This happened to me 5 years ago…. I was 19 years old at the time. I had been cross dressing on and off privately through highschool. Mostly trying on panties and lipstick and picturing myself as the girl in getting fucked while watching porn… On a lazy summer afternoon I was doing my usual routine, jerking off in some lace panties… when i finished I cleaned up and went out to the bar with some friends… still having some girly thoughts in my head. I ended up extremely drunk and wanted to smoke some weed so I texted a gay guy who I had met at a friend’s sisters birthday party – he gave me his number as I was looking to buy drugs off of someone. He texted me back and asked if I wanted to come over. So I hopped into a cab and met him at his apartment. He offered me a beer and we chatted for a minute before he asked me if I wanted to watch a movie because he had no weed. The tv was in his bedroom so we both lay on his bed and started watching the transporter. After about 5 minutes of laying next to him on his bed he touched my hand and we started to make out. This was my first time kissing another dude an it felt very weird. After making out for a few minutes I started taking his clothes off and grabbing his dick. The next thing I did was start sucking his nipples an eventually I had made my way down to his dick which I started sucking. Can’t remeber how long I sucked his cock for but he figured out it was my first time so he started to suck mine to show me how it was done. At this point we started making out again with myself lying face up and him lying ontop of me- I then asked if he had a condom. He put on a condom and put some lube on his fingers which he then rubbed onto my ass. Then he started to fuck me missionary style- it hurt at first but then I loosened up, lifted my legs up and squeezed them around his body- he really started to pound me hard at this point. I was so drunk at this point and was imagining myself being fucked as a girl – so I asked him to take me doggy style on the bed. I turned over and let him start pounding me from behind. When I started to push back on his cock he told me not to move and to let me fuck him. After a few minutes he pulled out, told me to stand up and bend over his bed- he then fucked me bent over. After this we got up onto the bed again, he lay down and I hopped ontop and rode his cock while facing him. At this point I was bouncing up and down and felt like a complete slut. I was riding him so hard he said he was going to bust. I slid off his dick and took the condom off – then I got on my knees and sucked his cock until he came in my mouth. I swallowed his cum and proceeded to put my clothes back on. He asked me if I wanted to be finished off – but I said no- I just wanted the experience of getting fucked like a slutty whore. He then drove me home and I never saw him again. I jerked off on my bed 5 times after getting fucked like that. I just imagined myself as a slutty drunk chick getting pounded after a nightout haha. I havent had any sexual desire toward a man since then. until now…
Category: gonewildstories
Last date until September [MF]
We arrived at the fair early, and since we had nothing better to do, we decided to take a walk. I can’t take the heat at all, but luckily there was a playground that was half in the shade. It was such a relief to be in the cool shade. After releasing our inner kids, we stop and sit at the top of the slides where it’s all very cool.
Being the type of girlfriend I am, I immediately start teasing him and he’s teasing me. (Don’t worry. No kids in sight). Before we knew it, he’s hard and so turned on, as am I. We leave our spot in the shade and make our way to a field…a cornfield to be exact. Once we’re far enough away from view, we immediately start making out. A rushed foreplay that goes quickly to me blowing him, but we’re both so horny, I don’t stay like that for long.
Sebastian D’Anconia’s Story (M/F) part 1, long
Out of the blue, I get a call the Friday of Labor day weekend. A number I haven’t seen in a long time. The thought paralyzes me for a moment.
Its been two years, but with someone like her.. the emotional charge her name popping up on my phone will not fail to affect. In a moment, the myriad of emotions swept over me. Surprise, fear, longing… I pick up as if controlled by someone else. Hers was a call that I could not ignore. I felt a prick of annoyance that someone could such a profound effect on me without saying a word.
I answer cautiously, and it turns out she’s visiting in town, and wants to see if I would get a drink. It’s been a long time and despite my emotions, I feel over her and fine, and in fact recently got out of a bad relationship, so I said fuck it, let's go.
(F) wanna go running with (m)e?
Hello reddit users. I recently stumbled upon my own gonewildstorie and really wanted to tell someone so here it is. Sexy part at **** I am 18 5'6 brown hair muscular buildish. I like running. Hell I love running. just go out and run to clear my mind, there is nothing better.
The summer was approaching me and my friends, some had plans to go to camp but some had no plans ( I had none). The people who had no plans included laura and my best friend matt. We starting stressing out about what we would do all summer (our past before college) so I suggested we do a running group. They loved it. Now we at least had something to look forward in the summer.
[F]inally fucked [M]y crush from freshman year of high-school and it only took me eight years.
Long time lurker, but I've finally had an experience that I think is worth posting so go easy on me. This is definitely not like writing the research papers I'm used to.
