High School Teacher's Spring Break

Spring break had finally arrived. My 48-year-old girlfriend had been hanging on by her fingernails for weeks. There's nothing harder than being a High School teacher, and she had survived until this day thanks to grit, hard work, and wine-in-a-box.

I knew exactly what she needed now, a nice big patch of sand, warm sunshine, good food, and spa time. The Fort Lauderdale Marriott was the perfect place for her to unwind and reenergize.

I knew this area is popular with Spring breakers, so I made our reservations months in advance. I'm retired and love the vibe of Fort Lauderdale, especially when it's filled up with young people partying and having a great time. This wasn't my first rodeo; in fact, it was my fourth visit here during Spring break in the last 15 years. It was, however, Stephanie's first time.

When we arrived at the hotel, the young male receptionist looked my girlfriend over carefully. The age gap was a real thing, with me in my late 60's and her in her 40's it was made worse because she looks at least 10 years younger than her actual age. Stephanie has long flowing blonde hair, a models face, and 34-DD boobs on a small frame. She draws a LOT of attention wherever we go. We're a relatively new couple, both recently divorced and looking to have fun and explore new places and have new experiences.

The young man, Matt, welcomed us and acknowledged my Lifetime Platinum Premier status with Marriott. That's not an easy status to obtain. It requires 1500 nights at Marriott properties and carries a lot of respect with the title. Matt was concerned that they had placed us on the 3rd floor, the same floor as the pool, and things were already getting pretty rowdy around the pool every night. When he offered to upgrade us to a larger room on the top floor, we were giddy with excitement. He said it was one of their most spacious rooms and had a lot of extra amenities including a large in-room jetted tub.

The room did not disappoint. The windows were huge and faced the Atlantic Ocean and the beach below. We had the best view possible, including the pool below us on the 3rd floor. It was more than we needed, but everything we could hope for. The room had two California King beds, a large area for entertaining, and a full bar.

We hated to leave the room, but changed into more comfortable beach clothes and headed out looking for an early seafood dinner. Stephanie was dressed in a flowing summer dress, braless (I didn't ask about panties) and some cute sandals. She was a vision.

We were joined in the elevator by several young men who were very excited to get out on the town. They gave Stephy more than a passing glance and communicated their approval between themselves with head nodding, raised eyebrows, and huge smiles.

As we passed through the main lobby there was some sort of commotion happening at the front desk. Matt was talking to two young men who were upset because they were being told their reservation wasn't valid, and they didn't have a room. In addition, Matt told them no other Marriott properties had any availability within 50 miles. How this had happened was a mystery, but I chalked it up to amateur booking behavior. (That's why I booked early and verified my reservation way in advance.) I felt bad for them, but I also knew it was likely their own fault. Marriott doesn't screw up reservations.

I made eye-contact with Matt and gave him a nod and mouthed thank you as we walked past the ruckus. He would get a very large tip before we leave town.

Outside the sun was warm and welcoming. I admired Stephanie's beauty as she laughed and skipped along the walkway. This is exactly what she needed. It was great to see her smile and leave the world behind. She got lots of admiring stares from people seated outside for dinner as we worked our way to Kelly's Landing, our dinner destination.

Once we were seated outside at Kelly's, we started drinking margaritas and had two before dinner arrived. We were both drinking on an empty stomach and I was surprised how quickly the alcohol went to my brain. We laughed a LOT, and enjoyed some of the best seafood around, while drinking a few more margaritas. I was quietly talking dirty to Stephanie and I couldn't stop staring at those tits... I was really looking forward to seeing them up close and personal later tonight.

We staggered out of the restaurant with plenty of daylight to spare, and started the journey home to our exceptional hotel room. We both felt very fortunate how our vacation had started. I was certain things would only get better.

As we walked and talked along the way, we ran into the two "homeless" young men who were causing the ruckus in the Marriott lobby. They both had obviously been drinking and were sitting on a bench enjoying the sunshine. Their luggage was close by, but they seemed pretty happy and I couldn't resist asking them if they had found shelter for the night. They paused and looked past me to Stephanie who was a vision standing at my side. They were just drunk enough that they couldn't really hide their admiration for those braless 34-DD's, the hair, and the angelic face.

