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So I finally got round to getting laid.
If folks check my post history, you would know that I go to an escort for sex. And as usual, I did go to the same escort for sex, but this time around something felt a little bit different. I wouldn’t say I didn’t enjoy the sex.
But at the same time I kind of realised that sitting around outside - but not loitering around her place to make it obvious that I was a client, waiting around for said escort to get ready (and I was on time - this is usual for this escort), getting in, having a shower, seeing her getting ready too, and then having the act of sex as well as half an hour of naked chit-chat while she smoked and talked about her heart condition… it really wasn’t where I saw my life going in terms of sex and relationships.
I think a large part is compounded by the fact that I have a new house (yes, I’m still banging on about this) and I’m learning to do so much stuff on my own. Next month I’ll be 35 years old, and yet in so many ways I feel like such a child in terms of learning to look after myself. I’m not going to go into too much, but I have some complicated feelings about the way my parents supported me the past 10 years.
That afternoon, I sent my escort a text saying that I think I’m ready for a relationship and because of that, I’m very much going to stop seeing her from now on. Of course she texts back that she’s available for support etc etc, but I deleted her number as well as other numbers of escorts I’ve considered and/or tried.
I remember the first time I had sex (with an escort - you can read that here: https://lemmynsfw.com/comment/2017322), I remember feeling super down about my penis size (again, I’ve talked about that my feelings towards small penis shaming: https://lemmynsfw.com/comment/749462). Now that I’m getting older and I have more experience, I’ve definitely stopped caring. It also helps that the lovely people on lemmynsfw are incredibly supportive, which helps a ton. In a nutshell, I’m feeling better about myself and my body than I was a few years ago.
So yeah, I feel like I’m reaching a point in my life. Not sure what I can call it, but it’s definitely a change.
Oh, and I made two posts on the /c/cocks community:
The first one was because I was super horny, and the second I posted last night was to remind me to make this thread lol.
I mean, if you were around I’d definitely have some fun with you, man. You got what you got, and I’d say it’s plenty for both receiving and giving pleasure. btw most of the nerves in the vagina/vulva are right near the opening. Women don’t even feel that much deeper inside! Most men also have their prostate pretty close to their hole, too, like 1-2 inches :-)
I’m really glad to hear you’re stepping into a new chapter and going outside of your comfort zone. I think you’re on a good path with these changes. I personally enjoy sex only when I feel connected to my partner, and I’m not sure I could feel that way with an escort who is being paid for their time.
It is going to be hard, especially if you’re only going after women (trust me lol), but even if you get laid less, those good feelings will last so much longer and be so much more intense. It will be awkward, funny, silly, sexy, and intimate all together. I’m rooting for you, and yes I think the whole lemmynsfw crowd is on your side!
If you ever want someone to chat with, msg me any time :-)
ETA: and yeah regarding size the other folks are right. I can leave bottoms sore for days. Which means it’s hard to have sex with the same person regularly! I’m not even that monstrously large or anything!
I personally enjoy sex only when I feel connected to my partner, and I’m not sure I could feel that way with an escort who is being paid for their time.
Yeah, and this was a big part of it. I remember reading/watching someone describing sleeping with escorts/prostitutes as drinking saltwater in that you think you feel refreshed, but are constantly thirsty. I think that’s a great analogy, except for the fact that my sexual needs were and are met tbh. It’s just my emotional/relationship needs aren’t being met, and no escort could deliver that tbh.
If you ever want someone to chat with, msg me any time :-)
Thanks dude, you’ve been really nice and helpful since I’ve met you. Who knows, I may end up just reaching out just to say hi :)
Sounds like a lot of self reflection happened this week. Good luck with the changes in your life! Fuck anyone who shames you, they’re not worth your time 🙂
I have always found it strange how women can shame penis size. We’re constantly judged ourselves for never being perfect enough, you’d think there’d be a bit more empathy.
