tagTranssexuals & CrossdressersMy First Transsexual

My First Transsexual


When did it all start. After the first few times with my best friend (Ed), I thought I would try another guy. That went well. By the time I was in my second year of college I knew I was Bi. Being Bi, I think is better then being just gay. You can have men or women. I had had about 6 different guys in college. And about 5 woman. They all knew I was Bi. By my third year I was thinking about a she-male. But it would be a few more years before I would get to go out with one. This is what happen.

After getting out of college I got a job working for the city. It gave me a chance to get around the city. Meeting new people. My job was to inspect houses, both new and old. One day I had to go to a old house near West 98th and Lake. When I got to the door I found a not to bad looking woman. She was about 25 years old. As we talked I kept looking at her. What was different about her. Being Bi, made me look closer at people. Never know when a guy might get lucky.

About a month earlier I met a guy at a house that was also Bi. We had talked and he told me that he knew all about me and we hit it right off. But then this is not about him. But a guy can get lucky.

Being Bi I thought I would hit on this lady. Might get lucky. We walked around the house and I told her the things that needed to be fixed before she sold it. Then, out of the clear blue she looks at me.

"Do you know anyone that can fix things?" Her eyes just looking at me. A soft blue. Her lips had on a little to much lip stick. It made them look real red. Her perfume was just right. Not strong like some woman wear. Light brown hair. And as for what I could see, her legs looked okay. I did look up her dress as we went up the stairs. Long legs, and I thought I saw a garter belt.

"We can not tell you about anyone, that fixes things. Its not right. But what is it that you need?" If my boss hears about this, I'm fucked.

"If you must know. I was just trying to." Her eyes looked away. Then back at me. "I was just talking and."

"Are you hitting on me?" Now it was I that was looking away.

She got a half smile and then looked right into my eyes. "Yes I am, your kind of cute. I was thinking would you like to go." She stopped herself. Her blue eyes moved around some then. "To go out for coffee sometime."

"Great. I'll pick you up at 8, and how about a drink. I never did like coffee. You pick the place." I thought I might let her know right off. "I'm very open minded, so what ever place you like is okay with me."

"What are you trying to say? Are you." She stopped herself. Her tongue wet her lips, first the top one. Then she sucked in her upper lip. Her voice got lower. "Are you gay?"

I got this half smile on my face. Then looking right into her eyes. "No, I'm what they call Bi. I enjoy both. If that is a..."

Her face lit up. "NO NO NO, that is great. I just wanted to let you know." She swallowed hard and then dropped it on me. "Andy, I'm a transsexual. If you would like to back out now is the time."

My eyes never moved from hers. "My dear sweet Tina. I would love to go out with you. I'll see you at 8."

I pulled up at 8 and out she came. Her blues eyes hit me first. Then her brown hair. Then I saw her legs. Long, long legs. She had put on a blouse. Her breast showing. I would say about 34c. A short skirt and black stockings. I got out open the door and she took my hand as she got in. She sat down and then put her legs in. One at a time. This girl knows what a guy likes to see.

One leg in and the other out. I could see that she had on a garter belt with black stockings. But what made me almost drop over was her black lace panties. I knew she was looking at me look at her legs.

"Something you like to say, or do?"

"No, NO, I was just." What could I say. She knew I was looking. And with a smile on my face I just said. "I was just looking up your skirt. Is that okay with you?"

"After our drink you can look all you like."

We went to a bar in Lakewood. We drank and talked. I told her that I had been Bi for years. She told me that when she was 19 she became a transsexual. She was taking shots and that she would never go all the way to a female. As she put it. "I'm having to much fun like this, I'm also Bi."

"Andy, have you ever, you know, been with a... girl like me?"

I was holding her hand. It was soft. I swallowed and looked down at her hand. "I have dreamt of it and thought of it for years. I have dated one but, not that I didn't want to, but we just didn't hit it off. But I might like to." What the fuck was I saying to her. I was asking her out right if I could go to bed with her. "Not that I'm asking you."

"Andy, I think it is time that we." When she said we it was as if the word came out as "WE." "That we should go back to my place. I have all the things that WE need. Would you like that?"

Would I like that. Fuck yes. But then I had to act like it was just okay.

