First Taste Of Cum For A Crossdresser! free porn video

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I had never really been with another man before and I had always thought about it as I dressed up as a slutty girl and played with my little toys to orgasm. I'm a little tall at 5, 9 and with heels a monster! I have an average body, nothing feminine, but not out of shape and a nice big bubble ass.

Until that night. I had been sent to Dallas for a business trip and was super excited to dress up in my hotel room and play around! I played around a couple days in my room and just got dressed did my make up and wore my wig playing with my little dildo before passing out exhausted from all the fun! It was one of my last days and I really wanted to go out, but since I am not passable and not fully confident I didn't know what to do. I had a bright idea! I would order something for delivery and let the delivery person see me all dolled up!

Well I was very nervous and excited! I had a few drinks to settle my nerves and I got to work on getting all dressed up just perfect! I slipped on some lacy red panties, trying hard to hide my excited bulge! I slipped into my baby blue bra and slipped in my breastforms. I grabbed my sexy red dress, which already had been used this week and had a small cum stain on it from my last orgasm, but it was the sexiest thing I had.

I slipped into the red dress that didn't quite reach my knees. I then pulled up some sexy black thigh high stockings. to complete my outfit I slipped on some very tall red pumps that I wobbled in when I walked. I took them off while I did my make up though, I didn't need to fall over!

I went to the mirror and applied my black eye liner and mascara very carefully, I needed everything to be perfect! I added some light green sparkly eye shadow and some powder to my face to make me more soft looking. I added a little pink to my cheeks and finally added some bright red lipstick, smacking my lips together as I tested out kissing, and a quick fake blow job ;). Everything was just about perfect! I went and got my brunette wig and put it on. I was a knock out gorgeous, almost passable girl! I would have definitely been excited to take me home!

I took a quick look around and my ass was eating my red lacy panties, just the way i liked it to.

I decided I needed to order and couldn't figure out what I wanted! It wasn't about the food, but the delivery person! I wanted to wow them with my sexy features and maybe steal a kiss! I finally decided on a chinese restaurant that delivered straight to my room. I quickly ordered, using my most feminine voice, and then quickly started another drink as I waited for my order. I was definitely feeling a little courageous now with a couple drinks in me. i slipped on my shoes and practiced what I was going to say.

When I heard the knock on the door I almost fell over! I quickly straightened out my clothes and cleared my throat for my most feminine voice.

I didn't peer through the peep hole, just in case I lost my nerve, I opened the door and there stood a short, white boy about 20 years old, not much taller than 5, 6. Much smaller than me with my towering heels on, I was well over 6 feet tall. He stumbled through his price and I cut him off asking him "what do you think? do you like this dress?"

He said yes right away, I knew I needed to ask him more questions! He was the first person to see me so fully clothed and vulnerable! I followed up with a quick direct question. "Do you have 5 minutes to dance with me?" he said he should probably get going, but after a soft touch from me and a little pull he came into the room, food and all he laid on the counter. I wrapped his arms around me and started slowly dancing with him, the door closed behind us. He seemed very nervous, but very excited at the same time. After a few moments of dancing with him I could tell he was getting turned on, I quickly lost no moment giving him a long deep kiss with my tongue in his mouth. He moaned a little and I almost lost it! I was turning on a man with my womanly prowess!

I felt his bulge right away on my body as we were touching very closely. I reached down and grabbed it, it seemed sizable, nothing special, but I was euphoric with my new power! I kissed him again and he was very willing to accept my tongue exploring his mouth, he even pushed back with his. I knew I didn't have too much time before he needed to go. So I did the only thing that seemed sensible.

I got to my knees and undid his pants. He was very hesitant and pushed back, but barely, he quickly accepted it and as I finished pulling his pants around his ankles his cock was protruding from his thin boxers into my face, he pulled it out. As it came out it gently slapped me on the cheek and I let out a quick laugh. He laughed too and before he stopped it was in my hand and my mouth was kissing the tip. He tasted so good! I had tasted my own cum several times, but his dick tasted so savory! A completely different feeling having a real cock in my mouth than my small imitation of a dildo. my own little cock had already sprung alive and was throbbing in my red lacy panties.

