LwL: Another Night With Rebecca

(This is a direct sequel to Harry Goes Cruising. I tried to make this as realistic an account of sex with a trans woman as possible, and I hope I succeeded)

It was 7 pm on a Tuesday, and Alexander's was barely half full.

"Tuesdays are 80s Night but that doesn't really get going until 9," said the bartender as he handed Harry his drink. "Were you hoping to meet someone?"

"Someone in particular, actually," said Harry, "it may sound weird, but I'm looking for a woman."

"Not as weird as you'd think, depending on the night," said the bartender. "What's her name?"

"Rebecca. Thin, pretty, blonde, kind of... enthusiastic?"

"Becks? Oh yeah," the bartender smiled, putting it all together. "She's in her a lot. Don't let her wild act fool you, she's a sweetheart."

Harry and Joan were visiting Carter Hills again, and Joan was having a night out with Marcy. The last time he had come to Alexander's he had danced and flirted with Rebecca, only to have her leave at the last minute. Fortunately Joan and Marcy had come by as "Jim" and "Mickey" and they had a memorable night back at the hotel room. However, Harry had not forgotten Rebecca or her sexy dancing.

Harry had switched from scotch to soda with lemon, as he wanted to pace himself. He ordered some dry cajun chicken wings and walked over to the jukebox. Dropping in some coins he chose some of his favourites from the 80s - Pet Shop Boys, Erasure, Fine Young Cannibals. He walked back to the bar to see that the bartender had brought out his wings.

Harry chatted some more with the bartender, whose name he found out was Keith. Keith had the shaved head and van dyke beard that was popular with both queer and straight men of a certain age, and he had kind brown eyes. Harry, of course, realized that bartenders worked for tips, so his kindness might have been a bit of an act. Nevertheless, he liked having the company. Harry stopped to respond to a text from Joan.

"That was the wife," Harry said. "She's out with a friend."

Keith smiled and said nothing but raised an eyebrow.

"She knows I'm here," explained Harry. "I know this is unusual but it works for us."

"Hey, I don't judge, I don't have a Gold Star," said Keith. "Also, my partner and I aren't exclusive, but I do like to make friends with the other guys."

The jukebox was playing "Good Thing" by FYC when Rebecca walked in. She was dressed a bit more sedately than the first time they met. Her blonde hair had grown a bit and was in a short ponytail and instead of a 90s Club Kid look she was wearing a yellow sundress and cardigan. She sat down at a table near the middle of the club.

"Looks like she just came off work," said Keith. Harry saw a waiter start to walk over to her and stopped him.

"Her first drink's on me." The waiter nodded and went over to Rebecca. Rebecca looked over to Harry, smiled and got up to walk over to him.

"Thanks," she said. "I never say no to a free drink from a stranger." She sat at the bar next to him. "But you look familiar. Have we met before?"

"About a month ago. You were wearing a red dress. It was 90s night."

Rebecca thought for a moment and then blushed.

"Oh god, I was on E that night, I must have looked a fright. I'm not usually like that. Wait a minute, I do remember you. Harry, right?"

"Right."

"Oh, I left you in the lurch, didn't I? I'm very sorry." Harry found Rebecca's accent intriguing. It didn't reveal a region as much as a milieu: she sounded like she was on stage, or in a movie from the 1940s. It was affected and yet somehow endearing.

"So what do you do for a living, Harry?"

"I'm an architect. And you?"

"I'm a receptionist at a clinic. I know, I probably came off as some crazy rave kid last time, but really I'm not."

"I don't think I'd be back here if I thought that."

Rebecca smiled and touched Harry's hand. When she felt the ring on Harry's finger she stopped.

"I knew it, you're married." She took a drink, rolling her eyes. Harry was about to speak when she held up a hand. "Save it Harry, I'm not down with being a test drive chick with a duck for some curious straight dude."

Rebecca tried to get up when Harry gently grabbed her arm.

"Wait. My wife and I have an understanding-"

"Harry honey, the line is 'my wife doesn't understand me.' It's older than both of us."

"No, really, we do. My wife is out with one of her girlfriends right now. I can text her if you want."

Rebecca sighed a sigh worthy of Rosalind Russell.

"You have five minutes, buster."

Harry texted Joan and explained the situation. He then sat there, looking at Rebecca as she fumed and sipped her drink. A couple minutes later his phone chirped an alert.

