Suddenly single, I found myself taking stock of my situation and where my desires should lead me. I knew what I wanted. I wanted to be another man's wife. Yes, that is a very gay thing to say, but it was what was inside me for so long. Earlier in life as my sexual journey evolved, I had incidences of having sex wearing panties and dresses for other males in high school and college. Due to family and societal pressures I always denied I might be gay and did everything to prove to myself and the world that I wasn't gay, even marrying a sweet young woman.
While married, I had a number of clandestine encounters with other men while I cross-dressed. The exhilaration I felt about having sex with a masculine man while I was dressed in women's clothing and how feminine it made me feel really defined my sexuality. I never viewed myself as trans, I just really relished the sensation of being a feminine acting homosexual.
One-time sexual encounters with anonymous partners were very shallow and for me, unsatisfying. I would rather have had a few encounters with the same guy than many encounters with many different guys. The one thing missing was any emotional connection, any continuity. I would have rather had a boyfriend who knew me and wanted me. While I was married, I did have a wonderful affair I had with another married man, that told me what was really in my heart.
There are a number of labels that are put on men who cross-dress for sex with other men; sissy, faggot, queer, fairy. These labels didn't particularly bother me because I am comfortable in my acceptance of my type of sexuality and I feel no shame that I have effeminate tendencies when it comes to sex. I have had sexual encounters with other men when there were no panties, no lingerie, no wig, no props yet my sense of femininity was still there. Having sex with a man always made me feel feminine.
There are "flaming" homosexuals who come off as blatantly over the top gay. With eye makeup, a lisp in the voice, a female scarf over boy's clothing, this is the stereotypical 'fag' society loves to make fun of. While I love wearing makeup, love acting fem and act faggy with a silly lisp at times and might lean androgynous, overtly that was not me. If you met me on the street or in a workplace, yes you might have imagined that I am gay; I was not the most masculine looking guy around.
Some people would peg me as gay while I was in denial that I really was gay. More than once, pompous Alpha males pegged me as a fag. After several years of marriage my wife didn't think I was gay, though as our marriage fell apart, she suspected and confronted me on this. Deep down inside, I came to know I was feminine and gay. Even being barefoot in jeans and a tee shirt and being with a guy I always felt feminine. It was always what I wanted; to be a masculine man's clingy, gay boyfriend, always wanting to take off my shirt and be topless for him and open up my jeans so he could fondle my cock as we kissed, to make me his girl.
Thinking back, I was always a bottom. Long ago there were these gay chat line numbers to call to hook up or phone sex with other guys and the other guys would ask "are you a top or a bottom?" Took me a while, many years in fact, years into a marriage to a woman to realize I am a total bottom. While married to Susie, the opportunity to cross-dress and explore my femininity blossomed. During this time, I had quite a number of anonymous sexual encounters with other men while crossdressing. It was one thing to put on panties and lingerie then masturbate. To learn makeup skills, learn how to walk in high heels, put on a dress (and look hot in it) and a wig and do this for sex with another man, that is another thing entirely.
There is a saying - "It is politically incorrect but factually accurate to say that cross dressing and homosexuality are closely related." I could not agree more. Straight men do not wear women's clothing to have sex with other men. Most gay men do not wear women's clothing to have sex with other men. Many crossdressers who are closet homosexuals do, and that was case with me. But it was more than just the women's clothing, it was how I felt inside. Even not wearing panties, makeup or a dress I still felt incredibly feminine climbing naked into bed with another man. A lot of bisexual men like to play with the cocks of other men, but have no desire for intimacy with another man. Not me, the way I would hungrily kiss another man and how feminine it made me feel was a strong indication how gay I really was.
So, knowing all this and being free to pursue my desires, I knew how I wanted to proceed. I did not want anonymous sex with strangers. Did not want to go to a gay bar to meet men. I was patient. I wanted to date and find a nice guy. What was my plan? Match.com. Yes, Match.com, old fashioned but reliable. I could put out there who I was and what I was looking for and take it from there, take my time, date and see what shakes out. Here was my ad:
"Tall, thin (5'10"/140lb) male 31, looking for a nice guy who knows how to treat a femininely inclined male like a lady. Equally comfortable in jeans and a tee shirt or panties and a dress. I'm a total bottom and quite possibly "wife" material. I know this is shallow of me but I am a size queen."
