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Advice needed

Discussion in 'LGBT Later in Life' started by Toromova, Feb 10, 2018.

  1. Toromova

    Regular Member

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    Location:
    Virginia USA
    Gender:
    Male (trans*)
    Sexual Orientation:
    Questioning
    Out Status:
    Not out at all
    Wow, where do I start? Maybe I’ll start with my current situation. I’m 43, good looking, married for 20 years, fairly successful at business, and unsure whether I am gay.

    My wife and I have not had a great marriage but we’ve been there for each other through good times and bad. We have both been mean spirited, loving, attracted to one another, and experimental in our sex lives.

    For me, it started when I was very young. Only about 5 or so. My older brother wanted to play a game. We would dress up as our sisters. He would be the oldest and I would be the younger of the two. I was the youngest of 5 kids, I did whatever my brother wanted. We stopped that after long but strange things kept happening around the house. My sisters’ things kept coming up missing and mis-sorted laundry couldn’t explain it all. I had no idea it was still happening but talk amongst siblings soon turned to the idea that there was a problem. One day while alone in the room we shared I found his stash. It was all silky and frilly things my sisters had “lost”. I remember touching it and feeling it and the uncomfortable urge to try it on. I fought that and came back to his stash a lot. I acted to myself like I was checking up on him but I was drawn to those girly clothes. It kept eating at me until I had to give up the fight. I started trying all of these things on. I wore the undies and nightgowns, their pink and yellow and blue silk things. I loved it. I remember thinking I was not really crossing a line until I tried on one of their training bras. That seemed like a line because then I was wanting to be an actual girl. To have breast like they did. I remember getting into a fight with my brother and calling him “fag” and telling him “you know what I’m talking about” and he did.

    One night when I was about 12 or 13 while he was out, I was home and dressing. He had stolen a pink and white flannel nightgown from one of my sister’s friends who stayed the night. I remember her wearing it and here it was for me to try on. I dressed and stuffed my little bra. I was going to lay down and act like I was her but I fell asleep. As I said before, we shared a room and he came home. He saw me laying in bed with my nightgown on. The next morning I snuck it back in his stash before he woke up. I avoided him all day and wouldn’t dare give him the chance to look me in the eyes. When I came home that Saturday from being out with my friends all day, I found the nightgown folded neatly under my pillow with a note that read “I saw you last night wearing this, now who’s the “fag?””

    Fast forward a few years, I was totally interested in sex now. All of my thoughts and actions led to how I would hook up with a girl. How would I see a girl naked? I learned to masturbate and while doing so I thought of being dressed as a girl. The two things were invariably connected. I was always sexually excited while dressing and more times than not dressing caused me to jack-off. There had always been a thought in the back of my mind that being a girl meant I’d have to have a boyfriend. As I rubbed one out though for the first time I thought of nothing but the idea of having a guy blow me. I remember having the most powerful orgasm and afterwards feeling so guilty. I wasn’t gay, I was totally into chicks and I only thought of that because guys always want to have sex and hooking up with a dude would be the easier way to do it. At least that’s how I rationalized it in my mind.

    Many times I dressed and got caught by my brother. Always sleeping, or pretending to be asleep. Always intentional. I don’t know how many times one of my other brother or sisters or parents were actually the ones who walked in the room. Me, laying there half covered in one of my sisters’ nighties, panties, or bra. At the same time my lustful thoughts were of guys, I entered my 20’s in the Army, away from home, and banging every girl I could. I was smooth, charming, and good looking. I was confident and cool. I was a US Army Paratrooper in the 82nd airborne. In shape, single, an loved to get drunk. So many times though the thoughts always returned to guys. I was not in a place, even when I had my own barracks room that I could still dress up. But I could whack-off all I wanted to and more times than not it was to thoughts of some mythical guy who was about the same age, height, weight, and look as myself. Maybe that’s narcissistic but that was my ideal man.

    I would drive to my hometown every chance I got, hanging out with my old friends and get drunk. Always looking for the next hookup. I had sex with dozens of women. My numbers were always better than my buddies. Not just in quality but quantity. While driving home one time I saw a porn shop. I would go in and check it out on my next trip, definitely. Every trip I would know it was coming up and say I’d do it but I’d chicken out. Finally one time on the way home I had time and I stopped in. They had the video booths and sex toys, movies & lingerie. I bought the tokens and went to the booths. It was the first time I had ever seen gay porn. Ever seen two guys going at it. It was the early 90’s before the internet was in everyone’s hands. I loved it. I had never felt like I did seeing it. It was all I thought about. I was obsessed.

    On one of my trips home I was going to arrive too late to hang with my buds. We had a guy my parents knew who would always buy us beer for a few extra bucks. I also knew he was gay. It was never talked about but when we were late teens he had hit on a buddy of mine while really drunk. It wasn’t unusual for us to stop by his place late and run him to the liquor store. So when I decided he would be the one to take my gay virginity he had no idea why I stopped by his door. I stopped in like a friendly visit. He offered me a drink and we sat at his place getting drunk. I finally asked him “are you gay?”. He hummed and hawed around the subject until I told him I knew. He caught on and asked me “why did you want to know this?”. I fessed up and told him I wanted to try sex with a man. I had never done it before and I wasn’t as much attracted to him as I was the idea of doing it. We got naked and had sex. I was younger he was older. He was a skinny 6’2” and I was a skinny and short. I guessed it was just assumed that when I told him I wanted to try anal that I was the bottom. It hurt and I didn’t like it. How could this be enjoyable? We finished and I left, I felt guilty and ashamed. For some reason I went back to him many other times.

