Winter Formal

It was the night of the Winter Formal and I was nervous.

Part of my nerves was that I just didn't know what to expect. It all sounded so great in the post-orgasmic bliss after a double blowjob and a bit of casual girl-girl cum kissing. But what did I really know about Kate? I'd only met her the one time. Who exactly would be at this party, and as for "coming out" -- coming out into what? Or as what?

Another part of my nerves was that Kate, via Brenda, had lent me a tuxedo. It was perfectly comfortable, but I didn't feel comfortable in it, and furthermore it seemed to make the rest of my family a little crazy. My step-mom yelled something incoherent about "putting on airs" and "wasting money", even after I explained that it was all free, for me, tonight.

In the end, though, I made it out of my house. Kate had set the date of the party a bit later than most of the reservations for the Central. "They should see you arrive," she said. Another thing I was nervous about.

I steeled myself and walked in the front door. And was immediately blocked by the maitre d'. "Do you have a reservation?" he asked coldly. I wasn't even properly in the restaurant and here I was, I thought, getting kicked out.

"Fred!" I heard. "That's Jason!" I looked and I saw Kate and Brenda at the bar. They each had a cocktail and were dressed to the nines, in long, flowing, sparkling, low-cut gowns. They were wearing heels as well, so they towered over me. Their hair had been done... they were radiant, beautiful, exemplars of sophisticated womanhood.

Fred blanched. "I'm sorry, madame, sir," he fumbled. I just walked past him and toward Kate and Brenda.

As I entered the restaurant proper, I heard a bit of a murmur, and even one girl say, "What is he doing here?" Five minutes before, this would have hurt, but now I only had eyes for my dates.

"Ladies?" I asked. "Shall we?"

Kate led the way as we passed between the main part of The Central and its bar, to the heavy padded door that led up to the Upper Floor. The bouncer opened it as we approached. I thought maybe I heard a gasp as I went through, but then the door shut and I left the high schoolers behind.

I went up the stairs in the low light of the hall way and into a kind of small foyer that also served as a cloak room, separated from the rest of the Upper Floor by thick curtains. Here was my first surprise of the night -- the Upper Floor's maitre d' was a young-ish woman -- late twenties (I later found out, 27) -- who had bright pink hair and a pretty, pixie-ish face and a pixie haircut to match. She had a pierced septum and pierced nipples, which I could tell because she was not wearing a shirt.

"I...." I couldn't form words -- something that would happen more than once this night. I looked past her into the cloakroom and saw that many of the hangars held women's shirts, not coats.

She carefully eyed Kate and Brenda, looking not at their eyes but at their chests -- a bit of a performance, I thought, because I knew she knew her own boss -- and said, "Ladies, your tops, please."

Brenda and Kate were wearing gowns, so there was nothing to remove, but instead they shrugged off the shoulder straps and I found their gowns had been designed so they could also be worn as a sort of skirt, with their breasts bare.

The young woman turned to me. "Welcome to the Upper Floor, sir. My name is Toni Smith, I'm the maitre d'. If you need anything at all, I'm at your service."

I was staring at her tits, I have to say. I'd never seen pierced nipples before, and I was fascinated.

Toni broke character for a second. "You can touch them if you want," she whispered. I reached out and fondled the small barbell in her left nipple. Her breasts -- of course -- were small. I cupped one briefly. "Thank you," I said. Sincerely.

"Follow me," she said. We walked through the curtains and into the restaurant proper.

It was not ostentatious, but still obviously expensive. About six tables were in the room, and Toni made a beeline for one in the corner -- one next to the one-way windows overlooking the Central. The best seats in the house.

Looking around the dining room, though, the first thing I noticed was that all the other tables already had patrons. Both men and women were there, but perhaps half the women, like Kate and Brenda (and Toni), were topless. They were sitting, eating, chatting with the other people at their tables as though nothing was out of the ordinary.

I saw a couple of women I knew. Sarah was there, shirtless, at a four-top with an older man who could only be her husband. Looking closer, I saw that Angela was also at Sarah's table, along with another shirtless woman I did not know. The next table over was a party of five at a round table. That table had just one shirtless woman, plus two other men and (shirted) women. I didn't recognize any of them. The rest of the room was similar.

