Halo 4

Life had been a financial struggle since finishing college. The economy sucked, and everywhere I looked seemed to require 10 years of experience for their "entry-level" positions. I was barely scraping by on what low-level employment I could find. I had just passed 30. And my only two girlfriends I'd had since college had left me because in spite of treating them like princesses, I wasn't able to financially provide for them in the style they wanted.

Turnabout is fair play, I decided. I posted my profile (being honest) on a dating site and started looking for older women who were financially secure. After some correspondence, one of them actually agreed to meet me for a date.

Jill was 48 years old and had retired a few years back, having made her pile. She was tall (matching my 5-foot-10), muscular, and had short salt-and-pepper hair. We were meeting at the local cafe for lunch.

I had purchased my beverage of choice (water: I'm allergic to caffeine) and a sandwich and had been sitting for two minutes when Jill arrived. She had a full meal and what looked like a sports drink.

"You must be David."

"Unless my identity changed walking over here, yes."

"I'm Jill."

"Nice to meet you in person."

"Let's eat first, then talk business. I never make decisions on an empty stomach."

15 minutes later, we had consumed our food and drink.

"We'll take my car back to my place," Jill said in an imperious fashion. I followed her out to her BMW.

"This is my casual car. I wouldn't risk any of my nice ones down in this neighborhood."

What the fuck must her nice ones look like?

"I had my researchers check you out thoroughly. Your previous girlfriends said that you were always a perfect gentleman and did your level best to put their needs first in bed."

"Um, thanks?"

"You're barely holding on financially and in spite of trying to be responsible, you had to take out a $10,000 loan so you could pay rent and eat, as a year ago your employer cut your hours to avoid making you a full-time employee so they wouldn't have to provide benefits. You had to beg your father for the money to have your teeth cleaned six months ago and to have a medical checkup at the doctor's office three months back. You now owe $10,700 on the loan, as you have made only the minimum payment every month."

"Uh..."

"Wait until we get to my place. I have a business proposition for you. I think you'll like it."

I fell silent. 20 minutes later, Jill pulled into the garage of an enormous mansion. It was surrounded by tall fencing on three sides, and the fourth side led to a beach by the lake.

"Come on in," Jill said, helping me out of her vehicle. We went through the garage and into a luxurious dining room. Three people were waiting inside with some documents.

"Tina, my notary, and that's Charlene and Debra, two of my friends and also witnesses to this."

I sat down and started reading through the documents.

"Take your time. The short version is that you sign yourself over to me as my personal slave, and in return, I promise to clear your debts, provide you with all your needs, and take care of you forever."

I read through everything very carefully. Jill's summation was correct.

"And, if I don't sign?"

"I will have Charlene escort you to the front gate, and you're free to go back to your life as it currently is."

I signed, Charlene and Debra signed as witnesses, and Tina thumbprinted me and properly notarized the documents. Everything was all legal.

"Thank you, Tina. You are dismissed for now."

Tina, carrying the documents, egressed the house. Charlene and Debra stuck around.

"I'll have your meager possessions transferred out of your current dwelling tomorrow, David. And of course have your former employer notified that you will no longer be working there. But in the meantime, have you figured out yet why I agreed to this deal?"

I looked at Jill, but said nothing and remained still.

"For you, the benefits are obvious. But for me, what do I get out of it? I don't need you as a housekeeper or a chef or a gardener: I have staff or have contracted employees for that."

I remained still and silent.

"The only thing I didn't have, until now, was someone to sexually service me and my friends, who I could rely on to know how to pleasure a woman. Hiring male escorts for the purpose is a crapshoot and there's always the risk it's a sting operation by the cops. You have one job in this household from now on."

I nodded.

"Well, no time like the present. Remove your clothes - you won't be needing them ever again, this house is temperature-controlled."

I removed every bit of my clothing.

"I'll have the maids dispose of your clothes properly later. Everyone, come along."

Debra and Charlene joined Jill as she led me to the master bedroom. It alone was bigger than my entire apartment. My eyes widened in shock.

"I'm even more rich than you thought, slave. Hold still."

I held still as a padded collar was placed around my neck. The leash attached to it, a very long one, was secured to a steel ring on the wall.

"You can reach anywhere in this room and access the entire bathroom. I'll have my maids bring you three meals a day and arrange for a stocked refrigerator and snack table to be put in here so you can munch and drink in between. When your body is not in use by me and my friends, you may entertain yourself with the books and TV set/DVD player present, plus, as I already stated, your possessions will arrive tomorrow."

That seemed fair enough.

"If anyone needs to make a pit stop first before we try out my new slave, now's the time."

10 minutes later, I was lying face-up in the center of the bed. Jill was muscular but not muscle-bound: she was actually quite well toned. I guessed her breasts to be somewhere between a B and a C cup.

