by Louis Friend
Was I enjoying this? I had to admit that I was.
My cock was rock hard in my pants. I heard another moan and realized that it came not from the man whose cockhead I was licking but from me. I took more of his cock in my mouth, wondering if I’d be able to fit the whole thing in. Does that really feel better than just the tip? I had to wonder because I had never had this done to me—by either a man or a woman.
I was twenty years old and still a virgin in quite a few senses of the word.
So, here I was sucking a guy’s cock when I hadn’t even “gotten my wick wet” as the saying goes. It felt so right though, and so good. I was taking him as deep as I could, afraid of gagging. I didn’t want to throw up! I just wanted to give this guy as much pleasure as I could. I began really sucking, making sure that my teeth weren’t hitting him at all, making my lips smooth and taut as they went up and down on his shaft.
I couldn’t believe it, but it felt like he was getting even harder and bigger as I moved my head up and down. And, suddenly, I heard him say “Oh, shit!” With that, he began bucking his hips, pushing himself deeper into my mouth than I would have liked, but I also felt the warm flow of cum filling the condom.
He slowed and pulled his deflating dick from my mouth. He yanked the condom off and went to throw it in the toilet behind me. I had to stop him and tell him that I wanted a souvenir.
“Whatever, freak,” he said, putting his cock back in his pants and leaving.
*
“Now, let’s see if you followed my directions,” she said. “Strip, all the way down and get on your hands and knees. Place your clothes on the chair over there.”
While I nervously unbuttoned my shirt, she got up and walked out of the room. I couldn’t believe either how fortunate or how dumb I was—I had yet to make up my mind on that one—as I stripped in this relative stranger’s house. It occurred to me then that I didn’t even know her name.
Eerily, the first words out of her mouth upon her return were, “You may refer to me as Mistress Lily.” And, with that, she menacingly snapped the rubber gloves she had donned.
I got down on my hands and knees, my cock hard and exposed. She kneeled down next to me and ran her latex-covered hands over me, inspecting me. I knew at that moment that I belonged to her and was powerless to do anything about it (not that I really wanted to do anything contrary to her wishes). It almost sounded as if she were purring as she gently touched and probed my body.
“Very nice,” she whispered to herself. When her hands found my cock she whispered, “Very nice indeed.”
“Thank you, Mistress Lily,” I responded, not sure if I should say anything but wanted to acknowledge her compliment.
Ignoring me, she began stroking my cock. While this may sound highly erotic—and it was—it also had an element of chore to it. She wasn’t masturbating me so much as she was milking me—testing my reactions and pushing me. I was getting hotter by the second, listening to her breathing get faster as she worked her hand harder. It was when she slid a finger from her other hand inside of my tight ass that I couldn’t take any more.
“You must ask permission before you cum,” she warned me, sternly.
I knew that I didn’t want to know or experience the consequences. So, as quickly as I could, I asked for permission.
“So soon? No. I’m rather enjoying this,” she said, starting to pump her finger deeper inside of my ass, working now in time with the hand stroking my cock.
I didn’t want to disappoint her but she was taking me right to the edge of orgasm, and it felt like I was going to cross that brink. Without even realizing it, I started whimpering.
“Oh, poor baby,” she said with open mockery. “Is this too much for you?” She slipped another finger inside of me. “Does he like to get ass-fucked?”
I whimpered again, hating to admit how much I enjoyed the feel of her fingers violating my ass.
“Does he?” she demanded.
“Yes, Mistress Lily,” I admitted.
“Good…. I’m sure that I can help out with that. I’ve got a big dildo that I’d like to fuck you with… if you can prove you’re a good boy. Prove it right now. Cum for me.”
With those three words, I exploded, my cum hitting the wooden floor beneath me, her hands milking the last few drops from me. I hated to admit it, but when she removed her fingers from my bottom, I missed them.
“Oh my, look at the mess you made,” she said, removing her gloves and sitting back down on her divan. “That simply won’t do. Get down there and clean that up. Don’t swallow it all though, leave some on your tongue.”
