Category: gonewildstories

New Years Eve and a lot of first for this [T]ransgender girl with [MF]

This year on New Years Eve I decided to go to the same place I have gone the past several years but this was the first year I went as myself since I transitioned. The theme this year was ABC which stands for anything but clothing. When I first heard this I thought it meant naked but its apparently wearing things that aren’t consider clothing. I instantly new what I was going to show up wearing when I found out the theme back in September. It was also to be a competition for the best male and female outfit.

I decided to let my inner kink flag fly and tied myself up in a rope bra which hardly covered my whole nipples and a corset that turned into more of dress that went just a couple inches under my ass. BTW for those curious I am about 5ft7 and pretty fit with a nice bubbly ass and am either a big 34A or small 34B in the breast department. It took me nearly 3 hours to get myself tied up in my out fit and about 400ft of rope which was a light gold color. Read more »

[FM] Showing up in nothing but a zip up hoodie, leggings, and a plug in my ass [Pt 2]

Part 1: https://www.reddit.com/r/gonewildstories/comments/7r28fg/fm_showing_up_in_nothing_but_a_zip_up_hoodie/?st=JCKT0LZE&sh=5f9cbe51

I took Jack’s thick, heavy cock in my hand and slowly started teasing him. Licking up his shaft, slowly sucking the tip, and gently caressing his balls before I suddenly took as much of his cock down my throat as I could. Even with the head hitting the back of my throat, I couldn’t take all of him.

Jack leaned back and groaned as I licked and sucked his cock. “Fuck, you’re a good little cocksucker,” he panted. I moaned around his cock, focusing on teasing the underside of his head and coating his entire cock in salvia, preparing it so he could easily slip into my tight, dripping pussy. I forced his cock deeper, gagging on him.

Finally, I got up off my knees and straddled him. Guiding his huge cock, I slowly sunk onto him. I gasped as he stretched me, feeling every inch of him splitting me open. His cock was so big that it pushed the plug out of my ass. I was too desperate for him to stop and put it back in. Read more »

Brittany fucked in the library (pics) [MF]

So Brittany and I are adventurous, and she likes when I take control. One day last semester, I told her to meet me at the library at 9 wearing a skirt with no panties.

I went to the library at 8 to actually do homework, but I had a very hard time focusing. When Brittany arrived at the library, she texted me asking where I was. I made her send me an upskirt pic in exchange for my location. My dick was throbbing through my jeans before she found me.

Brittany found me at a desk that was fairly isolated, but still had people around. I immediately made her sit in my chair as I knelt under the desk and ate her out under her skirt. After a few minutes, she covered her mouth with her hand as her thighs started shaking and she came on my mouth. We briefly switched so she could blow me, but pants get in the way more than a skirt, so we agreed to just find somewhere to fuck our brains out. Read more »

Revenge fuck [MF]

Years ago, I was dating this guy on and off for a while. He traveled a lot and wouldn’t commit to me. I’d go out on other dates, but never did much. He was fine with the dating as we weren’t together. I would send him pics of me on the date to get his jealous and draw him home. He enjoyed that. He knew all my friends and I all his, like I said..we dated for a long while. He hated one of my friends. A guy he used to play hockey with and the guy was a bit of a douche. This guy, James, was really hot, talk dark and handsome, with chiseled muscles. I don’t blame him for hating this guy, but he was always nice to me.

One morning I woke up and was looking at instagram and there were pics of my guy partying out of town with all these girls. Getting too close. After some sleuthing I found a pic of them kissing on her account. Him and I talked about it during the day, but I was mad. I needed to go out for a drink. I threw on jeans and a tight shirt and my bestfriend and I went to a local pub. I’m 5’3″ with 34DD. Pics in account. I just wanted to get drunk. We succeeded. There were lots of people we knew there. We didn’t talk to many. We were on a mission. I wanted to drown my thoughts, but instead I got more mad. Read more »

[MF] A couple of old friends… Part II [Kink]

Anyone interested in part one [can find it here](https://www.reddit.com/r/gonewildstories/comments/7qvtf3/mf_two_old_friends_in_a_public_park_kink/)

A couple of days later, and I hadn’t really gotten that night out of my head. She was texting me non-stop about how much she had liked it, so I decided to push things even more.

I texted her to come over, and as soon as she stepped inside the house, I stopped her in the mudroom. This front room was mostly just used for taking shoes off or putting them back on again. It had huge windows on all sides that looked out to the street and the neighbors. Anyone walking by, or any neighbor who glanced out the window, would be able to see right in.

