Telling Mom I'm A Crossdresser Part 17: Seven Days Of Sex, Days 1, 2 free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
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 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 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 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 say

Lemar 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. My ass felt so empty and I could feel my hole slowly puckering again as I watched Thomas’s cock slowly drip precum as he grunted to his impending orgasm.

I laid down flat and he got right on top and straddled my chest. I stuck out my tongue and licked his head until he was just about to shoot where I laid my head back and he finally came. He shot rope after rope that went from my hair to my forehead and down my face till it just oozed onto my chin. Then at the half way point I stuck out my tongue and he shot the last few globs into my mouth. He tasted salty and oh so creamy in my mouth as I swirled it around then swallowed it.

Now my face was covered in a massive facial as it dripped all over. I sucked Thomas’s cock head clean as Lemar recorded every second of this dirty act before giving it to Thomas so he could have his turn with their little cock starved cum bucket.

“You ready for the black snake you little cum whore?” he teased, shaking his cock in my face.

“God yes baby, I want your big black snake to burrow in my hole.” I said as I got up on all fours, spread my legs and opened my gaping asshole for him to plunge right in at will.

He again generously lubed his cock and my ass as he smirked at how good his little cum bucket was going to feel on his huge cock. I rested my head on the pillow with my ass as high in the air as I could get it as I felt Lemar rub his wet cock head all over my already worked hole. He pressed his cock head to my hole and he was instantly swallowed up by my hungry man pussy.

“Wow I guess T worked you pretty good. Your cd cunt is soft and warm like a real woman’s pussy but yours is still better.” He said with a little laugh and rimming my hole with his cock head.

“Thank you baby. I needed cocks like yours and Thomas’s so bad lately I may have even called you!” I said playfully.

“Then you should be thankful for our massive man fuck sticks then.” Lemar said as he gave my ass a slap then pushed his cock in only a little and pulled it back out again teasing me.

“Mmm Thank youuuuuuuu AHHHHHHH” I screamed as suddenly Lemar shoved what I think was the first 10 inches of his cock until he reached Thomas’s length.

The sudden penetration made my whole body shake at the shock and give me yet another orgasm just from putting it in! I moaned then panted as Lemar teased me and calling me a dirty little whore for cumming so quick on his cock.

I was so lost in the ecstacy that I couldn’t speak but when it started to subside Lemar could tell and he started to fuck me, starting out by pulling out his cock and shoving in the first 10 inches again. The cum on my face was so sticky and delicious and I could feel a chill between my thighs where my orgasm had peaked and was now drooling like a constant orgasm yet was still building to one. Lemar worked my ass furiously, pounding hard and forcing the last 2 inches in my ass so his massive black balls were slapping my taint.

I proved to be a tighter fuck then I thought as Lemar started to moan as well but I was way farther ahead then he was. My body was tingling and every muscle in my body was getting cramped and exhausted and I collapsed on my stomach as my cock gave a quick squirt that was like a rolling orgasm.

Lemar’s cock never left my ass as he laid on top of me and started pushing his cock back and forth in my ass. I started to think I was in over my head as his cock felt like it was going to break through my stomach and out of my body but I gritted my teeth and kept taking it like a whore and knew that it would all be worth it in the end.

About 15 or 20 minutes passed and no one said a word. I had reached about 2 more orgasms before Lemar grunted and pulled out of my ass. He flipped me over and straddled my chest like Thomas did as he stroked his cock furiously. I licked my lips and tasted the cum from earlier and knew I was going to get my second helping of his messy and musky seed. I reached up and massaged his balls until he finally came, exploding onto my face like a storm of jizz erupting from a volcano. Like Thomas he covered me from my hair to my forhead then down to my cheek, mouth and chin before shoving his cock in my mouth for the last few shots.

This load was a little more watery and was a lot saltier then the last one but it still drove me crazy all the same. Lemar got off of me and laid next to me as I heard a beep then a click. I looked over and saw Thomas turning off the video camera and setting it to the side as Lemar and him went out for an after sex smoke. I could feel my ass throbbing from the constant barrage of big cocks I had that night. I got up, picked up my thong from earlier and went to the bathroom to clean up a little. My legs were shaking like crazy so I had to take off the heels so I wouldn’t fall over. When I got there, I looked in the mirror and what a disaster I had become. My lipstick was so smeared I thought I looked like the joker from the newer batman movies and my mascara was running down my face. I guess I had teared up from getting fucked and just never noticed it and of course I was dripping with cum!

I wiped my face of some of the cum onto my hand before going down to my ass to asses the damage. I felt around, using the cum and spreading it all around my now “blossomed rosebud”. I slipped two fingers in easily, then three and finally four as I twisted them around to see how open I had become. I could feel how soft and wet I was inside and I finally understood why all the men who fucked me loved my ass so much. I pulled out my fingers and put my thong back on. Then I cleaned up my makeup and reapplied it but only mildly this time as I felt we were either going to bed or REALLY going to bed.

My baby doll was a little messy as well but I figured it was good enough for the night and went back out to the bedroom. I looked at the clock and saw that it was now 2am just as the boys came back inside and they were still naked.

“Time sure flies when your having fun right boys?” I said seductively as I crawled back onto the bed and laid down.

They just looked at one another then laughed before Thomas began to speak.

“Sorry baby, but it has been a long day. I’m afraid that is all we can do tonight.” He told me.

“Ahh and I thought we were just getting started.” I teased them but knowing that another round like tonight would kill me.

