[FF] I cheated on my HS boyfriend w/ my virgin best friend

Hey, this is my first reddit submission. Talking about my first (and only) experience with a girl.

We were 15 and I’d already been with my high school boyfriend for a year. I’d been sexually active for a few months, but my best friend, Nina was still a virgin. We were both young with dark hair and tan skin. I was a little tinier than her, with small tits and a cute butt. She was a more voluptuous, with full, developed boobs that I was jealous of. She’d always been kind of a homophobe, so I was surprised as to what happened that night.

As per usual, I spent Saturday night sleeping at her house, and after a night of popcorn and movies, we crashed out in her bed… I had a really hot dream that night; I woke up feeling super horny. I was laying on my side with my back to Nina.

Watching [F][Masturbation][Voyeurism]

The wine trickles loudly. In fact, it sounds just like the word – trickle. It irritates me. The purple liquor sounds to state it’s natural, innocuous state of being: just something that trickles. Meanwhile, I am left with an unnatural, corrupting eagerness to empty the entire goblet into my mouth and down my throat.
It should do the trick. It has to. With eyes and ears on me at all times, pulling over next to a couple of tramps or inquiring about a little something special from the bartender is not an option. I need to remember to buy some nutmeg next time the husband takes me shopping.
That car is idling out in the street again; some or other old 80’s station wagon. He sits there, donning his (rather fitting) pair of oversized, gold-framed bifocals. Altogether, it looks like a proper ‘I-touch-children’ starter kit. He’s not old, about my age. And he just sits there, car idling, never moving.
I started noticing him three days ago, late at night. I was going to mention it, but decided not to. He appears at a time when everyone else is occupied with weeknight soap operas. I hate soap operas. He gazes at the house, expressionlessly, the only bit of movement engaged by his eyes as he adjusts them to fix on me when I appear in the front door or a window. I wonder what he’s doing. I feel tired.
___
So, how do I take this? Do I snort it? Do I brew it into a tea? My heart is pounding. Why is my heart pounding? The husband walks past the kitchen. What will I say if he asks? I’ve already lapped up about a teaspoon of nutmeg from the palm of my hand – I told him it was for pumpkin pie, I should probably get started on that soon enough or he’ll get suspicious again. The spice burns, clumping and puffing as I try to stabilise it with my saliva. I take three more.
If only I’d read further than “four to eight spoonfuls of nutmeg can induce a high”, I may have learned the easy way. I want to vomit, but there will be questions. Instead, I lock the door and wrap myself cosily in the sounds of psychedelic black metal, careful about the volume. I can lunge into the creation: Watercolours, always. Just water. Just coloured water and paper.
When I consider the sea of possibilities, the multitudes of techniques and mediums and styles, it always leads me to consider histories and anecdotes of other painters and the sea of endless possibility and I have to stop. This is why watercolours. It is one thing. Maybe tomorrow something else. It feels like I have the flu.
Halfway through the emergence of a tree(?), the nausea begins to tug at the back of my tongue with dryness. I swallow it down, looking around for an empty vessel. Nothing. I suppose there’s no other choice. I swiftly and quietly release myself, and sprint towards the bathroom. I manage to paint the walls of the toilet bowl with little-to-no accompanying sound effects. The husband’s off to bed already, in any case.
I pass the kitchen, catching a glimpse through the window of the station wagon idling under the glow of the street light. His spectacles glimmer in my direction. I slip back into my studio. My heart threatens to break through the sternum; maybe she wants to run off and find a host with eyes that don’t see what these do, and with a brain that doesn’t dissolve the images the way mine is wont to, conducting its own watercolour symphony of life as it appears to be.
The fear vibrates through me. Could he actually see me from that distance? I haven’t the slightest what to do – all I know is that I should not nor want to bring anyone’s attention to it. It is meant for me; I am the object of scrutiny. At least this is all mine. He stays with me; the frames of his glasses glowing from without the darkness I cannot shut my eyes to. I must go to bed knowing he is still there.
He is always gone during the day – I check each morning. I’ve been asked to retrieve the weekly tabloid from the mailbox. The mailbox is affixed to one of the posts supporting and connecting the concrete slabs that wall in the house and front garden. This particular exercise excites me, as the mailbox would be the closest I’ve been to the site of the staring, the watching.
The sight of the space alone is enough to dig out a hollow in my stomach. It is as if he never left, and is merely imperceptible to me now. I poke my hand into the mailbox opening to retrieve the paper, struggle to grab a hold, and reposition myself in order to reach better. My eye is directed to the sudden, silent appearance of the long, slate blue nose of a familiar vehicle.
No eye-contact, not yet. He has been here every day, only hidden from sight. My eyes are fixed in their inspection of the front of the car, traveling back and forth between the headlights, the bumper, trying their best to avoid his face. They soon start to burn. I can no longer evade it. I am paralysed, but I can look up. His face bears no emotion; the half-smile is an empty default setting. The eyes are fixed, as always, on me – never blinking.
