Michael - Gigolo

If you are a woman that has fantasized about being with a man other than your lover (while he watches, participates, or in private) my American Gigolo and Cuckold series are for you. Maybe you are a man that fantasizes about watching your wife/girlfriend with another man? If so, you will also enjoy these series. The American Gigolo series is focused on my time as a “Select Male” (also known as Alpha Male or Bull) called upon by women in times of need. This is how it began…

Hi Michael, I’ve been fantasizing about something and need you to satisfy my curiosity. Have you ever measured your cock? Length and circumference? As you know, Roman has a fantasy of watching me with another man and I am considering the possibility if you would be interested. So…think about it.  Just a few thoughts and fantasies….

Take care and stay warm! Jenna

Jenna and Roman are a beautiful, highly-educated couple. In 2004, they were both in their late twenties and newlyweds setting out on a naughty adventure that included some exhibitionism and exploring his fantasy of watching her with another man. When I first met them, Jenna wasn’t quite ready to take this large step in their sexual relationship. She loved Roman and being with another man while he watched was a weighty decision. She worried about the consequences.

What if it wasn’t as exciting for Roman as he imagined and damaged their relationship?  Once done, there was no going back and pretending like it didn’t happen. While the idea of being with another man excited her, she was truly doing it to please him and spice up their sex life. It would become part of their history and experience together, and she needed to be sure.

As for me, this was my first time being courted by a couple for this type of service. Despite my lack of “practical” experience in this situation, I was well versed in the dynamics and erotic layers of the cuckold fantasy they wanted to experience. I understood what my new “friends” wanted and…I know my way around a woman’s body. I was confident I could give her and him exactly what they needed.

My first awareness of this sexual fantasy/fetish came as boy when I saw the movie, American Gigolo. One scene in particular resides in my thoughts still today as a blurred memory. It seems like it was near the beginning of the movie where the gigolo (played by Richard Gere) is fucking a woman. The camera pans in the scene and reveals another man sitting in a chair watching the scene unfolding before his eyes. The other man is this woman’s husband.

As a kid, I wondered about the man in the chair and the pain he must be feeling seeing his wife being taken by another man. I could see though at he was also enjoying it. I could sense his emotional and sexual connection to the moment. I imagined the gigolo’s pleasure too but sensed the superficiality and lack of emotional connection in his experience. Despite that, I sort of idolized the level of sexuality he had attained. He was fit, stylish and had an awesome car and seemed to be “living the dream”.

I don’t think it is a stretch to suggest many teenage boys harbor similar fantasies of being in high demand for sex. It seems we exhaust ourselves chasing the girls. What would it be like to have women and couples pursuing me for sexual pleasure?  I was just a boy having these thoughts. What would I need to do to find myself in such a position?  What form would I need to take as a man?

I knew early on this potential evolution would only be a facade. My inner spirit was gentle, kind, and sensual. I once failed a science project which required an insect collection because I couldn’t bring myself to kill the insects I needed for my collection which included a butterfly. Butterflies have always seemed magical and stir my soul. Like a butterfly, I too would morph but my metamorphosis would be a mask. The gentle, adoring boy would always be my true self.

Time passes and I spread my wings.

After my initial contact with Jenna and Roman, we stayed in contact and shared some erotic stories around what it might be like for the three of us. Then, Jenna sent me the email I opened this story with:

Hi Michael, I’ve been fantasizing about something and need you to satisfy my curiosity. Have you ever measured your cock? Length and circumference? As you know, Roman has a fantasy of watching me with another man and I am considering the possibility if you would be interested. So…think about it. Just a few thoughts and fantasies…. – Jenna

I was humbled to receive this email. I knew this was a big step for them as a couple and for her personally. I also felt honored that they had chosen me to be their “select” male. As I mentioned earlier, she was a twenty-something blonde bombshell and her options for men to fulfill this request were endless. It seems I had finally attained that vague status of sexuality I had envisioned all those years before. In doing so I had become a high-end, fuck toy. I’m sure they enjoyed my company and personality but she wasn’t looking for a boyfriend. She was looking for a man to fuck her in front of her husband. Nothing more.

I am fascinated and turned on by cuckolding as a form of sexual play and wanted to have this experience. I wanted to know how it felt like to be this man…and to see what it was like for the cuckold couple. It was intriguing to have this gorgeous woman asking me for my cock measurements. I wonder how many woman think about this in general and, more specifically, during cuckold sexual play with the desire for “more”? Maybe cock size is something most sexual women think about and it felt liberating for her to come out and say it? Or, was this something she wrote just to turn Roman on? If a man has a cuckold fantasy, it is definitely a turn on to have his lover reaching out to another man…even more so to be asking about his cock size. Jenna and I messaged back and forth and she shared this:

Michael, as far as your questions go…I guess to be honest I have always enjoyed the fantasy of being with another man while Roman watches or joins in but I have been hesitant to fulfill it and it isn’t something I want to do regularly. However, this is Roman’s biggest fantasy and I feel that I’m ready to fulfill it with the right person. Even though we haven’t seen you in a while, we really felt like we connected with you and I have fantasized about your cock since then. – Jenna

Whew, who hears these type of things? It was crazy to have another man’s wife admitting that she has been fantasizing about my cock. It is worth highlighting a subtle point here.  Jenna is fantasizing about my cock, not me. She is making a distinction I suppose that protects her emotional boundary with her husband. I represent sexual pleasure to her, not love or affection. Every couple has their boundaries, at least they should.

I sent her my measurements and accepted her offer. I will continue this true story in an upcoming post titled American Gigolo: Rise.