Sissy Idea Backfires
Here I was, on my knees, clad only in pink thong panties, sucking an amazingly large cock for all I was worth, while three women “encouraged” me – verbally and with their hands, at times, pushing rather firmly on the back of my head.
I realized that I had been headed in this direction for quite some time, at least a decade. How had I gotten to this point? I honestly didn’t know. All I knew for sure was that the raging cock ramming in and out of my mouth was getting close, dangerously close, to exploding! What then?
Some explanation is in order.
I had put myself in this new and rather awkward position quite unintentionally – I think – with one of my bright ideas.
You see, I like lingerie. I like it a lot, have for years. I absolutely adore wearing panties – and more when I am safely tucked away in a hotel room or some such place. I also like femdom humiliation. In fact, I crave it. But though an online mistress had “trained” me, from afar, for years, I did not really have a mistress. God, I wanted one, one who would force me to worship her pussy, one who would pound my ass with a strap-on, one who would humiliate me to no end. I craved that – all of that!
Once upon a time, my online mistress had actually taken me shopping at a renowned lingerie store. Though she went easy on me, no doubt, I loved it, absolutely loved being embarrassed in the store, in front of the salesgirl. I wanted more, more, more. But I had no real mistress to put me through my paces, so to speak. So I decided to “do it myself.”
I got the bright idea to venture to that same renowned lingerie store by myself, which I had done before, but this would be different. I had a typewritten note in a sealed envelope in the back pocket of my jeans, which I planned to pass off as being from my “mistress,” as if I did not know the note’s contents. In reality, I knew full well – because I had written it – that the note contained various instructions on how to humiliate me in the store – in front of customers and other workers. What would be the harm, I figured? I soon found out.
Upon entering the store and proceeding to a panties display, I was not surprised to be approached by a sales clerk. Of course, she was attractive – medium height, dark hair, which I love, a tight sweater displaying some rather nice assets and an adorable shape, top to bottom.
“Sandra,” her name tag informed me. Perfect, I thought. The first girl I ever fucked was named Sandra. Well, at least that’s the way I used to think of the experience, back when I thought I was a man, or at least on the way to becoming a man. In retrospect, quite some time ago, I had realized full well that it was actually Sandra who had fucked me. Or more precisely, she had fucked me over.
We were in college. I was a sophomore. Sandra was a freshman. But she was more experienced than me. Hell, everyone was more experienced than me. Sandra had had sex. In fact, being from New York, she had had sex with a famous stage actor’s son. She knew her way around the girl-boy thing. I certainly didn’t.
Every guy in our dorm thought Sandra was the hottest thing walking. The funny thing was, I didn’t. I really didn’t. For whatever reason, Sandra’s looks didn’t really appeal to me. She was knowledgeable and fun to talk to, but I didn’t find her particularly attractive. I think that’s why Sandra wanted me. I was the only guy in our dorm who didn’t fall all over himself for her, and I think she viewed it as a challenge to make me her conquest. To make a long story short, she did. We wound up fucking. Several times, in fact. Of course, I had no idea what I was doing. I didn’t even know how to insert my cock into Sandra’s pussy.
She had to do it for me. I remember after she abruptly broke it off with me because she hooked up with an older guy who undoubtedly had a much larger and more experienced cock, I worried that if I ever got another chance with a girl, I still wouldn’t know how to penetrate her without help. At the time, I was crushed. Hell, I had thought I was in love. I didn’t know the difference between sex and love. Sandra, though, wanted me to prove she could get me. At least I got a little experience, and certainly some fun, out of the deal. Many years later, I realized that Sandra had merely used me as if I were nothing more than a sex toy, a human dildo, if you will. That’s all I was to her.
So, now, I was standing beside this new Sandra, in the lingerie store, looking at panties. I told her that I had a rather unusual situation to deal with, that I had a note to give to her. She didn’t seem taken aback in the least. I imagine it wasn’t the first time for her, given her occupation. Anyway, I pulled the envelope out of my pocket and handed it to her, my hands trembling, and my heart pounding in my chest. I just wanted her to embarrass me in the store, and then I could race home and jerk off. I jerked off a lot, but this would be HOT!!
