After Jerry and I had a chance to meet and then go to his house for a massage I was feeling better about him, more safe. I was on the Internet in an IRC chat room channel I founded called #bi-married-men. I was moderating early that morning when he popped in to say hello and checking to see if I had a fun time. I told him that was one of the hottest experiences I think I have ever had.

You give great massages I told Jerry. He expressed how much fun he had and suggested it would be fun to get together again. I agreed but had to plan ahead so it would be while before we met again.

We talked briefly as to our options, and his house now was no longer an option for three to four months. His son was home from college and staying in the room. My house in the country was too far, and my house in the city now rented. I told him about the motels Doc and I use to use, and he seemed fine with the option.

Jerry expressed my ass was nicer than he was hoping for and told me several times during our chat that he would love to pleasure me with some fun anal play. I told him to let's see how things progress and take one thing at a time. He kept complimenting me on the shape and perfect size my ass was for him. I had been working out and doing leg strength training that was giving me better body tone; I guess my ass too.

Things were busy in life with the family and work. I was increasing my time moderating the #channel but had enlisted a few old friends to help me with the now growing group of men. The #channel was evolving to not just a place for us to exchange feelings and thoughts. It was becoming a pickup spot for some guys cruising for a quickie. The chat room was not supposed to be the primary purpose of the #channel if men met and clicked that was okay but not a place for quick hook ups only.

Doc was stopping in the chat room keeping in touch in his new home and how his family was adjusting. Doc was getting requests from guys in his area who knew what we had gone and wanted to meet him for some fun. He was feeling a bit tempted but with moving and the family and still thinking of the fun we had he was not ready for a new friend.

We were in private chat off #channel that he was missing our regular afternoon get together. We were reminiscing on the fun we had with each other. Feeling perfectly safe and comfort in having the same level of experience. I agreed and told him about my massage with Jerry; he said it sounded hot. He knew Jerry from talking to him, and I expressed my concerns about his level of experience. Doc understood my concerns and provided some thoughts that made me feel more at ease about Jerry.

Doc told me SueTx had contacted him if he needed some help adjusting to his new home. She is a sweet lady and knew all the people in #channel and the area he had moved too. Having met most of them, she was advising Doc who she felt was safe and who could be trusted. We talked a bit more about how we had some much more we wanted to try but sadly the time was cut short. We had a perfect set up, and both were expressing fond memories of our fun afternoons. We never did get to have an overnight trip as we had hoped for where we could have a lot of our extended cock sucking time and other fun for a whole night or weekend. The most time we spent together was maybe 4 hours as the longest.

Jerry was popping into the #channel at least twice a day now and was making sure he kept in touch with me. We were talking about what day and time would work best for us to meet again. It had been almost three weeks since our last meeting. We settled on a day and time the following week at one of the motels. Jerry told me to get a room and let him know the number. I was put off that he did not get the room, it always seemed to be. I always felt a little odd when booking the room at motels.

Jerry and I talked for awhile the night before to make we were on the same page as location and time. He was always complimenting me on my ass and how much fun it would be to enjoy it. I had mentioned condom to him a couple of times during our talks, and he said he was very safe and did not use them. After a talk with Doc, I was feeling a little more at ease but told Jerry we will see how things go when we meet.

I got there early like most times and picked up the room key and went up to the motel room. I turned the heat on to warm the area a bit and turned down the king size bed. I also turned on a couple of lights and headed to the bathroom. I undressed and went in to take a shower to freshen up. After drying off, I was just sitting at the end of the bed thinking about what we were planning to do and my concerns.
I heard a knock at the door and looked out to see Jerry.

I opened the door nude, and Jerry smiled; well now this is a pleasant surprise he said. The cold air was coming in behind him, so I quickly closed the door. He was carrying a couple of small bags one with some wine and snacks the other had some personal items. Soon as Jerry could put the bags down he came over and began to cup my package and hugged me looking deep into my eyes and with both hands now he grabbed my ass cheeks and pulled me close.

He was rubbing my cheeks and sliding his finger up and down my ass crack probing my anus softly. His rubbing hand making me grow as well as relax a little bit more. Jerry looked like he wanted to kiss but moved away toward the bathroom where he began to get undressed and to hang his clothing. I watch him as I sat nude on the side of the bed. Jerry was now naked and got out a couple of wine glasses from his bag. He popped the cork asking if I would like a drink of wine, I replied sure.

Jerry was a classic Irishman with pale skin and bright red short hair on his body. A nice firm ass for a man near fifty with a slim body shapes his body was showing it all well with the back glow from the bathroom light and large mirror. He was walking over toward the bed now sporting a beautiful hard-on out of his well trimmed red pubic hair. I reached for him and pulled him over toward me. His beautiful cock was now up and to the left and looking tasty.

