Telling Mom I’m A Crossdresser Part 17: Seven Days Of Sex, Days 1, 2

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May 15, 2023 // By:analsex // No Comment

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This is a fairly long story but I broke it into two parts so that you can read the first half in one sitting and find your place easier if you want to come back and read some more. Also, I would like to say that this will be the start of a seven day sexcapade for Missy involving two of her past flings. Please enjoy and rate and comment at the bottom. Happy reading!! ;)It was now Monday and mom had to work. I was left home alone and I had already began a 10 day holiday with about 8 days remaining. As such I thought I would check in on my other job on the Missy website to see if there was anyone who wanted to play during my holidays. I had previously gone to the glory hole with mom the pervious night but it wasn’t that exciting really. Just average sized guys looking to get off from a hot girls blowjobs but on a Sunday night it was slim picking. We did get to suck a couple cocks each but it no where near satisfied my lust however mom looked like she wasn’t really into going the extra mile tonight either so we just left it at that and went home.I logged in and found I had a request for the entire holiday to meet up with a guy in a hotel by the name of “Ten inch T”. He stated the time and the place and that all Missy had to do was bring the minimum requirements such as breast forms, nail polish her wig and makeup as well as heels and underwear along with an overnight bag.I was continued to read and saw that it wasn’t even necessary for me to arrive dressed and I was allowed to show up in my normal clothes as it was. This got me confused as to why someone would want me so plain but it could be that they just were going to bring things for me to wear. I packed up my Missy underwear such as thongs, bras and a few pairs of pantyhose to go along with the other items he had requested. I had recently gotten a Motorcycle as it was a lot easier on gas and easier to hide it while going to a hotel and I didn’t want to be seen. I packed an extra bag of my normal clothes as it was going to be a week and thought I better bring some of my every day items just in case.I arrived at the hotel room at 7:30 as requested. The hotel was one of those hotels that had doors to each room outside as well as inside so like the request said I made my way down the sidewalk, counting the doors until I found the room. As I was walking, I thought in my head that I really hoped I had the right room number as it may be embarrassing but on the door was a sign that read “Julie is welcome in without knocking” which was obviously meant for me.I opened the door and got the shock of my life, there was Thomas sitting in a chair at the far end of the room in a bathrobe and obviously naked.“Oh Thomas! I did not expect to see you here. You are Ten inch T?” I asked as the last time I remember him he was 9 inches if remember right not ten.“Well yes my dear but you see I have gained and inch from those pills I told you about before if you remember. Seems they had an extra side affect in about 42% in men who use it and I was one of those 42.” He said with a grin.He opened his robe and my jaw dropped, his 9 inch cock had gotten to now 10 inches long and I had to measure just to be sure. I started to drool and my knees quaked as I thought about the fact he booked me for a week and I had the privilege to play with this monster all that time.“That’s not all babe, I have another surprise I think you are going to like.” He smiled and laughed to himself just as the door clicked open once again.Now I was about to go crazy. Lemar, my first big black cock was in on this two and I was going to be group fucked by two monster dicks like those slutty porn stars in interracial videos.“Long time no see bitch.” He said playfully while rubbing his cock in his sweat pants.Lemar was different from the last time I seen him. His corn rolls were now a simple buzz cut and his gouty was now that simple short beard around his mouth and on his chin that looked professional yet sexy.“Guess what? I have been talking to Tom here and he told me about those pills to. So now I cum as much as he does and I grew 2 inches so I hope that ass of yours is ready for a 12 inch black snake.” He teased.My legs began to shake then gave out as I dropped to my knees and felt my face turn red and my heart Çukurambar escort speed up with anticipation. My mouth became dry and I licked my lips for some moisture. Lemar closed the door and started to strip, he wasn’t kidding his cock almost hung down to his knees and I could feel my ass squeeze tight at the site of it.I turned my head and Thomas was standing just inches away from me as well before he dropped his robe to reveal his 10 inch cock as it swayed back and forth just inches from my hungry mouth. I wanted to lick it but they stopped me.