In a Hole

I would never have gotten into the fix in which I found myself if I hadn't gotten into a really big fix. I was raised in a good home by good parents. We are still regular church-goers and my parents are involved in the community, volunteering in various things. I'm not going to get into any details, given the nature of my story.

To put it bluntly, I've been working as a prostitute. I looked it up in the google dictionary:

pros•ti•tute
ˈprästəˌt(y)o͞ot/
noun
noun: prostitute; plural noun: prostitutes
1. 
a person, in particular a woman, who engages in sexual activity for payment.

I was sure as hell raised up to believe that that was an illegal activity and surely immoral, against all of the things I was taught.

I checked it out in the local laws, too:

They prohibit prostitution, soliciting for prostitution, and pimping. When I read the statutes, it felt like I had a lead weight in my stomach, realizing what I'd done. The penalties were not trivial, either:

I'd surely done what the statute said I shouldn't. I'm just glad I wasn't busted and I don't do that any more. It was something I thought I had to do to deal with a major disaster during my freshman year in college. I'd been going to the local college, living with my parents to save money. Of course, I was a pretty dumb girl without the sense the Lord gave a dead goose.

Let me explain. I was drinking at a party with the rest of the girls on our cheer squad. There were some athletes there, lots of loud music, and some of the girls were using ecstasy, cocaine, or marijuana. In other words, a pretty basic college party and rave. I've never been interested in most of the drugs, but you see them around. I just like wine coolers and I'd had about five before I saw it was time to go.

I was driving my old junker car and I thought I was ok to drive home. It was only a mile or so away. Anyway, I backed out of the driveway and it was dark and I just didn't see the other car. It was my fault. No question about it. The thing is, my insurance was the least the law allowed. It only covered injuries. It didn't cover the damage I did to a late-model Toyota. The good thing was the driver was kind to a rather stupid girl who should never have been driving. He agreed to get an estimate for the body damage and I agreed to pay it off. He told me he had to have it fixed and I had to pay for it. If I got it paid off in time, he would not file a report with the police.

Naturally, being totally panicked, I agreed to anything if it didn't lead to my getting a ticket or especially going to jail for DUI. They're really fierce about enforcing DUIs here and I was still underage.

The smart thing would have been to confess my sins to my parents and let them hire me a lawyer and deal with it the right way. I panicked and this is my story.

I told my best friend, Angie, on the cheer squad. She was a pretty wild girl and would do pretty much anything for fun or on a dare. She listened to my story and she looked at me soberly.

"Shit, Heidi, you really put your foot in it this time, didn't you?"

I nodded mournfully. "Yeah, I'm not sure what to do. I don't have the kind of money this is going to take and I don't know where to get it."

We batted ideas around for a while before Angie got a look on her face. I knew that look usually meant trouble, but I finally took the bait. "Okay, what do you think? You got an idea?"

"How far did you get with Steve?"

Steve was my boyfriend that I'd just broken up with. He started dating one of the other girls on the squad. "Third base."

"You weren't doing the dirty deed?"

"Hell, no. I'm saving that for somebody really good. Steve's an asshole."

She laughed. "Was he any good?"

"Shit. He'd give a couple licks with his tongue and then try to stick his cock in me."

"Oh, yeah, that one. Well, did you give him head? Get him off?"

I nodded. "He got some really good head from me. I always got him off."

She laughed. "Not hard, is it? Guys are so easy."

I shook my head again. "Yeah. You give them head and they blow and go."

She shook with laughter. "Well, sometimes that's a good thing."

"It is? How? No satisfaction in it for me."

"What if they paid you to suck them off?"

"Isn't that just a little illegal? Like prostitution or something?"

"Not if all you do is suck on it 'til he shoots. It's not like you let him fuck you or anything."

I looked at her sidelong. "Are you crazy? You can go to jail for that and then no scholarship no nothing. You have to go work doing fast food or something to make my rent cuz my parents would toss my ass out of the house if I did anything like that."

"They don't have to know anything. I've been working at a glory hole for months and I've saved enough for my first year of college. It's easy and you never have to take your pants off."

"Are you crazy, girl? OMG I'd be caught first time I tried it."

