Plump and Plain

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Losing her virginity takes awhile - & an audience.
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tarkatony
tarkatony
254 Followers

"She was training to be a masseuse — had always wanted to be a masseuse, had always wanted to work on bodies, to help restore their health. But she had to quit her training. Know why?"

She shook her head, "No."

"Because she couldn't find anyone to work on after class! Isn't that pathetic? I mean, there isn't a guy in this entire city who wouldn't give his left nut for her to come over and rub him down. But she couldn't find anyone. I think that's just really, really sad."

She nodded her head, "It is, yes, I know the feeling."

"You do?" This kind of surprised me; I didn't know this woman very well so didn't know why she'd say this.

She told me. "I'm two weeks away from my 23rd birthday and I'm still a virgin. I find that really, really sad, too. Actually, it's pathetic."

"And you don't want to be?" That was all I could think to say.

"No, I don't and haven't for some time."

"So why don't you do something about it?"

"I am."

"What?" I didn't understand.

"I'm telling you I'm a virgin and I don't want to be."

"You're telling me this because ...?" I left the sentence open, hoping she'd fill in the blank.

She did. "I want to have sex."

I laughed, "Is that an offer?" I didn't think it was but I also couldn't figure what else she was getting at.

"Yes, it is."

I still don't think I got it. I hesitated a moment before saying, "You want to have sex ... with me?"

With a level gaze, she looked me in the eyes, "Yes."

'Why me?' I asked myself, then I asked her the same question.

"I like you and you're here, and we're talking about it, so why not?"

"Wouldn't you rather lose it to someone you really care about?"

"I would, yes, but there isn't anyone and there isn't likely to be anyone anytime soon."

"Why not?"

"Because, as you can see, I'm not very attractive, not the kind of girl guys thinks about when they want to have sex. And I'm not aggressive, either — not a great combination if your goal is to get laid."

She was sitting on a computer chair in our mutual friend's apartment; I was sitting across from her on the couch. I had met her a few times before, talked to her for a couple of minutes each time and that was the extent of our relationship: she was a friend of a friend, that was it; I couldn't even remember her name. I laughed, nervously, "Well, as a virgin, maybe you don't know that your approach isn't the normal route to sex, I mean with the line 'my goal is to get laid.'" I laughed again, "Don't get me wrong, I'm sure it'll work about 99.9% of the time."

She didn't laugh, she seemed frustrated. "Ya, well, the normal routes, whatever they are, are pretty much closed to me. I'm not particularly attractive, not aggressive, not very social ...," she hesitated, "what would you suggest my preferred route should be?"

She was right, she wasn't very attractive. She was plump and plain with a roundish face that exuded more intelligence than beauty and with the way she was dressed it was impossible to see anything sexy about her. She wore a pair of black slacks, a black vest over a grey-blue shirt buttoned at the neck and cuffs as if for protection. But even at that she wasn't noticeably ugly; she was just the woman you pass on the street a thousand times a day and never notice.

But I was noticing her now, her eyes were boring into mine, she was waiting for an answer. I shrugged, "I don't know what your preferred route should be, I guess whatever works."

"But that's my point, isn't it? Nothing has worked. That's why I'm still a virgin and that's why I've made you the offer. Betty won't be back for another 3 or 4 hours; we're here; I've explained my predicament; I've asked you to have sex with me; what do you say?"

As she studied me, I thought about it — quickly, I didn't want to appear to be agonizing over a decision — that would be a little insulting; she was obviously desperate. When I spoke I was as frank as she had been, "I'll do it but only on one condition."

She continued to scrutinize me, "And that is?"

"That the sex will be really memorable for you."

She seemed to relax now; a hint of a smile appeared, "Oh, I imagine it will."

I shook my head, "No, it won't. If I do what you're asking, I'll stick it in you, thrust a few time, we'll both cum and after a few minutes we'll both feel stupid. You'll have lost your cherry, we'll both have lost a little self respect."

The smile was gone; she seemed to be considering what I'd said. "So what do you suggest?"

"That before we do it you get hotter than you've ever been before, maybe even hotter than you've ever imagined you could be so that when we finally do have sex we'll both feel good about it; we'll have achieved a lot more than just a broken hymen; we'll have done something you'll always remember."

She smiled again, this time with enthusiasm, "OK, so how do we accomplish that?"

