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Introduction:

Time for a vacation
Another month passed by and I got even more adjusted to my new life. I started taking hormones which has helped lengthen my hair, have kept up with my maid “service” job and even got a promotion, and have been going to the gym every day to shape my body better. This, along with wearing a corset, has helped to shape my body into a more feminine form. My breasts are still an A cup but hopefully that will change.

Life with Kendra and Violet has been wonderful as well. My girlfriend, Kendra, and I have been getting closer and closer every day. Violet and I have had the occasional fooling around but she understands that I am with Kendra and that she has my heart. Not to mention I’m pretty sure that Kendra and Violet have fooled around a bit here and there as well while I’ve been out but we all have a deep understanding of each other.

Kendra and I always enjoyed going on shopping sprees here and there. Not to mention I loved going out and watching all the men’s heads turn as I passed by in my white deep V-neck shirt over my black corset, my micro dress that barely hid my pink G-string, and my thigh high socks in my black thigh high stiletto heel boots. I could almost feel there cocks harden as I would walk past then swaying my hips.

Of course clothes shopping wasn’t the only shopping we would do. We loved to frequent the sex shop and see what new toys they had in stock. We had definitely increased our toy collection ten-fold with all the dildos, vibrators, butt plugs, and anal beads of varying sizes and lengths. Not to mention a few other things to enhance our sexual encounters.

One day while I was lounging on the couch my girlfriend walked in looking very distraught. Her face saddened me and I asked her if there was anything I could do to make things better. She looked at me and her eyes widened as an idea popped in her head. She said that we needed a vacation and just to get away from there for a while.

I agreed and jumped up, hugging her and telling her that it was a wonderful idea. I raced to the bedroom and began to pack clothes that we would need. I heard her on the phone as she walked into the room, the look on her face was rather concerning. She held the receiver of the phone and explained that the tickets there were going to be really expensive and we were a little tight on money. Then she joked about it how it would be easier if she could just pack me in a bag.

I chuckled with her and then looked at the bags we had laid out. I smiled at her as I stepped into the largest bag, bending and sucking in as I pulled it up around me. I heard my girlfriend squeal as she quickly finished up the phone call. As I twisted myself around I felt her pull out the diamond plug she gave me and replace it with something else. Looking down at me she smiled wide as she zipped up the bag completely.

I was rather uncomfortable during the trip but every so often I felt the plug my girlfriend had put inside me vibrate again and again sending waves of pleasure up and down my body as it hit all the right spots. After a few hours of being stuck in the darkness I finally saw the light as the bag zipped open, releasing me from the cramped darkness. Stretching and bending, I looked around the gorgeous room with a huge balcony overlooking the beautiful ocean.

Kendra sits on the bed, her beautiful body sending shivers down my spine as she pays the bed beside her. I make my way over, swaying from one side to the other as I get closer and closer. Once I get to her I drop to my knees and engulf her semi-hard cock into my mouth, looking up in her eyes as I slide it easily down my throat. Her moans drive me wild as I slobber all over her cock getting it nice and wet.

She pulls me up and onto the bed on all fours, looking straight ahead I see my own reflection as well as Kendra’s staring back at us. She slides her hard cock up and down my ass crack, teasing me with her wet prick. Grabbing my hips she pulls back and slams her cock balls deep inside me, making me scream and moan with pleasure. Harder and harder she pounds my hole as start to push back against it, matching her thrusts with my hips.

After pounding me for a minute she tells me to order some food and drink. Between thrusts I reach for the phone and call room service. I try my hardest not to moan into the phone as she slams into me over and over again as I order the food and wine to the room. Hanging up the phone I start to push back again, renewing her vigorous thrusts inside me.

I feel her thrust inside and hold it as her cock pumps it’s loads of cum into me, my own little caged cock leaking furiously. I feel her cock soften as it flops out of me and she rolls into the sheets of the bed. A knock at the door reminds me that we have room service coming, so I get off the bed to go get it.

I answer the door, still completely naked with cum leaking out of my ass, and usher the boy in with the cart. As he places the cart in the room and locks the wheels I walk up behind him. He turns around a jumps back a little at my closeness but as he notices my nude body I can see the bulge in his pants growing. I drop to my knees and unzip his pants, pulling his cock out and sucking it all into my mouth. His moans grow louder as I suck harder, his cock getting thicker and thicker in my mouth. He grabs me by the hair and pulls me to my feet, pushing me against the cart. He lines up behind me and swiftly shoves his hard cock deep inside my used hole.

