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Anal

This is a true story. The dialogue took place over seven years ago, so it’s reconstructed here, rather that transcribed. But it’s pretty close.

I was in Dallas to see a client. I was with an account executive, a woman named Lorraine.

The first night we were there, we had dinner with the client at the Atrium restaurant of the hotel. The client is a runner and he has to leave us at 9:30. He wants to get to bed early so he can do about 5 miles before our meeting in the morning. Glad I’m not a runner.

The client is very good looking and obviously he’s fit. I mean, for one thing, the guy can run five miles. Despite these awe-inspiring pluses, on an off day I’m be willing to admit that I find him about as interesting as a Hollywood Squares re-run. But then, it occurred to me (this was not the first time) that I’m not a woman. Out of curiosity, I ask Lorraine if she found him attractive.

“No. I mean I guess he is technically. But he’s dull.” Right answer.

Lorraine’s skinny, very bright, 28ish, freckles, full of energy, has an amazing mound of red hair, pretty, looks a bit like Julia Roberts, but spoken of as “a slut” around the office. (I might say that it’s always other women who call her that and by that they seem to mean that she is fairly open about liking sex. I, personally, don’t see this as a big negative. But then that’s me.) I’ve worked with her for about eight months so far and, as you can tell by my description, I like her. Some fairly candid discussions with her in the past and we’ve laughed some together, but I’ve never laid a finger on her to this point.

Drinks throughout.

“Now you … well,” she says, “certainly not dull. You make me laugh. But … now don’t take this the wrong way, it’s a compliment really … but I could never think of you sexually because you remind me of my father.”

Well, an interesting way of putting me off. Effective too.

I laugh, but am maybe just a bit stung.

Still, it gives me an opening to have an open discussion about sex – and her sexual experiences — without her having to feel I’m making a pass. We know each other well enough and she has told me things about “Got my brains fucked out last night” or “He’s hung like a horse.” That kind of thing. So there’s not really a chance that she’ll think I’m stepping out of bounds. The boundaries were already pretty far out there.

(I tell myself that I like these kinds of discussions because they teach me about how women really see these things. How they really think about their experiences. How differently they see it all from the way men see it. Because, after all, getting women to open up (!) and tell their real feelings and attitudes is the only possible way I would ever find out about these things that are – by definition – outside of a man’s experience. Makes sense right? Of course there just might also be the tiniest bit of a turn-on for me in these talks. But that’s hardly my prime motivation, right?)

“First time?”

“Intercourse?”

“Yes.”

“In a car. He talked me into it, he thought. But I was very ready. If it hadn’t been that night it would have been the next or within the week. Not very satisfactory from my point of view, which I guess is too much of a cliché. Still it wasn’t his fault. I was just caught up in the sort of technical task of getting rid of my virginity. Getting myself off was probably about tenth on the list of things going through my mind.”

“Did he enjoy it?”

“What a dumb question!”

“Why?”

“Men always enjoy it as long as they get off. And he shot his wad after about four strokes. But I’m being unfair. He was only about 18: might have been a virgin himself, though he said he wasn’t – maybe just to give me confidence.”

“How old were you?”

“18 years, 107 days.”

“Late bloomer.”

“In some ways, I guess. In others no.”

“Meaning?”

“Well, when I was 13, I had an experience that really opened my eyes to all that. We had a summer place in the Hamptons and that year, one of my brother’s friends had come out to stay with us. His name was Jamie and he was about to go off to Boston University in the fall, so he must have been 18, maybe 19. I used to spy on the two of them in sort of a casual way. But one morning – there was a shared bathroom that opened on two bedrooms: mine and theirs – I heard someone go in, and I went to the keyhole to look. I had already seen both of them nude through this keyhole a number of times … seen them taking a piss, caught them taking showers, you know. It was a bit of a turn on, but it was as much educational as anything. This time though, Jamie locked both doors, turned on the tap to fill the bath (this was a bit strange, because the guys always took showers) and then took all his clothes off. But this time was different than the other viewings, because I was surprised to see that Jamie had a hard-on. It was the first “stiffy,” as we used to call them, I had ever seen. It so surprised me that it even took a moment for my innovia escort mind to register exactly what it was. Remember I was only 13. Anyway he got in the bath while it was still running and lay back with his head at my end of the tub, facing the other direction. I remember all of this vividly; I can still picture it clearly even as we sit here. I couldn’t see his head because of my limited viewing range, but I could see most everything from his waist down. And with the tub filling up, he started to stroke himself. He was left-handed. His cock was sticking straight up and was very, very hard (the way high school boys cocks get). And then he reached for the soap and got his cock totally lathered up and started really pounding himself off. Then suddenly I could hear a sort of groan/whimper and he shot his cum into the air – straight up – and then again and a third time. It’s a good thing the water was running because I was panting so hard, I’m sure he would have heard me otherwise. I was so excited I could have come right there kneeling at the keyhole. I thought this was the most amazing thing I had ever, ever seen in my life.”

