Earning Rachel's trust

Rachel looks sheepish and a little embarrassed at the suggestion. “No, that won’t be necessary.” She takes a deep breath. “No, I don’t have a boyfriend.” She looks like she’s fighting herself to say more. I want to ask for more information, but I don’t have the right. I’m about to ask the next question when she bursts out, “I’m still a virgin.”

At that, I’m sure the shock shows on my face, though I rein myself in as quickly as I can. Half-angry, half-pleading, and somehow also a little ashamed, Rachel lifts her tits in her hands and demands, “Do you see these?”

I want to laugh at the absurdity of the question, but I’m sure she’d take it wrong; and whatever’s going on, Rachel doesn’t deserve to be laughed at. I control myself and instead say quietly, “Rachel, of course I see them. I’m male, and I have a particular thing for perfectly-shaped large breasts. But I’ve been trying my damnedest not to look at them—to show you the respect to look you in the eyes—despite that shirt.”

To her credit, Rachel looks abashed, and more than a little ashamed of herself. She drops her eyes and mutters, “It was a test. I’m sorry, you’re right, it wasn’t fair.” She looks back up at me. “Do you want me to go change quickly?”

“That’s up to you,” I tell her. “Will you be OK if I look down in lustful admiration from time to time? If you can believe that I take you seriously and that I’m concerned about you even if I also like admiring your cleavage, then I’ll be perfectly happy. If that presses too many buttons for you, then yes, please change, because—this is an amazing challenge.”

Rachel blushes and looks oddly pleased. In a shy voice, she says, “I—I don’t mind if you look. So long as you keep talking to me.”

“Thank you,” I say, and smile. I let myself take a long look at her tits, drinking in the sight; then I look back up and say, “You’re breathtakingly beautiful, you know.” She blushes furiously and mutters something, which I decide to assume is her thanks. “That still leaves the question, though: what does having the most spectacular female body I’ve ever seen have to do with you being a virgin?”

Rachel looks angry again, though it’s different somehow. “Do you know what bra size I wear? No, of course you couldn’t. I wear a 30H.” She seems gratified to see my jaw drop. “I can’t buy those off the rack—I practically have to have them custom-built. I literally order my bras from a company that primarily serves the adult-film industry (and even from them, it’s a specialty item). You should see the junk mail I get as a result.

“I hate the idea of surgery, or I’d be tempted to have a major breast reduction. I’ve had to do some incredible back exercises, because my back has to be in great shape to lug these things around—and regular exercise is extremely difficult. Regular bras are only next to impossible for me to find. Sports bras are flat-out impossible. Seriously, I don’t know if you know how bra sizing works, but cup size is proportional to band size. My breasts are the same size cups as a 36DD, I think—but I’m only 30 inches around. That’s a six-inch difference. I exercise hard at what I can do, because these chest floats make so many kinds of exercise unbearable.”

I’m perplexed; I’m not sure what this has to do with anything—but she clearly needs to vent, so I listen attentively. “If I got any benefit out of having these things,” Rachel continues, “it would be one thing, but I don’t. The worst part is, when I started high school I was too small to need a bra. It’s really weird that my breasts grew so late, and then grew so much larger than any of my relatives have (though none of them are small). My hips were non-existent until that point, too. I’ve always been shy, and kind of a nerd, and I was generally ignored by the boys—until I hit a D-cup or so. All of a sudden, they gave my breasts all sorts of attention, and the bigger I got, the more they got. But they still weren’t interested in me, they just wanted to get their hands inside my shirt—and they were all so crude about it. I just shut them all out.

“But I still want a boyfriend, and I still have hormones; but I want—you said it—a guy who will look me in the eyes when he talks to me, not in the nipples.” Rachel flushes and looks ashamed again. “That’s why I tested you,” she says, after some effort. More naturally, she continues, “I haven’t found a boyfriend, and I haven’t had any good ideas how to look; but that doesn’t help the hormones. So when Connie mentioned you, I thought maybe you could at least help my sexual frustration.”

I’d love to take care of her relationship frustration, too, I think; but I’m smart enough not to say that. Instead, I say, “Is there someplace comfortable we could sit next to each other?”

For whatever reason, my question seems to calm Rachel a little. “Sure,” she says. “This way.” She leads me into another room with a comfortable loveseat. I sit down next to her and put an arm around her shoulders, and discover that she’s a mass of knots.

“Here,” I say, “you really need a backrub. May I?”

“Sure,” Rachel says gratefully. I get up and stand behind her and start working on the knots. After a while, she says with some surprise, “You’re really good at this.”

“I took a night class on massage at the community college when I was in high school. One of the things I tried to get the girls to notice me.” Suddenly it’s my turn to blush—Did I really just let that slip?

Fortunately, Rachel can’t see me blushing. She picks up on what I said, though, and asks, “Did it work?”

“Ummmm, no.” OK, how do I get out of this?

“Is that why you decided to try eating pussy for money?” she asks softly, pressing me.

“Well . . .”

“It’s OK,” Rachel says coaxingly, “you can trust me. I’ve told you my frustration; you can tell me yours. I’m not going to laugh at you; and there’s no one else I could tell.”

“OK, but you asked for it. It’s a long story.” As I work on her neck, shoulders, and upper back, I tell Rachel the whole thing, going back to that last get-together. When I’m done, she says softly, “I’m impressed. And I have to say, I think the girls at your high school were fools.”

“So were the guys at yours,” I reply.

Rachel blushes a little and says, “So you’re a virgin too, just like me.”

“Yes,” I say. “There’s been a challenge or two, but yes.” She ponders that in silence for a few moments. Before she can break it, I say, “You know, at this point, I could do more for you if I got some oil and you took off your shirt.”

“Trying to make sure you get a look at my tits?” Rachel teases. It’s a little awkward, but the fact that she’s trying is encouraging: it means I’m earning her trust and making her comfortable with me.

“Assuming you still want me to eat your pussy,” I reply, “I plan to do a lot more than just look at your tits. I don’t just pull down your panties, eat your pussy, and go my way. I believe in pleasuring the whole woman—waking up all your nerves and setting your whole body on fire, and only then bringing you to climax. That way, the whole experience is far more satisfying—for both of us.”