Rent Free or How I became Man Whore

Rent free or How I Became A Man Whore

Thanks to my editor for making this one better.

My job cut back on my hours, so I had to tell my landlady, Sue, I would be short on rent for my room that month.

We had a good relationship. I often did small projects for her, and she gave me rent credit. However, this would be the first time I actually needed it for financial reasons. Prior to this it was just chores for a little extra beer money, more of a courtesy than anything else.

Turns out I had no reason to be nervous, she was more than willing to work something out.

"You'll have to make it up, but I'll come up with something useful for you to do," she said, smiling rather mischievously.

I went back to my place relieved and oblivious to the things that were about to transpire, I really had no idea how much my life was about to change.

The first chores she assigned to me were common paint touch ups and small repairs. My work was always done under Sue's watchful eye, sometimes along with her friend Mary. Both were in their late forties, neither would ever be described as model material, but they truly had great personalities, which made them very easy to be around. After a few projects, it dawned on me that these ladies were actually enjoying the view of my toned body while I worked. It was a fun distraction, and I played up to the gallery more than a little.

Sue was a widow. I thought she had a decent body for her age, not fit or fat, just soft. Her hips were wide and her hair a premature gray. She wore unflattering glasses that sat on a big nose, and something of a life weary, worn out look. Mary was on the homelier side, none the less she sported a rather large set of fake boobs that sat high and proud on her chest. They were large but not gross, yet obviously fake.

Sue's husband left her very well off after his premature death. Her need for work or anything else was more for something to keep her busy, than any need for money. I think she rented the room for company because I heard from the neighbors that her previous renters were always good-looking, fit men in their early twenties, like myself.

Well, two months later, disaster struck. I was completely let go from my primary job, which only left me with a couple of side jobs, certainly not enough to pay any rent, just car insurance and credit card minimum payments. If I was really lucky, I might be able to afford a few things to eat. I went to Sue and told her about my situation, and my intention to move out, since I could not keep up our deal due to my lack of money.

"I think I have a way to help you out, Ben," Sue said. "But it's not quite like the stuff you've been doing so far." She blushed slightly before continuing, "You've done almost everything around here, except for one older project."

"I'm listening," I said, noticing her get a little uncomfortable, but still not having a clue where this was going.

"Not now, I'd rather discuss it over a meal, just to make sure the work appeals to you. How about we go out and discuss this over a couple of steaks and some fine wine? My treat, of course," she added with a smile.

I admit I was intrigued, I offered to move out because I knew she had been struggling to come up with meaningful work for me to do the last week or so. Yet, bottom line, I was having steak tonight, that was the main thing I was looking forward to.

I waited downstairs, watching some television, after we both had taken our turn in the shower. When Sue finally came down, she looked like a completely different woman. The glasses were gone, her makeup was perfect, as was her hair, and the dress she wore accented all the full curves on her body. In all the time I'd lived there this was the first occasion I ever saw her made up for going out. She still wasn't what you would call beautiful, but she was definitely worth a second glance.

After complimenting her, then leading her out to the cab, we proceeded to the local steakhouse, where we enjoyed each other's company and a fine meal along with several adult beverages. We were feeling fine, laughing easily and truly having a great night.

Then the conversation turned.

"I want to trade rent for sexual favors," she said, flat out, as casually as if she was asking me to pass the salt.

Had I been drinking at that moment; I would have worn my drink. I was momentarily speechless, but thankfully, it was she who continued.

Sue explained, "I'm not interested in some kind of weird older-younger relationship. I'm not expecting love, I value my independence, and don't want to complicate my life with a serious relationship. I still have needs though, but the thought of jumping into the dating pool just to get some sex is not really my thing either."

She went on to tell her story, renting to good looking guys just for the eye candy, and company. She really only ever loved her husband and anything else just couldn't hold a candle to that relationship. She had had a few "engagements" with other men since his death but nothing good.

She really enjoyed my company and had been toying around with this idea for some time. So, when I approached her with my rent issue she thought this was her chance. She could get some "quality dick" and I could keep a roof over my head.

