Brad and Mandy had grown up together and been best friends as far back as they could remember. Even though Brad was three years older, it was an issue between them. Mandy saw him as her big brother and deep soul, and a young man to lean on when she had problems at school or at home. Someone who was always there to support her and have a good time. All that changed one day when they were in their early teens. Brad’s father got a job on the other side of the country, and they had to move. Mandy and Brad stayed in contact over the years, and one morning, she received an email from him where he told her he had decided to transition to being a woman. At first Mandy was chocked, but the more she thought about the more it made sense. Brad had always been kind of feminine in his ways, and maybe that was why they got along so well.
As the weeks turned to months, she would get photos of him so she could follow his transition. At first, she didn’t notice much, but with time, his features became softer, his body began to change, and slowly but surely, Brad turned into Brenda. She asked him if he was going to operate, but he said he wouldn‘t, just breast implants later on when he got older.
The years passed, and Mandy began looking for a university and applied to a few. She got a couple of rejection letters, but one of her favorites accepted her, and she was so happy she called Brad.
“Hey, guess what? I got in!”
When he spoke, his voice was softer than what she remembered from the last time they spoke. “Congratulations, that’s great. That means you will only be an hour from me, and we can meet up on the weekends.”
“Fuck yeah, this will be awesome, I miss you so much.”
“Well, I’m not the boy I used to be, as you know, so don’t freak out when you see me.”
“I know, Brenda. I don’t care who you are; you are my best friend.”
It took another six months before they could actually meet. It was just after Thanksgiving that Mandy drove her car into the apartment complex where Brenda lived. It had been an easy drive, and she was looking forward to meeting her friend after all this time. She grabbed her backpack with a few clothes and toiletries and then walked up the two stairs to Brenda’s apartment. She knocked, and when the door opened, she took a step back, and her jaw dropped.
“Hi, Mandy. It’s been a long time.”
“Brand..sorry, I meant Brenda, is that really you?”
Brenda laughed and twirled around in the doorway. “New and improved, don’t you think? Get in here, I got cold beer and wine.”
Mandy dropped her backpack at the door and followed Brenda. The living room was small but cozy with photos of Brenda’s parents and a few of her and Mandy when they were young. The view was over the parking lot, so that wasn’t very exciting.
“Have a seat. Beer or wine?”
“Wine.”
A few minutes later, Brenda came back and gave Mandy a glass. “Cheers.”
In the dim light, Brenda’s oval face was so beautiful. Her large blue eyes seemed to look straight through Mandy. She wore a sweater that slipped off her shoulder, exposing the soft curve of her breast. Her jeans sat perfectly and enhanced her long legs.
“You look amazing. Are you happy?” asked Mandy after sitting down and drinking from her glass.
“Yes, I am. It has been a long road to get here, and there are still many miles to go, but I’m happy. I am finally the woman I was supposed to be.”
“You are beautiful. So, you got the breast enhancements, I see.”
Brenda giggled and cupped her boobs. “Yes, I did, D cups, big enough to note, small enough to be comfortable.”
“Yeah, they look great. I know a few girls who did D or even double D, but they were a lot shorter than you, and it kind of looks weird.”
“What about you? How was your first semester? Any boys in your life?”
“School is doing fine, no complaints here. Not much of a love life, to be honest? I have been focused on school.”
Brenda raised an eyebrow. “Are you still a virgin?”
Mandy blushed and drank more wine. “If you must know, yes, I am.”
“Oh, girl. What’s the hold up?”
“I’m not in a rush to get fucked by some random guy I met at a party. I want it to be Mr. Right, you know.”
“That’s bullshit. The odds of your first guy being the right guy are microscopic.”
“What about you? What’s the deal? Are you gay, hetero, or what’s going on?”
Brenda sighed. “It’s a bit complicated, to be honest, and sometimes I’m not even sure. I’ve been with guys and girls, and I have no preference, to be honest. I’m equally attracted to both.”
“But, how do you do it, I mean, do you tell them straight up that you are trans, or do you wait?”
“I’m always honest with them; it’s better that way. Funny enough, a few guys have rejected me on the spot and then came back a few weeks later. I guess they were curious.”
Mandy knew she was getting quite personal with her questions, but she was curious. “When you are with guys, who does what?”
