Pity Fuck

I guess you really couldn't call it a pity fuck because in the end there was no pity involved and for me, at least, I never got literally fucked. It all started in the hotel bar where I'd had a few drinks. I was traveling on business and normally don't drink at all but the meetings had ended early and since my flight didn't leave until the next morning I had a free afternoon and night.

Rather than attempt driving in a strange city after drinking and not wanting to worry about catching a cab I simply drove back to the hotel, parked my rent car and headed for the bar. Now, after a drink or two I would have been fine, but as the afternoon sneaked into evening I'd had more than a few drinks. I wasn't falling down drunk, but my judgment was obviously impaired. Yes, impaired enough to ignore any suspicion that might have arisen when a young and very attractive woman asked to sit at my table.

Hell, I began to wonder why someone like her would even think about joining an overweight, gray-haired, old clown like me, but those few extra drinks just set me up when she said, "Actually I prefer older men. You know the guys my age are only interested in me as a quick score, they could care less about me. Older guys, it's like they really care."

"Am I that old?" I asked.

"No, no of course not, it's just that..."

"I was just kidding, I know I am probably older than your father. How old are you, if you don't mind my asking?"

"How old do you think I am?" she asked, sitting up straight in her chair.

"I'd say twenty-five or so."

"Twenty-two," she said, running her fingers through the short, blond curls on her head. She sipped from her drink, took a deep breath and with a sly look on her face she continued, "So we're both consenting adults."

A bit stunned I let my eyes wander down her neck to where the lace of her bra just peeked from beneath her blouse. "And just what are we consenting to?" I asked. I had figured I'd buy her a couple of drinks, we'd continue the playful conversation for a while and then she'd head off to where ever twenty-two year olds head at just past eleven pm, so I was not prepared for her reply.

"Why don't you take me up to your room and we can find something to consent to."

I immediately waved down a waitress and asked her to charge the tab along with a healthy tip to my room. With that handled I then led the young woman out of the bar and into a nearby elevator. Once inside the room she immediately pushed me against the door and began kissing me. Before I could do anything I felt her left hand reach down and grab my cock while her right hand fumbled with my belt.

Reaching my hands down I briefly cupped her ass and squeezed but almost immediately, she dropped down to her knees and finished unfastening my belt and pants. As they fell to the floor, she slipped her hand under the elastic of my jockeys and took hold of my erection. She began to stroke it as I worked my way out of my shoes and stepped out of my pants. I unbuttoned my shirt and tossed it aside.

Suddenly she paused, leaned forward and kissed my cock. Just as I prepared myself for her mouth to descend upon me, she stood up and whispered, "Go sit on the bed while I undress."

I quickly moved over to the bed, pulled off my jockeys and sat down. While I removed my socks I watched her as she kicked off her shoes and then slowly unbuttoned her blouse. The black lace bra covered her small breasts but showed off her beautifully erect nipples. As I stared at the way her nipples poked out in two sharp peaks, she removed her pants and moved over next to the bed stand beside me. I reached a hand up toward her breast when she grabbed my wrist, pulled it back behind me and then snapped something metal around my wrist and then latched the other end to the bed post.

"What... what's happening?" I asked, figuring this was some kind of a sting or something.

She quickly straddled me, pushing herself against my now softening cock. "No, no, don't worry lover, this is all part of the fun." She then stood up and began to work her bra strap down over her shoulder, the dark material slowly folded back exposing more and more of her breast. Just as I was about to see the nipple slip out she stopped.

Smiling she said, "Just a moment," and then walked over to where my pants had dropped to the floor. She picked them up, reached in the back pocket and pulled out my wallet. As she peeked inside she said, "I'm so glad you didn't pay your bar tab with cash. Hmm, not bad. Do you have any other cash?"

"No, I never carry much cash, I only use credit cards."

"Are you being honest with me?"

"Yes, yes, I may have some change in my luggage but that's all... honestly."

I heard a knock on the door and just before turning to open the door she replied, "You know, I believe you."

It seemed odd to me that she'd leave without her pants and blouse. I heard voices and then the sound of the door closing. Suddenly the woman appeared again leading a tall twentyish man with some colorful tattoos down both arms. He simply nodded to me as he followed to woman over to the other bed and tossed a towel on it.

