[T]rans Girl swiping right on a Straight Guy [TM]

I was home on college break and swiping tinder, which can be pretty hard for a queer person in a small suburb. I matched with Rob and finally started talking about hooking up and I ask how he feels about hooking up with a trans girl. He seems super into it, and says he can’t wait to have me over, and that’s all the encouragement I needed to get dressed, prep my ass, and drive over to his place about 20 mins away. 

For the record, I’m like 5’4, slim with bubble butt and a cup tits, with bobbed dyed red hair. At this point, I still had my cock. 

I text him that I’m here and he opens the door. He looks just like his picture, tall (like 6’ish), tan, and short cropped black hair and a stubbly beard. He guides me down to his furnished basement and offers me a drink. I take one and we go to sit on his couch. I think we both wanted a little time to talk and get to know each other (and let the booze kick in a little) so we started playing some Super Smash Bros. 

We shit-talked each other in the game and kept moving closer together on the couch until I finally decided to go hard and end the match as fast I could. I beat him pretty quickly and turned my head to tease him, but I just found him looking me up and down before making eye contact with me. He started leaning in and met him halfway, moaning a little into his mouth as I melted into him. 

We both turned on the couch to face each other as he grabbed the back of my head and slipped his tongue into my mouth. My hands started on his chest but quickly made their way under his shirt to feel his bare skin. He broke the kiss to lift his shirt over his head and exposed his tight, lean body. We repeated the process with my top, and showed off my lacy purple bra. He reached around my back and unhooked my bra, kissing down my neck to get to my sensitive  nipples. 

He sucked, flicked, and rimmed my nipples, the waves of pleasure flowing down to the bottom of my stomach. My fingers clutched at the short crop of hair on his head while his hands started playing with the button on my jeans. I lifted up my ass to help him slide off my pants, and was left in my panties, a little bulged from my half tucked erection. I took advantage of the situation and before Rob could sit back down again guided his hips near my face, perfect dick height while sitting down. 

I could now see his cock just straining to escape those basketball shorts, so I pulled down the waistband and was almost smacked in the face by the biggest, thickest cock I’d ever seen in person. He had mentioned that he had a thick cock, and I had brushed it off, but I was truly blown away.  

I grabbed it and it felt hot and weighty in my hands, and Rob sat back down on the couch.  I followed his cock down with him and licked up and down his extensive shaft. I make sure to work my tongue over his uncut head and taste his precum that’s leaking everywhere. I attempt to take his cock into my mouth,  but don’t get much farther than his head with his girth. 

I feel his hands grabbing my hair and pushing me down into his dick,  and I keep sucking on his head while stroking his cock. After a few minutes, he puts a hand under my chin and guides me back up to his face to make out.b I’m sure he can taste his cock on my tongue.  

He breaks the kiss and starts lightly pushing me onto my back. “Let me take care of you now” He said, kissing down my stomach and pulling my panties to the side and pulling out my cock. I have a fairly above average peen, but compared to Rob’s it was nice to feel dainty. I’m not nearly as thick, so Rob had no trouble taking my whole cock into his mouth.  

Men really do give the best blow jobs, and Rob was no exception.  God he worked his tongue so well he practically made out with my cock,  bobbing on it, making me moan with pleasure. I grabbed into his hair and went along for the ride. Rob took a break from my cock and started focusing on my ass. 

Still stroking me, I felt a wet finger enter my ass, deep enough for ‘come hither’ motion to perfectly hit my g-spot. 

“Ahh fuck, that’s so good, don’t stop” i moaned, pushing my ass back onto his fingers.  “You can do more fingers, to warm me up for that huge dick of yours”

Rob complied and worked in another digit, then 2. I reached into my hookup bag and squirted some lube onto his fingers to keep everything slick, and after a few minutes I knew I had to be ready to take that cock.  I’m not a size queen, but that’s not an opportunity I wanted to pass up! 

We sat up and he handed me a magnum (of course)  that I rolled into his dick, making sure to use a copious amount of lube. I straddled him and guided his cock to my ass, slowly putting more pressure onto my hole until the entire head popped in at once, making me freeze with pain.  I held onto his shoulders for balance while he propped me up by my ass.  

Once the pain subsided, the process repeated for every inch of that monster, moaning as was slowly completely impaled. After I was (mostly)  adjusted, I started to ride him, slowly grinding against his abs, my hands in his chest and his hands gripping my hips, guiding me back down on his cock. 

He gave my ass a smack and started to fuck me back, making my ass quake and my tits bounce.  I couldn’t hold back my moans and my legs were starting to shake from the repeated long strokes to my p-spot. My hands dug into his chest to keep up. Rob could see me getting weaker in the legs and pushed me onto the couch and flipped me over on the arm, ass up, my semi-hard dick hanging under me. 

Rob grabbed my hips from behind and lined up to my hole, and with extra lube it went in a lot easier this time. With the couch arm pushing my stomach in, I felt even more full than while riding him.  Rob grabbed a handful of my hair and wrapped it around his hand, pulling my head back and arching my back up towards him. It felt so good being fucked so hard, and my long femme hair making me subservient to him sent those extra shivers down my stomach. 

“Oooooh, yeah keep fucking me, just like that, I’m gonna cum!”

I couldn’t hold back anymore and after a few more strokes against my prostate I started riding the waves of pleasure coming from my ass. My ass tightened up around Rob’s cock, and I heard him groan, “ah fuck, you feel so good, I’m gonna cum” his strokes got hard and faster until his hips sputtered and I could feel his cock twitch deep inside me, filling me up with his hot jizz.

Rob leaned over me and pulled my hair to make out with me before his softening cock slipped out of my ass. 

We cuddled on the couch a little bit before round 2, and hooked up again a few months later :)

Source: reddit.com/r/gonewildstories/comments/g5hbon/trans_girl_swiping_right_on_a_straight_guy_tm