Indiscretions of [m]y youth with a [f]riend’s mom

Sorry for the length of the story, but here it goes. Also, all names have been changed to protect others identities.

A few points about me…

I was nineteen years old and things were going pretty well. I had a job, and at that time it paid way better than minimum wage. I was in college, mostly trying to figure out what I wanted to do. At that time I was fairly muscular, 5'10", and about 175 lbs. I'm not big in the dick department, statistically average. In high school I didn't have a lot of luck with girls, but as I got to college things started to change. Women weren't throwing themselves at me, but I wasn't having much trouble.

Background of the story….

Anyway to the event for this story. I was single, partying my balls off, and generally was on the hunt constantly. This particular night, like many others, I went to a bar that was fairly relaxed about underage consumption laws. I mean this bar was ridiculously easy to get into and get drinks at. I got fairly drunk, and being the stupid, young dumbass that I was got in my car to go home. (Note to those reading, I don't condone my actions, but rather now find them reprehensible.) Anyway, I was halfway home when I realized a few things: a) a cop had just appeared in my rearview, b) I was way too drunk to be driving, and c) I really needed to urinate.

Life with Emily Part 1. Falling for my slut lover and her wife.

I hadn't really been that successful in my relationships with women until I met Emily. I had no trouble starting a relationship but each time, after a while something seemed to be missing. I always lost interest in them sexually as a growing sense of need would take over. I never knew what the need was for so it remained a sort of nagging psychic itch.

Of course the women I dated were not the women I was attracted to and I knew that. I was attracted to them physically and emotionally but I had to force the sexual interest. On the other hand, the best, most intense and fulfilling relationships I had were with escorts, strippers and porn actresses. Not just any escort or whore but those that were in the business because they loved being the business. Those relationships never worked out, never because of the sex but because after a while I didn't connect with them as people.

I was stuck. I dated women I liked as people and found them sexually unappealing, or I dated women I loved sexually but could not connect with them at any other level.

Watching Porn with my roommate [F/M]

The year after I graduated college I lived in an apartment downtown. Rent was pretty expensive so I had a roommate who had attended the same university. We met through mutual friends who suggested we split the place. Alan was an engineering grad but was looking for work all the time. He was getting short contract hires for a month or so to at a time to fix buildings but it wasn't very stable and he would be at home for weeks with no job.

There was a few times where I would walk into our apartment and could catch the few seconds of porn noises or the shuffle of turning off the TV quickly. My roommate would watch porn often when I was gone. I didn't care, it's not like I didn't watch porn myself. I usually watched it on my laptop in my room with headphones so he wouldn't know but he liked to plug his laptop in the TV to watch instead. It didn't bother me as much as he probably thought it did.

Bangang Her Skrillbox [M]

There are many ways one can infiltrate the forbidden zone through the means of Tinder, Ok Cupid, and if you roll that way Grindr. Yes of course I’m taking about the world of free online dating, because lets be reall If you’re paying for it you reek of desperation

People use these dating sites for multiple reasons. Some want a relationship, others just want a fling, and me being on my longest cold streak since breaking up with my ex, 8 weeks, I was just looking to smash something, yes something not someone, that’s into kinky, light bondage, and who isn’t afraid of a little ass play. My goal, as is for every one and done, is to establish that I’m only looking to paint their stomach with my man goo just as Bob Rosss paints a scenic picture on an easel.

So to make sure the girl knows this from initial contact my go to opener is always ”we should cuddle.” While 80% of girls think I’m a complete creep, a small fraction actually respond and I continue to push the cuddling aspect.

I fucked two married women yesterday

Sorry, this is a long story. But you're the only people I can tell.

Background. I'm married. Wife travels a lot. I like to have sex.

This story all started on Wednesday. I'd been seeing a girl for about a month, we'll call her Lynn. Asian, and about 10 years younger than me. Hot, fun and adventurous in bed. Then she got a little weird. Told me that she knew more about me than I'd told her (fake name, fake city, throwaway email and phone). Follows that up saying her husband found out. Not cool. I called her Wednesday morning and told her she needs to delete everything she has and cover her tracks; she gets upset and ends it. I followed the procedure here and deleted her number and all texts and emails. Burn it and walk away.

