Am I Gay?

By Chris Love

Published on Nov 23, 1997

Transgender

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Am I Gay?

Ok, here's the story and at the end, my confusion. The story is absolutely true in every detail and my dilemma is real. It happened October 31, 1997 in Portland, Oregon. What should I do?

I am 44, married 18 years, and have 4 children, 10 through 17. I am 5'7" and weigh about 155 and am bald in the back and very thin on the top with graying hair. I am a Consultant with an MBA. My wife and I use the missionary position most of the time with me on the top. I like being in control. I have never had an affair of any kind and never had any desire to. This is all told to you to let you know that I am a fairly boring straight arrow kind of guy.

In early October, my wife was talking with one of her girlfriends and decided that we needed more romance in our life. She heard about the "Johnny Limbo and the Lugnuts - Monster Mash Bash" masquerade concert at the Holiday Inn Convention Center and decided we were going. Her girlfriend told her about some kinky sex that she and her husband had done that he really liked. I was kind of skeptical, but decided to go along, because I had never done anything like that before and it seemed like a fun kind of racy adventure (especially when she explained the costumes),.but socially acceptable because it was Halloween.

She was going as a MIB (Man in Black) and I was to go as a sexy Woman in Black. We went shopping for the clothes at Goodwill. Her costume was fairly simple, black pants, coat, tie, shoes, hat, socks, glasses and a white shirt. Mine was rather complex and we shopped for weeks. We ended up with a black velvet dress with puffy lace sleeves that was very form fitting and low in the back, black size 10W high heels, a dark brown longer than shoulder length wig ($90 value for $20 because of Halloween closeout), black tights, red satin panties, a red and black satin bra, a gold necklace, bracelet, and earrings. In addition we bought a ton of make-up at Payless including false eyelashes and finger nails tips. At Payless you can return make up if it is the wrong color, so we figured that we would return all the stuff after the party. Pretty nifty, huh? We matched the nail polish and lipstick and got on the Internet and found out how to hide a beard using lipstick under the makeup and talk like a woman by pushing your voice high into the back of your throat.

After all the effort, I was kind of looking forward to the harmless, totally acceptable role playing. She was supposed to make all the arrangements, just like a man making a date with a lady, and she did, including a motel room at the Holiday Inn so we would have a place to change.

As we started the evening, she insisted that we get into character by her driving and opening doors for me, which we both laughed at. She checked in and we took our suitcases up to the room looking at each other and joking often.

I know nothing at all about putting on makeup. She did it all, started with the nail tips that were about half an inch long and had to be glued on with some filler to make them appear smooth and real. Once on, she put on two coats of color and a shiny top coating. As a final little touch, she put a coat on my toes and I wiggled them admiringly. She asked me several times if I was excited, and I kind of was in a medium soft sort of way. When she was done, I was amazed at the feel of the nails on my hands and kept tapping them on things and feeling the smoothness against my face. They were perfectly shaped and curved, very real looking. Amazing what they can do with acrylic.

She shaved the back of my hands, but that was all I would let her do, because it would be the only thing that would show. She was thinking about shaving my legs and chest, but I only let her do a little at the top of the chest where the dress was cut. I close shaved my beard, which is fairly heavy around the chin and upper lip so she could get started on the make up.

She had me strip and brought out a surprise, which was a red and black satin under thing with a lot of bows. She had to talk me into wearing it as I saw no reason to have it on under the costume, but it was part of the role. This was a little weird feeling, but I had agreed to do it. It snapped at the crotch. We used pink water balloons for breasts with warm water. Later that night, she kept feeling them, amazed that they stayed warm and bouncy all night.

When I had the dress on, I had to admit it looked rather like a female form. The puffy velvet covered up my shoulders, narrowed to form fitting at the elbow, and went all the way to my wrists in lace, making my forearms look narrow. The waist was narrow and I had to suck in to get it zipped. The waist was a little bunched so my hips looked a little bigger than they were.

With my bright red nails, it was pretty effective, although my hands looked a little too big to belong to a real woman. There was a little loose lace from the wrists that came over them and cover them a little bit.

She had me stand in the high heels and walk around. She told me to stand with one knee bent in front, slightly sideways to minimize my profile and walk with one foot directly in front of the other. The heel was only about 2-1/2 inches tall and half inch by 1 inch at the base (definitely not spikes) so they weren't too hard to walk in if I put my toe down first. I was supposed to pull in my pelvis, stick out my butt, push out my chest, and elongate my neck. I got the hang of it pretty quickly.

