Category: gonewildstories

My secret fantasy comes true [TM]

So I’m a normal guy that lives a normal life at least on the surface. I have a girlfriend and to everyone that I know I am a regular guy. But in the last year I have seen a few things that have sparked my curiosity to completely new levels. When I’m alone I have been experimenting with cross dressing, it started when I stole my girlfriends panties one day and it has snowballed from there.

So now I have a few female outfits that I bought online and I have been watching a lot of cross dresser/sissy porn. And I’m thinking more and more about it and getting more curious all the time. I have been chatting with some guys I met on Reddit that are into cross dressers/sissies and it’s normally nothing more than just fantasising and chatting.

But recently I got chatting with a guy who happened to live close to me and we really hit it off, sexting and getting really kinky with each other. So we have been talking about meeting up and he says he’s going to make me his little sissy and I call him daddy and everything lol. So today while my girlfriend was at work i got a sudden burst of courage and invited him over. He immediately agreed and straight away he was on his way over to mine. Read more »

Landlord Confessions: Student breaks washer and blows me for forgiveness [MF]

The usual boring background bit first: I’m a landlord who owns multiple properties all rented out as student accommodation for the local university. And it’s the fucking best. I have to deal with a lot of shit but on the bright side I’m a 37 year old guy who gets to spend his days surrounded by young hot students who are often grateful when I help fix their problems…

Vanessa is a 20 year old student with the most severe case of resting bitch face I’ve ever seen. But looking pissed off all the time doesn’t change the fact that she is sexy as fuck. A brunette with ringlet hair, blue eyes and always in makeup which is done perfectly. Best of all is her incredible chest. Big doesn’t come close. E’s minimum. Even just her walk is enough to get them bouncing and she’s always wearing something that shows them off.

So when I got a call from Vanessa telling me to come round urgently to help fix the broken washing machine I wasn’t as annoyed as I might have been by yet another fucking broken appliance. Read more »

[FMM] BF and I Invite a Stranger Into Our Hotel Room For Our First MMF

*Disclaimer* This story involves F on M and M on M action.

If you want to skip to the sexy bits, scroll down to the ******.

Pre-COVID, my boyfriend Roy won a company raffle (he’s in sales) for an all-expense paid trip to Vegas, where we would stay for an entire week at a very well-known resort on the strip. As soon as we arrived in our room, our clothes were on the floor and my legs were split open on the king size bed while Roy bottomed out inside of me. Roy and I have always had a wonderful time together, but there was something we had both wanted to try—sharing each other. We had previously confessed to each that we wanted to try threesomes with both Genders. I had had threesomes before, but Roy never had. Roy expressed more interest in an FFM, while I was more interested in an MMF. 

It was there in the resort hotel room, basking in the afterglow of our sex, that we decided this was the week that we were going to try both.  Since I would be the one fishing for the thirds, I argued that it was only fair that we try the MMF first, and Roy agreed. He got hard again while we were talking about it, and we fucked all over again, before hitting the casino and going to a show. Read more »

My (39F) new old friend (44M), now with benefits [MF]

It has been a long time since I’ve posted here on Reddit. In the past, I shared stories about my out of control libido and my struggle with lack of interpersonal connection during the pandemic. It has been a frustrating time- getting my hopes up when I meet someone, only to be disappointed and feeling stupid for getting excited in the first place.

Near the start of this year, an old friend (I’ll call him A, 44M) and I started spending more time together. We have known each other for about 20 years, somewhat peripherally, but always had good feelings towards one another. He had previously expressed interest in being more than friends, but I was hesitant. I didn’t see him that way and was afraid to start hooking up and possibly lead him on or hurt him. When we started taking the occasional masked walk together, our conversations grew deeper very quickly. We both have crazy high sex drives, and were both struggling without having safe places to explore that energy. Relating to people is hard, and trying to meet new partners and develop some intimacy during the pandemic was nearly impossible. It was nice to be able to confide in and support one another in such hard times. Read more »

How I got addicted to sucking older men’s cocks. [m]49 [f]19

I attended an all girls, Church of England High school. Because it was affiliated with the church, we would have visiting COfE priests come in to give lectures and lead assemblies. When I was 19 I returned to the school as a member of staff working in the school office and became close to one of the priests who would work there- Tim.

I absolutely *love* older men, especially if they occupy teaching, education or mentoring roles in authority- the idea of leading them astray and tempting them makes me wet; Tim was my first.
We started talking as friends when I saw him at school. He was at that time single and 30 years older than me, although he looked much younger. After a while we had a fun, casual friendship. He found my flirtation around him flattering, and he knew I fancied him. I would talk to him about his sex life (he had been married) and ask him naughty questions about his sexual history- he had a lot to learn and even at my much younger age; there was so much I wanted to teach him. Read more »

[MFF] How helping two coeds started off the best semester of my life (Part 9: The girls and I go out for drinks)

Shit, has it been a month already? ADHD is a bitch. This story is (as you might have guessed) part of a longer series.
You can find all parts [here](https://www.reddit.com/user/Bovrilandcock/comments/mng4pr/katemichele_series/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

The rain lasted for one more whole day. I studied a bit, went to the gym, met some friends and cleaned every part of my apartment that smelled like sex. And the whole time I was thinking about both of these sexy, slutty girls that made me feel like the luckiest guy in the entire town. I was aroused the whole time, and every few minutes, my mind darted back to the mental image I had of the girls. What didn‘t help were the actual images they sent me. I told them how much I love receiving nudes, and how much I like being teased, and it definitely hit a nerve with them.

