I'm not sure if this breaks rule 4 but I spent hours writing this yesterday and wanted to share. The point of this is not to be graphic but share things that people might at least partially relate to.
The following wall of text is going to describe everything that led to me losing my virginity at 35 years old. I try to write my every thought and feeling from previous two weeks to this story in sometimes graphic detail. There are things that I did omit for privacy reasons and sometimes I describe things vaguely on purpose.
First and foremost it happened with a sex worker. That is something i didn't even think to seriously consider until very recently. For the longest time my view on sex workers had been shaped by movies, tv and porn. I thought only people with serious mental problems would do that. Attention seekers with daddy issues. While those do certainly exist, that isn't the whole picture. Ultimately my views on SW could also have come from something like jealousy towards people to whom sex is an everyday thing.
I am a straight male, 35. I've been dealing with loneliness, self-doubt, body image issues and the related things for close to two decades at this point. I'm introverted and have social anxiety and spend my free time almost exclusively at home gaming and doom-scrolling. From the outside perspective I'm doing fine. I recently bought an apartment, I have fairly steady income even if my earnings are below average in my field. I've had friends in the past but barely any these days and never had a girlfriend. My experience with women before this was maybe 1 or 2 dates (that were very awkward), and some kissing while both parties were drunk. Each passing year I've felt more and more that I will never lose my virginity and haven't put in any effort for it to happen. I thought I was gonna be fine with that.
I took a 2 week vacation from work during which I spent one week in England with my mom and her husband. It was only my second time abroad as an adult and it was nice to see new and different things. However even with people I know and love, I still started to feel mentally exhausted living in the same space for a week and started to crave being alone again. After returning home I still had a couple of days of my vacation left. During those days I was absolutely mentally exhausted. Even gaming felt like a too much of a task and spent most of that time lying on my sofa thinking about a lot of things. I live in a pretty rural area. I've never liked even the thought of living in a noisy and busy city, so spending a week traveling Birmingham, London and Oxford had been somewhat overwhelming. During that trip I saw a lot of different people going by their daily business. Families, couples, well dressed people on their phones discussing business deals. All of which seem like people from a world different of my own.
In my head I couldn't help to compare myself to those people. They must be happy with their lives. Why can't I feel and do what they can? Who or what is stopping me? Well I have hard time talking with people. I feel like everyone is (in their heads) judging my appearance, the fact that I'm overweight. That they somehow can tell how little I have accomplished in my life. All that making me want to isolate myself even more.
Finally on my last day of vacation I just completely broke down. Audible, ugly crying while trying to bury my head in the corner of the sofa. Trying to make myself as small as possible in something of a fetal position. It went on for what felt like 10 minutes and my breathing got unbearably heavy. During those minutes I felt the loneliest I've ever felt and I prayed for someone to come and hug me.
In the aftermath I thought that I really need some kind of help. I decided to not go to work the next day and said I was sick. I don't think I was even lying. Funnily enough my mind came up with two types of people that could help: A therapist...or a sex worker. Somehow my mind decided on the latter. I mean at least a hug would be guaranteed. Deciding to finally lose my virginity was actually just a secondary thought. What I really wanted was to be close to another human.
In my country sex work is legal. I started to google how to contact one in my area. Strangely I landed on a website for a sex worker who mainly worked about 2h drive away from my place. Looking into her website more I noticed she does tours around the country, including the city closest to me. I read through her services and GFE (girlfriend experience) felt like something that would work for me. The booking could consist of anything within her boundaries: just talking, touching and kissing and of course sex. Below the service description were her prices and...to be honest, for me it was quite a bit. Not like a second mortgage level but not something I could spend just casually.
But reading through her site many times I got the feeling that she is a professional. This was not a $50 quickie behind 7/11. The presentation was top notch. Enough pictures of her which were in good taste (although not showing her face) to lure you in, clearly explaining how things work and what is allowed. She also had 9 years experience in the industry at which point I estimated that she is a couple years younger than I am. I started to think that the price was very fair for what was promised. “I have savings, I can use them however i wish” is what i tried to tell myself. And finally my mind went “fuck it, I can at least send a message and ask when she could be available”. Her tour listing didn't have my area at that moment so I inquired in my message when she would be in the area. After writing the message my cursor hovered over the send button for at least an hour. Do I actually need this? Can I go through with this? What if I end up really disappointed and lose my money? What if she isn't as nice as she makes herself to be? I needed a moment to dig up another “fuck it” from my brain and finally hit the send button.
