gonewildstories Archives — Page 4951 of 5640 — NSFW story

Mutual sucking with a straight, virgin crossdresser [MT] [M29,T20]

A couple of weeks ago I was browsing a fetish social network and saw there was a new user in my area. A crossdresser calling herself Lara, 20 years old, slim, 5’9”. There were two pictures, one of her ass in a black thong, showing a nice muscular ass, not hugely feminine, but more androgynous. There was a second photo or her crotch from the front, in black satin panties with a slight bulge and just the smallest hint of her cock head. She said she had no experience with guys and was looking to try everything from kissing to anal, but lived with her parents so couldn’t host.

I messaged her right away and we began chatting. Over the course of the coming days I found she was “straight” – or as straight as you can be when she’s telling me she wants a man to fuck her in the ass while dressed in her sisters clothes. We chatted back and forth for a bit and built up a good rapport. Eventually I suggested we meet last Friday night. She was kind of cagey about meeting, but did agree that we would meet at a car park close to my home and chat, before going to my house after if she was comfortable. Read more »

First Threesome with [M]y Boyfriend [MMF]

My boyfriend (25) and I (27) have been together for just over 3 years, and the whole time one of our biggest fantasies had always been to share a female partner. A few weeks ago, we finally decided to give in and gave the ol’ Craigslist a try. After a few dead ends we were contacted by a stunning 34 year old woman with short blonde hair, and a gorgeous petite body. After just a couple of short conversations, we agreed to meet and did so the very next day.

When she arrived, she came in, we got the pleasantries out of the way, and then almost immediately began making out. I’ve got my eyes closed, but we’re both kissing and touching her all over and pulling up her dress. In practically no time, I suddenly realize her dress is all the way up, and I’m rubbing her pussy throgh her panties. It was almost as though I had been hypnotized. Her panties were already completely soaked, and of course getting wetter. Read more »

Three days later, and my FWB[M] still has me[F] smiling.

After a few weeks of a change in our work loads and schedules, and then I was traveling on the west coast, it had been a little while since my FWB and I had seen each other. Fast forward to this past weekend; and I woke up Saturday morning extremely horny and deseprate for the taste of him.
I reached out, but he was busy on his one day off that weekend, and I didn’t want to push it and bother him. So I satisified myself and then made myself busy for the rest of the day as a distraction.
Sunday morning comes, and so do I. I wake up horny as all hell again and have a couple solo rounds before I even get up out of bed.
Later on that night, I reach out again, hopeful! Turns out he’s got some free time, but warns me it might be a quickie since he has some work to do once he gets home from work. I’m fine with a quickie, because my body is just on fire from the thought of him.
45 minutes later, he walks into my house, and up the stairs like he owns the place (I love that) and finds me on the bed in a skirt, tank top and no panties.
After he quickly gets undressed and lets me fondle that magnificent patch of chest hair, we make out for a little bit and then he peels off my clothes and starts touching and rubbing all the good parts. We quickly get to sex, and as usual, his rock hard cock slides in and fills me up and INSTANTLY feels amazing. This time, at one point we got into a good rhythm while doing it doggy style, and the best was feeling his balls swing forward and smack against my pussy. Or maybe the best part was while in missionary position as I asked for his thrusts to be harder, he would slowly pull out but then thrust so hard and firm it made my clit tingle. Or then the part when…Sorry, I could go on and on and on!
Compared to our previous 2-3 hour marathons, this was a quickie (only about an hour ;) ), but it was still pretty damn great. The best part was he was determined to make sure I came a few times before he left. Without me even saying anything, or asking, he took it upon himself to make sure I was fully satisfied. And that’s why, three days later, I’m still smiling like an idiot.

I just had to share. It does happen. Your spouse can change their mind. Invite a sexy [F] or [M] into your bedroom.

So if you’ll allow me, I’ve combined two stories, my first FFM and my best MFM. I wanted to share the contrast between the two stories. And this comes from a women who told her husband would never have a threesome. My how times have changed.

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FFM

Nervous as hell is at how it started. I starting drinking some amaretto sours (to try to calm my nerves). It wasn’t working. I went upstairs to put the kids to bed and told my husband to set it up. If we were good to go she’d still be downstairs, and gone if it wasn’t. After the kids finally fell asleep I went downstairs and she was still there. Fuck, what was I in for?

They asked if they should make me another drink, I poured myself another. I sat on the couch, kitty corner to the chair my husband was sitting in. A couple minutes later she joined me on the couch drinking her glass of wine. I texted my husband, and he replied the ball was in my court unless I wanted him to make the first move. I nearly froze… I placed the phone down and just sat there and finished my drink. Seconds passed, and she could sense my discomfort. She made the suggestion that perhaps she could give me a massage to help relax me. I jumped at it and said I’d be upstairs. Read more »

[MF] The Time with the Maid

Recently, I was with my lover in a seedy motel. We were being very dirty, porn level dirty.

All of a sudden the door whips open and the maid is standing in the doorway with a face of shock and awe.
We both stopped and looked at her, even more puzzled, as she slowly let the door close.

It lasted 10 seconds, but it was all in slow motion.

We belly laughed about it on and off the rest of the day.
We laughed about it today. We said, it’s too bad we can never tell anyone.

Ever have something like that happen?

I creampied a married Tinder hookup in town on business Part II [MF][cheating]

Part I is still toward the top of the sub, and I was actually a bit surprised at how popular it was. I’m glad there are so many like-minded horny Redditors.

One of the most interesting points made in the comments addressed how I was told that she was married – after the deed was done. She wanted to be truthful with me about it, but she also thought I was pretty hot (her words) and didn’t want that little fact to screw up her plans. I don’t blame her for going about it that way, and frankly I’m glad she did. I had an incredible time, and I *probably* would have had second thoughts if I knew up front. Just depends on which head I was thinking with at the time.

So to continue the story, she was returning on business about two weeks later and would be in town for about 4-5 days. She wanted to spend time with her team outside of work, otherwise we would’ve been in her hotel each night. Anyways, the first night I took her out to one of my favorite bars to catch up, play some trivia and have a few drinks. It was funny, because we were both a little nervous or shy when we met up. I can’t explain it, but it was more than just a hookup at this point and we both knew it. Read more »

[FM] Exploring our darker side pt3

And so we continue. (read [pt1](https://www.reddit.com/r/gonewildstories/comments/6dfune/fm_exploring_our_darker_side_pt1/) and [pt2](https://www.reddit.com/r/gonewildstories/comments/6ldzdq/fm_exploring_our_darker_side_pt2/) if you haven’t already).

So I was sitting back in my comfy chair, drinking some wine while she was working her mouth on my cock. Then she stopped and tried to climb on my lap. This seemed like a great idea, but I knew that I couldn’t let her take back control: if she wanted to ride my dick, she should at least ask.

So I stopped her, pressing her back on het knees while telling her that I demanded full control, at least on this night. She smiled, but I knew breaking her into full submissive would be harder than I thought.

I gave her instruction to take of her top and skirt, kneel down again and proceed. A little reluctant she now does as I tell her.

She is sucking it good now, as she always does. She is skilled and works my balls with one hand while deepthroating me. I relax and decide to cum. I cum hard in her mouth and like a real pro she shows me her tongue full of cum and swallows with a smile. Read more »