The Roommates

Waiting for Julie to respond, thoughts ran through his head. 'She-male' and 'trannies' they were called. He had seen it while porn surfing. He had even watched some of the videos. He knew he wasn't gay, but had been turned on by them. It wasn't the creepiest thing he'd seen on the internet. Some of them were actually hot. He'd never admit it to anyone that he'd even jerked off a few times to the videos. But this was real life.

Julie was finally awake, figuring out what was happening. "Oh dear, OH DEAR" she said. She was sitting up in bed now, her hands covering her mouth as though she was afraid of what she might say. At that moment, Karen came out of the bathroom in a robe, her hair wrapped up in a towel. There was still shampoo running down her face. "Oh my, Oh MY" said Julie.

Kevin was still shocked by what he had seen. He realized that Karen was standing right next to him. He retreated to the side of Julie's bed. He looked at her in her robe. When he couldn't see the penis, he had to admit she was sexy. 'She?' he thought, wondering if he should correct himself. 'What pronoun should I use?'

Karen looked at Julie, then at Kevin. Back and forth. No one was saying anything. She saw the shock in Julie's eyes. And when she looked at Kevin, she was sure he was checking her out.

Finally, Kevin shook his head, and broke the silence. "Julie, your roommate is a she-male, a tranny." He looked at her, waiting for acknowledgment.

Julie looked at Karen, then at Kevin. She couldn't think of what to say, or even how to start. She looked back at Karen who softly said "Tell him."

Kevin couldn't believe his ears. 'Tell him' she said, 'that means Julie knows.' This was getting weirder by the minute.

Julie reached to Kevin, and then patted the bed. "Sit down." When he did, she scooted over to him and wrapped her arm around him. "I know this is going to be hard to understand, but please, Kevin, please try to have an open mind. If you can promise me that, I'll tell you about Karen." She waited for his response.

Kevin felt better, maybe even safer, now that he was sitting next to Julie. He put his arm around her, looked at Karen, then said "OK."

Julie looked at Karen for a signal that it was OK to proceed. Karen nodded. Julie took a deep breath in and let it go. Then she began. "Kevin, Karen is a 'trans-gender.' That is the term they prefer. You see, she was born a male, but all her life has felt that she was a woman inside. It's hard to understand, but it's been a struggle all her life between what she felt on the inside, and what she was on the outside. When she became a teenager, she freaked out, and started therapy, and that is what saved her. She was able to understand her feelings. Her therapist helped her deal with that, and eventually told her about things she could do about it."

Kevin listened. He had heard all this before. So far he understood.

"About five years ago, she decided to start living as a woman. She wore make up, wigs, and dressed in woman's clothes, but it was not enough. So she went to a special doctor. After a complete medical workup, and months of intense psychoanalysis, she was approved to undergo a complete change to become a woman. She started taking hormones. She had breast implants. She's been as she is now for a year. In a few months, she's going to take the final step."

"You mean..." Kevin paused, he wasn't sure how to say it. It made him wince just to think of it.

"She's going to have surgery to transform her male genitals into a vagina. At that point, she'll perhaps be able to feel normal, and be herself both inside and out."

He looked at Karen. He had to admit that until he had seen her in the shower, she was knock out as a woman. Even her tits were spectacular. Then he turned to Julie and asked "So how long have you known about it? How long have you known her? How long have you lived together?" More questions rushed into his head, but he wasn't sure he could ask them.

"I met Karen about two years ago through my job. You see, I sell cosmetics to people with various medical conditions, and teach them how to use them. Most of the time I'm helping people with skin conditions. You know, like birthmarks, rashes, but I do have a few clients just like Karen. She was referred to me, and we just hit it off from the get go. So I knew about her issues even before I actually met her. We've been living together for a year now."

"Don't you worry about... Isn't it weird living with a..." He couldn't complete his questions.

Julie knew what he was asking. "Kevin, she's not really a man. As far as she's concerned, she's a woman. She just happens to have a penis. There's nothing for me to worry about. Karen and I are girlfriends, she's like a sister to me. And she lives like a woman. She even sits down to pee."

"Does she date?"

"Ask her, she's right there" Julie said gesturing to Karen.

Kevin turned to ask her, but Karen answered before he could. "No, I haven't dated any men yet. I want to, but the doctors say I should wait. And I have to admit that if things got serious or physical, it could lead to some problems, sort of like what is happening here."