I told her to strip down to her bra and panties right there. As she took off her jeans, I noticed she was wearing panties that completely covered her wide ass. Wanting to escalate the humiliation, I made fun of her for it, and told her next time she better wear a thong if she wanted to be a slut for me. Read more »

[MF] Virgin at 34 no more

I decided to write this up because the pinned one in r/virginityexchange made me push myself out of my comfort zone. I like to hit reddit random and I found the subreddit by accident. Really told me I wasn’t alone. I read a bunch of posts and posted a few myself but deleted them due to using the account to contact folks and didn’t want the ‘secret’ out. I am one of the most awkward people you’ve ever met and probably somewhere on the spectrum but was born 10 years too early to get any real help when it could have helped. Follow this up with some terrible sex ed I was terrified of sex and was told no sex before marriage and all that jazz when you have a conservative school board. College was confusing and I missed several opportunities. Now a decade out of college I feel gross and alone and literally given up the last few years. Cried myself to sleep on NYE with the promise I needed to make a better effort in 2018. Well 16 days in was well before I thought possible and I still have some dates this week. One simple rule to follow too; make HER say no. I am so worried about the rejection I refuse to put myself in danger. Well my back is sore two days later. Read more »

Sexy [F]un with [M]y ex at a tourist attraction

Just like most of the posts, I’m a long time lurker and finally decided to write a post. This story is about my time with my ex at one of the biggest tourist attractions in Singapore.

Description: I am a tall, brow skin guy. 6 foot tall and pretty lanky. Short spiky hair that’s normally gelled up.
Sally on the other hand was a bombshell. She had long brown hair and hazel coloured eyes. About 5″2 her best feature had to be her round 18 year old boobs that fit perfectly in my hands. She had a petite ass to compliment her figure but it was always second to her perfect tits.

This was one of our usual dates and we were talking a long walk by the river after visiting the 2 domes of Gardens By the Bay. One of Singapore’s most prominent tourist attractions. It was a cool night and it was about 1030pm. By this point most people had left the place and there were just a couple of cyclists crusing down the roads. Read more »

Pledging a Prestigious College Fraternity with the Help of a Sexy Crossdresser [MT]

I grew up in a small college city. A prestigious private university, a well-regarded state university, two small liberal arts colleges and a community college made for a very interesting environment.

Following high school I ended up attending that private university. After settling into classes, my friends and I began to attend some of the rush events hosted by fraternities tied to the different schools. The fraternities weren’t located on campus or on a fraternity row of any kind. They were located around town in areas largely populated by off-campus student housing.

It would have been absurd for me to actually pledge a frat. All locals were trained to dislike “frat boys” beginning at an early age. Joining a frat was unthinkable, but their beer was cold and free.

The parties were a lot of fun. Each frat house had its own character – and gang of characters that lived in them. My far the most prestigious frat in town was Delta Tau Omega (DTO) largely due to its beautiful building. The DTO structure was like a palace which had been sculpted out of marble – an edifice which had been requisitioned by a railroad executive in the late 1880s. Read more »

[MF] My South Asian adventure with a native escort.

I am a 24 year old enjoying vacation in Srilanka. I always had a sexual fantasy to have a safe sex adventure with a native woman. I posted here asking for advice and was told to hire a tuk tuk (a three wheeled taxi), so I asked a few people.

One driver said he knew some ‘new ones’ so I took a ride with him. He called someone while driving, and after a while we stopped at a small town. Driver waved to someone outside; a young woman waiting near a supermarket saw us and get into the tuk tuk. We said Hi to each other and shook hands.

She was a super shy and anxious girl in her mid twenties; a brunette with nice firm young breasts, full firm ass, with a great complexion. She was nervous as fuck and I could tell. We rode back to my hotel. I tipped 1000 rupees to the driver and we went inside and straight to my room. Read more »

[MF] new experiences

My (22f) girlfriend and I (21m) recently bought a butt plug. I’ve been itching for her to try it since we got it, as we’ve discussed and attempted anal play for quite some time as I’ve had a fantasy of taking her vaginally/anally while the other is occupied by a toy, which usually didn’t get too far. Cue last night, sexy times start, I start teasing her by kissing up and down her body as she slowly sheds layers of clothing. She absolutely loves when I eat her out, so I danced around it for effect. Right before I start I tape her hands above her head, then proceeded to eat like my last meal. We remove the tape eventually and I try to rim her but ” It tickles too much.”. We spend some time piv, as the new toy gets pulled out along with of course an ample supply of lube. She lubes up enthusiastically and then much to my surprise (as she struggled to this put to accept my average at best dick) takes the better part of the plug which was the 2nd size in the “beginner’s section”. Then she looks me in the eye and tell me she wants me inside. So of course I oblige while grinning ear to fucking ear. After I slip on a new cockring we transition to my favorite position which is doggy. And fuck me if it’s not the best sex we’ve had in quite some time. We tried for full on anal and she accommodated more than half of me before we agreed to come back to it at a later time. But in the mean time I’ve still got a raging hard on that needs to be dealt with, so back to fucking we go. Since we both like it rough I’m just pounding her sweet little pussy while her hair is wrapped up in my hand so she has no choice but to look me in the eyes, I lean in a growl into her ear as I finish.