His thrusts become faster and deeper as he gets closer and closer to finishing. I push back against him, feeling his cum heavy nuts slap against mine. I moan and crane my neck as I feel his lips sucking my pulsing vein, slamming his throbbing cock deep inside me and emptying himself into my bowels. His hot load coats my insides as I moan with pleasure, his eyes rolled in the back of his head. His cock slides out of me and he quickly dresses himself, thanking me for the “tip”.

I brought the food and wine into the bedroom and set it on the bed. Kendra and I took turns eating the food, sometimes off each other, and drinking the wine, sometimes in the glass and sometimes from elsewhere. We ate our fill and finally fell asleep in the luxurious bed, wrapping up in each other’s arms.

I smelled the salty breeze from the ocean as awoke the next morning. My eyes adjusting to the beautiful view of my girlfriend standing on the balcony overlooking the ocean. She turns to me and smiles telling me about a couple of beaches, one was a nudist beach and the other was a regular one. She asked which one we should go to and after some careful deliberation I chose the nudist. She smiled gleefully as she rushed over and kissed me full on the lips. Then she took the key and unlocked my cage telling me that I could take a break from that.

We dressed in our bikinis as we made our way to the beach. Upon arriving we found a nice location and proceeded to strip down to our bare skin. We race to the water and splash around a bit, the water feeling cool against my hot skin. Starting to tire I made my way out of the water to our blanket and parasol, motioning to one of the attending vendors for a popsicle.

The cold liquid tasted so good flowing down my throat as I watch my girlfriend in the water. Finally, she must have tired too, as she made her way toward me. As she nears an idea pops in my head and I take the popsicle from my mouth loudly, running it down my body to my crotch and ass. Turning to give her a better view I gasped as I slid the popsicle up inside me, pushing it in slowly as she watched with her mouth agape.

I can see her growing interest as she quickly moves on top of me, turning me over to my hands and knees. My ass instinctively pushes into the air as she pulls out the popsicle roughly and replaces it with her own hard cock. Harder and faster she thrusts inside me, not caring if others around us are watching. Our moans of ecstasy echo across the beach as she pounds me more and more, her cum-filled balls slapping my pathetic little ones.

She starts pulling her cock all the way out and pushing it all the way back in again and again. The melted popsicle juice squishes and smears between us. Finally, she shoves her cock in hard, holding it there as I feel her cum pumping deep inside me. More and more cum fills my belly as her cock throbs and pulses with each pumps. Finished, she pulls out quickly, rolling onto the blanket next to me as if nothing had happened.

As I lay there with cum and popsicle juice leaking from my hole I feel a deep rumble in my stomach. My eyes grew wide as I realize there is nothing I can do to stop it just as a huge fart makes it way towards my abused hole. Thick cum and fruit juice spew out as my anus reluctantly releases the brewing gas bubble sending globs in all directions. My face reddens as I try to bury it in the blanket praying no one saw or paid attention to my ordeal.

We spend the rest of the morning between swimming in the cool clear water and sunbathing on the shore. As the sun gets higher Kendra offers to rub sunscreen over my back. I lay flat on the blanket as she starts to massage it all over me. Something odd strikes me as the lotion seems to be a bit sticky and I ask her what she is rubbing on me. She laughs and continues to rub the “lotion” on my back as I realize she’s collecting the cum from my still leaking asshole.

A little while later a young black-haired woman approaches us and introduces herself as Tonya. She explains that she has thoroughly enjoyed watching us and would like to buy us a drink. Kendra and I exchanged looks and then readily accepted the invitation. Tonya smiled and then whispered something to Kendra who started giggling right before pinning me to my back with my legs flung up over me. My hole quivered as the breeze flowed over it. To ya reached into the big bag she was carrying producing several bottles of liquor.

Between Kendra and Tonya, they take turns pouring several different liquors into my slightly gaping hole, including the occasional ice cube or two. I can feel the liquid filling me up more and more until I begins running down my back. Tonya then produces a small tube and sticks one end in my ass and the other into my mouth. Kendra tells me to suck it all out and I swiftly comply. My head swoons as the mixed tastes of liquor, fruit juice, cum, and ass assault my taste buds and slide down my throat. Finally the tube runs dry as I finish the mixture and Kendra releases me, allowing my legs to flop back down onto the blanket. Tonya smiles at us and hands Kendra a card, thanking us again for the entertainment as she walks away down the beach.