"No you wouldn't. I've got it worked out. Nobody ever sees who you are. All they know is you're a cute teen girl giving head. Charge the guy $50, I take $10 and you keep the rest plus tips. You're in total darkness and he has to wear a condom. You can do 5 or 6 guys an hour and take home over $200 and get your debt paid off quick. After that, you keep all the money for school or clothes or whatever."

"Did you do that?"

"Yeah, I make a thousand a week and I'm going to pay for school with the money I make."

I thought about it for awhile and then I looked her up again after classes. "Tell me more."

"Not here. Come with me after school and I'll show you, k?"

Now I started to get butterflies in my tummy for real. I followed her to her car and got in with her. She looked at me. "It's good you're in your cheerleader uni. The guys just love that. You'll see. If you want, I'll let you do some, too."

I sat back and crossed my legs. "I don't know..."

"That's cool. You'll see soon enough how easy it is."

She drove me to a rough part of town and we parked in the back of an old house. She knocked on the back door and when it opened, she squeezed in, pulling me along with her. We walked down a hall to a room. Inside, there were partitions between chairs. I followed her into one and she sat down and flipped a switch, dimming the light. That seemed to be the signal. I saw a hand in a hole in the wall, fingers wiggling, holding $50. Angie took a rubber from a box next to her chair and swapped it for the money. The hand was replaced by a hard cock ready to go in his raincoat.

Angie took the guy's cock in hand and very gently began to stroke it. There were moans from the other side of the wall and she put the tip into her mouth and began to gently suck on it. He pushed as far forward as his pelvis could go. She took the hint ad began to suck and stroke the cock with abandon. She touched his balls and kept sucking him, letting him set the pace until he seemed to stiffen up as he filled the tip of the condom with his cum. When he relaxed, he pulled back out of the glory hole and I could hear the sounds of his cleaning up and zipping up. The next guy did the same thing, but he really liked how she treated him, moaning and fucking her face to show how much he appreciated it. When he was done, he passed another $50 through the hole and she touched his hand, giggling, "Thank you so much! I hope you come again."

He chuckled as he turned away, zipping up. "See? It's been what? 40 minutes and already I have $150. Wanna try one? I'll let you keep what you earn if you like."

I wasn't sure about this, but I was definitely getting wet panties. "Let me watch one more."

She grinned at me and turned back to her hole where another hand was wiggling money, ready to go. I watched amazed as she took care of this one, too. He had a small dick but Angie just took it in stride and made sure to suck it all into her mouth. She told me later she loved the guys with small dicks. They loved what they got and came back often.

She got up from the chair and pulled me to it. "Here, you do the next one. I've seen him before. I recognize the ring. He's really nice and he has a small dick, too. He's so grateful when I take it all into my mouth. Suck him good and I bet he gives you a good tip. You've sucked a guy off, right?"

"Hell yeah, I like sucking cocks."

She smiled at me. "Good girl. Try this one on for size, okay?"

I sat down and looked at the hand wiggling money at me. Putting a condom into his hand, I noticed the lovely ring on his middle finger. He gave me his cock. It was only about 4 inches long, but it filled the rubber nicely.

Taking a leaf from Angie's book, I took it into my hand and stroked it gently. I always loved doing that with my boyfriend before we broke up. My secret lover began to get stiffer as I stroked him. Angie whispered, urging me on. "Put it into your mouth and suck him off, love. He loves a great BJ. I told him you're the best."

Wondering about when she was able to tell him something like that, I put my full effort into sucking him off and was rewarded in a couple of minutes with the spasms of his cock and his spunk filling the tip of the condom.

I held his cock in my hand with the tip in my mouth for a moment until his spasms subsided and he began to pull back. In a second, he passed another $50 bill to me and, in a low gravelly voice, "Thanks. You're really good, you know."

Angie took the bill before he pulled his hand back and she kissed me on my lips. Her kiss thrilled me nearly as much as my making him cum did. She handed me the money and kissed me again. "You're really good and you like it. I can tell. Any guy who gets a BJ from you is pretty lucky. Wanna do it again?"

My panties were wet and I was definitely horny. "Yeah. I'd love that, Ange. I almost forgot how much I like giving a blowie."

