Long Strange Trip

"But you look like a girl."

"I am a girl."

"But are you a girl there?"

Obviously, he wanted to know what I had between my legs. I still wasn't quite to the point where I'd been cleared for vaginal sex, though I'd been dilating it very regularly. Still I felt insecure and felt his question was intrusive.

"At this point, it doesn't really matter what I am there. If we get to a point where it does matter, you'll know."

"So I would be going out with you not knowing if you're a girl or a boy?"

"I'm a girl, regardless of what I have there. If you have to know that before going out with me, then you shouldn't date me."

"I like you, and want to go out with you."

"Even if you don't know that?"

Tom looked at me, bit his lip and looked at his shoes. He shook his head very slightly, then looked back at me again.

"You'll let me know before we get - intimate?"

"I will."

"I ... I think I still want to go out with you."

"If you really mean it, then give me a kiss."

"A kiss?"

"On the lips."

Tom looked very uncertain. He seemed nervous, then he took a deep breath.

"I've never kissed a girl before."

"Then it's time to start."

Tom's eyes got very wide, as he leaned forward. His lips parted slightly, then he closed his eyes and touched his lips to mine. He didn't do much more than touch his lips to mine, but I leaned into him and kissed him. He began to kiss me back, and after about thirty seconds, I pulled back. Tom bit his lip again and looked at me.

"I enjoyed that."

"Assuming you still want to go out, at the end of our date, you can have a better kiss."

"You promise?"

"Just as long as you treat me right."

...........................................

I still felt nervous, even knowing that Tom knew I was trans. I didn't want him to pick me up at my house, so I met him at a restaurant for dinner. We had a nice meal and then went to see a movie next door to the restaurant. In the theatre, Tom put his arm around me, which made us both feel a little funny. I had not really been close to anyone since Rob broke up with me months earlier.

After the movie, Tom walked me to my car, and we talked for a long time. I realized that Tom was quite shy and nerdy.

"I have to admit, I've never really had a girlfriend before."

"But you've been on dates with other girls?"

"You're the first."

"So were you never intimate with any girls before?"

"None, at all."

"You should know, I'm no virgin. I've been with boys."

"You mean - . How?"

"I'm not going to give you any details, but if you want a girl who's as innocent as you are - that's not me."

"You're still not going to tell me - "

"Before we reach a point where it would matter, you'll know."

"I don't know if I feel comfortable being intimate with someone who is still a boy there."

"I understand."

"I'm not sure - . How would we -?"

I touched a finger to his lips and he stopped talking.

"I think it's time for you to give me a real kiss, and for me to go home."

Tom still looked uncertain as he moved toward me. I grabbed him and pulled him tight to me and lifted my head for him to kiss me. He very tentatively put his arms around me as he kissed me. He wasn't the greatest kisser, but he was sweet. He had one hand loosely touching my waist. I reached down and moved his hand down onto my ass.

Tom made a funny sound as we kissed, but he didn't stop kissing me. His hand rested loosely on my ass, so I reached down and pressed it more firmly into my ass. He kept kissing me, but through his clothes, I could feel his cock getting hard. He tried to turn so it was not pressed against me, but I held him tight so he couldn't.

I loved that fact that kissing me and touching my ass was getting him turned on and hard. I had gotten the okay for vaginal sex from my doctor, but for some reason wanted to take it slow with Tom. We kissed for a little longer, before I pulled back.

"I need to be getting home, but thank you. I enjoyed going out with you and I'm glad you asked me."

"Maybe we can do this again soon."

"I hope so."

I gave him a quick kiss, and got in my car. I was almost floating on air, but was brought back to earth by the thought that as we went along Tom might start to feel antsy about dating a trans woman. Not only that, but some of the other folks at school know I'm trans and might give him some crap about it. Would he still feel the same way if people teased or harassed him over dating me?

......................................

Tom and I began going out every weekend, in addition to studying together. At first I just let him kiss me and touch my ass. After a while, I let him touch my boobs too. I made it clear he was not to touch me between the legs. I wanted to get there and even beyond but after everything I'd been through previously, I wanted to take it slow with him.

"Stephanie, I almost don't care what you have between your legs now. But if we get serious, I hope you're willing to be a girl there too."

"I already am a girl there."

"I'm glad, even though I love you regardless."

"I told you I'm not a virgin, but I am a virgin there."

"But, how?"

"Anal and oral."

"I didn't think about how - "

"You've never been intimate with anyone?"

"No. Does that bother you?"

