My Girlfriend New Before I Did

--Cassie and I have graduated and it is now our summer before college. We never returned to the spa, but continued to have sex the same as before we went. Cassie decided we needed some excitement and booked us a trip to a small island resort hotel.--

The plane had just landed and we were all taking our bags out. On the plane all ages and kinds of people arrived with us, all couples. Cassie and I were clearly the youngest at 18.

We walk straight from the runway, towards the hotel. Cassie grabs my hand. "Babe I need to tell you something... This isn't an ordinary resort."

"What do you mean?" I ask her.

"Well I'm sure you've heard of tease and denial? This is a special vacation spot where they practice that..." She responds back.

Surprised I ask back, "Why would we come here then?"

"I just figured we haven't done anything crazy since that spa, and if I got you out here you couldn't say no... I'm sorry baby." She says looking down.

She knew me too well. Of course I couldn't say no after seeing paradise. What the hell, what's the worst that could happen, I thought.

"Don't worry, I'll do it."

"Really?!" She looked up beaming and jumped on me for a hug. "This is going to be so much fun! I'm not even really sure how it works, so it's a surprise for me too!"

We got to the front desk and got our keys. Before we left they gave us a small box and said it was for the "special" part of the trip, whatever that means. "And remember sir, there is a dress code for men, however women get to choose what they wear. I mailed the clothing to your girlfriend before the trip."

Finally we reach our room. We walk in to a huge room with a Jacuzzi bath tub and a king bed.

"So what's this dress code like?" I asked her.

"Well.." She said with a chuckle. "I think you'll look cute in it."

She pulled from her bag what I can only describe as a minimalist speedo. It was practically a string all around except for a triangle of fabric in the front to hold in my cock and balls.

"You're kidding me.. What about the box?" I ask.

"You might want to start with that first." She responds.

I turn around to see her holding a clear pink chastity cage and a key strung though a necklace. Just go along with it, this will be fun, I think to myself.

"Alright strip lets get you dressed up!" Cassie says walking closer to me.

After getting naked she puts the ring around my balls, and puts the top part over my flaccid 3 inch cock. After the pieces are in place she slides the lock through and clicks it. "There all snug." She says with a smirk. "Now these!"

I grab the thong swimsuit and pull it up. The string goes between my ass cheeks and just barely covers up the cage.

"Now it's my turn. Sit on the bed." Cassie says.

She slips out of the dress and panties she was wearing quickly. She walks over to me and straddles my lap cowgirl style. With her pussy on my caged cock and her tits on my chest she slowly grinds back and forth, making me horny. I feel my cock begin to press against its cage. She leans in and kisses me, then whispers in my ear, "I kind of lied about it being a tease and denial resort... This is a cuckolding resort." Cassie pushes me down on the bed get off me and grabs her bag, retreating into the bathroom.

I wait for her to come out and she returns wearing a one piece string swimming suit with just enough fabric to cover her nipples and pussy. "Like my new swimsuit?"

"Yeah it looks great, but did you say a cuck-"

"Shh.. Listen you have nothing to worry about. All that means is I am going to get some action every night we are here and you are going to watch. If you want to cum at all then you better do what I say" She told me, dangling the key to my cage in my face. "Now lets go to the pool." Flashing me a smile.

Cassie made me walk behind her on the way there, giving me a full view of her ass only covered by a piece of string.

We finally make it down to the pool, where about 10 couples already are. As I look around I see four other guys wearing swimsuits just like mine. I also notice that the rest aren't. These men are wearing what looks like a tan colored wool boxer that extends at least 8 inches below their balls. The more I look I notice I can see the outline of cages in the swimsuits like mine. The men with boxers all I can see is an outline of their cocks.

Cassie decides she wants to go the beach instead. I ,of course, had to follow her down again. At the beach we see chairs already set up and a little tiki hut bar too. A few of the chairs are taken by couples. Cassie finds two open chairs next to a slightly older couple. Probably around 40 the husband is still very fit with abs showing. The wife is very tan with big natural tits and a normal bikini.