I started licking his tip and he let out another moan, I was ecstatic! I loved being in this much control! I started putting my lips around his head, he was about 6 inches and cut, and I slowly started bobbing my head up and down his shaft. I would pull his dick out and lick the entire shaft every few seconds just to get it nice and wet! He grabbed the back of my head after a minute and pushed me down and forced his entire cock into his mouth. My lips were touching his balls! He did this a few more times in between thrusting straight into my mouth. I forgot I needed to look up at him, I was so focused on the cock in front of me! I looked up and he was looking straight at me, there was a hunger in his eyes! He wanted me so bad! my cock was already very erect in my little red panties and I felt them getting wetter by the second. I quickly started jerking his cock into my mouth and before too much longer he started to moan again.

When it happened, I wasn't fully prepared. He said "I'm cumming" just as I had started licking his shaft again. The first squirt landed right on my face the next several squirts landed in my mouth as I quickly put his cock back in. As he finished and sighed, I showed him my prize, just as i had seen every other slutty girl do! After a few seconds of holding it on my tongue, I swallowed emphatically and showed him my open, empty mouth, cum still streaming down my face. It tasted so good! I wanted more! I wiped it up with my finger and swallowed that too! He quickly pulled his pants back up and thanked me several times. He started to leave, I asked "I still owe you for my food!"

He only responded with a quick smile and said "I'm sorry, it took me too long to deliver it, it's on the house." With that he opened the door and left.

i was too horny to eat so I searched for any cum left on my face and sucked on it while I dildoed my tight ass in bed until I orgasmed. I orgasmed three times night before I ate my food! I was so turned on! Needless to say, my first time tasting someone's cum was amazing! I didn't wait so long before ordering food again!

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Before I start the story I want to describe the setting so you get a better idea: it’s a highway side motel, very rundown and not very cleanly, not a dump either but not the best place to have a family sleep that’s for sure. The layout of the motel is a rectangle. The rooms surround the rectangle’s perimeter, in the center there is a pool, a park area, and a parking lot. There is a walkway around the entire inside perimeter of the rectangle and every room has two doors, one facing the exit and...

4 years ago
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Natural Ingredients for a crossdresser

It was still snowing outside and I wasn't going to be recieving any visitors today so I decided to treat myself and while the day dressed how I wanted.... I had set the heating up high at my place, so I could wear one of my sexy side tie bikinis which show off my sweet little ass so well. Having enjoyed the view in a full length mirror and got some self shot snaps, I found myself sitting at my dressing table wondering how to amuse myself next.... Looking at my face in the mirror I noted a...

4 years ago
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The Chelmsford Stalker

The man sat at a corner table in the coffee shop surreptitiously eyeing off the woman sitting on a stool at bar. She was dressed in a navy blue suit; her jacket was open, revealing well-formed breasts swelling her white satin blouse, which opened to the second button so that a hint of lace bra was displayed. Her legs were crossed and her skirt had ridden up revealing most of her well-formed thighs atop long legs encased in sheer flesh-toned hose. He thought he could make out a subtle seam...

4 years ago
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Stepford Meat Swap

Story: #47 Copyright ©2010 Written: October 02 2010 A story By: KaosAngel Proofed by: KaosAngel Please send any comments about this story to ([email protected]) ********************************************************* ~~!! NOTE !!~~ This story is bassed on a fictional town within the game Second Life called Stepford, I would like to thank Ariana RoeCastle, Emilie Muggins & Jerrol Jarvinen of Stepford for thier approval of this...

3 years ago
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Cock sucking Crossdresser

When I was out on my own I started to buy a few things' mostly panties and thigh high stockings then a skirt and a blouse things that where ease to get to fit me. From there I learned to find my size in dresses and shoes this started to put my wardrobe to gather, but I still needed a wig and makeup so it was back online for more shopping, With lots of practice I became pretty good at putting on my makeup, plus doing my wig hair and a waste cincher I looked pretty darn good if I say so my...

2 years ago
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The feminine crossdresser

Chucky open’s his eyes as he awakes, looking around at his familiar surroundings in his bedroom. Band posters, comic books and video games all over the floor. His parents always gave him crap about the things he liked and tell him the typical “you’re too old to be into thoses kinda things!” He didn’t care though. He stepped out of his bed in his black t-shirt and grey track pant’s that he wear’s to bed and walks over to the window to look out as he...

