5.   Poor Little Rich Boy

One of the questions I’m most often asked is if I ever fall for the guys I talk to, or if I ever feel like I make real connections with them. Sometimes I do. The relationships actually become quite complex; the callers know that I’m a phone sex operator and that they’re paying customers, but the intimacy is real nonetheless. They are not just clients – they’re friends and even lovers.

Paul was my first regular caller, and the first person I ever spoke to for an hour or more at a time. He’s in his late 20s, divorced, no children, and he’s apparently obscenely wealthy. At first I was skeptical when he told me about his money, but now I’m not so sure. He spent well over a thousand dollars talking to me in the first few weeks, and never batted an eye.

I met him in a chatroom. He seemed nice enough, though a little dull. No, he’d never called a phone sex girl before, he said. I tried to ease my way out of the conversation.

“You’re leaving?” he asked.

“I’d love to stay and talk to you,” I answered without any real conviction, “but you don’t seem very interested.”

“How do you know that?” he shot back. “Maybe I’m just shy.” He had a point there.

He did call that night, and he was extremely quiet. He was fine when we were just chatting, but once we started on the actual phone sex, he said almost nothing and made almost no noise. I could barely tell when he climaxed. The few comments he made were all about how beautiful I was and how much he liked a woman to be in charge.

I couldn’t read him at all. He was clearly aroused, and I led the way without being especially domineering, which he also didn’t want. He was essentially passive throughout the experience, and when at one point I suggested that he might want to pull me down and fuck me, he said softly, “If that’s what you want me to do.”

I sensed somehow that it was not what he wanted, so I quickly suggested that I could instead take him in my mouth. He seemed relieved, and agreed that yes, he would like that better.

It was a somewhat sweet, somewhat awkward call – the early conversation had been pleasant – but I didn’t expect to hear from him again. Nonetheless, I sent him my standard little e-mail thank you note and a sexy picture, teasing him just a bit about how quiet he’d been.

I got an unexpected e-mail message from him the next day, doubly surprising because he was supposed to have left on vacation for the weekend. He’d been in a car accident and was stuck at home with no car, and a mass of cuts and bruises. In the note he thanked me for taking his phone virginity, and ended with, “Know any nurses who might be able to take care of me this weekend?”

Hmm. So he enjoyed himself after all. I figured that a nurse fantasy might be right up his alley because he’s so passive. I wrote him back a teasing e-mail about how he should come in for a check-up and a sponge bath, and that the procedure was so delicate that I might need to tie him with bandages to the bed just to insure that he didn’t injure himself. In the letter I addressed him as “Mr. Johnson,” as if I were his nurse.

He wrote me back, practically panting, making an appointment with Nurse Kristi for treatment later that evening. He was also mightily impressed that I remembered his last name. I decided not to point out that I had just talked to him the day before and I had his name and credit card number written down in my notebook. But I smiled, enjoying the idea of talking to the same person two nights in a row, and feeling more comfortable that he liked me.

Suddenly I had a panic attack, realizing that I had no idea what a typical nurse fantasy would be like. Most of my life I’ve been medical-phobic. Medical talk makes me nervous to the point where I’ve even refused to watch television shows like ER. Doctor sex scenes have always been on my “no way” list, so my medical-fantasy imagination file was mostly blank. And with Mr. Passive, I knew I’d need to do most of the talking.

I decided to take a look through the alt.sex.stories newsgroup on the Internet – surely there would be medical fantasies there! I’m creative, and I figured that if I could read a hot one or two,I could wing it.

It turned out to be much more difficult than I expected. Most of the medical stories I found involved lots of torment and humiliation. I found Sadistic Nurse (Parts 1-13), Doctor’s Torture Chamber and assorted stories about painful medical experiments. Not one single sweet, caring-but-sexy nurse.

I’m not good at this. I don’t generally associate sex with nurturing. I like it hot and rough. I stumbled on a bit of temperature taking and filed it away in the back of my head – I didn’t know if he’d like that. I also wrote down “latex gloves” and “ice bath” on a notepad, and then shut down the computer. I’d just play it by ear.

The call itself was uneventful for me, though a milestone, I think, for him. He enjoyed being completely quiescent, with no pressure to participate. In fact, I told him not to participate, but just to relax and accept the treatment. If I’d thought about it at that time, I would have pretended to give him an injection of a muscle relaxant to help him along.

