Swinging in Vegas
After the pandemic was finally over and I had two doses of vaccine coursing through my blood, my friends and I decided it was high time to blow of some steam. We booked a weekend getaway to Vegas. As soon as we started down the strip, I posted a story to Fakebook. “Weekend Getaway with the Bros!” Not 10 mins later someone slipped into my private messages. “Out here with the girls and would love to see you XOXO!” “Holy shit,” I said under my breath. The sender was a 50-year-old woman named Diana. She was a fit milf I had met at a wedding a few years back. I could not take my eyes off of her perfect body or elegant pixie style when we first met, but I’d never dreamed of anything like this. In fact, after the wedding she had tried to set me up with her daughter! I figured she was just another hot married lady that I would never have a chance with. Intrigued with her message, I messaged back, “Hope we do more than just seeing one another,” I added a winking emoji to go with it. Mere seconds went bye before she responded. “Room 1001 the Mandalay Bay, 7:30pm. I will leave a key for you. Tell the front desk you are Eduardo.” Holy Shit, I guess while my friends were hiring hookers, I’d be getting laid for free.
Coincidentally, my buddies and I were also staying at the Mandalay Bay. My best friend and I were in room 607. When we arrived at the hotel, it was only 2:00, so we went down to the wave pool and caught some sun, enjoying comped drinks while watching the other lock down free singles relax after a year of stressful pandemic living. We headed out to grab some food around 5, but when the guys decided to head to the casino to start gambling at 7:15, I knew I had somewhere else to be. I grabbed another drink just to calm my nerves, and then I stopped by the front desk. “Hello, I am here to pick up a key for room 1001, my name is Eduardo.” The front desk lady, who had seen me when I first checked in smirked and gestured for me to lean in closer. “With all the cougars staying up there, you’ll feel like you are in a Zoo.” My face flushed bright red, and I smiled, my mouth too dry to respond. I quickly headed down the hallway to the elevator. The long button at the top of the hotel was number 1001. I was headed up to the penthouse!
When the elevator dropped me off on the tenth floor, there was only one door. I took a deep breath and swiped the key card. As I pushed the door open, I could hear moaning from somewhere in the room. My eyes quickly scanned across the living area and landed on a couch where a dark-haired woman was locked in a 69 position with another person. I began to quietly pull the door shut. Maybe I had made a mistake? Perhaps she meant a different room? She was 50 after all! “John, is that you at the door? Get that cute little ass in here.” I sheepishly pushed the door open, and Diana sat up, straddling the black-haired woman. “Stella, this is that cute young guy I was telling you about, the one I tried to get to date Kayce.” The black-haired lady sat up and wrapped her arms around Diana, “oh my, he sure is cute, I can’t wait to sit on his face.” “Well, you heard the lady,” Diana said, “get that cock over here.” I shut the door and quickly stripped, nearly diving onto the couch I was so horny. Diana looked just as good as she had those few years before. Her body was still toned, and her chestnut pixie cut was stunning. Here tits were tight and perfect from years of working out. Stella, who was also Diana’s age, was also extremely fit. Her black hair was cut into a nice bob style and she was flaunting her fake tits as I began to establish a spot for myself in the 69 position. “No, this certainly won’t do,” Stella said, as I began to kiss Diana. “Diana, has this kid ever been the star of an all-female swinging group before?” Diana laughed, “No I would bet he hasn’t even had a threesome before!” She was right of course, and Stella knew it, but these two ladies were too excited to have a young stud to not take advantage of me. “Here, lay down and put that tongue to work.” Stella pushed me back onto the couch and positioned her shaved pussy over my lips. I began to work my tongue into her pussy and moving it side to side along her lips. Slowly she began to grind herself back and forth across my face. Meanwhile I could feel a mouth on my cock, which was already rock hard. It stopped all to abruptly, but a hand took hold, and I knew enough to expect the pussy that engulfed my shaft next. “Had to get a little taste of that cock before I felt it inside me,” Diana said breathlessly. Soon, both milfs were riding me: Stella riding my lips and Diana riding my cock. I opened my eyes, and I could see that Diana and Stella were passionately making out as They took advantage of my cock and youthful vigor.