"What do you think?" she asked.

I had remained silent while she spoke, but I must have looked like the cat that ate the canary, because she asked me what I was grinning about. "I just had some good drinks, a nice steak, great conversation with a pretty girl and now I'm going to get laid? Hell, it's going to take all night to wipe this grin off."

She laughed and blushed, "I don't know about the girl part, but I do see your point." She reached into her purse and handed me an envelope. It contained a credit card with my name on it, and a hundred dollars in cash.

"These are for expenses relating to our arrangement. Use the card to pay the check. Tip well. The cash is for incidentals or other needs." she explained. "Excuse me while I step into the ladies' room, while you settle the check."

I watched her with different eyes as she got up from the table and walked away offering me a great view of her ass. My mind was reeling as I processed everything that had happened today, and it was going to end with sex.

I snapped out of it and paid the tab, tipping generously as instructed, and made sure a car was waiting for us. When she returned to the table I noticed two things: one, the confidence and sexiness in her strut, and two, she did something to her dress that brought her tits out on display, and they looked great.

I must've been staring at them as she approached because when she got close she shook them a little extra while laughing at my googling eyes. "Come on hot stuff, let's go." she said and continued towards the door not waiting for me to get up.

The ride home was uneventful, we made small talk in the presence of our driver. Making our way inside, she asked me to make another drink and also bring some water up. "Meet me in my room in ten minutes or I'll start without you," she said.

I quipped, "Ten? I'll be there in five."

"No, ten I said, and not a minute sooner. A lady needs time to prepare". She laughed and headed up the staircase to her room, saying over her shoulder, "Ten minutes, starting now."

I made the drinks, and the water, and went upstairs to freshen up. Thankfully, the time went by rather quickly, and before I knew it, it was time to join her.

When I got to her room, the door was slightly ajar, and the lights were down. Sue was laying on the bed in a silk robe. I immediately felt overdressed and said so. She laughed and replied, "Well let's get some of those clothes off you."

She sat up and helped me remove my belt, as I took off my shirt and then pants. I caught a glimpse of her full breasts in the opening of her robe. Leaving my boxers on she pulled me down onto the bed. Everything that happens next seems incredibly natural, I held her in my arms kissing her neck and caressing her body. I found myself with her luscious tits in my face going back-and-forth between each one, sucking and nibbling on each breast. Teasing each nipple to its maximum hardness, before switching to the next.

Working my way down her body, getting myself between her thighs, I parted her lips and begin to familiarize myself with her hot snatch. I took my time, wanting to please her. She put her hands on the back of my head to guide me, letting me know just what she wanted. I could feel her getting close much sooner than I expected, so I continued until she came in one long gut wrenching cum. She finally pushed my face away.

Gasping for air, and glowing in post orgasmic bliss, she said, "Holy shit! Fuck, that was good."

I handed her the water and helped her sit up again. In the dim light, I took in her body while we were drinking and catching our breath. She had really nice boobs and looked pretty fucking good naked. We recovered quickly and started round two.

I went for her pussy again, but she pushed my hand away and reached for my underwear, finally freeing my cock from its prison. When it flopped out, it was stiff but still growing. She smiled and said, "I fuckin' knew it, you're hung. I've been looking at this bulge for months. Oh, it's so nice." Holding it in both hands she just stared at it for a minute.

She couldn't say much more other than "mummth gluck mumm" since she wasted no time putting it in her mouth. She practically worshiped it, kissing and licking it all over before sucking it into her mouth, working just the tip and making me feel things I never previously experienced, then she tried to cram as much as possible down her throat. She did this for a few minutes. I was as hard as could be and felt my orgasm mounting very quickly.

Holding back, I asked her if she wanted to fuck. "Absolutely" she said.

She laid back onto the bed and spread her legs open, allowing me full access to her dripping pussy. I wish I could say I took the time to slowly slide my throbbing cock into her, allowing her to adjust and be comfortable. Nope, I took my position, swiped it up and down her snatch just once, then drove it right in to the root.

