(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.