Chat Room Hookup Ch. 01

I must have been taking a while because Paul called out, " are you OK in there?"

"Yes, I'm fine. I'll be right out."

I had reached the point of no return and decided to finally add some excitement to my life. I put on the pink lace panties first, which felt so sensual against my bare balls and cock. My tight ass cheeks peeked out from the high cut sides. I then slipped on the stockings and pulled them up over my long, muscular legs. I then put on the pink lace chemise. It was tight but not uncomfortable.

With the outfit complete, I checked myself out in the full-length mirror. I ran my hands over the soft material as my cock started to stir. I hoped Paul would like it. Once I opened the door, I knew there was no turning back. I would be giving myself to Paul. I took a deep breath as I reached for the knob and slowly turned it. The door squeaked a little as I slowly opened it.

Hearing the door open, I remember seeing Paul's face as he turned; looking me up and down when he first saw me come out of the bathroom dressed up in his fantasy lingerie. I felt like a shy virgin on her wedding night. Paul's eyes lit up as he stared at me with lust in his eyes. He was wearing his t-shirt and boxer jocks. His half-hard dick pressed against the material of his underwear. I paused as I entered the living room, wondering what Paul's reaction would be.

"Come closer Jay, you look fabulous; just like I fantasized you would, actually, even better."

I was relieved and pleased that he liked me in the lingerie. I nervously approached him. I couldn't look directly at him yet. I was too embarrassed which I think added to the eroticism of the evening.

"Turn around slowly, Jay."

I followed his instruction and turned slowly as his eyes drank in every inch of my half-exposed body in the pink lingerie. I could feel his eyes roaming from my stocking-covered legs up to my panty-covered ass, cock, and balls, to my upper body in the chemise. I blushed as he stared at me.

He then grabbed me and pulled me closer to him. Staring directly into his eyes, he leaned forward and kissed me. I had never kissed another man before and I didn't know what to do so I just returned the kiss. As our lips were locked together, I felt his hands start to roam over my body, grabbing my firm ass cheeks and pulling so close. I could feel his growing erection against my thigh as his tongue found its way into my mouth. His hands ran over my stocking-covered legs and thighs. Gently cupped my balls through the lace then up to fondle my nipples.

My erection was growing as I was being fondled. As our breathing got heavier, I was still shocked that I was going through with this, but my nerves turned to excitement knowing I wanted it just as badly as Paul. I was submitting myself to acting out our mutual fantasy.

Paul broke our kiss and whispered into my ear, "Jay, you are mine tonight and I want you to do whatever I say. Are you OK with that?"

I knew what that meant from our chat room adventures.

I looked directly into his eyes and said "Of course Paul. I want to please you in every way tonight."

He smiled and kissed me again. He then turned towards the dresser and pulled out some lube and a butt plug from the drawer.

The nervous excitement returned when Paul said, "OK Jay, pull down your panties, and let's take the first step."

I leaned over a small table by the window and pulled my panties down just enough to expose my ass. I felt Paul's hand spread my cheeks and felt a finger of his other hand start to play with my ass. He was a big man with large hands and long, fat fingers.

The lube was cold but felt good against my asshole. His finger played with my ass a bit before I felt it begin to penetrate me. I couldn't believe I was in a hotel room, dressed in pink lingerie, bending over while a man I just met was finger fucking my ass but I knew this was just the beginning.

He pulled his finger out and I felt it being replaced with the butt plug. He pushed it against my asshole and began to gently insert it into me. It felt weird and pleasurable at the same time. He took his time, which I was grateful for. He pushed the plug deeper waiting to see my reaction before he pushed it further. When the plug was fully into my ass, Paul ordered me to stand up and pull my panties up again. There was no doubt that he was in full control of me.

He rubbed my ass with his hands, patted it, and said, "good boy."

I panicked when I heard a knock on the door and a man's voice, "Room Service."

I just looked at Paul in total shock when he said, "answer the door, Jay."

He must have called for room service while I was changing in the bathroom. I couldn't believe he was going to make me be seen like this in front of someone else. I hesitated.

"Jay, answer the door and let him in," he said firmly.