“Don’t worry slut we got all week.” Lemar said with a laugh.

They both crawled into bed on either side of me before turning out the light to sleep for the night. Our genitals and my ass throbbing from a good tight fuck with 6 more days to go.

The next day

We were completely exhausted and as such we didn’t wake up until almost noon. I slowly started to recall the events of last night as the dried cum all over me and the smell of musk surrounded me. I looked to my sides and found Lemar and Thomas laying next to me and still fast asleep. I pulled up the sheet that was covering us and a waft of musk completely engulfed me. I saw their limp dicks still oozing a little juice and thought I would wake them up the way any man would love to be waken, by a nice morning blowjob.

I slipped under the sheets and get between Thomas’s legs first and slowly pulled his foreskin back before starting to suck his cock head. He started to move and moan a little as he opened his eyes and lifted up the sheets. I looked at him and put my fingers to my lips telling him to be quiet and ill suck him good. He agreed and I sucked his cock as it grew more and more until he was at his full 10 inches. I slurped on his cock and bobbed my head as far as I could go in that position while stroking his shaft and massaging his balls. I continued to suck his cock for another 20 minutes or so until he tapped my head, telling me that he was about to cum. I gave a few more quick bobs then held the tip of his cock at the back of my throat as I stroked him. He came in a massive flood, filling my mouth as I swallowed again and again until he stopped and a little of his cum oozed from the sides of my mouth.

He just laid there and panted before getting up and going to the bathroom but I wasn’t done yet. Next was Lemar and I couldn’t wait to sample his big black dick. I wasted no time getting between his legs and put his dick in my mouth licking and sucking him slowly until he got hard to. Then I gave him the same treatment as Thomas and he enjoyed it to. Both of their manly scents were strong like a couple of hard working muscular men out in the sun all day coming back to their cross dressing princess slut to relieve their stress for the day and relax.

Lemar finally shot his massive load to and I have to say this one tasted a little better then his one last night but it still made me horny as hell.

Just then I heard the shower turn on then the curtain close. Obviously it was Thomas going to take a shower for the day. Lemar got up and told me that he was going to go next then it was my turn and we were going to go out for lunch with me dressed. I reminded him of the rules we agreed upon last night and just by looking at his face I could tell he remembered right away.

“Well in that case how about you put on something slutty and wear that sweater and jeans you had on last night. Then you can do up your eyes real nice and wear some sunglasses to hide it.” He said with a smile.

“I like that idea, ok sounds like fun.” I reply to him with millions of ideas running through my mind.

I just laid in bed and rested while under the covers while Lemar waited for his turn for the shower. I pretended to just be resting but instead I was fingering my ass and trying to feel at least a little bit of pleasure before it was my turn. I kept thinking of different ideas and what would be best to wear today and how I should do up my eyes.

Sometime later Lemar came out of the shower and Thomas had already went outside for a little walk as Lemar and I were getting ready. I went into the bathroom and removed everything I had put on last night from my thong to my makeup and wig before I hopped in the shower. I have to admit I was a little heartbroken to know I was washing away the cum but it didn’t bother me to much since my week was still just getting started.

Once I was done showering I once again sat at the bathroom mirror. First I applied my eye shadow, a nice dark blue one that was vibrant and very sexy. Then I put on a huge glob of mascara that plumped up my lashes and curled them nicely. I looked at myself in the mirror and my eyes looked absolutely stunning.

Next was my clothing as I rummaged through my underwear bag once again until I found some new lingerie that I had recently just gotten with mom. It was a black thong with lace in the shape of little hearts and the hearts were colored red. The top was similar in the fact it had little red hearts to but they only covered as much as the size of my nipples with four long strings so that you could tie two behind my back and two behind my neck in bows. I slipped those on but felt I could go the extra mile and put on something else. I grabbed a pair of black stockings and a garter and slipped those over my legs. I felt so erotic like a girl about to give her boyfriend a Valentines Day gift.

I walked out of the bathroom and found Thomas had returned and Lemar was still watching tv. I gave a quick turn and asked them what they thought. Lemar hooted at me and said that I looked like an amazing piece of ass and wish he had time to fuck me right there. Thomas agreed and came over as he gave my ass a squeeze making me blush and a little horny.

I slipped on my jeans and sweat shirt and we were off to get something to eat. Thomas had given me a pair of his sun glasses to cover up my eyes and they were even that wrap around type that covered them completely. When we got to the restaurant, the hostess showed us to our table. As we walked I couldn’t help but notice how hot she was. She had a sexy body with some curves but not overly busty. I would say she was at a happy medium that would work for her being a super model. Thomas nudged me then whispered in my ear that if I and her were in a competition of who was sexier that I would win cocks down. Of course this comment made me laugh and blush at the same time as Thomas reached over and gave my ass a quick pinch while the hostess wasn’t looking.

We got to our tables and the hostess left us to get our menus. Thomas pulled out my chair and they sat down on either side of me. We talked about our plans as we ate, each of them taking turns fondling me and teasing me. During the meal Thomas’s watch beeped and he reminded Lemar it was time for them to take their cum pills that make them erupt like volcanos. Eventually we left and went off to venture around the city. We got to one of those multi store malls and decided to split up so it wouldn’t look to obvious and strange that three completely different guys were spending so much time together and besides we each had something we wanted to do.

