Diary of a Sugar Baby Pt. 01

My name is Lucy. I'm a 20 year old Law student and I date older men for help with expenses.

I've rewritten the beginning of this story so many times because where does any story really start? I wasn't born a sugar baby. I started out 'normal', dating kids my own age, having frustratingly bad sex, wondering what the fuss was about.

My parents are both professional people. Mum's just turned 40 (she had me while she was at uni) and dad is some 23 years older. For as long as I can remember, mum has had boyfriends and dad has never seemed bothered by it. She'd either bring guys home for a weekend or stay up in their London apartment for a few days.

So my story starts when I've just turned 18. Mum had been staying in London due to work so I paid her a visit. She was bustling around, getting ready for a date. Mum's very glamorous for her age and has kept her figure. We're both blonde, size 10, and 5'4. She'd prefer that we were sisters, and she's never been hugely maternal; like, if I fell and skinned a knee, she'd be too busy and my dad would deal with it. But when she caught me giving a blow job when I was younger, she made sure I got on the pill asap.

Anyway, she was getting ready and said "Hey, my date Martin's colleague is in town too and at a loose end, why don't you come along for a double date?"

So I'm like "Eeww, the last thing i want to do is have a boring night out with old people."

Mum shrugged. "Up to you, but we have a reservation at the best new restaurant in the city, and Martin is paying. Free wine! And you can borrow my Louboutin boots you like so much...?

Yeah, so the call of the Louboutins was strong. I borrowed one of her cocktail dresses.

The date turned out to be a lot of fun. The restaurant was great, wine flowed as did conversation. Martin was charming as was his colleague, Dan, who turned out to be an attractive 5'11 43 year old American, well dressed and smelling good too.

Dinner was over all too soon and mum invited the guys back to the apartment for more drinks. They were both really good company and we talked for an hour or more before mum got up, took Martin by the hand and said "Time for bed. Dan, it was lovely to meet you, show yourself out when you're ready, Lucy, I'll see you in the morning. Good night!"

Mum and Martin disappeared. Dan and I looked at each other. He leaned in and kissed me and I let him. Probably my best kiss ever. Wow. He took my hand and put it on the bulge in his trousers. "Are you going to let me fuck you, Lucy? I very much want to."

I nodded. I stood up and led him to the spare room and let him undress me. Suddenly everything was happening quickly and I was naked and on the bed and he was kissing me, then my breasts, then my tummy then final OH MY GOD his head was between my legs and compared to the boys who had made half-hearted attempts to eat me before, this was a religious experience. He pushed my legs apart and peeled me open with his thumbs and connected with my clit and I think I had my first orgasm (and my first ever from oral sex) within a minute of him starting. And not just an "Oooh, that was nice" orgasm. It was so fucking intense I could hardly breathe, I'd never even given myself one like that.

He kissed his way back up my body, licking my sweat, and lay next to me.

"Was that OK?" I nodded breathlessly.

"I'm glad. So are you going to suck my cock?"

I nuzzled his chest, revelling in the smell of him, the scratch of his chest hair against my cheek, and worked my way down, wrapping my fist around his thick, throbbing prick, stopping to admire it (it was the first circumcised one I'd ever seen) before taking him between my lips. He smelled and tasted so clean, unlike all the boys I'd sucked off in the past, I took him deep into my mouth, swirling my tongue around his beautiful shaft, desperate to give him as much pleasure as he'd given me. I felt his hands on my head, holding me, guiding me up and down, so he was fucking my mouth, and I loved it, so much more pleasurable than when guys just tried to ram it to the back of my throat.

All the time he was talking softly to me... "that's it, baby, suck it, suck my cock, Jesus that's so good, suck it, you suck like a bitch, that's so fucking good... oh God, oh God, I'm gonna cum in your mouth..." I felt his body tense and his cock swelled and throbbed rhythmically and he emptied his balls into my mouth and I took it all... "Jesus fucking Christ, that it baby, swallow for daddy, swallow daddy's cum, swallow it all..."

Even his spunk tasted good and I swallowed it all, eagerly, then continued sucking him clean as the throbbing subsided and his cock softened.

I crawled back up the bed and rested my head on the pillow next to his. "Was that OK?"

He grinned and nodded, then leaned over to kiss me, his tongue inside my mouth, tasting himself. I reached down and held his cock, hoping he would get hard again, I was desperate to have him inside me. I'd already just had the best sex of my life and he hadn't even fucked me yet.

It didn't take long and his deep kisses were making my pussy hum. He was hard again, whispering in my ear "I'm gonna fuck you so hard..." then got up and knelt between my legs, looking down at me hungrily. Suddenly it didn't feel weird being naked in front of a man older than my mum, it felt right.

"Open your legs" he said. "I want to see your cunt."

I spread my legs wide for him, hearing that word making me want to be dirty for him. I reached down and spread my lips for him, making him gasp, and without warning he was on me, I grabbed his cock and pulled him into me and it felt so good, so right, as I felt his full length inside me, stretching me, filling me, owning me. He started thrusting, long, slow strokes and my body took over, my hips jerking against him involuntarily, trying to take him deeper and deeper. Already I could feel stirrings deep inside myself and I knew I was going to cum again. "Fuck me, Dan, please, fuck me, it feels so fucking good, make me cum..."

I felt his cock twitch inside me. "Jesus baby you are so tight... daddy's gonna fuck you up real good..." with that he paused and put my legs over his shoulders. "Daddy's gonna mess you up so good."

I was bent nearly double as he started ramming his cock into me, one hand roughly squeezing my boob and pinching my nipple.

"Take it, bitch, take it!"

He started fucking me hard and fast and I was lost in the moment, it felt like every part of me was throbbing and on fire, I was talking shit and had no idea what I was saying and then my pussy - my cunt - exploded. My head exploded, the force of my orgasm making me clench around him, which triggered his orgasm, and finally we were laying side by side again, both drenched in sweat and panting like dogs, grinning like idiots. I was totally wrung out, my skin hyper-sensitive, my pussy - my cunt, I love that word now - feeling bruised but happy.

We lay there for a while, talking shit, enjoying the glow.

"So," he said, "how do you know Sandra?"

"Oh she's my..." I stopped myself, not knowing if she'd like him knowing, or how he'd react. "She's my boss. I work for her sometimes". He nodded, and said "You wanna go again?"

He fucked me twice more that night, each time as good as the first, before we fell asleep.

I expected breakfast to be awkward, but mum took it in her stride, but giving me a wink when nobody was looking.

Dan flew back to the States later that day and I never saw him again, but I'll always be grateful to him for my sexual awakening, and turning me on to the idea of older lovers. He was the first, but by no means the last.