Sissy’s Spa Day
I had met her through the course of my employment rather than by chance. My job places me in the public eye to a small degree, and, on occasion, there are functions where co-workers and I interact with the public. We chat with people all the time, and usually, it is nothing more than small talk. When it’s over, it’s over. But this was different.
She approached me and wanted to talk. At first, it was businesslike, nothing more, but I recognized immediately that something was different. She had a certain quality, a confidence that I had never quite encountered before. Despite being much, much younger than me, she was so sure of herself, so self-assured. Honestly, I somehow felt intimidated from the very beginning. I guess my intuition was on to something.
We talked for much longer than I usually spent with anyone in particular at these functions. In fact, we all but closed down the place, as workers had begun to clean up. She looked me directly in the eyes and said, “Meet me in 10 minutes at Starbucks — the one by the theater. And don’t be late.” I knew the coffee house well. It was about four blocks away. But what was she talking about? I had been planning to go home. But she didn’t ask. She told me. And then she immediately turned and was on her way. I couldn’t help but stare. Did I not mention that she is gorgeous? I watched her tight little ass as she walked. My God! She was probably about 5-foot-6, brunette, with radiant brown eyes. She was pretty much the girl — no, woman — of all my sexual fantasies. She didn’t have huge breasts, but definitely good-sized, and oh, so perky! But that butt. I couldn’t help imagining my face buried between her ass cheeks.
Right then, my boss, a very good-looking woman in her own right, albeit closer to my own age, snapped me to attention. “What are you watching so intently?” my boss Katherine asked as if she didn’t know.
“Oh, um, I was… I guess I spaced out,” I stammered.
“No shit,” Katherine replied, very clearly perturbed. “She’s not even half your age, asshole. You should be ashamed. If I ever catch you looking at any woman like that again, I’ll fire your ass quicker than it takes you to jerk off your pathetic little cock!”
I couldn’t believe that Katherine had spoken to me in such a way, even given my indiscretion. But she was right. I was ashamed. I had to admit it. What the hell was I thinking? But then I realized that I had only a few minutes to get to Starbucks. Wait, was I actually going to go? Should I? Should I just say the hell with it and go home? I made a beeline for the parking garage, got to my car as quickly as possible, and drove the short distance to the coffee house by the theater. I jumped out and walked hurriedly. She was sitting outside, at one of the outdoor tables. It was a pleasant fall evening, after all. Two other couples were sitting in the area. Well, they appeared to be coupled. We certainly weren’t.
“Sit down,” she said firmly. I pulled out the chair across from her and started to sink into it.
“No, here, by me,” she said, motioning to the chair to her immediate left. I complied. I’m not even sure why.
It’s just that the way she said things, her manner, seemingly left no choice. She reached into her purse and pulled out a pair of pink thong panties, holding them up as if to display them. From where I was seated, I was facing a woman and a man, one from each of the couples that were sipping and chatting nearby. The panties quickly got both of their attention. The man, younger than me and very athletic-looking, got a shit-eating grin on his face. The woman, probably halfway between my age and that of my female companion, appeared startled at first but then seemed quite interested.
At this point, the young woman next to me twirled the pink thong panties around in her fingers and spoke in a firm voice loud enough for everyone to hear.
“Take these to the men’s room,” she said. “Put them on. And bring me whatever underwear you have on now.”
At this point, the other two members of the couples near us had turned to look. All four of them had heard the words and saw my face. I was in downright panic mode.
It wasn’t the thought of putting on the panties that had me so frightened. It was the fact that I was already wearing panties! I usually wore panties. I loved the way they felt, the way they caressed my ‘manhood.’ The truth was that I hadn’t had sex, other than plenty of masturbation sessions, in many years. Wearing women’s panties was as close to pussy as I ever got. But no one knew I wore panties! If I did as I was told, my secret would be out for sure!
The other men and women seated nearby stared at me with looks ranging from surprise to amusement. I was frozen in place.
“Hurry up, Panty Boy,” my tablemate commanded, pressing the pink thong into my right hand with her left. “I don’t have all night.”
