Chat Room Hooup

I'm an average guy in every sense of the word. I married my high school sweetheart right after college, got a job that I've kept since graduation, have two great, grown children, and have a house in a suburban subdivision. Life has been good to me. I'm now middle-aged in my late forties and my wife is going through menopause which has had a negative effect on our sex life. I thought after the kids went away to college, my wife and I could refresh our love life but that hasn't happened. She's a wonderful woman and I'd never think of cheating on her with another woman. She will accommodate me with an occasional fuck but it's not what it used to be, but what is as you get older? 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 future wife and I broke up for a while when we went to separate colleges. We both had a few partners when we weren't together but we've been with each other since shortly after we graduated. I had a few bi experiences in my college days with a close friend, Jeff, mostly when we didn't have dates when we were very horny, young guys.

It all started one dateless Friday night when we were both experiencing a dry spell in our sex lives. We sat down on the sofa with a couple of joints and a twelve-pack of cheap beer and decided to watch a porn video. I don't know why we did that because it only tortured us further and gave us both bluer balls than we already had. As we were watching the video, we were both trying to avoid adjusting our growing erections but after a while, it became too uncomfortable. Once I saw Jeff adjust his hard-on, I felt comfortable adjusting mine. However, Jeff began to lightly rub himself through the outside of his shorts. I tried not to look but I couldn't help but keep glancing over at him and the obvious lump in his pants. I was intrigued and curious but also high and horny.

The video was now showing a beautiful blonde blowing a guy and Jeff commented, "Man, I sure could use a blow job right now."

"No shit. Me too."

We continued to talk about the blow job we were watching on screen and about some of the women who blew us. Then Jeff took me completely by surprise.

"Have you ever had a guy blow you, Jay?"

"No, Jeff. Why? Have you?"

"Yeah, in my freshman year in college. My roommate was gay and one night he gave me a great blow job too. That dude could suck a dick."

"Are you shitting me, Jeff?"

"No, for real, man. It was great."

"Did you, uh, you know, return the favor?"

"No, but I thought about it but never had the courage."

I didn't know where Jeff was going with this conversation. I don't know if he was hinting at anything but it got me thinking about what it would feel like to have him blow me. I figured if he blew me, he'd want me to blow him too. I started to get nervous because I was considering asking him if he wanted some relief but I was too scared. I didn't want my roommate to think I was gay. Those were different times and people weren't as open about being gay as they are today.

The girl in the video was blowing a few guys which led Jeff to keep talking about needing a blow job. I have to admit, between being high, drunk, and horny, I kept thinking about needing one too.

After the girl in the video was sucking on her fourth dick, Jeff looked at me and said, "I'll do you if you do me."

"Do what?"

"You know, blow each other. It'll be better than jerking off again. Don't tell me you won't be rubbing one out tonight either."

"Are you serious, Jeff?"

"I'm dead serious. No one has to know."

I didn't know if he was messing with me and I figured I'd call his bluff so I said, "Okay, you go first."

Jeff replied, "Okay, whip it out but if you don't do me, I'll kill you."

I slipped off my shorts and underwear and threw them to the side. I lifted my hips a bit, my erection pointing straight up in the hair. I looked at Jeff, sort of daring him to blow me while still thinking he was bluffing. I was pleasantly surprised when he got down on his knees between my wide-spread legs and took hold of my erection.

"If I do this, you better suck me too."

"Don't worry. I won't leave you hanging."

Part of me still didn't think Jeff would do it but he leaned forward and I could feel his hot breath against the head of my dick. He opened his mouth and took me between his lips. I moaned in pleasure at my unexpected blow job from my roommate. To be honest, I've had better blow jobs before; he even scraped me with his teeth a couple of times, but it still felt fantastic. Feeling Jeff's warm, wet lips around my dick was still better than using my hand.

Jeff's head bobbed in my lap as he gave me a blow job. I wish I could have lasted longer but I had a load built up before we watched the porn video but my balls only filled up more watching the movie and from all the talk about blow jobs. I warned Jeff that I was about to cum thinking he might not want to swallow my jizz but he kept sucking me and I blasted wad after wad down his throat which he lapped up without a problem.

When I was done cumming, he lifted his head, took a couple of swigs of beer, stripped, and said, "Your turn."

Now was the moment of truth. I thought Jeff was bullshitting but now the pressure was on me. I was extremely nervous because even though I wanted to back out, I knew there was no way I could. However, not only was I curious about sucking a man's dick, I now owed it to Jeff to reciprocate. Jeff sat down next to me with his erection standing at attention like mine was earlier. I got down on my knees in front of him, took his erection in my hand, and looked up at him.

Jeff must have sensed my hesitancy and said, "Come on, man, suck it. Go ahead. It's not so bad."

I gave my shoulders a little shrug, figuring, "what the hell," lowered my head, closed my eyes, opened my mouth, and slid Jeff's dick into my mouth as my lips closed around it. As my head started to bob around the hard meat in my mouth, I decided it wasn't so bad. With my eyes still closed, my other senses were heightened and I could feel the veins in his shaft with my tongue and noticed how hard it was as opposed to the softness of the head. My tongue felt the ridge separating the head from the shaft and listened to him moan as my tongue swirled around the hard dick in my mouth. After a minute or two, I concluded that I liked blowing Jeff and wanted to do a good job. From his squirms and moans, I could tell I was succeeding.