The picture they sent me after getting home was only the start. It felt like I was constantly getting bombarded with pictures of Michele‘s boobs, Kate‘s ass, both girls completely naked, then Kate under the shower, Michele showing off some lingerie that barely counted as clothing, and so on and so forth. I didn‘t want to masturbate, so I could save everything for the next time I would meet them. But god damn it was hard. I was hard. But I managed to control myself. Read more »

[MFF] Getting some help to tied down a sassy little brat on a business trip

I really hate admitting to a brat that she’s right. But apparently I forgot to post this story about meeting up with her, for one of the most memorable struggles I’ve ever had. That’s what happens when nerds plan a scene and fuck.

I don’t know why the idea of the sexless nerd still exists. Because every now and then I find someone like Miss E (name changed for privacy), who wrote this on a profile about herself:

“The way I have decided to live my life is similar to the Harry Potter world. The wizarding world knows about the muggle world but only a few muggles know about the wizarding world. So Miss E is part of the wizarding world. If we meet in the muggle world, refer to me as E (I can explain it is a special nicknames for special friends) but don’t out me as a witch.”

I sent her a quick message – “I love the Muggle Clause. Which makes me have to ask – which house?”

Now, she knew on her profile there were some amazing pics of her tits and dick-sucking lips, along with a fun list of kinks that she likes to do. Instead I opened with Hogwarts. Connecting with someone mentally first leads to a lot more fun later. Read more »

I was studying for the bar exam and had a lot of built up tension [FM] [Part 6]

If you like foreplay check out:

[Part 1](https://www.reddit.com/r/gonewildstories/comments/mzxj63/i_was_studying_for_the_bar_exam_and_had_a_lot_of/)

[Part 2](https://www.reddit.com/r/gonewildstories/comments/n0fkwk/i_was_studying_for_the_bar_exam_and_had_a_lot_of/)

[Part 3](https://www.reddit.com/r/gonewildstories/comments/n0fn9g/i_was_studying_for_the_bar_exam_and_had_a_lot_of/)

[Part 4](https://www.reddit.com/r/gonewildstories/comments/n0nbwp/i_was_studying_for_the_bar_exam_and_had_a_lot_of/)

[Part 5](https://www.reddit.com/r/gonewildstories/comments/n17pw2/i_was_studying_for_the_bar_exam_and_had_a_lot_of/)

He smiled at me from above and picked me up off the floor, moving me to his bed and gently pushing me backward. Finally, he ripped off my dress which was really just bunched at the waist, and moved to put his head between my legs.

He started slowly, almost teasing me with tiny licks as he reached up to play with my breasts, moving his hand beneath my bra until I arched my back and removed it entirely. I begged him for more so he moved his hands behind my ass, pushing me towards him so he could bury his entire face in me and quicken his speed. I started moaning, rocking my hips back and forth as my hand found the back of his head to play with his hair. Finally, he slammed two fingers inside of me as he continued to lick harder. He was a magician with his tongue. Read more »

[f]55 let [m]26 watch me cum

Im a 55f and let a 26m stranger watch me cum for first time.

Hubby and I went to casino last weekend because I love to gamble and dress up sexy too! We have talked about letting someone watch us have sex or possibly do mutual masturbation (I love watching a guy stroke) but never have done anything like that. While walking around the casino i had tons of looks and several guys had enough balls to comment, I was definitely getting worked up sexually. I finally settled at a blackjack table where eventually a couple of younger guys sat down and we all played for about 30 minutes before the sexiest one and I started chatting. It was very difficult for him (or anyone else who looked at me)to keep their eyes off my tits. After being chatty and flirty for a bit I started touching his arm and leg when opportunity presented such as one of us winning or laughing, not really sexually at first then it turned into more of me rubbing his leg and eventually brushing my hand over his cock. I was so turned on and I could feel his excitement too.
I apologized for “accidentally “ touching him there and he whispered to me to please not stop. This is where I told the dealer i was going to the restroom and I immediately texted my hubby and asked if he would like me to put our fantasy into action and really do it. He was more than supportive! Read more »

A Great Payback – The Morning After [FMF]

I woke up to Allie stirring. The morning light illuminated the room through the blinds. I watched her slide out of bed and make her way to the bathroom. I peeled Matt’s arm off of me and followed her. She still was smiling as she sat naked on the toilet and peed. She got up and I took her place and peed as well. I scanned her body which had thinned out since I last saw her. After breaking away from Will, she focused on herself and got into great shape. I came up behind her and looked over he shoulder and saw our reflection in the mirror. She smiled and told me that I looked chipper. I pulled her hair back and kissed her neck. My hands moved upwards towards her breasts. She watched as I cupped her breasts and told me that they shrunk over the past few months due to working out. I laughed and told her that they were still bigger than mine. She then turned to me and told me that last night was over the top and completely unexpected and amazing. We hugged and she whispered in my ear that Matt’s cock was bigger and thicker that she had expected and then gave me a “mmm” in my ear. Read more »