My Road To Cross-dressing (Part 3) free porn video

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From the first time I dressed, there was always a sexual element. I used to find the time to wear something feminine and wank myself. It went hand in hand, so to speak. One of the things I loved doing was getting dressed up and laying on my bed with my legs over my head and wanking.

When it was time, I would cum in my own mouth. I did it so many times but it was always uncomfortable, but I used to cum anyway. I didn’t swallow but spat it out, every time. I also used to kneel in front of the mirror and wank and cum on a towel or tissues. When I look back I regret all that lovely cum had gone to waste. It took a long time to get used to swallowing. Once I got used to it I couldn’t stop. Still can’t. 

I knew that many girls and boys used to swallow cum and always wanted to but I really didn’t like the taste. Then one day, quite by accident I was watching a cookery program and the chef was trying to tell the presenter about taste. The presenter said that he really didn’t like that food and the chef told him something that was to have a profound effect on me.

He said that if he ate the food he didn’t like twenty times, that it would change. Either, he would like it or he would at the very least, not dislike it anymore and get used to it. As I sat there watching the program I was thinking that this was what I had to do to get used to swallowing cum. 

Over the next five days I wanked into my hand and licked it off, seven or eight times but still, I didn’t like it. I used to look forward to having a time during the day when I could wank without being caught but I realised that I stopped being excited. A few days went by and I decided to stop trying to swallow because I didn’t really like it and it bought a downer to the experience. But, I simply could not stop wanking. It was my only sexual pleasure at the time. 

As with most thoughtful people the idea still haunted me and I started to occasionally cum in my hand, lick it up and swallow. Ten, twenty, thirty, forty times and it did become less horrible. I actually quite liked it. I didn’t swallow every time I wanked, it was more like one in twenty but it became more and more frequent. It did depend on what position I was in when I played. If I was kneeling it was easy to cum in my hand and I did, then a few licks and it was all gone.

At the same time as the masturbation and cum swallowing there was also a desperate desire to film myself dressed and playing. I managed to get a video camera and when the time was right I got myself ready. I dressed in a woman’s swimming costume that was black and had loads of slits down both sides, unbelievably sexy for a swimsuit. I also wore a pair of fishnet stockings and I positioned the camera.

I was nervous because this was the first time I had seen myself wanking while dressed. I remember quietly talking dirty to myself and the orgasm was wonderful. I watched it later and wanked again. I only saw it on the video viewfinder but it was great. After about two days I got scared that I would be found out and deleted it. A couple of weeks later I did it again. 

I always dressed, wanked, then watched it and wanked again and always deleted it. I wish I still had all the films as there were some great times. It took some time before I decided not to get rid of them. I had a great time one night and kept the tape. I liked the beginning and started the next film over recording it and then again and again.

I managed to get a forty minute film of myself dressed in all different types of outfits, wanking, fucking my self with various dildos, and swallowing my own cum. Wow, what a film. I watched it and played with myself dozens of times and had a ball. Seeing Lucy Lou having fun was such a turn on and it made me experiment with outfits and makeup now I knew what I looked like.

As time went by the desire to have sex with a guy whilst dressed became overwhelming and it was apparent that this was what I had to do. I wanted to feel like a woman, suck cock, swallow and be fucked. One of the websites I had joined had some cross-dressers that lived not too far away and I got in contact.

They invited me over one night to have a meal and be girly. It was quite an experience but there was no sex, just dressing. I mentioned to them that I needed to go the whole way and it wasn’t long before they had arranged another night, except this time there was going to be a young guy there who loved trannies. 

Over the next few weeks, I waited in anticipation, feeling quite desperate. I wanted it so much that I used to get hard every time I thought about it. When the night actually arrived I remember feeling that this was the true moment when I could be Lucy Lou, the tranny slut. They had sent me photos of the guy and I liked what I saw, a lot. I couldn’t wait and made the decision not to tell the guy it was my first time. I knew what I had to do.

We had a great, light meal and ended up sitting together on the sofa. We chatted for a while and got on well. Then the other two left. I was alone with a twenty-five-year-old gay guy who loved cross-dressers. His name was Tom. I moved the conversation on to sex and asked him what he liked. He wanted his cock sucked like mad and asked if I swallowed. I told Tom how much I loved cock and always swallowed. He was ready and so was I. 

