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.

Sex with a man

I had always been curious about having sex with a man but had been in a long term relationship. One day I found out about gay saunas and just wanted to give it a go before I got married.

I was so nervous before going there my heart was pounding! I paid my entry went to the changing room, took my clothes off and wrapped the tiny towel around me.

Entering the different rooms I settled on the sauna room, took my towel off and sat down. It was so arousing seeing other men staring at my cock, I was close to getting an erection all the time. I carried on having a look around, I stumbled upon an area where there were loud moans and the smell of sex in the air. I couldn’t hold my erection and longer and became so hard.

I settled in a room where porn was being shown, I took my cock out and began stroking it. A man the joined me got on his hands an knees and crawled between my legs. I was so nervous, he took my cock so deep down his throat, much further than my wife has ever done, it felt amazing! I was about to cum when he stopped and said to follow him.

I [F] posted a request for a guy [M] to meet me and eat me

I was coming out of a marriage gone wrong, didn’t fancy the husband any more and so he was telling me that I didn’t like sex, but really I didn’t like him, he’d get drunk and be obnoxious and put me down, sulk about sex, that’s not sexy. So I was reading a lot of the casual encounters on Craigslist and getting turned on by them, the gay ones mainly as they were so hot! I went through a phase of giving away pussy shots to anyone who requested , plus videos of me and a vibe, I was enjoying the attention and emails. One day I decided to ask for a licker to just, well, lick me. I had a few replies …. :) I suggested that they get a room in the nearby travelodge. Ex was still living at the house. I arranged a meeting and turned up in a dress and no underwear. The first guy was really nervous (so was I to be honest ) and when I got into the room I just laid on the bed and pulled up my dress and nodded “do it”. He went to the foot of the bed and started to lick. I just laid back and enjoyed, not having to do anything to him or to give anything g back was totally liberating. I came at least twice this time and then left him in the room. We met up again for more of the same, that time we had sex with a condom and I wanted to be entered. I arranged another meeting with a different guy, he was intensely into licking and this lasted hours, 3 cums that time . Since then I haven’t advertised but I use the memory and thought of asking for. Someone to come over and just eat me makes me cum hard when I get that vibrator out. I was coming out of a marriage gone wrong, didn’t fancy the husband any more and so he was telling me that I didn’t like sex, but really I didn’t like him, he’d get drunk and be obnoxious and put me down, sulk about sex, that’s not sexy.
So I was reading a lot of the casual encounters on Craigslist and getting turned on by them, the gay ones mainly as they were so hot! I went through a phase of giving away pussy shots to anyone who requested , plus videos of me and a vibe, I was enjoying the attention and emails.
One day I decided to ask for a licker to just, well, lick me.
I had a few replies …. :)

[M]y first submission to a [F]emale happened at Burning Man

y first experience submitting to a female dominant makes a good first story. It happened at Burning Man several years ago. I was riding an art car, this one was a large bus with one of the long sides completely removed so people could hop on. All the seats were removed and replaced with pillows and blankets.

I saw one girl being … admired .. by two guys. It looked like a couple amateurs trying to submit to a seasoned femdom. Granted, I didn’t have much experience with male submission to compete with them, but by this point had plenty of experience in BDSM and Dom/sub activities in the reverse role (it had simply been much easier to find partners or girlfriends that wanted to submit).

I made my way to her, and made some confident sounding soundbite — I don’t remember exactly what I said but the gist was I thought I knew I could outperform the current guys. She suggested I try worshipping her, starting at her feet, and within a couple minutes she dismissed the other two guys.

Answered a craigslist ad from a guy willing to suck off straight guys, got more than I bargained for [MM]

*NOTE: I posted this story once before years ago on a different account. But I deleted that account and have since made a new one. I want to tell this and a few other stories and figure I should do it all from one account.*

I should preface this story by saying that I am straight, generally, and had never been with a guy before this story. This was a few years ago, when I was 24, living in New York City and dating a girl long-distance.

My girlfriend and I had been together for a few years, since college, but an amazing opportunity took her to another city for two years. I found myself on the Greyhound a lot and, when I wasn’t with her, often sexually frustrated–especially as I saw all my friends living it up as single guys in their twenties in NYC.

