The Helpful Roommate Ch. 02

A few weeks had passed, and neither of us had spoken about that night. There were a few shared glances here and there, moments in which both of us could easily tell that the other was thinking about it. Finally, one Friday evening as I came out of my office for the day, Samantha was standing there, right in front of the door obviously waiting for me.

"OK." She said, then switching to her impression of a movie trailer voice over, continued "It's payback time!"

I laughed at the joke, and continued laughing for far longer than justified, because I was suddenly very nervous. I had known since the night she asked me as a favor to go down on her exactly what I was hoping she'd be willing to do in return. However, I was scared to ask for all the same reasons I'd always been afraid to ask it of the women I had dated earlier in life. The same reasons that later, I couldn't even talk about it with my wife.

She eased my tension by stepping in close and placing her hand on my arm. Practically looking directly into my soul with all the beautiful depth of her golden brown eyes.

"I remember you said, when I told you that I'd repay you 'in kind', that you may have something else you were interested in. Can I take that to mean you don't just want a simple..." She smirked slightly; "... but I promise, amazing, blow job?"

For a moment I thought about chickening out, again, from asking for the thing I really wanted. After all, it had been a very long time since I'd had my dick sucked, and I believed her whole heartedly that it would be an amazing one. I was about to say so, when she interrupted my thought by saying;

"You know you can ask me for anything. I won't judge you at all. After the orgasms you gave me that night, I would be willing to do just about anything for you."

Steeling my resolve, I swallowed hard against my suddenly very dry mouth, and responded; "Alright, but promise me, if it's too weird for you, or you think you would be too uncomfortable doing it, I'll be totally OK with you saying no. I don't want you to feel forced in any way. Please promise me you won't go along with it only because you think you 'owe me.' I just ask that what I'm about to ask never leaves this house, OK?"

She took her hand off my arm, held it up in a loose fist with her pinky finger extended in a slight hook. "Pinky promise!" She said, with a wide inviting smile on her face.

I hooked my pinky in hers and said; "Pinky promise." in return. Then I said, "Alright, I need just a bit of time to prepare. I'd like to take a quick shower before anything else. I'll call for you in about 20 minutes, OK?"

"Anything special I should be wearing... or not wearing?" Sammy asked me with a slight smirk and a twinkle in her beautiful eyes.

I thought about it for a moment. What I was going to ask didn't have any special wardrobe requirements for her... however I wasn't going to pass up an opportunity to see her gorgeous body in a sexy outfit either. So I said; "Nothing specific, but just pick out what you think is your sexiest set of lingerie. I'm sure that will be more than satisfactory."

She said; "I have just the thing!" Turned on her heel and headed toward her own bedroom.

Leaving me still standing in front of my office, with knots in my stomach, but the undeniable stirring of arousal a bit lower down. This was going to take some thought. I knew exactly what I wanted, but I didn't know how to ask for it. I headed toward my room and hopped into the shower, already growing hard at the thought of what might be about to happen. Still feeling nervous about how to ask, and whether or not she would find it too weird to go along with.

I showered well, making sure I was very clean, especially in those 'hard to reach' places. Knowing that some of those places may soon be on display in a way they aren't normally seen, even by one's lovers. I got out of the shower, wrapping my towel around my waist and tucking it in to keep it tight. Which immediately reminded me how this all got started, with Sammy wearing nothing but a towel tucked under her arm, just covering her perky breasts. I had thought about changing back into some sort of clothing, maybe even just boxers. That memory, however, made me realize that the towel would be the perfect way to bring this full circle.

After running a comb through my hair, brushing my teeth, and just generally making sure I didn't look like a total scrub, I headed to my closet. Moving several boxes from the corner, full of things that I was sure I'd need again someday, but that would probably live forever in these containers. I finally found the one I was looking for, a smaller box I had cleverly labeled 'DS' code in my own mind for 'Dirty Stuff.' Opening the box, and moving aside the old newspapers I had used to pack, I found the items I was searching for.