I manage to resurrect myself from the state of upright death, and turn to head back into the house. Even as the distance gains between us, even as I step inside, even as I close and lock the door between us, he is with me. I’m trembling, and I didn’t need a glass of wine or a mouthful of nutmeg to get here.
Before I know it, I’m googling the contact number of the local police department on my phone. It takes me the better part of two minutes just to finish typing in the search with shaking, twitching fingers. But I do not want to call them. The terror is coiled around my chest like a python squeezing me down to size. I will not call them.
For the first time in a very long time, life is here. It pulsates, it vibrates, it crawls and it does not go away. The last time I felt this way, I had just then been released from a particularly intense sleep paralysis episode, and was surveying my room for demons by the light of my lamp. I remember the shallow inhalations and the dryness creeping over my eyes as I refused to blink. I remember the sudden impulse to comfort myself, which I achieved by drawing the covers, pulling down my knickers, spreading my legs as wide as I could and masturbating.
I parted my labia with my fingers so that all the intricate, rosy details would be visible to the invisible creatures that sought to torment me. In my delusion, I felt their eyes moving over my exposed, quivering body as I proceeded to massage my clitoris to the point of orgasm. I felt much better, and went back to sleep.
I know what to do.
I scavenge for a scrap of paper and a pen. When finished writing, I head down the hallway, out the front door and straight to the mailbox. I make sure nobody else is present, then I hold out the paper so that my admirer can see it. My head is bowed, but I’m watching him. No expression, only the message I imagine reflected in his spectacles: “Midnight. My window – at the back, on the left.”
In this moment, I am on the outside, looking at me. I feel absent. Or, perhaps I am someone else. I hold up the sign long enough to be sure he gets the message. It is only when I turn and head back inside that the rush of fear streams over me. What have I done? I begin to contemplate the number of heavy items in my studio that can be used as weapons.
The day passes slowly as I absentmindedly complete small household tasks and paint and play with the cat and paint again. It is grueling, to say the least – listening to the minutes tick-ticking away in your head and knowing all they draw closer to is the future, near and far. I’ve become adept at dragging with me this consciousness of time, every day listening to the ticking away, but this is different.
Midnight, on my open converter couch. I set the bottle of whiskey down on the floor next to me. I feel better now. The couch is conveniently positioned directly in front of the window and I am able to draw the curtains without stepping off. Holy fuck! The effects of the booze are nearly cleared from my brain as the bastard startles me, standing there like a mere silhouette in the moonlight, spectacle frames glistening.
I slowly back away, quivering. I slump to the bed, landing on my back as if in a faint. To my luck, I am still slightly intoxicated. I feel I need to, but I cannot keep my eyes off him. I slowly slide my knickers down, and decide to lift the night dress over my head as well. I am completely exposed. My skin ripples with goose bumps as my fingers glide down to spread the lips. I begin massaging myself, watching him watching me. I have to pull away every so often to avoid coming too early.
Next to me, I had set my secret toy: a glass dildo, and though I had never actually grown accustomed to using it, I thought it rather suitable for this occasion. It is plain, and if a light were to shine directly on the zone, my insides would be visible. I continue stroking my clitoris until I am sufficiently wet. He merely stands there, not moving.
I reach for the toy and first caress my clitoris with the tip, rubbing it down, down till it meets with my vaginal opening. I gently push it inside, taking quick breaks to relax and reset my vaginal muscles around it. At last, its entire length has disappeared into me, and the sight of this only arouses me that much more. He moves, as if fidgeting, and out comes a flashlight. He shines the narrow beam of light directly on my genitals.
He likes to watch, and only watch – a silent, black statue drinking in the sight of me getting closer and closer. The only part of me that exists is that which is illuminated while the rest of me trembles in the dark. I dig my heels into the bed and raise my hips as it comes closer and closer. The light follows, as if fixed, as if in actuality streaming from within me.
I’m beaming. I’m beaming brighter. And the world begins to melt. My fingers glide over and back and over my soaked, engorged clitoris. I pause to display her in the bright spot of light, watching him as he watches her. I press gently down on the base of the dildo, hugging it tightly and feeling its pressure against my vaginal wall. Then, I continue. Slowly, gently. My hips roll to the rhythm of my hand and… finally.
I crash back onto the bed, my torso curling up as I contract with the inward pull of the little death, and delight in the sensation of the dildo pushing back aggressively against the contraction. Mouth open, teeth bared, eyes forced open – fixed on him. My feet slide in under me as I thrust my pelvis forward. I attempt to keep my voice inside, but I need to shove the pillow in my face to do so. I stay with it as long as I am able, eyes rolling up and teeth grinding.
When I can bear it no longer, I release myself and feel the warmth of my lungs escape in great wafts. I open my eyes after scarcely five seconds of recovery to see that he had disappeared. I think that is the last I’ll ever see of him.

