The Story of Elaine

By the time that I was 30, I had been living away from home for a few years and I was fortunate enough to have been able to purchase a small house after a break up with a girl that lived with me for a year and a half. I accepted a job with a new employer which had me starting work at 5am. That was early for me. There was a small crew in at that hour and after a few days I was getting to know everyone and joking around with them as we worked.

Elaine was quickly warming up to me. She was high energy and maybe a little whacky, the 'talk your ear off' type but nice, and hard to not look at. Her brown hair was a little past her shoulders and she was always smiling. A smile almost always makes a girl more attractive but also she had a really nice ass in snug jeans and her tits that were just on the cusp of being big for her frame.

Those two features made her waist look quite small in comparison and set off the classic hourglass figure. I normally was drawn to smaller chested women but the roundness of her breasts definitely distracted me. She was a jeans and t-shirt girl but would probably look great in a prom dress or a summer dress. As it was, the workplace didn't have a dress code but did provide unflattering work clothing, which she managed to make look good.

After a couple of months I was pretty comfortable in the new job and Elaine and I had gotten to know each other fairly well on a superficial level. She told me stories of growing up and some high school stories, all about her dog, as well as her current living situation with her boyfriend, Dave. One morning Elaine came in and I could tell that something was not right. She looked like she was sick or something and later she told me that she had not slept and was crying all night. She looked terrible.

Elaine went on to tell me that she and Dave had a major blowout and throughout the rest of the shift, she told me of the ongoing troubles that she was having with him. It had come to a head the previous night and it ended up with him telling her that she had to move out in a very aggressive manner.

She said that when she went to bed the previous night, that Dave had started making moves on her and in her words "So, I let him." and as soon as he was done, he left her and said, rather mumbling "You fuckin' bitch". She began asking him what she had done to have him say that to her and that was when things really started to ramp up. He got very nasty with her and threw some things around.

It put Elaine in a bad situation because she still had feelings for the guy and she also lived far away from family, like me, and didn't really know many people. She had no support system. I thought that it might all just settle down and things would eventually get back to normal, however, as a couple of days went by, it looked like they weren't going to patch this up.

Elaine told me that she had contacted a few people with rooms for rent and that she had a meeting scheduled with one of them. She was rather restricted by the fact that she only had a part time position and she had her dog. Many people didn't want to rent a room to a person with a dog. She told me about being in a bad financial situation with a couple of years left to pay on her car as well as credit card bills. While in the relationship with Dave, she never paid rent or bills and was realizing now that she was spending just about everything that she earned and was worrying about where rent money would even come from.

I didn't ask her about the meeting in case it didn't go well but a few days later she was telling me that it went okay aside from the fact that she did not like that the older man was single, and that he was looking at her in a particular way. The rent for the room was reasonable, but not even close to something that she could afford now that she was aware of the reality of her finances.

She said that she had discussed reduced rent with the guy in exchange for house cleaning or other duties and he seemed open to it but it made her feel like he would try to use the situation to his advantage in a physical manner and everything that she said about the situation reinforced that. She was definitely more stressed after the meeting than she had been in the time leading up to it.

"So that would be a deal breaker then?" I said jokingly just trying to lighten the tension.

"In that situation, with him, it is." she answered.

Her response surprised me as if she unconsciously just told me that it would be a possibility if it were someone else, and not the old guy. Or was she not saying that and it was just the way that she worded it? I guessed that I was 10 years older than Elaine but I looked young and I thought that I was much different than what I envisioned the old guy looking like. "Well Elaine, I could offer you a room at my house. It isn't large but there is more than enough space." I told her.

"Really?" she said perking up, "I might be interested in that."

And I could see her energy and demeanour had an obvious lift. I thought that I would leave the 'physical requirement' out of the conversation for now. "When could you show it to me?" she asked.

"How about later today?" I casually offered.

"That would work good for me. Dave is becoming more belligerent by the minute. He's just mean. It's like I never knew him." she said, obviously stressed.

