Stripping Stephanie Pt. 02

The following story is fiction and does not describe any real person or situation in particular. All characters are at least eighteen. In "Stripping Stephanie" part one, two colleagues get really wild in a swimming pool at the hotel where a professional conference is taking place. Stephanie only has one rule: nothing goes up her ass. Part two takes place on the next night and Stephanie is going to have to make a hard decision.

*****

It was the second and final night of the conference and the clinics had been rather taxing today. Stephanie was still glowing at dinner from the wild time we had last night in the pool. She had mentioned that her muscles were sore from the light bondage fucking last night and the clinics today so I had offered to give her a full body massage. I'd given her those before many times but now things felt a little different. It's interesting how a woman's view of a man changes after he's been inside her.

We walked into her room at the hotel and Steph put her things down on the table. Her crimson business attire and black boots made her look very professional, but Steph couldn't wait to get into more comfortable clothes.

Taking some pajamas she walked into the bathroom and peeked back at me as she was closing the door.

"Give me a minute to change," she smiled.

I sat down on the bed and waited. Just knowing that Stephanie was behind that door taking off her clothes was enough to get me excited.

"Hey," I knocked on the bathroom door, "if you need some help changing I'll be happy to assist."

"Yeah I bet you would," Steph flirted back.

After a few minutes, Stephanie came out of the bathroom wearing a really tiny pair of white cotton pajama shorts and a cute black spaghetti strap top with the words "Here comes trouble" written on the front. I couldn't help but look her over. The shorts were small enough to tell that she wasn't wearing anything underneath and her perky breasts bounced freely underneath her top.

"You're doing me with your eyes again," Steph rested her hands on her hips.

"You caught me," I said shrugging my shoulders.

"Where do you want me?"

I smiled. "Let's do it on the bed."

Steph smiled back at the double meaning. "Now behave," she pointed at me, "I need you to loosen me up not feel me up. So remember, no sex with me tonight."

"Fair enough," I held my hands up as Steph sat on the bed facing away from me. I got on my knees behind her and began rubbing her shoulders and upper back. As my hands worked on her I was able to confirm that Steph had taken off her bra. I massaged her upper back firmly, pushing deep into her. She made intense little gasps of pleasure and relief as I loosened her up. After working her shoulders and upper back, I began running my fingers up the back of her neck and through her long straight hair.

"Mmmmmm," Steph purred with contentment as I relaxed her with my touch.

"That feels wonderful," Steph laid her head back, closing her eyes.

"Can you lie face down on the bed?" I asked. "I can do you easier."

Steph came out of her trance and smiled at me over her shoulder. "Remember, no sex," she restated.

"If you insist," I replied as she scooted her legs back behind her, lying flat and face down on the bed. I went to work on her legs. Steph was always very active so her legs were in fantastic shape. I gripped her firmly and began massaging up and down the entire length of her shapely legs.

After a few minutes I noticed that Steph began shaking whenever I worked the back of her calves. I leaned over to see if she was okay and noticed that Steph wasn't shaking, she was giggling.

I smiled at how cute and intimate this was. "Did I find a tickle spot?" I teased. I could see the back of Steph's head nodding as she gave a cute little giggle.

I lightly brushed my fingers across her calves and down to the bottoms of her feet. Already very sensitive, Steph twitched in small involuntary jerks as I lightly tickled her. Whipping her hair back Steph looked at me over her shoulder.

"Stop," she smiled playfully.

A final little tickle from me on the bottom of her feet made her jerk away in reflex. She wiggled her hips, drawing my attention to that perfect ass of hers.

Turning my focus to her rear I grabbed Steph's ass firmly with both hands and began working her hard. Steph smiled at me over her shoulder but did nothing to discourage me.

"You just can't keep your hands off my ass, can you?" Steph knew her rear was amazing, and part of her enjoyed teasing me with it.

I straddled her for better leverage and intentionally pressed my cock firmly between her legs. Even through our clothes, Steph could feel it throbbing against her pussy. It was such a turn on for both of us. Steph suddenly tensed up as I began thrusting my hips back and forth against her. She began breathing heavily, closing her eyes and gripping the bed tightly with her hands. I could tell Steph was beginning to weaken.

I reached down between her legs and began massaging her pussy through her shorts.

"Um!" Steph bit on her hand to keep from moaning. I worked her ass and her pussy firmly with the sole intention of getting Stephanie really turned on. When I moved my hand inside her shorts and found her clit she yelped, her body jumping out of reflex. I gently massaged Stephanie's most sensitive pleasure spot. It felt so good to Steph, but she wanted more, she wanted me to...