Basically I described giving him a full body massage, using lots of fake medical dialogue, followed by nurse-on-top sex. He even let me take his temperature and seemed to enjoy it. At the same time I encouraged him to verbalize, to moan, to make some noise. I told him how sexy I found it to listen to his arousal, and how much I wanted to hear him come. He wasn’t exactly talkative, but he relaxed a little, and I did hear his orgasm. I counted that as a major victory.

Just after we were done, I said, “Well, I think that went well, Mr. Johnson, but you will definitely have to come back for a follow-up treatment.” He burst out laughing, that exhausted, sated, lover’s laugh.

For the next week we chatted online whenever we saw each other. I teased him and turned him on, and generally considered it my duty to leave him with a raging erection every time he got onto his computer.

After the Nurse Kristi scene, Paul loosened up considerably, and we started chatting online on a regular basis. I was a bit concerned about spending non-paid time online, but as someone who had called two days in a row, he was the closest thing I had to a regular caller. He deserved some slack.

It’s an interesting thing, this being a professional friend. I’ve met a couple of people I genuinely like, and a lot of people I like reasonably well. Paul is not someone I’d choose for a friend in my everyday life, but he’s amusing and intelligent, so he’s easy to entertain. He’s constantly amazed at how well we get along; of course we do – I only show him the parts of myself that I know he’d like.

He has attributes I can’t stand – he’s got a big male-chauvinist streak, and if I were able to be myself, I’d never let him get away with some of the crap he spouts. His loves to watch wrestling and porn, and he thinks that only people with absolutely perfect bodies should allow themselves to be seen undressed. He also seems to be stuck in that college phase of  “let’s go out drinking with the guys” as his major form of entertainment.

On the other hand, he seems to be a genuinely good-hearted person, reasonably charming, sad about his marriage ending, sorry he and his wife had no children, considerate of his employees, and concerned for his parents.

He fell head over heels in love with Kristi, to the point where I started to worry. He told his friends about me and showed them pictures. He started dropping “If you ever came up here…” references into conversations.

I wrote to Trisha, the boss, for advice, because I didn’t know how to react. I didn’t want to give him the impression that a real-life meeting was even remotely possible. But if I did what my honest gut told me to do – interrupt and remind him that it’s absolutely never going to happen – I’d probably lose him as a client. And it might be losing a client for no reason. Maybe he was just enjoying the fantasy, not becoming a stalker.

She was helpful. Lots of guys fall for phone sex girls, apparently. There are men who call her for hundreds of minutes a week, she said. If he keeps mentioning real life, she suggested that I just don’t react – keep talking as if I didn’t hear him. That’s pretty much what I’d been doing. If it goes further, explain that my contract forbids me to meet clients. If that doesn’t work, remind him that what I do is about fantasy, not reality.

Do not under any circumstances tell him the truth about the pictures, she warned. The guy might say that he doesn’t care if it’s really you or not, but he does. Telling them the truth is the quickest way to get a whole bunch of charge-backs.

I kept ignoring Paul’s comments, and after a short time he re-connected with the boundaries. He started to tease me about wanting to be my official favorite client. That was easier to handle.

In some ways I still felt an occasional twinge about lying to him. Don’t get me wrong, I know that it was me – the real me – that he was interested in talking to, but it was some combination of Kristi and me that he liked. He’s a very visual person, and he was obsessed with Kristi’s body, muscles, flat stomach, and fabulous red hair. I may have been the one who fulfilled his fantasies, but Kristi was his fantasy. The look was very, very important to him. But even so, I became his phone lover and confidante, and I enjoyed it. He paid, and he was pleasant, and the sex was hot. This was a good customer.

Amusing story: he went out with an ex-girlfriend one night, slept with her, and as they were falling asleep, he called her Kristi. He’s lucky she had a sense of humor about it.

Anyhow, back to our encounters, which grew more erotic and wild each time.

The third time he called was the real breakthrough. We spoke for over an hour, the first time I’d ever done a call that long. We just chatted for at least 30 minutes, about life, phone sex, his ex-wife and what went wrong with his marriage, his business, his tattoos, how hot my red hair makes him – lots of things.

I asked him about his fantasies. He’d been insistent that he doesn’t have many wild fantasies, but I never believed him – he’s too sexually open for that to be true. He doesn’t seem to have any particular fetishes, but he’s certainly interested in all things kinky.

I coaxed a bit, and he admitted he had a recurring fantasy about being picked up by a gorgeous woman in a bar. I asked him to describe the setting, and to my surprise, he did so eagerly and in detail. He was sitting on a barstool, in faded jeans and no shirt (hell, it’s a fantasy), on a warm summer night.

