Read From College Boy to Toy Boy 1 Here.

*****

Part 3…

The next morning, I woke up around 9 o’clock. Janet sat upright next to me with her tablet.

“What are you doing, Babe? It’s 9 o’clock, and you’re already online?”

“I did some shopping for you. And I ordered a new bikini for me. You’ll love it.”

She winked at me and gave me a good morning kiss.

“Everything should be here after breakfast. Then we’re ready for the beach.”

Kate opened her door and peeked out. “Good morning, all together. Do we order breakfast on room service?” she asked.

Bryan’s door opened. “Good morning. That’s a great idea. It gives us some more time to wake up.”

Janet walked to Bryan and gave him a good morning kiss. “Good morning, my little boy,” then turned around, “Good morning Kate, hope you slept well.”

“Hmm, it took me some time to fall asleep cause you guys were pretty noisy. I guess you had lots of fun tonight.”

“Oops, sorry for that. Okay, I’ll place the order,” Janet said. “Any special wishes?”

No one answered.

“Okay, just regular breakfast then.” She picked up the phone and placed the order.

“Breakfast in about 20 minutes!” she shouted so that everyone knew how much time to spend in the bathroom and get ready for the beach afterward. As Janet and I already showered yesterday after sex, we just needed our toothbrushes and Janet that little Makeup table with a mirror.

We were almost ready when a knock on the door announced our breakfast delivery. It was a nice assortment for different tastes, so we all found something he liked and enjoyed chatting while eating. We were just done when there was another knock on the door.

“Those must be your clothes and my bikini,” Janet said, opening the door. She tipped the delivery boy and returned with several paper bags filled with clothes.

“You can check your stuff later, Robert, but I need that new bikini. And then we’re ready for the beach.” She dug through the bags, found a little extra paper bag, grabbed it, and disappeared into the bathroom. She wore another light summer or beach dress and beautiful flip-flops when she returned.

“Okay, let’s go,” she said, and we headed for the hotel’s secluded beach.

Bryan rented four sunchairs with parasols, and we were guided to a nice spot with three Palm trees surrounding our sunchairs to give us more sun protection and privacy. When Kate took off her beach dress, I was amazed by the perfection of her over sixty-year-old body. Everything looked well-formed and tight. Some girls my age would be happy to have a body like that. And everything was hugged by a sexy, skimpy black bikini. Kate looked gorgeous.

And then Janet took her dress off. My jaw dropped open. She wore a micro mini teardrop bikini, just with enough fabric to cover her Pussylips and her nipples. All in white, and I wondered if it would turn a see-through when wet. Bryan wore some tight speedos, which revealed the outlines of his cock cage. I guessed that this was the reason to wear speedos, since he’s into humiliation. I wore some regular boxer shorts like swim trunks.

“Robert, would you help me with the sun lotion?” Kate asked, and I happily agreed, giving me the first chance to touch her body. Kate lay her stomach on her sunchair, and I applied sun lotion to her shoulders and back.

“Robert, unhooking that bikini top makes it easier for you.”

I did as I told and massaged her back with sun lotion as lube. Kate started to moan slightly and enjoyed every touch of my hands. In the corner of my eye, I could see that Janet let Bryan give her the same treat, and she enjoyed it the same way as Kate.

“Hmm, Robert, that feels so good. Please keep going and lotion up my legs and ass.”

“It’ll be a pleasure for me to do that, Kate.”

I took first her left leg, applied lotion and massaged her calves. This gave me a great chance to have a close look at her sexy feet.

“If you want to kiss my soles and suck my toes, feel free to do that, Robert. I’ll enjoy that treat of yours,” she said, looking back and winking at me. I didn’t need a second invitation. Her feet smelled so good, and her soles were perfectly soft. I fantasized about rubbing my cock on them. It was just like she could read my thoughts, and her right foot started to massage my hard cock through my swimming trunks.

“Hmm, it seems like you’re enjoying what you do,” she giggled.

“Kate, you have gorgeous feet and a gorgeous body, and I appreciate it very much that you let me rub sun lotion onto your body. It feels very good for me.”

“Well, then, continue that job. There’s an ass that wants to be rubbed, and there’s still the front that craves your treatment.”

