Young Secret Cross-dresser’s 1st Experience free porn video

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Hello everyone. I am  Anuradha / Sameera, a Secret Crossdresser of 29 years old from Telangana. My breast might be around 34-36 as 36 size too fits well. I love sports bras and padded bras.

started in my junior college days when my friend became my boyfriend. It started with him sitting beside me. We used to stroke each other’s cocks secretly under the bench. The handjobs slowly turned into blowjobs.

I also had my boobs squeezed by a few others in the class. But I was too scared to tell my orientation. I didn’t want to be seen with suspicious eyes. Also, this was going on as a fantasy only.

So our sucking and stroking continued as the class kept on. Whenever he was in the mood, he used to jump and sit beside me. Whenever he did that, I knew what to expect. Even I keep waiting for him to come.

After he came, we would try to cover the top with books, bags etc. Then slowly play around with each other’s thighs in our hands. Then open the zip and sneak our hands in.

During the blowjob, we would act as if something had fallen. As we went below to table to pick it up and, in the meantime, would have a blowjob done. It was awesome not only because of obvious reasons but also because it felt like an adventure. We had to make sure we did not get caught.

He was talking about his crush as I gave him a handjob. I thought this was an opportunity. I made the bold move and told him that I liked his cock. He could fuck my asshole if he had no problem with it.

I wanted to take it to the next level by playing the role of the submissive partner. (Though I am versatile ). But on the promise that it will not be leaked in college. He was shocked at first but became ready for it.

He told me he would buy all the cross-dressing stuff for me. He likes to fuck me like a cross-dresser Transgender. I didn’t understand. So he showed me Trans videos, and I liked them. It took some time for me to prepare mentally for it as I had never had any form of sex.

So one fine day, after planning it, he called me to his room. He gave me the bra, barbie doll outfit, panty and wig. He told me he would wait outside till I got ready. It took me quite some time to understand how to wear the wig, but somehow I got it through.

Once I was ready, I didn’t know why. I felt awesome and called him in. He was astonished and started to praise me. I really felt so feminine in the clothes. I couldn’t take my eyes off the mirror when I was getting ready. I was getting arousal looking at myself.

He slowly pulled me towards him and looked into his eyes. For once, he couldn’t believe it was me. We started kissing each other hard. He also grabbed my ass with his hands and squeezed them as I held his head.

Later he kissed my neck and cleavage as he lifted my outfit and removed it. I, too, removed his shirt and pant. We were half nude now as I started to explore his body.

He made me go down and feel his cock as I kissed his chest. It seemed bigger than usual, probably more aroused. I bit his cock from his underwear to tease him slightly before removing it.

I was giving it a few hand strokes before kissing the tip. I pulled the foreskin and locked it like a lollipop. He was like, “Come on, suck it now.” He caught my head and pushed his cock deep into my mouth till I gagged.

I also played around with his balls and had a bite of them. After some time, he had a bit of pre cum. He threw me on the bed and came on top of me. He bit my cleavage and licked my navel.

He later slid my bra down to expose my sissy tits and started sucking them. He was alternatively sucking and squeezing each boob. I felt I was in heaven. I caught his hair and caressed it as he kept sucking and squeezing my tits.

He slowly went down, kissing my navel down and removing my panty, sucked my cock deep. I went on top of him, holding his head as he sucked my cock. Now, it was almost time.

He made me turn around and licked my asshole and fingered it. I felt I had done a good thing by expressing my desire to him. His tongue was magical. I was itching to take his cock in my hole. I told him the same, and he started to insert it in.

It was painful, so I told him to go slow. But he pushed it into my ass hole in the doggy style in one go. It was pain and pleasure at the same time. Later, we changed to missionary with him on top, and he continued banging my ass.

It was a slightly uncomfortable position for me, to say the least. My feet were facing up awkwardly. It added to the pain but no complaints. He drilled my asshole by looking into each other’s eyes.