“Then what happens?” I asked softly.

He started telling the story, and it was vivid. A tall, slender, beautiful woman approaches him, lures him away from the bar, and makes love to him, mesmerizing him somehow.

His description was erotic; I enjoyed it and told him so.

I caught a low mumble. “You know how much I like to be…”

I kept my voice soft, persuasive. “Like to be what, sweetie?”

“Bitten,” he answered low.

I remembered. He’d reacted intensely anytime I mentioned biting. I made encouraging noises.

“And so… I’ve always fantasized… about meeting…” he trailed off again.

I got it. “A gorgeous vampire.”

He breathed sharply. “Yesssssss.”

“Mmmmmmmm, that sounds sexy to me,” I whispered.

He didn’t answer.

“So go on,” I said. “You’re sitting at the bar. And then?”

It sounded as if he shook himself off. “I hear this clicking noise behind me, like high heels.”

If I’ve noticed one near-universal so far about submissive or passive men, this is it: the clicking sound of high heels. One guy asked me to “please please please put on a pair of high heels” so he could hear me walk. I obliged, and the sound really sent him.

“I feel a presence behind me. And I turn around on the stool,” he continued, “and I see… you… your red hair…”

“What am I wearing?” I encouraged him.

It’s difficult to convey the intensity of this conversation. Neither of us was speaking in our regular voice. It was low and husky and intimate.

“Boots,” he said, gasping a bit. “High boots.”

“Yes,” I agreed. “Shiny black leather boots that come up to mid-thigh….”

He moaned.

“With high spiked heels,” I went on.

His breath rasped. “Oh god,” he said. “I can just see you there.”

I kept talking, slowly, softly. “I’m wearing a short black dress, sleeveless and clingy… you can see that I’m not wearing a bra…”

We were both heated up by then.

“And your hair…” he said. He’s obsessed with the hair.

“Yes,” I agreed. “My long, red, hair falling all over my shoulders, my skin looking so pale…”

Unintelligible noises.

“You feel me coming up behind you…and you turn and see me there…watching you…”

“Yes, yes, I see you….” he whispered.

“I take a step closer,” I said, “and reach out one hand towards you, towards your chest. Then I run my fingers up, and tease your nipple with a long, red nail.”

“Oh god…”

“I step even closer, and slide my other hand up your bare chest… feeling your warm skin, trailing my hand up your chest to your neck, your chin, your lips…”

“I’m paralyzed,” he whispered. “I want to touch you, kiss you, but I can’t move at all.”

“I lean forward,” I said. “Even closer, and you can smell my perfume and me, and my lips are only a few inches from yours…”

Inarticulate moans across the phone line.

“I want to taste you,” I murmured.

“Oh yes, god yes,” he said.

“I lean forward and brush your lips with mine…letting my tongue snake out to lick your lips…kissing you softly…and then pressing my lips harder against you, letting you feel my teeth… and then…I press my teeth into your lower lip, cutting your lip, letting your blood spill over my lips into my mouth…”

“Ahhhhhhhhhhhhhhhhhhh…”

I’ve never found vampire erotica appealing, but at that moment I was right there with him. At that moment, biting his lip and licking the blood seemed like the most erotic thing in the universe to me.

I had an image in my mind, from a movie I saw about ten years ago. I think it was just called Gothic. It was about Mary Shelley and it was halfway between pornography and horror. I remember absolutely nothing about the movie except one image of a man leaning down to kiss a woman’s neck and then opening his mouth to the camera to reveal his teeth covered with her blood. In the context of the movie, I found the image incredibly erotic. It was the first time I’d ever found the blood/sex combination to be exciting, and a friend and I had a long talk about it. I remember it clearly.

That was the image I had in my mind that night on the phone: a handsome young actor with teeth covered in blood, in bed with a beautiful young woman.

“You’re mine now,” I murmured to my own young, handsome victim. “I have your blood inside me.”

Where did I get this dialogue? I have no idea. But it was really doing it for him, and truth to tell, it was giving me a charge as well. All I know is, at that moment our relationship changed. I was no longer just a phone sex babe. I took this secret wisp of a fantasy from his head and made it real for him. Not only that, it made me hot too, and he must have known that.

“Shall we… go somewhere more private?” the vampiress suggested.

A long moment.

“Yes,” he whispered. “Yes, I know the perfect place.”

“Mmmmmmm,” I whispered. “Let’s go then.”