I went to the adult part of the mall called erotic encounters. I looked around and found myself looking at the dildos again and thinking about my previous night with Lemar and Thomas as my thong and the ache in my man pussy made my knees shake as I thought it was all going to happen again in maybe less then an hour. I already met the woman who worked there and she knew I was a cd because she had seen my Missy site but I am not sure if she was a fan or not. What I did know was that she was very professional and helped me every time I had a question. I bought some special lube that made a tingling sensation when it got warm, some condoms and a latex two piece bikini that would stretch to fit my size.

I left the store and met the boys outside by the car. They pushed me into the back seat and we made out like I was a slut in the middle of a threesome. Lemar got in the front and drove us back to the hotel room as I wrapped my legs around Thomas and rode his lap and grinded his cock all the way there. He put his hands down the back of my pants and grabbed my soft ass, pulling on my thong and teasing my ass hole almost to the point I told them to stop and fuck me right there.

We finally arrived back at the hotel room and I tore off my clothes until I was wearing the lingerie I had on before I left. I made sure to grab my blonde wig and took off my sunglasses. Then Thomas picked me up and threw me onto the bed on my back and the boys jumped on after me. Lemar and Thomas each had a bottle of baby oil and started to pour it all over my body. Squirting and spreading it all over each and every crevice on my body making me glisten and slippery. I couldn’t help but feel all over my hardening nipples and the tingling I had in my ass. Then I got down on my hands and knees on the bed. I could feel them caressing and playing with my ass before moving my thong to the side to cover my ass with lots of the slippery liquid.

Lemar wasted no time and got behind me before slowly sliding his big cock back deep into my waiting hole. I was still a little sore from yesterday but at least I hadn’t tightened back up again and it was easy to take his big black cock without too much warm up. He started to grunt as he pushed the last inch into my ass and my entire body quivered as I was once again filled by his massive member.

I let out a loud moan as Lemar’s balls touched my ass and Thomas used this as his cue to join in the fun. Thomas got in front of me and put his cock in my mouth as I began to suck him while rocking back and forth on Lemar’s cock.

Time passed and we had gotten a good rhythm going as Lemar pounded me over and over again making me moan and my body shake with excitement. Lemar and Thomas grunted like a couple of animals working their way up to their first orgasm of the year as at once they came, filling up my ass and covering my face and mouth with their hot jizz.

We rested for a few minutes and I rolled onto my back with my head hanging over the side of the bed. Thomas and Lemar switched sides as Thomas filled my ass with his cock and wasted little time in fucking me. I could feel the cum in my ass sloshing and squishing around from Thomas’s thrusting which made me feel sick yet hornier then ever.

Lemar went to the side of the bed with my head over the edge and forced my head down to relax off the side. He took his cock and shoved it in my mouth making me taste the baby oil, cum and my ass all in one delicious flavor. By now my tongue was tired from swirling around so much and licking but it kept moving like all this was conditioned after doing it for so long. Soon Thomas was pounding me harder and Lemar was forcing his cock as far down my throat as he could, making me gag and lose my mind as I became all sticky yet slippery at the same time.

They continued to trade me off and use me over and over again for what seemed like hours as they kept cumming in my ass and on my face and down my throat over and over again until we were sweating buckets and the boys were completely drained of fluids. We laid on the bed and soon fell asleep as I thought to myself that the last two days had been great, but it was still only the beginning.

To be continued.

Same as Telling Mom I'm A Crossdresser Part 17: Seven Days Of Sex, Days 1, 2 Videos

4 years ago
  • 0
  • 29
  • 0

Telling Mom Im A Crossdresser Part 11 Girl time

Part 11It had been a while since my last time as Missy. I had been doing some jobs for people, nothing special mostly working on decks and mowing lawns for neighbors to not only keep up appearances so as to not give to much suspicion of where my money was coming from. This continued for what seemed like 2 weeks before and started to wonder if my fun as Missy had ended.I walked in the door to find mom on the phone. I decided to go to get a drink before I got in the shower to cool off so I got...

Crossdressing
2 years ago
  • 0
  • 28
  • 0

Telling Mom Im A Crossdresser Part 2 The Adult Store

I awoke the next morning a little groggy as I slowly recalled the events that had taken place last night. I rubbed my body up and down feeling how the latex had now become a little sticky and how my ass and cock were still sore from the pounding I had taken. I read the note again left by my mother and decided to make breakfast as I was for when she arrived. It was just past 9am when I heard a fumbling at the door, my mother had walked in with her heels in her hands and her clothes hanging loose...

Crossdressing
2 years ago
  • 0
  • 21
  • 0

Telling Mom Im A Crossdresser Part 75 Amateur Pole Dancers

After our time at the spa, I spent a lot of time in my room trying out all the new sex toys we got from Richard and Monica. They were all exciting in their own ways and I came so much with each one. Some vibrated, some went deep and some felt good stretching my ass wide. The feeling of all the sensations I could get from my new plastic and electric friends were amazing and found myself spending long hours with them. Once I was finished, I had to stop to rest as they had left me completely...

Crossdressing
3 years ago
  • 0
  • 26
  • 0

Telling Mom Im A Crossdresser Part 85 Cops and Prostitutes

When morning came, I told mom what had happened the previous night. She had a surprised look on her face and I could tell she was feeling uneasy at the thought of me getting arrested while dressed as Missy as well. We talked for a while and she was glad as well that the police officer was a Missy fan.“We can definitely let him have a free night in exchange for not getting a criminal record.” Mom said as she gave a sigh of relief.We started to talk about the sybian that mom had bought and some...