After a few more minutes of relaxing we decide to get dressed and walk through the town. Passing by different the shops we suddenly come across a strange sound coming from one of alleys in between. Kendra grabs my hand and we make our way to get a closer look. Further down the alley we see two girls making out, but upon further inspection find that one of them has a rather large cock sliding in and out of the other girls pussy. The girl notices us and tells her lover of the unexpected audience. Without stopping the shemale turns her head and smiles, pounding even harder. Looking down I notice that my own girlfriend is rather turned on by the sight.

I quickly drop to my knees, taking Kendra’s cock into my mouth, her moans of pleasure like music to my ears. I suck deeper and harder as her erection grows more and more. Precum dribbles onto my tongue as I flick the tip again and again sending a visible shiver up her spine. She pulls my up, turning me around up against the wall, pulling the string of my bikini to the side and shoving her rock hard cock up inside me. Her lustful thrusts are met by my grinding hips as we moan together in complete ecstasy.

After a while she pulls her cock out of my ass and grabs me by the hand. Rushing to one of the shops she grabs up a souvenir and quickly pays for it. Pulling me again she drags me into another alley and hands me the decorative brush with a jewel encrusted handle.

She bets me that I can’t orgasm with it. I smile coyly and snatch the object from her, quickly pushing it inside me. I can feel it hitting all the right places and soon enough I start to cry out as my little cock explodes onto the alley street. I pull the brush out, the handle covered in cum and ass juice, and Kendra quickly places it in her purse, giggling as she does.

We pass by more shops until Kendra tells me she wants something sweet. I make some rather lewd comments back to her and we laugh. She points out a small doughnut shop and pulls me over to it. I wait next to the building as Kendra stands in line and eventually gets a pink box that she brings over to where I’m standing. She turns around and opens the box and after about a minute she turns back towards me. There, stacked on her hard cock, we’re about three or four doughnuts. I dropped to my knees again biting and licking each of the doughnuts off of her hard prick, chocolate and icing smearing all over my face and she proceeds to eat the rest out of the box.

After our snack we make our way back to the hotel and up to our room to clean up. Later we decided it would be nice to have a dip in the pool. Swimming around and around I decided to get playful and started pulling on her leg as she was swimming. She dunked my head under water and as I came up I asked if she was trying to drown me. She told me that I have a pipe down there if need be and swiftly pushes me underwater again. This time I take the hint and grab hold of her enlarging cock, taking it into my mouth as much as I can. Sucking harder and harder as I get it down my throat, her balls pressed against my chin.

She pulls me up long enough for me to gasp for air. Spinning me around I feel her slide her throbbing cock into my ass. She tells me that she doesn’t want to cum in the water and drags me down with her as she pounds my ass harder. In no time I feel her cock twitch as it spews thick cum into my bowels again and again, filling me up once again with her cum. I clench my cheeks as she pulls out and swims over to the towels.

Grabbing something out of her bag she races back to me. I try to get away but she grabs my bikini string and pulls me to her. I feel her push something into my ass as she whispers not to make a mess. She giggles as she releases me and I feel the pool water rushing up inside me freely and then flowing out carrying the fresh load of cum with it leaving a trail flowing behind me. I made my way to the edge of the pool and quickly got out, the air whizzing by my open anal cavity sending a shiver up my spine. Kendra smiled at me and gave me a kiss telling me that I could keep the tunnel plug as it might come in handy next time we need drinks.

As we got back to the room and cleaned up again before heading into town once more. We passed by a parlor with several areas in it. Kendra dragged me in saying how we badly needed pampering as we made our way through the salon shops.

We stopped in the first shop which was the salon. We got manicures, pedicures, and nail extensions to start. Then I got my eyebrows trimmed, full body skin care done, some hair extensions along with dying it and all my other hair a reddish-pink, and to top it off I got my pubic hair trimmed into a nice little landing strip that I figured Kendra would love.

As we finished there we went to the next shop which was a piercing studio. Kendra told me how sexy it would be for me to get some piercings so I went along with it. She walked in dragging me by the hand and had me lay down in the chair. She whispered her request to the piercer and told me to close my eyes because she wanted it to be a surprise. My eyes flew open and a gasp ushered from my mouth as I felt the piercer grab my cock and pierce right through my taint. Kendra jumped up and down clapping her hands as I tried my hardest not to squirm, breathing as I laid back down. I closed my eyes again and felt the hands on my nipples, squeezing and pinching right before the needle went through each one.