It’s easier though, when the red flags are shown up front, so you know to walk away before making any serious time investment. Just don’t take it to heart, because it’s a reflection of them, not you.
Sounds like a lot of self reflection happened this week. Good luck with the changes in your life! Fuck anyone who shames you, they’re not worth your time 🙂
Thank you, and exactly! When I was in my twenties, this stuff used to hurt me much more. I’m not sure if it’s age or experience, but I’m giving less fucks about things as I get older. The world isn’t going to collapse because my x isn’t y or whatever. Especially dating - I’m more interested in someone liking me for the nerdy self that I am rather than any sexual prowess. That was the penny-dropping moment that really made me seal the deal and make these changes in my life.
I have always found it strange how women can shame penis size. We’re constantly judged ourselves for never being perfect enough, you’d think there’d be a bit more empathy.
Honestly it’s both men and women. It’s society - the same one that shames women for having “too many” sexual encounters (???) and men for not having enough. It’s all a load of bollocks to be honest, and I’m glad I’m a place mentally to not give it much mind.
It’s easier though, when the red flags are shown up front, so you know to walk away before making any serious time investment. Just don’t take it to heart, because it’s a reflection of them, not you.
Could not have said it better myself!!
You’re absolutely right, once you hit your 30s you stop giving a shit, you realise that the most important thing is your own wellbeing and mental health. I’m fairly new around here, but I love how supportive the male centered spaces are.
Definitely keep being your nerdy self, nerdy guys are the best 🥰
And keep sharing pictures because they’re great!
Thank you for the support! And I definitely will at some point!
It takes a magic combination of a man and woman, their chemistry, biology, and state of mind for many women to orgasm vaginally from a penis. Mouths, hands, and toys seem way more effective to me anyway :-)
I can cum vaginally, but I need lots of oral play first (suck my clit and I’ll fall into another dimension 😋) There’s also a different feeling for both kinds of orgasm, so they’re both great in their own way. The real fun is in exploring though, trying something new to see what works. Orgasms aren’t always the most important part of sex, being intimate with someone and having fun together is equally rewarding.
My week was pretty quiet! I had some hot and spicy chats and traded a few nudes… I thoroughly enjoyed all the action on /c/cocks this week 😍 all the posts were delightful and I l’ve really lived up to my username this week because of them all. My toys got a good workout that’s for sure!
As someone who posted to /c/cocks twice, I’m glad to have been part of the crew to help get you off! 🫡
Yes! Thank you, I’ve loved them all 🥵
😏 happy you’re enjoying all that as much as I am
New visit yesterday to the gay sauna. There weren’t a lot of guys (probably because of the Rugby World Cup), but still enough to have some oral fun in the steam room.
When I entered the hot dimly lit room, two guys were kissing. I sat down on one of the benches to stroke myself as I watched them. One of them had a very nice butt.
The other sat down too, so he could suck the guy with the nice butt. After a while, the guy standing reached out for me, and I moved closer to put my cock in his hand.
From then on, things got a bit confused. I sucked both of them, and got sucked while the other fingered my ass. I felt he was on the verge, and just had time to switch from his glans to his balls before he came.
Wow that sounds amazing! As a straight girl I’m super jealous 🤭 I’d love to be in a MFM or MMF threesome
I’ve heard that lots of guys were looking for swinger couples to be the 3rd. So, who knows? ;)
Maybe it’s time for me to move to this wonderful Sauna Land! 🤭
Hott! I’ve never been with more than one person, and also never been in a really anonymous naughty setting like that. Is this something you’d want to do more regularly?
I started going to gay saunas few monts ago, about twice a month. From my short experience, this kind of hot stuff is quite common.
I could go there more regularly, but I don’t feel the need to. But I love the idea that I could.
Oh nice! I heard that London has a few gay saunas, and from what I’ve heard there seems to be a fair bit of action!
It sounds like you had some good experiences, which thank goodness for that. Hopefully it was nothing but good experiences!