I could hear a good deal of chuckling from the other two tables as I started to rise out of my seat. What the hell was going on here? I stuffed the pink thong panties into my front pants pocket and headed for the men’s room, inside the coffee shop. I knew there was an exit on the other side of the building. Maybe I could make a run for it, although my car was on this side, in plain sight. Whatever. I didn’t have to get my car. I could walk back to my office from here and call a cab, maybe escape with my dignity — or what was left of it.
I entered the Starbucks and quickly faced the moment of truth, Left, toward the exit? Or right, toward the men’s room? I chose the latter. I opened the restroom door and was relieved that no one else was inside. I quickly entered a handicapped stall — more room to move around, you know? I thought for a second or two about the situation I was in, and really couldn’t comprehend it.
Just then, I heard the door to the men’s room open.
“Your date says to hurry the fuck up, Sissy Boy,” boomed a male voice.
I could only assume it was one of the men who had been seated near us. Then I heard the door close as he apparently exited the men’s room.
I took off my shoes and then my pants. I was wearing black, lace panties that left little to the imagination. I loved the way they looked at me, but that wasn’t the point right now. I slipped them off and hung them over a hook on the back of the door. I reached into my pants pocket and retrieved the pink thong. It was sexy, and I had to admit. I slid it up my legs and into place as best I could. There wasn’t much room for my, um, you know, but I did the best I could. I had worn thongs before, of course, so I knew the familiar feeling in the crack of my ass.
Ordinarily, I loved that feeling, but now it only added to my fear. I quickly put on my pants and then my shoes. I was just about ready to open the door of the stall when I remembered my black panties hanging from the hook. That would have been great, to forget those, I thought. I stuffed them as far into my pants pocket as I could and moved into the main part of the restroom, in front of the mirror. I looked at myself and realized I was quite a shade of red. I quickly splashed some water on my face and tried to regain some semblance of composure. Unfortunately, I’m not sure I succeeded at all.
Trying not to even think, I exited the restroom and walked out the door to the patio area. At my table, our table, she was sitting rather impatiently. The other two couples quickly ceased their respective conversations and were now watching me intently. I sat back down, where I had been before, feeling the thong ride up my ass as the front of the panties struggled to hold my male bits.
“So?” she asked, holding out her hand.
Momentarily confused, I just sat there like an idiot.
“Let’s have them,” she said. “Let me see what had been where that cute little girlie thong is now.”
Reluctantly, feeling five sets of eyes on me, I reached into my pants pocket, tried to wrap my fist around my own black panties to obscure them, and handed them over.
“I knew it!” she exclaimed, holding my panties out for all to see. “I knew you were a fucking slut! Black lace, see-through panties! Are you proud of yourself?”
I just sat there, petrified. The other two couples were laughing and giggling. But not her. Sitting right next to me, she wasn’t smiling at all.
“I asked you a fucking question, whore!” she barked.
“Um, no, I wouldn’t say I’m proud of myself. No. Not at all. I am… I’m… I’m not sure what I am. Why are you doing this to me?”
She laughed. Now it was the other four people in the area who were quiet, as if not knowing what to make of things.
“I’m not doing it TO you,” she said, rather sweetly. “I’m doing it FOR you. I could tell from about two minutes into our conversation tonight that you are a sissy, a panty-wearing slut who is just dying to have a hot, dominant woman take control of you. And you’ve proved it a hundred times over. Your life just changed forever, Sissy Boy.”
I was in something resembling a state of shock. The couples at the other two tables appeared to be, as well. Just then, she spoke to them.
“Look, I hope you all enjoyed this little show, but I’m afraid that’s the end of it. Ladies, take your men home and relive this any way you like. By watching both of them tonight, I can tell you that they probably wouldn’t mind being treated something along the lines of my little sissy here. Take them home, talk to them about it if you want, or just take control. My guess is they would both love to have some nice big girl-cock shoved up their tight, little asses.”
Then she looked at me, handed me my black lace panties, and told me to put them back in my pocket.
“Come on, Sissy. We’re leaving,” she said.
We got up; she took my hand and forcibly led me to my car.
“Give me the keys,” she said. “Get in the passenger seat.”
I did. She sat down behind the wheel and began to drive. For quite some time, there was nothing but silence. Finally, she spoke.