She wanted to pluck my eyebrows, and I let her do a little, but watched carefully to make sure there was no thin fine line to worry about later, more like Brook Shields. The bangs from the wig would cover most of my forehead and cheeks, anyway. After all that, she put on the make up including the false eyelashes, beard cover, eye liner, shadow, foundation, concealer, lip liner, and lip stick. I don't have definite cheekbones, so she used some dark and light blusher to make shadows to make it look like cheekbones, and finally put powder over the whole thing. She wouldn't let me look in the mirror during the whole process and looked very serious the whole time, like she was painting a picture. I put on the wig and she arranged it, fluffing and brushing and tucking. Finally she put on the jewelry and let me look.

I was utterly amazed. She was dumbfounded, even though she did it. I am not really that good looking, but when it was all put together, I looked pretty good. I couldn't pass for female in the light of day, but in a dark restaurant or the darkened dance hall I knew I would look pretty good and so did my wife. She was feeling very proud at what she had done, but I could see immediate hesitation. We took some pictures for posterity, and I had her take some extra of me.

She asked me if I felt ok going out like that, and I replied that it was just a costume and it was Halloween, so it was fine. She kept looking at me and shaking her head in disbelief. As we walked out the door and down the hall, I remembered all the stuff she told me about walking, standing, and sitting. I coyly took hold of her arm and subtly wiggled down the hall with one foot carefully placed directly in from of the other. We kept looking at each other and giggling, but since I was on the inside looking out, I really couldn't tell what I looked like.

It was chilly that night and we walked across the street to the dance. She gave the guy at the door the tickets and he stamped our hands and we went in. I was holding her hand and let her lead me through the crowd to the dance floor, looking at the costumes as we went, and aware that I was being looked at by others. It felt kind of good to be noticed. We sat at a table by the dance floor, and I tried to make small talk, but she kind of ignored me and looked around at the crowd. I curled a hand onto her shoulder demurely leaning down so I wasn't taller than her and talked in her ear, which she tolerated.

I was really into the role, but she told me that she was kind of embarrassed because she didn't really look like a man, but I really looked like a woman. She is only about 5'5" and about 130 and a very feminine face. She was afraid that someone would think that she was necking with a woman. She was embarrassed, after I had done this whole thing for her. She told me that she didn't like me to use the high voice, so I lowered it, but it kept slipping back into character as I talked, which kept annoying her. I didn't see what the big deal was, because, after all, it was just a Halloween party. Everyone was in costume and in character.

We left the dance to go to dinner back over at the motel. She performed her duties, opened doors, led me in and held my chair. I got a great complement at dinner. There were maybe three couples in the place. The waitress seated us with a smile. We ordered (I used my feminine voice which was pretty good), and she went away. I saw her talking with another waitress and looking at us. She came back and filled our water glass and finally said, "I have to tell you, we knew what your MIB costume was right away, but we were wondering what she was dressed up as until we figured out that she was a he in a black dress. You really look good. We were totally fooled. I was really flattered and flashed her my best smile and blew her a kiss. She laughed, and my wife smiled tensely.

I had two glasses of wine with dinner. I didn't eat very much and after dinner, I volunteered to go get my wife's sunglasses, which she had left in the room. I put on my sexiest walk with a little lift in my step so that my hair would wave and my balloons would bounce, crossed the large lobby, and hopped up the stairs to the elevator. At the room, I touched up my make up, went to the bathroom, gave myself a little grope, tucked myself in and started back to the restaurant. On the way back, I met a couple of guys in the hall and could feel them checking me out. I really enjoyed it

When I got back to the table, my wife complemented me about how elegant and real and sexy I looked, again shaking her head. I didn't know how she was really feeling, because I was so caught up in the act. We went back to the dance with me hanging on her arm.

We went back in and again sat over by the dance floor at an empty table because everyone was dancing. I was really to get ticked off at the way she was treating me. We danced a couple of dances, with her looking everywhere but at me and sat back down. She asked of I wanted a glass of wine and I said yes, so she went over to the other side of the large room and stood in a rather large line to wait for it. She was way across the room and I knew it would take ten of fifteen minutes.

While I was sitting there, it happened. A good looking, 6' tall 190 pound Dracula came over and asked me if I wanted to dance. I was totally embarrassed and I looked shyly down and shook my head no. I felt really hot and flushed. He took my manicured hand and pulled me up and said, "Come on, I won't bite." I had to smile at the line and he took that as an ok. He pulled me really close and put his hand on my waist / rear and started dancing this slow dance. The way he was holding me forced my head onto his neck and my arms up around his shoulders and he kind of bent over and rested his chin on my neck with the hair from my wig between our cheeks. I was scared to death, really terrified. He was taller than I was, and I could feel his telltale bulge just below my navel. I was tucked down into the tights, satin underthing, and underwear, so you couldn't see anything, but I was kind of hard myself. After about 30 seconds, I kind of loosened up and relaxed into him, which was a mistake, because he pulled me so close it kind of took my breath away. I really didn't know what to do. I had obviously had no training for this type of encounter. He kept talking to me in my ear, about how smooth I felt, and how good I smelled (which was my Wife's Lace perfume that she dabbed on me earlier), and rubbing his hands on the black velvet.