I went to London once, for work. You make me think that I could go to saunas in other cities when I travel alone. That could be fun.
Okay, here we go! By the way my goal after this past week is to take the next week as a pause from naughty fun and really recenter myself. I think things swung a little too far towards sex.
Lots of fun this week! Almost all of it was very good to excellent! Apologies it’s long, I’ve been busy.
tl;dr: a bunch of new firsts, summarized here:
- being gently dominated
- having a toy used on me
- fingering a guy while he cums
- feeding someone my cum by hand
- fingering a guy for his first time
- being the first cock in someone’s mouth
Now the details:
- Monday Grindr bi bro fun I got back to the city and was feeling pretty horny for a quick hookup. My neighborhood is filled with hotels so there’s always someone around. I was thinking about a quick mutual bj or something. Found a slightly older married bi guy a block away. He said he was 6.5" hard, but was way smaller – didn’t really care, he could have just told the truth. He had a dominant streak, and held my arms over my head a few times. This was new to me, and that gentle dom felt kind of nice. I’m usually the dominant partner. I teased his cock with my hole, and came in that position from him jerking me off. He said he never fucked a guy before, and I didn’t have the heart to tell him that he still hasn’t :-) said it was the best sex he’s ever had with a guy.
- Wednesday Scruff traveler pain Hooked up with a different guy in a different nearby hotel for work. I was still just looking for a bj, but guy was bottom and really wanted the D. Also a little older, but very smooth and nice body. Great cock, too. At one point he got so excited, he grabbed my cock from the base so tightly that it really hurt. It actually hurt for days after that. I couldn’t stay very hard after that, and definitely wasn’t interested in fucking. I had him blow me, take my load, and let him take care of himself. It really hurt guys.
- Thursday Grindr pleasure dom for bottom My cock was out of commission today, but I still wanted to make someone feel good. I offered a bj to a bottom, and he came over on his way home from work. I ended up giving him a prostate massage while sucking him off. Once we really got started, he came so so fast. Uncut cock which was a lot of fun to suck and swallow. Also a nice size where I wasn’t choking on it. He works in the neighborhood, quite handsome, and wants to meet up for the same or more. This was the first time I had a guy cum with my finger up his ass! Also yeah, I’m more dominant, but I think I’m more of a pleasure dom than a “mean” dom kind of guy…
- Friday afternoon tanatric lesson #2 I met up with my local tantric expert to learn about tantric massage. Our time was limited, so we focused instead on having some fun and working on tanatric lingam (penis) and prostate massage. I first showed him what I did to the bottom yesterday, and he then showed my a proper massage technique by demonstrating on me. My prostate is unusually far up inside me, so I brought an nJoy wand for him to use instead of trying to use his finger. It felt very good, so relaxing and arousing at the same time. Neither of us came, and with tantric that’s totally fine. In fact, I stayed really soft the whole time!
- Friday evening reconnect with my power bottom boy Power Bottom and I had been planning this meet for a while, and even if I was sore he still wanted to come over. We had a really nice time just being intimate to start. He shared his past trauma with me, so I let him blindfold me and explore my body. Maybe one day we’ll build up to blindfolding him and doing the same. I was also really excited to bring him to the bedroom and show him the new tantric techniques I was learning. I did a combo of lingam and prostate massage at the same time, and with that I brought him to an incredible intense internal orgasm. We started at 9pm and it was almost 3 when we were done, so I had him spend the night. He hadn’t eaten, so I whipped up some quick high protein (Vite) ramen for him. I actually haven’t had an overnight guest in a long time! Slept decent, and got really horny in the morning. After some warmup, I was feeling pretty good. So we were gentle, but did end up fucking at that point. We ended up taking two showers together over the course of the day. I can tell he’s catching feelings, I’m not sure I feel the same way, but he’s a lot of fun to spend time with!
