My First Time, Yes, THAT First Time

In the interest of complete honesty my first time as described here was not really my first time.  Fifteen years earlier as a young man of twenty-five I had gone to a gay bar to take in their drag show.  One of the performers and I ended up going back to her place after the show and I lost my anal virginity that night.   However, that was the choice of a young man confused by his sexuality who was weakened after a night of drinking.

In the 1990s the challenge for transgender women and crossdressers was that they were generally not welcomed in straight club and totally unappreciated in gay clubs.

Fast forward, fifteen years, I am once again out at a gay bar.  However I am not there as Glen.  I am there as Veronica.  Sitting alone at my table, I was approached by two women.  ‘May we sit down?” one asked.  Bringing me up to speed they were out celebrating a birthday as girlfriends.  They fully intended to get drunk so had wisely arranged for a designated driver, the male roommate of one of the lesbians.  He had not gone home but had elected to stay at the club with the women.  Being straight, he was according to the women feeling quite uncomfortable in the bar and ‘not having a good time.’  Then came the reason for their decision to approach me.  “Would you be interested in keeping him company?”  I was open to an introduction and I ended up sitting on a bar stool beside his as we became better acquainted.

When one is in a crowded bar, with the music pounding and the whole place rocking with couples on the dance floor, it is difficult to simply sit and ignore it.  So after he had become somewhat comfortable with me, he asked me if I would like to dance.  I could not have wanted anything more at that time.  As we danced, he made it clear that we were ‘just dancing,’ that he was totally straight.  While I cannot recall his specific words, he added that he loved to dance but he could never dance with a guy.  Whether he realized it or not, it was already conceding that I was not a guy.

At the end of the evening, the four of us went back to his place.   Myself and the two lesbians were drunk and he wanted to catch up with us.  We sat in the living room rambling on about a range of topic, probably none of which made any sense at that hour of the evening.  I cannot recall what expectations I had regarding him when we left the bar.   However, we had spent a couple hours together at the club, danced several songs and had become very relaxed with each other.  Not long after we got to his place, I stood up and headed down the hallway in the direction of the bathroom. After using the bathroom,  peeking through an open door, I saw his bedroom.  I stepped into the room and sat down on the bed.  I was waiting for him so at that point in time I had the expectation of sex.  After a few minutes, I decided to return to the party.

While i cannot say I was quite this bold as I waited for him in his bedroom, that I was in his bedroom at all and sitting on his bed would have been all the clues he needed if he had followed me to his bedroom.

I did not sit there too long before I once again stood up and headed down the hallway.   This time I went directly to his bedroom.  Once again I sat down on his bed and waited.  I waited a bit longer this time, but as with my first visit ended up returning to the party.  I had no sooner sat down when one of the girls said to my new friend, “I think Veronica is tired of drinking and wants to do something else.”  He responded a bit unaware of what that could be so she added, “Well she has already been to your bedroom twice.”

The very next memory I have is of him pushing me face down onto his bed as he began to undo his trousers.  He was straight and I was inexperienced so I doubt that he used any lube.  What happened?  I can recall screaming.  I can recall one of the women in the next bedroom yelling out, “Tone it down a bit Veronica.”  I can recall telling him I needed a break and leaving the bedroom.  I found myself standing in the open doorway of the other bedroom when one of the women said, “Go back to your own fun Veronica.’  I did so.  And we took up where we had left off a few minutes before.

The next time I spoke of a break I told him I had to be getting home.  I recall him begging to ‘let me finish.’  But I was exhausted.  How long had we been at it?  I cannot say.  But we had left the bar at 2AM and it was approaching six when the cab came to pick me up,  He gave me his phone number and I lost it before I could ever give him a call.  I had not thought to get the address of his home.  So we never met again.

I have not gone into much details about the most intimate aspects of this story.  Suffice it to say I had a great time.  It was everything I wanted it to be and yet at the same time left so much more for me to explore as I became more comfortable with my sexuality in the months and years that followed.  Since then I have not been with many men.  However I have never been with a man who described himself as gay.  There have been men who were tagged themselves as bisexual.  But for the most part the men in my life have always been straight men.  And that is just the way I like it.

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