He got hold of my boobs again and squeezed them hard. The pain in my ass and boobs was unbearable, and I let out a scream. He loved that.

After some time, he reached an orgasm and slept beside me. I started to stroke myself with one hand on his chest. I lay beside him with memories of my first sex.

I wanted to get ready as usual and go, but my ass was hurting. He told me to get into a sissy dress again and have one final long kiss.

Secret Crossy sissies and CD Admirers, mail me your suggestions and comments at .

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So I decide to write an ad on Craig’s List. The ad went something like this: First off, I am new to this. About me: I am a 30 year old female. I am 5’ 3” 120 lbs brown hair and blue eyes. Guys hit on me a lot so I guess fairly attractive,lol. So why am I posting here? I have been having a fantasy that I want to act on. I have never been with a well endowed man. I have a steady boyfriend so I am only looking for some no strings attached fun. This would be a “one- time only” fling for me...

4 years ago
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My 1st Sex experience with a female in my life

first time in my life had a sex with a female when i was 17 year old. this is the story about that 1st incident.at that age i was masturbating 2 -3 times everyday about thinking a woman. she was then 38 years old [ 21 years older than me ] and a married wife of 2 c***dren and her husband was not with them. he was working in another country and this family came to locate in our neighbourhood without husband.this woman [ im calling priyanka from here ] bought a land with a half built home very...

3 years ago
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laylays 1st

**This story is pure Fiction & isn't True!**Baby Sitting!8yr old girl “lay lay” Comes downstairs after putting pj’s on! (shes only wearing her pj top & nickers) as lay lay jump across sofa her skinny legs wide open 4 few secs! “Revealing a hairless pink pussy!” covered only by thin cotton fabric! Sitting next to me on sofa with her legs across mine her smooth legs & cute white ankle socks! As she wriggled around her legs rubbing between mine & my hands resting against her legs...

3 years ago
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My 1st time anal mmf

My 1st time anal was done on me was with a bi-couple I met on Adultfriendfinder. They lived in the country in a nudist colony. That was quite an experience showing up there. C met me naked at the entrance gate. That was kind of shock but it is what it is. We had agreed to lots of oral fun & me fucking her. I got to their place, I walked in and met B, she too was naked. She was an older brunette with medium tits that sagged a bit with a shaved pussy with a little landing strip. The pics I...

2 years ago
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My new cuckold wife 1st fuck backstory to video

This story takes place Vegas Wed Oct 5th 2016 at Aria hotel Casino. This is the back story to the Video "My New Cuckold Couple 1st fuck video". Its best if you read this then watch the video. I just finish work and go to my room wash up and go to the tables and play blackjack. I have a hour and 45min until my poker game starts. So I start playing and I'm sitting in the 5th spot out of 6. To my left in the last spot is this bad bitch who looks Colombian with a huge rack and beautiful face...

1 year ago
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My 1st experience with a Special Girl

Let me tell you something about myself. I'm your average Hispanic male. I can honestly say I'm not gay or attracted to men. In contrary, I'll truly get turned off by that scene. Im also turned off by hair/hairy skin and bad hygiene (who isn't... LoL). It's just not for me. Yet something about a cute shemale with a booty is something i cant resist. I found myself enjoying shemale porn. A cutie with a booty takibg it up her booty hole. My favorite scenes involve a passable tranny (Ts Foxxy,...

3 years ago
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my 1st time with anothe guy pt3

I was laid back on the sofa stroking my hard cock when I heard " oh danny, sorry I didn't think you'd still be here" it was mr smith back earlier than I thought"oh shit" I cried as I jumped up and scrambled to pull up my white briefs, the rest of my clothes folded on the dining table out of reach"whoa,whoa calm down ,its ok! calm down, its alright no need to be embaressed" he said in a soft tone of voice as I unsuccessfully tried to tuck my hard on into my briefs" i've told you before all boys...

