[Group] The Trans Girl, the Lesbian, and the ‘Virgin’ (part 1)

So a user asked for more on this from an ask reddit after dark comment I made, so here’s a first story. (Mobile writen)

 
My first year away from home as a college freshman didn’t work out so well. I had some fun, met some cool people, but ended up back home a year later with little to show but some core credits. Never hit it off with any girls at any parties, never even came close… Well this one time but that lead to an emotional burn so we repress that. But in case you’re wondering, im a pretty average guy i’d say. 6’1″ with a bit of meat on me, feathered brown cut on my head, and average below the belt.

 
Anyways, fast forward a few months. I’ve been slumming around dating sites for a while now and I meet this cute looking girl. 
She’s 6’2″, broad in the shoulders with a solid C set of tits. Cute dyed pixie cut with the whole neko cat ears. Small and cut, heavy into BDSM and a total pet (‘pet’ for later). 
So we chat and long of it she’s been transition for the last 2 years. We hit it off pretty well, hang out a day here, get a blowjob there, you know, the college kid stuff.

[MM] Having My First Hand-Free Orgasm in the Sluttiest Sex Ever

*This story just happened recently. I already made a [post](https://www.reddit.com/r/askgaybros/comments/7qnssu/annoucement_just_had_my_first_time_handfree/) on it in another sub. All the details in this story is written as correct as possible from my memory and with the help of Josh*

Thanks to Mather Luther King Jr. Day, every school had a day off on Monday and every student had a three-day weekend to enjoy themselves. My buddy Josh and I decided that we would go to Florida to enjoy some tropical sun and beaches and stay away from the cold winter in our town. For those who don’t know, Josh was my best friend since our childhood and then we processed to be also fuckbuddies (our detailed relationship can be found [here](https://www.reddit.com/r/gaystoriesgonewild/comments/7q4amn/josh_part_1/) and [here](https://www.reddit.com/r/gaystoriesgonewild/comments/7q81m1/josh_part_2/)). Anyway, Florida was great. The weather was awesome. Girls were hot, and guys were even hotter. And our sex was still incredible.

[mmf] Got first ever blowjobs from a couple I met on Craigslist

Story time! Throwaway account of course.

In high school and college I was awkward, overweight, self conscious, and watched too much porn. This led me to going though college without as much as getting my dick touched.

After college I move to a new city where I don’t know anyone. Just for shits and giggles I start making ads on casual encounters just to see what comes through. M4F ads don’t really yield much since there are so many guys and so few girls, so I start making M4MF ads. I’m not gay, and don’t think I’m bi, but I am a post college virgin and open to new experiences so why not?

One night I made an ad posting as a submissive bi guy looking for a couple to play with. I got a response from a woman who sent a picture of herself. She was older than me (mid 30’s maybe), blonde, big boobs, and she said she was looking for a guy for her and her husband to play with. We exchange phone numbers and test a couple times and she sends me her address.

Diary of a Call Boy, Entry 1 & 2 [MMF][bi][rape]

Entry 1 – The Rules!
Follow these or pay the price:
-Keep your business and personal life separate.

-Everyone pays. No exceptions.

-Safe sex is more than a condom.

-Play to the clients fantasy, but NO is OK.

-Have an exit plan!

Good Luck!

Hale

Entry 2 – Where to Begin?

I was told it would be good for me to write what happened to me down. I think I understand the necessity as there aren’t really a lot of people I can or even should talk to about this. Additionally I need to get some of this off my chest. So I guess here I go, though I didn’t know it at the time this is my story of how I became a Call Boy.

The beginning of going from bi-curious to cumslut [MM]

Even though I always dated women, I always wondered what it would be like to suck a cock. I always rotated in bi, gay, and trans porn, and loved watching someone work a nice cock and get rewarded with hot, delicious cum. However, given my relationship status, I didn’t have a chance to experiment with it until my mid-20s.

Now that I was finally single, I knew it was time to try some new things. I went online and bought a butt plug and a suction-cup dildo. I also started watching sissy hypno videos, and even though the whole lifestyle didn’t resonate with me. The passion for cock was growing rapidly.

The morning I decided I could no longer put off the thirst, I had woken up and immediately started lubing up my plug. It didn’t take long before I rolled out of bed and slid on to my dildo. I loved the way it filled me up and the way those seven inches would stretch me out. As I was grinding on it, and looking over my shoulder at the mirror so I could see it slide in and out of my thick ass, and I couldn’t resist anymore.