Paul was such a big man with a deep voice, I felt I had to obey his order. I went over to the door, placed my hand on the knob, then looked back at Paul, hoping he was joking but he just motioned for me to continue and gave me a stern look. I hid behind the door as the room service waiter came in with more drinks and some snacks. He hadn't noticed how I was dressed at first but when he turned around and saw me he almost laughed and got a huge grin on his face. My face turned beet red. I was never so embarrassed or humiliated, after all, I was a grown man in a hotel room dressed in pink lace lingerie but I had agreed to this submission with Paul. It was part of our shared fantasy but this was a total surprise and I played along. It felt like an eternity before Paul signed for the order while they both stared at me.

As the waiter was leaving he said, "thank you, and have a good evening,"

Giving me a little wink as he left. I almost died from humiliation.

After having another drink, some snacks, and some playful fondling and flirting, Paul led me over to the bed and we started kissing and making out again. His hands were all over me and mine were all over him. He was muscular and his hard body excited me. I felt his strong arms and shoulders as we kissed and he had a nice firm ass too. I got so turned on when he pulled my chemise down and started sucking on my nipples. I never knew how sensitive they were until then. My nipples got hard from his playful hands and sucking. I was so hot, I wanted more.

I knew I would do anything Paul asked me to do. I then stripped off his t-shirt and underwear. I stared at his beautiful, hard 7" cut cock. I had dreamed of this moment in the chat rooms and jerking off fantasizing about a potential encounter. Now, his real life manhood was right there before me. I wanted to suck it and please him the best I could.

Before he would let me blow him, he led me over to the floor-to-ceiling window. He opened the curtains and in the dark of night with all of the lights on in the room, anyone would be able to see what was about to happen. There were condos across the street and they would have a clear view of our room.

Paul sat against the small table, spreading his legs, and said, "I want the whole world to watch you blow me tonight."

I was so hot I didn't care who saw us. I got down on my knees with Paul's luscious cock staring me in the face. While holding the back of my head he started rubbing his hot, dick all over my face. I saw it as a show of his dominance over me. I had no choice but to submit. Feeling his hard-on touching my skin was electrifying and made me want him even more. All the years of pent-up cocksucking desire were being released. I could feel the traces of his pre-cum being left all over my face.

When he was done teasing me, I instinctively reached for his erection. It was hot to the touch and drops of pre-cum were still oozing the tip. I didn't want to rush so I began by leaning forward and licking his balls, lightly kissing them, then licking underneath them between his balls and ass. I even let my tongue brush against his asshole a few times which was another first for me.

Paul was moaning and gently rubbing my head. I continued to lick and suck his balls then worked my way up to mouth and licked the base of his cock. It had been so long since I'd had a hard-on before me, I wanted to embrace every precious moment. I was using my lips and tongue on the base of Paul's shaft, moaning as I worked it over, then slowly worked my way up towards the head.

I stopped just before I got to the head. I was stroking him and looked into his blue eyes, then stared at his manhood, worshiping the hard meat before me. It was so close to my lips I'm sure he could feel my hot breath on his shaft. I then squeezed more pre-cum from his dick and began to slowly lick the drops, sticking my tongue into the hole at the tip. I wanted to savor the taste of his juices. Paul continued to moan softly which let me know I was doing a good job. His hands were trying to force his cock into my mouth but I wouldn't let him.

"You are such a little cock tease, bitch"

His words sent a chill of excitement through my mind and body. I swirled my tongue around the head, taking time to concentrate on the most sensitive area. I then rubbed the underside of the head against my tongue then let the tip slip between my soft wet lips into my waiting warm mouth. My lips closed around the meat in my mouth as it slid along my tongue. He let out a loud moan as my head started to bob. It's hard to describe the feeling of having a hard cock in my mouth again after all these years. I didn't realize how much I missed it. I loved blowing Paul and giving him pleasure. I knew this wouldn't be the last time I ever sucked a dick. I was addicted.

Paul grabbed my head and started to fuck my mouth as my head bobbed. More of his manhood penetrated my mouth with each thrust. I started to gag so he slowed down a bit but would still try to get more into my mouth. I wanted more of his cock too. My head was bobbing, my lips tightly wrapped around his shaft as my tongue swirled around it, tasting his luscious meat as I sucked it. It tasted wonderful; like a gourmet meal to a starving man.

As I was sucking, Paul exclaimed, "Oh shit, there are people in the condo watching us. Show them what a good little cocksucker you are Jay."

The thought of others watching me suck Paul drove me wild. I wanted to do a good job now. I wanted our audience to know I was a good cocksucker just like Paul ordered. I'd never see them again anyway so I didn't care who saw us.

Paul kept saying things like, "suck my dick, bitch. Show them how much you love sucking me. You're such a cocksucking whore"

I never knew I liked to be called dirty names but he was driving me wild with it. I felt like such a slut.

My head continued to bob, my lips and tongue working on the cock in my mouth. I would slow down at times to just enjoy the taste and feel of it, catch my breath, and tease Paul. I didn't want him to cum too soon. I wanted to enjoy every moment of having him in my mouth. I would then pick up the pace, working feverishly on him. His moans energized me as I sucked. Other times I would just let him control the action by simply fucking my mouth, treating me like the slut I was. At last, he was able to get his entire cock into my throat which gave me a feeling of pride for my accomplishment. I could feel his balls slapping against my chin as I sucked him deep into my throat. I could hear the sounds of my sloppy blowjob filling the room. I wished I could continue sucking him all night but that wasn't going to happen.

We were both so turned on when he announced, "I'm going to cum. Take it all, you cumslut?"

I moaned as I continued sucking on Paul's hard-on. I looked up at him to see him biting his lower lip; his eyes were closed. I could tell by the look on his face that he was enjoying my blowjob. Then I heard him grunt loudly and then I felt him plunge deep into my throat and his cock began to pulsate. I braced myself for my first taste of a man's cum in almost 25 years. He thrust a couple more times, then it happened. The first wad of cum shot into my mouth. I don't know why but I was still a little surprised but it tasted wonderful. Paul was using my mouth like a pussy and shooting cum into my throat. I savored the taste and moaned as I sucked, swallowing his tangy nectar. He pulled out for a couple of seconds to shoot some onto my face then pushed it back between my lips to finish off.

I was thinking to myself, "I did it. I finally blew another guy and drank his cum."

I was in heaven. I waited so long to suck another cock. It was ecstasy but at the same time, I was disappointed that it was over. I felt a sense of pride knowing I satisfied Paul's urges.

Paul slipped his half-hard cock from between my lips and said, "Wow, that was better than I ever imagined it would be. You suck a mean dick, Jay"

He then rubbed his half-hard cock across my face to show his domination over me again and to wipe some of his cum onto my face as an exclamation point but I was fine with it. I wore it with pride.

"I want you to leave the cum on your face for a while."

I replied, "anything for you Paul," as I swiped my tongue around my lips to taste the remnants of his orgasm.

I then squeezed the last drops from his softening erection and cleaned it off of him. Paul went to get us a couple more drinks as I got up. Paul then went over to the phone and ordered more food.

"It's still early. Is that ok?"

"I have nowhere to go, Paul. I'll be your little slut all night if you want"

In what seemed like a few short moments, room service knocked at the door again. Paul just motioned for me to answer it again. Then I remembered that I still had cum on my face, then smiled and realized that's what Paul wanted.

I looked through the peephole and saw it was the same waiter as before so I opened the door without hiding myself this time. He immediately noticed the cum on my face and giggled. He walked in with the refreshments and saw Paul with a towel wrapped around him, hiding his nakedness underneath. We just smiled at each other. Then Paul ordered me to come closer.

"I'm sure you've noticed the cum on my friend's face. Well, this is what's next."

Paul pulled down the back of my panties and made me show the waiter the butt plug. I felt humiliated again and blushed. This was part of my submission and I was embarrassed but it also turned me on.

Paul looked carefully over the bill, taking his time before he signed for it and the waiter left with a huge grin on his face shaking his head. I was so humiliated but I had decided earlier to totally give myself to Paul. My balls were aching from all the cum that was building up from being his sex toy.

We rested while having another drink and snacks still dressed in my lingerie. I felt sexy wearing it mostly because I know Paul liked it. I made sure I teased him by bending over in front of him a few times, then looking over my shoulder with a wicked smile on my face or giving my ass some extra wiggle when I walked around the room. Paul would run his hands up and down my stocking-covered legs which felt so good. He knew I was OK with whatever was going to happen next.