    At the same time I knew I had my newfound sexual freedom. I went back to the base and the town we were in had a large underground gay and trans population. Our “safe sex” briefings every year told us about the prostitutes as if letting us know exactly where to find them. The trans prostitutes would hang out along the main drag (no pun intended) tempting me every time I drove by. I would see them there and never work up the courage to stop by one. Sure enough I got by that as well. One night I saw a large black “woman” selling her wares along a side street. I pulled up and she got in. She looked every bit like a woman except that it was obvious she was a transsexual. Being young and innocent I could always play it off that I didn’t know. I paid her $20 and she gave me oral in my car. I was then hooked.

    I would sneak away from my buddies on base every chance I got cruising the strip. Usually driving up and down there enough you’d have someone in another car to give you a look. I had never acted on them until the one night I met “Janice”. She was pretty in an unconventional way. Slutted up just enough that you knew what she was out for. She waved me to the side of the road and we parked in a parking lot and talked. As soon as she talked it was obvious what she was. She talked me into going to an ATM and I followed her to an out of the way place and she gave me oral sex for $40. While she did it she did something nobody had ever done, she took her finger and started to rub a place that most girls would never think of. I remember asking her right before we started “you’re not a dude are you?”. She said “no honey, you got nothing to worry about”. I knew what she was and I didn’t care.

    After several hookups and my first threeesome (all guys) I was out on the strip every chance I got. I’d meet a guy, hook-up, feel guilty, swear off of it, and then do it again. Meanwhile every chance to go back to my hometown I would. Some trips involved getting there at the right time and hookup with the older man who took my gay virginity. Being the bottom always still hurt and I still enjoyed being the submissive. One night off base a few months after meeting Janice a burgundy Camaro pulled along side me. She waved me over and I stopped. It was Janice in a new car. Business must’ve been good, we went to a house she knew of. She asked how much she charged me last time and I told he $40. She said ok and started doing her thing. Again with the finger in a most inappropriate place. I said “you did that last time”. She said, “and did it feel good?”. I told her yes but that it wasn’t something most girls would do. She said “I’m not like most girls”. I asked her what she meant and she said “remember what you asked me last time we were together?”. I said yes and acted incredulous. I said “you’re not are you? Oh my God I can’t believe I had sex with a man”. As if I hadn’t done it before. She was sweet and reassuring, she showed me her driver’s license that showed her sex as “F”. She said she had just not had her “bottom surgery” yet. So excited I told her, there’s another $40 in my pants if I can see you all the way naked. She told me to wait a minute and I did. She left the room for a few minutes and came back in. She was standing there in a bra and panties I could tell she had real breasts. I asked her to take it all off and she took off the bra, she pulled her penis out of her panties and I could not shut up about how hot this was. She smiled and even though I was paying for it I think she knew what an experience this was for me. Seeing a naked transsexual for the first time. She said “do you want to suck it?” and sheepishly I said yes. I hesitated acting like it was the first time I ever did that. I said something dumb like I was going to try to do it as well as her or some other girl who’d done it to me. After a while she gently rolled me over & proceeded to have sex with me as the bottom. It was great and we finished and she held me in her arms. She asked if I was ok and I said yes. I told her how hooked I was on this now. I even asked if she had a boyfriend. I know, asking a prostitute if you can be her boyfriend is like asking it if a stripper but I was young and infatuated with her. Another time One night a few months after that the same burgundy Camaro pulled along side me. The two women in it waved me over so I stopped. It was Janice and she had a friend with her. She asked if I wanted to go to her place. It was a trailer in a scruffy part of town. We went in and to this day it was the best sexual experience of my life. The two women proceeded to use me as their play toy. They put me on bottom and I serviced both of them for at least three hours. Janice had asked at the start how much she’d charged me last time and I said “$40 bucks, I always carry that much on me when driving through here just in case I see you”. I explained I didn’t have enough for both of them but I know she didn’t care. I know when someone enjoyed it and she enjoyed using me. Unfortunately that was the last time I saw Janice. She actually sold the car and the trailer to the other girl she was with. Last I heard she had met another man and he paid for her bottom surgery. I hope she is happy. Nonetheless the other girl fooled me one time while she was riding with another trans woman. The third girl had not really started her hormones yet and at that point may have been considered a crossdresser but I’ll always remember her as a woman. They too took me back to that trailer and had their way with me. The girl in the Camaro left and while we were there we talked. She asked me if I wanted to go out some time. I couldn’t believe it. All the guys she had and she wanted to date me. When we were supposed to go out on our first date it was a to a gay club. I chickened out and dropped her and another of her friends at the door. I called her one night and she told me to come by. I was waiting for her and her friend came on to me. We had sex and I thought it would be secret. But her friend told and she dumped me. I don’t remember her as fondly as I will always remember Janice.