Crossdressing
3 years ago
  • 0
  • 37
  • 0

Telling Mom Im A Crossdresser Part 14 Back to the spa and a familiar face

Part 14: Back to the spaI'm sorry this story is a fair bit longer then my usual ones however I didnt want to separate thes and have another story with almost no sex in the first one so soon. Having said that I hope you enjoy my story and please read the whole thing. I promise you will not be dissappointed. I woke up the next morning lying next to mom in her bed. I was wearing a pair of white stockings and a corset and mom had her bra on. After Thomas had left Mom and I spent the night licking...

Crossdressing
2 years ago
  • 0
  • 33
  • 0

Telling Mom Im A Crossdresser Part 7 The Spa

I could barely sit for days after Mistress Keri thoroughly tanned my hide and I had to take almost a week off so that I could heal. My mom knew this to and said we should go on a “girls” weekend to a spa for cross dressers and women, she also said that since it was for others like me then I could spend the entire trip as Missy.I loved that idea and hurried upstairs to pack Missy’s bag. I packed the essentials including a mini dress, a few different pairs of bras and panties, a very sexy and...

Crossdressing
4 years ago
  • 0
  • 24
  • 0

Telling Mom Im A Crossdresser part 10 Another Day With Mom

It was about 11am by the time I woke up and found myself still in bed with mom. I looked over to see she was still sleeping and still in her lingerie as was I. I got out of bed carefully and as soon as I did I felt how sore my ass really was. I decided to tighten up my stance a little by putting my legs together and squeezing the muscles in my ass tight as I walked. It was a lot like my sexy walk and to be honest it gave me my morning erection as I walked to my room.Once I got there, I took off...

Incest
4 years ago
  • 0
  • 16
  • 0

Cd crossdresser sissy caught by mom and dad

Backstory - I just turned 19, in college and still live in my hometown with my parents. I've been crossdressing on and off for the last probably 10-12 years. Till I was about 15 it was just whatever my sister or mom had that I could get my hands on while they were gone. Then when I was 15, I would order some online, or sneak out and go to a store right before they'd close. I've only told two girls, one who didn't believe me and the other who was supportive but didn't really care. For the last...

2 years ago
  • 0
  • 26
  • 0

Telling Mom Im a Crossdresser Part 9 A New First for Missy

It was a few days later after my night with Greg and being his police bitch for the night when I found myself sitting on the couch in a pair of nylon stockings, thong, bra and of course my new brown hair wig and breast forms. That night mom had to work late so I had the house to myself. For the first half of the night, I walked around the house and watched some of my favorite zombie movies. Eventually, I got horny (as usual) and decided to try out that Sybian that mom had gotten me so many days...

Incest
2 years ago
  • 0
  • 25
  • 0

Telling Mom Im A Crossdresser part 13 Missys Turn

Sorry not much sex in this one but its a lead up to 13.5 and I hope you enjoy both of them. Once mom and I had gotten our car back, we took it out for a spin and I have to say it worked and looked like new. It had everything from a new paint job to new parts in the engine. Now in all honesty, I did have to go back a few times and give Ray a few blowjobs to help pay for them but it was definitely worth it and I didn’t mind sucking his huge cock anyway. Mom helped as well by going over to “visit”...

Crossdressing
4 years ago
  • 0
  • 36
  • 0

Telling Mom Im A Crossdresser Part 12 Tow Truck Drivers Big Score

Sorry it has been so long since my last story. I have been busy with alot of things and I thank you for your patience.Lately, I’ve been working part time at a restaurant to make a little extra cash on the side along with my nights as Missy. I was saving up for a cruise I wanted to go on that I heard was for like minded people such as Missy. When people ask me about what I want to do with the money I am saving I just tell them I am thinking of getting a new car or something, but that’s not the...

Crossdressing
3 years ago
  • 0
  • 39
  • 0

Telling Mom Im A Crossdresser Part 15 2 Kinky Girls

It had been a week since Mom and I spent the 4 days at the spa and hung out with my old babysitter Laci and for a while it was back into our old routine of working and coming home. Day after day I kept thinking about how her warm wet pussy felt wrapped around my cock while the feel of a sexy thong rubbed against my asshole.I came home one day to find my mom was packing a bag. I asked her what she was doing and she told me that she was going out for the weekend to visit an old friend from high...

Crossdressing
2 years ago
  • 0
  • 30
  • 0

Telling Mom Im A Crossdresser Part 5 Movie Night and Gangbangs

I had decided to take a few days off from being Missy after Stan and Roger had left and my mom and I were finished with our little girl time. I spent the next few days just continuing with life as normal except for the throbbing pain in my asshole and my cock from the 3 days of constant sex. I couldn’t stop thinking about all the things I had done as Missy and all the kinky fetishes I had experienced since I came out to my mother, but I guess I have her to thank for all my new wonderful clothes...

Crossdressing
4 years ago
  • 0
  • 25
  • 0

Telling Mom Im A Crossdresser Part 8 Bus Drivers and Cops

My mom and I spent the next few days practicing and exercising with the stripper pole until we felt confident and extremely sexy while doing it, which I have to admit did not take long.One night I came home late from my part time job I had at a local restaurant and took the bus home. I didn't have a car because I hadn’t decided on what car I wanted to get yet and what I could afford. I was sitting at the back of the bus and saw how there wasn’t any other person on the bus besides me and the bus...