"With words." I almost laughed when her smile turned to a frown of doubt. "I want you to sit there and I'll sit here and we'll start talking about things sexual and we'll go where it seems best to go and if it works, if we both get turned on, and I stressed BOTH here because I'm not just going to service you, this isn't going to be a pity fuck, so if it works, we're both going to want to go at it, and if we both really want it, the sex will have a good chance of being memorable. That's my condition."

There was only the hint of a smile again, "Fine, accepted, but I think you'll find I'm pretty dim on the subject."

I shook my head, "I'll bet you aren't. Do you have sexual thoughts?"

"Of course."

"Had them for awhile, for years?"

"Yes."

"Are they always the same?"

"What do you mean, 'the same?'"

"Do all your thoughts about sex have the same theme, are they always about the same person?"

"No."

"So you think about sex in a variety of ways?"

"Yes."

"How big a variety?"

"I'm not sure ..."

"In your head have you had sex on a boat, a plane, in a kitchen, on a beach, standing, sitting, in a shower ..."

Her laugh interrupted me, "I get your point, yes, most of the above."

"So, in your mind at least, you have quite a lot of sexual experience?"

She smiled more brightly this time, "Put that way, yes, I'm a real aficionado."

"That's why I don't think you're going to be 'dim' on the subject: you've had lots of experience, if only in your head. So do you want to get started?"

She laughed, "I've already started."

"Are you feeling a little hot?"

"I've never talked about sex with anyone before, so it's kind of, ... a bit of ... a thrill."

"Never to anyone? Not even girl talk?"

"The poodles don't share their thoughts with the bulldogs."

"A little harsh."

"But accurate. When you're plump and plain people, even of the same gender, they just assume you're sexless. You did, didn't you?"

"No, I just didn't think of you in a sexual context."

"It's the same thing. If I was attractive, you would have put me in a sexual context."

I thought about this for a moment, "Probably, ya, I probably would have." I wanted to get this back on track, "Describe your breasts to me."

She shifted in the chair, as if preparing for a long grilling. "What do you want, the measurements?"

"No, describe them as you think of them, I mean, you're dressed as if you're ashamed of them, they're covered by a vest and a shirt and I'll bet you have some kind of jog-type bra thing on that flattens them. I can't see them, can't imagine them, so describe them for me."

"I like my breasts. I usually wear a sports bra, as you say, because they're more comfortable ..."

"But if you flatten them aren't you missing an opportunity?"

She shrugged, "I've never sexualized my breasts, they just are."

"But you like them?"

"I do, yes."

"Describe them."

She snickered uncomfortably, "Well, they're both a few pounds of fat with a nipple on them ..."

"Come on. When you look in a mirror, what do you see, what do you like about them?"

If she was uncomfortable with this, she wasn't showing it. "People like me don't look into mirrors but if I did, I'd see two what I consider to be medium sized breasts which give me a nice cleavage, which I like and I like my aureolas, I like the colour of them. They're large and darkish red with nipples that are, at this moment, probably pretty prominent."

"Can you feel your nipples right now?"

"They're tingling."

"Anything else tingling?"

She seemed to blush a little, "Yes."

"Do you have names for them?"

She smiled, "I'm waiting for a husband for that."

"Do you feel them when you're masturbating?"

She didn't flinch, "Sometimes, when I want to draw it out."

"How about bras? Do you have a favourite bra that shows your breasts at their best?"

She thought a moment, "A yellow one, kind of see through, I wear it when I want to feel sexy."

"And when's that?"

She laughed, "When my hormones tell me to."

"Have you ever worn that bra to impress a man, to try to turn him on?"

"No."

"Why not?"

"I guess I've never thought I could turn on a man. That has never occurred to me."

"If you had that bra here and I asked you to put it on, would you?"

"Of course. If I'm going to show you my breasts I'd far rather have them in a sexy, flimsy bra than the one I've got on."

"How about your panties. What colour are they, what kind?"

"They're coloured, I don't remember which, and cotton."

"You don't know what colour they are?"

"No, I didn't notice. Do you know what colour yours are?"

I shook my head and changed the subject, "If we were married and I told you I wanted to take a video of you masturbating, would you let me?"

"I don't know, maybe, I guess it would depend on how much I trusted you, which must be a lot, otherwise I wouldn't have married you, so, yes, probably, I would."