“Not happening kid, these are for Missy. Have you seen her?” Thomas asked with a smile as he looked at Lemar then back at me.I got up off my knees and put my normal clothes bag in a corner before taking my Missy bag to the bathroom as I said “Let me go get her.” With a wink and a wiggle of my ass.I could hear Lemar and Tom talking in the next room as I opened my bag and stripped out of my clothes. I began with my makeup as I sat down on a little chair that was in the bathroom. I started with my Mascara, lipstick, eye shadow and lip liner. I thought I would try to look a little sexier then usual since they booked me for so long and had worked hard to give me a good experience. The least I could do was make their fantasy come true as well and be the little whore they wanted me to be.Once I finished with the makeup, I put on my blonde wig and I even got a Velcro head cover to put on my head underneath the wig so it could stay in place easier. Next was the underwear. Since it was all I had to bring, I brought almost my entire stash of women’s underwear and sexy night wear. I went into my bag and pulled out my blue baby doll that was see through on my tits and was so smooth you would think the cum is going to drip right off without even being absorbed by the fabric. I decided not to wear the breast forms as I did have a little bit of boob that filled the space enough and maybe I had to bring those for a different reason anyway. Lastly were my heels and my underwear. For my panties I chose a blue thong that matched my baby doll in both color and fabric with a little bow on the back just above my ass. My heels were a little trickier though but I ended up putting on my silver and glittering strappy heels with a 6 inch high ball and heel. I reached into my bag and pulled out the digital camera. It was cleaned of the previous videos I had shot and I got extra memory sticks for the week ahead and took it out with me.I left the bathroom just as Thomas and Lemar were bringing in a couple suit cases filled with clothes. I looked over and saw their bags by the corner so naturally I asked them what they had as I placed the camera on top of some drawers and hit record. At first they just looked at me and smiled as I knew their first thought was how fucking hot I looked and how much fun it was going to be to make me squeal in pleasure. Then Thomas spoke up and told me that they were new and sexy clothes that I was going to wear for them for the next 7 days, and that is why I only needed to bring underwear and the likes.I smiled with glee as I hopped on the bed and watched as they finished before closing and locking the door once again. Lemar opened one of the suitcases and threw me a dildo and some lube.“So Missy what do you think about all this?” Lemar asked with delight and lust on his face.“Well I think we need to lay some ground rules.” I teased.Looking puzzled they asked what kind of rules. They asked as I rolled over and onto my stomach.“First if you 2 have as much cum stored up as you say you do then tonight the first shots go on my face, my mouth and on my body. Second it has been a while since I have taken a cock that big so if its ok I would like Thomas to go first since his cock is a little smaller but he can still rip me in two!” I giggled to myself as I licked the head of the dildo and started to rub my ass hole from through my thong, teasing their cocks as I watched them grow.“Third, everyday we are going to get a little kinkier leading up to a massive fuck fest. Fourth I will wear something sexy everyday but if we go out in the day light I will wear my normal clothes over top however at night I will wear whatever you want me demetevler escort bayan to and we can go out on the town if you so choose.” I watched as their cocks started to twitch and drip as my words were like an aphrodisiac to their ears.“Rule number five, the first day or so you have to take it easy and fuck me one at a time and slowly until I can every inch of both of you no problem but from then on you are to pound me as hard as you can until I can no longer walk. Finally since there is two of you, I want you to take turns fucking me day and night from the time you wake up in the morning until you pass out from cock exhaustion at night or even until dawn if that’s what you want.”Thinking back on what I had just said I started to think that maybe some of my rules were a little overboard and I was biting off more then I could chew, but they looked at me and Lemar spoke:“Slut, that is exactly what we had planned to do with you from the very beginning. By the time we are done with you, the only comfortable position you are going to be able to be in is doggy style on your knees or one of us holding you in the air with our massive peckers!” Lemar exclaimed and taking command.Thomas walked up to me beside the bed and I put the dildo to the side for the time being but kept the lube on the bed with me. Lemar sat down in the chair Thomas was sitting in earlier and slowly rubbing his cock as he watched Thomas get the first fuck. I watched as Thomas’s cock swayed back and forth like a pendulum counting down the time before it probed between my lips and soon my tight little rosebud.I slowly picked up his cock and pulled back the foreskin. The smell of a man after a long day was strong as his musk wafted into my nose and pushed me past the point of no return. I took his cock in my mouth and slowly bobbed my head back and forth, tasting his salty cock as his precum gushed out from the tip. I began to moan as I could no longer hold my lust and got up onto all fours with my legs spread wide and gobbling down Thomas cock until I had his previous 9 inches in my throat. Then I pulled back, freeing his cock from my warm wet throat as he stroked it for me and slapped my face a few times.I could feel as his precum left sticky trails as Thomas drew lines all over my face, causing my lipstick to smear a little. I felt so hot and swallowed Thomas’s cock again and swirling my tongue around his head. Suddenly I felt Lemar on my ass. He was pulling my thong down and caressing my ass tenderly. Then there was a sudden slight cold sensation drooling on my ass hole as it slowly warmed up and Lemar used his fingers to probe inside my ass and thoroughly massage my hole. It took my focus off Thomas’s cock as I moaned and looked back at him for a short time as Thomas grabbed my head and stuff his cock back in my throat.