Valentine's Day with Eve [mf] | 2016

This wound up much longer than expected. Part 1, Part 2.1-2.3 (main sex story), Part 3 and an Epilogue.

I would have to lead this by saying that I have a... thing for married women. I don't actively convince them to cheat on their husbands but if it's presented to me as an option that certainly gives me a little more fire. After all, I didn't promise to love/honor/obey/etc. anyone. I, myself, have never even vaguely cheated on someone - and when I'm a regular sidepiece for a married woman, I try to remain monogamous myself.

Such things have ended... badly, more than once. A stupid, stupid pregnancy scare, another woman deciding she loved me more than her husband, a 13-year old seeing a text on his mother's phone about my desire to cum down her throat that evening. As such, I had sworn off married women. Too much potential drama for the thrill. Never say never...

After putting aside my commitment issues I entered into a two year relationship with a younger woman (30/20 at the beginning) - it started to fray with her being in college without a job, me needing to get seven or eight hours of sleep regularly rather than drinking with her friends on weeknights and as graduation neared I knew I didn't love her enough to ask her to stay rather than pursue grad school elsewhere. I couldn't ask someone to make that choice and then have it end.

To recover, I started hanging out with a group of older friends more regularly. Mostly married guys a few years older, we'd sit around dive bars and talk shit for a few hours once or twice a week - it was a low-stress way to get my introverted ass some socialization post-breakup. A few months into the social club, a woman starts coming along - initially just every so often and soon to our twice-weekly meetups.

I didn't know her from Adam but it came out that Eve had been a regular drinking buddy before twins and hormones had sent her down a spiral of depression and weight gain a few years back. As she came back to the group, she had dropped 50 pounds and gotten (or so it seemed) her head on right and decided she needed some time away from the kids and her husband.

I was attracted to her from the start as she was exactly my type. A few years older (not quite 40), short, curly dark hair, glasses, a smart mouth - and married. In a low-cut top and bra her breasts looked fantastic for a woman her age and while she wasn't necessarily beautiful she was distinctive, with mischievous eyes and a wicked grin after two or three drinks. Even if I hadn't been attracted to her physically her quick wit and sarcasm would have done it for me.

It all seemed irrelevant, as she was married and part of a close-knit friend group. It's rarely a good idea in one's 30s to start fucking a friend, certainly not a married one.

Initially I'm pretty sure she thought I was a cocky young loudmouth and wasn't particularly friendly but quickly warmed up to me - two shit-talkers can't help but get along if neither is a dick. We talked more and maybe flirted a little, but only in the context of our bar meetings, I didn't even have her phone number.

I should have picked up on things the night she let another female friend motorboat her cleavage for laughs, then grabbed my head to do the same. When it came time to leave I walked her to her car and chatted for a moment but looking back she expected me to get in. I never said I'm not clueless.

A few weeks later I get a text after I left the bar from a mutual friend saying Eve had asked for my phone number. Okay, cool, guess we're friends now. At 3AM that night, I'm still up reading and my phone dings - it's a number I don't recognize reading "Your existence distracts me." I quickly realize who it is and decide to not push and boundaries, thinking she might be drunk.

I respond with a simple "Oh, really?" and quickly get my response - "Yes, and I think we need to talk about it." I say I'd enjoy that and wish her a good night.

The next day I have a quick chat with the mutual friend who had given her my number and he filled me in on some backstory: Eve had been married for 15 years and cheating on her husband here and there for most of it. All the other friends knew and generally ignored it - if it it didn't cause them problems, what did it matter?

At this point, I decided she was fair game. The history of cheating assuaged any potential guilt on my part and the desire to see her looking up at me with those glasses on with my dick in her mouth clouded any judgement about involvement with a friend.

So began the process of making it happen. To be honest, this is a bit of a blur - a couple of weeks of missed opportunities, a lot of dirty talk via text, the occasional discreet grabbing of my crotch if we were getting drinks at the bar at the same time and finally a picture of her on all fours fingering herself. She preferred anal to vaginal penetration, wanted to be dominated and openly questioned whether I could do it properly - I don't seem like the type. I explained to her that as a rule I'm kink-equivalent and just on size difference alone tend to be aggressive. I'm into whatever gets my partner going, whatever gets her moaning and gasping. The sounds a woman makes during sex are a treasure and if it takes treating her like a sex toy to get them, that's fine with me.