Debra's platinum-blonde hair color obviously came from a bottle. She was about 5-foot-zero and pleasantly plump: nice curves, a chest that fit her frame, and a round ass, without being obese.

Charlene was about 5-foot-4 and looked almost emaciated. She couldn't weigh more than 100 pounds soaking wet. Her barely-there breasts were maybe A-cups.

The three women teased their bodies for a few minutes, not letting me touch them. I supposed they were warming themselves up.

"I purchased him, so it's only right I get his tongue first," Jill announced. "You two can play with him in the meantime."

Charlene and Debra nodded. Jill lowered her box to my tongue. I licked along her slit to taste her. The intoxicating scent made me drive my tongue into her box to get more of her nectar. Jill didn't raise an objection.

I swirled my tongue in a circular motion to get as much as I could. In the meantime, two tongues were teasing my nipples and four hands caressing my legs. I moaned, my voice muffled by Jill's pussy, and my body shivered.

Jill tightened her legs around my head, and I sped up my licking. I placed my hands on Jill's butt and pulled her down more firmly onto me. My efforts were quickly rewarded, as Jill flooded my face with her juices.

Jill lifted herself up and shifted so that she could ride my cock. Debra adjusted herself so she was now sitting on my face, while Charlene was off to my side in a position where Jill and Debra could suckle her nipples.

I felt something tighten around my balls. Jill was tying them off with twine. "This way you stay hard, but don't cum yet."

I gave Debra the same treatment I had given Jill. A couple of exploratory licks to taste her (not bad, but not quite as sweet as Jill) and then slipping my tongue within her. Debra pressed herself downward onto my face.

Jill, meanwhile, already heated from being licked to orgasm, was sliding up and down on my rod. She bounced up and down with a very fast rhythm. Now I understood why she had tied off my balls: in my current state, I wouldn't have lasted five minutes.

Charlene's moans as Jill and Debra sucked on her breasts only made me hornier. There's nothing that turns me on more than hearing a woman in the throes of sexual satisfaction. I worked my tongue with more intensity inside Debra. Soon she, like Jill before her, flooded me with ambrosia.

Meanwhile, Jill's rhythm was getting faster and faster. Her legs clamped around my hips as she had an explosive climax. My body shuddered beneath her and my hips bucked spontaneously, but I couldn't cum because of the twine.

Jill climbed off me and Charlene took her place. I continued to tongue Debra, who was now actively grinding her pussy against my face. I continued working my tongue and brought a hand up to search for her clit. Debra guided my fingertip to the correct location, and I gently brushed her button, triggering another gusher of honey.

Charlene happily bounced on me, though she didn't lock her legs around me like Jill had. I moved my hips in time with hers, and she got into a slower, steadier rhythm. I licked Debra to another climax, and Debra lifted herself off of my mouth and then gave me a deep kiss, tasting her own juices.

Jill and Debra then got on either side of me and began kissing my neck as Charlene rode me. I gasped and moaned as two tongues teased my sensitive flesh. Then they traced patterns downwards and eventually reached my nipples. Charlene finally got close and sped her rhythm. I thrust upwards into her and she orgasmed.

Debra then took her place on my cock and Charlene decided to try my tongue. Charlene's juices were much milder than the other two ladies' honey had been. Or perhaps by now my senses were becoming fatigued. In any case, I licked at a slower pace than I had for Debra or Jill. Charlene seemed to enjoy it greatly. She had gone at a slower pace when fucking me, too.

Debra, by contrast, was moving very fast up and down on me. I thought I would see smoke rising from her box as she placed her hands on my chest to brace herself while she pistoned her hips up and down. I tried to move my own hips in the same rhythm but couldn't keep up.

Debra clamped her legs around me very tightly. "Just hold still, stud." I obeyed and let her do her thing. She orgasmed about five times in the amount of time it took me to tongue Charlene to a single climax.

All three women climbed off and let me catch my breath for a moment. They noticed my very swollen, full balls and nearly purple cock.

"He's done a great job of servicing us. Let's reward him."

The twine was untied, and three tongues traced their way along my throbbing shaft. Then Jill positioned herself between my legs, while Debra and Charlene flanked me. Jill stroked me, slowly, while the other two teased my balls. I trembled and moaned.

Jill's hand sped up, and my sperm burst from my pole. She aimed me so that I shot on my own chest and belly. She kept moving her hand until every drop was released from my balls. Then three tongues eagerly licked my skin clean of every drop.

I lay still, utterly exhausted. The ladies gave me big smiles and flounced out of the room, still naked. Jill said over her shoulder, "When you have the energy to move, go take a shower."

I took a moment to get oxygen back in my muscles before getting off the bed. It appeared life from now on would certainly be interesting...