"It doesn't, and I'm not sure I'm ready to go all the way, but I can make you feel good, If you'd like."

"How?"

We were in a basement room at his parent's house, and his folks were out for the evening. I slid off the sofa and got on my knees on the floor in front of Tom. He looked uncertain, even though I could see that his dick was hard in his pants. I gently spread his legs, moved forward and unzipped his pants. I reached in and pulled out his cock which looked like it was trying to tear its way out.

"Are you sure about this?"

I leaned forward and took the head of his prick in my mouth. Tom moaned and slumped back in the sofa. I slowly took it in my mouth as deeply as I could. I'd never learned to deep throat, but Tom seemed to enjoy whatever I was able to do. I used my lips and tongue, getting it most of the way in, then slowly back out until I had only the head still between my lips.

I did my damnedest to make it slow, sensual, and loving as my mouth made love to his rod. It took almost no time before Tom erupted in my mouth. He had several spurts over about twenty or thirty seconds, and I wanted to get every bit of it. I kept working him in and out of my mouth as he unloaded his cum in me. As he stopped spurting and started to soften, I eased him out, cleaning him off as I went.

I tucked him back in his pants and zipped him back up. Tom almost looked like he was passed out on the sofa. I climbed back up and sat beside him on the sofa and he started to rouse slightly. I leaned over him and kissed him, giving him a taste of his own cum. He was almost frantic in his kisses for a few minutes, before he settled back down.

"That was wonderful, Stephanie. I just wish I could make you feel as good as you made me feel."

"We'll get there. We're just not there quite yet."

I heard his parents come back in the house, so I hopped up and smoothed my skirt and blouse. I ducked in the little powder room in the basement to check my makeup, which was a little askew after what I'd done. I touched that up and came out to find Tom's dad had come down to check on us. Tom was standing talking to his father.

When Tom's father turned to look at me, Tom tried to discretely adjust his dick in his pants.

"I hope I didn't interrupt anything." Tom's father said with a look that said he knew damned well he had interrupted something.

I smiled at him before replying. "No, it was getting to be time for me to go home anyhow."

Tom rushed over to me. "I'll walk you out to your car."

We went out to my car, and I felt certain one or more of his parents were watching us. Tom hugged me and gave me a long kiss.

"That was great, but I want so much more."

"We'll get there - soon."

..................................

Several days later at school, I saw Tom and he appeared very upset.

"My father did some asking around and found out that you used to be a boy."

"And he didn't like that."

"He told me to quit seeing you."

"I'm sorry."

"I told him I wouldn't."

"How did he react to that?"

"He turned purple and I thought he was going to hit me."

"He didn't, I hope."

"No, but he threatened to kick me out of the house."

"What will you do?"

"My mother put her foot down and said he wasn't going to do that."

"Thank God."

"But he told me I'm never to bring you in the house again."

"Not too surprising, I guess."

"My mother is not angry like my dad, but she wants to talk with you."

"You and I together?"

"You and her alone."

Something told me this would not turn out good, but I agreed to meet with his mother. We set up a meeting where she and I could talk privately and not be overheard. I was almost afraid that I'd never be seen or heard from again.

"So you are 'Stephanie'?"

"I am."

"So why did you latch onto my son?"

"Tom asked me out. I wasn't looking for any guy."

"And just how 'close' have the two of you gotten?"

"Not that close, physically."

"If you did, are you even capable of being close the way a man and woman would?"

"There's more than one way that a man and woman can be close, but we could be close in all the ways a man and woman normally could."

"And where do you expect the relationship with Tom to go?"

"I don't know where he wants it to go."

"Where do you want it to go?"

"I'm almost afraid to have any expectations."

"Most normal guys would have no interest in the likes of you."

"Don't I know that? And some just want the kinky pleasure of saying they fucked a trans woman."

"My son isn't like that."

"Which is why I agreed to go out with him."

"Do you expect him to marry you?"

"We aren't anywhere even close to considering that."

"But you want to get married?"

"I'd like to get married to a man, if I can find one who truly loves me."

"The word is that you slept with a couple of other guys."

"I'm not proud of that, and I told Tom I'm no virgin."

"If you do get married, you could never have a baby."

"I have some female equipment but not the equipment for that."

"My husband and I want grandchildren."

"There's always adoption."

"Tom seems to be in love with you."

"There are lots of romances that never go anywhere."

"What do you want with Tom?"

"Just a normal relationship between a man and a woman."

"Some people wouldn't even consider you a woman."

"Those are people that I'd never want a relationship with."

