An Interesting Turn Of Events

An Interesting Turn Of Events

Jim was a construction company owner. He was a tall man with black hair who kept himself in good shape. He got married, but five years later it ended in divorce. Dating proved frustrating. He was still fairly young, in his late 30's, but the women he dated left him frustrated. He just couldn't make the right connection.

It was one night at a bar when he met Stephanie. Stephanie was an attractive woman with long brown hair, breasts that seemed perfect, not too big or too small, and a shapely ass. Stephanie was flirtatious and very friendly, a contradiction to her quiet demeanor at work as a librarian, They got along well, and Jim took her home that night.

Before some of the most amazing sex he'd ever had, Jim learned that Stephanie was a pre op transsexual woman, who preferred being treated like a woman. This was just fine with Jim. A whirlwind romance began, and two months later he asked her to move in with him. Life was good on all fronts for Jim. However, there was somebody he was worried about.

Brian was Jim's best friend since childhood and the co owner of the construction business. They did everything together and looked out for each other in different ways. Growing up, other kids learned quickly not to mess with Brian when Jim was around. Brian helped Jim with his studies. Brian did most of the paper work in the company. However, he seemed to be getting nowhere fast with women.

That's when the idea came to Jim. What if he introduced Brian to the idea of dating a transsexual woman? Jim was happy and in love. Stephanie was all woman in the bedroom, attentive to his needs and truly she had become his life partner. He decided this needed to happen, and he brought up the topic to Stephanie after sex one night.

"Mmm, that was wonderful baby, " said Stephanie with a kiss.

"Yes it was. You really know how to make me feel special." There was a hint of concern in his voice. "I feel so lucky right now."

"What is it sweetie, " she asked? "I can tell that you have something on your mind. Tell me."

"I was just thinking about Brian."

Stephanie giggled. "I must be doing something wrong if you're thinking about him while you're making love to me."

Jim rolled on top of her and kissed her. "Am I gonna have to tie you down and teach you to be a good girl?"

"Promises promises, " she teased as she kissed him. "What's wrong with mopey?"

"See, that doesn't help things when you keep teasing him like that, honey. You know he's my best friend, and I can tell that he's depressed. He hasn't dated anybody in over a year."

Stephanie pushed him off and rolled on top of him with another kiss. "I'm sorry. What do you want me to do, fix him up with one of my girlfriends? You haven't told him about me yet, so..."

"I'm getting to that." Jim could feel himself getting hard again. "I was thinking I could bring him here for dinner and we could talk about that and then..."

"So, what do you want me to do?" She was grinning. "Let him fuck me? I have a feeling he'd rather me fuck him."

"Stephanie, you've got him all wrong."

"Fine, I'll make dinner and we can see where it goes from there." She kissed him. "Sound good to you?"

They shared a long and passionate kiss. "Perfect. Now that that's settled, it's time for another round."

"I thought you'd never ask."



Jim and Brian came home from work in a good mood. "That was amazing, Brian. The company wouldn't be where it is if it wasn't for you."

Brian was blushing. "Oh please. You and the crew work your asses off. That's why it's so successful. I just sit at a desk on a computer and talk on the phone all day."

"Dude, don't even start with that, " Stephanie was there to greet Jim with a kiss. "Did you know that Brian just landed the company a six figure deal?"

Stephanie smiled at Brian and gave him a hug. "That's awesome. Congratulations."

Brian winced for a moment and recovered as be blushed. "Just doing my job."

Jim sniffed the air. "Something smells good."

"It's meat loaf and it's ready, " Stephanie replied as she went to set the table.

They made idle chit chat as they enjoyed some wine with their meal. Afterwards, Brian and Jim went to the living room. Stephanie cleaned up the kitchen and joined them afterwards, wasting little time getting to the point. "So, Brian, Jim tells me you haven't been dating in a while."

Brian started blushing again and was stammering. "Well, I, um... It's not... I've been talking with this amazing woman online for a few months now. She's..."

Stephanie was laughing. "Online? Are you serious? You need the real thing, sweetie."

"What she means is we think you should get back out there and start dating again, " Jim added. "And we think we have the solution."

"What are you talking about?"

Stephanie was sitting between the two on the couch and put her hand on Brian's leg. He whimpered. "Is everything okay, " she asked?

"I'm fine. What are you guys talking about?"

"Have you ever thought about dating a transsexual woman, " Stephanie asked as she rubbed her hand on his leg? Brian bit his bottom lip.

"A, um, transsexual woman, " he nervously asked?

Stephanie smiled flirtatiously. "Yeah. You know. A chick with a dick?"

"Oh, I, um... I don't think they liked being called that."

"So you have thought about it, " Stephanie replied as her boyfriend just listened. "Would it surprise you if I told you I was transsexual?"

Brian was whimpering and looked nervous. "No, I mean, um. You're so beautiful, and, um... Why are you talking about this?"

Stephanie stood up in front of Brian and looked at Jim, who nodded. She lifted up her red skirt and pulled down her panties, revealing a smoothly shaved, semi hard, six inch cock. "Surprise, " she grinned.

Brian was transfixed by her cock. He didn't say a word, but he was whimpering. He thought about getting up and leaving in that moment before he did what he really waned to do.

Stephanie had other ideas. "Do you want to touch it?" He said nothing. "It's okay sweetie," she added. "You can touch it."