Sandra excused herself momentarily and told me that she would return shortly. I thought that seemed odd but didn’t think a whole lot about it. After a few minutes, Sandra returned with another woman, an older, beautiful woman. Soon, I would find out that her name was Megan, and she was the store manager. Megan explained that the note I had given Sandra was quite inappropriate and that she would have to discuss it with me – in her office!
“Um, that’s OK. Never mind. I’m sorry. I’ll leave,” I stammered.
“Oh no, you won’t,” Megan responded, in a stern, extremely forceful manner. “Sandra, bring him along.”
The next thing I knew, Sandra grabbed my arm and, for a rather small girl, displayed amazing strength in yanking me toward the back of the store. We followed Megan through a curtain, down a short hallway, and into a relatively small but nicely decorated workspace. There was a lengthy sofa on one wall and two chairs in front of a rather large desk. Megan took a seat in the large office chair behind the desk, while Sandra pushed me down into one of the chairs in front of the desk. Sandra sat in the other.
“Just exactly what the fuck do you think you’re doing?” Megan barked at me.
Not knowing what to say, I offered nothing.
“You think we have the time and energy to deal with pussies like you?” Megan snapped.
“Um, I … I … don’t know what you mean,” I stammered.
“Who wrote your ‘note?'” Megan demanded.
“My, my mistress,” I said, my mouth completely dry, my palms sweating profusely, and my heart racing.
“Like hell,” Megan fumed. “Why didn’t she sign it? It’s self-evident that you wrote the note and just came in here looking for your jollies. What a pathetic little bitch!”
Just about this time, there was a knock on the door. Sandra rose and opened the door. Another woman entered, a policewoman! She was so hot that even though I was scared to death, my tiny, little cock got hard in no time.
“Serena,” Megan said. “This is him. Or perhaps I should say her. Unless she cooperates, I fully intend to press charges.”
“P-press charges,” I asked. “For what? What did I do?”
Serena grabbed the nightstick out of her holster and began wielding it as she started to speak. She began to stroke it as if it were a huge cock. It wasn’t all that thick, but God, it was long. I glanced at Sandra. Even she looked a little bit scared.
“Strip,” Serena ordered, looking straight at me.
“Um, what do you mean?” I asked.
“What the fuck do I mean?” Serena yelled. “I mean, take off your fucking clothes.”
Not knowing what to do, I hesitated. I mean, what had I done here? I hadn’t committed any crime. What could they possibly press charges for? I was scared, confused – bewildered, really.
Figuring I had no other choice, I began to undress. I took off my shirt and then my shoes and socks. I was wearing jeans, and I figured I had better follow orders. I unzipped my pants and pulled them down, revealing the tiny pink lace thong I was wearing. It was all that was left.
The women immediately started laughing.
“Look at this fucking sissy,” Megan said, looking at Sandra. “I don’t even see a cock. It must be the tiniest one known to man.”
Sandra just smiled as Megan opened one of the drawers in her desk. After a bit of rustling around, she pulled out a strap-on cock, and then another!
“I only have these two here,” Megan said, looking at Sandra and Serena. “You two go ahead.”
Not needing to be told twice, Sandra removed her slacks and sweater, leaving her merely in panties and her bra and stepping into the harness. Soon, she was stroking the big cock in front of her. Serena did the same, taking off her police uniform, revealing her underwear. God, what a sight.
Megan just watched, snickering.
“Who’s going where, girls?” Megan asked.
“I want his boy pussy,” Sandra said. “I’m going to fuck his ass until he begs for mercy.”
“That’s fine,” Serena said. “I’ll fuck his slutty little mouth. On your knees, bitch!”
“Isn’t there some way we can…” I began.
“Shut the fuck up,” Megan commanded. “On your fucking knees!”
Giving up, I kneeled, looking in Serena’s direction. Her strap-on cock was at eye level, and I knew what to do. I opened my mouth, and she thrust that cock inside. I almost choked. Serena didn’t care. She kept humping. I wasn’t sucking her cock, or giving her a blowjob. She was, indeed, fucking my face.
“I need some ass,” Sandra said. “Serena gave me a few more thrusts, hard, and pulled out. I nearly collapsed, face-first.
That was perfect for Sandra, who jumped behind me. Fortunately, she had a handful of lube. I didn’t know where, or when, she got it, but I was grateful as she pushed aside my little pink thong and started to grease up my ass, as well as her cock! Sandra eased it inside my ass at first, but her patience didn’t last long. Soon, she was hammering away. Of course, I had fucked myself in the ass with dildoes many times and had enjoyed it, but the difference was that then I was in control. I certainly wasn’t now.