Snapping herself out of it, Steph whipped her head around and shot a fiery look at me that could melt ice. Her attitude said "how dare you do this to me," but her eyes were saying "please don't stop". We stared at each other for a moment as Steph tried to think rationally. If she was going to stop me this was her last chance. Steph knew it too. It was either stop right now, or surrender her body entirely to me. Finally, decision made, Steph lowered her eyes in submission and laid her head back down on the bed.

"Tie me down," Steph spoke softly, spreading her arms and legs wide.

I reached back behind me for the pillows on the head of the bed. Taking the pillowcases off one at a time, I began tying Stephanie down, looping a pillowcase around each ankle and tying them to the legs of the bed frame.

Steph was not pleased with herself for giving in. She knew as soon as I suggested giving her a massage in her room that it would lead to this. But, as she felt her wrists being tied down to the bed, and my hands sliding her cotton shorts down over the curves of her ass, Steph realized that the only thing she really wanted right now was for me to take control of her body and fuck her.

Wasting no time, I reached between Steph's legs and used two fingers to gently massage her clitoris.

"Oh!" Steph jumped at the sensation. Her clit was so sensitive from all the massaging and teasing that she felt like she could orgasm at any moment.

She squirmed, and twitched, giving little tiny sighs of pleasure as I found just the right spots to drive her crazy. Steph pulled on the knotted pillowcases that held her down. She grasped the air with her hands and feet. She rolled her head around, moaning in pleasure, knowing she wasn't going to be able to escape until I had my way with her.

"Oh! Oh! OH! OH!!" Steph's ass began humping in fast tiny thrusts, almost involuntarily as jolts of pleasure lanced through her body.

Just as I got her panting with desire, I took my hand away from her clit and began lightly caressing her inner thighs. "Now Steph we don't want you coming too soon do we?"

Steph gasped in frustration and raised her head to look at me over her shoulder. "Oh, you're so mean to me," she said breathlessly, "you get me soooo horny and then tease me until I'm about to explode."

"Exactly," Only giving her a moment to rest, I reached into my shoulder bag and produced a small vibrator. Steph looked up at me upon hearing the whirring start as I set it in motion.

"Oh no," she protested, half-pleading, "you wouldn't do that to me."

"Get ready," I answered inching it closer to her quivering pussy. Steph bit her lip in tension and closed her eyes as I inserted just the tip inside her and glided it in and out ever so slowly.

"Oh! Please stop teasing me," she laid her head back, "please just let me come."

"Horny, are we?" I taunted her, moving the tip of the vibrator faster into her.

"Yes! I'm horny!" Steph fired back at me. "I'm so horny! Ohgod! Please put it in deeper," Steph begged in frustration, thrusting her hips as if trying to fuck the vibrator herself, "please let me come."

"No, Steph," I teased her by pulling the vibrator out of her, "I'm in charge."

Steph yanked on her bonds in frustration. Too exhausted to fight, she gave in, looking up at me with submissive eyes.

"Okay," she said breathlessly, "you win." Her eyes locked on mine. "Torture me."

I leaned over and kissed her hard. Steph responded aggressively, sighing deeply as we attacked each other's mouths savagely.

Steph then braced herself as I moved the tip of the vibrator to touch her swollen clitoris.

"OH! OH! OH!! OH!!" Steph bucked uncontrollably, thrashing about as the vibrator stimulated her most sensitive spot.

"OH!! OH!! OH!! OH!!" Stephanie's gasps got louder and higher as she felt the orgasm she longed for building within her.

OH FUCK!! OH FUCK!!" Steph's whole body shook, building to a climax as I made circular motions on her clit with the powerful vibrator.

"OH FUCK!! FUCK!! FUCK!! I'M GOING TO COME!!" Steph squealed as she felt herself about to explode in orgasm.

Then, suddenly, as if flipping a switch, I stopped, pulling the vibrator away and leaning back, leaving Steph breathless and panting.

"No! Don't stop! Please!" she begged me. Steph was so close to an orgasm that would rock her world. One more touch inside her pussy would do it. One more stroke of her clitoris would send her over the edge.

The time to fuck her was now. Steph panted as she heard the sound of my pants zipper coming down. Stephanie was ready to be fucked into next week. She raised her hips as much as she could being tied down to the bed and wiggled her ass up against my cock.