I hastily shoved the boxes just far enough back into the closet to close the door, and took the 'DS' box to the bed. I pulled out the three carefully packed items, each in their own velvet bag, and placed them in order of size on the bed. Now was going to be one of the hard parts... I could ask Samantha to use all three, or I could let her choose. Since this was going to be a first time thing - as far as I knew - for her though, I opted to make the choice and picked up the two larger items and placed them back in the box. Closing the box, I slid it under the bed leaving only the one remaining velvet covered object on top of the duvet.

I looked at the black velvet bag, knowing that the object inside was either about to be used for the first time in many, many years... or it was going to scare off the one woman with whom I'd had any intimacy since my wife passed. I was suddenly very nervous again, thinking that I was an idiot to even think about bringing this part of my sexual desire out again after all this time. Thinking that Sammy was going to bolt out of the room as soon as I told her what I wanted. Or worse, that she'd go through with it, but be so disgusted that we would no longer be able to even speak to one another.

I had come very close to picking up the remaining object, putting it away with the others and just telling Samantha to never mind when I heard a soft knock at my door, and her voice from the other side saying; "Are you about ready for me?"

In that moment, I remembered her sweet smile, and the sincerity in her perfect eyes when she had pinky promised just a short time earlier that she wouldn't freak out, wouldn't tell anyone, and most importantly, wouldn't go through with it if she was uncomfortable. I decided, the hell with it, it's now, or it's quite literally going to be never. So I headed to the door to open it and let her in.

I was not prepared for the sight I beheld when I opened my bedroom door. Standing in front of me, backlit perfectly by the light of the setting sun coming in from the main room, was Samantha. She was standing tall in a pair of white strappy heels that had to be at least 4 or 5 inches high. Her lacy white bralette, just sheer enough for me to see the darkness of her nipples, with a thinner lace kind of wave pattern hanging down from the base of it just long enough to touch the top of her belly button. A pair of very sheer, white lace boy short style panties completed the outfit, giving me a wonderful view of her long, lean legs.

She caught me staring, cocked her head slightly and smiled. She did a quick little turn around on one foot to show off all angles of the ensemble and stopping again to face me said; "Well? Does this work, or do I need to change," After which she put on a frowny little pout that was obviously fake, as I could still see the smile in her eyes.

"You look, simply, and literally... stunning." I told her honestly. "Please, come in."

I moved aside to let her through the door and watched closely as she stepped in. Walking slowly and deliberately, to accentuate every move her body made. Stepping one foot in front of the other to force her hips to sway back and forth showing off her amazing ass. I was transfixed for a moment, until I realized how close to the bed, and the object still lying atop it, she had gotten.

"Holy fuck, you're gorgeous." I said, both honestly and to get her attention.

She turned back toward me and said; "Thank you, I haven't worn this outfit in a while, I didn't think a certain someone was worthy of it."

She was of course referring to her ex-boyfriend, the one with whom she'd broken up the night before our prior encounter. Thinking about her holding back such an amazing looking outfit from him, but wearing it for me turned me on even more, and finally pushed me from too nervous to ask, to too horny to care. It was time, I was going to finally pull the trigger and shoot my shot.

"So... you know I want to ask you for something a little, um, out of the ordinary." I started. Moving a step closer to her. "Something that I have always enjoyed, but also always been really scared to ask for from the women I've been with."

Sammy took a big step closer to me, once again resting her hand on my arm, and once again staring into my soul with those eyes, said; "Go ahead. It's OK." then, in a more seductive tone she added; "What can I do to please you right now?" Still looking me right in the eyes, but with a softness on her face that said 'you can tell me anything' and the slightest of bites to her lower lip that said 'I want this as badly as you.'

I stepped past her to the bed, and picked up the object retrieved from the recesses of my closet. I held it in both hands for a moment, looking at it, then looked up to her.

While carefully opening the black velvet bag, I said, slowly, and deliberately; "Samantha, may I please have a spanking?"

While that hung in the air, I removed the bag. Revealing the smallest of the paddles I owned. This one the basic size and shape of a hair brush, minus the bristles. About 8 inches long including the handle, 3/4 of an inch thick, made of solid oak polished to a bright shine. The feel of the wood in my hands gave me renewed courage and I continued.