“But you didn’t come?”

“Not for at least another minute! I kept watching during his come down, but I reached down to my cunt and felt that it had just sopped my panties. And then I lay down on the floor, on my back, right by the door – I remember feeling my heart which was violently pumping – scrunched my panties down, not even bothering to take them off and jiggled myself off in record time. One of the best orgasms I’ve ever had.”

“You already knew how to do that at thirteen?”

“Oh yes, I certainly did.”

“Did you ever tell this Jamie what a big role he’d played in your life? You know, like years later?”

“No, but I wasn’t finished telling you about that summer.”

“You saw him again?”

“Shhh. Quit asking questions and let me tell it. God, I can feel myself getting wet right here just thinking about all this stuff again.”

“Are you really?”

“Oh yes. I’m dripping. But it’s as much the second part of the story that gets me there. So, do you want to hear it?”

“Yes. Very much.”

“I thought you would. It was the day after the bathtub scene and my brother and I and Jamie were out in our rowboat on the Sound. We were all wearing bathing suits. I had on a pretty modest bikini with an oversized t-shirt on over it and the guys were just in trunks. It was very hot, but there was a little breeze, and Bobby suddenly decided that he wanted to go wind surfing, so he left Jamie and me in the boat, jumped overboard and swam back to the shore. I had known Jamie since he was maybe the age I was then – 13 – so he pretty much thought of me as the tag-along little sister. I’m sure he didn’t think of me as having anything to do with sex. I was very shy and insecure about myself sexually, but I was pretty strong-willed and independent-minded even then (as may not surprise you). And I was overcome with the thought that here I was alone in this boat with this guy who I had seen shooting his rocks off. I wanted to talk to him about sex – really I wanted to see his cock up close – but I didn’t have any idea how to get this to happen. Of course, now I would simply say something outrageous and blunt and I would be on my way. But I wouldn’t have even considered it then. So I started by asking him about the girls that he and my brother knew, and who he liked and that kind of thing. Finally I asked him if he thought one particular girl was sexy.

‘Yah, she’s okay.’

‘You mean just because she’s got big tits, is that the reason she’s sexy?’

He laughed at my question and probably because he had never thought of me as anyone who would even consider using the word “tits.”

‘Yah, well that’s one reason. I mean they are pretty nice.’

‘Have you ever seen them without clothes?’

Like all boys, he wanted to brag, to show himself experienced – they can’t resist.

‘Yah I’ve seen them: I’ve touched them.’

I was impressed, but more than that I knew the conversation was going where I wanted it and I squeezed my legs together – I could feel myself getting excited. As innocently and in sort of little-girl-wanting-to-know-more-about-sex-from-this-experienced-man kind of way I asked more questions. He fell fully into his role. Had he ever gone all the way? Yes. (But he wouldn’t tell me who.) What did it feel like? Did the girls like it? I could see him trying to keep an educational feeling to his answers. But at the same time I could also see that he was starting to get a bit of a bulge in his trunks as he rowed.

Finally he said – ‘Too many questions!’

‘Okay, it’s just that I don’t have anyone to ask about these things, you know.’

‘How about Bobby [my brother]?’

‘No, that would be too embarrassing. But, you see, I’ve never even seen a male penis.’

‘Well, you’re only 12!’

‘13! And I don’t want to wait until I’m like in college.’ istanbul escort Pause. And then impetuously, ‘Jamie, I’ll give you ten bucks if you’ll show me yours.’

He laughed, but the way he did it, I could tell that he was thinking about it, and I doubt it was for the ten dollars.

‘You mean like “you show me yours and I’ll show you mine” like we were little kids?’