Crossdressing
3 years ago
  • 0
  • 25
  • 0

Telling Mom Im A Crossdresser Part 6 Missy and Mistress Keri

Up until now, I have enjoyed my time as Missy. My mom had kept me busy with clients and we pulled in a lot of extra income and I was able to experience a lot of different fantasies, However I had not had the chance to try anything involving BDSM, or not yet at least.One day I came home from mowing the lawn for an elderly woman when I walked in the door to find my mother smiling deviously at the kitchen table. I instantly knew that Missy had been hired for another job.I sat down next to my...

Crossdressing
2 years ago
  • 0
  • 34
  • 0

Telling Mom Im A Crossdresser Part 4 Repeat Business and Roleplays

When my mom and I had gotten home, I immediately ran into the house to take a shower and change as quick as I could. I re-shaved my entire body and removed my makeup so that I could start from scratch and apply it again.Once I was finished with my makeup, I see a new outfit laid out on my bed. This was a cute nurse outfit with a short tight skirt that barely covered my ass. It was also pink with white stockings and long lace gloves that went up to my shoulders. Finally the top was like satin...

Crossdressing
4 years ago
  • 0
  • 29
  • 0

Telling Mom Im A Crossdresser Part 3 Missys Weekend

One day while watching T.V, my mother had come in and told me Missy’s services had been requested for the entire weekend and we needed to go shopping. I smiled as we got into the car and went to the store to buy lots more sexy clothing for me to play in.After we had bought all the clothes and makeup needed for the weekend, my mother and I went home so that she could give me the details of what was to happen. She told me that I was to live with a couple this weekend and do everything they say....

Crossdressing
2 years ago
  • 0
  • 29
  • 0

Telling Mom Im A Crossdresser Part 25 My New Toy

It was a few days later after my night with mom at the adult shop, and my ass was still sore and I could still remember the taste of the cum in my mouth from that man. I could also still feel the pain in my ass from having to walk all the way home with my mom’s dildo in my ass.My mind wandered as I thought about how my mom reacted to getting her dildo and how horny she got just by looking at it and me during that night. After we got home, my mom told me to have a bath and go to bed because it...

Incest
4 years ago
  • 0
  • 24
  • 0

Telling Mom Im A Crossdresser Part 14 Back to the spa and a familiar face

Part 14: Back to the spa I’m sorry this story is a fair bit longer then my usual ones however I didnt want to separate thes and have another story with almost no sex in the first one so soon. Having said that I hope you enjoy my story and please read the whole thing. I promise you will not be dissappointed. I woke up the next morning lying next to mom in her bed. I was wearing a pair of white stockings and a corset and mom had her bra on. After Thomas had left Mom and I spent the night licking...

4 years ago
  • 0
  • 25
  • 0

Telling Mom Im A Crossdresser Part 85 Cops and Prostitutes

When morning came, I told mom what had happened the previous night. She had a surprised look on her face and I could tell she was feeling uneasy at the thought of me getting arrested while dressed as Missy as well. We talked for a while and she was glad as well that the police officer was a Missy fan. “We can definitely let him have a free night in exchange for not getting a criminal record.” Mom said as she gave a sigh of relief. We started to talk about the sybian that mom had bought and some...

3 years ago
  • 0
  • 18
  • 0

Telling Mom Im A Crossdresser Part 11 Girl time

Part 11 It had been a while since my last time as Missy. I had been doing some jobs for people, nothing special mostly working on decks and mowing lawns for neighbors to not only keep up appearances so as to not give to much suspicion of where my money was coming from. This continued for what seemed like 2 weeks before and started to wonder if my fun as Missy had ended. I walked in the door to find mom on the phone. I decided to go to get a drink before I got in the shower to cool off so I got...

3 years ago
  • 0
  • 25
  • 0

Telling Mom Im A Crossdresser Part 15 2 Kinky Girls

It had been a week since Mom and I spent the 4 days at the spa and hung out with my old babysitter Laci and for a while it was back into our old routine of working and coming home. Day after day I kept thinking about how her warm wet pussy felt wrapped around my cock while the feel of a sexy thong rubbed against my asshole. I came home one day to find my mom was packing a bag. I asked her what she was doing and she told me that she was going out for the weekend to visit an old friend from high...

3 years ago
  • 0
  • 14
  • 0

Telling Mom Im A Crossdresser part 13 Missys Turn

Sorry not much sex in this one but its a lead up to 13.5 and I hope you enjoy both of them. Once mom and I had gotten our car back, we took it out for a spin and I have to say it worked and looked like new. It had everything from a new paint job to new parts in the engine. Now in all honesty, I did have to go back a few times and give Ray a few blowjobs to help pay for them but it was definitely worth it and I didn’t mind sucking his huge cock anyway. Mom helped as well by going over to...

2 years ago
  • 0
  • 15
  • 0

Telling Mom Im A Crossdresser Part 16 Hot talk With Mom

My night with Laci was amazing, It was like I could tell what she wanted and when she wanted it by instinct and she could do the same for me. All that weekend it was all I could think about as I continued on with a normal weekend. Nothing to special really just washing my normal and my Missy clothes as well as taking care of chores around the house. I went off with some friends at times to because even though I do have my Missy life I also like to keep my normal life as well. Eventually my...

4 years ago
  • 0
  • 16
  • 0

Telling Mom Im A Crossdresser Part 8 Bus Drivers and Cops

My mom and I spent the next few days practicing and exercising with the stripper pole until we felt confident and extremely sexy while doing it, which I have to admit did not take long. One night I came home late from my part time job I had at a local restaurant and took the bus home. I didn’t have a car because I hadn’t decided on what car I wanted to get yet and what I could afford. I was sitting at the back of the bus and saw how there wasn’t any other person on the bus besides me and the...