I could see that she was a little more upbeat for the rest of the shift and we spoke briefly at shift end about what time she should come over and my address. So later in the day I had taken a nap and set the alarm for 15 minutes before her expected arrival time. She showed up about five minutes after our agreed-upon time saying that she had taken a wrong turn and so on. I had told her that it was no big deal but she kept talking about it for a few minutes.

I showed her through the house and explained some things to her. She seemed to really like the place and liked that there was a main bathroom, ensuite bathrooms for each of the 2 bedrooms, and a fenced back yard.

"Can I get my dog from the car?" she asked.

"Sure!" I said.

So she went to her car and brought the dog in.

"Kevin, this is Ace." she introduced. The dog was really nice...friendly and well-behaved black Lab. Pretty much fit to a 'T' her lengthy descriptions at work. I knew that Elaine was really into her dog and would have spent a lot of time with him training as she had told me some training stories as well. After 15 more minutes or so she thanked me and left.

I felt bad for Elaine and I wanted to help her but I also had carnal thoughts about her and although I thought that what her boyfriend did was terrible, I could not help but think that I would like to have a situation with her, in which I had control and she was obligated to me. Thinking about it made my cock swell. The next day at work she was very much like her energetic self prior to the blowout with her boyfriend. When no one else was around, she said "So Kevin, do you want to rent me that room?"

I said "Well, let's talk about it at break time and see what we can come up with." and she agreed.

At break we went off to my car and started discussing it. "You and Ace can move in any time." I stated.

"Oh god that's really great!" she said "Dave is out of control. He's scaring me and I don't have any options."

"Fuck. That sucks Elaine." I replied "I know it's a tough time for you. People don't often plan a break up."

"Yeah." she agreed.

"Now the thing with rent is this..." I explained "you told me that you don't have the money, but I am willing to let you have the room anyway. The thing is that you will have to allow me some things."

"Like what?" she asked "I can clean. I can cook."

"Well, you'll have to do some of that anyway." I awkwardly stated. "I mean like the things that you suspected that the guy who you met about the room the other day might want."

"Oh." she paused. Just when I thought that she wasn't going to say anything else she said "Okay..." as if to suggest that she wanted to know details.

"Do you think that might be ok, since you know me a little, and I'm not an old stranger?" I asked.

"Yes it could be ok." she said, a little tension in her voice. "I'll have to think about it."

"No problem. It's a tough decision so take your time." I calmly laid out.

"Ok." she replied "I'll think about it."

"You could come over after the shift and we could do a sort of trial run so you would have an idea of what it would be like." I offered.

Elaine looked at me with a little desperation and got out of the car.

"Think about it." I said as gently as I could before the door closed. I was a little anxious as it was uncomfortable to suggest those demands and have her so stressed, particularly because I wanted good things FOR her - I just wanted to do bad things TO her. It was one of those situations where I had a little angel on one shoulder and a little devil on the other.

A couple more hours went by and about 10 minutes before shift end, Elaine approached and said "Maybe the trial run thing is a good idea."

"Ok." I replied "After shift today?"

"Yeah. If that's OK. I am just going to get Ace before I stop by." she explained.

"No problem." I said "Today is good."

On the way home my cock swelled thinking about Elaine's body and the possibilities. By the time that I got home I had a full erection and my underwear was wet where it was stretched over my knob. I was definitely too fired up so I had a beer and hit the shower. About an hour later, a knock on the door announced her arrival and I let her and Ace in. She looked like she just had a shower too and we just chatted and went to the back yard with Ace. After 45 minutes or so throwing a ball with Ace and chatting with Elaine, Ace decided that he was just going to lay in the sun with the ball.

"Ok. Come on in and I'll show you the trial run stuff." I told Elaine as I stepped back inside. She got up and followed me in. I was anxious as anything and gave my hands a good rinse and dried them before taking her hand and leading her to my bedroom. My dick pulsed and lengthened and as we got past the threshold, I turned to her and kissed her. My anxiety was elevated and I wanted her to relax but I couldn't resist reaching down behind her and gently squeezing her ass. "This might be the perfect place for you to live." I said in between kisses.

