Colourful Socks

I knew I wanted to lose my virginity to an older man and I knew that I didn't want him to be gentle.

I had a boyfriend when I was 15/16 - didn't enjoy the drama he came with. He was 3 years older than me. I then dated a man who was 25 years my senior when I was 18. I didn't lose my virginity to him, but that's another story.

Late last year, I was in the process of moving out and freshly heartbroken from my last relationship. This was my chance to finally explore a little more because I'd be in and out of a bigger city, staying at hotels. I made a profile on a sugar daddy website, because where else am I going to find older men? I was 19 and wanted to lose my virginity before I turned 20.

My first date was a bit of a flop (read 'fucking disaster'). I won't go into much detail, but I tried to suck his dick and couldn't go through with it. Second date was boring. Zero attraction to either men.

By February, I was giving up. Of the four months I'd spent on the site, I was only responding to messages for about two weeks. Then I got a message from someone that implied he was into dd/lg. My interest was piqued.

We started chatting. Exchanged pictures. He was in his late 50s, white, fit, still had his hair and seemed unlikely to want to kill me then dump me in a ditch. I agreed to meet up. We met at a hotel bar.

He told me to wear something cute. I hadn't thought to bring anything cute. I wore a tight white top and a green skirt (yes, the same green skirt I'm always wearing). He also requested for white panties, but I wore light pink ones instead to match my bra.

He was very attractive, but the first thing I noticed were his colourful socks.

Once we were sat in a cushy corner of the lounge, we started chatting. Normal stuff. Work. Family. Life in general. I wasn't as cheeky as I would have been because he ordered a juice and I didn't want to be the only one drinking.

As our conversation carried on, he gradually started asking me naughtier stuff- most importantly , what I'd done before - I lied and said I'd been with two men, but by technicality I had "been" with two men. I didn't want him to know that I was a virgin.

He told me what he liked about dd/lg, referred to himself as daddy, asked me to spread my legs for him to show him my panties, showed me how stiff his cock was for me in his trousers. There were people around us, but we were a little more isolated and in dim light.

We'd spent almost 3 hours chatting before he said he needed to leave soon. I told him I wanted to suck his cock before he left. Little me thought I would just get him off in his car. He looks at me and then he says we can head to my hotel but he needs to stop for condoms.

Condoms???

I asked him why we would need condoms if I was just sucking his cock. He said he wanted to have his way with me. I was nervous, but I still didn't tell him I was a virgin.

Next thing I knew, I had condoms in my purse, we were in the elevator and he was grinding his cock against my ass. I was in just my panties within 2 minutes of getting in the hotel room. He followed suit after. Birthday suit, to be specific. His cock was average - I'd say 5/6 inches, average girth.

He pushed me on the bed and I asked to suck his cock. I got on all fours and sucked his cock. He touched my ass, rubbing it, spanking it, then he fingered my pussy.

I started bleeding. No biggie. He asks me if I'm on my period and I told him I wasn't. I think my mouth on his cock was enough to stop his questioning. He lays back and I suck his cock again. His hand in my hair kept trying to make me take more, but I kept gagging. I was rusty - it had been a year since I last sucked dick. He loved the gagging, though.

Then he tells me to ride daddy's cock. I thought it wouldn't fit. I watched him put the condom on. Straddled him. Aligned his cock to my virgin pussy.

He fit. I felt the typical 'elastic band snap'. My eyes rolled back. It didn't hurt at all.

Then he started bouncing me up and down. Playing with my little tits. Telling me he loved how tiny and perky they are. Wrapping his hand around my throat. During this, I was just in my head thinking, 'wow, it's really happening'.

It wasn't long before he rolled us over and fucked me hard. He gripped the headboard and was just slamming into me. I gripped his shoulders, caressed his hair. Then he told me he was going to cum and he went even harder.

He came and collapsed on top of me. The actual intercourse lasted about 5 minutes.

I didn't cum, but I was just too busy thinking about how I was losing my virginity rather than actually enjoying it.

We cuddled for awhile after. Then he asked why there was so much blood again (I still had my panties on and they were a mess and yes, I still have them). I told him I was a virgin.

He was a little shocked. He said he felt bad that he'd fucked me so hard. I told him that I wanted it like that. Then he teased me with the idea of him fucking me even harder if I'd told him, but it was done.

We cuddled a little more before he had to leave. Then I went to bed and I could still smell the fresh sex in the room when I woke up, but that was just my pussy wanting more.