4 years ago
  • 0
  • 18
  • 0

Telling Mom Im A Crossdresser Part 6 Missy and Mistress Keri

Up until now, I have enjoyed my time as Missy. My mom had kept me busy with clients and we pulled in a lot of extra income and I was able to experience a lot of different fantasies, However I had not had the chance to try anything involving BDSM, or not yet at least. One day I came home from mowing the lawn for an elderly woman when I walked in the door to find my mother smiling deviously at the kitchen table. I instantly knew that Missy had been hired for another job. I sat down next to my...

3 years ago
  • 0
  • 16
  • 0

Confession and testament of a crossdresser

Italy, september 2011. Sorry for bad english, I try to write correctly but don't know if I did. From tonight, I was a crossdresser. I'm been crossdresser from 12 to one day before my 27th birthday. Irony. I begin to have an answer to the question: "What feel girl?" Yes, a simple question. What feel girl when wear panty, tights, dress, skirt? What feel a woman in heels, purse, with her hair falling down the shoulder? What feel a teenage when begin to make up herself? When wear lipstick,...

2 years ago
  • 0
  • 35
  • 0

Telling Mom Im A Crossdresser Part 4 Repeat Business and Roleplays

When my mom and I had gotten home, I immediately ran into the house to take a shower and change as quick as I could. I re-shaved my entire body and removed my makeup so that I could start from scratch and apply it again. Once I was finished with my makeup, I see a new outfit laid out on my bed. This was a cute nurse outfit with a short tight skirt that barely covered my ass. It was also pink with white stockings and long lace gloves that went up to my shoulders. Finally the top was like satin...

2 years ago
  • 0
  • 31
  • 0

Telling Mom Im A Crossdresser part 135 Missy Brings Home A Stud

I told Thomas all the details of why I was out this night and he loved the idea. He took one of his Viagra and he led me out of the bar. I felt a little embarrassed at all the cum leaking down but some of the cross dressers were just smiling at me like they were saying “you go gurl!” which made me a little proud. Thomas followed me in his car until we got to my place and I took him by the hand until we got in the door. When I walked in I heard a thumping upstairs and asked Thomas if he would...

4 years ago
  • 0
  • 28
  • 0

Telling Mom Im A Crossdresser Part 5 Movie Night and Gangbangs

I had decided to take a few days off from being Missy after Stan and Roger had left and my mom and I were finished with our little girl time. I spent the next few days just continuing with life as normal except for the throbbing pain in my asshole and my cock from the 3 days of constant sex. I couldn’t stop thinking about all the things I had done as Missy and all the kinky fetishes I had experienced since I came out to my mother, but I guess I have her to thank for all my new wonderful clothes...

2 years ago
  • 0
  • 17
  • 0

Telling Mom Im A Crossdresser Part 7 The Spa

I could barely sit for days after Mistress Keri thoroughly tanned my hide and I had to take almost a week off so that I could heal. My mom knew this to and said we should go on a “girls” weekend to a spa for cross dressers and women, she also said that since it was for others like me then I could spend the entire trip as Missy. I loved that idea and hurried upstairs to pack Missy’s bag. I packed the essentials including a mini dress, a few different pairs of bras and panties, a very sexy and...

3 years ago
  • 0
  • 24
  • 0

Telling Mom Im A Crossdresser Part 75 Amateur Pole Dancers

After our time at the spa, I spent a lot of time in my room trying out all the new sex toys we got from Richard and Monica. They were all exciting in their own ways and I came so much with each one. Some vibrated, some went deep and some felt good stretching my ass wide. The feeling of all the sensations I could get from my new plastic and electric friends were amazing and found myself spending long hours with them. Once I was finished, I had to stop to rest as they had left me completely...

2 years ago
  • 0
  • 23
  • 0

Telling Mom Im A Crossdresser

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5'10" in height. She is also a fairly busty woman with a 30DD chest with about 35" hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first few times she had a surprised look on her face and left. However, after a few times she seemed not to care...

Crossdressing
1 year ago
  • 0
  • 15
  • 0

Telling Mom Im A Crossdresser

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5’10’ in height. She is also a fairly busty woman with a 30DD chest with about 35′ hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first few times she had a surprised look on her face and left. However, after a few times she seemed not to care...

1 year ago
  • 0
  • 42
  • 0

Crossdresser porn story 1

Ray Hirsch sat at a desk filling out form after form. It was amazing, the information that an employer required before you could start working at a new job: health insurance forms, Social Security, etc., and etc. He was now filling out a questionnaire on his background which would be used to conduct a security investigation, since his work might involve working on classified government projects. He stopped for a minute at the question: List any aliases you have used. “I wonder if I should...

1 year ago
  • 0
  • 24
  • 0

Telling Mom Im A Crossdresser Part 12 Tow Truck Drivers Big Score

Sorry it has been so long since my last story. I have been busy with alot of things and I thank you for your patience. Lately, I’ve been working part time at a restaurant to make a little extra cash on the side along with my nights as Missy. I was saving up for a cruise I wanted to go on that I heard was for like minded people such as Missy. When people ask me about what I want to do with the money I am saving I just tell them I am thinking of getting a new car or something, but that’s not the...

