Unforgettable summer

We spend the rest of the night drinking and having fun. Dick was mixing cocktails, I had no idea what he was putting in them, but we were getting drunk. Danced around all night, and some of us even went for a swim. We were laughing and teasing each other, spam on the ass, sticking bottles in each other, Ed even mounted the male sex doll and rode it like a cowboy. We all went to sleep in our rooms, I was hammered. The next morning, I woke up with a heel of headache, I got up and went to the bathroom. I went to grab my dick to pee and I felt something. Those fuckers had cock caged me, with a cock cage while I was asleep. I still peed true the hole and went to the mirror to check it out. It was a small pink plastic cage, with a small lock. I went downstairs, to ask what the fuck it this. The guys were in the kitchen, joking around.

“What the hell is this”- pointing down at my dick.

“Our little surprise, don’t you like it?”

“You could have just asked me to put in on”

“Yea but this is a nice surprise, there is more, we have hidden the key, so you will have to earn your freedom. We bought 2 of them just in case, but it worked out we locked in Tom two. This will help you fill more girlish since you can’t get hard now” – they said while laughing.

Well I have to admit, I didn’t like it at first, but I liked the idea, and when I found out it was their surprise and I have to earn my freedom I got existed, and a little hard, not that you could tell with the cage on. After a while, Tom also got down, he was so fucked up that he didn’t even notice it. His was blue, and when we asked him what it that, he was shocked. After that, they explained to him too and we all had breakfast together. We also got served 2 glassed of “protein” to help us out during the day, and that was our first task in earning our freedom, so we drank them, I took my time with me to savor the flavor. I feel like every time I act as a slut and do stuff like that the guys get turned on. They didn’t tell us anything else, except that we will find out later. We decided to get dressed and go around for some exploring.

We dressed normally, and under the shorts, you couldn’t even notice it. We took 1 car, Dick was driving with Tom in the front seat and I was in the back between Ed and Sam. They were joking around, asking me how I feel, grabbing me truly the shorts and pulling my caged cock. We stopped in town and decided to go on foot. Picked up some bars we wanted to visit, and sat at a restaurant for lunch. Tom even joked about how he loved to fuck the cute waiter, but we reminded him that he can’t at the moment. After that, we walked down the beach area, picked up some tows, and lay under the sun. There were a lot of cute guys and girls there. I still like girls and got hard at the sight of ones I like, but it was painful at the moment so I ignored them. While in the water Sam joked around and pulled my shorts down, exposing the cage, I quickly pulled them back up and no one saw me. He said,” What do you care no one around knows us”. And he was right, it was time to be free. We got tired and head back to the car. On the way back Ed told us he got sucked by the lifeguard while we were swimming around, and that he invited him to a specific bar tomorrow night.

The house was not too far away maybe 2-3 miles away, on one side of the road was the sea, on the other hand, and in the distance, you could see the town. As soon as we started the ride home, Dick asked “So you 2 ready to start earning your freedom?” We nodded in agreement. He grabbed Tom by the neck and pulled him down, in the meantime Ed and Sam had already wiped their dick out in waiting, so I got to work. After a mile, Dick pulled over to the side of the. I was confused, we were in the middle of the road, and there was only sand and cars passing by. “Get out, and get undressed,” he said. We complied, Ed sat in the back seat, while Sam pushed Tom towards him and started to fuck him, Tom didn’t think twice and started sucking Ed’s dick. Dick grabbed me and put me over the hood of the car. I was there in the middle of nowhere, spread on top of a car, with a pink cock cage, getting rapped by a big hairy man, while cars were passing by. It’s a good thing no one bothers us. Some cars blew their horns, and we heard some whistling, and some guy shouted – “Yea baby you get some”. We kept fucking and changing positions, around the car. Tom and I ended up on our knees next to each other waiting for our reward. Our 3 loves came all over our faces, dripping down our chests. We swallowed as much as we could, then we all got back in the car. I didn’t want to get it over my clothes so I stayed naked, well mostly I still had my cage on.

