Man #49, first time with an escort

At the start, he didn’t seem an escort. He approached me on grindr and we talked with various delays during one week: we shared some pics, mainly body, talked about sex, about where we lived. One morning I found a message sent the previous night where he said: I didn’t mention that I’m a masseuse. I offer moments of total relax and pleasure with absolute cleanness. I’m 32, Italian, graduated and refined. For massages I use techniques of tantra in 3 steps. First: deep massage of total body. Second: body-to-body massage, more intimate, with real body contact and simulation of your genitals. Third: after the orgasm, I’ll relax you again with a more delicate massage so that you will almost fall asleep. The environment will be decorated with candles, incense and music.

Sometimes serendipity happens not only in romantic love, but also in paid sex: I had just completed a marathon and I wanted to take a morning off to have a massage. So I decided to engage with him in this conversation.

I asked if he had been trained as a masseuse, and he said he had attended courses while living in Belgium: it is a country so unrelated with wellness that I believed it was true. I wanted obviously to know more about sex. Well, here was the deal: the massage was naked, both of us, he was responsible for my pleasure and would make me come but couldn’t say how. Jerk off for sure, blow job only if he felt like it. Was I allowed to suck or rim it? It could happen, he couldn’t say beforehand. Kissing? Sometimes, it depends. Fucking? Never.

He liked to insist that he was a refined person, graduated, a pleasant guy with a good job (responsible of IT in a big company), his house was nice and could guarantee a very relaxing experience. He was, most of all, obsessed with privacy: nobody should know about this, he was not willing to give his number (bad experiences in the past), he needs as much reassurance as me about discretion and cleanness.

So many feeling crossed my mind: excitement, fear, curiosity, doubt, thrill, suspicion. I asked for a discount, which he gave me immediately. He sent me his address,which was in a very nice area. I had a shower, dressed nicely, took the underground, tried to read a book without success and I arrived to his house. When I was in the lift I had suddenly a slight worry about my safety, checked the money that I had (just what was given and a debit card), the charge of my phone and stepped outside.

What happened next was completely different to what I had imagined.

First, the hallway was almost dark, I could barely see him through a dim light from another room: he seemed nice, he was wearing just a white t-shirt and briefs. I told me to undress and follow him to his bedroom. While undressing, alone and in the dark, I noticed a frame with the photo of a clown: this almost scared me for good, I hate clowns. I went cautiously to the other room, thinking if there is anything weird, just go away. The room was nice, some music in the background, a lamp of the kind that changes colors, the bed ready for me with pillows and clean towels. I laid down keeping my brief to his surprise: he invited me to relax completely and be totally naked. I did. He went to the bathroom to take oils and creams and I noticed two more clowns on the walls. What the fuck. He came back and started massaging my shoulders and neck: I couldn’t really relax. As soon as he changed position, I turned my head to control him. He noticed my reactions and told me that he got it, I needed to trust him more before letting myself go.

He went on the bed and started massaging my back. I felt his body against my legs and my ass, and his hands caressing my body. He was surprised by my muscles. He asked me again how old was I and told me that he was attracted by me. Then he was naked over me, massaging my lower back and pushing his cock between my legs. This made all my feelings to turn into excitement: I felt my boner pushing against the bed and wanted to turn around. He laid over me and grabbed my hands. I turned my head and we started kissing with passion. I spread my leg and started moving, feeling his cock getting harder and harder. He told me to turn and stood up to massage my shoulders and chest. I leaned down my head, started licking his balls and then blowing his cock as deep as I could. He stopped to moan and started repeating my name, as if surprised by what was happening. He went down on me and we blew each other for a while, with the room getting orange, green and blue and the sound of water feeling the air. He began to massage my legs, but I grabbed his ass and started rimming him. I drove him crazy, so crazy that he told not to jerk him off, he didn’t want to come.

Then we simply had sex. We kissed intensely after blowing and rimming, feeling the taste of our bodies, we played with nipples, we entwined our legs so I could push my cock against his ass: he wanted to be fucked, but this was the only rule he asked me to respect. I kept rimming his smooth ass and we started talking dirty. A couple of times he stopped me to watch me right in the eyes and ask me what are doing to me? What are you making me doing? I had my cock against his hole, slightly inside, I was telling him how hard he needed to be fucked and jerking him while he came. He felt embarrassed and sorry, as if he wasn’t allowed to come first. I laughed, and since he started immediately to blow me, I told him to relax. I said I was already satisfied as things were, but he wanted to see me coming, to give me the same pleasure. He did and I came on his body. He went to wash himself and told me to relax, so he could end his massage.

I really couldn’t stay alone in that room, I felt unease again and dressed up. I waited in the dark hallway, watching his books, his thesis on a shelf, looking for some details about his life, I noticed a mannequin with a jacket on it, which made me think of the silence of the lambs. He seemed sorry to see me there, we chatted a bit, I said you really like clowns, he was surprised, told me I was a better observer than most of his friends, I added you don’t seem an IT guy, more a fashion guy, he told me I could leave the money on the shelf and turned his head discreetly while I paid. I went out.

I walked slowly towards the underground, gratified, not miserable, confused, surprised. Another surprise was about to come later in the evening. He sent me a smile, he wanted to chat. We commented our encounter, he seemed more surprised than me by how things had gone and told me again how much he liked my body and how unexpected was for him to come before me or to come at all.

I have no idea if he is truly an escort or just an IT guy with kinky fancies, or something different, or if escort are different from what I had always imagined. I cannot know if he found me so attractive that he forgot his role and had sex with me just the way he liked not the way he was paid for. I really don’t know if this is the way every escort behave, they gratify you, tell you are so hot and come whenever they want to come. Then you pay.

Do I care? No. Why I did it? No idea. Was it good? A lot. Would I do it again?

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