A declining man's diary of sorts: Mandy (M+F) | 2016

I've been lurking here for some time, and finally decided that I should share some of my previous adventures. I'll be attempting to post them in chronological order, starting with my first memorable experience. I apologize if there are any inconsistencies, my memory isn't what it used to be.

A little about myself before we get started. My name is James and I'm a six foot, skinny, brown haired, average looking white nerd. At the time of this story I was 20, at least I think I was. Maybe it was 19? Who cares, let's get onto the story!

It was the early 2000’s and I had been single for quite a few months, and I thought I would try out this online dating thing. Living in a small town I did not expect that I would match with anyone, but my luck would change a few weeks later. I had matched with a nice young woman in my area, and she to was looking for a casual encounter, not necessarily into dating at the moment. Sounds like a win win situation for all parties involved. We messaged back and forth for a few days before we decided to meet up at a coffee shop near my apartment.

I wasn't expecting much out of a coffee date, and I had heard the stories of the ol’ bait and switch. Boy was I wrong. “Are you James?”, asked a voice directly in front of my newspaper. I probably looked foolish at this point and my mouth may or may not have been hanging open, but when I looked up and saw a stunning young woman that looked just like her profile picture, I was in shock. “Hi! Hello… Yes, I'm James. So that must make you Mandy?”, I asked hopefully. “Yep, that's me” she exclaimed, sitting down.

Let me describe Mandy now, to get us all on the same page. She was a whole foot shorter than me, shoulder length red hair, pale skinned, and in a long winter jacket. Damn, I thought to myself, I'm going to have to wait to see her body until later.

We had barely finished our coffees when Mandy suggested we head back to my place so we can get a little more comfortable. We bundled up and walked a whole five minutes in a light snowfall back to my place. When we got inside, she wasn't taking her jacket off and just seemed to be hanging out while I took my boots off. “Need help?”, I asked. She giggled, “No silly. I have a surprise for you from our conversation the other night. Go wait on the couch and I'll be right over after I freshen up”. I pointed around the corner, “First door on your left”, and walked over to the couch.

It felt like a thousand years had passed already, when in reality it was probably a whole minute by the time I heard the door open. As a fan of surprises, I kept my eyes directly ahead and waited for Mandy to come around the side of the couch. I would have waited an actual thousand years to set eyes upon this gorgeous woman in front of me. She was in a plaid knee length skirt, white top that looked like it was a size too small. Her C cup breasts were preventing the top couple buttons from being done up, and I wasn't going to complain. “It's from my days in Catholic school. And I can't believe it still fits… sort of anyways,” as she gestured to her chest. “I see...that,” was all I could think of to say, as my blood started rushing to my loins.

Mandy giggled again and then walked in front of me, told me to relax, and slowly lowered herself onto my lap. Everything was moving in slow motion. I reached around her waist and cupped her firm yet ample ass with both hands, pulling her body closer. Moving my hands up her sides, holding her closely, I finally kiss her. Our tongues explore each other's mouths while our hands explore our bodies, our shirts came off. Finally coming up for air, I start kissing her neck while I fail at unclasping her bra with one hand. I reach around with my other hand and manage to unclasp it. She makes a joke about me being out of practice or never learned to do it one handed. I pull my head away from her neck and look her in the eyes, smiling sheepishly. She shrugged her bra off and lets it fall in between us.

Her breasts didn't really move when the bra fell away, at least not that I noticed, and I was staring pretty intently. Now they were moving left to right and back again, rather casually. That was odd. She was clearly trying to break me out of the spell her magnificent perky tits had put me in, and it worked. I looked back up to see her eyes closed with a smile on her face. I grabbed her ass again, firmer this time, helping her move back and forth on the bulge in my jeans. She leans forward, kissing up my neck, breathing heavily into my ear, “I need you inside me”. I lifted her up and carried her over to the kitchen table, sitting her down on the edge. Kissing slowly down her body, stopping momentarily at her breasts to lick and nibble at her nipples, I kneel down on the floor and start kissing her thighs. I can see how wet she is, she's soaked through her panties. I pull them aside and give her pussy a quick kiss. “Seriously, get in me. No more foreplay”, she lightly moaned. Standing up, I pull her towards me. Taking the hint, she stands up. I go in for a kiss, our lips barely grazing when I spin her around and bend her over the table. Flipping her skirt up, I have a realisation, her panties are still on. Fuck it, I can just move them aside, I think to myself. I unbutton my jeans and pull my cock out, letting it briefly rest between those amazing ass cheeks.

Pulling her panties aside, I can feel fingers lightly graze my shaft before she fully gripped it and pulled me towards her. I slowly entered her tight pussy, pushing all the way in. Pumping slowly in and out to get her accustomed to my girth. After a little bit of that I start to pick up the pace and before I know it I'm fucking her with reckless abandon. I've never fucked anyone this hard from behind. She's moaning and I can feel a light flutter near my balls when I'm all the way in. She's playing with herself. She starts moaning louder. This is it. I can feel it. I'm about to blow. I pull out and she immediately spins around and kneels down. I unload onto her neck and tits, and the floor, and her skirt. Oops.

I help her up and she goes to clean off in the bathroom. I wipe up the mess on the floor. She comes back over to the couch, picking up her clothes on the way. “We will have to do this again! I have to leave soon, sorry about the rush,” she said while sitting down and putting clothes back on. “Don't be sorry. We all have lives. Understandable”. I walked her to the door, gave her a hug and kiss goodbye. We continued to fool around for six months before she told me she wants to try things with this new guy to see where it goes.

I apologize if this is too long and drawn out for you, but I wanted to put as much detail as I could remember. I learned a valuable lesson from this, besides not putting a condom on, if you're pulling her panties to the side, pull it further than you think. Chaffing is bad, mmkay?