[MF] Heroine Lipstick. (And yes, it’s a real color)

The lipstick color was ‘Heroine’. Not ‘violet’ or the sweeter, passive ‘lilac’: something to be plucked and displayed in a vase, sniffed delicately. The color of an insignia on a page, an action-movie costume. Panned up to reveal a direct gaze, holding with an adversary in the face of certain danger.

And though not dangerous in the usual way, I looked up into an unfamiliar face, wide, dark eyes sliding lower in tandem with the movement of my lips on his shaft. Halfway down, his lashes screened his eyes, giving him a shyly lazy look. I popped him out of my mouth: a wet, thick, treat of a cock, glistening under the fluorescent lights. His gaze flicked from my smile further downward, exhaling in a sharp huff; I didn’t need to look to know he was seeing the smudge of purple lipstick near the base, shading faintly upward toward the foreskin and shiny, delicate head. The pinks of my tongue and that sensitive skin shockingly close, intimate, as I lapped while he was watching, enveloping him once more between soft and clever – if slightly less brightly colored now – lips. Read more »

The night I got incredibly lucky and lost my virginity [MF]

When it comes to my early sex life, I like to think I got by on sheer, dumb luck. I was an awkward kid in high school into early adulthood, not bad to look at, and pretty funny, but also weird, shy, and not very fashionable. So imagine my surprise when I lucked up and got myself a smoking-hot girlfriend my junior year, whom I’ll call Carina. She was 5’2”, medium-brown complexion, lithe figure, nice tits, and later, a tattoo on her lower back.

Long story short, I fell for her hard. When we broke up, I went to pieces. I was a mess. I spent that summer out of the country with relatives and came back with my head on straight and ready to move on. After I graduated, I got my first job at a department store and was getting ready to start college on a scholarship. All in all, things were looking up.

Then one day, I got a phone call. It was Carina, looking to reconnect. She extended an open invite to hang out at her place, anytime. Literally anytime. In my naïveté, I thought nothing of it other than she was trying to be friendly. Yes, I was once that clueless. Read more »

mischievous checkout chick [MF]

I should set the background of this story. I was working for a supermarket chain at the time that i couldnt stand being at, so i didnt really care about what I was doing day to day. Im a younger guy, what do younger guys tend to do? Anything sexual.

So there was this cute girl that would work the checkout most mornings during the week, 4 years younger than me, legal by a few months. I would always catch her staring at me. So i thought fuck it, il flirt in the mornings a little bit and lay some ground work. It didnt take very long for some teasing to happen and some not so safe for work things started to happen.

Now, we worked in quite a small local supermarket. Open some weird hours, not a lot of staff on. So we would try to catch each other up stairs in the offices with nobody around to catch us out (as id previously been caught having sexual relations with a staff member at a different store i worked at, being the reason i got moved to the one where all these proceedings went down) Read more »

I love giving my boyfriend road head… this time, we almost got caught [MF]

Hey y’all, this is a separate account from my main one for obvious reasons. I wanted to be able to post some of my crazy sex stories since me and my boyfriend are pretty adventurous to say the least. I have a bunch of these so let me know if you guys enjoyed this one and want to hear more.

My boyfriend (22) and I (20) have been together for about 5 months now officially, but we liked each other and we’re best friends for a long time before that. There had been so much sexual tension that when we finally fucked it was phenomenal and we haven’t been able to stop since then. We have sex or do sexual things almost every single day and it has not slowed down since we first started dating.

I have a very high sex drive and he definitely keeps up. Usually, he teases me for a few days before letting me cum, that way I’ll be desperate for a while and when he finally does give me an orgasm it’s one of those super intense ones where I’m flailing and screaming and can barely walk afterwards. Read more »

Unexpected [MFM] from a Craigslist hookup many years ago

This origins of this encounter go back a while and I don’t really want to bore you with the details (at least not this early on). Put simply, I had been broken up with and I had a lot of demands that I wanted met for my own personal gratification before I could commit to another relationship. This is the story of one such instance.

I had swapped emails with what I assumed (correctly) was a woman on the now defunct Craig’s List personals. She was looking for a guy. I could tell by the word choices that she was a real person. She used the word groovy once… that pretty much sealed the deal for me. We met, had quality sex and when I was cleaning up, I noticed she had some other condoms in the bathroom trashcan. When I came out of the shower, I asked how many others had accepted her invitation. She said it had been “worth her efforts.”

