Ann: A Love Story Ch. 90

The skirt was shorter than most I'd seen her wear to work, the hem a little more than halfway up her shapely thighs. Taking the bottom of the skirt between her middle finger and her thumb, she extended the rest of her fingers as she daintily pulled it up, exposing more of her upper thighs.

When her mound came into view, I smiled. "Maybe I am feeling slutty today," she giggled.

"I think you are," I replied, staring at her wet, bare pussy. "Somebody beat me to it."

"I did. They were so soaked I had to take them off as soon as I got here."

Her pussy lips were glistening, and I grinned. "I can see why."

Letting go of the skirt, she moved toward me, falling into my arms, her left leg lifting sexily at the knee. "So...what are you going to do with me now, Neil," she said as she licked at my ear.

Lifting up the back of her skirt, I patted her bare ass. "I'm going to do what I should have done last night," I growled.

~*~*~*~*~*~

"Good evening, sir. Welcome to the Sheraton. I'm Heather...how can I help you?" she said cheerfully.

"Hi. Reservation for Green," the gruff voice replied.

As she shuffled through the packets of paperwork in the file folder on the counter, searching for Mr. Green's reservation, my hand brushed against her inner thigh, making her flinch. Moving my head further up under her skirt, I flicked my tongue over her exposed clit, causing her knees to buckle slightly.

"Are you okay," he inquired.

"Just a little light headed," she answered as she grabbed the edge of the counter to steady herself. "I must have gotten up too fast a little bit ago."

"You look a little flushed. You're even perspiring. Maybe you should sit down for a little bit."

"No, I'm okay," she said as I slipped my tongue back inside her pussy, digging deep once more. "Besides, the last time I sat down, I wasn't sure I was going to get up again," she said, her voice cracking.

"Can I get you a glass of water or something?" he asked, the concern in his voice seeming to be genuine.

Then again, I couldn't really tell. It's not like I could see him from where I was sitting on the floor behind the counter. Not to mention with her straddling me like she was. I'd been there for a good five minutes, playing around between her legs, licking her pussy. I wasn't necessarily trying to get her off as much as I was trying to keep her totally turned on. I brought her to the edge a couple of times, but it was more the idea that she was there working while I was below playing.

It didn't hurt my cause that she was out in the open either. Up until Mr. Green walked into the lobby, we'd been left alone. But that didn't matter at the time. She was exposed in a way, which was another new experience for her. The first had been what we'd done in the back before she had to go out to answer the phone.

When I'd patted her on her ass earlier, telling her I wanted to make amends in a way for what I neglected to do the night before, she didn't get my meaning. In fact, she wrinkled her nose, questioning me with her eyes. I pulled out my hard cock through my fly and sat back down on the loveseat, motioning for her to come over to join me.

She got on her knees at first, sucking me as deep into her mouth as she could, thinking that was what we hadn't done. And we really hadn't. She'd sucked me awake, but that was the extent of any oral play. Even though the way she was mouthing me felt incredible, she soon found out that a blowjob wasn't what I had in mind at all.

I waited until she had my entire shaft covered with her sloppy saliva before using my fingers to lift her chin gently.

"It's time," I smiled. "Stand up, turn around and spread your legs, Heather." Standing up behind her, I pressed my hand gently on her lower back. "Now bend over and grab your ankles."

"Ooo...I think I like where this is headed," she said as she bent at the waist. Her jacket fell toward her head, exposing her bare back from the waist of her skirt to the blouse tied midway at her shoulders. "I'm glad I locked the door."

Lifting her skirt over her ass, I rubbed the head of my cock back and forth against her wet pussy, coating the tip with her juices. "I hope you still feel that way in a couple of minutes," I laughed.

"Why wouldn't I?"

"Just a feeling I have," I responded as I moved my hips, running my cock along the crack of her ass. Using my thumbs to spread her cheeks wider, I pressed the head against her asshole.

"Oh...NEIL!" she shrieked, her body tensing.

