My first experience with a crossdresser [M18, T25]

For this story, I’m returning right back to the beginning. This was about ten years ago, but as with first experiences for many people, the vivid details have stayed with me to this day. I was 18, and at the time had begun partying. I live in a jurisdiction where the drinking age is 18, so as you can imagine, we liked to let loose at the weekends. I don’t drink now, and drank very little alcohol at the time, so my partying usually consisted of me driving my friends to a club, dancing a bit, try to get a girl and then head home. Obviously being relatively sober around drunk girls had its advantages, and many times I had girls hanging over me because I could make them laugh. Or more properly, I could speak coherently, while they couldn’t.

I’d already been into crossdressing porn for a few years. This was 2005, YouTube had only just started, and streaming video was very much in its infancy. In fairness, we already had broadband Internet, so it wasn’t terribly slow, I think in or around 2mbps. Despite that, streaming porn had barely taken off. I constantly fantasised about crossdressers, but usually I could only get that fix by images. Hardcore porn movies mostly featured so-called “shemales” in those days, which weren’t then and to this day aren’t my thing. The odd crossdressing video I could find left me cumming for days. I fucking loved it.

Masturbating in the Uni parking lot.

This took place a few years ago. I had decided to take a couple of difficult classes at a much smaller uni in the same city, as opposed to my regular uni. The reason reason for this was because the class sizes were smaller, I could have greater access to the profs.

This campus was on the other side of the city from where I lived. Despite this, it made more sense for me to drive as opposed to taking the train. It would have been a shorter commute. In those days I didn’t have my own car as I didn’t need one. So my dad used to let me borrow his van.

I loved this van. It was this sleek black Toyota Sienna. We had bought it brand new and it was so roomy! On my insistence, we had gotten all the back windows tinted to a limousine tint so you couldn’t see inside at all. This thing was a beast and I loved it.

My most recent time fucking a crossdresser [M28, T19]

I’ve always had a voracious sexual appetite that has led me into the rabbit hole on more than a few occasions. For my first story, I’m going to retell my most recent night with a crossdresser. This happened in February 2016 and is as accurate as my memory will allow.

I’m 29, tall, a fraction overweight, but I would imagine reasonably attractive. I am single, live alone and have no dependants. I did well at school and at university, and have found success in the financial sector. I am not objectively rich, but do make a six figure salary and have the toys to go with it. I only mention that as for the purpose of some other stories, I have managed to use it to my advantage to sleep with women very much out of my league. Sexually I am very much of a hedonist, but in my day to day life I am boringly ordinary. I do not drink, do drugs or smoke. My cock is just a hair over 7 1/2 inches, although it’s not particularly thick. It’s perfectly straight, something that has been commented on by lovers a few times.

Young Lust – [MF]