He stood in front of me as I sat on the bed cupping his ass cheeks I guided his manhood toward my now wet warm mouth. Holding his balls, I was licking around his cock tasting him. I took his cock head into my mouth swallowing it as I moved his cheeks forward with my hands as Jerry put his hands on my head and was running his fingers through my hair.

I slid my tongue in a swirling motion down the bottom of his hardening cock deeper into my encircling lips and mouth, Hmm... I mumbled as I began to bob up and down on his well-shaped penis. Jerry was just standing there enjoying the moment. You are one good cock sucker Jerry said as I worked his cock and balls over pretty well. He stepped back and with a giggle told me if you do that much longer there will be no fun later.

He went back over for the glasses of wine, and I had moved and was leaning on the headboard of the bed in the pillows. I was now also sporting a hard woody as Jerry handed me a glass of wine. Jerry got in bed next to me as we rubbed our legs and thighs gently. Sipping on the wine we just talked about things going on in the #channel the wine tasted splendid and I was becoming even more relaxed. Jerry began rubbing my inner thigh and asked if I was feeling ready to be fucked. I took a gulp of wine and looked back at Jerry I think so, we need to take it slow. Jerry had a huge smile and replied I will be very gentle. I asked him again if he was sure he was safe and disease free and he nodded yes I am very sure.

Jerry asked me if I would like to be ass rimmed a little and I said sure that would be very nice. I had finished my wine as Jerry still sipped on his glass. I put my glass on the nightstand and leaned over his big red cock as started to suck his, and he was oozing some precum, and I was cleaning it off his cock head. Jerry leaned over and began to rub my anus and cheeks saying such a nice smooth ass so fuckable. He pulled me up slowly and said lay here on your stomach. I repositioned, and Jerry spread my cheeks and began a slow rimming of my hole with his tongue. It was feeling good; he knew what he was doing.

He was slowly probing my ass with his tongue as my cheeks rose up to help him get a better angle.

Jerry was rubbing my balls and cock as Jerry ass rimmed away he had spread my legs. I was still not sure I wanted this, but Jerry was doing everything right to make me want it. I guess Jerry thought I was ready and moved his body up, and his cock head poked my anus causing a sharp shooting pain. I quickly rolled over on my side while I yelled showing I was in pain. Jerry was saying over and over again I am sorry, I am sorry are you okay? I was now lying on my back with my eyes closed still in some pain that was slowly subsiding. Are you all right he kept asked? I am so sorry; Jerry was worried what he had done to hurt me.

The pain had subsided, and I was able to talk Jerry asked me to turn over so he could take a look to see if there was any damage or marks. He was looking while still apologizing and saying I do not see anything wrong. All I could think could have happened when he started unexpectedly I tighten up, and he poked a sensitive spot. I told Jerry I am okay just let me have a few minutes. He got up and got a bottle of lube from his bag and turned all but one light off.

After consuming another glass of wine to calm myself; I was lying on my stomach relaxing next to Jerry, who was there sipping some wine and softly rubbing my tush. Do you want to try again he asked? I think you need me to loosened up your ass hole. Jerry applied some lube to my anus. Jerry was lubing up my anus in a circular motion with his finger

He said I am going to try a finger, and I said okay. His finger started to probe tenderly, and I began to relax. One knuckle was in then two, and soon his whole finger was inserted. I felt good as he rubbed my prostate. Fingering with a smooth slow motion, he added more lube. Jerry did this for awhile while moving his digit in a circle motion while moving in and out. Jerry said now I am going to try two fingers. Jerry applied more lube to anus and fingers pressing in my softly in my hole I accepted the two fingers and he kept slow finger fucking my now stretched anus. Jerry was enjoying this and had moved up pressing his body against mine. His cock was now hard and leaking with anticipation.

Jerry was increasing the insertion speed in and out while spreading his two fingers wider open. He murmured I am going to try three fingers. Feeling very relaxed as Jerry fingered away he applied more lube on all three fingers and pressed again, this time, my anus opened quickly to all three. It felt good as Jerry fingered and stretched my ass. I was well lubed, and Jerry kept ensuring I was not in pain. As he continued to finger me, he asked, do you want the real thing now? You are taking three fingers, and you feel relaxed. I said I think so, yes let's try. Fucking me is what Jerry had been dreaming of doing for some time.