“Why not call one of them, see if they’re not too busy,” I said. I had wanted a threesome, but instead of with two women, I wanted it a woman and another man. There were certain things that two men can do that two women simply cannot. Read more »

The Submissive Professor (18)

Jessica kneels at my feet, looks into my eyes and wraps her lips around my dick. We looked into each other’s eyes and I can see the love and desire she still has for me …. but I also see distress and fear. Would her feelings be a threat to Mistress Michelle’s sadistic domination? I didn’t think so. There is something else I sensed in her, something deeper, more insidious. My Femdom Mistress kept me in a cage for six days exciting me to “keep me in shape,” she said. I wanted to cum since I did not want Jessica to get whipped.

So I focused on my pleasure since I suspected if I didn’t cum my mistresses would be merciless on her. Jessica knows the most effective caresses to get me excited. Mistress Michelle gives the time every 30 seconds to put pressure on us to finish quickly and to distract us so that I can not cum on time. I don’t want to think about it. To return to my cage after having my love’s mouth wrapped around my dick, then having to deal with her punishment would be beyond what I can deal with at this moment. Read more »

[FM] I travelled for 2 hours to get fucked in a park at 10 a.m.

Originally posted this elsewhere but it got removed, so I’m hoping GWS is a better home for it.

Here’s a story about [a guy called J](https://www.reddit.com/user/deeprixx) (25M) and what is probably the most effort I’ve put in for nothing but abuse in return. Side note: I’m exploring masochism, I got hit really hard and J is kinky/mean, if that’s not your thing you may not enjoy this. I may well post more because god knows I have a few stories.

I responded to J’s ad on my local r4r sub looking for girls who got turned on at the idea of torture. Yeah, I knew what I was getting into. We met up for a casual drink so I could check he wasn’t catfishing me or a creep (he was actually weirdly shy, it was kind of sweet). We got along, and basically established next time we saw each other I’d be getting abused. Read more »

Circumnavigation, pt.2 (NSFW, mf, romance, autobiographical)

Chapter 3, Sint Maarten

My new found friend and I made our way from the beachside café up toward the point of land between the two bays on the southern coast of the island of Sint Marten. Our ship had anchored about a mile out in the Great Bay and we’d rode an overloaded water taxi to a pier on the East end of the boardwalk.

We’d been looking forward to getting off the ship to be by ourselves for a while as we had recently discovered that our uncanny ability to get along had a pretty intense new physical aspect to it. In other words, we were horny as hell and wanted to bone each other’s brains out!

Unfortunately, Sailors on a US Navy warship are under military regulations forbidding any and all such activities aboard ship. Just a day ago, we had been caught up in the moment and forgot all such rules and I had fingered her to orgasm which she then sucked me off until I had climaxed in her mouth, all just a few inches above the ship’s bridge crew on the deck below us! Read more »

Circumnavigation, pt.1 (NSFW, mf, romance, oral, autobiographical)

Circumnavigation, risking it all

Prologue

Note: This series is autobiographic, the events are true as I can get ‘em to memory, but it’s been 22 years and a few details may have run together. It’s long and takes a while to pick up steam, hopefully not too boring ^_^

In 1996 I was active duty Navy and assigned to my first ship, a guided missile frigate home-ported in Mississippi. I was 23 years old, happily married, full of myself and from what I could tell, at the start of a successful career.

I had already completed one deployment to the Middle-East and had the obligatory “Sailor experience” under my belt of wandering from bar-to-bar, sampling food from cafes and street vendors, shopping in bazaars and boutiques in Barcelona, Haifa, Hurghada, Massawa, Djibouti, Manamah, Dubai, Muscat and Marseilles.

Through all of that I maintained my marital vows and thought myself all the better for it. I had been tempted, tested and tried numerous times and escaped with my virtue unscathed. I wore my fidelity like a crown and secretly judged my shipmates who failed the test. *Sigh* The higher the pedestal, the farther the fall. Read more »

Tee (NSFW, crossdresser, CD, mm, oral, anal)

“Tee” is very special to me. Our relationship started after my first deployment to Afghanistan and my first experience with a trans person. I suppose I had a whole new world opened up to me sexually, one where the sex wasn’t defined by gender roles, but rather the connection and passion alone. The “equipment” used was meaningless!

Aria was unavailable due to incompatible schedules and I had duty at the base again. The base was in the next town over from where my family and I resided, so I was confident that my extracurricular activities were safe from being discovered (I was right about this too, which allowed me many more experiences than I’ve been able to have since).

Once again I placed an ad, but this time specifically seeking a transsexual. I stated that I had my first experience and wanted more. Tee answered my ad, but stated up front that she was a full-time crossdresser. No hormone therapy and no intentions of physically changing genders. She had a prosperous beauty salon business and lived, dressed and existed as a woman. Read more »