Yes, of course as an adult I realize I should know better. Given that I faced being “dumped” versus finding some adult company, I chose fun. I miss being sexual, I miss sharing that with a man. Of course I would have preferred to spend all my time with just one guy, not try to craft the perfect man from a bunch of different ones. If a man can sleep around, why can’t I? All of these encounters were safe, we used condoms, and a few men even left wearing masks!
I am writing this up as sort of a memoir, as well as to recount the events of the last two weeks. This is WORDY, so grab a cook drink, settle in, and buckle up. A bit of backstory: I was planning to travel for personal reasons, and about a month before my trip I met two men online who were both very interesting, very nice, sexual… men I would normally be attracted to. However, one of these men seemed much more my type, and as we got to know each other over the next few weeks I started to wonder if the connection would translate to real life. Both of these men lived in the place I was visiting, but I made the crazy decision to ask one of them if he was interested in us staying together during my visit to see if anything real happened between us.
About a week before the flight, this man started to show signs that things have changed. I was bracing for the worst, but as my trip began, I hoped I was wrong. The afternoon after I had landed, he reached out and told me he wouldn’t be able to continue… that his child had covid (ftr, that child is a fully capable over 18 college student). I was honestly devastated, but resumed my 2nd plan which was to stay in a hotel (ended up being 7 hotels over the course of 2 weeks). I absolutely hate hotels, so I only booked a few days at a time… That evening… feeling sorry for myself and honestly really lonely, I (stressing safely) posted on a r4r sub Reddit looking for a man (yes, just one) to do what this other guy [1] couldn’t, and included a few fun pics and almost immediately began receiving messages. It was a little overwhelming, but before I shut down for the night I read one last message and he and I exchanged some really great chat. Two nights later he visited me and spent the night. I thought he was amazing and intense, funny and handsome, charismatic and a good listener. He was really sexual… he REALLY enjoyed very vocal sex, and he even lifted me up on his cock, like he was bucking into me! What was truly amazing was the fact that he had me on all fours on the hotel floor in front of a full length mirror (I don’t like hotels in general, nor do I enjoy looking at myself in mirrors). What a trooper… we went four rounds, and he came 3 times (long day, he was tired). I thought it was adorable that he snores, and slept on his back with his arms crosses over his chest. He promised that we would meet up again, and sadly that’s when I knew I wouldn’t see him again. I messaged him a few times and the replays I received were good-natured, but didn’t promise anything more like he had before.
The next day, I met up with someone else [2] who seemed very openly sexual, nice, and real. He was completely comfortable giving me his address, and us possibly having a sleepover. Unfortunately it was obvious from the beginning that we weren’t going to click. We kissed and it was a bit awkward, he addressed me and it was very awkward, we showered and it was awkward. We went into his bedroom and were kissing in the nude, holding and touching each other, and just enjoying our company. He had a Hitachi charged and waiting for me. I honestly have never used one before, and truthfully I didn’t really enjoy it. It was just too much, too fast, and just not my thing. He also complained after playing with me that his hand was starting to hurt. When I played with him he couldn’t maintain his erection, My guess was that he was used to extreme kink and being simple was not in his sexual repertoire… perhaps he’s simply used to women who are less work? I wanted to keep in touch and said so, of course no reply message yet.
I kept chatting with others that answered my post. However, later in the week upon finishing some personal business I was browsing on Reddit and saw on a not safe for work post on my feed, a comment someone [3] had made about a 3way. I clicked on that guy’s /u and saw a very amusing dick pic. I sent him a comment of my own, and the reply back was if I was interested in “applying” for him. And I thought that was both funny and very arrogant. Of course, two days after that at around 6:30 in the morning he came to my hotel room and probably spend The next 20 minutes with me. The entire Interlude took less than an hour. He was definitely his dick pic, but certainly not the ideal man he and I’m sure others considered him to be… he told me details of his life, sent his number and multiple videos, but kept it no name.
Frustrated, and angry, I posted on a different sub /r Friday morning immediately getting messages. Almost immediately one reply stood out and we began chatting back-and-forth. He [no number, as he also bailed] had suggested meeting for a date later that afternoon, and I was incredibly excited to see if this will work or not. suddenly he had replied that he had forgotten a job interview that was scheduled and that he may have to cancel entirely. This was unfortunate because of it could have been, but also because it look like he was a regular contributor on Reddit and he had been furloughed from a place that I was personally Invested in.
