I think I'm basically over being freaked out by finding Mary Anne's old chat logs where she was telling that guy all about her previous sex adventures. It remains to be seen how I can use the fact that I know things about her past that she doesn't think I know to my own advantage. The opportunity presented itself to quiz her gently about her past last night and I found out a few things (mainly that the last guy she slept with before me wasn't who I thought it was). I asked her about some things in her way-back past to see where the discussion would go, but that quickly led into a truly horrific incident that happened to her when she was young, and that killed the mood pretty effectively.

Honestly, she would have every excuse in the world to be completely fucked up about sex. All things considered, it's a miracle that she's even as comfortable with it as she has shown me, much less what she hasn't shown me yet.

Basically, I asked her to tell me about her first date and her first kiss - you'd think that would be pretty innocuous stuff (my answers certainly would be). To make a long story short, those were both on the same occasion. When she was 15, she went out on her first date with a guy who was a year older than she was. They went to some church youth group thing, and then to a party at someone's house. At the party, this guy proceeded to get Mary Anne (who'd never had a drink in her life up to this point) really drunk, and then raped her.

If she has some issues today, well, that's understandable.

She didn't ask anything about my past, even though I'm perfectly willing to talk about most of my adventures up until I was about 25 or so. I figure I can tell her the truth about my life up until about the time I was 22, and then just be really vague about the time between that and when I got involved with Vicki. That should be relatively safe - she already knows (because I've alluded to it) that between the time I graduated from college and the time I got serious with my first wife that I went through a "phase" where I was "kinda wild". So I'll just avoid too many specifics on exactly how wild and how I didn't really settle down from it as much as you might think I would have.

You know, she's never really asked much of anything about my past. I've volunteered various details over the years, but I can't recall her ever actually asking about my relationships before Vicki. Maybe she just doesn't want to know. But I think it's really that she just doesn't care and isn't curious about it (which I just cannot comprehend, but I am perhaps the nosiest person on Earth, so it's perfectly possible that I'm the weird one with my interest in it). What's more, she has no interest and no jealousy about anyone from my past (this is something she alluded to in one of her chat conversations, that she is never jealous or feels weird around any of her ex-boyfriend's new girlfriends or current boyfriend's old girlfriends, though usually the feeling isn't mutual).

I find this extremely difficult to comprehend, but it seems to hold true and - being me - I'm not above taking advantage of it.

About a year ago, I had to make a trip to the Northeast for business. As it happens, I have an old friend from high school, Alexandra (Ally) who lives up there that I had't seen in seven years. She was someone who really wanted to come to our wedding, but she wound up not being able to make it because of a work conflict of some kind (it was a very good excuse, and I do know she really wanted to be there). So when it came up that I was going to go up there, it may have even been Mary Anne who suggested I should get in touch with Ally and stay with her rather than get a hotel room. I did and Ally was delighted to have me come stay with her.

If Mary Anne had ever quizzed me about my past, she might not have thought that having me stay with Ally was such a great idea. Maybe she wouldn't have cared had she known, but I would have been leery of the idea if I were in her shoes.

Ally is the girl who took my virginity.

We dated for a year in high school, and we were both each other's first. Even after we broke up, we kept fucking all the way through the rest of high school and all the way through college. She was my regular booty call fuck for my last year of high school and all four years of college. We'd probably hook up once a month or so - a few times I'd go over there and she'd make dinner or something, but usually I'd just go over there and we'd go straight back to the bedroom, or she'd come over and we'd get right to it. Sometimes I'd stay over, other times I'd go over there and bang her a couple of times and then go home. She was multiorgasmic, and she gave world-class blowjobs on top of it all. Unfortunately she tended to get on my nerves after a while, which is why we couldn't keep dating. But luckily for me, that never stopped us from fucking. And despite not having seen each other for seven years (and not having fucked for more than ten years), it didn't stop us this time, either.