I kept massaging her legs, kissed and sucked her feet, I was in heaven. Her thighs were as firm and tight as her calves, and her ass just felt fantastic. Again, I thought, there are young women around my age who’d love to have a body like that. I kneeled and rubbed her ass cheeks up to her bikini panty line when Kate looked back at me: “Don’t be that shy. I won’t bite. Get your fingers in every spot you want. I want them there.”

I started to let my fingers slip under her G-string bikini and massaged her ass crack and then her rosebud. She moaned and spread her legs more apart. I intensified my rubbing, and when my fingers went down to her clit, she lifted her ass slightly to give me easier access. My thumb was placed on her rosebud, and my middle finger massaged her clit, when a shiver ran through her body. I had given her the first orgasm of the day. I slowed down with my movements and waited till that wave of orgasm faded away. Kate turned around, now lying on her back, exposing her beautiful tits for me to admire.

“Now take care of the front, Robert. Let your hands do magic things to me,” she said with a big smile.

I spread the lotion over her breasts and massaged it in. Her tits were magnificent firm, with nice poking nipples, which were nice to kneel between my fingers. Then I went down to her amazingly flat stomach. I played a little bit with her belly button before my hand pulled her bikini panties aside. My thumb massaged her clit with my middle finger placed on her rosebud. Kate started to moan again and then looked at me and said: “Stick that finger inside my ass and give it a nice massage.”

I did, and Kate exploded with a shivering orgasm that lasted for almost over a minute. That gave me time to check for Janet and Bryan, and Bryan almost did the same with her, what I did to Kate, only without the finger up her ass. Both women were gasping for air, and Bryan had a wet spot on his Speedos from leaking Precum. I checked my swim trunks and found the same traces of arousal.

Kate smiled at me and said: “Sorry, Robert, no relief for you now. I want your balls full of cum for tonight. I want you to ache for an orgasm. I want you to beg me to please let you cum. This day will be full of teasing, and you’ll learn to please a woman so she can’t do anything other than reward you. And I promise you’ll love your reward. All you have to do is to serve my needs, and you will be a very satisfied man tonight. You think you can do that?”

“It will be my pleasure to fulfill your every wish, Kate. Even though my balls are already aching.”

“Haha, already blue balls? You still have a long way to go till tonight,” she giggled.

“Same for you, Cucky,” Janet said to Bryan. “But if you’re a good boy, I might reward you tonight. We will see,” she giggled teasingly.

“But anyway, Robert, I’m also applying sun lotion to your body. Lay down on your stomach.”

I did as I was told, and Kate gave my neck, shoulders, and back a nice rub. Then she moved down to my ankles and worked her way up until her hand slid up under my swimming trunk, and she found my rock-hard cock.

“Hmm, you have a nice Pack here. Now I know what Janet was talking about,” she said and started to jerk and squeeze my cock slowly and gently. When she had me on the very edge of an orgasm, she said:” Turn around, time for the front.”

I turned around, and my cock produced a nice tent with my trunks. She started to lotion first my chest, arms, and stomach, then again from my ankles up until she had my cock in her hand and edged me again.

“You would love to cum right now, Robert, wouldn’t you?” she asked teasingly, “but not yet, big boy, there’s still so much time till tonight, so much time to build up a big, big load in your balls,” she smiled.

“Ohh, I guess it’s going to be a hot day for me,” I said.

Janet and Kate laughed, and Janet added: “And so will it be for my Cucky.”

When our skin had absorbed the lotion, we went for a little swim in the Pacific. And again found Kate’s hand on my cock, and gave me the third edge of the day.

“How about you, Cucky, wanna get edged all day, too, like Robert?” asked Janet.

“I don’t know if I can stand that, and I’m caged,” Bryan answered.

Janet took that little key from her necklace, pulled his speedos down, and opened the cage.

“No self-touching. If I see you jerking your little dick, I’ll lock you up for the rest of our vacation, understand me?” she threatened Bryan.

“Yes, Mistress, I’ll keep my hands off myself.”

“That’s a good boy,” Janet said, and started to jerk his little dick with just two fingers until he was right on the edge, then stopped.