I did as she said. It was difficult, tasting more cum. But I wanted to make her floors spotless. With a tongueful still present, I kneeled before her once again, my limp cock twitching as she leaned over to taste a drop, touching her tongue to mine.
“Mmmm…” she moaned. “I told you that I could tell if you came in that condom. I’m glad to see that you didn’t. I’m glad to know that I now own a cock sucking whore. You passed your first test. Tomorrow will be your second. But, for now, you’ll crawl behind me to my bedroom. We have a little more business to take care of before I need to sleep.”
I knew that I needed to crawl, rather than walk behind her as she made her way down the hall to her boudoir. I loved the look of her ass in motion as she walked before me, leading the way. I felt exhausted and exhilarated all at once.
Her bedroom was awash in candlelight. I wasn’t sure if it was a vast or small space as everything quickly went off into blackness. The only light apart from the candles seemed to come from Mistress Lily herself; her skin so pale that it seemed luminescent. Without ceremony, she told me to kneel as she lowered her underwear from beneath her skirt.
“You did well tonight, subbie. I’m going to give you two rewards. Here is the first,” she said as she draped her panties over my head, allowing me to smell her scent. I inhaled deeply, enjoying her aroma. All too soon, she removed them and threw them in her hamper.
She bent over the bed and raised her skirt. “Here’s the other. Lick my asshole until I cum.”
This hit me in the face like a bucket of ice water. The idea of licking someone’s anus seemed deeply repulsive to me. Wouldn’t I get sick? Weren’t there germs there?
But, yet, somewhere inside of me I knew that I had to do what she commanded. And, moreover, I knew that she wouldn’t have me do something that would harm me. And, for some reason, I assumed that she, like all girls, kept herself very clean. Still unsure, I took her ass cheeks in my hands and spread them wide. I looked down to see her pretty pink pucker and knew what I had to do.
I lowered my face and put my tongue against her tight sphincter. I began licking it like I had read that a man should lick a woman’s vagina. I started with small circles and then darted my tongue into her quickly. It was after I heard her moan that I knew I was doing something right.
My repulsion soon diffused and was replaced by pure pleasure. I began licking her with abandon, pushing my tongue deeper and deeper. She actually tasted delicious, a bit like candy. I buried my face between her fleshy ass cheeks. Just as I had felt lost in her eyes, I was now lost in her ass. Time stood still for me. I felt that I could do this all night and into the next day. I was absolutely in love with the sensations I was experiencing and the knowledge that I was pleasing her.
It took me a while to hear the noise that I realized had been in the room for a while now. It started like a low purr but had turned into a higher pitched wail. At first I thought it was an air raid siren or a cat in heat. Instead, it was coming from Mistress Lily. I almost slowed but realized that she wasn’t in pain but in extreme pleasure. I began tonguing her deeper and deeper—flicking my tongue around the entrance to her ass. I could feel her begin to shake, her legs coming up and going over my shoulders, pulling me closer and deeper inside. I could smell her scent again, fresh and overwhelming. I could feel the heat from her sex on my chin as I tongued her faster now.
Mi
stress Lily let loose with a string of muffled obscenities. Her legs began twitching and shaking like mad. I didn’t stop and I didn’t want to stop. I wanted to lick her forever. Finally, she moved her hand back and pushed my forehead back, removing me from her ass. “Good boy,” she said, exhausted.
She crawled up onto her bed and patted the spot next to her, inviting me to join her. She reached into her bedside table and pulled something out. She handed it to me and told me to put it on. It was a short pink nightgown—I think it might be called a “baby doll nightie.” In no mood to argue—and knowing that I shouldn’t—I put it on over my head and lay down next to her. She wrapped her leg over me and soon fell asleep. I felt like I was in my skin for the first time.
Riding the Wave
I don’t think that I give off a “BDSM Vibe” but apparently I do. I think that I emit this peculiar wavelength that comes from an incident at my first “real job”—one that wasn’t held down part-time while attending classes, or where I had to wear a uniform.