3 years ago
  • 0
  • 18
  • 0

mature crossdresser 18 year old PART 1

Myself being a fulltime crossdresser and wear mini skirt and dresses all the time an high heels. A few weeks ago some new people move in across the street from me to be extact it was a woman and her 18 yr son.I talked to her few times and she was very nice and in our talks asked her if it bother her that i was a cd/tv she said nope. Well after couple weeks we became good friends and found out her son was shy and kind of a nerd. One day she came over to me and was little upset over something she...

4 years ago
  • 0
  • 16
  • 0

The Crossdresser Body Swap Part 1

The Crossdresser Body Swap Chapter 1 Ashleigh finished polishing her toenails with a final dab of red nail paint. She rolled onto her belly whilst letting her feet dangle off the bed to dry. She noticed the time on her phone and let out a sigh of annoyance, her neighbours would be coming around for another dinner night soon. Ashleigh always thought they were a weird bunch, always practicing meditation in their garden, plus their house was littered with all this voodoo and spiritual...

4 years ago
  • 0
  • 26
  • 0

Room 209 First Sex as a Crossdresser

crossdresser – trans – interracial – lgbt – first time – virgin – black cock – crossdressing – natural tits – braI've been crossdressing for much of my life, as far back as I can remember. I would even go to sleep as a k** and pray that I would wake up in a girl's body. In the last few years, now that I live by myself, I spent about $1,000 on a whole wardrobe of women's clothes for myself - bras, thongs, dresses, tops, stockings, lingerie, make-up, perfume, etc... I have also been overweight...

4 years ago
  • 0
  • 13
  • 0

Portrait of a Crossdresser as a Young Man

Portrait of a crossdresser as a young man By Sara Keltaine I didn't write this for others but instead as an outlet to release the demons that have haunted me since I was a child. Some might think this story funny, others might think it sad, and the people that think they know me the best would be shocked. I'm writing under a pseudonym that has become my alter ego but I will get into why's of that later. I've been told I was a happy infant and my memories of that time...

4 years ago
  • 0
  • 17
  • 0

Amazing Night With A Sexy Crossdresser

Any ways, it had been awhile, and I wasn’t in any sort of relationship at the time, and the thought of being with a tranny again had started to be on my mind. Luckily, this was before Craigslist dropped its casual encounters section, so it was relatively easy to look for hook ups, and being there was a TS/Crossdresser section, I could easily contact one. I remember looking through postings, hoping to find one that was attractive enough, because as I’m sure you know, many cross dressers and...

4 years ago
  • 0
  • 14
  • 0

Telling Mom Im A Crossdresser Part 3 Missys Weekend

One day while watching T.V, my mother had come in and told me Missy’s services had been requested for the entire weekend and we needed to go shopping. I smiled as we got into the car and went to the store to buy lots more sexy clothing for me to play in. After we had bought all the clothes and makeup needed for the weekend, my mother and I went home so that she could give me the details of what was to happen. She told me that I was to live with a couple this weekend and do everything they say....

4 years ago
  • 0
  • 20
  • 0

Telling Mom Im A Crossdresser Part 2 The Adult Store

I awoke the next morning a little groggy as I slowly recalled the events that had taken place last night. I rubbed my body up and down feeling how the latex had now become a little sticky and how my ass and cock were still sore from the pounding I had taken. I read the note again left by my mother and decided to make breakfast as I was for when she arrived.   It was just past 9am when I heard a fumbling at the door, my mother had walked in with her heels in her hands and her clothes hanging...

4 years ago
  • 0
  • 16
  • 0

CD crossdresser sissy caught by mom and dad pt3

Please go back and read part 1 and 2 before reading this or nothing will make any sense. I ended part two after going to the pool with my mom and dad, having sex then coming home and showing together. That was a few days ago. Not much happened between now and yesterday but I've been wearing girls clothes when at home, basically a bra and thong, heels, and normally a dress. My mom ordered me a romper and some skirts and blouses to wear too. I've also been wearing the chastity belt all the time...

2 years ago
  • 0
  • 16
  • 0

Cd crossdresser sissy caught by mom and dad pt4

Sorry to all those waiting on another post - been busy and haven't gotten to it.So my mom, dad and I just returned from a wonderful trip to the Bahamas on our boat and we had some wonderful sex.I had totally forgotten about this trip until the day before we left when my dad brought our boat home from the place we keep it about 20 minutes from our house. My mom had rented a house on one of the islands in the bahamas with a small private beach and a place to put our boat. Well I started packing,...

3 years ago
  • 0
  • 18
  • 0

CD crossdresser sissy caught by mom and dad pt2

So I left off my true story last right when I woke up the morning after getting caught by my mom and her and my father having sex with me, go read that before you read this otherwise it wont make since.That was about a week ago now. Well that next morning I woke up naked in my parents bed at about 9:30 naked from the sex the night before, walked into my kitchen and saw my mom sitting at the table in lingerie with a coverup just wrapped around her but not hiding anything with my one of my dress...

2 years ago
  • 0
  • 20
  • 0

A Crossdresser Gets Caught

Johnny was gentle and had slightly feminine mannerisms for a guy. He had had quite a few escapades with women, a couple of failed marriages and a dozen or so relationships but all had fizzled out. He had never thought about the fact that maybe he was gay or bisexual and although he was not homophobic he thought the idea was not for him. He found women attractive and loved them wearing sexy lingerie and became almost obsessed with lingerie and all its variations, sometimes even more than the...