More perks of being a Substitute [Mf] [blkmail]

As I walked down the hall to the class I would be subbing for I saw Samantha walking towards me, I gave her a little smile and told her good morning. I was still thinking about our encounter earlier in the week, I had been replaying in my head every day. “Good morning!” Her cheerful reply let me know it was going to be a great day, and I hoped that she would be in one of my classes.

I sat down at the teacher’s desk and looked through my roll sheets, but I did not see her name, “damn… oh well, it’s probably for the best.” I muttered to myself. I made it through several classes with little excitement, as far as I could tell Samantha had not told anyone about what had happened, so I had that going for me.

Happy ending [mm]

According to the title it would seem like any other typical happy ending story. But it isn’t BC in this story the masseuse got the happy ending!

I’ve been going to a legal normal massage spa facility for sometime now. And there’s this one guy who is gay and I love his work. I try to make appointments with him as often as I can. He’s good looking not normal body. The norm. He always flirted with me and I’m not gonna lie, I like it and didn’t turn them away .

Normally I do hour massages but this one time I booked a 90 massage when I found out he was available. At this point the flirting was getting advanced and I’ve been dieing for a dick to suck on Bc it’s been so long :(

So as we enter the room I told him to stop massaging when an hour is up saying I want a half hour to relax. So he agreed. The massage went normal as usual, along with the flirting.

I had sex with a man for the first time and now I think I’m fucked in the head [MM]

I’m a 28yo man, fairly fit, and I’ve been told by more than one girl that I’m quite good looking. I’ve been curious of what it would feel like being with a man for as long as I can remember, but until now I had never acted on it. I’m sexually attracted to women and I’ve had many girlfriends, but I’ve always had this nagging feeling that I might be missing on something that I’d enjoy.

So last week I chatted up a guy on Craigslist and I told him about my situation. I told him that I had never been with a man (even though I’ve masturbated with toys many times) and that I wanted to try. We exchanged some photos, he asked me a full pic with body and face and I obliged him. The mere fact of taking nude photos of me for a complete stranger excited me to no end. In return I asked him to send me a pic of his dick. I realized I was not really interested in how the guy looked, I just wanted to see what the dick that was going to pop my man cherry looked like.

The Questgiver [M] [GRP]

Inspired by [this post](https://www.reddit.com/r/WritingPrompts/comments/6bwc4u/wp_you_go_about_your_day_as_normal_but_notice_a/dhq1ojq/) in r/WritingPrompts

 

I started the first day of my new life the way I always did. I had my morning coffee, my morning wank, my morning shower. The drive to work was *okay*, except I kept feeling like I should’ve tried for a second wank. That’s Mondays for you.

The guard at the office opened the door for me. She always did that, but this time she smiled.

“Can I help you with anything?” she asked.

“I don’t think so,” I said, and tried not to finish the sentence with *Cupcake.* In my defense she did look like a cupcake, with a
sprinkling of freckles and a rather soggy bottom.

“I mean, really,” she said. “Anything I can do for you? Anything you want?”

I bit my tongue. There were many things she could do for me. But this was no way to behave in a professional setting. She kept
pestering me, though.

“Look, why don’t you just go and pick up my dry-cleaning?” I said.

If only I’d known.

 

Everyone at work was giving me funny looks.

The Questgiver [MFFF] [bdsm] [fantasy] [Fsub]

Inspired by a post in WritingPrompts

 

I started the first day of my new life the way I always did. I had my morning coffee, my morning wank, my morning shower. The drive to work was *okay*, except I kept feeling like I should’ve tried for a second wank. That’s Mondays for you.

The guard at the office opened the door for me. She always did that, but this time she smiled.

“Can I help you with anything?” she asked.

“I don’t think so,” I said, and tried not to finish the sentence with *Cupcake.* In my defense she did look like a cupcake, with a
sprinkling of freckles and a rather soggy bottom.

“I mean, really,” she said. “Anything I can do for you? Anything you want?”

I bit my tongue. There were many things she could do for me. But this was no way to behave in a professional setting. She kept
pestering me, though.

“Look, why don’t you just go and pick up my dry-cleaning?” I said.

If only I’d known.

 

Everyone at work was giving me funny looks.

A favorite Memory [MF]

“Let’s go find the mixer!” I mischeiveously suggested to Emma. The glint in her eye told me I was on to something and we rushed upstairs to give Landon and Veronica some
space.

