Gangbang Chaperone

It had been her first date without a curfew so I had no idea when Janie got home. It had to have been sometime between two AM, when I fell asleep on the couch watching old movies, and eight, when I woke up with the TV turned off and Jamie's window-rattling snore reverberating down the hall. I went to check on her and the sight of her bare leg poking out from under her comforter made me smile. She was eighteen years and one day old, safe at home and not pregnant. In our family, that last point was something to celebrate.

It was an unwanted family tradition. I had given birth to Jamie when I was sixteen, my mother had given birth to me when she was seventeen, my grandmother had given birth to my mom when she was fifteen and she wasn't even her first child. And so it went, a long string of very young mothers stretching back into the mists of time. Whether it was a blessing or a curse or just a simple function of genetics, the matriarchal side of our family tree has always had three things in common; big boobs, raging libidos and frightfully fertile loins. As a result, our fore-mothers had been subjected to strident religious indoctrination, social chastisement, arbitrary punishments, and even quarantine, but they always ended up with a baby in their belly and a disappointed family reluctantly committed to helping raise yet another unwanted bastard infant.

Obviously the old ways didn't work.

It seemed to me that the only alternative was to arm my daughter with knowledge. So I started her sex education when she first started asking where babies came from and continued teaching her ever since. I was honest and no topic was out of bounds, even when she started asking me about my sex own life. And when she started getting interested in boys I immediately took her to get contraception. My mentoring may have been a little too thorough since she had developed a reputation as her high school's biggest slut, perhaps justifiably, but at least she was partying on her eighteenth birthday and not getting up early to feed a toddler like I had been.

Excuse me for patting myself on the back, but I was full of contentment that morning for having finally broken the family curse.

Janie didn't get up until almost one. I was spending a lazy Saturday doing the crossword and listing to all of my Garth Brooks albums on shuffle when she wandered into the kitchen looking worn. I smiled at her and saw that something was bothering her almost immediately. A mother can tell.

"Good afternoon sunshine. How was your date?" I said, figuring that if something was wrong it probably had to do with her date. She had been seeing some guy named Tom for the last couple of weeks but she had been uncharacteristically stingy on the details.

"Fun," she said as she opened the refrigerator door to find a Coke.

"What'd you guys do?" I asked, trying to sound nonchalant.

She didn't answer right away. She sat at the table across from me and took a long pull on her can of Coke while looking off at nothing in particular. I could almost see her mind working back behind those big, dark eyes of hers; trying to decide how much to tell me. I was willing to let her decide. While it is true we were very open with each other I realize everyone has their secrets and all relationships have their boundaries.

Finally she put her can down and looked at me. From the hard gleam in her eye I knew she had decided to share something big. "I... um, I mean we... had a three-way last night."

Now personally, I'm not a big fan of three-ways. Unless you're truly bisexual you almost always spend a lot of time waiting for your turn and not one man in twenty can properly satisfy two women at once. Besides, every long term three-way I've been in ends up with everybody pissed off at each other. I'd told Jamie all of this years ago when a boyfriend had been pressuring her and another girl to give it a try. She had gone ahead with it only to find out that I was right. That's why I was so surprised she was trying it again.

"Really?" I said, keeping cool about it. "Who was your third?"

"Tom's friend Brian."

Well, I almost spit out my water. A two guy three-way was like a home made rocket ship; apt to blow up and scorch you badly, but totally worth the risk if it holds together. It had been almost ten years since I'd last had two guys at once and I still masturbated to the memories.

"Oh," I managed to say. "Did they use protection?"

"Of course," she said with a roll of her eyes. She frequently grew tired of my lectures on birth control.

"Did it go well?"

Janie smiled. Her relief at having told me without having me lose my cool was palpable and her enthusiasm for her new experience came bubbling through. "Oh mom it was awesome. Both those guys touching me, kissing me, moving inside me... I came so hard. It was like the best sex ever."

"How did they do it, oral and vag or anal and vag?"

"Oral. They wanted to try the other way but I was nervous and told them we could try that some other time."

"So Brian is going to join you again?" I asked, feeling guilty for feeling jealous.