"I'd think I'd like to see how you masturbate, if I ask you to show me later, would you?"

"If I'm feeling then what I'm feeling now, yes, I probably would. Would you masturbate for me?"

"Would that make this coming-out party of yours more memorable?"

"It would, yes."

"Then I will, but we're not there yet, are we."

"We're close."

"You're getting wet?"

"Yes."

"Do you shave your pubic hair?"

"No, I have no need to, I don't do bathing suits."

"How about if your boyfriend asked you to."

"I would, yes. Is that important to you?"

"I like women the way they like themselves."

"Do you really mean that?"

"You're a lot more attractive now then you were a few minutes ago."

"You're probably hornier."

"It isn't that, it's because you're a little turned on now and that's making you appear a lot sexier. I think when women are turned on they like themselves more and when they like themselves more, they look a lot sexier. That's what I meant when I said I like the way women look when they like themselves; I think they're a lot sexier then, a lot more confident — they just seem to be a lot more interesting."

"So I'm more interesting to you now then I was?"

"Ya, but not as interesting as you're going to be. Will you take off your vest and shirt?"

She continued to look me in the eyes, "Will you take off your clothes, too?"

"I will but I'd rather wait a bit. I'd like to see you out there, all alone. I think you'll remember that."

She laughed nervously, beginning to undo her vest, "I think I'll remember this, too."

I watched her fumble with her buttons, "Is this the first time you've ever taken your clothes off for a guy?"

"Yes," she had her vest off and was undoing the buttons on her shirt.

"Tell me how you're feeling?"

"Nervous, I don't have a very good body and there's way too much light in here — I'm feeling really, really vulnerable ..."

"Is it a turn on, too."

"Maybe, but I'm way too nervous to notice." When she had all the buttons undone she hesitated, "Can I just wait a bit?"

"Wait in your bra."

"No, once I get my shirt off I'll want that off as soon as possible; it's really ugly, my breasts are better."

"OK, I don't want you doing anything you don't want to do."

She responded quickly, as if to reassure me, "I want to do this ... but maybe not quite so fast."

"Have you ever fantasized about sucking a man's cock?"

"No." She sat back in the chair looking straight into my eyes again.

"When we have sex, if I asked you to, would you?"

She shrugged somewhat helplessly, "If you wanted me to."

"But you wouldn't necessarily want to?"

"No."

"Does it seem revolting to you?"

She shook her head, "No, it's just that I don't feel the need to want to. Maybe if I did it, I'd love it, I guess that's what sex is all about, finding out what you like and what your partner likes. I think that's one of the big reasons why I want to lose my virginity; because I want to start learning about something that can be so important to my development."

"Do you think sex is important to development?"

"I do, yes, if not to development, I think sex is important for expression, at least I hope it is."

"Why?"

"I feel that sex is bottled up inside me like a great mystery. I've thought a lot about it and I've wondered about the mystery, how will it express itself?"

"How do you think sex will express itself?"

"I don't really know."

"Well, do you think you'll be into it, be dominant, be assertive or do you think you'll lie there and just take it?"

She laughed, "That's one of the mysteries, isn't it? I guess I'll find out."

"What do you hope for?"

She shrugged, "I'd like to think of sex as a kind of creative expression. I hope it is, I hope that my approach to sex will be interesting, both to me and to my partner."

"Would you like me to go down on you?"

She held her steady gaze, "I wouldn't expect you to."

"But would you like me to?"

"I'd like to know what that feels like," she laughed a little nervously, "I guess ... like you'd like to know what it'd be like for me to suck you."

"When we have sex, I will."

"Then I'll suck you." Her words couldn't have been more matter-of-fact.

"Have you ever had any kind of sex with a woman?"

"No. Never."

"Ever wanted to?"

"I was in a room one time when two girls were having sex. If they had asked me to join in, I would have — I was just that horny. But they didn't."

"If we were married, and I had one fetish, what would you like it to be?"

"I don't know much about fetishes ..."

"But you have an imagination. What fetish would you like me to have?"

She thought for almost a minute and while she did I thought about the subject, too. "Fantasies. I have a good imagination. I think I'd like to play sexual fantasies with my husband."

"Roll playing?"

"Ya, that sort of thing, maybe something like: you sit in that couch over there, and I'll sit in this chair here and we'll imagine we just met and I'll tell you I'm a virgin and you ..."