Kevin's curiosity was getting the better of him. The frank discussion had helped to calm him down. He wasn't freaking out anymore. "Karen, can I ask you some questions that might be extremely personal? You don't have to answer if you don't want to."

"Sure."

"I don't want to offend you in any way, but.." Again, he paused. How could he ask this in a delicate manner. "Karen, do you get erections?"

"The hormones, the female hormones I take make that difficult, but not impossible. If I wanted to get an erection, it helps to take a pill, like Viagra."

"Oh yea, that makes sense." Kevin stopped for a bit. He wanted ask more, but it would mean admitting to Julie things he wasn't sure he wanted to admit to anyone. But he continued "Have you ever done that?"

Karen frowned, then quietly said "I don't want to answer that question."

'Fair enough' he thought. In order to go any further, he might have to reveal his 'knowledge' of she-male pornography. He realized he never get another opportunity to find out these things, so he continued "Sorry." He decided to change tactics by being more general. "Have you heard of people in your situation, those who hadn't had vaginas made, have you heard of them having anal sex?"

Karen looked at Julie, then back at Kevin. She felt better about answering these type of non-personal questions. "Some do. They have such a strong desire to be a female, that they have a need to have sex with a male, and the only way to do that is anally."

Kevin had only had anal sex with a woman once before. It was OK, different, but it was always walking on treacherous ground to even bring it up as most women were offended by it. The time he did fuck a girl in the ass, it was the girl's suggestion. She was such a kinky freak.

He stood up and walked over to Karen. She was a bit scared, wondering what he was going to do, especially since he had just asked about anal sex. But he stopped in front of her. "Karen, I'm sorry I freaked out. I want you to know that I think you are a beautiful woman, and I understand, at least a little bit, what you're going through." He held out his hand to her. "Friends?"

Karen broke into a huge smile. She took his hand, but then stood up and gave him a hug.

"Why don't you finish you shower. I think you at least need to rinse off." He opened the bathroom door for her.

"Thank you, Kevin" she said as she walked into the bathroom and closed the door.

He heard Julie call to him "Come here" and walked back to the bed. She stood up and kissed him, then held his head as she looked into his eyes. "That was nice. You were so understanding. Thank you" she said, and then kissed him once more.

All of a sudden Kevin chuckled. "What's so funny?" Julie asked.

"For some reason, and I know this may be a bit insensitive, but I just thought about what would have happened had Ted hooked up with her." He chuckled again, but then straightened up when he saw that Julie was not even smiling.

"Kevin, did you mean it when you said you thought Karen was beautiful?"

"Sure, she is beautiful."

"Even though you know she has a penis, you think she's beautiful?"

"Well" he paused, "yes, I do"

Julie knew Kevin wasn't gay, but .. "Kevin, are you bisexual?"

He was taken aback by the question. "No. No, I"m not. I'm not gay, and having sex with another man doesn't appeal to me in the least. It's not my thing. I mean, how can you ask that after what you and I have done?"

"Well, I knew you weren't gay, but still, you find Karen, who has a penis, to be beautiful. Are you attracted to her?"

Kevin thought about the answer. He knew his answer, but had to reason out to himself, and maybe to Julie, what the answer meant. He was attracted to Karen. Karen the woman. But would Julie understand that. It was time to come clean.

"Julie," he started "you know most guys masturbate, you know, jack off, right?" He waited for her to agree. "I'm one of those guys. And the internet has made it a lot easier. You can watch video of just about anything you want to see, or to fantasize about, you know, when you're doing it. And sometimes you'll be flipping though links and you end up watching stuff that is totally bizarre."

"OK" she said in a way that pushed him to continue.

"Well, I've ran across videos of people like Karen before, only on the web sites they are called she-males or trannies. And it was stimulating to me. I fantasized about it and jacked off watching them." He paused to see what reaction Julie would have.

She kept a straight face, showing no visible emotion. "Go on." was all she said.

"I've done it more than once. Now I know I'm not gay, not even 'bi' but I do find it erotic. I guess I view them as females, just as Karen views herself. They just happen to have a dick."

"Are you saying you want to have sex with Karen?" Julie asked, again, not showing any emotion that he could see.