Brenda laughed and went to get more wine for both of them. “It depends, sometimes I’m on top, sometimes they are, and sometimes we just switch around.”
“Analsex. I never understood it. I mean, women have a clit in our pussy but nothing in the ass, so what’s the point?”
Brenda took in her friend. She had changed since the last time she had seen her. Back in the day, Mandy wore braces and glasses. The braces were gone, and she must be wearing contacts. Her face was still freckled, and her honey-blonde hair was long down to the middle of her back. As always, she dressed conservatively in a large sweater and baggy jeans.
“Well, guys have a prostate, which, when stimulated, can lead to an orgasm.”
“Really, I had no clue. At least you get pleasure out of it, I guess. Are you serious with anyone right now?”
“No, like you, school takes up a lot of my time.”
“I guess. You are graduating this spring, right?”
“Yes, and I have a few job opportunities when I’am done with university.”
“I’m sorry, I have to ask. What do women find attractive about you?” I mean, you don’t have a vagina, so lesbians wouldn’t find you interesting.”
“Curiosity, I would say.”
“Why? If they want dick, then there are plenty to be had who are not trans.”
“I don’t know, to be honest. But the ones I have been with seemed to enjoy the experience.”
“That’s just weird.”
“One benefit is that I can’t get them pregnant, and many girls like to fuck without a condom, even though it’s not recommended.”
“That’s a valid point. Not that I know what the difference is, since I have never had a cock in me.”
Brenda laughed. “One day you will find out.”
They continued talking late into the night, and when they had polished off two bottles of wine, they went to bed. There was only one bedroom, so Mandy slept on the sofa, which was quite comfortable.
Mandy woke up to the smell of coffee, and when she made her way into the kitchen, Brenda was at the stove. “Morning,” she said, and Brend turned around.
“Oh, shit,” said Mandy and put her hand to her mouth. Brenda wore a long T-shirt, and her morning erection was clearly visible under it.
“Oh, sorry, at least it still works sometimes,” said Brenda and laughed.
“What do you mean?” Mandy poured coffee into a mug and sat down at the kitchen table.
“The hormones, they affect my performance, so to speak, and it can be quite frustrating sometimes.”
“I can imagine. But it seems to work fine today.”
Without any warning, Brenda lifted her T-shirt, exposing herself. The head had slipped out from under the foreskin, large and dark red. “Yeah, it sure does. Too bad I don’t have anyone to enjoy it with.”
Mandy noticed there were hardly any testicles left. “What happened to your balls?”
“Hormones again. As I told you yesterday, I don’t produce sperm.”
“What comes out, I mean, what comes out when you have sex?”
“Clear liquid, pretty much. No squirting, it just kind of pours out.”
“Oh.”
Brenda didn’t lower her T-shirt, but stirred the scrambled eggs in the pan. “Do you mind if I jerk off? Watch the eggs.”
Before Mandy had a chance to say anything, Brenda went into the bathroom and locked the door. After a few minutes, she moaned, and then Brenda heard the water run, the toilet flush, and Brenda came out again.
Mandy turned off the stove and served the eggs on the plates Brenda had put out. The whole situation was strange, and Mandy wasn’t sure what to say, so she blurted out. “Was it good?”
“Hell, yes. It was great.”
Brenda placed the plates on the table, and they ate in silence. After a while, Brenda said, “I’m sorry if I made you uncomfortable. It’s just that when I do get a hard-on, I love to take care of it.”
“Hey, I know. I have a dildo which I use, so I’m all for it, don’t think anything about it.”
“Thanks, when did you get a dildo?”
“A couple of months ago. Bought it online. It’s quite nice, if I’m to be honest. It’s one of those silicone models, so it’s quite flexible.”
“Cool, and how do you use it?”
Mandy looked up from her plate. “What do you mean, how?”
“Well, do you stick in there quickly, or do you like to let it buzz around your clit first?”
“That’s an intimate question, don’t you think?”
“Yeah, but we have known each other for a long time, so I don’t see any problems with it.”
“If you must know, I like to use it around the clit until I’m really wet and then work it inside slowly.”
Brenda adjusted her seating a little. She was having another erection from listening to her friend describing how she masturbated. In her mind, she could see Mandy on her bed, her legs wide apart, thrusting the dildo in and out until she buckled and came hard.”
