A Young Cross Dresser's First Gay Experience free porn video

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I was just a young boy then, senior in high school, horny as hell and dreaming of my first gay experience since sitting in my sisters red lace thong and white lacy bra and discovering the one porno in the house everyone kept hiding from me. I guess they thought my sisters panty drawer held no interest for me......they were wrong.

It had been a great afternoon jacking off in my sisters bra and panties and watching my first porno when it happened, I saw the most beautiful thing ever, Peter north titty fucking a hot blonde and cuming all over her face. I was besides myself I could not believe how hot that was and how fucking much I wanted to suck a big cock and feel it explode all over my face, in my mouth.

I’d had been stealing my sisters clothes for years and jacking off in my room dreaming of the day a man would finally fuck my face and give me his sweet, sweet cum. giving myself self facials and needing to jack off five times a day, fuck I was horny.

Finally on a quiet morning in spring I found myself all alone in the house, my friend James had come over, he would do it a lot and we would listen to records, look at girly magazines and from time to time jack off together. we had never touched each other but god how I wanted it, he was smooth, had a nice sort of fem body and a hard 7” that I would fantasize about when we looked at porn together.

That day we were looking at some mags and I said “don’t you think that girls lingerie is sexy” all he said was yes referring to the slutty blonde in white garters, stocking and push up bra.

Next I asked “have you ever wore your sisters panties?” he paused for a second gave me a confused look and said “fuck no” couple of minutes went by and I asked “have you ever thought about it?” he looked down at the magazine and in a barely audible whimper said “well....uhm...yeah” I smiled and gathering up some courage I said. “you know I do it all the time” he quickly looked up and said with wide eyed amazement “really?, you do? do you like it” I smiled “I love it” and we both fell silent a bit awkward moment but you could feel the tension rising up.

Then after a few minute of silence I asked “James can I ask you for a favor?” he looked up sand aid “sure just ask” I hesitated for a second and then went for it “would you video tape me in my sisters panties?” he was taken aback for a sec and I could see his cock which he had been stroking while looking at the mags getting instantly hard. “ok i guess” was his reply “really you don’t mind?” and he said “no go ahead I think it be fun”

I smiled and quickly grabbed the camera from under my bed and handed it to him, excuse myself for a second and ran into my bathroom I could barely believe it. could this be it? the moment I’ve been waiting for? quickly I stripped out of my boy clothes, slipped my sister lacy red thong, lacy white push up that felt tight against my flat chest. white knee highs and my sisters red 3” pumps. I took the hair out of my pony tail and let it fall over my shoulders and in a final touch I broke out the red lipstick. I looked in the mirror and smiled, I looked hot, my hard cock bulging from my panties, about to be a CD for the first time in front of another guy.

I was nervous, I reached for the door handle and I could see my hand tremble, was I really about to do this???? and a that moment I could only think of the years I had spent fantasizing about this very moment. I took a deep breath and open the doors and stood smiling at the door way.

He looked up at me, camera in his hand, I smiled, he was startle for a second and then began to videotape me, I swayed seductively on the door way for a second “what do you think?” I asked, he said nothing I stepped out of the bathroom and started walking across the room, the camera following me, I stood in front of the mirror and could see him in the reflection, the camera pointed at my sweet young ass, I smiled again.

I pointed for him to stand at the foot of the bed to film me and I laid on it, kept smiling, pulled out my cock and started to stroke it. he stood still. “do you like it?”I asked he nodded, I smiled, “do you want to touch my cock?” he gave me a faint nod and I smiled again. “would you like me to touch yours?” again faint nod.

I told him to put the camera down I looked at him “I have an extra pair of panties would you like to wear them?” he nodded, I reached under my pillow and pulled out a pair of white, satin bikini panties, I wrapped them around my cock and stroked it for a minute and then handed them over to him “take of your pants I said”.

He nervously stripped while I enjoyed watching his smooth sexy and untouched body, he took the panties from my hand and slipped them on, I kept lowly stroking my cock, I was so excited I could not think straight......lol.....nor did I want to.

Finally there he was, the object of my desire, in my sisters white panties, his cock hard, throbbing an bulging. a spot of pre cum I was so fucking horny.

I spread my legs and asked him to kneel in front of me, between my legs, I asked “how do you like wearing panties?” he nervously laughed “its nice” I grabbed my cock from the base and pulled it to touch his through his panties. “do you think I’m hot?” he smiled, “pull your cock out, jack of for me, with me” I said and he did, he pulled out his beautiful cock and I laid there for what it seemed hours gazing at our bodies.

“I’m gay James” I said “I’m gay and I am really hot for you” he said nothing “I want to have panty boi sex with you” again nothing, he just looked at me and kept stroking.

