Most amazing night of my life whilst on a business trip [MF]

This (totally true) story is about the most amazing thing that has ever happened to me. Apologies if it’s a bit long, but I think it’s important to set the scene. First, a little bit about me. I’m a 36 year old divorced but recently remarried dad, not in terrible shape but not the fittest guy by any means. I think I present reasonably well, and my new wife obviously thinks I’m attractive! Personality wise, I’d describe myself as very shy and rather socially awkward – I typical introvert, in other words. I must admit, in all my 36 years, I’ve never actually been confident enough to manage a “one night stand”. I’m just not the sort of guy who has the skills to end up in bed with a random stranger. I should also point out that I’ve never been unfaithful whilst married. Well, not in the past, anyway…

So, last week, I needed to travel to another state for a few nights for work. As I’d recently lost some weight, bought some flattering new shirts, and had just had a snazzy new haircut, I was feeling quite confident about myself. Waiting for my flight out, I decided to take off my wedding ring, and buy a packet of condoms, just in case I somehow managed to get lucky and meet a girl for a hookup during my time away. I knew in the back of my mind that I was just being wishful and nothing would actually happen of course, but better be prepared just in case…

Long story short – night one of three, got into the city quite late, I was tired and didn’t feel like going out, and knew I had a big day at work the next day, so I just went to bed.

Night two of three is where things got VERY interesting. A short walk from my hotel was a trendy area with a few lively bars/restaurants. I strolled down at dinner time, and had a look around to see if there happened to be any eligible single women hanging around (yes, I know – ever the optimist). One of the bars had communal tables out the front, so I ordered some food and deliberately sat down next to a group of three very attractive girls. Contrary to my usual shy self, I managed to strike up a conversation with them. They turned out to be visitors from Amsterdam, and were very friendly, but unfortunately they said goodbye and left after a short but pleasant chat. Oh well – so much for that potential opportunity.

It was a pleasant evening, so I went for a walk around the city. There wasn’t much to see though, so I ended up back at my hotel around 9pm. Not wanting to go to bed yet, I figured I’d grab my book to read, and head down to the hotel bar/restaurant for a drink or two and maybe see if anybody interesting happened to be there. I found the restaurant almost empty, with just a couple of tables occupied. I think I was the only customer under 70 though! My attention was immediately caught by the very pretty young waitress who seated me – Beth, according to her name tag. Even though she was wearing a generic sort of hotel waitress work uniform (black pants and a tailored shirt) I could see that Beth had an incredibly sexy round ass, slim body, and perky but large breasts which were filling out her shirt very nicely. Her hair was shoulder length, dark brown, a slightly quirky style with a fringe. From the moment Beth started talking to me, she was relaxed and playful, and (possibly just wishful thinking on my behalf) a tiny bit flirtatious. I wanted an excuse to talk to her as much as possible, so rather than just ordering off the menu, I asked for her suggestions, and enjoyed some cheeky banter about ordering the most expensive thing on the menu. I tried to read my book, but found myself too distracted, watching Beth work, and thinking to myself “should I somehow ask her out? How would I do that? She’ll say no of course, but what if?…”. Every time I had an opportunity to speak to her, it seemed that she was acting just a bit more friendly than was strictly necessary, or was that just my overactive imagination playing tricks on me?

After a couple of strong drinks, when it looked like the place was winding down for the evening, I had made my decision: If I don’t ask her, I’ll regret it for the rest of my life. If I do ask her, the answer will almost certainly be “no”, but at least I won’t have to wonder what could have been. After playing out many different scripts in my head, I waited until Beth was at the service counter, and went over to pay my bill. Again, Beth was very friendly, so, my blood pumping and feeling very nervous, I sucked up all my courage and asked my well prepared question: “can you help me out please – hypothetically speaking, how could I politely ask if I can buy you a drink after work without offending you?”. Beth giggled and smiled broadly “that works!” she said, “the answer would be yes, I’d like that, but I won’t get off work until very late tonight, and I need to be up early tomorrow morning. How about tomorrow night? I shouldn’t be doing this, but here’s my number. Call me or message me tomorrow”. What? Seriously? That actually worked?! We exchanged a few more pleasantries and I found out a bit more about her, then I went up to my room.

As soon as I got to my room, I put Beth’s number into my phone, and messaged her so that she would have my number. Of course, it did cross my mind that she had just written down a fake number to get rid of me, so I was fully expecting a “who’s this?” message back again. I tried to get to sleep, but I was too wired, thinking about what had just happened and what may or may not happen the next day. Sometime after midnight, while I was still trying to get to sleep, my phone lit up with a message. Yes! It was Beth! And she confirmed that she was looking forward to seeing me! I eventually managed to get some sleep, though not without regularly waking up feeling incredibly excited but also anxious.