They both stood, but didn't speak for a good 30 seconds while they gathered their wits about themselves. Finally, they looked at me and asked, "How did you know we needed a room?"

At this point I introduced myself and Stephanie and explained that we were in the lobby when they found out they had lost their reservation. The lightbulb turned on and they smiled mostly at Stephanie and introduced themselves as Keven and Michael. They were from Ohio, and here for Spring break. I noticed them for the first time, as people, instead of lousy reservationists.

I have no idea how old they were. I'm old, and everyone looks young to me. But if I had to guess, I'd say mid 20's. Both were athletic, both brown haired and brown eyed, Kevin had a football build, but Michael was built more like a swimmer. I would say they were both very attractive, and looking at Stephanie admiring them I would say she agreed.

They told their story, and none of it surprised me. Marriott had managed to get them a room in the same hotel as us, but they couldn't get them in until tomorrow night. They had tried everything they could think of and so far, but hadn't been able to find anything they could afford. They had just resigned themselves to spending the night on the beach, if it's legal.

I told them Marriott would hold their luggage for them so they don't have to drag it around overnight. That hadn't dawned on them, but they said that was the best idea they had heard today. I asked them if they'd like a margarita, and they both replied in the positive. I excused myself and walked into the bar beside us and got four margaritas in plastic cups to go.

While I was waiting, I was watching Stephanie interact with the boys. High School teachers are gifted that way. They were laughing and enjoying themselves. Someone my age would be devastated if I didn't have a room for the night. It didn't seem to phase them in the least. I noticed Michael reach out and touch Steph on the arm, in an innocent way. They were both very masculine and they were captivated by Stephanie, even though she's a good 20 years their senior.

Surprisingly Stephanie reached out and touched Kevin on the cheek, brushed it really. It was obviously an act of affection. The three of them were really hitting it off. Don't get me wrong, I'm not the jealous type, and Stephanie and I had already had a threesome with Joseph early in our relationship. But he was my age and I didn't feel inadequate with him in bed with us. I assume these two guys can run circles around me the bedroom. And watching the three of them I was starting to think maybe Stephanie would like to find out!

I rejoined the happy group and gave everyone their margarita. Keven proposed a toast, "To Stephanie!!!" All I could say was, "Here, here!" The conversation was fun and it was hot outside and the drinks disappeared quickly. I went for another round and enjoyed watching through the window as Stephanie flirted with these young men. She literally had them eating out of her hand. Everyone was now a little drunker than we should be in public so I suggested we drop their bags at the Marriott and have a nightcap in the hotel bar. Everyone was thrilled at any idea that popped up, and we worked our way back to the hotel.

We were getting attached to the two young guys, and they really were a lot of fun. After we ordered a drink at the hotel bar, I told Stephanie I needed to talk to her alone for a minute. She looked concerned and jumped up to follow me. When we were out of earshot, I asked her, "What do you think about letting Michael and Keven sleep in our extra King bed tonight? I can't really see us putting them out after drinking with us all night."

Stephanie's eyes got really big, she bit her lower lip and swallowed hard. I knew something was up, and she was going to tell me. "When you aren't around, they keep telling me the things they'd like to do to me. Naughty things. I've been playing along because I assumed I'd never see them again. I may have led them on a little."

"And that's not the worst of it. Their dirty talk has me really, really horny right now. Like my pussy has soaked through my panties. I need you to fuck me when we get back to the room, and that might be difficult with two guests."

"Okay, I get it. You know me, I'm okay with anything, but I do think it would be really rude to send them to the street now that we know them. How about we invite them up, but tell them we have an early day tomorrow so we need to go to sleep early. Then when they are asleep, you and I can have our fun. It will make it hot having sex with them in the bed next to us. What do you think?"

"Damn, I like how you think. That does sound kind of hot. Let's see what they say."

Michael and Keven were a little too excited about the prospect of spending the night with us. I was trying to figure out if that's because they won't have to sleep on the beach or if they were hoping to catch a glimpse of those beautiful titties. Probably both. They retrieved their bags from the bellhop and joyfully joined us in the elevator. They had no idea how truly wonderful the room was going to be. When we walked in, their jaws hit the floor. They had never seen anything like it.