"Uh, here's the thing Julie. I am very attracted to you, and I am hoping that our relationship can continue. I want to keep on seeing you. I don't want to say anything that would upset you. But, if we weren't seeing each other, I think I would be interested in seeing Karen. I know that I wouldn't want to fuck her in the ass, or be fucked by her. But definitely everything above the belt, and oral sex. Does that upset you?"

Julie stared into his eyes, then smiled. "No, I'm not upset. I totally understand." She put her hand on his dick and rubbed a bit, then said "You are a bit of a pervert, aren't you?"

"Guilty as charged" he offered. He was about to grab her breasts, when Karen came out of the bathroom. This time she only wore a towel around her head. Kevin watched her as she walked past them with a grin, leaving the room to go to her own.

Feeling that most of the barriers had dropped, he turned to Julie and asked "Julie, since we're being so open and honest, do you have sexual feelings towards Karen? Are you bi?"

"I'm not sure what I am, but I do have feelings for Karen."

"Have you two..." he paused again, searching for a word that wasn't judgmental or demeaning, "...messed around any?"

"What if we have? What would you think of that?" she asked.

"I think it would be kind of hot. You know it's every guy's fantasy to be with two girls at the same time, so any time a guy sees two girls together, he thinks somehow it will lead to his involvement."

"Even if there's another penis involved?"

"Like I said, the she-male thing was a little interesting to me."

She had noticed his cock getting firmer as the conversation had progressed. Now she grabbed it tightly, saying "A little interesting? Looks like you're very interested, boy!" She pulled him onto his back on the bed, then took him into her mouth. She was too into it to mess around with going slow, so she began moving her head up and down.

Kevin was enjoying himself, but as Julie was sucking him off, he started to think about Karen. He wondered if Karen gave a good blow job. What did she think of when she did it? He guessed she would think of herself as a woman pleasing her man. He wondered how she would feel pleasure. His mind drifted to the videos he had seen, then thought about Karen taking one of those pills, and blowing him while she jerked herself off.

Julie felt Kevin tense up, and she went all the way down. She felt his sperm spurt into the back of her mouth and down her throat. She pulled back up and massaged the tip of his dick with her tongue, coaxing every last bit of his love juice out.

It was an intense orgasm. It seemed to Kevin that each of the orgasms he had experienced with Julie had been better than the one before, and this one was the best. Was it because he was fantasizing about doing it with Karen? He felt Julie kiss her way up to his neck, and then they kissed each other. "Julie, that was unbelievable. You're so good to me."

"Why don't you go take your shower?" She asked.

"Want to join me?" he asked, pulling her up as he got out of bed.

"No, not this morning" she said. He went into the bathroom and took a quick shower. After getting out and drying off, he thought he'd borrow some of her toothpaste. He opened the medicine cabinet and grabbed the toothpaste. On the next shelf, he saw a box of condoms. 'Look's like there's an optimistic outlook' he thought to himself, then he put some of the toothpaste on his finger and rubbed it over his teeth as best he could.

When he came back into the bedroom Julie was already dressed. Before he could indicate his disappointment, she said "I've got to go to the office today to get ready for next week." She stepped up to him. "I had a great time last night. And thank you for your understanding and honesty this morning." She turned to go downstairs and he followed. As they passed Karen's bedroom's closed door, he hollered "Bye Karen."

"Bye Kevin" he heard.

As he was going out the door to leave, he asked Julie when he could see her next. "How about we get together Tuesday night? I'll give you a call when I know more." She kissed him and almost shooed him out the door.

Tuesday

Kevin replayed the morning's events in his head over and over as he drove home. Each time he thought about what had happened, he found himself thinking about Karen more and more. He thought about her great figure, her breasts, and he even thought about her penis. He wondered if she had ever taken a Viagra and had sex with anyone. He wondered if she had done anything with Julie. She had said they were 'sisters' but he wondered if that was some code word for some type of lesbian-she-male liaison. 'Roommates with benefits' he thought.

He had seen she-mail with female videos. But if she were into girls, why go through the trouble of becoming one. Why not just stay a man and enjoy women? He couldn't figure that out - it didn't make sense. Maybe they were just friends. Maybe this 'I'm really a woman inside a man's body' thing is truly hell. He was glad he was a man, inside and out.

Julie called Monday afternoon. "Still open for tomorrow night?" she asked.

