The Helpful Roommate Ch. 01

I'd been living with Samantha for just over a year now. She'd just recently signed a new lease agreement with me to continue on as my roommate for another 18 months. This was great news for me, as the house I had purchased just before my wife passed was too big for me, and felt lonely when empty. I didn't have the patience, or energy to put myself back out into the dating world at my age, and didn't have a lot of friends in town. Plus the fact that I worked from home, meant that I was there most of the time. For several years, the place had just felt... empty.

Living with Sammy had been a true blessing. She was clean, neat, and organized... but not compulsively so. She was respectful of my work from home hours, never playing music or watching the television too loudly when she knew I was in the office working. We shared a meal or two each week together, when our schedules permitted it, and on rare occasions would watch TV or a movie together in the main room when she didn't have something else going on.

Samantha was quite a bit younger than I. having just turned 30 prior to moving in, compared to my upcoming 47th birthday. She was also quite beautiful in a very 'girl next door' kind of way. Standing about 5'8" on flat feet, but had a predilection towards wearing heels or wedge shoes that added a good 3 to 4 inches to her natural height. She wore her dark hair just below shoulder length, with natural looking waves most of the time. Sometimes taking the time to straighten it, which made it appear much longer. Her face was what most would probably describe as cute, rather than hot, however she knew very well how to apply makeup in a way that could change that perception. Having seen her plenty of times with no makeup whatsoever, I knew how naturally pretty she really was. Especially her deep golden brown eyes, regardless of what she was wearing on a given day, it was never hard to look into her eyes, as they were almost impossible to turn away from. Her body was perfectly shaped for her height, not too skinny, not chubby or overweight. When dressed for a night out, she'd often wear bras and tops that made her breasts look much larger than their natural size, but having seen her around the house in a tight fitting tank top I knew them to actually be on the high end of a B cup. Besides her amazing eyes, her next best feature were her long, lean legs. She went to the gym at least 3 times a week, and I don't know what she did there, but it was working. Her legs were lean and toned without being thick or too muscular looking. They were just perfect stands leading up to one of the best asses I'd ever seen in a pair of jeans.

However, while I was obviously very attracted to her, I never tried to act on it. Not even basic flirting. I didn't think it would be appropriate as her 'landlord' first of all, and secondly the age difference made it even more inappropriate. So I was content to steal glances at her around the house and was simply happy to be sharing a home with a beautiful woman.

I tried to stay out of her affairs, but I did notice that although she had a long term boyfriend, she never brought him over or had him inside the house. I asked once if she thought it was against some rule or something, which she assured me was not the case. I had never never placed, nor would I have even thought to place, any restrictions on her comings, goings, or inviting of guests. All I had ever asked was that the rent and bills be paid on time, and that the common areas of the house kept a respectable level of cleanliness.

Then came the night that started a new chapter in our relationship. I had just gotten off work, and was coming out of the office to head to the kitchen for a beer when I noticed Sammy was in the main room crying. I took a couple steps into the room, keeping a respectful distance, and gently cleared my throat to make sure she knew I was there.

She stopped, looked up at me, sniffled a little, and said; "I'm sorry, I didn't realize how late it had gotten. I'd better go to my room."

As she started to get off of the couch I replied; "You don't have to go anywhere, you're allowed to cry wherever you need to. I'll leave you be if you want, or we can talk if you want?"

She looked at me with those perfect eyes, red around the deep brown from the crying, and said, to my surprise; "Yeah, I'd like that. Let me just clean up a bit first."

Then she got up and headed toward her bathroom, turning back about halfway there and saying; "Were you going to grab a beer? If so, would you mind grabbing me one of my hard seltzers while you're in there?"

I was a little surprised at how well she knew my daily routine, but didn't think too much about it as I went to the kitchen and got our drinks.

I sat down on the far end of the couch she had previously been sitting on, then thought to myself 'No, this is too close, too personal. If she wants you closer, she'll let you know.' So I set down her drink on a coaster near where she had been sitting and moved myself to the chair adjacent to the couch on the opposite side. Where I could easily talk to her face to face without being 'in her face' so to speak.