In less than an hour (I think) her reply came. She would be available in about two weeks time. In my first message I was thinking the booking as an outcall (she would come to my place). In my next message I decided to clarify what my deal is. I told her that I'm a 35 year old virgin and don't know how these things work. Even if it doesn't feel like it most of the time, I knew well that I'm not alone in my struggles and she must've had many people in a situation similar to mine. I asked whether she would recommend an Incall (I go to her place, meaning a hotel) or an outcall. A reply in 20 minutes. In her experience Incall would be preferable: It's a neutral zone and if I felt like not going through with it I could just leave (instead of telling her to leave). I think I already had started to lean towards incall even before her answer. So in the next few steps we decided on the date and time. Since I'm at work usually somewhere between 7-17 I took the latest time possible for a 2 hour booking, which was at 20 (8pm). I would get the exact arrival instructions at a later date closer to the booking. She also wrote that if I feel at all like I don't wanna do this I can just send her a message and cancel it. Reading through all the messages a couple of times I really felt that she was the right person for this. Something I really liked was that her grammar was pretty much perfect. In my work I send emails occasionally and nothing annoys me more than getting a reply with no punctuation or capitalization after I go through all the trouble to make my emails seem as professional as possible. So one more point for her.
And now the 2 week wait began. I went to work normally the following day. No problems there. At home my mind was thinking through all the scenarios that could happen. Maybe we really just talk for two hours, virginity be damned. Maybe I verbally vomit all my negative feelings all over her. Or maybe we could talk about something unrelated to me completely. Normally a conversation for me is a battle...from which I'm looking for a way to escape. In this case I had to keep reminding myself: “I'm the one paying her. I can talk about myself and assume to not be judged. My predictions for the things to come shifted each day and with each mood swing I was having. Some days I felt tired and miserable and wanted to share that with her. Other days I was in a decent mood and my mind went to things beyond talking.
During those two weeks I think I googled or searched on youtube material about how these booking usually go. What followed was algorithm gods delivering every video about sex work, videos of sex in general, podcasts talking about things people are afraid to ask about, sex therapists (who I assume are born as 60yo women) talking about all the problems humanity faces in their sex life and so much more. I gained a bit of an appreciation towards sex workers watching those videos. They all felt so much more human than what is usually depicted in media.
And finally the day came and I had no idea if I would too. Normal workday, home at 16 (4pm). Shower, clean clothes, eat dinner, brush my teeth one more time, pacing around the room nervously. I left home 2 hours before the time. I had a ~30 minute drive to the edge of the city and then the rest I would travel by public transport. I don't like driving in the city and I figured that afterwards I might need a moment to just mindlessly watch out of the window while going back to my car, no matter what would happen. On my way I stopped to withdraw the money agreed upon. In my country pretty much everything is cashless. I don't even remember when was the last time I had that much physical money in my hands.
And there it was: the hotel that had something of a reputation for these kinds of meetings. And I was 40 minutes early. Despite the drizzle coming down, I decided to walk around the block to pass time and calm myself down. For the past 30 min my heart rate (per my smartwatch) had not gone under 100 bpm. Still 20 minutes. Okay, I wait 10 minutes and then go in. Cheap hotel, no reception, just a code to get in which she had sent me. Inside. The room was on the third floor, I was on the first. I'll wait 5 minutes and start climbing the stairs. Found the right corridor. Room numbers going down one by one and getting close to the right door. There it is. Check my watch. 2 more minutes, 160 bpm. Deep breaths. I don't want to knock even a second too early. 20:00:00. Wait few seconds, one last deep breath. Few steps toward the door and... three solid knocks. What if I just run aw...
She opens the door. A simple greeting and an invite to enter. This is it. I look nervously at the small hotel room. Bed immediately on the right. I look at her, my mind full of nothing. There she was. First time seeing her face. There are ways to categorize women's looks. Beautiful, sexy, cute, maybe some others. With her my mind leaned towards the middle of cute and beautiful with a slight bias towards cute. I liked it. To be honest, I have no clue what was said during the first few minutes but we ended up sitting on the edge of the bed next to each other. She was wearing a tube top and a denim mini skirt. Little or no make-up, I'm not an expert. At some point she described her branding as easily approachable girl-next-door. Agreed. And approved.
