[MF] Taking her virginity / holiday fling

(If you want to skip the intro go to the …..)

When I was 21 I went on my first proper lads holiday with 7 other friends to a party island. We stayed in a hotel full of similar aged groups all with the same intention of getting blackout drunk every night. It was one of those hotels with holiday Reps, and as none of us had been here before we decided to go out with them for the first few nights.

So we leave the hotel on our first night with about 25-30 other people from our hotel and the Reps lead us to the first bar. As soon as we get the first lot of drinks in the Reps start to pull people to the middle of the bar to play a game, which I didn’t know was going to be happening lol. Both me and my friend were picked and despite our efforts to get out of it we were being pushed in by the rest of our friends. The game was to pass ice cubes along a line of people, but by only using your mouth (it’s been done on some tv shows apparently). Grim for anyone involved but clearly funny to watch.

They lined us up in two teams of 5 in an order of girl-boy-girl-boy-girl. I was trying not to look at the girls either side of me in fear of it being immensely awkward but I noticed the girl to my right was quite attractive. She was blonde, about 5’10, slim figure but with a great ass. Then the game starts and she passes me an ice cube using her lips which I have to bend down for a little as I’m 6’2, and I pass it to the girl on my right who luckily is much shorter than me which made it easier. After almost 5 minutes of this our team eventually won, and the bar cheers knowing the other team now had to do a forfeit. Our team sort of awkwardly said bye to each other and went back to our own friend groups.

Later on in the night the Reps took us to a club doing 2 for 1 drinks for the next hour, so people queued up and got their rounds in. I was waiting away from to bar for my friends to be served when I felt a tap on my shoulder. I turned to see a girl who says to me, “My mate thinks you’re hot you know”, and points over to the blonde from the game earlier. She was stood looking a little shy with two other friends either side of her. “Do you think she’s pretty?” She asks me. I replied saying I thought she was very pretty and that I had noticed her earlier. Her friend grins excitedly at my response and runs back to tell her.

The four girls huddled round and began to talk, occasionally giggling or looking over at me. Then the blonde girl turns and starts to walk over, with her friends cheering her on. She laughed nervously as she got closer so I greeted her with a hug hoping it would help. Considering I first met, and essentially kissed, her a few hours ago I thought I better ask her name (We’ll say Lucy). She was wearing shorts that hugged her big ass and a crop top which showed off her great figure, as well as two nipple piercings poking through it. I also counted at least 3 tattoos on her too. We talk for a minute and we notice her friends are still watching us, so I place my hand on the side of her face, point her lips up towards mine and kiss her. Her friends cheer and laugh as she smiles and looks shyly at the ground, and some of my friends were also now watching this too and joined in the cheering. The rest of the night involved more drinking, a bit of dancing and a lot of kissing before we left the club before any of our friends did.

…..

As Lucy and I stumbled back to our hotel she began to ramble on about different things, clearly feeling less shy now. That was until we got back to the hotel and blurted out that she was 18 and still a virgin. In embarrassment she rambled on even more, at some point saying she’d only ever given one blowjob. She said something about knowing that I was expecting to have sex with her because we left together, so I reassured her by saying we didn’t have to do anything at all if she didn’t want to. This did calm her down, surprisingly enough that she still asked me to come back to her room. As we walked in I went to use the toilet and I stood there thinking to myself that the night was done and I’d just go back to my room soon.

However, I opened the bathroom door to see Lucy stood at the foot of her bed with her back to me, with nothing but her tight shorts on. She turns around and shows me her small but perky tits and says, “I want you to fuck me”. My jaw dropped, did I just hear her right? “Wait slow down, are you sure?”, I asked as I tentatively took a few steps towards her. She looked me up and down and replied by taking her shorts off, “Yes, I’m sure”. I was still unsure at this point but she started to kiss me and I couldn’t help but trace my fingers over her tits as I had never been with anyone with nipple piercings. Then she started to undress me, taking my top off and trying to undo my belt which I helped her with. I could see now that she was completely shaved, she must have come on holiday knowing she wanted to lose her virginity, or at least that she might do.

