Crossdresser's 1st Time! free porn video

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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 was enough and started making my way onto the street looking for - well I don't know what really. but I just walked until I saw a dark looking guy having a piss in a courtyard not far from where I was. I mad my way over to him shyly and was trying too look over his shoulder while he was relieving himself. he turned and saw me and I think his words were 'what the fuck are you looking at'. all I could say was 'do you want a hand with that?'. he stood still for a moment - I thought he would just turn and hit me being a pervy crossdresser in the street. but he turned after a pause and held his cock in his hand looking at me. I needed no further introduction and grabbed his cock with both hands. it felt great to feel a nice black cock in my hands. I grabbed his balls with my left hand and cock with my right. he sighed and I stroked back and forth slowly. I couldn't help it anymore, I needed it in my mouth so bad. I pointed to a quieter spot as we were still only 3 yards from the high street. he nodded and pulled his jeans up and moved to where I had pointed, his cock soon flopped out again. I slowly made my way to my knees for the first time. with this nice big black cock staring me in the face, I kneeled looking at it, taking it all in before putting all my mouth over it and trying to take it down my throat. I couldn't straight away but I kept sucking him back and forward, playing with his massive balls. he was loving it and kept saying 'good girl'. I knew my place and that getting this mans cum in my mouth was my goal. however, whilst I was enjoying this hot black cock with my mouth and tongue, he had other ideas. he said 'stand up', being smaller than him I did so, 'turn around slut', again I did so, after all I had been sucking him off for about 15 mins. not fully knowing what to expect I bent forward and I will never forget the next part, he pulled my leggings down and gstring to one side and ploughed his tongue so deep in my ass I jolted forward and nearly came there and then. I couldn't help but scream out in joy. he continued tonguing my ass hard until he suddenly stopped and done up his trousers. I was stunned, bent over, ass out turning around to see what was going on! I heard footsteps, it was woman walking through the courtyard. I pulled up my leggings and sat on the wall from which I was bent over just seconds ago having the feeling of my life getting my virgin hole licked. he just pretended to pee whilst I sat there waiting for her to drift past so I could have his tongue back in my ass. she past without battering an eyelid. he looked at me, pulling his trousers down and with a devilish look and told me to turn around and bend over again. I was so pleased he said that and pulled my pants down so quick, but what happened next shocked me. I was expecting that long tongue back in my ass but instead I was greeted with something much bigger and much more wet. I felt no breath on my ass this time. instead I felt hands on my hips. I knew what was about to happen, I protested and said I didn't want to, but with that he slammed 2 fingers up my ass and I again was putty. I couldn't help it, I wanted it now. and he wanted my ass so bad. he grabbed my shoulders and pressed his cock against my virgin asshole. I kept protesting saying I wasn't ready but he just said 'you shouldn't have sucked my dick then, I only wanted a pee'. he put his right hand index finger in my mouth and slammed his cock into my ass with his left hand in one movement. my god I could have came there and then but he grunted and slowly eased out and hard back in again. causing me to gasp. he was loving my virgin ass. and if im honest, I loved his big black cock in me. he kept chaging his hands from grabbing my teen ass cheeks to holding my face and throat. he was in control of me, pounding away at my tight ass. it hurt so much at first but it started to feel great after a few mins. he carried on, absolutely smashing my asshole for about 15 mins until he uttered the words, 'where do you want my cum slut'. the only words I could say were 'keep going, please'. he took the hint and started slamming he harder and harder until my legs went straight while I was bent over the wall infront of me. he finally managed to say the words 'im gonna cum' in such a deep angry voice. he was really going at me now and my ass was on fire but I wanted nothing more than for him to cum in me hard. and omg did he. with those final words he went so deep and I could feel his hot cum shoot deep inside my tranny ass. he grunted on ever stroke and grabbed my ass cheeks as I was still bent over straight legged, with my gstring around my ankles. he slowly slid out of me after a minutes pause of his cock pulsing in my ass. I turned around just to see him leaving the courtyard. I will never forget that cock and that is what made me the slut I am now...

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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...

4 years ago
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Farheen 1st Experience

Hi iss ke site ke deewano, main bhi is site ki fan hoon aur kai saalo se is site ki story padh padhkar apne aapko mast huyi hoon aur apna ek real experience share karne jaa rahi hoon aapke saamne. I will 1st intro myself mera naam Farheen (name changed) hai aur main mumbai mein rehti hu, i m single and my figure stats is 36(boobs) 34(waist) 40(hips) hai. Bohot saare ladke mere body parts ko dekhte the mujhe achcha lagta tha par i always had an attitude of my figure, ab main sidhe story par aati...