‘You want to see my vagina?’ Unfortunately, even though I had actually heard the word pronounced at least a few times, I was much more familiar with it written so I pronounced it “va-GEEN-a.” He burst out laughing at my error, probably as much to relieve the tension he was feeling at my proposal as from any real humor. But his laughter angered me. I must have turned a hundred shades of red and I said, ‘Well, do you want to see it or not?!’

He stopped laughing and thought for a second. ‘I wouldn’t mind,’ he finally said.

‘Okay then. I promise I’ll show you, but you have to go first.’ He tried to negotiate me going first or a simultaneous showing, but I was pissed off and remained adamant and he finally agreed. He looked around on the water – no one within a hundred yards – and then he put the seat cushion down on the floor of the boat and scrunched down on it. Slowly he then pushed his trunks down to his thighs and his cock sort of popped free.

With an involuntary intake of breath I said, ‘Oh that’s great. It’s beautiful. Is it always that size or is that an erection?’ From seeing him the day before I knew that it was only about half hard.

‘No, it gets bigger when I get turned on.’ And then with a bit of difficulty he pulled his trunks back up and tried to rearrange his cock inside them.

‘Enough, now it’s your turn.’

‘Can’t I see yours with an erection? I want to see how big it can get.’

‘A deal is a deal. It’s time to show me your cunt.’

‘But what if I show you mine while yours is still out. Wouldn’t that turn you on? Then I could see it get bigger. Please.’

‘Show me your cunt first, then I’ll decide.’

I took off the long t-shirt (embarrassingly I could see that there was a big wet spot on my crotch.) ‘I guess I’m getting a little turned on myself,’ I said as sort of a half apology. And then sitting on the back plank seat I hooked my thumbs in the sides of my bikini, which came up almost to my waist, lifted my ass a bit and with my legs together, and pushed the bikini down below my knees. Then, looking away from him casually out over the water, I slowly spread my legs to give him a look.

‘Yours is too,’ he said.

‘Is what?’ I asked looking at him now.

‘Beautiful.’

‘Is it really? Do you really, really think it’s a pretty cunt? (Probably the first time I had ever used the word. Certainly the first time with a boy.) You’re the first boy that’s ever seen it.’

‘Yes it is. Don’t worry, any guy would think so. [I will always love Jamie for saying that to me then.] Would you open it up and let me see how wet it is.’

‘Only if you show me your penis again.’

This time there was no arguing. He pulled his trunks down to his knees again and this time it was definitely bigger. Then I slipped my bikini bottom off one of my ankles so I could fully spread my legs for Jamie to see how shiny and wet my cunt was. We were both extremely turned on and I put my fingers down to spread my pussy lips so he could see a little deeper and coincidentally tease myself very gently. He was breathing hard now. But it was hard to work out what the next step might be. We both watched in awe for a few moments. Finally I asked if he could make it bigger by stroking it.

‘Why don’t you stroke it for me?’

‘No! I couldn’t.’

‘Would you like me to touch you?’

In fact I could think of nothing in the world I would have liked better, but I said definitely not. It would have been all too scary.

‘I’d just rub it on the outside, very softly,’ he said.

‘No. But I’ll do it to myself if you’ll rub your penis.’

A deal. He started to slowly fondle his cock and it got bigger and harder as I teasingly started rubbing my cunt.

‘Can you make yourself ejaculate?’

‘Probably.’ But I could see that the real answer was ‘certainly.’

‘I want to see it ejaculate, please. Pump it. I’ll let you touch my cunt if you let me watch you come. Wouldn’t you like to touch it? It’s so wet.’

Then I started encouraging him, helping him verbally, so I really was feeling that it was me making him get off. I only remember sort of constantly cooing admiration at him, but I obviously said stuff to him too, like:

‘oooo yes it’s sooo big and hard oooo spread that sticky stuff around like that yes ooooyes does it feel good oooh it feels very good down here … see it? it’s sssooo wet … stroke it a little faster now I want to see it shoot, are you going to shoot? You look soooo close, are you? Come on now come on come on oooo come on …’ and so on.