I kept kissing her and after squeezing her ass for a few seconds, I moved my hands around in between us and reached for her tits. My dick was getting harder by the moment. Those breasts felt as firm as I thought that they looked in her work t-shirts and I wanted to grope them heavily but I thought that it would be wise to just brush the sides of them for now.

Moving my hands back down to hold her ass again, I gently squeezed her firm cheeks and noted her breathing getting deeper. My hands moved back up and between us and I more brazenly rubbed at her tits again. Her nipples stiffened a bit as I squeezed and rubbed them again more thoroughly, appreciating the weight and firmness.

In between me kissing her mouth and moving down to kiss her neck, Elaine said very softly "I...I haven't done this much."

"Don't worry Elaine. You're beautiful. It will be fine." I reassured her, kissing her again while moving a hand back down to squeeze her ass gently.

My cock was throbbing and my lust was starting to really push me so I went for the button on her jeans and popped it, quickly following up by taking her zipper down and putting my hand inside her jeans against her panties which bulged to contain her pussy mound. She had a nice pelvic bump with a firm cushion on it that felt awesome to the palm of my hand and stroking fingers.

"I will be so good to you if you move in Elaine." I whispered to her as I pushed my other hand down the back of her jeans, wondering if she noticed my trembling voice.

"Ohhh..." she moaned in response. She wasn't the 'talk your ear off' type co-worker today.

My cock was straining and throbbing. I hadn't had any sex for months since my recent split, so my excitement was at a really high level. All through my torso was that nervous butterfly feeling which didn't subside as I pulled and pushed her jeans until they got down over the swell of her ass, hips, and the tops of her thighs as her gasps and moans urged me to continue.

Moving the blankets aside, I pushed her gently to sit on the bed and I discarded my own clothing as I continued working her jeans off of her legs. The feeling of relief I got, freeing my erection from my pants was incredible as my rod waved back and forth in the open air and I tossed her jeans aside then grabbed at her round tits, smoothly pulling her t-shirt off. My cock lurched and I felt the precum running down over the big head as I looked at her in her bra and panties.

I leaned in and kissed her mouth, flattening her out on the bed. My throbbing meat pressing against Elaine's mound and belly as I lowered myself on top of her felt incredible and I groped a full hand full of breast before working my hand inside her bra. Fumbling with the clasp, I opened and removed the slightly undersized garment, setting her tits free. Her nipples were beautiful with the areola the size of a quarter and the point rising out like a mini pencil eraser.

Both of my hands grasped at her beautiful tits from below and I kissed and sucked both of them, moving from one to the other and back again to her audible moans. They only compressed a little when she was on her back but not in the way that fake tits did - just as if the skin was pulled a little tightly around them. As I worshipped her breasts, I humped against her and felt my knob rubbing in a slippery patch that it had leaked onto her belly.

I moved down and grabbed her panties, pulling them with both hands. As soon as I got them off of her, I spread her legs with my hands and looked at her splayed out in front of me. Her cunt looked amazing, with a nicely groomed patch of short hair on her mound and the flesh all around her slit shaved smooth. "So nice." I stated and moved in, planting a sucking kiss on her clit causing her to gasp obviously.

Moving up, I licked and sucked at one of her nipples before covering her mouth with mine. I was sucking her mouth with her firm tits pushing against my chest as I squeezed her ass with both hands and pushed my hips forward, rubbing against her rhythmically, feeling the wetness from my cock head transfer again to her flat belly with each movement. "Elaine, you are gorgeous. Dave is an idiot to have dumped you." I told her between wet kisses.

Moans and grunts of discomfort from Elaine's mouth put up little protest as I lowered my hips but kept gently bucking forward against her. My fat wet knob pushed against her pussy clumsily making contact for a moment then suddenly slipping between us as I pushed and it slid over her mound. The hard shaft of my rod rubbed against her after the errant thrust missed its mark. I would have been happy if my cock would have sunk into her pussy right then but after that slippery deflection caused it to wave between us, I decided to move up and push my pulsing wand toward her mouth.

