by Clara James
“We all have needs Chris,” I reminded him. “And as for being attractive to women,” I added, smiling warmly. “You’ll find that looks aren’t the most important thing to a lot of them.”
“Well,” he mumbled hesitantly. “My experience suggests differently.” Again, a small spell of silence descended on that large room. It was quiet enough to hear a pin drop. He shuffled in his seat, drawing a hand through his thick, gelled hair. “You see, I’ve only ever...” he lost steam as things began to get tricky. “I’ve only ever...Once,” he mumbled, his eyes focused on my feet.
“You’re still young,” I reminded him. “There’s plenty of time,”
“Maybe” he said, clearly unconvinced. “But this one time, it was just pity sex. A friend I went to high school with agreed to pop my cherry, but it was...well, it wasn’t anything like I imagined.”
“First times rarely are,” I assured him, sympathetically.
“Anyway,” he sighed. “That was nearly three years ago, and since then...Nothing.”
“Okay,” I said calmly, ensuring that he knew none of these things were a problem. “So what is it that you want from me? Anything special, I mean. Do you have particular tastes, fantasies?”
He looked panicked, his eyes moving quickly to my face. “I...I just want to have sex,” he muttered weakly, seeming worried that his answer wouldn’t please me.
“That’s fine,” I nodded. “If there’s anything that you think of, just let me know. Okay?” I was getting to my feet, and as I did so, he looked a bit like a deer caught in the headlights.
“You wanna?” he blurted. “I mean, now?”
“We can do whatever you want to do, Chris,” I quickly tried to sooth his concern. “If you want to sit and talk some more, we can do that. But I think it’s one of those things that won’t get any easier no matter how long you wait.”
“Oh,” he whispered.
“You just need to relax, Chris. There’s no pressure and I promise everything will be fine.”
“O...Okay,” he stumbled.
I moved to him, placing my hand on his shoulder when I was within reach. Slowly, I moved my hand up to his neck and then caressed the underneath of his chin. This caused him to lift his face to mine. Making no sudden movements, I bent my head to his and gently pressed my lips to his.
He made no effort to kiss me back, still too scared to do anything but sit there like a stunned possum. His eyes however, showed the agitation and arousal that was brewing beneath them. His gaze drifted to my cleavage which was eye-level as I bent over him.
“You like what you see?” I asked, reaching down and slipping my fingers over the back of his right hand.
“I didn’t,” he quickly uttered, shaking his head. “I mean I was, but I didn’t mean to.”
“It’s fine,” I chuckled good-naturedly, lifting his hand leisurely to my face. I turned it over, dropping a kiss into the palm, before moving it back down to my chest. As I pressed his fingers to my left breast, he shuddered and sucked in a quaking breath. “You like that?” I asked rhetorically.
He didn’t respond verbally, but his eyes fixed on the flesh beneath his fingers and he nodded.
I guided his hand, showing him how to cup the breast, and encouraging him to massage it. “Don’t be frightened,” I told him. “It won’t bite.”
With a much need release of nerves, Chris laughed lightly at the joke. “I just, I don’t know how hard,” he said, voicing his concern.
“No two women are exactly alike, we all enjoy being touched in different ways,” I told him, still calmly guiding his hand over the globe of flesh beneath it. “But it’s best to treat them with care,” I added. “Firm, but gentle.”
“Firm, but gentle,” he echoed, committing the statement to memory, as he clenched his fingers lightly and squeezed me.
“Hmmm,” I moaned. “That’s the right kind of thing.”
He gasped at the noise of pleasure, and his breath became more labored. Glancing down, I saw that there was already a large tent in his pants. When he noticed my line of sight, he quickly tried to cover his groin with his free hand.
“There’s nothing to be ashamed of,” I assured him. “After all, that’s an important part of the process.”
“It’s just too soon,” he muttered. “I shouldn’t be this excited so soon, should I?”