The company I worked for hired a new office manager, Marla Strom. She was an unimposing slip of a woman. She was likely in her fifties. She looked like she would have fit in best at one of my mother’s Book Club discussions.
There was little cause for me to interact with Marla. She spent most days on the phone in her office, managing supply vendors, repairmen, and who knows what else. Yet, occasionally Marla would play “Den Mother” to the pack of web developers. She’d make an appearance, going through the rank and file to socialize. I had engaged in a few pleasant conversations with her, nothing out of the ordinary, until about two months after she’d been there when she was bemoaning how empty her social life had been since moving to our metropolitan area.
“I just don’t know where to find the kind of fun I’m used to,” she said.
I suggested that she take a gander at some of the free newspapers that were available at the record store in the neighborhood. This seemed to pique her interest. She asked if they had any “club listings” and I started to jaw on about the live music establishments downtown.
“No, not that kind of a club,” she said.
She left this door wide open, waiting for me to step into it. More than a statement, it was a question and she was awaiting my answer.
Oddly, I knew that I wasn’t reading too much into her question. Whatever wavelength I was riding, I knew she was sharing the same ride. I don’t flaunt who or what I am, so the moment it took me to decide what to say next seemed to take an eternity. I felt like I was standing at a precipice so I plunged over the side.
“I think I know what kind of club you mean. There’s one downtown, The Grasshopper, at Debussy and Bartok. It’s only open Friday and Saturday night after eleven.”
She nodded, knowingly. “And what night can I count on seeing you there?”
“I haven’t been in months but was thinking of going there this Friday, as a matter of fact.” It wasn’t the most truthful answer. I had no prior plans of going there but now it seemed suddenly to be in my best interest.
“Great, hopefully I’ll see you there,” she said, touching my arm as she walked past me on the way back to her office.
It didn’t take more than a second for a hot cold flush to come over me, one that made me question both my judgment and my sanity. I’d let the cat out of the bag about my proclivities and I got the image of Marla putting in a call to the Human Resources department in Washington to file a complaint about the pervert in her local office. My head was swimming with ill-fated scenarios but, still, in the back of my head, I wondered if Marla was simply just a “freak” like me.
The rest of the week I didn’t see but passing glimpses of Marla in the office. The debate went on inside my head on whether to show up on Friday night or not. Yet, somewhere inside, I knew that I would be doing so, no matter how many reasons I gave myself not to.
Friday found me in the smoky shadows of The Grasshopper with the thump, thump of house music matching the nervous patter in my chest. I was nursing a drink when I saw Marla across the room. She was talking to a rather striking, tall brunette. Marla was barely recognizable outside of the context of our office and in a rather revealing outfit that included a leather skirt and a blouse that revealed her brassiere from certain angles beneath translucent black material.
Before I could think to do anything, Marla noticed me and nodded. She flagged me down with a wave and I made my way through the crowd of twenty-to-sixty-somethings that comprised the Friday night crowd.
It was more than a little difficult to make conversation over the music. I caught that Marla was with her friend, Dee, and that they were glad to be out on a Friday night for a change. Dee wasn’t one for making much eye contact, I noticed, as I tried to listen to her and Marla.
After one particularly lengthy speech, Marla leaned into my ear and asked, “You didn’t hear a word I just said, did you?”
I sadly shook my head.
She smiled wide. “Okay, let’s get out of here.” She said something to Marla who slugged down the last of her drink before adjusting her purse and nodding her ascent.
Outside in the crisp winter air Marla seemed happier than I’d ever seen her. I don’t throw this word around much, but she seemed “giddy.” The same couldn’t be said for Dee, who was far more reserved. After walking with the two women for a while I realized that I hadn’t a clue where we were headed. They were walking with a purpose and destination in mind and I tagged along like a puppy hoping to get a treat.
We walked for only a few blocks to what looked like a warehouse.