Still in a euphoric state I felt Kendra pulling me along to the next store although I wasn’t sure where we were going at first. As I looked around I took notice of all the artful designs on the walls and the tattooed lady at the counter. Kendra dragged me into the back and had me lay face down on the table as I heard a buzzing turn on behind me. As the needle struck my lower back all I heard was her sweet voice echoing in my ear about how sexy I looked and how much she loved me for doing this for her.

After about an hour the tattoo artist announced that he was done and as I gingerly lifted myself up off the table I made my way to the mirror in the corner. My girlfriend helped me to get the best angle so that I could see what she had gotten the man to tattoo on me. Right there at the base of my spine was a nice tramp stamp with the words “KENDRA’S 4 LIFE” written across the upper part of my ass. She kissed me deeply, which helped a little with dulling the pain. Emboldened by this I strut my new additions with slutty pride as we continued to walk through town.

We walked into another store looking for drinks and snacks. Going through the aisles we got separated until I heard her whispering my name from the end of the aisle. As I made my way to her I could see the devious look in her eyes. She said that it would be hot as hell to take some pictures here…some lewd pictures. I asked her what she meant and before I could say anything she lifted my skirt, pulled my g-string to the side and proceeded to shove a decent sized bottle of wine up my ass. I heard clicking as she took pictures of the ordeal, pushing more and more inside me until it was all in. Then she handed me a few more items to stuff in my bra as she slid things into her own pants and bra as well. Cautiously we made our way out of the store, giggling as we made it back to the room and marveled over our stolen treasure.

Kendra began to undress to get a shower and I took it as my opportunity to get back at her for all the things I have had to endure so far. Not that I didn’t like all of it or wouldn’t do it again but how many chances like this was I going to get. As she pulled her shirt up over her head I took my opening, tossing her to the bed and pinning her legs under me but over her head. My cock dangled there in front of her as I laughed maniacally. The head of my cock pushed into her mouth as I roughly shoved two, then three, and finally four fingers into her ass making her suck the head of my cock even harder. Harder and harder I finger fucked her while I rocked my cock in and out of her mouth.

After getting her loosened up a bit I rolled back, pulling her on top of me. She protested a little and began to threaten me when I cut her off by impaling my cock hard inside her. Her moans pierced the night as I rocked my hips up harder and faster meeting her hips with every thrust. Her hole tightened around my cock as her own bounced against my stomach leaving a trail of precum. We moaned together as I thrust one finally time before shooting my load up inside her hungry hole just as she spilled her own all over my stomach. She leaned forward and kissed me passionately but as she pulled back I saw the devilish look in her eye.

She rolled over, pulling me on top of her. She situated herself and reminded me that she had warned me. With my tunnel plug still in place she had no problem with sliding her hard cock up inside my hole. I moaned as I felt her filling me up. Then she started to suck on my tender pierced nipples causing my brain to swirl in a mixture of pain and pleasure as she nibbled and pulled on each one. Harder and harder she thrust and with each thrust came another wave of pleasure as she flicked my piercings with her tongue and sucked on them again and again. Soon she was flooding me with her seed as her cock exploded inside me sending the warm sensation throughout my body. Exhausted we wrapped up in each other’s arms as we regained our strength.

We started packing our bags to return home in the morning when Kendra came across the card Tonya had given her earlier. Her eyes and smile grew wide as she suggested one last wild night before we went home. We dressed up in our sluttiest outfits, did our make-up, and called down for a taxi to pick us up and take us to the red light district.

We enter the whorehouse and are immediately greeted by a beautiful woman in a tight flashy outfit. She explains that there are different rooms in the establishment and that we have free reign to go to any of the doors we would like as many times as we would like. We agreed to try things out for a couple of hours on our own and then meet up and decide further.

