Tag: Anal

The first time I had sex [MF]

Well, I don’t know if there is too much to tell. She wouldn’t take her top off. She told me that her boyfriend was asking her to do anal in exchange for money. Her boyfriend wasn’t there at the time, but she did have her webcam on, or maybe a chat window open, so she got super paranoid after we fooled around.

I think I lasted 30 seconds. I was 30 years old, she was 20 years old or something. It wasn’t great, and I told her “Hey, if we don’t stop this, I’m gonna, you know…” and maybe she was fine with that because she didn’t stop me.

So, after the first time, I figured, “In for a penny, in for a pound” and I went back for two more pounds, throughout the night. It was really beautiful, like an allergic reaction to peanuts.

As to how we ended up together, all I can say is that she gave me the crazy eye, and I knew it was over for me. She worked with me and flirted heavily, but then she got fired so I thought I was in the clear. Then she got re-hired, and I didn’t have the time to make a good defensive posture. She just kind of got me alone once and started kissing me. Then later, she texted me and it was all over. Read more »

[MF] That time an older man introduced me to anal

First time posting a story, hope you like it…

Background: through complicated events I started a relationship with a man who was 50 when I was 18.

So we’d been seeing each other a few months and our relationship had been sexual from the very beginning.

One night we were playing with massage oils. He would rub some into me, I would do the same to him. A great way to relax. After a while I was on my belly with him rubbing oil into my back and my ass. Every now and then some of the oil would run down my ass crack and find its way down to my asshole and pussy. The oil trickling down to my butthole was kind of a nice feeling if a little ticklish.

We hadn’t played anally before which made him a little hesitant, but after a while I noticed he was rubbing more and more oil into my ass and deliberately spilling some more between my cheeks each time. Before long he started to massage that area too but I wasn’t expecting the finger he slid into my butt.

I drew breath and turned my head to look at him for reassurance. Read more »

[FM][Kink] From vanilla into his ass. (thanks reddit) ;)

For a while I have been looking for someone who could be rough, but not too rough. My wish came true couple of days ago when I hooked up with a redditor. Here is the story:

I was overseas for work and I posted in reddit looking for cybersex with someone in DC. Few days later I found this message: “Forget voice chat… I’d love to grab a drink and see where things take us. What part of the city are you in?”

He read one of my stories, sent his picture, and we decided to hook up on Weds, the day after I come back from travel. He is 5’9, muscular build, brown hair, blue eyes, and well endowed. I am 5’4, full figured, brown eyes and dark hair, 36 DD. He asked me for a pic, and I sent him one but did not hear back from him for 2 days, so I assumed he was no longer interested. I scheduled for an appointment at the spa for a massage and a bikini wax. I was dreading responding to the other many redditors cause I just didn’t have the time. And my sexual urge was starting to fade as I was giving into the daily pressures of DC. Read more »

[FM] From vanilla into his ass! Thanks reddit :)

For a while I have been looking for someone who could be rough, but not too rough. My wish came true couple of days ago when I hooked up with a redditor.

I was overseas for work and I posted in reddit looking for cybersex with someone in DC. Few days later I find this message: “Forget voice chat… I’d love to grab a drink and see where things take us. What part of the city are you in?”

He read one of my stories, sent his picture, and we decided to hook up on Weds immediately after I come back from travel. He is 5’9, muscular build, brown hair, blue eyes, and well endowed. I am 5’4, full figured, brown eyes and dark hair, 36 DD. He asked me for a pic, and I sent him one but did not hear back from him for 2 days, so I assumed he was no longer interested. I scheduled for an appointment at the spa for a massage and a bikini wax. I was dreading responding to the other many ridditors cause I just didn’t have so much time to look into this. And my urge was starting to fade. Read more »

[Group] Our first foursome

*Sorry for not posting any stories in a while!

We had been keeping our threesome routine going for some time, but also had all become occupied with other things that had kept us limited from all meeting up as often as usual. The 3 of us were all graduating soon, but didn’t really ever talk about the fact that we all wouldn’t be in the same area anymore, since college required some of us to move. We finally discussed the issue during one of our hook ups, and while we weren’t too happy about facing reality, we accepted it and agreed we’d all keep in touch as much as possible. Stacey, however, proposed we try something new, as somewhat of a “graduation present” to us all. Chris and I were up for it, but Stacey admitted she didn’t know what to do. We all lay on Chris’ bed naked, watching TV and brainstorming what we could do next. Read more »

I[m]promptu Wi[f]e Swap 2 – The Giving Season [Public] [Anal]

So I got approval to use a few pictures, so I figured I’d pepper some pictures throughout this one and include any images I could to help with the telling. Some of these are real pictures of us, others are placeholders that are as close to us as possible (I’ll let you guys guess at which ones are real and which aren’t). The image quality is poor in some and better in others so I apologize for that but hopefully it helps get the story in your head a little better! I also stopped taking pictures after a little while because, well, sorry guys, you aren’t my top priority and they were just ruining the flow of things.

