This is the third part of my true story, or I should say "stories", I guess. At least they will all be grouped together. Thanks to everyone for their very positive responses.
Encounter with an older man, part 3 by Riley
March 2000
I read my email and sure enough, an email from Trelane was waiting for me. My heart started to pound as I read it, then it was pounding even faster! Trelane told me that he had a friend, another top, who was wanting to join us for a threesome. I had often fantasized about being with two men at once, and here was my chance. I sent a reply stating that I would be happy to meet his friend, but being sexual with him would just depend on what happened at our first meeting.
A couple of days passed, along with a few e-mails. We finally decided to meet at Trelane's place on a Sunday afternoon, which was the 5th of March, 2000. The weather was nice as I drove to Trelane's, and I arrived right after lunchtime. I laughed as Trelane met me at the door, and I said, "What's with all the clothes? Last time I came over, you were naked." He was wearing shorts, a t-shirt and was barefoot. We hugged after he closed the door, and we walked inside to meet his friend "Tom". (Not his real name.)
Tom made my heart skip the first time I saw him. He was probably 6'1" tall, around 225 - 250 lbs, very masculine in appearance, with a great smile and marvelous blue eyes. I shook hands with Tom and I guess he could tell that things were going to happen soon. We all sat down and talked things over while having a beer. Tom, married for 25 years, not exactly "gay", but very bi, hadn't been sexual with a man for almost 15 years. Tom was a true top, like Trelane, and wasn't into sucking or being fucked. Our discussion continued for about 30 minutes until I announced that I had to take a leak. I went to the closest bathroom and shut the door, then removed all my clothes. I pissed in the toilet and flushed, then walked back to the living room, stark naked.
When I got to the living room, Tom and Trelane weren't there, so I walked to Trelanes bedroom and there they were, both stark naked. We all laughed and Tom said, "Well, I guess we're all on the same wavelength!" I went to Trelane and gave him a hug and a kiss, then I moved to Tom. Tom was very hesitant as he embraced me, so I took my time, rubbing his back and his bare asscheeks, until he brought his lips to mine and gave me a very passionate kiss. I reached down to feel Tom's cock and was amazed that it was hard as a rock already. I felt Trelane move behind me, then I was sandwiched between two masculine, sexy men. My right hand found its way back to Trelane's cock, and I sighed as it was already pretty hard and very thick.
Trelane's hand found its way between my cheeks and I felt him start to lube me with something. Tom was kissing me again, and I moaned into his mouth as Trelane's fingers probed in and around my ass. Before I knew what was happening, Trelane had three fingers buried inside me, then he was stroking them in and out, very slowly. I started leaning forward a bit, and Tom took that as a cue to back up. I kissed my way down Tom's hairy chest until I was bent over at the waist and his cock was at eye level. Tom's cock was a little longer and thicker than Trelane's, and it was cut. I enjoyed seeing his large cockhead up-close, and smiled as I noticed large amounts of precum oozing out the tip. My lips had a life of their own, and I soon discovered that they were wrapped around Tom's thick meat and I was sucking him for all I was worth.
As I sucked Tom's wonderful cock, I realized that his cock was really flowing with precum. It seemed to fill my mouth, and it had a wonderful taste! In a moment, I found myself facing Trelane's cock and I started sucking it, but felt myself being pushed down till I was on my knees, Trelane's cock still in my mouth. I was moaning and groaning, totally enjoying my first threesome with two manly men. Trelane knelt in front of me and I went back to sucking his cock. I felt Tom's fingers in my ass, then I felt them being replaced with his big cock. I groaned really loud as Tom's big cockhead invaded my ass, but my groan was muffled because Trelane's cock was stuffed in as far as it would go. Thanks goodness that Tom took his time! He was talking to me and rubbing my back as his cock slipped inside me. After a while, I'm not sure how long, I felt Tom's skin touch my bare ass and I knew that he was all the way in. Tom's hands slipped back to my waist and he held on as he started pumping his big cock in and out of me, very slowly at first.
Trelane seemed to be very turned on by what was happening. His precum was flowing and his cock was throbbing, then he started to fuck my face like a real man. Long, smooth manly strokes, and I felt like I would just have to relax and enjoy the ride. Tom and Trelane seemed to find a common rhythem... their cocks seemed to slide out at the same time, and slide back in at the same time. They seemed to keep the same pace for a LONG time, until Trelane started moving faster and faster, his cock stretching my mouth and making sexy squishing sounds. I could feel the familiar shaking in Trelane's body and was rewarded with a hot mouthful of cum! I swallowed, and was rewarded with another mouthful, and another, and one more. Trelane sat back, spent, but still interested in watching. Tom seemed to be VERY turned on now, and his hips started smacking into my ass, faster and stronger... I could only gasp and grunt as my manly lover fucked me good! Suddenly, my ass seemed to stretch more and more and it was hurting a little again, then it stretched even more! Tom was shaking now, almost vibrating, and it felt like he was so deep inside me with every thrust. Then, I could feel my asshole spasm, and I was cumming and cumming and cumming... I was crying and groaning at the same time because it was just overwhelming! I grunted and my breath went out of me as Tom pulled me to him, his fat cockhead reaching deep inside me, then deeper, and I could feel it expand as his cum started to fill me... a nice warm glow deep in my ass.
It felt like Tom was going to collapse on top of me, but he kept his composure and massaged my prostate with his still hard cock. He kept up a nice stroking motion while his cock got softer, until it squished out of my ass. Trelane and Tom helped me up and we all went to the bathroom where we took turns in the shower. Trelane went first, then me, then Tom. I leaned against the bathroom counter and watched Tom dry his wonderful body. I went to him, knelt down in front of him, and started sucking his cock. I sucked and licked and sucked some more, enjoying every second of it. Tom's cock was hard again in no time... but his staying power was compromised this time! :-) In a very short time, I felt Tom shiver and start to groan. He gently held my head as it bobbed on his cock, then he groaned VERY loud as his cum filled my mouth. I gulped over and over again until it was all gone.
Tom lives about 150 miles away, but he says that he will visit me and Trelane every chance he gets. I somehow believe that he will! lol