4 years ago
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Made My Friend A Crossdresser

I am having a tsunami of mixed feeling about this friend of mine who’s name shall remain anonymous but for now lets call him Anshul. He’s a good guy and a hot one. He got flawlessly creamy skin with awesome bubbly butts. This started a few years ago when we met for the first time in India. We worked in same company and he was a friend of a friend. At that time I was crazy about my physique and was well built up and he got motivated and asked about my workout routine and slowly he started...

3 years ago
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indian crossdresser

hiiiiiiiiii every one here’s kiran from india ,punjab first of all its not a fictitous story ,it is  a real part of my life my actual name is rahul and me a guy now of 20 yrs old. so lets start frm my age of 12 yrs…………………………. me frm starting was very likely to kiddish me always remain at home .not to go any where else than in my street. in mid of june when our holidays were going on my parents were with at home ,i asked them about there relationship .they bit were not happy with each other...

4 years ago
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My Night with a Crossdresser

I am not a good writer but this was the hottest night of my life.I was out of town on a Business trip, staying alone at a nice hotel. After a long day of meetings, I was sitting at the Hotel bar drinking a glass of Scotch.The bar wasn’t crowded but wasn’t empty either. The seat next to me was open. Wasn’t long before what I initially thought was a woman came in and sat next to me. She said hello and ordered a glass of white wine. I realized then that she was a Cross Dresser. she looked to be...

4 years ago
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Halloween cd crossdresser

TinkerbelleMy sister , Candy, and I were fraternal twins, but looked nearlyidentical. Pretty much the same height weight and build. In high school,she was always teased about having small tits and I was always teasedbecause I was small, thin and had a big ass for a guy. Because of this wewere extremely close. Best friends really. We spent nearly all our timetogether.After college she became a consultant and I became a math teacher. Becausewe were so close, I spent lots of time at her house...

3 years ago
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Uber driver fuckes teen Crossdresser

Hi guys im a cd from Orange County and i had the sex ever last night with someone I never expected. So it was around 1 and i had just soent the night with my “friend” well I had just blew him and watched a movie and he got me an uber so i kissed him and left when tge uber came and I went on my night. He told me it was a white truck and espanic i went in and told me my “friends” name and we drove off. It wasnt even 10 seconds and he said what was my name i told him i was “. “ and he said nice to...

3 years ago
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My first time as a Crossdresser

Its 18 months ago. I had now become comfortable wearing womens clothes. I had been experimenting for around 3 months. I gradually started to get more confident in both my clothes ......and without. I started to dress more like a slut. Short skits. Suspenders. Corsets. I had also become more comfortable with my body as well. My hole was tight as could be. Like everyone, i started with fingers, one, two .....before moving on to small toys. After a few months, i had graduated to a 9 inch...

2 years ago
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My First Crossdresser

Only a few years back in my young 20's i discovered Craigslist. I had no idea something like that existed and was immediately drawn to it. After building up the courage to meet up with a few guys a couple times i found an add in the T4M section. I got instantly hard when i seen this girls pictures. A slim sexy girl with an ass to die for and a desire for Cock. After some back and forth emailing for a few days we agreed to meet in her place.I went around to her place late that night when the...

2 years ago
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Made My Friend A Crossdresser

I am having a tsunami of mixed feeling about this friend of mine who’s name shall remain anonymous but for now lets call him Anshul. He’s a good guy and a hot one. He got flawlessly creamy skin with awesome bubbly butts.This started a few years ago when we met for the first time in India. We worked in same company and he was a friend of a friend. At that time I was crazy about my physique and was well built up and he got motivated and asked about my workout routine and slowly he started joining...

2 years ago
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How I became Jayne The Crossdresser

It started in 1976,around August,I had just met John a guy my around my age,who lived alone near me. He wasn't shy to admit he was gay,and I was curious,and I told him one Friday after we got back from the pub about my interest. Before I knew it John & I had undressed & I had Johns cock in my mouth,sucking him off,& he soon quaked into an orgasm,cumming in my mouth so fast I gagged slightly before I managed to swallow most of it.John was keen to make it a pleasure for me &...

3 years ago
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Patni Patni A Crossdresser

“Oh Ramesh! I am so happy that you came today.”, I pressed my boobs against his chest and wrapped my arms around him, as soon as Ramesh entered in my flat. And he grabbed be in his arms too like a real man. He began to touch my body and moved his hands all over my back and lower waist. I was titillated by his sensual touch. “Where else I could be, my darling.”, he said and slowly slipped one of his fingers from the back of my saree blouse. He was feeling my bra strap with his finger. We two...

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