There were two bathrooms so I assigned one to the boys. I told them to change into their pajamas in the bathroom before they came to bed. They both laughed out loud. I took the other bathroom and did my nightly routine. I came out before the young men and Stephanie took our bathroom to change into her nightwear. When she was in the bathroom, us three guys jumped into our respective beds and were laughing about the funny situation we were in.

When Stephanie came out of the bathroom we all just stopped laughing and talking. We stared. She was wearing a green negligee; it was fairly transparent and hot as fuck. When I came around to my senses, I looked at Michael and Keven, their mouths were hanging open and then a huge smile formed on their faces. Jokingly Keven patted the bed between he and Michael with a come-hither gesture. We all started laughing.

Not to be outdone, Michael suggested we all hop in the jetted tub before we go to sleep. That caused us all to start laughing again. They really were funny guys and we both genuinely liked them. Meanwhile, I was the lucky bastard who got to sleep with her.

I turned out the lights and opened the drapes and the big sliding door facing the Atlantic Ocean. The moon was nearly full and the scene was amazing. You could hear the ocean waves and music drifting up from the pool. The moon cast a soft light across the entire room and you could see clear enough that we could visit with boys and still see their faces clearly. They thanked us profusely and I knew they really appreciated us. Stephanie snuggled her face into my chest and feigned sleep.

The next thing I remember was being snapped awake by movement in the room. I was still drunk but I saw Stephanie heading to the bathroom. When she came out, she walked out onto the veranda. The party at the pool had gone silent.

Stephanie was a sight. Her hair and gown were moving with the ocean breeze. The moonlight gave her a sexy, healthy glow. I slipped out of bed and came up behind her, wrapping my arms around her and kissing her on the back of the neck. She moaned and leaned into me. It was good to see her relaxed and happy. My body responded to her and my hands moved under her negligee and I felt her breasts. She was beautiful and sexy. We watched the ocean for a few more minutes, felt the breeze, and breathed in the ocean air. Then I led her back to bed by the hand.

Steph and I quietly made love. It was much different than our previous sexual encounters. We were usually really active and the objective was orgasm. This was different and very nice. I was softly touching her, smelling her hair, feeling the warm grip of her pussy on my cock. Tasting her mouth with my tongue.

Neither of us had climaxed when we heard a soft moan from the bed next to us. Michael was having a dream of sorts and had kicked off the covers. He was rolling around and softly moaning. Keven was dead to the world, but had a different problem. His large erect penis was sticking out of his boxer shorts and clearly visible in the moonlight. Without the covers it was openly available for inspection and Stephanie was very interested in doing the inspection.

Michael, who was farthest from us, gave a small whimper and seemed in distress. I had no idea what to do and froze, but Stephanie detached herself from me and took a few steps to the far side of the bed where Michael lay. She began softly nudging him, trying to get him to wake up without disturbing Keven. I just smiled and watched this beautiful girl, trying not to stare at Keven's big cock and nudging poor Michael who was now clearly having a bad (or good) dream. It was hard to tell which.

In one quick move Michael tossed around and knocked Stephanie into the bed between him and Keven. Neither man was awake yet, but the optics were very bad. She fell across Michael and was straddling Keven with her arms. To make things even worse Stephanie's face was within inches of Keven's throbbing boner. She was having a stare down with one of the largest cocks I had ever seen. Stephanie looked at me, we made eye contact, and I started laughing. This was a circus.

I realized I was still drunk and not really thinking clearly. I'm sure Stephanie, Michael, and Keven were all in the same boat.

I saw the confusion on Steph's face staring at this massive, young, and super hard cock. All of her natural instincts were to throw a leg over and slide down on that beautiful erection. At the same time Keven was still passed out and hadn't given consent to do anything of the sort. (Although he sure implied it earlier in the evening, making all of us aware he'd fuck her if given the chance.)

