Telling Mom I’m A Cross Dresser Part 19: Christmas Special

Christmas Special

It was now around Christmas time and I couldn’t have been happier. Any other year we would have had family over which meant I had to dress normal because the other members of our family still had no idea or at least weren’t talking. However this year we had no plans at all, our cousins were off on vacation to Mexico until new years, my grandparents were not in a visiting mood because of some family matters that keep us from talking to each other at the moment and others we just lost contact with.

Anyway, this year mom and I decided that since we had no visitors that we would spend the time by ourselves and doing girly things and trying out some of our new clothes that we liked in the privacy of our own home. I was so excited because we made a deal, on Christmas eve we would give each other a gift that involved lingerie and we would sleep in it that night so we could wake up and spend Christmas day as our sexy, feminem, and slutty girls that we liked to be. However this was on one condition, that neither of us had sex, masturbated or even pleased another person sexually (man or woman) for at least two weeks. This seemed a little unfair from a guys perspective I know but when you take into account how slutty mom has been in the past I feel I may actually have the edge instead of the short end of the stick so to speak.

It was Christmas eve and part of our deal was to spend the next few days dressed up starting with the morning as soon as we got up. I got out of bed, took a quick shower and shaved my whole body clean once again before sitting at my new dresser with vanity mirror to apply my makeup. I made sure to apply extra on my eyes and on my lips to make them stand out the most and apply just a little bit of blush to hide the other boyish features I may have had on my face. I just loved the way I looked and even gave myself a few flutters of my eye lashes just to see how flirty I looked. It felt nice but it also made me giggle a little.

When I was finished, I went to my closet and got out some of my lingerie. I decided that since it was Christmas time, I would get out my green chemise with spaghetti straps over the shoulders and my red with white lace thong. It wasn’t very flashy but I wanted it to be Christmas themed and I didn’t exactly have a lot of that and I’m sure that mom would give me something better tonight, she always knows how to coordinate clothes best for the occasion or pick out exactly what she or I would need. That is why it is always fun to go shopping with her.

I went downstairs to eat breakfast when I found mom already out of bed and walking around. She was in her green teddy with stockings, garter belt and sexy booty short panties that hugged her body tightly and even spread her cheeks as they only went half way down her beautiful buttocks.

“Morning mom.” I said with a smile and catching her off guard. I guess she never noticed me walking down the stairs or was lost in thought at the time.

“Oh hi sweetie, did you sleep well?” she said cheerfully then walking over to give me a hug.

“Yeah mom and merry Christmas by the way.” I said happily

“Oh yeah, this is Missy’s first Christmas isn’t it.” She said coyly and trying to act like she had no idea.

“Yep” I said to her with a big smile and my hands behind my back and twisting back and forth in a girly way.

“Well this year is going to be a special one then.” Mom says smiling and leaning over forward at her waist while tapping my nose with her finger in a playful way before continuing

“We are not going to open the majority of our gifts until Christmas morning however this year since it is special we can open one gift at 2 o’clock this afternoon.”

I sighed with a little disappointment but also relief because I hadn’t quite finished wrapping all my gifts yet and figured I should do that.

It was finally about 2 in the afternoon and our agony was almost finally over. All week I was aching to cum or have sex but since I made a deal I did everything I could to resist. Even mom was having a tough time as well as I see she was frustrated more with things then she normally would. I even noticed that she would stare and bite her lower lip whenever she saw another sexy woman her age bend over or a guy in his underwear on tv. We went to open our gifts and I got to go first. My gift was a Pink secret santa lingerie set with triangle bra top, matching garter skirt and black vinyl belt. The flirtatious bikini style bra top features white plush trim, a cute black bow and black halter straps that are adorned with silver sleigh bells. The hot little pink velvet garter skirt has plush faux fur trim and attached black garter straps with silver sleigh bells. Finally it came with some candy cane striped white stockings and matching heels and a Brazilian thong that was green and red.

I looked up to see mom smiling and I thanked her for my gift. Next she opened hers and it was a Heavenly Holiday babydoll set with a sparkling sequined bust with underwire and fur trim all wrapped up in a pretty Christmas bow. Luscious, sheer red fabric reveals a sexy, peek-a-boo center slit. A festive red sequined bust is contrasted by soft white snow trim. The Christmas babydoll is then wrapped with an attached red bow highlighted by a rhinestone charm and features adjustable straps and finally a sexy thong panty with the words “My Christmas Box” written along the front. It wasn’t until she opened her gift that I had realized that we had gotten eachother the exact same stockings. I gave her striped stockings with candy cane colors just like she gave me but the heals I gave her were 4 inch heels and bright red and I added a mistle toe hair clip as well.

