The Alluring Valentine

Author's Note: This is one of my entries for Literotica's Valentine's Day 2025 Contest. It features the return of Eric, Jade, and Nate from "The Alluring Stranger".

All characters are 18 or older. Comments and feedback are welcome, enjoy!

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Hey, it's been a while. Here's a brief recount, Jade is my boyfriend, a crossdresser that I once knew as "Jayden", back before he was being true to himself. A friend of ours, Nate, cooked a plan up with Jade to get the two of us together and save my heart and soul from sinking even lower into the darkness and self-pity I was drowning in. Jade had always had a crush on me but could never approach me out of fear of exposing himself. I was too busy chasing women, with no success, so I never noticed. I suppose it was fate that I would finally lose my virginity to Jade and none of the women I pursued. My body, soul, heart, was meant to be shard with him, no one else.

Anyway, you want to know about our first Valentine's Day together. But first, some updates. We spent a lot of time together as new couples do, going on dates, spending the night with each other, and of course having sex every night. For Christmas, Jade asked me to move in with him and I accepted, we have lived together since. As for our jobs, I got promoted to Assistant Manager of my department in the factory I work at, we make textiles. Jade was between jobs for a few weeks before finally landing a job at a boutique that has a large cross-dressing clientele. He became quite popular for his beauty and knowledge of fashion. I guess you could say we both work in fabrics, though in vastly different industries. With that out of the way, I'll get to the actual story, it begins fifteen days before the holiday. Well, the night before the fifteen days technically.

That night, Jade and I were in the throes of passion, both of us naked as we were at birth. He was lying on his back while I was inside him, pistoning in and out of his hole. His legs were up, his shins resting against my chest. His penis was hard and swaying as I fucked him. It isn't very big but not small either, I can hold it in my hand with the tip poking out. Mine is bigger but I would never make it as a pornstar. Despite that, he loves having it inside him.

Jade has a very feminine body, lithe with an almost hourglass shape. He kept his body, pubes, and legs shaved, though he once told me that he never had much body hair to begin with. As I fucked him, he looked up at me with adoring eyes and his arms drawn up to his chest, whimpering and moaning. He is so cute when he does that, he knows it pushes my buttons and makes me fuck him harder, which I did.

"Oh baby.. yes.. fuck me.. breed me.." Jade begged. I fucked him even harder, our flesh loudly popping with each collision. I held onto his thighs, grunting and groaning as I rammed away. He began letting out girly screams as his cock spat out strings of hot white goodness onto his belly. I felt the inside of his rectum tighten around my cock and contract, which sent me over the edge. I roared when I unleashed a flood of cum deep inside him, my orgasm made his own more intense.

"Yes!! Give me all of it!!" He closed his eyes and received everything my balls had to offer.

I pulled my penis out of him, his gaping anus leaked my seed and let it run down into his crack, getting some of it onto the towel he was laying on, we didn't want to stain our sheets after all.

"I LOVE being fucked by you! You're so dominant and make me feel like a real girl!" Jade chirped. I laid next to him and made out with him for a bit.

"And I love fucking you, and you are a real girl." I responded. "But after tonight, you're going to have to do without it until Valentine's Day. No fucking until then."

"But whyyyyyy...?" He whined a little.

"You know Valentine's Day is special! We're going to have a romantic evening, and a sexy night. I want to store up some nut so I can blast it all inside you."

"Yeah? Will it be more than usual?" I clearly piqued his interest.

"Oh yeah. It'll be like the first time I fucked you!"

"Really? Yay!!" He giddily clapped his hands. "What a way to top off what I know will be a wonderful evening! Okay, no sex until then! But what about teasing?"

"We can do that, but we have to be careful. We don't want to end up fucking before that night."

"Deal! Buuuuuut, we still have tonight..." Jade grinned as he moved down to lick the cum off my cock, then began sucking it.

I shook my head. "Fine you little horndog. But you're going to get it too!" I shifted his waist so that we were lying on our sides and sucking each other. Since we had both climaxed, we were able to suck for a good few minutes until we came again, both of us swallowing a salty load. With that, it was time for bed. We laid naked together, I held him in my arms. While we still slept together every night, that was the last night we did so fully nude until Valentine's Day.

