Losing my [F22] Virginity to a [M] stranger in Jamaica

Like many of you, I too am bored during lockdown and looking for something fun to do. After enjoying your stories from afar, I decided to share one of my own :).

At 22 I had just finished grad school, landed a full time job, and bought my first car. I grew up in a strict religious household and hadn’t dated, let alone done anything remotely sexual. I had spent so much time focused on my academic achievements that I’d missed out on a lot of social experiences. I was proud of my accomplishments, but was sexually repressed af and dying to explore. I started exploring my sexuality using Tumblr (lol!) and got comfortable with masturbating.

My best friend (who’s upbringing was similar to mine) and I decided it was time to see the world, and we booked an all inclusive vacation to Jamaica – our first time in another country.

Pretty much immediately after arriving, I realized I was a hit amongst the male staff members. I’m about 5 foot 6, light brown skin (think Rihanna’s complexion), with thick curly hair down to my mid back. I was pretty curvy back then as well, I had gained the freshman 15 and hadn’t dropped it yet.

I have a few stories I could share from this trip, but the one you’re here for is how I lost my virginity.

One of the staff members/entertainers was pretty aggressively eyeing me for the first few days of the trip. Let’s call him Tristan. Tristan made a point of chatting with me and my friend often, and often pulled me to dance during the interactive activities. He made it clear he was interested in more – rubbing his crotch on my thigh, grabbing my ass when people weren’t watching, that kind of thing.

So one night, my friend and I get pretty drunk, and at the end of the night Tristan asks me to come walk with him around the resort. I drop my friend off at our room and help her into bed, and then I go for a walk with Tristan. We end up in the secluded staff parking area, and start making out. (I want to add a very non sexy disclaimer that I’m aware this was super unsafe, and that looking back it’s clear that he knew what he was doing. He knew just how to avoid the other staff and we walked along a secluded path. I’m not condoning unsafe behaviour – especially while drunk in a foreign country!)

Tristan sits me on the hood of his car and pulls my shirt and bra down so he can suck on my nipples. I’m only a 34C, but men dont seem to mind. I haden’t made out with anyone like this … ever. The thrill had me soaking through my panties. The combination of alcohol and my inner slut gave me the courage to just go for it. I put my hand on his dick.

Now I had never seen a dick in real life, let alone touched one. Who told me to grab the massive dick of a 30-something year old Black man?? I was in way over my head.

Anyways, I played it cool, and stroked him awkwardly through his pants. Tristan suggested we move into his car. He flips the back of the passenger seat back so I can lie comfortably, and he helps me in. He slips in on top of me and shuts the door. I hike my skirt up so I can open my legs, and show him my soaked panties. Tristan immediately pulls them to the side and slooooowly pushes one finger inside me. I’ve never had anyone else touch my pussy, my head is spinning. He starts thrusting his finger in and out, and then slips the second one inside me. I’m moaning pretty loudly at this point, focused on myself and forgetting that I should probably be paying attention to his dick.

Tristan took a break from fingering me to pull off his shorts and boxers. He moved to rub his dick against my pussy … and for the only time that night I make a smart decision to ask him to put a condom on.

After he gets a condom on, he starts rubbing his dick on my clit and at the entrance to my pussy. I reach back and play with his balls and pray to every imaginable god that I don’t embarrass myself. He lines his dick up so it sits perfectly at the entrance to my pussy, and starts to push. And I start to moan, because it fucking hurts like hell. But again, being drunk and incredibly horny is a lethal combo, so I try to play it off. Except he’s now confused about why he can barely get the head of his dick into me.

At this point, the months of porn watching kicked in. I wrapped my hand around his dick, and started stroking while his head was still inside me. I started rubbing my clit with the other hand. “You like my tight little pussy, dont you? I’ve never had a big dick like yours, you’re so fucking thick. You’re stretching me out with that thick head. I want you to fuck me so badly.”

The encouragement worked. He pulled out and pushed back into me again, getting a little deeper this time. He continued to pull out of my pussy and then push back in, eventually managing to fit about half of his dick inside me. It still hurt, but I was soaking wet with the thrill, and he was clearly enjoying how tight my pussy was. I think he gave up trying to get any deeper inside me. I didn’t have the energy to keep up the dirty talk, and just moaned and rubbed my clit as he continued to fuck me.

After a while I felt him stiffen, and he grabbed my face so I was looking straight in his eyes. With a groan, he came inside me, and stayed there until he had emptied his load.

At that point the thrill wore off, and I felt like I had pushed my limit for the night. We cleaned up, threw the (very full) condom out, and he walked me back to my room. I showered, crawled into bed, and dealt with the not-so-glamorous side effects of losing your virginity in the morning. I told no one, until a few years later when I much more sexually experienced, and shared the story with pride.

And that’s all folks. The story of how I lost my virginity to a stranger in another country at 22.

Source: reddit.com/r/gonewildstories/comments/ifi1dz/losing_my_f22_virginity_to_a_m_stranger_in_jamaica