So Hard to Shop For

"What?!" I said, freezing in my tracks.

"You heard me."

"Tempting, but no." We laughed it off, and I let the comment go. But several days later, while I was making coffee, she made the same comment.

"Seriously, I'm still pissed at Eric. If you want, I'll totally give you a hall pass for Kaitlyn." I nearly spilled the creamer I was pouring into my mug.

"Please stop doing that to me."

"Why? Fuck Eric, he hurt her."

"Yes, but even if she were interested, and believe me, I'm tempted, I wouldn't want to do that to you. Besides, if you keep offering, I might actually get weak at some point and try to act on it."

She laughed, smiled at me, and said, "You're a good man."

"Maybe, but if you keep offering that, I might forget I am for a night." Instead of answering me, she just grinned.

So life soldiered on. I got promoted and my workload actually lightened a bit, and my wife and I started going to the gym a bit more in an effort to be healthier. We both dropped a few pounds and began to have sex a bit more, which was nice. For her birthday in January, I surprised her with a trip to Las Vegas, and we went to see the musical Hamilton with our daughter Annabelle and her husband John, who flew in for the event. She was ecstatic at all of the attention, and kept saying "I've got to do something big for yours, now."

"Forget it, you know I hate birthdays. Besides, I don't need anything." I really am the worst guy to shop for, as I have a ton of toys, plenty of clothes, and I'm kind of picky.

"Yeah, but you've set the bar higher now."

I told her my usual spiel, that I just wanted us to have a romantic dinner and maybe a staycation for a night at a hotel—I do genuinely dislike birthday celebrations, and it was nice to get away to a place with no kids, dogs, and other assorted noises. I made her promise me nothing too big or silly for my birthday, and she gave me a weird little smile, saying "If I do anything, it'll be something I'm sure you'll like, okay?"

"Okay, but I don't want anybody singing to me, please."

"Deal."

Finally, a couple days before my birthday rolled around in October, she couldn't stop grinning. I asked what she was planning, and she wouldn't say, only saying "I made arrangements for your present, and it's the best one I've ever given you."

As luck would have it, my birthday fell on a Friday that year. When the day came, I was nervous. We got two packages that day, and I was terrified that she had ordered something silly, but when I opened the boxes, they were a shirt for my son and an adapter for my computer, nothing crazy. At about 4, I got a text from my wife. "First birthday surprise. I got us a table at Nobu. Meet me there at 6:30, and dress sharp." That restaurant was notoriously hard to get into, you have to reserve a spot weeks in advance, but it's some of the best seafood and sushi you'll ever have.

I quickly finished up my work, showered, shaved, put some cologne on, and picked out one of my best suits—working from home, I tend to spend my days in tees and jeans, so it was actually nice to get dressed up. I wound my way across the 101 towards the restaurant, and actually made it with a few minutes to spare. When I walked in I was floored, Melissa was wearing an evening gown with her hair up, and looked amazing. I went over to her, kissed her, and she whispered "Happy birthday, big boy. I can't wait for you to unwrap your gift." I cupped her ass in my hand and leaned in to her ear, lowly replying "I can hardly wait." We waited for a couple minutes, chatting aimlessly, until we were called to our table.

The meal was exquisite, and the service amazing, and my wife was being extra teasing and flirty. She pulled her foot out of her heel at one point, lightly teasing my prick through my trousers with her toes. As I started to tent, she quickly withdrew it, and then said "No, we don't want you getting too excited yet. You're going to need every bullet in the gun tonight." I was starting to get excited thinking about all of the birthday sex I was going to get, since normally responsibilities and lack of time tended to limit our romps to once a night, maybe twice once in a blue moon. "Hang on, I have to get something set up," she said, digging her cell out of her purse. She made a quick call, and said "Yes, we're ready for the gift." I raised my eyebrow quizzically, but she just grinned her evil little smile. "Just you wait, sir."

The waiter came up and asked, "Ma'am, are we ready for the desert?"

"Absolutely."

He quickly disappeared. Almost on queue, her face brightened, and she waved someone over who appeared to be walking through the door. I turned to look, and was surprised to see Kaitlyn come through the door. "Happy birthday!" she beamed at me, giving me a big hug and kiss on the cheek, dangerously close to the corner of my mouth.

"Thank you. I had no idea you were coming."

"Well, I needed to be here to see you open your present." She was seriously dressed to the nines, with a fantastic bodysuit-type garment that seemed to hug everything, and a keyhole cutout hinting at her breasts. I had to remind myself to keep my eyes up.