She picked me up from the airport, and took me back to her place. We proceeded to talk for several hours, and drank most of a bottle of wine between us. Pretty soon we were sitting close together on the couch, then we were touching each other on the legs and arms, then we were cuddling, and before you know if we've got our hands in each others clothes and we're kissing and fondling and licking as we proceeded to get naked. She wrapped her lips around my cock and starting giving me one of those heavenly blowjobs as I played with her pussy, then we moved into a side-by-side 69. She was so wet and I was so hard.

Panting, she kissed her way up my hips and my chest. Breathlessly she asked, "Is this okay?"

"I want to fuck you," I replied.

"I'm not sure I have any condoms," she said.

"I do," I told her.

"Go get them," she answered with a smile.

I retrieved the condoms and tube of lube that I'd stashed in my luggage before I left that morning. If you're thinking that it sounds like I planned to go up there and fuck Ally all along, congratulations on your insightfulness.

I sat back on the couch and rolled on a rubber. Ally straddled me and guided my cock into her pussy. "Ohhhh yeahhh," she murmured as she sank down on my eight inches of hard cock. She started to ride me as I ran my hands over her C-cup tits, playing with her nipples, and then down to her hips and her ass, urging her on as she gradually fucked me harder and faster. With my feet braced on the floor I raised my hips to fuck her back, penetrating her pussy all the way to her cervix as she moaned with increasing intensity. "Oh yes, oh yes, oh fuck... oh fuck... so fucking good... oh yes oh yes oh yessssssss..."

She was pounding herself on my cock, thrashing around and screaming, her hands with a death grip on my shoulders, impaling herself on my rock-hard cock until finally she came all over me. She came so violently that I slipped right off the couch and we wound up on the floor with her still riding my cock. We giggled about that a little bit and kept fucking, slowly.

"Have you ever had anal sex?" I asked her.

"Yes," she answered, with a twinkle in her eye. "Sorry."

"I want to fuck your ass," I told her, looking deep into her eyes.

"Okay," she replied huskily.

She climbed off my dick, and as I got up she pulled the couch out (it was a futon) and got on her hands and knees. I grabbed the lube and positioned myself behind her. Before I greased up her back door, I slipped by cock back into her pussy, this time from behind, and fucked her doggy style for a bit. With my cock still buried in her pussy, I squirted some KY onto my fingers and started working it into her asshole. Then I withdrew from her cunt, slathered my dick with lube, and placed the head of my cock at her asshole. Gradually I applied pressure, forcing her ass open and slowly sliding my cock inside her. I slipped deeper and deeper into her willing asshole, until I was finally fucking Ally's ass for the first time.

Slowly I pumped my dick in and out of her, giving her time to adjust to having my big cock filling her ass. Buried up to the balls in her, I leaned forward with my mouth by her ear and asked, "You okay?"

"Uh-huh."

"Your ass feels so damn good."

"Fuck me."

I pumped her ass with increasing fervor. She was so fucking tight, her asshole was like a velvet glove milking my cock with every stroke. I felt the pressure starting to build in my balls as I fucked her asshole harder and faster.

"Oh my God... I'm going to cum in your ass now."

"Oh God, yes," she answered, prostrated beneath my fucking body, completely submitting to me as I violated her ass over and over again.

An electric shock went up my spine as I felt the cum explode from my balls and through my spasming cock. Sixteen years after shooting my first load of cum inside Ally's pussy, I came in her ass for the very first time. I grabbed her hips and pulled her to me, shoving my cock as deep inside her as I could get, every muscle in my body seizing up, as I was cumming, cumming, cumming in her tight hot ass. I may have screamed. I know I nearly passed out from cumming so hard.

As I gradually came back to myself some time later, I withdrew from her asshole. The condom came off as my dick came out, but I grabbed it and pulled it out of her. We collapsed on the futon in a heap, trying to catch our breath and panting like we'd both just run a marathon.

(Tomorrow: I'm not finished fucking Ally just yet...)

A Return of Regular Action? - 2005-03-31
Patience Rewarded - 2005-03-29
Infidelity... It's Everywhere - 2005-03-25
3 A.M. Eternal (KLF is gonna rock you!) - 2005-03-24
A Different Twist - 2005-03-21