Their Monthly Date Night

Darren had started the bath running and poured him a glass of Rose as was his ritual. Tonight was date night, and when Cheryl got home, he needed to have everything ready.

The soft romantic music was already playing as he dropped in the bath bomb that smelled of roses and climbed in. He lays back in the warm water and takes a deep breath, and closes his eyes.

The eyes that open are no longer his, or at least that is how the ritual goes. They are Debra's, and tonight is the one night of the month that she gets to come out and play.

*****

It had begun innocently enough, or at least as far as Darren knew. A few of their friends had invited them to a costume party a couple of years ago, and Cheryl had come up with the idea of going as Debra and Chet.

Chet wore a pair of jeans and a polo shirt with a sport coat. She looked good, but she was still obviously one very attractive woman even with the enormous bulge she had added in her jeans.

Debra wore a simple black dress that came off the shoulders, and thanks to a bra and some shapers that Cheryl used from time to time, Debra had the appearance of a little cleavage. The hem of the dress came to her knees, and the shiny black flats were easy on his feet but looked right. Cheryl had provided a shoulder-length red wig that she styles, and she also applied simple makeup to his smoothly shaved face. Was anyone fooled into thinking Debra was real? He doubted it, but it was a costume party, so it didn't matter.

From the time they had arrived at the party, Chet had been showing her off, introducing her as Debra, bringing her glasses of Rose, and putting moves on her just as if she was his date that he wanted to take home and seduce later.

On the way home, the many glasses of Rose had put Debra, Darren found that the role he had been playing all night was almost natural at this point. He sat in the middle of the backseat of the Uber, and Chet sat by the door. Debra leaned against him with his arm around her shoulders.

Debra didn't know what started things off at the time, but in hindsight, it was Chet sliding his hand down to touch her breast. Debra had looked up into Chet's eyes, and he had kissed her. Not in the same soft way that Cheryl usually kissed him but more forceful, more masculine, and way more hungry. After a few minutes of heavy kissing, Debra being aggressively felt up by Chet and caught up in the role she had been playing all night, moved her hand to Chet's lap. The hard bulge was not what she expected to find.

Cheryl had gone a little farther with her costume than Darren had been aware of and the large but not to firm dildo that she had strapped inside her jeans was a sign that she might not have had so innocent a motives this evening. At the time, though, Debra was too caught up in the moment to think about it.

Her hand just naturally started to rub and stroke the hard shape it found. The kisses grew even more passionate after that, and soon Chet made it clear he wanted more and began to push Debra down toward his lap.

Debra knew what Chet expected. She unzips his jeans freeing Chet's hard cock. It looks and feels real for being silicone, and when her mouth closes around the head, it is warm and smells of Chet.

For the remainder of the ride home, Debra sucks on Chet's hardness, guided by his hands in her hair. A few blocks from their house Chet pulls her off his cock and kissed her while zipping up.

Once the door is closed, Debra drops to her knees in front of Chet and hungrily pulls out Chet's cock and shoves it in her mouth.

The night ended with Chet fucking Debra's ass until she came with his well-lubed cock.

*****

After that night, it had become a regular event that Darren would become Debra for an evening. She would get ready, make dinner, and have a drink ready for her man when he came home. Cheryl would change into Chet, and after dinner, he would put on the charm and fuck her senseless. For the past three years, that was how it played out.

Debra soaked in her bath, her hand lightly feeling her freshly shaved thighs as she remembered that first night. She was turned on but needed to get moving as Chet would be home soon, and she wanted everything to be perfect. About an hour later, dinner was in the oven, and she is wearing a short dress that drops way down in the front. The fillers and pushup bra had been replaced long ago by a pair of breast forms that perfectly matched her shape. She is wearing a pair of short heels. The frilly apron she wears completes the hot housewife look.

Could she pass as a woman out in the world? She doesn't care as this isn't about the world but about Debra and Chet and that feeling she got when he came home to spend the evening seducing his way into her panties. Darren never felt as relaxed as when he lay in bed as Debra, with Chet spooning her as he drifts off to sleep in the aftermath of their lovemaking.

*****

At 8 pm, she hears the beeps of the front door unlocking and rushes to greet him, only to receive a big surprise. Cheryl is not alone, but an attractive man walks in behind her.

Seeing the lovely Debra instead of Darren, Cheryl covers smoothly and gives her a soft hug and a kiss on the cheek.

"What a pleasant surprise but where is Darren?" she says softly.

Debra is off balance but tries to recover. "He had to go into work, something about a server crash. Darren said it might be a long night and asked me to make dinner for you. He knows how hard you work and didn't want you to have to fend for yourself.

Cheryl smiles, "That husband of mine is so thoughtful. I will have to return the favor later." she says, winking at Debra, who blushes a little.

Despite the unexpected company, she finds herself in character and very much looking forward to Chet showing his appreciation later.

"Tom, I would like you to meet Debra, Darren's sister. She lives close by, and they both look after me since I seem always to be working."

"Debra, this is Tom, an old friend from college that called me when he was in town this morning. So I invited him home for dinner. I guess it slipped my mind to let Darren know. I hope there is enough food." she said, sounding sincere.

Tom stepped forward and put an arm around Debra, leaning in to kiss her cheek. Up close, the strong manly smell of a little sweat mixed with an earthy cologne had an impact on an already aroused Debra.

