This is a companion piece to "Money Well Spent," told from Sean's perspective rather than Maggie's. You shouldn't need to read the original story to "get" this one, but if you do read both, I hope they make for an interesting comparison.
I pulled into the driveway and around back to the garage per the client’s request. “Must have nosy neighbors,” I thought to myself. It wasn’t the first time I’d had to skulk around. I’m not sure what they all think they’re hiding from prying eyes, though. If anything, I look like an accountant or lawyer delivering papers to sign when I get out of my Audi with my leather messenger bag over my shoulder. I guarantee the neighbors would never guess what I really was if I were allowed to come to the front door.
“But such is the life of a male prostitute.” I sighed. The agency I worked for termed us “companions,” but whether I was called a companion, a gigolo, or an escort, the fact remained that I prostituted myself for a living.
And it’s a good living. It wasn’t my planned career path, of course, but I have a natural “gift” that causes me to be in demand. I’ve accumulated a list of clients whom I have regular appointments with in addition to a few one-offs—generally women in town on business looking for a little fun. My regulars are mostly divorcées and bored housewives, but there are some single women, too. Most are just lonely and needing to feel desirable, but some are into some truly freaky stuff.
This afternoon’s client was brand new and waiting at the open garage door as I pulled up. I always try to be punctual, but I wondered how long she had been standing there in the dark. She was either really nervous, or really horny.
I got out of my car and introduced myself, “Hi, I’m Sean. You must be...”
She cut me off, “Maggie. Just call me Maggie.”
“Alright,” I thought. “‘Maggie’ it is. I’m not really ‘Sean,’ either.”
The garage was shadowy, but I knew Maggie was staring at me intently, sizing me up. Apparently she found me acceptable because she finally invited me to follow her into the house. I didn’t get a good look at her, but it didn’t really matter, anyway. I was there to do my job regardless of what Maggie looked like.
The garage led directly into the kitchen. It took a moment for my eyes to adjust to the light after the darkness of the garage, but when they did, I found myself unprepared for what I saw. Simply put, Maggie was beautiful. Her light brown hair was thick and wavy, with golden highlights framing her face. She had high cheekbones and soft blue eyes, but I was most drawn to her lips. She didn’t have a large mouth—more like a small Cupid’s bow—but her lips were full and sensual and just begging to be kissed. She wore a pretty blouse, open at the neck to reveal just a hint of cleavage, and her jeans hugged her hips and ass perfectly. I couldn’t imagine a woman as hot as Maggie needing my services, but I sensed there must be more to the story. There was a wedding band on her finger, after all.
“Um, how does this work?” Maggie asked, her voice shaking. She was clearly unnerved, and I needed to put her at ease, or neither of us was going to have a pleasant afternoon.
I suggested we sit down and talk before the festivities commenced. Maggie offered me something to drink, and it took her quite a while in the kitchen to fetch a simple glass of water. I wondered what was running through her mind, and if she was going to back out before we had even begun.
While she was futzing in the kitchen, I looked around the living room. The furniture and décor were clearly expensive. There were photos of a pretty, blonde girl arrayed on the mantel. What I didn’t see were any photos of a happy couple.
When Maggie finally returned with my water, I invited her to join me on the couch. She did, but sat as far away from me as possible. I joked, “I don’t bite—unless you’re into that,” but Maggie clearly didn’t find me funny. I needed to figure out what made this chick tick, and fast. I took a chance, and reached out and touched her hand, “Tell me why I’m here.”
Once she started talking, it all came spilling out. She worked from home, so she was alone all day. A man had never given her an orgasm. Her husband ignored her, which I found hard to believe. If I had a woman who looked like Maggie at home, you wouldn’t be able to get me off of her. I’m a pretty good actor, and I think most of my clients buy into the fantasy I create—namely that I just can’t control myself around them—but I wouldn’t be acting with Maggie. Truth be told, I couldn’t wait to get our session started.
When she was done pouring her heart out, I used my thumb to brush a tear from her cheek. I told her she was beautiful and deserved to be treated as such. Then I committed a cardinal sin, and took money off of the table. I had to collect the agency’s fee, but I found myself promising not to collect my own cut if I failed to give her an orgasm. “What the hell am I saying?” I wondered to myself. But such was my desire for Maggie that I was willing to potentially forgo my compensation just to be with her.
Whether it was my orgasm guarantee or something else I said, I’ll never know, but Maggie rose from the couch, retrieved $250 from her purse, and handed it to me. “Let’s get started,” she said.
I hoped I didn’t seem too eager as we passed back through the kitchen on our way upstairs to her bedroom. I needed to remain in control of this encounter. I grabbed my messenger bag—my bag of tricks—because it held condoms and my “toys,” just in case she wanted to get weird.