The waiter appeared and set down a small cheesecake in front of us. "We understand you're celebrating a little milestone tonight, so please accept this from us. It's an almond-caramel cheesecake. Thank you, and enjoy." He set down three dishes and spoons. I raised my eyebrow at her again.

"Eat your cheesecake," came her reply. I looked from her to Kaitlyn, and shrugged as I dug in.

"So I needed to top your present," she began.

"No you didn't, that was the first time I was able to really do something big for your day..." I interrupted her, but she held up her finger the same way she always did with our kids when they were trying to cut her off. I took the hint.

"Yes, I did. So I got you something you're going to really enjoy tonight." She reached in her purse and pulled out two envelopes, which had numbers on them. She handed me the first one, emblazoned with a number 1. "Go ahead."

I opened it, taking in the two of them—I hadn't fully taken her in before, but Kaitlyn was really dressed to kill as well, with a gorgeous, form-hugging dress that really conformed to every curve. I reached in, pulling out a card, which was a cute one with a little dog on it and some joke, but as I opened it, a key card to the hotel Kimpton fell out. I looked up at her, and she just smiled as she said "Yes, tonight will be fun."

"That was really all I wanted, I hope you know." They both giggled in unison. "What?"

"Open this one now," she said, sliding the envelope with the giant 2 on it.

I ripped it open, and I reached in to pull out a piece of nice stock paper, and as I went to flip it over, Kaitlyn grabbed my hand and said "Wait, Matt, I have to ask you a quick question before you look at that." I looked up, and she put her hand up to her neck as she tilted her chin up slightly. "What do you think of my choker?" I was a little confused, my eyes automatically drawn to her lovely neck and creamy, pale skin.

"Um...it's very nice..." I began.

"We both agreed a bow was way too corny for me to wear in public."

I was confused. Surely she wasn't...no, ridiculous thought. I turned the card over, to see a printout in a calligraphic font. "This document entitles the holder to one weekend hall pass for the person of his wife's choosing. He shall have full privileges and enjoy it in good health and good fun. I love you, baby."

I was a bit dumbstruck. I looked up, and didn't know what to say.

"We talk," was all my wife said.

"I...um, I thought you were..."

"Joking?" she finished. I nodded and quickly gulped a bit of the club soda in front of me. "Partially, at first. But we talked about it." I looked from her, to Kaitlyn, to her, and back to Kaitlyn.

"Are you sure?" I finally asked her.

"So sure," she said. "I haven't been laid well in months. Plus I adore you, so I'm really looking forward to it."

"Are you sure?" I asked Melissa.

"Yes. You treat me so well. Plus you haven't had a different woman in over 24 years. What better gift could a woman give the man she loves that a horny and gorgeous 24-year-old?"

"And I'm so horny, Matt. I'm seriously dripping in my panties right now."

"You're really sure about this?" I asked Melissa again.

"Yes. You're going to take her to the hotel, and spend all weekend fucking her brains out. And you're going to order room service, and fuck her some more, and then come back to me on Sunday."

"Seriously?!"

"Yes, this isn't some kind of cruel joke." She signaled the waiter to bring the check, and pulled her card out. "I want you to get in your car, bring her to the hotel, and fuck her mercilessly. Make her cum again and again, and have fun." She leaned across the table, kissed me, slipping her tongue deep into my mouth, and then added. "Happy birthday, babe." She pulled back, gave Kaitlyn a quick peck on the lips, and said "Wear his ass out." Kaitlyn grinned, and then got up and held her hand out to me. I rose and took her hand just as the waiter arrived with the bill and she handed him her card without looking at it. "Go have fun, I'll talk to you both soon." She blew me a kiss and laughed, right as Kaitlyn began to pull at my hand and lead me out the door.

As we got to the parking lot, I looked over at her. "Not the gift you were expecting?"

"No, not really." She laughed. "Where's your car?"

"I Ubered it. I knew I was leaving with you." I nodded, still a tad disbelieving.

I led her to my car, opening the door for her. "Wait...what if I'd said no to this?"

She quickly turned around, grabbed the back of my head, and kissed me deeply, and I barely hesitated before returning the kiss. She giggled. "Yeah, like that was going to happen. Listen, I've seriously been fantasizing about you for a long time. We've been planning this for a couple months, and Melissa has told me so much about what a great lay you are. I'm going to absolutely drain you dry this weekend." She snuck her hand down, gave my cock a quick caress through my trousers, and then pulled away and sat in the seat. "Drive," she ordered. I closed the door and quickly got in, surprised that I didn't peel the tires as we pulled out of the parking lot.

Amazingly, we got to the hotel in great time, though Kaitlyn kept teasing me the whole way. She kept bantering, telling me how much she was looking forward to having my cock in her mouth, and inside of her. "She told me your cock is nice and thick, curved, long, and just the right size. Is it true you blow big loads?" she asked. "I can swallow a lot, but I'm curious if I can swallow all of you."

"Decently big, yeah. Uh, do we need to stop and get protection?" I asked, it just occurring to me.

"I'm on the Nuva ring, so no. I want to feel you bare tonight," she added, tracing a finger down my chest, slowly going towards my crotch, circling in slowly until she began drawing her fingernail across my rapidly swelling cock. "Ooh, someone likes that idea," she cooed, reaching over and undoing my belt. "Let's let him get a bit of air, shall we?" She unzipped my fly, and reached into the waistband of my boxer briefs, freeing me from my cotton prison, inspecting my prick as it hardened in the cool air. "Mmm, that's nice," she said, gripping it, sliding her thumb over the head and foreskin gently.

She unbuckled her seatbelt, bent over, and took the head gently into her mouth, giving me just a couple of light sucks and rolling her tongue around the head. "Tastes nice, too," she added, looking up at me with those big green eyes. "But, since we can't really do too much in the car, let's not get into a crash, now," and she tucked my member back into my underwear. I groaned, and she laughed. "Don't worry, I'll be swallowing all of that gorgeous meat soon." I sped up as much as I could in traffic, probably only about 10 mph before I had to let off, and she laughed, patting my turgid rod lightly, and said "Soon, dear. Soon."

As we parked in the garage, I got out of the car and buckled my pants. I went toward the lobby elevator, and she pulled me towards the next bank. "You're already checked in. Melissa took care of everything." We got in the elevator, and stood side by side a little awkwardly as we rode up with an elderly couple—well, awkwardly for me, as I was still in amazement I was going to be fucking this lovely creature in a few minutes time. Kaitlyn, for her part, was all over me, my arm draped over her as she absently toyed with my chest, driving me nuts. As the couple exited at the sixth floor, she leaned in to whisper "I'm so wet it's dripping down my leg."

When the doors closed, I quickly turned on her and attacked her, pressing my body into her and snaking one arm behind her back. She snuck her leg around me and moaned into my mouth as I kissed her. "Just a bit more, babe, we're almost there. You can be inside me in a few more minutes. God, you're so hard already. I'm so ready for you." She reached under her skirt, and then brought her hand back up, her finger glistening. She put it in front of my mouth, and I sucked her finger in, tasting her juices, sweet and a tiny bit tangy, and felt myself steel even more. Finally, our floor came, and she virtually dragged me by the hand as she ran to our door. She reached into her clutch, pulled out the card, and opened the door, dragging me by the coat as we entered.

As I wandered into the room, I saw that Melissa had sprung for a slightly upgraded suite, and in addition, the room had already been spruced up a bit. The bed was turned down, there were fresh cut flowers in a vase, and there appeared to be a bag or two in the bathroom. "We figured if you knew about this, you'd prepare, so Melissa got me flowers from you. Thank you, by the way," she added, leaning in to give me a kiss that started tenderly, but then slowly moved into an almost burning passion. She was in my arms, pressed so tight against me there was no room for even oxygen, and then she pulled back slightly. "Give me a second to get into something a little sexier, okay?"

"What you're in is pretty damn amazing, already."

"Trust me, babe, you haven't seen anything yet."

"Hang on, just a second. Can we talk for just one minute?" I was kicking myself internally, but I knew I had to do this. I gestured her to sit beside me on the bed, which she did reluctantly.

"You're worrying, aren't you?" she asked.

"Well, yeah. I have to ask—why do you want to do this? I kind of get why Melissa came up with this whole crazy idea, but I need to know why you went along with it."

"Long answer or the short answer?"

"Detailed. Maybe the medium one. Don't get me wrong, part of me wants more than anything to just tear your clothes off now and go to town, but I'm just a bit surprised you're so agreeable about the idea of sleeping with me." She smiled one of her dazzling, pure joy smiles, and closed her eyes for a few moments before taking a deep breath and affixing those mesmerizing eyes on me. Every time she did it, my breath paused for just a second, it was like a reaction I couldn't help.

"There's about a hundred reasons, and a lot of them are selfish. Yes, I want you to have a good birthday and all of that. But it's also that you already make me feel good. You have always treated me with kindness, respect, and love, like I was part of the family. Most men perv out over me, and have since I was about 15..."

"I haven't exactly been entirely innocent of that..." I interrupted.

"I know," she shot back. "I've caught you looking at my butt a couple of times, and I know you're a fan. But you never leered at me. You never made an inappropriate comment or gesture. You treated me like an equal, asked me my thoughts, and were always so kind and caring. I've often felt like I could talk to you about almost anything."

"Well thank you."

"There's more. Melissa and I have had plenty of private girl talk. Eric wasn't a terrible boyfriend or bad in the bedroom, but he also wasn't anything like what I wanted or needed. He seemed to regard making me cum as if it was an ego boost for him. Woohoo, I did it, I'm a stud, type of shit."

She paused, closed her eyes, shook her head, and continued, "From what she's told me, you're...way, way different than that. And to be honest, all of my boyfriends since the first boy I slept with have been either the same, or worse. I've never been with an unselfish lover. Plus, the last couple of months, I started looking at you a tad bit differently. At first, I started to notice the physical stuff. You're in really good shape for a man your age, especially since you've gone back the gym. That little gut you had is virtually gone, and your biceps and chest are looking nice. You're cute, genuinely, with a little swagger you don't even realize you have. But mostly, it's in the way you look at me. When you look at my face, you look right at me. You actually see the woman you're talking to, and I can see that you care..."

"Of course I care, you're part of the..." she stopped me with the gentlest, sweetest kiss. She put her finger against my lips and smiled a little half-grin.

"Exactly. You care. I don't really want a one nighter with some random guy that probably doesn't give a shit. I don't want crappy, throwaway sex. I want the real thing. Passion, caring, and touching. I know you'll deliver that. Plus, from what Melissa says, you'll leave my legs shaking and me begging for more, and I don't know if I've ever been fucked that good, so I feel like I might be ready for that." She leaned in and kissed me again, but this time, it was a little less gentle, and a lot more insistent. As I kissed her back, her mouth slowly opened and her tongue playfully pressed into mine, neither insistent nor lazy, and I couldn't help but push back. I could feel her grin as she began to devour my mouth, pulling me in insistently.

"But most importantly, I want you," she said, huskily, her mouth still loosely on mine. "I'm so horny for you I'm nearly ready to burst. I want to climb on top of you and ride you and take every inch of that beautiful cock and do it again and again until the sun comes up." She invaded my mouth again, rawly, leaving me panting for breath as she broke away. "And then I want to sleep, wake up, and do it again." She pulled back, smiled wryly, and then said "I'm going to change. I'll be right back." She backed up, took a few steps, then looked back over her shoulder. "You might want to lose some clothing."

As she shut herself in the bathroom to change, I got up and began to hang up my suit on hangers in the closet. I noticed a couple of my shirts and pants already there, and I noticed a slight shake in my hand as I threaded my pants through the hanger. They completely planned this out, I thought. I was actually nervous. I hadn't slept with another woman in 24 years, which coincidentally was Kaitlyn's age. I hadn't exactly been a choir boy before Melissa, but all of that was so long ago that it seemed like another life, or maybe someone else's life. Could I go through with this, and assuming I could, would I even be any good? I suddenly was filled with a touch of trepidation. Would I be able to relearn another woman's favorite touch? Would I be able to make her cum?

I reached down last and took off my socks, balling them up, but left my boxer briefs on, feeling a tad bit insecure, and sat down on the edge of the bed. I reached over, grabbed a bottle of water out of the minibar, and took a sizable pull. The door clicked, and she came out in black sheer lingerie, which incorporated a very short skirt-like feature, and a black garter belt with stockings. "Do you like?" I nodded vigorously. She moved forward and indicated a small ribbon between her breasts. "Did you want to unwrap your present?" I realized the narrow ribbon was tied in a bow, and I reached out a hand and pulled it tentatively. It came undone easily, and the top part of the nightie came undone, exposing her cleavage a fair bit more, which was almost amusing considering that her entire breast was already on display through the material. I think she sensed my slight nervousness, so she reached down, kissed me gently, and asked "Do you want to take this off of me?"