This happened to me almost exactly a year ago. I'm a 33-year-old guy. I'd say I'm reasonably good looking. Athletic build, 5'10. But moving on...

I had fairly recently moved to a new city in a new province. I had only been here for about three weeks. I was on facebook one night and noticed that an old friend posted that she was in my new town for the weekend. She didn't even know I had moved there, so I messaged her to see if she'd like to meet up while she was in town.

This was a girl I hadn't spoken to in about two years. Back then, she was in a serious long-term relationship with another girl friend of mine. I always really liked her, but when they broke up, it was one of those situations where it would have just been awkward to stay close.

So anyways, she was in town for the weekend and was excited to find out I was living there. We made plans for a drink the next night. Her name is Sam. She's 29. She's blonde, with a cute short haircut. Actually, everything about her is cute. She's petite. Probably 5'1. Barely 100lbs.

We're out for drinks and it's really great to see her again. Even though we only knew each other through her ex, we always got along very well. The conversation was easy and fun. Eventually I asked about their breakup and we got into a larger discussion about relationships. We both confessed to each other that we've been pretty bad over the last year. While I wouldn't say either of us had been slutty, we had each been enjoying really non-committal relationships based primarily on sex.

We were a few drinks in by now, and talking quite openly about our sex lives. That's when she finally dropped the bomb on me:

"I don't know what's come over me lately, but I've suddenly been really curious to know how it feels to be with a guy."

I was pretty floored by this. Sam is not some experimental-stage lesbian. She's 29 and has only ever been with girls. She was living with my friend for years. And so I had never really thought about her sexually, other than noticing that despite her petite frame, she's got great tits and a high, tight ass.

I'm no dummy, so when she confessed that over drinks, I was pretty sure she was implying that she might be hoping for my help with that situation. I played the game with her for a while:

"Really? You never had a boyfriend in high school first or anything?"

"Never."

"So why now, do you think?"

"I don't know. I definitely don't want a relationship with a guy. I just feel like I could easily get into something serious again with a girl. But maybe while I'm single and still young, maybe I should try it once."

(Coyly) "What do you mean by it?"

"You know..."

"No, what? What do you want find out?"

(laughing) "You're going to make me say it, aren't you? I want to know what it feels like to have a dick inside me."

"That shouldn't be difficult. You're super cute. Any guy would love to help you with that."

"But I'm scared too. I need someone I trust."

"Do you trust me, Sam?"

She nodded. Looking both scared and excited.

So I just flat out said it. "I would love to fuck you, Sam."

Still looking slightly scared, she broke out in a big smile. I quickly picked up the cheque and we headed to my place. Luckily I live only a few doors from the bar, because it was an awkward, silent walk.

When we got into my apartment, I took her for the five cent tour, ending in my bedroom. She started to say "it's nice" or whatever pleasantries, but I cut her off by leaning down and kissing her. She froze at first as I grabbed her by the back of the neck, but quickly melted into me, returning my kiss and wrapping her arms around me.

I made quick work of her clothes, getting her down to bra and panties. She pulled off my shirt and fumbled with my belt so I ended up taking it and my pants off as she laid down in my bed.

I got in after her and we explored each other furiously. Kissing deeply, hands wandering. I unhooked her bra and her perfect, perky little B-cup tits sprung out. Her nipples were rock hard.

Now on my back, she straddled me, kissing me. She then sat up, and I could see she was taking in what she was about to do. She slid down and took my boxer briefs at the waist. She paused and looked up at me and giggled nervously.

She finally worked the courage and pulled my briefs down. My cock sprung up, rock fucking hard. Sam just looked at it at first. Then slowly she reached for it. She began stroking it gently, eventually picking up a bit of pace. She was grinning widely as she played with her new toy. She got her face right up close to my dick and I prayed that she'd take me in her mouth. But this was not the night to press her and ruin everything. So I let her stroke me until, still smiling, she came back up and kissed me again.

I rolled her over on her back and this time it was my turn. As I took her panties by the waist, I felt a moment of hesitation, but then she lifted her hips and let me slide her panties off.
She had a beautiful pussy. A well manicured little patch hair above a tiny little, unblemished pussy that was all mine.

I slide up to kiss her. My dick was now right up against her pussy and I could feel the heat. I took my cock in my hand and began to rub it up and down her slit. She was soaking wet and let out a soft moan.

I asked "are you ready?"

She nodded slowly.

I said, "do you want me to get a condom?"

She said, "no. I want to feel you inside me. Just you."

And with that, I pushed my dick deep inside her. She gasped and her eyes went WIDE open. I was about to ask her if it hurt when suddenly she cried out and I felt her pussy spasm and tighten on my cock. Her whole body seemed to convulse and she practically screamed out. Her nails were deep in the flesh on my ass holding me in deep. When she stopped shaking she yelled out:

"Oh my god, I came! Oh, god!"

I remained still. Deep inside her pussy. My cock still throbbing. I leaned in and kissed her. For the next 30 seconds I stayed inside her and felt, what I can only describe as aftershocks. Brief spasms. Mini orgasms.

When it seemed to have subsided, we looked at each other. She smiled and kissed me. That's when I started to slowly fuck her. Super slow at first. Inching back and forth. And immediately she was moaning in pleasure.

A little faster now, building a good rhythm. Her moans were getting louder and louder. Suddenly she shook and screamed in another orgasm. I felt her wetness all over my cock and down onto my balls. I started to slow my pace to let her recover. I asked her if she needed a break and I felt her legs clamp around my ass, pulling me in deep.

"Don't you dare stop fucking me."

This time I built up a faster pace. Faster. Harder. Deeper. I was holding her by the shoulders so I could really fuck her hard and deep without sending her flying up the bed. She was loud and that only made me fuck harder. She had a wild, crazed look in her eyes. This time when I felt her orgasm building, with her screaming out my name, it put me over the edge.

She came again and when I felt that pussy tighten on my cock, I came too. I yelled out myself, as I shot ropes and ropes of cum deep inside her pussy. I'm not sure I've ever had such an intense two-person orgasm. We both held on to each other for dear life as she shook and I pumped her full of cum.

I stayed inside of her as we both tried to catch our breath. We were staring into each other's eyes, seemingly both in disbelief.

Eventually I pulled out and collapsed by her side. After a few minutes, I apologized for cumming inside her.

She said it was fine. Apparently she took the pill to "regulate her cycle." "And besides," she said "I really liked it."

"Yeah?"

"Yeah. I really, really did. I can feel your cum dripping from me now. I like that too."