Back at the house, we washed up and Tom asked them if we have earned our freedom. With big smiles on their faces, they said “NO”. We rested for a couple of our and played some board games. Early evening, they asked us if we are ready for the next task. It was a reminder of our previous adventure, they told us to go up and get ready to “serve them”. We didn’t have a maid dress, but we put on our wigs, put on some pantyhose, with tight short skirts and white tank tops. We got down to the living room and started doing chores, that that there was nothing to do but we got into our roles. Tom and Ed had grabbed on to the (the girl one) and were tearing it apart, well that’s why I bought it. They called us to them, and said “Fuck us while we fuck her”. Confused at first but then remembering all the vibrators I bought, we took 2 of the bigger ones and started fucking them. In the meantime, I saw Dick standing there, playing with his ass and one of the dildos. I was so happy to see him like that, I made that happen. The guys came all over the floor and told us to lick it up, and so we did. After that, they laid back on the couch to rest. Dick told Tom as this is his first-time “serving”, remember before I was around Tom was normally the one getting fucked, but nothing that intense, I feel like that is why he was looking for guys to fuck on grinder. Anyway, he told him he can rest for now. I didn’t have that pleasure and to be fair I didn’t want to rest. Dick told me to put on a show for him and pointed to the male sex doll. He didn’t have to tell me twice. I put it right in front of him and started to suck the dildo. But that was not what he meant, he pulled me up and just dropped me on top of it. I was ridding it hard, while everyone was watching, I moaned and sweated, mostly to put on a show. Dick was still paying with his ass, he called him to come over. Still riding the doll, he was laying in the armchair and pushed my head towards his asshole. I was eating his ass while riding a fake doll, with 3 guys screaming from the other side of the room. After that, he pulled me up, placed me on his cock, and said “Ride me just like you rode him”. The whole time I was leaking pre-cum from the cage, but after Dick turned me down on my head, legs in the air, and started to fucking me, I couldn’t hold it anymore, and with a soft caged cock, I started Cumming on top of myself true the cage. Dick didn’t stop until he filled my ass up.

Still, in “uniforms”, pantyhose torn at the knees, I covered and filled with cum, we looked like we had earned our freedom. I was going upstairs to wash up, but they stopped me.

“You are not done yet”

“I was just going to was up a bit”

- “No, you are not allowed to, come back here”

He took out 2 plugs and stuck one inside Tom and one inside my cum leaking ass.

“You have more job to do before, you are free”

We spend the next couple of hours, crawling around, as we were not allowed to walk like normal people, we were sluts. Our 3 “masters” were laying around the room, watching TV or on their phones, and ordering us around. Telling us to make them drink or bring them a snack. After a while, they started to call us by our female names, I was Sasha again and Tom was Natalie. They called us and expected us to crawl to them as fast as possible and they. Then, for example, pointed a dick to our face and expected us to start sucking it, or scratched their ass and expect us to eat it, sometimes they just pointed down and we are expected to sit on their cock and fuck ourselves. Of course every time we had to pull out the plug and then put it back in again. That lasted for a while since we are running around every minute or so to a different guy, doing different things. When they got bored, Dick took Natalie out the back, I saw then true the window, Natalie was pinned down on the ground while big D was ripping her ass apart. Ed and Sam took me to the beach. They said every whore needs to get fucked in the sand, I sucked them for a bit underwater, I hated that, then they fucked me together in the sand. We went back in, and Natalia and Dick were finished. Natalie even had her cock cage removed and he was masturbating on the couch, as he didn’t get the chance to cum once today. I on the other hand came twice today so I was happy. They gave me the key, but I said I would like to keep it no true the night. I slept with a cage on my cock and a plug in my ass, all covered in cum. That was just the beginning of the adventure.

