The confession of a cocksucker

This happened about 10 years ago, and I’ve never told anyone about it. It happened in various scenarios, several times, over the course of a few years. Even after our business relationship ended. I’m pretty sure it would be considered rape, I could have had him arrested if i didn’t end up enjoying it, or blackmailed him.

I had just got my first job, about 2 weeks prior to this. I needed my boss to fill out an employment verification letter (can’t remember what it was for). So I went in on my day off, to try and have him fill it out. It also happened to be his day off. The deadline was the next day, though. So, the assistant manager called him for me. He said I could come to his house, and he would do it. He lived about 1/4 mile away, and I headed over.

When I got there, he was sitting on the porch drinking bourbon. He did the paperwork, and we sat and talked for a bit. He offered me a drink ( I enjoyed bourbon, and was not 21.) And I started to drink with him. I ended up having several shots.

[M]et up with a guy for [M]y first bi experience

I consider myself straight and have only ever been interested in relationships with women, but I can’t deny getting turned on thinking about trying something out with another guy. Can’t deny that occasionally when I watch porn my eyes drift away from the beautiful female body and over to the guy’s hard cock, and I imagine gripping it in my hand and maybe, despite how unflinchingly straight I thought I was, slowly putting my mouth on it.

I peruse craigslist late at night, looking at the mostly faceless pictures of male bodies and hard dicks, fantasizing about meeting up with one of them and finding out what it’s like. Eventually I jerk off to a mixture of straight and gay porn and forget the whole thing. I decide it’s not a fantasy I’ll ever act upon. This happens frequently, at least three nights a week. But one night I’m feeling particularly restless and I can’t allow myself to repress the urge with masturbation any longer. I quickly make a new email address to preserve anonymity, and I reply to a few of the posts. I go for the ones with the sanest, most reasonable descriptions, and the ones closest by.

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.

Spring Break got a little crazy [m/m/f]

So I just got back yesterday from a 4-day cruise and really want to share this story with you guys. I’m a 21 year old college student going on my first real vacation where I can drink alcohol and not with my parents, and going with a bunch of other college-aged people so I was excited on the partying that was sure to happen over the week.

After I strike out the first night, the second night on the cruise I hook up with a smoking hot blonde named Sarah from a southern school. I’m from the north and was turned on by her southern bell accent and her great ass I saw on the pool deck at the start of the day. She was about 5’5″ and looked stunning in a bathing suit or in a dress. She had curly-ish hair and had a more cute than hot face, if you guys know what I mean. This story really isn’t about that night though, I’ve hooked up with girls before and the sex was nice, but nothing totally awesome. We fucked in doggy and missionary and I came on her back.

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.

Jackson [MFM?]

Jackson

I had lost two stupid cases in as many preceding days. I wasted time after I got home from work because a girl that works in my office, that I have had sex with, said in her emailed invitation to happy hour that it went until 7. So I changed into my finest lumberjack/hipster/skater attire, drank two medium-sized glasses of rye whiskey alone, and ambled down the sidewalk to the designated bar which is five blocks from my house.

Arrival at 7:15 and nobody was there with the exception of a young woman from my office who was still attired in her somewhat ill-fitting suit from doing her own trial that day. She informed me that the others had been there, but had left prior to 7pm, babies.

Had my [M] first jerk off buddy [M] today, things escalated quickly

TL;DR: found a jerk off buddy after a year of looking at this stuff, but the jo bud part lasted 10 minutes before it goes into make out, kissing, bj and 69. Did satisfied both my jo bud and bi-curious side in an hour, feel good now!

First off, its been almost a year that i stumbled onto r/jobuds subreddit and since then I was hooked to the stories and the community. I had a few jerk off sessions on kik in and off during the year.

I lurked on craigslist last week because I wanted to “get done with it once and for all” and actually do a real jo session with another. Found a guy that was about my age and shape, but the wording of the post sounded that he was more gay than straight bi-curious. I didnt mind because im a bit bi-curious so i wouldn’t have minded if during the jo session we would stroke each other.