“Don’t forget who your sucking Missy, I want my cock all the way down your throat. Besides, He will have his turn yet.” He smiled deviously.I felt Lemar stick his 3 rd finger in as Thomas pushed the last inch of his cock down my throat, making me gag and drool all over. My lipstick began to smear and my mascara was starting to run.This continued for another 10 minutes as Thomas was now moaning like crazy. I was on fire and completely lost in my blank mind as the taste of Thomas’s delicious cock brought back the memory of his massive load. This made me want him even more, and I could no longer stop myself as I fell over backward and onto my back where I lifted my legs and spread my ass cheeks.“Oh god Thomas, I need your big hard cock in me now! Please fuck me like your slut I beg you!” I moaned as I felt the lube in my ass slightly gush and ooze around inside me making my love tunnel a wet and wild ride for his massive member.“Ha ha ha” he laughed. “Always the impatient one for cock aren’t you Missy?”Thomas came up and rested my legs against his firm body before pulling my thong off and throwing them to the side. I could feel Thomas rubbing his cock head against my hole to feel how wet I was and I was glistening from the lube and my own anal juice.“Beg me slut! Beg for my cock in your little boy cunt!” he commanded.“Oh god Please baby! Fuck my boy cunt, Loosen me up like a whore Escort dikmen and cover me in your hot sticky man juice!” I begged.Just then Lemar flopped his big black cock on my face and I started to stroke it while I licked his shaft and teased his cock head. I could feel his precum starting to drip and he moved me back on the bed so my head was hanging over the edge of the bed. I knew what was coming next as I opened my mouth as wide as I can and relaxed my throat. I waited for Lemar to put his cock in my throat but Thomas surprised me and shoved his cock in. I let out a loud yelp as Thomas’s cock slowly made it’s way deeper into my ass.With my mouth wide open like a target for Lemar, he put his cock in my mouth and muffled my whorish moans. I could feel as Thomas inched his way in me little by little. God I missed the feeling of being filled up like a car at a gas station. I started to shake my hips and grind as Thomas reached about his 8 th inch inside my ass before he had to stop because I wasn’t used to anything bigger. Thomas stopped and slowly moved his cock only a little bit in and out of me like he was trying to loosen me up. I could feel my ass tighten around his cock which made him twitch and moan. Lemar watched this with pride as he began to fuck my mouth also moving only slightly as to not hurt me but still fuck my throat. He had a nice taste to as my tongue traced his veins right to his cock head where all his bitter goo was leaking like a sieve and coating my mouth.“Open your mouth as I pull out my cock.” Lemar demanded.I did as I was told and felt as Lemar slowly removed his cock from my mouth which left a sticky clear rope of saliva connecting his cock head to the inside of my mouth. I slowly moaned as the taste of his warm manhood left a taste in my mouth that only made me crave more.Suddenly I felt something touch my ass and I looked down to where Thomas had now inserted the whole 10 inches of his cock into my sodomized cd cunt. He held it there and I bucked and grinded my hips all over until I got used to his girth and his length so far inside me. I don’t know where Lemar went but at that moment I was too entranced by the fucking that the hotel could have been demolished and I wouldn’t have known.“Get ready Missy, I’m going to start moving now.” Thomas said as his hips began pulling his cock out a little then going back in.I felt him slowly come out then back in only in small strokes as my ass was being reamed out. Every thrust took my breath away as everything went numb. I started heaving and yelling dirty things that would drive almost any man with lust like “Fuck my ass big boy, fill me with that huge meat rod in my boy cunt!” and “Fuck me! Fuck me! Make me a dirty little slut whore for big juicy cocks like yours and fill my rosebud with your cream filling!” I cried out.Suddenly Lemar caught my eye and he had my camera recording Thomas fucking me and getting every hot and slutty angle of me he could get. Thomas pressed my knees up to my chest and I reached down and spread my cheeks wider allowing Thomas to get deeper into my ass. Between my dirty talk and being filmed like a porn star made him fuck me harder and was now feeding me almost half of his cock with each thrust and making my body quiver with each one. The camera made me want to get more into it so I kept on talking dirty but this time looking into the camera.“Oh fuck I love it, I love my tight ass being fucked by a big fat fucking dick. I love cocks I want them everywhere and anywhere I can take them.” I sayLemar holding the camera right in my face but then moved down till he was giving a “person over viewing” type of shot before starting a little interview.“You like that dick up your ass?” he asked.“Yeah” I said sheepishly.“Which do you like better, when they cum deep into your ass or when they shoot it all over your face.” Lemar asked trying to make it dirtier.“I love it both, I wish I could get fucked and have cum splatter in both ends at the same time.” I said as best as I could but it was hard now because Thomas was really getting off on the dirty talk as he was now slamming his cock about 8 inches worth in and out of my ass furiously and making wet slapping noises with each thrust. Thomas was now reaming out my ass and I could feel as his cock head bumped my insides hard with every thrust and burned inside as his cock felt like it was on fire.After about another 10 minutes of Thomas pounding me and around my second orgasm he finally yelled out “I’m Cumming!” and pulled his cock from my ass as he stroked just inches from my face.

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