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(Author's note: This is another true story from the P. O. V. of a young transguy. If you're not into age gaps, trans guys, or eventually some furry stuff, find another story to read. You've been warned. Otherwise, enjoy! I sure did when it was happening...)
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January 14th:
I pulled up to a garage on the opposite side of town. I didn't think I would actually follow through with this hook up out of nervousness but my hormones got the best of me and I found myself face to face with a perfect stranger. He had a good couple inches on me and shook my hand with nice strong grip. I tried to keep my eyes away from the crotch of his grey sweatpants even though we both knew why I was there. Instead, my eyes focused on his face, which was decorated with a grey mustache. Normally I'm not into facial hair, but it looked like it belonged there and he was too hot for me to complain about something so simple.
I mentally scolded myself for getting into such a situation.
He could murder me, ditch my car somewhere, and chop me up into little pieces and no one would ever know where to look...
But there I was. My mouth became dry, and I tried to suppress my shivering. I stuffed my shaky hands into my jacket pockets like I was cold. Well, I was cold, but I was also nervous despite being horny as hell. Ever been so nervous that you shake? Well, that's how bad it was. So... Why had I gone to some stranger's house without telling anyone where I was going or what for? Because another thing that makes me shake is being insanely horny. Ever been so horny that you shake? I have. And I was. Stupid. But we're all stupid when we're young. Today I was too horny to not be found in the arms of the man that I had been trading very naughty messages with. So I found myself face to face, and soon lip to lip, with the stranger.
It was hardly past 7AM, and I was already melting into the warmth of his hug. He was in no hurry, caressing my shoulders, chest, back, waist, pawing at my ass cheeks... I felt his hard on through his sweatpants pressing against the front of my pants and couldn't resist grabbing it. I was so stiff and awkward compared to his confident smooth strokes. I could tell he was big, and as our clothes came off I was greeted by a gloriously shaped 7 inches. He was shaved too! I would have drooled if my mouth wasn't so damn dry. I've seen and sucked a couple different ones, but his cock was shaped just like the ones I would fanboy over in porn videos. Thick, big head, subtly veiny... It looked so much yummier in person than in the picture he sent before I came over! I dropped to my knees and parted my lips for this treat. My mouth was so dry I felt like I probably wasn't even doing a good job, but he was patient with me and encouraged me with a hand on the back of my head. After a minute or two I felt his hands hook under my armpits and lift. The sensation of being pulled up like a parent would a little kid... Oh, it fucked me up in the best way! He stood me up and then pushed me gently to sit on the edge of his bed.
I hadn't expected to be on the receiving end of oral, but his mouth went to work and made me breathe even harder than I already was. If my mouth got any dryer I'd choke! Eventually I ended up on my back. I think my pupils must have dilated to three times their normal size when I watched him climb onto me. He rubbed the tip of his cock up and down my slit, pushing gently into my pussy. The pressure of him trying to get into me had me crazy turned on. He pushed a little harder and I felt the tip pop in fully. I hissed out a breath of satisfaction. He wasted no time in sliding in further, making me moan softly. My legs were spread wide to give him plenty of space to work, but he grabbed my ankles and shoved my legs up high, letting them rest on his shoulders as he picked up speed. His cock was now really hitting deep inside my pussy. As soon as he put my legs up like that I could feel he was hitting my cervix with every thrust.
By now any hint of nerves had left me and were replaced by a hot burning lust in the pit of my stomach. I was getting fucked by some hottie I had found over the internet. Before now I had only written stories about something like this, a young trans guy getting it on with an older man. Now that it was happening I almost couldn't believe it, despite my legs being up by my ears and my pussy getting so perfectly filled up. All seven inches and the flared tip... Mmmph, there's a reason people mention their love for thick tips, and my pussy was telling me exactly what that reason was! In my head I could perfectly picture a sine wave made of flesh. Amplitude and frequency corresponding to diameter of being stretched and speed of thrusting respectively.
Every few thrusts were punctuated by a sloppy kiss. I wasn't in danger of choking to death with my dry throat and mouth anymore. His spit was minty, and even the air from his fucking lungs smelled so damn good! Earlier, I had my reservations about kissing, but every kiss from him tasted amazing and now not only did I enjoy it, I think a good fuck session (which we'd have plenty more of) would be incomplete without it!
In a few minutes he pulled out and spurted his load onto my tummy. I realized I hadn't said a word, despite telling him how into dirty talk I was. I was just in awe of how hot he was and how good he made me feel.
"I'd be embarrassed if I wasn't so turned on." He chuckled as he got up off me.
Him? Embarrassed? I couldn't help but smile. I felt like I was the one who should be embarrassed. As soon as he touched me I felt like any former knowledge of how sex was supposed to go vanished. I was nearly paralyzed, simply admiring everything I felt, saw, smelled, tasted...
I guess he came quicker than he meant to, but I wasn't going to complain. I'd finally gotten my fantasy fulfilled and I was still in the clouds.
There didn't seem to be any awkward moments after we were done. Still naked as the day we were born, we sat side by side on the edge of his bed and chatted about our lives just as casually as if we had been fully clothed and sipping coffee in a cafe. The room was a little cold but I felt warm. My nerves were gone. Normally I would have felt the urge to put my clothes back on as soon as it was over. So why didn't I feel it now? As I listened to his anecdotes, he quickly started to become a real person to me, not just some guy I used to satisfy my need for cock. Something told me this wasn't going to be just a one time hookup. I was right, but I wouldn't see him again for a month.