I walked into the first room after making my ***********ion of whores. The room was empty except for a chair and a bed. I made my way to the chair, removing my clothes as I sat down. No sooner had I gotten seated the door opened and a young girl shyly walked in. I motioned her to come closer and as she got near I grabbed her shoulders and put her down on her knees. She cautiously opened her mouth and I pushed my cock into it, causing her to gag and spit. I grabbed the back of her head and slammed my cock in again, reveling in the thrill of being in control. She gagged again, this time causing her to vomit all over my cock and herself. I angrily pulled her up by her hair and threw her onto the bed, her ass sticking straight out towards me. Without giving her a chance I pounced in behind her slamming my cock into her wet pussy. Just then I heard the door open again and another beautiful woman walked in but she had a little extra. As she walked up behind me I gripped her hardening cock, stroking it faster and harder. I laid the shemale on her back the bed next to the girl and straddled her, lowering myself on her hard cock. Harder and harder I ground my hips until I felt my cock about to explode. I gripped the girls hair again and pulled her to my cock, shooting my load in her mouth and all over her face just as the shemale erupted inside of me. I let go of the girl and stood up, cum dripping from my hole as I walked out and into the next room.

The room was dark when I entered and the little light the open door allowed in was cut off as it slammed shut. Hands grabbed me and I was pushed forward, my face pushed into a wet mass. I knew the smell instantly and began furiously licking the pussy in front of me, greeted by the heavy moans of the woman. Next I felt something behind me probing my back door when suddenly a huge cock ripped into me, my moans and shouts muffled by the wet snatch my face was buried in. Harder and harder the cock thrust into me, using me like the rag fuck doll I had been so used to being in the past. I felt the huge cock throb and pulse as it spewed its hot load inside me, my belly bulging slightly at the sheer amount of cum being deposited. Once he was done the man flopped his penis out of me and I was released from the wet pussy mask I was forced into. I stood up and thanked them both before turning and leaving the room.

In the hallway I saw Kendra and raced to her quickly elaborating the past events as she told me about her experiences as well. As we walked through the next door together we saw another chair and a huge bed. On the bed was a single maids outfit. We agreed that she should wear the outfit and I would watch from the chair.

As soon as she finished putting it on a big black man came in with the biggest cock I had ever seen. He laid in the bed, pulling her on top of him while I just sat and watched, my cock getting harder and harder. I watched her face contort and her eyes grow wide as he slowly impaled her with his massive cock. Slowly inch by inch disappeared inside her and the look in her eyes turned to total bliss as her hole opened to accommodate the huge intruder. Moans and screams filled the air as she began to bounce up and down on his gigantic member, his thrusts lifting up to meet hers, her own cock slapping against him as it dribbled precum all over his stomach. Harder and faster they moved until finally he thrust hard, grunting as he filled her with his seed. The bulge in her stomach caused by the huge cock imbedded in her twitched as it shot it’s load, her own cock shooting all over his chest as she slumped forward from exhaustion. As he lifted her up off of his cock I walked over and crawled onto the bed, taking his semi hard cock into my mouth sucking the cum and ass juice off of it completely.

As Kendra recovered we made our way to the last room, finding only a bed, a nightstand, and a list on the nightstand. We looked over the list of available whores and made our choices together. The three of them walked in together, a young woman, a young man, and a young shemale. They climbed into bed with us and we took our turns with each of them, sometimes sucking cock, sometimes licking pussy, and other times biting nipples. There was even a time that while Kendra was sucking the young mans cock I was licking his ass while the girl sucked my cock and the shemale sucked Kendra’s. The rest of the night was like that, sucking and fucking and cum sprayed everywhere until we were all to exhausted to even move. How we made it back to the hotel room I will never know.

We woke up the next morning groggy and sore but a smile on both of our faces. At least until we looked at the time. We rushed to pack the rest of our bags and ran down the stairs to the waiting cab. Barely making it to the airport and onto the plane in time. As we took off I looked over and noticed that Kendra was passed out in the seat as a beautiful femboy stewardess handed me a drink. She winked at me and whispered that she would be in the stall if I got the urge. Seeing the opportunity for one good fuck before we got home I quietly got out of my seat. I headed for the stall and opened the door to see the femboy naked and waiting for me. She took my cock into her mouth and sucked it all in making me hard as hell. I pulled her up and turned her around, slamming my hard prick into her waiting rectum. She squealed as I grabbed her cock and began stroking it as I thrust into her again and again. After a bit I felt her cock twitch as it spewed cum onto the sink just as I thrust into her filling her with my own hot spunk. I pulled out of her ass and dropped her to her knees to clean my cock while I licked her cum off the counter. Finishing up I returned to my seat and to my sleeping companion, letting the darkness take me as well into a deep sleep home.
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