She came back from the bathroom with her hair tied back behind her head in a messy ponytail, she had dried her eyes and washed all traces of her makeup off. She was still stunning, maybe even more so with the soft vulnerability of the recent crying still fresh in her eyes. She picked up her drink and coaster and moved over to the end of the couch next to the chair in which I was sitting.

"Todd and I broke up." She stated bluntly.

Todd, that was his name, the boyfriend she'd been with since before she moved in with me. I think I had met him all of three, or four times. She rarely spoke of him, yet somehow I had always just had a general feeling of dislike towards him. I suppose I had always written that off as a bit of jealousy, since she had never once shown any signs of the relationship being abusive in any way, nor had she ever complained openly about him to me.

"I'm so sorry." I replied, stopping myself from immediately asking what had happened. Instead I let those three words hang in the air as an invitation for her to elaborate, or not as she desired. While keeping a steady gaze into her eyes.

She took a big gulp of her drink and said; "Don't be. He's an asshole. Always has been. I left him. Been wanting to for a long time, but always told myself that I'd never do any better." Then she took another long drink, looked at the can, said; "I'm going to need something stronger after this one."

I chuckled slightly, unsure if this was the correct response or not, but picked up my beer and took a long drink myself. "Well, I've got a bottle of Scotch I've been looking for an excuse to open up, if you're up for getting sloshed on a work night."

She tipped her can towards me in a gesture of mock toasting, raised one eyebrow slightly and drained the rest of her can in one long chug. Setting it down, and saying; "Yeah, I think I'm up for that."

I laughed out loud and said; "Well alright then, let's start the serious drinking!" Drained the rest of my beer, got up, retrieved her can from the table and headed to the kitchen to get the whiskey.

Over the course of the next few hours, we talked about anything and everything. Everything that is, except Todd and her break up. I learned more about her that night than I had gleaned over more than a year of living together. I'm sure she did the same about me. As the level of Scotch in the bottle got lower and lower, the conversation got heavier. Slower, and a bit garbled as well, but the topics started to get more personal and serious.

"Can I ask you a personal question?" she said, suddenly a little less slurred than before.

"Haven't most of these been personal?" I asked, chuckling; "Do you mean more personal?"

Samantha tossed back the half a finger of whiskey currently in her glass, set it down on the coaster, and leaned toward me. Her face, and those beautiful eyes, seemed suddenly to be mere inches away from my own.

"Do you eat pussy?" She asked, not breaking eye contact for a single moment.

I stared back into those eyes, going through a range of feelings I'm not sure I fully understand, for several long seconds. Finally replying with a simple; "Yeah, of course." Then I took a sip of my drink, sat back in my chair a bit and added; "I haven't for a while, of course. I haven't really had the opportunity."

She looked genuinely shocked for a moment and asked; "Why not? You're a good looking guy, single for a while now, are you not putting yourself out there?"

"No, not really." I replied. "I just never felt the need to get back into the dating world. I tried a couple apps a few years ago, but never even met anyone in person." Trying to get the subject off of my lack of social and love life, I steered back to the original question by asking; "But why do you ask about that in particular?"

She sighed heavily, and looking at the ground said; "Todd never ate me out." she paused for a moment; "Not once, in the three years we were together."

"He wasn't a fan of oral?" I asked.

"Oh, he liked oral just fine if I was sucking his cock." She said angrily, looking back up towards me. "He just wouldn't return the favor, you know?"

If I hadn't already thought this guy was a douche bag before, I would have thought it now. So I said so, telling her; "Fuck him, he's a douche bag, and will be some other unsatisfied woman's problem in the future."

She laughed loudly, and then paused, looking at me with an expression on her face I didn't quite understand but looked like a question was forthcoming. However, a question never came, instead, she said; "Thank you for tonight, I needed that. I'd better get to bed. Work is going to be hell tomorrow."

Still a little shell shocked at the previous turn of the conversation, she was almost into her room before I called after her; "Drink some water before bed! I'll put a few Gatorades in the fridge for us, for tomorrow."