“This is the best night of your life, isn’t it, Bitch?”
I didn’t know what to say.
“Answer me, Cunt!” she roared.
“Um, I don’t know,” I began. “I don’t know what’s happening. Where are you taking me?”
She just laughed and kept driving. She was a damn-good driver, if seemingly a bit reckless. She took curves like nobody’s business and seemed to enjoy my concern.
Pretty soon, she screeched to a stop in front of a high-rise apartment complex.
“Take off your clothes,” she ordered. “Everything but the g-string.”
“Are you serious?” I asked. “I can’t…”
“Oh yes, you can. And you will,” she said. “From now on, you will do exactly as I say. Everything I say, Pussy Boy. Without hesitation. Or else!”
It was almost as if I was in a trance. I knew I shouldn’t. I mean, we were on a busy street, near the middle of a good-sized city, with plenty of light all around. It was dark enough inside the car, but still… I pulled off my shirt, kicked off my shoes and socks, and slithered out of my pants, leaving me clad only in the skimpy pink thong. She removed everything from my pants pockets — my wallet, cell phone, comb, some loose change, and placed them all in the center console. She pulled a large plastic bag from her purse and placed my clothing inside it. Then she handed me a piece of paper with a phone number on it and got out of the car, taking the bag of my clothes with her. Leaning in the window, showing off her ample cleavage, she told me to slide over into the driver’s seat. I did, moving ever closer to her gorgeous breasts.
“Do you like my tits?” she asked.
“Yes, ma’am,” I said. “Very much.”
“OK, Sissy, time for you to get home. Call me as soon as you get home. And I mean as soon as you get home. Ask for Mistress Monica.”
With that, she was gone. And there I sat, wearing only a pink thong, sitting in my car on a busy street, scared to death. I just hoped to God that I could drive home without being pulled over by the police, or getting into an accident, or…
I lived nearly all the way across town. It was at least a 20-minute drive. And, somehow, I would have to get from my car into my own apartment. Christ, I could get arrested for indecent exposure. I drove. I found myself racing and knew I had better slow down. It was an agonizing drive, with me constantly checking the rear-view mirrors. At one red light, a woman on my left noticed that I was topless. She winked. Jesus. Thank God she couldn’t see what was, or wasn’t, below.
I made it home, somehow. Fortunately, I didn’t see anyone outside my apartment complex. I had a blanket in the trunk of my car. The question was whether I should take the time to get into the trunk. Fuck it, I thought. I got out of the car, closed the door gently, and raced to my apartment. I don’t think anyone saw me. I hope no one saw me.
Then I realized that I had left my phone, wallet, and everything else in the car. I quickly ran to the bedroom, threw on a pair of shorts and a T-shirt, and went outside to retrieve them. At this time, I saw my neighbor from two doors down, Missy, coming around the corner. She was alone — no sign of her husband, Tony.
“Hey,” Missy said. “What’s up?”
“Nothing. Just forgot some things in my car,” I said.
“Like your outfit,” she said. “Of course, I liked the other one better.”
Fuck me! She had obviously seen me.
“Um, yeah, well,” I stammered. “Sorry about that.”
“Oh, I didn’t mind,” she said and playfully slapped my ass. “Looked like you were a little chilly, though.”
Missy’s husband, Tony, was a stud. I’d seen him in swim trunks at the pool. It was obvious that he was very well-endowed. I had fantasized about seeing him fuck Missy, about watching her take his big cock. I had wondered if she could possibly fit the whole thing in her mouth — or her pussy. I knew my average-at-best-sized member was no comparison.
As Missy entered her apartment, I retrieved my things and went back inside. Then, knowing I had probably already taken too long, I quickly called the number that Monica had given me.
Trying to slow my heart rate and stop sweating, I prepared for her to answer.
“Hello,” came the soft, sweet response on the other end of the line.
Remembering that she had told me to ask for her, I said: “Hello, may I please speak to Mistress Monica?”
“Took you long enough,” she said.
“I apologize,” I responded. “I had a bit of a, um, situation. I ran into one of my neighbors, and it took a bit of time.”
“Did she see your thong?” Mistress Monica asked.