The next morning, I messaged Beth as soon as I woke up. To my alarm, she didn’t respond. Maybe she had changed her mind in the cold light of day? Maybe she was just toying with me all along? All day at work, I kept on checking my phone, hoping for a message from Beth, but no luck. I don’t know how I managed to get through the day, but somehow it was time to leave, and I still had no idea if I actually had plans with Beth or not. She had mentioned that she needed to do some things in the early evening and would let me know when she was going to be free, but by around 7pm I still hadn’t heard from her. I didn’t want to seem pushy, but I was getting very anxious and starting to convince myself that the whole thing had fallen through, so I messaged her to check how she was going. To my immense relief, she replied straight away, confirming that yes, she was still planning on meeting up later! Now, I should explain at this point that I didn’t really know what to expect of this meeting – was it just going to be a drink or two, or was it going to be more than that? Beth answered this question during our messaging conversation by explaining that she couldn’t come to my room at the hotel because she worked there, but I was welcome to come to her place and she could even pick me up and take me there. O.M.G. This was actually happening!

We still didn’t have a precise plan though – I was waiting for a message from Beth, confirming that she could pick me up from the hotel, and when this would be. Having nothing better to do, I just watched TV in my room, my eyes getting more and more droopy after barely having slept the previous night. I think I actually dozed off a few times. Around 9:30pm, I still hadn’t heard from Beth again, so I messaged asking for an update. I was starting to feel a little pessimistic. It could still be just a cruel game – why would such a gorgeous creature really be interested in boring old me? Was I just being silly? My phone buzzed with a message: “I’m leaving soon, I’ll pick you up from the street behind the hotel in about 15 minutes”. Whoohoo! I brushed my teeth, and made sure I was ready to go (condoms in my pocket – check). 15 minutes later, I was at the agreed meeting point, and there she was, waiting in her car for me! Unbelievable! I got in the car, and we started chatting about her day, and getting to know each other better. In conversation, she found out that I was 36, and I found out that she was only 20. We both agreed though that age is just a number and really didn’t matter, and she mentioned that she had been with a guy my age before anyway. This comment gave me further confidence that she really was planning on “being with” me. I could barely contain my excitement.

We arrived at Beth’s house. She lived with a couple of housemates, but neither was home, so we had the house to ourselves. Beth’s room was what might one expect of a young and carefree student – not exactly neat and tidy, but who cares? I was there! I felt a little uncomfortable, not quite knowing what to do with myself – remember, I’d never been in anything like this sort of situation before. Beth, however, immediately made herself comfortable by (right in front of me) taking off her pants and putting on some comfy pyjama pants instead, and also took off her bra. I love seeing the true shape of a woman’s uncontained breasts underneath her t-shirt, so I found this an incredibly sexy tease. Not having packed anything else to wear, I was feeling rather over dressed still wearing my formal work clothes, so I said something like “would it be too forward of me to take these clothes off?” Beth laughed and said that she’d like that, so I stripped down to just my underwear, and hopped into her bed. Beth lit a couple of candles she had on her dresser, and came to sit on the bed next to me.

Eager to get my hands on her gorgeous young body, I offered to give her a massage. I sat at the head of the bed, legs apart, and she nestled in front of me, her body pressed against mine. I started massaging her neck and back, whist we chatted about anything and everything. My hands began to roam closer to the front of her body, stroking the sides of her breasts and lifting up her shirt a little to caress her bare skin. Beth nestled in even closer to me, so that our bodies were as close as possible. I pushed her pyjama pants down slightly, exposing just a hint of dark brown pubic hair. I must admit, I’m really not a fan of the shaved/waxed look, so I was ecstatic to find a real bush down there. Feeling bolder, I worked one hand down to start gently stroking her pubic hair, whilst the other hand cupped her breast. Lifting her top up further, I found that she had one pierced nipple, which was something I’d never encountered before. Her breasts were full and round, with perfectly sized pink nipples. My fingers worked their way further down, finding her moist, wet slit. This continued for a while, me exploring Beth’s perfect, sexy body, whilst we continued to chat, occasionally stopping to kiss passionately. We both knew it was time to progress to the next level…