Harry read the text, chuckled, and showed it to Rebecca. The text was accompanied by a blurry photo from a downward angle of Joan's legs, with Marcy's face buried between them. The text itself was in all caps.

"YES. HAVE YOUR DAMN HALL PASS. SORRY I'M A LITTLE BUSY RIGHT NOW."

Rebecca read text and laughed a loud, husky laugh.

"Well. Even if this is some kind of put on it's a funny one. Okay, Harry, let's see where this goes."

The DJ was setting up but in the meantime people were plugging the jukebox. Somebody had put on "Domino Dancing" by the Pet Shop Boys and Rebecca lit up. "Okay we're dancing my friend," she said, grabbing Harry by the arm and moving onto the dancefloor. She took off her cardigan and tied it by the sleeves around her waist. Harry had forgotten just how sensual a dancer Rebecca was. Rebecca ground her crotch into Harry's, and while her cock was not erect it did the job on Harry's. Rebecca spun around, swaying with her arms on Harry's shoulders. Harry wasn't a terrible dancer for a middle aged white guy, and Rebecca's boldness brought out his own funkiness.

The next song was "Crazy For You" by Madonna, and while they both slowed down Rebecca did not let this stop her from gyrating on Harry's body. It felt like she was making love to him in front of everyone. Rebecca moved up to kiss him and Harry responded in kind.

Harry realized that for all of his newfound sexual adventurousness he had not kissed a total stranger in a long time. Rebecca's lips were soft and sensual, and Harry found himself instinctively nibbling on them, which caused her to bring herself in closer. As with the last time Harry had the momentary fear that he might come right then and there. After a moment Harry broke the kiss feeling like he was coming up for air.

"Would you like to go to my hotel room? Joan will be with her girlfriend probably for the rest of the night."

Rebecca smiled.

"Okay but I don't want you to think I do this weigh every guy I meet. A girl has a reputation to live with."

As they walked to the hotel Harry realized he had not met anyone quite like Rebecca. He knew a few transgender people and he had enjoyed times with Joan when she dressed up as "Jim," her masculine alter ego. Rebecca, however, was something else. Harry could not imagine how anyone had ever thought she was male. It was slightly chilly so she draped her cardigan over her shoulders without actually putting it on. As they walked Harry got to know her better. She was 34, had dropped out of college around the time she began transitioning, and was taking night classes so she could become a licensed therapist. The clinic she worked at was a walk-in in the inner city, which meant that they encountered everything. In whatever spare time she could manage she read trashy romcom novels.

As they walked Harry realized that Rebecca's 40s glamour girl image was not affected at all. This was truly who she was, and it really turned him on.

They got to the hotel room and Harry put on the the Do Not Disturb sign and locked the door. He stopped to read a text from Joan and laughed.

"Now my wife wants to know if she can join us later."

Rebecca smiled.

"She sounds nice but I'm not really into other women, sorry."

Harry clicked on his phone and brought up a picture of Joan as "Jim."

"What If she was dressed like this?" He showed the phone to Rebecca, whose eyes widened.

"Ooh You two are wilder than I thought. Tell her yes but to give us some time. I want you all to myself."

Harry texted back "She wants to meet Jim. Mickey can come too. Give us an hour."

Harry offered Rebecca a hanger for her cardigan and handbag. After thanking him and hanging them up she turned to Harry and kissed him again, harder and stronger than before. Harry grabbed a hold of Rebecca and fondled her chest with one hand while holding her close with the other. Rebecca was a thin woman, and her breasts, while not large, felt in proportion with her body.

"When I got my tits done I told the doctor not to make them too big," Rebecca said, as if Harry was reading her mind. "I'm not going to give myself back problems just for the sake of being sexy."

"They're nice as they are," said Harry, continuing to kiss her. Stepping away for a moment, Harry took off his shirt he began unzipping his pants. Rebecca took the opportunity to take off her sundress and reveal her body. She wasn't tanned but her skin was slightly olive. Her panties revealed her bulge, which was not large or erect.

"It'll be awhile before I can get my bottom surgery," she explained. "It doesn't get hard anymore unless I take a viagra. Just think of it as a big clit."

Smiling, Harry led Rebecca to the bed where she lay down and Harry began kissing her whole body. He approached this the way he would going down on Joan - giving attention to each area, from the neck to the breasts to the navel while stroking lower. It a bit odd at first, considering that Rebecca was unlikely to get an erection, but Harry kept going stroking it like he would a clit until his mouth met his hands under Rebecca.