Marla produced a set of keys and unlocked the door saying, “The best thing about that club, it seems, is that it’s so close to my space.” She unlocked the door and we went inside.
I still didn’t know what was in store for me, at least consciously, but I think I knew on some level that Marla’s ‘space’ was her ‘play space’. An elevator ride later, my inkling was confirmed. Without even needing to explain, Marla and Dee ushered me into a large loft which sported a decorative theme somewhere between medieval torture chamber and college student apartment.
There was no negotiating or verbal sparring. There was no polite offer of tea, coffee, or wine. Things fell into place like a puzzle piece finding its slot.
Without ceremony, Dee began liberating herself of most of her outfit. Marla started to do the same then looked over at me. “Put your clothes on the shelf by the radiator.”
I had been trained well enough by the women that I had served previously to know better than to affect an attitude of shock and awe. I knew my place in this kind of situation, despite never having been in one before, and did what I was told, removing every inch of clothes and, with it, any artifice of control. Naked, I knew I was not in charge of anything any longer and belonged completely to these two ladies until told otherwise.
It was chilly in the loft at first. I wasn’t cold for very long after the blows began to fall. I was bound to the crux decussata. Marla and Dee took turns using various implements on my flesh, starting with a flogger and moving on to a riding crop, small belt, and even a wooden spoon. They started off slow but soon were determined to see how long and hard they could beat me until I begged for mercy.
Marla’s body was incredibly tight. Her gray hair was cut short in a spiky ‘do’ that gave her a lot of sass. Her blue eyes shone with glee as she administered blows to my ass; I could see the look reflected in the mirrored wall before me. I prayed that neither she nor Dee would blindfold me; it was wonderful seeing them strut their stuff, working up a sweat as they beat me. Occasionally Dee would opt out of the beating and stand in front of me, my eyes level with hers. She’d reach between the crux of the St. Andrew’s Cross to find my penis, half hard between being turned on and being in pain. She’d take me to full mast with her hand, staring me down while she manipulated me expertly.
“You like that, huh, slut?” she hissed, her husky voice making me harder. “Did you get hard when you saw us
at the club tonight? Did you think about getting down on your hands and knees right there and kissing our feet? Did you want to put your face between Marla’s ass cheeks and lick her tight hole? Tell me, slut. Tell Miss Dee everything.”
And, as the lash fell across my stinging, hot bottom, I confessed my sins. I admitted to how flush with excitement I was when I saw them and to the carnal sins I committed in my mind. Her skilled hands took me up the flights of stairs of my orgasm but stopped just before I jumped off the roof. She repeated this process several times as Marla continued to redden my flesh.
The slap of the lash was replaced by an odd buzz. I looked in the mirrored wall to see Marla with a new toy—a long white-handled tool topped with a purplish globe at the end. She applied it to my backside and I wailed out of surprise and a newfound sensation of pain as electricity seemed to rip through me.
“Shhhhh,” Marla chided as she put her cool hand on my warm neck.
Her touch was reassuring. I realized that this was the first time she had touched me. Her hands were soft but firm. She grasped to steady me as she applied the violet wand once again to the backs of my thighs. I tried to not wail as loudly as before, pushing air through my clenched teeth as the electricity crackled over me.
She held the wand to my thighs, my low moan turned into a sharp cry and finally I begged for mercy. She continued to shock me as she decided if she would show me any mercy or not.
Finally, she stopped the current. She began unbuckling me from the cross while Dee did the same. Weakened, they lead me to a low table in the middle of the room, laying me down on the padded surface.
Dee moved my feet up so that my knees were bent and my legs were open. I stared dumbly at the ceiling until I felt something cold and hard pushing against my anus. I looked down to see Marla holding the full enema bag in one hand while she inserted the nozzle with the other. I felt so vulnerable and humiliated as she opened up the flow and allowed water to enter me, flooding my bowels. I was even more embarrassed when the sensation set off my cock, making it hard enough for her and Dee to comment about.
