Steve

I was a bit of a loner with very few friends, curious about my sexuality and wanted to dabble in cross-dressing. I was also looking to move out from the family home, but I wasn’t working and couldn’t afford my own place. With all the confusion in my head, I just didn’t feel right staying at home. Anyway, I got chatting to one of my good friends about moving out and he told me that his dad had a spare room in the flat above his café. He then phoned his dad and told him I was looking for a job, and a place to stay.

The next day, my friend introduced me to his dad Steve. He was a handsome man in his mid 40’s, and recently divorced. Anyway, he was looking for waiting staff for the café and offered me a job on a week’s trial. I accepted the offer and asked when I could move in. He said I could start work the next day and move in anytime I wanted, and set the room rent at £30 per week. I was happy with the arrangement, and then headed home to break the news to my parents.

That evening came round quickly, and I started to pack my bags. My parents seemed happy enough to let me move out, and my dad even dropped me off at Steve’s flat, handing me £30 for my first weeks rent.  I got out of the car and pressed the buzzer on the flat door. The door lock clicked open and I went inside with my bags.

 Upon my arrival, my friend Gareth was there and stayed a while until I got myself settled.  He left about 9pm, leaving just me and his dad. I sat down on the armchair, and Steve started asking me questions, like why I wanted to leave home and how I liked to spend my free time. He seemed trustworthy, so I told him the truth.  I explained that I felt confused with my sexuality, but was scared of what my family would make of it, and that I thought about cross-dressing. Steve looked at me with a smile on his face, and told me that his ex-wife had left some clothing behind when she left, and that I was welcome to help myself to it. He also told me that whatever happened in this flat, stayed there. I said thank you and the subject changed to sex.

Steve continued looking at me, before asking why I felt sexually confused. I told him that I had seen gay porn magazines and liked what I saw, but never had the courage to experiment with other guys. Steve then beckoned me to come over and sit beside him on the sofa, and I did. He put his arm around me and kissed the top of my head, before saying that I could practice sexual acts on him if I wanted to. I told him I was only 16, but that didn’t deter him. He then stood up and took me into his bedroom, asking if I would sleep in with him. Nervously, I said yes and we both stripped down to our underwear and got into bed together. Nothing sexual happened that night, we just cuddled in bed.

The next morning, Steve woke me up with his hand inside my boxer shorts, wanking me off. His cock was pressed firmly against my bum, and he was dry humping me as he stroked my hard cock. I reached behind me and grabbed his throbbing manhood, thinking to myself, how big he was. I started to wank him off making him moan with delight. I couldn’t believe what was happening, and with my best friend’s dad. Anyway, we continued wanking each other off until we both ejaculated. He had cum right up my back, and I had cum in his hand.  He then got up, went for a shower and got dressed ready to go open the café. I laid on a while longer, and then went to have a look what clothes his ex had left.

In the bags and boxes, there were all sorts of stuff. Knickers, bras, sexy lingerie and other stuff including skirts, skinny jeans and leggings. I pulled out a royal blue and black Basque and matching thong and suspenders, before trying it on. It fit perfectly and felt amazing on me, so I kept took it off and put it to one side. I needed to get some stockings to put with it for the outfit to work. Then I tried on a pair of the skinny jeans, and again, perfect fit. They even showed my ass off beautifully, so I added them to the keep pile. There was plenty more to rummage through, but I had to get ready for my first shift in the café. But, as I went downstairs, Steve told me I wasn’t needed yet as it was quiet. I whispered to him that I had tried some of his ex’s stuff on and it fit perfectly.  He asked if I needed anything to go along with it, and I said I needed stockings. Steve pulled me aside and told me there were a couple of packets in the top drawer of the chest in the spare room.  I said thank you and that I’d have a nice surprise for him when he got time.

Seeing as I wasn’t needed, I went back up to the flat and found the stockings. I then undressed and put on the sexy lingerie again. I struggled with the stocking clips a little, but eventually figured them out and was soon ready. The material felt amazing against my skin, and I began to get aroused when I saw myself in the full-length mirror. All I needed now was for Steve to come up and see for himself.

Half hour had passed and I heard the flat door open. Steve was back, so I stepped out into the living room for him to see me dressed up. He took one look and whipped is cock out, which was throbbing hard. I moved slowly towards him, kneeling down at his feet and asked if he liked what he saw. He did, so I took hold of his massive cock and began to lick the tip and the shaft, before taking him in my mouth for a short while. Steve was really horny, and asked if I wanted to try anal with him. I was weary of it due to his cock size, but I really wanted to try it and said yes if he went easy on me, and stopped if I told him to.  He then asked me to kneel on the sofa, so he could prepare me. I did as he asked and he proceeded to pull my thong aside and stick his tongue in my anus. Steve gave my hole a good licking, making it nice and wet. He did that for a few minutes, and then got into position ready to penetrate me.

The feel of his cock pressing against my opening, and the tip entering me made me let out a loud squeal as it did hurt a little. Then slowly, Steve pushed himself in further, inch by inch until the initial pain went away. My whole body shuddered with excitement as I managed to take the entire length of his huge tool. He asked me how it felt, and if he was okay to carry on. I said yes and he slowly began to push in and out, picking up speed every few thrusts. It just felt so good and made me cum several times before he finally reached orgasm and filled my hole with his jot sticky load. Now, I was no longer confused about my sexuality and was more than happy to give my anal virginity to Steve.