"You've been such a gentleman to me and even though you didn't have much cash I thought I'd give you a treat. You see my boyfriend and I, well... we have a particular kink and ah, we'd like you to watch." She then kneeled in front of the tall man and unfastened his pants. In a scene similar to what happened with me earlier, she slipped her hand into his underwear and began stroking his cock.

She worked it out from beneath his underwear and leaned forward to give it a kiss, much like she did mine, however, she didn't stop there as she did with me. Opening her mouth, she slipped her lips over the purple head and began sucking wildly. The man pressed his hips forward and grabbed her head, pulling her to him. He thrust his cock hard into her mouth several times before she finally could turn her head and slip out of his grasp. She then pulled off her bra and panties and sat on the bed, opening her legs giving me an unimpeded view of all of her.

All too quickly her boyfriend pulled off the rest of his clothes and moved over in front of her. She turned slightly and slid back toward the middle of the bed, where he followed, kneeling between her legs. Rather than looking up at him, she kept her eyes locked on mine and as she guided his cock into her pussy her lips moved as if she was saying something to me.

In the periphery of my vision I could see between their legs where his cock began working in and out of her, but I kept focused on her eyes and face. I noticed an initial wince of pain when he first thrust hard into her but noted that it soon turned to a look of pleasure as she began to respond to him. She moaned softly but was quickly drowned out by his deep guttural groans. I watched as her expression changed from the pleasure as she got closer and closer to coming to sudden disappointment as her boyfriend arched his back, cried out, "Oh yes, yes," and then collapsed upon her.

After a few minutes he pulled out of her and reached for his clothes asking, "How was it?"

I wasn't sure if he was asking me or her, but she quickly responded, "Great, just like always."

The guy looked at me, smiled and then pulled on his underwear. She remained on the bed as he dressed and when he finished she said to him, "You go ahead and take the money, go down and start up the car. I'll be down in a few minutes."

"Just the money?"

"Yes just the money. Now go on, I'll get dressed and be down in a minute. I got to make sure he won't get loose until we get away."

"Okay, don't take too long," he said heading out the door.

When he was gone she looked at me and said, "You see, just a quick score. But I bet with you it would be completely different," she said crawling up on the bed beside me. Straddling my left leg, she reached out, took hold of my cock and slowly began stroking it. As she worked my cock she moved herself back and forth over my thigh, sliding her wet pussy up and down my leg.

"Yes, I bet you'd run your tongue up and down my pussy, push it inside and then slide up to my clit," she whispered while moving her hands up and down the length of me, pressing her pussy and clit against me. "You wouldn't stop until I came would you?"

"No, I'd lick your pussy until you came, again and again," I replied, gasping for breath.

"And after I came would you gently slip your cock inside me?"

"Yes, slowly, gently..."

"And would..."

"Yes, first slow and deep, then..."

"Then faster?" she asked, working her hands faster and faster, sliding up and down my thigh, coating my leg in her juices.

"Yes, faster, faster," I moaned, lifting my leg up, pressing against her pussy.

"So I'd come... come... coming, yes yes," she cried out just as I felt the pleasure shoot through my body and my cock spurted up onto my stomach in spurt after spurt. She rolled onto the bed beside me still holding my cock in one hand. She milked the last few drops from me and then moved off the bed. She grabbed the towel on the other bed, dried the juices dripping from her and then ran it over my leg. Walking around the room she gathered up her clothes and quickly dressed. She then grabbed the towel and then looked over at me.

"I'm gonna leave now. I actually enjoyed it... I mean not just getting the money, what just happened. Just keep in mind when you call the..."

"I'm not gonna call the police."

"No?"

"Hell, I'd gladly have paid what you got for something like that. Seeing you two and then, I only wish..."

"I liked having you watch us, if only he weren't so quick. Of course it was fun watching you watching me, your cock twitching so, and then after, damn you were hard. Anyway, I've got to go, but hey, you were such a good sport, take a look in that pillow case." She pointed to a pillow at the lower corner of my bed. She then disappeared around the corner and I heard my door open and then close.

It took me several minutes to work the bedspread to where I could reach the pillow. I found the key to the handcuffs inside the pillow case. I considered throwing on some clothes and following, but they were probably long gone. I didn't consider calling the front desk or the police, not I figured I'd chalk this up to one fine pity fuck... well almost.