Hollie

Hollie by Stephanie Silver (sjtw69@yahoo.com)

Chapter Seven -- Finally a Woman

That was our last date with Eddie. Hollie never told me why. In hindsight I think I know why, but at the time I just expected we would see him at least a few more times. I mean, to me he was perfect. He was bisexual and attractive to both me and Hollie. But in the end I think that might have been his problem. At least as far as Hollie was concerned.

At the risk of getting ahead of my story, I think that what happened is Hollie didn't like the fact that we were suddenly competing for a guy. That wasn't supposed to happen. At least not in her mind. In her plan. maybe I'm just flattering myself here, but I really think that she saw what was developing between Eddie and me, and decided to stop it before it went anywhere.

I'm not confrontational, and obviously that's what got me into a lot of what happened with Hollie and my interest in cross-dressing. It was not part of my nature to ask, to confront her, about Eddie. But underneath, I think I knew. And because I knew, or even if I only suspected it, it sowed the final seeds leading to the destruction of our marriage.

I know what you're thinking, that those seeds were there from the very beginning. What marriage? I know. I know our marriage sounds to most people like a joke or a travesty. I'm willing to take the blame for a lot of that. I was never able to be the husband Hollie needed. Was that my fault? Was it my fault for being who I am?

Perhaps what I really mean then is that it sowed seeds of doubt into my mind. I began to suspect something I hadn't before considered - that being married to Hollie might not be in my best interest. Hollie, I began to realize, was really kind of a bitch.

But, like I say, I'm getting ahead of my story, and there was still a lot going on, despite the mysterious disappearance of Eddie from our lives and despite my doubts.

There was Stanley. I called him Flat Stanley. Flat Stanley was a book I once read about a completely flat boy named Stanley. Stanley Lambchop. Hollie's newest boyfriend was named Stanley Lambert. And he wasn't completely flat - he had the bulging biceps and pecs and other musculature needed to get Hollie's attention. But his most striking feature, as long as he wasn't wearing a shirt - and Stanley Lambert could often be found not wearing a shirt, for what I think you'll agree are obvious reasons - were his abs. Impeccably defined. Flat. Washboard. If he lay on his back, and tensed his stomach muscles, I'm certain you could drop a quarter onto his stomach and have it bounce right back into your hand. To cover such magnificence with a shirt would have been, in Stanley's mind, at least, a crime.

He even looked a bit like Flat Stanley - same color hair, same hair style, same lopsided grin.

I guess I already knew that Hollie had an exhibitionist streak in her when it came to me. She liked - she really got off on having me watch her with other men. And, truthfully, I liked it too. It was kind of like having my own personal porno movie. Only better.

Stanley had one too - an exhibitionist streak. He liked - and seemed to really get off on having me watch him screw my wife. And talking about it. "I'm screwing your wife, Cam. Do you like watching me screw your wife? Do you like seeing me make her tits jiggle and shake? Do you like hearing her moan like a slut in heat? Huh?"

"Yeah, Flat Stanley, you're really something in bed," I would think of replying with just the right amount of sarcasm. But of course I just nodded and agreed that it was really sexy to watch.

And watch I did. From every angle and every position. I think... Yeah, I'm pretty sure that Hollie and Stanley were doing it at least twice a week. At least every weekend, and at least once more during the week. I did have to admit that Stanley had a lot of cum, because he seemed to be putting a huge load of it into my wife every three or four days. And who knows how often they were doing it when I wasn't around to watch.

And of course I dressed up in lingerie to watch their show. Hollie insisted on that. Stanley would comment on the way I was dressed, saying that I was obviously a "faggot" and a "queer" for dressing that way. Hollie would just laugh, even though I tried to tell her at least once how much that hurt my feelings. Her laughing, her joining in with his insults, I think was what hurt the most. If not for that, I think I could have passed Stanley's comments off as the kind of thing you'd expect from an insensitive jerk. As it was, I found myself being stung by them and forced to face them as Hollie urged me to get closer and closer to the action.

