Note: This story was dynamically reformatted for online reading convenience. ï>¿My Girlfriend Knew Before I Did byKatiethesissyÂ(C) My Girlfriend Knew Before I Did Pt. 01 --I'd just turned 18 and I was in the perfect relationship. Cassie, my girlfriend, was also 18 and had the most perfect petite body with red hair. 5'1" and 105 pounds, with perky little B cups and a tight firm ass. We had a lot of fun together, not to mention the sex was great for me. -- It was December of our senior year when I decided to spice things up a bit. I let Cassie know I'd made reservations for a couples massage at a resort/spa about an hour away from where we lived. What I conveniently forgot to tell her was the massage was nude, and it was at a co-ed resort. Oh well, minor details aren't important. We arrived at the resort on a Saturday and checked in. At the front desk was a cute blonde girl, probably about 25. She gave me a flirty smile and handed me two towels. "You can go get undressed and ready in the locker room to the left, down the hall a little." We walked a little bit and Cassie grabbed my arm, "Did she say undressed?" she said with a little bit of shock on her face. "Well yeah, I'm sure there will be a towel over the parts you don't want them to see. Besides I am sure you'll have a female masseur and I'll have a male." She gave me an uneasy look and turned to keep walking, "Alright we will see how this goes." I reached forward and gave her ass a little smack. "Trust me this will be nice for both of us." We entered the locker room and to me and Cassie's surprise we found both men and women in various states of undress. She turned to me with her eyes wide. "You didn't tell me this was a nude resort!" "I didn't know! It said clothing optional, but I just figured maybe they meant just the sauna." "I can't get naked in front of all of these people!" she said. "Don't worry baby we will still have a good time. We can just wear our towels around." Cassie looked at me with a slight hint of anger for a few seconds, then finally she gave me a half-smile. "Alright if you say so" she said to me. We went further into the locker room and found they had private changing stalls. After stripping our clothes off I turned to get a look at Cassie's nude perfect body. I noticed her nipples were hard, so I reached up and twisted her left nipple. This made her bite her lip and her knees buckled slightly. She just gave me a wink and a smile. "Come on get covered up, we don't want to be late!" We left through the other side of the locker room, me with my towel around my waist and Cassie with hers wrapped around her chest ending around her mid thigh. As I spotted our assigned room, we went in. Inside a male and female masseur were waiting. They both look around 30 years old. The women was brunette with tits about the size of Cassie's but she was a little curvier, in a good way. Todd had short brown hair and was very fit and muscular. Both of them had on thin white clothes and I could see the outline of her tits through it. 'Hello, welcome to the Happy Couples Massage. Before we start I want to introduce ourselves. I am Brandy and this is Todd. We are both trained masseurs so there is nothing to worry about. Now lets begin." She said, while leading Cassie over to one of the tables. Todd pointed mine out too me. "Okay we are going to leave for a second. I want you both to take your towels off and use it to cover your rear end while laying on the table." Todd explained to us and they left through another door. Cassie and I removed our towels and I gave her a quick kiss. We laid down on our stomachs and both of us covered our asses up. There was a knock and the door opened. The two returned and set their things next to the tables. There were holes in the table to lie with our faces through them, we couldn't see each other just the floor. I felt oil get poured onto my back and two hands began to rub it in. It felt amazing and I was very relaxed. Suddenly I realized the hands were a little too small to be a man's. Lifting my head, I opened my eyes to see Brandy was the one beside me rubbing my back. I looked the other way and saw Todd rubbing oil into Cassie's back. I was feeling a little worried seeing another man rub all over my girlfriend's naked body. Cassie seemed to be enjoying her massage and I didn't want to ruin it. So finally I laid my head back down and relaxed again. Slowly Brandy moved down to my calves and began to work up my legs. It felt amazing. I decided to see how Cassie was doing. Todd was also working on her thighs. I watched as he started from above the knee and rubbed all the way up to about 2 inches below her pussy. "Good, keeping his hands where they belong." I thought. From my side of the room I could hear Cassie letting out faint deep moans. "He must really be working her legs" I concluded in my head. Brandy rubbed my legs for another minute or so before she leaned down very close to my ear and whispered "Care if I move this bad boy to do the rest of your back side?", while tapping the towel covering my ass. I didn't see any harm so I nodded back. She took the towel off and I felt oil pour onto both of my cheeks. Rubbing oil in she massaged my glutes deeply. By this point I was so relaxed I could have fallen asleep, until i felt more oil, this time between my cheeks. She continued to rub my ass, occasionally letting a finger run through my crack on accident. (Or so I thought) I looked over again to see how Cassie was doing to find she didn't have a towel on her ass anymore either. There she was naked laying on her stomach while Todd was now putting the oil on her ass. Cassie didn't seem to be disliking it, and besides I had taken mine off its only fair. I could see her bikini line on her ass from where I was. No doubt Todd had the better view though. She looked so sexy laying there naked on the table all covered in oil. While I was admiring her I felt one of Brandy's fingers wander again, this time brushing over my asshole. This shocked me and my body jolted a little. Brandy leaned down again and whispered into my ear, "Don't worry sweetie, it's all a part of the massage." I wasn't really sure what that meant, but I laid my head back down and relaxed. She kept massaging, with her wandering fingers coming more and more. At first I wasn't sure what I thought, but the more she did it, the better it started to feel. Suddenly one of her slippery, oily fingers pressed into my hole and I felt it slip in. My body was instantly washed over with pleasure. Brandy went in and out with her finger, loosening my hole. Brandy eventually slipped a second finger in and I was in heaven. Then she went