About 3 years ago some friends and I went on a weekend away to a different city. For just a bit of backstory it was for a friend’s 22nd birthday, we stayed in a hotel in the city and paired off in rooms of 2 when we arrived. That night we went drinking in as many bars as we could to take full advantage of our new surroundings. This obviously led to us drinking a lot, and when that happens with us we usually move on from bars and end up in a club instead, and that night was no exception.
Skipping forward to about 3am when the club we ended up in started to close, I notice one of my friends is stood away from us and is talking to a brunette. It’s the same friend “Ross” that I’m sharing a hotel room with. This is quite typical for him to do so none of us really took any notice apart from me, because I guessed he was going to try and bring her back to our hotel room. The girl had a blonde friend stood behind her, who was staring at her phone looking bored and obviously waiting to leave. The rest of us guys decide to go and get food before going back to the hotel, so we tell Ross to find us outside.
We find a fast-food place round the corner that was still open and we eat while waiting for Ross. When he turns up a few minutes later the two girls are still with him, and the three of them went to order food too. My friends were done and didn’t want to wait for him, so they left for the hotel while I stayed with him seeing as we were in the same room. I went over and Ross was still flirting with the brunette, while the blonde was also still on her phone not saying much. So I struck up a conversation with her, and jokingly apologised that my mate had stolen her friend away from her (who I’ll call Gemma but I genuinely can’t remember the brunette’s real name to give her an anonymous one). She laughed a little and finally lowered her phone from her face as we started talking. The blonde’s name was “Caitlin”, she was 20, maybe 5’9 or 5’10 with her heels on and had a slim figure but with such perky tits. I wasn’t horny or looking to have sex that night, but I found her attractive so I turned on whatever charm I have, and she picked up on it and flirted back. Ross clearly noticed that we were getting on well because next he chimed in asking if the girls wanted to come back to our hotel to “chill”, he could barely stop himself from smirking as he said it.
The girls were both reluctant at first and laughed it off, until Gemma said she was tempted but didn’t want to leave Caitlin to go home on her own. Ross instantly starts sweet talking them again saying Caitlin can come too and it’ll just be chilled, having drinks etc. I didn’t even need to say anything to help sway Caitlin, she kept looking between me, Ross and Gemma until she turned to Gemma with a grin and took her hand saying “Oh come on then”, which made Gemma giggle a little. Ross turns to me grinning again, clearly pleased with himself, I turn to hide my reaction too as we lead the way back to our hotel. As we entered the lobby we got an odd look from the security guard at the desk, who mustn’t have had to think too hard to work out what was going on. We get in to our room and Ross and Gemma sat on one bed with me and Caitlin on the other. We had some beers in the room so handed them out and the four of us talk for maybe 5 minutes or so, mainly about where we were from and our slightly differing accents. Caitlin and I were talking about something else when we notice the other two were silent, we look over and they had started kissing.
I turn back to see Caitlin already looking at me, and we both laugh a little as it was obvious what was about to happen. So I lean in and kiss her, going almost straight in with tongues. She reciprocated my movements as we lay down on the bed and I started feeling up and down her body, with Caitlin running her hand up my shirt onto my chest. I remember her complimenting my kissing and that I had soft lips, which made me laugh to myself as I’d been told that before. One of the others then turned the lights off so they were obviously getting busy already. So I slipped my jeans off and Caitlin did the same as we got into bed, and I ran my hands up and down her inner thigh which made her twitch a little. I moved to rub her clit over her knickers which I could now feel was a lacey thong, and I could feel a hint of how wet she was through the mesh material. She spreads her legs a little more which encouraged me to pull the thong to one side, placed a finger either side of her clit and rubbed her in slow circles. Her whole body shudders instantly and she sharply exhales in to my ear, trying to keep quiet. As I’m toying with her clit and teasing her entrance, she whispers more compliments and says how good I am, asking how I know what to do so well. This confused me a little, I’m confident in bed but her previous experiences can’t have been too great. So I cockily respond by saying, “Oh I know I’m good, and I’ve not even got started yet”, as I nibble her ear and feel her cheek smile against mine.