Kate slid her arm into mine. "Any woman without a shirt is one of yours," she said. Those were her exact words. "You'll have their contact info before the end of the night. In fact..." she tapped Toni's shoulder. "Toni, please give this young man your phone number."

Toni said, "Of course ma'am. How could I forget." She held up her phone and took a selfie with her fingers in a "V" and her lips puckered as if she was kissing. I told her my number and she texted the photo to me with a note: "Come play with my piercings any time! Toni." (When I got home that evening and checked my phone, I saw that Toni later texted me her address)

Then we were at the seats. Toni showed me to my seat first, which was in the corner, so if I turned slightly to the left, I could look down and see the other diners below. Kate sat to my left, her back toward the one-way glass, and Brenda to my right, her back to a wall. No one sat across from us, and instead we were able to see the entire Upper Floor dining room.

Toni handed out menus and Kate gestured toward the other patrons. "They're all here for you, Jason," Kate said. Toni turned and left. At this moment, I could tell Brenda was very excited -- we'd spent a lot of time together and I could see she was breathing a bit hard. I knew something was up, but I wasn't prepared for what happened next.

Toni returned after a moment, and stood directly across the table from me. With her was another woman, also topless, who I did not know. She had medium-length brown hair, firm (but small) tits, and striking blue eyes, and was wearing black tights. Aside from her eyes, she looked like any one of a hundred yoga moms. Toni said, "I'd like to introduce your cocksucker for tonight. Assuming she meets with your approval. Jason, this is Deborah Morenci."

Deborah held out her hand. "It's a pleasure to meet you, Jason. I've been looking forward to tonight," she said.

I shook her hand unsteadily. My hand shook and I couldn't think of what to say. "Are you... are..."

Brenda was already pulling my pants down. "She's Mike's mom," she said. "And, Jason, I want you to just go along with this next part. It might seem a little **** -- but I know you're going to enjoy it, and remember it for a long, long time."

"I... ok..." I mumbled. My pants were off now, and my heart was racing. His mom! And I had to admit, she looked pretty hot.

Toni, I noticed then, was carrying a bag, and she set it on the table. Deborah reached into it and pulled out a small gadget, consisting of an O-shaped metal ring and a leather strap. She opened her mouth and carefully inserted the ring, then held the strap up. Toni took the strap and buckled it on -- it was a gag to **** her to keep her mouth open.

Deborah looked at me and wiggled her tongue playfully, then winked. Then she reached into the bag again and took out what looked like a tangled mess of webbing. After a minute or two, she and Toni got it untangled and then she fit it carefully over her head. It had buckles, too, but she didn't fasten them.

Instead, she reached in the bag one last time and with a dramatic tilt of her wrist, lifted out a pair of handcuffs. Looking at me and batting her eyes, she handed the cuffs to Toni and then ostentatiously put her hands behind her back. Toni clicked them into place and then put one hand on Deborah's head and gently pushed down.

Deborah sank to her knees as Toni, with her other hand, lifted the tablecloth. Then with a bit of shuffling, Deborah slid under the table, to reappear between my legs. I could easily feel her breath on my balls in the cool air of the restaurant.

My cock was already hard, and only got harder when Brenda firmly grabbed it and pointed it at Deborah, who then slid forward, engulfing my cock in her mouth. It fit nicely into the O-ring, I noticed -- they must have planned ahead to find the right size.

Then I noticed that Kate had picked up the ends of the webbing and was pulling it taut behind my back. She buckled it into place, locking Deborah onto my cock, which was lodged deep in her mouth. It felt heavenly.

"Won't she..."

"****?" laughed Brenda. "Maybe a little. But she'll be ok."

"What if ... like if I need to..."

Kate brushed the side of my face. "Cum? Just cum in her mouth. In fact, I think you should try to cum right now. Face fuck her a little, see if you can get in her throat. Go ahead, grab her head."

Brenda grabbed my hands and placed them on Deborah's head. "There you go," she said.

I started thrusting my hips a little, looking down at my arch-enemy's mom, who for her part was looking up at me as I slowly fucked her mouth. She nodded when I held her head more tightly, as if to tell me it was ok.