Josh [MM] [Best friend]

**This is a long post, but I don’t feel comfortable cut short the details as I feel that if I decide to tell this story, I need to tell you guys as detailed as possible**

I was a victim of bully. You know the typical skinny shy nerd who has no taste in clothes and always carry a thick book around? I was once that kid. And everything started to change when I get into high school.

My family moved to a new house the summer before freshman year started, and my best friend Josh was also living there. Some background information about us. So Josh and I have been best friends for like forever. Our families were very close to each other when we were small as his parents worked with mine. For years of our childhood, we were inseparable. But then when we started middle school, due to family business, both families moved to different places. We didn’t see each other for years, but we still kept in touch frequently, and despite the distance, our friendship never seemed to get cold.

[MF] backseat drivers (contains consensual spanking)

**TLDR:** I’ve spanked seven different women in the backseats of five different vehicles over the past 23 years.

+++++

**Mazda 626**

The first time I gave a backseat spanking, it was in my Mazda 626. My girlfriend and I had already experimented with spanking, but when you’re in high school, you have to make do with what you can. I distinctly remember parking at a park near her house and turning her backside bright-red. I won’t go into detail beyond that because of our ages, but it did happen more than once.

+++++

**Toyota Prius 2G**

You’d be surprised how much room there is in the back of a second-generation Prius — you know, after they stopped looking like Tercels but before the taillights started looking ridiculous.

[MMF] My ass is no longer a virgin.

*I’ve posted quite a bit on the Chastity subreddit and just the other day I came across this sub and I figured my story was worth sharing here.*

I’m a male who’s kept in chastity 24/7. If you’re not familiar with the practice this goes a long way towards explaining it:

*(edited slightly from Wikipedia) Chastity belts may be used as part of a practice of orgasm control, to prevent the wearer from engaging principally in sexual intercourse without the permission of the dominant, who acts as “keyholder”. A chastity belt will also prevent other sexual activity such as masturbation and oral sex involving the wearer’s genitals.*

*The putting on of a chastity belt, by a partner, is an indication of the dominance by the “keyholder” over the wearer’s sexual activities. By accepting the chastity belt the wearer accepts surrender of control over their sexual behavior to a partner, who may grant permission to the wearer to engage in sexual activity by removing the belt. The dominant may decide when, where, how, how often, and even if, the submissive is allowed sexual release.*

It’s pronounced boo-car-kay, actually. [fmmmmmmmmm][buk]

I just couldn’t help myself. I know it’s lame, and I know it’s a stupid thing to be pedantic about, but for some reason, it just really grinds me. It’s like, I have this friend on Facebook who goes completely mental when someone mistypes “there” or “their” or “they’re”, and I had a boyfriend once who would get red-faced over the “10 items or less” signs at the supermarket.

I’m not that weird, is all I’m saying. Not really.

I was standing behind another customer, in the dimly lit basement of _Dirty Dreams_ and I was half-listening to him. “Do you have, uh, any of that Japanese stuff? You know with the girl and all the guys?” He looked more or less like you’d expect. Big sweaty guy whose ass-crack was winking nauseatingly at me from the too-tight waist of his pants.

“Bukkake?” asked the clerk.

I couldn’t help it. I cleared my throat, “Actually,” I said, “it’s pronounced boo-car-kay”. The guy swivelled to look at me. He inspected me like I’d shown up at his doorstep trying to sell him religion.

He snorted, “‘Boo-car-kay’, huh? And you’re some kind of – ” he waved his hand dismissively – “expert?”

Bi-Curious playdate [MM][First person]

I’m a pretty straight guy living in a strong long term MF relationship. But I’m also bi-curious, and have permission to occasionally play with others via contact made thru Gaydar and similar sites.

What follows in this post is a fictional story I’ve written and am sending to a bi-curious guy who I found through gaydar and who I hope to meet soon. I split into “chapters” for easier chunks to send him via kik.

For extra context: I don’t have much bi/gay experience, but it seems I have more than him. I’m adept at anal play; and he has never played down there. He seems interested in me guiding him along.

I hope someone enjoys ……

Chapter 1 – Hello There

I check into the hotel room first and send you a message with the room number. You leave your car and come to the door, which I’ve left open.

Inside the room, it’s awkward. We’re both shy and unsure what to do. I suggest that we undress and take a shower together.

You think that’s a good idea, so we take turns taking the other’s clothes off, one item at a time. We’re both feeling very self conscious and embarrassed.