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.