“Chris,” I sighed, releasing my hold of his hand and sinking to my knees. “There are no rules to this. Everyone is different, some men take a little longer to get ready than others. Young men, like you, can usually get aroused pretty quickly. And I think just about every man who ever walked the face of the planet has had it suddenly happen when they don’t want it to.”
“So,” he said weakly. “You’re not upset?”
“Of course, I’m not,” I told him, reaching out to remove the hand that was trying unsuccessfully to mask his erection. “Why don’t you let me help you with that?” I suggested, taking his hand to his knee and depositing it there.
His pants were straining at his waist, because of his husky size. It didn’t bother me. I simply aimed for his zipper and pulled it gently down. “Just relax,” I reminded him, looking up into his concerned face once more. “Trust me.”
With his fly open, I carefully reached between the folds of fabric and found the opening of his boxers. Without the aid of my eyes, I found the tiny button and popped that open, too. It was then easy, to place my fingers around his shaft and guide it through the gaps in his clothes. I felt him tremble as I touched him, and his cock jolted even more violently when it was brought out into the open air.
It, like the rest of him, was stout, but I would guess that if he lost weight, his dick would remain the same. It had a really nice girth to it, the kind of size that could really give a woman pleasure. “Hmm,” I hummed my approval. “This is nice,” I told him.
“Really?” he asked, quickly. “You’re not just saying that, because I’m paying you?” he added gracelessly.
“No,” I insisted. “It’s a nice size, not too big but plenty big enough” I told him. “Smooth and soft,” I added, as my hand wrapped around him and stroked from the base to the head. “Straight,” I whispered, smoothing my hands back down on the return journey.
Chris was panting, his hands gripping the fabric of his pants. “Ugh, please,” he mumbled. “I don’t think I-”
I knew what was happening; knew he wanted me to stop before it did. But I thought it would be better in the long run to get it out of the way.
“Arhh,” he groaned, as his penis lengthened and four strong spurts of semen shot from the head in long ropes that splashed my face, the section of chest exposed in my dress and the dress itself. “Oh, shit,” he mumbled. “I’m so sorry, I didn’t mean to-”
“Shhh,” I hushed him, sitting up so I could kiss him on the mouth. “I told you to relax,” I smiled. “It’s perfectly natural, you said it had been a long time. There was a lot of pressure needing to be released,” I chuckled, looking deliberately down at my splattered body and clothes. “Now, when we go again, you’ll be able to last longer,” I informed him.
“Again?” he asked, breathlessly.
“Yeah,” I nodded. “We’re not done yet,” I promised him. “This is just the beginning.”
Chapter Six
Teacher
Over the following three weeks, I saw Chris on five more occasions. Paul was perfectly satisfied that I’d spent those evenings at the gym. And although I always took a sports bag with me, I was grateful it didn’t ever seem to strike him as strange that I didn’t leave the house dressed for a work out. In fact, I don’t suppose he noticed what I’d been wearing at all.
But much more importantly than what was or wasn’t registering with Paul, Chris was growing in confidence with each date. As he began to relax, he was able to keep his ejaculation at bay for longer stretches at a time. I choose to move gradually though, first treating him to leisurely periods of fellatio before moving on to penetration.
I had a hunch that the sensation of vaginal sex would be intense and he’d once again experience premature ejaculation.
I’d told him to relax and let me do the work. But, sure enough, the first time I lowered myself onto his chunky erection, he almost immediately shuddered, jerked and filled the condom he’d been wearing. However, thanks to the fifteen minutes he’d managed to last when I’d performed orally for him four days before, I was able to convince him that it was no big deal.
“You can last longer,” I told him. “You just need to get used to that pressure.”
He was panting, his fingers trembling violently, as he tried to hold onto my hips. “I...I...Oh, God,” he mumbled. “It’s so tight,” he gasped. “It was just too much, I couldn’t hold it back,” he added between deep, ragged breaths.