I got to my knees and kneeled in front of him, our cocks touched and we looked at each other, I leaned forward and kissed him, he stepped back for a second and looked at me, I just stared back, it seemed like an eternity and he lunged forward kissed me deep and full, his hands grabbing my ass pushing me back to on my back. We were making out with fury, our cocks touching, his hands pulling me close, our tongues flying it was amazing.

I stopped him for a second and said “James I want to suck your cock so bad” he smiled and I smiled back. I pushed him off of me and made him lay on my bed. I kissed him again full and deep, made my way down his neck, chest, nibbled on his nipples and finally got to the promise land, what I had been waiting for all this years.
eagerly I pulled down his panties, and held his cock in my hand, stroking it, admiring it and for the first time, with a lot of care I kissed it, I kissed the head of his cock, felt a little bit of pre cum coat my lips and I rubbed it all over, I smiled and with joy held his cock by the base and started to suck him, up and down, slobbering all over it, stroking it loving it.

Nothing like your first cock, when you put another mans dick in your mouth and you realize “fuck I worship cock” and you feel him throb, hear him moan, feel his hand on your head pushing it deeper in you and you realize “fuck I am a sexy, slutty panty boy sucking cock.

I sucked him and kept enjoy his cock for what seemed day but was probably minutes, he stopped me and said “Alex I want to taste your cock too” I smiled and was happy to comply, we got into a 69 position and sucked, sucked, sucked cock with passion. it was delicious, heavenly it was cock in each others mouth.

But we were young and inexperienced, we sucked cock with such eagerness that soon we felt each other shudder and in and explosion of warm silk we started to cum together in each others mouths, we just could not stop, it was wonderful.

Cum was dripping out of our mouths, we could not bare the idea of taking our cocks out of ours mouths as we laid in my bed, finally we pulled ourselves up to sit on the bed and our eyes locked as we saw our faces dripping with hot, sweet cum, our chins covered, our lips glistening. we smiled and slowly leaned forward and kiss, kissed in the most wonderful way two your gay lovers can, tongues licking and lapping our hot cum, we were in ecstasy, so much so we got hard again instantly, we reached to stroke each others cocks again, our hands dripping with cum again and stroked each other as we kept on kissing.

I smiled at his and asked “so how do you like it? having sexy with a boy?” he kissed me “I like it, I like it a lot, I specially like you in your bra and panties” I smiled and kissed him and slowly made my way back to his cock to keep sucking him.

as I sucked him he kept playing with my ass, I loved every second of it, “”I want to fuck your ass” he said I stopped for a second but kept sucking his cock “I really want your ass” he said as he slipped a finger inside of it. it made me jump, I kissed him and said “yes, fuck yes please make me your bitch”

We put a couple of pillows down on the bed and I laid on top of them so my ass would be up in the air, he spread my legs and started to tongue my ass “you are a sexy panty boi” he said “fuck me I said, make me your bitch, fuck me” the anticipation was killing me, finally he started rubbing his dick on my ass, it was driving me wild, he would push like he was going to go in me and i would brace myself but he would pull back, finally I felt the baby oil on my ass, I bit the pillow, braced myself, held my breath and it a wonderful second my gay ass was being fucked for the first time by a wonderfully hard 7 inches of man meat. it was pain........it hurt.......I held my breath, clenched my fist......and slowly, with the movement of his hips pain begat pleasure and he fucked my ass more and more and with each pump, each thrust of his hips, he would bite my ear, reach around and feel for my cock.

As he pushed faster and deeper in me I would arch my back looking for his lips and finally in a final thrust of gay ecstasy I reached back, turned my neck to kiss him, our lips barely touched, reached again and as his teeth caught my lower lip I started to cum as he started to cum inside of my ass in the best orgasm of my life, his teeth drew blood from my lips, I gasped and fell to the bed exhausted, with the cock of my gay lover still in my ass, full of cum and satisfied we fell into a slumber that had awaken the gay crossdresser slut in me.

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I had met Steve thru a gay dating site, we exchanged messages over a few weeks and then finally agreed to meet. I was very nervous on the way over to Steve's for two reasons. One was it was going to be my first gay encounter. The Second reason, and one i had only agreed to after Steve's insistence, was that i was going completely cross-dressed. I'd gotten dressed at home as Steve wanted. Putting on a satin and lace garter belt which i attached to lace top suspender stockings, then a lace bra...

1 year ago
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My First Gay Experience

My name is Phil and I’m 24 and have been heterosexual all my life. Like many guys I’ve fantasized about having gay sex since my teenage years but a few weeks ago I decided to see what it was all about. I headed off to the seaside and went to a well-known gay club there. I’d had a little bit of Dutch courage and was a little off my head! I’d never been in a gay venue before and was amazed at the way blokes blatantly eyed each other up. In the state I was in I found it really exciting when guys...