2 years ago
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The 1st Orgy I ever Hosted

have been having these parties for a while now and a lot of people always ask me what happens at the parties. I mean from novice swingers, to people that frequent swing clubs. I guess because bisexual men being such a taboo, they figure something different happens with us than with every place else. I have been to several swing events too and the only difference with us is everyone get naked and plays. So let me tell you what I saw last time.About 6:00 a lady we had never met before, that was...

2 years ago
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Tim and myself 1st trip to Hedonism 2 in Jamaica

Tim and myself 1st trip to Hedonism 2 in JamaicaBy: blondeslutforblacks It was 1998 and we have settled into our lives as a BBC cum loving slut and my supportive hubby Tim. Our lives had changed a bit since I became a BBC lover. Tim’s had started a new business and it was really doing well. It did afford us the ability to allow me not to have to work which meant I could spend my days looking for BBC. Tim came to me one day and asked if I wanted to go to Jamaica and of course I said yes. I...

3 years ago
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1st time meet

[Desmond2tu][/user]It was the middle of the Summer..temperatures were already high. Liam, a very well packaged, passionate, lad about-town in his late 30s is driving, to meet someone for the first time,in the next town. His fat cock is swollen already in his Calvin`s. You see although he was brought up well and most of his family were naïve about sex only having a few partners each in their lifetime, he was different. Although many people claim to be obsessed with sex, he actually was, totally...

2 years ago
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My 1st encounter with real boobsschool friend

Its a true incident, not a made up story.I hope u all would appreciate it, & comment & rate it.Hello everybody, I want to share all my sexual incidents with all of you, which started early at the age of 12. I was a cool, very friendly, peace loving guy in my class, & also the tallest guy in the class. I was being instructed by my parents never to have a girl as a friend once I entered class 8(2002 yr). But you all will be surprised that the no of girl as friends as compared to...

1 year ago
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1st time with her

i had been divorced for about a year, met a (divorced) woman in a chat room on the net. we got to be pretty good friends,talked about her k**s, jobs ect. her bday was coming up, i asked her what she wanted. her answer was for me to take her out to dinner, well thats gonna be difficult, we're 1400 miles apart. the more i thought about it, i said wtf, why not? i told her i'd be there sometime on friday, when i got close i'd call. she figured i'd never show, or come up with some lameassed...

2 years ago
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True Story Our 1st date Still together

I've decided I should post here to let everyone know how we met..... you can never judge a book lets say.... so here is how our 1st date went.I had an ad in a popular dating site and was getting a bit hacked off with it. Plenty of offers, but nothing that really floated my boat. I knew what I was looking for.... someone who was, underneath it all, more like me..... willing to swing!!So, one morning I checked my mail and found a message from an older lady. She looked really nice, quite plain on...

4 years ago
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1st Class Coach Me Chudd Gai Me

Diwali k aggey ki raat thi mujhe mumbai se ahemdabad apne ghar jana tha. Mumbai me mera college hai aur me apna mba kar rahi hun. I was very tired that day and mujhe bahut zyada nind aa rahi thi. I was waiting fr my train at the station and wishing that train jaldi aa jaye. Jese hi train ayi me apne 1st class coach me ja kar beth gayi. Kyuki mere father railway me hain me 1st class me hi travel karti hun. Thodi hi der me vaha ek ladka aya jiski height average si thi well built tha and he was...

2 years ago
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1st BBC Back Seat Hook Up Sex Pts13

1st BBC Back Seat Hook Up Sex ``````````````````````````````````````````````~ Pt.1 ~8/27/2020```````````````MAN Oh MAN! I can't believe I did it...I Invited a Man to my car late at night & Let Him have his way...Fuck the Pandemic! Im Horny! No Parties and "scene" to mention nowadays. So I reached out with grasping hands to my social networks.I've had countless fellas hitting me up, and have kept in contact with a few. There is a great site here in LA for Gurls and the Men who Luv them...

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