The Helpful Roommate Ch. 04

"Hmm... I think that's warmed up nicely." I then reared back and smacked her ass hard on each cheek, eliciting a yelp from Sammy. She put her arm behind her, hand trying to block mine from raining down more hard swats. "Uh, uh." I said while grabbing her wrist with my left hand, holding it at the small of her back. "Let's keep that out of the way." Looking at my work, I added "I think it's time to lose these." I gripped the waistband of the smooth, red panties and pulled them down over her ass cheeks. Without my asking she shifted slightly to allow me to easily pull them completely down her thighs, settling in the nook of her slightly bent knees.

The view I had now was incredible. Samantha's bright pink ass cheeks were on full display and between them just a hint of her soft pussy, already glistening with a hint of moisture. I adjusted myself just enough to pull her up a bit higher on my lap and spread her legs slightly, giving me an even better view of her sweet slit. I licked my lips unconsciously at the sight. Regaining my composure, I resumed the hand spanking. Swinging my arm hard, I brought down my hand against one cheek, then the other pausing for about a full second between swats. After about eight swats, Sammy finally started getting more vocal and squirming about my lap more forcefully. I held her tighter against me with my grip still on her wrist, to continue the spanking. Swinging nearly full force now, I gave her another ten swats. Smacking each cheek five times in a row, my hand stinging enough to tell me that her ass must have been on fire.

"Ow, ow!" she called out breathily.

"Stand up." I commanded, releasing her arm from behind her back.

Breathing deeply, she first slid down my leg to her knees, then pushed herself up to a standing position. Her panties falling down her toned calves to her feet as she did. Her eyes glistened with a hint of tears forming, but none had fallen yet.

"Strip. All the way, now."

Once again, she didn't hesitate a second. Taking a single small step forward lifting her toes out of the panties to step out of them, while simultaneously starting to unbutton her shirt. I watched with pure lust as she finished removing her blouse and placed it over my jacket on the bed. Then by unzipping a small zipper on the side of the skirt, allowed it to fall slightly down to her hips. She tugged at the hem to allow it to slide over her hips and fall to the ground. She took another small step to get her toes out of the skirt on the floor. Then turned around pointing her hot, red ass toward me again, and bent at the waist to pick the skirt and panties up. Turning back toward me, she placed the skirt atop the shirt, and the panties on top of the small pile. Standing inches away from me, now wearing nothing but a thin red satin bra with lace trim that matched the panties now piled on the bed.

Looking into my eyes, she said "Help me, please sir?" and turned around again gesturing to the clasp of the bra at her back.

I reached up and released the two small hooks from their loops, allowing the straps to fall aside. Sammy had placed an arm across her chest to keep it from falling off instantly; instead waiting to turn back towards me before moving her arm and removing the bra. I inhaled sharply at the sight of her perky breasts, hoping that I would never start to take this vision for granted. She crossed her arms behind her back again, face downward, waiting for my next move.

Standing up, almost fully erect inside my suit pants, I turned slightly toward the bed. I picked up the riding crop and inspected it. This wasn't a cheap sex toy, this was obviously the real deal, probably purchased at a feed and tack store, not your neighborhood novelty shop. It had to be at least 2 1/2 feet long, with a leather wrapped handle and brushed stainless steel pommel. The shaft was also covered in a smooth black leather, all the way up to the double leather tongue which was about an inch wide and twice as long. Giving the shaft I gently bend, I was sure it was probably a sturdy fiberglass rod inside. I glanced at the tawse, but I'd already made up my mind, it was going to be the crop tonight.

"Assume the position." I gestured toward the side of the bed with the crop while stepping out of the way myself.

"Yes, sir." She moved to the side of the bed where I had been sitting, and bent at the waist again, placing her forearms on the bed, hands flat on the duvet.

Looking at her already well spanked ass, the speckling of potential bruises poking through the deep otherwise solid pink, I said "I'm going to give you twelve of the best. You're going to hold your position, and keep as quiet as possible. If you move out of position, we start over, am I understood?"