Eventually, as was her plan, I found myself lying beneath Hollie, my head between her legs, as Stanley fucked her. Okay, if you're a voyeur, there's nothing quite as arousing as the site of a cock splitting open a pussy just inches from your face. I came more than once that way. Which, of course, brought more teasing and ridicule from Stanley. What kind of a man wears his wife's underclothes and cums watching her get screwed by another man?

Okay, well, first of all, they weren't Hollie's underclothes, they were mine. And second, I'd pretty much abandoned the idea that I was any kind of a man. So in that sense, Stanley's comments had no effect on me. That doesn't mean I liked hearing them. And it doesn't mean that hearing Hollie laugh in agreement wasn't still incredibly painful.

Okay, I told you I was starting to think of her as a real bitch.

But leaving her, just for being a bitch, wasn't something I was ready to do. So I kept watching, and eventually Stanley decided - or maybe Hollie suggested it and Stanley agreed - that, since my mouth was already so close to Hollie's pussy, that we would start taking turns - a few strokes in her pussy followed by a few strokes in my mouth and then back to her pussy again. Making me suck his cock, of course, was just more of the degradation they seemed intent on inflicting upon me.

Which is funny. Because frankly, I was perfectly willing to suck his cock. There was no reason to humiliate me into it. If anything, it just made me want to do it less. I guess I got through it by thinking about Eddie, and imagining it was his cock I was sucking. Only without the insults.

And of course when Stanley would cum, it was my job to lick his cum from Hollie's pussy and to swallow all of it. And, yes, that subjected me to more ridicule.

Eventually Hollie said I was ready to have a guy turn me into a "real woman" by fucking me. I don't know how she knew it was time or how she knew I was ready, but that's what she said.

And obviously Stanley wasn't the right man for that job. Not that he wouldn't have enjoyed "humiliating" me that way. And I'm sure Hollie would have enjoyed watching him humiliate me that way, and would have laughed along with him as I blinked back the tears. But Stanley... Well, it was one thing for him to stick his dick in my mouth while he was fucking Hollie. It was one thing to know I was licking his cum out of her and swallowing it. It was quite another, in his mind, to stick his dick into my boy-pussy and fuck me as if I was a girl.

Guys are funny. What you think won't bother them sometimes does, and what you think will bother them sometimes doesn't. But, whatever, Stanley wasn't the guy.

That was Dave. Dave Warner. Do I even need to mention muscles at this point? Let's see... bench press 280, biceps curl 175, squat 400 - I felt it wasn't a good idea to tell him I could squat 400, too. I might not have much upper body strength, but my leg strength was better than average. To be honest, Dave looked a little soft. You could tell he was strong, and everything about him was firm, but he didn't have that sculpted look that a lot of other gym guys go for.

Personally, I found that refreshing. Dave was... Well, he liked to make fun of me, too, for dressing in Hollie's lingerie (I keep telling you, it's MY lingerie, not hers!) and allowing other guys (him) to fuck her. (Hey, it's none of my business who she has sex with.) But other than that, he was a pretty decent guy. And even when he was making fun of me, he seemed to do it in a nice way. If you can imagine that. It's hard to explain. I just never felt completely like he didn't at least like me a little, or respect me in some unknown way. Or at least want to help me out a little.

And, hey, I wish it had been Eddie, but... I wasn't exactly man enough to say that then... Or do I mean woman enough? Hmm, strange, isn't it? Because eventually I think I reached a point where I learned to stand up for myself, and I reached it not by being more manly, but by going the opposite direction and becoming more of a woman. Which kind of makes sense when I keep saying how, as a man, I had so little confidence, but dressed as a woman I would suddenly find some.

Anyway, we did a lot of the same things we'd done with Stanley. Dave's sex needs weren't quite as demanding as Stanley's and so their sex dates, with me watching, were mostly on weekends with the occasional mid-week frolic for variety. At first I watched from across the room, but gradually I moved closer and closer, until eventually I was beneath Hollie and between her legs, with Dave's... ahem ... very impressive member going in and out of her pussy a few times and then into my mouth.