Sucked. I kinda liked her. I don't get emotionally involved, but mostly I was pissed because I was planning to meet her Thursday and now I found myself without a place to insert my penis.

Stupid me without a plan B, I get to work immediately.

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[f/m] Bathtub Blowjob

My boyfriend [21m] have I [22f] been together for five years, currently living together in a little one bedroom apartment. I'm May and he's Tim. I've always had a higher sex drive than him, but to be honest, in the 1.5 years we've been living together, sex has fucking skyrocketed. I'm pretty naturally submissive, so there's a whole lot of quick casual blowjobs. I figured I'd share a cute, simple thing that happened the other night.

We have a full bathtub in the apartment, which is cool because all through college we'd been dealing with shitty dorm showers. Well I love the bathtap and the cetain…ahem…pleasures that it brings me, but both of us just like sinking in and soaking in hot water.

The other night we'd just finished up a movie and Tim decided to hop in the bath for a bit. I was settled into the couch with my phone and reddit when I see his face pop out of the bathroom. He gave me a little look and I knew it was on. We've fucked in the bathroom a ton, but I decided that this would be different. I know how much he loves being in the water.

Weird but hot? I fucked my girlfriend next to her sister, who was being fucked by her boyfriend. [mf] [mf]

This story happened some years ago, and it was awesome and weird at the same time. My then girlfriend Julia was an amazing girl. We had a fun relationship but it ended very abruptly. She was hipster, but in a good way. She wore little make up but was still extremely sexy and sexual. She had an amazing body, curvy with amazing big breasts and ass.

We were both out of town (and out of country) students in this city and we met through mutual friends while partying. Her parents had plenty money and rented her an amazing apartment together with her sister, Christina. Christina was dating Luiz, a very cool but shy guy who lived in Mexico at the time. Luiz tried to come over as much as he could, but she had a hard time with the long distance and time difference thing.

Third (and best) time visiting a hooker

EDIT: First time visiting a hooker

Second time visiting a hooker

My experience with the memorable handjob by my busty friend in Pimlico provided plenty of wanking material for the following months. It was my default memory anytime I jerked off without porn and I'd replay it over and over, picturing those milky white tits and my cum glistening on them.

I moved to Finchley in North London not long after. My new place was big and soulless, my housemates friendly enough though. One of them was a girl called Sarah who was a bit chubby and had decent sized tits. She was timid and quiet and her boyfriend spent a lot of time at the house. I once caught a glimpse of her naked arse through her slightly ajar door. I stopped and looked but as quick as I had spotted it she had moved out of view. I would often find myself staring at her bosom when she wasn't looking, imagining my cum spraying as she wanked my hard dick. It was pure fantasy though. There was no way anything would happen there.

20 – [F4M] [Oral, Fantasy, Island, Master]

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Mom and Dad insisted we do the big summer family vacation thing over all of our objections. Robby was pissed he was missing hanging out with his buddies over the last summer before leaving for college. Sarah was constantly texting her latest boyfriend and refused to speak to anyone. That suited me fine because she's a bitch. And me? I wanted to squeeze my new bigger boobs into last year's bathing suit and finally convince that hunky life guard at the YMCA to show me what I've been missing. Oh well…

I have to admit the island resort was great, but as soon as we got checked in Mom did her whole take over the schedule thing and dragged Sarah and me to the spa. Don't get me wrong, I love being pampered but I want it on my terms. When the girl at the front desk greeted us, I asked for the gorgeous, dark-skinned masseur to rub me all over, but Mom insisted I get a masseuse instead. Then she took the masseur for herself with a barely suppressed smirk.

Canada the prude

I was reading Nabokov's Lolita this week and was inspired to chase down the Canadian Child Pornography laws. I considered this a grey area, but upon reading the Wiki article I find the description of child pornography to be very harsh.

And of course, who can say anything… won't someone think of the children.

FTA:

Prohibition covers the visual representations of child sexual abuse and other sexual activity by persons (real or imaginary) under the age of 18 years or the depiction of their sexual organ/anal region for a sexual purpose, unless an artistic, educational, scientific, or medical justification can be provided and the court accepts that.

If I were to write a story about my sexual adventures with my wife back when we were under 18, I could be thrown in jail. Or how about a graphic novel?

If we were to act by the letter of the law, Canadians would not browse ASSTR or many other Erotica Sites due to the prohibition.