“I think I need a drink. Let’s return to our sunchairs, and Cucky can get us Drinks from the Beach Bar.”

When we arrived at our spot, Bryan’s little dick still tented his speedos, and Janet said teasingly: “Oh, they’re all going to see your little tent, Cucky. And I dare you, don’t try to hide it.”

We could observe Bryan going to the Beach Bar, and every woman crossing his way stared at his little tent and started to laugh at him. The same on his way back, his little dick was still tenting his speedos, and everyone laughed about that. He handed us our drinks, his face bright red in embarrassment, and Janet asked: “So, Cucky, how was your walk of shame? Any new Jokes?”

“Nope,” he replied, “heard them all before.”

“But you enjoyed it anyway. Your little dick is still rock-hard. Come here. I’ll edge you once more.”

While Janet slid her hand into Bryan’s speedos to play with his little dick, I asked Kate: “You want to get a foot rub?”

“Yes, please, very thoughtful of you.”

I sat at the foot end of her sunchair and took one foot to give it a nice massage. Kate’s other foot found its way up my trunks, and her toes softly tickled my hard cock. Again, she stopped before I’d reach the point of no return.

“Kate, how do you do that? How do you know the exact point to stop stimulating my cock? I don’t say anything, I avoid to moan, but each time you stop at the very last second, so I don’t cum.”

“Oh, decades of experience. My hubby loved to be teased by me. Sometimes, I edged him for days until he had blue balls. I enjoyed those sessions as much as he did and became an expert. It’s just a little twitching that goes through your cock shortly before you cum, and when I feel that, I stop touching your cock.”

“I hope you don’t plan on edging me for days?”

“Not if you don’t want me to do that. And I guess our time is too short for only edging you. Janet and I want to fuck you, so I guess you don’t have to worry. But anyway, I told you, I’m going to teach you some things.”

“First lesson learned,” I laughed.

“Time for the other foot and to deepen your experience,” she answered, shoved her foot up my trunks, and started to fondle my cock again with her toes while holding her other foot in position, ready to be massaged. Bryan was smart enough to give Janet the same treat, and Janet returned the favor with another edge to his little friend.

“You have very skilled hands, Robert. I’m all hot and bothered. I think I need your hands a little higher now,” said Kate, extending her legs. I could see her juices wetting her G-string, and I moved my hands up her legs. With one thumb, I gently massaged her clit, while my middle finger fondled her rosebud and then slid into her ass. Didn’t take long till Kate quietly moaned and climaxed in a wet, squirting orgasm.

Janet orgasmed shortly after her. Both women rewarded Bryan and me with our next edge.

We were zipping our Drinks and chatting about slippery sexual-related stuff. Janet would humiliate Bryan once in a while by telling stories from sexual encounters with better-endowed men than her Cucky, how pathetic her Cucky was watching her getting her brain fucked out and jerking off, and how some men laughed at him when he first ate his load out of his hand, and then their creampie out of Janet’s pussy. Bryan’s face was dark red, but his little cock tented his speedos, which showed that it aroused him hearing Janet telling me those intimacies.

“What’s more important for you, Janet, the length or girth of a cock,” asked Kate?

“As long as the cock is not shorter than 7.5 inches, it’s the girth. I love the feeling when a cock stretches my pussy to its max. And when I get such a perfect cock like Robert’s massive beast, then I’m like Alice in Wonderland. You’ll love it, Kate, I promise. And I can’t wait myself to fuck that beast again.”

Now, it was me who blushed a bit. Kate moved her hand again into my trunks and fondled my stiff cock right to the next edge, and so did Janet with Bryan’s little pecker.

“I can confirm that it feels fantastic in my hand. The rest I’m going to find out tonight,” Kate said and smiled at me.

A little later, we decided to go for a snack—nothing special—and then walked around to get to know our surrounding area better before returning to our sunchairs.

“Time for a second layer of lotion,” Kate said, “don’t want to miss fucking that big cock because of a sunburn.”

Janet laughed.

“Yes, and my pussy could use another gentle rub from Cucky, and I need to edge him again. I wonder how big his load will be if I let him cum tonight.”

She grinned at him with a devilish smile.

“Robert, my pussy is craving some attention, too, and then back to your Joystick. I’m not done yet filling your balls,” Kate giggled.