"It's marked in ink on my calendar. What you want to do?"

"I thought we could have dinner at my place. I mean I want to cook you dinner at my place. How's that sound?"

"It sounds great. Do I need to bring anything?"

"Just your sweet self. Is seven OK?"

"Seven is perfect" he said, thinking 'not too early, and that'll probably mean some post-dinner activity.'

"Call me when you get to the gate, and I'll buzz you in. See you then." She gave a kissing sound before hanging up.

Kevin made a mental note to drop by the liquor store the next afternoon. She said he didn't have to bring anything, but social convention was otherwise. He'd pick up a bottle of wine. He didn't know shit about wine, so would have to trust the clerks at the store. That should be OK as they were usually dead on when it came to recommended beers to try as well as spirits.

Tuesday evening he pulled up to the gate, punched her apartment number. Her voice came over the speaker "I'm buzzing you in now. Come on in." The gate slowly opened and he drove to her building, parked, and walked to the front door. He knocked, and heard Julie holler "It's not locked, come on in."

He went in. Julie was in the kitchen, apparently in the middle of a critical phase of putting the meal together. The whole place was full of the aroma from the dinner. There was some good rock music playing, likely for his benefit. He walked over to the kitchen, lifted the bottle of wine and said "I brought some wine. I don't know wine so I had to rely on a recommendation at the store."

Julie stopped to look at the bottle. "Oooh, that's actually pretty good." She opened a drawer and pulled out a corkscrew. She handed it to him. "Go ahead and open it and put it on the table. It'll go great with dinner." She gave him a quick kiss and returned to her work.

"Sure smells good" he said as he tried to figure out the corkscrew. He eventually pulled the cork, and placed the bottle on the kitchen table. He noticed two place settings. Perfect. Karen must be out for the evening. He smiled to himself thinking of where things would go after dinner. "Karen's out, huh?"

"She's working late. Said she didn't know what time she was coming home. Look's like we're on our own."

He watched her as she moved around the kitchen. She was a sexy little thing. She was wearing jeans and a t-shirt, but looked great in it. She looked great no matter what she wore. Finally, Julie pulled a pan out of the oven, and filled two plates with food. She carried them to the table. "Kevin, the wine glasses are in the cabinet to the left of the stove. Get a couple and pour us each a glass. Dinner's ready."

The wine was actually pretty good. The meal was unbelievable. He hadn't had a home cooked meal in ages, and this was restaurant quality. "Julie, this is delicious!"

Julie smiled and said "Thanks. It's just something I threw together."

Kevin knew she was being modest. He thought she must have planned the meal and spent most of the afternoon preparing it. After they finished eating Julie said "leave the dishes, I'll get them later. Let's take the wine into the living room."

They sat next to each other on the couch. Talk turned into kissing and soon he was lying on top of her, fondling her breasts.

"Kevin, let's go upstairs." They pulled apart, got up, and went to her bedroom. When they got there, Julie faced Kevin and started to deliberately undress him. T-shirt, jeans, and then his shorts. She took them off, folded everything neatly, and placed them on her dresser. She motioned to the bed and said "Sit down."

'What is up with this' he thought. 'Maybe tonight is the night.' Not that anything was wrong with the blow jobs, but surely they were ready for real honest to good dick sliding in and out of vagina sex tonight.

She slowly pulled her t-shirt up and over her shoulders, revealing those wonderful tits. No bra, just out there for his enjoyment. She took the shirt off and Kevin started to reach for her, but she quietly said "Wait."

Then she unbuttoned her jeans and wriggled them down to the floor. She stepped out of them, then bent over to pick up the shirt and jeans. She folded them and placed them on the dresser next to his clothes. She was standing in front of him, wearing only light blue lacy panties. Kevin thought how pretty they were next to her dark skin. She walked over to the door, and turned off the lights. Before his eyes could adjust to the darkness, he felt her get onto the bed. Instead of lying down next to him, she stopped at his waist.

He felt her hand touch his upper thigh, then slide to his dick. He was already fully erect. 'Julie sure knows how to get things going' he thought. She softly grasped his penis in her hand, and he felt her caress it up and down. He felt her weight shift on the bed, then noticed her breath on the head of his dick. In a moment, she had taken it into his mouth. 'Girl,' he thought, 'keep on doing that and I'll have nothing left for later.'