"Yes, sir. Thank you, sir." she replied.

I swung the crop through the air harshly with a loud swish a few times, watching her flinch and clench slightly with each swipe. Taking up position to her left, I tapped the crop against her cheeks aiming for the upcoming strokes.

I pulled the nasty little whip back and with a flick of my wrist brought it hard across her ass. The heavy tongue struck her right cheek, while the rod impacted both cheeks.

"Ah! Fuck!" Sammy yelped loudly and jumped up, involuntarily reaching behind her to grab her stinging ass with both hands.

"That one doesn't count, you better stay in position and watch your mouth, young lady."

She quickly got back in position, and through clenched teeth choked out a "Yes, sir. Sorry, sir."

I picked up her soft red panties from the bed. "Here, let's see if we can control that filthy mouth of yours. Open up."

Turning her head toward me without moving her body from position, she opened her mouth. I pushed the panties between her lips, wadding them up until her mouth was full.

"Now where were we? Oh, right, we're starting over." Without waiting, I repeated the first stroke, this one just a bit lower than the stripe already formed from the first.

"Mmmmffff." She grunted through her fabric filled mouth, but held position.

"One." I flicked the crop again, just as hard, a little higher this time. Watching the red stripe rise out of the deep pink already there. "Two." I said, as she grunted again, now clenching the duvet in her fists.

I continued striking her buttocks with the crop for another nine strokes, about half with the tongue landing on the right cheek, the remainder only on the left. As I counted each stroke, I saw tears start to freely flow from her eyes, but she held position. "Last one," I said "better hold position until I say, I'd hate to have to start all over again."

Sammy made a sound around the panties stuffed in her mouth that sounded like "Yes, sir."

Lining up the last stroke, I pulled the crop far back and whipped it forward with more force and speed than the previous swipes. Just after the blow landed, I saw a wave of tiny involuntary tremors shake through her legs. She struggled, but stayed upright and in position. "Twelve."

Placing the crop on the bed, I could see she was breathing very heavily through her nose, but as the tears continued it was getting harder as her sinuses were stuffing up. I reached up to her mouth and gently removed her panties, allowing her to breathe more freely. I then focussed on her blistered backside, gently stroking the hot raised welts left by the crop's rod, and looking at the dark splotches that would definitely be bruises tomorrow.

After a moment, I said "You've done well, your punishment is now complete."

"Thank you, sir." she sniffled, and collapsed forward on the bed.

I laid down on the bed beside her and wrapped my arm around her. She buried her face in my shirt between my neck and shoulder and sobbed openly. I was just about to apologize for going too far, when she looked up and said "That. Was amazing! Thank you." planting her lips on mine for a kiss that tasted of her salty tears.

Running a hand over her sizzling bottom, and giving it a playful, light pat I said "You can take it harder than you thought, it seems." With that I stretched my arm further to get my fingers under the curve of her cheeks and down to her pussy. I found it hot and very wet, as she rocked her body slightly to allow my fingers better access. I pulled my arm back and rolled her over part way so I could really work her slit with my fingers.

"Mmmm. Fuck that feels so fucking good!" Sammy moaned "Don't stop, please don't stop."

I continued finger fucking and kissing her until her body rocked and clenched in orgasm. When her breathing returned to normal, she looked at me quizzically, saying "Why do you still have clothes on?" And promptly started to undo my poorly tied tie, and unbuttoned my shirt. While she worked on my shirt, I quickly undid my pants and awkwardly shoved them and my boxers down, kicking my legs to get them to fall to the floor beside the bed. My cock was painfully hard again, something it seemed Sammy was very good at making happen.

She grabbed my engorged penis with a hand and stroked, firmly and slowly. Then pulling her lips away from mine, she got up on her knees and bent down, wrapping her mouth around my hardness. I lay back with my arms up, hands behind my head holding it up so I could watch her work. Bobbing her head up and down, she'd push me deep into the back of her throat, then pull back to circle the head with her tongue before repeating the process.