Brian got on his knees in front of her, gently grabbed it and started sucking it. Stephanie laughed as she looked at Brian. "See. I told you."

"Brian, would you like to fuck my girlfriend, " Jim asked?

"I can't, " he replied as he continued sucking.

Stephanie laughed. "He's a sissy, Jim. I knew it all along." She looked down at Brian. "Tell me sweetie. Are you wearing panties?"

Brian stood up. "No, um." He looked at Jim. "I just remembered I need to go. I'll, um... I'll see you later."

Jim stood up in front of Brian, towering over him. "Brian, don't. You're among friends here. You don't have to leave. We won't judge you, will we honey?"

Stephanie stood, slowly playing with her she cock. "Of course not. Show me your panties, Brianna, I mean Brian." She giggled. "I bet they're pretty."

Brian looked at both of them. He removed his shoes and pulled down his pants, revealing smooth legs and a pair of frilly pink panties. "Oh, those are cute, " Stephanie remarked. "What else are you hiding?"

Brian was still nervous as he looked at Stephanie, then Jim and back to Stephanie again. He removed his socks, revealing toe nails painted hot pink. "Oh, those are cute, " said Stephanie. "Wait a minute." She reached out and grabbed Brian's right hand. "You painted your finger nails clear."

"I um..."

"What else are you hiding from us?"

Brian removed his shirt to reveal a pink bra. Stephanie walked up to him and kissed him. "What a cute little sissy girl you are, Brianna, " she took his hand and led him to the bedroom. Standing in front of the bed, she embraced him with a kiss.

Then she reached down and felt something hard in Brian's panties. "What's this?" She pulled down his panties to see a small pink chastity cage. "Really? Chastity? Where's the key, sweetie? I want a taste."

Brian blushed. "I can't. Mistress Alice won't let me, and she has the key."

Stephanie laughed. "Your online girlfriend?"

"Mistress, " he corrected her. "She's my Mistress."

Stephanie guided Brian's hand onto her clitty. "I see. What does Mistress Alice say about you sucking cock?"

Brian blushed. "She wants me to please any cock I am asked to please."

Stephanie smiled. "Oh, this is precious." She lay on the bed and spread her legs. "Are you going to please my she cock for me, sissy Brianna?"

Brian nodded and got on the bed with his head quickly over her crotch, sucking her cock with his ass in the air.

Stephanie looked over at Jim in the doorway, who had his eight inch cock out and was stroking it. "Just in time, sweetie." She ran her fingers gently through Brian's hair. "You wanted to help your best friend. I think you know what he needs now, don't you?"

Jim went to the bed stand for some lube and Brian took his mouth off of her cock and looked at Jim. "But."

"Did your Mistress say anything about taking cock in your ass, " he asked with a grin?" Brian nodded. "And, what did she say?"

Brian was as nervous as he'd ever been as he uttered his next words. "Um, that I. Um, I have to take cock in my sissy pussy whenever I get the chance."

Jim walked up behind Brian and laughed. "Oh my God, Stephanie. You won't believe this?"

"Butt plug, " she replied?

He pulled out a large butt plug. "Fuck an a, you've got it bad, don't you Brian?"

Brian didn't answer. He seemed resolved to what was going to happen as he went back to sucking Stephanie's she cock. Jim lubed him up more and entered his ass without too much effort. "You and I have some talking to do later."

"Hmm, this sissy has some great oral skills baby, " Stephanie quipped to her boyfriend. "You should try them out."

Jim was fucking his best friend pretty hard. "I plan to."

Stephanie grinned. "I bet his Mistress has him practicing on a dildo every night."

All of the toy play had prepared Brian for this moment, and for the ability to have a sissygasm. He was pushing back and taking Jim deep. "Fuck Brian. You should have told me you wanted to be fucked a long time ago. We could have made this happen."

Stephanie didn't get a lot of oral from Jim, but she was enjoying the experience from Brian. Soon enough, she popped her load inside his mouth, and he swallowed all of her sweet girlie juices.

Brian was next as he had a slow orgasm inside the confines of his chastity. If he were honest, he had fantasized about this moment with Jim's cock deep inside him for years. The grand finale came about ten minutes later as Jim erupted inside his ass. The three lay on the bed, kissing afterwards. "Fuck, that was amazing, " Brian finally admitted.

Jim kissed Brian. "Are you transgender, Brian? Do you want to be a woman and transition like Stephanie?"

"Yes, " he replied. "I have for a long time. I recently started hormones too."

"Why didn't you tell me?"

"I couldn't. I just couldn't."

"Well, from now on, you dress the way you want to, " Jim insisted.

Stephanie kissed Brian. "I'll help you out, sweetie. You have a lot to work with."

"But, what about the guys at work?" Brian looked uncertain about the idea.

""Haven't I always looked out for you?"

"Yes, you have."

"Then, you'd better dress as you want to, " he said with another kiss. "Or, I'm not gonna be happy with you."

"I will, " Brian replied.

"Good, " Stephanie said with a smile. "Now that that's settled, could you lick my pussy so it's ready for daddy's cock. Once he gets started, he likes to keep going."

"It's true, I do like to fuck, " Jim remarked as he kissed his girlfriend.

With an ass full of his best friend's manly seed, Brian soon had his tongue buried in Stephanie's t-girl pussy hole. "Mmm, this is another thing you're good at, Brianna."