So Bryan and I did our lotion applying for Jobs once again and then massaged the lady’s pussies to their next climax. But this time, I already inserted two fingers into her anal entrance. No complaints. It seemed like she loved that because she was not tense. She almost sucked my fingers in and exploded in another squirting climax. Again, Bryan held back a little more, but Janet also had a trembling orgasm. Now it was our time again to get lotion and edged again. I lost count of how many edges I already had, but I was horny as hell, and my balls started to ache.

We had a couple more drinks and fooled around until we decided to return to our Suite. Janet took Bryan with her to shower, and Kate took me along into her room and her shower, only to tease and edge me some more. Janet moaned when we left the shower: “Oh, your tongue is so good. I wish your dick could do the same to me. Keep licking, keep licking, I’m cumming, I’m fucking cumming!”

Kate smiled at me and said: “1:0 for Janet. We better start playing now.”

“At your service, Ma’am, whenever you’re ready.”

I lay next to her, we kissed passionately, and my fingers squeezed her hard, erect nipples softly. Then I sucked on them and kissed my way down to her delicious, shaved pussy. My tongue played with her clit, and I inserted two fingers into her pussy. I sucked so soft and slightly until she exploded, and her squirting orgasm flooded my face in pussy juice. Kate was breathing deeply, and it took her some time to get to normal breathing, but then she ordered me to lay on my back. She crawled on top of me in 69, lowered her soaking wet pussy onto my face, and started to suck my cock. My tongue again played with her pussy. I was close to the edge, and Kate rolled off from me and looked me in the eyes, and said, “Time to stretch that pussy. I want to feel that cock inside of me.”

I moved for missionary between her spread legs and slapped my cock a few times on her swollen Clit and then entered her Love Tunnel. Kate was tight for her age, and I needed a few steps until my balls were slapped against her ass. Slow and rhythmic, I pumped my cock in and out. Kate was enjoying it and pressed her legs on my butt to push me even deeper.

“I’m cumming Kate, no way of stopping now. I need to cum right now.”

“Give it to me, Robert, pump your load deep inside my pussy. I want to feel it real deep inside of me.”

And I did. I shot spurt after spurt of hot cum into her pussy, and when she felt that first spurt, Kate also came with a screaming, intense orgasm. I kept lying on her, still pressing my cock deep into her pussy until the orgasm faded away, and I felt my cock becoming soft. I rolled off her and lay in silence next to her, staring at the ceiling, trying to understand what had happened those last two days and nights. Kate kissed me and said: “That was amazing, Robert, Janet is right, your cock is a beast.”

“Thank you, Kate, but you’re amazing, too. What you did all day today with me made this orgasm the strongest, most intense I ever had.”

“I told you I’m going to teach you a few things, and when you want to go for a second round, there’s still something I want to show you.”

“What is it, Kate? What more can you show me?”

“Did you ever fuck a woman in the ass?”

I looked at her, surprised. “No, I never had a girlfriend that was into it. Are you into Anal sex?”

“Well, when the male Partner knows how to open that rear entrance gently and keeps being gentle when pumping in and out of the lady’s ass and just does what she likes, it can give her the most intense orgasms she ever had. And I want your beast pumping gently balls deep in and out of my ass.”

Just the thought of fucking that beautiful ass of hers made my cock twitch, and it became hard again.

“Looks like someone is ready for his next lesson,” she smiled with a wink at me, leaned over to the nightstand, and grabbed a tube of lube out of the drawer.

“Now, worship me, worship my body, pay special attention to my ass. Show me that you want and that you deserve to fuck my ass.”

I caressed her body literally from head to toe and ended up licking and tongue fucking her anal entrance.

She moaned: “That’s it, Robert, that’s how to convince a woman that she wants it, too. Now take that lube, lube your cock, and then my sphincter, place your glans on it, look deep into my eyes, and penetrate me.”

I did exactly as she told me, and she gasped when my glans popped into her ass. Her expressions in her eyes were indescribable and motivated me to move in and out as gently as possible.

“Yes, Robert, that’s exactly what I was talking about, take me, claim me, FUCK ME!!!”