- Saturday Grindr random bj finally! Yet another guy in town for work, hotel 2 blocks away. We chit chatted on the street for a bit while he smoked a joint. Turns out he’s basically on the same career path I am, and we have A TON in common. Super cute guy, too. He understands I’m really just looking to give a bj, but we still end up getting really intimate and connected in the process. He has a nice thick and long cock, probably about the same size as mine, which is both challenging and fun to suck. I really take my time going slow and working him over, until finally he gives me a nice big load. We spend a long time cuddling, and I enjoy massaging his body while we embrace. He’s been swimming, and it really shows from his well defined back and shoulders – very sexy. He’s pretty much ready for round two and wants to reciprocate, so we jack off together. As I’m getting close, he says he’ll cum once I’ve fed him my cum. Once he said that I climaxed pretty quickly :-) I should be exhausted by somehow a decent load comes out, which I collect in my hand and feed to him. I’ve never done that before! We kiss and he ends up cumming, too. We’ve swapped numbers since he’ll be coming to NYC from time to time, even if we don’t have more sexy times (but we will) he’s a great guy and it’s good for us to know each other. He messaged me a lot later at night that he was still feeling this great energy, and I was too. For me, that’s the sign of having actually good sex! He started dating a guy, and told me it doesn’t feel that way with him, and we agreed that might be a sign it’s not really working with him. We spent about 2.5 hours together. He really wants to take my load, so maybe one day?
- Saturday dinner party girl update I went on a first date with this girl a few weeks ago, and I thought she really didn’t like me for a few reasons. I learned from the hosts of a dinner party that she actually does want to see me again, and is just waiting for me to ask! I’m giving myself a day to figure out if I want to or not. Maybe the vibe I got was my own sense of not feeling really connected with her.
- Sunday Grindr inexperienced guy many firsts I really thought I was done after Saturday, but this morning an inexperienced top finally reached out to me and was free. He has wanted me to be the first guy to top him, and our schedules have never matched up for like a month. But oh no, he is only free for 1.5 hours! That’s not enough time to start from nothing and get to first penetration enjoyably. I still go over. He’s a super sweet guy, younger grad student, with incredible soft lips. We make out, enjoy each others’ bodies, and explore our manhoods. He wants to suck me for a while. Apparently it’s his first time sucking dick! For a first timer, he’s really quite good, I’m above average, and many guys (and all girls) struggle. He was great. His is smaller and uncut, and so a lot of fun for me to suck on, too. He knew we aren’t getting to penetration, but I do offer to finger him. I rim him for a while first, which is his first time being rimmed! I get one finger and eventually two fingers in to massage his prostate. It’s his first time being fingered by someone, too! He’s really sensitive, and really good about providing feedback. I keep checking in with him, and he’s absolutely in heaven. Eyes rolling back as I finger him and jerk him off or massage his taint at the same time. Eventually he cums while I’m fingering him, and shoots all the way up to his neck :-) Apparently he never shoots that far – that’s the magic of prostate massage! We enjoy his afterglow for a while, then offers to jack me off, which wasn’t necessary but appreciated. I also manage a decent load, which was surprising. Cuddle and chat a bit more, and are ready and clean with 5 minutes to spare on his timeline! He still really does want me to fuck him, and I think that will be easier for both of us now that we’ve connected and enjoyed our time together.
It’s been interesting reading about your experiences these past few weeks and thanks for sharing! I’ve been amazed at the sheer number of reasonably positive encounters you seem to have had in such a short period of time. Just to be clear I don’t say that as a statement of judgement, but coming from the perspective of an introvert who if I meet one new person a month I’m exhausted!
Thanks so much! Guys are so horny and also comfortable hooking up, so even my shyness is trumped by horny energy :-)
In terms of mostly positive, I think Scruff is much better than Grindr for that purpose. I usually take time (days or more) chatting with guys before I’m going to meet. I also look for guys that have well written profiles and ideally have at least one pic with a genuine smile.
