Best 24+ hours of my life – losing virginity [M/F]

So I didn't think I'd be writing anything like this for a while. I've always been quite shy, don't drink or go out much, and up until just over a week ago I was a 27 year old kissless virgin. But somehow, with very little effort on my part that has now finally changed. Mostly writing this so I can try and remember it all. Changed the names – It might be a little long, but hopefully it'll show other quiet guys it can happen.

I was travelling on a group tour in S.E. Asia with about 15 other people. We'd been travelling together for about 4 weeks, but as I'm a quiet guy I didn't really speak to her much (I'll call her Kate). She didn't really catch my eye properly at first, but the longer we travelled together, the more I liked her. She was 26, fairly attractive (nice curves), pretty outgoing, very funny and one of the more fun people to be around.

It was getting to the end of the tour, and we still hadn't really spoken that much or spent any time just one on one. I was starting to like her quite a lot but didn't have the confidence to do anything. But then one night just after midnight as I was falling asleep I got a Facebook message from her. She said she didn't have the confidence to say it to my face, but she really fancied me. She didn't think I felt the same and wasn't expecting anything, but just thought I should know. I've never had anyone say something like that to me before, so I wasn't really sure what to do. I really wasn't expecting that so actually thought it was a dare or something another girl had sent as a joke. Needless to say I was obviously happy about it, and was awake for another 2 hours just thinking about what to do, if it was real and how to reply. I tried writing out a few messages, but being shy and having no experience with this I didn't have the guts to send them.

The next morning she pretty much avoided eye contact with me, and to be honest it was a little awkward. But I got the idea that it was really her that sent it. I really wanted to talk with her, but there was no time it was just us together, and I tried to write a message again that day but still couldn't send it. Another day went by and it was our last night of the tour and we were going out for the final group dinner. I tried to send a message before going out, but waited too long to send it. I didn't want to have sent it and have her not see it, and have things maybe be more awkward. So I headed to the hotel lobby hoping I could tell her later that night. The first minivan to the restaurant had already taken most people, and I was part of the second group so I was waiting for a while in the lobby with my roommate. A few other people came to the lobby, and then Kate arrived too. I'd thought she'd already gone to the restaurant, but was glad she was in the same minivan as me. And she looked amazing. 4 weeks basically backpacking, you mostly see people hot, tired and not at their best. But she was looking pretty perfect with long blonde hair and in a blue dress.

Anyway fast forward a little, it was her birthday in 2 days so during the final dinner we had a little birthday celebration for her. We then said goodbye to a couple of people, but most of us headed to a bar nearby. Kate was at a separate table with some other girls from the group. I was sitting with the other half of the group. I don't drink, but figured this was a night I should try it, so asked one of the people what I should get and ordered a cocktail (really don't like beer). I only ordered the one but could feel it a little already, and stayed watching the live band with everyone until the bar closed around midnight. We said goodbye to more people who were leaving the next morning. 2 couples had already been formed and roommates had been organized so they could each get a room that night, so they headed back to the hotel too. Weirdly all the people who usually stayed out drinking had gone to the hotel. And Kate along with 4 other girls were wanting to go somewhere else, so I stayed and joined them to a bar/club further down the road.

I told one of the girls who I'd travelled with the longest (Ellie) that I'd had a drink at the last place, and asked what I should order here. She was really surprised and said she wanted me to get drunk, but she'd look after me, and that night my goal was to get drunk, dance and have a 'cheeky snog'. Knowing Kate liked me I agreed, and let them order me a mojito. I sat at the side with a couple of other people that had joined us from the last place while most of the girls danced, and finished the mojito. They asked what I wanted next, and I figured I'd go for the Long Island Ice Tea, knowing it was pretty strong. They were all pretty surprised by that, but I ended up having 2 of those. I'm pretty sure most of the girls knew Kate liked me as one asked if I liked her (I'll call her Monica), while she was off dancing. I'm not really a dancer (apparently even while drunk) so stayed at the table. I was feeling pretty drunk, and it was at this time that Kate had stopped dancing and stood at the table next to me. We both had our hands on the table, she was leaning against me a little, and after a while we were playfully touching hands (but not looking at each other). And shortly before we left she had grabbed my hand under the table. She later told me she thought I was interested in her when I stayed out, and then knew I was when I started drinking so thought she'd make a move. We left holding hands started heading back to the hotel with the others. And eventually all got in a taxi back to the hotel.