When all of my cock length was inside her ass, she gasped: “God, you’re so big and thick. You stretch me out. I love it. Now fuck me, faster and stronger, until you get the feeling it’s too much for me. Then, just slow down, don’t stop. Don’t give me the chance to prevent you from entering me again. When you find out what your lady wants, you can have lots of fun with her.”

I was quite happy that she told me to go slow. After all that edging, I was close to cumming, and I didn’t want that yet. I fucked her ass just nice and easy, steady with the full length of my cock. But when her orgasm erupted in another fountain of pussy juice, it was too much for me, and I unloaded deep in her ass. When we returned to breathe, she looked at me: “You’re such a quick-learning guy. You did great tonight. I haven’t been fucked for a while, and even longer, not as good as you did. Thank you, Robert, you’re fantastic.” She gave me a passionate kiss. “I have to thank you, Kate. I won’t forget this Hawaiian Trip for the rest of my life. You’re gorgeous.”

“It’s a pleasure with a student like you. You’re a natural stud. I bet you’ll fulfill many female needs in your life. But let’s take a quick shower and then go to sleep. I’m exhausted, and I guess tomorrow you’ll have another “busy” day with Janet,” she laughed.

After the shower, we cuddled and fell asleep pretty quickly.

*****

Part 4…

A little beep and the blinking light of my mobile phone, which announced an incoming new message, woke me up early in the morning. I grabbed my phone and opened the messenger app. The message was from Janet. A picture of her glistening, wet pussy popped up on the screen, and the words: “I NEED A BIG COCK”. I turned my head towards Kate. Without opening her eyes, she said: “Go, Robert, it’s okay, I’m fine.”

“How do you do that, Kate? How do you know who messaged me?”

“Female intuition. And I know Janet,” she giggled.

I was halfway to the door when Kate stopped me. She raised her head slightly, looked at me, and said with a wink: “Don’t forget the lube if you want to try what you learned.”

“You’re unbelievable, Kate,” I laughed.

I gave her a Kiss, grabbed the lube, and left the room. I just saw Bryan disappear into his room and close the door. I crawled into the warm bed and gave Janet a deep Kiss.

“Nice to see you. I hope Kate didn’t exhaust you too much last night. My pussy needs you,” she giggled, looking me deep in my eyes.

For now, I let the lube disappear under the pillow and started to caress her body. My hands cupped her tits, and I nibbled on her erect nipples. Then I worked my way down, my tongue playing with her belly button piercing for a few seconds before I placed my head between her legs and lapped her soaking wet pussy. When she was close to cumming, I pushed her legs in the direction of her head so that her ass lifted from the bed. My tongue played with her rosebud, and then I pushed it in and tongue fucked her ass. Janet moaned in pleasure, and her anal entrance relaxed, and my tongue went even deeper into her ass.

“Robert, what are you doing? That feels so good, my God, I think I’m cumming.”

Said that and exploded with a leg-shaking orgasm. I crawled up to her and kissed her. She grabbed my head and looked me in the eyes: “Fuck me, Robert, I want that cock, please fuck me.”

My cock slid into her wet pussy just so easily, and with full strokes, I pumped in and out of her, nice and slow. It didn’t take long, and Janet moaned again.

“I’m close, fuck me, fuck me harder, give me all you’ve got.”

Now I sped up and thrust hard into her, my balls slapped against her ass, and Janet came again.

With my cock still in her pussy I leaned forward, looked into her eyes, and asked: “Have you ever been fucked in the ass?”

Looking at me, slightly disturbed, “Hell, no, why should I?”

“Want to try it? You liked me licking and tongue fucking your ass, didn’t you?”

“Did Kate do that with you? Did you fuck her ass?”

“Yes, she taught me the secret of anal sex. And I would love to do that with you. I’ll be very gentle, and when you say stop, I’ll stop, I promise.”

“I don’t know, your cock is so big and thick, it’ll hurt me.”

“All you have to do is trust me and relax. And you won’t find out if you don’t try.”

“That’s true. Okay, I’ll give it a try. If I lose my anal virginity, then it should be with you.”

I grabbed the lube from under the pillow, but before lubing up, I gave her ass another good licking. Then I lubed my cock and smeared a good amount onto her rosebud. I placed my glans on her anal entrance and pushed it slightly in.