And so I kept looking. Chatting here and there with me and replying to my new post. I was in a bookstore when I received a reply from a man [4] who claimed to live in Venice. He sent a dick pic, but it was what he said that reached me. His reply seemed genuine, and even though I was upfront with him about my looks and body type, he didn’t act like that was a problem. However when I gave him my number, he called me but didn’t share HIS number. He sent me his address, and then changed his mind and sent me a hotel address. Fully respectful of his privacy, I agreed to meet him at the hotel. I had yet to see a picture of his face but from our conversation I felt comfortable with him. We met out front, went upstairs, had a heart-to-heart conversation, and then he began kissing me and I started dry humping and I was very close to having an orgasm with all my clothes still on. I had purposely left all of my things in the car because I didn’t want it to just seem like I was expecting things to happen in the hotel. To cool off, I went back downstairs to collect my things, while he took a shower and relaxed. When I came back, it was my turn for a quick shower and then I joined him on the bed. We kissed and touched and talked more. He claimed that he didn’t like doggy style because he wanted to see his partner’s expression. The next thing I knew he was a little rough, pinning my wrists, which I LOVE and honestly wish there was more… he was kissing and touching me and holding me close moving me how he wanted me. And when the condom was rolled onto his cock he had me on my hands and knees while he mounted me from behind DOGGY STYLE, slid into me so deeply that I felt every inch stretching me. So much so that it was honestly difficult to move on him. After a few minutes, he then rolled me onto my back pulled out about halfway and watched himself as he filled the condom. After that he got up to wash off, checked his phone and claimed he had a work situation, and that he would be back after he took care of that. He sent a message around 10 that he would try and wrap things up soon. Around 1 AM he said he wasn’t coming back and check out in the morning. I was honestly devastated and sad that this man let me down. That he couldn’t have been honest and communicative, that’s so far all of these men had all been the same. I slept for a little bit, which was difficult since the room stank of cigarettes. In the morning I showered, packed, took my things to my car, and then checked out of the hotel as he asked. Apparently he had booked a hotel for two days, but could only stand me for one hour. if that. A shame really, as it would have definitely been an enjoyable weekend given how initially hot it had been. Honestly, at this point I wonder if guys #3 & 4 just couldn’t deal with all my daddy-talk? Was it my fuller body? Was I too tight for their size?
…. and then things got interesting. That morning before I left that mistake of a hotel, I got my period. I figured that meant it was over for my experiences, and went to stay overnight with a friend. Not sure why I’m surprised (maybe I’m just out of practice), but apparently many men are into the red wave… I met with someone [5] new, who I had been talking to over the weekend. He was actually really sweet and friendly… tatted chest and arms. We talked and after he admitted that he had always wanted to meet someone on Reddit for a hookup. We kept up the conversation, drank a bit more, and of course I was tired as always. NOT “a line,” I’m always sleepy (and love sleep fucking). We were making out in bed, and things escalated quickly. I laid down on a towel and he went at it. It was kind of shocking how into it he was, oral… penetration, a simple handjob… he even used his finger all the way deep up my ass, something I haven’t had done to me by someone else in YEARS.
I didn’t go on a date with any of these Men. Had a proper sleep over with three of them, but still no one held me as I slept… guys on Reddit just don’t read!! Of course that’s a generalization, but true as maybe only 5% actually bothered to meet my listed qualifications of exactly what I wanted. Is it slim pickings or just laziness? Are guys just ready to pounce at anything? Am I just that starved for attention?
Ultimately on my last night, I’d had enough. I kept going back and forth with one guy [also no number, sorry] who seemed both very interested and very arrogant. He seemed willing to compromise with me, and then turned mean when I didn’t immediately meet him. We said goodbye and then suddenly he opened up to me about relationships. There was a another guy [no number either, sadly] who was honest about a past Reddit experience… and I was interested in getting to know him more, but timing didn’t work out (later, he admitted that he wasn’t even 21 yet!). Funny enough, I was messaged (after the 2nd post) by a 20something guy who ghosted me back in March. He used the same pic and everything, except we both had new throwaway accounts!
So on my last night as I was packing, a long time friend (an ex) texted me and we got to taking. He said he didn’t want to hang up, and knew I probably had to hunt down food. He sent me door dash for dinner, told me to hurry up and eat, pack, and call him back. We then had phone sex… seems archaic, but kind of the low key night I needed – definitely helped restore my sexual balance, especially with those previous unfortunate experiences.
I’m still honestly sad about what could have been with the potential friends with benefits guy who canceled on me. Ultimately on a very basic, physical level I needed to do all of this. I just really wanted one man to “borrow” during my stay, and instead got five (six, if you count my friend on the phone in another state). Maybe I’ve had enough. Maybe I’ll look again in the future. We shall see…
Source: reddit.com/r/sexystories/comments/j3hge8/success_or_failure_a_cautionary_tale