"WE," walked into the bedroom. I had not seen this room before. I looked around. I saw some ropes, a few nipple clamps, about 5 different belts and some poles that looked like broom handles cut up. The bed was a four post bed. It must have been 3 and 1/2 feet off the floor. I looked up over the bed. Not only a mirror but she had about 25 different hooks.

"Andy, you are telling me that you are a virgin when it comes to." Her words stopped, she took my hand, held it and then. "Ladies like me?"

All I could do was look at her eyes. "I have told you that I have done oral and a few anal times' but this is all new to me. Are you going to?"

"No, I'm not going to hurt you. But I like to play games. I'm going to be real nice to you. I'll go nice and slow. I would never hurt you. Trust me."

As she spoke she was taking off her things. Her blouse, then her bra, and she was stepping out of her skirt. Now standing in front of me in her panties garter belt and stockings. All of 5'5" and all I could do was look.

"I'm going to sit on the bed. You undress for me. Do it slow. Let me see each part. Then move on.

I took off my shirt. One button at a time. She looked at my nipples as I open it. Then the belt. I pulled it open and unhooked my pants. I pulled the zipped down very slow. Then I bent to take off my shoes. I opened my pants and let them fall. Now, my shorts I hooked my fingers on the side and pulled down. I shave and I'm soft and smooth, all over. I got them almost to the point that you could start to see my cock and I turned to the side. If she was going to see it was going to take me a few more minutes.

"Stand up and look at me. Turn so I can see what I'm getting." It was more of an order then anything else. I turned to face her.

Her eyes were looking right at my cock. I'm not all that big. About 6 and 1/4" But I think that I can use it okay. By now I was hard. Hard as a rock and she looked right at it.

"Nice, I like that you shave. It feels better when a suck it. And it is also better when you. But not now.."

Tins stood and put her hands on my hips. She knelt in front of me and licked the tip. I felt myself going up on my toes. I took a deep breath as I felt her mouth go down on me. My cock was now about 3" inside her mouth. Her right hand was holding my balls. Her tongue was licking my cock as she moved it in and out. She squeezed my balls and I felt a sharp pain in them.

"No, I'm not going to hurt you like that. If the pain gets to much, just say the word, Parma. That will be our safe word. Now put your ass on the bed, keep your feet on the floor for now."

And that is what I did. Tina was still kneeling on the floor in front of me. Her mouth went back to my cock. I felt like I was going to die. Her mouth on my cock, going in and out of her mouth. Her one hand holding and squeezing my balls, the other jacking-me-off. I put both of my hands on her head. I was now starting to fuck her face. In and out, in and out. Faster and faster. I was going to cum I grabbed her face. She pulled back and my cock popped out with a soft sound.

"Lie back on the bed. Trust me. I have better use for that cum of yours then in my mouth. Safe sex is a must. Now lie back. That way I can." And with that I was on my back. My ass on the edge of the bed. She grabbed my legs and pulled them up. She licked my cock a few times and then my balls. I felt her tongue on my ass. Now this was nice. I love when I get a ass licking. She stood and told me to turn over.

"Put your feet on the floor and bend over onto the bed." The bed was just the right size. I could bend over it and have my feet on the floor. Tina went back to licking me. I could hear her. She was tell me how great I tasted and how she was going to be the first trans to fuck me. All this time she had my cock in her hand. Still jacking me off. I felt her pull away I could her open the drawer. I could hear her open a condom, and put it on. I felt her putting something cold on my ass. It must be K Y.

"Now my sweet Andy. I'm going to fuck you. You need to get fucked don't you?"

"Yes Please. Go slow. Remember I'm a virgin. I'm your virgin. Please don't hurt me." I felt her pushing in. It felt like all the other times. But I knew that it was a girl cock going in.

"You do have a nice ass. Tight. Hot. Smooth. And it is going to get fucked by me. Feel my cock going in? Tell me what does it feel like?"

"Tina, it feels so nice. I can feel the heat coming from you cock. Faster. Push it all the way in. Let me feel you fuck me. Please. Please."

It felt great. It felt like she was sticking in a foot of cock. She went that slow as she pushed it in. Then I felt her balls slap my balls. That is one thing I like when I bend over. I get to feel balls on my balls. My cock was about half hard.