"Samantha." I said again, looking directly at her; "Tell me now if this is too weird. I don't need to be scolded, I don't want to be dominated, but I do want it to be hard, very hard. I want to feel the sting and tingle on my bare ass, and know that a beautiful woman is the one holding the paddle. I want to have bruises that last for days, reminding me of this moment anytime I sit down." I stopped hoping that I hadn't gone too far.

She looked confused for the briefest of moments. Then looked at me with her sly little smirk, reached out her hand and said; "If you want a blistered ass, then a blistered ass is what you're going to get. Give me that paddle, and lose the towel."

Tossing the velvet bag on to the night stand, I placed the handle of the hard wood paddle in her open palm. She rubbed her hands over the wood, much in the same way I had done when taking it out. Finally, she gripped it firmly and gave a few light smacks to the palm of her other hand.

"Oh!" She exclaimed, "This is going to be a good spanking! You'll definitely feel this for days." At this point I hadn't yet taken off the towel, Sammy pointed at it with the paddle and said; "I thought I said to lose the towel?"

Doing as she said, and mirroring her actions from the night she'd asked me to eat her pussy. I tossed the towel aside, now standing naked and very much erect in front of her.

"How do you want it?" She asked me and she moved close enough that I could feel the heat of her body on my skin. "You want me to take you over my knee? Or should I have you lay on the bed?"

I was fully engrossed in the scene now. She was playing it perfectly, unlike the few women I'd tried to bring up my fetish with in the past. Who were either too timid to make it work, or became so domineering that it turned me off. As I had told Sammy, for me, it wasn't about being dominated, or punished. It really was just about the feeling of the paddle stinging my ass cheek, then the tingle as it radiates out from the spot of the strike.

"Will you please spank me over your knee, Sammy?" I said.

Without a word, she moved to the side of the bed and sat down. Adjusting herself for comfort, she ended up with her thighs positioned about half on, half off the bed. She spread her legs slightly and motioned me closer. Taking my hand and guiding me silently to get between her legs, and lay across one knee. Most of my weight being held by the bed to her left side. She lifted her right leg, and brought it back down across the back of my thighs, effectively holding me in position.

I was beginning to think this wasn't her first time taking someone over her knee for a hard spanking. She was so deliberate about her movements. Positioning my ass perfectly in front of her so she'd have easy access to both of my bare ass cheeks.

She rubbed the smooth wood of the paddle against my butt for a few moments, gently making a sort of figure 8 across both cheeks. Finally, she spoke again; "Do you need a warm up?" She asked.

This definitely wasn't her first time. "No." I replied, "I'm ready. Please paddle my ass, Sammy. Please spank me." I hadn't meant the last part to come out so desperately, yet it did. Samantha heard the need in my voice and didn't wait any longer. Bringing the paddle down hard against my right ass cheek five times in rapid succession on the same spot. Then switching to the left cheek and administering the same five hard, fast swats.

Those first ten took me by surprise and I squirmed a bit over her knee. Her response was to tighten her grip on my legs with hers and repeat the five swat pattern to each cheek again, this time even harder than the first.

I didn't cry out, but I did let out an exhaled "whoooo" sound and rocked back and forth just a little over her knee. She set the paddle on my back and touched my ass with her finger tips. Lightly tracing the edges of the spots she had just beaten.

"Looks like we're off to a good start!" She said, picking the paddle back up and bringing it right back down against my bare ass. This time ten swats rapid fire, two on each cheek, then two on the other back and forth.

I was in heaven. This woman knew how to spank. She kept up the pace, spanking hard, and fast. Sometimes going back and forth between cheeks, sometimes repeatedly spanking the same cheek. I never knew where the paddle was going to hit next. She covered both ass cheeks thoroughly, from the tops down to the 'sit spots' just above the thighs. Only stopping when she could tell I'd gone from feeling the sting of each swat to starting to become numb to them.

She set the paddle on the night stand and gently rubbed her fingertips across my well spanked butt. "Well, did I do OK?" she asked, jokingly.

"That was amazing." I replied breathlessly but honestly. "Thank you so much."

She moved her leg so I could get up and scooched over so there was space beside her. I got up from her lap and gently sat down on the bed with her. My cock still (or again) hard and the slightest bit of pre-cum glistening at the tip.