"Weeell," she began with obvious trepidation. "That's the thing."

"What's what thing?"

"Well, Brian and Tom have some friends they want to introduce me to. Tonight. I'm curious, and seriously turned on by the idea, but I'm a little scared."

This little piece of news about knocked me out of my chair. I've always tried to be a cool mother but this was too much for me. "A gangbang!" I sputtered. "They want to get their friends together to gangbang you?!"

"Jeez mom, I didn't say I was going to do it."

"That's really dangerous Janie. You could get seriously hurt."

"Tom's a nice..."

"I don't care. You get that many men together and they start acting like animals. What if they decide they want to take off their condoms halfway through? What could you do about it?"

"I'm on the pill too, remember?"

"You know what I'm talking about Jane."

"He said they're all going out to get tested today."

"Sure they are. How do you know they won't just show you some bogus documentation?"

"That's just it. I don't know what that shit..."

"Watch your language young lady."

"I don't know what that stuff looks like. I need someone there who has some experience and can supervise things; someone who can check their documentation and can stop the party if I need help."

"And who exactly will do all this for you?"

"Well, I already said Tom is nice, but you said he didn't count because men are animals."

"That's right. They are."

"Well, I guess Tom will have to do."

"I thought you said you weren't going to do it," I said, almost lapsing into a yell.

"I said I hadn't decided yet, but the more I think about it the hotter it seems. Doesn't it sound awesome having all those guys around you, waiting to fuck you?"

"I said watch your language," I reminded her. But she was right. It did sound hot. Frankly, it was a long held fantasy of mine but had long ago put it in the category of 'Things That Never Actually Happened Outside Of Pornography'. Maybe if I had been dating around when I was eighteen instead of potty training Janie I would have had my chance. I had aged well and looked at least half a decade younger than thirty four, but God I was a hot little bitch when I was that age; the guys would have been lining up for a chance to share me.

Suddenly I realized that my mind had wandered off as I thought of men lining up for a poke at me. I looked back to Janie and she had an intense look to her face as she stared into my eyes. "So I guess Tom will have to chaperone," she said again.

My stomach flipped over as I belated realized what she was hinting at. "Oh Janie, no..." I said slowly.

"Come on mom," she whined; sounding like the teenager I sometimes forgot she was. "It's my birthday."

For a long time I just looked at my horny young daughter, my jaw hanging open. Then I forbid her from going, of course. And, of course, she claimed I couldn't stop her since she was legally an adult. Then things got ugly as we had our worst fight in over a year. We both ended up screaming at each other until she slammed her bedroom door and I collapsed sobbing on the couch.

As I started considering my options I realized I was making the same mistake as my mother and grandmother and great-grandmother, on down the line, back to infinity. I knew I couldn't stop her; not forever. I remembered the bone deep horny impulses that used to drive me to climb out of my bedroom window on school nights and sneak off with boys during Sunday school. Heck, I still felt it every day; it was just simpler to act on now. So, with a sinking feeling I realized that the only way out of this gangbang situation was straight through it and the only safe route for Janie was for me to go along and supervise.

So, reluctantly, I knocked on Janie's door and told her I'd take her to Tom's.

As we prepared that afternoon I was glum and nervous at first, but Janie's giggling excitement was infectious. Before long I had caught her feverish anticipation. I treated us both to lunch, after which we got Brazilian waxes, facials, mud baths and colonics. We left the day spa sparkling clean from head to toe, inside and out. I told myself I'd gone through the whole regimen with Janie to lend moral support, but I was already imagining scenarios where I had to step in and take over as Janie sobbed that she was wrong and I was right and would I please, please, please do this gangbang for her because she was so scared, and I'd just shrug and step into a crowd of horny young men who would take me in their strong hands and use my every orifice as a playground while my daughter just shook her head in wonder at my sexual acumen and parental wisdom.

Quite honestly, I was growing hornier by the minute.

Finally we were ready. Janie wore a very short, very tight black skirt and a tight pink halter top that showed of her young, naturally firm breasts and abdomen. I was wearing a tight and short dark blue dress that showed my cleavage to a scandalous degree and exhibited the hard body I'd crafted during my dozen years as an aerobics instructor. Janie wore her long, straight, sable colored hair down, I wore my blond locks the only way you can wear loose curly hair; loose and curly. We looked good. Better than good; we looked stunningly sexy; eminently doable.

