I was eighteen, had a great circle of friends, a beautiful girlfriend and a great sex life. I was also completely in the closet about being bisexual and a crossdresser.
The only people that knew about that were the strangers that I hooked up with from chat rooms or had played with at the local glory hole. Not one of my friends of family had any idea.
I stayed at my girlfriend's most of the time as her mum stayed at her then boyfriends, future husband and step dad to my girlfriend, house most nights. If I wasn't going to college that day I would just stay there while she went to school so I ended up in the house all day by myself a lot of the time.
At eighteen I was a skinny guy, about 168cm, very boyish face and long brown hair. I was a heavy metal kid so the long hair that nearly went down to my bum wasn't out of the ordinary. My girlfriend was just a little shorter than me and a similar size with a great wardrobe full of the cutest skirts, dresses, tops and every other thing a closeted crossdresser could want. Even our shoe sizes were similar and she had some amazing and sexy heels and sandals but my favourite were a pair of black leather lace up knee high high heeled boots.
The thing about my girlfriend is that she was also really kinky and if I had just told her about the dressing up she would most likely have been into it. If I wasn't dealing with some kind of internalised homophobia I guess I would have, I know better now.
One of the things she loved was getting fucked in her mums bed and once she discovered her mums collection of sex toys she really got off on using them too or dressing up in her lingerie.
Anyway …
On this particular day I had the boots on, a short green mini dress, her mums white hold up stockings, matching white lacey panties and bra. I'd styled my hair nice and had just a little eye makeup and lipstick on. I had a bottle of poppers, some lube and one of her mums dildos lying on the bed.
I'd enjoyed a couple of hours getting all dressed up and ready and now it was time to really enjoy myself. For the next half hour I made the most of the poppers and the dildo. I was really getting into it. Face down, ass up and working that dildo in and out of my hole. My cock was leaking and I was having a good old time moaning away, poppered up and pounding myself.
Now, I'm not quiet during sexual activity and especially not when there's anal play involved so I didn't hear the door opening downstairs or anyone coming into the house. The first I knew that anyone was there was when I heard the voice.
"Holy fuck. What the fuck."
I jumped up, turned around and there was her mums boyfriend standing there with his mouth agape and wide eyed taking in the sight of me all dressed up and still holding on to that dildo. He made a couple of noises trying to speak but he clearly couldn't get the words out. After what felt like an eternity, but was probably only thirty seconds, he turned around and walked out the room and I heard him going down stairs, pacing about and muttering to himself.
I was fucked and I could see my whole world collapsing round about me. For the first time ever I had been caught by someone I knew and to make it worse he had caught me in his soon to be step daughters clothes using his soon to be wife's dildo. I just collapsed onto the bed and started sobbing. I knew he was going to tell her, I would be dumped and she would tell everyone else. My life was over.
That seems a bit melodramatic now but at the time that was exactly how I felt.
I don't know how long I had been lying there for when I heard a knock at the bedroom door and him speaking.
"I'm coming ok, you're alright, I'm not going to freak out"
He came in and sat on the edge of the bed, I was lying facing away from him. I didn't want him to even look at me I was so embarrassed and ashamed to be caught like this. He started talking to me, telling me that it was just a shock to walk in to see that. He was actually just coming in to see if I wanted to go for a game of pool because my girlfriend had told him I was just sitting about bored most days. He chuckled a bit and said I guess you're not really that bored after all.
I felt his hand on my waist and he asked me to turn around and talk to him. When I did he actually wiped the tears from my cheek and told me my makeup was running a bit which made me laugh. He patted the bed beside him and got me to sit up. When he told me not to worry, that everything would be alright I burst out in tears again and he put his arm around me. I was really sobbing but he was trying to put me at ease. He told me he wouldn't tell anyone and that it would be our secret.
He started asking me about the crossdressing and I found that the words just tumbled out of me. I told him everything about it. The relief of telling someone about it after so long was amazing.
Eventually i realised what the present situation was and i started to feel a bit awkward. I stood up and said to him that I should probably change. The next thing I knew was that he was standing up and putting his hands on my hips. I looked at him and he was eyeing me up and down. He said to me that, actually, I looked really good and that I must have been practicing. His hands moved to my waist and I could see him breathing heavier. I could feel things turning weird.