“It’s okay,” I soothed, gently stroking my fingers at the back of his head. “Next time it’ll be better.”
That had become my mantra, and clichéd though it may have seemed to him, he knew that it was true, because he’d seen the evidence of it. Over the course of our next two dates, we had sex four times; each one lasting a little longer than the first. During our final encounter, I began to encourage him to take control. He was worried that his size would hinder him, but I tenderly proved him wrong by showing him several positions that worked well. He seemed to particularly enjoy a sideways entry with me lying on my side, with my knees drawn up close to my chest. He was able to kneel on the mattress by my butt. After slipping a pillow under my hips, we were good to go. While able to control the speed and depth of his own thrusts, I told him to slow down or even stop if he felt the desire to ejaculate becoming too strong.
He was a wonderful student, eager to learn and, by the time he’d got to grips with controlling the response of his own body, he wanted to know how to give pleasure to a woman. I gently explained that all women are different, as are their tastes, but I gave him a brief introduction to the clitoris and the G-spot.
When we were next due to meet, he surprised me by handing over a much larger stack of bills than usual. “Umm,” I smiled, peering down at the cash, which was a thousand dollars more than I charged him for an evening. “What’s all this?” I asked, chuckling.
“It’s a parting gift,” he said, smiling a little bashfully.
“Parting?”
“Yeah,” he nodded. “See, I...umm...well, I’ve met someone and I just think it wouldn’t be right to keep meeting with you.”
I grinned warmly. I didn’t have to pretend to be pleased for him; I really was. Chris was obviously the kind of man who was desperate for the security and support of a relationship. Sure, he enjoyed sex, but to him, I think, it felt mechanical when there was no real love attached to it. He’d found himself caught between a rock and a hard place, feeling inadequate sexually had made him reluctant to get involved with anyone. He needed a guiding hand from a woman he wasn’t in love with; a woman who he didn’t have to please in order to keep. It had all worked out very well.
“I mean,” he added, “it’s not that I don’t want to see you anymore. For a while there....” he scoffed at himself, before leaving the sentence unfinished. “Anyway,” he briskly sighed. “I don’t wanna risk messing things up with this girl and it would just feel wrong, you know?”
Nodding, I dropped the cash onto the thick glass coffee table and stepped forward. “I’m so pleased for you,” I told him, smoothly wrapping both arms around his waist and pulling him toward me.
He returned the hug, but seemed uncomfortable. It was only a second before he was pulling back.
As he did, I realized what the problem was – a huge erection. “Well,” I chuckled. “I think someone else wants to say goodbye.” I reached for his belt, but he quickly stepped back.
“I can’t,” he said. “It really has to end now. I don’t want cheat on this girl.”
“But,” I smiled, jerking my thumb over my shoulder toward my purse. “You’ve paid me for tonight. And some!”
“Yeah,” he nodded, smiling. “I wanted to thank you, for everything.” Drawing his fingers through his always perfectly style hair, he shuffled awkwardly on the spot. “I know I owe you so much more than that, but I hope it goes someway to repaying you.”
I didn’t see Chris again after that. I never found out how things turned out with his girlfriend. I hope they’re still together and he’s found happiness. He was a sweet soul; nothing like I’d expected when I realized he was a rich, young man who had never, and would never, have to work a day in his life. Some men stay with me, I still think about them often and I wish I could have met them under different circumstances – Chris is one of those men.
Weeks quickly turned into months and as the late summer heat gave way to a decidedly chilly fall, I was probably happier than I’d ever been in my life. Paul hadn’t been away for several weeks, but he still spent a lot of time at the office and very little at home. There were a couple of occasions when the lack of opportunity for his clandestine affairs caused him to try to instigate sex with me. The first time, I’d told him I had a mild bladder infection. A complete lie, but it was certainly enough to put him off the idea of making love. The second time, almost a month later, Paul had stood behind me while I was brushing my hair. Gradually, he rubbed his fingers over my shoulders, before working his way around to my breasts. It was Dylan who saved the day by barging into our bedroom without knocking, as had become his habit.