The Submissive Professor (19)

As I expected, Mistress Michelle cums several times while I ate her pussy. I deeply love to eat her pussy. It is a real reward for me and Mistress knows it. Sometimes, between classes, she returns to her apartment, to be worshiped with a quick cunnilingus by her submissive slave. Then she leaves, calm, leaving me in a state of indescribable excitement.

[MM] Sharing a Hotel Room with my Boss, part 2

**Part 1:** https://www.reddit.com/r/gonewildstories/comments/9v5l4s/mm_sharing_a_hotel_room_with_my_boss_part_1/

When I woke up I felt a familiar feeling of comfort and safety. I was unsure of what it was at first but I quickly realised it was Alex’s arms around my waist and his body pressed up against me from behind. Somehow in the night I rolled over away from him and we must have met in the middle and begun spooning. My instincts told me to immediately move away but I couldn’t help but enjoy this feeling for just a few more seconds. Alex’s strong arms were around my waist and his hands were resting on my stomach. I could feel his muscular chest against my back and his face close to the back of my head. I also felt, to my surprise, something poking my in the backside which I then realised was a bulge in Alex’s underwear. What made me eventually extricate myself was the realisation that I had a bulge in my underwear to match. I moved away from him and sat up on the edge of the bed, a movement which caused Alex to be slowly roused from his sleep.

The Morning[M][M][M][oral][gay]

My head felt heavy. A thick fog filled my skull. I tried to open my eyes and the fog spilled out over my vision. I blinked a few times and reached up to rub my head. I felt dizzy, the memories of the night flooding back to me. I remembered going out with the guys, I remembered tequila, and that was all I could wrap my head around.

I blinked one more time and looked up at the ceiling. It took me a few foggy seconds to realize that the white popcorn ceiling above me wasn’t my own. I looked a little around the room. The grey walls, the pale beige curtains, the dark wooden desk in the corner beside the bed. None of it was mine. It was in this moment that I looked down. I hadn’t felt the sucking before then, my mind was reeling and I finally realized what was happening. I looked down my bare chest and saw that I wasn’t alone.

[MM] Sharing a Hotel Room with my Boss, part 1

I couldn’t believe my bad luck. First I was being forced to fly halfway across the country for a work seminar, and then, due to a problem with the hotel, I was forced to share a hotel room with my boss, Alex. It’s not that I didn’t like the guy, its just that we weren’t close or even acquainted by any stretch of the definition, and I didn’t feel too comfortable sharing a bedroom with him for 3 days. At least I was able to take some solace in the fact that the room had separate beds. It’s the little things, you know?

When we got to the hotel it was already almost evening. I popped into the shower quick to wash the smell of airplane off of myself and when I emerged I saw Alex unpacking his luggage into the little dresser that they have in hotel rooms like this. I never saw the point in doing such a thing, I was fine just keeping my clothes in my suitcase. For someone who works in an office, Alex was a large man. He was muscular and worked out regularly. I, on the other hand, was quite slim. I did some biking here and there so I wasn’t completely soft, but I wouldn’t call myself fit either.
“Some day huh?” I sighed. “This trip is off to a great start.”

Soul Binder – Chapter II [Gay] [MM] [Urban Fantasy] [Horror]

**Chapter II**

We made good time getting home, despite the car accident and traffic jam that forced us to wait for almost thirty minutes. But I didn’t mind. Idle time meant busy hands, and boy, were our hands busy. We pretty much fondled each other all the way home; his hand in my pants and mine in his. Tinted windows hid so many things, just like dark shadows and I could never get enough of John’s rough hands on my skin. I would drink that sensation every time it became available.

We pulled into the garage around 5:00 pm and with a single press of a button, the large doors closed behind us. The garage was triple wide, though the BMW and Spider ate up the other two spots. And don’t get me started on the attached two-story house that was pretty much a mansion nestled in the woods, at the end of a long, private driveway. It was insanely beautiful and spacious. The perfect place to feed, store hosts, and grow.

“You hungry?” said John.

“Always!” I responded.

We walked inside via the adjacent doorway, and I planted myself down on one of the kitchen chairs.