Getting Topped for the First Ti[M]e by a Big Dick La[T]ina Girl

Family vacation v27.4, and I was alone once again in my bedroom. Another long day of watching bikini clad girls on the beach had come passed. This day our spot was particularly ripe for Instagram stories, and watching model-worthy girls make magic in real time was a little too much to bear.

I knocked back a few beers and, as a I sat on my bed, awaiting a reply from a Tinder match, I downloaded Grindr for the third or fourth time during that trip. I was right in that sweet spot of buzzed, horny, indignant, and verging on depression. Right where I had found myself so many times before. I had yet to admit to myself that I am not completely straight, and I justified my repeated forays into the virtual world of queer dating with my preference for femininity. *I* *was into women*, and transgender women are basically just girls with dicks. Bottoming was out of the question, but I would top one without thinking twice. Maybe even suck her off. That did not make me gay or bi.

Narrator: “His search history would suggest otherwise.”

As if sent from above the hookup gods above, there, within the first few profile panes, was a gorgeous trans woman. A tall, smirking brunette dressed in sparkling club wear. I sent a standard greeting. Staid yet enthusiastic. I did not want my salaciousness to show. These girls are sick of being lusted after. I did not expect her initial reply to come in photographic form. The dusky bedroom shot of her standing in a jean skirt, hand creeping tentatively under the waist band. Her grey blouse was scrunched over the top of her chest, leaving her retrousse C-cups pointed up and away from the pane. Her three-quarter profile masked a coy grin. It nearly sent me through the roof.

“You verse?” she asked, getting straight to the point.

Riding the wave of endorphins that followed, I hurried to the bathroom in my skin-tight, blue and yellow-striped Calvin’s, and I opened the door to a yet undiscovered room of my sexuality. I opened my iPhone camera and began to carefully attune its lens with my ass, posturing my hips as I did so. I had spent years ogling girl’s derrieres, but I had never looked critically upon my own. I was immediately aroused in trying to envision myself as a piece of ass, ripe for the taking. I finally got the lighting and the angle exactly right and sent my work expectantly to Lisa, as I shall call her, for the sake of this story.

“Do you want this?” I asked.

A second picture came in response. A POV shot of a massive, erect dick.

“Do you want *this?*” she asked.

“Location?” I replied quickly. In the chat window, a map pin appeared fifteen miles away. Below that, her number.

Despite a nervous tremble that worked through my body, I got dressed in record time, and snagged the keys to the family convertible. It was 11:30, and most of my family was in bed, but some of them would undoubtedly hear my departure.

“Fuck it,” I thought. I would come up with an excuse before I came back.

I drove the fifteen miles along a mostly dark and desolate two-lane highway. As I fiddled with the radio dial, my nervousness materialized in the tunnel vision of a Lynchian fever dream. I finally arrived at the designated spot, a quaint Arts and Crafts Style bungalow in the outskirts of an old fishing village. I texted Lisa, and she came to the driveway to greet me. I exited the vehicle and found myself in the embrace of a figure taller and broader than my own. She was dressed in the very same jean skirt and grey blouse of my previous fascination. She planted a wet kiss on my lips.

“So nice to meet you,” she said, as she motioned me inside.

We passed through a picket gate, through the darkened abode, and into her room, where we sat next to each other on her bed. We spent a few minutes exchanging pleasantries. She told me about her own trip to the area. She came to visit from L.A. with some friends. Apparently, they were still out on the town.

“Well, I’m humbled you sacrificed the rest of your night out for me,” I remarked.

She chortled, almost condescendingly as she gripped my leg with a powerful hand. I leaned in to kiss her, and she reached for the nape of my neck as she slid her tongue into my mouth. For a few minutes we made out vigorously before I found myself down on my knees. She pulled down her skirt, and, like a samurai drawing sword and striking in the same motion, she cupped her massive cock and balls with her right hand and lifted them to my mouth. I instinctively gripped her massive cock with my lips and slid up and down her shaft, lapping at it with my tongue as I moved. I worked all the way down to the base of her shaft, letting the head of her dick penetrate the back of my throat, until I nearly suffocated. I took a break to lift her cock with my hand and suck enthusiastically on her horse-sized testicles before returning the rod to my mouth. Rinse and repeat.