We kissed and my hand went down between his legs and I felt his hard-on. He quickly took off his shirt and undid his trousers. My hand slipped inside and I grabbed his cock. Tom pulled his jeans off. He wasn’t wearing any shorts. This turned me on. He sat there opening his legs and winked at me.

I immediately dropped to my knees and kissed his helmet. Both my hands were on his cock and I sank his shaft into my mouth. Such a wonderful sensation. I opened my eyes and saw that I was in between a gay guy's legs giving head. I knew what to do and he told me that it was really amazing.

“You have obviously sucked loads of cocks, slut, ‘cause you’re good. You suck it good, bitch and you swallow what I give you.”

It didn’t take too long before he shot, either because he was well ready or I was doing a good job. As he got close I tasted his pre-cum and readied myself. I wanted to act as if it was something that was totally natural to me. I heard him groan and felt the first spirt, and then another really big one and then another.

I licked his juice around his helmet and it tasted lovely. He shot a few more spirts and then he relaxed. With a large load of his cum in my mouth, I pulled his cock out, opened up to show him. I held my breath and swallowed it all down. It was an awesome moment and I was thinking to myself that I wanted to do it again straight away. 

Tom was very content but I kept sucking. 

“That was amazing, Lucy.”

“I haven’t finished yet. You can’t leave a girl wanting. I always suck a guy twice before he fucks me. That ok?”

“Fuck, yes. God, I didn’t realise that you were such a slut. Two blow jobs and a fuck. Now that’s what I call a session. You keep sucking, bitch.”

I did what I was told, even though I was the one who had instigated it. I was enjoying myself and so was he. As I sucked I looked down and saw my panties and my rock hard cock. I felt so right and just gave it everything I had. He came again after a few minutes and I gulped it down. 

“Now, it’s my turn,” I said positioning myself next to his head. I moved my panties to one side and took out my hard cock and started to wank slowly.

“I always swallow my own. I like to cum in a guy's mouth and then cum-kiss him and take it for myself.”

“Ok, Lucy, no problem. You really are a dirty slut. Do what you have to do.”

I placed my cock on his lips, with my hand gradually wanking faster, I held the back of his head. I slipped inside and could feel him licking my helmet. It was turning me on like mad. Looking down and seeing myself wanking off into a guys mouth would make me cum really quickly. As I got close, I couldn’t stop thinking about the fact that I was going to cum-kiss and swallow my own. Then the feeling rose inside me and I came.

As soon as I had finished, I quickly sat beside him and put my lips on his and opened my mouth. My tongue entered his mouth and I could taste my juice. It was lovely. He pushed it into my mouth and I gulped it down, loving every second. This really was turning into the most incredible experience.

I pulled my panties off and laid on the sofa with my legs open and started fingering myself. I ordered Tom to lube his cock and slide it inside my sissy cunt. He wanted a rest but I was having none of it. Still hard, he pushed his cock inside me and started fucking me gently. My hands moved around and I grabbed his bum and started pushing him in and out of me.

This went on for about twenty minutes, he got faster and more intense and I made him pull out and put it in my mouth then back inside again. He called me the dirtiest slut he’d ever been with and after much pounding, he emptied his load into my mouth. I was so turned on that I grabbed my cock and wanked and came within thirty seconds. As I shot, I started collecting my cum up from my stomach and licking my fingers. Tom was impressed. 

“Wow, Lucy. You really are one serious slut. I had no idea that you were like this. Fuck, babe, can I see you again? Next time I might bring a couple of mates too if you are up for it?”

“That sounds nice, three guys. I love being fucked and sucking three guys. My favourite.”

Of course, I was lying. He had no idea and neither did his friends that this was my first time but I had practised so many times on my own, it seemed like old hat to me. We had a few sessions together and I honestly felt so wonderfully right. 

The only other thing that I knew, I not only wanted to do but needed to do, was rimming. I knew that he had to be clean and I would insist that he showered just before. It was something that I had thought about and had had a lot of pleasure playing with myself fantasising. 