I put the glasses and nearly empty bottle in the kitchen, put a few sports drinks in the fridge as promised, and, forgoing my normal bedtime shower, went to bed myself.

The next morning, I got up for work as usual, a slight headache being my only real punishment for the previous night's indulgences. As I made my way down the short hallway from my bedroom to the office, I heard the unmistakable sound of a 'hangover moan' come from Sammy's bedroom. I smirked to myself, a little too proud of my body's tolerance to heavy drinking.

Normally, Samantha leaves the house for her job shortly after I start mine in the morning. I'm usually able to hear her moving about and getting ready, then leaving long before I take my first break of the day. On this day, I heard nothing. No shower, no getting ready, and certainly no leaving the house. When I did take my break, I went towards the kitchen for a coffee to see Sammy curled up on the couch, nursing a bottle of Gatorade and watching some reality TV show in the living room. The sound was off, but the captions told me that Brad was very upset over something Tiffani (not to be confused with Tiffany) had done to Mike (not to be confused with Michael) at the previous episode's event.

"You know, you can turn the sound on. It won't disturb my work unless you're absolutely blaring it out here." I said, fairly quietly to her.

She nearly jumped out of her skin, turned to me angrily with a finger to her lips and said; "Shhhhhh!" before grabbing her head, then her stomach, then putting one hand on each while slowly shrinking back into the couch.

Understanding her pain, I quietly made my way into the kitchen and made myself a cup of coffee. Before going back into the office for work, I detoured to my bedroom to grab a few medications from my medicine cabinet that I thought might help her out. As silently as possible, I put the bottles of Tylenol, tramadol, and diazepam on the table near her and said in a hushed voice; "If you haven't taken anything yet, one of each of these, and a lot of hydration is a great hangover killer." Then I went back to work.

A few hours later, Samantha messaged me on my phone, asking 'If I take a shower, will it disrupt your work?' To which I replied, 'Of course not, feel free. I still have to take one after work, since I didn't last night.' Shortly after, I could faintly hear the running of water through the house that always let me know when water was traveling from the heater in the garage to the deeper parts of the house.

When I was done with work for the day, I walked through the main room to the kitchen to deposit my coffee mug in the sink, and grab a beer as usual, only this time with the intention of taking that beer with me to go shower right away. I noticed as I walked by that Sammy was back on the couch, but now wearing just her towel, sitting upright, sipping a bottle of water and watching her shows on a low - but audible - sound level.

Just as I passed into the hallway, I heard her call after me; "Hey, when you're out of the shower, I have a question for you. No rush."

After getting showered, putting on an old T-Shirt and a pair of sweatpants, I headed back out to the main area and kitchen. To deposit my shower beer bottle in the recycling bin, and to find out what Sammy had wanted to ask.

Coming out of the kitchen with a fresh beer, I found her with the TV show paused, bare arm over the back of the couch looking at me.

"Can I ask you a huge favor?" She asked, in a slightly ashamed tone, as if she was about to ask to borrow money.

A bit surprised, I responded; "Well, you can ask, but I make no guarantees until I know what it is." and chuckled a little, more to display that I was teasing than for any other reason. She looked down, and made noises that sounded like she was starting to say; 'Never mind...' but I cut her off, saying "I'm just kidding, you can ask me for anything, if I'm able, I'll help you out."

She paused for a good several seconds, then looked up, making contact with those perfect dark brown eyes, and said; "Will you eat my pussy, please?"

As shocked as I was by the question, and the timing of the delivery, I did my best to not show it. I kept eye contact, searching the deepness of her eyes for any hint that this was a joke. Finding none, I finally said; "Yes. As long as you're sure."

She smiled, and those eyes I was still staring into lit up bright as she said; "Oh, I'm 100 percent sure!" She paused for a moment, and then said; "And don't worry, I'll repay you in kind of course... but, can that wait for tomorrow? I kind of want this to be just for me right now. Is that OK?"