And kadıköy escort then it was obviously getting very serious for him. He was pumping harder and harder and he was having trouble keeping his eyes on my cunt, they kept closing slightly, and finally he groaned and shot like a rocket with some of the cum from the first spouting even hitting him on the chin. It was my dream. And I was unbelievably excited by the sight – even more than the day before because I was right there in the boat with him. I was frigging away on myself, but, under the circumstances, could only manage a small little orgasm, but I gave out a little squeal and a groan, faking it a little as a kind of tribute to the glory of his wonderful geyser act done just for me. Afterward, I praised him, telling him how excited I was when it shot out of him and he was groaning his pleasure.

Then, as I had promised, I told him he could touch me, but I held his wrist when he did. Enjoyable but a little scary. Then we both went for a swim to wash off all the sweat and newly excreted fluids, and rowed back to the shore.”

Sitting in the Atrium restaurant after hearing this story, all I could say was “Wow! I believe I might be just the teensiest bit turned on myself just listening to all that.”

“Well you can imagine how exciting it was for me at 13.”

“Seems like kind of a long dry spell from 13 to 18 years, 107 days.”

“Well, it wasn’t totally dry. There were about six or seven guys that I jerked off at various times during those years. In fact, I did it for Jamie later that summer – in the bathroom where I had first seen him. And there were others.”

“And that was enough for you. Giving hand jobs?”

“Yes, for the most part. You see, as much as I like fucking or giving blow jobs, I find myself most turned on by actually seeing the jizz shooting out of a convulsing cock and the wild-eyed look on a guy’s face in the throes. It’s like that’s what it’s all about for me. It’s such a feeling of power when you’ve got this totally helpless man in your hands (literally). For a few seconds there you have the feeling that he’d do anything for you – he’d kill, he’d let you whip him, he’d tell you he loves you, he’ll do absolutely anything as long as you’ll take him over the top and throw him into a space where he can get that wild, ecstatic release. Because, at any other time, men will always hold something back, will always be cool – or in your case, articulate – and measured. But when I’m churning away and the buttermilk starts to fly, that same man will cry like a little baby and will love me for the luscious angel of release I am. It’s a fabulous feeling. Sometimes when a guy is plowing away on me and I can tell he’s getting close, I lie and tell him it’s the wrong time of the month and he has to pull out. But then I pound him off with a passion and – if I might brag – a skill he’ll remember far better than just another shot in the hole. And when he’s gushing spurts of jam all over me and it’s splashing on my stomach and tits and neck and chin and cheeks and nose and hair, I spread it over me like golden cream and give him an honest smile of pure sensual, animal love and lust. And watching it all happen in his contorted face and the burst of aching-with-pleasure groaning and puffing, then the almost shy little ‘was-that-okay-to-lose-it-all-over-you-like-that?’ smile on his face, that’s what I love. He’s always sort of half embarrassed because he knows you’ve seen him surrendering everything to you. But even though he’s shown his total helplessness, give him an hour or a day or a week and he’ll be back for more. He can’t help it. He’s all mine.”

“Articulate?”

“Don’t play dumb with me, Mitch. I know you better than that. I know you make love to women with your brain and with words. You like to think that you’re in control. But I’d bet you big bucks that at this very moment you’ve got a hard-on and a cock as sloppy wet as my cunt.”

“I won’t take that bet. But I will say that you’ve been extremely effective with words in the last few minutes. Making me react in a way I — or certainly a father — never should.”

“I’ll just ignore that ‘father’ comment. But you see what I’m talking about. It’s all because most women think of a hand job as the easy way to get rid of a man when he’s pressing. They learn that when they’re young and they never realize the pure exultant joy of jerking the sap from a guy. For me it’s kinetic art. And the final catharsis is seeing the sticky fuzz fly.”

“You certainly tell it well.”

“Well, I’ve thought a lot about why I like it so much.”

Obviously. But now it was late, and though I could have listened to her give her Ecstasy-Of-The-Hand-Job speech another ten times and maybe cum in my chair, I said it was time to go to my room.

“Going up to jerk off, are you?” she asked with a knowing grin.

I probably blushed.

“Come on, Lorraine, you’ve made your point, don’t be a tease.”

She looked a little hurt. “I wasn’t teasing. In fact, if that was your intention, I was going to offer to … help.”

She wasn’t teasing and on the way up in the elevator she started the process, finishing it off pretty much as she had promised in my room.

Afterwards with a smile on her face, “Disappointed?”

No.

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