Tom came around and I told him to shower and put on a very short dressing gown. I was dressed and ready when he walked in the room. I could see his hard-on as he walked towards me. I sat on the sofa and pulled him in front of me. Both my hands slid round to his sexy bum and I moved him around. I lifted his gown and kissed both cheeks.

Then, I parted his cheeks and kissed his hole. My tongue came out and I gave him a little lick. My passion got the better of me and I put my mouth around his hole and started snogging it. My tongue worked like mad and I caressed his cheeks as I kissed, licked and tongued him. 

Then I moved back and asked him to put one leg on the sofa while the other was on the floor. I moved so I was sitting in-between his arse. This was a great position and I just got so into it. I was in heaven. I was enjoying it so much that I just didn’t want to stop. He loved it and groaned as I got more and more passionate. Tom took off his dressing gown. I carried on and then heard him start to wank his cock. ‘Wow I was going to get a mouthful too,’ I thought. 

“God, Lucy, that is just so amazing. You are turning me on like crazy. You keep doing it girl, I will tell you when I want to turn around. You are going to get the biggest load I have ever given you.”

Hearing that made me tongue him more and I was lost in this fantasy. I was enjoying it so much that when he quickly turned around I was taken by surprise. Tom pulled my head towards his cock, pushed it inside and with a big grown he shot his massive load into my mouth. He was right. It was the biggest load I had ever had from one guy.

Obviously, rimming him drove him mad and me too. I just wanted to keep doing it. This was something that I really loved doing and didn’t realise how nice it was until I had done it.

 

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Tiffany The Cross Dressing Slut

I was at the swimming pool with a couple of friends and my cousin. I was 15 at the time, My Cousin, Mark, being 13 and my friends John, 14, Steve, 14, and Henry, 16. We were all drinking beers we asked a guy to buy us at a local grocery store, and were relaxing. We were all chilling in our shorts, with all our upper halves revealed, with John and Mark were the only ones to have six packs. Everyone was drinking, we were having a blast! 20 Min Later, we walk over to the Jacuzzi, and sit down...

2 years ago
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SRU Cross Dressing Blessing

SRU - Cross Dressing, Blessing By Lisa B "Damn it" Joe thought, "There isn't too many stores I know of which don't get suspicious when they see me looking at the lingerie section..." Joe had just wandered out from his usual store, after finding that they had no tights left on the shelves, and was heading towards the back of the shopping centre when he noticed a strange, awkwardly placed store which looked like it had just jumped out of a medieval fantasy story. Its dark...

3 years ago
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Started as cross dressing

This is my true story that happened with I was 26 yrs old. I am currently 28, married for 4 yrs now. I have been a horny guy every since I was in my 6th class and was always turned on by girls. I even made full use of the opportunity of co-ed and used to have fun with most of the innocent girls. I got married when I was 24 to a girl who was two years younger to me. She was a typical traditional girl with a very reserved and religious view of sex. She hardly liked variety and soon I discovered...

2 years ago
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Crossdressing self bondage in an empty apartment

Tonight is the night that I am going to try a daring crossdressing self bondage experience that I have been planning for some time.First of all I start with my complete feminisation. As I am going to be a total slut tonight I apply my make-up accordingly. Once I have applied foundation and powder, I use a dark eye shadow to give me a smokey eye look. Then black eye-liner under the eye and I apply long false eye-lashes. I paint my lips a deep red and then lip gloss on top, making them full and...

2 years ago
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My First Crossdressing Experience

Hi indian sex stories dot net dosto mera name jiya he aur ye meri pahli kahani he thodi bahot bhul ho jaye to maf ker dena. Me apne bare me bata du me ahmedabad ki rahne wali hu. Meri size 28 26 32 he. Aur me thodi gori hu aur me apni body her month wax kerti hu. Jise meri body ekdam girl ke jesi lagti he. Abe jayada time na lete huye story pe ati hu. Ye kahani 6 month pahle ki he jab meri college off tha. To me net pe search ker raha tha to muje ek post mili cd ki . Fire mene cd ke bare me...