I left it at that and figured that was enough to get things rolling, I could screen the responses as they came in. And boy, did a lot of responses come in! I only posted a few pics, some were of me in "guy" mode but I also posted a few glamour shots of me all dolled up in a dress, heels. a wig and perfect makeup. I was flattered I received so many responses, I had the pick of the litter. I also had a plan, wanting a lasting relationship more than just fleeting sex. My method was simple; date with the 1st date being at neutral site like a coffee shop to break the ice. Talk on the phone after that and let the man take the lead on suggesting/asking out for a second date, and if there seemed to be enough chemistry, he could take charge for a third date.
And in the initial contact with my suitors, I let them know up front there would be no sex on any of the first three dates. I knew that if there was any spark or potential there would certainly be a "goodnight" kiss at the end of the second or third date. That was my plan and I stuck with it. The first two dates I would be in male clothing and also the third date more than likely as well, it would just have to be how I felt about the guy, what we would be doing, where we would be going.
Despite maintaining a male-to-male persona in this dating ritual's early stages, I knew that if it ever got further and the opportunity ever presented itself for me to dress femme for a suitor would be lightning in a bottle. In past experiences dressing femme around other males my true nature blossomed. Though I fought it that I might be gay all my life up until deep into my marriage with Susie, in the back of my mind something told me I was really gay. Perhaps the two incidents incidents of cross dressing and having sex with other guys galvanized this behavioral sensation in me. One incident was in high school, the other was in college.
In this less than "organic" method of online dating things started slow and I was leery to proceed too fast. There was a half dozen "first" dates at coffee shops and a few "second" dates at various locales but nothing seemed to be clicking. Tony, Jason, Martin, Andrew and John were some of the first and second dates. Martin seemed like the best prospect and we actually hit it off pretty well but after the second date on a bike ride in City Park, I never heard back from him.
Tony was very interested and we actually had a third date which ended in some kissing and heavy petting. It took everything I had in me not to have sex with him, but in the back of my there were a few dots that I could not connect. Something told me that sex with Tony would be heaven but a long-term relationship would be less so. Still, Tony was pressing the issue when Martin called me nearly a month later while Tony was still in the picture.
Seems that Martin had some loose ends with his ex-wife and teenage daughter to deal with in the middle of a calamity of events at his tech firm. He was sincere and apologetic asking if he still had a chance with me. It caught me a little off guard but something about what I felt inside led me to a third date with Martin. After a casual meal and a stroll through the shopping district we ended up hand in hand in a gazebo in the park on a fall evening. It was warm but a hint of crispness in the air as we leaned together on the railing. I felt like a girl; I felt butterflies in my stomach as Martin put his arms around my waist and pulled me close.
A soft kiss followed by his nuzzling my neck and face with his short scruffy beard led to a hungry, passionate kiss. Any trepidation I may have had about Martin evaporated as we romanced like teenagers in the gazebo. Certainly, I felt a spark with Martin that any of the others failed to ignite. In our kissing and petting we could both feel each other's hardness. With his mouth forcefully on mine and his manly paws grabbing my ass cheeks through my pants our passions were close to spilling over. Remaining true to my plan I found a way to disengage somehow without being total slut and blowing him then and there. While I wanted Martin to want me, like any good girl I was not going to throw myself at him, he'd need to earn it.
Nearly fifteen years older and taller than me, stockier and hairy, we were very opposite in terms of masculinity; he came off as very masculine, even with short greying hair and receding hairline his piercing blue eyes and wry smile seemed to tickle my sense of femininity. I was the opposite at best; still boyish, nearly hairless even when not shaving, lithe, soft features and looks that were overtly androgynous. If Martin was a gay man seeking attraction to an equally masculine man, it certainly would not be me.