Wait, how did she know that my neighbor had been a woman? She just knew. She seemed to know everything.
I explained the whole thing, how I had gotten into my apartment, put on shorts and a T-shirt, but that Missy had apparently seen me beforehand. So yes, she had seen the g-string.
“Whatever,” Mistress Monica said. “Doesn’t really matter. Tomorrow, I have booked an 11 o’clock appointment for you at a spa. It’s in the strip mall behind my apartment complex. Ask for Tess. She knows what to do.”
Tomorrow was Saturday. I didn’t have to work. But I did have plans. I was supposed to go to the track with a couple of buddies. Just as this was running through my mind, I realized there was no point in even mentioning it.
“Yes, Mistress Monica,” I said.
“Good slut,” she responded. “Oh, and be sure to shower, shower really well before you go. It’s important.”
“OK,” I said. “Is that all?”
“For now, Pussy Boy,” Mistress Monica said. “Oh, and one other thing. Absolutely, positively no jerking off tonight or tomorrow before your treatment. I don’t care how much you are fantasizing about me, about my tits, and about my ass. No playing with yourself. Is that clear?”
“Yes, Mistress Monica,” I said. “Although that is not going to be easy.”
“I’m sure it will be quite HARD,” she said, laughing. And then she hung up.
What the hell had I gotten myself into? Who was this woman? And what was she doing to me? I felt powerless, absolutely powerless. And my rock-hard cock had busted out of the thong and was threatening to rip a hole in my gym shorts.
Fortunately, it was late and time to get to sleep if I possibly could. I stripped, carefully removing the pink thong and hanging it on a lampshade by my bedside. Then, knowing it would be impossible to get to sleep in my current level of arousal, I jumped into a cold shower and calmed down — some.
I put on a pair of tightie-whities to try to contain my horniness and crawled into bed. I played the night over in my mind. How in the hell? Who IS this woman? She can’t be even 30, I thought. Probably mid-20s. What gave her the right? And what was this appointment tomorrow? At a spa? I had never been to a spa in my life.
Eventually, sleep came. I woke up once in the middle of the night with a raging hard-on, took a piss, and fortunately was able to get back to sleep in not too long a time. I had set my alarm for 9. I wanted to make sure I had plenty of time to grab some breakfast and shower — really well, at Mistress Monica’s instruction.
I left home at about 10:15. I didn’t want to be late. So I pulled into the strip mall at about 10:35. At first, I didn’t see a spa, but after driving around for a bit, I saw it tucked back in a corner between a dry cleaner and a women’s gym. “Tease and Please Spa,” read the sign out front.
I parked my car and walked inside. A somewhat heavy-set woman with very large breasts looked up from the desk and asked if she could help me. She seemed to have a glimmer in her eye.
“I’m here to see Tess,” I said. “I have an 11 o’clock appointment.”
“OK,” the woman said, handing me a clipboard with some paperwork attached. “Have a seat and fill these out. Tess should be free shortly.”
Most of the paperwork was routine — name, address, employer, that kind of thing. But the last page was a sexual-behavior agreement. The gist of it was that there were to be no sexual advances or innuendo whatsoever. Having never been to such an establishment, I was somewhat taken aback, but figured it must be the standard operating procedure. I completed the paperwork and returned it to the woman at the desk. I noticed that her nametag, sitting on her left breast, said “Betty.”
Without a word, Betty took the clipboard, glanced through the papers briefly, and placed it in a slot to the right of her desk. I sat in the waiting area. No one else was there.
Several minutes passed. I glanced at my phone and saw that it was 11:15. Well, I was on time, I thought. Then, finally, a door opened, and a shapely blonde appeared.
“Dan,” she called, looking right at me.
“Yes,” I said, getting to my feet. “How are you?”
“Oh, I’m fine,” she smiled. “It’s you I’m concerned about. First door on your right.”
As I entered the relatively small room, I saw what appeared to be a massage table in the middle and a couple of chairs on the right. The blonde closed the door behind her.
“I’m Tess,” she said.
“It’s nice to meet you,” I replied.
“Yes, so Monica made this appointment for you. Do you have any idea what it’s for?”