After another reprieve for some air, she looked down at me.

“Someone’s had a lot of practice,” she said defiantly.

“Uhhh, first time actually,” I said trying to hold back a laugh.

“No fucking way!” she said.

Apparently, sucking cock is the one thing in life you can get pretty good at through the pure power of imagination, and, despite previous denials of my sexuality, I had done a lot of imagining. I capitalized on the break in the action to remove my own clothes, and Lisa undressed herself the rest of the way. I pushed her onto the bed and laid on top of her as we started to make out again. I moved downwards to those sumptuous, organically grown C-cups and replicated my blowjob routine with her nipples. After a few minutes of enjoying myself, I asked her if we could 69. She nodded, and I turned over so that our bodies laid next to each other in opposite orientation. We laid on our sides as we concurrently engorged ourselves on meaty cock. Drool began dripping down the side of my face, and I could feel the same on the other end. Like a couple of heated rivals, we matched each other turn for turn until I could feel myself almost ready to explode. I removed her member from my mouth and turned towards her.

“I want to sit on your cock,” I said.

Likely sensing that this really was, in fact, my first time, she cautioned me about the size of her dick.

“Yeah, I think I noticed,” I said.

“Doggy or cowgirl would probably be easiest,” she said nonchalantly.

Lisa reached over to her nightstand, and she pulled out a condom and some Astro Glide. Without hesitation, she flipped me onto my back. After applying the condom to herself, she pushed my legs back until I clutched them around the underside of my knees. She then emptied a generous dollop of lube onto my sphincter and began working it in with her fingers. She penetrated my rectum with one finger before adding a second and distracting me with sensuous fellatio.

“You ready?” she asked after a few minutes.

I nodded, and she got onto her back. Facing her, I straddled her large frame, and, taking her cock into my hand, I guided myself into position. My eager anticipation immediately gave way to a flight response, as her tip entered my cavity. My slightly drunken, lovesick stupor was broken by an unmistakable pain in my rear.

“It’s okay if you can’t,” she said with the most gentleness she had displayed all night.

I thought to myself, “Hell, I came this far.”

It was undoubtedly awkward for a few minutes, as I tried nobly to ease myself onto her impressive spear of a penis. Eventually, with some forced conviction, I was able to slide down a few of what had to be nearly eight inches. No imagination here, just sheer willpower. Finally, things became a little less strenuous, and I started to preform my best interpretation of all the girls who had once ridden my own cock.

“Woah, woah, easy there cowboy,” she bridled.

I was admittedly not the most graceful in the saddle.

“You’re gonna kill me,” she said, laughing.

I apologized, and I began a slower and more methodical dressage on what was, at that point, only half of her dick. Feeling a little more in control, I reached for my own dick that had gone limp over the preceding struggle. I started feeling more invigorated, and my size grew in turn. My movements quickened, and my member, swelled. Then, without warning, I felt a sensation of my entire being collapsing inward. A veritable implosion of delight. With my mouth agape and my eyes bulging, I shot a resounding volley of cum against the headboard behind Lisa. The successive streams, becoming gradually less forceful, splashed onto her face, neck, and chest in turn.

“Holy fuck,” she said.

Yeah, holy fuck.

I dismounted and laid down next to her. I alternatively kissed her and licked drops of l warm ejaculate from her face. Overcoming her surprise, she kissed me back and started to bite my neck, as she began stroking her still engorged cock. In no time, she ponied up to me and answered my orgasm with a mess of her own, all over my torso.