We then went to our rooms and put on our new lingerie that we got from each other. A few minutes later we came back out and gave a little turn to each other to see how it looked. The skirt on mine was pretty short but it was just the way I liked it. As for mom’s, I think hers was suppose to completely cover her ass but she had a bit more bust then I thought and it gave more sex appeal and teasing then I had originally thought.

Anyway after we got changed and complimented each other, we spent the rest of the day just taking pictures of ourselves doing erotic poses or just spending time together.

The next day was Christmas, and we got up around 9am so we could open gifts. That night we both slept in our new lingerie so we could get up and be sexy as soon as we woke up. We ran to the tree and sat on our knees as we separated the gifts by hers and mine before we opened them.

My gift was a new set of breast forms that were much bigger then the ones I had and even some implants for my ass as well. I wondered why they were so big but then my mom jumped in and said she had them specially made.

“You see Missy, those were actually made from my body. In fact, they took molds of my chest and my ass to make those and now when you wear them you will have the same measurements as me.” She said while fondling and bouncing her huge tits in her hands.

She also included a book of home made coupons that involved sexual requests of all kinds of things from a one on one fuck session with her to being allowed a lesbian orgy or a fantasy party at the house. I was very surprised and was impressed at how much thought mom put into my gift. It was special and I loved it a lot.

Next was mom, I got her a gift certificate for a few lap and private dances at a male strip club that was in the city as well as some bath and massage oils. She loved those and even bit her lip as she was incredibly horny at the thought of going to see naked men dance for her. I was sure she would have left to cash them in right away if it wasn’t for the fact that everything was closed on Christmas. However there was one gift that made her tear up and it was the one I worked the hardest to get. It was a photo album with “precious memories” labeled on the front and pictures inside it of all the special times in moms life including pictures from when she was a kid and having fun with her friends and even the special times she had with me from the day I was born and even some of our “Missy” days we spent together that we had pictures of.

She began to cry and I gave her a big hug. She was so touched by gift we held eachother for quite some time and I gave her a kiss on her cheeks to help her stop crying. However the kissing went to making out and soon I was on top of mom and we were sticking our tongues in each others mouths. I started to roll my hands all around her body as I heard a slight moan escape my moms mouth. I took that as a hint that she was enjoying herself so I slipped my hand my hand down the top of her shirt until I felt her erect nipple between my fingers and pinched them. This made her ache for more and gasp as she turned her head to the side, giving me access to her neck so I could kiss and make love to it like a man but in a sensual way that only a woman is familiar with. I started to move my hand down her body and reached under her body until I could grab her ass and squeeze it tight as I licked her nipple through her babydoll.

I wanted more and I know she did as well. Her scent was filling the air and both of our panties were soaking wet with juices but I stopped us and got off of her before getting her to her feet.

“I know you want more mom but I think you should check to see what Santa left in your stocking.” I winked at her as I caressed my hands down her body and over her sopping wet pussy.

She purred then told me I should do the same before she rushed upstairs to check her stocking that was just beside her bedroom door. I ran up to and checked mine but by the time I got up there moms stocking was gone and she had disappeared in her room. I checked my stocking and found a cock pump in it. I took it out and pumped up my cock from its 6 inches to a full 9 inches and thick. It sucked on me so hard that I thought it was going to pull the cum straight from my body but thankfully it didn’t.

I made my way in my moms room just as she was rubbing the vibrator along her pussy lips. I jumped on the bed and took the vibrator from her before holding my hand over her mouth. I told her to shush with a smile on my face as I turned on the vibrator. I ran it slowly over her lips then moved down her body until I found her breasts. I moved it from side to side, going from one nipple and gliding around her areola before pressing it on her nipple. This drove her crazy so I did that a couple times to each nipple before once again going down. By now her pussy was soaking wet like a flood and her body was shaking with anticipation. I moved down to her navel and slowly touched it to her body as I gave it little kisses all the way down until I met her thighs where I danced it all over them and finally coming to rest on her clit. The sudden touch of it made her body shutter and she came, squirting through her already soaked panties and making a pool on her bed.