It wasn't the same as the night before, when she looked at me wild-eyed, telling me she was willing. I'd misread those signs, going with that she'd told me earlier. Yet this time, I couldn't see her eyes. Plus, she had no way to brace herself like she had on the barstool. She was bent over and vulnerable, and with the way she said my name, reading her tone and body language on the surface, I came up with the same conclusion, which was she didn't want me to fuck her ass.

I ignored those signals, choosing instead to trust Ann's assessment of what Heather wanted all along. Grabbing her hips, I slowly pulled her toward me as I locked my legs.

"NEIL...I -- "

"Ssshhh. Relax, Heather. I promise I won't hurt you," I calmly reassured her.

To my surprise, she took a deep breath and quietly moaned, "Okay."

It really wasn't the best position for her to be in for trying anal sex for the first time. The angle was going to make it a bad one, actually. But I didn't intend to fuck her that way. I just wanted to get started. Pressing forward, the head began to enter her, slowly stretching her back entrance wider and wider. I took my time, trying to read her again. She took the guesswork out of it, by flexing her thighs a little and leaning back into me.

My cockhead slipped past her anal ring with a sudden pop. "Fuuuckkk," she winced, her voice low and hushed.

I stayed still for a couple of minutes, gently rubbing her lower back as I let her get used to the feeling. She was breathing deeply, in through her nose and out of her mouth, the pain she was feeling from being stretched coming out in the way she was exhaling through her clenched teeth.

"Stand up," I finally said, breaking the silence. As she did, I bent down and grabbed her underneath her knees, lifting her up.

"OH MY GOD, YOU FUCKER," she snapped as she felt herself suspended in the air, the tip of my cock still wedged in her ass.

And I was, knowing it hurt, but also knowing she was too far gone to stop. I wasn't trying to do any sexual acrobatics. I was more concerned with making her as comfortable as possible. The position we'd started in had been a mistake, and I wanted to rectify it. Slowly lowering the two of us to the loveseat, I tried to hold her in place so that I wouldn't give her more than she could handle. Of course, it wasn't as easy as I thought it was going to be. As my ass settled onto the cushion, hers settled down onto me, forcing more of my cock inside. She winced again, but she caught herself and quickly put her stilettos up onto the seat next to my thighs.

"FUCK!" she growled, before taking a deep breath "Is this what you had in mind?" she finally said as she looked over her shoulder. I was struck by her odd smile, which belied the fact that she was hurting. She actually looked happy.

"Well, I'd hoped to get here a little smoother, but yeah. Now take your time, Heather."

Wrinkling her nose again, she squinted, her smile putting me at ease. "It's a little late for that now. Besides, I'm more of a 'rip off the Band-Aid' kind of girl. Where's the fun of going slow?"

With that, she started moving her legs and hips, inching more and more of my cock inside her tight little ass with each downward movement. She was hurting, yet she never stopped; she never considered even slowing down. It took her a little time, but she eventually forced my entire cock into her ass, whimpering as she went.

"You okay?" I asked, my hands massaging her bare back underneath her blazer.

"UNHH, never better," she groaned, leaning forward a little as she started fucking me faster.

"Funny, you don't sound okay."

"Shut up and let me fuck!"

I chuckled, but I also let her have her way. That fact that she barked at me wasn't upsetting. I was more turned on, because she wasn't going to let the momentary discomfort get the best of her. She wanted to concentrate on what she was doing to help take her mind off any pain, wanting to get on to the pleasure as fast as she could.

We both did shortly afterward. She was playing with her pussy as she fucked me, while I could feel my load starting to build in my balls. She was much nearer her orgasm than I was, but it was a wonderful start to what we both knew was going to be an explosive ending.

At least until the phone rang at the front desk and she had to go do her job. "FUCK!" snapped again as she pulled off my cock, running toward the sound.

~*~*~*~*~*~

If it were just the one phone call, I would have gladly kept stroking my cock, waiting for Heather to return to the couch to finish what we'd started. When I heard it ring for the third time, I put my cock away, deciding to take matters into my own hands. Well, my mouth, actually.