She stepped back, blushing even more. "I think there is more than enough."

Debra has the pair sit in the living room while she gets them a drink. She mixes them each, Chet's favorite cocktail, a Bourbon Manhatten.

Cheryl takes hers with a wink that further stokes the fire in Debra. Tom takes his with a smile that has a similar effect. In the far back of Debra's mind, Darren is not sure what to make of those feelings, but he is too engaged in his role as Debra to do anything other than smile back and add another place setting on the table.

The conversation and wine flowed throughout dinner, with Tom sharing quite a few interesting stories of his and Cheryl's college adventures. If Darren had been here, he probably would not have been as open, but he seemed to be trying to impress Debra by expounding on what it had been like dating Cheryl in her wild days. Debra made a note to ask Cheryl for more details.

After dinner, Tom and Cheryl retired to the living room as Debra mixed another round of drinks. SHe found Cheryl in the armchair talking across the coffee table to Tom.

"Come join us and let those dishes wait till later," Tom says, so she goes and grabs her glass of wine and sits down beside him on the couch.

After a few more stories and another glass of wine, Debra hardly notices as Tom's rests on a hand on her knee. Cheryl can't help but smile as her plan begins to come to life.

Tom suddenly turns to kiss a completely surprised Debra, who returns the kiss. Cheryl leans back with her drink and watches.

Tom slowly pulls Debra to straddle his lap, hands under her short dress, cupping her ass. Debra is kissing him passionately now, lost in the moment. Not that it isn't how she expected the evening to progress except that it is not Chery/Chet she is kissing but one of Cheryl's former lovers.

Fingers begin to pull down the zipper on the back of Debra's dress. Looking back, she finds Cheryl standing behind her.

"I think Tom needs to see how lovely you are under this dress, don't you?" Cheryl says quietly.

Debra stands in front of Tom, her dress sliding to the floor. The lingerie underneath is black lace and made to show off the shapely breast forms and hide the other additional features of Darren's body. In the soft light of the living room, the effect is nearly perfect. The bulge in Tom's pants shows that he approves of her look.

Debra looks unsure as she stares down. Role-playing with his wife is one thing but having sex with another man is quite another. Cheryl stops Debra's thoughts by placing her hands gently on her shoulders and pushing her to her knees in front of Tom.

Debra reaches out to undo Tom's belt and pants to gain access to his hard cock.

As it comes into view, it is much larger than the one Chet straps on. The male taste on her tongue as she licks the head is intoxicating. She moans softly and takes it into her mouth. Then it is Tom's turn to moan.

Debra begins to slowly bob her head up and down on Tom's large cock. She doesn't think of anything but the need burning in her and the desire to please him.

Cheryl sitting in the chair across from them, slowly fingering herself. She had imagined how erotic it would be to watch Debra embrace her desires, but this is much hotter than she ever imagined. Tom's cock was everything she remembered, and while she did not intend to partake of it for herself because, as twisted as it seems, she would keep her vows to Darren, she had no problem letting Tom have his way with Debra.

Tom began to feel the cum rising, and while he wants to cum all over Debra, he also wants to take her virginity as well, so with a bit of effort, he pulls Debra up off his cock and up to kiss him. As she settles down to once again straddle him, he slips his fingers inside the back of her panties to rub her opening. Her breath catches as she thinks of how large his cock is and in anticipation of what is coming next. She leans over and pulls a tube of lubricant from the end table, where the couple keeps it for date night.

Soon Tom's fingers move in and out of her, stretching her ass in preparation for his cock. After he can work three of his large fingers smoothly, he removes them and replaces them with the head of his even larger cock. Debra's moans echo in the room as he pushes into her. She is lost in the fullness as the man's large balls touch the fabric of her panties.

She begins to ride him slowly. Soon, they are moving with complete abandon. Behind her, she hears a loud moan and turns to see Cheryl, her fingers buried in her pussy, watching them intently. She pulls up from Tom and slides the coffee table away, falls to her knees, and burying her face in her wife's sweet pussy. Tom moves behind her and shoves his cock back into her tight ass.

Cheryl screams as Debra's tongue is pushed hard into her by the force of Tom's fucking. Her orgasm is one of the strongest she has ever had. Debra is close to her release as well, and her ass tightens on Tom's cock. After a few more minutes of hard strokes, he pulls back to sit on the couch, stroking his cock. Debra instinctively turns around to face him in anticipation. His cock explodes all over her face and into her open mouth. Debra moans as her orgasm fills her panties.

Debra continues to kneel in front of Tom, covered in his cum, as he finishes. A click from above them awakens Debra, and she opens her eyes to see Cheryl with her cell phone taking pictures.

"Sorry, I wanted us to be able to relive this anytime we want." is all she says.

Eventually, Tom heads to the bathroom to clean up before kissing them both goodbye, Cheryl on the cheek and Debra hot and deep.

After he leaves, Cheryl leads Debra to the bathroom, and she slowly removes the remainder of her lingerie, breast forms, and the red wig. In the shower, she washes the cum and makeup from Debra/Darren's face.

Then she turns around, and Darren, now back and painfully hard, rams his cock deep into her, showing her that while he may have a definite feminine side he needs to let out, he is a man as well.