She kissed me again and pointed to the fingers wiggling in the opening. This time they were a lovely shade of chocolate brown. His fingers were longer and more delicate than the guys on the football team, but this was part of a fantasy long held, to have sex with a black guy. I kissed Angie back and nodded. She grinned and pointed to the money. I took the bills and handed him a condom. His dick was through the hole in a minute and I knew what to do. I treated him gently as I did the other guy and, after a moment of teasing him, I put the tip in my mouth and began to swirl my tongue around the tip. Stroking his rod up and down slowly, I took my time getting this one ready to come. He was beginning to stiffen when I backed off and squeezed the base of his cock firmly in my fingers until he began to relax again.

More stroking and deeper sucking and I got most of his cock into my mouth and took my time finishing him off. He went off like a rocket and I just barely kept hold of his cock as he shot the condom full of his seed. I enjoyed the feeling of his spunk lubricating the inside of the rubber, making it easy for me to stroke him.

He moaned and pulled back, saying, "too sensitive, man. That was awesome."

Again, his hand slipped through the hole, handing me another $20. "I'm sorry I don't have more. You're really worth it. I hope you're here next time I come. I'd love to do more if you want some time."

Angie shook her head at me and said, "Thank you, darling. This is only a glory hole for oral. None of the guys get more. I'm so sorry. You're a sweet man."

She kissed me again and I felt her hand under my skirt, touching my mound through my dance pants and panties. "You're so wet. You wanted that black boy, didn't you?"

I kinda hemmed and just didn't say anything, but she could see right through me. "It's okay, Heidi. Sometimes, when it's slow, I've let a guy or two stick it in me through the hole. It's really hot to get a totally anonymous fuck and you can always call the shots."

She grinned at me and moved to the cubicle next to mine and began taking care of her own customers and I took care of three more before I was ready to quit. My jaws were aching and I was tired. At the end of the night, I'd sucked five cocks, collected $370 total and gave $40 to Angie for my "rent".

I was amazed how easy and how pleasant it was to earn $330 for a night's work. I owed the car guy $2,000 for the body work and I was already 1/6 of the way there. Angie and I sneaked out the back and got into her old car, but not before she checked things out, shining a flashlight into the car, into the back seat, and even into the trunk. "You can't be too careful. I knew a girl who got raped by a guy who hid in her back seat. It was bad. Always check the car out."

That woke me up. It seemed an easy way to make some money, but pretty dangerous. "Hey, you did pretty well for your first night. When do you want to do this again?"

I thought about it for a moment. We had cheer practice Wednesday night, I was going to my girlfriend's house for a sleepover on Friday, and the 'rents had me tied up for the weekend. "Thursday?"

"That works. Friday is better. It's pay day and there are lots of guys who get pretty needy. They tip pretty good. Friday possible for you?"

I sighed. "No, I got family stuff on the weekends. How about Mondays?"

She considered it for a moment. "I'll come with you Monday, but it's not always a busy night. If there's nobody to play with, we could find other things to do. Wear a short dress or skirt, okay? The guys like to see a little leg or thigh."

I nodded and put my hand on her thigh to squeeze her. She smiled sweetly at me and touched my hand with hers as she drove me back to school to get my car.

That set the pattern for our activities. She was able to get out more nights than I, so she made better money, but I didn't mind. I was made more comfortable with the situation by the presence of my worldly friend for a few weeks as I made what I needed.

I saw her at school the next day. We had a game that day, so we were wearing our cheerleading outfits, mainly a short tunic in school colors that let my dance panties show whenever I did anything. Angie seemed to approve. She pulled me into the girls bathroom and we crowded into the end stall when nobody was looking.

She hugged and kissed me, rubbing my ass under my uniform. "You look so cute. Are you ready for tomorrow night?"

Just the mention of our plans started to moisten my panties. I kissed her back, caressing her cute ass through her dance panties. "Mmmmhmmm. I've been thinking about this just ever since my first time."

"I know what you mean. After my first time, I had my hand in my panties all the time. I couldn't give it a rest, I was so horny. I'm glad you like this. You should come over to my house for a sleepover the next time."

I moaned as she squeezed my butt. "I'd love that, but mom never lets me sleep over on a school night. She doesn't think I get any sleep. Has to be either a Friday or Saturday night."

She kissed me for a long moment. "Well, my loss, but can you get out on a Thursday night?"