I'm going to say it was seven inches long. I have no idea. Mine is five inches long and about as big around as my hand can grip. Dave's - yes, I gripped it a few times - was bigger around than I could grip and seemed to be at least two inches longer. And the damn thing was going in my ass!

The one thing that saved me, I think, was it had no head. I mean that little helmet ridge that some guys have. It was just smoothly tapered from stem to tip. So once it started that journey in, there was nothing really to stop it from continuing all the way.

But I'm getting ahead of myself again, and I have a terrible habit of doing that when I write.

For as much as I paint her to sound like a bitch, Hollie still had concerns for me and wanted to make me happy. I mean, it really would have been pointless for us to get married if there hadn't been at least some kind of mutual love. And that's why Stanley wasn't the one who introduced me to "true womanhood."

We tried to choreograph it in advance. We traded positions, so that I was on top of Hollie, with my skirt raised up to my waist, my garters stretched tightly across my bare bottom, my panties somewhere on the floor beneath the bed. After letting Dave fuck Hollie for a minute or so, it was my turn. "Use plenty of lube," Hollie cautioned. Then turning to me she said, "He's really big."

Dave applied a small amount of Anal-Ease - guys never use enough and prepared to enter me. "No, use more lube," said Hollie, who had her fingers in my butt crack, feeling how the preparations were going. "He's never done it before. Don't worry about wasting it. You need to make him nice and slippery."

As Dave rewetted my hole, she kissed me very sweetly and added, "Like a woman's pussy."

I guess you had to hear the tone of her voice. It was a mixture of love, concern, and admiration. In a way, it was a signpost, pointing the direction I knew I needed to go. I wasn't a boy, about to get sodomized. I was a woman - or a woman-in-training, about to experience what it meant to be female.

And then... The only way to describe it is ouch. Some people I've heard describe it as a fire. It wasn't a fire. The Anal-Ease took care of that, I guess. It just hurt. A lot.

And then came the feeling of needing to relieve myself, as if something very embarrassing was about to happen several feet away from the toilet where it was supposed to happen. "Don't worry, that's normal," Hollie assured me with more kisses. "Just keep pushing back."

And maybe that's the secret. You have to want it in there. And I did. I wanted to know what it felt like to have a guy completely inside me. Dave, for his part, was perfect. I can't imagine anyone going more slowly and being more patient than he was that first time.

And every time I asked him to stop, he did. And how many times did I ask? About twenty? "Stop!" Pause. "Okay, go. No stop!" Until that magical moment when it stops hurting and your body finally accepts it, and it doesn't matter that he's seven inches long and bigger around than your hand can grip, it just feels good. And you suddenly realize that a man is fucking you. That his dick is inside you. And you can feel his balls slapping against your crotch, and even though you have balls of your own, there's just something so much different about the feel of his balls there, as if yours are useless and you finally understand what it really means to have balls between your legs.

Only you don't know, 'cause they're not yours. You're only borrowing them. And part of you realizes that you're not really a man at all, despite what people have been telling you for most of your life, but somehow none of that matters anymore, because now you're something better - you're a woman. And you're finally being fucked the way a woman should be.

And I'm sorry if all that sounds very sexist, so please don't send me letters telling me how sexist I am for writing it and how woman are more than mere sex objects put here for the pleasure of men, because my experience is that all I've ever really wanted was what women naturally possess, and telling me that's not a good thing.... I can only quietly disagree and say that for me, it's different.

I have no idea how long it took before Dave came. It seemed like a long, long time. Meanwhile my body was racked back and forth by his thrusts, a prisoner to his demands. But finally I felt the deep thrust signaling his impending orgasm, and then the moment as he held it there, deep inside me, as deep as he could plant it, followed by what can only be described as two sudden swelling motions, as if a surge of liquid was being violently and forcefully shot outward. Oh, wait, that's exactly what was happening, so no wonder it felt like that. I felt the swellings of his cock, and then the few urgent thrusts as he pulled back and recharged, then thrust forward to release more semen into me.

And then I was a woman.