Caitlin moves her hand down my chest and brushes my dick which has been hard since I felt she was wet. She brushes past it a second time and I impatiently grab her wrist and place her hand where I want it, and she gropes my dick through my briefs. I feel her thumb slide under the waist band and I help her pull them down, then she traces her fingers back up my leg, wraps them around my length and slowly jerks me off. My hand is now playing with her tits underneath her bra, toying with her hardening nipples. Soon I sat up and moved her onto her back and got into missionary, but she stops me and asks if I have a condom. I look over at Ross because I know I don’t, and before I say anything he drops a handful of them on the floor between our beds so he must have heard her. I pick one up and rip it open, putting it on as quick as I could, then I lean over her again and tease her by running the length of my dick over her clit.
Then I line myself up with her entrance and slide deep inside her pussy, and she gasps as I fill her up. I go back and forth slowly to try and keep the noise down, it was obvious what was going on under our sheets but for what ever reason I tried to hide it a little. That’s when I thought to myself that an barely an hour had passed since I first saw this girl, let alone since I first spoke to her and now I was already fucking her. This was new to me, and it made me even more hard. I gave her some long and deep strokes, causing little noises to escape her mouth as she held in her moans. After a while she pulled me in and whispered if she could go on top, so I lay on my back and watch her straddle me while trying to hide under the sheets still. She slowly rides me with her hands on my chest to hold herself up, I reach up and slide the straps to her top and bra down her shoulders and she looks across at Ross and Gemma, clearly worried about exposing herself in front of them. But they’re under their sheets and facing the other way, so I pull down her top and bra in one movement and her small but perky tits drop out. I grab them both, pinching her nipples slightly and sat up to use my tongue on them too.
Caitlin now gives up on trying to cover herself with the sheets and leans back to ride me better, and she speeds up too. This was the first time she took the lead as I had initiated everything up ’til now, so I laid back and watched her now that my eyes had finally adjusted to the dark. I glanced across the room and Ross was also watching Caitlin ride me, he was clearly more interested by the view of us fucking than Gemma giving him head. It seemed neither of the girls noticed his wandering eyes. As Caitlin started to tire a bit, I laid her next to me and fingered her. She was dripping wet which made only made me go faster, and I kept going until she couldn’t hold her moans back any longer. Then she grabbed a handful of my hair as her pussy tightened around my two fingers and she came, her body relaxes but twitches away as her orgasm pulses through her. She tells me again how good I am, which is always what you want to hear.
Now I want to cum, but I know I probably won’t at this slow pace so I tell her to come to the bathroom. Ross and Gemma are under their sheets so I grab another condom and walk into the bathroom with Caitlin behind me. I shut the door behind us and in the light of the bathroom I can see her cute and tight body properly. She asks why we’ve come in here, so I turn her around and bend her over the counter to the side of the sink. I put on the new condom and re-enter her pussy from behind, getting a great view of her nice round ass. She looks up at me in the mirror as I fuck her and watch her face change as she takes my dick, with one of my hands on her hip and the other pulling her hair tight. I keep going much quicker and harder than before, and she’s moaning more now that we had some sort of privacy. We go for maybe another 10 minutes of hard fucking until I feel that I’m going to cum, so I give her a few last hard strokes as I fill up the condom inside her.
Caitlin turns while catching her breath and says “Mmm that was great, you’ve worn me out”, as we kiss again. We go back to our bed with Ross and Gemma now kissing again, I think he was struggling to stay hard after all the alcohol. We both fell asleep quickly before being woken up by the sun rising only a few hours later. Ross and I walked the girls out of our room back to the hotel lobby, and in my hungover state I bought a bottle of water from a vending machine there. In that short time the two girls had already got in a taxi and that was that. We didn’t exchange phone numbers or even know each others surnames. I’d go as far to say that we could walk past each other and I’m not even sure I’d recognise her now that it’s been 3 years.