For those that missed the first round: [My Side of the Story](https://www.reddit.com/r/gonewildstories/comments/56cljk/impromptu_wife_swap_a_lake_trip_gone_awry/) [My Wife’s Side of the Story](https://www.reddit.com/r/gonewildstories/comments/
56z7cd/impromptu_wi_fe_swap_the_other_pairing/)

The past three months have flown by and yet also seemed to move at a snail’s pace at times. Since the lake trip and Sarah, Dan, Lauren and I’s first adventure I have replayed that night over and over again in my mind and I’m still shocked it happened. The anticipation of what was to come next had me all riled up and clearly it had the same effect on everyone else. We tried not to discuss the lake much and were fairly successful in keeping things as normal as they had been before our first swap. Read more »

Best sex of my life with during a year long affair with a co-worker. [MF]

I met Mike when I started working at the same place he worked. We became friends and started hanging out a lot outside of work. Both of us were married and somehow struck a rare cord that were we’re both interested in more while still wanting to stay with our spouses. We knew from the get go it wasn’t going to be a long term thing. But boy did we have fun while we were together. So many fantasies fulfilled. We really enjoyed the dom/sub relationship. I never would have thought denial could be so hot….but when he wouldn’t let me cum for days, longest was 8 days I think., and then would come over a fuck me hard and fast and I would have to ask if I can cum. Nothing hotter, or him coming over and not giving a damn if I came or not, just lifting my skirt, bending me over the couch and fucking me till he came, slapping my ass and leaving. He was my first anal experience. It was amazing. Don’t know how I will go back to not having it. I wore a butt plug to work knowing he was the only one who knew it was there. Correction, I asked if I could wear a butt plug to work. He came to my house one night, informed me before hand that I was to be sitting at my kitchen table back facing the door and not to move when he came in. He very forceable grabbed me pulled up and tied my hands with a tie he brought from home. It was the break-in fantasy I had told him about months before and he was doing a great job. He brought me down to the bedroom and pulled my pants down and told he’d been watching me for months. Seeing what a dirty slut I am for everyone else and now I was going to be his dirty slut. It was sooo hot. And I was his slut. The whole time. I would have done whatever he wanted and think I pretty much did. We had movie night where we just hung out on the couch and made out, touched, groped, sucked, did everything but sex. It was so good. But the oral…..I’ll miss that most of all. He loved doing it. And was soooo good at it. The hottest thing that I have heard to this day was when he was licking my pussy while I was laying on the coffee table. I kept sitting up to pull his head up so he could fuck me and he would push me down and said ‘ I want more.’ And go right back to licking and fingering my pussy. I am so wet right now just thinking about that happening. We decided that my birthday would be the end of it, one last night of doing everything crazy. Tie ups, hard fucks, oral, anal…everything. We had both taken the day after my birthday off to get a whole day of it in. Something came up, a pretty huge, life changing event, so we didn’t end up getting our last time. As disappointing as it was not to end it end it. It was great while it lasted. We are still great friends and I hope to remain that way for a long time. This will go down as the best sex I have ever had and likely the only affair I will ever have, and I am totally ok with that. I don’t regret a thing. Read more »

[MF] My Girlfriend – Dreams, Fantasies and Reality

For those who missed it:

Here is part one of the new chapter:

My Girlfriend – A New Chapter from gonewildstories

Here is part two of the new chapter:

[MF] My Girlfriend… Honeymoon’s Over (?) from gonewildstories

Here is part three of the new chapter:

[MF] My Girlfriend – Doing it in a Magical Place from gonewildstories

Here is part four of the new chapter:

[MFF] My Girlfriend – "Guess who’s back" from gonewildstories

And all five parts of the initial story.

Here’s part one: https://www.reddit.com/r/gonewildstories/comments/4hhvtt/my_girlfriend_and_her_sisters_nude_habits/

Here’s part two: https://www.reddit.com/r/gonewildstories/comments/4j1qkr/my_girlfriend_and_her_sisters_nude_habits_part_ii/

Here’s part three: https://www.reddit.com/r/gonewildstories/comments/51flec/my_girlfriend_and_her_sisters_nude_habits_part/

Here’s part four: https://www.reddit.com/r/gonewildstories/comments/51rgd5/my_girlfriend_and_her_sisters_nude_habits_part_iv/

Here’s part five: https://www.reddit.com/r/gonewildstories/comments/52qhsu/my_girlfriend_my_girlfriend_and_her_sisters_nude/

Erin was the golden child of her family. If her parents were to be believed, everything she did she did well. Erica was perpetually the little sister. Erin was toasted by her family as the first one in two generations to graduate with honors from High School and go to college, a very good one at that. Read more »