“Oh fuck, I have another one,” Brenda moaned and pushed her plate away and stood up.
“What the fuck?” Brenda’s cock was maybe two or three feet from Mandy’s face.
“Sorry, I have to go again, that is, if you don’t want to help me?”
“Help you?”
“Yeah, and at the same time, help yourself. I mean, one of these days you are going to meet a guy you like, and then it would be great if you had some experience, right?”
“I guess, but what does that have to do with you?”
Mandy couldn’t take her eyes from the cook in front of her. She had only seen them in porn videos, and now, close up and personal, she thought it was pretty cute. She didn’t know what a normal size was, but she figured Brenda was on the bigger side of medium-sized cock. The girth was about the size of a toilet paper roll, and she guessed its length at seven or eight inches. A drop of clear liquid formed at the tip.
“You are leaking, you better take care of that,” Mandy said, giggling.
Brenda stepped closer, and her cock was just inches from Mandy’s face. Involuntarily, her mouth formed an O, and she closed her eyes. Why did her body react that way, she wondered? She had fantasized about sucking cock and being fucked, but this was absurd; she had never done it with Brenda in mind, and yet, it felt only natural. Maybe it was the fact that she trusted her friend and knew she would never take advantage of or hurt her.
“Just kidding, I’ll be back soon,” said Brenda and laughed.
Mandy opened her eyes and saw her walk back into the bathroom. What the fuck, she thought. She had been sure she would feel the cockhead against her lips at any moment, but Brenda had left her hanging. She felt cheated but at the same time relieved. It would have been quite an awkward moment, she figured, if she had sucked the cock.
A few minutes later, Branda came out, and there was no sign of an erection under her T-shirt.
“Did you really think I would make you give me a blowjob?” she said when she sat down to finish her eggs.
“Shit, what do I know. You were all about getting experiences, and then suddenly you shove your dick in my face.”
“True, but you also know I’m a practical joker, and like to have fun.”
“Sure, you did that a lot when we were younger and got us into all kinds of trouble.”
They finished breakfast, and while Brenda did the dishes, Mandy took a shower. Brenda thought back to the moment Mandy had closed her eyes earlier and opened her mouth slightly. She had loved the sight of that, and had wanted to stuff her cock right down her throat, but she didn’t. She wanted Mandy to ask for it, for her to be the instigator. Not that Brenda was shy or anything, she had been the mover and shaker on many occasions with both men and women, but for some reason, Mandy making the first move was important to her. She might tease her friend, but not go all the way.
Mandy walked out of the bathroom and had a towel wrapped around her, covering her body up to her boobs. She opened her backpack and took out new panties and a few other items. She unwrapped the towel and laid it on a chair. She was naked with her back to the kitchen and was about to bend forward to pick up her panties when she felt Brenda standing right behind her. Then her warm hands were on her hips.
“You know, I love to fuck from behind it, it’s so sexy,” her friend said in a husky voice,
Mandy didn’t move. She stayed where she was and realized that something was moving between her ass cheeks. “Is that what I think it is?”
“What do you think it is?”
“Your dick, but it’s not hard.”
“Well, there is my T-shirt between my dick and your skin.”
“What are you doing?” Mandy turned her head and looked at her friend over her shoulder. Her eyes were laser sharp, and her gaze met hers. “It depends, what would you like me to do?”
Mandy took a deep breath and turned back, staring at the backpack that lay in front of her on the sofa. Brenda kept on moving her limp dick against her ass, and it felt good. It was exciting, and Mandy was curious. She slowly moved a hand behind her and then under Branda’s T-shirt. The dick was soft but oh so warm in her hand. Her thumb played with the exposed head, and she heard Brenda gasp in the silence.
“What are we doing?” said Mandy quietly.
“I’m not sure, but it feels amazing.”
“I’m holding my best friend’s dick in my hand who used to be a man and is now a girl with a dick, this shit is so fucking weird.”
Brenda closed her eyes and breathed deeper as Mandy’s hand began to stroke a bit faster, and with a smile, she felt her cock filling with blood and growing bigger.
“Oh fuck, wow, that’s so cool,” said Mandy and turned around, and quickly grabbed the cock again.
She sat on the armrest, naked, with Brenda standing between her legs. Her cock was pointing right at her navel and was growing harder by the second.