"That's it," she said as I placed the tip of my cock at the entrance to her pussy. "Fuck me! Fuck me now!"

Steph braced herself, waiting for my cock to spread the walls of her pussy and push into her. Waiting...

Suddenly realizing I had stopped, Stephanie quickly looked at me over her shoulder.

"Sorry Steph," I said apologetically, "you said 'no sex tonight'."

Steph's mouth fell open. "No! Please!" she begged. "I...changed my mind."

"No no," I pretended to be indifferent, "I wouldn't want you to do anything you'd regret."

"Come on," Steph yanked on her restraints in frustrated anger, "quit being a pain and fuck me!"

"I'll make a deal with you," I said caressing gently up and down her body. "I'll give you an orgasm, but only if I can give it to you by going up your ass."

"What?!?" Steph said in disbelief. "Are you kidding me? No...I'm not doing that."

"Okay then, I'll see you tomorrow," I started to get off the bed.

"No wait," she said quickly, realizing how desperate she was.

"Well?" I asked.

"Is this the only way I'm going to get some tonight?" she asked coldly.

I nodded.

Steph spoke softer now, "and you promise you'll let me finish?"

"You'll be seeing stars before I'm through with you," I said placing my hands firmly on her bare ass.

Steph moistened her lips nervously. Last chance to say no. She had already made her decision though and was trying to gather the strength to surrender herself.

Finally, Steph turned back around to face forward and lay her head down on the bed. She raised her hips up, presenting her perfect ass to me.

"Go for it," she said a little hesitantly.

"Oh no, Steph," I said playfully slapping her rear, "I want to hear you ask me...nicely."

Her mouth fell open. "You're kidding right?"

I shook my head. "Nope, I want to hear you beg for it."

Stephanie sighed to herself, "Mygod I hate you sometimes."

"No you don't," I teased.

Steph put on her most submissive look for me and lay her head down on the bed. "Please, please, please put your cock in my ass." She wiggled her rear up against me and began pumping her hips. "I would really love to feel your huge shaft go up my ass over and over and over again until I come."

"There now, that wasn't so hard," I said patting her on the top of her head.

When Steph saw me reach for some lubricant out of my bag she realized that she'd been set up. "You planned this all along, didn't you?"

I nodded.

"You're a real pain in the ass," Steph fired at me.

I grabbed Stephanie's rear with both hands. "That's next."

Steph became very nervous as she felt me place my rock hard cock against her ass. She closed her eyes as I held her rear for support and began to push. My cock parted her ass cheeks as it entered her, and she realized just how large my shaft really was. Steph held her breath and tensed up, convinced that she couldn't take something that big up her ass.

"Relax Steph," I said softly, "take some deep breaths."

"I...can't...do...it," she said clinching her jaw.

"Yes you can," I insisted. "You just need to loosen up and push out a little."

Even though it made no sense to her, Stephanie nodded quickly in obedience. Deliberately taking long deep breaths, Steph managed to relax herself enough to allow me to enter her.

The head of my cock popped in, two inches of penetration followed, and then Steph's ass spasmed wildly on my shaft.

"Ahhhhh!" Steph screamed as she threw her head back, overcome by the intensity of the feeling. She felt so submissive. How did this happen to her? What makes a woman go from a professional colleague to a desperate girl begging to have her ass violated?

I rested inside her for a moment, giving her a chance to catch her breath. Steph grasped the corners of the bed tightly in anticipation as I prepared to go deeper. There was more to go...much more.

Steph panted violently as I pushed several more inches inside her. Methodically I started to pull out, then push back in, then pull out again, going a little deeper each time. Steph cried out and whimpered as I defiled her. Stephanie felt violated, degraded, and guilty that she had allowed me to do this to her. Worst of all, she was enjoying it.

Suddenly my cock stopped as if I'd hit a brick wall. Steph's whole body locked in tension as I tried to push deeper into her.

"No! I can't take any more!" she said in a pleading voice.

"Yes you can," I assured her.

Steph shook her head and looked back at me over her shoulder, "Its too much! You're too big!"

"You can do it Steph," I encouraged her. Reaching up underneath her shirt, I cupped Steph's cute little breasts and began to rub them sensuously with my hands.

"Um!" Steph closed her eyes and laid her head back as I methodically rubbed her breasts, gently pinching and drawing down on her hard nipples. It gave Steph the stimulation she needed to help her into a more relaxed state of arousal. Her tightness faded and she moaned deeply at what I was doing to her. Slowly, the muscles in her ass relaxed and Steph felt the rest of my cock tunnel completely inside.