As we walked down the hallway, Maggie closed the door to a room decked out in purples and pinks, which I assumed belonged to her daughter. I don’t know why, but that simple gesture touched me. It was as if she were trying to protect her daughter’s innocence somehow.
When we got to her bedroom, Maggie closed the door behind us and started to remove her clothes. I stopped her because I always like to be the one to take my clients’ clothes off. I’ve found being undressed really turns most women on, and it also allows me to find out how sensitive they are to my touch.
But before we got that far, Maggie’s lips beckoned. I wanted to feel her kiss, and her tongue in my mouth. “I’d really like to kiss you. Would you like that?” I asked.
“Yes,” she whispered. “I would like you to kiss me.”
I told her again how beautiful she was as I leaned in for the kiss. Her lips were as soft as they had appeared. She opened up her mouth, and I felt around eagerly with my tongue while I began to run my hands over her body. When I was done with her mouth, I transferred my attention to the hollow of her neck, which made her press her hips against me. I couldn’t help whispering in her ear, “God, you’re sexy. I want to fuck you so bad.”
I was elated when Maggie responded, “And I want you to fuck me.” In just a few minutes, she had transformed from that timid woman on the couch into a sexual being, full of need.
I started working at the buttons on her blouse, and when I had them undone, I slid it off of her shoulders. I reached behind to unhook her bra, and her small, but perfectly formed breasts came tumbling into my hands. I teased them for a while, sensing she was becoming more and more aroused.
To see if I was correct, I unfastened her jeans, and pushed them down. I slid my hand down the front of her panties and immediately knew we wouldn’t be needing any lube. Maggie seemed embarrassed, but feeling how her body was responding so strongly to my touch was incredibly powerful. I had started getting hard from our first kiss, but feeling how wet she was made my cock even firmer.
Touching Maggie made me want to feel her hands on my body, and I invited her to undress me. Keeping myself in shape is important in my line of work, so I was gratified when she stopped in the middle of removing my shirt to run her hands over my chest and abs, clearly appreciating what she felt.
Maggie was bold enough to take off my shirt, but she seemed too shy to go any farther. I decided it was time to show her what women pay me for. “Take off my pants, baby. I have a present for you.”
Feeling her finally go for my belt and fly was almost irresistible. I could tell she was a bit taken aback by my size—most women are—but I hoped that my foreskin wouldn’t be an issue. I was born in Ireland where they just don’t think about hacking off bits of your dick, and I wasn’t about to have it done now just because Americans are used to circumcised cocks.
After her initial shock, she seemed fascinated rather than repulsed, however. She took hold of my partially-erect penis with both of her hands and ran them up my shaft and back down again. She exposed the glans, and I had to start doing math in my head to avoid getting too excited too quickly.
“I don’t know where we’re going to put all that,” she said, skeptical that we would be able to comfortably have sex, but I had a feeling she would be able to handle me. Besides, I was planning on working her up to that point first.
I pulled Maggie over to the bed and relieved us both of our underwear. I situated us on the bed, spooning her in my lap, so we could start to play. To gauge how gentle or rough she wanted me to be, I asked her show me how she touched herself. After a bit of hesitation, she started to finger her clit, which made my cock surge against her back. I don’t know what it is about watching a woman pleasure herself that gets me so excited. Maybe I’m a bit of a voyeur.
Although one of her hands was occupied, both of mine were free, so as she stroked her pussy, I fondled her lovely breasts and kissed her neck. I didn’t want her to actually bring herself to orgasm, so after a few minutes I slid my hand over the top of hers and took over. I teased her to the brink several times before finally allowing her to come, which she did, hard against my hand. God, she was hot as she shuddered in ecstasy, pressing back into me, and exciting me even more.
I was feeling very pleased with myself, and planning my next move, when she broke into my thoughts, “Well, I guess you get the rest of your payment.”
“Oh, Maggie,” I thought to myself. “Why did you have to remind me what this really is?” I had been perfectly happy pretending that Maggie was mine and that we were making love because we wanted to, not because there was money involved.
“Shh, Maggie,” I admonished. “Let’s not think about that now. We still have a lot of time left, and I want to see what else I can do for you.” I moved her to the edge of the bed, spread her legs and began to lick her luscious pussy. I could feel her getting aroused again as I alternated between tonguing her clit and lapping at her slit. I wanted to give her an orgasm this way, too, but I wanted to make it even stronger than the first, so I asked if I could try and find her g-spot. Once again, she seemed skeptical, but I had confidence I would find it. Over the years, I’ve found the spots of dozens of happy clients.
