Honey, Let Me Explain

 Honey, Let Me Explain

 

Jeffrey was feeling all of his old urges coming back as he was folding his wife’s laundry. Recently he had started dressing up in her clothes when she was gone. He was happy to find out that they actually fit him. About six months ago, he started dressing up in her clothes and playing whenever he could.

There was always a part of him that felt like he was born in the wrong body, but Jeffrey suppressed it. These aren't the thoughts a boy should have. Since he was very young, he had been grabbing his mother's or his sister’s clothes and dressing at home. It was only when he met Abigail that he stopped.

He reasoned that he could stop for his wife. He dearly loved her, and he had since high school. Abigail had the body of a goddess, and he was jealous of her. From her shapely ass to her wide hips to her still firm DD Cup breasts, he imagined having that body for himself.

Now, Jeffrey had a pretty good body of his own. He wasn't overly masculine, but he was in good shape. He had gotten involved in the swimming team in college, and since then he has kept his body shaved. His wife never said anything about that. He also kept his hair somewhat long, though tied back.

At one time or another, he had even tried taking hormones. He dreamed of having breasts, and the hormones actually grew him small breasts. Abigail joked with him that he had man boobs. There was one time about a year into their marriage when she even put a bra on him. "If you're going to have girls like these, you should go ahead and wear a bra like me."

That wasn't the only moment when she indulged him. She had no idea what it meant to him, but soon she was putting panties on him and dressing him in a nightgown. She then started to paint his nails and put on some makeup. The resulting night of lovemaking was one that neither would forget.

Jeffrey had hoped that they would continue to do that, but it stopped after that. Abigail enjoyed it deep down, but she was ashamed to admit it. Jeffrey bought some clothes to dress privately but within a month he threw them out.

Now, the old urges were stirring within him again. He held her pink satin chemise in his hand and walked into the bathroom. He held it up against his body. It felt soft to the touch. "No, " he told himself. "I can't."

He continued to fold her clothes when there was a knock upon the door. It was his best friend Alan, who just walked in after knocking. "Hey dude, what's up?"

"Not much, just folding my wife's clothes."

Alan knew all about Jeffrey's dressing up when he was a kid. He actually thought he looked like a pretty girl when he was all made up in his sister's clothes and his mother's wig. There was one time when he caught Jeffrey at just the right moment. What happened next was something they never talked about in the years that followed.

They spent the entire day at Jeffrey's house with Jeffrey dressed up. Jeffrey gave his first blowjob that day and also took his first cock in his ass. It was the first sexual encounter for either of them. The next day, they just talked to each other as if nothing had happened the day before.

Alan smiled at Jeffrey, who was holding a pair of his wife pink panties. "See anything you like in there?"

Jeffrey blushed. "What are you talking about Alan?"

He shrugged. “Oh, you know, if you want to slip into one of your wife's outfits and prance around the house, I don't care. Hey, do you got any beer, " he asked as he walked into the kitchen and grabbed one.

Jeffrey just looked at Alan, who walked back into the living room with a beer in his hand. "What are you talking about?"

"Nothing, " he said casually as he took a drink. "I seem to remember that you liked to dress up back in the day. If you want to, go right ahead."

"What are you talking about? These are my wife's clothes, " he replied as he was blushing.

He took another swig. "Yeah, I bet you would look sexy in those clothes. Especially in that red thing right there."

"I'm not going to do that." He grabbed the clothes basket and headed back to the bedroom, but Alan grabbed his arm. "What are you doing?"

"Suppose you had no choice, " he said with a smile. "What if I told your wife what a little prancing sissy you were back in the day?"

Jeffrey laughed uneasily. "You wouldn't."

"Well, " he said as he downed the rest of his beer, "I wouldn't if you dressed up for me. It would just be our little secret and nobody would have to know."

"And if I don't?"

"Well, let's just say Abigail would find out all the details of how you liked to dress up back in the day. Remember that time we went out to the drive in together?"