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The following day began our fifteen days without sex. I had filled Nate in on my plan with Jade for Valentine's Day, omitting the more personal details. He was partially responsible for Jade and I being together, so I wanted him in the loop. During lunch that day, I received a text from him, telling me to come to his apartment after work and that it was "urgent".

I replied, "Is everything okay?" He was active, as my messaging app let me know he was typing.

"It is if you want to make Valentine's Day special for Jade!"

"Dramatic much?"

"Just come to my apartment later, you'll thank me for it!"

"Fine, I'll be there" While I spent the rest of my shift wondering what he was going on about, I didn't expect much. Nate had a habit of making a mountain out of a molehill at times.

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I pulled into the parking lot around 5:30, then made my way to his door and knocked. He answered.

"Hey brother, glad you could make it! Get your ass in here!" Nate stepped aside and invited me in. His apartment was a typical bachelor pad, pictures of women in bikinis with beer on the walls, piles of dirty clothes piled up in corners, a ridiculously large TV and a gaming system in his living room. I hope he didn't bring women over, or at least cleaned up first if he did. I have to admit though, this was exactly how my old apartment looked before I met Jade, so I couldn't give him too much shit about it.

"Wow, Jade would kill me if I let our apartment become anything like this."

"I'll clean up when 'the spirit' moves me." An excuse to be a lazy bastard. "We have an urgent matter to discuss. You're taking Jade to Serenata's, right?" Serenata's is one of the fanciest Italian restaurants in town, and the hardest to get into. I made a reservation the week before Christmas to get us in for Valentine's Day and got the last available table!

"Yeah. If you're worried about me finding a suit to wear, I've already got that covered."

"Suits are important, but it's your dancing skills I'm worried about." Ah, there it was.

"I admit that I wouldn't make it past the first round on one of those shows, but I'm not THAT bad."

"Eric, buddy." He put his hand on my shoulder. "I have seen you dance. You dance like a drunk with two left feet standing on banana peels." Ouch.

"Damn, isn't that a bit harsh?"

"The truth often is brother."

"Wait, are you saying that you are going to teach me?"

Nate smirked. "I'm not a dance instructor or anything, but I think I can teach you well enough to keep Jade from getting any broken bones on your big date!"

"Okay, but I'm sure I can get away with slow dancing the entire evening. That shouldn't be too difficult."

"Agreed. I don't have enough time to teach you any extravagant dance moves, so slow dancing will be our focus. Now, let's get started." He held his hands up.

"What are you doing?"

"You're gonna have to dance with me if you want to learn."

"Fine." I took his hands and stood uncomfortably close to him. Many people assume that every gay man is attracted to all men, I thought that at one point myself. After entering a relationship with Jade, I discovered otherwise. Despite being in a relationship with a biological male, I was not suddenly attracted to men. As a matter of fact, women don't attract my attention anymore either. Jade is the only one, male or female, that catches my eye.

"I'll let you try leading first so I can see what you've got." I began to dance with him, taking the lead, and it soon became obvious that he was right. I sucked at this; I had no idea what I was doing. I had no rhythm, stepped on his feet a few times, and almost fell with him at one point. We stopped, much to our relief.

"Hoo boy, you're even worse than I thought." He scratched his head.

"Is there any hope for me?" I thought Nate was blowing hot air to begin with, but I became deeply concerned after that near disaster.

"Don't worry man, I can help you. I'll lead now, pay close attention to what I do."

We danced again with Nate leading. He wasn't a bad dancer; I wonder who taught him. For two hours, we practiced dancing. I took mental notes on his movements and applied what I had observed to a small degree of success.

When I returned home that evening, I explained to Jade that Nate wanted me to spend time at his apartment for two hours every day until Valentine's. I told him it was a surprise.

"Are you two having some 'guy-on-guy' action?" He teased.

"Something like that, but not what you're suggesting, perv."

Jade laughed and nudged my arm. "You're too cute! Sit and relax, today is my turn to do the chores."