For the second time in my life, albeit in a markedly different fashion, I was getting fucked by a girl named Sandra. As embarrassed as I was, once I adjusted to Sandra’s pace and the rather large size of her strap-on, I rather enjoyed the sensations. I had always wanted to be fucked by a woman. I had never envisioned it happening this way, or happening at all, for that matter. But now that it was, I decided to enjoy it.
At one point, I looked up at Megan, who had the most satisfied look on her face. She was very much enjoying watching “her girls” use and abuse me. Soon, Serena stepped in front of me, pulled my shoulders up, and again thrust her cock into my mouth. For the first time in my life, I had a cock in my mouth and another in my ass, both working me over but good.
Well, they were cocks, but not real cocks. That was soon about to change.
Megan left the room for a short time, and when she returned, she brought along a very tall, very athletic-looking man. From the looks of him, he either played football or had played in the not-too-distant past.
Without a word, the man, whose name I later learned was Alan, stripped naked. His cock, the largest I had ever seen other than in a porn flick, was significantly larger than either Sandra’s or Serena’s strap-on. And he wasn’t even completely hard. Alan laid on the couch against the wall and said he was ready.
“Crawl on over, sissy,” Megan said. “You have a job to do.”
Almost in a daze, I did as she said. Still on my knees, I moved over to the couch, looked at Alan’s growing cock, and thought there was no way I could take it in my mouth. It was simply too big.
“Suck that cock, slut!” Megan ordered.
And for the first time, I realized that she was taking pictures with her cell phone. At about this same time, Serena began smacking my ass – hard! – with a paddle.
“Get to it, whore,” Serena snarled.
With no choice, or at least that’s how I felt, I leaned over Alan’s prone body, picked up his cock to point it at my mouth, and deliberately started licking the head. Never in my life had I touched another man’s dick, let alone had one in my mouth. It didn’t taste bad, really. Honestly, I didn’t even taste anything at all. I had given blowjobs to dildoes on many occasions, even fantasized about the real thing, but I never thought I would actually do it.
Again, Serena slapped my butt with the paddle. It fucking hurt!
I figured that it did a good enough job sucking Alan’s cock, maybe Serena would stop spanking me, and maybe I could eventually get out of here. So I began really going to town on that monster, doing the best I could. Honestly, I hadn’t received many blowjobs in my life, but I had certainly seen plenty while watching porn. I had a pretty good idea of what to do.
While sucking as much of his cock into my mouth as I could, I stroked the remainder of his cock with one hand and used my other to play with his balls. At least Serena stopped whipping my burning ass.
The more I sucked Alan, the more I began to enjoy it. I guess it was obvious.
“Look at his tiny, little dick,” Megan said. “Have you ever seen anything so pathetic?”
Megan, Sandra, and Serena all giggled. Alan, meanwhile, began to moan softly. He was getting close.
What the hell? I mean, I had tasted my own cum, on many occasions, but never another man. I wasn’t ready for this.
It was as if Megan had a sixth sense.
“Either you swallow every drop, or else these pictures are going to be all over everywhere,” she said. “Everyone in this town will know what a cock-sucking little sissy bitch you are!”
Soon, Alan exploded in orgasm, his cum jetting into my mouth and out. There was no way I could contain it all.
“Lick it up, all of it!” Megan snapped.
At that very moment, without any physical stimulation other than friction against my little panties, I came, too. My thong was drenched!
“Looks like he has another job,” Sandra said gleefully.
“Get those panties off – and in your mouth!” Megan barked as I felt yet another painful smack across both my ass cheeks.
I did as she said, tasting my cum along with Alan’s.
With my wadded up thong panties in my mouth, I cast a look down at my little cock, and then at Alan’s. While mine had shriveled up to next to nothing, Alan’s proud penis seemed to be just about as hard as it ever was, probably 10 times my size.
“What a fucking pussy,” Serena sneered.
I could not, in good conscience, disagree.
*This story has been edited to fix spelling, punctuation, & basic grammar, but the narrative and plot have remained the same. Just remember, even with the limited editing we do, it doesn’t mean any possible major flaws in this story were fixed.