This is story of the first time I crossdressed with someone else and my first time with a much older guy.
I had been secretly crossdressing since a very young age. Not an unusual story I guess. I used to be home alone a lot and would take every opportunity I could to do it. It was mainly my mums stuff. I loved nylons, tights, stockings and heels although I also enjoyed the feel of panties and a bra too. I would stuff it to feel like I had tits.
As I got older I still loved doing it. Still using mums stuff, sometimes a girlfriends if I had one at the time and very occasionally I would get my own stuff. Still too scared to buy from shops I would buy stuff from Halloween stores.
I was a heavy metal guy and that actually helped a lot because it was totally normal when I grew my hair long. I had it so long it was almost down to my bum. Combine this with being so skinny, I was only around 98 pounds, I could pull off a very feminine look.
My mum worked a lot of hours and night shifts so I essentially had a house to myself most of the time which was great for inviting people over for hook ups and I sure made the most of it.
Ever since I was sexually active I had always had a thing for older guys and to be fair they were pretty in to me too. Still to this day its something I love. There's probably some deep seated psychological reasoning behind it but let's not get all Freudian.
One night I was on one of the old hook up chat rooms and got talking to a guy. He was in his late sixties. We were talking about sex and I was clearly getting very turned on when he asked me if I ever dressed up. So I explained that yeah I did but had never done it with anyone else before. Well he asked if I would like to and I nearly chickened out but he seemed nice and was really into the idea of it so I gave him my address and told him to come over in an hour.
I picked out an outfit from the little stuff I had and tried to make myself look like a goth girl. I had on purple and black striped tights, a black mesh puffed up mini skirt, a black kind of bustier top and a pair of black heels. I did some eye makeup and purple lipstick then brushed my hair into a flicked over look.
I thought I looked pretty cute but as the minutes ticked by I started getting more and more nervous about how I looked. What if I actually just looked silly and he would laugh at me?
About ten minutes later a car pulled up and I watched him walk towards the house. It genuinely crossed my mind to not even answer the door. I heard his footsteps coming down the path and my heart was racing. I couldn't believe I was actually doing this.
I opened the door, he came in, took his jacket off and looked me up and down. I just kinda stood there shuffling nervously and not really looking at him. He stepped forward, put his hands on my waist and pulled me close to him.
Hes asked me how I was feeling.
"Ok, a bit nervous."
He told me I looked really cute and his hands started moving over my body. He pulled me in, started kissing me and really started groping my ass. It was quite overwhelming at first. I wasn't inexperienced but this was a first, all dressed up with the oldest guy I'd been with by some distance.
I was just stood there while his hands went up my skirt. One grabbing my cock and the other groping my ass.
He pushed the tights down below my ass and my cock sprang out. His fingers started pushing into my ass, rubbing my hole. His other hand wrapped around my cock and started working it. He was kissing my neck. I honestly felt like I could explode. He was just manhandling me.
I started rubbing his cock over his jeans and it was already hard so I undid his belt, unbuttoned his jeans and pulled them open. They fell to his feet revealing tight black boxers, that bulge was feeling big.
I got on my knees in front of him and pulled his boxers down.
Now, it's not like this was the first cock I'd ever seen but I actually gasped when it sprung out. It was maybe about six inches long but about the thickness of a coke can and absolutely rock solid. My hand couldn't even fully wrap around it.
I was stroking it up and down and he pulled my head towards it, brought it to my lips and sucked that big helmet into my mouth. It tasted amazing and I tried to get more in. It was so thick I could barely fit it in.
He kicked off his shoes, Jeans and boxers and sat down on the sofa. He spread his legs and pulled me towards him, guiding my mouth back onto his cock.
He started to gently fuck my mouth while holding my head in place. Every few strokes he got a little deeper and was able to really open up my mouth. It was now hitting the back of my throat and making me gag a little but he didn't stop. He just held my head and kept fucking away at my mouth.
All the time he's pumping my face he was talking dirty to me. Telling me I'm a good girl for taking his cock and a little slut for loving it. I just let him use me how he wanted.
After about ten minutes he stood up and moved me around so that my head was on the edge of the sofa. He stood over me and forced his cock into my mouth again. This time he really went for it and started pumping hard. I was gagging like crazy and there was drool, spit and precum just pouring out of my mouth and down the front of me.
A couple of minutes later he was really groaning and started telling me that he was about to cum. He told me to take it like a good girl and open wide.
The first squirt went right in my mouth and then he pulled back and started wanking that huge cock furiously. Rope after rope shot all over my face and into my mouth. There was so much that is was just dripping off of me and all down my front. I was breathing so hard from the face fucking that I couldn't move. Once he had stopped shooting he told me to stick out my tongue and then wiped the last drop of cum from the tip of his cock onto it.
I was just lying there half on the floor, half on the couch, unable to move. He pulled his clothes back on, told me I was a great little cock sucker and walked out the door. I didn't move for a few minutes but realised what a state I was in. Tights pulled down, covered in cum and my cock was still hard as a rock.
I scooped up the cum from my face and body and used it as lube to rub my own cock this time. Within a minute I was shooting hard and covering myself with cum again.
I lay there for another few minutes trying to collect myself. Picked myself up, went for a shower and tried to wash it all away.
And that was my first time dressing up for someone else and my first time with a much older guy.