Gay
2 years ago
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Gayu8217s Journey In Her Life 8211 Part 4 5

Part 4 Gayu was still feeling shy, she did not want to look in to her FIL’s eyes directly, and did not want to take any kind of initiative. Suguna asks Gayu and Shankar to come out for dinner, Gayu tries to reach for her cloths, but Suguna says no need to wear any dress, Suguna takes shy Gayu holding her hand to dining table, makes Shankar and Gayu sit by each other side and she sits on the opposite side, all the dishes are kept on the table, Suguna asks Shankar to feed Gayu, and asks Gayu to...

4 years ago
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  • 59
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Gayu8217s Journey In Her Life 8211 Part 9

Part 9 Both of them wake up at around 1PM, and go for lunch, they do enjoy good simple lunch, and sit and start chatting again, Ganesh first thanks Gayu for a wonderful bath she gave, he had always missed after his mom stopped giving bath to him. Gayu tells that, since you said you missed it I just wanted to give you a good bath like giving to a young kid, but I had not realised that you were a grown up kid. Gayu asks Ganesh, whether did he have sex with anyone before? He says know this was my...

3 years ago
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Gayu8217s Journey In Her Life 8211 Part 2 3

Part 2 They all had lunch together, than Gayu went to her bed room with her hubby, and suguna with her hubby, as soon as Gayu went to the bed room and closed the door, she wanted to make love to her hubby, who again removed his dress and went under the bed spread and asked Gayu to join him, she wanted to removed her dress too but he refused saying if someone comes, and as soon as she came to the bed under the bedspread he pulled her went over her inserted his dick in Gayu’s pussy and 5 strokes...

3 years ago
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Tuition Teacher Bana Lover 8211 First Gay Experience

Main Pehle apne barein mein batata hun mera naam Ankit hai; age 20, body type slim rang gora and lund 6.5inch ka hai. Yeah kahani aaj se 2 saal pehle ki hai. Main 12th std mein tha.waese to main padhne mein acha tha par Physics mein thoda weak tha. Mere dad k friend ne unhe ek Professor k barein mein bataya jo ghar aake tuition padhate they, mere dad unse mile aur unhe woh thik lage toh bas meri tuition wahan lag gyi. Mere teacher mujhe ghar aake padhate they aur jis room main padhta woh baaki...

2 years ago
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Young Teen Gay Experience

Introduction: Wanted to share this real experience This all happened when I was just 14. I was playing videos games at my male friends house for a number of hours now and it was getting late so I decided it was time to head home. I said goodbye and left, About half way to my own home I had the sudden urge to go to the bathroom, luckily I knew of a public one very close by I had never been there and wasnt sure if it was safe but I thought fuck it. So I headed right there. I entered the bathroom...

1 year ago
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  • 28
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Nenu Crossdresser Nunchi Gay

Hi, na peru ajay. nenu tenth class ki vachinappatiki naku crossdressing alavatu ayyindi. enduko emo telidu, kani adavalla laga chira, jackettu vesukovatam istham. mukhamga Bra and Panty. ma inti venaka oka portion lo vunde oka ammayyi thana battalu vutiki bayata aresedi. ala aresina vatilo thana Bra lu kuda vundevi. mamuluga avi sayantram avi tisesedi. kani oko sari marichipoyo emo battalu tisedi kadu. ala tiyanappudo leka oko sari Valla bathroom lone vadilesina battallono (valla bathroom...

4 years ago
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  • 54
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Gayu8217s Journey In Her Life 8211 Part 1

Suguna was 45 years old and she had recently got divorced as her hubby found out that he cannot handle her as was very demanding sexually, and he was contended simple man and he had found someone who matched his requirement, they had a son Ganesh who was 18 years old studying in engineering and staying in the hostel 300 kms away and a daughter Shruti who was 22 years old, who had gone abroad for higher studies. They had left enough money for both the children that they don’t have to worry about...

4 years ago
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  • 57
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Gayu8217s Journey In Her Life 8211 Part 7 8

Part 7 Ganesh & Gayu come out to the dining table, where the maid has already arranged for lunch, as per instruction from Gayu, a kheer or payasam & sweet also has been made for MIL’s son. They both have lunch slowly enjoying the delicious food. Gayu with small wicked smile without giving any hint to Ganesh asks whether Ganesh was able to take some rest. He says he slept well and woke up only she came to call him for lunch. Again the discussion goes back to the family, Gayu asks about the...