She laid there panting and I kissed her body, taking in her magnificent scent and cleaning up her thighs as I made my way to her soaked panties. I got between her legs and tugged on her panties as she lifted up her ass and then her legs as I pulled them off and threw them on the pillow just next to her head. I got up on all fours and stuck my ass in the air with my now 9 inch throbbing hard on swaying from side to side between my legs. I crawled into a 69 position with my mom and spread her legs by reaching around her body and holding her open by her inner thighs. I swayed my hips back and forth to make my cock dangle just inches from my mothers mouth. I could feel her hungry lips try to catch it and when she finally did she took just the head in and licked it like a popsicle. At the same time I started licking her pussy, spreading her lips with my fingers and dragging my tongue from her clit to the bottom of her pussy and sucking on her clit as hard as I could. I began flicking my tongue along her opening and making my tongue swirl around it over and over again.

I knew she wanted more so I grabbed the candy cane shaped vibrator she had and slowly pushed it into her pussy. Another moan escaped her mouth but this was louder and a lot more satisfying.

“Ohhh! Missy! Oh god baby the feels great! Mmmmm please fuck mommys pussy with your big toy. Mommy wants to feel it pulsing inside her!” she moaned while grabbing my cock and rubbing my ass.

I went along with her demand and shoved it back into her pussy but this time harder and faster with the vibe on max. As soon as it went in, mom came again making her give a loud orgasmic scream which I can only assume made her jaw drop and her eyes roll back in her head just from the intensity of her moan. I took that moment to shove the toy in again and shove my cock in her mouth and move my hips in a way that both pushed my cock down her throat but also made it look like I was giving a booty shake dance for her eyes to watch. I grinded, twisted and mixed her insides as her juices began to flow wildly. I picked up speed even more and made sure to angle it just right to hit her gspot and used only my hips to pull my cock from her mouth so I could hear her moan again.

“Oh god baby I need your cock! It looks so big and thick I need it inside me! Please baby fill mommy with your big fuck stick in both of my dirty holes!” She pleaded.

With that said I flipped her over and shoved my cock in her dripping cunt. Her screams became louder and just at the moment of her orgasm, I stuck 2 fingers in her ass and pinched her clit as hard as I could. This made her buck her hips wildly and shutter for what seemed like forever.

“Oh your dirty boy! Oh Jesus I’m cuuuuuuuming! AHH! Oh fuck, oh god yes! Fuck your Momma with that huge cock you dirty mother fucker!”

Finally she relaxed and I pulled my cock from her dripping cave. I still hadn’t came yet but I knew there was still some time for that so I decided to get out the lube for the next act as well as my cock pump. When mom saw it, she immediately grabbed it and started telling me exactly what it was all used for.

It turns out it wasn’t just a cock pump, it also sucked out nipples and made them harder and more sensitive as well as engorged a pussy or an asshole depending on how the person uses it. With that being said I wasted no time and sat up and straddled my moms stomach as I laid my cock between her wonderful tits. It wasn’t until that moment that I really understood how much bigger my cock was. It now reached between her tits and past to be in the perfect area for her to suck on the head and tit fuck me at the same time but that wasn’t I was there for.

I grabbed the pump and put it on her nipples. Mom just smiled and bit her lower lip as I pumped them up as far as I could and make them hard and almost an inch and a half long each. I gently poked one and mom gasped like I just pierced her clit and I knew this would be fun. Until it was too late, I got between her legs and rammed my cock before she even noticed. Her eyes got wide open and I fucked her furiously until I filled her with some of my “holiday cheer”.

It felt great and she must have came twice during it and now she laid there all sweaty and almost exhausted but I told her it was not over yet. I flipped her over on her knees and bent her over so her ass was stuck up in the air and her legs wide apart. Then I got some duct tape we kept under the bed (for obvious reasons) and made ropes out of them to secure her hands in front of her with her arms extended. Next I took the pump and put it to her asshole and began to pump, making it engorged and puff up like a blow fish. Then I got out the lube and coated her hole and my two fingers as I applied it to her hole. First kneading it in circles then inserting a finger and slowly moving it back and forth. She started to moan and breathe heavier with every passing second. I slipped in a second finger and she began to moan a little more and lifted her head slightly as I felt her clamp down on my fingers hard. I could keep moving them but it was like pulling her inside out.

I did this for a while until she relaxed enough that I could fit in my inflated cock. I made sure to apply lots of lube to my cock before pressing it to my moms asshole.

“Oh god baby its soo big. Oh I don’t think it will all fit inside my ass!” she moaned and wiggled her ass around my cock head.

“Don’t worry mom it will fit, ive seen you take bigger.” I teased and slammed my cock balls deep into her ass.