“No, I really don’t,” I said.
“That figures,” Tess said, smiling. “Monica has booked you for a full Brazilian wax — ass, too. So strip.”
“I beg your pardon,” I said. “I didn’t know…”
“I know you didn’t know,” Tess said impatiently. “That’s why I just told you. Now get your clothes off. There is no need for modesty here. Besides, from what I gather, I don’t believe you have anything to be particularly proud of.”
It was true, of course, but how did this woman know that? I mean, Mistress Monica had seen me in the thong, but…
Slowly, I began to undress while Tess prepared the wax with her back to me. She was wearing something like a nurse’s outfit, but I couldn’t help but notice her nice ass and well-rounded breasts. I guess this is where the sexual-behavior document enters the equation, I thought.
“Everything off?” I asked.
“Everything,” she said.
What the hell? My neighbor, Missy, had obviously seen me nearly naked just last night. And it didn’t seem as if I had any choice. Completely naked, then, I was wondering if I should get up on the table when Tess turned around.
“I see I was right,” she smirked. “I see a lot of guys in my line of work, and I have to say, that is one of the smaller penises I have ever seen.”
“Well, it does get bigger,” I said, trying to salvage some sense of self-worth.
“Sure it does, Honey,” Tess said. “Lie down on your back. You do have quite a bit of hair. At least you are somewhat manly in that regard. Of course, we’ll have to trim it before we get down to the real business.”
I felt so embarrassed. I had known my entire life that my cock wasn’t very big. That had become evident when I was in school when I saw other guys in the shower. I had only been with a handful of women in my life, and while none of them had ever flat-out commented on my lack of size, I was pretty sure I could tell they had all been disappointed. I tried to make up for my shortcomings with enthusiasm and oral skills, but I knew from plenty of reading that size really did matter to women. Especially a woman as good-looking as Tess. I could only imagine that she had enjoyed plenty of big cocks in her life.
As I laid there and Tess trimmed my bush, I couldn’t help but laugh inside at my situation. Here I was, stark naked in front of a woman I didn’t even know, and she had made it crystal clear that I have a little cock. And I was here, about to get waxed, on the orders of another woman who had dressed me in a frilly pink thong and had basically taken full control of me.
“Ok, time to start with the waxing,” Tess said. “I assume you’ve never done this before?”
“Um, no. No, I haven’t,” I said.
“Well, there is going to be some pain. We’ll see how much of a pussy you are.”
Great, I thought, steeling myself against both the impending physical pain and the emotional torment. I was determined to handle the pain so as not to be a “pussy.”
As Tess applied the wax and subsequently ripped it off, it did hurt, but it honestly wasn’t that bad. I was proud of myself, thinking that maybe I wasn’t such a pussy after all. Tess had me adjust into different positions to get to all the proper spots. Some hurt more than others, but overall, it was manageable.
“Time to turn over,” Tess said. “Let me see that cute little girly ass.”
Girly ass? Embarrassed, I rolled over. As I did, I pressed my cock against the table. It felt good. I wasn’t hard. But I was most definitely very aware of the sensation in what Tess had called ‘one of the smaller penises’ she had ever seen.
Tess went to work on my butt and the backs of my legs, and then after a while, she told me to get on all fours. Well, this was embarrassing, with me in a position as if I were a filthy slut just begging to take a cock up my ass. Actually, I had thought about that quite a bit. Not a real cock, but a strap-on, from a sexy woman like Tess. Obviously, that wasn’t going to happen now, though. Next, Tess applied wax to the crack of my ass. For some reason, the wax felt much hotter than it had anywhere else. As she ripped the wax away, she told me to roll back over and relax.
Yeah, right, relax.
“I’m going to do your nose and your eyebrows, too,” Tess said. “They certainly need it.”
The eyebrows weren’t so bad, but her doing my nose hurt like hell. I couldn’t help but whimper a bit.
“See, I knew you were a pussy,” Tess said.
“OK,” she continued. “Just lie there for a bit. I need to see how your skin reacts over the next few minutes to determine if you need any lotion applied. I’ll be back in a few minutes. Would you like a magazine or anything?”