"Ok, " Jeffrey sighed. "Let me go back to the bedroom and get dressed."

Alan shook his head. "No, strip in front of me and put that on, " he pointed to the red satin babydoll and matching panties.

"Are you serious, " he protested?

"Very. Strip. Now!"

Jeffrey quickly took down his shorts and underwear and removed his t-shirt. He was naked in front of his longtime friend. Alan laughed, "Oh my god. You still shave your whole body?"

"What? I like it that way."

He laughed and shook his head. "Well, you always were a little bit of a sissy, weren't you?"

Jeffrey slid the panties up his legs, and they felt good against his body. He was starting to get a little bit aroused. "Oh, take down your hair. I want you to wear it down for me, " Alan instructed.

He let his hair down. It went down to his shoulders. Alan winked at him. "Starting to look like a lady already, " he said as he headed back to the kitchen for another beer.

Jeffrey blushed, but he liked being called a lady by his best friend. He slipped into the nightie, and it felt exquisite against his body. Alan returned to the room and took a swig as he looked at his friend. "Oh, I'm sure your wife has some makeup, make yourself nice and pretty for me."

Jeffrey began to do his makeup. He and his wife had a similar skin complexion, but there was a redness around his mouth and nose that he was able to conceal with her foundation. A little bit of mascara, blue eyeshadow, luscious red lipstick and some blush and a splash of Abigail's Chanel Number 5 perfume, and he was about to go back to the living room. He paused. A thought occurred to him. He reached into the closet for a pair of five-inch red heels. They were a little tight on him, but he managed to get his feet into them.

What he found when he returned to the room was a sight. Alan was sitting in the reclining chair drinking his third beer. He had his pants down with his cock in his hand. He looked over at his friend and smiled. Damn Jeffrey, or would that be Jessica?"

Jeffrey was surprised by what he saw. "Alan!"

"Yes.  I remember Jessica. She is quite the cutie.  I think I need her help."

"Alan, " he protested.

"Of course, if you want your wife to know what a little slut you are. Oh, that reminds me. He reached into his pants pocket on the floor and grabbed his camera phone. He snapped a couple of shots of Jeffrey dressed as Jessica. "There, that's better. As I was saying."

"Alan, what about Rebecca?"

"Hey, " he chuckled. "What she doesn’t know won't hurt her. Why don't you put your pretty red lips to use there darling."

Jeffrey felt trapped in the moment. If he did nothing, he might not get in trouble with his wife at this point. However, doing something meant cheating on her with his best friend. Instinct took over and he crawled between Alan's legs. He took his seven-inch member inside his mouth.

"Oh fuck yeah, " said Alan. "Rebecca doesn't do this shit for me anymore. Oh yeah, right there. You're hired".

It was a weird scene as Alan took another swig of beer while Jeffrey had Alan's cock in his mouth. He was already tasting his cum. "Damn, girl, you really like sucking my cock, don't you?"

Jessica was on automatic pilot with her best friend’s cock in her mouth, about ready to shoot a load down her throat. His words were echoing in her mind. "Why did it take so long for you to suck my cock again?"

Jessica just continued to concentrate on sucking his cock, taking it deep at times, and the taste got stronger as he was about ready to erupt. Then it happened. "Ah yeah, there it is, " Alan proclaimed as he began to shoot spirits of his love juice down his best friend's throat.

Jessica remembered this scene from years ago, and she repeated her actions from back then. She swallowed every drop.

Alan looked down in amazement of Jessica. Wow, that was so hot. "So, why didn't you?"

"Why didn't I what?"

"Suck my cock after that day. You remember that day, don't you? How could you forget?"

Jessica blushed. "Oh, I never forgot. You don't forget being fucked by your best friend. You didn't even wear a condom that day."

Alan ran his hands through Jessica's hair. "I don't seem to recall you protesting, but why didn't you ask for a repeat performance?"

