tagGay MaleChat Room Hookup

Chat Room Hookup

byJay142©

I'm an average guy, 6 ft. 200 pounds, brown but graying hair, in my late 40's with a wonderful wife and 2 grown children. I'm in decent shape for my age. I work out regularly but I'm carrying a few more pounds than I should, but who isn't at this age? My wife and I are empty nesters and our sex life hasn't been that great for a while now. I guess just with age and life taking its toll, things just aren't what they used to be, but what is? I had a few bi experiences in my college days with a close friend mostly when we weren't dating when we were just very horny, young guys. I have to admit that from time to time over the years I did miss having a hard cock in my mouth or a dick in my ass but the opportunity to relive my younger days never presented itself and I wasn't really looking that hard anyway.

As my sex life with my wife started to cool, I started looking to the Internet for excitement. I'm just amazed at the extent of porn that is available. I found the stories on Literotica to be extremely exciting. I could live out my fantasies through the imaginative stories of others.

I gradually drifted over to the gay section at times and it reignited my desires to relive my bi experiences. I never planned on acting upon those desires; it was just a fantasy. I started visiting the adult chat area. I would role play in various rooms based upon my mood and eventually drifted over to the Cock 4 Cock room out of curiosity and that's where I met Paul.

We chatted and role played more than a few times in the chat room and I found it to be so exhilarating. I would either jerk off while we were role playing or I would jerk off shortly after we signed off.

We hit it off from the beginning as Paul was a top and I loved being the bottom so were a natural fit and continued our chat room playing for a few months. I knew what he liked and he knew how far I would go. It was nice to expand my fantasies too, after all, role playing is the safest sex out there, and I could do things I would never even think of doing in real life, or so I thought.

As Paul and I got to know each other through the chat room, we found out that we actually didn't live too far apart. We never talked about actually meeting because we both admitted these were just fantasies that would probably never be acted upon.

That is until one day, my boss told me he was sending me to a 3 day conference where Paul lived. My mind immediately thought of Paul. Would he want to meet or do I even want to meet him? It's one thing being friendly on the Internet,sharing fantasies but to actually meet was exciting and frightening too.We wouldn't actually do anything but I was curious to meet my roleplaying partner.

A couple of weeks before my trip I told Paul I would be in his city for a conference. It was Paul that suggested we meet up for a drink one night.

My heart was beating double time when I answered, "Sure. That would be fun."

He even said, "we don't have to do anything but it would be fun to meet over a couple of beers and put faces to the chats we've had."

That put me at ease, as these were roles and fantasies that I never expected to live out. After all, it was over 25 years since I had a bi experience. I wasn't sure I'd go through with it even if I had the chance. Paul and I agreed to meet for a drink after the conference the first day.

During the first day of the conference, I was kind of distracted. My mind kept drifting to drinks with Paul after the last session. I wondered if he really looked as he described himself. I wondered what he would think of me. I did lie about my age by a few years and my weight by a few pounds but who doesn't lie about those?

I got to the brew pub a few minutes early and waited for Paul. I sent him a text to tell him I was sitting at the bar and what I was wearing. He never responded so I didn't know if I was going to be stood up or not. In those few minutes that I was waiting, I was both excited and scared. I felt like I was going on a blind date, maybe he came in and saw me then decided to leave.Maybe it was just a prank. I felt foolish.

Just as I was thinking we would never meet, a good looking man about my age or even a few years younger came up to me.

"Jay, I'm Paul."

I checked him out as I stood up and shook his hand. He was 6'5" around 250 pounds, a big guy with salt and pepper hair, deep blue eyes and wearing a perfectly tailored dark blue, pin striped suit. He looked like a banker. I was pleasantly surprised. I was expecting Paul to be nothing like he described himself. He was actually better than I had imagined.

"Well Paul, it's nice to finally meet you. Can I get you something to drink?"

Paul ordered a beer and sat down on the bar stool next to me. We started making small talk about the weather and sports. You could tell we were both nervous afterall, it was a bizarre situation. We meet in an Internet sex chat room and here we were, sitting in a bar having a beer with each other.

We were on our second beer when we started to relax and began to discuss why we went into the chat rooms. Our stories were similar, our wives had lost interest in sex, we were probably having some mid-life issues ourselves and we were just looking for some harmless fun. We hit it off like two college buddies who hadn't seen each other in years. We had a few more beers, ordered some Buffalo wings and exchanged stories about life, girls we've been with and I told him about some of my bi experiences in my younger days. I knew he was a top and he told me flat out he had no desire to suck a cock or have one up his ass. We joked about it a little. It put me at ease that he had a sense of humor. As we were drinking and talking, we would look deep into each others eyes at times, then nervously look away. Paul placed his hand on my leg for short periods of time and I did nothing to stop him of course. I don't know if he was testing me or what, but I didn't feel at all uncomfortable with what was happening.

We had both finished our fifth beer and were deciding if we wanted another when Paul said, " I hope you don't think I'm being presumptuous Jay, but I took the liberty of renting a hotel room around the corner. Do you want to continue talking there?"

My heart almost stopped. I guess I wasn't expecting this but in hindsight, I shouldn't have been so surprised in the way we were getting along and looking at each other.

He made me feel more at ease when he said, "we don't have to do anything if you don't want to but it's kind of crowded and noisy in here."

My heart was racing but we were getting along so well I replied, " I, uh, I guess it would be ok."