“Uh, no, thanks,” I said. “I’m feeling a little bit tired. I think I’ll just rest.”
“Suit yourself,” Tess said. “I’ll be back. Oh, and no playing with yourself.”
Yeah, sure, I thought. I’m not sure I even want to, right now, but now I don’t even have control over that? Jesus.
I actually did doze off, lying there. I have no idea how long it had been when I heard Tess’s voice again.
“Wake up, Sleepyhead,” she said.
As I opened my eyes, I realized that Tess was not alone.
“What did I tell you?” Tess said.
She was speaking to the woman from the front desk! What was her name? Oh, yeah, Betty, that was it. She was standing right there, along with Tess, both staring down at my nudity.
“You’re right,” Betty said. “I’ll admit that I thought you were exaggerating. But it is probably the smallest one I’ve ever seen, too. I bet he never gets any pussy!”
“Yeah, and even if he did,” Tess said, “It’s not like a woman would even feel that little, tiny thing.”
They were talking, comparing notes, like schoolgirls, as if I wasn’t even there. The absolutely gorgeous Tess and the slightly oversized, but still sexy, Betty. They laughed. Clearly, I was nothing more than an object of their pity.
And with that realization, just as Tess had turned away to do some clean-up, my cock began to get aroused. I couldn’t help it. Lying there, naked, in front of these women, I suddenly became turned on. Had Tess been the only one there, my predicament might have escaped unnoticed, but that wasn’t the case.
“Uh, Tess, our little friend here is getting worked up,” Betty said.
Tess turned around and smiled.
“The poor, little fucker,” she said. “Well, fucker isn’t the right word. It’s not like he could fuck anyone with that little thing.”
Betty laughed heartily.
“I gotta go,” she said. “Good luck with little dinky dick.”
“See ya, girl,” Tess said. “OK, little man, time for you to get dressed and be on your way.”
“So, my skin is OK,” I asked.
“Oh yeah,” she said. “It was fine all along. I just made that up to buy some time until Betty could come in and see your ridiculous excuse for a penis. Although, to be honest, it’s more like the size of a clit. A little sissy clit.
“Boy, Monica is going to have some fun with you.”
I had almost forgotten. Mistress Monica. She was the reason I was here in the first place.
“I’ll be giving her a full report,” Tess said. “I don’t imagine she will be too happy that you got hard in front of Betty and me. I suppose you’ll be punished for that.
“Anyway, you can pay on your way out. I’ll see you next time if that’s what Monica wants.”
With that, Tess breezed out the door, leaving me to dress. I didn’t even know what to think or how to feel. I was beyond embarrassed. I proceeded out the door and to the front of the spa, where Betty was waiting.
“So, how’s it feel?” she asked.
“Not too bad, I guess,” I said. “Different, for sure.”
“No, I mean, how does it feel to be objectified, embarrassed, and humiliated in front of a couple of sexy women and to owe $200 for the privilege? After all, being that small can’t feel good for anyone who views himself as a man.”
“Uh, yeah, well, I’ll manage,” I said, reaching into my wallet. I forked over two C-notes and was about to leave when Betty spoke again.
“Did Tess give you instructions for the after-care?” she asked.
“No, I don’t believe she did,” I responded.
Betty explained that I avoided sweating, swimming, and hot tubs for 24-48 hours.
“Oh, and no sex, either — not that that would be a problem for you,” she continued. “But what might be a problem for you is no masturbation, either. Your skin is far too sensitive for jerking off. Believe me, and you’ll regret it if you do.”
Christ. There was nothing I wanted more than to get home and stroke my little cock. I wanted to ask how long I would have to wait. How embarrassing. But Jesus. I had been humiliated so much already. Did it really matter?
“For how long?” I asked.
Laughing, Betty looked at me and then looked beyond me to the remainder of the waiting room. For the first time, I realized two young women were sitting there, two sexy, young women who obviously had heard everything and were laughing under their breath.
“Probably going to be the longest 48 hours of your life, Sweetie. Good luck!”
I glanced at the women in the waiting room and then back at Betty one more time. Again, her bountiful breasts caught my attention.
I am totally fucked, I thought. Then I wondered what else Mistress Monica had in store for me.