Seeing this, she reached over without a word and gave my dick a gentle squeeze, bringing the drop of pre-cum fully to the surface. Which she then used the tip of a finger to scoop up and put into her mouth.

"Mmmm... I guess you really did enjoy that?" She said, then grabbed the sides of my face and pulled my face to hers in a long, deep kiss.

Finally pulling back from the kiss, she grabbed by cock again. Slowly stroking it up and down. I was so lost in the moment that I just put my hands on the bed behind me to hold myself up, leaned back and let her work.

After such a build up, an absolutely amazing spanking, and now a gorgeous woman giving me a hand job, I didn't hold out long. Soon, I was making the unmistakable sounds of a man about to explode.

"Yes," she said; "cum for me, I want to see you cum!"

That was all it took. I let myself go and had one of the most intense orgasms of my life. The position I was in, coupled with how Samantha had pointed my dick meant that almost every drop landed on my stomach and chest.

Keeping one hand on my cock and continuing to apply gentle pressure and strokes, she used her other hand to scoop some of my cum from my torso, collecting as much as she could in her cupped fingers.

Without a word, she brought the small handful of cum slowly towards my face and looked into my eyes with a silent question. Somehow, I knew what she wanted, and although a little nervous, I opened my mouth to let her feed me my own cum.

I watched her closely as she carefully tipped up her fingers and allowed the first dollop of cum to drip into my mouth. The delight on her face was unmistakable. I smiled to let her know I wasn't turned off, and to my own surprise I found that it was an honest reaction. I was also surprised by the lack of any real flavor to my cum. Having never tasted myself in such a direct way before.

It was similar to a raw oyster, but without the fishy smell or taste I'd associate with that. The texture was a little off-putting at first, but that very quickly dissipated simply by glancing left and seeing the absolute raw passion on Sammy's face. I kept eye contact with her now noticeably sparkling eyes, closed my mouth and made a bit of a show of swallowing the load she'd just fed me. I smiled, completely honestly this time, and continued to look at her with a passion of my own I hadn't felt in many years.

"Fuck me! That was so goddamn hot!" She cried out, finally breaking the silence. Then leaned over and kissed me hard, and deep. Her tongue practically danced around the inside of my mouth, as if searching for any hint of the cum I'd just eaten for her.

She looked down and started to scoop up some more of my cum from my chest and stomach, bringing her fingers back to my mouth. This time, I met her hand willingly licking and sucking my own jizz off her fingers while watching her breathing get heavier and heavier.

She finally let go of my cock, used one hand to push aside her panties, and started fingering herself. While using the other hand to find any last drops of my cum she could and feed them to me. Every drop she brought to my lips I eagerly devoured for her. Keeping eye contact while swallowing each and every drop of my own cum. The pure desire in her deep brown eyes made me completely willing to do anything she wanted. The sound of her fingers working quickly in and out of her wetness filled the room.

Having found, and I having eaten, just about every drop of my - for me - fairly impressive load. She dropped back onto the bed to focus entirely on working her slick pussy with her fingers. Arching her back in ecstasy as the wave of an orgasm quickly overtook her.

I turned to my left, one elbow on the bed, hand propping up my head and just watched in fascination at how fucking gorgeous she was in the throws of passion. Although it had been a very long time since I had been able to go more than once in a single night, I felt the stirring of desire already, and was actually a little shocked when I glanced down to see that my cock had started to chub back up a bit.

At this point, I also started to notice the aftertaste of the cum I'd been so eagerly swallowing just moments before. Somehow more potent than the taste of the cum itself. It wasn't a bad taste, but it was definitely different. I decided there was an easy way to cleanse my palate, as it were, and it was staring me right in the face.

I picked myself off the bed, grabbed Samantha firmly by the waist without interrupting her continued manual stimulations and moved her just farther enough up onto the bed to allow me room to climb between her legs again. Lowering my face to her pussy again, as I had during our last encounter.

Without a word she moved her own fingers out of her dripping cunt, moving them up to her clit and continuing to rub herself, but giving me room to add my tongue to the stimulation of her sex. I could feel heat on my face, more so even than the previous time I had gone down on her. She was wetter than before too, something I hadn't thought possible after our first encounter.