I stopped licking, and began to explore her with my finger. I could tell she was getting restless when I finally found what I was looking for. Along the top wall of her vagina was the exquisite swelling. I removed my single finger and replaced it with three, filling her and exciting her g-spot even more. I bent my head and resumed sucking on her clit. Within moments, she arched her back and moaned. I had been successful again. She pushed her pussy against my hand, and clenched her thighs around me in the sexiest headlock I’ve ever been in. Feeling her climax made me want her so badly that my erection was now legendary—swollen, pulsing, massive.
“I’m sorry,” she said when she was done shaking. “It was just so intense, I couldn’t help myself.”
“No need to apologize. That’s what I’m here for.”
I immediately regretted my words. The illusion was broken. I had just made her my client again instead of my lover. I could tell she didn’t like being reminded of that fact either.
I had to get us back on track, so I stood up, and showed her how hard I was for her. “I need you Maggie. I need you like I’ve never needed a woman before.” I often say things like that to my clients, but this time I wasn’t acting, and she could see that. I was in agony from my throbbing cock, and only Maggie could relieve me.
To my complete surprise, she leaned forward and cradled my prick in her hand, then bent down and took it into her mouth, swirling her tongue around the head. I groaned with pleasure. What other woman would think about my needs in the midst of her own appointment?
What she was doing felt amazing, but I wanted our session to finish with intercourse, not me coming in her mouth. Besides, we were breaking all sorts of rules. The agency made it clear we were to have no oral-genital contact without some sort of barrier, and here Maggie was fellating me without a condom after I had gone to town on her without protection. Tasting her had been completely worth it for me, though I knew I needed to keep her safe.
I told her I wanted to be inside her, and when she took her mouth off of me, I bent down to get a condom from my bag. At least I would follow the rules for this part. I had her help me roll it on, and told her to lie back and open herself as wide as she could for me. She was still a bit uncertain, but I knew she was more than wet enough, and her previous climaxes had relaxed her muscles so penetration would be easy.
She looked so beautiful lying there waiting for me that I wanted to just take her, but I had promised to be gentle so I entered her in stages. At first, I just sank in the tip, letting her get used to my size. With my next thrust, I got my dick about halfway in, which is where I have to stop with a lot of women. I was able to get myself balls deep with my final thrust, and although I could tell I was stretching her a bit, I could also see that Maggie liked it. So did I. It’s rare that a woman can take my whole shaft, so I was so happy that gorgeous, sexy Maggie was one of the few who would be able to make my pleasure match her own.
As I got into rhythm, Maggie moved her hips up to meet mine. She was clearly into it because she kept her eyes locked on me the whole time as I supported myself above her, a gentle smile on her face. We were both getting close when she grabbed me by the ass and somehow pulled me even deeper inside of her. I was now sunk to the hilt in this incredible woman and trying desperately not to come before she did. When she squeezed her hand between us to massage her clit, I took it as my signal to let go, and I felt myself ejaculate in her over and over in the most powerful release I have ever had. Maggie shuddered and threw back her head while having her own intense orgasm.
I collapsed on top of her, sweaty and exhausted, but more satisfied than I have ever been. We stayed like that for a good, long time as our breathing slowed, and we regained our composure. I stroked her cheek, and opened my mouth to tell her I loved her when I suddenly remembered where—and what—I was. I could feel my cum leaking out between us, and I grew alarmed that the condom had failed. I didn’t know exactly how old she was, but Maggie gave every appearance of being a healthy, fertile woman. The last thing I needed was to get her pregnant.
I carefully pulled out my softening cock and was relieved to see that the condom was intact. “Sorry about that,” I said. “I guess I got a little carried away.”
“Never apologize for what just happened between us,” she reassured me.
I glanced at my watch and was disappointed to see that it was time for me to go. Maggie had gotten inside my head, and I wanted to remain with her longer and do terrible and glorious things to her. I wanted to bend her over furniture and take her from behind. Do it with her on top so I could play with her perfect breasts while she rode my cock. Sixty-nine her so I could taste her sweet pussy while she sucked me off. Throw her against the wall and take her standing up. Mostly, though, I wanted to make slow, gentle love to her, then fall asleep in her arms. But I had to remain in control, and I had to be going.
Reluctantly, I got dressed and walked downstairs. Maggie put on a robe and followed me. She opened her purse and handed me the remaining $250, cementing for both of us the fact that she was a client and could never be anything more. I knew it was for the best, still I couldn’t go without telling her that I would remember her for a long time.
As I pulled out of her driveway on my way to shower and then see one of my regulars, I called in to the agency. “I don’t think the client I just saw will be calling back, but in case she does, please don’t schedule me with her again.”
“Lord, no,” I said, and then sighed.
“Afraid of it getting too personal, huh, Sean?”
“Something like that,” I said. “Something like that.”