 

As soon as we got upstairs and before we even got through the hallway, I grabbed for Emma’s hand pulled her around so she was looking at me. I gave her one last chance to protest before I moved in.

 

Her gaze darted between my lips and my eyes. She seemed shy or coy, but she ever-so-slightly bit one side of her lip – one of my personal favorite tells.

 

All of the sudden our tongues clashed as she attempted to climb up my body, her leg wrapping around my ass and her mouth was pulling mine into hers. I wasn’t used to such a vigorous partner, and it emboldened me. I used my body weight to pin her back on the wall. I grabbed her wrists and held them above her head.
She flushed red and I could practically hear her wetness flowing as she pushed her mound into my hip. I spread her lips with my mouth and our tongues fucked each other. It was animalistic, urgent. Each volley of thrusts was bolder, deeper than the last.

The Questgiver [MF] [BDSM]

Inspired by [this post](https://www.reddit.com/r/WritingPrompts/comments/6bwc4u/wp_you_go_about_your_day_as_normal_but_notice_a/dhq1ojq/) in r/WritingPrompts

 

I started the first day of my new life the way I always did. I had my morning coffee, my morning wank, my morning shower. The drive to work was *okay*, except I kept feeling like I should’ve tried for a second wank. That’s Mondays for you.

The guard at the office opened the door for me. She always did that, but this time she smiled.

“Can I help you with anything?” she asked.

“I don’t think so,” I said, and tried not to finish the sentence with *Cupcake.* In my defense she did look like a cupcake, with a
sprinkling of freckles and a rather soggy bottom.

“I mean, really,” she said. “Anything I can do for you? Anything you want?”

I bit my tongue. There were many things she could do for me. But this was no way to behave in a professional setting. She kept
pestering me, though.

“Look, why don’t you just go and pick up my dry-cleaning?” I said.

If only I’d known.

 

Everyone at work was giving me funny looks.

[MF] My Girlfriend’s mom [Cheating]

okay….time to admit it…My girlfriend is 5 months into her pregnancy and it was an unexpected one but decided to get along to with it. BTW I am Jay (23) and my girlfriend Lizzy is 22. So as you would expect I was deprived of sex for the last few months and I was just wanking and watching porn like what a usual guy would do. Last week my girlfriend wanted us to spend sometime at her mom’s place for a week. We went there and I gotta say her mom, Mrs Patterson, has a great big house, although she is a divorced woman but a very attractive woman. I always had respect her because of how kind and loving she is. As we spending time at that place, I get my urges to have sex and then I usually go into the toilet and wank for bit and come out. It was about 6 in the evening, I went into the toilet and started wanking thinking the door was closed, but the lock was loose and her mom walked straight in and saw me with my dick in my hand ”ooooohhh….im sorry …” she rushed back outside. I got myself all embarrassed and got back up quickly and open the door slowly and walk back into our room feeling all weird and shy. I did not tell my gf about this and just acted normal. Later that day, I was watching TV while Lizzy was sleeping upstairs and her came downstairs wearing one of them black transparent nightie. She got be off guard and sat next to me with her on my shoulder. ”Jay ….I know what you are going through at the moment…it is okay,…every guy goes through this at this time” she said. I was like ”i mean….im sorry….i feel so embarassed” i told and she replied ”no need to be embarrassed…you should be proud”
I could not understand what she was saying and i turned to face to ask her that but by that time she was all on her knees. i had the shock of my life but i did not want to let this opportunity go as i desperately needed a cunt. I took my willy out not even bothering about the fact that she is my gf’s mom. She took it in as if she had never seen a cock in life. Gotta admit that she was better than lizzy in giving a blowjob. I was thinking to myself what am i doing… am i doing the right thing….but i could not careless and carried on with it. She blowed me for like 5 minutes and then asked me sit on the sofa and she wanted to ride me…and she needed some attention. I was like ”are you sure Mrs Patterson” and she replied ”call me Sarah…Jay” in a seductive tone which caught me by surprise and made me so horny.I pulled my pants down and sat on the sofa with my willy straight facing 12 o’clock. she slowly pull down her panties and came close to me and stood on top of the sofa and slowly coming down. that site alone would have made me cum so much….but i waited and she slowly slided me into her and she felt so tight…”you are so tight sarah” i moan to her … she replied ”i am having sex after a long time” and i was stunned by that given how she looks and her body shape…”come on you must have had guys” i say while she goes for quick ride.
she giggled at me and moaned so much and then changed position to look at me and it carried on for a while ….before she eventually stopped and wanted to cum over her face and i got up and squirted a load on her face and then she blowed me for few mins and went back into her. i cleaned myself and went and slept next to lizzy…