collection of stories you shouldn't read at work
Yesterday, for the first time, I felt capable playing a dom top.
While visiting the college I graduated at (mid 20s) I popped open Grindr, setup a top hookup, and make my way to the dorms. In my few experiences topping, I’ve never known what my partner wanted and always felt I was messing things up, so I had stuck to bottoming for a little while. Today, I was resolved to get better and wanted to try some of the things I’d want a top to do to me, but only if my partner reacted well.
I would usually get naked when giving James head. I mentioned before it turned me on when he would talk dirty to me when I gave him head, but even more so when I would be naked and going down on his cock and he would reach down and spank my bare ass or begin to play with my ass. Eventually, he began to play with my asshole, fingering me and making me shiver as he pushed into me up to his first knuckle and pressing into my prostate.
The fact that James was playing with my ass as I gave him head made me wonder if he wanted to fuck me, but he never brought it up. Still, I was fascinated with the idea and wanted to give him the opportunity. I wanted to see if I could take it. So I went to the local sex shop to see if I could find a toy I could use on my ass. I found it in a black, vibrating butt plug that was about 1.5″ wide at its base. I wasn’t sure if I could take it, but it seemed like a good start. While I was at the store, I also noticed a super cute, skimpy, leopard print bikini that I was so drawn to that I had to buy it as well.
#2
Vienna Austria or: when college boys need a break from finals.
It was a sunday in Vienna, my last in the city, and I was perusing the local gay saunas on offer from the comfort of my hotel room. As I narrowed down my two best options for the evening my phone chimed, another grindr message arriving. I opened grindr and saw my pet peeve, a photo-less profile. For whatever reason i decided to open this message where normally I would have deleted it straight away… i am so glad i did. He was my type: lean and athletic, light hair and smooth pale skin with a warm smile. He is a 24 year old master student in vienna and looking for a break from writing papers. We messaged back and forth for a while, exchanging photos and desires. He is a vers top and explained he didnt usually bottom and might be too tight for me. This seemed to truly concern him so i let him know i would go to the saunas and if he wanted to come over later he was welcome to. I went to the first sauna and it was empty ?, so much for group fun that night. Walking back outside i checked grindr on a whim, my college boy had just messaged me a minute prior. He needed a break and wanted to come over. Thirty minutes later we met outside my hotel and made our way up to my room. He was gorgeous. Wavy blonde hair and a shy yet warm smile. I grabbed him close and kissed him deep exploring his tongue with mine. He pulled my hips tight into his pressing our growing cocks together, separated by too much clothing. He peeled my shirt off as i unbuttoned his jeans and slid my hand in to feel his now hard uncut cock. He pulled his own shirt off between us kissing and i pushed him firmly back onto the bed. There was a moment of levity as his skinny jeans got stuck at his ankles, we both laughed before i gently manipulated them off of him, adding them to the growing pile of cloths on the nearby chair. His body was just as nice, firm from youth and exercise, very little body hair and a smooth uncut cock already dripping in anticipation. I straddled his chest and pushed my cock towards his waiting lips. He hungrily took me in, sliding his tongue around my tip while bobbing and twisting his head. I grabbed him by his soft hair and slowly deeply skull fucked him. I wanted to be in him and so it was time to start warming up my prize. I slid off him and onto my back pulling him on top of me. He was a voracious kisser, seemingly in need of what my lips and tongue had to offer. While kissing i moved a hand down from his firm softly fuzzy ass to our cocks that were glued together by lust and a glimmering layer of precum, i started to stroke us both slowly. It was early, but he was close. He asked if he could cum soon so that the rest of our night could be about me. I granted him permission so long as i got him off, he wasnt allowed to participate actively. He nodded submission and sat up on my thighs. Still holding our cocks together i stroked us while working a finger around his tight tight hole. After minutes he let out a weak whimper “im going to cum,” i slid my finger fully into him aiming for his prostate, he exploded! He shot hot wads on my stomach and chest as he pulsed around my still inserted finger. His lips crashed into mine again while i used his hot load to lube up his still tight hole. Between kissing and fingering him i slid on a condom and lubed my head and shaft with his load. I pulled his cheeks apart and aimed for him, he slid his hips back and down in an attempt to take me in, but he was still too tight. During the next ten or so minutes we kissed passionately while i continued warming him up with fingers and the slow steady pressure of my now throbbing cock. At last I felt it! One of the three best moments of tight anal sex 1) my tip breached, squeezed tightly by his ring where my shaft and head meet. He let out a gasp and a slight shudder. Another ten minutes of making out and complimentary hip movement: him rotating while pressing into me, me thrusting slowly and consistently up and into him, then the second best moment of tight anal sex 2) he slid fully down onto me. The feeling is of this total pressure at every point of sensitivity around my cock, a full and complete envelopment. This time we both let out a gasp of pleasure. I pulled him hard to me spreading his muscled cheeks apart and his body fully to mine and rolled him under me and me on top. Kissing him still i started thrusting harder and faster into him slowing only when it seemed i was overly pressing his comfort levels, but he loved it. He warmed up to being my bottom bitch, moaning and whimpering as i continued fucking him harder and faster. I was getting close so i grabbed him by the hips with one hand and the throat with my other, slightly choking him while pulling him hard back into me. I felt that sudden rush as i exploded inside him, my cock pulsed again and again as i came and his asshole squeezed tightly around the base of my shaft in shared pleasure: the third best part of tight anal sex. Breathing hard I collapsed on him where our sweat and his lingering cum mixed. He released his grasp on my hips and melted into the bed searching again for my mouth while i lingered inside him savoring the moment. Finally our lips parted and i pulled slowly from inside him then from on top of him and to standing. I pulled him to his feet and to the shower with me. Scrubbed and redressed we parted ways. The next morning I was off for another adventure.