The harness meant she didn't have much range of motion, so I settled for just rocking her head back and forth slightly, trying to push my cock even deeper into her throat. I could feel the tightness of the back of her throat as the head of my cock pushed at it. I had never had a woman deep throat me, and I was hoping to get there...

... when Brenda said, "There's more, you know." I kept face-fucking Debora -- feeling very driven now, and close to cumming -- as I looked over at Brenda. From my left I could feel Kate, stroking my thigh and I could sense her running her fingers through Deborah's hair.

Brenda leaned in conspiratorially. "Deborah told us she wants you to be very comfortable tonight, and to know that you don't need to get up if you have to take a piss." With these last words, she also stroked her hand through Deborah's hair. "Isn't that right, honey?" she asked, toward the woman in my crotch.

"Oh my God!" I shouted. I started cumming then, deep in Deborah's mouth. For her part, she tried to swallow it all, but I heard some gagging and **** sounds -- and did not care. Other patrons in the restaurant turned to look at my outburst, but quickly resumed their meals. They seemed aware of what was happening -- nobody could have missed Deborah getting handcuffed -- but indifferent.

I felt a little embarrassed, and I saw that Toni was still just standing there, with a smile on her face.

Kate said, "My, my... Toni, I think Jason here would like a beer. Something with a lot of volume, if you know what I mean."

"Yes, ma'am," said Toni, and she turned to go get me a drink. My cock started getting hard again at just the thought of it.

"Kate," I said, coming to my senses a little. "Isn't she... uncomfortable? And isn't, umm... pee pretty gross?"

Kate touched my arm. "You are so sweet!" she said. "Brenda was really right about you! Anyway, Deborah here has a pillow under there, and she is happy to do this, believe me. Really any of us would be. And as for pee... Jason, you just do what you like and let us worry about that. It's really no big deal. Now, dear, don't you worry about Deborah any more. Just pretend like she isn't there, at least not until you're feeling horny again."

Toni arrived with a beer in a large stein, accompanied by our waitress, a curvy 20-year-old who was wearing a shirt. The waitress set glasses of water down, and Brenda and I examined the menus. I tried hard to ignore Deborah, whose face was basically chained into my crotch. Every now and then she would suck gently on my limp cock, making it pulse a little... it was hard to ignore, really.

We ordered dinner and I listened while Kate and Brenda talked about the restaurant, Kate's other businesses, and the politics of the high school faculty. After about twenty minutes, Brenda grabbed my shoulder. "Look," she said, pointing down into the dining room of the Central.

I looked and saw Mike Morenci, his girlfriend, and another couple getting up from a table. They had just paid and were getting ready to leave. He looked a little angry, and I found out later from the grapevine that his girlfriend's parents had decided not to let her go to the afterparty -- so no sex for Mike.

The juxtaposition of seeing Mike downstairs while his mom had her mouth full of my cock got me hard again, and so while Kate and Brenda continued their conversation, I put my hands on Deborah's head again and started rocking it back and forth, trying once more to get my stiffening cock past the back of her mouth and into her throat.

Kate noticed and stopped talking mid-sentence to say, "That's a good boy. Fuck that whore's mouth hard. Try to get your dick down her throat."

"God, Kate," I said.

"Takes one to know one, Kate," chimed in Brenda. "Maybe you should be getting face fucked, you whore."

Kate said, "Maybe I should! It looks pretty fun... then later he could switch whores and take a piss down your throat."

Hearing them verbally spar a little was enough for me, and I came down Deborah's throat for the second time that night. This time, there was less cum, and she didn't ****, but instead swallowed it easily.

Our food arrived and we ate. The food was excellent and paired well with my German beer, which was low in **** but made up for it in volume. I also drank a lot of water and by the end of the meal I could feel the pressure building in my bladder.

If you'd told me on my birthday that I'd be here, doing all this, I would never have believed it. And I could scarcely even believe it now. And while I think I'm a pretty nice and considerate person, overall, I was also a bit buzzed from the beer, and the sex, and just the general bizarreness of my situation.

That's why, without mentioning it to anyone, I looked down, directly into Deborah Morenci's stunning blue eyes, relaxed a little, and let out a tiny squirt of piss.