When Jeff's breathing started getting faster, I could tell he was close to orgasm which was confirmed when he clutched my head and said, "I'm about to cum."

He was holding my head so tight, I couldn't have stopped sucking him if I wanted. The fact was, I wanted to deeply satisfy him and was looking forward to making him cum. I remember being a little concerned about what a man's cum would taste like but there was little time to think it over. Jeff began to cum in my mouth, splashing my throat with his seed. My initial concerns were resolved when I decided the taste of his cum wasn't so bad, as a matter of fact, I liked it. He shot several loads into my mouth before his dick began to shrink.

I was disappointed when he withdrew himself from between my lips, but that disappointment turned to joy when Jeff said, "Damn, dude, that was a pretty good blow job."

Both of us quickly put on our shorts and awkwardly tried to pretend nothing happened but that was impossible. We agreed this would be our little secret and opened another beer and continued to watch the porn video in silence. I couldn't get over the thoughts of how much I enjoyed having Jeff's hard dick in my mouth. I could see a lump growing in Jeff's shorts which, in turn, got me going again.

When Jeff asked, "Do you want to do it again?" I quickly agreed to another swap of blow jobs.

I went first this time but with no hesitation. I enthusiastically got down between his legs again and began to blow him. This time, I savored every second. Thankfully, Jeff took longer to cum this time so I was able to enjoy blowing him for a longer period. His second load wasn't as big as the first but it was just as delicious. Jeff returned the favor and drained my balls for the second time before we both called it a night and went to bed.

Things were a little awkward the next morning when we sobered up but we both agreed it was a one-time thing, even though we both gave pretty good blow jobs. I was concerned that I liked sucking a dick too much and made more of an effort to find girls to date to keep me from being tempted to suck Jeff off again. That only lasted so long before Jeff and I found ourselves dateless again on a Saturday night and ended up blowing each other again. Over the course of that senior year in college, Jeff and I blew each other on average about once or twice a month. Our bisexual trysts stopped at the end of the semester but not before we tried butt fucking on our last night together before the summer break. That was the last time Jeff and I got together as we went our separate ways after graduation.

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. It had been a long time since I had been with Jeff and we were both happily married so he wasn't an option. I had no idea how to find someone else either. There was no way I was going to ask any of my current friends if I could suck them off.

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 as I jerked off.

I gradually drifted over to the gay section at times and it reignited my desires to relive my bi experiences of my younger days. I never planned on acting upon those desires; it was just a fantasy. I then started visiting the adult chat area. I would role-play in various rooms depending 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 several 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 we were a natural fit and continued our chat room role-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. Paul let me explore my submissive bi side. I think I liked the idea of being coerced into being submissive because it took away the guilt I felt for desiring to blow another man.

As Paul and I got to know each other through the chat room, we found out that we 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 at the same time. We wouldn't necessarily 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 my deepest, darkest fantasies that I never expected to live out. I could barely admit to myself that I enjoyed being dominated in a chat room. Besides, it had been 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 first day of the conference.

During the first day, I was more than a little distracted. My mind kept drifting to drinks with Paul later that evening. 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 brewpub 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. He was a few minutes late so my anxiety was increasing the longer I waited.

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. Sorry, I'm late."

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, pinstriped suit. He looked like a banker. I was pleasantly surprised. I was expecting Paul to be nothing like he described himself. He was 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 barstool next to me. We started making small talk about the weather and sports. You could tell we were both nervous after all, it was a bizarre situation. We were both married men who met in an Internet gay 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 decided to get a table, had a couple more beers, ordered some Buffalo wings, and exchanged life stories about the 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 dick 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 other's eyes at times, then nervously look away. Paul placed his hand on my leg for short periods and I did nothing to stop him. 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 fourth 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, especially by 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 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 the bill. Part of me felt like I was his date. As we were sitting there waiting for the waiter to settle the bill, Paul got closer to me, our bodies touching. I felt a sense of excitement. Then I felt Paul's hand brush across my upper thigh. 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 Paul's 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. It's one thing to fantasize about a sexual encounter but completely different actually living the dream.

As Paul led me into the room, I saw that it was a suite with a living room, bedroom, and minibar; nothing real fancy but it wasn't cheap either. Paul walked over to the minibar 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 got us another beer as we talked. We would stare into each other's eyes for short periods just like in the bar. We would nervously 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 you being here is making me horny."

Paul was looking at me anxiously waiting for my response. I could tell he had to gather up the courage 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 also a little drunk and horny myself.

Paul was waiting for my answer when I finally replied, "Well, 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 it 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 undressed him with my eyes, wondering what he looked like naked.

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. This was going to be the most adventurous sexual experience I had in years, maybe my entire life. I saw Paul walk over to the closet and bring out a box that 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. Reality had just sunk in as to what I was about to do with Paul and I almost backed out. My heart was racing and I needed a moment to calm down.

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, 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. If I backed out, I may never get the chance to live out a sexual fantasy again.