"Care if we lay out here?" Cassie asks them with a smile.

"Not at all! Go right ahead." The wife says back. "This is Alan and my name is Angel."

I go to shake their hands and look down to see Alan in tan boxers. Uh oh.

"Let me get us some drinks." Says Alan as he gets up. As he shifts I catch a glimpse and see at least a 6 inch cock outline in his boxers, and that's not even hard. I'm assuming Cassie saw too because she got up and whispered back and forth with Angel. Then she came back over to our chairs and took off her bikini. She decided to tan her back I guess and laid on her stomach.

Alan comes back with four drinks and definitely takes notice of Cassie. She looks up at me and smiles, wiggling her ass in the air as she does it. We sit in silence for a few minutes just enjoying the sun.

The silence is broken by Cassie, "Alannn, will you come rub tanning oil on my back?"

Alan turns to her, "Of course dear, I'd love to." He comes over from his chair and sits beside Cassie on hers. She leans up to hand him the bottle, flashing him her tits while she does it.

Alan begins by pouring the oil over her entire backside, then started rubbing it in on her back. I could see his dick starting to stiffen up. He made sure to spend plenty of time around the side of her back moving his hand under her to get a feel on her tits. After he's done with her back (and tits), he moves to her legs. He rubs the oil all around her legs and leans up to Cassie's ear. "You have beautiful legs baby." He whispers to her. She says nothing and simply leans in for a kiss. They broke it off after about 5 seconds but it felt like forever to me.

He returns and finishes her legs, leaving the main course. Her perky tight ass. He poured extra oil on her ass and began to work in into her cheeks. When he got those done he moved to her inner thighs. Very slowly working his way up until he was less than an inch from her pussy. By now my cock was straining against the cage.

"Why is this turning me on?" I thought, "Another man with his hands all over my naked girlfriend? It must be seeing her enjoy it so much."

My thought is broken by the sound of Cassie's moan. Alan had put one of his fingers in her pussy. "Soaking wet already?" He asks her.

"I guess my pussy wants something in it." Cassie says looking straight into his eyes. "Why don't you take my spot on the chair." Alan lays down in her chair next to me.

She straddles his legs and immediately pulls down his shorts. His 7.5 inch cock springs out and she smiles. Cassie grabs his cock and starts to slowly lick up and down on it. Then she moves down, licking and sucking his massive balls. After a little bit she moves back up and takes his cock in her mouth. Shallow at first, eventually she tries to take it all. While she can easily get my entire 5 inch dick in her mouth, Alan's thicker and longer cock doesn't quite fit. After about 5 minutes she spits on his dick and begins to move her body up.

She spreads her legs and slowly lowers down on Alan's cock. Letting out a loud moan, she sits all the way down, his cock balls deep in her. Slowly she rises and falls taking him in fully each time. "Oh my god this cock is bigger than anything I've ever felt!" She cries out while riding him. They fuck like this for at least 10 more minutes when Alan tells her to get off and lay down.

She lays back down on her stomach and Alan gets on top. Slowly he slides into Cassie's dripping wet cunt. He slowly builds up speed until he is pounding her as deep as he can go. She lets out a moan every time he bottoms her out.

"Fuck Alan you're going to make me cum!" She cries out to him. This only makes him pound her harder. I see her knees bend and her toes curl. Her body starts to quiver as she climaxes all over Alan's big hard dick. Cassie doesn't recover from her orgasm for at least 45 seconds, but Alan kept fucking her the whole time. Suddenly he pulls out quickly. "Roll over baby girl." he commands her and she listens.

Alan stands over her face and tits stroking his cock. Soon he blasts a massive load all over her tits and face, some making it into her hair. She swallows what made it in her mouth and sits up. Without cleaning any of the cum off her face she leans in and french kisses me. "That's a good start to the day, lets go back to the room." Cassie said.

So we did.

To be continued...