"Now I'm going to fuck you. I'm going to fuck you like you have never been fucked." And she did. Her soft hands held my hips and kept me from moving. Her hips pull back and that shot forward. Her cock came out and then back in. Out and in. Out and in. Slow and then fast. Then faster. Slower and faster. I could hear her, talking and telling me what she was doing.

"I'm fucking you virgin ass. I'm pulling my cock out of your tight ass and then pushing it back in. Hard and then soft. Now I'm going to."

And she did. Tina fucked me like no one has ever fucked be before. I could feel her all the way in my ass. She had only 6 and 1/4" but it felt like a foot. I had tears in my eyes and I knew I would come soon. I only hope that she cum with me.

"Turn over." She pulled out of me and my ass was crying for her to put it back in. "Turn over."

I did and she pull my legs up. With one hand she grabbed a rope with a stick on it. She pulled my legs higher and put the stick behind my knees. She pulled the rope and my legs could stay up without holding them. Not bad I thought.

I then felt her push back in. It felt different. It felt like she had about 3 more inches then before. I could now see her. Her blue eyes looking right at me burning a hole in me. Her mouth open. Her red lips with her tongue licking them. I could see her tits. Damn did they look great. Nice nipples. I thought of what they might taste like. But then I felt her pull all the way out. She bent and took me in her mouth. Sucking and sucking till I had a hard on once more. Then my cock came out of her mouth and her cock went back in.

"Now for the real fun." That is all she said. She fucked my ass for a minute and then grabbed my cock. She stopped fucking me and jacked me a few times. Then stopped that and started to fuck me once more. She pushed and pulled her cock in and out a few times and then stopped. Then jacked me off a few more times. What the fuck was she doing.

I know that when I get fucked I never had a hard on. But she was fucking me and I did have a hard on. I'll have to remember this.

After about 5 minutes of this she pulled the rope. I felt my ass come off the bed. She knelt on the bed and pulled the rope more. I was now on my back with my ass up in the air. I was like bent over. I could see my cock about 5" from my face. I felt her push back into me. In all my years of fucking and getting fucked I never thought of this one.

"I'm going to make you cum. when you cum, I'll cum. I'm going to fuck you and then jack you off. Then back to fucking you. Remember I said safe sex."

I felt her cock going back in me. I also felt her jacking me off. "Yes I remember. Why?"

"When you cum I want you to cum in your mouth. It will feel like I'm coming in your mouth. I'm going to jack you off into your mouth. So open up. Get ready."

Tina went back to fucking me. I could watch her not only jack me off but I could see her cock going in and out. I could see her tits. I could see the look on her face. Her blue eyes looking at me. Faster and faster she fucked me. Then jacking me off. Then fucking, jacking, fucking.

I felt like I was crying. I had tears in my eyes. It felt that nice. Nice is not the word. But it was FUCKING GREAT. I could not breath. Then I felt it.

"NOW..... NOW." Tina fucked my ass faster. How I do not know. But just as I felt myself going to cum I felt her cock go all the way in and stop. I could feel it coming out of her. I felt it from the bottom of her cock till it came out the tip. AT the same time she held tight onto my cock. The first shot I felt in my ass she let go. Not only did I feel it in my ass. But I felt it hit my face. Then the next one. I felt it push deep into my ass. And then I felt a shot in my mouth. Tina was doing just what she said she would. Making me think it was hers. I tasted my cum as she came.

I felt her cum about 4 more shots inside her condom covered cock. I felt myself shoot about 3 more times into my mouth. Some hitting my face. I had my eyes open and just could not believe how it felt. It was like I was sucking her cock and taking her cum. But I felt safe. It looked like she was crying. Tears in her eyes. Her blue eyes looking down at my cum covered face.

"I have never felt anything like that. You my dear are a doll. I only hope that I can do the same for you. But it is going to have to be later. I think I might die if I try it now."

"Andy, we have all night."

And we did. I have never met a woman that could do what Tina did to me. Or a man. But we see each other from time to time. (About ever two weeks). We only have safe sex. But one day I might let her. If I do I'll try to write about it.

If your over 25 years old write me and I'll e-mail you back...

Report Story

byiser21© 0 comments/ 149607 views/ 11 favorites

Share the love

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartRwmstout0904, algolfcrazy and 9 other people favorited this story! 

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: