
Valentine's Day Date with Dad
Pt. I


COOPER:
At 27 years old, I'd never spent Valentine's Day with a partner before. This year was supposed to be my first one. My boyfriend and I were going strong for nine months, so I decided to go all out and book us a weekend full of pampering at a spa in Las Vegas. Yes, it was expensive, but it was a nice little break from the winter in Wisconsin. Until… two weeks before Valentine's Day, my boyfriend and I broke up.
"Hey Dad," I said morosely as I answered my phone that evening. I wasn't in the mood to talk to anyone, but my dad had called me without texting first, which made me wonder if this was an emergency.
"Hey, son. How you doing?" he asked.
"Not too good," I confessed. "My boyfriend broke up with me earlier today. Ex-boyfriend, I should say."
"Aw. Well if it makes you feel better I'm not having the best day either," Dad said. "You wanna meet for a drink?"
"Like, the two of us?" I asked.
"Yeah. We haven't seen each other since Christmas, and I need a drinking buddy."
"Yeah, okay," I agreed. "Better than moping around the house, I guess."
"That's my boy," my father said, suggesting we meet at his favorite bar in half an hour.
Even though Dad and I lived in neighboring towns, we only saw each other during holidays and special occasions. Most of the time, we met at my sister's house. She had four kids, so there was always a birthday or a graduation being celebrated there. Unlike her, I lived alone in an apartment that felt way too quiet for my liking. I walked to the liquor cabinet, downed a shot of tequila, and ordered an Uber to drive me to the bar to meet with Dad.
To my surprise, my father was wearing a pale pink dress shirt when he arrived. I literally couldn't remember the last time I'd seen him wear anything except a hoodie. We sat at a table, ordered a couple of beers, and I immediately addressed his choice of clothing.
"You look pretty in pink," I teased.
"Thanks. I had a date tonight," he said, taking a long swig of his beer. "Thought I'd do something different."
"Did she like your shirt?" I asked.
"She never mentioned it. It was our first date, and most likely our last."
"Didn't go well, huh?"
"Nope," Dad shook his head. "No surprise there. Your mom and I have been divorced for over ten years. And I can count on one hand the number of dates I've been on that went well."
"Cheers to that. Dating sucks," I said, raising my beer bottle in commiseration with Dad. "I finally thought I was done dating for good. I mean, nine months… It's the longest relationship I've ever been in. And now it's over," I said.
"Why did it end?" my father asked.
"He just said he wasn't feeling the chemistry anymore," I shrugged, peeling the label off my beer bottle and avoiding eye contact because I felt embarrassed. "It came out of the blue. I thought we were doing okay. I had a trip booked for Valentine's Day and everything. Oh shit, the trip! None of it is refundable," I realized with frustration.
"Where'd you book a trip to?" Dad asked.
"Two nights in Vegas," I said. "I got a Christmas bonus at work and I spent all of it on this trip. What a fucking waste."
"I'm sorry, son. Maybe you can go on your own," my father suggested.
"Nah, it's meant for couples. Couple's massage, dinners, all of that. It'll just be depressing if I go on my own," I explained.
"Don't you have a friend you can take with you? It doesn't have to be romantic, you could still have a nice time."
"All my friends have plans, I bet. They're all in relationships," I said. "You're the only single person I know."
Suddenly, it dawned on me.
"Hey. You're the only single person I know," I repeated.
"Thanks for reminding me," Dad said. "Rub it in, why don't ya?"
"No, I mean: do you wanna come with me to Vegas? Like you said, it doesn't have to be romantic. It's all paid for already. And you'd only need to take one day off work."
"I'll see. When is it?"
"Valentine's Day is on a Friday, and we fly out in the morning. We fly back on Sunday evening," I said, slowly getting excited by the prospect of leaving town for a couple of days.
"Yeah, I think I can swing that," Dad nodded. "A father-son Valentine's Day date. What a trip."
—
Two weeks later, Dad and I met at the airport, rolling our eyes at the people carrying bouquets of flowers or heart-shaped balloons. It wasn't until we took our seats on the plane that we realized we hadn't flown together since I was in middle school, back when my parents were married and the three of us went on a trip to Florida.
"So what's on the itinerary for this trip?" Dad asked me as the plane began to take off.
"I have a massage booked for us this afternoon," I said, "and dinner and a show tonight. And have you ever gotten a facial?"
"Is that a sexual thing?" Dad asked, making me laugh out loud. He and I never really talked about sex, so hearing him crack a sexual joke was something novel and fun.
"I mean, a facial treatment at a spa," I said, still chuckling. "That's what we have booked for tomorrow."
After about four hours, we arrived at the hotel in Vegas and headed up to our room on the 14th floor. There was a small box of chocolates and a card that said "Happy Valentine's Day" on the table, but at least there were no rose petals scattered all over the mattress.
"I guess we're sharing a bed," Dad pointed out, placing his bag on the king-sized bed.
"Yeah. I'm gonna go shower, and then we can grab a bite to eat. Our couple's massage is at one o'clock," I said.
I carried my bag to the bathroom, where I showered and put on a fresh set of clothes. When I went back out to the room, I was somewhat surprised to see my father walking around in his underwear.
"Bathroom's all yours, if you want it," I said, trying not to stare at my father in his white briefs. It had been many years since I'd seen him in his underwear, so I was kinda curious what he looked like. A few quick glances revealed that he was in decent shape, rocking a dad bod that could be the envy of many other men in their late 40s.
Rather than take his whole bag with him, Dad simply took out a toothbrush and what looked to be a pair of black boxer briefs. Fifteen minutes later, he came out of the bathroom, freshly showered and wearing the black underwear. He dropped his worn white briefs on the floor by the bed, and he proceeded to get dressed in front of me. Pretending to scroll through my phone, I once again found myself glancing at Dad's bulge and his ass, before silently chastising myself for being such a creep.
We had a quick lunch in the restaurant attached to the lobby, before walking around the hotel's casino. I wasn't a gambler and neither was Dad, but it was fun to walk around since it was our first time here. Afterward, we headed to the spa in time for our appointment. Once there, the receptionist greeted us both with a warm smile.
"Welcome! Happy Valentine's Day to you two," she began, assuming my dad and I were a couple. "You can both follow me."
Neither of us bothered to correct her, since it didn't matter anyway. Besides, it would've been weird to explain that this was my father and we were getting a massage together. She led us to the room and pointed to a cupboard where we could leave our clothes.
"Go ahead and get undressed and wait under the towels on the tables. They'll be right in for you. Enjoy the massage," she said with another smile and then excused herself, leaving us alone. Dad and I chuckled nervously.
"Do we take everything off? I've never had a massage before," my father asked me.
"Umm, you can leave your underwear on if you want, but that's up to you," I said.
"Are they gonna be using oils and stuff?" Dad asked, looking at a bunch of massage oils placed in the room. "Seems more comfortable to go naked."
As my dad pulled off his shirt and dropped his pants, I started to undress as well but I kept him in the corner of my eye. I held my breath when – to my astonishment – he tugged at the waistband of his boxer briefs. For a brief moment, I got a glimpse of his tight ass. Then, Dad turned to face my way, and I saw his dick swinging. Although soft, his tool was plump, cut, and surrounded by neatly trimmed pubic hair. I almost gasped, and my cheeks burned as I looked at it a few seconds longer than appropriate.
Finally, I turned away from him and took off the rest of my clothes. I didn't want to leave my underwear off if he was going to be nude. I wasn't sure if he caught a glimpse of my exposed ass, but at least my ass was the one body part that I was proud of the most. I tugged my cock for a second, just in case Dad saw it – I didn't want it to look all shriveled up.
We both got onto our respective tables and under the towels, lying on our stomachs. Soon, the therapists knocked on the door and let themselves in. I had specifically booked two men for me and my ex-boyfriend. At the time of the booking, I wondered if the masseurs would be gay as well. Now, as they walked in and said hi, my gaydar definitely went off.
My therapist seemed to be my age, with thick muscled arms that were covered in tattoos. The other guy was older than me, but younger than my dad. He was bald, with arms equally as toned but without any ink. If I wasn't lying face down, I would've had a difficult time not staring at them.
"Have you ever had a couple's massage before?" Dad's therapist asked.
"No," Dad replied, once again not bothering to explain that we weren't actually a couple.
"You two just relax," my therapist chimed in. "We're here to make sure you have a perfect massage date."
Suddenly, I felt a drip of oil on my back, followed by the touch of two strong, capable hands. I was putty in the masseur's hands as he worked my tense back muscles. He started at the shoulders, gradually working his way lower. To my left side, Dad moaned and whispered "fuck" a few times as his therapist worked on him.
Within fifteen minutes, the tattooed guy was kneading my glutes. He was standing in front of my head, leaning over me, and I could swear I felt his bulge brushing against my head a few times. That, combined with his magical hands on my ass, soon had me popping a boner. I wanted to grind my hips against the table, but did my best to stay still. I hadn't had sex since my breakup, and it didn't take much to get me aroused these days.
"Alright gentleman, time to turn over," the tattooed therapist said, taking a break from touching my body.
My father and I flipped over. I had to grab the towel to keep it from falling off. I looked at my dad, who had his eyes closed while the bald guy worked his forearms. Now that I was lying on my back, it was glaringly obvious that I had a boner. Fuck! This was so embarrassing. My masseur acted professional and ignored my erection. Thank God my dad wasn't looking.
Next, the hunky tattooed therapist began working on my quads. His hands kept going higher and higher up the inside of my thigh until eventually, the edges of his fingers grazed my balls. The unexpected touch set my cock throbbing and even leaking precum onto the towel. I was going to just brush it off as an accident… except, he did it again. This time felt more purposeful, with the contact lasting longer.
As his hand slid up, I felt his wrist against my shaft. I didn't stop him, which led to him full-on grabbing my hard cock under the towel. He gave it a squeeze, unaware that he was doing this with my father in the room!
I didn't move a muscle, except for the pulsing of my cock. As horny as I was, I was hoping that this would continue. Dad still kept his eyes closed, so hopefully he wouldn't see anything. The masseur held onto my boner with his oil-slick hand, which made the perfect lube. Up and down, he jerked me gently, smothering the oil all over my shaft. Long, deliberate strokes followed, even squeezing my cockhead in his palm when he got to the top. I moaned softly, unable to contain myself.
The other massage therapist was either completely ignorant of what was happening or doing a very good job at ignoring the handjob his coworker was giving me. Either way, he was still focused on making sure Dad had an amazing experience. Based on the moaning coming from my father, he was definitely enjoying himself as well – albeit in a different way than I was.
The tattooed masseur added a bit more oil, making our contact even more slippery. His touch had my senses tingling like crazy and my whole body was quivering as he pumped his fist up and down. Dad groaned again, making my breath stop. I looked over to check if his eyes were still closed. Just then, the masseur gripped me tighter and made me blow my load! My pulse raced and I clenched my toes. And while all that was happening, my father opened his eyes and looked at me, smiling. I tried to smile back, but it wasn't easy to act normal in the midst of an orgasm. I shot my load under the towel, hoping my dad couldn't see that the masseur had his hand in there.
Moving discreetly, the therapist pulled his hand away, wiped it off on another towel, and resumed the massage as if nothing had happened. I couldn't believe this Valentine's Day could get any stranger than spending it with my dad, but here I was lying in post-orgasm bliss right next to him.​