Losing my virginity, again

The day started as usual, without any knowledge of what was about to come… losing my virginity to a woman as a now so-called bi-sexual high class male escort.

When I woke up, I started journaling about my boyfriend who coincidentally (you will get the reference later in the story) told me he had sex with a woman for the first time last year, at the time he was 34 years old. My boyfriend, who at the time only offered services to men described the experience as liberating and as an empowerment, he quoted ‘’Then I really knew being an escort was cut out for me’’. I had one question in mind; but what was his thought on the matter of repeating that pleasure? He didn’t seem interested in doing it again, which made me wonder how it would be to have sex with a woman after exclusively being with men. The chance of getting struck by lightning is approximately one in a million, then how come I also had my first sexual encounter with a woman at age 21 two days after the conversation with my boyfriend, only knowing the matter would happen the day of the request.

Sexuality; men, women, or both?

A background story of my sexuality and experience as an escort is needed, especially before we get into the juicy (quite literally) details. As a young escort, I only offered my services to men, with a couple of requests from women that never happened, not because I didn’t want to but because they simply canceled. Around the age of 15, I had a couple of girlfriends, most of whom I met at high school, which never progressed into more than making out on a bed. That being said, I never had a ‘’freighting’’ feeling about the vagina, as some ‘’gay’’ men do. My essence was always ‘’I like the person, not the gender’’. But even with this mindset it never happened, until today.

The request

My phone buzzed while I was in the shower, and the message appeared on the screen from my Jake Dean phone: ‘’Hey, are you also available for women? We would like to meet you as a couple around 07:30pm at the W Hotel in Amsterdam’’. This message spiked my adrenaline as I sensed it was a serious request, besides that I was in the mood to work after a relaxing weekend with my boyfriend. I replied: ‘’It’s a pleasure to read your message, I’d love to make your fantasy happen. I’ll meet you at your room around 07:30pm’’ followed up by ‘’It’s important for me to point out that I mostly provide services to men, is that alright?’’. They replied with a positive and short message, pointing out it was fine: ‘’As long as you can perform’’. That last matter was something I started to doubt with my nerves, but I chose to agree anyway.

Slowly I was getting ready to get into the role of Jake Dean, already starting to imagine what this session would be like. I felt the urge to almost give myself a different name ‘’Is Jake Dean the man for this woman that awaits pleasure?’’. This is what my mind does when I get nervous about an inquiry, which I hardly get lately. I grew into becoming an escort, knowing that I am a professional who actually loves what he does. On the note of being professional I decided to take a small dose of Viagra (60 mg), just to make sure she is satisfied. Amongst the pill, I also asked my lady friends for advice: ‘’What do women really want when it comes to intimacy?’’. The general answer was ‘’Take it slow and read their body language, it’s much more of a mental stimulation’’.

‘’You look like your photos.’’

The time had come for me to enter the hotel after a short travel through the city, listening to my playlist that gets me in the mood. I did decide to go as Jake Dean, thinking ‘’As an escort Jake enjoys seeing others pleasured, so why limit it to men only?’’.

‘’knock, knock’’ that’s the sound I made on the room we agreed on at the second floor, which felt like an hour of walking with my mind racing a hundred miles an hour. The door opened up and an Asian man with a staggering smile and big muscled shoulders greeted me at the door, then I saw his wife sitting on the bed; a beautiful American red-haired lady with a body that would stop most faces in the street. ‘’You look like your photos; we don’t see that often’’ coming from the husband. I replied ‘’Thank you, I must say that you and your wife look better than the photo you sent me at the windmill as well’’. My comment was honest, I can hear what you think. We laughed and they told me that they took the photo when the wind was almost blowing them from the tulip fields. They both lived in America and were on a vacation, for the first time in two years. The couple looked truly happy and in love, which made me feel at ease.

The act of pleasure

Earlier when the husband messaged me, he pointed out that they both liked watching each other, which came down to the fact that I had to pleasure his wife while he was watching. Knowing this the nerves kicked in and I needed to take a breath in the bathroom, I thought ‘’This will be an experience to never forget’’. I got back in the room and started kissing his wife sensually as the opening of the experience; I thought ‘’It might be smart to start on a familiar note, giving me time to mentally prepare for the rest’’.

The kissing gradually progressed into taking off my white blouse and black trousers, and also realizing that I must be gentler as I’m used to be getting a little rougher and more passionate right away. Before I knew it, we were both naked and I was rubbing my naked body against her belly, I said ‘’your body looks and feels amazing’’. She replied with a sensual and daring moan, indicating she was ready for more. My mouth was going from her neck slowly to her breasts which surprisingly turned me on quite a bit, besides that she smelled like a rose garden. With a seductive look in my eye, I went down on my knees and started licking around and inside her vagina, trying to see what movement was comfortable for her. The first thing I noticed was that she liked it when my tongue would go up and down from side to side, sometimes going in a bit deeper with my tongue. I thought ‘’Not bad for somebody that hasn’t even touched a vagina before, as she clearly liked it (thanks to the tips of my lady friends)’’. One interesting matter was also the taste, it was better than cum if I’m quite honest. After about 10 minutes of licking and gliding into her vagina with my tongue, the time came that she wanted to sit on top of me, which I was ready for. I vividly remember being quite hard from the excitement and surprising elements that came into play. Gliding in didn’t feel a lot different than anal, except that I didn’t need half a tube of lube. The sensation felt less tight around my intimate parts, not saying it was a bad thing. Seeing she was comfortable made me ease into taking control, which we both enjoyed immensely at this point. We made love quite roughly after a slow start; both moaning of the pleasure we were sharing.

At one point I didn’t think I could be more surprised, but there it was; she came! And I knew that it’s a lot less common for a woman to climax as for a man, perhaps it was the trick of putting pressure on the underbelly. This was the cherry on top, the ultimate satisfaction for the couple that was beyond lovely.

Aftermath

After she came, we talked a bit, and they told me ‘’We want to see you again, later this week. You exceeded our expectations’’. Which made me smile even more, what a date! And all this happened within one day, during a date that lasted two hours.

My vision of women was always seeing them as holy beings, the creators of life; being around women empowered me, especially having more female energy around me than male influences. This made the experience all the more interesting, it felt like I was crossing a line of respect, but it was consensual. This showed me that my sexual liberation still had a long way to go, as these are mental boundaries that can shift.

Would I repeat this experience? Yes! But I wouldn’t want to make it my main service as I still feel like I prefer men more for now, for as far we can speak about gender; as an escort, you see sex more fluid than just somebodies’ gender, it goes beyond something that you can put in a box (metaphorically speaking). For now, I have to let this experience sink in, hoping you enjoyed this unique event that happened over the course of just a day.