2 years ago
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True tales of submission and crossdressing Chapter Three Tale of Two Sisters

Another true tale... I've told it as accurately as I can from memory. Hopefully someone out there might enjoy this! Background ---------- The year was 2004. I had built up something of an online presence, with profiles on most of the personals sites out there - both as a guy, and as my girly alter-ego. That summer, two rather interesting women got in touch with me. Introducing Mistress Pink... ---------------------------- I had a profile on a well-known UK BDSM site. This...

2 years ago
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Crossdressing the beginning

I would assume that for most men, interest in women’s clothing started at a young age. For me, this occurred when I was 11 looking through the Littlewoods, Gratton and Freeman catalogues that my mother used to have.At the time, I lived with my mother Jane, who was divorced, my brother Anthony and sister Sharon, who were five and three years older than me. It was quite easy to sneak one of the catalogues up to my room and thumb through them. If one of them had bothered to look at the catalogue,...

1 year ago
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Cross Dressing for Ann Again

About a week after my first amazing session with Ann, the neighbour from downstairs who blackmailed me into modelling her lingerie, I was again accosted by her on the stairs.“Hi,” she said, coming out of her front door as I was passing. “I’m glad I bumped into you” (I knew she was lying in wait behind the door watching out through the spyhole) “are you doing anything on Wednesday night?”I said I wasn’t and she said that as John and Ian (her husband and son) were going to Aberdeen to watch the...

2 years ago
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my first cross dressing play time

i sucked my first cock the other day. i posted a ad on craigs saying i like to cross dress and would like to find somebody to dress up with and take turns being sluts to each other and then i posted a few pics of me from my xhamster profile and actually got alot of replies. it took a few weeks but i finaly found somebody that like to dress up and he came over during the day and we started watching porn and i pulled out all my slut clothes and we picked out things that we wanted the other person...

4 years ago
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Cross dressing gay fantasy

I would wear black stockings and no other clothes. My whole body would be shaved. I put on cream that makes my skin look even whiter and blemish free. I want my skin to look as feminine as possible. I would wear a jet black wig like a messy bob. One were I can pull the hair over to partially cover my face. I would wear oversized black sunglasses with dark red lip stick and maybe some temporary acrylic nails. I sit on top of the kitchen work top with my knees up at my chest and feet crossed...

4 years ago
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All day crossdressing twosome

This experience was a twosome with my closest tranny friend.We got together one Sunday morning and transformed ourselves fully into hot sexy sluts. We were both wearing well stuffed bras, suspender belts, crotchless panties, stockings and high heels.We lay on the bed together kissing and stoking each other. We had made sure we had full balls for each other, so we were very horny.I got a pair of handcuffs and we closed them tight around our genitals, joining us closely. The twist was that the...

1 year ago
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Bi MMF FemDom Cross Dressing Cuck Part 3 Oh M

All dressed up super sexy, I was setting out for my erotic date with my new lovers, former friends. I felt so desirable and sexy as I drove to my erotic destination. I couldn't help but have a boner the whole time I was driving. I kept feeling myself while I drove. Feeling my exposed thighs, my smooth legs, my silicone tits, my sexy cock.... I was insanely turned on. I also kept looking down at my fuck me pumps. I'm addicted to heels more than anything else so just the sight of my sexy...

3 years ago
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First Cross Dressing Experience

Let me start the story and sorry if I make any mistake because I am excited to share my fun time with you people so I am an engineering student from Mumbai 20 years old. My name is raj (name changed) and used to have a big fantasy of dressing like a girl and wearing all those ladies cloths. I would like to make it clear that I am not a gay but when I dress like a girl. I feel like a girl and make me comfortable with a guy; at that time I get a girlish feeling which makes me horny and takes me...

3 years ago
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Cross dressing first time out

Now I had been seeing mike for a few months now and the relationship was going well. He had introduced me to paul he work friend for a three some which was amazing and the dressing up was getting more and more kinky!!! He hadn't never pushed the boundaries with me kept it simple and sweet, until now!! I always did as as he asked to a point, never anything abusive or nasty he knew what I was into. So when he asked me to dress up and go to a night club i was shaken and a bit scared!! I had never...