She got on the bed and laid back so I went to lick her pussy but she stopped me, saying she didn’t want me to, so I rubbed her clit instead. I went to slide my finger inside her and it was easy to start with but I could tell she was tight. “Put your dick in”, she says, but I warn her she’s not warmed up enough. She starts pulling my underwear off anyway and she sees how hard I am. I get in missionary and as I’m leaning over her with my dick almost touching her, I ask again, “Are you absolutely sure?”. “Yeah”, she nods, then closes her eyes to prepare herself. So I slowly ease the tip in but I couldn’t get it in much further, and I could see it was hurting her a little. I say again that she needs warming up more and that eating her out would help. She reluctantly opened her legs a little, barely enough to fit my head between I work away licking her clit. I felt her legs relax more and more as I kept going, eventually to the point where they were as wide open as possible and she had a handful of my hair. I put my finger back in and moved it to her g spot which got a very good reaction from her.

After hearing her moans I was now rock hard, so I came back up and tried to fit my dick in her. I eased it in much better this time round and damn it was tight, it made me let out a moan. She seemed to not be in pain this time so I gave her a long stroke and her eyes rolled back instantly. Still going slowly I give her a few more before she looks up at me and says, “Harder”. I oblige and speed up gradually, building up to the point where I’m fucking her properly. She was making almost whimpering noises as she held back from being loud but they soon became moans as she came for the first time, her body twitching away.

Now since Lucy had said she was a virgin I had been questioning in my head if she actually was, but what she said next confirmed it for me. About 5 minutes in I thought she came for a second time I so asked her if she had. She said yes, but then asked me if I had cum yet. My reply, while trying not to laugh, was something along the lines of “If I had you’d have known about it”. Then she said she thought I had came at least once already. At least once already?? I thought, jesus ok yep definitely a virgin lol.

Then after about 10 minutes the front door opens and the girl she’s sharing a room with has come back. Lucy pushes me off and tells me to get dressed as she scrambles for her clothes. The girl realizes I’m there and goes straight into the bathroom to get out the way. Embarrassed that she’s been caught, Lucy tells me to leave before she gets out the bathroom. I get dressed quickly and leave, carrying my shoes and shirt in my hands as I walk through the hotel back to my room.

–

That holiday I fucked Lucy another 4 times, with much more success. With being in the same hotel I bumped into her most nights so we just ended up having sex after going back together. She was much more confident with me now and had obviously watched porn or something because she had positions she wanted to try. She was good at giving head and liked forcing herself down my cock until she gagged. She liked doggy with me pulling her hair, and liked me pinning her down by her throat. I felt like I was creating a slut, and by the end of the week she was texting me during the day saying she couldn’t wait to fuck later.

On one of the most memorable nights we were fucking in my room doing doggy, when the two friends I shared a room with came back. They opened the door slightly and asked if I was ‘busy’ but before I could reply Lucy said, “They can come in if they want”. What the fuck this girl was mental! She apparently didn’t mind when it was my friends catching us and not hers. So I shouted back to my friends “not really”, and they slowly peaked round the door to see me blowing this girls back out, with her big ass bouncing away. They both hid back round the door laughing and shouted to hurry up so they could sleep.

We kept them waiting and fucked for another 20 minutes or so, with my phone blowing up with texts saying to finish already which we both found hilarious. When I was about to finish, I pinned Lucy down and told her I was going to cum inside her for the first time. She looked up and told me to do it, so I fucked her hard until I shot my cum deep into her, no longer virgin, pussy. I tell her to go to the bathroom and wait for it to drip out, while I text my friends that I’m no longer busy.

Source: reddit.com/r/gonewildstories/comments/kd4vkh/mf_taking_her_virginity_holiday_fling