The Turning [NSFW] [M/F] [Oral]

I was enjoying a quiet sit down in the park that Thursday afternoon, coffee in hand and the sun on my face. A perfectly, warm autumn day. I took a sip of coffee.

“Ah-BOO!” my interloper yelled from behind me.

I almost dropped my takeaway cup on my lap, dislodging the lid in the process. Coffee dripped through my fingers and sprinkled over my shirt.

“Hello Kelly. You’re late”, I said, ignoring the provocation. It would never do to appear rattled with this one. She would enjoy it too much.

The girl sat down on the grass next to me and took a cup of takeaway coffee from the disposable cardboard tray next to me.
Please meet Kelly: a jolly elf of a lass, 27 years old and quite stunning. My only complaint, if I should be forced to own one, is that her hair was cropped too short for my liking. She wore a Ramones t-shirt, blue jeans and sneakers. Or, as I tended to think of it as – Kelly’s all round year uniform.

“Hardly late”, she replied. “Blame the bus, Mr Anal”.

His wife wants to see him fuck a boy (m/f/m)

Okay so the reason im sharing this story now is because it might sound wierd to some of you and it’s supposed to be a secret so I guess it isn’t anymore. Okay last year we had a new neighbour (couples), they just moved in to the neighborhood. My first thought on them were they were pretty awesome people, They both went to different gyms. I was 19 and at that time and quite tiny and I would mostly visit them since they lived just next door and were quite friendly, little did I knew they both had a weird fetish. Okay so moving on, I kinda liked him and I would peek him every now and then while coming home from the gym.,I think he noticed me but whatever, I never thought I was gay though. One day they invited me over for dinner which I wasn’t sure at first but then I accepted it anyway. All I remember was that @10:30pm or so he was fucking me and his wife was watching *pause* okay now just a thought of it even makes me feel gross , okay back to the story. I remembered it really turned her on. I have heard of stories like these but never imagined it would happened to me. And by the way his dick is the biggest I’ve ever seen maybe 9inches (not sure) but it was big. He fucked me a doggy position with my ass up and face down on a the pillow while his wife kept urging him to fuck me harder (that bitch). It felt good though, I almost felt like I was going to cum every time he pounded me with my hands tied behind my back , he untied my hands and made me lie on back that’s when the wife came and unexpectedly sit on my face making me eat her pussy while her husband fucks me. At this point i couldn’t think of anything but feel the big dick inside me. Finally his wife got off and he lifted me with holding both of my legs which I guess isn’t a problem since I was tiny. Then he fucked me while lifting me, as he start to pound me faster and harder. Then finally he suddenly made me bend down on my knees and splash his cum on my face. At that moment i was feeling like a slut, he was beating his cock on my face I guess. From that moment I couldn’t recalled much . I woke up in their couch in their loving room the next morning. But only his wife was there saying that I better get home as soon as possible . I left quitely feeling confused. Did they drugged me?

[fm] Bullying and emotional/sexual rescue/nursing, [reluc] witnessing [Bullying] light [huml] light [Msub][Vanilla]

I was no snob in school. Despite being beautiful, meaning I had some lucky genes, I still hung out with a rag-tag group of retards. Just nerdy, strange, people. People who didn’t exactly fit it. Mostly because a lot of them were androgynous or gay/trans, also because they played games, watched anime, the typical considered geeky stuff. So I wasn’t by any means the top of the social food chain. Though even my friends considered me out of place among them. Having come from an extremely wealthy family I dressed well, was white, female, straight teeth, great vision, couldn’t gain an ounce of fat even when I tried. Like I said not stunning but rather lucky genetically. Enough to feel like an outsider in my insecure group of dorks. Also weird enough mentally and emotionally to feel like an outsider among the preppy rich kids.

No where was right for me. Trying to fit in I held a lot of thoughts and emotions back. About life, depression, sadness, I was very angst ridden for a while.