First times

Do you remember each time that you lost your virginity?
I am not sure that I do. I remember the first time I had sex with a woman, her name was Sally. It was in college and I just really wanted to loose it. She was somebody I barely knew, a couple of years older than I, a bit larger and we had both been drinking. I took her to the house that I shared with several other people and took her to my single bed where we did the deed, it lasted about 3 minutes. I then left her in the bed and went to sleep on the couch. I later learned that another one of my roommates had taken the virginity of another casual acquaintance that same night and yet another roommate came staggering in the next morning having also had a one night stand to get over her ex who had decided that he was gay. I also got crabs from that first experience.
A couple of weeks later, I was hit on by a male bartender at one of my favorite bars. I excused myself and left quickly thinking that would be the end of it and that I had handled myself very well. Instead I was plagued with thoughts of what I had not done and decided that if the situation came up again, I would act on it. After all, I was in college and that was where you were supposed to learn about all that life had to offer. So I went back to the bar a couple of days later and hung out till it was closing time and we went to the office in the basement and had very awkward sex, basically just mutual masturbation. Again I thought that would be that, but being young and horny I went back and we tried several other things. I was also hanging with a very nice girl at the time but we never had sex, not that she didn’t want to, but I figured I should try to make up my mind about what I wanted before I do anything with her as I didn’t want to hurt her. When I decided I was gay, she was the first person I told. It still hurt her.
I remember the first time that the bartender and I tried anal sex. I was on the receiving end and just could not relax enough, I was very scared. I thought that the bartender and I were dating and exclusive but alas one day he announces his engagement to a girl from the college. She and I ended up getting into a bitch fight when she discovered that he also played with boys. Whatever. I left town. He later got married to another girl from college and about 5 years later got ill and died of Aids.
What I don’t remember is the first time that I successfully had anal sex. I know that it was after college. Aids was in the news every day and I was terrified of anal sex, even if condom was involved, so you would think that I would well remember who, when and where I lost that cherry either as a top or as a bottom. For whatever reason, it is gone from my mind, I don’t know if it was good or not. I know that when I had my first long term relationship it was not that big of a deal anymore, I still played safe but I was in love. We were both very proud to be "versatile" but in reality we were both wanting to be tops.
So why is this on my mind? Well, I know that on several occasions in my business, I have been somebody’s first time with another man. I am not their first anal experience, unless you count first prostate massage, but still, in a world of so many firsts, where do I fall and will I be part of that list that they remember for ages to come?
I have seen how my time with a man can change them forever. After several sessions with me, many men gain the confidence to look for male to male sexual experiences on a non professional basis. They will often tell me of their other experiences, good and bad. I have heard from men how they never knew that sex could be that good until they started experiencing male to male sex. I have no idea if any of them have ever found love with another man, at least none have told me about that. I would hate to think that our experiences together lead them to believe that sex with men is to be void of emotions, especially when those that fall for me I often have to end up pushing away.
I have often also been the first extramarital experience for several men, straight or gay. It is a safe place to have an outlet when things are dull at home. Here is where the exchange of money and lack of emotional demands is usually appreciated. Though there have been a couple of these situations where feelings developed over time which made things incredibly awkward. I was suddenly in the roll of a possible home wrecker, not exactly what I had signed up for, and they often feel very hurt.
On the other hand maybe I will be forgotten as well, like I cannot for the life of me remember actually losing my anal virginity. I guess it doesn’t matter, but I do think about it at times.
Though I would never break my self made vow of discretion, I do worry about the wives of the "straight" men who come to me. Knowing that eventually they will look elsewhere for more than I am willing to offer, I hope that they will play safe and not take anything home to their wives. I often feel, and have told a number of them that like to chat, that the wife should be told if man to man sex is something that the husband has decided that he needs in his life. Most will never say anything. I think that most spouses are aware when their significant other is getting something on the side, especially if it goes into the emotional realm. Generally speaking, if you suspect something, there is something to worry about. I believe in open communication so that the spouse can make up their mind what it is that they want. Who knows, maybe they will be fine with it. Maybe they have their own thing on the side. Maybe they are looking for permission to explore their own sexuality, or maybe they want a "don’t ask, don’t tell" policy. You just don’t know until it is brought out in the open. There are number of reasons I hear for not telling the spouse like "I don’t want to hurt them" or "I don’t want them to leave, I still love them" or my personal favorite "the bitch would take all my money."
To bring this around to the beginning, if I am their first, then let me be the first to give you my advice as well. Always play safe and be as honest with yourself and your other as you possible can be.