I laughed, she seemed to be getting a little more confident. "Do you think of this as a kind of roll playing game, I mean what we're doing?"

"It sure seems like a fantasy; to me it's unbelievable; it's almost surreal, but I'm not playing a roll here, I'm trying to be honest with you, I assume that's what you want."

"It's not what I want. The objective here is to get you unbelievably hot, whatever it takes. So lie if you want to."

She laughed, "Honesty is working just fine for me right now."

"You're getting hot."

"Very."

"So you like talking about sex?"

"It seems I do, yes."

"Have you ever thought about when you lose your virginity? About how you'd like it to happen?"

"Sure."

"And?"

"And, nothing. There was never a single scenario and never a face. If I'm actually going to lose my virginity here this afternoon this will be great."

I laughed, "And the face?"

She laughed, too. "It's a handsome face, a kind face."

"When you think about sex, is there one predominant scenario or theme?"

She thought just for a moment, "Probably being dominated."

This surprised me, "You don't seem the type."

She shrugged, "I probably want a man to dramatically take me away from myself ..."

"Like the homo erectus dragging the woman out of the cave by the hair?"

She laughed, "Sure, but without the club."

"Rough?"

"No, but insistent, like you're demanding something from me, like I perform, you challenge me. Like I said, I think I think about sex as an expression. I think I'll need an accomplished leading man; I'll need to be challenged."

"When we get naked, what part of your body do you first want me to feel?"

She laughed, "The way I'm feeling now, when that happens I don't think it will matter."

"You're there?"

"I'm fighting it off."

I thought I'd give her a rest. I stood up, "Can I get you something to drink?"

She looked up at me, "Water, I'm a bit dry." Then she laughed and looked away, "We'll, no, that's not true."

I got her a glass of water and myself a beer and sat back down again. "Will you take your shirt off?"

She did and quickly followed it with her bra. When she sat back in the chair her arms were across her chest in modesty.

"A little uncomfortable?"

She smiled, "A little."

"Then put your shirt back on."

She thought for a moment, "This is a bit too clinical for me. I want you to want to see them; I want you to ask to see them; I don't just want to strip and flop; I'd like you to pretend you care."

I stood up, reached under the waistband of my pants, then sat down, holding up my glistening finger. "This is called pre-cum, the name kind of explains what it is. I don't need to pretend to care, I'm really enjoying this; I'm really enjoying being here with you, doing this, so yes, I care, I'd like you to show me your breasts."

"Thank you," she whispered, as she removed her arms from her chest.

She was right, she had magnificently coloured aureolas and terrifically stiff nipples but she was clearly plumper than I like. "You have beautiful breasts, it's a pity society makes you hid them."

"Silly, isn't it, one day it won't matter but ...," she shrugged.

"Why are you over-weight?"

She didn't look at me, "It's a food-exercise thing, or so I've heard."

"And a self-image thing?"

She nodded her head as she looked at the floor, "Getting to be."

"If I was a smoker and I asked you to marry me, would you?"

"I know where you're going with this." She looked up at me, "Would I lose weight for you?"

I shrugged to show her she was right.

"It would be easy for me to say yes I would but it would be just as easy for me to say something like, if you loved me you would ..."

"... love me the way I am." Now she shrugged and I changed the subject. "How do you feel about anal sex?"

"I don't, I've never thought about it," and she laughed, "and I hope I never have to."

"Against it?"

"Fear of the unknown."

"How about a manage a trois?"

She shrugged, "Unknown, also, but I'm probably less fearful of that."

"Do you think when you're married you'll do much sexual experimenting?"

"I hope so, it's the expression thing: I'd like to think I'll be creative, but I'd have my limits ..."

"Do you know what they are?"

"No, I have no idea. The anal thing? I'd probably try it and I'd try most anything else, but I'd be cautious and I don't think I'd do things just to please my partner, I'd have to get pleasure out of them, too."

"So if I asked you to show your breasts to my best friend?"

"I can't see me marrying someone who would ask me to do that."

"Could you imagine sitting across from a relative stranger, talking to him with your shirt off?"

She laughed, "Point taken."

I got up and started taking off my clothes.

"Do you want me to take mine off, too."

"No, I don't think seeing me is going to get you anywhere near as hot as we want you so just hang on a while," I finished and sat down, not trying to hide my hard on.

tarkatony
tarkatony
254 Followers