The Roommate Pt. 16 - Miranda

So now, Lori, the former Josh, intrepid college teacher and author, was again without a roommate and forced to scrimp to afford her apartment. After Miranda and Leigh Ann, the apartment felt quiet and empty, and she was unable to completely celebrate living as a woman. However, she could afford to shop used clothing stores -- looking, looking and looking to find some adventurous and colorful Lori clothing and accessories.

About this time she learned about a bar in an adjacent city where trannies and the transgendered gathered. At Janie's Place, one could meet attractive and not-so-attractive crossdressers, their spouses, transsexuals such as herself (mostly male to female, but also a scattering of FTM), along with those straight people -- 90 percent men -- who were attracted to them.

There, Lori felt at home, and could let down her hair so to speak, and could chose to dress very demurely or very sexily. She visited mostly on Friday and Saturday nights and made sure she bought enough drinks to endear her to the management.

After having been a regular for a couple months, and not yet having found a roommate, Lori was sitting at the bar nursing a glass of wine when she noticed a young man of college age (the age of her students), sitting nearby. Lori was just a bit tipsy.

"Do you come here often?" Lori asked in her most feminine, sexy voice close to his ear, over the loud music. She was wearing a rather tight, red blouse gathered in strategic places to accentuate her breasts, and a short skirt over patterned black pantyhose. It had become her custom to never come without applying Leigh Ann-ish makeup and nails.

"Only the second time," he answered, venturing a quick glance.

"What's your name?"

"Nathan."

"Your real name."

"Yeah; Nathan."

"I'm Lori; hi. And that's my real name too."

Nathan was of average height; had fairly long, wispy brown hair but not enough to look feminine; his voice was of average timbre but Lori detected a bit of a country accent and word choice. He was slender, but not overly so, and he tended to wear finely maintained corduroy trousers, along with a turtleneck top.

Over time, Lori learned that he was a law school grad who'd passed the state bar and was now very low on the totem pole at a law office. There, he felt he was a gofer spinning his wheels, going nowhere.

Lori would buy him drinks to loosen him up, and he opened up gradually over time. He had a girlfriend of sorts who was still in law school and spent gobs of time studying.

"Why do you come here?" asked Lori one night.

"Sometimes I get tired of vanilla types of people," he admitted. "I like to be kept guessing about people."

"What'd'ya think I am?" asked Lori with a darting glance.

"That's putting me on the spot," said Nathan.

"Yes, but come on, I want to know."

"When I first met you I thought you were a natural born woman, to be honest," said Nathan. "But the longer I came here and I was better at picking up on little clues, I began to see a little bit of maleness in you. Just a little bit." He laughed nervously.

"Well, you're right, Nathan. At one time I was Josh. But I feel much, much better being Lori."

"Good."

"Are you attracted to me?"

Nathan nervously cleared his throat. "I don't know."

They had been sitting much closer to each other than the first time they met. Lori impulsively took his hand and placed it on her thigh, on her sexy nylons. And there it stayed for a few minutes, until they both felt a little awkward and he withdrew it.

A week later at Janie's, Lori didn't see much of him, but as the closing time grew near after midnight, Lori went over to the young lawyer and put her arm around him. She knew he could smell her perfume and feel her breast touching his arm, and she felt his loneliness.

"Nathan, Nathan. Would you like to come to my apartment for a nightcap?"

When he learned she was in the next city, he was reluctant. She offered to drive him in her car, and then return him to his nearby car after an hour.

In the car ride, Lori broke the ice. "So Nathan, who are you most attracted to at Janie's? I could guess, but one never knows."

She was thinking of Tyler, the M to F transsexual who could easily pass for a model, or Sherry, who had the most fabulous figure this side of Las Vegas.

"You. I'm most attracted to you. There, I said it."

"I'm truly surprised and flattered, Nathan." (And she truly was.)

After arriving at Lori's building, she led him up her stairs. Somehow it all seemed slightly illicit, like she was having an affair, and this made her feel sexier.

Inside, she turned the lights down low, and poured him a beer while she sipped a glass of wine. With urging, Nathan began to talk about his girlfriend and his family -- while sitting in a corner of Lori's sofa. Midway through his story, she calmly took his beer and set it down on the coffee table, and began tracing his lips with her red fingernail.

Nathan froze a little and Lori didn't know if he were about to bolt -- or relax. Then she gently slipped her finger into his mouth and moved it in and out slowly. Nathan wasn't moving.

"When's the last time you had sex with a woman?" she asked.

"That's a very personal question."

"Come on, you can say."

"Well, I'm just getting to know you."

With that, Lori moved closer to him, gently turned his face toward her and moved her lips within an inch of his. She looked into his eyes, and she knew that her sexy Leigh Ann-inspired makeup was inflaming him.

He moved forward to kiss her but in his awkwardness ended up kissing her nose and cheek.

"You can try again, Nathan."

This time both she and Nathan slowly came together. His lips were surprisingly soft and yielding, and of course, tasted of beer. Lori put her arm around him, and they explored each other for a good minute. Then she began unbuttoning his shirt. He had a fair amount of chest hair, and she enjoyed running her hand through it.

She knew he was getting worked up, and he soon just lay back with his eyes closed as she played with his hard nipple.

"Do you want to fuck me, Nathan?" she whispered into his ear.

"Yes ... yes."