She gasped, and yelped, as her pussy stretched painfully open allowing my cock to slam into her deeply and fully. Her reaction snapped me back and I started to pull out before she grabbed my hips forcefully holding me in place. I started to apologize and was stopped by her hand pulling me in for a kiss. Our lips met and she slowly started to grind beneath me. I took it as a cue to start my motion, and we began to fuck.

So, we fucked for what seemed like a very short while and I could feel my impending climax as her pussy seemed to have its own plan. She had some pussy control skills that I not yet experienced, and expertly milked my cock. She motioned she wanted to be on the top, so we rolled over and I let her lead.

After riding my cock and grinding her clit against me, we were both getting very close. She began to cum, and I couldn't hold back any longer as her tight pussy convulsed around my cock. I exploded inside her and coated her insides with a thick load of cum. Our bodies were in sync throughout the entire experience. I was surprised when she didn't stop.

She just slowed down and relaxed her pussy, continuing our motion, but resting also. She could reach one of our water bottles and we shared a drink. Then she leaned down and fed me her breasts, slipping each nipple between my lips and allowing me to nibble and occasionally bite them. We continued like this for some time just enjoying the sensations.

I noticed that my cock had fully recovered again, so did she. "Do me doggie?' she asked. Never being one to deny a lady I agreed, and we switched positions. I was rooting around that pussy really good as she came again. Not letting her catch her breath, I continued to rail her while pulling her hair, sometimes reaching forward to grab and squeeze her boobies and pinching a nipple. She seemed to be in utter ecstasy as she was overcome again by yet another orgasm.

She collapsed in a heap. "That's it, my pussy can't take anymore!" She exclaimed. Rolling over, her gaze was drawn to my pulsing tool. "Come over here," She pulled me down to the bed and gently cupped my balls with one hand and used the other to place my cock into her mouth.

She engulfed me in one motion, expertly sucking my cock. The sensations that followed really were too much for me to handle. I could feel myself ready to explode. I tapped her shoulder and moaned some sort of warning. She doubled down on my dick and then squeezed my nuts just the right amount. Overcome with sensation, I emptied myself into her mouth, as she expertly milked me completely, allowing my spent cock to fall from her mouth with a gentle flop.

We laid there for a while recovering, even finished off the drinks I'd made earlier. I got up and went to the bathroom and relieved myself. Upon returning I saw she had made herself comfortable and looked ready to sleep.

She looked at me and smiled, "Thought we should get this out of the way right now. No sleep overs. You can go now." She kind of shooed me off pointing the way to the door. "Good night, see you tomorrow."

Feeling dismissed, and just a little used, I slunk away to my room and crawled into bed. I must have been exhausted from my experiences that day, because much to my surprise, I quickly fell asleep.

The next morning, I woke up, remembering the night before. I wondered if things would be strange between us. I met her in the kitchen and was relieved, the Sue I knew before was still there, her glasses and comfortable, but unfashionable, clothes were back. Again, she was that middle aged almost frumpy widow that I had come to know so well, not the sexy, seductive creature I was with last night.

I opened with my usual cheery good morning, and it was returned. She offered some coffee as I came in, still waking up, "Coffee would be great, thanks." I responded. We spent the next few minutes in relative silence, and we looked at our emails and caught up on our news feeds like normal. There was some small talk about the things we had planned for the day.

She began, "I set up some rules and guidelines for this new rental agreement, I'll send it to your email, look it over. Feel free to suggest any changes you might want and send it back. We can bounce it back and forwards until we have agreement on the contract. Then we can print and sign it."

"That's great, I did have some concerns," I admitted. "How often will I be providing service? Also, I'm not exactly sure what my role is."

She smiled and agreed "I was thinking the same thing this morning, I think the rental agreement will make you feel better."

Later that day I checked my email and sure enough there it was, a rather official looking rental agreement, month to month, with all the standard terms and clauses except for the payment. It basically said rent would be provided as long as the tenant continued to provide "Quality Personal Services", which made me laugh.