And it was time to go.

I drove us there as the day was giving way to evening. We were both quiet and jumpy with anticipation as I drove into the city on unfamiliar streets. As I piloted the car I heard a telltale humming sound from my right and looked over to find Janie with a vibrator up her skirt, head back and eyes half closed as she buzzed herself towards climax.

"What the heck are you doing?" I demanded.

"I'm going nuts over here. I just need to take the edge off."

"Darn it Janie, you're going to have half a dozen guys pushing to get at you in a few minutes, get a hold of yourself."

"Oh mom..." she whined.

I sympathized with her. I really did. I too was about ready to crawl out of my skin from nervousness and fear and desire and a whole host of freaky conflicted impulses. I wished I could've got myself off, if only to settle my mind, but the afternoon just got away from me. But I wasn't about to sit there and drive while my daughter masturbated in the seat next to me.

"I'm serious young lady. You're a woman now and you need to grow up and learn to control your desires."

"Well you don't sound in control of yours," she said in a pout as she pulled the six inch long device from under her skirt.

"What's that suppose to mean?"

"Just that you seem pretty freaked out."

"I'm taking my daughter to a gangbang. How the heck do you expect me to act?"

"Like you won't take out that pepper spray I saw you put in your purse and start randomly spraying people at my party."

Maybe Janie had a point. I was on edge and jumpy. She didn't even know I also had a taser and a handgun in my purse. I considered what she'd said. It was kind of a recipe for disaster. But I was feeling stubborn. "I'll be fine," I said

"When was the last time you even got laid?"

"Gosh. I guess it was four, or was it five, days ago. Some customer at TJ's." I recalled the encounter. It had been at my other job bartending at Tiggle Jitz; a too brief encounter in the back room with a customer who talked a better game than he was able to produce.

"FIVE DAYS? Holy shit mom, no wonder you're on edge. Did you even come?"

"No. And I'm tired of telling you to watch your language."

She looked over at me for a long time then, in a low voice, said, "Come on mom, you need some relief." She reached over and held the still buzzing vibrator against my inner thigh.

"What are you doing?" I said with alarm as I jumped in my seat.

"Come on mom, if you're going to be my safety net I need you chill. Let me help you out." She moved the tip of the vibrator up under my dress. I felt it lightly touch my pussy.

"Please Janie, stop it," I said unconvincingly.

She didn't stop it. She pushed the vibrator more firmly against my vulva and began moving it up and down over the thin fabric of my panties. I began panting, I knew I should stop her, but, as she said, I needed to stay 'chill'.

She pulled my panties to the side and found my clit. She slid the vibrator down across it, along my lips and into my vagina. I gasped as I clutched the wheel tightly. I opened my mouth to tell her to stop, but I couldn't bring myself to speak. Soon she was thumbing my clit as she pulled the humming plastic phallus against the front wall of my vag, hitting the G spot behind my pubis just right. I moaned as we pulled up to a red light and I let my thighs open wider.

"That's right, relax. Let it go," said Janie to me softly as her lips gently kissed along my collarbone.

"Janie, this is..." I meant to say "wrong", but I couldn't. I felt the orgasm welling up from within me now; filling every cell with the trilling power of animal release. I let my head fall back against the car seat as my breaths started panting out in ragged huffs. Janie's face was down between my boobs now, her tongue licking down along my cleavage. Her thumb circled my clit as the vibrator buzzed inside me. I was so close; just a few strokes away from climax.

An impatient honk brought me back to cognizance and I looked up to see the light had turned green. I slammed my foot down on the gas and we leapt forward as I pushed Janie away from me. I'd almost let my own daughter get me off. What kind of monster was I?

"You want to pull over?" she asked.

"No," I answered.

"But you didn't come. I thought it seemed like you... Hey, that's Tom's building right there."