3 years ago
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First gay experience

My wife had become uninterested in sex which left me beating my meat but still horny all the time. I was at a training out of town and staying in a hotel. I was watching porn and went onto one of the adult hook up sites to look at people and fantasize. After about an hour of trolling, someone sent an IM to me. He said he wanted to suck my cock. I do not think of myself as gay but have had a few gay experiences a long time ago.After a few minutes, the person sent another message. I replied,...

3 years ago
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First Gay experience

I remember my first gay encounter as if it were yesterday. I had just turned 21 and was fresh out of Navy boot camp on my way from Philadelphia to NYC via Greyhound bus. I saw a guy in his early 30's waiting to board the bus with me and I could tell that he was showing some special interest in me. Maybe he liked the way I looked in my dress blue Navy uniform! He was in back of me in the boarding line and I would occasionally glance back to see if he was still paying attention to me. As I...

3 years ago
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  • 174
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ldquoThe Clubhouserdquo First Gay experiences

It was more of a shed really, but we all called it “The Clubhouse.” It was in the back of a friend’s house a few streets over from where I lived and it would become the place of many first experiences for many of us. All of us young, with parents away at work til the evening hours, we all found ourselves free, horny and curious.It started with Brian. He had some “girly” magazines he had taken from his father’s collection and Mike got some from his older brother, also. Of course, we all wanted...

4 years ago
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Young Cross Dressers Secrets

Young Cross Dressers Secrets *Sandy was busting at the seams to tell someone some very exciting secrets she was keeping. She couldnt tell anyone she knows. She decided to tell them here. __After reading My Bra and Panties are Missing, my own real story kept nagging at me to be told, but I wasnt sure how. I decided to change all the names and write a story all about this secret world I stumbled into. I started getting very horny just thinking about all that had happened&hellip,. __My story...

3 years ago
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My Ultimate Gay Bukkake Experience

I would not call this the second part of my first story but it is in some kind still related to it, well to what hapened after the first story hapened. Some of you might have allready have read my previous story, it was about my first glory hole experience where I ended up sucking a much older men's cock nice and sweet and loved it even more that I could expect it. At the point where it is even my best sex experiment I ever had... Until this story hapened. A few days after the first story...

4 years ago
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My first gay experience

I was around 20-21 when I had my first gay experience. I was never really attracted to men, but I occasionally would have fantasies about cock, and having thoughts about sucking and having a cock in my ass, and being a cum slut. Over time these fantasies grew and I started to jerk off to shemale porn and eventually gay porn. Over time I bought a dildo and started to play with my ass. The dildo felt so good in my ass that I knew that I had to have the real thing. So I went online to find to find...

4 years ago
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first gay experience

In college I thought I was straight. Always did, even though every once in awhile I imagined being gay. I never thought that I was. I love gay sex, bukakes, anal, blowjobs all of them I do it all the time. But, before this experience I wouldn't even let a guy see me naked. It all started when I was a sophmore in college. I loved sex and I slept with girls all the time. I could almost always get laid. There was one place were every guy knew he could have sex any time he wanted. That was in the...

First Time
3 years ago
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My First Gay experience

My First Gay Experience by Johnnno Allthwaite.We was down the Dog and Duck, Big Norman, Harley Charlie, that's the bloke with the 50cc Honda Moped and me and a few other lads drinking Stella and Strongbow like, while we waited for a Lib Dem meeting in the back room to finish so we could meet up with Al and play pool. Their meeting dragged on like Lib Dem meetings always does, see like if we can't agree we does arm wresting or first double top or tosses a coin, but they just talk, and 'Seek a...

3 years ago
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First gay experience

The first time I went to an adult video store, I was 18 years old. I went because I wanted to buy some porn magazines because there was no internet in 1994. I discovered some booths in the back where I could put money in and watch porn in private. I started to go there and masturbate in the booth. One time the door didn't close all the way and while I was masturbating some guy opened the door a little and watched me. At first I closed the door quickly, but then I realized how much it excited me...

4 years ago
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Wife Turned Husband Gay GayMaker

Tracy was home from Vegas after a week away with her girlfriends. Seeing her and being around her again, the events of the past few days—my deal with Simon—suddenly seemed like just a fantasy again, a rough dream. I was feeling guilty, and maybe thinking of it as a fantasy was just a way to ignore the guilt. We planned to go out to a bar for dinner, so I poured us both a glass of wine while Tracy showered and got ready. When I came into the bedroom she was sitting up in bed with her eyes...

2 years ago
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My First Gay Experience

My name is sunny. I’m a 27 years old bi sexual guy with an athletic body and 6 1/2 inch dick. I have been with iss for quite a long time so thought of posting my story here. My first experience was happened near marina swimming pool loo. For the people who don’t know about marina swimming pool, it is one a gay cruising spot in Chennai. I have read many articles about this place so I wanna try this place once. So one weekday evening I went to this place to explore what kind of things are...

Gay Male

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