[M] [22] [F] [26] A vacation that neither of us would forget

My GF (26) and I(M) (22) love each other very much.

It just so happens that we don’t have that much sex because there’s so much stuff to do and also because we live together w/ my mom so we have to be very quiet.

She sometimes asks me what my phantasies are and I being who I am wiggle myself out of that question knowing exactly that I should tell her what I am into.

This one time though I told her that one of my interests is chastity, she showed a much calmer reaction than I would’ve expected and was even interested in the details like how long and in which situation.

She then said that she’d be open to it but not for a long term thing, she wanted me to have it on in sexy sitiuations when she would tease me.

I was very happy about her being open to it and we made love that day talking about me being locked up.

A few days later (we haven’t gone through with the chastity yet) she surprised me by standing naked in the doorframe, bent over revealing a shiny little “crystal” in her butt.

She went through with the buttplug which was a surprise for me because she always said that she would never have anal sex and if at all with her future husband only.

fast forward a couple weeks we sit on the train kind of chatting but also browsing our phones i glance over on her phone and see chastity cages. Instantly I get a rock hard boner which she sees and starts smiling and touching my leg/penis “how do you think it’s gonna feel if you have one of these bad boys on” she says now rubbing my dick through my pants.

Together this night we look at different models/sizes and go for a knockoff holy trainer
https://cdn.shopify.com/s/files/1/1825/4895/products/Clear-Holy-Trainer-2_1280x1280.jpg?v=1488894342

Of course because it is a knockoff it comes from china and takes an eternity to arrive so while waiting for it we talk about this chastity thing and we aggree to test it first and if we like it we might extend it.

When it arrived we both where so excited and aroused by the idea we first tried to put it on me which didn’t go well with a boner so she said we should have sex 1 last time before locking me up for 1 week.

So we did and after making her cum and then blowing my load on her belly she quickly cleaned my cock with her mouth and grabbed on to the cage and put it on my dick.

I heard the click while still recovering from the awesome sex we just had when I opened my eyes seing her jump of the bed excited putting the key onto a necklace I bought her for last valentines.

The following week every day she texted me naughty texts when I was at work and the longer the week was the naughtier I replied opening up to the idea of using some of her toys on me, like the buttplug or the vibrator.

Every night she told me to come to bed naked and eat her out. While playing with her clit she told me the things she wanted to do with me when I was out of that cage.

On sunday, the end of the week of my sentence she told me to come to bed naked again, she then reached over to get the lube. I got very excited to finally get out of this cage when she told me to get on all fours. I did as I was told as she went behind me and I had an idea of what would come. She lubed up my butthole and slowly shoved in the buttplug while massaging my balls.

Slowly popping the plug out and in again she increased the pace asking me if I liked it. I only able to answer with a moan nodded my head.

“do you wanna go further?” she asked. I still only able to moan nodded again to which she reached over to her Vibrator/Dildo which she lubed up as well and slowly pushed it in my asshole.

After a minute or so she also increased pace with this toy and I started shaking from the pleasure it gave me. She was worried about me but I told her to go on.

She was still massaging my balls/dick through the cage which was as hard as it could get in its little cage.

After a couple minutes I had a feeling that I’ve never had before, I had my first anal orgasm. I spurted my load out of my tiny cage while my GF was fucking me with her dildo. She made a suprised “ohh wow” when she stopped penetrating me and leaned forward to kiss me.

“Well, that is a happy surprise my dear” she said “You don’t even need training to be able to cum from anal penetration. Now that you’ve had your fun I want mine. Make that tongue of yours go to work”

I ate her out like there was no tomorrow and we fell asleep arm in arm.

It was the next day I realised that I was still in my cage. I asked her if she had remembered that we aggreed on making it a 1 week thing to which she replied “yeah, but u know we also aggreed on extending it if we both like it. And yesterday it seemed like you didn’t just like it but you also don’t necesseraly HAVE to come out to have an orgasm”

I didn’t have an answer to that because after all she was right.

We aggreed on taking it from week to week figuring out the lock down time while we are doing it but I said I wanted to have her penetrate me a bit more often that once a week. Also I didn’t want it to be a scheduled thing to which she aggreed.

So we went on like this for 2 more weeks before a package arrived for her. She unwrapped it and showed me the new strap on she had bought.

“it’s for both of us” she said. I laughed and kissed her “both of us?”

“Yeah, I mean we both know that you like to get fucked in the ass :) but even though you give me some amazing orgasms with you tongue you can’t replace your cock with it” she said.

“But why don’t you just unlock me then if you want to have me fuck you?” I said.

“Honey, you know that we are on a really good streak here, you don’t want to ruin that do you? Also don’t you have amazing orgasms from me fucking you?” She said.

“Yes, you are right. Let’s test if you are happy with this strap on fucking you” I said.

We continued like this for another couple of weeks before we started packing for a vacation that we had planned together.

We packed all our kinky toys including the key to my cage which I paid a lot of attention to because I had seen many chastity captions which excplicitly had the “forgot the key at home” theme to it.

