[M]y School Colleague Sally

My confession involves a teacher. A truly hot teacher. She was one of those teachers you always wanted to get when the timetables were handed out at the start of the academic year.

Every boy wanted to be taught by her, because she had a stunning figure. And she wore clothes that showed it off brilliantly. Plus serious heels.

Every girl wanted to be taught by her because she had a figure to die for. And she wore clothes that showed it off brilliantly. Plus a collection of shoes that were all their envy.

Only I was not one of those pupils. I was a colleague of hers.

My confession starts one cold, drab winter’s lunchtime and as luck would have it I was on duty with her. She was in a long black woollen coat, scarf, leather gloves and long, black stiletto-heeled leather boots.

Sharing a duty with – let’s call her Sally – was a dream. Not only was she gorgeous to look at, she was also fun. Up to now our discussions on our weekly playground duty had ranged from marking and problem pupils, to what we watched on television to what we were cooking for supper. We had talked about our other halves – how we met, how long we’d been together; what we liked about them, what annoyed us about them.

A Birthday Surpise

“I have a surprise for you!”

I sent the message to Sophia while sitting in the cafe a short walk from the apartment. It was her birthday and I wanted to make it extra special. Besides the presents I had already bought her, and despite the plans I’d made for a special meal out together, I had now come across an opportunity far too good to pass up.

“Ooh, what is it?”

“You know that’s not how surprises work. I have some instructions for you, Doll:”

We had started using codewords a few years ago to signal that one of us wanted to initiate a “special” interaction; I would call her Doll, and she would call me Sir. We’d been doing it so often, for so long, that it now had an almost instant effect on both of us, triggering a change from our typical husband & wife relationship to one of sub & dom.

“Yes Sir, whatever you say Sir!”

“Careful! You don’t want to be a brat tonight.

“I want you stripped naked, on your knees, waiting for me in the living room. You will be harnessed, blindfolded, hands cuffed to your thighs with your hook in.

Playing with his wife after I [M]ow their lawn.

I will start out light and if I get any comments I will continue.

To begin with I was a young guy that was in a broken home and we had very little money so I did odd jobs for people.

At 18 I had saved up and bought on old lawn mower and pushed it around looking for anyone that would hire me so I could buy my school clothes instead of having mom buy my stuff out of a goodwill store.
I was lucky and met several couples that would help me out and one couple stands out more than others.

Jess and his wife Naomi were very nice and the summer when I turned 18 they put me to work helping dig a swimming pool for them and Jess and I would go out back as the guy running the back hoe worked then it was my job to get into the pit square out the sides.
I never saw him and Naomi argue at all and they were very close kissing and fondling each other openly in front of me and when Jess would get carried away Naomi would laugh and push him away saying not in front of Jim now be good.
They were both very affectionate and she would always hug me whenever I came around and Jess always remarked about a young man willing to work.

Yours… On My Knees

I am kneeling before you. Eyes downcast, waiting. A shadow passes across my face and for a moment I forget myself and glance up to see what cast it… and my eyes meet your cock, standing ready, so close… a tiny gasp catches in my throat, and then I remember and lower my gaze.

Then your fingers, so gentle, are playing across my features, tracing my brow, my cheekbone, my jaw, sliding underneath to my throat. I am trembling. Still gentle and yet demanding now, your hand closes slightly, grasping, tilting my face upward. Permission to meet your eyes has not been given and so I carefully keep my lashes lowered, peeking through at what still stands ready before me, pulse quickening, mouth and tongue heating, lips wanting, dying to part but held firmly shut by my last scrap of will.

A rumbling chuckle from you. I know you must be amused.

You move your hand again, this time sliding up my cheek and into my hair. Your touch is so soft… until you make a fist, clenching where hair meets scalp, the stinging shock bringing tears to my eyes. With this leverage you tilt my face upward even further, and I understand your unspoken bidding and meet your gaze… gentle, playful, and yet I cannot miss the steel beneath. The command, quiet and soft, holds the same:

[MF] Quarantine anal with my girlfriend on the mountain.

As the coronavirus quarantine continued to linger on, week after week. My girlfriend and I sex life has never been better. With all this time locked up inside alone, we have been finding new ways to explore kinks and fantasies. My girlfriend Liz has explored her body in many new ways. One of the interest we have been exploring is anal play. I bought Liz earlier in the year one of the jewel butt plugs, which had a bright green emerald on it. Liz was hesitant to put me in her butt where she could only take the plug or a few fingers at the time. Seeing that bright emerald sticking out from her hole while I pounded her from behind was driving me crazy with lust.

During our fuck sessions, my fingers would wander towards Liz’s hole. I would rub, press against and if the mood strikes, tongue her asshole. Liz would always press my face harder into her ass while I ate her out. As she came to like it, me teasing her hole would only lead to braver moves. Liz is short, barely 5 foot with D cup boobs and a large round ass. She doesn’t wear bras most of the time, and with both of us working from home. We have been fully naked more often.