“Damn it,” Paul yelled, his hands snapping away from me and his whole body moving angrily to the doorway. “How many times?” he bellowed.
Poor Dylan looked wide-eyed between his furious father and me. This time, quite the opposite from being upset with him, I was grateful.
“What’s the matter sweetie?” I asked, slowly getting up from the stool at my dressing table and calmly approaching.
Paul’s anger was not abating. “I’m serious, Dylan. How many times?”
Gripping Paul’s arm, I coaxed him away from our startled son. “Let me handle this,” I urged.
“Because you’ve handled it so fucking well in the past?” he shouted, quite loudly enough for the neighbors to hear, never mind our four-year-old, who was standing not three feet away.
I was about to say something about his choice of language, but with a huff of resignation, I simply turned away from him and offered my open right hand to my little boy.
Dylan took it obediently, and let himself be led from the bedroom. “Why is Daddy so mad at me?” he whispered as we walked a little way down the hall.
“Oh, it’s not just you, sweetheart,” I shook my head. “He’s mad at me, too. He’s just in a bad mood, that’s all.”
“I’m sorry that I didn’t knock,” he dolefully added. “I thought I saw something in my room and...and I was scared, so I just-”
“It’s okay,” I quickly offered. “I know you didn’t mean any harm. Dad knows that, too. He just needs some time to calm down.”
I thoroughly checked Dylan’s room for any signs of monsters and ghosts. There was nothing, and I attempted to explain what he thought he saw by gesturing to the shadows that came from moonlight filtering through the bottom of his curtains. Eventually, he seemed to believe me, and climbed back into bed.
When I returned to our bedroom, the door was slightly ajar. I thought I heard a breathless pant, so didn’t waltz right in. Instead, I carefully bent my head to the door and sneaked a peak through the gap. I could only really see part of Paul’s back. He was sitting in front of the computer and I could see his hand pumping furiously at his lap. Leaving him to expel some of his desires, and hoping he wouldn’t still be interested in me afterward, I tiptoed downstairs and made some chamomile tea.
At around that time, I was starting to see some light at the end of the tunnel. I had tens of thousands of dollars stashed away in an account under my own name. I was so close to being able to finally leave Paul that I’d begun looking at houses and apartments online. I’d estimated I needed to work for another month,
maybe two in order to be completely settled financially. Then, I would be able to start looking for a ‘regular’ job; one that I could work part time. However, I had also considered the possibility of going back to school. If I got a degree, I’d be able to get a much better paying ‘regular’ job. I didn’t yet know what subject I’d study, but it was an idea I was becoming fonder and fonder of.
With some rough calculations, that meant maybe another six months escorting and living under Paul’s roof. Still, by summer of the following year, I would be free and in a much better position to get my life on track – with enough money to pay a mortgage and bills for a couple of years, and cover the cost of college tuition.
The positive news was that I now had four regular clients: submissive Steven, who was always a lot of fun; Marty, who was in his early fifties and always wanted to talk for three hours and then fuck for five minutes, which suited me fine; Tom, a young man who had the stamina of a marathon runner; and Damon, who had been in a motorcycle accident and was confined to a wheelchair. Damon had been told that his spinal injury wouldn’t allow him to ever experience sexual sensations. However, the doctors were wrong – and he lapped up every single moment of that pleasure with a fervor I’d never seen in any other man.
And then, of course, there were the one-offs; the men who were drifting through the state on business. All told, I was working at least one night per week; sometimes two and, at very busy times, I’d have three dates in a week. When Paul was around, it was easy to claim I was heading out to a late night gym class. The now odd times he was spending away, I’d take the kids to their grandparents (my folks or Paul’s), or arrange a sleepover at friends. When I was really stuck, or didn’t want to incite the suspicion of Paul’s Mom, I called on Becky, the babysitter I’d used for years.