We finally got here. She grabbed my hand and led me to her house. She fumbled for her keys, then finally found the right one and opened the door. She jerked my arm in her direction and once I got inside she slammed the door shut. All I can hear is my heart pounding away inside my chest and the heavy breathing. She pushed me up against the wall and finally had her way with me. With no hesitation, she ripped my shirt off and began kissing my ear and teasing me. I was slowly melting, moaning while she kissed down my chest inching towards it, then, quickly, she licked her way up my chest. I knew what she was getting at, I delivered. I teased her to get back at her; I ran my hands up and down her sides while I kissed and bit her neck, I grabbed her by her arms, picked her up and wrapped her legs around my hips and arms around my neck. I tasted her tongue in my mouth. I threw her on her back on top of her bed and jumped on top. Fuck. This is great, every time she claws my back, every time she bites my neck and every time she makes me want to be inside her more and more, this is definitely worth getting off the drugs, especially for her. I put a hand between the buttons of her shirt and without a beat, I ripped her shirt off her back. I couldn’t fathom how much I loved her and every inch of her body. Her hand in my hair, our skins against each other, the way her mouth and skin tasted, the heat of the moment, even the aggressiveness. I rubbed my hands down her back, slowly, finger by finger, down to her thighs. I slowly rubbed her thighs, I could tell how much she wanted it from how rough she made out with me. I put by hand on her and grabbed her ass. Her breathing quickened even faster giving off the cutest moan I’ve ever heard. She got even more aggressive with me and got rougher with how she grabbed me. She ripped me off her, threw me to the ground and ran her finger down my chest and slowly kissed me from my neck down to my chest, slowly down my abs. She then stopped, grabbed eye contact and slowly unbuttoned and unzipped my pants. I couldn’t think straight. I kept breathing faster and harder. She yanked my pants off, ran her finger over my member and kissed it through my boxers. I was finally putty in her hands. She pulled it out, took a minute to admire it and kissed the head. Slowly took it in her mouth, slower and slower to tease me. I clawed at the ground, moaning louder and louder. This was better than all the heroin and pills I’ve done. I grabbed the back of her hair and forced her head down harder and deep. I could feel it all. Her tongue wrapping around me. Every lick from the base to the tip. The warmth of her mouth. It all drove me to a rush I’ve never reached. I pushed her off, undid her pants and yanked them off. I ran my finger down her panties. It wasn’t hard to see how well the foreplay effected her through her panties. Then, in one instant, I’ve never had my heart pound so hard. She looked me dead in the eyes and softly said,
“Fuck me. Now,”
“Beg,” I commanded.
“Oh, please, Honey. Treat me like a slut. Your slut,” She begged.
I was satisfied. I kissed her through her panties and she let a tiny moan slip. I slid them off and climbed deeper into the fun. I lightly kissed her inner thigh leaning closer in. Once I got there, I took a glance at her, she was in somewhat of a trance, I wanted to take it further. I took one long lick, there wasn’t a distinct taste, but it was sweet, I wanted more. She slowly let out a gasp, then a moan and then grabbed my head with a tight grip on my hair. I rubbed her tits as I licked her and played with her. A kiss here and there. I slowly slid one finger inside her and moved back and forth slowly and before I could tease her clit, she was fed up. She put me on my back, hand on my chest and got on top.
“It’s my turn now,” She commanded.
She let her hips slide down onto place and mounted herself. She was taking her time with every thrust. Allowed herself to engulf herself into the lust. She moved quicker. Every moan made me want more, every thrust pushed me further to snapping closer to the temptation of the animal I was. Before I knew it, just like that, I didn’t just snap, I was devoured by madness and became the sex hungry monster I am. I lifted her off of myself, ass in hand, legs wrapped around my waist and mounted herself onto me. I moved in and out, started off slow. Pushed her up against a wall then fucked her harder and faster, moved deeper in and further out. I’m sure I broke the wall, but who cares. Once we were up against the wall, pounding was an understatement of what I was doing. She was screaming for more and alternating between clawing my back up and balling my hair up in her hand. This was fun, but we wanted more. I threw here on the bed and grabbed the handcuffs from the dresser by her bed. She kept her ass up begging for more, I pulled her arms back together and cuffed them. I jerked her hair back and fucked her against the bed. I slowed down, I knew if I went further, I’d cum on the other hand though, she loved it, the change in speed really toyed with her. I noticed the mirror behind us, I moved her to make her watch me fuck her. I finally put her on her back and got on top, I wanted to taste her some more, I was ready to finish. I grabbed her hair, encased myself on top of her and we moaned in each other’s ears. I finally succumbed to my lust and came inside her. It was so warm and relaxing inside her, I didn’t want to move or leave. I could tell by the look on her face she loved the feeling even more than I did. Her eyes almost looked as if they rolled back, I undid the cuff and hid into her chest. She played with my hair, I’m not sure why, but I absolutely loved that and never wanted to leave.
“Darling, don’t ever leave me,” she whispered.
As I held her closer, I responded, “I would never.”.
We laid there, enjoying each other. We held each other close to one another and played with each others hair and hands as we drifted off.

