gonewildstories Archives — Page 2123 of 5640 — NSFW story

[M] My first sissy blowjob ?

Soo I was 24 last year when I did this… still my only crossdressing experience pleasing another man.

My girlfriend was out for the night having drinks with friends, so I took the opportunity to get dressed up in her black lace bodysuit, and put on some red lipstick, mascara, and blush with glittery eyeshadow. I loved the risk because I didn’t know when she’d be coming back.

Anyway, I’m watching sissy hypnos and edging whilst talking dirty to guys on grindr and kik which I usually do secretly when I’m really feeling like a sissy. One guy pops up with a cock pic demanding a facepic from me. Now I never usually do this due to risk but because I was so fucking horny I sent him some pics pouting and winking and stuff.

He messages back saying I’m sexy and he wants to come through to me, he’s a half hour drive away. I bite my lip while I’m playing with my clitty and say OK.

He dawdled and actually took an hour to come through, which got me so fuckin nervous my gf would walk in. I left the door unlocked and sat in my front room, heart beating out of my chest. I text him saying to just let himself in and lock the door behind him. Read more »

[MF] Three Months Of Delivering Food For Extra Money Has Some Unexpected Perks

As a dude in his 20s trying to make it out in Los Angeles, I needed to take on an extra gig. Maybe “needed” is the wrong word. It wasn’t like I either delivery food or set up camp on the side of the street. More like, “Wow, I’m tired of having no money after paying all the bills.”

So around three months ago, I signed up for a delivery service. The process was rather easy. They even sent me a nice little bag and card a few days later. I was told doing food delivery in LA is difficult with only one person because you’re always looking for parking. I tested it out, and yeah, during the rush times? Fucking sucks. Would not recommend. But if you take the night shift? It’s really not so bad. You may not make as much, ah what the fuck, you don’t care about this shit.

Point is, I’ve been delivering food at night, and for the most part it’s been uneventful. I had been dropping most items off at the door, so I barely had to interact with anyone, which was cool with me. Here lately though, people have been more willing to accept the food, so I’ve had some strange interactions. Read more »

12 Orgasms altogether and I got 10 of them [MFF]

After my last breakup, I decided to finally fulfill my goal of being a unicorn for a couple. I had participated in some threesomes years previously with my ex-husband, but those ended badly and, to be honest, was not the girl I would have chosen to lose my bisexual virginity with. This was a new mission to undo what a threesome was in my head as well as get spoiled by a hot couple and spice up their relationship.

Enter Eric and Britta. He managed the Tinder account that I matched with. He said that they both found me attractive and after a pretty dry conversation, we met up at a bar near their house when I got off work. But this story isn’t about that first time. I don’t remember enough of the gritty details to keep you entertained for that time. Or the next time. This is the third time that we met up. The memories are fresh, my sheets still smell like sex, and I finally have a good story to share with my favorite subreddit. Read more »

Last night my partner [NB] discovered I [TM] have a thing for them in a skirt.

It’s been a couple months now of seeing my current partner, A. Neither of us is sure exactly what we’re doing at this point, but we’re both enjoying it immensely. There was some pretty immediate chemistry between us, but I don’t think either of us expected this.

On our first date we ended up making out on their couch with me sitting in their lap, grinding on them through their jeans while we kissed. It wasn’t until later that they told me that isn’t the norm for them. Funny thing is, it’s not the norm for me, either. It took about four or five incredibly hot fucks over three weeks or so before either of us brought it up, and then we both ended up laughing about it on their bathroom floor, until we remembered we’d been in the middle of showering together and got back to soaping each other up. Read more »

I [F] left something behind on my chair at a fancy restaurant

I’m not the most adventurous person, but one of the embarrassing naughty stories I’ll never forget is when a cute guy offered to take me out to dinner while I was visiting Italy. I gave him my number and he told me about a restaurant that I’d never heard.

Back at the hotel, I could tell from a quick google search that the restaurant was expensive: the way the tables were set with too much cutlery for it to be an average joint.

I thought carefully about my outfit, and settled on a black silk dress that just about covered my bum.

During our date, the guy was charismatic and asked lots of questions, but I wasn’t sure if he was interested, he seemed a little distant overall. After dinner, I offered to pay half of the bill, as I always do (so long as the guy hasn’t been a total knob!). But my date surprised me that night – he was so smooth, before I had finished getting my purse from my handbag, he told me nonchalantly that it was already taken care of. The owner of the restaurant must have been a good friend of his, or maybe he took care of the bill while I was in the bathroom fixing my hair… Either way, it was incredibly sexy. I felt my face hotting up, and I remember realising that my father must be able to see me blushing. I looked away to hide my face a little, and he softly brushed my hair behind my ear so he could see my face and he smiled. Read more »

Dressing room romp [FM]

It was a beautiful warm spring day the other day when Tiff called me up wanting to hit the mall for a bit of shopping and flirting. I put on sundress but no panties or bra. I decided to put in a sparkly plug that contrasted well with the dress. The dress was short enough that it provided just a glimpse of my pussy mound and little sparkle of the plug if I bent over far enough. Tiff decided to wear a similar outfit.

We got to the mall and it was fairly crowded. Before we started shopping for clothes we went shopping for any man/men that we could attract. Our plan was to look for any good looking guys standing around and as one of us would stand back and observe the other would go close to the guys and bend over and or adjust our dress top to see what kind of attention we could draw. Read more »

[MF] Well, THAT was fucking quick!

One night I caught a girl’s eyes at a local bar. The atmosphere was chill. The TV’s featured silent sports as pop/rock music played through the speakers. Sporadically, when she liked a song, she would dance in front of and brush up against me as I sat in my chair. Over the course of a couple drinks, we didn’t have a proper conversation – more like flirty interactions as she migrated between her friends and me. Her mischievous grin turned me on to no end. More than once, just as I thought I could command her attention, she would turn back to her friends. During one of our “moments” I invited her to my place, albeit almost jokingly. To my surprise, she accepted.

When we walked in everything was fun and hot as we made out, stripped, felt each other up and worked our way to my bed. I grabbed a condom and entered her in missionary. She was very wet, and I slipped out before I could find a rhythm. Read more »

[F] Putting my frenemy [F] on the hot seat

My frenemy and I both live in a large city in North America but we are both from originally from the middle east and come from conservative families. She is 26 and and I am 25. I say frenemy because even though she considers me her friend and we hang out a lot together, I don’t really consider her my friend. The reason is that in college, she betrayed me by cheating on me with my bf at the time. I found out accidentally because we both dated in “secret” since our families are conservative, I never told anyone about it. She does not know to this day that I know what she did.

Fast forward to about two years ago. I made a bet with her (on a hockey game) and the loser of the bet would have to give a semi-nude picture to the winner which they could use however they wanted. We both agreed to this and took the pictures in advance to make sure no one backed down. I ended up winning but decided to just keep the picture with me for now (even though she is dying to know what I plan to do with it). Read more »

[18][f] Warning to all wives: “I’ll steal your husband and your money”

The other day I hooked up with a married man? and tbe wife had no clue

This is a fair and honest warning… If you have a husband that is on reddit get him off, because you will have a lot less spending money. Also a lot less sex. Your husband will see there are much younger hotter girls, that would love his dick. Husbands love to talk shit about their wives with me, and I would be lying if I said I didn’t love it also.

[Homewrecker](https://i.imgur.com/kVGgTrf.jpg)