I walked out to see what was taking her so long and found her taking a reservation, the phone cradled between her left ear and shoulder, her back to me as she keyed in the information on the computer. I looked around the lobby to make sure we were alone before easing up behind her, wanting to continue our fun, but aware that she was still on the job. Snaking my right hand around her waist, my hand slipped under her blazer, startling her as I cupped her left breast.

She stopped typing and took the phone away from her ear, covering the mouthpiece as she mouthed, 'Sorry,' as if I was upset that her job was interfering with our extracurricular fun. She continued talking as I pressed my crotch up against her ass. Reaching behind, she found that I'd put my cock away and she made a cute pout with her lower lip before putting the phone back where she'd had it so she could type some more.

With her hands tied up, she couldn't stop me from pinching her nipple. Closing her eyes for a second, she tilted her head back as she let out a little gasp, having to excuse herself to the person on the other end of the phone. It almost slipped off her shoulder and she had to rush to catch it.

Covering the mouthpiece again, she whispered, "You're bad!"

"Do you want me to stop," I whispered into her free ear, tweaking her nipple again.

Biting her lip, she shook her head, trying to return her attention to her caller. Removing my hand, I lifted the back of her skirt, my fingers finding her wet pussy. I began fucking her with two of them, all the while my thumb toyed with her newly deflowered ass.

She was having a hard time concentrating on her work, which was starting to concern me. Yet every time I tried to stop, she'd let me know in some way that she didn't want me to. At first, it was just the soft, dreamy glance out of the corner of her eye, pleading with me to keep going. She became more blatant later, when she reached down and grabbed my forearm, forcing me to put my fingers back inside her wet slit.

She no sooner hung up with that call when she had to answer yet another one. Resigned that it was going to be a while before we'd get to resume what we'd started in the back room, I decided to take a different approach to what I was doing to her. Rather, I decided to look at things from a different point of view, dropping first to my knees, then turning to scoot myself under the countertop.

I found myself between her thighs, which she eagerly spread as she straddled me, placing her feet near my hips. Folding my legs underneath me, I settled in, leaning up to replace my fingers with my tongue. At that point, I quit caring about what she was doing above the counter. I focused on what I was doing, content that if I couldn't fuck her for the time being, I could put my energies into something that still gave her an incredible sexual thrill.

I'd already brought her to one orgasm once she hung up the phone, and she was well on her way to another when Mr. Green showed up to sign for his room. That interrupted things a little, because she had to move around front desk area, leaving me there on the floor to watch her.

When she moved to the wall across from me to get some information and his room keys, I removed my cock from my pants once again. Turning around, she froze for a brief second, our eyes fully meeting for the first time since I'd snuck up behind her while she was on the phone. She blushed as she watched me for a moment, my hand slowly stroking my bare cock in front of her.

"Heather, are you sure you're all right?" the voice above me asked again.

"Huh?" she responded. Shaking her head, she gave me a quick wry smile before saying, "Oh...I'm sorry Mr. Green. I'm fine."

"You just seem a little out of sorts," he laughed.

She put her left foot by my hip bending her right leg at the knee like she was crossing her leg. Reaching down, she slipped off her shoe and placed it on the counter. "My toes were cramping in these heels," she said as she massaged her foot. Then she placed it squarely on my shaft, playing with it.

"Oh...well, I can understand that." Letting out a laugh he added, "Actually...no I can't. I've never worn heels before."

"It's not as easy as it looks. They can hurt your feet after a while, especially if you're on them a lot."

"Makes me wonder sometimes why women wear them."

"Do you really have to ask that?" she giggled, her toes playing with the precum she'd squeezed out of the head of my cock.

"You're right...that was silly to say."

"Sign here please," she said. I could hear the pen scribbling, and Heather let out a little snort. "You know, now that you bring it up, every woman's answer is different."

"What do you mean?"

"Well, some like the way the shoes make their legs look, or their hips sway," she as she leaned forward over the counter. I could just make out her whisper when she giggled, "I wear them because I love how they make my breasts bounce."