I quickly ran across the road for a bottle of water, then joined the others in the lobby. The other girls went to sit by the pool, and I walked back to the rooms with Kate still holding hands (conveniently her room/cabin was opposite mine). It was probably a little after 3am by then and we got to the rooms, and as I said goodnight I went in to kiss her. She kissed me back pretty aggressively and we must have made out for at least 30 minutes. She said she was so scared I was going to ignore her for the rest of the trip after I didn't reply to her message. I told her I wanted to reply but didn't know what to say to it, and she said she was expecting a reply by the next morning. Our hands were all over each other, I dropped my water bottle in the pathway and had to lean against a tree to keep my balance. Her hands were going down the back, and front of my shorts. She guided my hand to her boobs, and my hands were all over her too. Shortly after that her roommate came back. We were kissing in the middle of the pathway but stopped while her roommate ran past, just saying sorry as she went into the room. We laughed and then kept kissing. Being a little drunk I kept losing my balance a bit and she said did I want to sit down. I sat down on the porch in front of her room, expecting her to sit beside me. Instead she pushed me back so I was laying down and then straddled over me and started kissing me again. We thought we heard someone else coming so stopped for a second, then started laughing again, trying to keep quiet as we were right outside lots of the rooms. She then started laughing even more. I asked why she was laughing, and she said she wondered what people would think if they opened the door and saw us there. We both laughed a bit more and then kissed for a while longer. I was a little tired by then and she asked if I wanted to go to sleep. I wanted to keep kissing her, but not having slept well the night before and laying down I was getting close to falling asleep, so said I should probably get to bed. We got up, kissed a little more and went to our rooms. My roommate had gone back a few hours before, so I just went straight into bed as I was. Yes I was 27 when I had my first kiss. Much later than I wanted. But as far as first kisses go, I couldn't really imagine a much better one.

The next morning I didn't feel too bad from the alcohol, and before breakfast replied to her message. At breakfast she had a headache, and didn't speak to me much, but we were with a few other people. I'm sure they knew we got together that night though.

Fast forward to that afternoon. The tour was now over, so a few of us had moved to another hotel. The roommate I was meant to have had coupled up with one of the other girls, so he stayed in her room. Leaving me with a twin room to myself, so I pushed the beds together. Another girl (Monica) we'd travelled with for 6 weeks had another twin room and was going to be sharing with Kate, and then one more girl had joined us too to stay at the hotel, along with Ellie who was leaving that night. So during the evening, before dinner Monica sent me a message asking if one of them could shower in my room as 4 of them were using her room. I said sure, so she came down later to shower. Before she left she asked if maybe someone could sleep in my room if they needed as I had the spare bed. Kind of seeing where it was going I said sure.

Later the 4 girls came to my room to get me for dinner, as they wanted to eat before Ellie had to head to the airport. I'd been given an upgraded room so they looked around a little, including Kate. Again looking good in a black dress. We hadn't really spoken much that day as she'd come to the hotel later and spent the afternoon with the other girls. So we went down to dinner and shortly the other guy and girl came down to join us. Details came out about us kissing the night before, most were pretty surprised that had happened and that I'd been drinking. Then after dinner we said goodbye to Ellie.

We then headed to a club that was meant to be good with a rooftop bar. We went and paid the entrance, which gave us free drinks for an hour and then a voucher for another free drink after. I've never been in a big club before – it was almost like a weird adult theme park, with different themed rooms. We went up to the rooftop, lined up for drinks and got a seat. I must have had 8 vodka/cokes/sprites, deciding I might as well drink for this night too with everyone else. Then we headed into a dance floor. I still wasn't a dancer and not really my type of music, so I sat on the side. The girls tried to drag me up but I was feeling pretty drunk and was fine staying on the side. It was now Kate's Birthday. After a little while Kate tried to get me to dance, I still didn't want to and she started kissing me again. I was sitting down and she was pretty much on top of me again. She kissed me for a while, then went back to dance. This happened quite a few times, with our friends apparently taking pictures of us. I didn't even notice them though. This must have gone on for a few hours. At one point she got me on the dance floor, guilting me into it by saying it was her birthday, but it wasn't long before we were kissing again. I was getting thirsty again so went for my other free drink, and then sat on the side again. She came back and was all over me and when we stopped around 3am, the dance floor was pretty much empty. I didn't even notice the people leaving, but we left with the others around then too.