The next morning, I got up, took the cage off, felt like that was enough, and finally took a shower. We were all pretty tired since last night, so we chilled during the day. After dinner, we all got dressed up, in shorts and shirts, and headed to town, to the bar that Ed got invited to by the lifeguard. We met him there, sat at a table on the terrace, and ordered some drinks, it was an open bar at the beach, music was not too loud so we could still hear each other. The lifeguard started to tell us, that there is a couple of bars there, that all are welcome, that they were free-minded and no one was judged. We looked around and they were a straight couple, a girl party, and even some guys were making out at the tables. I also noticed a couple of sissies like me, dressed in summer dresses hanging around the bar. I was too afraid to go out in public like that, but after tonight who knew? After a few drinks we, all split up, Ed was with the lifeguard, Sam found a girl he likes, and was dancing with her. That was not strange since both he and Ed, till a few months ago had girlfriends. I was surprised to see Dick hitting it off with the waitress, he was very big and strong and women always feel for him, but I didn’t know he liked them as well. I saw Tom (or Natalie to use his new name), making out with a girl at the bar, which was strange I didn’t know Dick liked girls, but I was 100% sure that Tom was gay and only liked guys. After she turn around I saw her face and realized that she is a He. So I laugh to myself and moved on. There was a really cute girl at the bar, with a nice yellow dress, and amazing but, long dark hair. I took a sip and went to talk to her. She was really cute and feminine and we hit it off, I was even surprised how easy that was, me working out paid off. After some making out we went to the bathroom. No one was there, and I was backed up on the sick when suddenly she turned me over, pulled my pants down, and started to eat my ass. Surprise at first, not knowing to be surprised at how fast we got to that point or that she was eating my ass. She then let me turn back and took her dress down, to reveal 2 magnificent fake tits. She then grabs my cock and started to give me the most amazing blowjob ever. I came in her mouth, and she got up and kissed me transferring it back to me. We kissed like that for a minute, swallowing all of it. She had a few drops on her boobs, so I started to kiss her neck, go down to lick them off, and I stuck my face between them, grabbing her ass. She pushed my head down and I was kneeling in front of her. She pulled up her dress, moved aside her panties, and there it was a beautiful 6.5-inch cock. I was shocked and stunned at the sight, I thought she is a girl, so feminine, with such a nice figure and an amazing ass, turn out she is a tranny. She didn’t wait for me long before pushing my head towards it and fucking me in the mouth. I was sucking this delicious cock, still surprised. Sam walked on us while she was stuffing it down my face, I saw him with the end of my eyes, he just smiled and left. She was fucking me like that for a while, then told me to stand up and turn around. She lifted one of my legs on the sink, and my dick was hanging down off the counter, with one leg up and ass sticking out. She spits a little more on my hole and started to penetrate me slowly. Realizing this is not my first time and that I am loose, she pushed it all the way and started to fuck me. I was moaning so much, with her mouth breathing in my ear, and cum dripping out of my cock. A few more people walked in on us, some left some didn’t care, I’m pretty sure the bartender took a piss, stopped looked at me, slapped her ass, and left. She started to speed up until finally she pushed it all the way and started to shake, the warm liquid was filing my ass ones again, only this time after she jazzed every one last drop, she kneeled behind me and started to lick it off, I pushed a little bit and she just to fill her mouth. Then she got up and kissed me once again. We got dressed and went back to the bar. I told her that I was surprised that she was a tranny, I was sure she is just a regular girl. She told me that, that is her game she likes to lure normal boys and then show them what a real woman feels like. I was surprised to find out that most guys don’t run away, but just go with it. She said that my ass didn’t feel virgin and that this was my first time. I smiled and replied, “First time with a woman like you, not my first time getting fucked”. She asked me if I was gay, but I told her that I like, both men and women, and now also trannys. She was glad, then she needed to head out so I walked her out. We kissed goodbye, and she whispered in my ear:

“Btw my name is Venus.” And left.

Sadly, I didn’t get to fuck that juicy ass, that time. But I was admiring it while walking away from me.

I was enjoying the fresh air when I hear some moans, from the back inside some bushes. I was surprised to see Tom, bend over, and the crossdresser whom he was kissing earlier, still on her high heels with her dress pulled up fucking him without mercy. I even saw him throwing, but she didn’t care and kept slamming her balls into his ass. It was a little gross and hot at the same time. I’m pretty sure he was hoping to do the fucking tonight, but maybe later. I went back to the table, Sam and Ed showed up from somewhere after a bit, and then came the waitress walking a little funny, and after her, Dick came back. They asked me where is Tom, but I said that was busy. We waited for him, then walked home.

It was day six of our vacation. Nothing much happened after last night. We walked home, told each other what happened to us, and went to bed. During the day, nothing special happened, we went to the beach to get some tan, the beach in front of the house I mean. We were alone so bathing suits were not needed, and we wanted an even tan. We played some water polo, and build up a sand castle, even buried Ed in the sand. Everyone was in their rooms; I went to check on Dick if he wants to maybe go to town for some lunch. Slowly cracked open his door, to find him mounted on top of the male sex doll, riding it, he grabbed the girl doll as well, and he was fucking that one. What a sight to see, I thought to myself that maybe by the end of the weekend I might get the chance to try that ass. I left him be. Went to Sam’s room but he wasn’t there, went into Ed’s room only to hear the shower, when I looked in the bathroom, I found him bend over under the shower, and Sam behind him rubbing the sand off his back while fucking him in the ass, guess he already cleaned his asshole out of the sand. I left them to fuck in peace, I went to Tom’s room, but he wasn’t in a mood to go out to eat. He told me to check with the others, but I told them what they were up to.

