Chapter 8: Indecent Proposals I Didn't Resist

Bill and I comfortably and openly discussed our sexual fantasies all of the time. Bill was quite unapologetic to admit he could get a hard-on just thinking about a ‘tranny’ who looks like a beautiful, voluptuous woman from the waist up, but who is stroking a huge, erect cock. These men are referred to as ‘passable’ trannies because they can ‘pass’ as beautiful women.

Transvestite prostitutes have been known to fool unsuspecting men who pick them up thinking they have just scored a stunning woman.  You might recall in 1991, Danny Bonaduce, the red-head, freckled face child star from the Partridge Family, was arrested for beating up a transvestite hooker, Darius Barney, in Phoenix, AZ. after learning his pickup was a man and refused to return Danny’s $40.

 Our sexual fantasies only had a few things in common.  We were both interested in a threesome, but while I was interested in another woman, Bill was interested in a threesome with another man. Bill did not divulge this preference right away. It would be six months after we were married in 2015 before Bill would suggest it after posting a profile on a few swinger websites for another woman to engage in pegging Bill produced no replies. Bill made it clear he was not interested in another couple because most of them would want some form of ‘swapping,’ and he was not at all agreeable to see me with another man. Besides profiles on swinger sites, we also visited a local adult club, but Bill walked in with the demeanor of a cop and was so uptight that neither one of us enjoyed ourselves, and we never went back.

At some point, Bill suggested we try poppers. I learned that poppers are a slang term for a class of chemicals called alkyl nitrites that create a ‘high’ or ‘rush’ when inhaled. Poppers not only have a euphoric effect, but they also relax specific involuntary muscles, such as the anus and throat.  They are commonly used in the gay community and can be purchased legally online or in sex shops. I was never a heavy drug user and did not like the idea of inhaling anything, much less something that is sold as ‘video head cleaner.’

As is my nature, I conducted research. I learned that the Merck Manual of Diagnosis and Therapy reported insignificant hazards associated with inhalation of alkyl nitrites, and they are placed among the less harmful of recreational drugs. [1]

Poppers generally make you feel dizzy or woozy and your face becomes flushed. Some people report that poppers don’t necessarily make you horny, but I experienced a strong head rush and a loss of inhibition that made sex extremely powerful and intense. In a sense, they do make one horny because of the heightened sense of arousal and sexual excitement you feel. (I found the morning after headache not worth it.)

All the experimentation with poppers, the increasing size of our sex toys, and the frequency of their use made traditional intercourse seem boring for Bill. While I was thoroughly enjoying my newfound sexual freedom, I was beginning to miss the intimacy of making love with a man you care about and with whom you hope cares about you beyond your willingness to strap on dildos.

Eventually, Bill got the nerve to ask what I thought of the idea of trying to find a man as a play partner. Knowing Bill was staunchly against me being in a sexual situation with another man, I knew right away the idea was aimed at finding a play partner for him. Bill claimed he had never been with another man, and I naively believed him.

We talked at length about what this scenario would involve. Bill easily expressed the desire to find another crossdresser or at least a guy who would be open to him being dressed and willing to stroking each other, sucking each other off, and perhaps being pegged by me playing the dom.

Being so eager to please Bill, I agreed with only a slight hesitation. I expressed my concerns that going from large, rubber, squirting dildos to the ‘real thing’ may cause Bill to like the ‘real thing’ too much and would anything but a real cock be a disappointment. Bill assured me that could never happen, so we set forth the boundaries and rules of engagement and even came up with a safe word if either one of us got uncomfortable we could signal the other to stop or change directions immediately.

Instead of using the swinger sites we had been on, Bill suggested we use Craigslist Personals[2], which I had no idea existed. (Oh, how naïve I had been all those years!) I thought Craigslist was where people went to sell used cars and furniture – not to find sex partners.

Bill pulled up the Personals section, and I was shocked at the nature of the propositions, the ads’ graphic descriptions, and the sexually explicit photos that Craigslist allowed to be posted. When I asked Bill how he knew about these swinger sites, adult clubs, and Craigslist, he always associated it with his police work and undercover missions. However, when he wrote the ad, he seemed to know exactly how to use the filters and craft it in the familiar language of this unique community.

Within 24 hours we had multiple replies. One response seemed to be exactly what Bill was looking for.

[1] O’Malley, Gerald F.; O’Malley, Rika (January 2016). “Volatile Nitrites”. In Porter, Robert S.; et al. The Merck Manual Online. Merck & Co. Retrieved 2017-09-16. 

Nutt, D.; King, LA.; Saulsbury, W.; Blakemore, C. (March 2007). “Development of a rational scale to assess the harm of drugs of potential misuse”. Lancet. 369 (9566):

[2] In March 2018, Craigslist shut down its “personals” section to avoid potential criminal and civil liability after Congress passed the Fight Online Sex Trafficking Act.