His hand came under my chin and tilted my head up towards him. He was a big guy, easily at least six feet, and I really had to put my head back to look up at him. He moved a hand behind my back and pulled me closer while telling me that I didn't need to get changed if I didn't want to.
I just kind of croaked out an OK.
I couldn't believe that this was actually happening.
He leaned down and kissed me and it was an amazing kiss. I'm not lying when I say I just melted. It was in the top ten.
With his mouth on mine he started moving his hands over me. I was putty in his hands.
He pulled me down on to the bed, got me lying on my back and then he was over me. His tongue was mixed with mine and his hands were all over me. I was spreading my legs and he was grinding on top of me, pushing me down into the bed. My arms and legs were wrapped around him as his crotch was grinding against mine through my panties.
He pushed off and stood up while pulling his shirt off. He kicked off his shoes then dropped his jeans and briefs. Now I'm not going to say that he had this perfect body and cock but it was pretty damn nice. A bit of dad body, quite hairy but groomed all over. His cock was uncut and about six inches with a big set of balls.
He reached down and started pulling my panties down my legs over the stockings and boots then got to his knees in front of me and pulled me to the edge of the bed. His mouth was on my cock, taking it to the base on the first suck, and it felt amazing! I started moaning louder and louder as he started licking and sucking my balls. My legs were pushed right back and for a moment he stopped and just looked at me.
He told me to get some of those poppers so I grabbed the bottle, had a few hits and then he did the same.
My head was flush with that slutty feeling and right then I just wanted him to use me however he wanted. With my legs pushed back and wide open again I reached down and spread my ass so that he would be able to see me totally exposed. He leaned in and slipped his tongue into my ass. Poppers and rimming drive me absolutely wild and he was eating my ass like it was the greatest meal he'd ever had. I don't even know if words were coming out of my mouth by that point or if it was just incoherent noises but either way this guy really knew how to treat an ass.
His mouth went back to working on my cock while his fingers started to rub my hole. I felt one slipping in, followed by another and then another. The dildo I had been using wasn't exactly small so I was already opened up nicely for him. He kept fingering me for a few minutes while sucking my cock and I could feel the cum building and my balls tightening getting ready to shoot. I was gasping and writhing around the bed when he stopped and stood up in front of me. I looked at him and his cock was so hard. The foreskin had rolled back and he had this lovely big helmet that was leaking precum. That's when he asked me to tell him what I wanted.
"Please fuck me, I want it"
He pushed me further back onto the bed and climbed on, pushed my legs back and started guiding his cock towards my hole. His helmet rubbing against it was such a tease and I was trying to push my ass towards it. Slowly I felt it start to push into me a little bit at a time. He was now lying on top of me with my arms wrapped around him pulling him close to me. He was kissing me, my mouth, my neck as his cock went slowly deeper inside of me and I started begging him to fuck me, to give it to me, to fuck my ass.
Our bodies were wrapped up together as he started building up the speed of his strokes and going deeper and deeper with each one. It could only have been about ten minutes into it and he was pounding me while u made the filthiest guttural noises. I was talking some filth into his ear. Telling him to fuck me hard, to make my hole his and that I wanted his cum inside me. That seemed to be the thing that sent him over the edge. He sat up, grabbed my cock and then started going really fast and deep with every stroke. He was calling me a dirty little slut, telling me to beg for his cum if I wanted it and then he let out a massive roar as he buried his cock deep inside of me. I could feel his cock pulsing as he shot every bit of cum in me and that was enough to send me over the edge too. My cock squirted cum all up and over the dress, a bit hit me on the chin and he milked every drop from it.
We just lay there for a minute, him collapsed on top and still inside me, both of us breathing heavy, both probably realising what had just happened. I know I was.
He climbed off of me. I felt his cock leave my ass with a plop and felt his cum running out of me. He told me I'd better get cleaned up and he started getting dressed.
A couple of days later we spoke about what had happened and things were OK. We hooked up some more times over the next couple of years before my girlfriend and I split up and that was the end of that.