a little deeper and hit my prostate, which sent a chill through my whole body. While my asshole was getting a massage, I looked over and saw Cassie was on her back now with a towel over her pussy and tits. Todd placed a small towel over her eyes and began the massage at her calves on this side. I was afraid she had seen me when she turned over, but I think Todd put the towel over her eyes for a reason. Back on my side Brandy was still working my hole to great effect. She brought her thumb down and started to massage my balls with it and I knew I wouldn't last much longer. Brandy must have felt this and pulled her fingers out. "Time for the other side sweetie." She told me. I rolled over so see Cassie's eyes still covered, but the towel from her chest was gone. Her little pink nipples were rock hard. Todd was working over her upper body with oil. Starting just above her waist he worked up until her was cupping her perky tits. After he let go every time he gave her nipples a light pinch. Every time he did this she let out a moan of pleasure. Cassie was loving this stranger rubbing her naked tits. Brandy oiled the front of my body and rubbed it in. She worked from the chest down to my legs. She avoided my cock, which honestly surprised me. As she worked back up my legs she spread them a bit. She bent my knees so my feet were flat on the table and my legs were spread open. I was in bliss once again, as she slipped a finger into my ass again sending pleasure through my body. After a couple seconds the second one went in and she was back to working my hole. As she stimulated my prostate I could feel myself getting close to cumming once again. This time she didn't stop. By now my 5 inch cock was sticking straight in the air. It began to twitch while Brandy kept plunging her fingers into my ass. Right as I am about to blow my load, Brandy leans over. In one motion she grabs my cock and deepthroats it all the way to my balls. Overcome with pleasure, I drain my load into the back of Brandy's throat. My orgasm seems to last forever and Brandy is swallowing all the cum I can give her. Finally she swallows it all and cleans off my cock. After I recover she runs her hands down my chest and tells me to look over. At the other table Cassie now has no remaining towels and she's completely naked. Todd has his arm around her back while the other is on her pussy. Cassie is squeezing his muscular upper arm while he has two fingers inside of her and his thumb rubbing her clit. I can see her eyes rolled back while she lets out moans of pleasure. Brandy says to me "I thought you might want to see this." with a smile. Todd brings her to a powerful climax and she begins to squirt! Covering Todds hand and part of the sheet on the table, her body begins to quiver. Todd lays her down and she stays there for a minute, tired from the overwhelming orgasm. Wrapping my towel at my waist I walk over and grab her hand. "Lets go take a shower babe." I say to her helping her up off the table. Slowly she gets up finding her towel. "You two come back soon! You were a lot of fun." She says with a wink as they both leave. Cassie has her towel around her waist as she turns to me. "I think I'm going to just wear it like this if that's okay with you?" She says sheepishly. "Umm.. yeah if that's what you want babe." I mutter. We leave the room and walk down the hallway to find the steam showers. On the way we pass several people. Mostly older men, but we encountered a few couples. The last person we saw in the hall was a completely nude blonde girl. As we get closer I recognize her as the girl from the front desk. With nothing but the towel in her hand, I get a clear look at her perfect C cup tits and her flat, fit stomach. Her pussy is completely smooth and she has a nice even tan. "Hey! Hope you guys enjoyed the Happy Couples Massages!" She exclaims as she recognizes us. Cassie quickly spits out, "Oh we absolutely loved it!" "It was pretty good." I say to her. She reaches out to shake both of our hands. "Well I'm Daniella. You will see plenty of me if you come back." She says and walks away with a strut. Daniella had the type of ass where me and my girlfriend stood and watched her slowly walk away, with a slight jiggle in every step. We turn and enter the steam shower room to find it empty. Hanging our towels on the hooks outside to get in. The shower is one big stall with about 8 different spots. Standing next to each other we enjoy the hot steam. Cassie turns to me and reaches down to my 5 inch cock. Watching her shower had made me horny, and she noticed. She strokes my cock and brings herself in so her perky tits are rubbing against my chest. "That was amazing babe. I have never cum so hard, I mean he made me squirt and I've never done that! You haven't ever made me cum that hard before! I didn't even know I could have such a strong orgasm!" Cassie is now rubbing her pussy with one hand and stroking me with the other. Both of us are getting close. "I.. just cant stop... thinking about it.." Her body starts to quiver as she has another orgasm. Seeing her like that pushes me over the edge and I blow another load of hot cum. We stayed in the shower a few more minutes, then dried off. Both of us walked back, with our towels at our waist, to the locker room. Inside we got back to our locker. On the other side of the room I see a fit, muscular guy with a towel on his waist. Cassie sees him too and waves over to him. He waves back, clearly checking out her bare tits. She turns back around to the locker smiling, but I just brush it off. "Do you think we should just change out here?" Cassie says to me. "Uh sure, I guess." I respond. Cassie rips the towel off her waist, leaving her completely naked. "Oh darn I forgot to get my clothes out of my bag." she says, bending over to open her bag. She takes her sweet time fumbling through her bag. First pulling out her panties, then her shorts, and finally her shirt. Behind her on the other side, I see the man she waived at enjoying the view. With her bent over, he has a clear view of her bare ass and I'm sure her shaved pussy. Finally she puts on her thong and then her shorts. Still without a shirt she stands up turns her back to me, and slowly puts her shirt on. The man has a smile on his face from the sight. Finally we get all of our stuff and walk out the front. "What was that about?" I ask her. "What do you mean? What was what about?" She says looking confused. "Nothing, nevermind its no big deal." I respond. "Okay babe. We should come back soon. That was a lot of fun!" She says. My Girlfriend Knew Before I Did Pt. 02 --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.