My one time with a married woman [Part 1 – ff]

*(This story is from a couple of years ago, again some of the details may be a bit off. Apologies. And it’s long, so here’s part 1. Part 2 is on its way. I promise.) *

Spring was finally here. It was a dreary winter that dragged on and on and on but it was finally over. It was probably the first chance we had that spring to actually go out. Plus it was a Friday, so it was a perfect chance to unwind. We ended up going to a pretty shady bar that at least had an outdoor area right by the river for some fresh air, which was awesome. The biggest selling point of the place was that it had cheap beer. But I don’t drink really like drinking beer, so that was no help to me. I had a couple of overly watery margaritas, so at least I stayed hydrated, if not a little more sober than I had planned to be.

Overseas Orgy [M20,F19,M21,F21,M23]

So this happened last summer in Brazil. For some context, My name’s Jack, I’m 23, 6’2” with a fairly average build, leaning very slightly to athletic – but not by much. I’d like to think of myself as pretty funny in a self-deprecating, slightly nerdy sorta way, and I somehow managed to luck my way into sleeping with two 9/10’s in the same night.

I was lucky enough to be over in Brazil for the summer doing some work with a charity, usual stuff – you spend your days doing manual labour in the middle of nowhere, in exchange, travel for basically nothing and get good CV fodder.

The first month went very quickly, stuck in the sweltering jungle, made great friends with a lot of the other folks there. Folks from lots of different countries, maybe 20 of us in total. It was exhausting work, but the good kind of exhausting; where you don’t realize it until you’re about ready to drop. We all got along really well pretty much instantly. There was no real chemistry at this point, in fact – sex was the absolute last thing on my mind.

(M/F) My wife’s niece sucked my cock, and now I want more… (It Finally Happened) (Part 4)

Part 1: https://www.reddit.com/r/gonewildstories/comments/49l0gz/mf_my_wifes_niece_sucked_my_cock_and_now_i_want/

Part 2: https://www.reddit.com/r/gonewildstories/comments/49q26d/mf_my_wifes_niece_sucked_my_cock_and_now_i_want/

Part 3: https://www.reddit.com/r/gonewildstories/comments/4a172l/mf_my_wifes_niece_sucked_my_cock_and_now_i_want/

Things continued on pretty much as normal after that past Monday night where Candace watched my wife and I fuck from the hall. Busy schedules for both Candace and I took over, and that prevented us from having much interaction over the next 4 to 5 days. Candace had pretty much stopped sending me any nude pictures or anything like that, and we weren’t talking much, but I could still tell she was interested in me by the way she looked at me when we were around each other (not often) those 4 to 5 days.

How I [M18] ended up having some fun with my hairdresser [F39] in the salon Pt. 2

-Just some info before you start reading the story. This does not take place in a salon again, regardless of the title. I just kept it the same and put part 2 because it’s after the original story (just go to my profile if you want to check it out because I have no idea how to link stuff on reddit LOL). I recommend you read part one because I describe Diana in a lot more detail, and I think it would be a lot more fun to read this after you read the first! Also, I’m sorry to everyone for holding this off for so long. I was busy with school for the past week and a half and I also didn’t feel like writing the story that much after I’d finish my homework late or come home after a night out with friends because I’d then just fall asleep. I’m feeling it now though so let’s get on with the story :D-

[fFM] Fun with my neighbors 2

So I received a lot of questions about what happened and requests for more stories. I have one where they came to visit me. They decided to fly out to visit the city I live in. I offered for them to stay at my place but they insisted to stay at a hotel. I was excited to see them again. After the first time when I went back home we had fooled around a few more times that week before I came back. We fooled around a lot between me and her and me and him and me just watching them so at this point we were very open about most things..

They landed on a Thursday and took a cab into the city. I didn’t get off of work for a while so they went to the hotel and began exploring the city. We decided to meet up for dinner at a restaurant in my neighborhood. I showed up very early, probable just anxious, so I sat at the bar. I wore a black dress and heels. While I was at the bar I felt a hand in my lower back and when I turned around both of the hugged me. At dinner we talked about home and any fun things they have done lately. They had spent a weekend camping with another couple and had some interesting group sex involving some male on male. I was surprised. I knew he like to have a finger in there but I didn’t expect full penetration. The dinner went a long time but by the time we were ready to leave it was still early.