We walked back to the hotel with the rest of the group. Kate and I holding hands. Getting to the hotel 2 of them went on to McDonalds. Monica and the other girl were going to their room, and then Monica said Kate should sleep in my room since there wasn't enough space. So still a bit drunk I walked with Kate back to my room, kind of guessing we were about to have sex. I put my phone and wallet on the side, took my shoes off. Kate put her bag down. And we stood there for a second, then Kate and I were kissing again. I lost my balance and fell onto the bed. We laughed a little, and she sat on top of me again kissing me. She told me to move up onto the bed more so I did. After kissing for a few minutes she said something and I said this was my first time. She was great about it and asked what I wanted – I could do anything I wanted and she wanted it to be memorable for me. I said I just wanted to do what she liked, and that I just wanted her and we kissed a bit longer. I started fingering her, feeling for her clit. She was really wet and told me she was that wet just for me. She was breathing a little faster. Apparently I wasn't bad at it as she said I was too good for it to be my first time quite a few times (I can thank the internet for that). She then got a little more bossy, telling me to take off my shirt. She took off her dress too. We made out a bit longer and she said to take everything else off. So I took off the rest of my clothes. She was getting even wetter. I tried to take off her bra but had a little trouble. I knew what to do but it wouldn't come undone. She tried to direct me but she ended up taking it off herself – also struggling a little bit. This is where I wish I hadn't drunk so much as my memory is a little fuzzy in places. Her boobs were pretty nice but can't completely picture them properly. I think I was just so into kissing her I didn't check out her body properly. She started giving me a blowjob. We kissed again. I kissed her neck which she loved. She said that was the reason for her hickeys from last night. I asked if I should stop but she said no. I then moved down her body and went down on her. Again I don't remember seeing what her pussy was like, but she had a little landing strip and she tasted pretty good. I ate her out for a few minutes, and think she was pretty close to cumming. She was laying with her head back, arching her stomach a little and shallower breathing. She then wrapped he legs round my head as I kept going. I started fingering her, trying to find her g-spot while licking and sucking on her clit. She made me stop and said she couldn't cum before me. I really wanted to make her though. I got close another couple of times but she stopped me. We made out a bit more and she said she wanted me inside her (wasn't really expecting someone to actually say that) but it was very hot. I asked if she had condoms and she did. I don't know if it was first time nerves, or all the alcohol but I had a little trouble 'performing'. I was thinking I would have the problem of not lasting long for my first time, but slightly had the opposite. So I went down on her a bit longer, and she did the same to me. By now it was around 4:30 am – we hadn't slept much the night before since we were kissing for ages and went to bed late, and I think we were both falling asleep. So we stopped and I turned off the lights. And we fell asleep naked next to each other.

We woke around 10 the next morning. I said happy birthday, kissed her and we were all over each other again. The twin beds were splitting apart and we both almost went down between them a little. She asked did I want to finish what we started. I said yes. She got up naked and went to her bag to get the condoms, her butt was pretty great and she looked good from behind. I pushed the beds back together and she came back to the bed. Again I still felt a little drunk so really wish I could remember exactly how her body looked. She got on top of me, and we struggled to get the condom box open. I got her to put the condom on me, she hadn't actually put one on someone before, so we both had a little trouble. It was a little tight but got it on most of the way. She then guided me in her and rode me a little. A pretty awesome view. Kissing me she then said technically I'm no longer a virgin now. I got on top of her for a bit but then had a little trouble again. She said she just wanted to make me cum and started giving me an amazing blowjob, using her hands and playing with my balls. Again watching her do that was awesome. I couldn't really believe it was finally happening, and it felt great. I told her I was getting close and shortly after had the best orgasm I've ever had. She kept sucking and I almost had to tell her to stop as I was so sensitive and felt close to passing out. She swallowed everything – also pretty hot. She got on top of me and kissed me again, then lay down beside me just staring into my eyes.

Her flight was that evening and we kissed goodbye. Not knowing if/when we'll see each other again. I was so close to changing my flight to join her for longer. She's travelling longer and going to work in Australia for a year, and I'm now back in Europe. I wasn't really sure if it was just a hookup or something more. I was the last person on the trip I thought that would happen to. But we've messaged each other every day since, flirting a bit and we want to see each other again. I haven't really stopped thinking about being with her since that morning. So I'm sure I'll end up heading there soon to see her. Within 24 hours I had a lot of firsts and it was honestly worth the wait, and luckily with a very cool person. She said she just wanted to please me and make it something good for me which it definitely was. I hope there is another time and I can return the favour a few times.

Source: reddit.com/r/gonewildstories/comments/3tklik/best_24_hours_of_my_life_losing_virginity_mf