Jerry moved between my legs and spread them apart. He was savoring the moment as he spread my ass cheeks several times fingering and rubbing my bottom. He said Ben you have one nice ass, are you ready? I nodded yes as I lay relaxed like I already had been fucked. Jerry did some butt rubbing and back rubs as he was sliding his slick cock between my cheeks as he did during my last session.

He knelt one last time thumbing my hole then spreading my cheeks he slid is cock head in my wet steamy hole. Opening as it wanted his dick Jerry pushed his engorged in a smooth motion that felt like never before, so natural and soft as he entered me. Does it feel good he whispered in my ear? Yes, it seems like a perfect fit. Jerry was taking things easy as his cock was fucking my ass like a pro. When he first inserted Jerry moaned and put his head on my back and his arms up under my armpits holding me.

His head was against mine as he was thrusting cock up my ass, nibbling and kissing the back of my neck and shoulders. Relaxing my sphincter as he trusted in I would tighten up as his cock was moving out. After I was doing this a few times, Jerry said wow! You are a more a far more rounded bottom than I thought. Jerry was coaching me with soft whispers of how to relax and contract when his thrusting paced began to pick up.

He was now really getting in fucking me, and I pulled my hips up slightly for a better angle for him to plow my ass with his throbbing cock. I enjoyed the smooth gliding motion of his manhood sliding in and out of my ass hole using a grinding movement.

My ass had never felt like this before, and it was a beautiful feeling as Jerry tenderly fucked me. The curve and angle of his penis made the inside my ass feel his manhood pulse and throb deep inside me. I felt the hardness and softness of his penis bobbing around inside me.

Jerry asked to turn over, and I did slowly, I pulled my legs up exposing my wet hole. He looked me in my eyes as Jerry pushed his cock his in my wet warm ass hole and my eyes rolled back. He moved closer while slow thrusting deep as our balls slapped together softly. My cock was rock hard, and Jerry was stroking me with his soft hand.

His lips were now touching my lips I accepted his kiss as our tongues and lips combined as passion had taken over we kissed deeply. Jerry is now thrusting his cock harder and deeper into my anus. You have one tight ass, Ben; I love this moment Jerry said. Jerry was grunting with every push into my anus.

We began to kiss again, and Jerry was breathing heavy, and his fucking speed was increasing. My cock had precum dripping out since we switched positions. Jerry’s cock curved up and left it now was massaging my prostrate with every long smooth stroke of his cock. Jerry stroked my lubed cock as precum oozed out. Enjoying your prostrate massage Ben said, Jerry, then we kissed again locking lips and tongues. My legs spread wide open wrapping around him with my ankles resting on Jerry's ass.

 Jerry was now tightening up as he was now fucking me harder and faster. I was going to blow soon and now moaning my cock started pulsating while shooting out ropes and wads of cum all over me. My back arched up, and my body pushed down on Jerry's gyrating pelvis. I made primal sounds of pure enjoyment as my spunk thoroughly coated my chest. Jerry's thumb was milking my cock entirely with his thumb trick. I was helplessly under his full control.

I felt Jerry’s cock head beginning to swell. My cock oozing drops of cum out with every pounding of my ass that Jerry was giving me. Still feeling great being fucked by him. He groaned loud when he let out his first huge cum load I could feel that one as his cock head exploded his ejaculation. My ass hole could feel the pulse of wads of cum squirting up his cock into my ass. He drove his cock deep into my sweet hole his hips swinging wildly.

His throbbing cock delivering loads of spunk flowing into my warm wet hole. Now my ass was so full it was oozing his man seed out of my anus as he kept fucking me. Jerry was still thrusting quickly but was beginning to slow down. Jerry was savoring every moment as my sphincter squeezed his cock draining him dry. Jerry was gasping and sweating as his cock was going soft and slowing to a stop buried in me.

Moving my ankles, I pulled him into me using my sphincter to drain his cock further. I sat up as spunk, lube and sweat flowed down my torso to my penis and balls. I reached up kissing Jerry saying that was a great fuck. Jerry smiled you fucked me better than any bottom I have had in years. Ben, you are one great fuck, and he slapped my ass playfully.

Both being exhausted we wandered to the bathroom double shower. My ass was still dripping his cum down my legs. We lathered up with soap and hot water cleaning each other off, me more so. We did not talk much we just were relaxed and glowed at the fun we just enjoyed.

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I hope you enjoyed the event.

Jerry got his wish, and I got to feel what it was like to be well fucked.
The story in part is a true story that took place back in the early 1990s.

IRC was the first Internet chat area, and #bi-married-men was a #channel I started. The main network EFnet was where it once was located. The event is real, but not all details are entirely correct. The story is what I still fondly remember.

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The story is my first attempt and I am open to helpful feedback.