Valentine's Day:
Numerous circumstances in my personal life prevented us from getting together again for a month. I wasn't sure if he was truly interested. My cynical nature refuses to let me believe in good things until I'm overwhelmed with proof. We worked ourselves up over text that morning again and when he finally came over for "lunch", things played out similarly to our first meeting. As we gave ourselves over to pleasure on my bed and my legs were up all the way by my ears again, I could feel my new friend's cock beginning to pulse a little. I knew what that meant and it made my stomach fill with butterflies. Then he asked me something that took me by surprise, and my answer surprised me even more.
"Can I cum in you?" He asked. I tried to be smart, but the pulsing I felt told me he was so close already.
"Fuck it, yes." I panted.
No sooner had I finished speaking than he let out a loud moan and the throbbing of his cock became even more intense. The rush multiplied and moved from my stomach to my head and inside my pussy. Fuck! Had I really just let him cum inside my pussy?! What the hell was I thinking? Well, I was thinking with my pussy, not my brain. After we were done he had to hurry back to work.
Then he disappeared.
March 29th:
A few weeks had gone by. I sent him a couple messages, maybe one every other week since I last saw him. No response. This was either a classic ghosting, or maybe he was dead. After all, he was nearing the same age as my grandpa, who passed on only a few months earlier. I had almost given up on ever seeing him again, but for some reason that morning my gut was telling me I should reach out one last time before giving up. Well, maybe it was something other than my gut...
As I stood under the hot water in my shower and quickly typed out the most honest message I could to try and provoke an answer. Any answer at all! Even if he would have said "Fuck you! Take a hint!", it would have satisfied my curiosity. What I got instead made my heart skip a beat. He explained some things, and at the end of the message, there it was.
"... I know I can't resist you."
He invited me to go out on a trail ride with him that afternoon. It was a beautiful day. Perfect for a fun time off-roading. As soon as I saw him again, the lustful feelings hit me just like we hit the trails- fast and hard. We took our first little break behind a small ridge line. He popped a beer and we chatted about conspiracy theories and bigfoot. I was standing by the open door of the side-by-side in a sort of bent over position rummaging in my backpack for a snack. I felt him appear behind me. Goosebumps immediately started raising up along my skin all over. Then when his hand touched my back I thought I might just explode. The tingles from just his hand told me how desperate I was for more. I was still in "public awareness mode", so I didn't reciprocate by touching him back. That would quickly change within a few more stops.
As we took our third and final break on the top of a hill sipping our drinks, I leaned my back against the back of the side-by-side. We were chatting again, about what I don't remember. But I remember clear as day what happened next. I had no polite escape route unless I wanted to seem prudish, and he took advantage of it. He positioned himself right in front of me, capturing me by hooking his fingers into the pockets of my pants. My heart was pounding and blood rushed in my ears. We were nose to nose for a moment and my mind was screaming, "You hear that motor in the distance! Do you really want to be seen like this?"
Then he pushed his hips against mine and I felt his hard-on. I went "deaf" and leaned in to meet his lips. Suddenly the world vanished. I wasn't on top of a hill with a 360 degree view of the whole town below us. I was somewhere else. I was in la la land as I nursed at his mouth. I still couldn't believe that even something as simple as kissing could turn me on this much.
Fuck! My pussy was screaming for attention and I had to use every ounce of strength not to just yank my pants down right there and beg him to fuck me senseless. I don't know how long we were sucking each other's faces off but I finally came out of my lustful trance when he had to pull away. Suddenly the world was so loud and bright. I came back to reality. Someone on a dirt bike was close and approaching our spot quickly. He let go and quickly put an appropriate distance between us. We eyed each other and laughed quietly.
We high tailed it back to his place and the ride was over. I hopped out, giddy and dizzy still thinking about us kissing on the hilltop.
We hung out for a while and I honestly didn't expect anything else to happen. Then he pulled him into his room and began kissing me again. He told me to bend over his bed and my heart nearly leaped out of my chest. I immediately followed his commands with anticipation buzzing through my body. My pants were around my knees and he planted his legs on either side of mine, trapping my knees together even more. He leaned over me and shoved his cock into my pussy. Aaah! Ffffuck... so... big! All sorts of naughty words flew through my head but again, I couldn't really speak. With my legs pressed together like this, his cock felt huge but didn't hurt, so every thrust made my legs weak. I wanted so badly to cum but I didn't want to sacrifice even one moment of his perfectly timed thrusting. The toes of my boots scraped helplessly at the floor, just one of my many signs of desire and enjoyment.
His fingers laced firmly with mine from the top, his palms warming the backs of my hands. We were both breathing heavily. Slap, slap, slap. His balls slapped against the inner back of my thighs. I meditated on the sound and focused on the feelings inside my pussy whenever I'd hear the slap.
I heard a far away voice speak.
I opened my eyes briefly and remembered who was giving me such good feelings in my body. Oh, that's what he said.
"I'm going to cum inside you."
Fuck me! Again I was faced with a choice. Tell him no? Beg him for it? I just kept my mouth shut. His moans of release pleased my ears. The spasming of his bare cock held balls deep alerted me to the flood of liquid heat about to be unleashed. As he pumped his cum into me and moaned, I closed my eyes again and savored the sensations.
We pulled our pants up and meandered towards my car as if we were ready to part ways. We weren't, and ended up chatting by my car. I felt his cum dripping out and soaking my underwear. Holy fuck was I turned on again already. I imagined him using my sloppy cum filled pussy right there in the yard. I may have zoned out a bit while he was talking and couldn't focus because of how horny I still was. I tried not to make it obvious that I was squirming and spreading his cum around between my pussy lips. As I tried to focus on our conversation, I kept admiring the sun as it crept closer towards the horizon.
Yes, it really was a beautiful day.
We'd be seeing each other a lot more in the coming weeks.
(To be continued...)
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