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.

Selena’s Book of Shadows

*This story is a re-imagining of my already published story “Enchanted Panties”. I’m rewriting the story as a whole and creating new stories from chapters that didn’t fit the main plot line. For those of you who haven’t read Enchanted Panties, this story follow Kate who happens upon an old spell book and animates a pair of panties for some fun solo play.*

*I have other works on my Deviant Art page if you wanna check them out :).* [*https://www.deviantart.com/calx86*](https://www.deviantart.com/calx86)

The end of the day was creeping ever nearer and Kate couldn’t wait. All day she had eyed the clock on the other side of her uncle’s antique shop rolling her fingers on the side of the cash register. “5:00 pm”, it displayed seemingly teasing her as the last thirty minutes of her shift slowed to a crawl. She couldn’t complain too much since it helped pay for college and it was only for the summer after all.

The store was all but vacant, so Kate walked around to check things out. It had been a year after all since she had started and there were possibly new items she had yet seen. As she neared the back, a black Gothic antique mirror caught her eye. It was a full-length mirror nearing her height from the floor and had cobras carved into the sides.

First Threesome [MFF]

Hello ladies and gentlemen, sorry for mobile formatting and all that. This is kinda a long one (seriously its long as hell) with a fair amount of behind the scenes relationship flavor. If it’s not your thing i feel ya, you do you. Well here we go.

The set up. I’ve been with my girl, Sam, for a over 3 years now. We both are in our mid 20s. Sam gets me in ways no one else ever has and we are very much happy and in love. It’s just easy being with her. One day she told me she had a sex dream but was shy to share, which isn’t like her. Sam is usually very open with me especially about sex. After some coaxing and pleading she finally opened up it was a dream of us having a threesome. Of course inside my head was fireworks, I asked how she felt and if she enjoyed it. She did but she was was already seeing where my mind was attempting to sprint too, and told me she was wary of actually acting it out.

Flying interstate to fuck a Tinder sex goddess [FM] [part 1 – long]

So I’m writing this because a) I like reading stories here b) it’s fun to relive and c) Alice told me I should.

Who’s Alice? basically a sex maniac/goddess who has very happily decided to come into my life. Exhibitionist, wildly kinky, and appreciates a well-crafted sext, hence her wanting me to write this (when I send her the link she’ll have a lot have fun getting off to it knowing how many people are reading about the way she gets fucked). I’ll give the background on us because to me it makes things way hotter – skip down depending on your level of horniness/patience

Who am I? mid twenties, shortish brown curly hair and stubble, not a male model or anything but in pretty decent shape. Did gymnastics when I was younger so forearms also get some good feedback. People say nice things about my face sometimes. Eyelashes are apparently a highlight. I guess this is the part where I describe my cock – I honestly never felt like it was that big when I had less experience, but I’ve been told it is (and checked they weren’t stroking my ego) and more importantly been told that it FEELS big . Anyway, 6.5” long and 5.5” around, apparently the girth is where it’s at. It gets the job done and gets compliments. Personal favourites have included “that belongs in the Sears catalogue of dick”, “dick prince” (thanks Alice) and “you have a classically beautiful penis” (not a sentence I would ever have expected to hear…).

I had sex with a prostitute for the first time in the Red light district Germany, and it was surprisingly amazing! [MF]

I am writing this because I want to share my experience with you. There are not so many of these post as I searched for them. it was really stressful for me so maybe there are some others that want to do it for any reason and find this story helpful. Also, I am sharing it here as I can not share it with anybody else in real life because of Judgments.

And Also I am really shy and never done that before or even never did some one night stand. I was always with mid to long-term girlfriends. this experience for me is still unbelievable, that is so not me doing these stuff. But I wanted to experience it and I did.

I had a trip to Karlsruhe, Germany and I was staying close to the Red light district (Eros-Center) of the city just for 2 days. Before going there I had this plan to probably do it because I haven’t had sex in 2 months and I have a really high Libido. That was my first time I wanted to sleep with a prostitute. So the night I went out and Walked to the street. First round I just passed the street and I was thinking if I should do it or just get back to the Hotel. There were other guys coming and going and watching the girls together or alone, in all ages, young, old, but It was OK as everybody was there for the same reason and not awkward at all.