    Another few years passed and I did as expected. I met a woman and we had great sex. I was not only attracted to her but I fell in love. She had deceived me not telling me she was still married. She had three kids & was running around on her current husband who was abusive. We made plans to get married but that fell apart. She told me she got the divorce and we got married. She wasn’t divorced yet, but when the marriage certificate showed up he finally did it and left her. I had transferred bases and moved her with me. I found out her deceit and early on the trust was broken. We stayed together because that’s what Catholics do. I raised her kids as if they were my own. We still had great sex and were wild and experimental. Our favorite was “shameful sex” because we were both embarrassed to look at each other the next day. One time she was telling me she would want to see me with another guy. I asked her if she would get with another girl and she said “yes”. I got her to admit she had tried it once before. She said two of her friends had talked her into it one night. After talking it up for a while I told her I had something to tell her. I admitted I had sex with a guy before. I lied and told the story of the threesome. We decided we try swinging and that we’d try it with the same sex. In swinging it’s always assumed only the woman is bi. Bi males in that community are pariahs. We found couples with the same interests and fooled around quite a bit in our late 20’s. We aged and got away from it. But I was always thinking of men. There was something else…

    Some secrets are too dark even for couples that are sexually liberated. She had put a pair of panties on me once but I wanted more than that. Much more. Any chance I got, only when it was extremely safe, I would put on her lingerie. As we got older and in our 30’s we took a lot of drugs. Once on a coke binge I admitted to her that I had not only had sex with those two guys before we met. I told her it was a lot of guys. Maybe 20 or so. She asked if that was what I preferred and I said no. At the time that may have been true. I never admitted my love for women’s clothes. 10 or more years has passed since then. I’ve done all of the things married closeted guys do. I have traveled and screwed around. I’ve snuck chances to dress in her clothes. I’ve snuck off and met a few other men who like to dress up, and I’ve grown deeper into wanting this all of the time.

    There are times when I think I’m gay, times I think the dressing is something much more and that I want that. What there are not anymore are feelings that she is all I want. I’ve resolved myself to the fact that I’m going to have to tell her. I used the drugs to hide my disparity but I’m off them now. I didn’t mean for this to read like a letter to Penthouse. The sex stuff was important to my story. I just have to know what people think who are like me, should I come out? I’m about 80% sure I’m gay. The only hesitation I have are the consequences of coming out.

    So what do I do?
     
  2. BiBiBaybee

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    Many believe that sexual preference is a point on a spectrum from hetero to gay, and for me the actual locus changes. Some days I'm more gay, and others, I'm leaning toward the other end. The actual variance has other poles, other than gay or straight, but the actual identity for me would be the same. That was a lot harder for me to accept than the old fashion notion of binary choices. For years, I could not accept that I could be in between!
    Gender identity may have similar variation, but most people have a strong feeling where they are.
    Maybe you are in a similar position.
    Have you thought of posting your story in a separate thread?
     
    Richard321 likes this.
  3. Toromova

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    Well, posting in a different thread is an idea. And I get that you don’t have to be one polarized side of sexuality. The more immediate concern is, one, I definitely couldn’t ever tell her about cross dressing or that I could ever feel like I was possibly trans. Two, I grow more towards that polarized side of being gay with each passing year. Maybe my orientation is just more solidified, whatever it is, is it enough that I should tell her that? Should I break up a 20 year marriage? Is it selfish of me to even think of doing that? Should it matter how I feel if I don’t take her considerations into it? How would she live knowing that she lost me to other men? Would it be demeaning, demoralizing, depressing? Alliterations aside, is it the right thing to do?
     
  4. NoName87

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    It is selfish to live a lie for a feeling of security at the expense of others. I realize that now.
     
  5. Toromova

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    I do not disagree with you, that would be selfish. But it’s not my security I worry about, it’s her’s. Is it selfish or selfless to live a lie for her security and her sense of self worth? I wouldn’t be offended if you answer this question honestly, do you think I live the lie for her security or my own?
     
  6. NoName87

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    If I were to sort this out, my logic would be as follows: It would be selfish if your lie is negatively impacting her. Is she unhappy? does she sense you are becoming more distant? Is it making her insecure? Those are the questions I would reflect on. If no and she can ultimatley remain blissfully ignorant then by all means go for it and live a selfless life.

    To answer your second question it is probably both. To expand and reiterate the lie will always plague you it will only plague her if it begins to negatively impact your marriage.

    Hope that helps
    Be strong, be present, be honest!
     
  7. Toromova

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    I appreciate your honesty, I’m not afraid to hear constructive comments. I hope that those will always help me to get better. I believe there will be no way around the hurt when/if I come out to her. The only choice I have is to mitigate that hurt either by softening the blow as much as possible or not striking the blow to begin with. Sacrificing my own happiness for her’s may never hurt me or it could be corrosive. I hope that if I decide to hold it in it’s not the latter, because I’m sure that will make it worse.
     
  8. NoName87

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    Best of luck
     
  9. Toromova

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    Thank you for that and for your insights. They were helpful.