[MT] My first time with a transwoman

As a disclaimer, I know it can be a touchy subject so if I say something wrong or don’t properly respect what it means to be trans, I’m sorry but I’m still new to this. I’m going to try my best to be respectful but if I fail in that, please don’t go apeshit on me.

After Emily and I broke up, I was kind of a mess for a couple months. I was 31 years old and I realized I wasn’t getting any younger. I wasn’t 20-something anymore and my body reflected that. I felt disgusted with myself and my life. Practically every day on my Facebook feed I saw all my friends out living life. One friend was backpacking across Europe, another one was surfing in Hawaii while someone else was posting pictures of their visit to Turks & Caicos. Many others were celebrating anniversaries, marriages, or the birth of a child. The whole time I was living in my parent’s house with no one to share my life with. I had a job making good money but it still only paid my bills while leaving me with a couple hundred dollars a month for everything else.

I started to fall into depression. I would wake up, go to work, come home, and go to sleep. That was about it. Mom noticed and suggested that I talk to my aunt about staying in the beach house she rents out to people during beach season. I wasn’t going to but I caved just to get mom off my back. My aunt said she was fine with it because it was still another couple weeks before the season would start. I took the next week off work, packed a bag, and headed to the beach.

The first night I was still shaking off my routine and so I fell asleep on the couch watching a movie. I woke up and couldn’t get back to sleep but since the house was right on the beach, I figured I might as well watch the sunrise over the Atlantic. I sat there watching the sunrise when this gorgeous woman comes jogging towards me.

She’s looks like a goddess. She seems like she’s some mix between Asian and Hispanic. Her jet black hair is tied up in a ponytail. She’s wearing a white sports bra and some tiny black yoga shorts. Her honey colored skin has a thin sheen of sweat on it. She seems to sparkle in the light of the rising sun. She’s looks to be maybe 5’ 6″ or 5’ 7″, with legs that seem to go on forever, and what looks like an amazingly tight runner’s body.

She asks me if I have any water and says that she forgot to pack her water bottle. I only have a water bottle I’ve been sipping on since I woke up but that’s good enough for her so I toss it to her. She downs it in one go and thanks me before turning around to leave. She takes a few steps before she quickly turns around and pulls her sports bra up, putting her glorious tits on full display. They’re pretty much perfect for her frame. They’re gorgeously round and full, seem to completely defy gravity, and are topped with beautiful brown nipples about the size of a silver dollar. She gives them a shake and I stare at them as they wobble back and forth ever so slightly. She tells me to consider it payment for the water before fixing her bra, stuffing her breasts back in their prison, and resuming her morning run. Over her shoulder she yells that they’re fake and I stutter back something appropriately stupid and she laughs as she runs.

I think about her as the day goes on, disappointed that I probably won’t ever see her again. As I sit on the deck stargazing that night, I see a familiar figure emerge from the darkness and into the light provided by the deck’s fire pit. She has a bag with her, out of which she pulls a bottle of Jameson along with two shot glasses. She says she didn’t want to drink alone tonight and figured that she’d come by to see if I’d drink with her. We start drinking and talking about all manner of things. As the night wears on, and the alcohol starts to take effect, the conversation turns sexual.

During a lull in the conversation, she hops up from her seat and declares that she wants to dance under the stars. She starts up some music on her phone and starts dancing. I’m not a good dancer so I just sit awkwardly while she dances alone. Eventually she lets out an exasperated sigh and pulls me up out of my chair. It’s readily apparent what her ulterior motives are because she’s quickly grinding her ass against my crotch and pressing her glorious body up against me at every opportunity.

I start running my hands over her sinfully tight body. She’s only wearing a top from a string bikini and a tiny pair of cutoff denim shorts. I untie her top and let it fall off her, exposing her perfect tits to the cool night air. I play with her nipples and she just starts to purr. She moans some stuff in Spanish that I don’t understand but it makes it even hotter. Eventually I unbutton her shorts and help her out of those as well as her tiny panties. Once she’s out of them, I reach my hand down to her crotch to find a tiny cock instead of a soft pussy. I kind of freeze when I realize it. All the years of being told that transpeople are unnatural or disgusting or mentally sick are thrown into a pitched conflict with my primal desire to simply fuck. What she purrs in my ear is one of the sexiest things I think I’ll ever hear.

She grinds her ass into my crotch and my rock hard cock is settled right in between her ass cheeks. My hand is wrapped around her cock when I feel her breath on my ear, “Is everything okay, *papi*?” Her accent combined with the lust dripping off her voice turns me on immensely. I get a whiff of her perfume and feel her curvaceous ass cradling my turgid cock. In that moment, I realize that she’s just as much of a woman as Emily is and I nod.

At this point she steps away from me and walks to the edge of the light provided by the fire pit. She stalks around that border between the two realms of light and dark and begins to circle back to me, taking the long way around. As she does so, the flames cause shadows to flicker and writhe over her body. It instantly makes her seem curiously mysterious, wildly exotic, and incredibly dangerous. She takes very pointed steps as she walks. With each step, the corresponding hip is thrust out and a tiny shockwave rolls through her flesh which causes her tits to jiggle ever so slightly. She gets to the opposite side of the fire pit before she breaks the silence between us. She speaks slowly as she moves between two completely disparate dimensions.

“I’m completely naked. You’ve learned my most closely guarded secret. You’ve touched the most forbidden part of me. Despite all of that, you’re still fully clothed… ” The lust that continues to drip off of her sensual voice is intoxicating. I jump when she speaks again because she’s now behind me and speaking directly into my ear once more. The low whisper comes out a little husky, and oozes with sexual energy. “Does that seem fair to you?”

I pull my shirt off and step out of my shorts and boxers. Now that I’m as naked as her, she struts around me and kneels facing me. She wraps her delicate, tiny hand around my cock and slowly strokes it. Before long she has both her hands on me, one on the base of my shaft and one on my balls, with me deep in her mouth. She clearly has no gag reflex and she’s definitely taking advantage of it. All of the sensations just blend into one massive sensory overload. To all you women who genuinely love sucking cock, who constantly strive to be the best cocksucker you can be, and freely share your talent with the rest of the world, you da real MVP. This woman is the best I’ve ever had and it’s not even anywhere near close.

It’s not long before I’m about to explode and when I tell her she forces as much of my cock in her mouth as she can and begins swallowing. The sensation is so intense and it feels like she’s trying to rip every last ounce of cum out of me. I fire rope after rope of cum down her throat. My orgasm obliterates all conscious thought as it tears through me. When it subsides, my legs turn to jelly, my knees buckle, and I fall to my knees in front of her.

She pulls me close to her, resting my head on her wonderfully soft flesh pillows, and purrs in my ear. “Mmmmm… Thank you, papi. Your cum was delicious.” She runs her fingers through my hair as I sit there panting like an exhausted beast.

This is long enough so I’ll end it here. However, if there’s enough interest, I’ll write about the remainder of our evening, about us fucking as the sun rose on the following morning, and about the visit I received from the cops later on that day.

Source: reddit.com/r/gonewildstories/comments/8zxq39/mt_my_first_time_with_a_transwoman