There was an additional attachment that stated the frequency, and details about the expectations. I was worried I would be "on call" all the time. In fact, she only required weekly encounters. they could include going out like an actual couple, in which case all expenses would be covered by her through the card or supplied cash. We could also skip past all that, occasionally spending the whole time in bed. Additional encounters could be negotiated at any time agreed upon by both parties. She proposed having set days scheduled and suggested Tuesdays.

This all seemed really great to me, and I accepted the terms of the agreement without any changes. However, I asked that we revisit the agreement in one month. I also told her I thought last night shouldn't count towards payment since the contract wasn't in place yet. Actually, I really just wanted to fuck her again and didn't think I could wait a week.

I sent my response and she responded with 2 words.

AGREED, Tonight.

*******

Two weeks past, and things were amazing. Our friendship didn't really change, the sex was great, and I was looking for work. However, there came a morning when Sue came down the staircase with a troubled look on her face.

"Is everything ok?" I asked.

"I'm not sure," she said, "I might have made a mistake." Then I think I saw the beginnings of a tear.

"Hey, hey, whatever it is I'm sure it will be fine. Tell me what's happening? How can I help?" I was pretty sure the agreement was the problem, in my head it was too good to be true, so it couldn't last.

She looked at me for a long moment, then blurted, "I told Mary about our arrangement."

"Okay," I responded warily, trying to quickly assess the implications of the situation.

"Then Mary told Alice, Alice told Lori, and basically the whole ladies' auxiliary." The tears had definitely come when she said, "I outed you as a prostitute."

"Holy shit, you had me worried for a minute there." I laughed heartily at that point. "You didn't out me, Mary did that. Let them talk. I honestly don't care what they or anyone else thinks. Now if you do, that's different. I'll do whatever you need to be comfortable, we've got a good thing going here."

"Not done, Big Boy....." She wiped away the tears that had been forming and said in a surprisingly deadpan tone, "Some of them want to hire you."

"Oh." I could feel the redness crawl up my neck as I became quite embarrassed.

"See, I ruined it by opening my big mouth!" she said. Then tears returned and she babbled on about ruining my life and reputation.

I had to stop her there. I stood up and wrapped her in my arms and said soothingly, "I think you're looking at this completely wrong."

She stopped crying and looked at me with a puzzled look.

I suggested we turn this around and consider the offers. I explained it would protect us making sure these ladies kept this in check lest their reputations come into question. I also explained I wasn't having great luck getting any responses to my job search, so the additional income could be beneficial to me.

I paused hoping she was considering it when she picked up the ball and ran with it. Saying she could handle the calendar and the payment process so they could have the illusion of real romance or whatever they wanted. She grabbed a pad and started taking notes.

By lunch time we had concocted all the details. Sue would pimp me out. We agreed that each "encounter" should be a unique experience tailored for each client, not just a quick bang. This had the advantage of justifying the charge for my time being priced at a premium. At first, I wasn't sure about this, but she insisted I was worth it.

After setting all this up, it made us both rather horny and without a word found ourselves naked, orally exploring each other. I had my face between her thighs and was feasting on the sweet juices she supplied.

Sue nursed gently on my cock, not trying to push me towards orgasm, but just enjoying my meat sword and it's slightly salty precum. She shifted herself and lowered her pussy onto my fierce erection. She rode me like this for a while, slowly, making sure my dick reached all the places she wanted it. We both were enjoying the sensations, steadily reaching towards a crescendo. We came close together. She first, that hot pussy milking me and pushing me over the edge, as I filled her with cream.

She laid back and said "Pimping makes me so horny"

We both broke out in laughter, then casually went about our business. At dinner, she said she already had one booking and three in the pipeline, pending payment. I was surprised at how quickly this was achieved. She explained that when she told Mary I was available, her friend couldn't say yes fast enough. As a matter of fact, Sue thought we could have charged Mary double, and she'd still would have booked me.