"Oh my God, that's amazing!" I breathed through my staggered panting.

She lifted her mouth off my cock with an audible POP, and said "You like that? Wait until you feel this." With a sly grin, she turned and picked up the lube.

"Oh, my."

She smiled widely as she opened the bottle and drizzled a good amount of the slippery clear liquid over the head of my dick. Using her hand to spread it all over, coating my shaft completely. "I'll have to start slow, it's been a while, okay?"

"However you want it, baby."

She threw one leg over my body so she was straddling me facing away, letting me have a good view of her beautifully marked ass cheeks. After squirting a little more of the lube into her hand, she reached behind herself and used her slick fingers to work some of the lubrication between her red, striped cheeks into her tight anus. Grabbing my cock to help guide, she carefully lowered herself to it, stopping briefly as the glistening head pushed against her puckered asshole. Then pushing her hips down, I watched as it stretched to allow my hardness to slowly penetrate.

"Ooooh." She exhaled as she dropped her ass millimeter by millimeter down my shaft. Until I reached a point where she paused again for a moment.

"Holy shit!" I said "You're right, this is amazing!"

Looking over her shoulder at me, she flashed a wide grin. "Just wait." Then she pushed past the point at which she'd stopped and dropped herself all the way down the remainder of my cock. When her hot, well spanked ass hit my stomach, I knew what she'd been talking about. The feeling was like nothing I'd ever experienced.

"Ohhhh!" I let my head fall back on the bed "my God!" I propped myself back up so I could watch as she rode me. Up and down, I watched in fascination as her eager asshole swallowed my cock over and over. She started to lose a little rhythm and I noticed that she only had one hand on my leg holding herself up, because the other had been diverted to playing with her pussy. I could feel her anus clench as she brought herself to another orgasm, and that was the point of no return for me. "Fuck, I'm going to cum!"

She responded by bouncing on my dick harder, faster, and somehow even deeper than before. It didn't take long for her to draw out one of the most intense orgasms I'd ever had, pumping my load deep inside her. When she felt this, she pushed herself hard against me, making short quick motions up and down, backward and forward, prolonging the sensation so long I thought I may never stop cumming.

"Hhggghh..." I made a guttural sound that couldn't have been mistaken for words under the best of circumstances.

Sammy climbed off of me, and lay beside me. Whispering into my ear, "There's one to check off the list." Then kissed me on the cheek and added "I'll be right back." as she hopped gingerly off the bed and did a weird sort of waddle toward her bathroom.

While she was gone, I thought back on our conversations earlier. We'd been discussing our sexual preferences, likes, dislikes, and things we've never done. The topic of anal had come up, and I'd admitted to Sammy that in all my nearly 47 years, I'd never done it. The fact that she'd remembered that, and specifically set up the evening's encounter to include it reminded me why I'd fallen so hard for her.

She returned from the bathroom with a hot, damp and slightly soapy washcloth which she handed to me, saying with a chuckle "Here you go, you don't want to sleep with that gel still on you, who knows what might happen if you get up in the middle of the night to pee and forget about it."

Taking the cloth from her, I laughed loudly and replied "I bet that could make a hell of a mess."

We both laughed while I wiped up the lube and cum mixture saturating my groin area. A silence fell between us for a few moments, then "I don't know about you, but I'm starving!" Samantha finally said.

"You cooked breakfast, so I should do dinner." I started, "however, you've made my knees so weak, I doubt I could stand long enough to cook anything. Pizza?"

"Pizza sounds great! You know what I like."

I got up to find my phone and order the pizza, looking back before I left the room to catch her propped up on one elbow, staring right back at me. A soft, satisfied smile on her gorgeous face. Her porcelain skin glowing with a thin sheen of sweat. "I love you." I blurted without thinking.

Her eyes shone despite still being slightly puffy from the crying she'd done, "I love you too."