crossdress fantasy leads to popped cherry [m/m]

As a teenager, I had a grown from admiring and jerking off to hot girls in porn, to slowly becoming jealous of them wanting to BE them, instead of wanting to fuck them. This fantasy grew into some experiments with lipstick, panties, and stockings during my later teens – but never more than that. However – everytime I jerked it to porn- i was picturing myself as a girl on her knees sucking dick and getting fucked.

one summer evening, my little fantasy got the best of me – I was slipped into the lace panties I had hidden in my room and pleasured myself watching a girl get fucked – pretending in my mind I was her.

After my session – I decided to go out to the bar with some buddies and forget about my secret slutty desires. After a few drinks I got bored with bar scene and decided to text a gay guy I had met a few days before.

My first threesome [MFM]

Let me preface this by saying that I'm a virgin and have very little sexual experience besides porn, which I've been watching since I was about 12. Yes, even after this happened I'm still a virgin at 19.

Alright a little set up. My best friend of nearly my entire life and his girlfriend, my best friend of a few years had recently got an apartment and I had been spending a lot of time over there. We all became very close, forming a trust circle where we all felt comfortable telling each other anything. We do the average adolescent stuff. Talk about sex, life, and our secrets. Well, little did I know that something that I'd wanted for a long long time and had jokingly suggested between the three of us would come true on one of our drunken nights.

I've always been self conscious about my penis but James and I were pretty drunk, and I guess alcohol gives me a bit of a confidence boost so I was very open. I'm circumcised and he's not. We got to talking and thought it was odd that despite the fact that we've lived in the same house together at times, we still haven't seen each other's penis.

I’m back: Sex with the girl from my apartment building [m/f]

Some of you might remember me. I posted under a different ironman name up until recently. I deleted my account, because it got hacked. Some of the stories I posted over the last couple of years are gone forever from reddit, so I figured I would come back and start posting some old ones to make sure they aren't lost. I will post new stories as well when I have a chance. (New Stories Will Come I Promise). Here is an old one. Hope you enjoy:

Like I've said in previous posts. I figured it would be fun to go back to my promiscuous (man-whore) days and recall some of the stories from back then. I'm generally considered a really good-looking guy (used to model, 6’3”, dark hair, blue eyes, swimmers build, workout regularly), so that enabled me to have quite a fun sex life. These stories are 100% true and not embellished in any way. I think that a straight honest story even if not as exciting at times is a bigger turn on, so that is what I will continue to try to give.

[M/F] I had my first time in a Laundromat, and it was amazing.

I shared a short version of this story before on /r/offmychest because as hard as it may be to believe. I felt burdened by what happened.

Anyways, I was 19 and pretty down on my luck. I had dropped out of college and things weren't looking great, I was unemployed and suffering from real depression. I missed my friends from Highschool who had all gone off to great colleges out of state. On top of that I was feeling pretty restless about being a virgin. I had no real reason to be a virgin, as a tall tan and muscular Hispanic dude. I used to have no shortage of opportunities in terms of girls that I could experience sex with. But my self confidence was shot after my recent college mishap.

Since I was basically either at the gym or at home playing video games I was in charge of doing the laundry which I had no issues with, it was only fair. So I started to frequent the local Laundromat as the machines made the job way quicker than doing it at home.