I swear I could hear him staring at her cleavage, the silence echoing louder underneath the counter where I was sitting. She continued to play with the head of my cock as she lingered over the countertop, and I knew she was giving him time to take in the sight she was offering.

Finally, I heard the telltale sound of room keys jingling. "The bottom line is we all wear them to make us feel sexy, and to please men."

"Well, speaking for men...we thank you."

"You're welcome Mr. Green," she snickered. "You're on the third floor. Elevators are down the hall to the right. Turn left off the elevator and your room will be down the hall on the right."

As he thanked Heather for helping him, I reached up and dipped my fingers back into her cunt, coating them with her slippery juices, making her shiver in the process. She leaned back, gripping the counter top to hold herself steady.

He didn't comment that time, perhaps because he'd found a way to tear his eyes away from her tits and leave. Looking down at me, she pressed her foot into my balls, teasing me in her own way like I was doing to her.

"You are a very naughty man, Neil Thomas."

"And you're a very horny woman, Heather Watkins."

Handing me her shoe, I slipped it back on her sexy foot so she could straddle me again. She was waiting for Mr. Green to come back through the lobby with his things, and while she did, I resumed satisfying my oral fixation. All the while, I stroked my cock, using the wetness from her pussy as a lubricant on my shaft.

She had another small orgasm as she wished Mr. Green a good night's sleep on his way to the elevator. As soon as I heard the ding of the car arriving, I quickly stood up.

"Good idea...let's go in the back," she said as she started to turn around.

Holding her in place, I pulled the back of her skirt up, placing my cock against her ass once again. "I think we'll just stay here."

"Neil...no! We'll get caught."

"I believe you said a little while ago that it wouldn't be any fun if it wasn't risky," I groaned as I slid my shaft along her crack.

Reaching behind her, she spread her ass cheeks for me. "Hurry...before I change my mind!"

Entering her ass a second time was much easier. In fact, I was able to slide all the way inside in one long slow stroke. After that, I fucked her...hard. What we were doing wasn't just risky; it was stupid. Yet the thrill we were both experiencing was so incredible, the ending was fast approaching.

Bucking into her tight ass, I felt my balls moving. Heather let me grope her tits, silently responding to my humping. That is, until she knew I was about to explode inside her.

"Cum in my ass, Neil. Make me a slut," she hissed. I held in my scream, grunting as I spewed my big load deep inside as I thrust forward and pinned her against the counter. She moaned happily, feeling my hot sperm hit her in places she'd never felt before. "Oh fuck," she exclaimed, her body shuddering.

As I pulled out, I quickly tucked away my cock before anyone discovered us. The entire encounter couldn't have taken more than three minutes from the time I slid my cock inside her to the time I came. It was that hot and intense.

Turning around, she smiled, kissing me on the cheek so as not to make a scene. It was an odd reaction, really. The lobby was like a ghost town; there wasn't anyone there to see us. And I'd just cum in her ass; a simple kiss seemed a bit odd to be worried about. But I understood.

"That was incredible, Neil. God...that's one more thing I never would have done if I hadn't met you. Well, more than one, actually. I never imagined I'd ever let someone fuck me here...let alone do it in my ass."

"Well, for the record, one of those is a first for me too."

"I can't believe Ann let us do this."

"Well, she doesn't know we did...yet. She only told me I could fuck you tonight as long as I just fucked your ass. In fact, there should be some kind of permission slip in my inbox, in case you didn't believe me."

"Well bless her heart," she said as she slowly made her way over to the little cubby on the desk along the far wall. Pulling out the paper, she opened it. "I should have known," she grinned.

"Known what?" I asked.

"It's in Carol's handwriting. She wrote down what Ann told her to say. And then she put her own postscript to it."

"What does it say?"

Heather laughed, her hand slightly covering her mouth and nose when she said, "She told me not to chicken out...and to enjoy all the cum that's going to be leaking out of my ass for the next couple of hours."

"Wow...I'm glad you didn't read that ahead of time. It would have ruined the surprise."

"What makes you think I didn't read it before now?" Heather winked. "Ann and Carol aren't the only ones that can pull off a surprise!"