Elaine took my swollen cockhead into her mouth with gentle wet sucking sounds. "Oh God, yes Elaine!" I whispered to her as I humped at her face. A pull back removed my wand from her mouth exposing my saliva covered cock and a push forward reintroduced my throbbing dick back into her warm mouth which sucked and licked around the top of my shaft and the engorged head. Pulling back from her mouth I moved down and beside her on her left side, lifting her leg to get my cock against her cunt from that angle.

With me on my side and her still on her back, I put the hard shaft against her slit with my right hand while I pushed my left hand under her ass. Kissing her from the side, I reached up and fondled her tits while stroking my cock against her slit, the head sticking out past her mound and the side of the shaft making good contact with her labia. Elaine gasped and sighed as I sucked on her mouth and tongue.

The middle finger of my left hand found her ass hole and slowly rubbed it in little circular movements as my dick rubbed against her pussy lightly. Every once in a while I would stop fondling her breasts and reach down and push my cock against her slit which was getting wetter with each passing second.

I adjusted a little and felt the end of my throbbing member lodge against her warm wet hole and I pushed gently. Her pussy was tight but incredibly wet so the puffy head popped right in. "Ohhh..." she whimpered and I pulled my hips back just enough to withdraw the the fat end from her then immediately stick it in again. She whined as the swollen head pushed inside her for the second time so I pulled out and positioned myself on top of her, pulling her legs up and putting my shoulders behind her knees.

Planting half of my cock in her hot cunt I said "Yes Elaine. So nice!" drowning out her whimper as I worked my hands under her to hold her ass.

As I pushed deeper into her she gasped again "Ohhh..." and I withdrew again before pushing my fleshy invader into her once more. I pulled her toward me with both hands firmly gripping her ass and reached my middle finger to press it lightly against her ass hole. Each forward thrust was met with a gasp from Elaine and more slippery wetness from her warm cunt. By the fifth push, I was fully buried in her velvety enclosure and she had flung her arms around my neck, her warm mouth panting in my ear.

My cock was pulsing and my breathing was heavy so I just held still in her. My heartbeats were smashing in my head and I could almost hear them from my throat as I panted, fighting to calm my senses and I took my finger away from her ass hole to help me calm myself more thoroughly.

Moving ever so slightly inside her I could feel myself gaining some control back. "How is that Elaine?" I whispered to her and sucked onto her mouth sloppily.

"Uhhhn...I..." she moaned as I cut her off with my tongue in her mouth and my lips moving on hers as if I were attempting to devour her.

"Free rent - just take my cock whenever I want to give it to you." I said as I lengthened my strokes in her, still gripping both of her ass cheeks firmly. I hunched down to lick at her tits and with much determination, I was able to push her legs further out to the side, and wetly paint her nipples with my tongue as my cock slapped into her moist cunt with a wet smack.

Watching my cock push into her I saw the edges of her pussy lips disappear, and as I drew away from her, removing my veiny pole from her hot cunt, I saw the edges of her labia expose themselves. Her pussy was tight and felt amazing on my pistoning cock while she moaned and panted and I put my finger against her ass hole once more.

I lewdly tongued her mouth as I pumped my cock into her. With each thrust I moved my middle finger on her ass hole rubbing around it in circles and pressing against it. Elaine's gasps had elevated into panting and her moans increased in volume when only seconds later, I felt her muscles contract on me. Realizing that she was coming, l pushed my slippery finger through the tight obstacle of her tiny ass hole. My finger slipped inside and her ass contracted around it in time with the muscular spasms of her cunt as her gasps filled my ears, sending my lust into overdrive.

Her pussy was milking my cock with incredible contractions as I withdrew it from her shaking body and pulled my finger from her snug, flexing anus. I directed the fat head of my tingling member to her tiny shiny ass hole and pushed. "Oh!" Elaine gasped in the throes of her orgasm as I pushed again against her unyielding hot ass hole. I felt her anus flex against my swollen knob and pushed again desperately, lodging the fat head in her ass. "Oh god!!" she groaned as I pushed again, and my cock head slid past the tight entrance of her ass and her anus gripped the shaft of my tingling rod just below the head.