"I don't know." Jessica thought about it for a while. "Maybe I was waiting for you to say something."

"Shit, I thought it might get weird between us, so I didn't say anything. I didn't want to lose you as a friend."

Jessica looked up at him with her blue eyes. She shook her head. "That was never going to happen. You've always been my best friend."

"To be truthful, I always thought you were one of them transsexuals that I've heard about on the talk shows. I was surprised when you married Abigail."

"Oh shit, " Jessica said. "Abigail. She cannot find out about this. She'll kill me, and I can't lose her. I'm going to get a beer. Want one?"

"Yes, I do, " he reassured Jessica. "And don't worry. I'm not going to say anything to her. But I would like a repeat performance of that day, if you don't mind."

"What are you talking about, " Jessica said as she handed him the beer?

"Oh, I think you know what I'm talking about. When is the last time you had a good fucking?”

Jessica took a drink. "You're the only man I've ever let inside me."

Alan was surprised by that revelation. "No shit?"

"It wasn't that much longer after that day that I started dating Abigail, and I do love her."

"Alan took a big swig. Dude, don't worry about it. So, you're bisexual. Most of us are."

"I don't know if she can handle it, " she said. She was worried about what her wife's reaction might be to this.

Alan got up and walked to the bathroom. "You might be surprised, " he said with a laugh.

Abigail was to be gone till later in the evening, so the two spent the day together. Soon, Jessica had her mouth around Alan's cock again. What was weird was that as Jeffrey was dressed as Jessica, Alan started treating her more like a woman. And, she liked it.

“Get it good and hard, " Alan told her. "I want to feel it inside you."

"Wait, really?"

"Jessica, do you have any idea how many times I’ve thought about the day we spent together?"

"I always thought of you as a straight man. I know you love the women. Why were you thinking about that?"

Alan surprised Jessica with a kiss. "Well, for starters, you're my best friend. Also, I always did think of you as more feminine than masculine. You're pretty much a woman to me in my mind, I guess."

"Really?"

Alan laughed. "You're not really mechanically inclined, you weren't involved in physical sports and I had to bail your ass out of how many fights? You were always a bit of a sissy."

"But why did you hang out with me for all those years, " Jessica asked with a hint of sadness in her voice?

"Isn't it obvious, " he said kissing her again. "I could talk to you about anything. You always had good advice, and you made me laugh."

"Oh, I had good advice?"

"Yeah, " he said with a bit of a grin. "Like for instance, where would you like me to nail you at?"

Jessica was becoming overwhelmed with her sexual desires in this moment. She wanted him inside her, and she felt guilty for that. Still, it was going to happen. She looked around and pointed to the kitchen table. "Right there, on my back."

"Missionary it is, " he replied. "Got any lube?"

"Medicine cabinet in the bathroom," she said as she lay on top of the kitchen table.

When Alan returned to the kitchen, he saw Jessica with her arms wrapped around her legs exposing her tight sissy love hole. "Oh my, " he said with a smile. "It looks like somebody wants to get fucked."

"Shut up and do the deed, " she said with lust in her voice.

Alan retrieved a jar of Vaseline and liberally applied some to his fingers in her hole and shoved two fingers inside her. She squirmed. "Damn, you are tight." He continued to finger fuck her, and he could tell from the movement of her body that she was really getting into it.

"Are you ready for my cock,”  he asked as he pulled his fingers out?

"Uh huh, " she replied lustfully. "Do me right here on the kitchen table."

"As you wish." He positioned his cock at her rear entrance.

"It's not as if I have a choice, " she said with a smile. "You were going to tell my wife."

"Oh stop, " he said as he shoved his cock inside of her slowly. "You know you want this. I bet you've been prancing around your house in your wife's clothes for a while now." He continued to push inside as he spoke. "Just waiting for me to come in here and fuck you again."

"No I haven't, " she protested. "Fuck, that hurts."