“You are pretty good at that, for being your first time,” said Brenda.
“Yeah? You think so?”
“Mm, I do. Do you want to have a taste?”
Mandy looked down at the now completely erected cock that was pointing straight up. “Why not?”
She slid off the armrest onto the floor, where she knelt before her friend. She opened her mouth and then licked the head. It was warm and soft like velvet. She grabbed the cock by the base and moved her head closer so the dick slid into her mouth. She moaned at the erotic sensation of her lips stretching around the shaft as she began to move her head back and forth.
Brenda watched her sucking her cock, and it was a beautiful sight. Considering it was Mandy’s first time, she was great at it. Brenda didn’t feel any teeth, just those soft lips sliding up and down her, the tongue teasing her head.
Mandy had never in her life thought that sucking cock would be this exciting. She had always figured it was just part of the foreplay to get the guy hard, not something she would like to do for any longer time, but it was. She felt Brenda’s hand around her neck, and then she was being mouth fucked, hard, and after a few seconds, she gagged. At first, she was afraid she would throw up and tried to wiggle loose, but Brenda held her in place.
“Relax, it just feels like you will throw up, but you won’t,” she said in a soft voice and continued. Five or six normal thrusts and then one or two much deeper ones, and as she continued, Mandy began to love the sensation, and saliva dripped from the corner of her mouth. She moved a hand to her pussy, and she was soaking wet.
“Do you want me to fuck you, fuck your tight little pussy right now?” asked Brenda.
Mandy nodded the best she could. Brenda pulled out her cock and helped her up. She gently pushed her back so she ended up on her back on the sofa and her hips right on the armrest. Brenda stepped in closer and grabbed her cock. She moved the head along Mandy’s slit.
“You got such a sexy pussy. I love those tiny lips and how your clit is poking out from the folds.”
Mandy tensed as she felt Brenda begin to push inside her, and she opened up for her. The cock was so hard, much harder than she had thought a cock would be. It worked itself inside, inch by inch, and Mandy began to gasp.
“Oh, shit, you are going to fuck me, aren’t you? Oh my god, oh my god.”
Brenda didn’t answer, just pushed in deeper until she was balls deep. “Thank god you have used your toy, or that would have been a lot more difficult and possibly painful.”
“Brenda, I can’t believe that after all these years you are going to fuck me.”
Her friend grabbed her hips and began to thrust, deep and hard, and for every thrust, Mandy’s boobs bounced, and she relaxed more. It felt so good, and nothing compared to her toy. The cock filled her up, and her stretched pussy wanted more and more of it.
“Harder, fuck me harder, please!”
Brenda did, and a few minutes later, Mandy arched her back and closed her eyes. Her pussy tightened around the cock a few times and then relaxed.
“Quickly, blow my cock before I lose the erection,” begged Brenda.
She walked around the sofa, and Mandy sat up with her feet on the floor. She grabbed Brenda’s dick when it was close enough and went down on her. This time, sucking and licking harder than before.
“Yes, yes, just like that, don’t be afraid, do it hard, stroke that cock, make the skin stretch down, oh fuck, it feels good,” moaned Brenda with her eyes closed.
Mandy did what she was asked to do, sucking and stroking hard, and then Brenda gasped and held Mandy’s head when she had her cock as far back as she could. Mandy felt the dick shudder and then a warm liquid run down her throat. She swallowed a few times, and then Brenda let go, and she pulled back.
They didn’t say a word at first, just looked into each other’s eyes, realizing that they had just fucked, and at some deeper level, they both knew that it was something that they had waited for a long time. What they didn’t know back then was that Brad would be Brenda when they did, but that didn’t matter.
“Wow, that was pretty cool,” said Mandy, finally, and stood up. Her hand slid down Brenda’s front, and she fondled her limp cock. “I’m looking forward to it being hard and ready again.”
Brenda giggled. “I knew it, you were a horny slut all along, you just didn’t want that part to show.”
Mandy kissed her neck. “You brought out the slut in me, and I’m grateful for it.”
She went to take another shower and left Brenda standing there, with a few drops dripping down on the floor from her cock. She turned and followed her friend into the bathroom. She knew from experience that it might be a good while before she could get hard again, but meanwhile, she could lick her friend and finger her to multiple orgasms. This would be an amazing weekend together.