As a fellow penis-owner you don’t need to explain horny energy 😁
I get the impression that you’re around the City or maybe LI so you probably will have a lot better luck with any app in general than I ever would. One of the fun things about living rural is that your options are usually pretty limited.
A confession: as you’re (probably) bi I looked through your comment history to try and guess your sex. I only posted that line because I found myself totally unsure 🙂
And yes you’re right I’m on NY Metro so yeah options are amazing. Maybe too amazing. I might need to become more picky 😅
A reasonable and tactful approach as not everyone simply posts pictures of themselves to make things easy 😝. I will confirm for you that I am a bi man haha.
Have your fun while life lets you. Just be safe in the process!
Wednesday dude needs to chill tf out. You can grab people, but if you end up hurting people, then just chill. Good lord!
This week seemed to end a lot more better than last time, so hurrah for that! And party girl might be coming back in the mix, so who knows where that’ll take you!
My heart broke for power bottom dude - he seems so sweet, but at the same time, you got to go with how you’re feeling. Hopefully he doesn’t feel like he’s been strung along - if he’s catching feelings and you aren’t, then it’s probably best to have a conversation (I’ve been on the receiving end of this many times, and while these conversations suck, it ripping off that band aid sooner rather than later helps with the healing process).
Lots of very promising experiences, I hope something blossoms from it!
Oh, and the Monday grinder bro - poor dude. I’m so glad you let him have his moment lol
Thanks and I’m happy you enjoy following my sexploits. I’m all healed now thankfully.
Thanks also for the perspective. It’s really hard for me to develop feelings in general. I’m really hoping I can get Power Bottom to be a fwb. I need to have a chat with him at some point for sure. Same with my Saturday career-parallel bro from LA. We have some good chemistry.
lol Monday bro 🙃
Sounds like an ace plan!
So much fun this weekend! Went to a Friday the 13th house party that ended up getting pretty crazy, her friend group gets a lot wilder than I’m used to! Shots and weed and Molly had people openly hooking up out in the main rooms, girlfriend and I didn’t get that crazy, but we did get pretty handsy with each other enjoying the show. Nothing that would’ve blown up PornHub, but we definitely would’ve gotten kicked out of a Beetlejuice the musical production!
Saturday she introduced me to her treasure box of toys, she has an amazing collection and my first instinct was, “Try everything right now!” She showed me her favorite, it’s a vibrator designed for scissoring, and I felt like an idiot because I honestly believed that scissoring or tribbing wasn’t a real thing women did, I assumed it was made up for porn. She loves it though, and I was more than happy to give it a try! It was really nice, I like how romantic and personal it feels, and this toy just helped make it out of this world!
Eee this is amazing. That house party actually sounds like a lot of fun 😅
Love the topical humor! I’m imagining a scissoring vibe and yeah it does sound super intimate and sensual. I’m glad your gf is helping you explore new stuff!
Haha thanks, it was a ton of fun! And yeah, seeing all the stuff she has was a bit intimidating at first, but I’m loving getting to try new stuff with her!
The Maddie romcom continues!!
It sounds like a lot of fun, but also a very controlled and stable relationship too! So glad to hear it!
And don’t feel bad about scissoring - I didn’t think doggystyle existed out of porn until I tried it. In my head I thought I looked like a pornstar, but the reflection in the mirror looked like someone who was attempting to move a box across the room by thrusting his hips at it. Astronomically shameful display, truth be told 🤣🤣🤣
I tried doggy in front of a mirror exactly once. Seeing how silly I looked in the moment meant I could fuck for about 10 seconds like that before I started going soft lol.
Haha, I could totally see that for like reverse cowgirl, the only person that’s good for is someone watching! But doggy style is a lot of fun, I really like that position! Especially great for hair pulling, if you’re into that!
It’s nice that things go well with your new girlfriend. It seems to be a perfect mix of hot and sweet.
Thanks! I’m having a lot of fun, almost feels too good to be true sometimes!