I have been asked to tell more about my encounter with Wilson, so here goes. Again, this is a true story that happened in the late 1980s and all characters were over the age of 18 at the time of the encounter.
Let me start with a quick recap from my story “Meeting Wilson” He was a tall, lean Puerto Rican Man with a massive dick that was just under 13”. Our first encounter centered around me sucking his giant dick before he demonstrated his ability to suck his own cock. It was hot as fuck!
I wouldn’t say that we started dating, but Wilson and I got together as frequently as we could to relieve bottled up tension – me from schoolwork and him from the stress of military life.
I came to realize how difficult the folks who defended our country had it back in a day when it was illegal to be gay and serve. The logic never made any sense. Being a mechanic in the Air Force, Wilson had to be on the DL and stay as low as possible on the military’s radar. As a result, we would travel on some weekends to visit gay bars in Tallahassee, Florida which was a little over 2 hours from were we lived. It was a breath of fresh air for us both, but especially for Wilson, who got a little taste of freedom.
Up until this point we had limited our sexual contact to strictly oral, but we both wanted more. As I explained in the previous story, Wilson was paranoid (for good reason) about anything that would betray his gay tendencies to the military. He wanted to bottom but suspected that random military physicals could give him away.
On one outing, he seemed distant and distracted. I asked him what was wrong, and he reluctantly told me that he was being transferred overseas. He only had a few weeks before he would be going to Saudi Arabi. We were both bummed but enjoyed as much time together as we could under the circumstances.
Ultimately, I made a decision to show up at Wilson’s apartment a few days before his deployment. I am usually passive sexually, but that night I wasn’t going to be denied. I kissed Wilson deeply and started unbuttoning his shirt. He responded with a heavy sigh. I removed his shirt and pushed him down onto his sofa. He smiled and asked what I was doing. As I pulled his pants off, I told him that I was giving him a going away present.
I started sucking on his massive cock and he moaned appreciatively. “I am going to miss this” he confessed. I backed off his dick long enough to start removing my clothes. Once I was naked, I slid a condom and a bottle of lube from by pants pocket.
At first Wilson looked at bit stunned.
“What are you doing?” I had caught him off guard.
I started rolling the condom onto his engorged penis and told him “I am going to do something that I have wanted to do from the moment I met you. I want you to fuck me and I want us both to enjoy one last night together.”
I had expected more resistance, but Wilson helped me finish sliding the tight condom onto his cock. The condom only went about halfway down the massive length. It was a very snug fit. Wilson took the lube and squeezed a bit onto his palm and then slid it up and down the condom to get it good and lubricated. He then reached behind me and inserted a finger into my aching hole. It felt amazing and it made my already hard cock even harder. After a moment, he was pressing two fingers in and finally a third. I was in lustful heaven and pressed my ass back as far as I could to take as much of his digits as possible.
Satisfied that my hole was sufficiently lubed, I straddled Wilson and slowly lowered myself onto his massive cock. I wasn’t scared of its 12+” length nor its girth. I wanted it like I had never wanted anything else in my life. Still, I halfway expected there to be pain given the circumference of his dick, but I didn’t resist as his cockhead pushed past my sphincter.
It was total bliss. I have always enjoyed the act of penetration, and this was unlike anything I had experienced before. My heart was pounding, and I was enraptured. Wilson let me stay in control as I slowly lowered myself onto his shaft a little at a time. I slid up and down a few inches before having him apply more lube to the lower part of his cock.
Wilson surprised me by not only rubbing more KY onto his dick, but he worked a couple of fingers into my ass while his monster cock was still inside of me. I nearly came, but fortunately didn’t. I willed myself not to.
Wilson removed his fingers, and this allowed me to continue lowering myself onto his cock. I was suddenly feeling his thick, manly pubes pressing against my ass cheeks. Once I had him entirely inside of me, I took a moment to get used to the intense feeling. It was amazing. Never any pain, only pleasure.
I started to gyrate my ass onto his cock before lifting myself up and down. Wilson responded accordingly with sighs and heavy breathing. He grabbed me by the waste and started slowly pumping his horse cock into me. Eventually he picked up the pace and I would slam my ass down onto his pelvis as he rammed me with that gorgeous cock.
I rode him like that for a good 10 minutes before he flipped me onto my back without breaking stride, keeping the full length of his manhood inside of me. He leaned into me and kissed me deeply. We were both stating to sweat, and our moaning was getting louder. Wilson picked up the pace and started slamming his cock deep inside of me. I’m not sure who was enjoying it more.
Fortunately, we were both young and had plenty of stamina. Wilson fucked me hard for a solid half hour before gasped that he was going to cum. He started to pull out, but I grabbed his ass cheeks and pulled him closer and wrapped my legs around him.
“Are you sure.” He asked. I simply nodded.
After a few more thrusts of his hips, he threw his head back and moaned “I’m cumming!” and I could feel his already thick cock swelling and spasming as he shot his juice into the condom. This was enough to trigger my own orgasm and I shot several heavy ropes of cum onto my face, chest, and belly.
Wilson pulled out of my stretched ass hole and removed the condom. He tied a knot into the end and placed it in a glass that was on his coffee table. He collapsed on top of me, and we kissed a bit more, enjoying our body heat and the warmth of the semen that had rocketed out of my dick. This surprised me considering Wilson’s long-term paranoia, but in the end, he had trusted me enough to get lost in the moment.
Reluctantly I cleaned myself up and said one last goodbye. I knew that I would never see him again but was thankful that we both would have a fond memory. At least I would remember it.
A few years ago I tried to track Wilson down on social media. I did locate him, but he was married and still in the military. It was best not to reconnect, but I would love to sit on that giant dick again.