We pulled up to a very swanky high rise and found a parking spot around the corner. I was surprised this Tom fellow lived in such a ritzy neighborhood. I was even more surprised when the doorman showed us to a special elevator to the penthouse. I had envisioned Janie's friend Tom as another of her college boys, but as the elevator brought us quickly skyward I began to wonder who exactly she'd been dating. However, my stomach was turning somersaults in double-time now, so I couldn't bring myself to quiz her in the few seconds we had before we reached the top.

The door opened and we stepped into a richly appointed apartment with large paintings, full windows and high ceilings. Arrayed before us was a group of men in dark blue bathrobes. They mostly seemed to be in their forties and late thirties. Their eyes bore into us with unconcealed lust.

"I was expecting five or six guys Janie, there's like fifteen men here," I said quietly as we walked out towards them.

"I know," she said. I could hear the nervousness in her voice.

"Is everything well, ladies?" said a dapper man with a gray flecked, old fashioned handlebar mustache and thinning, slicked back hair. His voice purred with a slight Italian accent. He walked up and gently kissed Janie on the cheek.

"Yeah Tom, I just wasn't expecting so many guys," said Janie.

So this was Tom, I thought; an aging pervert eager to hand my naive daughter to his horny friends. I bristled when I realized this was probably a game for these men; enticing young women into this swank penthouse, using them up and tossing them away. I wondered how many other young women had come before my Janie.

"And Tom, I'd like you to meet my friend, Patty," she said, indicating me. I'd asked her to not let them know I was her mother. For some reason I didn't want this roomful of perverts to think I was a bad parent.

"It is a pleasure to meet you," he said smoothly.

"I'm just here to make sure my friend stays safe. I don't want you guys screwing her over," I said.

"Of course Jane will be safe, but, to be blunt, screwing is the entire point of this party, no?" he said calmly. Everyone laughed but me.

"Look," I said curtly. "I want to set some rules here. The safe word for tonight is 'stop'. Not just 'stop', it is any word that means stop or wait or hold on or quit; anything. Also, no pictures, no videos, no recordings of any kind. Thirdly, you're all going to wear condoms..."

There was a moan from the assembled men. Several complained vocally that they spent good time and money getting blood tests this afternoon and they'd be damned if they were going to wear rubbers. Tom approached me and gently took my elbow to invite me to talk with him privately. My eyes glaring hard at him, I followed him to the corner of the room where two huge windows met at a right angle and presented a million dollar view of the city as the setting sun reflected on the slow moving river in the distance. Tom handed me a folder with a set of nearly identical papers.

"Would you like to inspect these?" he asked.

I opened the folder and leafed through them. They were genuine alright. One doesn't remain as sexually active as I'd been most of my adult life and not get to recognize a valid HIV test result. I'd even used that lab. I counted through them and there were seventeen separate reports. I did a quick count of the room and counted seventeen men. In amongst them was Janie, shooting me a look of profound irritation.

"I assure you your daughter will be safe," said Tom as I slowly looked over the medical reports again. They'd had the darn things notarized and everything.

"I just don't want her..." I paused when I realized he'd referred to Janie as my daughter. "Did she tell you?" I asked with an air of betrayal. Looking over at her I saw she was sitting on a barstool drinking what looked like a coke and laughing as men gathered around her closely. A big black guy had his hand on her knee.

"No. It is very obvious. You two look so much alike; your mouths, the shape of your faces, your eyes, your, if I may be so forward, exceedingly sexy bodies. She already told me she had no siblings so I deduced the relationship rather quickly."

"You must think I'm I horrible mother."

"No. Quite the opposite. You are a very kind parent to not only permit this, but to chaperone it to ensure your daughter's safety. It must be very difficult for you. If I had a daughter of my own I hope I could be as liberal."

I looked over at Janie again. A man had moved behind her and was kneading her shoulders. The black man's hand had moved off her knee and now rested well up on her thigh. Another let his robe fall open and she reached down to take his penis in her hand.

I handed the test results back to Tom. "Is it really that important that you don't wear condoms?"

"We would greatly prefer it. But it is important to Jane. She's told me she's never experienced many of the tactile facets of, um, let's call it 'primitive' sex. She has fetishized semen as a missing piece of her sexual life. It would probably be best for her if she has this experience now, while it's safe."