At the very end of the dance, he put his lips on my neck and nipped me. I pulled back with a wide-eyed look on my face and my mouth slightly open. He said, "I lied," referring to his earlier comment about biting. Then he pulled me close. My arms were hanging out to the side with my wrists dangling, but one of his was on my behind pulling my pelvis in and the other was on my bare back just below where the hair ended. And he kissed me! Right there on the dance floor for about 5 full seconds. I was stunned.

And I let him, and it was very juicy with a hint of tongue, and it was very very sensuous, and I hate to admit it, but I really liked it, and I kind of moaned through my nose, and I kissed him back. He had no right to do that.

We were right in front of my table, so he helped me sit down and said, "Thanks for the dance beautiful," and walked off through the crowd. I was stunned. Just stunned. My stomach ached and my lips were actually tingling and my knees were weak.

My wife showed up with the wine about five minutes later, and I was still stunned. I gulped the wine down in two swallows. She asked me if I was hot because I looked flushed and I said, "Yes, let's go up to the room."

I felt like everyone was watching me as we left, but of course no one was. He must have known I was a guy, didn't he? I was really confused, in more ways than one. I didn't see him on the way out. He had to have felt my beard. I should have slapped his face. Actually, I should have punched him out. I was also wishing that he would have kissed me again.

We got back to the room and my wife decided to go through with the rest of her plan. She slowly undressed me all the way down to the satin underthing and undid the crotch. She got on top of me and straddled me. She still had on her men's cotton underwear. I was hard as a rock now and instead of our usual foreplay, whenever I went to touch her, she firmly moved my hands back into the pillows so she controlled the whole event. She sucked hard on my nipples just like I usually do with her. She played with my testicles and all around my anus not touching the penis. Then she had me roll over and spread my legs apart with my butt in the air. She slipped a small white tube into my rear that she had pre-lubricated with Vaseline and started moving it in and out as she pressed with her pelvis against me. It felt strange at first, but when I got into the rhythm, it was really stimulating. I was moving in rhythm against it and moaning when she pushed it in and removed the tube. It was a tampon and she had left it in my bottom with the string hanging out. She reached around to grab my crotch with one hand and gently tugged the string with the other. I was out of my mind, and thinking about Dracula as she nibbled on my neck and breathed in my ear.

Then she started laughing and just stopped everything. I was really mad. I asked what she was doing and she told me the she just couldn't do this anymore, it was too much like making love to one of her girlfriends. It was too kinky and too weird, just like the whole evening. She was actually kind of angry with me because I seemed to be enjoying it. She had me go into the bathroom and remove everything, even the nails, and shower. After every trace was gone, we had sex the normal way with her on the bottom and she really seemed to enjoy it, but I was thinking about many other things.

When we were on our way home, she said that things hadn't gone the way she planned. She was jealous that I didn't look ugly as a woman, which she expected. In fact, she was afraid that I looked much better dressed up that she did. I told her that that was ridiculous, but she insisted that I looked like another woman, not like me. She told me that when we got home, we'd better throw all the costume stuff away, so I put it in a big plastic bag and threw it in the garage. I asked her if she might not want to go to another costume party around New Year's Eve if we could find one. She said, "Only with you as a man and me as a woman. Actually, I don't want to go anywhere for a while dressed up at all."

Now for my dilemma. Am I gay? I really liked the whole evening. I didn't think I would, but I did. Am I crazy? Why did I get so into the dance and the kiss? It should have repulsed me. I feel like I want to dress up again, but I know that it is out of the question. My wife has told me in no uncertain terms that she was pretty disgusted by the whole evening. I was happy before, so why did she have to mess with this? I saved the whole outfit anyway. I have secretly dressed up a couple of times since then. I even masturbated with a tampon the other day while I was on the toilet, because I saw them sitting there. I am nuts. This isn't me.

So if I wanted to do this again, is there a guy or gal out there that would help me? Where would I go so I wouldn't be recognized and be safe? Do I have to wait for a costume party? Does anyone else out there do stuff like this? I don't think I would like a guy to kiss me if I wasn't dressed up. I wouldn't mind having a woman do that stuff my wife was doing. I am nuts.

Please write me and tell me I'm not crazy.

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