Stella was the first to cum, her sweet juices poured out over my chin as she moaned and furious grinded her pussy into my quivering tongue. This didn’t stop Stella though, she kept gyrating her hips from side to side, clearly appreciating the endurance I had for eating her wetness. Diana was next, she screamed in ecstasy as her pussy tightened on my manhood. . I felt her juices leak onto my balls and drip down onto the couch. Just like Stella, though, Diana did not stop moving. She kept riding me and even began to get faster Finally, I felt my cock pulse. I heard Diana say, “Wow, he lasted longer than our last little entertainer, I think I’ll even let him explode inside me!” “What’s the use of getting our tubes tied if we can’t have a little cum in there every once and a while?” Stella said. With that, my cock erupted, and I filled Diana’s pussy with a huge load. “I love it when they cum inside me,” Diana said, “It’s the best lube out there after all.”
Even after blowing my load, the two milfs did not stop “playing” with me. Diana began to slow down, but she did not dismount me until Stella got off first and bent over to plant a passionate kiss on my lips. Her tongue explored my mouth, and when she stopped and said, “Wow I do love to taste my own pussy on a young stud’s lips,” I knew that this was going to be unlike any experience I had ever had.
The two women led me by the cock to the shower, where they proceeded to wash me and shave every hair off my manhood and my ass. They said they wanted to appreciate the meat without all of the trimmings. Then they took me into the bedroom where they alternated bringing me drinks and making out with me. These ladies really knew how to make a man feel like a king. After one particularly vigorous session with Diana, Stella came in with another fresh mojito and my phone. “It looks like your friends have been trying to get in touch with you, this thing is going crazy.” I took a glance at it. It was 9:15. The guys were texting the group chat about when they should order the “entertainment” for the evening. My roommate was trying to see if I wanted a blonde or a redhead. I simply grabbed the phone and texted back “Found some girls already, you have the room to yourself.”
As I put the phone down, I heard a buzzing sound fill the room. Stella and Diana were laughing about something in the bathroom. When I walked in, what I saw could not have excited me more. The hair on the top of Stella’s head was pinned up and Diana was buzzing the bottom half. “Oh John, you caught me just updating Stella’s style. She said she wanted an undercut, so I’m obliging.” At the rate my cock was coming to attention I knew they could sense my infatuation with all things hair cutting related. “It looks like our friend has a thing for hair shaving Diana.” Diana smiled, “Oh yes, I think he loves to see our hair get shorter and shorter, isn’t that right John.” I just stood there with my jaw to the floor, nodding my head as the two milfs laughed. “Maybe I will let you clean up my haircut, what would you say to that John?” Diana said seductively. I gulped, my mouth was so dry I barely got out the next words, “Sounds like a dream come true” I responded. Stella laughed, “Man, if you are that excited about it come take over for Diana, she barely knows what she is doing anyways.”
Diana relinquished the clippers to me. She had only gotten about three fourths of the way through shaving the right side of Stella’s head. My cock was directly in her face as I bent over her to begin buzzing the rest of her undercut down to the skin with the guard less clippers. Three- and four-inch pieces of black hair fluttered to the ground, as I shaved her undercut to the skin. Each timed I plowed through a fresh crop of hair, the locks would brush past my rock-hard cock on their journey to the ground, bringing me closer and closer to ecstasy. As I was halfway through buzzing the back of her head all the way up to the occipital bone, Stella shrugged. “I can’t stop staring at this cock right in my face. I just have to do something with it.” Her perfectly manicured fingers wrapped around my cock and began stroking it as she brought it into her mouth. It was quite a task maintaining accurate clipper work as this sexy milk who was letting me buzz her head sucked me off but focusing on the task at hand helped me not explode in her mouth immediately. I was able to buzz the back of her head and begin on the left side. In fact, it was not until Diana reappeared that I exploded in Stella’s mouth.