Jade and I take turns cooking, doing laundry, and keeping our apartment tidy. One of us does the chores while the other cooks. I took his offer and sat on the couch, turning the TV onto the football game. He had stepped into the bedroom for a moment, then came back out wearing a maid's apron and nothing else! I should have turned the TV off, because I didn't watch a second of the game after Jade began cleaning. He was constantly bending over, exposing his rosy pink anus to me. Even when he was standing, his bare slender hourglass frame, wide hips, and bubble butt were enough to keep my eyes glued to him.

That is how the fifteen days passed, daily practice with Nate after work, or earlier in the day on weekends. When it was my turn to do the chores, I did so shirtless. It wasn't nearly as sexy as what Jade would do, but there were many times when I caught him staring.

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At last, Valentine's Day arrived. Our morning was normal, preparing for work, breakfast, the works. I pulled up to the front of the clothing store to drop Jade off like I do every morning.

"Don't pick me up later, I have something to take care of, a friend will bring me back home. I'm sure you have something to do as well?"

"Okay. Yeah, I something to get after work." A suit and roses.

"M'kay! I'll see you later, love you!" He leaned forward to meet me with a quick kiss.

"Love you too!" We said our goodbyes, then Jade got out and went inside. As I drove to my own job, I imagined all sorts of outfits he could wear. There isn't an outfit I can think of that he wouldn't look stunning in. The excitement stayed with me throughout my shift.

With the work day over, I went to Nate's. He got off work early and got my suit for me, I would get the roses on the way home.

"Hey brother! I got the suits, they look awesome!" He had gotten one for himself, so that's why he insisted on getting mine.

"You got one too? Going on a hot date too?" He never mentioned getting one for himself.

"Maybe."

"Is this one going to be a fling?"

"We'll see. Watching you and Jade together has made me realize that I want something more, I want what you two have. Now don't get me wrong, I'm not jealous or anything like that. I just want to try harder to find a mate, more than one night stand with someone I'll likely never see again, you know?"

I was impressed, the swinging bachelor was serious about this. "Dating is hard, you know how hard I failed at it. I got extremely lucky, thanks in large part to you. If I can find someone, you can." I patted his arm. "I only wish I could do something similar to what you did for me and Jade."

"I don't call you 'brother' because it's the 'bro thing' to do. I've got your back, man."

"And I've got yours, brother." We embraced in a one arm 'bro hug'. Call it cheesy, but everyone needs a 'Nate' in their lives. I left soon after to pick up the bouquet of roses I had ordered in advance, they came in an empty glass jar that could be filled with water. On my way back to my car, my phone dinged.

"I'll be another half an hour; I hope you'll love my outfit! See you at home! <3"

"I'll love anything you wear, see you soon!"

I got home first with a few minutes to spare. Since Jade was coming home dressed up, I thought I would return the favor and be properly dressed when he walked through the door. After filling the jar with water and leaving it on the kitchen table, I got to work. The suit was a sight to see, dark heather gray with a snow-white undershirt included. There was a rose sewn onto the pocket on the left breast, I thought it was real at first glance. It even came with some glossy black shoes. There were no black socks, but I had some myself. It took a few minutes, but I was "suited up" when I heard the door unlocking. What I saw was.. stunning..

Jade was wearing a dark red form fitting dress with matching heels and black full arm length gloves. His makeup consisted of black eyeliner with mascara and red lipstick. The dress was strapless, barely covering his chest, and the hem stopped around the middle of his thighs. His blonde hair had been changed from straight to a wavy style tied into a small heart-shaped bun on the back of his head. He would turn heads at Serenata's, I assume he did on the way home.

"My, you look so dapper and handsome!" He placed his hands together, smiling.

"I... I can't find the words to describe how beautiful you are..." I wasn't lying, I couldn't believe what I was seeing! "Oh, these are for you." I picked up the bouquet and gave them to Jade. He beamed and sniffed them.

"Thank you! I love them!

"I knew you would. Are you ready to go, Cara Mia?" I offered my hand.

He giggled and took it. "You haven't called me that since Halloween! Yes, let's go, Mon Cher!" We walked hand-in-hand to my car and left for Serenata's.