"What if I told you to stay away from my son?"

"I didn't pursue him, he pursued me. You'll have to convince him to stay away from me."

"I honestly expected something different from you, Stephanie."

"I'm sure I'm not what you want for a daughter-in-law, but I don't know that it will ever get that far."

"And if Tom dumps you tomorrow?"

"It'll hurt, but I'll go on. I've already lived through hurt and abuse that you could never imagine."

"I'm not sure you're the right person for Tom, but he has to make his own decisions."

"If he decides I'm what he wants, and if he's what I want, I hope you can accept that."

......................................

Tom was already working part time, while going to school. He managed to get full time hours and given the hostility of his father began looking for a place of his own. I was still working full time, so between it all, we didn't have as much time for dating as we'd like. My brother Carl had moved away from home, and when my parents took a vacation, I brought Tom back to my house.

We spent some time making out on the sofa, then I took Tom to my bedroom. I still was in the little attic bedroom. I guess I could have moved into the bedroom that Carl vacated, but that still held some memories that I wanted to put behind me. When we got to my bedroom, Tom was afraid to think that it could mean something more.

We sat on the bed and kissed and I asked Tom to unbutton my blouse. His hands were shaking as he did, and he fumbled with a couple of the buttons before he finished. I shrugged off my blouse, and Tom sat there with a look of nervous anticipation on his face. I took one of his hands and put it on a bra cup. He hesitated before beginning to stroke my boob through my bra.

We kissed as he caressed my breasts through my bra, before I asked him to unhook my bra. I had to turn around so he could see the back of my bra, since he couldn't unhook it without looking. I almost felt shy as I turned back around and let my bra fall off me. Tom saw my boobs and looked amazed. I put his hands on my titties and his eyes got very big.

He began to fondle by breasts as I lay back on the bed. My stroked them for a while, before I pulled his head down to one of them. He took the nipples in his mouth and began to suck on it, as though he could get milk out of my boob. I loved it. Rob was the only other guy to touch my boobs and they were smaller and less sensitive then.

Tom loved my titties and gave them the attention they had never had before. As he played with them, I could feel a heat rising through my body, and I almost felt like I was on fire, before waves of pleasure began to roll over my body. I'd never had a female orgasm before and it was like nothing else I'd ever felt. I sure wanted to feel it some more though.

I took off Tom's shirt and pants, and had him take off my skirt. We got completely on the bed and kissed more when I took his hand and put it down between my legs. He fondled my pussy through my panties as we continued to kiss. After a while, I lifted my hips and told him to pull my panties off. As he got them off, I spread my legs and for a few seconds, Tom just stared at my pussy.

"Lick it please. You're the first guy to get my pussy."

I had shaved the hair from between my legs, so I was completely bare down there. Tom leaned over and did a tentative lick up my slit.

"More, please, baby."

Tom dove in and licked and kissed my pussy like there was no tomorrow. He licked me to my second orgasm before I made him take off his boxers and move back up my body. I know I don't have quite the natural lubrication of a normal pussy, so I had some lube and I lubed up his cock and had him range over me. I kissed him and then grabbed his prick and eased it into the entrance of my cunt.

I had been dilating, so I had things in there, but this was the first real dick I had there. Dilation felt good, but it was nothing compared to the feel of Tom's cock in my pussy. I wrapped my legs around him, as Tom began to slowly and sweetly fuck my cunt. More than a year ago, I had guys in my ass, and that felt good, but this put that to shame.

I began to fuck Tom back as he fucked me and before long he was fucking me hard and fast. In one sense, I was sorry I had waited, but I needed to make sure that it meant something to Tom before we did this. I was panting and moaning as Tom drove his prick deep in my pussy. I looked at his face and it was like he was on another world and his being was centered on his dick in my cunt.

"Oh God, baby, I'm cumming."

"Do it. Fill me up with that cum. I need you."

Tom stiffened and drove his cock deep in my pussy as I felt it throb and pulse inside me. As he finished, he almost collapsed on me. As he regained his senses, we kissed for a long time before he rolled off me. We fucked several more times before falling asleep together in my bed. For the rest of my parents' vacation, we spent the nights together in my bed fucking in every way we could.

...................................

Tom and I have a place together now. Tom's mother and my mother seem to have reconciled themselves to the relationship. Tom's father still hates me, and my father seems largely indifferent. Will this be forever? I don't know, but for now it seems to be everything either of us could want. I am truly Stephanie, and for now, my long, strange trip has brought me someplace good.