Diana came into the bathroom silently and wrapped her arms around me as I was shaving the left side of Stella’s head down to the skin. She whispered in my ear, “wouldn’t you like to buzz my head while I suck that cock?” I swallowed hard as she continued, “but for that to happen, you have to earn it. You have to give Stella something to swallow.” I just finished buzzing the left side of Stella’s head, and turned off the clippers, when something slippery entered my ass, and at that moment I exploded into Stella’s mouth. Stella was furiously sucking me at this point and working my whole shaft with her hands, while Diana was busy massaging my asshole with her vibrator and kissing me on the neck. The whole experience was opening my world.
Soon my cock was ready for another round. It was then that Diana took her seat on the toilet, with my cock at attention right in her face. Her long, slender, manicured fingers wrapped around my cock and slowly stroked back and forth as her tongue periodically flicked out to lick the tip. Embracing the role of MILF barber, I asked “And just what kind of haircut could I treat you to milady? Something short perhaps?” “Oh, very short,” she said seductively, “I was thinking you could take my sides and back to a zero and leave my length and bangs on top, maybe blend it nicely? Like a stylishly shaved pixie.” “I know exactly what you mean,” I said. “Oh,” she added, “I hope you have no problem with my friend and I paying you in hot MILF sex?” “Actually,” I responded, “that’s the only type of payment I accept.” “Perfect, in that case, I’ll start with your tip,” Diana said as her mouth engulfed my cock. I began by pining her bangs and the hair on the top of her head up. It was not long, maybe one and a half or two inches at the most, but it would help get it out of the way while I buzzed the sides and back of her head. It was tough being a barber while also having my dick sucked by such a beautiful woman, but I was too excited to live out my hair cutting fantasy to turn down this opportunity just to have more sex. Besides, I knew I was going to be fucking these ladies for the rest of the weekend. As I fired up the clippers, I heard the door open, and Stella’s began welcoming someone new into the “Swinger’s Penthouse.” Then I heard moaning as the two got down to business.
Meanwhile, I was busy clipping the right side of side of Diana’s head. Each pass of the clippers sent more chestnut hair down to the ground and exposed more of Diana’s white scalp. Each pass pushed Diana to suck my cock faster while driving me closer and closer to orgasm. As I made my way to the back of her head, Diana began to stroke her pussy, rubbing her perfect fingers over her shaved lips. By the time I began buzzing the left side of Diana’s head, she was furiously rubbing her own pussy, all while nearly gagging on my cock each time she sucked the length of my shaft. I was lucky I had already cum twice otherwise I would have exploded into her mouth before her haircut was finished. I briefly stopped buzzing Diana’s head to slip a guard on the clippers and Diana looked me in the eyes. “Give me some more of those clippers baby. I want to feel you buzzing me.” I quickly obliged, as I used the new guard on the clippers to blend the hair on the top of her head into the white walled sides and back. Soon she was left with a perfect pixie on top, which blended perfectly into her shaved sides and back. By the time I switched off the clippers, Diana was practically pounding on me. She forced me to the floor in the bedroom and slid my penis inside of her faster than any other woman I had ever been with. “Oh yeah fuck me barber boy,” she said as she rode my cock side to side. For the second time today, I felt her juices drip down my shaft. And for the second time today, I exploded inside of her as her pussy tightened on my cock and rode me into ecstasy.
With my cock still inside of her, Diana collapsed on my chest and whispered in my ear, “I really don’t care if my husband told me not to come home bald, I need you to use those clippers on me again, that really was something.” I smiled and kissed her deeply. It was then that we heard Stella’s voice again as she told the new arrival to “put her stuff away and get ready for their boy barber to give her a haircut she wouldn’t soon forget.” “After all,” Stella’s voice echoed throughout the penthouse, “You and I have always wanted buzz cuts right?”
To be continued…..