Paul then led me over to the edge of the bed as he sat down and told me to bend over his knee. My heart started racing again but I did as I was told. He pulled down my panties and removed the butt plug and began to finger fuck my ass again with his huge finger. I could feel my cock grow and press against his naked thigh. I was so hot and felt so vulnerable.

He then said, "You've been a naughty boy tonight and you know what naughty boys get, don't you?"

With that, he gave me a quick slap on the ass with his large hand as the other pressed on my lower back holding me in place. I cried out, mostly in shock as I clenched my ass cheeks together. When I relaxed, he struck me again and again on my bare ass. Here I was, a middle-aged man, bent over another man's knees; my ass getting spanked but it felt wonderful being dominated by this big man. Paul held me across his lap while he spanked me 25-30 times. My ass must have been red from being disciplined before he finally let me up. I rubbed my ass trying to get rid of the pain from the spanking I just received.

Paul took my hand, led me over to the small table by the window, and told me to bend over. He told me that we were being watched and I turned to look out the window to see a group of people in the condos across the street watching. It looked like a small party going on and I was the entertainment. Paul grabbed some more lube and began to finger fuck my ass again. I wiggled my ass in pleasure as his fat finger penetrated my asshole one more time. I felt so submissive bending over that table offering him my ass.

As he finger fucked me he told me, "you've been teasing me with that nice tight ass of yours in those panties all night. You can't just tease me like that Jay. Do you know what I'm going to do to you now don't you Jay? "

"Yes Paul, I know what a cock tease like me deserves."

"What's that Jay, tell me what you deserve for teasing me with your fine ass."

"I deserve to let you fuck my ass, Paul."

"That's right Jay. If you are going to tease me, you better be prepared to please me."

I turned to see him applying some lube to his erection. He waved to our admiring audience as he spread my ass. I could feel his hard-on pressing against my asshole. I was scared that it might hurt. I had only been fucked one other time many years ago so it was like losing my virginity all over again.

I pushed back a little to help him gain entrance and then it finally happened; the head of his dick pushed into my ass. The deed had been done. It hurt a little but not as much as I thought it might. The butt plug and Paul's fingers helped prepare me for this final submission. I was bent over a small table in front of a hotel window letting another man begin to fuck my ass while who knows how many other people watched from across the street. I felt so slutty.

Paul kept pushing while I pushed back. Inch by inch, he plunged into my ass. When he was about halfway in he began to slowly fuck me. With each thrust, he would push a little deeper until finally, I could feel his hips against my bare cheeks and I knew he was balls deep in my ass. A feeling of pride came over me for a moment as Paul started to slowly fuck me with long, deep, and slow thrusts. His hands were fondling my cheeks as he fucked me.

"You have such a nice tight butt, Jay. It was meant to be fucked. Tell me that you like my cock up your ass Jay."

"I like having your cock up my ass Paul. It is yours tonight."

"That's right, Jay. Your ass is all mine tonight," Paul replied as he began to thrust faster into me.

I was so happy he liked fucking me. I just wanted to please him. I felt my dick grow hard as he sodomized me. Holding onto my ass, he picked up the pace thrusting faster and faster. I could hear him grunting as he pummeled my ass. It felt so good; I fucked him back, trying to drive more of himself into me. It was better than I remembered. Here I was letting another man that I barely knew use my ass for his pleasure. I squeezed my butt tighter around his cock as he pumped in and out of me. I was so turned on that I started to stroke myself as he fucked me. I was moaning, begging him to fuck me as my hand worked on my dick.

"Fuck me, Paul. Use my tight ass. Fuck me, Paul."

"How would you like a cock in your mouth now Jay? I bet you'd love to be sucking on something nice and hard while I fuck you. I want to make you my whore. Would you be my whore Jay?"

"I would love to be sucking on a hard cock right now as you fuck my ass. I'll be your whore, your cum slut. Fuck me, Paul. I'll fuck and suck anybody for you."

"Your ass is so tight. It feels so good to be fucking you Jay. You're just a little whore aren't you?"