Beth got up and turned out lights, so that the room was lit only by candlelight. She came back to bed and lay down, pulling the covers up high as it was getting a little chilly. We kissed and cuddled some more, before I cheekily said “you definitely have too many clothes on”. She must have agreed, because she immediately sat up and helped me pull off her top, revealing her perfectly sized and shaped breasts for the first time. She lay back down again, and I quickly pulled down her pants and underwear, revealing her dark brown bush in all its glory. I took off my own underwear, and snuggled under the covers, again kissing and cuddling. This was incredible. I was actually in bed, completely naked, with an unbelievably sexy, gorgeous, 20 year old girl! I made my way down to her breasts, licking and sucking each nipple whilst caressing her body all over. I love to go down on a girl, so I continued down lower, kissing my way down her torso, heading toward that inviting brown bush. She stopped me, saying “you don’t have to do that if you don’t want to – other guys I’ve been with didn’t want to do that, so I’m not really used to it”. I assured her that I very much wanted to, as I love to give a girl pleasure. I started working my tongue up and down her already very wet slit, finding her clit and flicking my tongue side to side over it. With one hand squeezing her breast, I brought the other hand down, and teased my finger around the entrance to her pussy, pushing it just a little way inside. Beth was squirming and moaning, very much enjoying the attention I was giving her. Normally, I wouldn’t stop until I’ve made the girl cum at least once, but I could tell that she couldn’t totally relax with me down there, so I came up for air. “How about you just fuck me?” Beth whispered.

I positioned myself on top of her, cock nestled against her pussy. I guided her hand down to touch me – I wanted to feel her hand on my cock. She touched me gently, stroking my cock, making sure it was hard and ready for her. Neither of us had mentioned whether or not a condom would be necessary, and seeing as I’m not a fan of them and not wanting to kill the momentum, I slid slowly inside her. It was pure ecstasy. I was taking my time, wanting to enjoy this moment for as long as possible, so I could feel her warm, wet pussy accepting my now extremely hard cock. Beth put her arms around me and pulled me tight, pulling me into her as far as I could go. Beth whispered that she had just been tested and knew she was clean, and I confirmed that I was definitely clean as well. Beth’s pussy felt utterly amazing as I slowly stroked in and out. I didn’t want to cum too soon, so I was going slowly, enjoying the feeling of every slow and deliberate thrust sliding in and out of Beth’s welcoming pussy. I asked her if she wanted to switch positions and be on top, but she replied that she prefers to be fucked, so I continued enjoying the amazing sensation of my hard cock fucking this gorgeous 20 year old. After a little while, I repositioned so that her legs were up around her ears, giving me even better access to drive even deeper inside her. Beth was moaning in pleasure, we were both getting lost in the moment, and I whispered to her “are you close?” She replied “oh baby I’m not going to cum until you do”. “Can I cum inside you?” – “Yes, yes, cum inside me, I want your cum inside me!”. I pumped harder and faster, I could feel I was getting close. No more taking it slow and gentle now – it’s time to cum. I fucked Beth how she wanted to be fucked, driving deep inside her, my cock getting lost in that beautiful brown bush, until I felt her pussy starting to pulse as she came, tipping me over the edge as I shot my load deep inside that sexy young pussy. It was truly amazing. I collapsed on top of her and held her tightly, kissing her and telling her how special the experience had been.

I didn’t know what time it was, but I knew it must have been very late by then, and we were both exhausted, so it was time to get some sleep. We cuddled and chatted for a while, before settling into a comfortable caress to relax and go to sleep. Gently stroking and kissing Beth’s back, I felt a stirring down below. I was getting hard again… I whispered in her ear “I know we’re supposed to be going to sleep, but you’re just too sexy to resist”. With Beth lying on her front this time, I straddled her, my cock nestled between her legs, stroking her pussy. I very much enjoyed the feel of her perfect, round bottom pressed against me, as I teased her pussy with my cock. When she was wet again, she reached down and guided me in. It felt just as good as it had the first time. Again, I started slowly, but gradually picked up the pace until I was pounding her hard and fast. Beth was really enjoying getting fucked, swivelling her hips to increase the sensation, looking back at me pounding her from behind and saying “wow, that’s so hot”. Again, I felt her pussy pulsing as we came together, a fresh load of cum finding its way deep inside her. Utterly exhausted but well and truly satisfied now, I rolled off her, and we eventually went to sleep after some more kissing and cuddling.

The next morning, we had to be up early, as Beth had a breakfast shift at the hotel and I had to get ready for work. She drove us back to the hotel, but dropped me off down the road so that I wouldn’t be seen getting out of her car. We kissed and said goodbye, and of course when I saw her again at breakfast, I didn’t give any indication of just having spent the most amazing night of my life with this most amazing and special girl of my dreams.

Source: reddit.com/r/gonewildstories/comments/5ftuwr/most_amazing_night_of_my_life_whilst_on_a