One of the things I found myself doing when I would suck James’ cock was I would strip down completely naked. Like I said before, I loved it when he talked dirty to me while I gave him head, telling me I was a good little cocksucker and a good little slut. It was even better when he would spank me as I went down on him. He took it further when he began to occasionally play with my asshole, sticking a finger into it, sometimes pushing deep into me. The first time he pushed up against my prostate, it sent a thrill up my spine. As he do this, he’d take me by the hair and push my face down on his cock so it was deep down my throat.
I wasn’t sure if he wanted to fuck me, because he never came out and said it. But I became really curious about what it would be like. I went to a local sex shop to buy an anal plug so I could see what it would be like to have my ass filled. I found this cute, medium sized, vibrating, black butt plug that was about 1.5″ in diameter. I thought it might be a little bit too big, but I couldn’t resist buying it to try it out.
As I flop onto the deep blue damask couch I happen to lookup and catch the look that I dread.
“And what is it that you are forgetting right now pet?” You say quite evenly as your eyes gleam with a mischief that makes my mind race.
With a start that makes my eyes go wide it dawns on me… “I should be cleaning up because we have to leave tomorrow.”
Grinning at me you point to the floor at your feet, a sign I know very well. I slide off the couch to the dark hardwood floor and crawl to your feet, kneeling and kissing each of your toes before looking up at you. “That’s better pet, now get on all fours and put that cute little ass in the air with your legs spread as wide as you can.”
As quickly as I can I press my face against the coolness of the wooden floor and lift my hips in the air, knees spread wide apart. You must have had the crop hiding somewhere because you bring it down on my cheeks so swiftly it takes my breath away for a moment. The loud smacks fill my ears as I try not to wiggle my ass too much. After a few good swats I feel you begin to rub my ass and spread my cheeks. I moan softly at your sensual touch and relax my face against the rapidly warming floor.
Chapter 1
Both of us had been looking forward to this event for the whole week. Lola and I were beginning to feel the slow come up as we sat in the back of the Uber, stroked each other’s legs and settled into the sensation of the MDMA we took about a half hour before. I could feel her palms sweating against mine as we held hands. I was nuzzling my head on her shoulder when I turned to face her, and smiled. She looked back at me and grinned, “hey” she said warmly, and we kissed. Her lips felt extra soft and lush so we luxuriated in that kiss. Her hand was resting on my chest and she nibbled my lip and pushed her tongue into my mouth. I was getting excited, and I reached behind her. My right arm moved beneath her crop top that exposed her lower back and belly. The left hand reached down her skirt, and beneath her panties…
The car stopped but the driver didn’t say a word, we noticed him checking us out in the mirror and we laughed and said our thanks, and then got out of the car.
So to start, no I am not gay but this will make you question that lol. So about 3 years ago, some buddies of mine gave me a huge black dildo as a gag gift. I kept it as a joke and show it to people randomly.
So recently I have been taking an interest in anal play. So when I was masturbating today, I stuck a finger in my ass. It went in easily amazingly (this is seriously my first time trying this) I start trying to push my prostate to make my orgasm a lot better but it wasn’t working out to well. So since I was about to shower, I decided that I was going to get the dildo and see if I could get it in. As an experiment.
When she opened the door, the look in her eyes was a mixture of fear and excitement. Her big green eyes looked up at me and followed a path across my wide shoulders and down to the whip coiled in my right hand. I had the strap of a duffel bag slung across my chest. I had been given a list of things that she wanted and it contained the tools that I would need to accomplish them. This was a bit out of the ordinary. Usually, I show up and take instructions, but this five and a half foot, dirty blonde beauty wanted to be dominated.
She had a sheer white robe, tied in front, and I could see that she was wearing an outfit of leather straps, with no cups covering her breasts, that stopped at a belt just above her hips. She was wearing heels and stockings that came to a stop, mid-way up her gloriously thick thighs. She was clean shaven, or waxed, and she had a small gap just below her vulva. She was breathtakingly beautiful and her dark blonde hair was pulled back revealing a leather collar with a large metal ring in the front. In her hand was a long, leather leash, which she offered to me with a submissive smile.
My favorite game is where one of us wakes up first and tries to wake the other one up with their lips and tongue. I’m not exactly sure how you beat me to it this morning, but you did. The thought that you probably stayed up all night plotting this floats through my mind for only a moment before you apply enough suction to the head of my cock that it takes everything I have not to react. That’s the other part of this game, pretending to be asleep as long as possible. You always win that part, but that’s largely due to how much I enjoy having my face between your thighs.
I feel you slide a hand up my thighs and playfully caress my balls as you idly suck on my head. I’m just barely able to stifle a moan as you tug on balls pulling them down away from my body as your whole mouth devours the length of my cock. I am not however able to stifle the twitch in my cock as you twist my balls a little upping the pressure.
My former husband ruined these lands. He was a miserly, stubborn old man who let his people starve and succumb to disease for years as madness clouded the end of his reign. Most wicked of all was that he had the audacity to use his authority to force me to marry him, then to die, leaving me without an heir to retain control of the crown yet shouldering the responsibility of it.
I have done things I shouldn’t. Made deals with beings whose names couldn’t be uttered by human tongue. Entities who it would be called mad to commune with, much less bargain. The Inquisitor would see me burn for what I have done…
…if he wasn’t currently on his knees at the foot of my bed.
I have entertained many lovers in these bedchambers since my husband passed. Men who offered a young woman comfort only to act like beasts behind closed doors. Others who offered aid and guidance, at the price of letting their obese, sweaty forms gyrate between my legs. I’ve had…many lovers, yes.