She screamed and shuttered as another orgasm hit her like a brick wall and coated my balls in her sweet juices. She panted but that just drove my lust to its maximum as I started to pound her, starting out slow but getting faster as I pulled my cock back then pushed it deeper but not quite all the way just yet. I kept up that pace, going deeper and deeper again until I was almost completely out of her leaving only the head just to ram ¾ of it back in. This made mom grasp the sheets tight and shake wildly as her head rocked back and forth until I finally had to get up onto my feet and mount her as I fucked her ass. Then I decided to make more use of her vibrator as I licked it from base to tip and slowly pushed it back into her pussy while it was on max once again.

Harder and harder my cock reamed out her hole as what started out as gentle moans became screams of pure ecstacy so loud I thought the neighbors would call the police. My legs started to tingle and my balls began to boil as soon I was going to cum and fill moms ass with my cum.

“Oh god mom I’m cumming!” I yelled.

“Oh god yes son, fill mommies ass with your cock juice! I want to taste it in my ass!” she begged.

That was all the encouragement I needed as it sent me over the edge and I came, shooting gob after gob of cum deep into her rectum. This trigged one last orgasm for mom to as her body shook and she erupted in one last squirt, ejecting the vibrator like a missile and falling between moms legs and onto the bed.

My cock went soft and mom was panting heavily as her body was cascaded in sweat and tears ran down her face, not from sadness or regret but from happiness and complete satisfaction of what I can only guess was her idea of the best Christmas ever. I cut the duct tape on her wrists and let her finally relax on her bed.

I turned over and laid on my side to go to sleep when I suddenly felt a hand on my ass and rolling me onto my back once again.

“You didn’t think I would leave your ‘pussy’ un-touched now did you?” mom teased.

Then she took off my thong the same way I took off hers. God it felt so erotic, no wonder she was so wet when I did it to her. Then she rolled me over and picked up her vibrator as she put me on my hands and knees. Then I felt her finger start to probe my ass, first dancing around it and plunging inside. The sudden wiggling inside me sent shivers down my body and just by instinct caused me to relax my ass enough for mom to slide in another finger. She didn’t need as much with me as I did with her but she still added some for good measure. A moan escaped my mouth as well but it was short lived as she brought the vibrator to my mouth and pushed it passed my lips and into my throat. Then I felt as she separated her two fingers and then twisted them around as she started to move the vibrator in and out of my mouth like she was fucking my mouth with a cock. I could taste her sweet nectar all through my mouth which just made me hornier then before and made my cock grow to its full length once again.

Mom pulled the vibrator from my mouth, leaving a gob of my saliva that trailed from my lips to the vibrator. I relaxed my ass and gaped for my mom as I heard her giggle and pull out one of her fingers so she had enough room to move her index finger from side to side in my hole. I felt so ready as mom slowly pushed the vibrator in my ass, it felt as if my legs instantly went numb and my body froze as she switched on the vibrator once more, causing my cock to orgasm once again.

“Like mother, like daughter.” Mom teased with a giggle.

That made me so happy to hear, but my smile turned to moans once again as mom picked up the pace and fucked my ass again. Then she reached down and stroked my cock vigorously.

“Oh god you dirty mommy slut! You are such a dirty cunt, fucking your cross dressing son with your vibrator covered in your own dirty cunt juice while you stroke his throbbing cock. Ahhh! Harder you bitch! MMMM.” I moaned in a playful taunt.

Mom took the hint and played along.

“Oh yeah bitch? Then you can eat more from your dirty ass pussy!” she teased as she fucked my ass hard and stroked my cock even faster.

This went on for a little while and I finally had my orgasm.

“Oh god mom, gonna cum, gonna cum, gonna CUUUUUUUUUUUUM! Oh fuck YES!” I squealed as mom shoved the vibrator all the way to the hilt in my ass using her palm as I shot my final load of the night all over mom’s hand.

When my orgasm finally subsided, I layed back on the bed next to mom and we licked her hand clean.

“I’m sorry you didn’t get to enjoy your gift yourself sweetie. I was hoping I could have used that pump on you because it felt just wonderful when you used it on me.” Mom said sounding a little regretful but happy she had fun.

“What makes you think I didn’t mom? I had fun just making you orgasm over and over again. Maybe next year it could be my turn for you to do the same to me.” I said with a wink and a giggle.

“Merry Christmas sweet heart, this was the best Christmas I ever had.” Mom said cheerfully and slightly tearing up.

“Merry Christmas mom.” I said smiling and holding her close before we drifted off to sleep.

Merry Fuck-mas to all, and to all a good CUM!

To be continued…..