We talked some more about last night, and I asked him:

“Did you end up fucking that Crossdresser you were with last night?”

“No I didn’t get the chance, he just finished in me and left”- sadly replied Tom.

“Hey you want to fuck? Or maybe just let me fuck you like old times? I’m so horny.” – he asked me.

That was a bit strange, normally before he didn’t ask, we just did it, and he never asked to be the only one who does the penetrating. Yes, usually I was the more passive one, and I was up to it, I didn’t mind it now either. But the fact that he asked me, showed he is really horny and this allowed me to ask for something in return.

“Sure Tom, you can fuck me, but I have something to ask as well”

“What? I don’t want anything up my ass at the moment” – said Tom.

“No nothing like that, I want to go out again tonight, try a different bar maybe”

“Yea sure, I’m up to going out tonight, what do you need me to convince the boys or something” – he replied.

“No I can handle that, and if not we can still go just the 2 of us.” “I had something else in mind, after last night and considering no one knows us here and thinking that this opportunity might not come up again.”

“What” – he asked.

“Well I wanted to dress up, you know like a girl again, and go out like that, will you dress up with me please.” “I prefer if I’m not the only one, and we looked so good together”

He was not super existed by my proposal, he wasn’t so into the whole crossdressing and being a sissy for someone shit. But after I laid down, and started to beg, while gently touching and licking his cock, he couldn’t say no to me. Of course, after he agreed, I gave him a proper blowjob, then let him fuck me for as long as he could, I was on my back, on all fours, on the side, and even rode him when he got tired. I was so excited about tonight. I also didn’t mind the sex with Tom. As I said we use to do it all the time, with me taking it up the ass every time we saw each other, and I still loved it and I enjoyed it every time. But I had to take a shot of the opportunity first.

We rested for a couple of hours then sat down to have dinner. When I asked the boys to go to a new bar tonight, they all said they were tired and didn’t want to. Tom was relieved for a moment, thinking he is off the hook, but after dinner I grab him and we went to my room. I told him to put some makeup on and dress up. I picked up for him a green summer dress and I took a cute little blue one. We put on our wigs and stuffed our bras a little, no way we can fill them on our own, he even put on some seamless pantyhose, I guess he was cold at night. Matched some heels and went down. When the boys saw us like that, they were amazed and asked us what it this about.

“Well me and Natalie are going out, you boys planning to leave us girl to go alone?”

The next moment they were getting ready and we all head into town. I also meant to put my cock cage back on but got distracted by how hot I looked, so I left it at the house.

We got to the bar, this one wasn’t on the beach it was all inside. We walked in the music was very loud, the security guard let us down, and let me and Natalie in for free. I was feeling good about myself. We found a free table and ordered some drinks. This was more of a heterosexual bar, they were couples sitting down, guys hitting on girls and failing, and everyone was dancing. My friends did like it as much, it was stuffy, smelled of cigarettes and alcohol, and the music was so loud you could hear anything. The surprising part for me was that no one gave us any funny looks, or stared at us weirdly, guess in the dark, we looked like 3 guys and 2 girls just sitting at a table. I had to pee so I went to the bathroom, I was headed towards the men’s room as normal, but paused in front of it, thinking if I should just go to the women’s. Then a young guy got out of the men’s room in a hurry, and he was walking kind of funny. The next moment I saw my lover from last night walk out, it was Venus, I guess she got another one. At the first sight, she didn’t recognize me, with a wig, makeup, and a blue dress on high heels. But when I stopped her, she recognized me and threw herself on my neck. We started to make out for a minute, I could taste the sperm on her lips. Then she took me by the hand and we walked outside.

“What the hell is going on, why are you dressed like this”

“After our talk last night, I decided you were right, no one knows we here and people are more open, so I decided what the heck”

“So what you like to wear dresses and get fucked in the ass is that it?’

I lifted out my dress to show her my panties and heels.