"Ooooooooooooooooooh!" Steph cried out as she felt the deep penetration of my invading cock. It slid into her ass until the entire shaft disappeared.

I rested inside her for a moment, letting Steph's panting and twitching settle down as she tried to steady her breathing. I stroked her long beautiful hair, calming her as her body adapted to having my cock thrust up her ass. Finally, Steph managed to catch her breath, and knowing what was coming next, readied herself as I began to pump in and out of her.

My cock literally throbbed inside her and Steph could feel it pulsing. Slowly she started to push backwards to meet my thrusts, my cock driving long and deep into her with each push.

"Oh! Oh! Oh! Oh!" Steph jerked out of reflex each time I drove into her. The head of my cock rubbed against her sensitive nerve endings over and over, causing Steph's entire body to twitch in gratitude for the pleasure it was receiving.

"I...can't...believe...fuck!...you're...ohgod!...doing...this...to...me!" Steph could hardly get the words out.

Still pounding her ass from behind, I moved my hand to touch Steph in her most private places, using two fingers to touch her clitoris and moving my thumb inside her pussy to stroke her g-spot from within her moist depths.

"Ahhhhhhhhhh!!" Steph threw her head back and cried out as waves and waves of pleasure washed over her.

"Oh yes there!! Ohgod! There!!" Steph begged, tightening the muscles in her rear around my cock, heightening the contact with my thumb stroking her g-spot. The sensations made us both cry out.

"Oh Steph," I said pulling on her long silky hair as I pumped her hard. Her ass muscles were squeezing my cock like she was milking me, pulling wave after wave of pleasure out of my body. "Oh yes, Steph!"

Steph was in another world though, unable to register my voice. Her body trembled and shook uncontrollably as I pounded into her from behind.

"Oh!! Ohgod!! This is so wrong! FUCK!! It feels soooooo good! OH FUCK!!" Steph's pleas for mercy were marvelous to hear. Each stroke that glided over her clitoris or inside her pussy sent her body into wonderful convulsions.

We both could feel it coming. It was big too. An orgasm like no other ready to come pouring out of us. Bracing ourselves, we began thrusting faster and faster, Steph panting like an excited puppy. She yanked hard on the fabric that held her wrists and ankles as she climaxed.

Steph's ass clamped down on my cock and her entire body locked in tension. She threw her head back, her mouth fell open unable to scream as the tidal waves of orgasm crashed over her.

For a moment Steph couldn't move, her mind shut down as she became a slave to her own body. The degradation no longer mattered. All that mattered was the overload of pleasure she was feeling right at that moment. Finally, Steph managed to find her voice, screaming as she felt her entire pussy, inside and out, explode in orgasm.

"OOOOOOOOOOOOHHH!!" Steph's scream was beautiful to hear as she let the waves of pleasure wash over her. The warmth filled her ass with a rush of pleasure she had never experienced before as I poured into her. Her hips bucked on the mattress in involuntary spasms, and her arms pulled so hard at the pillowcases restraining her they began to tear. Letting go of Steph's hair I brought my hand down to spank her ass hard over and over.

"OW! OW!! OH FUCK!! OW!!" Each time I spanked her, Steph's ass jerked involuntarily, sending more jolts of pleasure through her body as her pussy wiggled on my fingers and her ass contracted around my shaft.

"NO MORE!! OH PLEASE NO MORE!! NO MORE!!" Steph begged as another orgasm pounded her hard.

I pulled my fingers out of Stephanie's pussy, giving her one more fast stroke across her g-spot which made her gasp. Then, grabbing her hips, I pumped her ass slowly as I finished emptying my cock into her.

Stephanie collapsed on the mattress completely defeated as I finished and slowly pulled out of her. Her gasps became moans as Steph's panting began to slow down to normal breathing. For a while Steph just lay there, still tied down and completely exhausted. Finally I got off of her and gently pat her on the top of her head like a puppy.

"Good girl," I said approvingly, "relaxed now?"

Steph turned her head in my direction. "I can't believe you just did that to me."

I gently brushed the hair from her eyes. "It was your choice."

"Like heck it was." Steph fired back.

"You enjoyed it though." I said beginning to untie her restraints.

"Yeah you got me there," Steph admitted reluctantly. "I'm just glad this is only a two day conference."