[F]ucking [M]y boss at the gym I worked at in college.

When I was 18 and first starting college, I looked around campus for a work study job. One that would be flexible with my school hours and pay a decent rate. One of the first spots I applied for was at one of the gyms on my campus. My campus was fairly large and where the freshman dorms were, a smaller run down gym resided in an older building. There was a work-study program through the student activities union to work the front desk at the gym, sign in students, and maintain the minimal equipment. I applied and was called for an interview later that week.

I met with the director of student activities, her name was Alicia. She was tall, a little shorter than my height of 5’10inches and looked fairly in shape. Alicia had to be in her mid-thirties, she had dark tan skin and curly brown hair down to her shoulders. The interview was very casual. We talked about school and working out, which I was very into at the time. Alicia complimented my physique, saying I looked like I spend many hours in the gym, so why not get paid for it. Alicia offered me the job right there, we shook hands where I noticed no ring on her finger. Our hand shake seemed to linger too long, both of us staring into each other’s eyes.

[MF] My breeding agreement with an older woman.

Back when I was in college, sophomore year, Tinder and Okcupid were all the rage. As a horny 19-year-old, access to pussy with the swipe of a finger was gaining traction. The benefit of Okcupid was having the full profile of the person. Well, one bored Sunday evening, I set my Okcupid age range to 45+. Soon I was flooded with potential profiles of older woman.

One woman caught my eye very quick. Her name was Clara. She was 47, was 5 foot 10 and very curvy. Clara’s pictures were elegant, where she was dressed in tight form fitting dresses that barely contained her massive breasts. Her long auburn hair flowed neatly down her back. Her body looked even tan, silky and smooth.

I sent her a message, saw that she viewed my profile and sent me one back. We chatted for a bit, basic small talk. I sent her one message looking to gauge her interest.

*“Well what brings you on here”* I typed.

*“That is a funny question you may ask, one that has a bit of a long story. Mind if I call you”* Clara typed back. We exchanged numbers soon after. I dialed Clara, very old fashioned of her. She picked up quickly, her voice was silky smooth.

[F]ucking [M]y girlfriends best friend in the ass [Part 2].

I came home from fucking my girlfriend Tara’s(T) best friend, Bell (B) that evening. Tara and I spent some time talking about what it was lie with Bell and if we obeyed the rules, no fucking her pussy and no kissing. I sheepishly lied and told her no kissing, even though there was peck here and there. I let her know that I only fucked her ass and fingered her pussy to help her relax a bit.
*“Where did you finish”* Tara asked me, avoiding eye contact.

I suddenly felt nervous, almost ashamed *“Well, inside her”* I said.

*“Ah, I see”* Tara said, avoiding eye contact further *“Did you enjoy?”*

*“I did, but nothing beats you babe”* I playfully said, wrapping my arms around her.

Tara hugged me back. I pulled her in closely and our lips met for a passionate kiss. We made love that night, soft and gentle. I couldn’t help my mind wandering to Bell’s tight asshole. Morning came and I headed to work, Tara works from home. Giving me kiss goodbye, I slapped her on the ass and headed out. Bell texted me later the day, saying that it hurt for her to sit down and that she hadn’t been fucked like that in her ass in a while. I apologized and told her I’ll be gentler next time.

[F]ucking [M]y girlfriends best friend in the ass.

It was a cool fall weekend following my girlfriends and I’s 4-year anniversary. We were deeply in love and had plans to spend the rest of our lives together. At that point in time, we had many sexual escapades and were very attracted towards one another. My girlfriend, well call her T has a great ass. Round, thick thighs, very jiggly and all natural. Whenever we would fuck, my fingers would eventually find their way to her virgin asshole. Eating her wet pussy out, I would always slip a finger into her asshole. She’d moan and grind against my finger but that was it. Any discussion of anal sex would be shot down. She had a boundary and I was willing to respect that. Fingering and eating her asshole out were fine but no fucking. Times where I would be jerking off, my mind would wander to videos of anal sex. I was at the point where fucking T doggy style, I would imagine pulling my wet cock out of her pussy and pressing it against her tight asshole. My ultimate fantasy was to cum in her ass.

[M]ovie theater horror [F]lick

One summer, I was browsing Okcupid when I matched with the profile of a beautiful petite Asian girl well call M. Her pics were nothing too revealing as I scrolled through her bio. She had a lot of similar interests that I had. I sent her a message and not too long after, she replied.

We chit chatted for a bit, both recently moved back home from college for the summer, in our quiet, boring town. Our Okcupid chats turned into regular texting and snapchatting. After a while, I asked if she would be down for coffee.