understand why it was that I enjoyed dressing up and playing with myself. I thought it just kind of felt good, but that was about it. Psychologically I didn’t get the rush I got out of how naughty it felt to be cross dressing.

That all changed.

It was around holiday time and my roommates at the time were all going out of town to be with family. This was unusual because I had about 3 roommates and at least 1 was always home regardless. I was overjoyed with excitement knowing that I would have a whole few days to myself to dress up and play with myself. I was so excited that I went to a sex shop, got a ton of new outfits, garter belt, wig, heels, fishnets and a dildo to play with! I figured it would just be a great weekend to take photos, play with myself, and chat with guys online. I was wrong.

I woke up that day excited to play. The last roommate to leave the house said goodbye and as I closed the door, I knew it was game time! I immediately shaved all my body hair yet again to be perfectly smooth and began chatting online with a few guys who responded to my craigslist post the night before. In the ad I specifically said I wanted a man who knew how to use me and that I was okay with being totally dominated. One guy in particular claimed to be a military man. He had beautiful arm muscles, one arm in full sleeve (which I thought was so hot) and was saying things that just started to melt me. He was extremely dominant and assertive, saying that he knew that I needed to be punished for being such a bad boy. Saying that “real men don’t wear bitch clothes and present themselves online for other men.”

He sent me a photo of his cock, which looked about the same size as my dildos, circumcised, and delicious – about 7-8 inches. Included in the photo of his dick, he captioned, “a real man wouldn’t feel his ass pucker up and his mouth water at the sight of this.” He was right. The second I saw the photo I could feel my ass clench and my thoughts raced with wanting to put it in my mouth. I wanted it.

I figured I had been with two guys previously (on separate occasions) and that this guy was hot as fuck, wanted me to dress up, and knew how to say all the right things to me. I had the whole house to myself, so why not? He asked to come over, I agreed. I sent him some photos of myself in different outfits and asked him which one he wanted me to wear for him. He said he wanted me in “the maid outfit, as slutty as possible.”

When I sent him my address, I panicked. I had never been in front of another guy while dressed like a slut. I didn’t know what to expect. I quickly grabbed a drink to settle my nerves and started to dress. I put on hot pink fishnets, a matching garter belt, and crotchless panties. I slipped into my heels, put on pink fishnet sleeves to cover my arms, and then put over my pink and black maid costume. It wasn’t much, just enough to cover my chest, with a strap in the middle going to my waist, and then expanding around my stomach to clip behind my back. I wore a blonde wig, as much makeup as I knew how to apply. And then, to finish off the job, I put a pink gemstone plug in me and my pink chastity on.

I remember pacing around the house like this for what seemed like hours. I looked in the mirror constantly thinking to myself, “what the fuck are you doing?? Look at you! You look ridiculous!”

The doorbell rang and I thought I died.

My heels clunked on the hardwood floors over to the door. I looked through the peephole and there he was. About 6 feet tall, white, broad shoulders, shaved head, muscular, and hot as fuck. I, clearly was no match for this man. He was a real man, and I was a sissy. The comparison couldn’t have been clearer.

I opened the door, stood there fully exposed, chastity and all and said, “hello” in the most feminine voice I could. Before entering, he looked at me, saw his next prey to conquer, and let out this deep laugh, “HAH!! Look at this little bitch!!” He entered, and my heart sank. With the closing of the door behind him, I became his property to use. I didn’t even know what to think. He just laughed at me and humiliated me after I had put time and energy into looking as good as I could for him and he just laughed at me! I felt my dick shrivel in my chastity.

I just stood there and he circled around me, like a lion about to pounce, eyeing me up. As he circled around to my back, my ass was exposed, and he gave it a hard but SLAP. I jumped and let out a “Oooh!” and he responded “shhhhh, you know you like it sissy.” I did. He asked me to fix him a drink, so I got him a beer from the fridge, bending over nice and low for him. He asked me how rough I wanted it, and I said “I want to your little bitch.” “Good” he replied, “because I’m going to make you forget you were ever a man.”