3 years ago
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Gita Anty ke sath 1st experience

Hi,Me a punjabi hot guy with a young and dashing personality, size 8″ length 3″ dia.here I would like to tell you a real story of mine, but let me put this in hindi as it will be much more enjoyable. Baat un dino ki hai jab mai 1st year mai tha.. Aksar mai college se late he ghar aya karta he, but aj jab mai ghar aya to ghar par mere liye 1 surprise that… Hamre family friend Anuj Uncle apni nai naveli dulhan ke saat hamre ghar aye huye the… Wo bhi chandigarh mai he shift ho gaye the… Mai unhe...

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...

2 years ago
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No limit Aaliya 1st Pussy and Threesome

This is Part 2 of "No limit Aaliya" Read part 1 first, called "No limit Aaliya - 1st time Hijabi Whore" Please comment what you thought, and feedback is much appreciated! This is the 1st time I'm writing, I know I will have loads of improvements to make, so please be considerate. Any requests as to how depraved you want Aaliya the Hijabi Whore to get, please let me know via comments or PM! Aaliya was sitting in sex ed class, staring in shock at what was transpiring in front of her. The youth...

3 years ago
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Witnessing sex for the 1st time

This is a true story, and it was life changing! Until this night, I had never witnessed people having sex, not even on video. I had never seen a cock either. I had been very curious about sex, and had asked my friend about it. We had many conversations about what we thought it would be like. My father was a professional baseball player. My mom is a gorgeous lady from Spain. My mom had a great friend that she spent a lot of time with. She was a beautiful petite woman, with a...

3 years ago
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my 1st time

Introduction: this is 1 part of my 1st story Ive had a lot of sexual encounters in my 28 years of life. My favourite was my first, it happened 14 years ago, when I was 14. Ill tell you more about that later. It was my sisters wedding and was a bridesmaid. It wasnt till the reception that I realised that I might be confronted by Marcus. Marcus mom is friends with my sister and I had been in love with him since I was 10 and he was 12. When anyone in our family has a wedding they choose to have...

3 years ago
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My 1st time

The wife and I were on our holiday in Jamaica and we loved this place so friendly and they couldn't do enough to please you. Our 1st week had gone by and Susan was all tanned up and she was looking so good, Susan is a size 20 and she is not shy to show it off, yes she gets some looks cos she has it all hanging out but she is a proud lady and I am a proud husband. Some people around the pool and estate we were stopping on you could hear them "Why does she have to show it all" so one day I over...

3 years ago
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Emilys 1st Time

Brian was a married man and had been for about 22 years. He was in his late 40’s and so was his wife.He had a daughter called Sally who was 18. They lived on the outskirts of London where Brian a predominant commuted to daily.One day Sally came home with a new friend.Hi dad this is Emily she said as she came in to the lounge, we can’t stop long I came back for my mobile and then we have to go back to Emily’s as it her 18th birthday party today. Brian looked round, he thought he would be polite...

4 years ago
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Laceys 1st time

This is my 1st (and probably last) attempt at writing a story.It was the day before Lacey's 18th Birthday. She was planning something special to celebrate only she couldn't tell the family. She phoned her cousin Steve who was 28 and casually asked if he was coming to her party. Wouldn't miss it for the world k**do he said. k**do she thought did he think of her still as a little k**? She hoped not otherwise her plan might fail.The day of the party arrived and everyone came and enjoyed...

4 years ago
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Summer the 1st time

It was a hot afternoon,the last day of June,and the sun was a demon.These were the words of bobby goldsborough,and as they came out of my pocket size radio,I thought how apt that song is at the moment.I was on my way to meet the lovely nikki,and my hopes of something happening between us were all I could think of.I'd been seeing her for about 2weeks now,and we had never been all on our own for more than few minutes. I had been to her house,but her mum never let us go out of her sight. She was...

2 years ago
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very 1st time

Fictional storyHi my names Andy I’m 67 years old never been married, had my own business and now retired, my Business was import & export, I would like to tell you about my 1st sexual experience when I was 17 yrs old. I was working for a family business as a store person there was about 30 people working for this company always treated well and always got a great Christmas bonus from the boss, I had not long been with the company and had the usual pranks played on my, go get a rubber...

4 years ago
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Curious 1st Timer

“Ok sexy, see you when you get here.” I’d been emailing “BlackStallion281” since 7pm. I’d always been curious about what it would be like to be with a man. Since high school, I’ve read and seen erotic material about gay sex on the internet. It always gave me a hard on. But this was it, I’m 21 and a man and I can do whatever I want. We’d been emailing each other after I found him on Craigslist. He seemed like a nice guy. Much older, which was ok with me. He was willing to “show me the...

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