[m/f] I ended up in janitor porn scenario last night

I felt like posting this to offmychest at first because it feels dirty, and I feel really guilty but I thought you might enjoy it more here. I am a 22 year old male in a relationship of 3 years with my college girlfriend going into my senior year of college, and I currently work as a janitor. I clean a few locations each night, and rarely if ever see anyone while I work. Last night I entered a medical center I clean to find it still occupied by two ladies working late. They were not expecting anyone and it really freaked them out at first with me walking in, but they both soon warmed up to me, and I was working as usual pretty quickly. If I had to guess I would say they were in their early 30s. Both were wearing scrubs girl 1 was much better looking than girl 2. Girl 1 looked like a dead ringer for Amy Shumer, same body and everything, but I honestly didn't pay much attention for the first half an hour while I cleaned. It was about 8:30 P.M when I made it to their shared office and had to start cleaning around them, and immediately they became incredibly flirty. They were joking about having a handsome janitor and how they've watched porn with a plot like this, and even made me do a little show tunes style cleaning dance. I was a little frustrated but still enjoying the attention I was getting from them, and sent a text to my girlfriend that I was getting sexually harassed by some ladies and how it was a double standard thinking it was going to be over soon. 9 P.M roles around and they get up to leave and let me know they're on their way out, but on her way to the door girl 1 touches my chest really seductively and says "keep up the good work handsome". As soon as the door shut behind them I called my girlfriend to complain but noticed that even though girl 2 jumped in her car and left, girl one was sitting in the parking lot still. I told my girlfriend I had to go a little worried that girl 1 was sitting outside still. As I round the office I see girl 1 walk back in, she smiled at me and said she forgot something. I was shaking at this point and my heart felt weak in my chest because it seemed like something bad was going to happen and that I wasn't over reading the situation. Sure enough she calls out to me and asks me to help her carry a box to her car. Hands trembling I walked in and to my relief there was a box and she was sitting back in her chair. She said she hurt her neck picking it up and asked me to rub her shoulder. I knew it was real at this point, I was shaking but also rock hard. I told her no very sternly and said I was leaving and she should lock up, but she insisted and I let my baser instincts take over. As soon as I touched her shoulders from behind she grabbed my arms and slid them down to her breast, and as if we had been planning it all night, our bodies were all of each other. She turned around facing me as we kissed and immediately started fumbling at my pants. I sort of had become singularly focused on her breast at that point and pretty aggressively ripped her scrubs shirt off of her and unhooked her bra. She had a pretty decent body honestly, large breasts which coned out like a pears with large nipples. She had a little belly fat which I didn't find too unsightly and a little dangly cheap belly ring. She dropped to her knees and started giving me absolutely expert head, but oddly the more I started to realize what the fuck was happening the more angry I felt. I felt like this lady had just ruined my whole future with my girlfriend and grad school by seducing me and it really made angry like I've never felt before with a hot ball of rage filling my stomach. I pulled her to her feet and turned her away from me ripping her scrubs down to her ankles and then using my feet, kicked her legs apart and bent her over forcefully at the hip so she was bent over the table. She had an inny kind of pussy, but at the moment I was so mad and turned on and confused I hardly looked. I got on my knees behind her and started eating her out from behind, feeling how wet she was already and listening to her moans as I sort of haphazardly rolled my tongue around her, and then for no reason I looked at her ass hole and decided it had to be eaten out too. Never done it before in my life, never thought of doing it to a stranger, certainly not after she finished a long work day, but wtf it happened anyways I guess. I think that shocked even her a little but she seemed to be really into quickly and started spreading wider for me, which brought me back to reality a little and shocked me into stopping. I stood up and lined my cock up with her, she asked me if I had a condom and I asked her why the fuck I'd bring a condom to clean toilets and drove into her. Maybe it was the angle, but she was especially tight, and soaking wet. I could see pictures of her and her boyfriend on her desk, I grabbed her hair and held on as I pumped furiously into her. All that anger and passion made me go harder than I ever have before, her knees went out and she slapped the table and feeling her hot juices running down my leg, I latched on hard and filled her up. My first thought was how good it felt, followed by immediate and horrible regret that I came inside a stranger with no condom, followed by the urge to throw up after realizing what had just happened. She walked pantless to the bathroom and scolded me for doing that to her, mentioning her boyfriend. I was disgusted with myself and packed my car and left her inside. I have no idea what her name was, I don't know if she is going to report it, or if there were cameras, or if she will find me somehow, or if shes pregnant, or what the fuck to do about my girlfriend. Stupid fucking decision and I hate her more than I can say, but maybe one of you guys will enjoy the story, or not, I just had to confess to someone.