“Yea I like to dress up, and I consider myself to be a sissy slut from time, I was too afraid to go out in public like that before, but I have to admit it feels nice”

We talked outside for at least half an hour. I told her the short story, how I like to dress up from time to time, about the house we got, and how we fuck each other every day. Then told her how I met Tom, how it all started and about the weekend we spent together. I also mentioned, that I was not always the passive one and that I would love to fuck that ass of hers. And that this was the main reason I went and talked to her last night. Venus was flattered, she again had to go, but gave me her number, and told me to text her tomorrow, and we can see what we can about my desire.

I went back in, took a quick piss in the ladies’ room, and went back to the table. My people were still just sitting down, looking around not doing much of anything. I whispered in Natalie’s ear that we are dressed up like that for a reason, and I pulled him to dance. I told the rest of the guys to come up as well. We were dancing, I was rubbing my body in theirs, touching them on their cocks, and teasing them. We had fun for a while, but after they decided to sit down again. It was only me and Nat dancing now. I saw a guy checking me out, no idea how I even noticed him in the dark, but his eyes were glued to me. I started to touch Nat’s body, went up and down her, moved the hair off her face, and started to kiss each other. We kept that going for a few more minutes until Natalie got tired and went back to the table. I was determined not to waste the night, so I went to the guy that was staring at me before. I just straight up sat on his lap and said hello. He grabbed my ass, and replied with:

“You are new here, I haven’t seen you around”

“Yea me and my friends are just here on vacation”

“Yea, is any of those friends your boyfriend by any chance?” – he asked.

“No, I don’t have a boyfriend” – I replied while gently touching my lip.

“You up for a little fun then?”

I nodded yes in agreement. He smiled and we stood there for a couple more minutes. His hand was all over me. Touching my ass, my legs, he even tried to put his hand between my legs but I stopped him. Not that I mind but didn’t want to ruin the surprise. He grabbed me by the waist and we started to head to the bathroom. He walked fast, so I was tipping as much as I could on my heels. We went inside one of the cubicles. I sat on the toilet, with him in front of me, he took his dick out and told me to get to work. This guy was a bit older, maybe 40-45, he wasn’t the best looking, somewhat grayish hair and beard, fit for his age, he didn’t have abs but didn’t have a gut either, his dick was normal, maybe about 5 and a half 6 inches, with a lot of pubic hair around it. He was smelling of alcohol and cigarettes. His cock was staring at me, again I thought I don’t waste this night so I kissed it, and started to take it in my mouth slowly, inch by inch. He was looking up and moaning while I was sucking his cock. He started to caress my hair, and he wasn’t pushy, he let me do it on my paste, he just enjoyed it. He grabbed my bra, but I spanked his hand a little, while his dick was still in my mouth. After a few moments, he reached down my dress again. This time I let him, his hand grabbed my dick and he jumped back, shocked. I just stood up lifted my dress, took my panties down to my ankles, touched myself with one arm whole spat on the other, and rubbed it on my asshole. All the time keeping eye contact with him, he was still a bit shocked, I turned around, bend over to the toilet seat, and started to shake my ass. He snapped out of it, came close to me, adjusted his dick in my hole, and started to push slowly. It was still a bit dry so he spat on my ass, rubbed it with his cock, and tried again. This time it went in, I exhaled and pushed back on it to go all the way in. He was fucking me very slow, very gently. I was quietly moaning, but I don’t know what came to my mind, and I said:

“Yes daddy, fuck me, fuck me harder daddy, Yes”

The next moment I felt him speeding up. I could hear his thighs slapping against my ass.

“Oh you are a bad girl, you want daddy to punish you, don’t you”?

“O yes daddy I have been bad, slap me, daddy”

I don’t know where that idea came from, but we were both into it. He started to slap me, not very hard just enough to make my ass red. He was still going, longer than I expected to be honest, not that I expect him to come fast but still. He grabbed my waist and pulled me up, my head leaned back, and he was kissing my neck, while with his other hand he grabbed my dick. He started to masturbate me while fucking me, I was amazed he was into it. We kept going like that until, I felt myself Cumming, at that moment my ass got tight up around his dick, and I guess that triggered a reaction since he started to cum in me.

He buckled up his pants, thanked me, kissed me on the cheek, and left. I pulled my panties up, cum still dripping down my legs, pulled my dress down, fixed myself up a bit, and went back to the table.

“Where have you gone to?” – they asked me.

“O, just having a little fun”

“Let’s get out of here”

To be continued in Part 3