A minute or two of silence and kissing followed before we went to the bathroom in turns to clean up and relieve ourselves. We laid down next to each other, her arm around me, and next thing I knew, she was asleep. Just like that. After all those one-night stands in my college years, after all those times I drunkenly bedded a girl, only to ignore her and find her gone in the morning, it was finally happening to me. Feeling tired myself, I cuddled up next to her right side, draped my arm around her, and placed my head on her warm chest. Stirring for a moment, she pulled me in closer with her left arm. My initial dismay was replaced with a curious sense of comfort, as I settled into her large figure.

I laid like that against her for several hours. Though I was tired, sore, and AWOL from the family cottage, I could not find sleep. My emotions were too mixed up, and, before long, my newfound creature comfort was replaced with another bout of horniness. Lying next to Lisa, I could not prevent myself from continually getting aroused. I studied her features: those high cheekbones, dark eyes, and pursing lips. I marveled at her ample bosom, her sumptuous thighs, and the piece between her legs, still imposing in its flaccid state. She seemed so comfortable, so at peace, that, despite, my yearning, I was scared to wake her.

A cycle of gratification, arousal, and trepidation played out for at least another hour, until I could not bear it anymore. I stroked her cock with my hand, watching it come back to life, and I pecked gingerly at the side of her face and neck. She slowly came to and grinned with her eyes still halfway shut.

“Round two?” she asked.

Before I could answer, she was pinning my chest with her enormous weight and humbling me with her package. It was approaching 4:00 AM, no time to mess around, so she sent her humongous shaft straight down my throat. Despite my best efforts, she found my gag reflex and apologized for being so rough. I indicated that that is exactly what I wanted, so for several minutes on end, she proceeded to use my throat like a Fleshlight.

After a sufficient throat fucking, she pulled out the condoms and lube again, and, deciding that she would take matters into her own hands this time, she mounted me in the missionary position. At her mercy, I braced myself against her body, as she struggled to fit herself into my still tight hole and I struggled with the pain. After a minute of false starts, a concerted push sent the entirety of her member into my body. With her finally deep inside of me, I felt the relief of having summited a figurative mountain, and I took comfort once again in her imposing figure. I sensed all her weight, as she thrust into me with lascivious passion, and her enormity felt like a big therapeutic blanket draped over my entire being.

As Lisa made her way with me, I could feel my head getting lighter and lighter. Eventually she dismounted and flipped me onto all fours, facing away from her. She entered me from the back and sent me into a state of unmitigated bliss with her ceaseless pounding. The fleeting feeling in my head gave way to a pulsing in my midsection. I arched my back in a battle wit the newfound sensation, until, in a moment of clarity, I released what was left in my tank. As she thrust into me, spurts of cum rained in a zigzag pattern across her bedsheets.

“You little fucking slut!” she exclaimed, as she smacked me on one cheek.

Her verbal diatribe continued along with repeated rakes across the ass I had so eagerly and innocently offered her in the beginning of the night. Her strokes increased in ferocity, as the bedsprings croaked under the onslaught. Then, she pulled out. I stared ahead expectantly for several seconds before I felt a shower of warm liquid drench my backside, which began to slowly trickle into my crack. I put my face down into the mattress and let her revel in satisfaction as she tugged the last remaining drops out of the hose pointed at my rear. When I sensed she was done, I turned to face Lisa. Facing each other on our knees, on the mattress, we embraced again and kissed passionately. Lisa got up, scrounged up a towel and helped to clean me off. Feeling the urgency of the oncoming morning, I gathered up my clothes.

“I have to go,” I said. “But, let’s do this again.”

“I would love that,” she replied.

We dressed together, I in my street clothes, and her in a silk robe that left little to the imagination. I knew I had to leave before I started getting turned on again, so, in reverse order of operation, she walked me back through the bungalow, out through the gate, and to the convertible. We embraced and kissed once more.

“Text me,” she said.

“You can count on it,” I said as I entered the vehicle.

I drove away, into the encroaching light of day, with perhaps a few hours to catch some sleep and to think of an excuse that would satisfy everyone waiting back at the cottage.

Source: reddit.com/r/gonewildstories/comments/k5kr18/getting_topped_for_the_first_time_by_a_big_dick