I nodded. "Yeah, I just tell her I'm doing some schoolwork with a friend. She's okay with that."

Angie giggled. "School work? I love it. It's almost time and I have to get to class. See you tomorrow night. Ride with me?"

I gave her a quick hug and broke away. "Yes, please. Your car is better for that than mine."

"I'll see you after school, the usual place."

On my way out to the parking lot, I ran into another friend from our squad. Mary Jane is a compulsive gossip and can talk your ears off if you let her. She's cute and always has interesting things to share, but I was a girl on a mission. I shook her off with a promise of coffee and a good chat later on.

I trotted down the rest of the way to the parking lot where I found Angie leaning against her car door, talking with a couple of the boys. She smiled at me and then at the boys. "I'm sorry, guys, but my date's here and we're going out together."

I laughed as I threw my things into her back seat and then I swatted her butt through her jeans. "You wish! The mall first? Or the library?"

She grinned. "I think I want something to eat, first. I'm hungry. You like sausage? I know a place that serves it hot and good."

I laughed, too. "Yeah? Where's that?"

She threw me the keys and I took the hint and got into the driver's seat. She flirted with the boys for a second and got into the car when I started it up. I drove us to the exit and looked to her. "Which way, chica? Hey, I thought we were going to wear short skirts."

"Turn right to the light and right again. We are wearing short skirts."

I looked at her for a second, raising my eyebrows. She giggled and then reached into the back, pulling a little dress out of her bag. I watched out of the corner of my eye as she skinned out of her jeans, revealing a rather skimpy thong. Her shirt came off next, showing off her matching bra.

She smiled at me and winked. "What do you think? Turn onto Broad Street, next intersection."

I watched as she turned her dress around and pulled it on over her head, smoothing it over her hips and thighs, lifting up to pull it down to about mid-thigh level. I whistled at her. "You're a real hottie, Ange."

She touched my knee below the hem of my skirt. "You, too, Heidi. The guys just love you. I think the denim mini is way cute. Wearing panties tonight?"

I giggled and opened my legs, pulling my skirt up to my waist for a second. "You like?"

She leered at me. "Oh, wait 'til the boys get a peek up your skirt. You gotta let them have a little peek. They tip much better when they get a look at what they hope for."

"Then why don't you take your panties off?"

She looked pensive for a second, then squeezed my knee for a second. "Heidi, I'm not sure I understand it, but the tease is better than the show. I've tried it both ways. Wearing panties I get better tips than showing off my little kitty."

"Really?"

"Fo' shizzle. Try it yourself. See what happens."

I shivered for a second. "I'm not sure I could go commando."

She laughed. "Honey, take my word for it. You don't have to. Show them a peek at your panties, just a peek. I bet the guys will be jacking their little cocks just thinking about what's under that cute little skirt of yours, even after you make them happy."

I smiled shyly at her. She directed me to the decrepit house. We got our purses and went inside and we got set up to make another round of guys happy. I'd set my personal record last visit of 9 guys and I wanted to get a full 10 tonight. I was doing pretty well and close to my goal of paying off the guy whose car I slammed into. He was surprised about how fast I was paying him off. In fact, I began to hold back some of the money I earned, both to save for myself and also to keep him from getting too suspicious.

Within an hour, I'd taken care of three guys and I was ready for my fourth. I was kneeling in front of the hole, letting my legs part just enough to entice the next guy. I heard him make a comment to somebody with him and I recognized his voice. He said something to his friend and then the hand that came through my hole was shockingly familiar. I recognized the watch he wore and the bandaid he had on his finger.

I was momentarily panicked. Angie was involved with her current customer, which meant I was about to give a BJ to my little brother. He was a year younger than me, barely 18, and my first inclination was to kick his sorry underaged ass out of our little glory hole. I realized what a disaster that would be and, in something of a state of shock, I took his $50 bill, wondering where he got such money. I mechanically passed him the condom and, when his cock came through, I had enough presence of mind to take it and begin to stroke it softly.

Jimmy has a surprisingly nice cock. It was six inches long and of a nice thickness. I thought for a moment how nice it must feel inside a girl's vagina. I knew he was screwing his girlfriend, a really cute sophomore whom I really liked. I thought she was good for him. I even envied her a little bit.