I couldn't handle it anymore - I told her that the next time we saw each other, I expected us to find a way to make this happen, even if it meant renting a hotel room.

As it turns out, that was unnecessary - the next drinking night happened two blocks from my office and warehouse. After a couple of hours of barely being able to pay attention to conversation I decided I needed to take my leave - on the way out, I texted her the address of my office down the road. It was now or never - if I didn't get some action that night I was ending it, as now her existence distracted me as I apparently distracted her.

A quick detour for descriptions - I'm a slightly taller than average, slightly bigger than average white guy. I'm strong but not ripped, reasonably attractive I think but generally more likely to get laid because I can make a girl laugh. I'm no porn star when it comes to the dick but I've been told the head is "bulbous and feels fantastic when [I'm] thrusting" and even now in my mid-30s I can get it up 4-5 times a night when called upon.

Eve is, again, short (5'1" if she's lucky), now-thin (I would guess 105ish) with long dark hair, naturally curly and dark eyeglass frames. She looked like a sarcastic, dirty librarian - appropriate, as that's what she was. With her clothes off, she did not have the greatest body I had ever seen - twins just a few years back, weight loss, so on and so forth. Nevertheless, it was quite a play thing. I appreciate being able to 'pick up and toss around' partners, figuratively speaking and Eve was very tossable.

Detour over, on to the first encounter with Eve -

I unlock my office and step inside - I've gotten a text from Eve that she'll soon be on her way and I sit down to wait. I'm already hard and it takes some willpower to leave my dick alone. Earlier in the day I had masturbated so I expected no issues with the 2-3 month dry spell I had been going through. You don't want to finish in 20 seconds your first time with a woman - first impressions count.

I hear a knock on the office door and quickly open it, Eve steps inside. Immediately, without thinking, I lean in, grab the back of her head and kiss her. It's wild and passionate, weeks of pent-up energy being expended. I nibble her lip as I withdraw and tell her "Hello."

She's flushed and smiling and reminds me to lock the door. Good call - there was a 24-hour bail bondsman next to me and occasionally people opened the wrong door. We chat for just a moment and I finger the three pack of condoms in my pocket, eager to find out what it feels like to be inside her. That's when she breaks the bad news - she had started her period the day before and was not a fan of period sex (no worries - neither am I and to be honest

"But I want to suck your dick until you collapse."

I leaned in to kiss her again but quickly decided to start fulfilling her fantasies - as I broke the kiss I grabbed her hair and pulled her hair back just enough to elicit a light moan. Into her ear I whispered “good girl.” I quickly discovered that those were magic words - she would do anything to earn her “good girl” status and just hearing it soaked her pussy. It would become difficult after a time not to abuse the privilege - but along with my distaste for demeaning dirty talk (whore, bitch, etc.) it did make for some inventive language. More than once she would start an evening together asking me to use her as my personal “fuck-toy.” I was always more than willing to oblige

Pushing her to her knees, I started to undo my belt and she stopped me - she wanted to do it. Freeing my erection, she started by gently licking my balls and the underside of my shaft, swirling her pierced tongue

For the next two hours we made out in every room of the office, stopping for her to blow me in every conceivable position and situation. She went crazy the first moment I took her by the head and started fucking her mouth, pulling out every so often to lift her up to me and kiss her deeply. Between the alcohol and the earlier masturbation and the nerves of a first time meeting I simply could not cum. I'd get close and could never quite cross the finish, or I'd get close and her jaw would get tired - eventually I could tell she was starting to get discouraged, asking if there was anything she could try. I admitted that I had taken care of things earlier to ensure more than two pumps and in one of the stranger juxtapositions of my life, a woman with deep-throating drool and pre-cum mixing on her chin told me that was sweet.

It was late and she had to drive home and I was clearly not going to finish so we decided to wrap things up. After another quick makeout, I helped her dress and we stood outside smoking. I kissed her goodbye and promised that I'd save myself for her the next time we could meet - no pregaming necessary.

So began my affair with Eve.