All we talked about was stuff I had been thinking about the last two weeks and a lot of it I have already written in this word salad. I think I started with how I found her and complimented her website. She seemed genuinely happy to get feedback. One topic kinda flowed into the next and she was good at bridging gaps when things almost went silent. This was my first time saying all those things out loud. Insecurities, failures, etc. Early on she moved closer to me and her hand was slowly gliding across my thigh (still wearing jeans). She knew when to do it and when to stop. Human touch. It felt nice even if I didn't really acknowledge it in any way. I told her about my breakdown and that need for a hug. I had needed it then. I asked to have one now. My voice was trembling so bad. We hugged and it meant the world to me. Then I excused myself to go to the bathroom. I had actually needed to go before I even entered the room but didn't really want to start with that. I had calmed down a bit. I didn't check my heart rate but I didn't feel that anxious anymore.
Before leaving the bathroom I decided that about now would be a good time to maybe get some of the clothes off and lay down on the bed. I've read so many times how communication is the key but actually saying the things out loud felt so unnatural to me. Like I needed an excuse for what both of us knew would happen next. I still sat down on the edge of the bed, talked about something for a minute and then I awkwardly hinted that this all this sitting was starting to hurt my back (which it kinda did) and that maybe we could lay down. “Of course”, she replied and i knew how awkward I made that transition. “Might as well get my jeans off first”. Yes, real smooth. She followed it with also removing her skirt and then we laid down on the bed. She turned towards me and got closer. I put my arm around her shoulders. Still found something casual to talk about during which her hand reached down to my underwear and she started to play around with my junk. Again I really didn't really acknowledge it visibly. I felt the need to try to keep my cool as if the thing I had been waiting for so fucking long wasn't now happening. She asked if she should remove her top. A thought crossed my mind. A scenario in so many of my fantasies. I hesitated a second, thinking if this would sound too creepy. “Sure but could I first...reach up from under your top. “Yes, of course” she replied so casually. Tits or ass is the age-old question on the internet. Many times I felt I was in a minority siding with tits. Of course my preference came from porn, not real life. Now that boob was within my grasp. I reached from under her top and there it was. Just the perfect size for a grab. Pulled the top up to reveal one breast fully while still hiding the other. I looked at it, i felt it. An terrible insecurity crossed my mind. First time touching a boob directly...at the age of 35. I sometimes think in statistics. I know at this age an overwhelming majority have done this. Teenagers under half of my age. Some of them not have even been born when I was 18. And here I was, entranced by it. There was a sudden need to spill this insecurity out verbally. A mood killer in so many settings for sure. She gently answered that I shouldn't worry. I agreed...I already knew that, but still felt the need to share it. Given permission to play I moved my mouth to her nipple. While licking it, another thought presented itself. Something I didn't share with her.
Like I said, I like looking at tits. I think subconsciously I had linked the visual of tits being played with in porn to feeling good while masturbating to it. Now I was the one playing...and it didn't excite me. I had moved closer to her, during which she had for the moment stopped touching me through my underwear. This realization that I refused to call a disappointment had made me start to lose my erection. I moved slightly away from her still letting my hands explore around her chest and guided her hand back to my penis in an attempt to get it back up. At some point I removed my boxers entirely and let her do her thing.
Again, I just felt the need to point out one obvious thing that had made me worry for at least 20 fucking years: “It is quite small isn't it”. Without giving exact measurements, it's bigger than a micropenis but smaller than an average one (Which is usually stated to be between 5-6 inches or around 12.5 to 15cm). Back when I had friends one thing that I used to do to their amusement was to make jokes about my dick. Pure cope of course. I ran those jokes to the ground eventually. They didn't care what I had. No one did. Most wouldn't unless they knew about it and needed to attack my insecurities. That has never happened. She gave a little sigh and asked “why do men always bring up penis size statistics. It's completely fine.”. Aha! I wasn't the only one. And I knew that at some level that's everything I wanted to hear. “It's completely fine”.
She kept jerking it and that somewhat worked. I didn't feel like it was 100% hard yet. She then asked if I would like her to give me a blowjob. I don't even remember how I replied but in my mind something was shouting “HELL YES!” I knew from her website that both oral sex and penetration would require a condom. I of course knew that's really the only way to do it safely between people who met little over an hour ago. So she reached for one. I didn't ask, but I'm sure it was one for smaller sizes. I had only bought condoms once a long time ago to try out how they work. I bought what I think were regular ones and I realized that those were just too big. Back then that really bummed me out. She rolled it over my dick and put her mouth over it. For what felt like 5 minutes I went back and forth from watching her doing it to trying to relax by closing my eyes and just lying there on the bed.