Luckily my cage is made of plastic so I had no problems goign through security. We arrived at our destination, sunny jamaica with no problems.

We just threw our bags in our room and put on bathing suit / bikini and layed on the beach.

My GF with a shy wearing her white bikini received some complimentary looks/comments to which she replied smile
https://media.gettyimages.com/photos/young-girl-wearing-bikini-lying-at-the-beach-maldives-picture-id56224435

https://thoughtcatalog.files.wordpress.com/2014/06/shutterstock_124623844.jpg?w=1000&h=664

After an hour or so I told her that I was pretty jet lagged so I would go to our room and have a nap. She said that she was feeling fine and would stay at the beach and maybe have a drink.

So I went to our room, got myself a water and put an alarm up for 2h so I wouldn’t miss dinner.

When I turned to close the blinds to our room I saw my GF laying on the beach “what a beauty” I thought before I saw someone approaching her and handing her a coconut which she drank out of.

I closed the blinds and went to bed.

2h later my alarm woke me up. I got up and looked around, no GF ok I thought maybe she’s still at the beach, so I opened the blinds to which surprise I didn’t see my GF.

Unfortunately she didn’t bring her phone to the beach so I couldn’t call her. I walked to the beach and had a look for the closest bar where I saw my GF making out with a huge muscular black guy

http://i368.photobucket.com/albums/oo126/theybf/MAY%202011/682eab1d.jpg

I slowly approached them kind of angry but also turned on.

She saw me just a couple seconds after I saw them and I looked as if I still would be searching for her so she quickly got away from him. After about 10sec I “spotted her” and increased my speed waving at her. She also faked “spotting me” at that time waving back and introducing the guy she just had made out with to me as Shamar.

“Do you know what his name means?” She asked me. Of course I didn’t

“It means, the one who is ready for the battle” She told me, while touching his massive bizeps.

“Well, I can surely believe that” I said, laughing.

We made conversation in which he told me that I was a very lucky guy to have a GF like her while having his hand on her thigh.

Shamar gave out a couple rounds before invitung us both to a party. My GF pretty drunk already aggreed at once for both of us and hugged Shamar as a thank you. I thanked him and told them that before we would go to the party I would have to pay a visit to the restroom. They said they would wait of course and I turned to go.

Coming back I saw my GF rubbing Shamar’s dick through his bathing suit and making out before seeing me and quickly flinshing back. I quickly faked studying the menu of the bar before walking back to them.

We all where ready to go and Shamar invited us to drive with him in his car, my GF jumping in the front seat giving me the only the option to go on the back of his pick up truck.

It was a 15min drive and the window to the driver compartment was black so I couldn’t watch in.

When we arrived Shamar again told me I should be very happy to have my GF before helping her out of the car. Her hair was a bit messy which she explained by pointing at the opened window.

At the party Shamar had invited about 15 of his friends, all of them where build like him. Very muscular, some taller than others all of them shirtless.

They started a barbeque, handed us drinks and joints. My GF always get very horny when she smokes weed so I knew I’d be in for a treat later.

Something must’ve been in that weed or I wasn’t used to that strength because after about 10min I wasn’t able to move while my GF was drinking and laughing with the guys.

She, geting more and more drunk/high got more touchy with the guys forgetting about me sitting quitly in a corner on a couch.

She got up and started lapdancing one guy before handing him one end of the loop knot that secured her bikini top. He pulled it and she was lapdancing him showing her perky boobs to 15guys that where cheering and spraying their beers on her.

Shamar then asked her what that key was for she was wearing around her neck.

Before I could interfere she had turned to me with a big smile on her face and pulled my swim suit down.

Everyone started laughing except for 2 people. Me of course and my GF. She was still smiling looking around and waiting for the laughing to die down.

“You know guys, that’s not it. He also loves to get fucked up the ass” She told them with a hot glare at Shamar.

She then ran towards him pulling down his pants to reveal a gigantic black cock that she started sucking until she gagged.

When Shamar was hard she then guided him towards me. Shamar lifted me as if I was a little kid and placed me so he could easily fuck me.

He slowly pushed in the first time, then increased speed rapidly. I moaned and would’ve begged him to stop but all I could say was “ohhh Yeeaaaahhhhh”

My GF was taking 3 cocks at the same time while watching me getting fucked by Shamar.

When he pulled out, she quickly got up and kneeled to take is cock in her mouth to which he spurted his load on her face.

That didn’t mean that he was done though, he picked her up and started pounding her pussy making her squirt. The next guy approached me and started fucking my gaping asshole.

This continued for another 2h before everyone had fucked both my gf at least once.

Shamar then offered to give us a ride to our hotel. I of course rode on the back again and could just imagine what my GF was doing in the front.

We got off at our hotel and I had another look at Shamar and my GF, she was tangled around him giving him a deep kiss before taking off her necklace and handing it to him.

I looked at them shocked but didn’t dare to say anything against “the one who is ready for the battle”

He then approached me telling me that I really should be lucky to have a GF like that.

Source: reddit.com/r/gonewildstories/comments/b84p8e/m_22_f_26_a_vacation_that_neither_of_us_would