3 years ago
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First Time Cross Dressing

Lisa Smith was always a bit spoiled. She was a sexy and teasing little minx. She was 22 years old with a smoking hot body. She loved to tease and be treated like a princess. She acted all sweet and pretty but she had a wild side. She loved to control men. She loved to make her buy her stuff. She loved to cock tease. She made a lot of money on it. She loved the power and intimidating them. She prided on getting a man to anything just by using seduction. One thing she wanted to do but never got a...

Fetish
1 year ago
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My Crossdressing Urge

Having previously enjoyed my lustful dalliance with my first cross-dresser, the thought of him clad in beautiful lingerie was an image in my mind that I could not shake for weeks. I had discovered my liking for women's underwear in my teens when I used to visit my grandmother, and she always had beautiful stockings in her hosiery drawer. I would slip them on when I would stop overnight, delighting in their feel, the smell of the smooth nylon as it encased my teenage legs. Sometimes, I would...

4 years ago
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Wife indulges her husband8217s crossdressing fetish

When my wife Jane asked if I would be a volunteer worker at her company’s western night, I said sure, why not? She told me she would fill me in on the details as the time drew nearer. A couple of weeks before the event, Jane started making a satin saloon girl outfit. I teased her and told her to be sure to make it extra frilly and sexy, and she said I could be sure of it. It wasn’t until two days before the party that I got the rest of the story. When our costumes were ready, my...

3 years ago
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cross dressing fantasy i didnt know that i had

went on a stag holiday to ibiza with about 20 of my mates a couple of years ago.the holiday mostly consisted d**g taking copius amounts of drink and sl**ping with llots of women. the main stag night was fancy dress,and id already planned before i came away id already decided that i was gonna wear i toga and my girlfriends flat gladiator sandals and go as troy.a few of us got quite pally with the girls in the appartment opposite and the daytime before the main nite out one of them commented that...

3 years ago
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cross dressing fantasy i didnt know that i had

went on a stag holiday to ibiza with about 20 of my mates a couple of years ago.the holiday mostly consisted d**g taking copius amounts of drink and sleeping with llots of women. the main stag night was fancy dress,and id already planned before i came away id already decided that i was gonna wear i toga and my girlfriends flat gladiator sandals and go as troy.a few of us got quite pally with the girls in the appartment opposite and the daytime before the main nite out one of them commented that...

4 years ago
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Xena Versus The Spartans

It was a time of horrible raids by terrible marrauding hordes, which caused untold misery, fear and poverty in all of Pelopones. It was a time when Xena and Gabrielle were needed by all the towns, before it is too late, but she was nowhere to be found. The century before had been a good time for all, under the Cooperation Accord of Olympia, there was piece between all the polises, and Xena could concentrate on petty crime and feuding Gods. But now Xena had been on a mission in Asia for years,...

1 year ago
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Cross dressing

Hello is my story. This happened. It was the mid 80’s and I just turned 17 so I thought I would go to the mall near my home town on Long Island and go shopping with my birthday money. I was looking for clothes with and I need to use the rest room. I walked into the bathroom, and the floors were wet so when I made a turn, I slipped. I put my hand against the door of a stall that was closed as not to fall, and the door it flung open because it was not locked properly. I looked inside and a man...

3 years ago
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The Cross She Bore

Memories are sometimes not to be trusted. In looking back on the past, what one believes to be a memory is in actuality what one prefers to think the past was like. We do this unintentionally -- whether as a defensive mechanism or the result of the layering of visions of the past, one on top of another, until the distant past is obscured. For Rebecca her fascination with the cross and with the practice of crucifixion seemed in retrospect to have been acquired at an early age. Now as a single...

2 years ago
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Road Trip Jim Mellons Erotic Journey Across AmericaChapter 26 Montana

After seeing Yellowstone National Park, I knew that I wanted to come back in warmer weather. A few of the side roads through the park that looked interesting were closed to traffic. I headed for Livingston, Montana for an overnight stop before getting on Interstate 90 and heading west to Coeur d'Alene where I had an ex-Army friend. The day had started sunny, and according to the forecast, clouds would roll into the region before a small front swooped through with a chance of light snow...

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