"Well, you know I still have my rod, Nathan, but tell you what, we can still do it." Lori began unbuckling his belt and pulling down his trousers. Underneath was the most lacy, frilly, girly pair of panties Lori'd seen in a long time.

"So Nathan, this is interesting! Sexy panties! I love them! And they are so wet. And you are so big, such a nice big cock." With that, she pulled the panty crotch aside, releasing his prick to swing in the air, with drops of pre-cum dripping from its slit.

She ran a finger along his organ, beginning from balls to tip and back again, and the penis jerked involuntarily when she hit the most sensitive spot.

Now Nathan's hand was running through her hair and he was sighing.

She circled his dick with her fingers just above his balls, and pulled forward, essentially milking him of some more of his pre-cum. After several of these moves, his erection was freely dripping his body's lube, which Lori smoothed all over his penile head. Then she moved the head around her cheek, and finally when she couldn't wait any longer she popped it into her warm mouth.

"Oh-h-h-h," gasped Nathan, involuntarily making a thrust to push it in further.

But Lori would have none of that, and returned to just sucking his penis's tip. To her, it seemed like a small, slick fruit, like a big strawberry. She ran her tongue around it, all the while keeping a tight grip on his dick just behind its head.

But Nathan could no longer contain himself and began thrusting. Lori knew he was going for it, and this time didn't fight it. He held her head with his two hands and began using her as his fuck vessel, and that was fine with Lori, who wanted to blow his mind, figuratively. His balls were now bouncing off her throat and chin ...

Soon, there was one final mighty thrust and he began to gush hot sperm down her throat, unable to stifle a short scream.

Lori removed her mouth and milked some more ejaculate, sending it onto her face with a salty taste.

She looked up at him, still sitting on the sofa, with his eyes closed and laying back in exhaustion. "Well, panty lawyer, now you've fucked a shemale. Another notch for your bedpost."

"Oh, god," said Nathan. "You make it sound like I'm a frat boy."

"But now, you must think about my pleasure too. Do you want to give me a blowjob?"

He was strangely silent as though thinking it over.

"Listen, Nathan, I'm kidding. This is enough for one night. But I'll take a rain check on some sort of return favor, OK? I am very, very flexible on stuff that might appeal to us both. Think it over and imagine what you might like. On the other hand, I'll understand if you never want to see me again because you feel too guilty."

And with that they cleaned up, she drove him back to his car, and he drove on home, taking with him a pair of Lori's panties.

The next week he didn't appear at Janie's, and that didn't surprise Lori at all, but he did show up the following week.

"Are you wearing my panties?" Lori asked.

"Yes."

"How do they feel?"

"Nice and slick and tight."

"Have you had any fuck time with your girlfriend? Oops, sorry about being so inquisitive."

"No. Spent a little time together, but nothing x-rated."

"Maybe you could steal a pair of her panties."

Nathan laughed and said he'd been tempted.

That evening back at Lori's, they didn't waste any time with preliminaries. He seemed eager to give her a blowjob, which Lori didn't discourage, and he more or less imitated the technique she'd used two weeks before. Then Lori grabbed his dick and licked all the pre-cum off, and poor Nathan was breathing heavily. Lori grabbed a condom and rolled it down his shaft.

"What?"

"I want you to fuck me. I'm the woman, you're the man."

Lori could see the lightbulb slowly brightening in his lawyer's brain.

Nathan: "Hate to say it, but I would find that repulsive."

"Look, Nathan, I'll turn the lights off, and there will be just a tiny light from a candle. The fit will be nice and tight, and I'll guide it in for you."

"I'm sorry, Lori."

"OK then, I'll give you a couple of my bras; and think about it -- next time I could fuck you."

"You're trying to turn me gay."

"You see me as a woman, right? You're not fucking a man."

"Yeah."

Lori made the room nearly dark and returned to her paramour wearing a babydoll nightie with a bra top, along with a spritz of perfume.

She began to kiss his neck and ears, and then very gently his lips, and his cock rose to the occasion. He was primed and ready.

On the floor, on the deep-fleeced rug, she assumed a doggy position and lubed her male vagina. She then added lube to his condom, and he fell in behind her, and she guided his organ into her flower of a hole.

"Be gentle, Nathan. Be gentle. Push into my pussy just a little, baby."

And he did, with a little grunt of pleasure.

"There, there, you big bear. Now push in a little further."

My first time being fucked by a guy, thought Lori. Now I'm a little more like a woman. How will it feel with the real thing?

"I'm going to fuck you deep," said Nathan, beginning to thrust.

Lori wished he wasn't wearing a condom so she could feel his release, but that wasn't to be.

"Nathan, baby, imagine me dressing you up with a tight corset and tits and dress and nylons and high-heeled shoes ... "

With that, he had a powerful orgasm, and slowly stopped thrusting.

But afterward, with the lights up again, he couldn't look her in the eye and seemed guilty about having given in.

And that was the last she saw of Nathan. He didn't return to Janie's.

But Lori didn't feel heartbroken. She'd gotten what she wanted and she'd expanded his sexual repertoire. Maybe he'd find a warmer girlfriend. Maybe he'd begin to dress up as a woman in private. He did have her two bras (ones she was going to throw out, anyway). Maybe he'd develop an alternate personality as Nancy or Nina or Nadia or Noelle.

Lori was again by herself.