At that point, I hadn't even fully processed what it was that I had already agreed to, so the prospect of 'repayment' hadn't even crossed my mind. I said; "Yeah, for sure, this will be just for you." I paused for another moment, thinking about something I'd been wanting for a very long time, and said; "We can figure out what you can do for me another time."

Visibly relieved, Samantha turned off the TV, and said; "OK, where do you want to do this?"

"Well, this is for you, so wherever you will feel the most comfortable, and get the most pleasure from it is fine with me." I said.

She thought briefly, then stood up, came round the couch, took my hand in her's and led me toward her bedroom.

This was the first time I had been in this room since she had moved in, as I respected her privacy, I had no idea how she had chosen to decorate her space. I looked around very quickly, not wanting to get too distracted from the purpose of my invitation to this space.

She finally let go of my hand as we got next to her queen size bed, perfectly made, with about 14 or more pillows against the padded gray headboard.

She turned to me, looked me up and down and said; "Since I'm going to be completely naked, would you mind stripping down also? It would make me feel a little less vulnerable."

I said; "This is a personal favor for you, to which I have already agreed. So, you don't have to ask for anything from here on. You just tell me how, and where you want me, and I'll be there."

She smiled and said; "You have no idea what this means to me, really. I just need you to promise me one thing. I don't want to fuck tonight. I just want to get my cunt eaten out until I cum like a fucking porn star, ok?"

I was shocked at her sudden change in language and tone, but I quickly got over it and said; "Absolutely. You're running this show, just tell me what you need."

"From this point forward; know that I do NOT want to fuck tonight. Even if I say things while you're... down there..." she was suddenly back to the more demure version of Samantha I knew, "please don't do anything else. Can you promise me that?"

When I looked in her eyes to make the promise, I could see the slight fear there. I knew in that moment that she'd never been in complete control over her own sexual experiences before, and was terrified that the grip on it she had right now was going to be lost.

I looked directly into her gorgeous eyes and swore; "What I'm going to do tonight is tongue fuck your pussy until you cum so hard you're seeing stars. Nothing more, nothing less."

In a blink I could see that she believed me and was relieved, excited and ready to go all at once. She reached for the part of her towel that was tucked under her armpit holding it in place and paused while looking at me. I took off my shirt, tossed it aside and started taking down my sweatpants. By the time I looked up from removing my feet from the pant legs, she had removed the towel and was now standing in front of me completely naked.

Her naked body was even more remarkable than I had ever imagined. Her tits were pert and perky like a woman 10 years younger, and every curve that should be on a woman was exactly where every curve should be. Her pussy was completely hairless, having been obviously shaved or waxed very recently. The lips were perfectly shaped and inviting. If I hadn't already been there with that intention, I still would have immediately wanted to have a taste.

As I lowered my boxers, and Samantha saw my erection growing, there was a slight bit of fear again in her eyes and she whispered; "Remember your promise."

"I will." I said, keeping eye contact as I finished removing my underwear and stood, waiting for her to make the next move.

She looked at me, standing naked, cock hardening each moment I looked at her and then turned slightly to climb into her bed. She spread her hair out behind her head and lay back on a few of the many pillows. Positioning herself with her knees in the air at first, she slowly opened her legs, and spread her feet. The invitation might as well have been engraved at that point. I climbed on from the food of the bed, slowly crawling my way closer and closer to her waiting pussy.

When I was just close enough to smell her wetness, and could almost taste the sweet tang of sex on my lips, I slowly reached out my hands to find hers. Once our hands were touching, my face still barely an inch from her slick womanhood, I placed my hands, palms up in her hands and whispered just loud enough for her to hear; "You control these, put them wherever you want, they won't touch anything you don't want them to." and without waiting another moment I pushed my mouth against her dripping pussy.

Using only my lips and tongue, I spread open her lips and searched for the elusive clit. Finding it, I started to really go to work. As I continued to use my tongue and lips to stimulate Sammy's entire pussy, I kept my hands palms up on the bed beside her. I desperately wanted her to guide them to her tits, or to her hips and ass... but I kept them still as promised while keeping up the mouth work on her now extremely wet cunt.