“What do you say? Does it hurt so far?”

“No, to my surprise, not at all. To be honest, it gives me a slight tingle. Okay, go deeper now, nice and slow, okay?”

“Yes, Janet, I promised I won’t hurt you.”

With rhythmic back-and-forth movements, I went 1/2 inch by 1/2 inch deeper into her until I was totally in. I paused for a brief moment, checked Janet, and then started to fuck her as gently as I could. First, with short, steady moves in and out, always with my eyes on Janet’s face, to see if she’s still comfortable with what I’m doing. Then, I increased the length of my movements, but still nice and slow. Janet was still completely relaxed, with no spasms of her rectal muscles.

“How does it feel, Janet? Are you okay with it?”

“Yes, it feels great. Go faster, Robert, fuck me, take my ass, fuck me like your little anal whore. I want to cum from this, fuck me fast and deep and hard. Make me your anal slut.”

I looked her deep in the eyes and started to pound her with the full length of my cock. I increased in speed and intensity of movements into her ass.

“Oh fuck, Robert, that’s it, fuck me like a whore, fuck me deep and hard, give my ass your big cock, fuck me, I’m cumming, I’m cumming!”

Her whole body twitched, and she exploded with a huge fountain of squirting pussy juice. Her fingernails scratched on my back, and her legs and feet pressed against my ass so that I couldn’t move. I was close to cumming myself, but I let her enjoy that moment. It took some time until the sensations of her first anal climax faded away and until she loosened her grip on me.

“Thank you, Robert, thank you for that new experience. That was wonderful. I think I never had such an intense orgasm. But how about you, you didn’t cum, did you?”

“I was close, but your grip was so tight, and I didn’t want to disturb that moment for you. I wanted you to enjoy your feelings, every second of it.”

“You’re so selfless. You’re a real gentleman. But I want you to cum. I want your cum deep inside of me. Now fuck me again and fuck me until you cum, until you shoot your load up my ass.”

So I started again to pump in and out her ass. The expression on her face was priceless when I fucked her harder and harder. She enjoyed it, and there was another climax building up in her.

I fucked her like there was no tomorrow. Sweat was running down my forehead. My whole body was sweating, but there was no way to stop me. When she screamed: “I’m cumming,” I exploded in her and pumped uncountable streams of jizz up her ass. Exhausted and out of breath, I leaned forward and gave her a deep kiss. Slowly I pulled out my softening cock. Janet’s ass gaped, but no cum was running out of her hole. It was too deep inside her, and then her ass closed slowly. We lay next to each other, breathing deeply to recover. Janet was the one who broke the silence.

“Two days, we know each other for two days, and we’re fucking so hot, we could melt icebergs.”

“And there are still days and nights to come. In 50 years, I’ll say this was the best time of my life! I still can’t believe what is happening.”

We kissed each other, cuddled, and fell asleep.

*****

The next days we spent together doing some sightseeing or shopping or exploring other beaches but found out pretty soon that the secluded beach of our hotel was the least crowded. I fucked Janet every day and almost every second day, also Kate. Both women were impressed by my stamina, and to be honest, I was impressed myself. Janet got almost addicted to anal sex now, and she loved to make Bryan eat out her anal creampie, which he did whenever he was asked to without hesitation.

By that time, I learned the difference between ‘Alpha Men’ and ‘Beta Males.’ I was sure happy to be an ‘Alpha’ or a ‘Bull.’ But it seemed like Bryan wasn’t unhappy with his place in his relationship with Janet. She was fair enough to release his tension now and then when she teased and humiliated him for some time. Kate, on her side, always teased me all day long when she was up to get fucked by me that night. That lady knew how to drive a man crazy.

After two weeks of fucking and sucking, kissing and licking, smelling and pumping cum in every hole the two women offered, it was time to say goodbye. We were booked on different flights, and there was no chance to change anything in the booking system because all flights were overbooked for some reason. But we promised each other to stay in contact, and we did. Now and then, mostly for some holidays, we visit each other. I have to admit I avoid having a long-term relationship with another woman because, right at this moment, I’m not ready to give up this adventure.

 

The End.

 

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