College JO Buds [MM] – Chapter 6

Friday came and Steve had class throughout the day while Joe and I only had a morning class. Brad, being smarter than all of us, had no classes on Friday.

Joe and I were pleasantly surprised when we got to class….a big note on the door saying class was cancelled. “Fuck yeah” we both thought as we read it.

Joe: “Back home to stroke and smoke? Brad usually goes to the gym in the mornings”

I didn’t answer, I didn’t need to; Joe knew I was down. As we drove home I could feel myself getting hard. I looked over at Joe and could see a bulge forming in his pants. I reached down and grabbed my cock through my pants.

Me: “Looks like we’re both getting excited”

Joe: “Hell yeah, bud. I need a nice stroke. I need to hear the details about Sara, too.”

I began to tell him all the details as we drove home and Joe was clearly enjoying it. I couldn’t help but notice how hard he was. Campus was only about a 5 minute drive from our apartment so we got home pretty quickly.

My 47[M] Colombian [F] sex slave, sort of.

Preamble:

I read the stories here and call BS on most of them. It seems everyone that can write is a 6 foot 2 college athlete packing a 7 inch cock or a 5’9 blond with huge tits that can deep throat with no training- and how come no-one gets shit on their dick when they try anal.

Saying that I do not expect anyone here to believe a single word of this account because, well because of the wealth involved. My Wife’s family, whom we shall form now on call THE FAMILY is richer than the Kings of Vint.

Also this is a long story with not much sex in it. Accounts of sex all end the same: get naked, have an orgasm, story ends, perhaps with a hint of more sex to come if anyone is interested. Where is the excitement?, the peeking through keyholes, the knowing someone is peeing through a keyhole at you? It’s the other stuff that goes on and around the naked bonking that make a story interesting.

Background:

[MF] “I have no gag reflex.” – Part 2

If you want to read the previous entry go here:

[MF] "I have no gag reflex", she said to me. from gonewildstories

Part 2 continues….

Last time I ended with me waking up around 4am with a cock harder than londsdaleite and a warm, wet pussy at my disposal. The night before I had met Casey, we had flirted, and she had sent me to the moon and back via the depths of her throat. She had no gag reflex and fucking my cock with her mouth was not an issue, but it was the soaking pussy presented to me now, as I spooned her and she grinded, that had my full attention.

It was still dark and I could only barely make out her shape, I had already thrown off the covers so I could access her whole body. Yes she would be considered overweight, but I’ll be damned if she wasn’t the fucking hottest thing I’d laid eyes on recently.

The Neighborhood: Part 13 [MF][Handjob][Exh][Mast][Mdom][Oral][Sex][MC][SciFi]

**Note:** This is going to be it for a little while. I’ll be on vacation for a bit, and writing trashy erotica is typically what I do in lieu of vacation, so… Anyhow, more will come, it’ll likely be a trickle, at best, through the rest of the year.

—-

**Chapter 28: Kristie Comes on Board**

Back at his office, still feeling frustrated, Colin buzzed in Natalie. She walked over and stood in front of his desk, pad and pen ready.

“None of that.” Colin said. “I want to talk about your training.”

“Um, yes, sir?” She prompted him.

“First, why don’t you take off your clothes.”

“Of course, sir.” Natalie didn’t hesitate, but she never looked thrilled about it. He would have to check her responses in the system, maybe amp up her arousal. She carefully folded her blouse, jacket, and skirt, and set them on the couch at the side of the room. She stood in front of him in some of her newer lingerie, tan thigh highs, the rest still fairly conservative—he couldn’t see if she waxed or not—but she was really emphasizing her breasts, which suited him fine. Her nipples were hard behind the lacy fabric, though he couldn’t see them. Colin wanted to tell her to start wearing something a little more revealing—he had told her to, in fact—but she was interpreting the word ‘revealing’ on her own terms.