So this story begins back during my freshman year of high school, eight years ago. Shit, it does not seem like it's been that long… Anyways, I had gym class with this girl named Christina. She had long dark hair, olive skin, and lovely brown eyes. Of course, we were in gym together so I also saw that she had a wonderful looking ass and long thin legs to go with it. Her breasts were small, but we were freshmen, so it would have been unusual for them to have been otherwise. She was a soccer player. For some unknown reason, she seemed to like talking to me. I was more than happy to oblige.
I fell for her, managed to get her number, and we started texting and became close friends. Needless to say, I didn't make a move. After all, what if she rejected me? About a year passed and I finally decided to ask her out but got denied. She had wanted to date me earlier on, but had lost interest when I failed to make any move for so long.
The one where I [m] finally gave in to temptation and fucked my girlfriend’s best friend/roommate [f]
For as long as I can remember, I was one ugly motherfucker. From birth, all the way to the beginning of my freshman year in college, I would send women fleeing to the hills shortly after first contact. It wasn’t that I was naturally hopeless, you see—more that I was unhygienic, socially clueless, overweight, a bit of a late bloomer, and had a set of teeth that looked like they belonged to a British boxer who had a bit too much of an affinity with tea time. All of these things weren’t too pleasant, and of course it took me some time to develop the self-awareness and maturity to recognize them, but they were things that I always saw as alterable so long as I put in the effort and energy to change them.
One day, towards the start of my time at University, I decided I had had enough of my virginal, depressing life and changed my life for the better. I hit the weights, bought clothes that fit me, scheduled monthly haircuts, got fitted with braces to fix my teeth, and began integrating myself in the American college lifestyle of parties, drugs, and social gatherings to improve my communication skills.
While you’re out cheating on your pregnant wife, your pregnant wife if at home cheating on you with me.
Last weekend my neighbor had a bbq at his place and invited me over, i didn't have anything else better to do so i ended up going. At the end of the night i was the last one left at their house. I figured while i was there i might as well help clean up the mess. Not long after i started cleaning my neighbor got a phone call and said he was called into work and within minutes was in his car and gone.
Now it was just his pregnant wife and me which made me feel slightly awkward. We wound up talking and for whatever reason i asked if her husband gets called into work this late a lot. After i asked that her whole demeanour changed and she responded with "more then you might think".
I wasn't trying to pry but i asked what she meant by what she said. She went on to tell me that when he "goes into work" he's off fucking someone else. Apparently since he found out she was pregnant he refuses to have sex with her and on top of that has been cheating on her for at least the same amount of time and things she's so dumb she doesn't know what he's doing.
[MFF] FWB freak leads to threesome and creampie eating.
I had met a girl who was a waitress at a restaurant I had gone to every week. She was half white and half Vietnamese, with smooth brown skin, a muscular body covered with tattoos, and amazing tits. , Even though she was 22 and I was 35, I hit on her and she flirted back, and eventually I asked her to a formal event, and got her to say yes. . I picked her up in nice car I had borrowed, took her to a gala my work put on.
Affairs of a Life – The Seminar
My name is Laine, and almost one year had passed my first affair. Unplanned and unexpected, it had taken me places sexually that I had never known. When it ended, I kept it to myself, and my husband Jack never learned what had happened.
I have worked very hard at making our marriage stronger, including trying to improve our sex life. Jack would have continued being happy with a quick five minute ritual on Saturday nights — missionary position only, of course. However, I continued at trying to make him more adventurous. One night I even got him to try fucking me from behind, my head on the pillow and ass in the air, but he made it obvious that he thought that to be strange. And when trying to share oral sex, that was totally off limits with him. I do not know if it was that Jack's penis was not very large, that he came almost immediately, or if it was something I was doing wrong. Regardless, I kept trying.
The night I didn’t plan to try BDSM or have sex with a woman (MFFM & Dom) (Part One)
One recent Friday night I had plans to have dinner with a girlfriend. A long-standing FWB of mine, Jason (he's featured in some other posts here) asked whether I could see him on Friday night. I knew dinner with my friend could easily go for a few hours but relished the thought to forget my troubles with him. We left it that I would text him when dinner was over, which would probably be around 10pm.
My girlfriend and I had a great dinner. I hadn't looked at my phone in three hours. I went to the bathroom before we left and saw a text from Jason which he'd sent two hours earlier:
"Mind if I see if I can get a couple to meet for drinks and maybe more tonight with us? :)"
Fuuuuuck.
He and I have talked about this multiple times. After all, he's the one who procured a threesome for me, and joined me my first night as a unicorn at a swingers club, and was supposed to come to a gangbang night (which he still feels guilty about). But he's wanted to play with another couple for as long as he and I have talked about playing with others.