Harry felt like he was in uncharted territory as he licked and stroked the shaft. Sensing his apprehension, Rebecca instructed him on what gave her the most pleasure, and Harry was an eager and willing student. Rebecca finally came, squirting a tiny bit of fluid and letting out a loud moan.

"That was wonderful, Harry," said Rebecca. "Now it's my turn."

Rebecca kissed down Harry's chest and stomach, stroking his balls with one hand and the shaft with the other. Rebecca's skills were great, and it wasn't long before Harry came, with Rebecca swallowing it all. Harry then helped Rebecca off her knees, kissing her and tasting his own cum on her lips. They lay in the bed cuddling for a few minutes, when Rebecca noticed an anxious look on Harry's face.

"What's wrong?"

"Nothing, it's just... I haven't been with a woman without Joan being there in a long time. I know she's okay with it, but it still feels weird."

"But you fool around with guys, right?"

"Yeah, but this is different."

Rebecca laughed and kissed Harry on the lips.

"I'll be honest, the fact that you see me as a woman makes me feel good. But also, it sounds like Joan doesn't mind at all."

They kissed and cuddled and soon Harry was hard again. Rebecca smiled.

"Do you want to put it in my ass?"

"No, I gave a better idea." Harry pushed his hard cock up against Rebecca's soft one, teasing it like he would a woman's clit. Rebecca smiled and began matching Harry's thrusts, grabbing Harry's ass and moving her whole body towards Harry. Soon Harry was coming again, spraying all over their genitals. Harry grabbed both of their cocks and used the cum to lubricate. Harry's cock was softening but still tingling, and it felt good to continue thrusting at Rebecca. This was obviously effective as Rebecca soon came again herself.

"Oh my, Harry, that was wonderful. Most guys don't put up the effort."

They lay there for a few minutes, kissing and fondling each other. Suddenly there was a knock on the door. Harry got up with a start. He draped a sheet around his body and went to the door?

"Excuse me, there's a DO NOT DISTURB sign on the door."

"Hotel Security," said a high-pitched but gruff voice from behind the door. "We've heard reports of lewd acts being performed in this room."

"Oh really?" said Harry with a smile. He looked through the peephole and saw "Jim" and "Mickey."

"Yeah, and we want in on them," said "Jim." Harry unlocked the door and let them in, embracing the two of them. Rebecca came up to them, entirely nude.

"Mmm..." she said, "look at these two studs you brought me. You guys ready to party?" Jim and Mickey looked at each other and smiled.

"Sounds like a plan." Jim and Mickey hung up their jackets and began to strip. They both had their breasts bound, but Jim's had slits to accommodate "his" nipple piercings. As they both took off their pants they revealed their strap-ons. Jim took the lead, kissing Rebecca with lusty passion. Rebecca returned the kiss, embracing Jim and leading him to the bed. Mickey pulled out a bottle of lube and began to prepare Rebecca's ass. Jim broke off the kiss and lubed Mickey's ass.

Harry sat on a chair, nude except for the sheet. He decided to just watch, stroking his semi-hard cock as the others got together. The three got on the bed and Mickey entered Rebecca while Jim in turned entered "him." Harry couldn't quite believe what he was seeing: he knew this was his wife and her friend mating with a trans woman, but it truly seemed more like two hot men double fucking a woman.

The three kept thrusting until they had all come. Mickey and Jim removed their strap-one and binders and embraced each other, kissing each other hard on the mouth. Then Rebecca surprised them by joining their kiss.

"I thought you weren't into other girls," joked Harry.

"I'm reconsidering a lot of things," said Rebecca with a smile. She fingered Joan while kissing down Marcy's chest.

"Forgive me, I'm new to this," said Rebecca. Marcy smiled and pulled Rebecca onto her, trying to give her space to work with as well as encouragement.

Joan got off the bed and joined her husband in the armchair. Harry was still edging to all this, and Joan grabbed his cock. His hands free, Harry began to stroke his wife's vulva and clit while enjoying the show.

Rebecca was a fast learner, and Marcy grabbed her head and pushed it into her wet cunt. She lay on her back as the other woman explored her sex.

"You're a natural, girl," said Marcy with a grin, her eyes heavy lidded as the other woman brought her to new heights of ecstasy.

They spent the rest of the night in various combinations, letting each member of their foursome have their moment to enjoy the pleasure of the others. They finally collapsed on the bed, everyone satisfied and exhausted.