I couldn't help but wonder if we were going to bring our chat room fantasies to life. It did cross my mind while we were drinking and part of me was hoping we could but I was still caught by surprise. I wasn't sure I could actually go through with it anyway even though I did find Paul attractive. He did say we didn't have to do anything which would give me an excuse if I wasn't comfortable.

I stood up to reach for my wallet but Paul said he would take care of it. Part of me felt like I was his date. As we were standing there waiting for the bartender to settle the bill, Paul got real close to me, our bodies touching. I felt a sense of excitement. Then I felt Paul's hand brush across my ass. I didn't say anything but I felt more attracted to him than before. He paid the bill and we walked around the corner to the hotel. It was such an odd situation with me walking to a hotel, with a guy I had just met for the first time.

I had mixed feelings while we were in the elevator. I felt excited to be in Pauls' company but I was also nervous as hell. I had no idea what would happen in the hotel room but from our chat room experiences, I did know what could happen. I wasn't sure I was ready for that.

As Paul led me into the room, I saw that it was a suite with a living room, bedroom and mini bar; nothing real fancy but it wasn't cheap either. Paul walked over to the mini bar and got us a couple more beers. He complained that it wasn't well stocked. We sat around the living room just talking like we were in the bar. Paul kept getting us beers as we talked. We would stare into each other's eyes for short periods just like in the bar. Nervously we would look away and there was a certain sexual tension in the air but no one wanted to say anything.

After Paul got us another beer he said what we were both thinking, "well, are we going to do this Jay? I mean, we don't have to but just meeting you brings to mind all those chat room sessions we've shared and just you being here is making me really horny."

Paul was looking at me anxiously waiting for my response. I could tell he had to gather up the courage just to ask the question we were both contemplating. I didn't say anything. My mind was racing. I was thinking all evening what I would do if he asked. I would flip flop on what I would say or do. I did find him extremely attractive and I knew from the chat rooms what would be expected of me. I was a little drunk and horny myself.

Paul was waiting for my answer when I finally replied, " I guess we're here and may never get this chance again so sure, let's do it."

I couldn't believe I just said that. I don't know if was me, the alcohol or my horniness that responded but Paul got this huge grin on his face along with a sigh of relief. I could see a bulge forming in his pants which increased my nervousness and excitement.

I knew that by agreeing to go forward, I was agreeing to comply with all of Paul's wishes. I would be totally giving myself to him. I saw Paul walk over to the closet and bring out a box which he handed to me.

"You can go into the bathroom and change and I'll get ready too."

I reached out, took the box from Paul and retreated to the bathroom. I started to have second thoughts as I knew what was in the box. I opened it and found a pink lace chemise with matching high cut panties and matching stockings just like he described in our online chats. I almost backed out.

Part of me wanted to run out the door and back to my own, safe hotel room. I was never into cross dressing, but when I felt the soft lace material and thought of how good it would feel and I started to remove my clothes. I was about to embark on a new sexual adventure and figured my apparel was only a minor part of what was about to happen.

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 then up over my long, muscular legs. Then I 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 cock pressing 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.

"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. His eyes roaming from my stocking covered legs up to my panty covered ass, 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 cock against my thigh as his tongue found its way into my mouth. His hands ran over my stocking covered legs and thighs. Gently cupping my balls and cock through the lace then up to fondle my nipples.

My own cock was growing as I was being fondled. 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 his 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 just want to please you tonight."

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

The nervous excitement returned when Paul said, "OK Jay, pull down you 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 asshole 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 deeper. When the plug was fully into my ass, Paul ordered me to stand up and pull my panties up again.

He rubbed my ass with his hands 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 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 but 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 embarrassment.

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 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 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 cock in the chat rooms and jerking off fantasizing about a potential encounter. Now, his real live cock was right there before me. I wanted to suck his cock and please him the best I could.

Before he would let me suck his cock, he led me over to the hotel room window. It was a 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 suck my cock tonight."

I was so hot I really didn't care. 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 by rubbing his hot, hard cock 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 cock touching my skin was electrifying and made me want him even more. All the years of pent up cocksucking desire were being released. When he was done teasing me, I instinctively reached for his cock. It was hot to the touch and drops of pre-cum had formed on 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 lick the base of his cock. It had been so long since I've had a hard cock before me, I wanted to embrace every precious moment. I was using my lips and tongue on the base of Paul's cock, moaning as I worked his cock, then slowly worked my way up towards the head.

I stopped just before I got to the head of Paul's cock. I was stroking him and looked into his blue eyes, then staring at his cock, worshipping the hard dick before me. It was so close to my lips I'm sure he could feel my hot breath on his cock. Then I began to lick the drops of precum from slowly and softly, sticking my tongue into the hole at the tip of his cock. I wanted to savor the taste of his juices. Paul just moaned again. His hands were trying to press his cock into my mouth but I wouldn't let him.

"You are such a little cock tease, bitch"

His words sent a rush of excitement through my mind and body. I then swirled my tongue around the head, taking time to concentrate on the most sensitive area. I then rubbed the underside of his cock against my tongue then let the tip slip between my soft wet lips into my waiting warm mouth. My lips closed around his hard cock 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 sucking Pauls' cock. I loved giving him pleasure. I knew this wouldn't be the last time I ever sucked a cock. I was addicted.

Paul grabbed my head and started to fuck my mouth as my head bobbed. More of his cock 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 cock as my tongue swirled around it, tasting his cock as I sucked it. It tasted wonderful; like a gourmet meal.

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byJay142© 10 comments/ 15601 views/ 28 favorites

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