Crossdressing
3 years ago
  • 0
  • 26
  • 0

AutoRide Made Me A Crossdresser Whore 8211 Part 5

Except for some dirty and humiliating ones, most of Raghav’s dialogue will be in English in this part about the crossdresser whore. I thought that it is easier for me than translating each of the dialogues. The ride home was uneventful. I just sat dumbfounded in the back seat while Ragahv just fled the auto fast. In a short time, we reached my place. I picked my bags and climbed the stairs. Raghav followed me, carrying another small bag. Where did he get it from? I am sure he was spotting a...

Gay Male
2 years ago
  • 0
  • 23
  • 0

My first Crossdresser Part One

When she walked in to the restaurant I knew I was in trouble. It was the end of three long days at the convention and I was tired. I had come down to the NASCAR Cafe for a sandwich, mainly because it was the only bar in the Sahara that didn't have video poker...I lose a lot of money playing video poker. Well there I am with my beer and sandwich, and I glance toward the entrance just as she's strutting toward a table.Convincing she was not, a crossdresser without question. But pretty, really...

3 years ago
  • 0
  • 21
  • 0

Jaq Invites Crossdresser Over

Anyone who follows our adventures will know what type of lifestyle we lead.A short while ago Jaq got chatting to a crossdresser online. It turned out that he only lived a short drive from where we live. Kieran was twenty-two, his pictures looked amazing. Jaq asked me if she could invite Kieran to visit, an offer that I could not refuse.All was set for the Friday evening. To say we were excited would be an understatement. Jaq and I showered and dressed. Jaq looked amazing as always in a very...

Crossdressing
2 years ago
  • 0
  • 121
  • 0

Milwaukee Cuckoldrsquos Wife and the Crossdresser

Judy used several sites over the years to find her friends with benefits. She never tells me until afterwards what she has done. It’s rare she tells me anything in advance. One day she advised me the k**s were at my parents and she was entertaining that night and I would have to stay in the family room. My curiosity was getting the better of me.She went and took a shower and asked me to come in and shave her pussy. She had me paint her fingernails and toenails. Once she was ready she put on her...

2 years ago
  • 0
  • 19
  • 0

Crossdresser for mature couple

I am a bi crossdresser....love some pussy or cock. I registered on an fabswingers looking for a meeting with similar people.I was actively looking for an older couple to have some fun with. To cut a long story short, I finally got talking to a guy called Bill. He and his wife could entertain a gurl like me for a fun filled evening, if I was game. We both had a list of dos and donts for the night and we went over a few ground rules etc.I was to be their maid and waitress for the evening. They...

1 year ago
  • 0
  • 31
  • 0

A Crossdressers Night in the Park

Last night I was on line in a crossdresser chat room where I was talking with Master Brian about me being a pain loving, submissive, bisexual crossdresser who was looking a master to use and abuse me. As we talked Master Brian asked me if I was dressed as a woman while I was on line with him. I told him that I was and then he asked me what I was wearing. I told him that I was all dressed up wearing a black silk mini skirtwith a black stretchy lace blouse. Master Brian then asked me what I had...

3 years ago
  • 0
  • 28
  • 0

Teenage crossdresser

Here are the usual disclaimers this story is for adults only if you are viewing this andare not 18 years of age or older please close this page immediatly.There is no cross dressing in the story but this is how I began my transformation fromregular boy into cock suckking teenage crossdresser.We were having a really hot heat wave. i meat with my older brother (wear red shorts, and a black T-shirt) wanted me to get out of the house and off the computer so she suggested a movie. I felt wierd going...

4 years ago
  • 0
  • 43
  • 0

crossdressers 1st time

hi, im new to this. this happened about 3 years ago now.I had started off the night being at my ex gfs house looking at her sexy underwear thinking how it would feel etc. so, having just started a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from this simple thought I became massively aroused and started trying on her underwear, make up, and even a wig that was in the apartment. soon enough, I was looking like a slutty crossdresser.I thought enough...

3 years ago
  • 0
  • 25
  • 0

Crossdresser Got Caught By The Neighbor

Hello readers, my name is Rajesh, a 24-year-old guy who likes to dress like a girl. I am in Australia now.  This story will tell you how a crossdresser got caught by a neighbor and had to do whatever the neighbor ordered. His name is Roy (name changed), he is 6’1 height with a well-built body, and he is in his late 50’s. I recently had to move to another unit as my old unit’s lease got finished. On a Friday morning, I was leaving for my office. I saw an old man (who lives in the next door unit)...

Gay Male
4 years ago
  • 0
  • 21
  • 0

Crossdresser to Trans Escort Part 3

This is a continuation of my Crossdresser to Trans Escort series.After my first fuck for money with the restaurant owner, things escalated. I arrived at work the next morning wearing a pair of black trousers, black blouse and flat ballet shoes. The owner called me into the back office before we opened up for the customers. He was sitting behind his desk wearing a tight black t-shirt which showed off his tanned skin and bulging muscles. 'I really enjoyed our transaction last night' he grinned,...

3 years ago
  • 0
  • 28
  • 0

Cd crossdresser sissy caught by mom and dad pt5

Sorry I haven’t made any posts. Have been very busy with school and work. I started to write a story, would get about halfway through It then quit and not safe any of what I wrote. Last story was a few months ago when my parents and I went to the Bahamas on our boat. It was really fun. I’ve been taking hormones for a few months now and have little 36B boobs. My nipples are crazy sensitive now too! I haven’t really been wearing a chastity belt very much recently. Weirdly find It pleasing to wear...

Porn Trends