This was a test on my part, to see how she'd react. I watched her face carefully to see what impact it would have, but she just continue to gaze up at me as she swallowed with a gulp. Feeling encouraged by this, I relaxed a bit more, and put my right arm around Brenda's shoulder, then released more piss, but this time instead of a squirt I let out a slow stream of urine.

Deborah closed her eyes as if she was concentrating very hard, or perhaps in bliss, and swallowed my piss as it came out of my cock. I tried not to let it out too fast, and for her part, she suckled my cock like she was drinking from a bottle.

Brenda noticed how relaxed I was and she said, "Kate!" and then pointed down at Deborah. I continued to piss for a long time, and Kate and Brenda watched for a while, seeing Deborah's throat move as she swallowed the urine as it came out.

Have you ever pissed in a woman's mouth? It is an incredible experience. The sensations themselves aren't really different from urinating anywhere else, but the depth of relaxation is incredible, and of course the act itself is extremely submissive, like her mouth is just there for you to use, any way you would like.

I peed a long time -- the beer I had was quite large. Deborah, to her credit, drank everything; and when I finished, I felt her tongue probe my cock as she tried to suck out the last drops.

Kate, with a smile, raised her hand and had the waitress bring me another beer.

We had dessert first, before I drank my second beer. When we finished dessert, that seemed to be a signal to the other patrons, because I noticed that, one at a time, a table would finish up and then come over to us to say good-bye before leaving.

The first table to go was Sarah and Angela's. Angela introduced me to the third woman from the table -- her wife, Louise. Then Sarah introduced me to her husband, who gave me a firm handshake. "Thank you for everything you've done for Sarah," he said, without explaining any more.

Kate spoke up, "Phone numbers and addresses, ladies."

Sarah took a selfie where she looked regally at the camera, with her breasts clearly visible, and texted it to me. Angela and Louise took a selfie together, then they both texted me so I would have both their numbers. Louise also texted "Stop by our place any time for some fun 3-way action!"

I continued to sip my beer as the other tables emptied. I lost track of all the women I met. I couldn't remember their names, but I did get quite a catalog of names, addresses, and topless selfies.

The very last party to go was a somewhat older woman, who had dined alone. At first I thought she was very old, but I saw that, despite her grey hair, which was tied back quite severely, her skin was not as wrinkled as I would expect. I'd find out later that she was on the older side -- she was 55 -- but she had gone prematurely grey. She was short, but not petite -- she was very muscular, with very pronounced muscles, like a weight lifter or a rock climber. She wore glasses with a heavy black rim, and introduced herself as Doctor Ellen Patton.

"Very pleased to meet you, Jason," she said in a somewhat clipped tone. "How did the gag work out? Did she spill any urine?"

Kate explained, "Ellen here came up with the harness."

"Thank you," I said. "I think it worked great!"

"Very good," was all she said. Then she took a rather stern-looking -- but still topless -- selfie and texted it to me. She included two addresses -- "You should have my work address as well, I'm often there," she said, and then also texted "Dr Ellen Patton, blowjob theorist".

I had to stifle a laugh at that, as it seemed plainly ridiculous, especially coming from someone as weird and stern as she was.

When she left, the room was empty except for our table. The wait staff was busy cleaning up, and Toni came over to see if we needed anything else. I openly ogled her pierced nipples. When Toni left again, Kate addressed me.

"Toni is very sexy," she said. "And you should definitely visit her. But a word to the wise, Mr Kraus -- Ellen Patton is the real deal. You should prioritize seeing her first."

"Really?" I said with a little laugh.

Brenda agreed, "Oh, yes, Jason. Trust me, you won't regret it."

"Ok," I said. "If you say so. Now, before we go, if you don't mind, I have to take another piss." I looked down at Deborah and started.

Later, I realized I had forgotten to get a few addresses: Kate, Brenda, and of course Deborah. Kate didn't forget, though, and the next day she made sure I got all three. Deborah's selfie was evidently taken before she left the restaurant for the night, because she still had the O-ring gag in her mouth. She wrote a little additional text as well, "Jason, it was an honor be your first urinal. Thank you. Please stop by any time for more of the same, I still have the harness. xxoo Debbie."