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To say the restaurant was one of the fanciest in town doesn't do it justice. It looked like it was plucked out of Italy, not that I have been. It was a two-story building with balconies on the second floor full of couples enjoying their meals. We confirmed our reservation at the door and went inside.

The interior of the first floor was a marvel, walls of green and burgundy with golden lining. Artwork depicting landscapes and various Italian historical figures hung on every wall, mere feet apart. Golden chandeliers were placed evenly across the ceiling. The workers wore white dress shirts and black pants. Italian opera played throughout the building. We were led to the second floor, which was the main dining area, the scenery was very similar. The waiter seated us on a balcony. Our table sported a white cloth drawn over it and the chairs were elegantly carved out of some kind of wood, oak I'm guessing. We ordered wine, then the waiter left.

"I can't believe you got reservations here for tonight! How long ago did you call??" Jade was stunned.

"The week before Christmas, I was told I got the last one!" Talk about a close call.

"What luck! You're such a wonderful man." He batted his eyelashes at me.

"I try." I smiled and took his hand. "I hope you enjoy dancing later; we're going to after dinner."

"I've never done it before, but I would love to!"

The waiter came back with our wine and took our orders. We sipped wine and talked until our food came. It was delicious on a level far beyond most restaurants in the area! I think I will try to take him there every year, but maybe I should make the reservation sooner. I got lucky the first time but now I know better.

After dinner, we went back downstairs to the ballroom. Couples were dancing together; it was a very romantic setting. Jade and I joined the fray.

"Shall I have this dance?"

"You shall!" Jade smiled and took my hand.

I pulled him close to me and interlocked our fingers while holding his back with my other arm. Leading, I started moving, thank God for Nate's lessons. The limited space worked in my favor too, I didn't learn anything for wide open areas.

"I had no idea you knew how to dance! Is this what you and Nate were doing?" He chuckled.

"You got it." I admitted. "I wanted to dance with you without stepping on your feet or kicking your shins."

"That's sweet! I hope I won't do any of that to you."

"It's alright, all you have to do is follow my lead."

I quickly became lost in his eyes as we danced. Due to the crowd, we mostly stayed in place, taking only a few steps in any direction and moving slowly in small circles. We barely spoke a word, letting our movements speak for us. I don't know how many songs we danced through; we were in our own little world. When we stopped, half an hour had passed.

"Did we really dance that long?"

"Yeah, wow." I was astonished I went that long without stepping on Jade's feet, I owed Nate another drink.

"You are a wonderful dancer!" He leaned upward to peck me on my lips.

"You're pretty good yourself for this being your first time. I was horrible, even while letting Nate lead. But you're a natural!"

"I'm full of surprises!" He winked.

"That you are!"

He certainly was, especially when our relationship began. Due to his feminine body, mannerisms, and voice, I never would have guessed that Jade was once "Jayden", an old buddy of mine from school. Looking back on it, the signs were all there. He was very demure compared to the rest of us rowdy guys and was easily the smallest in our group. His "manly" voice seemed unnatural and forced.

Every time we all went out together, he would leave with a woman without fail, it baffled all of us. It turns out that he never slept with any of them, they took him home to let him wear their clothes and gave him an outlet to be himself. Eventually, Jayden began living as Jade, the person he truly is. We lost most of our old friends when we came out as a couple, which is fine with me, fuck 'em. Nate is the only one that has stood by us and regularly hangs out with us, I hope he finds someone one day.

"Thank you for tonight." Jade wrapped his arms around one of mine.

"You're welcome. Ready to head back? I have one more surprise for you."

"Oh yes. If it's what I think it is, I'm eager. I'm puddy in your hands and you could do whatever you want with me right now." I felt him melt into my arm.

"Oh, it's going to get steamy." I winked. As we exited the building, I noticed men checking Jade out, which drew the ire of the women with them. I was right, Jade was a head-turner. I wonder how they would have felt if they knew the truth.

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We returned home after 10, which was close to the time we normally make love and go to bed.

"This has been such a wonderful day." He gave me another peck on my cheek.

"It's not over yet. It's time for the last surprise." I winked.

Jade grinned. "You having your way with me?" He was getting excited.

"Well, it will lead to that. But first, I'm going to give you a massage."