He described taking my hand, bringing me outdoors to a secluded field by a lake. His words made me visualize the darkness, the enormous tree, the moon, the sounds of birds and animals, the wind. I was completely caught up in the fantasy with him. As I’m writing this, I realize that I invented an image in my head – a ramshackle and abandoned farmhouse in view, something he and I never discussed.

He kissed me in the moonlight, wrapping me in his arms, touching my body and my hair feverishly. I stepped back from him and pulled my dress over my head, tossing it aside.

“I stand in front of you,” I murmured, “just in my boots, hair falling down over my nipples.”

Memory is a strange thing. I don’t have any idea how we got from there to the ground, with him facedown and naked in the grass.

“I approach you,” I said, “and stand over you, straddling you…I drop to my knees, pressing my wet pussy against the small of your back.”

He moaned louder.

“Can you feel me?” I asked. “Can you feel against your bare skin?”

“Oh yes, oh god, oh yes…”

I described running my hands up and down over his back, gripping his sides hard, digging my nails in, and scratching. I told him how I leaned forward and rubbed my hard little nipples against him, sliding my arms around his chest and squeezing him.

He had been an active participant in the description earlier, but he was less than coherent now.

“I let my hair fall forward all over your bare back and neck. And I lean forward, open my mouth, and sink my teeth deep into your shoulder.”

He groaned loudly.

“I dig my teeth into you, scraping and scratching you with my nails…then I raise my head and sink them hard into your neck…”

I could almost feel him rocking and bucking underneath me.

As I said, memory sometimes fails, even the most intense memory. I remember nothing of that conversation past that image – Paul naked and facedown on the grass in the moonlight, with Kristi straddling him, wearing just her boots, pressing her chest into his back, her red hair streaming, and teeth sunk into his shoulder.

There must have been more, but I don’t remember any of it. He told me later that it was one of the most erotic experiences he ever had, bar none. I have to admit, I feel the same way myself.

More and more, Paul became comfortable about the idea of my being a phone sex girl whom he was paying. I was glad because I’d been feeling so guilty about him liking me so much.

He was opening up a new branch of his business and moving to a new state. He had a great time telling me about his going-away party and the little surprises his partners and friends kept sending him for the last few days.

“Besides the silly going-away gifts, I also made some new friends this week,” he said, too casually.

“What kind of friends?” I asked.

“Um, naked friends.”

We laughed. His partners sent him three strippers, three nights in a row. He’s your basic red-blooded American boy with raging hormones. Loves his beer, loves his truck, loves those naked babes.

“And last night they sent Jackie to my house,” he said.

“Jackie?”

“Yeah, Jackie is a dancer, a stripper…” he replied, “We, um, know her pretty well.”

“Oh really?” I grinned. “Just how well do you know her?”

“Well, she works in this club, you know, and we go there once in a while…”

“Ohhhh,” I teased. “Once in a while.”

He laughed loud and long. “She gets almost as much money from me as you do.”

I giggled too. Actually that comment made me feel better about the whole relationship. I’m just one of the sex indulgences. He buys porn videos, he stuffs money down g-strings, and he calls his favorite phone sex operator. All of a piece. I haven’t bewitched a poor, innocent boy into running up his credit cards.

“Does Jackie do lap dances?” I inquired.

“Oh yes.”

“Oooh, tell me about them!”

One of the hottest scenes Paul and I had was about money, in a sense. He just loves sex and all the associated toys, and he talks a lot about wanting to buy me this or that.

One night he revealed that he loves idea of watching someone masturbate, or having someone watch him.

“Did you and your ex-wife do that?” I asked. He’d often spoken about their sex life and how adventurous it was.

“Yes,” he said quietly. “A little bit.”

“Did you like it?”

“Oh yes.”

“Mmmm, I think it’s exciting to watch.”

“Yes,” he said. “I think that’s so hot. Actually, I have this fantasy…”

I tuned in right away. He rarely said that – he usually liked to let me create the scene. “Tell me.”

“I’ve always wanted to see a woman use a; you know, like a dildo… I’ve never seen that.”

“Mmmmm,” I answered. “I just happen t… have one of those.”

“No,” he said. “Not that one.”

“No?”

“No. Let me tell you my fantasy,” he began. “I want to take you to an adult store and hand you $5,000 in cash.”

“Oooh,” I said. “I like that. And…”

“Yes,” he went on. “And I want you to spend every dollar, on anything in the store you like.”

“Oh my… what a choice!”

“But of course, there’s a catch.”

“Oh?”

“Yes. Anything you buy you have to demonstrate for me.”

“Ohhh, that’s not much of a catch,” I said. “I’d do that anyway.”