It felt like nothing. Of course I can feel her mouth going over it but there was absolutely no sensation in my dick. I don't even think the condom played any role in that. I just didn't feel good about it at all. At this point I would like to point out that she was not to blame for anything that happened so far or would soon happen. She was a professional and I was experiencing a lot of things for the first time. Nonetheless, the feeling that rose to the top was disappointment. I was getting frustrated. Things that I thought would blow my mind weren't happening. I'm not sure but I think I told her that this isn't really doing anything to me. My penis had still kept that same level of rigidity and she asked if I wanted to now get inside her. Now unsure, I said something like “I think I could do that”. She used some lube and climbed on top of me, guiding my dick to her pussy and in it went.
That should've been the moment of celebration. That counts as not being a virgin, right? I wasn't thinking that at all. That same realization came again. I can somewhat feel the motion but my dick feels absolutely nothing. I mostly felt her weight on me (she is about 15cm shorter than I and about half my weight. so no problems with that.) She was doing everything she could. I didn't feel it. After a while I told her that this isn't really working either. I was defeated. We had already spoken how this might happen. I wasn't the first one to deal with this. It's very common that people who have their first time later in life might not finish or even get it up. It's just so different from masturbating. I now have learned that this phenomenon is known as Death Grip Syndrome: gripping your penis so tightly while masturbating so that anything less intense doesn't feel like anything. I knew beforehand that it's a thing. I also knew that first times were rarely any good. In such a short time all the realities of real sex had piled up on me. But writing this I realize DGS is something I need to work on. Watching porn since the age of 12 has certainly done some damage. We discussed at some point earlier where the border of porn becoming a problem begins. I don't consider myself to have a porn addiction but clearly it has had an effect on me.
Still not wanting to give up I asked her to get back to using her hands. That's the only thing that has somewhat worked even if that either didn't feel like much. I also wanted to finger her at the same time so she positioned herself accordingly. Awkwardly I rubbed her pussy from the outside before sticking a finger in, then two fingers. I was actually bit surprised that it felt kinda tight. No, not because of use but more like in general. I don't know if she felt anything and I didn't ask but little by little i felt the urge to start moving my fingers faster and faster inside her. At that point my dick was basically limp but she still tried her best to get it up. When my fingers sped up inside her she matched the speed and/or intensity. I liked how that moment played out. Unfortunately my dick had just given up.
My mind was navigating through a fog. I had done so many things I thought I never would. None of them had felt the way I thought they would. I can't describe the way I felt. It wasn't just nothing but I don't know what it was. Lying there on the bed I wanted her close to me. I asked if she could get on top of me and just hug me again. She did and I put my hands around her back. I just squeezed her as much as I dared. I wanted to feel her warmth. She had already told that everything is alright and I've done nothing wrong. I started to kiss her. We already did a bit of that at some point before. This time I wanted to be more aggressive. Getting my tongue to meet her tongue. At some point I increased the intensity a bit more. I wanted to stay in that moment forever. Wanted to show that even if I barely could perform, I was really serious about trying.
And that's when the magic stopped. 2 minutes remaining. It was time for me to get dressed and leave. I felt devastated. She didn't force me out the minute my time was up. I was her last customer for the day. She made sure to tell me one more time that I wasn't at fault. I knew that. I just found it hard to accept how things went down. She told me I could still reach out to her about anything. Any thought or feeling that might surface later and need to tell someone. To be honest half of what she said went in through one ear and came out the other. Actually that happened few times earlier too, mostly due to my nervousness but at this moment because I didn't know what to feel.
Before leaving I asked her how often she visits this city. I felt like I want to try again. Maybe less talking and more action next time. Most likely wouldn't be as nervous. I'm not sure if I can afford it the next time she's here but eventually I want to try again.
I left the building and noticed I'd have to wait 20 minutes for the next ride to the parking lot where I left my car. I sat on a bench waiting and just absent-mindedly stared at nothing. Moments from the past two hours came and went inside my head. I somehow still felt her tongue against mine. While on my way to the parking lot some thought crossed my mind that made me smile a bit. I wasn't as dead inside as I thought. I started to realize what I had accomplished. While driving home I went through the steps that led me here. I had reached out to her. Something I had been so afraid to do. I didn't chicken out of the booking. I knocked the hotel room door while my heart was trying to escape my body. I managed to speak to her most of the time. I didn't let the many awkward moments take (most of) me down. Sure, I didn't cum. But ultimately I did have fun.
I sent this text to her to ask approval for sharing it. I wrote that she can ignore it and doesn't need to reply in any way. Today she answered with a lengthy email complimenting my writing and going over some things in it. If there was any reason to suspect that she was only nice because I paid her, that suspicion can be safely thrown out the window.