First Visit to a strip club

ok I must begin with excuse my writing as I am not a very good in writing. so here it is yesterday I got pretty bored and read about new penthouse club open in Perth Australia, so i decided what the heck why not. I went down, got to the gate, get in very easy there was no fuss. now it was my first visit ever, I walked in and i was like a slap a cross the face, so many naked girls everywhere, there was also one Porn star her name start with Tasha Reign.

[m/f] How I slept with a group member before a class presentation

So apologies beforehand, I am in no way a master writer. I can write History papers like a champ, but when it comes to stories, eh. This is a throw-away account, as my friends and girlfriend browse Reddit, and I don't need this on my post history, you understand.

A little backstory: I am in my first semester of graduate school, hoping to graduate in Spring 2017 with my Master’s. Part of my program requires an unbelievable amount of presentations/group projects, things I normally despise. I’m also a graduate assistant (which is basically a full/part time job that helps with tuition, housing, meal, etc) in one of the departments on the campus. I grouped up with two girls from the same department as we all work crazy hours, but we know when each other works and we spend most of our time on a certain section of campus so we’re not far away if we have to meet and work on the project. Our professor wasn’t happy with the idea of three people from the same department working together, so he attempts to break our group up. Our saving grace, we’ll call her Kristen, she works in another department and basically says “No worries! They look cool, I’ll work with you.” Which was a huge relief, because a lot of the other students are snooty Type-A pricks who drive me nuts.

Reconnecting with and fucking an old crush. (m/f)

This past weekend I hooked up with an old High School crush I hadn't seen in about 13 years. We'll call her Storm.

My wife and I decided a long time ago to have an "open" marriage. Like a lot of such things, this started with a few threeways with an ex-girlfriend of mine that I was still friends with. Since those trysts came to an end I've been unsuccessful in finding a woman good enough to actually sleep with me.

I went looking for Storm a few weeks ago on Facebook, but to no avail. She was one of those girls who never went by her given name, but none of her old nicknames turned up. Thinking Oh, well to myself I moved on.

One night I got a friend request from a name I didn't recognize. I went poking around her pictures (which were a lot of drawings) until I found an actual picture of her, and holy shit! there she was!

I added her and we immediately began chatting. It was one of those weird times where things just seemed to fall in to place, and within twenty minutes we were trading dirty pictures and making nasty comments about each other. About how we missed so many opportunities back in "the day" since we didn't know we liked each other.

A Tale of Two Sluts Pt. 1 [fSubs](MMMff)

This was the hottest night of my life. Literally, the sun had set but the temperature lingered in the mid 90s. We were at a cheer competition for my sister. She was 16 and had just gotten her first boyfriend. She's the kind of blonde that makes you think she moved straight for Norway. She was short – 4'9 at most – and weighed less than 100lbs. Her skin was a deep brown from too many visits to the tanning bed and her perky B cup tits went perfectly with a shapely toned ass.

We were near opposites to the point where most people thought we were friends instead of sisters. I was 18 at the time and the Captain of the Cheer team. I was the "base" to my sister's "flyer" and at 5'9 130 I dwarfed her. I had a huge ass (my pride and joy later in life) and thick thighs, and with DD tits I was the envy of every girl and the object of lust for every boy in high school. I wore my hair short around my ears then and dyed it a darker shade of brown.

live sexystories from other redditors! [m,f 18-45] [chat group]

Hi all –

Miss the old AOL chat rooms?

Jump on board with an ongoing chat group (all 18+, good mix of nationalities, mostly guys, some lesbians, a few couples, a few single women)

Topics: mostly truth or dare, lots of over-sharing, and of course, lots of over-eager men.

Moderators: We have moderators to help keep the comedy and mutual respect to a maximum, and the creeps to a minimum.

Please Do come if you're over 18, an exhibitionist (or like those that are), you like chatting (about sex mostly), and have a great sense of humor.

Please Do NOT come if you're just looking for naked girls. There's a web of porn for that. Not saying it doesn't happen, but… it'll be on their terms.

Send me your screen name to join the 50 people already chatting!