He liked that.

I think I’d actually be hard-pressed to spend that kind of money in a sex store. I’m not a person who buys recklessly, and it was difficult to spend even an imaginary $5,000, though it was easier to imagine buying for Kristi – everything looks good on her.

I started easy: clothing. Lots of latex and leather and high heels. A full catsuit. A satin corset. A leather bikini. A big feather boa. A pair of black silk boxers for him, which he obligingly donned.

Then I moved to leather floggers, which would truly be my indulgence if I had $5,000 to spend. One heavy, one light, one soft, one stiff – I described the texture of each one, and what it would feel like on the skin.

Think expensive, I told myself. Videos of all kinds, one for every fetish we both liked. Some books of hot stories for me to read him. And then toys: clips and clamps, dildos and vibrators of varying sizes, a rainbow of flavored lubricants, and some big, soft feathers.

Neither of us was actually keeping track of the dollars, and soon we gave up on shopping and got to the good stuff. I ran my hands over his black silk-clad erection, and then stripped off everything I had on. I asked him if he wanted a lingerie fashion show, but he said no, he’d pick out something for me to wear this time. He held out a pair of white thigh-high stockings, but I shook my head.

“You put them on me.”

He knelt down in front of me and slid the stockings up my legs. He spent far longer than was technically necessary adjusting them, smoothing them, and letting his fingers wander. Then he slipped a pair of high-heeled shoes onto my feet. I almost lost my balance and had to hold on to his shoulders for support, accidentally pressing my hips against his face. Oops.

When the shoes were on, he sat back and just gazed up at me.

I gestured to the pile of expensive lingerie. “What next?” I asked.

“Nothing else,” he said. “I like you just like this.”

“I just picked out $2,000 of lingerie!” I protested.

“Later,” he said. “This is all I want you to wear for now.”

I felt unaccountably shy and told him so. I think he liked that best of all. He stood up and crossed the room, leaned against the wall, and watched me.

“I want to see you touch yourself,” he whispered.

Talks with him always created vivid pictures for me, and I could see him clearly, standing in the shadows, leaning back against the wall, arms crossed, eyes fixed on Kristi running her hands over her body.

Like a long-time lover, I knew what excited him. I knew which places to touch, what words to say, exactly what buttons to push to make him helpless to his own lust.

So I knew that approaching him, turning away, and grinding my ass against the front of his boxers would drive him wild. I knew that watching me suck on my finger would almost overwhelm him with lust, especially if I reminded him that he could be doing that to my nipple, or I could be doing it to his cock.

“Now,” he said. “Now use the dildo.”

I wanted to lie down on the bed, but he wouldn’t let me. He wanted me to stand in front of him. I described running the piece of silicon up and down my body, and finally pushing it inside myself little by little, working it in and out for several long, slow minutes.

He sounded as if he was in pain. He could barely speak as he told me to push it inside myself as far as it would go, and then he came up behind me and bent me over the bed. He reached inside me to pull it out, fucking me with it, making me groan and thrash, holding me down so I couldn’t move.

I don’t know why I didn’t guess his intention, but at last he pushed the dildo deep inside me and slid his cock into my ass. Anal sex turns him on almost irrationally, so I should have known. People had talked about fucking me while a dildo was in my ass before, but never the other way around. It was a wild image, and we both enjoyed ourselves tremendously.

In the quiet aftermath, as we both caught our breaths, he said softly, “I don’t care if you are faking this, it’s still incredible.”

“I’m not faking it,” I whispered back.

Not exactly. The orgasm, yes. But money or no money, the sexual excitement, the heat – that was real.

Sometime after that I was telling him that I bought a new bed. He likes to chat about homey things like that. He asked if the new bed included a nice place to strap me down to.

“Of course!” I said, and indeed it does. I bought a headboard and footboard, both with lovely metal bars. Nope, not kinky, not me, just a regular bed from a regular store…

“Good,” he said. “I was going to be upset if you’d forgotten that.”

“Me too!” I exclaimed. “I’ve always wanted a bed like this one that I could get tied to.”

He started to say something, then stopped.

“What?” I asked.

“I’m glad you got it,” he said. “I feel like…”

He stopped again.

“Feel like what?”

“Like I sort of paid for part of that bed.”

I was uneasy, not sure if this was good or bad.

“Um, a big part of it,” I told him, giggling a little. It was true. As my best customer he probably paid for most of it.

“Cool,” he smiled. “I like that. Now I feel like my phone sex money has gone to do something worthwhile for you.”