"You'll get used to it, " he said with a smile. "And you can deny it all you want, but I know you've been prancing around in your wife's clothes."

"Oh God, that feels good, " she moaned. "How the hell would you know that? We haven't even spoken about me dressing up in years."

"Because I told him, " said a female voice from behind the two of them in the living room. It was Abigail, who was watching the whole scene, and yet she didn't appear to be upset in the least.

"Honey, let me explain, " Jessica said as her friend continued to fuck her as if her wife wasn't even in the room.

"Explain what Jeffrey, or is that Jessica? Explain how you’ve been prancing around the house in my best lingerie and now you're getting fucked in the ass on our kitchen table by your best friend?"

Jessica was totally embarrassed, but there was nothing she could do. Her best friend's cock was sliding in and out of her while her wife watched. "Oh god, I'm so sorry."

"Don't be sorry, " she said sarcastically. "You're enjoying this, and I want you to finish it up. Alan, fuck her good."

"Okay, " he laughed. "That, I can do."

“This is as much my fault as yours, “ said Abigail as she walked up to the kitchen table and looked into her husband's eyes. “I saw the signs for years, and we just sat here and pretended nothing was going on. Admit it, you're a girl trapped in a man's body. Well, not too much of a man's body, but you get my point."

"Oh god, honey don't leave me. I love you."

She leaned down and kissed her sissy wife on the lips. The pleasure Jessica felt from her friend's cock hitting her in the right spot was overwhelming. “I arranged the whole thing, you silly little sissy slut, " Abigail explained. "I've known what you've been up to all along, but I had to figure out a way to get you to admit it."

"Damn, she's got a tight ass, " Alan proudly proclaimed.

"And that's a bad thing why, " Abigail kissed Alan on the lips? "I know how you men are. Always looking to stick your cocks in a tight hole."

"Yeah, but Rebecca won't do anal, " Alan remarked as he continued to plow his sissy lover's ass like there was no tomorrow.

"That's too bad, " Abigail said with a smile. "She doesn't know what she's missing."

Jessica was mystified by that comment as she hadn't gotten to do anal with her wife either. In this moment, she was surrendering to the pleasure that Alan was giving her.

Abigail reached down and began to massage her sissy husband's clitty. "There's going to be some changes around here, my dear."

"You aren't leaving me, " Jessica asked with a bit of terror in her voice? "Please don't leave me."

Abigail squeeze her sissy's clitty. "Hell no, I'm not leaving you. I told you I loved you, you silly sissy. But from now on, I want to see more of my sissy wife here. If our marriage is going to work, we both need to be happy, and I could see you were struggling to be happy."

"Why don't you show me how happy you are, sissy Jessica." She squeezed her sissy's clitty again. "Cum for me."

The combination of Alan's pulsating rod and her wife's grip on her clitty caused Jessica to pop in her wife's hand. There was quite a bit of it. As her ass spasmed from her orgasm, that drove Alan over the edge as he erupted inside of her.

Abigail began to lick her hand of her sissy's cum. "Why, you naughty little slut. Look at the mess you made." Jessica could feel Alan's love juices inside her.

Alan leaned down and kissed Jessica on the lips again with his cock still inside of her. Then, he remembered he needed to be someplace. "Oh shit, what time is it?"

"7 o'clock, " Abigail replied. "Why? Are you late for something?"

Alan pulled out of Jessica's well-used love hole. "I hate to bang and run, but Rebecca is going to kill me if I don't get going."

Abigail kissed him on the lips as he got dressed. "Well, thanks for helping me out here."

"Anytime, ” he replied with a wink, "and I mean that."

"I'm sure you do, " she giggled.

The door slammed shut behind Alan as Abigail directed her attention to her well fucked sissy husband on the kitchen table. Jessica looked up at her, uncertain what her reaction was going to be. "There's going to be some changes around here, my dear, " Abigail explained. "But, don't worry. I have a feeling you're going to like what I have in mind."