I was so turned on at this point. I was ready for this. He had a few sips of his beer, walked over to me, grabbed me by my throat, and pressed me against the wall behind me. He looked me right in my eye and said, “You can only refer to me as “sir” or Daddy” from now on, understand.” “Yes, Daddy,” I said with short breath. His body was tightly pressed against mine and I could feel his cock bulging through his jeans. I went to feel it with my hands and he laughed again and said, “look at you you fucking faggot, you cant wait can you!?”

I couldn’t, I wanted it in my mouth. He ordered me on my knees, and I obliged. I pulled his pants down and staring directly in front of me was one of the most beautiful cocks I have ever seen. Hard, cut, eager to use. Without hesitation I opened my mouth and began to suck. I have a pretty good gag reflex and had practiced sucking dick many times with my dildo. I immediately went to town. He just continued to call me names, called me a fag, a bitch, a slut, a sissy princess. He me I was worthless, that the thing between my legs was a waste of a cock. I just kept sucking. I had never been so degraded.

Here I was, being made fun of, with another man’s cock in my mouth. I was for some reason, in heaven. I sucked him for a while, pressing the plug inside me as I did. He saw and said, “look at you, you love this! You cant help but play with yourself while sucking me!”

Eventually, he stopped me. He pulled me up onto my feet, with saliva all over my chin, chest, and hand from sucking him. As I got up, he slapped me right across my face and said, “you’re a worthless sissy bitch, and now you’re going to get fucked like one.” I couldn’t wait. The slap rushed me with emotions that I did not expect. I was shocked, pissed, and yet so helpless to do anything. He could easily beat me up if he wanted. So I moved on, because I liked it.

We moved to my bed, he bent me over on my knees and I was there, ass exposed, pink gem staring at him. My cock limp yet bulging in my chastity. He grabbed my caged cock from behind and held it in his hand. He said, “look at you, you got all dressed up for me, a real man. This is what a real man does, he fucks bitches like you. You’ll never be a real man, never again at least.” I was so powerless to whatever he wanted to do to me at that point. He held my “manhood,” laughed, and said “this is a waste.” He then grabbed the lube, put a condom on, and pulled the plug out of me. He slid his cock slowly into me and began to pound.

I moaned in ecstasy, and I could hear him laugh with every moan I let out. It was heaven. He pounded for a while, getting faster over time. I was in heaven. I began to touch my chastity cage and he saw. He slapped me in the face from behind, stopped fucking me, and said, “NO! You don’t get to use this! If you want to cum, it will be from me fucking you! Understand??” The slap made my ass tighten around his cock. Again I seemed to enjoy it more than I didn’t. What was I going to do? Argue with him? I said, “Yes Daddy.”

He then began to fuck me again, and I focused on the cock going in and out of me. He grabbed my neck with both hands from behind and started to choke me. Nothing too rough, but clearly chocking me. My cock dangled in the wind, his balls slapped my ass, his hands around my throat, and my masculinity disappearing with every pump.

I looked down and saw that I was dribbling tons of precum, a long stream ran from my cock cage to the bed underneath me.

Daddy then turned me over on my back. He saw all the precum there and just laughed and said, “I knew you’d love this.” He scooped my precum up with his fingers and put it in my mouth. He put my legs behind my head, grabbed my throat again and fucked me into oblivion. I felt myself cum, but never let out a full r/cumfromanal explosion, but I knew I was cumming.

He pumped hard, fast, and unforgivingly. He ripped the condom off and came all over my chastity cage.

It was complete. I was a sissy bitch boy and I loved every single second of it. From the moment I opened the door to the moment he came on my caged little clitty, I loved it.

We cleaned up, I walked him to the door, he slapped my ass again, and walked out never to be seen again.

From then on, I found myself craving to be used and humiliated the same way I was with this guy. It set me on a path of cock lust forever.

__

I hope you enjoyed reading, I know it was kinda long. I got kind of carried away with excitement as I recalled this memory and didn’t want to leave anything out because this story turns me on so much every time I think about it.

Source: reddit.com/r/gonewildstories/comments/9yvfpy/first_time_crossdressing_for_a_man_tm