Michael suddenly woke up and tried to sit up but he couldn't because Steph was laying across his stomach. His upward movement pushed Stephanie's face right into Keven's boxers and Keven woke up confused as fuck about what was going on. At this point I was laughing so hard I couldn't even breathe. Stephanie started laughing too, and the young men were getting excited thinking the absolute worst was about to happen.

Realizing he had a hot woman in his bed, Michael reached up Stephanie's nighty and found her pussy. Of course, it was wet as fuck from having my cock inside her a few minutes earlier, and from her staring at Keven's monster for the last few minutes. Michael inserted a couple of fingers and she moaned really loud. Like loud enough I was worried it would wake the people in the next room. She looked back over her shoulder at Michael, but she didn't say stop.

Then she met Keven's eyes, and could see the pleading in those brown eyes. She grabbed his fat cock at the base and licked it from his ball sack all the way to the head with one long lick.

I started to try and explain what had happened but soon realized no one cared. It was a win/win situation and nature had taken over.

I had ringside seats and was amazed by everything I saw happening. I was most impressed with the quality of their erections. I used to have an erection like that, but I had forgotten what it was really like. I reached over and turned on the bed lamp so I could see more detail.

Keven didn't last long. Stephanie was sucking his cock and jacking him at the same time. She doesn't swallow, so she pulled back and rubbed one out while licking around the large head. He shot string after string of thick white cum onto his own stomach and chest. Again, the quantity and quality was amazing to me. Oh, the power of youth. (By the way, he never lost his erection. It was immediately available for round two.)

Michael had seen everything. He removed his fingers from her vagina and stood up beside the bed. He rubbed his average sized cock (almost a clone of my own cock) up and down her sloppy wet pussy. I'm sure she was by far the oldest woman he had ever fucked, and I think he was super curious what it was going to be like. There wasn't much resistance when he entered her. I had been in there for 30 minutes and he was the same size as me.

Stephanie looked back over her shoulder and said to him, "Don't wait, give me your cum. You feel so good inside me."

I don't know if was her words, or if it was the silk lining for her beautiful pussy, but he pounded hard for a dozen strokes and came immediately. His stroking stopped, and his leg muscles tightened and he convulsed up and down on his toes while he emptied his balls into her pussy. She lifted her ass in the air and pressed her tits against Keven's cock and midsection and she had a small orgasm herself when she felt all of that young cum shooting into her vagina.

It was pretty cool to watch. I was super proud of Steph. She took what could have been a disastrous situation and made it into a night of pure ecstasy for all of us. It was going to be difficult to top this vacation.

I knew Stephanie well enough to know what she really wanted was Keven's cock in her tight pussy. His erection didn't even soften at all after the blowjob. She threw one leg over him and slid up towards his face for access to the head of his cock. When she grabbed his cock and aimed it at her already gaping hole a large amount of Michael's cum slid out and down Keven's cock and smeared on her inner thighs. Michael reached in and pulled her panties to the side and placed Keven's cock at the opening of her pussy, then she sat up tall and removed her negligee top.

These two young guys were so obsessed with pussy they forgot what a beautiful set of tits she has. Once free, they dangled in Keven's face and he reached up, one in each hand and pulled them down to where he could suck on them.

For her part, Stephanie was focused on devouring this monster cock in front of her. She slowly slid down the shaft, feeling the oversized head stretching her insides to new widths. It took several minutes to get even half of it inside her small pussy. When it was halfway in, she started to have an orgasm. I've given her dozens of orgasms, but I've never seen her erupt like this before.

It started with uncontrollable quivering leg and glute muscles. It looked like she was having a convulsion and her face was sheer ecstasy. She froze in that position for a good minute, then suddenly pulled up and off of his cock. When she did, she gushed a large quantity of pussy juice and cum onto Keven's midsection and boxers. I was astounded. Not only have I never seen Stephanie do that, I've never seen any woman do that. It was so fucking hot.

After she gushed, she put his huge cock back inside and worked it all the way in. I'm pretty sure no woman has ever been able to take the whole cock, and Keven was really enjoying how it felt. She bounced on him for a while, then he came. When he came is cock got even larger than it was. His head grew in size and Stephanie later told me he was ripping new territory in her pussy. It hurt a little, but she wanted to take it all. She felt like he deserved that.